Organic electroluminescent materials and devices
This invention discloses phosphorescent metal complexes with novel ligand structures of Formula I: wherein X, Z 1 , Z 2 , Z 3 , rings A and C, R A , R B , R C , and ligand L A are as described herein. These complexes are used as emitters in phosphorescent OLEDs.
1. A compound comprising a ligand L A of Formula I:
wherein X is selected from the group consisting of a single bond, NR, CRR′, O, S, Se, BRR′, and SiRR′;
wherein Z 1 , Z 2 , and Z 3 are each independently selected from the group consisting of carbon and nitrogen;
wherein rings A and C are each independently selected from the group consisting of aryl ring, and heteroaryl ring;
wherein R A , R B , and R C each independently represent from mono-substitution to the possible maximum number of substitution, or no substitution;
wherein R A , R B , R C , R, and R′ are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein any adjacent substituents of R B , R, and R′ are optionally joined or fused into a ring;
wherein the ligand L A is coordinated to a metal M; and
wherein the ligand L A is optionally linked with other ligands to comprise a tridentate, tetradentate, pentadentate or hexadentate ligand.
2. The compound of claim 1 , wherein M is selected from the group consisting of Ir, Rh, Re, Ru, Os, Pt, Au, and Cu.
3. The compound of claim 1 , wherein ring C is phenyl.
4. The compound of claim 1 , wherein X is selected from the group consisting of a single bond, CRR′, O, and S.
5. The compound of claim 1 , wherein Z 1 , Z 2 , and Z 3 are each a carbon atom.
6. The compound of claim 1 , wherein one of Z 1 , Z 2 , and Z 3 is a nitrogen atom, and the other two are each a carbon atom.
7. The compound of claim 1 , wherein ring A is phenyl.
8. The compound of claim 1 , wherein ligand L A is selected from the group consisting of:
9. The compound of claim 1 , wherein ligand L A has the formula
and is selected from the group consisting of L A1 to L A716 :
Ligand L Ai , i
X
R A1
R A2
R A3
R B1
R B2
1
Single bond
H
H
H
H
H
2
Single bond
CH 3
H
H
H
H
3
Single
CH 2 CH 3
H
H
H
H
bond
4
Single
CH(CH 3 ) 2
H
H
H
H
bond
5
Single
CH 2 CH(CH 3 ) 2
H
H
H
H
bond
6
Single
CH 2 C(CH 3 ) 3
H
H
H
H
bond
7
Single
H
H
H
H
bond
8
Single
H
H
H
H
bond
9
Single
CH 2 CH 2 CF 3
H
H
H
H
bond
10
Single bond
H
H
H
H
11
Single
CD 3
H
H
H
H
bond
12
Single
CD 2 CH 3
H
H
H
H
bond
13
Single
CD 2 CD 3
H
H
H
H
bond
14
Single
CD(CH 3 ) 2
H
H
H
H
bond
15
Single
CD(CD 3 ) 2
H
H
H
H
bond
16
Single
CD 2 CH(CH 3 ) 2
H
H
H
H
bond
17
Single
CD 2 C(CH 3 ) 3
H
H
H
H
bond
18
Single bond
H
H
H
H
19
Single bond
H
H
H
H
20
Single
CD 2 CH 2 CF 3
H
H
H
H
bond
21
Single bond
H
H
H
H
22
Single
H
CH 3
H
H
H
bond
23
Single
H
CH 2 CH 3
H
H
H
bond
24
Single
H
CH(CH 3 ) 2
H
H
H
bond
25
Single
H
CH 2 CH(CH 3 ) 2
H
H
H
bond
26
Single
H
CH 2 C(CH 3 ) 3
H
H
H
bond
27
Single bond
H
H
H
H
28
Single bond
H
H
H
H
29
Single
H
CH 2 CH 2 CF 3
H
H
H
bond
30
Single bond
H
H
H
H
31
Single
H
CD 3
H
H
H
bond
32
Single
H
CD 2 CH 3
H
H
H
bond
33
Single
H
CD 2 CD 3
H
H
H
bond
34
Single
H
CD(CH 3 ) 2
H
H
H
bond
35
Single
H
CD(CD 3 ) 2
H
H
H
bond
36
Single
H
CD 2 CH(CH 3 ) 2
H
H
H
bond
37
Single
H
CD 2 C(CH 3 ) 3
H
H
H
bond
38
Single bond
H
H
H
H
39
Single bond
H
H
H
H
40
Single
H
CD 2 CH 2 CF 3
H
H
H
bond
41
Single bond
H
H
H
H
42
Single
H
H
CH 3
H
H
bond
43
Single
H
H
CH 2 CH 3
H
H
bond
44
Single
H
H
CH(CH 3 ) 2
H
H
bond
45
Single
H
H
CH 2 CH(CH 3 ) 2
H
H
bond
46
Single
H
H
CH 2 C(CH 3 ) 3
H
H
bond
47
Single bond
H
H
H
H
48
Single bond
H
H
H
H
49
Single
H
H
bond
CH 2 CH 2 CF 3
H
H
50
Single bond
H
H
H
H
51
Single
H
H
CD 3
H
H
bond
52
Single
H
H
CD 3 CH 3
H
H
bond
53
Single
H
H
CD 2 CD 3
H
H
bond
54
Single
H
H
CD(CH 3 ) 2
H
H
bond
55
Single
H
H
CD(CD 3 ) 2
H
H
bond
56
Single
H
H
CD 2 CH(CH 3 ) 2
H
H
bond
57
Single
H
H
CD 2 C(CH 3 ) 3
H
H
bond
58
Single bond
H
H
H
H
59
Single bond
H
H
H
H
60
Single
H
H
CD 2 CH 2 CF 3
H
H
bond
61
Single bond
H
H
H
H
62
Single
H
H
H
CH 3
H
bond
63
Single
H
H
H
CH 2 CH 3
H
bond
64
Single
H
H
H
CH(CH 3 ) 2
H
bond
65
Single
H
H
H
CH 2 CH(CH 3 ) 2
H
bond
66
Single
H
H
H
CH 2 C(CH 3 ) 3
H
bond
67
Single bond
H
H
H
H
68
Single bond
H
H
H
H
69
Single
H
H
H
CH 2 CH 2 CF 3
H
bond
70
Single bond
H
H
H
H
71
Single
H
H
H
CD 3
H
bond
72
Single
H
H
H
CD 2 CH 3
H
bond
73
Single
H
H
H
CD 2 CD 3
H
bond
74
Single
H
H
H
CD(CH 3 ) 2
H
bond
75
Single
H
H
H
CD(CD 3 ) 2
H
bond
76
Single
H
H
H
CD 2 CH(CH 3 ) 2
H
bond
77
Single
H
H
H
CD 2 C(CH 3 ) 3
H
bond
78
Single bond
H
H
H
H
79
Single bond
H
H
H
H
80
Single
H
H
H
CD 2 CH 2 CF 3
H
bond
81
Single bond
H
H
H
H
82
Single bond
H
H
H
H
CH 3
83
Single bond
H
H
H
H
CH 3 CH 3
84
Single bond
H
H
H
H
CH(CH 3 ) 2
85
Single bond
H
H
H
H
CH 2 CH(CH 3 ) 2
86
Single
H
H
H
H
CH 2 C(CH 3 ) 3
bond
87
Single bond
H
H
H
H
88
Single bond
H
H
H
H
89
Single
H
H
H
H
CH 2 CH 2 CF 3
bond
90
Single bond
H
H
H
H
91
Single
H
H
H
H
CD 3
bond
92
Single
H
H
H
H
CD 2 CH 3
bond
93
Single
H
H
H
H
CD 2 CD 3
bond
94
Single
H
H
H
H
CD(CH 3 ) 2
bond
95
Single
H
H
H
H
CD(CD 3 ) 2
bond
96
Single
H
H
H
H
CD 2 CH(CH 3 ) 2
bond
97
Single
H
H
H
H
CD 2 C(CH 3 ) 3
bond
98
Single bond
H
H
H
H
99
Single bond
H
H
H
H
100
Single
H
H
H
H
CD 2 CH 2 CF 3
bond
101
Single bond
H
H
H
H
102
Single bond
H
H
H
H
103
Single bond
H
H
H
H
104
Single bond
H
H
H
H
105
Single bond
H
H
H
H
106
Single bond
H
H
H
H
107
Single bond
H
H
H
H
108
Single bond
H
H
H
H
109
Single bond
H
H
H
H
110
Single bond
H
H
H
H
111
Single bond
H
H
H
H
112
Single bond
H
H
H
H
113
Single bond
H
H
H
H
114
Single bond
H
H
H
H
115
Single bond
H
H
H
H
116
Single bond
H
H
H
H
117
Single bond
H
H
H
H
118
Single bond
H
H
H
H
119
Single bond
H
H
H
H
120
Single bond
H
H
H
H
121
Single bond
H
H
H
H
122
Single bond
H
H
H
H
123
Single bond
H
H
H
H
124
Single bond
H
H
H
H
125
Single bond
H
H
H
H
126
Single bond
H
H
H
H
127
Single bond
H
H
H
H
128
Single bond
H
H
H
H
129
Single bond
H
H
H
H
130
Single bond
H
H
H
H
131
Single bond
H
H
H
H
132
Single bond
H
H
H
H
133
Single bond
H
H
H
H
134
Single bond
H
H
H
H
135
Single bond
H
H
H
H
136
Single bond
H
H
H
H
137
Single bond
H
H
H
H
138
Single bond
H
H
H
H
139
Single bond
H
H
H
H
140
Single bond
H
H
H
H
141
Single bond
H
H
H
H
142
Single bond
H
H
H
H
143
Single bond
H
H
H
H
144
Single bond
H
H
H
H
145
Single bond
H
H
H
H
146
Single bond
H
H
H
H
147
Single bond
H
H
H
H
148
Single bond
H
H
H
H
149
Single bond
H
H
H
H
150
Single bond
H
H
H
H
151
Single bond
H
H
H
H
152
Single bond
H
H
H
H
153
Single bond
H
H
H
H
154
Single bond
H
H
H
H
155
Single bond
H
H
H
H
156
Single bond
H
H
H
H
157
Single bond
H
H
H
H
158
Single bond
H
H
H
H
159
Single bond
H
H
H
H
160
Single bond
H
H
H
H
161
Single bond
H
H
H
H
162
Single bond
H
H
H
H
163
Single bond
H
H
H
H
164
Single bond
H
H
H
H
165
Single bond
H
H
H
H
166
Single bond
H
H
H
H
167
Single bond
H
H
H
H
168
Single bond
H
H
H
H
169
Single bond
H
H
H
H
170
Single bond
H
H
H
H
171
Single bond
H
H
H
H
172
Single bond
H
H
H
H
173
Single bond
H
H
H
H
174
Single bond
H
H
H
H
175
Single bond
H
H
H
H
176
Single bond
H
H
H
H
177
Single bond
H
H
H
H
178
Single bond
H
H
H
H
179
Single bond
H
H
H
H
180
O
H
H
H
H
H
181
O
CH 3
H
H
H
H
182
O
CH 2 CH 3
H
H
H
H
183
O
CH(CH 3 ) 2
H
H
H
H
184
O
CH 2 CH(CH 3 ) 2
H
H
H
H
185
O
CH 2 C(CH 3 ) 3
H
H
H
H
186
O
H
H
H
H
187
O
H
H
H
H
188
O
CH 2 CH 2 CF 3
H
H
H
H
189
O
H
H
H
H
190
O
CD 3
H
H
H
H
191
O
CD 2 CH 3
H
H
H
H
192
O
CD 2 CD 3
H
H
H
H
193
O
CD(CH 3 ) 2
H
H
H
H
194
O
CD(CD 3 ) 2
H
H
H
H
195
O
CD 2 CH(CH 3 ) 2
H
H
H
H
196
O
CD 2 C(CH 3 ) 3
H
H
H
H
197
O
H
H
H
H
198
O
H
H
H
H
199
O
CD 2 CH 2 CF 3
H
H
H
H
200
O
H
H
H
H
201
O
H
CH 3
H
H
H
202
O
H
CH 2 CH 3
H
H
H
203
O
H
CH(CH 3 ) 2
H
H
H
204
O
H
CH 2 CH(CH 3 ) 2
H
H
H
205
O
H
CH 2 C(CH 3 ) 3
H
H
H
206
O
H
H
H
H
207
O
H
H
H
H
208
O
H
CH 2 CH 2 F 3
H
H
H
209
O
H
H
H
H
210
O
H
CD 3
H
H
H
211
O
H
CD 2 CH 3
H
H
H
212
O
H
CD 2 CD 3
H
H
H
213
O
H
CD(CH 3 ) 2
H
H
H
214
O
H
CD(CD 3 ) 2
H
H
H
215
O
H
CD 2 CH(CH 3 ) 2
H
H
H
216
O
H
CD 2 C(CH 3 ) 3
H
H
H
217
O
H
H
H
H
218
O
H
H
H
H
219
O
H
CD 2 CH 2 CF 3
H
H
H
220
O
H
H
H
H
221
O
H
H
CH 3
H
H
222
O
H
H
CD 2 CH 3
H
H
223
O
H
H
CH(CH 3 ) 2
H
H
224
O
H
H
CH 2 CH(CH 3 ) 2
H
H
225
O
H
H
CH 2 C(CH 3 ) 3
H
H
226
O
H
H
H
H
227
O
H
H
H
H
228
O
H
H
CH 2 CH 2 CF 3
H
H
229
O
H
H
H
H
230
O
H
H
CD 3
H
H
231
O
H
H
CD 3 CH 3
H
H
232
O
H
H
CD 2 CD 3
H
H
233
O
H
H
CD(CH 3 ) 2
H
H
234
O
H
H
CD(CD 3 ) 2
H
H
235
O
H
H
CD 2 CH(CH 3 ) 2
H
H
236
O
H
H
CD 2 C(CH 3 ) 3
H
H
237
O
H
H
H
H
238
O
H
H
H
H
239
O
H
H
CD 2 CH 2 CF 3
H
H
240
O
H
H
H
H
241
O
H
H
H
CH 3
H
242
O
H
H
H
CH 2 CH 3
H
243
O
H
H
H
CH(CH 3 ) 2
H
244
O
H
H
H
CH 2 CH(CH 3 ) 2
H
245
O
H
H
H
CH 2 C(CH 3 ) 3
H
246
O
H
H
H
H
247
O
H
H
H
H
248
O
H
H
H
CH 2 CH 2 CF 3
H
249
O
H
H
H
H
250
O
H
H
H
CD 3
H
251
O
H
H
H
CD 2 CH 3
H
252
O
H
H
H
CD 2 CD 3
H
253
O
H
H
H
CD(CH 3 ) 2
H
254
O
H
H
H
CD(CD 3 ) 2
H
255
O
H
H
H
CD 2 CH(CH 3 ) 2
H
256
O
H
H
H
CD 2 C(CH 3 ) 3
H
257
O
H
H
H
H
258
O
H
H
H
H
259
O
H
H
H
CD 2 CH 2 CF 3
H
260
O
H
H
H
H
261
O
H
H
H
H
CH 3
262
O
H
H
H
H
CH 2 CH 3
263
O
H
H
H
H
CH(CH 3 ) 2
264
O
H
H
H
H
CH 2 CH(CH 3 ) 2
265
O
H
H
H
H
CH 2 C(CH 3 ) 3
266
O
H
H
H
H
267
O
H
H
H
H
268
O
H
H
H
H
CH 2 CH 2 CF 3
269
O
H
H
H
H
270
O
H
H
H
H
CD 3
271
O
H
H
H
H
CD 2 CH 3
272
O
H
H
H
H
CD 2 CD 3
273
O
H
H
H
H
CD(CH 3 ) 2
274
O
H
H
H
H
CD(CD 3 ) 2
275
O
H
H
H
H
CD 2 CH(CH 3 ) 2
276
O
H
H
H
H
CD 2 C(CH 3 ) 3
277
O
H
H
H
H
278
O
H
H
H
H
279
O
H
H
H
H
CD 2 CH 2 CF 3
280
O
H
H
H
H
281
O
H
H
H
H
282
O
H
H
H
H
283
O
H
H
H
H
284
O
H
H
H
H
285
O
H
H
H
H
286
O
H
H
H
H
287
O
H
H
H
H
288
O
H
H
H
H
289
O
H
H
H
H
290
O
H
H
H
H
291
O
H
H
H
H
292
O
H
H
H
H
293
O
H
H
H
H
294
O
H
H
H
H
295
O
H
H
H
H
296
O
H
H
H
H
297
O
H
H
H
H
298
O
H
H
H
H
299
O
H
H
H
H
300
O
H
H
H
H
301
O
H
H
H
H
302
O
H
H
H
H
303
O
H
H
H
H
301
O
H
H
H
H
305
O
H
H
H
H
306
O
H
H
H
H
307
O
H
H
H
H
308
O
H
H
H
H
309
O
H
H
H
H
310
O
H
H
H
H
311
O
H
H
H
H
312
O
H
H
H
H
313
O
H
H
H
H
314
O
H
H
H
H
315
O
H
H
H
H
316
O
H
H
H
H
317
O
H
H
H
H
318
O
H
H
H
H
319
O
H
H
H
H
320
O
H
H
H
H
321
O
H
H
H
H
322
O
H
H
H
H
323
O
H
H
H
H
324
O
H
H
H
H
325
O
H
H
H
H
326
O
H
H
H
H
327
O
H
H
H
H
328
O
H
H
H
H
329
O
H
H
H
H
330
O
H
H
H
H
331
O
H
H
H
H
332
O
H
H
H
H
333
O
H
H
H
H
334
O
H
H
H
H
335
O
H
H
H
H
336
O
H
H
H
H
337
O
H
H
H
H
338
O
H
H
H
H
339
O
H
H
H
H
340
O
H
H
H
H
341
O
H
H
H
H
342
O
H
H
H
H
343
O
H
H
H
H
344
O
H
H
H
H
345
O
H
H
H
H
346
O
H
H
H
H
347
O
H
H
H
H
348
O
H
H
H
H
349
O
H
H
H
H
350
O
H
H
H
H
351
O
H
H
H
H
352
O
H
H
H
H
353
O
H
H
H
H
354
O
H
H
H
H
355
O
H
H
H
H
356
O
H
H
H
H
357
O
H
H
H
H
358
O
H
H
H
H
359
S
H
H
H
H
H
360
S
CH 3
H
H
H
H
361
S
CH 2 CH 3
H
H
H
H
362
S
CH(CH 3 ) 2
H
H
H
H
363
S
CH 2 CH(CH 3 ) 2
H
H
H
H
364
S
CH 2 C(CH 3 ) 3
H
H
H
H
365
S
H
H
H
H
366
S
H
H
H
H
367
S
CH 2 CH 2 CF 3
H
H
H
H
368
S
H
H
H
H
369
S
CD 3
H
H
H
H
370
S
CD 2 CH 3
H
H
H
H
371
S
CD 2 CD 3
H
H
H
H
372
S
CD(CH 3 ) 2
H
H
H
H
373
S
CD(CD 3 ) 2
H
H
H
H
374
S
CD 2 CH(CH 3 ) 2
H
H
H
H
375
S
CD 2 C(CH 3 ) 3
H
H
H
H
376
S
H
H
H
H
377
S
H
H
H
H
378
S
CD 2 CH 2 CF 3
H
H
H
H
379
S
H
H
H
H
380
S
H
CH 3
H
H
H
381
S
H
CH 2 CH 3
H
H
H
382
S
H
CH(CH 3 ) 2
H
H
H
383
S
H
CH 2 CH(CH 3 ) 2
H
H
H
384
S
H
CH 2 C(CH 3 ) 3
H
H
H
385
S
H
H
H
H
386
S
H
H
H
H
387
S
H
CH 2 CH 2 CF 3
H
H
H
388
S
H
H
H
H
389
S
H
CD 3
H
H
H
390
S
H
CD 2 CH 3
H
H
H
391
S
H
CD 2 CD 3
H
H
H
392
S
H
CD(CH 3 ) 2
H
H
H
393
S
H
CD(CD 3 ) 2
H
H
H
394
S
H
CD 2 CH(CH 3 ) 2
H
H
H
395
S
H
CD 2 C(CH 3 ) 3
H
H
H
396
S
H
H
H
H
397
S
H
H
H
H
398
S
H
CD 2 CH 2 CF 3
H
H
H
399
S
H
H
H
H
400
S
H
H
CH 3
H
H
401
S
H
H
CH 2 CH 3
H
H
402
S
H
H
CH(CH 3 ) 2
H
H
403
S
H
H
CH 2 CH(CH 3 ) 2
H
H
404
S
H
H
CH 2 C(CH 3 ) 3
H
H
405
S
H
H
H
H
406
S
H
H
H
H
407
S
H
H
CH 2 CH 2 CF 3
H
H
408
S
H
H
H
H
409
S
H
H
CD 3
H
H
410
S
H
H
CD 2 CH 3
H
H
411
S
H
H
CD 2 CD 3
H
H
412
S
H
H
CD(CH 3 ) 2
H
H
413
S
H
H
CD(CD 3 ) 2
H
H
414
S
H
H
CD 2 CH(CH 3 ) 2
H
H
415
S
H
H
CD 2 C(CH 3 ) 3
H
H
416
S
H
H
H
417
S
H
H
H
418
S
H
H
CD 2 CH 2 CF 3
H
419
S
H
H
H
420
S
H
H
H
CH 3
H
421
S
H
H
H
CH 2 CH 3
H
422
S
H
H
H
CH(CH 3 ) 2
H
423
S
H
H
H
CH 2 CH(CH 3 ) 2
H
424
S
H
H
H
CH 2 C(CH 3 ) 3
H
425
S
H
H
H
H
426
S
H
H
H
H
427
S
H
H
H
CH 2 CH 2 CF 3
H
428
S
H
H
H
H
429
S
H
H
H
CD 3
H
430
S
H
H
H
CD 2 CH 3
H
431
S
H
H
H
CD 2 CD 3
H
432
S
H
H
H
CD(CH 3 ) 2
H
433
S
H
H
H
CD(CD 3 ) 2
H
434
S
H
H
H
CD 2 CH(CH 3 ) 2
H
435
S
H
H
H
CD 2 C(CH 3 ) 3
H
436
S
H
H
H
H
437
S
H
H
H
H
438
S
H
H
H
CD 2 CH 2 CF 3
H
439
S
H
H
H
H
440
S
H
H
H
H
CH 3
441
S
H
H
H
H
CH 2 CH 3
442
S
H
H
H
H
CH(CH 3 ) 2
443
S
H
H
H
H
CH 2 CH(CH 3 ) 2
444
S
H
H
H
H
CH 2 C(CH 3 ) 3
445
S
H
H
H
H
446
S
H
H
H
H
447
S
H
H
H
H
CH 2 CH 2 CF 3
448
S
H
H
H
H
449
S
H
H
H
H
CD 3
450
S
H
H
H
H
CD 2 CH 3
451
S
H
H
H
H
CD 2 CD 3
452
S
H
H
H
H
CD(CH 3 ) 2
453
S
H
H
H
H
CD(CD 3 ) 2
454
S
H
H
H
H
CD 2 CH(CH 3 ) 2
455
S
H
H
H
H
CD 2 C(CH 3 ) 3
456
S
H
H
H
H
457
S
H
H
H
H
458
S
H
H
H
H
CD 2 CH 2 CF 3
459
S
H
H
H
H
460
S
H
H
H
H
461
S
H
H
H
H
462
S
H
H
H
H
463
S
H
H
H
H
464
S
H
H
H
H
465
S
H
H
H
H
466
S
H
H
H
H
467
S
H
H
H
H
468
S
H
H
H
H
469
S
H
H
H
H
470
S
H
H
H
H
471
S
H
H
H
H
472
S
H
H
H
H
473
S
H
H
H
H
474
S
H
H
H
H
475
S
H
H
H
H
476
S
H
H
H
H
477
S
H
H
H
H
478
S
H
H
H
H
479
S
H
H
H
H
480
S
H
H
H
H
481
S
H
H
H
H
482
S
H
H
H
H
483
S
H
H
H
H
484
S
H
H
H
H
485
S
H
H
H
H
486
S
H
H
H
H
487
S
H
H
H
H
488
S
H
H
H
H
489
S
H
H
H
H
490
S
H
H
H
H
491
S
H
H
H
H
492
S
H
H
H
H
493
S
H
H
H
H
494
S
H
H
H
H
495
S
H
H
H
H
496
S
H
H
H
H
497
S
H
H
H
H
498
S
H
H
H
H
499
S
H
H
H
H
500
S
H
H
H
H
501
S
H
H
H
H
502
S
H
H
H
H
503
S
H
H
H
H
504
S
H
H
H
H
505
S
H
H
H
H
506
S
H
H
H
H
507
S
H
H
H
H
508
S
H
H
H
H
509
S
H
H
H
H
510
S
H
H
H
H
511
S
H
H
H
H
512
S
H
H
H
H
513
S
H
H
H
H
514
S
H
H
H
H
515
S
H
H
H
H
516
S
H
H
H
H
517
S
H
H
H
H
518
S
H
H
H
H
519
S
H
H
H
H
520
S
H
H
H
H
521
S
H
H
H
H
522
S
H
H
H
H
523
S
H
H
H
H
524
S
H
H
H
H
525
S
H
H
H
H
526
S
H
H
H
H
527
S
H
H
H
H
528
S
H
H
H
H
529
S
H
H
H
H
530
S
H
H
H
H
531
S
H
H
H
H
532
S
H
H
H
H
533
S
H
H
H
H
534
S
H
H
H
H
535
S
H
H
H
H
536
S
H
H
H
H
537
S
H
H
H
H
538
C(CH 3 ) 2
H
H
H
H
H
539
C(CH 3 ) 2
CH 3
H
H
H
H
540
C(CH 3 ) 2
CH 2 CH 3
H
H
H
H
541
C(CH 3 ) 2
CH(CH 3 ) 2
H
H
H
H
542
C(CH 3 ) 2
CH 2 CH(CH 3 ) 2
H
H
H
H
543
C(CH 3 ) 2
CH 2 C(CH 3 ) 3
H
H
H
H
544
C(CH 3 ) 2
H
H
H
H
545
C(CH 3 ) 2
H
H
H
H
546
C(CH 3 ) 2
CH 2 CH 2 CF 3
H
H
H
H
547
C(CH 3 ) 2
H
H
H
H
548
C(CH 3 ) 2
CD 3
H
H
H
H
549
C(CH 3 ) 2
CD 2 CH 3
H
H
H
H
550
C(CH 3 ) 2
CD 2 CD 3
H
H
H
H
551
C(CH 3 ) 2
CD(CH 3 ) 2
H
H
H
H
552
C(CH 3 ) 2
CD(CD 3 ) 2
H
H
H
H
553
C(CH 3 ) 2
CD 2 CH(CH 3 ) 2
H
H
H
H
554
C(CH 3 ) 2
CD 2 C(CH 3 ) 3
H
H
H
H
555
C(CH 3 ) 2
H
H
H
H
556
C(CH 3 ) 2
H
H
H
H
557
C(CH 3 ) 2
CD2CH 2 CF 3
H
H
H
H
558
C(CH 3 ) 2
H
H
H
H
559
C(CH 3 ) 2
H
CH 3
H
H
H
560
C(CH 3 ) 2
H
CH 2 CH 3
H
H
H
561
C(CH 3 ) 2
H
CH(CH 3 ) 2
H
H
H
562
C(CH 3 ) 2
H
CH 2 CH(CH 3 ) 2
H
H
H
563
C(CH 3 ) 2
H
CH 2 C(CH 3 ) 3
H
H
H
564
C(CH 3 ) 2
H
H
H
H
565
C(CH 3 ) 2
H
H
H
H
566
C(CH 3 ) 2
H
CH 2 CH 2 CF 3
H
H
H
567
C(CH 3 ) 2
H
H
H
H
568
C(CH 3 ) 2
H
CD 3
H
H
H
569
C(CH 3 ) 2
H
CD 2 CH 3
H
H
H
570
C(CH 3 ) 2
H
CD 2 CD 3
H
H
H
571
C(CH 3 ) 2
H
CD(CH 3 ) 2
H
H
H
572
C(CH 3 ) 2
H
CD(CD 3 ) 2
H
H
H
573
C(CH 3 ) 2
H
CD 2 CH(CH 3 ) 2
H
H
H
574
C(CH 3 ) 2
H
CD 2 C(CH 3 ) 3
H
H
H
575
C(CH 3 ) 2
H
H
H
H
576
C(CH 3 ) 2
H
H
H
H
577
C(CH 3 ) 2
H
CD 2 CH 2 CF 3
H
H
H
578
C(CH 3 ) 2
H
H
H
H
579
C(CH 3 ) 2
H
H
CH 3
H
H
580
C(CH 3 ) 2
H
H
CH 2 CH 3
H
H
581
C(CH 3 ) 2
H
H
CH(CH 3 ) 2
H
H
582
C(CH 3 ) 2
H
H
CH 2 CH(CH 3 ) 2
H
H
583
C(CH 3 ) 2
H
H
CH 2 C(CH 3 ) 3
H
H
584
C(CH 3 ) 2
H
H
H
H
585
C(CH 3 ) 2
H
H
H
H
586
C(CH 3 ) 2
H
H
CH 2 CH 2 CF 3
H
H
587
C(CH 3 ) 2
H
H
H
H
588
C(CH 3 ) 2
H
H
CD 3
H
H
589
C(CH 3 ) 2
H
H
CD 2 CH 3
H
H
590
C(CH 3 ) 2
H
H
CD 2 CD 3
H
H
591
C(CH 3 ) 2
H
H
CD(CH 3 ) 2
H
H
592
C(CH 3 ) 2
H
H
CD(CD 3 ) 2
H
H
593
C(CH 3 ) 2
H
H
CD 2 CH(CH 3 ) 2
H
H
594
C(CH 3 ) 2
H
H
CD 2 C(CH 3 ) 3
H
H
595
C(CH 3 ) 2
H
H
H
H
596
C(CH 3 ) 2
H
H
H
H
597
C(CH 3 ) 2
H
H
CD 2 CH 2 CF 3
H
H
598
C(CH 3 ) 2
H
H
H
H
599
C(CH 3 ) 2
H
H
H
CH 3
H
600
C(CH 3 ) 2
H
H
H
CH 2 CH 3
H
601
C(CH 3 ) 2
H
H
H
CH(CH 3 ) 2
H
602
C(CH 3 ) 2
H
H
H
CH 2 CH(CH 3 ) 2
H
603
C(CH 3 ) 2
H
H
H
CH 2 C(CH 3 ) 3
H
604
C(CH 3 ) 2
H
H
H
H
605
C(CH 3 ) 2
H
H
H
H
606
C(CH 3 ) 2
H
H
H
CH 2 CH 2 CF 3
H
607
C(CH 3 ) 2
H
H
H
H
608
C(CH 3 ) 2
H
H
H
CD 3
H
609
C(CH 3 ) 2
H
H
H
CD 2 CH 3
H
610
C(CH 3 ) 2
H
H
H
CD 2 CD 3
H
611
C(CH 3 ) 2
H
H
H
CD(CH 3 ) 2
H
612
C(CH 3 ) 2
H
H
H
CD(CD 3 ) 2
H
613
C(CH 3 ) 2
H
H
H
CD 2 CH(CH 3 ) 2
H
614
C(CH 3 ) 2
H
H
H
CD 2 C(CH 3 ) 3
H
615
C(CH 3 ) 2
H
H
H
H
616
C(CH 3 ) 2
H
H
H
H
617
C(CH 3 ) 2
H
H
H
CD 2 CH 2 CF 3
H
618
C(CH 3 ) 2
H
H
H
H
619
C(CH 3 ) 2
H
H
H
H
CH 3
620
C(CH 3 ) 2
H
H
H
H
CH 2 CH 3
621
C(CH 3 ) 2
H
H
H
H
CH(CH 3 ) 2
622
C(CH 3 ) 2
H
H
H
H
CH 2 CH(CH 3 ) 2
623
C(CH 3 ) 2
H
H
H
H
CH 2 C(CH 3 ) 3
624
C(CH 3 ) 2
H
H
H
H
625
C(CH 3 ) 2
H
H
H
H
626
C(CH 3 ) 2
H
H
H
H
CH 2 CH 2 CF 3
627
C(CH 3 ) 2
H
H
H
H
628
C(CH 3 ) 2
H
H
H
H
CD 3
629
C(CH 3 ) 2
H
H
H
H
CD 2 CH 3
630
C(CH 3 ) 2
H
H
H
H
CD 2 CD 3
631
C(CH 3 ) 2
H
H
H
H
CD(CH 3 ) 2
632
C(CH 3 ) 2
H
H
H
H
CD(CD 3 ) 2
633
C(CH 3 ) 2
H
H
H
H
CD 2 CH(CH 3 ) 2
634
C(CH 3 ) 2
H
H
H
H
CD 2 C(CH 3 ) 3
635
C(CH 3 ) 2
H
H
H
H
636
C(CH 3 ) 2
H
H
H
H
637
C(CH 3 ) 2
H
H
H
H
CD 2 CH 2 CF 3
638
C(CH 3 ) 2
H
H
H
H
639
C(CH 3 ) 2
H
H
H
H
640
C(CH 3 ) 2
H
H
H
H
641
C(CH 3 ) 2
H
H
H
H
642
C(CH 3 ) 2
H
H
H
H
643
C(CH 3 ) 2
H
H
H
H
644
C(CH 3 ) 2
H
H
H
H
645
C(CH 3 ) 2
H
H
H
H
646
C(CH 3 ) 2
H
H
H
H
647
C(CH 3 ) 2
H
H
H
H
648
C(CH 3 ) 2
H
H
H
H
649
C(CH 3 ) 2
H
H
H
H
650
C(CH 3 ) 2
H
H
H
H
651
C(CH 3 ) 2
H
H
H
H
652
C(CH 3 ) 2
H
H
H
H
653
C(CH 3 ) 2
H
H
H
H
654
C(CH 3 ) 2
H
H
H
H
655
C(CH 3 ) 2
H
H
H
H
656
C(CH 3 ) 2
H
H
H
H
657
C(CH 3 ) 2
H
H
H
H
658
C(CH 3 ) 2
H
H
H
H
659
C(CH 3 ) 2
H
H
H
H
660
C(CH 3 ) 2
H
H
H
H
661
C(CH 3 ) 2
H
H
H
H
662
C(CH 3 ) 2
H
H
H
H
663
C(CH 3 ) 2
H
H
H
H
664
C(CH 3 ) 2
H
H
H
H
665
C(CH 3 ) 2
H
H
H
H
666
C(CH 3 ) 2
H
H
H
H
667
C(CH 3 ) 2
H
H
H
H
668
C(CH 3 ) 2
H
H
H
H
669
C(CH 3 ) 2
H
H
H
H
670
C(CH 3 ) 2
H
H
H
H
671
C(CH 3 ) 2
H
H
H
H
672
C(CH 3 ) 2
H
H
H
H
673
C(CH 3 ) 2
H
H
H
H
674
C(CH 3 ) 2
H
H
H
H
675
C(CH 3 ) 2
H
H
H
H
676
C(CH 3 ) 2
H
H
H
H
677
C(CH 3 ) 2
H
H
H
H
678
C(CH 3 ) 2
H
H
H
H
679
C(CH 3 ) 2
H
H
H
H
680
C(CH 3 ) 2
H
H
H
H
681
C(CH 3 ) 2
H
H
H
H
682
C(CH 3 ) 2
H
H
H
H
683
C(CH 3 ) 2
H
H
H
H
684
C(CH 3 ) 2
H
H
H
H
685
C(CH 3 ) 2
H
H
H
H
686
C(CH 3 ) 2
H
H
H
H
687
C(CH 3 ) 2
H
H
H
H
688
C(CH 3 ) 2
H
H
H
H
689
C(CH 3 ) 2
H
H
H
H
690
C(CH 3 ) 2
H
H
H
H
691
C(CH 3 ) 2
H
H
H
H
692
C(CH 3 ) 2
H
H
H
H
693
C(CH 3 ) 2
H
H
H
H
694
C(CH 3 ) 2
H
H
H
H
695
C(CH 3 ) 2
H
H
H
H
696
C(CH 3 ) 2
H
H
H
H
697
C(CH 3 ) 2
H
H
H
H
698
C(CH 3 ) 2
H
H
H
H
699
C(CH 3 ) 2
H
H
H
H
700
C(CH 3 ) 2
H
H
H
H
701
C(CH 3 ) 2
H
H
H
H
702
C(CH 3 ) 2
H
H
H
H
703
C(CH 3 ) 2
H
H
H
H
704
C(CH 3 ) 2
H
H
H
H
705
C(CH 3 ) 2
H
H
H
H
706
C(CH 3 ) 2
H
H
H
H
707
C(CH 3 ) 2
H
H
H
H
708
C(CH 3 ) 2
H
H
H
H
709
C(CH 3 ) 2
H
H
H
H
710
C(CH 3 ) 2
H
H
H
H
711
C(CH 3 ) 2
H
H
H
H
712
C(CH 3 ) 2
H
H
H
H
713
C(CH 3 ) 2
H
H
H
H
714
C(CH 3 ) 2
H
H
H
H
715
C(CH 3 ) 2
H
H
H
H
716
C(CH 3 ) 2
H
H
H
H
5
10. The compound of claim 9 , wherein the compound is selected from the group consisting of Compound A-1 through Compound A-716, and Compound B-1 through Compound B-115992;
wherein each Compound A-x has the formula Ir(L Ai ) 3 , each Compound B-y has the formula Ir(L Ai )(L Bj ) 2 ;
wherein x=i, y=716j+i−716;
i is an integer from 1 to 716, j is an integer from 1 to 162; and
wherein L Bj is selected from the group consisting of:
11. The compound of claim 1 , wherein the compound has a formula of M(L A ) n (L B ) m-n ;
wherein M is Ir or Pt;
wherein L B is a bidentate ligand; and
wherein when M is Ir, m is 3, and n is 1, 2, or 3; and
wherein when M is Pt, m is 2, and n is 1, or 2.
12. The compound of claim 11 , wherein the compound has a formula selected from the group consisting of Ir(L A ) 3 , Ir(L A )(L B ) 2 wherein L B is different from L A , and Ir(L A ) 2 (L B ) wherein L B is different from L A .
13. The compound of claim 11 , wherein L B is selected from the group consisting of:
wherein each X 1 to X 13 are independently selected from the group consisting of carbon and nitrogen;
wherein X is selected from the group consisting of BR′, NR′, PR′, O, S, Se, C=O, S=O, SO 2 , CR′R″, SiR′R″, and GeR′R″;
wherein R′ and R″ are optionally fused or joined to form a ring;
wherein each R a , R b , R c , and R d may represent from mono substitution to the possible maximum number of substitution, or no substitution;
wherein R′, R″, R a , R b , R c , and R d are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and
wherein any two adjacent substituents of R a , R b , R c , and R d are optionally fused or joined to form a ring or form a multidentate ligand.
14. The compound of claim 1 , wherein X is selected from the group consisting of NR, CRR′, O, S, Se, BRR′, and SiRR′.
15. An organic light emitting device (OLED) comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the cathode, comprising a compound comprising a ligand L A of Formula I:
wherein X is selected from the group consisting of a single bond, NR, CRR′, O, S, Se, BRR′, and SiRR′;
wherein Z 1 , Z 2 , and Z 3 are each independently selected from the group consisting of carbon and nitrogen;
wherein rings A and C are each independently selected from the group consisting of aryl ring, and heteroaryl ring;
wherein R A , R B , and R C each independently represent from mono-substitution to the possible maximum number of substitution, or no substitution;
wherein R A , R B , R C , R, and R′ are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein any adjacent substituents of R B , R, and R′ are optionally joined or fused into a ring;
wherein the ligand L A is coordinated to a metal M; and
wherein the ligand L A is optionally linked with other ligands to comprise a tridentate, tetradentate, pentadentate or hexadentate ligand.
16. The OLED of claim 15 , wherein the OLED is incorporated into a device selected from the group consisting of a consumer product, an electronic component module, and a lighting panel.
17. The OLED of claim 15 , wherein the organic layer is an emissive layer and the compound is an emissive dopant or a non-emissive dopant.
18. The OLED of claim 15 , wherein the organic layer further comprises a host;
wherein the host comprises at least one chemical group selected from the group consisting of triphenylene, carbazole, dibenzothiophene, dibenzofuran, dibenzoselenophene, azatriphenylene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.
19. The OLED of claim 15 , wherein the organic layer further comprises a host and the host is selected from the group consisting of:
and combinations thereof.
20. A formulation comprising a compound comprising a ligand L A of Formula I:
wherein X is selected from the group consisting of a single bond, NR, CRR′, O, S, Se, BRR′, and SiRR′;
wherein Z 1 , Z 2 , and Z 3 are each independently selected from the group consisting of carbon and nitrogen;
wherein rings A and C are each independently selected from the group consisting of aryl ring, and heteroaryl ring;
wherein R A , R B , and R C each independently represent from mono-substitution to the possible maximum number of substitution, or no substitution;
wherein R A , R B , R C , R, and R′ are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
wherein any adjacent substituents of R B , R, and R′ are optionally joined or fused into a ring;
wherein the ligand L A is coordinated to a metal M; and
wherein the ligand L A is optionally linked with other ligands to comprise a tridentate, tetradentate, pentadentate or hexadentate ligand.