Organic electroluminescent materials and devices
Provided are organometallic compounds including a ligand L A having a structure of Also provided are formulations comprising these organometallic compounds. Further provided are OLEDs and related consumer products that utilize these organometallic compounds.
1. A compound comprising a ligand L A having a structure of
wherein:
one of Z 1 and Z 2 is C and the other is N;
each of K 1 or K 2 is independently a direct bond, O, or S;
moiety B, moiety C, and moiety D are each independently monocyclic or polycyclic ring structure containing 5-membered or 6-membered carbocyclic or heterocyclic rings;
X 1 -X 4 are each independently C or N, with at least one of X 1 or X 2 being N if both moiety B and moiety C of Formula I are monocyclic 6-membered aromatic rings;
Y is selected from the group consisting of O, S, Se, NR, CRR′, BR, BRR′, SiRR′, and GeRR′;
W is selected from the group consisting of O, S, S═O, SO 2 , NR, C═CRR′, CRR′, SiRR′, BR, BRR′, GeRR′, PR, P═O, and P═S;
each of R A , R B , R C , and R D independently represents zero, mono, or up to a maximum allowed number of substitutions to its associated ring;
each of R, R′, R A , R B , R C , and R D is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, boryl, selenyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and
any two adjacent R, R′, R A , R B , R C , or R D can be joined or fused together to form a ring, wherein the ligand L A is coordinated to a metal M by the two indicated dashed lines;
wherein M is selected from the group consisting of Ru, Os, Ir, Pd, Pt, Cu, Ag, and Au;
wherein the ligand L A can be joined with other ligands to form a tridentate, tetradentate, pentadentate, or hexadentate ligand; and
subject to the following provisos:
when moiety B in Formula I is a monocyclic ring structure that is a 5-membered heterocyclic ring that comprises a nitrogen atom as the only heteroatom, at least one of the following is true:
i) W is selected from the group consisting of O, S, S═O, SO 2 , NR, C═CRR′, SiRR′, BR, BRR′, GeRR′, PR, P═O, and P═S;
ii) one of X 3 or X 4 is N; or
iii) two R B are joined to form a fused ring;
when moiety C comprises a sulfur atom, at least one of the following is true:
iv) the compound is heteroleptic; or
v) W is selected from the group consisting of O, S, S═O, SO 2 , NR, C═CRR′, SiRR′, BR, BRR′, GeRR′, PR, P═O, and P═S;
when W is BF 2 , at least one of the following is true:
vi) X 1 is a ring atom of a 6-membered aromatic ring; or
vii) one of X 1 or X 2 is C;
if W is CRR′, at least one of the following is true:
viii) X 1 in moiety B in Formula I is a ring atom of a 5-membered aromatic ring;
ix) the compound has the structure of Formula II; or
x) the compound is a heteroleptic compound comprising at least one substituted or unsubstituted acetylacetonate ligand and moiety C is a 5-membered ring.
2. The compound of claim 1 , wherein each of R, R′, R A , R B , R C , and R D is independently a hydrogen or a substituent selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof.
3. The compound of claim 1 , wherein W is O, S, NR, CRR′, BR, BRR′, or SiRR′.
4. The compound of claim 1 , wherein Y is O, S, NR, BR, or BRR′.
5. The compound of claim 1 , wherein X 1 is C; or X 2 is C; or one of X 1 and X 2 is C and the other is N; or X 1 and X 2 are both C while one of moiety B or moiety C of Formula I is a 5-membered ring.
6. The compound of claim 1 , wherein X 3 and X 4 are both C, or X 3 is C, and X 4 is N.
7. The compound of claim 1 , wherein moiety B or moiety D is a 5-membered or 6-membered aromatic ring.
8. The compound of claim 1 , wherein moiety C each is independently a monocyclic 5-membered or 6-membered aromatic ring, or a multicyclic ring structure containing a total of two, three, four, five, six or seven fused rings containing 5-membered and 6-membered aromatic rings.
9. The compound of claim 1 , wherein the ligand L A is selected from the group consisting of:
wherein X 5 , X 6 , and X 7 are each independently C or N; Y 2 for each occurrence is independently selected from the group consisting of O, S, Se, NR, CRR′, BR, BRR′, SiRR′, and GeRR′; and each of ring Al and ring B1 is independently a 5-membered or 6-membered carbocyclic or heterocyclic ring.
10. The compound of claim 1 , wherein the ligand L A is selected from the group consisting of:
wherein:
X 5 -X 10 are each independently N or C;
Y 2 for each occurrence is independently selected from the group consisting of O, S, Se, NR, CRR′, BR, BRR′, SiRR′, and GeRR′; and
R, R′, and the remaining variables are the same as previously defined.
11. The compound of claim 1 , wherein the ligand L A is selected from the group consisting of L Ai-m wherein i=1 to 1240 and 1361 to 1560, m=1 to 18, and based on formula L Ai-1 to L Ai-18 ; L Ai-m′ wherein i=1 to 1240 and 1361 to 4420, m′=19 to 54, and based on formula L Ai-19 to L Ai-54 ; and L Ai′-m″ wherein i′=4421 to 4740, m″=55 to 69, and based on formula L Ai′-55 to L Ai′-69 , wherein each structure of L Ai-1 through L Ai-54 , and L Ai′-55 through L Ai′-69 is defined as follows:
wherein for each i in L Ai and L Ai′ , R E , G, and W are defined below:
i
R E
G
W
1
R 1
G 11
W 1
2
R 2
G 11
W 1
3
R 4
G 11
W 1
4
R 5
G 11
W 1
5
R 7
G 11
W 1
6
R 8
G 11
W 1
7
R 10
G 11
W 1
8
R 12
G 11
W 1
9
R 14
G 11
W 1
10
R 15
G 11
W 1
11
R 19
G 11
W 1
12
R 27
G 11
W 1
13
R 28
G 11
W 1
14
R 33
G 11
W 1
15
R 38
G 11
W 1
16
R 39
G 11
W 1
17
R 41
G 11
W 1
18
R 46
G 11
W 1
19
R 47
G 11
W 1
20
R 49
G 11
W 1
21
R 1
G 12
W 1
22
R 2
G 12
W 1
23
R 4
G 12
W 1
24
R 5
G 12
W 1
25
R 7
G 12
W 1
26
R 8
G 12
W 1
27
R 10
G 12
W 1
28
R 12
G 12
W 1
29
R 14
G 12
W 1
30
R 15
G 12
W 1
31
R 19
G 12
W 1
32
R 27
G 12
W 1
33
R 28
G 12
W 1
34
R 33
G 12
W 1
35
R 38
G 12
W 1
36
R 39
G 12
W 1
37
R 41
G 12
W 1
38
R 46
G 12
W 1
39
R 47
G 12
W 1
40
R 49
G 12
W 1
41
R 1
G 13
W 1
42
R 2
G 13
W 1
43
R 4
G 13
W 1
44
R 5
G 13
W 1
45
R 7
G 13
W 1
46
R 8
G 13
W 1
47
R 10
G 13
W 1
48
R 12
G 13
W 1
49
R 14
G 13
W 1
50
R 15
G 13
W 1
51
R 19
G 13
W 1
52
R 27
G 13
W 1
53
R 28
G 13
W 1
54
R 33
G 13
W 1
55
R 38
G 13
W 1
56
R 39
G 13
W 1
57
R 41
G 13
W 1
58
R 46
G 13
W 1
59
R 47
G 13
W 1
60
R 49
G 13
W 1
61
R 1
G 16
W 1
62
R 2
G 16
W 1
63
R 4
G 16
W 1
64
R 5
G 16
W 1
65
R 7
G 16
W 1
66
R 8
G 16
W 1
67
R 10
G 16
W 1
68
R 12
G 16
W 1
69
R 14
G 16
W 1
70
R 15
G 16
W 1
71
R 19
G 16
W 1
72
R 27
G 16
W 1
73
R 28
G 16
W 1
74
R 33
G 16
W 1
75
R 38
G 16
W 1
76
R 39
G 16
W 1
77
R 41
G 16
W 1
78
R 46
G 16
W 1
79
R 47
G 16
W 1
80
R 49
G 16
W 1
81
R 1
G 17
W 1
82
R 2
G 17
W 1
83
R 4
G 17
W 1
84
R 5
G 17
W 1
85
R 7
G 17
W 1
86
R 8
G 17
W 1
87
R 10
G 17
W 1
88
R 12
G 17
W 1
89
R 14
G 17
W 1
90
R 15
G 17
W 1
91
R 19
G 17
W 1
92
R 27
G 17
W 1
93
R 28
G 17
W 1
94
R 33
G 17
W 1
95
R 38
G 17
W 1
96
R 39
G 17
W 1
97
R 41
G 17
W 1
98
R 46
G 17
W 1
99
R 47
G 17
W 1
100
R 49
G 17
W 1
101
R 1
G 18
W 1
102
R 2
G 18
W 1
103
R 4
G 18
W 1
104
R 5
G 18
W 1
105
R 7
G 18
W 1
106
R 8
G 18
W 1
107
R 10
G 18
W 1
108
R 12
G 18
W 1
109
R 14
G 18
W 1
110
R 15
G 18
W 1
111
R 19
G 18
W 1
112
R 27
G 18
W 1
113
R 28
G 18
W 1
114
R 33
G 18
W 1
115
R 38
G 18
W 1
116
R 39
G 18
W 1
117
R 41
G 18
W 1
118
R 46
G 18
W 1
119
R 47
G 18
W 1
120
R 49
G 18
W 1
121
R 1
G 21
W 1
122
R 2
G 21
W 1
123
R 4
G 21
W 1
124
R 5
G 21
W 1
125
R 7
G 21
W 1
126
R 8
G 21
W 1
127
R 10
G 21
W 1
128
R 12
G 21
W 1
129
R 14
G 21
W 1
130
R 15
G 21
W 1
131
R 19
G 21
W 1
132
R 27
G 21
W 1
133
R 28
G 21
W 1
134
R 33
G 21
W 1
135
R 38
G 21
W 1
136
R 39
G 21
W 1
137
R 41
G 21
W 1
138
R 46
G 21
W 1
139
R 47
G 21
W 1
140
R 49
G 21
W 1
141
R 1
G 22
W 1
142
R 2
G 22
W 1
143
R 4
G 22
W 1
144
R 5
G 22
W 1
145
R 7
G 22
W 1
146
R 8
G 22
W 1
147
R 10
G 22
W 1
148
R 12
G 22
W 1
149
R 14
G 22
W 1
150
R 15
G 22
W 1
151
R 19
G 22
W 1
152
R 27
G 22
W 1
153
R 28
G 22
W 1
154
R 33
G 22
W 1
155
R 38
G 22
W 1
156
R 39
G 22
W 1
157
R 41
G 22
W 1
158
R 46
G 22
W 1
159
R 47
G 22
W 1
160
R 49
G 22
W 1
161
R 1
G 23
W 1
162
R 2
G 23
W 1
163
R 4
G 23
W 1
164
R 5
G 23
W 1
165
R 7
G 23
W 1
166
R 8
G 23
W 1
167
R 10
G 23
W 1
168
R 12
G 23
W 1
169
R 14
G 23
W 1
170
R 15
G 23
W 1
171
R 19
G 23
W 1
172
R 27
G 23
W 1
173
R 28
G 23
W 1
174
R 33
G 23
W 1
175
R 38
G 23
W 1
176
R 39
G 23
W 1
177
R 41
G 23
W 1
178
R 46
G 23
W 1
179
R 47
G 23
W 1
180
R 49
G 23
W 1
181
R 1
G 24
W 1
182
R 2
G 24
W 1
183
R 4
G 24
W 1
184
R 5
G 24
W 1
185
R 7
G 24
W 1
186
R 8
G 24
W 1
187
R 10
G 24
W 1
188
R 12
G 24
W 1
189
R 14
G 24
W 1
190
R 15
G 24
W 1
191
R 19
G 24
W 1
192
R 27
G 24
W 1
193
R 28
G 24
W 1
194
R 33
G 24
W 1
195
R 38
G 24
W 1
196
R 39
G 24
W 1
197
R 41
G 24
W 1
198
R 46
G 24
W 1
199
R 47
G 24
W 1
200
R 49
G 24
W 1
201
R 1
G 11
W 11
202
R 2
G 11
W 11
203
R 4
G 11
W 11
204
R 5
G 11
W 11
205
R 7
G 11
W 11
206
R 8
G 11
W 11
207
R 10
G 11
W 11
208
R 12
G 11
W 11
209
R 14
G 11
W 11
210
R 15
G 11
W 11
211
R 19
G 11
W 11
212
R 27
G 11
W 11
213
R 28
G 11
W 11
214
R 33
G 11
W 11
215
R 38
G 11
W 11
216
R 39
G 11
W 11
217
R 41
G 11
W 11
218
R 46
G 11
W 11
219
R 47
G 11
W 11
220
R 49
G 11
W 11
221
R 1
G 12
W 11
222
R 2
G 12
W 11
223
R 4
G 12
W 11
224
R 5
G 12
W 11
225
R 7
G 12
W 11
226
R 8
G 12
W 11
227
R 10
G 12
W 11
228
R 12
G 12
W 11
229
R 14
G 12
W 11
230
R 15
G 12
W 11
231
R 19
G 12
W 11
232
R 27
G 12
W 11
233
R 28
G 12
W 11
234
R 33
G 12
W 11
235
R 38
G 12
W 11
236
R 39
G 12
W 11
237
R 41
G 12
W 11
238
R 46
G 12
W 11
239
R 47
G 12
W 11
240
R 49
G 12
W 11
241
R 1
G 13
W 11
242
R 2
G 13
W 11
243
R 4
G 13
W 11
244
R 5
G 13
W 11
245
R 7
G 13
W 11
246
R 8
G 13
W 11
247
R 10
G 13
W 11
248
R 12
G 13
W 11
249
R 14
G 13
W 11
250
R 15
G 13
W 11
251
R 19
G 13
W 11
252
R 27
G 13
W 11
253
R 28
G 13
W 11
254
R 33
G 13
W 11
255
R 38
G 13
W 11
256
R 39
G 13
W 11
257
R 41
G 13
W 11
258
R 46
G 13
W 11
259
R 47
G 13
W 11
260
R 49
G 13
W 11
261
R 1
G 16
W 11
262
R 2
G 16
W 11
263
R 4
G 16
W 11
264
R 5
G 16
W 11
265
R 7
G 16
W 11
266
R 8
G 16
W 11
267
R 10
G 16
W 11
268
R 12
G 16
W 11
269
R 14
G 16
W 11
270
R 15
G 16
W 11
271
R 19
G 16
W 11
272
R 27
G 16
W 11
273
R 28
G 16
W 11
274
R 33
G 16
W 11
275
R 38
G 16
W 11
276
R 39
G 16
W 11
277
R 41
G 16
W 11
278
R 46
G 16
W 11
279
R 47
G 16
W 11
280
R 49
G 16
W 11
281
R 1
G 17
W 11
282
R 2
G 17
W 11
283
R 4
G 17
W 11
284
R 5
G 17
W 11
285
R 7
G 17
W 11
286
R 8
G 17
W 11
287
R 10
G 17
W 11
288
R 12
G 17
W 11
289
R 14
G 17
W 11
290
R 15
G 17
W 11
291
R 19
G 17
W 11
292
R 27
G 17
W 11
293
R 28
G 17
W 11
294
R 33
G 17
W 11
295
R 38
G 17
W 11
296
R 39
G 17
W 11
297
R 41
G 17
W 11
298
R 46
G 17
W 11
299
R 47
G 17
W 11
300
R 49
G 17
W 11
301
R 1
G 18
W 11
302
R 2
G 18
W 11
303
R 4
G 18
W 11
304
R 5
G 18
W 11
305
R 7
G 18
W 11
306
R 8
G 18
W 11
307
R 10
G 18
W 11
308
R 12
G 18
W 11
309
R 14
G 18
W 11
310
R 15
G 18
W 11
311
R 19
G 18
W 11
312
R 27
G 18
W 11
313
R 28
G 18
W 11
314
R 33
G 18
W 11
315
R 38
G 18
W 11
316
R 39
G 18
W 11
317
R 41
G 18
W 11
318
R 46
G 18
W 11
319
R 47
G 18
W 11
320
R 49
G 18
W 11
321
R 1
G 21
W 11
322
R 2
G 21
W 11
323
R 4
G 21
W 11
324
R 5
G 21
W 11
325
R 7
G 21
W 11
326
R 8
G 21
W 11
327
R 10
G 21
W 11
328
R 12
G 21
W 11
329
R 14
G 21
W 11
330
R 15
G 21
W 11
331
R 19
G 21
W 11
332
R 27
G 21
W 11
333
R 28
G 21
W 11
334
R 33
G 21
W 11
335
R 38
G 21
W 11
336
R 39
G 21
W 11
337
R 41
G 21
W 11
338
R 46
G 21
W 11
339
R 47
G 21
W 11
340
R 49
G 21
W 11
341
R 1
G 22
W 11
342
R 2
G 22
W 11
343
R 4
G 22
W 11
344
R 5
G 22
W 11
345
R 7
G 22
W 11
346
R 8
G 22
W 11
347
R 10
G 22
W 11
348
R 12
G 22
W 11
349
R 14
G 22
W 11
350
R 15
G 22
W 11
351
R 19
G 22
W 11
352
R 27
G 22
W 11
353
R 28
G 22
W 11
354
R 33
G 22
W 11
355
R 38
G 22
W 11
356
R 39
G 22
W 11
357
R 41
G 22
W 11
358
R 46
G 22
W 11
359
R 47
G 22
W 11
360
R 49
G 22
W 11
361
R 1
G 23
W 11
362
R 2
G 23
W 11
363
R 4
G 23
W 11
364
R 5
G 23
W 11
365
R 7
G 23
W 11
366
R 8
G 23
W 11
367
R 10
G 23
W 11
368
R 12
G 23
W 11
369
R 14
G 23
W 11
370
R 15
G 23
W 11
371
R 19
G 23
W 11
372
R 27
G 23
W 11
373
R 28
G 23
W 11
374
R 33
G 23
W 11
375
R 38
G 23
W 11
376
R 39
G 23
W 11
377
R 41
G 23
W 11
378
R 46
G 23
W 11
379
R 47
G 23
W 11
380
R 49
G 23
W 11
381
R 1
G 24
W 11
382
R 2
G 24
W 11
383
R 4
G 24
W 11
384
R 5
G 24
W 11
385
R 7
G 24
W 11
386
R 8
G 24
W 11
387
R 10
G 24
W 11
388
R 12
G 24
W 11
389
R 14
G 24
W 11
390
R 15
G 24
W 11
391
R 19
G 24
W 11
392
R 27
G 24
W 11
393
R 28
G 24
W 11
394
R 33
G 24
W 11
395
R 38
G 24
W 11
396
R 39
G 24
W 11
397
R 41
G 24
W 11
398
R 46
G 24
W 11
399
R 47
G 24
W 11
400
R 49
G 24
W 11
401
R 1
G 11
W 21
402
R 2
G 11
W 21
403
R 4
G 11
W 21
404
R 5
G 11
W 21
405
R 7
G 11
W 21
406
R 8
G 11
W 21
407
R 10
G 11
W 21
408
R 12
G 11
W 21
409
R 14
G 11
W 21
410
R 15
G 11
W 21
411
R 19
G 11
W 21
412
R 27
G 11
W 21
413
R 28
G 11
W 21
414
R 33
G 11
W 21
415
R 38
G 11
W 21
416
R 39
G 11
W 21
417
R 41
G 11
W 21
418
R 46
G 11
W 21
419
R 47
G 11
W 21
420
R 49
G 11
W 21
421
R 1
G 12
W 21
422
R 2
G 12
W 21
423
R 4
G 12
W 21
424
R 5
G 12
W 21
425
R 7
G 12
W 21
426
R 8
G 12
W 21
427
R 10
G 12
W 21
428
R 12
G 12
W 21
429
R 14
G 12
W 21
430
R 15
G 12
W 21
431
R 19
G 12
W 21
432
R 27
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1484
R 5
G 14
W 11
1485
R 7
G 14
W 11
1486
R 8
G 14
W 11
1487
R 10
G 14
W 11
1488
R 12
G 14
W 11
1489
R 14
G 14
W 11
1490
R 15
G 14
W 11
1491
R 19
G 14
W 11
1492
R 27
G 14
W 11
1493
R 28
G 14
W 11
1494
R 33
G 14
W 11
1495
R 38
G 14
W 11
1496
R 39
G 14
W 11
1497
R 41
G 14
W 11
1498
R 46
G 14
W 11
1499
R 47
G 14
W 11
1500
R 49
G 14
W 11
1501
R 1
G 15
W 11
1502
R 2
G 15
W 11
1503
R 4
G 15
W 11
1504
R 5
G 15
W 11
1505
R 7
G 15
W 11
1506
R 8
G 15
W 11
1507
R 10
G 15
W 11
1508
R 12
G 15
W 11
1509
R 14
G 15
W 11
1510
R 15
G 15
W 11
1511
R 19
G 15
W 11
1512
R 27
G 15
W 11
1513
R 28
G 15
W 11
1514
R 33
G 15
W 11
1515
R 38
G 15
W 11
1516
R 39
G 15
W 11
1517
R 41
G 15
W 11
1518
R 46
G 15
W 11
1519
R 47
G 15
W 11
1520
R 49
G 15
W 11
1521
R 1
G 19
W 11
1522
R 2
G 19
W 11
1523
R 4
G 19
W 11
1524
R 5
G 19
W 11
1525
R 7
G 19
W 11
1526
R 8
G 19
W 11
1527
R 10
G 19
W 11
1528
R 12
G 19
W 11
1529
R 14
G 19
W 11
1530
R 15
G 19
W 11
1531
R 19
G 19
W 11
1532
R 27
G 19
W 11
1533
R 28
G 19
W 11
1534
R 33
G 19
W 11
1535
R 38
G 19
W 11
1536
R 39
G 19
W 11
1537
R 41
G 19
W 11
1538
R 46
G 19
W 11
1539
R 47
G 19
W 11
1540
R 49
G 19
W 11
1541
R 1
G 20
W 11
1542
R 2
G 20
W 11
1543
R 4
G 20
W 11
1544
R 5
G 20
W 11
1545
R 7
G 20
W 11
1546
R 8
G 20
W 11
1547
R 10
G 20
W 11
1548
R 12
G 20
W 11
1549
R 14
G 20
W 11
1550
R 15
G 20
W 11
1551
R 19
G 20
W 11
1552
R 27
G 20
W 11
1553
R 28
G 20
W 11
1554
R 33
G 20
W 11
1555
R 38
G 20
W 11
1556
R 39
G 20
W 11
1557
R 41
G 20
W 11
1558
R 46
G 20
W 11
1559
R 47
G 20
W 11
1560
R 49
G 20
W 11
1561
R 1
G 2
W 1
1562
R 2
G 2
W 1
1563
R 3
G 2
W 1
1564
R 4
G 2
W 1
1565
R 5
G 2
W 1
1566
R 6
G 2
W 1
1567
R 7
G 2
W 1
1568
R 8
G 2
W 1
1569
R 9
G 2
W 1
1570
R 10
G 2
W 1
1571
R 11
G 2
W 1
1572
R 12
G 2
W 1
1573
R 13
G 2
W 1
1574
R 14
G 2
W 1
1575
R 15
G 2
W 1
1576
R 16
G 2
W 1
1577
R 17
G 2
W 1
1578
R 18
G 2
W 1
1579
R 19
G 2
W 1
1580
R 20
G 2
W 1
1581
R 21
G 2
W 1
1582
R 22
G 2
W 1
1583
R 23
G 2
W 1
1584
R 24
G 2
W 1
1585
R 25
G 2
W 1
1586
R 26
G 2
W 1
1587
R 27
G 2
W 1
1588
R 28
G 2
W 1
1589
R 29
G 2
W 1
1590
R 30
G 2
W 1
1591
R 31
G 2
W 1
1592
R 32
G 2
W 1
1593
R 33
G 2
W 1
1594
R 34
G 2
W 1
1595
R 35
G 2
W 1
1596
R 36
G 2
W 1
1597
R 37
G 2
W 1
1598
R 38
G 2
W 1
1599
R 39
G 2
W 1
1600
R 40
G 2
W 1
1601
R 41
G 2
W 1
1602
R 42
G 2
W 1
1603
R 43
G 2
W 1
1604
R 44
G 2
W 1
1605
R 45
G 2
W 1
1606
R 46
G 2
W 1
1607
R 47
G 2
W 1
1608
R 48
G 2
W 1
1609
R 49
G 2
W 1
1610
R 50
G 2
W 1
1611
R 1
G 4
W 1
1612
R 2
G 4
W 1
1613
R 3
G 4
W 1
1614
R 4
G 4
W 1
1615
R 5
G 4
W 1
1616
R 6
G 4
W 1
1617
R 7
G 4
W 1
1618
R 8
G 4
W 1
1619
R 9
G 4
W 1
1620
R 10
G 4
W 1
1621
R 11
G 4
W 1
1622
R 12
G 4
W 1
1623
R 13
G 4
W 1
1624
R 14
G 4
W 1
1625
R 15
G 4
W 1
1626
R 16
G 4
W 1
1627
R 17
G 4
W 1
1628
R 18
G 4
W 1
1629
R 19
G 4
W 1
1630
R 20
G 4
W 1
1631
R 21
G 4
W 1
1632
R 22
G 4
W 1
1633
R 23
G 4
W 1
1634
R 24
G 4
W 1
1635
R 25
G 4
W 1
1636
R 26
G 4
W 1
1637
R 27
G 4
W 1
1638
R 28
G 4
W 1
1639
R 29
G 4
W 1
1640
R 30
G 4
W 1
1641
R 31
G 4
W 1
1642
R 32
G 4
W 1
1643
R 33
G 4
W 1
1644
R 34
G 4
W 1
1645
R 35
G 4
W 1
1646
R 36
G 4
W 1
1647
R 37
G 4
W 1
1648
R 38
G 4
W 1
1649
R 39
G 4
W 1
1650
R 40
G 4
W 1
1651
R 41
G 4
W 1
1652
R 42
G 4
W 1
1653
R 43
G 4
W 1
1654
R 44
G 4
W 1
1655
R 45
G 4
W 1
1656
R 46
G 4
W 1
1657
R 47
G 4
W 1
1658
R 48
G 4
W 1
1659
R 49
G 4
W 1
1660
R 50
G 4
W 1
1661
R 1
G 2
W 11
1662
R 2
G 2
W 11
1663
R 3
G 2
W 11
1664
R 4
G 2
W 11
1665
R 5
G 2
W 11
1666
R 6
G 2
W 11
1667
R 7
G 2
W 11
1668
R 8
G 2
W 11
1669
R 9
G 2
W 11
1670
R 10
G 2
W 11
1671
R 11
G 2
W 11
1672
R 12
G 2
W 11
1673
R 13
G 2
W 11
1674
R 14
G 2
W 11
1675
R 15
G 2
W 11
1676
R 16
G 2
W 11
1677
R 17
G 2
W 11
1678
R 18
G 2
W 11
1679
R 19
G 2
W 11
1680
R 20
G 2
W 11
1681
R 21
G 2
W 11
1682
R 22
G 2
W 11
1683
R 23
G 2
W 11
1684
R 24
G 2
W 11
1685
R 25
G 2
W 11
1686
R 26
G 2
W 11
1687
R 27
G 2
W 11
1688
R 28
G 2
W 11
1689
R 29
G 2
W 11
1690
R 30
G 2
W 11
1691
R 31
G 2
W 11
1692
R 32
G 2
W 11
1693
R 33
G 2
W 11
1694
R 34
G 2
W 11
1695
R 35
G 2
W 11
1696
R 36
G 2
W 11
1697
R 37
G 2
W 11
1698
R 38
G 2
W 11
1699
R 39
G 2
W 11
1700
R 40
G 2
W 11
1701
R 41
G 2
W 11
1702
R 42
G 2
W 11
1703
R 43
G 2
W 11
1704
R 44
G 2
W 11
1705
R 45
G 2
W 11
1706
R 46
G 2
W 11
1707
R 47
G 2
W 11
1708
R 48
G 2
W 11
1709
R 49
G 2
W 11
1710
R 50
G 2
W 11
1711
R 1
G 4
W 11
1712
R 2
G 4
W 11
1713
R 3
G 4
W 11
1714
R 4
G 4
W 11
1715
R 5
G 4
W 11
1716
R 6
G 4
W 11
1717
R 7
G 4
W 11
1718
R 8
G 4
W 11
1719
R 9
G 4
W 11
1720
R 10
G 4
W 11
1721
R 11
G 4
W 11
1722
R 12
G 4
W 11
1723
R 13
G 4
W 11
1724
R 14
G 4
W 11
1725
R 15
G 4
W 11
1726
R 16
G 4
W 11
1727
R 17
G 4
W 11
1728
R 18
G 4
W 11
1729
R 19
G 4
W 11
1730
R 20
G 4
W 11
1731
R 21
G 4
W 11
1732
R 22
G 4
W 11
1733
R 23
G 4
W 11
1734
R 24
G 4
W 11
1735
R 25
G 4
W 11
1736
R 26
G 4
W 11
1737
R 27
G 4
W 11
1738
R 28
G 4
W 11
1739
R 29
G 4
W 11
1740
R 30
G 4
W 11
1741
R 31
G 4
W 11
1742
R 32
G 4
W 11
1743
R 33
G 4
W 11
1744
R 34
G 4
W 11
1745
R 35
G 4
W 11
1746
R 36
G 4
W 11
1747
R 37
G 4
W 11
1748
R 38
G 4
W 11
1749
R 39
G 4
W 11
1750
R 40
G 4
W 11
1751
R 41
G 4
W 11
1752
R 42
G 4
W 11
1753
R 43
G 4
W 11
1754
R 44
G 4
W 11
1755
R 45
G 4
W 11
1756
R 46
G 4
W 11
1757
R 47
G 4
W 11
1758
R 48
G 4
W 11
1759
R 49
G 4
W 11
1760
R 50
G 4
W 11
1761
R 1
G 2
W 21
1762
R 2
G 2
W 21
1763
R 3
G 2
W 21
1764
R 4
G 2
W 21
1765
R 5
G 2
W 21
1766
R 6
G 2
W 21
1767
R 7
G 2
W 21
1768
R 8
G 2
W 21
1769
R 9
G 2
W 21
1770
R 10
G 2
W 21
1771
R 11
G 2
W 21
1772
R 12
G 2
W 21
1773
R 13
G 2
W 21
1774
R 14
G 2
W 21
1775
R 15
G 2
W 21
1776
R 16
G 2
W 21
1777
R 17
G 2
W 21
1778
R 18
G 2
W 21
1779
R 19
G 2
W 21
1780
R 20
G 2
W 21
1781
R 21
G 2
W 21
1782
R 22
G 2
W 21
1783
R 23
G 2
W 21
1784
R 24
G 2
W 21
1785
R 25
G 2
W 21
1786
R 26
G 2
W 21
1787
R 27
G 2
W 21
1788
R 28
G 2
W 21
1789
R 29
G 2
W 21
1790
R 30
G 2
W 21
1791
R 31
G 2
W 21
1792
R 32
G 2
W 21
1793
R 33
G 2
W 21
1794
R 34
G 2
W 21
1795
R 35
G 2
W 21
1796
R 36
G 2
W 21
1797
R 37
G 2
W 21
1798
R 38
G 2
W 21
1799
R 39
G 2
W 21
1800
R 40
G 2
W 21
1801
R 41
G 2
W 21
1802
R 42
G 2
W 21
1803
R 43
G 2
W 21
1804
R 44
G 2
W 21
1805
R 45
G 2
W 21
1806
R 46
G 2
W 21
1807
R 47
G 2
W 21
1808
R 48
G 2
W 21
1809
R 49
G 2
W 21
1810
R 50
G 2
W 21
1811
R 1
G 4
W 21
1812
R 2
G 4
W 21
1813
R 3
G 4
W 21
1814
R 4
G 4
W 21
1815
R 5
G 4
W 21
1816
R 6
G 4
W 21
1817
R 7
G 4
W 21
1818
R 8
G 4
W 21
1819
R 9
G 4
W 21
1820
R 10
G 4
W 21
1821
R 11
G 4
W 21
1822
R 12
G 4
W 21
1823
R 13
G 4
W 21
1824
R 14
G 4
W 21
1825
R 15
G 4
W 21
1826
R 16
G 4
W 21
1827
R 17
G 4
W 21
1828
R 18
G 4
W 21
1829
R 19
G 4
W 21
1830
R 20
G 4
W 21
1831
R 21
G 4
W 21
1832
R 22
G 4
W 21
1833
R 23
G 4
W 21
1834
R 24
G 4
W 21
1835
R 25
G 4
W 21
1836
R 26
G 4
W 21
1837
R 27
G 4
W 21
1838
R 28
G 4
W 21
1839
R 29
G 4
W 21
1840
R 30
G 4
W 21
1841
R 31
G 4
W 21
1842
R 32
G 4
W 21
1843
R 33
G 4
W 21
1844
R 34
G 4
W 21
1845
R 35
G 4
W 21
1846
R 36
G 4
W 21
1847
R 37
G 4
W 21
1848
R 38
G 4
W 21
1849
R 39
G 4
W 21
1850
R 40
G 4
W 21
1851
R 41
G 4
W 21
1852
R 42
G 4
W 21
1853
R 43
G 4
W 21
1854
R 44
G 4
W 21
1855
R 45
G 4
W 21
1856
R 46
G 4
W 21
1857
R 47
G 4
W 21
1858
R 48
G 4
W 21
1859
R 49
G 4
W 21
1860
R 50
G 4
W 21
1861
R 1
G 2
W 28
1862
R 2
G 2
W 28
1863
R 3
G 2
W 28
1864
R 4
G 2
W 28
1865
R 5
G 2
W 28
1866
R 6
G 2
W 28
1867
R 7
G 2
W 28
1868
R 8
G 2
W 28
1869
R 9
G 2
W 28
1870
R 10
G 2
W 28
1871
R 11
G 2
W 28
1872
R 12
G 2
W 28
1873
R 13
G 2
W 28
1874
R 14
G 2
W 28
1875
R 15
G 2
W 28
1876
R 16
G 2
W 28
1877
R 17
G 2
W 28
1878
R 18
G 2
W 28
1879
R 19
G 2
W 28
1880
R 20
G 2
W 28
1881
R 21
G 2
W 28
1882
R 22
G 2
W 28
1883
R 23
G 2
W 28
1884
R 24
G 2
W 28
1885
R 25
G 2
W 28
1886
R 26
G 2
W 28
1887
R 27
G 2
W 28
1888
R 28
G 2
W 28
1889
R 29
G 2
W 28
1890
R 30
G 2
W 28
1891
R 31
G 2
W 28
1892
R 32
G 2
W 28
1893
R 33
G 2
W 28
1894
R 34
G 2
W 28
1895
R 35
G 2
W 28
1896
R 36
G 2
W 28
1897
R 37
G 2
W 28
1898
R 38
G 2
W 28
1899
R 39
G 2
W 28
1900
R 40
G 2
W 28
1901
R 41
G 2
W 28
1902
R 42
G 2
W 28
1903
R 43
G 2
W 28
1904
R 44
G 2
W 28
1905
R 45
G 2
W 28
1906
R 46
G 2
W 28
1907
R 47
G 2
W 28
1908
R 48
G 2
W 28
1909
R 49
G 2
W 28
1910
R 50
G 2
W 28
1911
R 1
G 4
W 28
1912
R 2
G 4
W 28
1913
R 3
G 4
W 28
1914
R 4
G 4
W 28
1915
R 5
G 4
W 28
1916
R 6
G 4
W 28
1917
R 7
G 4
W 28
1918
R 8
G 4
W 28
1919
R 9
G 4
W 28
1920
R 10
G 4
W 28
1921
R 11
G 4
W 28
1922
R 12
G 4
W 28
1923
R 13
G 4
W 28
1924
R 14
G 4
W 28
1925
R 15
G 4
W 28
1926
R 16
G 4
W 28
1927
R 17
G 4
W 28
1928
R 18
G 4
W 28
1929
R 19
G 4
W 28
1930
R 20
G 4
W 28
1931
R 21
G 4
W 28
1932
R 22
G 4
W 28
1933
R 23
G 4
W 28
1934
R 24
G 4
W 28
1935
R 25
G 4
W 28
1936
R 26
G 4
W 28
1937
R 27
G 4
W 28
1938
R 28
G 4
W 28
1939
R 29
G 4
W 28
1940
R 30
G 4
W 28
1941
R 31
G 4
W 28
1942
R 32
G 4
W 28
1943
R 33
G 4
W 28
1944
R 34
G 4
W 28
1945
R 35
G 4
W 28
1946
R 36
G 4
W 28
1947
R 37
G 4
W 28
1948
R 38
G 4
W 28
1949
R 39
G 4
W 28
1950
R 40
G 4
W 28
1951
R 41
G 4
W 28
1952
R 42
G 4
W 28
1953
R 43
G 4
W 28
1954
R 44
G 4
W 28
1955
R 45
G 4
W 28
1956
R 46
G 4
W 28
1957
R 47
G 4
W 28
1958
R 48
G 4
W 28
1959
R 49
G 4
W 28
1960
R 50
G 4
W 28
1961
R 1
G 2
W 36
1962
R 2
G 2
W 36
1963
R 3
G 2
W 36
1964
R 4
G 2
W 36
1965
R 5
G 2
W 36
1966
R 6
G 2
W 36
1967
R 7
G 2
W 36
1968
R 8
G 2
W 36
1969
R 9
G 2
W 36
1970
R 10
G 2
W 36
1971
R 11
G 2
W 36
1972
R 12
G 2
W 36
1973
R 13
G 2
W 36
1974
R 14
G 2
W 36
1975
R 15
G 2
W 36
1976
R 16
G 2
W 36
1977
R 17
G 2
W 36
1978
R 18
G 2
W 36
1979
R 19
G 2
W 36
1980
R 20
G 2
W 36
1981
R 21
G 2
W 36
1982
R 22
G 2
W 36
1983
R 23
G 2
W 36
1984
R 24
G 2
W 36
1985
R 25
G 2
W 36
1986
R 26
G 2
W 36
1987
R 27
G 2
W 36
1988
R 28
G 2
W 36
1989
R 29
G 2
W 36
1990
R 30
G 2
W 36
1991
R 31
G 2
W 36
1992
R 32
G 2
W 36
1993
R 33
G 2
W 36
1994
R 34
G 2
W 36
1995
R 35
G 2
W 36
1996
R 36
G 2
W 36
1997
R 37
G 2
W 36
1998
R 38
G 2
W 36
1999
R 39
G 2
W 36
2000
R 40
G 2
W 36
2001
R 41
G 2
W 36
2002
R 42
G 2
W 36
2003
R 43
G 2
W 36
2004
R 44
G 2
W 36
2005
R 45
G 2
W 36
2006
R 46
G 2
W 36
2007
R 47
G 2
W 36
2008
R 48
G 2
W 36
2009
R 49
G 2
W 36
2010
R 50
G 2
W 36
2011
R 1
G 4
W 36
2012
R 2
G 4
W 36
2013
R 3
G 4
W 36
2014
R 4
G 4
W 36
2015
R 5
G 4
W 36
2016
R 6
G 4
W 36
2017
R 7
G 4
W 36
2018
R 8
G 4
W 36
2019
R 9
G 4
W 36
2020
R 10
G 4
W 36
2021
R 11
G 4
W 36
2022
R 12
G 4
W 36
2023
R 13
G 4
W 36
2024
R 14
G 4
W 36
2025
R 15
G 4
W 36
2026
R 16
G 4
W 36
2027
R 17
G 4
W 36
2028
R 18
G 4
W 36
2029
R 19
G 4
W 36
2030
R 20
G 4
W 36
2031
R 21
G 4
W 36
2032
R 22
G 4
W 36
2033
R 23
G 4
W 36
2034
R 24
G 4
W 36
2035
R 25
G 4
W 36
2036
R 26
G 4
W 36
2037
R 27
G 4
W 36
2038
R 28
G 4
W 36
2039
R 29
G 4
W 36
2040
R 30
G 4
W 36
2041
R 31
G 4
W 36
2042
R 32
G 4
W 36
2043
R 33
G 4
W 36
2044
R 34
G 4
W 36
2045
R 35
G 4
W 36
2046
R 36
G 4
W 36
2047
R 37
G 4
W 36
2048
R 38
G 4
W 36
2049
R 39
G 4
W 36
2050
R 40
G 4
W 36
2051
R 41
G 4
W 36
2052
R 42
G 4
W 36
2053
R 43
G 4
W 36
2054
R 44
G 4
W 36
2055
R 45
G 4
W 36
2056
R 46
G 4
W 36
2057
R 47
G 4
W 36
2058
R 48
G 4
W 36
2059
R 49
G 4
W 36
2060
R 50
G 4
W 36
2061
R 1
G 2
W 37
2062
R 2
G 2
W 37
2063
R 3
G 2
W 37
2064
R 4
G 2
W 37
2065
R 5
G 2
W 37
2066
R 6
G 2
W 37
2067
R 7
G 2
W 37
2068
R 8
G 2
W 37
2069
R 9
G 2
W 37
2070
R 10
G 2
W 37
2071
R 11
G 2
W 37
2072
R 12
G 2
W 37
2073
R 13
G 2
W 37
2074
R 14
G 2
W 37
2075
R 15
G 2
W 37
2076
R 16
G 2
W 37
2077
R 17
G 2
W 37
2078
R 18
G 2
W 37
2079
R 19
G 2
W 37
2080
R 20
G 2
W 37
2081
R 21
G 2
W 37
2082
R 22
G 2
W 37
2083
R 23
G 2
W 37
2084
R 24
G 2
W 37
2085
R 25
G 2
W 37
2086
R 26
G 2
W 37
2087
R 27
G 2
W 37
2088
R 28
G 2
W 37
2089
R 29
G 2
W 37
2090
R 30
G 2
W 37
2091
R 31
G 2
W 37
2092
R 32
G 2
W 37
2093
R 33
G 2
W 37
2094
R 34
G 2
W 37
2095
R 35
G 2
W 37
2096
R 36
G 2
W 37
2097
R 37
G 2
W 37
2098
R 38
G 2
W 37
2099
R 39
G 2
W 37
2100
R 40
G 2
W 37
2101
R 41
G 2
W 37
2102
R 42
G 2
W 37
2103
R 43
G 2
W 37
2104
R 44
G 2
W 37
2105
R 45
G 2
W 37
2106
R 46
G 2
W 37
2107
R 47
G 2
W 37
2108
R 48
G 2
W 37
2109
R 49
G 2
W 37
2110
R 50
G 2
W 37
2111
R 1
G 4
W 37
2112
R 2
G 4
W 37
2113
R 3
G 4
W 37
2114
R 4
G 4
W 37
2115
R 5
G 4
W 37
2116
R 6
G 4
W 37
2117
R 7
G 4
W 37
2118
R 8
G 4
W 37
2119
R 9
G 4
W 37
2120
R 10
G 4
W 37
2121
R 11
G 4
W 37
2122
R 12
G 4
W 37
2123
R 13
G 4
W 37
2124
R 14
G 4
W 37
2125
R 15
G 4
W 37
2126
R 16
G 4
W 37
2127
R 17
G 4
W 37
2128
R 18
G 4
W 37
2129
R 19
G 4
W 37
2130
R 20
G 4
W 37
2131
R 21
G 4
W 37
2132
R 22
G 4
W 37
2133
R 23
G 4
W 37
2134
R 24
G 4
W 37
2135
R 25
G 4
W 37
2136
R 26
G 4
W 37
2137
R 27
G 4
W 37
2138
R 28
G 4
W 37
2139
R 29
G 4
W 37
2140
R 30
G 4
W 37
2141
R 31
G 4
W 37
2142
R 32
G 4
W 37
2143
R 33
G 4
W 37
2144
R 34
G 4
W 37
2145
R 35
G 4
W 37
2146
R 36
G 4
W 37
2147
R 37
G 4
W 37
2148
R 38
G 4
W 37
2149
R 39
G 4
W 37
2150
R 40
G 4
W 37
2151
R 41
G 4
W 37
2152
R 42
G 4
W 37
2153
R 43
G 4
W 37
2154
R 44
G 4
W 37
2155
R 45
G 4
W 37
2156
R 46
G 4
W 37
2157
R 47
G 4
W 37
2158
R 48
G 4
W 37
2159
R 49
G 4
W 37
2160
R 50
G 4
W 37
2161
R 1
G 1
W 1
2162
R 2
G 1
W 1
2163
R 4
G 1
W 1
2164
R 5
G 1
W 1
2165
R 7
G 1
W 1
2166
R 8
G 1
W 1
2167
R 10
G 1
W 1
2168
R 12
G 1
W 1
2169
R 14
G 1
W 1
2170
R 15
G 1
W 1
2171
R 19
G 1
W 1
2172
R 27
G 1
W 1
2173
R 28
G 1
W 1
2174
R 33
G 1
W 1
2175
R 38
G 1
W 1
2176
R 39
G 1
W 1
2177
R 41
G 1
W 1
2178
R 46
G 1
W 1
2179
R 47
G 1
W 1
2180
R 49
G 1
W 1
2181
R 1
G 3
W 1
2182
R 2
G 3
W 1
2183
R 4
G 3
W 1
2184
R 5
G 3
W 1
2185
R 7
G 3
W 1
2186
R 8
G 3
W 1
2187
R 10
G 3
W 1
2188
R 12
G 3
W 1
2189
R 14
G 3
W 1
2190
R 15
G 3
W 1
2191
R 19
G 3
W 1
2192
R 27
G 3
W 1
2193
R 28
G 3
W 1
2194
R 33
G 3
W 1
2195
R 38
G 3
W 1
2196
R 39
G 3
W 1
2197
R 41
G 3
W 1
2198
R 46
G 3
W 1
2199
R 47
G 3
W 1
2200
R 49
G 3
W 1
2201
R 1
G 5
W 1
2202
R 2
G 5
W 1
2203
R 4
G 5
W 1
2204
R 5
G 5
W 1
2205
R 7
G 5
W 1
2206
R 8
G 5
W 1
2207
R 10
G 5
W 1
2208
R 12
G 5
W 1
2209
R 14
G 5
W 1
2210
R 15
G 5
W 1
2211
R 19
G 5
W 1
2212
R 27
G 5
W 1
2213
R 28
G 5
W 1
2214
R 33
G 5
W 1
2215
R 38
G 5
W 1
2216
R 39
G 5
W 1
2217
R 41
G 5
W 1
2218
R 46
G 5
W 1
2219
R 47
G 5
W 1
2220
R 49
G 5
W 1
2221
R 1
G 6
W 1
2222
R 2
G 6
W 1
2223
R 4
G 6
W 1
2224
R 5
G 6
W 1
2225
R 7
G 6
W 1
2226
R 8
G 6
W 1
2227
R 10
G 6
W 1
2228
R 12
G 6
W 1
2229
R 14
G 6
W 1
2230
R 15
G 6
W 1
2231
R 19
G 6
W 1
2232
R 27
G 6
W 1
2233
R 28
G 6
W 1
2234
R 33
G 6
W 1
2235
R 38
G 6
W 1
2236
R 39
G 6
W 1
2237
R 41
G 6
W 1
2238
R 46
G 6
W 1
2239
R 47
G 6
W 1
2240
R 49
G 6
W 1
2241
R 1
G 9
W 1
2242
R 2
G 9
W 1
2243
R 4
G 9
W 1
2244
R 5
G 9
W 1
2245
R 7
G 9
W 1
2246
R 8
G 9
W 1
2247
R 10
G 9
W 1
2248
R 12
G 9
W 1
2249
R 14
G 9
W 1
2250
R 15
G 9
W 1
2251
R 19
G 9
W 1
2252
R 27
G 9
W 1
2253
R 28
G 9
W 1
2254
R 33
G 9
W 1
2255
R 38
G 9
W 1
2256
R 39
G 9
W 1
2257
R 41
G 9
W 1
2258
R 46
G 9
W 1
2259
R 47
G 9
W 1
2260
R 49
G 9
W 1
2261
R 1
G 10
W 1
2262
R 2
G 10
W 1
2263
R 4
G 10
W 1
2264
R 5
G 10
W 1
2265
R 7
G 10
W 1
2266
R 8
G 10
W 1
2267
R 10
G 10
W 1
2268
R 12
G 10
W 1
2269
R 14
G 10
W 1
2270
R 15
G 10
W 1
2271
R 19
G 10
W 1
2272
R 27
G 10
W 1
2273
R 28
G 10
W 1
2274
R 33
G 10
W 1
2275
R 38
G 10
W 1
2276
R 39
G 10
W 1
2277
R 41
G 10
W 1
2278
R 46
G 10
W 1
2279
R 47
G 10
W 1
2280
R 49
G 10
W 1
2281
R 1
G 25
W 1
2282
R 2
G 25
W 1
2283
R 4
G 25
W 1
2284
R 5
G 25
W 1
2285
R 7
G 25
W 1
2286
R 8
G 25
W 1
2287
R 10
G 25
W 1
2288
R 12
G 25
W 1
2289
R 14
G 25
W 1
2290
R 15
G 25
W 1
2291
R 19
G 25
W 1
2292
R 27
G 25
W 1
2293
R 28
G 25
W 1
2294
R 33
G 25
W 1
2295
R 38
G 25
W 1
2296
R 39
G 25
W 1
2297
R 41
G 25
W 1
2298
R 46
G 25
W 1
2299
R 47
G 25
W 1
2300
R 49
G 25
W 1
2301
R 1
G 26
W 1
2302
R 2
G 26
W 1
2303
R 4
G 26
W 1
2304
R 5
G 26
W 1
2305
R 7
G 26
W 1
2306
R 8
G 26
W 1
2307
R 10
G 26
W 1
2308
R 12
G 26
W 1
2309
R 14
G 26
W 1
2310
R 15
G 26
W 1
2311
R 19
G 26
W 1
2312
R 27
G 26
W 1
2313
R 28
G 26
W 1
2314
R 33
G 26
W 1
2315
R 38
G 26
W 1
2316
R 39
G 26
W 1
2317
R 41
G 26
W 1
2318
R 46
G 26
W 1
2319
R 47
G 26
W 1
2320
R 49
G 26
W 1
2321
R 1
G 27
W 1
2322
R 2
G 27
W 1
2323
R 4
G 27
W 1
2324
R 5
G 27
W 1
2325
R 7
G 27
W 1
2326
R 8
G 27
W 1
2327
R 10
G 27
W 1
2328
R 12
G 27
W 1
2329
R 14
G 27
W 1
2330
R 15
G 27
W 1
2331
R 19
G 27
W 1
2332
R 27
G 27
W 1
2333
R 28
G 27
W 1
2334
R 33
G 27
W 1
2335
R 38
G 27
W 1
2336
R 39
G 27
W 1
2337
R 41
G 27
W 1
2338
R 46
G 27
W 1
2339
R 47
G 27
W 1
2340
R 49
G 27
W 1
2341
R 1
G 28
W 1
2342
R 2
G 28
W 1
2343
R 4
G 28
W 1
2344
R 5
G 28
W 1
2345
R 7
G 28
W 1
2346
R 8
G 28
W 1
2347
R 10
G 28
W 1
2348
R 12
G 28
W 1
2349
R 14
G 28
W 1
2350
R 15
G 28
W 1
2351
R 19
G 28
W 1
2352
R 27
G 28
W 1
2353
R 28
G 28
W 1
2354
R 33
G 28
W 1
2355
R 38
G 28
W 1
2356
R 39
G 28
W 1
2357
R 41
G 28
W 1
2358
R 46
G 28
W 1
2359
R 47
G 28
W 1
2360
R 49
G 28
W 1
2361
R 1
G 1
W 2
2362
R 2
G 1
W 2
2363
R 4
G 1
W 2
2364
R 5
G 1
W 2
2365
R 7
G 1
W 2
2366
R 8
G 1
W 2
2367
R 10
G 1
W 2
2368
R 12
G 1
W 2
2369
R 14
G 1
W 2
2370
R 15
G 1
W 2
2371
R 19
G 1
W 2
2372
R 27
G 1
W 2
2373
R 28
G 1
W 2
2374
R 33
G 1
W 2
2375
R 38
G 1
W 2
2376
R 39
G 1
W 2
2377
R 41
G 1
W 2
2378
R 46
G 1
W 2
2379
R 47
G 1
W 2
2380
R 49
G 1
W 2
2381
R 1
G 3
W 2
2382
R 2
G 3
W 2
2383
R 4
G 3
W 2
2384
R 5
G 3
W 2
2385
R 7
G 3
W 2
2386
R 8
G 3
W 2
2387
R 10
G 3
W 2
2388
R 12
G 3
W 2
2389
R 14
G 3
W 2
2390
R 15
G 3
W 2
2391
R 19
G 3
W 2
2392
R 27
G 3
W 2
2393
R 28
G 3
W 2
2394
R 33
G 3
W 2
2395
R 38
G 3
W 2
2396
R 39
G 3
W 2
2397
R 41
G 3
W 2
2398
R 46
G 3
W 2
2399
R 47
G 3
W 2
2400
R 49
G 3
W 2
2401
R 1
G 5
W 2
2402
R 2
G 5
W 2
2403
R 4
G 5
W 2
2404
R 5
G 5
W 2
2405
R 7
G 5
W 2
2406
R 8
G 5
W 2
2407
R 10
G 5
W 2
2408
R 12
G 5
W 2
2409
R 14
G 5
W 2
2410
R 15
G 5
W 2
2411
R 19
G 5
W 2
2412
R 27
G 5
W 2
2413
R 28
G 5
W 2
2414
R 33
G 5
W 2
2415
R 38
G 5
W 2
2416
R 39
G 5
W 2
2417
R 41
G 5
W 2
2418
R 46
G 5
W 2
2419
R 47
G 5
W 2
2420
R 49
G 5
W 2
2421
R 1
G 6
W 2
2422
R 2
G 6
W 2
2423
R 4
G 6
W 2
2424
R 5
G 6
W 2
2425
R 7
G 6
W 2
2426
R 8
G 6
W 2
2427
R 10
G 6
W 2
2428
R 12
G 6
W 2
2429
R 14
G 6
W 2
2430
R 15
G 6
W 2
2431
R 19
G 6
W 2
2432
R 27
G 6
W 2
2433
R 28
G 6
W 2
2434
R 33
G 6
W 2
2435
R 38
G 6
W 2
2436
R 39
G 6
W 2
2437
R 41
G 6
W 2
2438
R 46
G 6
W 2
2439
R 47
G 6
W 2
2440
R 49
G 6
W 2
2441
R 1
G 9
W 2
2442
R 2
G 9
W 2
2443
R 4
G 9
W 2
2444
R 5
G 9
W 2
2445
R 7
G 9
W 2
2446
R 8
G 9
W 2
2447
R 10
G 9
W 2
2448
R 12
G 9
W 2
2449
R 14
G 9
W 2
2450
R 15
G 9
W 2
2451
R 19
G 9
W 2
2452
R 27
G 9
W 2
2453
R 28
G 9
W 2
2454
R 33
G 9
W 2
2455
R 38
G 9
W 2
2456
R 39
G 9
W 2
2457
R 41
G 9
W 2
2458
R 46
G 9
W 2
2459
R 47
G 9
W 2
2460
R 49
G 9
W 2
2461
R 1
G 10
W 2
2462
R 2
G 10
W 2
2463
R 4
G 10
W 2
2464
R 5
G 10
W 2
2465
R 7
G 10
W 2
2466
R 8
G 10
W 2
2467
R 10
G 10
W 2
2468
R 12
G 10
W 2
2469
R 14
G 10
W 2
2470
R 15
G 10
W 2
2471
R 19
G 10
W 2
2472
R 27
G 10
W 2
2473
R 28
G 10
W 2
2474
R 33
G 10
W 2
2475
R 38
G 10
W 2
2476
R 39
G 10
W 2
2477
R 41
G 10
W 2
2478
R 46
G 10
W 2
2479
R 47
G 10
W 2
2480
R 49
G 10
W 2
2481
R 1
G 25
W 2
2482
R 2
G 25
W 2
2483
R 4
G 25
W 2
2484
R 5
G 25
W 2
2485
R 7
G 25
W 2
2486
R 8
G 25
W 2
2487
R 10
G 25
W 2
2488
R 12
G 25
W 2
2489
R 14
G 25
W 2
2490
R 15
G 25
W 2
2491
R 19
G 25
W 2
2492
R 27
G 25
W 2
2493
R 28
G 25
W 2
2494
R 33
G 25
W 2
2495
R 38
G 25
W 2
2496
R 39
G 25
W 2
2497
R 41
G 25
W 2
2498
R 46
G 25
W 2
2499
R 47
G 25
W 2
2500
R 49
G 25
W 2
2501
R 1
G 26
W 2
2502
R 2
G 26
W 2
2503
R 4
G 26
W 2
2504
R 5
G 26
W 2
2505
R 7
G 26
W 2
2506
R 8
G 26
W 2
2507
R 10
G 26
W 2
2508
R 12
G 26
W 2
2509
R 14
G 26
W 2
2510
R 15
G 26
W 2
2511
R 19
G 26
W 2
2512
R 27
G 26
W 2
2513
R 28
G 26
W 2
2514
R 33
G 26
W 2
2515
R 38
G 26
W 2
2516
R 39
G 26
W 2
2517
R 41
G 26
W 2
2518
R 46
G 26
W 2
2519
R 47
G 26
W 2
2520
R 49
G 26
W 2
2521
R 1
G 27
W 2
2522
R 2
G 27
W 2
2523
R 4
G 27
W 2
2524
R 5
G 27
W 2
2525
R 7
G 27
W 2
2526
R 8
G 27
W 2
2527
R 10
G 27
W 2
2528
R 12
G 27
W 2
2529
R 14
G 27
W 2
2530
R 15
G 27
W 2
2531
R 19
G 27
W 2
2532
R 27
G 27
W 2
2533
R 28
G 27
W 2
2534
R 33
G 27
W 2
2535
R 38
G 27
W 2
2536
R 39
G 27
W 2
2537
R 41
G 27
W 2
2538
R 46
G 27
W 2
2539
R 47
G 27
W 2
2540
R 49
G 27
W 2
2541
R 1
G 28
W 2
2542
R 2
G 28
W 2
2543
R 4
G 28
W 2
2544
R 5
G 28
W 2
2545
R 7
G 28
W 2
2546
R 8
G 28
W 2
2547
R 10
G 28
W 2
2548
R 12
G 28
W 2
2549
R 14
G 28
W 2
2550
R 15
G 28
W 2
2551
R 19
G 28
W 2
2552
R 27
G 28
W 2
2553
R 28
G 28
W 2
2554
R 33
G 28
W 2
2555
R 38
G 28
W 2
2556
R 39
G 28
W 2
2557
R 41
G 28
W 2
2558
R 46
G 28
W 2
2559
R 47
G 28
W 2
2560
R 49
G 28
W 2
2561
R 1
G 1
W 5
2562
R 2
G 1
W 5
2563
R 4
G 1
W 5
2564
R 5
G 1
W 5
2565
R 7
G 1
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2566
R 8
G 1
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2567
R 10
G 1
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2568
R 12
G 1
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2569
R 14
G 1
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2570
R 15
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2571
R 19
G 1
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2572
R 27
G 1
W 5
2573
R 28
G 1
W 5
2574
R 33
G 1
W 5
2575
R 38
G 1
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2576
R 39
G 1
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2577
R 41
G 1
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2578
R 46
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2579
R 47
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2580
R 49
G 1
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2581
R 1
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2582
R 2
G 3
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R 4
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2584
R 5
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2585
R 7
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R 8
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2587
R 10
G 3
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2588
R 12
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2589
R 14
G 3
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2590
R 15
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2591
R 19
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2592
R 27
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2593
R 28
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2594
R 33
G 3
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2595
R 38
G 3
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2596
R 39
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2597
R 41
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2598
R 46
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2599
R 47
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2600
R 49
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2601
R 1
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W 5
2602
R 2
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2603
R 4
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2604
R 5
G 5
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2605
R 7
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2606
R 8
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R 10
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R 12
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R 14
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2610
R 15
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R 19
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2612
R 27
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2613
R 28
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R 33
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2615
R 38
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R 39
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R 41
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R 46
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R 47
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2620
R 49
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2621
R 1
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2622
R 2
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R 4
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R 5
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2625
R 7
G 6
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R 8
G 6
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2627
R 10
G 6
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R 12
G 6
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2629
R 14
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2630
R 15
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R 19
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R 27
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R 28
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2634
R 33
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2635
R 38
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2636
R 39
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2637
R 41
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2638
R 46
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R 47
G 6
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2640
R 49
G 6
W 5
2641
R 1
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W 5
2642
R 2
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2643
R 4
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2644
R 5
G 9
W 5
2645
R 7
G 9
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2646
R 8
G 9
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2647
R 10
G 9
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2648
R 12
G 9
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2649
R 14
G 9
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2650
R 15
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2651
R 19
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2652
R 27
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R 28
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R 33
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2655
R 38
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2656
R 39
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2657
R 41
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R 46
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R 47
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2660
R 49
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2661
R 1
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2662
R 2
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W 5
2663
R 4
G 10
W 5
2664
R 5
G 10
W 5
2665
R 7
G 10
W 5
2666
R 8
G 10
W 5
2667
R 10
G 10
W 5
2668
R 12
G 10
W 5
2669
R 14
G 10
W 5
2670
R 15
G 10
W 5
2671
R 19
G 10
W 5
2672
R 27
G 10
W 5
2673
R 28
G 10
W 5
2674
R 33
G 10
W 5
2675
R 38
G 10
W 5
2676
R 39
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W 5
2677
R 41
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W 5
2678
R 46
G 10
W 5
2679
R 47
G 10
W 5
2680
R 49
G 10
W 5
2681
R 1
G 25
W 5
2682
R 2
G 25
W 5
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R 4
G 25
W 5
2684
R 5
G 25
W 5
2685
R 7
G 25
W 5
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R 8
G 25
W 5
2687
R 10
G 25
W 5
2688
R 12
G 25
W 5
2689
R 14
G 25
W 5
2690
R 15
G 25
W 5
2691
R 19
G 25
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2692
R 27
G 25
W 5
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R 28
G 25
W 5
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R 33
G 25
W 5
2695
R 38
G 25
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2696
R 39
G 25
W 5
2697
R 41
G 25
W 5
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R 46
G 25
W 5
2699
R 47
G 25
W 5
2700
R 49
G 25
W 5
2701
R 1
G 26
W 5
2702
R 2
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W 5
2703
R 4
G 26
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2704
R 5
G 26
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R 7
G 26
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2706
R 8
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2707
R 10
G 26
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R 12
G 26
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R 14
G 26
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2710
R 15
G 26
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2711
R 19
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2712
R 27
G 26
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2713
R 28
G 26
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2714
R 33
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2715
R 38
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2716
R 39
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2717
R 41
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2718
R 46
G 26
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R 47
G 26
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2720
R 49
G 26
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2721
R 1
G 27
W 5
2722
R 2
G 27
W 5
2723
R 4
G 27
W 5
2724
R 5
G 27
W 5
2725
R 7
G 27
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2726
R 8
G 27
W 5
2727
R 10
G 27
W 5
2728
R 12
G 27
W 5
2729
R 14
G 27
W 5
2730
R 15
G 27
W 5
2731
R 19
G 27
W 5
2732
R 27
G 27
W 5
2733
R 28
G 27
W 5
2734
R 33
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W 5
2735
R 38
G 27
W 5
2736
R 39
G 27
W 5
2737
R 41
G 27
W 5
2738
R 46
G 27
W 5
2739
R 47
G 27
W 5
2740
R 49
G 27
W 5
2741
R 1
G 28
W 5
2742
R 2
G 28
W 5
2743
R 4
G 28
W 5
2744
R 5
G 28
W 5
2745
R 7
G 28
W 5
2746
R 8
G 28
W 5
2747
R 10
G 28
W 5
2748
R 12
G 28
W 5
2749
R 14
G 28
W 5
2750
R 15
G 28
W 5
2751
R 19
G 28
W 5
2752
R 27
G 28
W 5
2753
R 28
G 28
W 5
2754
R 33
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W 5
2755
R 38
G 28
W 5
2756
R 39
G 28
W 5
2757
R 41
G 28
W 5
2758
R 46
G 28
W 5
2759
R 47
G 28
W 5
2760
R 49
G 28
W 5
2761
R 1
G 1
W 6
2762
R 2
G 1
W 6
2763
R 4
G 1
W 6
2764
R 5
G 1
W 6
2765
R 7
G 1
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2766
R 8
G 1
W 6
2767
R 10
G 1
W 6
2768
R 12
G 1
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2769
R 14
G 1
W 6
2770
R 15
G 1
W 6
2771
R 19
G 1
W 6
2772
R 27
G 1
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2773
R 28
G 1
W 6
2774
R 33
G 1
W 6
2775
R 38
G 1
W 6
2776
R 39
G 1
W 6
2777
R 41
G 1
W 6
2778
R 46
G 1
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2779
R 47
G 1
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2780
R 49
G 1
W 6
2781
R 1
G 3
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2782
R 2
G 3
W 6
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R 4
G 3
W 6
2784
R 5
G 3
W 6
2785
R 7
G 3
W 6
2786
R 8
G 3
W 6
2787
R 10
G 3
W 6
2788
R 12
G 3
W 6
2789
R 14
G 3
W 6
2790
R 15
G 3
W 6
2791
R 19
G 3
W 6
2792
R 27
G 3
W 6
2793
R 28
G 3
W 6
2794
R 33
G 3
W 6
2795
R 38
G 3
W 6
2796
R 39
G 3
W 6
2797
R 41
G 3
W 6
2798
R 46
G 3
W 6
2799
R 47
G 3
W 6
2800
R 49
G 3
W 6
2801
R 1
G 5
W 6
2802
R 2
G 5
W 6
2803
R 4
G 5
W 6
2804
R 5
G 5
W 6
2805
R 7
G 5
W 6
2806
R 8
G 5
W 6
2807
R 10
G 5
W 6
2808
R 12
G 5
W 6
2809
R 14
G 5
W 6
2810
R 15
G 5
W 6
2811
R 19
G 5
W 6
2812
R 27
G 5
W 6
2813
R 28
G 5
W 6
2814
R 33
G 5
W 6
2815
R 38
G 5
W 6
2816
R 39
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W 6
2817
R 41
G 5
W 6
2818
R 46
G 5
W 6
2819
R 47
G 5
W 6
2820
R 49
G 5
W 6
2821
R 1
G 6
W 6
2822
R 2
G 6
W 6
2823
R 4
G 6
W 6
2824
R 5
G 6
W 6
2825
R 7
G 6
W 6
2826
R 8
G 6
W 6
2827
R 10
G 6
W 6
2828
R 12
G 6
W 6
2829
R 14
G 6
W 6
2830
R 15
G 6
W 6
2831
R 19
G 6
W 6
2832
R 27
G 6
W 6
2833
R 28
G 6
W 6
2834
R 33
G 6
W 6
2835
R 38
G 6
W 6
2836
R 39
G 6
W 6
2837
R 41
G 6
W 6
2838
R 46
G 6
W 6
2839
R 47
G 6
W 6
2840
R 49
G 6
W 6
2841
R 1
G 9
W 6
2842
R 2
G 9
W 6
2843
R 4
G 9
W 6
2844
R 5
G 9
W 6
2845
R 7
G 9
W 6
2846
R 8
G 9
W 6
2847
R 10
G 9
W 6
2848
R 12
G 9
W 6
2849
R 14
G 9
W 6
2850
R 15
G 9
W 6
2851
R 19
G 9
W 6
2852
R 27
G 9
W 6
2853
R 28
G 9
W 6
2854
R 33
G 9
W 6
2855
R 38
G 9
W 6
2856
R 39
G 9
W 6
2857
R 41
G 9
W 6
2858
R 46
G 9
W 6
2859
R 47
G 9
W 6
2860
R 49
G 9
W 6
2861
R 1
G 10
W 6
2862
R 2
G 10
W 6
2863
R 4
G 10
W 6
2864
R 5
G 10
W 6
2865
R 7
G 10
W 6
2866
R 8
G 10
W 6
2867
R 10
G 10
W 6
2868
R 12
G 10
W 6
2869
R 14
G 10
W 6
2870
R 15
G 10
W 6
2871
R 19
G 10
W 6
2872
R 27
G 10
W 6
2873
R 28
G 10
W 6
2874
R 33
G 10
W 6
2875
R 38
G 10
W 6
2876
R 39
G 10
W 6
2877
R 41
G 10
W 6
2878
R 46
G 10
W 6
2879
R 47
G 10
W 6
2880
R 49
G 10
W 6
2881
R 1
G 25
W 6
2882
R 2
G 25
W 6
2883
R 4
G 25
W 6
2884
R 5
G 25
W 6
2885
R 7
G 25
W 6
2886
R 8
G 25
W 6
2887
R 10
G 25
W 6
2888
R 12
G 25
W 6
2889
R 14
G 25
W 6
2890
R 15
G 25
W 6
2891
R 19
G 25
W 6
2892
R 27
G 25
W 6
2893
R 28
G 25
W 6
2894
R 33
G 25
W 6
2895
R 38
G 25
W 6
2896
R 39
G 25
W 6
2897
R 41
G 25
W 6
2898
R 46
G 25
W 6
2899
R 47
G 25
W 6
2900
R 49
G 25
W 6
2901
R 1
G 26
W 6
2902
R 2
G 26
W 6
2903
R 4
G 26
W 6
2904
R 5
G 26
W 6
2905
R 7
G 26
W 6
2906
R 8
G 26
W 6
2907
R 10
G 26
W 6
2908
R 12
G 26
W 6
2909
R 14
G 26
W 6
2910
R 15
G 26
W 6
2911
R 19
G 26
W 6
2912
R 27
G 26
W 6
2913
R 28
G 26
W 6
2914
R 33
G 26
W 6
2915
R 38
G 26
W 6
2916
R 39
G 26
W 6
2917
R 41
G 26
W 6
2918
R 46
G 26
W 6
2919
R 47
G 26
W 6
2920
R 49
G 26
W 6
2921
R 1
G 27
W 6
2922
R 2
G 27
W 6
2923
R 4
G 27
W 6
2924
R 5
G 27
W 6
2925
R 7
G 27
W 6
2926
R 8
G 27
W 6
2927
R 10
G 27
W 6
2928
R 12
G 27
W 6
2929
R 14
G 27
W 6
2930
R 15
G 27
W 6
2931
R 19
G 27
W 6
2932
R 27
G 27
W 6
2933
R 28
G 27
W 6
2934
R 33
G 27
W 6
2935
R 38
G 27
W 6
2936
R 39
G 27
W 6
2937
R 41
G 27
W 6
2938
R 46
G 27
W 6
2939
R 47
G 27
W 6
2940
R 49
G 27
W 6
2941
R 1
G 28
W 6
2942
R 2
G 28
W 6
2943
R 4
G 28
W 6
2944
R 5
G 28
W 6
2945
R 7
G 28
W 6
2946
R 8
G 28
W 6
2947
R 10
G 28
W 6
2948
R 12
G 28
W 6
2949
R 14
G 28
W 6
2950
R 15
G 28
W 6
2951
R 19
G 28
W 6
2952
R 27
G 28
W 6
2953
R 28
G 28
W 6
2954
R 33
G 28
W 6
2955
R 38
G 28
W 6
2956
R 39
G 28
W 6
2957
R 41
G 28
W 6
2958
R 46
G 28
W 6
2959
R 47
G 28
W 6
2960
R 49
G 28
W 6
2961
R 1
G 1
W 11
2962
R 2
G 1
W 11
2963
R 4
G 1
W 11
2964
R 5
G 1
W 11
2965
R 7
G 1
W 11
2966
R 8
G 1
W 11
2967
R 10
G 1
W 11
2968
R 12
G 1
W 11
2969
R 14
G 1
W 11
2970
R 15
G 1
W 11
2971
R 19
G 1
W 11
2972
R 27
G 1
W 11
2973
R 28
G 1
W 11
2974
R 33
G 1
W 11
2975
R 38
G 1
W 11
2976
R 39
G 1
W 11
2977
R 41
G 1
W 11
2978
R 46
G 1
W 11
2979
R 47
G 1
W 11
2980
R 49
G 1
W 11
2981
R 1
G 3
W 11
2982
R 2
G 3
W 11
2983
R 4
G 3
W 11
2984
R 5
G 3
W 11
2985
R 7
G 3
W 11
2986
R 8
G 3
W 11
2987
R 10
G 3
W 11
2988
R 12
G 3
W 11
2989
R 14
G 3
W 11
2990
R 15
G 3
W 11
2991
R 19
G 3
W 11
2992
R 27
G 3
W 11
2993
R 28
G 3
W 11
2994
R 33
G 3
W 11
2995
R 38
G 3
W 11
2996
R 39
G 3
W 11
2997
R 41
G 3
W 11
2998
R 46
G 3
W 11
2999
R 47
G 3
W 11
3000
R 49
G 3
W 11
3001
R 1
G 5
W 11
3002
R 2
G 5
W 11
3003
R 4
G 5
W 11
3004
R 5
G 5
W 11
3005
R 7
G 5
W 11
3006
R 8
G 5
W 11
3007
R 10
G 5
W 11
3008
R 12
G 5
W 11
3009
R 14
G 5
W 11
3010
R 15
G 5
W 11
3011
R 19
G 5
W 11
3012
R 27
G 5
W 11
3013
R 28
G 5
W 11
3014
R 33
G 5
W 11
3015
R 38
G 5
W 11
3016
R 39
G 5
W 11
3017
R 41
G 5
W 11
3018
R 46
G 5
W 11
3019
R 47
G 5
W 11
3020
R 49
G 5
W 11
3021
R 1
G 6
W 11
3022
R 2
G 6
W 11
3023
R 4
G 6
W 11
3024
R 5
G 6
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3430
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3475
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3476
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3478
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3480
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3481
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R 2
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R 5
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3493
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W 21
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W 21
3500
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W 21
3501
R 1
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W 21
3502
R 2
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W 21
3503
R 4
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W 21
3504
R 5
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W 21
3505
R 7
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W 21
3506
R 8
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W 21
3507
R 10
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W 21
3508
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3509
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W 21
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R 15
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R 49
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3521
R 1
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W 21
3522
R 2
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W 21
3523
R 4
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W 21
3524
R 5
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W 21
3525
R 7
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W 21
3526
R 8
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3527
R 10
G 27
W 21
3528
R 12
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W 21
3529
R 14
G 27
W 21
3530
R 15
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W 21
3531
R 19
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W 21
3532
R 27
G 27
W 21
3533
R 28
G 27
W 21
3534
R 33
G 27
W 21
3535
R 38
G 27
W 21
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4325
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4425
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4426
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4427
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4435
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4436
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4437
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4438
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4439
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4440
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4441
R 21
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4442
R 22
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4444
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4445
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4446
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4448
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4449
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4450
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W 42
4451
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4452
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4453
R 33
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4454
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4455
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4456
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4457
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4459
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4460
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R 42
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4464
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4465
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4466
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4468
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4469
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4470
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4472
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4473
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4486
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R 17
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4488
R 18
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4489
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4490
R 20
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4491
R 21
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4492
R 22
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4493
R 23
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R 24
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4495
R 25
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4496
R 26
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4497
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4498
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4502
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4503
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4504
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4505
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4506
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4507
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4508
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4509
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4523
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4526
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4527
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4528
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4529
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4530
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4531
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4532
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4533
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4534
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4535
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4536
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4548
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4551
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4554
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4556
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R 46
G 3
W 42
4559
R 47
G 3
W 42
4560
R 49
G 3
W 42
4561
R 1
G 9
W 42
4562
R 2
G 9
W 42
4563
R 4
G 9
W 42
4564
R 5
G 9
W 42
4565
R 7
G 9
W 42
4566
R 8
G 9
W 42
4567
R 10
G 9
W 42
4568
R 12
G 9
W 42
4569
R 14
G 9
W 42
4570
R 15
G 9
W 42
4571
R 19
G 9
W 42
4572
R 27
G 9
W 42
4573
R 28
G 9
W 42
4574
R 33
G 9
W 42
4575
R 38
G 9
W 42
4576
R 39
G 9
W 42
4577
R 41
G 9
W 42
4578
R 46
G 9
W 42
4579
R 47
G 9
W 42
4580
R 49
G 9
W 42
4581
R 1
G 10
W 42
4582
R 2
G 10
W 42
4583
R 4
G 10
W 42
4584
R 5
G 10
W 42
4585
R 7
G 10
W 42
4586
R 8
G 10
W 42
4587
R 10
G 10
W 42
4588
R 12
G 10
W 42
4589
R 14
G 10
W 42
4590
R 15
G 10
W 42
4591
R 19
G 10
W 42
4592
R 27
G 10
W 42
4593
R 28
G 10
W 42
4594
R 33
G 10
W 42
4595
R 38
G 10
W 42
4596
R 39
G 10
W 42
4597
R 41
G 10
W 42
4598
R 46
G 10
W 42
4599
R 47
G 10
W 42
4600
R 49
G 10
W 42
4601
R 1
G 12
W 42
4602
R 2
G 12
W 42
4603
R 4
G 12
W 42
4604
R 5
G 12
W 42
4605
R 7
G 12
W 42
4606
R 8
G 12
W 42
4607
R 10
G 12
W 42
4608
R 12
G 12
W 42
4609
R 14
G 12
W 42
4610
R 15
G 12
W 42
4611
R 19
G 12
W 42
4612
R 27
G 12
W 42
4613
R 28
G 12
W 42
4614
R 33
G 12
W 42
4615
R 38
G 12
W 42
4616
R 39
G 12
W 42
4617
R 41
G 12
W 42
4618
R 46
G 12
W 42
4619
R 47
G 12
W 42
4620
R 49
G 12
W 42
4621
R 1
G 13
W 42
4622
R 2
G 13
W 42
4623
R 4
G 13
W 42
4624
R 5
G 13
W 42
4625
R 7
G 13
W 42
4626
R 8
G 13
W 42
4627
R 10
G 13
W 42
4628
R 12
G 13
W 42
4629
R 14
G 13
W 42
4630
R 15
G 13
W 42
4631
R 19
G 13
W 42
4632
R 27
G 13
W 42
4633
R 28
G 13
W 42
4634
R 33
G 13
W 42
4635
R 38
G 13
W 42
4636
R 39
G 13
W 42
4637
R 41
G 13
W 42
4638
R 46
G 13
W 42
4639
R 47
G 13
W 42
4640
R 49
G 13
W 42
4641
R 1
G 16
W 42
4642
R 2
G 16
W 42
4643
R 4
G 16
W 42
4644
R 5
G 16
W 42
4645
R 7
G 16
W 42
4646
R 8
G 16
W 42
4647
R 10
G 16
W 42
4648
R 12
G 16
W 42
4649
R 14
G 16
W 42
4650
R 15
G 16
W 42
4651
R 19
G 16
W 42
4652
R 27
G 16
W 42
4653
R 28
G 16
W 42
4654
R 33
G 16
W 42
4655
R 38
G 16
W 42
4656
R 39
G 16
W 42
4657
R 41
G 16
W 42
4658
R 46
G 16
W 42
4659
R 47
G 16
W 42
4660
R 49
G 16
W 42
4661
R 1
G 17
W 42
4662
R 2
G 17
W 42
4663
R 4
G 17
W 42
4664
R 5
G 17
W 42
4665
R 7
G 17
W 42
4666
R 8
G 17
W 42
4667
R 10
G 17
W 42
4668
R 12
G 17
W 42
4669
R 14
G 17
W 42
4670
R 15
G 17
W 42
4671
R 19
G 17
W 42
4672
R 27
G 17
W 42
4673
R 28
G 17
W 42
4674
R 33
G 17
W 42
4675
R 38
G 17
W 42
4676
R 39
G 17
W 42
4677
R 41
G 17
W 42
4678
R 46
G 17
W 42
4679
R 47
G 17
W 42
4680
R 49
G 17
W 42
4681
R 1
G 22
W 42
4682
R 2
G 22
W 42
4683
R 4
G 22
W 42
4684
R 5
G 22
W 42
4685
R 7
G 22
W 42
4686
R 8
G 22
W 42
4687
R 10
G 22
W 42
4688
R 12
G 22
W 42
4689
R 14
G 22
W 42
4690
R 15
G 22
W 42
4691
R 19
G 22
W 42
4692
R 27
G 22
W 42
4693
R 28
G 22
W 42
4694
R 33
G 22
W 42
4695
R 38
G 22
W 42
4696
R 39
G 22
W 42
4697
R 41
G 22
W 42
4698
R 46
G 22
W 42
4699
R 47
G 22
W 42
4700
R 49
G 22
W 42
4701
R 1
G 23
W 42
4702
R 2
G 23
W 42
4703
R 4
G 23
W 42
4704
R 5
G 23
W 42
4705
R 7
G 23
W 42
4706
R 8
G 23
W 42
4707
R 10
G 23
W 42
4708
R 12
G 23
W 42
4709
R 14
G 23
W 42
4710
R 15
G 23
W 42
4711
R 19
G 23
W 42
4712
R 27
G 23
W 42
4713
R 28
G 23
W 42
4714
R 33
G 23
W 42
4715
R 38
G 23
W 42
4716
R 39
G 23
W 42
4717
R 41
G 23
W 42
4718
R 46
G 23
W 42
4719
R 47
G 23
W 42
4720
R 49
G 23
W 42
4721
R 1
G 24
W 42
4722
R 2
G 24
W 42
4723
R 4
G 24
W 42
4724
R 5
G 24
W 42
4725
R 7
G 24
W 42
4726
R 8
G 24
W 42
4727
R 10
G 24
W 42
4728
R 12
G 24
W 42
4729
R 14
G 24
W 42
4730
R 15
G 24
W 42
4731
R 19
G 24
W 42
4732
R 27
G 24
W 42
4733
R 28
G 24
W 42
4734
R 33
G 24
W 42
4735
R 38
G 24
W 42
4736
R 39
G 24
W 42
4737
R 41
G 24
W 42
4738
R 46
G 24
W 42
4739
R 47
G 24
W 42
4740
R 49
G 24
W 42
wherein R 1 to R 50 have the following structures:
wherein G 1 to G 40 have the following structures:
wherein W 1 to W 42 have the following structures:
12. The compound of claim 11 , wherein when the compound has formula Ir(L Ai-m ) 3 , i is an integer from 1 to 1240 and 1361 to 1560; m is an integer from 1 to 18; and the compound is selected from the group consisting of Ir(L A1-1 ) 3 to Ir(L A1560-18 ) 3 ;
when the compound has formula Ir(L Ai-m′ ) 3 , i is an integer from 1 to 1240 and 1361 to 4420; m′ is an integer from 19 to 54; and the compound is selected from the group consisting of Ir(L A1-19 ) 3 to Ir(L A4420-54 ) 3 ;
when the compound has formula Ir(L Ai′-m″ ) 3 , i′ is an integer from 4421 to 4740; m″ is an integer from 55 to 69; and the compound is selected from the group consisting of Ir(L A4421-55 ) 3 to Ir(L A4740-69 ) 3 ;
when the compound has formula Ir(L Ai-m )(L Bk ) 2 , i is an integer from 1 to 1240 and 1361 to 1560; m is an integer from 1 to 18; k is an integer from 1 to 324; and the compound is selected from the group consisting of Ir(L A1-1 )(L B1 ) 2 to Ir(L A1560-18 )(L B324 ) 2 ;
when the compound has formula Ir(L Ai-m′ )(L Bk ) 2 , i is an integer from 1 to 1240 and 1361 to 4420; m′ is an integer from 19 to 54; k is an integer from 1 to 324; and the compound is selected from the group consisting of Ir(L A1-19 )(L B1 ) 2 to Ir(L A4420-54 )(L B324 ) 2 ;
when the compound has formula Ir(L Ai′-m″ )(L Bk ) 2 , i′ is an integer from 4421 to 4740; m″ is an integer from 55 to 69; k is an integer from 1 to 324; and the compound is selected from the group consisting of Ir(L A4421-55 )(L B1 ) 2 to Ir(L A4740-69 )(L B324 ) 2 ;
when the compound has formula Ir(L Ai-m ) 2 (L Bk ) 2 , i is an integer from 1 to 1240 and 1361 to 1560; m is an integer from 1 to 18; k is an integer from 1 to 324; and the compound is selected from the group consisting of Ir(L A1-1 ) 2 (L B1 ) 2 to Ir(L A1560-18 ) 2 (L B324 );
when the compound has formula Ir(L Ai-m′ ) 2 (L Bk ), i is an integer from 1 to 1240 and 1361 to 4420; m′ is an integer from 19 to 54; k is an integer from 1 to 324; and the compound is selected from the group consisting of Ir(L A1-19 ) 2 (L B1 ) to Ir(L A4420-54 ) 2 (L B324 );
when the compound has formula Ir(L Ai′-m″ ) 2 (L Bk ), i′ is an integer from 4421 to 4740; m″ is an integer from 55 to 69; k is an integer from 1 to 324; and the compound is selected from the group consisting of Ir(L A4421-55 ) 2 (L B1 ) to Ir(L A4740-69 ) 2 (L B324 );
when the compound has formula Ir(L Ai-m ) 2 (L Cj-I ), i is an integer from 1 to 1240 and 1361 to 1560; m is an integer from 1 to 18; j is an integer from 1 to 1416; and the compound is selected from the group consisting of Ir(L A1-1 ) 2 (L C1-I ) to Ir(L A1560-18 )(L C1416-I );
when the compound has formula Ir(L Ai-m′ ) 2 (L Cj-I ), i is an integer from 1 to 1240 and 1361 to 4420; m′ is an integer from 19 to 54; j is an integer from 1 to 1416; and the compound is selected from the group consisting of Ir(L A1-19 ) 2 (L C1-I ) to Ir(L A4420-54 )(L C1416-I );
when the compound has formula Ir(L Ai′-m″ ) 2 (L Cj-I ), i′ is an integer from 4421 to 4740; m″ is an integer from 55 to 69; j is an integer from 1 to 1416; and the compound is selected from the group consisting of Ir(L A4421-55 ) 2 (L C1-I ) to Ir(L A4740-69 )(L C1416-I );
when the compound has formula Ir(L Ai-m ) 2 (L Cj-II ), i is an integer from 1 to 1560; m is an integer from 1 to 18; j is an integer from 1 to 1416; and the compound is selected from the group consisting of Ir(L A1-1 ) 2 (L C1-II ) to Ir(L A1560-18 )(L C1416-II );
when the compound has formula Ir(L Ai-m′ ) 2 (L Cj-II ), i is an integer from 1 to 1240 and 1361 to 4420; m′ is an integer from 19 to 54; j is an integer from 1 to 1416; and the compound is selected from the group consisting of Ir(L A1-19 ) 2 (L C1-II ) to Ir(L A4420-54 )(L C1416-II ); and
when the compound has formula Ir(L Ai′m″ ) 2 (L Cj-II ), i′ is an integer from 4421 to 4740; m″ is an integer from 55 to 69; j is an integer from 1 to 1416; and the compound is selected from the group consisting of Ir(L A4421-55 ) 2 (L C1-II ) to Ir(L A4740-69 )(L C1416-II );
wherein each L Bk has the structure as follows:
wherein each L Cj-I has a structure based on formula
and
each L Cj-II has a structure based on formula
wherein for each L Cj in L Cj-I and L Cj-II , R 201 and R 202 are each independently defined as follows:
L Cj
R 201
R 202
L Cj
R 201
R 202
L Cj
R 201
R 202
L Cj
R 201
R 202
L C1
R D1
R D1
L C193
R D1
R D3
L C385
R D17
R D40
L C577
R D143
R D120
L C2
R D2
R D2
L C194
R D1
R D4
L C386
R D17
R D41
L C578
R D143
R D133
L C3
R D3
R D3
L C195
R D1
R D5
L C387
R D17
R D42
L C579
R D143
R D134
L C4
R D4
R D4
L C196
R D1
R D9
L C388
R D17
R D43
L C580
R D143
R D135
L C5
R D5
R D5
L C197
R D1
R D10
L C389
R D17
R D48
L C581
R D143
R D136
L C6
R D6
R D6
L C198
R D1
R D17
L C390
R D17
R D49
L C582
R D143
R D144
L C7
R D7
R D7
L C199
R D1
R D18
L C391
R D17
R D50
L C583
R D143
R D145
L C8
R D8
R D8
L C200
R D1
R D20
L C392
R D17
R D54
L C584
R D143
R D146
L C9
R D9
R D9
L C201
R D1
R D22
L C393
R D17
R D55
L C585
R D143
R D147
L C10
R D10
R D10
L C202
R D1
R D37
L C394
R D17
R D58
L C586
R D143
R D149
L C11
R D11
R D11
L C203
R D1
R D40
L C395
R D17
R D59
L C587
R D143
R D151
L C12
R D12
R D12
L C204
R D1
R D41
L C396
R D17
R D78
L C588
R D143
R D154
L C13
R D13
R D13
L C205
R D1
R D42
L C397
R D17
R D79
L C589
R D143
R D155
L C14
R D14
R D14
L C206
R D1
R D43
L C398
R D17
R D81
L C590
R D143
R D161
L C15
R D15
R D15
L C207
R D1
R D48
L C399
R D17
R D87
L C591
R D143
R D175
L C16
R D16
R D16
L C208
R D1
R D49
L C400
R D17
R D88
L C592
R D144
R D3
L C17
R D17
R D17
L C209
R D1
R D50
L C401
R D17
R D89
L C593
R D144
R D5
L C18
R D18
R D18
L C210
R D1
R D54
L C402
R D17
R D93
L C594
R D144
R D17
L C19
R D19
R D19
L C211
R D1
R D55
L C403
R D17
R D116
L C595
R D144
R D18
L C20
R D20
R D20
L C212
R D1
R D58
L C404
R D17
R D117
L C596
R D144
R D20
L C21
R D21
R D21
L C213
R D1
R D59
L C405
R D17
R D118
L C597
R D144
R D22
L C22
R D22
R D22
L C214
R D1
R D78
L C406
R D17
R D119
L C598
R D144
R D37
L C23
R D23
R D23
L C215
R D1
R D79
L C407
R D17
R D120
L C599
R D144
R D40
L C24
R D24
R D24
L C216
R D1
R D81
L C408
R D17
R D133
L C600
R D144
R D41
L C25
R D25
R D25
L C217
R D1
R D87
L C409
R D17
R D134
L C601
R D144
R D42
L C26
R D26
R D26
L C218
R D1
R D88
L C410
R D17
R D135
L C602
R D144
R D43
L C27
R D27
R D27
L C219
R D1
R D89
L C411
R D17
R D136
L C603
R D144
R D48
L C28
R D28
R D28
L C220
R D1
R D93
L C412
R D17
R D143
L C604
R D144
R D49
L C29
R D29
R D29
L C221
R D1
R D116
L C413
R D17
R D144
L C605
R D144
R D54
L C30
R D30
R D30
L C222
R D1
R D117
L C414
R D17
R D145
L C606
R D144
R D58
L C31
R D31
R D31
L C223
R D1
R D118
L C415
R D17
R D146
L C607
R D144
R D59
L C32
R D32
R D32
L C224
R D1
R D119
L C416
R D17
R D147
L C608
R D144
R D78
L C33
R D33
R D33
L C225
R D1
R D120
L C417
R D17
R D149
L C609
R D144
R D79
L C34
R D34
R D34
L C226
R D1
R D133
L C418
R D17
R D151
L C610
R D144
R D81
L C35
R D35
R D35
L C227
R D1
R D134
L C419
R D17
R D154
L C611
R D144
R D87
L C36
R D36
R D36
L C228
R D1
R D135
L C420
R D17
R D155
L C612
R D144
R D88
L C37
R D37
R D37
L C229
R D1
R D136
L C421
R D17
R D161
L C613
R D144
R D89
L C38
R D38
R D38
L C230
R D1
R D143
L C422
R D17
R D175
L C614
R D144
R D93
L C39
R D39
R D39
L C231
R D1
R D144
L C423
R D50
R D3
L C615
R D144
R D116
L C10
R D40
R D40
L C232
R D1
R D145
L C424
R D50
R D5
L C616
R D144
R D117
L C41
R D41
R D41
L C233
R D1
R D146
L C425
R D50
R D18
L C617
R D144
R D118
L C42
R D42
R D42
L C234
R D1
R D147
L C426
R D50
R D20
L C618
R D144
R D119
L C43
R D43
R D43
L C235
R D1
R D149
L C427
R D50
R D22
L C619
R D144
R D120
L C44
R D44
R D44
L C236
R D1
R D151
L C428
R D50
R D37
L C620
R D144
R D133
L C45
R D45
R D45
L C237
R D1
R D154
L C429
R D50
R D40
L C621
R D144
R D134
L C46
R D46
R D46
L C238
R D1
R D155
L C430
R D50
R D41
L C622
R D144
R D135
L C47
R D47
R D47
L C239
R D1
R D161
L C431
R D50
R D42
L C623
R D144
R D136
L C48
R D48
R D48
L C240
R D1
R D175
L C432
R D50
R D43
L C624
R D144
R D145
L C49
R D49
R D49
L C241
R D4
R D3
L C433
R D50
R D48
L C625
R D144
R D146
L C50
R D50
R D50
L C242
R D4
R D5
L C434
R D50
R D49
L C626
R D144
R D147
L C51
R D51
R D51
L C243
R D4
R D9
L C435
R D50
R D54
L C627
R D144
R D149
L C52
R D52
R D52
L C244
R D4
R D10
L C436
R D50
R D55
L C628
R D144
R D151
L C53
R D55
R D55
L C245
R D4
R D17
L C437
R D50
R D58
L C629
R D144
R D154
L C54
R D54
R D54
L C246
R D4
R D18
L C438
R D50
R D59
L C630
R D144
R D155
L C55
R D55
R D55
L C247
R D4
R D20
L C439
R D50
R D78
L C631
R D144
R D161
L C56
R D56
R D56
L C248
R D4
R D22
L C440
R D50
R D79
L C632
R D144
R D175
L C57
R D57
R D57
L C249
R D4
R D37
L C441
R D50
R D81
L C633
R D145
R D3
L C58
R D58
R D58
L C250
R D4
R D40
L C442
R D50
R D87
L C634
R D145
R D5
L C59
R D59
R D59
L C251
R D4
R D41
L C443
R D50
R D88
L C635
R D145
R D17
L C60
R D60
R D60
L C252
R D4
R D42
L C444
R D50
R D89
L C636
R D145
R D18
L C61
R D61
R D61
L C253
R D4
R D43
L C445
R D50
R D93
L C637
R D145
R D20
L C62
R D62
R D62
L C254
R D4
R D48
L C446
R D50
R D116
L C638
R D145
R D22
L C63
R D63
R D63
L C255
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R D49
L C447
R D50
R D117
L C639
R D145
R D37
L C64
R D64
R D64
L C256
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R D50
L C448
R D50
R D118
L C640
R D145
R D40
L C65
R D65
R D65
L C257
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R D54
L C449
R D50
R D119
L C641
R D145
R D41
L C66
R D66
R D66
L C258
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R D55
L C450
R D50
R D120
L C642
R D145
R D42
L C67
R D67
R D67
L C259
R D4
R D58
L C451
R D50
R D133
L C643
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R D43
L C68
R D68
R D68
L C260
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R D59
L C452
R D50
R D134
L C644
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R D48
L C69
R D69
R D69
L C261
R D4
R D78
L C453
R D50
R D135
L C645
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R D49
L C70
R D70
R D70
L C262
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R D79
L C454
R D50
R D136
L C646
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R D54
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R D71
R D71
L C263
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R D81
L C455
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R D58
L C72
R D72
R D72
L C264
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R D87
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R D59
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R D73
R D73
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R D88
L C457
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R D78
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R D74
R D74
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R D89
L C458
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R D145
R D79
L C75
R D75
R D75
L C267
R D4
R D93
L C459
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R D81
L C76
R D76
R D76
L C268
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R D116
L C460
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R D149
L C652
R D145
R D87
L C77
R D77
R D77
L C269
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R D117
L C461
R D50
R D151
L C653
R D145
R D88
L C78
R D78
R D78
L C270
R D4
R D118
L C462
R D50
R D154
L C654
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R D89
L C79
R D79
R D79
L C271
R D4
R D119
L C463
R D50
R D155
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R D145
R D93
L C80
R D80
R D80
L C272
R D4
R D120
L C464
R D50
R D161
L C656
R D145
R D116
L C81
R D81
R D81
L C273
R D4
R D133
L C465
R D50
R D175
L C657
R D145
R D117
L C82
R D82
R D82
L C274
R D4
R D134
L C466
R D55
R D3
L C658
R D145
R D118
L C83
R D83
R D83
L C275
R D4
R D135
L C467
R D55
R D5
L C659
R D145
R D119
L C84
R D84
R D84
L C276
R D4
R D136
L C468
R D55
R D18
L C660
R D145
R D120
L C85
R D85
R D85
L C277
R D4
R D143
L C469
R D55
R D20
L C661
R D145
R D133
L C86
R D86
R D86
L C278
R D4
R D144
L C470
R D55
R D22
L C662
R D145
R D134
L C87
R D87
R D87
L C279
R D4
R D145
L C471
R D55
R D37
L C663
R D145
R D135
L C88
R D88
R D88
L C280
R D4
R D146
L C472
R D55
R D40
L C664
R D145
R D136
L C89
R D89
R D89
L C281
R D4
R D147
L C473
R D55
R D41
L C665
R D145
R D146
L C90
R D90
R D90
L C282
R D4
R D149
L C474
R D55
R D42
L C666
R D145
R D147
L C91
R D91
R D91
L C283
R D4
R D151
L C475
R D55
R D43
L C667
R D145
R D149
L C92
R D92
R D92
L C284
R D4
R D154
L C476
R D55
R D48
L C668
R D145
R D151
L C93
R D93
R D93
L C285
R D4
R D155
L C477
R D55
R D49
L C669
R D145
R D154
L C94
R D94
R D94
L C286
R D4
R D161
L C478
R D55
R D54
L C670
R D145
R D155
L C95
R D95
R D95
L C287
R D4
R D175
L C479
R D55
R D58
L C671
R D145
R D161
L C96
R D96
R D96
L C288
R D9
R D3
L C480
R D55
R D59
L C672
R D145
R D175
L C97
R D97
R D97
L C289
R D9
R D5
L C481
R D55
R D78
L C673
R D146
R D3
L C98
R D98
R D98
L C290
R D9
R D10
L C482
R D55
R D79
L C674
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R D5
L C99
R D99
R D99
L C291
R D9
R D17
L C483
R D55
R D81
L C675
R D146
R D17
L C100
R D100
R D100
L C292
R D9
R D18
L C484
R D55
R D87
L C676
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R D18
L C101
R D101
R D101
L C293
R D9
R D20
L C485
R D55
R D88
L C677
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R D20
L C102
R D102
R D102
L C294
R D9
R D22
L C486
R D55
R D89
L C678
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R D22
L C103
R D103
R D103
L C295
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R D37
L C487
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R D93
L C679
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R D37
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R D104
R D104
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R D116
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R D105
R D105
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R D106
R D106
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R D107
R D107
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R D108
R D108
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R D109
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R D59
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R D113
R D113
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R D114
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R D59
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R D146
R D79
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R D115
R D115
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R D146
R D81
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R D116
R D116
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R D79
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R D146
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R D146
R D87
L C117
R D117
R D117
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R D81
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R D146
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L C118
R D118
R D118
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R D9
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R D55
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L C119
R D119
R D119
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R D9
R D88
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R D55
R D151
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R D146
R D93
L C120
R D120
R D120
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R D9
R D89
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R D55
R D154
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R D117
L C121
R D121
R D121
L C313
R D9
R D93
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R D155
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R D118
L C122
R D122
R D122
L C314
R D9
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R D55
R D161
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R D146
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R D123
R D123
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R D124
R D124
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R D125
R D125
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R D133
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R D134
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R D161
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R D135
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R D116
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R D136
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R D137
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R D138
R D138
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R D58
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R D133
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R D139
R D139
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R D155
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R D59
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R D133
R D18
L C140
R D140
R D140
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R D161
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R D78
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R D20
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R D141
R D141
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R D79
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R D22
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R D142
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R D81
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R D157
R D157
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R D158
R D158
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R D93
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R D159
R D159
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R D59
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R D147
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R D133
R D117
L C160
R D160
R D160
L C352
R D10
R D78
L C544
R D116
R D149
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R D133
R D118
L C161
R D161
R D161
L C353
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R D79
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R D116
R D151
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R D133
R D119
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R D162
R D162
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R D163
R D163
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R D164
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R D168
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R D169
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R D170
R D170
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R D171
R D171
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R D120
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R D22
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R D154
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R D172
R D172
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R D37
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R D155
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R D173
R D173
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R D134
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R D40
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R D133
R D161
L C174
R D174
R D174
L C366
R D10
R D135
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R D143
R D41
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R D133
R D175
L C175
R D175
R D175
L C367
R D10
R D136
L C559
R D143
R D42
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R D175
R D3
L C176
R D176
R D176
L C368
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R D143
L C560
R D143
R D43
L C752
R D175
R D5
L C177
R D177
R D177
L C369
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R D144
L C561
R D143
R D48
L C753
R D175
R D18
L C178
R D178
R D178
L C370
R D10
R D145
L C562
R D143
R D49
L C754
R D175
R D20
L C179
R D179
R D179
L C371
R D10
R D146
L C563
R D143
R D54
L C755
R D175
R D22
L C180
R D180
R D180
L C372
R D10
R D147
L C564
R D143
R D58
L C756
R D175
R D37
L C181
R D181
R D181
L C373
R D10
R D149
L C565
R D143
R D59
L C757
R D175
R D40
L C182
R D182
R D182
L C374
R D10
R D151
L C566
R D143
R D78
L C758
R D175
R D41
L C183
R D183
R D183
L C375
R D10
R D154
L C567
R D143
R D79
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R D175
R D42
L C184
R D184
R D184
L C376
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R D155
L C568
R D143
R D81
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R D43
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R D185
R D185
L C377
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R D161
L C569
R D143
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L C761
R D175
R D48
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R D186
R D186
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R D175
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R D143
R D88
L C762
R D175
R D49
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R D187
R D187
L C379
R D17
R D3
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R D143
R D89
L C763
R D175
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R D188
R D188
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R D5
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R D93
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R D58
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R D189
R D189
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R D18
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R D116
L C765
R D175
R D59
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R D190
R D190
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R D20
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R D143
R D117
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R D191
R D191
L C383
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R D22
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R D143
R D118
L C767
R D175
R D79
L C192
R D192
R D192
L C384
R D17
R D37
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R D143
R D119
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R D175
R D81
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R D193
R D193
L C877
R D1
R D193
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R D4
R D193
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R D9
R D193
L C770
R D194
R D194
L C878
R D1
R D194
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R D4
R D194
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R D9
R D194
L C771
R D195
R D195
L C879
R D1
R D195
L C987
R D4
R D195
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R D9
R D195
L C772
R D196
R D196
L C880
R D1
R D196
L C988
R D4
R D196
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R D9
R D196
L C773
R D197
R D197
L C881
R D1
R D197
L C989
R D4
R D197
L C1097
R D9
R D197
L C774
R D198
R D198
L C882
R D1
R D198
L C990
R D4
R D198
L C1098
R D9
R D198
L C775
R D199
R D199
L C883
R D1
R D199
L C991
R D4
R D199
L C1099
R D9
R D199
L C776
R D200
R D200
L C884
R D1
R D200
L C992
R D4
R D200
L C1100
R D9
R D200
L C777
R D201
R D201
L C885
R D1
R D201
L C993
R D4
R D201
L C1101
R D9
R D201
L C778
R D202
R D202
L C886
R D1
R D202
L C994
R D4
R D202
L C1102
R D9
R D202
L C779
R D203
R D203
L C887
R D1
R D203
L C995
R D4
R D203
L C1103
R D9
R D203
L C780
R D204
R D204
L C888
R D1
R D204
L C996
R D4
R D204
L C1104
R D9
R D204
L C781
R D205
R D205
L C889
R D1
R D205
L C997
R D4
R D205
L C1105
R D9
R D205
L C782
R D206
R D206
L C890
R D1
R D206
L C998
R D4
R D206
L C1106
R D9
R D206
L C783
R D207
R D207
L C891
R D1
R D207
L C999
R D4
R D207
L C1107
R D9
R D207
L C784
R D208
R D208
L C892
R D1
R D208
L C1000
R D4
R D208
L C1108
R D9
R D208
L C785
R D209
R D209
L C893
R D1
R D209
L C1001
R D4
R D209
L C1109
R D9
R D209
L C786
R D210
R D210
L C894
R D1
R D210
L C1002
R D4
R D210
L C1110
R D9
R D210
L C787
R D211
R D211
L C895
R D1
R D211
L C1003
R D4
R D211
L C1111
R D9
R D211
L C788
R D212
R D212
L C896
R D1
R D212
L C1004
R D4
R D212
L C1112
R D9
R D212
L C789
R D213
R D213
L C897
R D1
R D213
L C1005
R D4
R D213
L C1113
R D9
R D213
L C790
R D214
R D214
L C898
R D1
R D214
L C1006
R D4
R D214
L C1114
R D9
R D214
L C791
R D215
R D215
L C899
R D1
R D215
L C1007
R D4
R D215
L C1115
R D9
R D215
L C792
R D216
R D216
L C900
R D1
R D216
L C1008
R D4
R D216
L C1116
R D9
R D216
L C793
R D217
R D217
L C901
R D1
R D217
L C1009
R D4
R D217
L C1117
R D9
R D217
L C794
R D218
R D218
L C902
R D1
R D218
L C1010
R D4
R D218
L C1118
R D9
R D218
L C795
R D219
R D219
L C903
R D1
R D219
L C1011
R D4
R D219
L C1119
R D9
R D219
L C796
R D220
R D220
L C904
R D1
R D220
L C1012
R D4
R D220
L C1120
R D9
R D220
L C797
R D221
R D221
L C905
R D1
R D221
L C1013
R D4
R D221
L C1121
R D9
R D221
L C798
R D222
R D222
L C906
R D1
R D222
L C1014
R D4
R D222
L C1122
R D9
R D222
L C799
R D223
R D223
L C907
R D1
R D223
L C1015
R D4
R D223
L C1123
R D9
R D223
L C800
R D224
R D224
L C908
R D1
R D224
L C1016
R D4
R D224
L C1124
R D9
R D224
L C801
R D225
R D225
L C909
R D1
R D225
L C1017
R D4
R D225
L C1125
R D9
R D225
L C802
R D226
R D226
L C910
R D1
R D226
L C1018
R D4
R D226
L C1126
R D9
R D226
L C803
R D227
R D227
L C911
R D1
R D227
L C1019
R D4
R D227
L C1127
R D9
R D227
L C804
R D228
R D228
L C912
R D1
R D228
L C1020
R D4
R D228
L C1128
R D9
R D228
L C805
R D229
R D229
L C913
R D1
R D229
L C1021
R D4
R D229
L C1129
R D9
R D229
L C806
R D230
R D230
L C914
R D1
R D230
L C1022
R D4
R D230
L C1130
R D9
R D230
L C807
R D231
R D231
L C915
R D1
R D231
L C1023
R D4
R D231
L C1131
R D9
R D231
L C808
R D232
R D232
L C916
R D1
R D232
L C1024
R D4
R D232
L C1132
R D9
R D232
L C809
R D233
R D233
L C917
R D1
R D233
L C1025
R D4
R D233
L C1133
R D9
R D233
L C810
R D234
R D234
L C918
R D1
R D234
L C1026
R D4
R D234
L C1134
R D9
R D234
L C811
R D235
R D235
L C919
R D1
R D235
L C1027
R D4
R D235
L C1135
R D9
R D235
L C812
R D236
R D236
L C920
R D1
R D236
L C1028
R D4
R D236
L C1136
R D9
R D236
L C813
R D237
R D237
L C921
R D1
R D237
L C1029
R D4
R D237
L C1137
R D9
R D237
L C814
R D238
R D238
L C922
R D1
R D238
L C1030
R D4
R D238
L C1138
R D9
R D238
L C815
R D239
R D239
L C923
R D1
R D239
L C1031
R D4
R D239
L C1139
R D9
R D239
L C816
R D240
R D240
L C924
R D1
R D240
L C1032
R D4
R D240
L C1140
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R D240
L C817
R D241
R D241
L C925
R D1
R D241
L C1033
R D4
R D241
L C1141
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R D241
L C818
R D242
R D242
L C926
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R D242
L C1034
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R D242
L C1142
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R D242
L C819
R D243
R D243
L C927
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R D243
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R D243
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R D243
L C820
R D244
R D244
L C928
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R D244
L C1036
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R D244
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R D244
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R D245
R D245
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R D245
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R D245
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R D245
L C822
R D246
R D246
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R D1
R D246
L C1038
R D4
R D246
L C1146
R D9
R D246
L C823
R D17
R D193
L C931
R D50
R D193
L C1039
R D145
R D193
L C1147
R D168
R D193
L C824
R D17
R D194
L C932
R D50
R D194
L C1040
R D145
R D194
L C1148
R D168
R D194
L C825
R D17
R D195
L C933
R D50
R D195
L C1041
R D145
R D195
L C1149
R D168
R D195
L C826
R D17
R D196
L C934
R D50
R D196
L C1042
R D145
R D196
L C1150
R D168
R D196
L C827
R D17
R D197
L C935
R D50
R D197
L C1043
R D145
R D197
L C1151
R D168
R D197
L C828
R D17
R D198
L C936
R D50
R D198
L C1044
R D145
R D198
L C1152
R D168
R D198
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R D17
R D199
L C937
R D50
R D199
L C1045
R D145
R D199
L C1153
R D168
R D199
L C830
R D17
R D200
L C938
R D50
R D200
L C1046
R D145
R D200
L C1154
R D168
R D200
L C831
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R D201
L C939
R D50
R D201
L C1047
R D145
R D201
L C1155
R D168
R D201
L C832
R D17
R D202
L C940
R D50
R D202
L C1048
R D145
R D202
L C1156
R D168
R D202
L C833
R D17
R D203
L C941
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R D203
L C1049
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R D203
L C1157
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R D203
L C834
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R D204
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R D204
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R D204
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R D204
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R D206
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R D208
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R D208
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R D211
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R D211
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R D50
R D212
L C1058
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R D212
L C1166
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R D212
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R D213
L C951
R D50
R D213
L C1059
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R D213
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R D213
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R D214
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R D215
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R D215
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R D216
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R D216
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R D217
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R D218
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R D219
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R D220
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R D220
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L C1067
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R D221
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R D221
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R D236
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R D237
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R D237
L C868
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R D238
L C976
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R D238
L C1084
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R D238
L C1192
R D168
R D238
L C869
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R D239
L C977
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R D239
L C1085
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R D239
L C1193
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R D239
L C870
R D17
R D240
L C978
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R D240
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R D240
L C1194
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L C871
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R D241
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R D245
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R D246
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R D246
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R D194
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R D194
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R D195
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R D195
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R D196
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R D196
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R D196
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R D197
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R D198
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R D198
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R D198
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R D199
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R D200
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R D200
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R D200
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R D201
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R D201
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R D201
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R D201
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R D10
R D202
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R D202
L C1318
R D37
R D202
L C1372
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R D202
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R D203
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R D203
L C1319
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R D203
L C1373
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R D203
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R D204
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R D204
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R D204
L C1374
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R D204
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R D206
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R D208
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R D208
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R D208
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R D209
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R D209
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R D209
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R D210
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R D210
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R D211
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R D211
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R D212
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R D213
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R D213
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R D213
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R D214
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R D214
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R D214
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R D215
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R D215
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R D215
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R D215
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R D216
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R D216
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R D216
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R D216
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R D217
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R D217
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R D217
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R D217
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R D218
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R D218
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R D218
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R D218
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R D219
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R D219
L C1335
R D37
R D219
L C1389
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R D219
L C1228
R D10
R D220
L C1282
R D55
R D220
L C1336
R D37
R D220
L C1390
R D143
R D220
L C1229
R D10
R D221
L C1283
R D55
R D221
L C1337
R D37
R D221
L C1391
R D143
R D221
L C1230
R D10
R D222
L C1284
R D55
R D222
L C1338
R D37
R D222
L C1392
R D143
R D222
L C1231
R D10
R D223
L C1285
R D55
R D223
L C1339
R D37
R D223
L C1393
R D143
R D223
L C1232
R D10
R D224
L C1286
R D55
R D224
L C1340
R D37
R D224
L C1394
R D143
R D224
L C1233
R D10
R D225
L C1287
R D55
R D225
L C1341
R D37
R D225
L C1395
R D143
R D225
L C1234
R D10
R D226
L C1288
R D55
R D226
L C1342
R D37
R D226
L C1396
R D143
R D226
L C1235
R D10
R D227
L C1289
R D55
R D227
L C1343
R D37
R D227
L C1397
R D143
R D227
L C1236
R D10
R D228
L C1290
R D55
R D228
L C1344
R D37
R D228
L C1398
R D143
R D228
L C1237
R D10
R D229
L C1291
R D55
R D229
L C1345
R D37
R D229
L C1399
R D143
R D229
L C1238
R D10
R D230
L C1292
R D55
R D230
L C1346
R D37
R D230
L C1400
R D143
R D230
L C1239
R D10
R D231
L C1293
R D55
R D231
L C1347
R D37
R D231
L C1401
R D143
R D231
L C1240
R D10
R D232
L C1294
R D55
R D232
L C1348
R D37
R D232
L C1402
R D143
R D232
L C1241
R D10
R D233
L C1295
R D55
R D233
L C1349
R D37
R D233
L C1403
R D143
R D233
L C1242
R D10
R D234
L C1296
R D55
R D234
L C1350
R D37
R D234
L C1404
R D143
R D234
L C1243
R D10
R D235
L C1297
R D55
R D235
L C1351
R D37
R D235
L C1405
R D143
R D235
L C1244
R D10
R D236
L C1298
R D55
R D236
L C1352
R D37
R D236
L C1406
R D143
R D236
L C1245
R D10
R D237
L C1299
R D55
R D237
L C1353
R D37
R D237
L C1407
R D143
R D237
L C1246
R D10
R D238
L C1300
R D55
R D238
L C1354
R D37
R D238
L C1408
R D143
R D238
L C1247
R D10
R D239
L C1301
R D55
R D239
L C1355
R D37
R D239
L C1409
R D143
R D239
L C1248
R D10
R D240
L C1302
R D55
R D240
L C1356
R D37
R D240
L C1410
R D143
R D240
L C1249
R D10
R D241
L C1303
R D55
R D241
L C1357
R D37
R D241
L C1411
R D143
R D241
L C1250
R D10
R D242
L C1304
R D55
R D242
L C1358
R D37
R D242
L C1412
R D143
R D242
L C1251
R D10
R D243
L C1305
R D55
R D243
L C1359
R D37
R D243
L C1413
R D143
R D243
L C1252
R D10
R D244
L C1306
R D55
R D244
L C1360
R D37
R D244
L C1414
R D143
R D244
L C1253
R D10
R D245
L C1307
R D55
R D245
L C1361
R D37
R D245
L C1415
R D143
R D245
L C1254
R D10
R D246
L C1308
R D55
R D246
L C1362
R D37
R D246
L C1416
R D143
R D246
wherein R D1 to R D246 have the following structures:
13. The compound of claim 1 , wherein the compound has a formula of M(L A ) p (L B ) q (L c ) r wherein L B and L C are each a bidentate ligand; and wherein p is 1, 2, or 3; q is 0, 1, or 2; r is 0, 1, or 2; and p+q+r is the oxidation state of the metal M; or the compound has a formula selected from the group consisting of Ir(L A ) 3 , Ir(L A )(L B ) 2 , Ir(L A ) 2 (L B ), Ir(L A ) 2 (L C ), and Ir(L A )(L B )(L C ); and wherein L A , L B , and L C are different from each other, or a formula of Pt(L A )(L B ); and wherein L A and L B can be same or different.
14. The compound of claim 13 , wherein L B and L C are each independently selected from the group consisting of:
wherein:
T is selected from the group consisting of B, Al, Ga, and In;
each of Y 1 to Y 13 is independently selected from the group consisting of carbon and nitrogen;
Y′ is selected from the group consisting of BR e , NR e , PR e , O, S, Se, C—O, S—O, SO 2 , CR e R f , SiR e R f , and GeR e R f ;
R e and R f can be fused or joined to form a ring;
each R a , R b , R c , and R a independently represents zero, mono, or up to a maximum allowed number of substitutions to its associated ring;
each of R a1 , R b1 , R c1 , R d1 , R a , R b , R c , R d , R e and R f is independently a hydrogen or a substituent selected from the group consisting of the general substitutents defined herein; and
and any two adjacent R a , R b , R c , R d , R e and R f can be fused or joined to form a ring or form a multidentate ligand.
15. The compound of claim 13 , wherein the compound has a structure of
wherein:
M 1 is Pd or Pt;
each of moieties E and F is independently monocyclic or polycyclic ring structure comprising 5-membered and/or 6-membered carbocyclic or heterocyclic rings;
Z 3 and Z 4 are each independently C or N;
K 1 , K 2 , K 3 , and K 4 are each independently selected from the group consisting of a direct bond, O, and S, wherein at least two of K 1 , K 2 , K 3 , and K 4 are direct bonds;
L 1 , L 2 , and L 3 are each independently selected from the group consisting of a single bond, absent a bond, O, S, SO, SO 2 , C═O, C═CRR′, CRR′, SiRR′, BR, BRR′, and NR, wherein at least one of L 1 and L 2 is present;
X 5 -X 7 are each independently C or N;
R E and R F each independently represent zero, mono, or up to a maximum allowed number of substitutions to its associated ring;
each of R E , and R F is independently a hydrogen or a substituent selected from the group consisting of deuterium, fluorine, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, boryl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, and combinations thereof; and
two adjacent R, R′, R A , R B , R C , R D , R E , or R F can be joined or fused together to form a ring where chemically feasible.
16. A consumer product comprising an organic light-emitting device (OLED) comprising:
an anode;
a cathode; and
an organic layer disposed between the anode and the cathode,
wherein the organic layer comprises the compound of claim 1 .
17. A compound selected from the group consisting of:
18. An organic light emitting device (OLED) comprising:
an anode;
a cathode; and
an organic layer disposed between the anode and the cathode,
wherein the organic layer comprises the compound of claim 15 .
19. An organic light emitting device (OLED) comprising:
an anode;
a cathode; and
an organic layer disposed between the anode and the cathode,
wherein the organic layer comprises a compound comprising a ligand L A having a structure of
wherein:
one of Z 1 and Z 2 is C and the other is N;
each of K 1 or K 2 is independently a direct bond, O, or S;
moiety B, moiety C, and moiety D are each independently monocyclic or polycyclic ring structure containing 5-membered or 6-membered carbocyclic or heterocyclic rings;
X 1 -X 4 are each independently C or N, with at least one of X 1 or X 2 being N if both moiety B and moiety C of Formula I are monocyclic 6-membered aromatic rings;
Y is selected from the group consisting of O, S, Se, NR, CRR′, BR, BRR′, SiRR′, and GeRR′;
W is selected from the group consisting of O, S, S═O, SO 2 , NR, C═CRR′, CRR′, SiRR′, BR, BRR′, GeRR′, PR, P═O, and P═S;
each of R A , R B , R C , and R D independently represents zero, mono, or up to a maximum allowed number of substitutions to its associated ring;
each of R, R′, R A , R B , R C , and R D is independently a hydrogen or a substituent selected from the group consisting of deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, heterocycloalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, germyl, boryl, selenyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carboxylic acid, ether, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and
any two adjacent R, R′, R A , R B , R C , or R D can be joined or fused together to form a ring,
wherein the ligand L A is coordinated to a metal M by the two indicated dashed lines;
wherein M is selected from the group consisting of Ru, Os, Ir, Pd, Pt, Cu, Ag, and Au;
wherein the ligand L A can be joined with other ligands to form a tridentate, tetradentate, pentadentate, or hexadentate ligand; and
subject to the following provisos:
when moiety B in Formula I is a monocyclic ring structure that is a 5-membered heterocyclic ring that comprises a nitrogen atom as the only heteroatom, at least one of the following is true:
i) W is selected from the group consisting of O, S, S═O, SO 2 , NR, C═CRR′, SiRR′, BR, BRR′, GeRR′, PR, P═O, and P═S;
ii) one of X 3 or X 4 is N; or
iii) two R B are joined to form a fused ring;
when moiety C comprises a sulfur atom, at least one of the following is true:
iv) the compound is heteroleptic; or
v) W is selected from the group consisting of O, S, S═O, SO 2 , NR, C═CRR′, SiRR′, BR, BRR′, GeRR′, PR, P═O, and P═S;
when W is BF 2 , at least one of the following is true:
vi) X 1 is a ring atom of a 6-membered aromatic ring; or
vii) one of X 1 or X 2 is C;
if W is CRR′, at least one of the following is true:
viii) X 1 in moiety B in Formula I is a ring atom of a 5-membered aromatic ring;
ix) the compound has the structure of Formula II; or
x) the compound is a heteroleptic compound comprising at least one substituted or unsubstituted acetylacetonate ligand and moiety C is a 5-membered ring.
20. The OLED of claim 19 , wherein the organic layer further comprises a host, wherein host comprises at least one chemical moiety selected from the group consisting of triphenylene, carbazole, indolocarbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, 5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene, aza-triphenylene, aza-carbazole, aza-indolocarbazole, aza-dibenzothiophene, aza-dibenzofuran, aza-dibenzoselenophene, and aza-(5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene).