Phosphorescent organic metal complex and use thereof
Provided are a phosphorescent organometallic complex and a use thereof. The metal complex has a ligand with a structure represented by Formula 1 and may be used as a light-emitting material in an electroluminescent device. These novel metal complexes can not only maintain low voltage and improve device efficiency in electroluminescent devices but also greatly reduce the half-peak width of light emitted by these devices so as to greatly improve color saturation of the light emitted by these devices, thereby providing better device performance. Further provided are an electroluminescent device and a compound formulation.
1. A metal complex, having a general formula of M(L a ) m (L b ) n (L c ) q , wherein
M is, at each occurrence identically or differently, selected from the group consisting of Cu, Ag, Au, Ru, Rh, Pd, Os, Ir, and Pt;
m is 1, 2, or 3, n is 0, 1, or 2, q is 0, 1, or 2, and m+n+q equals the oxidation state of the metal M; wherein when m is greater than or equal to 2, the multiple L a are the same or different; when n is equal to 2, the two L b are the same or different; when q is equal to 2, the two L c are the same or different;
L a , L b , and L c are a first ligand, a second ligand, and a third ligand coordinated to the metal M, respectively; L a , L b , and L c can be optionally joined to form a multidentate ligand;
L a has a structure represented by Formula 1:
wherein,
Z is selected from the group consisting of O, S, Se, NR, CRR, and SiRR, wherein when two R are present, the two R are the same or different;
X 1 to X 8 are, at each occurrence identically or differently, selected from C, CR x , or N;
Y 1 to Y 4 are, at each occurrence identically or differently, selected from CR y or N;
at least one of X 1 to X 8 is selected from CR x , and the R x is cyano;
at least two of Y 1 to Y 4 are selected from CR y , and wherein at least one of the R y is deuterium, and at least one of the R y has a structure of -L-R d ;
L is, at each occurrence identically or differently, selected from a single bond, substituted or unsubstituted alkylene having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkylene having 3 to 20 carbon atoms, substituted or unsubstituted arylene having 6 to 20 carbon atoms, substituted or unsubstituted heteroarylene having 3 to 20 carbon atoms, or combinations thereof;
R d is, at each occurrence identically or differently, selected from substituted alkyl having 1 to 20 carbon atoms, substituted cycloalkyl having 3 to 20 ring carbon atoms, substituted heteroalkyl having 1 to 20 carbon atoms, a substituted heterocyclic group having 3 to 20 ring atoms, substituted arylalkyl having 7 to 30 carbon atoms, substituted alkoxy having 1 to 20 carbon atoms, substituted aryloxy having 6 to 30 carbon atoms, substituted alkenyl having 2 to 20 carbon atoms, substituted aryl having 6 to 30 carbon atoms, substituted heteroaryl having 3 to 30 carbon atoms, substituted alkylsilyl having 3 to 20 carbon atoms, substituted arylsilyl having 6 to 20 carbon atoms, substituted amino having 0 to 20 carbon atoms, or combinations thereof; the substitution in the above-mentioned group of R d contains at least one deuterium atom;
R, R x , and R y are, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof, and
adjacent substituents R, R x , R y , L, and R d can be optionally joined to form a ring; and
L b and L c are, at each occurrence identically or differently, selected from the group consisting of:
wherein,
R a , R b , and R c are, at each occurrence identically or differently, represent mono-substitution, multi-substitution, or non-substitution;
X b is, at each occurrence identically or differently, selected from the group consisting of: O, S, Se, NR N1 , and CR C1 R C2 ;
X c and X d are, at each occurrence identically or differently, selected from the group consisting of: O, S, Se, and NR N2 ;
R a , R b , R c , R N1 , R N2 , R C1 , and R C2 are, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; and
in structures of L b and L c , adjacent substituents R a , R b , R c , R N1 , R N2 , R C1 , and R C2 can be optionally joined to form a ring.
2. The metal complex of claim 1 , wherein the ligand L a is, at each occurrence identically or differently, any one selected from the group consisting of:
3. The metal complex of claim 2 , wherein the ligand L b is, at each occurrence identically or differently, any one selected from the group consisting of:
wherein the ligand L, is, at each occurrence identically or differently, any one selected from the group consisting of:
4. The metal complex of claim 3 , having a structure represented by any one of Ir(L a ) 2 (L b ), Ir(L a )(L b ) 2 , Ir(L a )(L b )(L c ), or Ir(L a ) 2 (L c ); wherein
when the metal complex has the structure of Ir(L a ) 2 (L b ), L a is, at each occurrence identically or differently, any one or any two selected from the group consisting of L a1 to L a1089 , and L b is any one selected from the group consisting of L b1 to L b87 ;
when the metal complex has the structure of Ir(L a )(L b ) 2 , L a is any one selected from the group consisting of L a1 to L a1089 , and L b is, at each occurrence identically or differently, any one or any two selected from the group consisting of L b1 to L b87 ;
when the metal complex has the structure of Ir(L a )(L b )(L c ), L a is any one selected from the group consisting of L a1 to L a1089 , L b is any one selected from the group consisting of L b1 to L b87 , and L c is any one selected from the group consisting of L c1 to L c360 ;
when the metal complex has the structure of Ir(L a ) 2 (L c ), L a is, at each occurrence identically or differently, any one or any two selected from the group consisting of L a1 to L a1089 , and L c is any one selected from the group consisting of L c1 to L c360 .
5. The metal complex of claim 4 , the metal complex is selected from the group consisting of metal complex 1 to metal complex 530;
wherein metal complex 1 to metal complex 448 and metal complex 513 to metal complex 530 have the structure of Ir(L a )(L b ) 2 , wherein two L b are the same, and L a and L b separately correspond to structures listed in a following table:
Metal
Metal
Complex
L a
L b
Complex
L a
L b
1
L a9
L b1
2
L a10
L b1
3
L a11
L b1
4
L a12
L b1
5
L a13
L b1
6
L a14
L b1
7
L a15
L b1
8
L a16
L b1
9
L a17
L b1
10
L a18
L b1
11
L a33
L b1
12
L a34
L b1
13
L a37
L b1
14
L a38
L b1
15
L a41
L b1
16
L a42
L b1
17
L a45
L b1
18
L a46
L b1
19
L a49
L b1
20
L a50
L b1
21
L a53
L b1
22
L a54
L b1
23
L a61
L b1
24
L a62
L b1
25
L a65
L b1
26
L a66
L b1
27
L a73
L b1
28
L a74
L b1
29
L a77
L b1
30
L a78
L b1
31
L a85
L b1
32
L a105
L b1
33
L a133
L b1
34
L a145
L b1
35
L a157
L b1
36
L a181
L b1
37
L a201
L b1
38
L a217
L b1
39
L a297
L b1
40
L a305
L b1
41
L a321
L b1
42
L a345
L b1
43
L a357
L b1
44
L a361
L b1
45
L a369
L b1
46
L a373
L b1
47
L a377
L b1
48
L a393
L b1
49
L a413
L b1
50
L a425
L b1
51
L a505
L b1
52
L a510
L b1
53
L a513
L b1
54
L a515
L b1
55
L a534
L b1
56
L a537
L b1
57
L a629
L b1
58
L a653
L b1
59
L a661
L b1
60
L a665
L b1
61
L a775
L b1
62
L a782
L b1
63
L a836
L b1
64
L a838
L b1
65
L a9
L b3
66
L a10
L b3
67
L a11
L b3
68
L a12
L b3
69
L a13
L b3
70
L a14
L b3
71
L a15
L b3
72
L a16
L b3
73
L a17
L b3
74
L a18
L b3
75
L a33
L b3
76
L a34
L b3
77
L a37
L b3
78
L a38
L b3
79
L a41
L b3
80
L a42
L b3
81
L a45
L b3
82
L a46
L b3
83
L a49
L b3
84
L a50
L b3
85
L a53
L b3
86
L a54
L b3
87
L a61
L b3
88
L a62
L b3
89
L a65
L b3
90
L a66
L b3
91
L a73
L b3
92
L a74
L b3
93
L a77
L b3
94
L a78
L b3
95
L a85
L b3
96
L a105
L b3
97
L a133
L b3
98
L a145
L b3
99
L a157
L b3
100
L a181
L b3
101
L a201
L b3
102
L a217
L b3
103
L a297
L b3
104
L a305
L b3
105
L a321
L b3
106
L a345
L b3
107
L a357
L b3
108
L a361
L b3
109
L a369
L b3
110
L a373
L b3
111
L a377
L b3
112
L a393
L b3
113
L a413
L b3
114
L a425
L b3
115
L a505
L b3
116
L a510
L b3
117
La 513
L b3
118
L a515
L b3
119
L a534
L b3
120
L a537
L b3
121
L a629
L b3
122
L a653
L b3
123
L a661
L b3
124
L a665
L b3
125
L a775
L b3
126
L a782
L b3
127
L a836
L b3
128
L a838
L b3
129
L a9
L b4
130
L a10
L b4
131
L a11
L b4
132
L a12
L b4
133
L a13
L b4
134
L a14
L b4
135
L a15
L b4
136
L a16
L b4
137
L a17
L b4
138
L a18
L b4
139
L a33
L b4
140
L a34
L b4
141
L a37
L b4
142
L a38
L b4
143
L a41
L b4
144
L a42
L b4
145
L a45
L b4
146
L a46
L b4
147
L a49
L b4
148
L a50
L b4
149
L a53
L b4
150
L a54
L b4
151
L a61
L b4
152
L a62
L b4
153
L a65
L b4
154
L a66
L b4
155
L a73
L b4
156
L a74
L b4
157
L a77
L b4
158
L a78
L b4
159
L a85
L b4
160
L a105
L b4
161
L a133
L b4
162
L a145
L b4
163
L a157
L b4
164
L a181
L b4
165
L a201
L b4
166
L a217
L b4
167
L a297
L b4
168
L a305
L b4
169
L a321
L b4
170
L a345
L b4
171
L a357
L b4
172
L a361
L b4
173
L a369
L b4
174
L a373
L b4
175
L a377
L b4
176
L a393
L b4
177
L a413
L b4
178
L a425
L b4
179
L a505
L b4
180
L a510
L b4
181
L a513
L b4
182
L a515
L b4
183
L a534
L b4
184
L a537
L b4
185
L a629
L b4
186
L a653
L b4
187
L a661
L b4
188
L a665
L b4
189
L a775
L b4
190
L a782
L b4
191
L a836
L b4
192
L a838
L b4
193
L a9
L b8
194
L a10
L b8
195
L a11
L b8
196
L a12
L b8
197
L a13
L b8
198
L a14
L b8
199
L a15
L b8
200
L a16
L b8
201
L a17
L b8
202
L a18
L b8
203
L a33
L b8
204
L a34
L b8
205
L a37
L b8
206
L a38
L b8
207
L a41
L b8
208
L a42
L b8
209
L a45
L b8
210
L a46
L b8
211
L a49
L b8
212
L a50
L b8
213
L a53
L b8
214
L a54
L b8
215
L a61
L b8
216
L a62
L b8
217
L a65
L b8
218
L a66
L b8
219
L a73
L b8
220
L a74
L b8
221
L a77
L b8
222
L a78
L b8
223
L a85
L b8
224
L a105
L b8
225
L a133
L b8
226
L a145
L b8
227
L a157
L b8
228
L a181
L b8
229
L a201
L b8
230
L a217
L b8
231
L a297
L b8
232
L a305
L b8
233
L a321
L b8
234
L a345
L b8
235
L a357
L b8
236
L a361
L b8
237
L a369
L b8
238
L a373
L b8
239
L a377
L b8
240
L a393
L b8
241
L a413
L b8
242
L a425
L b8
243
L a505
L b8
244
L a510
L b8
245
L a513
L b8
246
L a515
L b8
247
L a534
L b8
248
L a537
L b8
249
L a629
L b8
250
L a653
L b8
251
L a661
L b8
252
L a665
L b8
253
L a775
L b8
254
L a782
L b8
255
L a836
L b8
256
L a838
L b8
257
L a9
L b43
258
L a10
L b43
259
L a11
L b43
260
L a12
L b43
261
L a13
L b43
262
L a14
L b43
263
L a15
L b43
264
L a16
L b43
265
L a17
L b43
266
L a18
L b43
267
L a33
L b43
268
L a34
L b43
269
L a37
L b43
270
L a38
L b43
271
L a41
L b43
272
L a42
L b43
273
L a45
L b43
274
L a46
L b43
275
L a49
L b43
276
L a50
L b43
277
L a53
L b43
278
L a54
L b43
279
L a61
L b43
280
L a62
L b43
281
L a65
L b43
282
L a66
L b43
283
L a73
L b43
284
L a74
L b43
285
L a77
L b43
286
L a78
L b43
287
L a85
L b43
288
L a105
L b43
289
L a133
L b43
290
L a145
L b43
291
L a157
L b43
292
L a181
L b43
293
L a201
L b43
294
L a217
L b43
295
L a297
L b43
296
L a305
L b43
297
L a321
L b43
298
L a345
L b43
299
L a357
L b43
300
L a361
L b43
301
L a369
L b43
302
L a373
L b43
303
L a377
L b43
304
L a393
L b43
305
L a413
L b43
306
L a425
L b43
307
L a505
L b43
308
L a510
L b43
309
L a513
L b43
310
L a515
L b43
311
L a534
L b43
312
L a537
L b43
313
L a629
L b43
314
L a653
L b43
315
L a661
L b43
316
L a665
L b43
317
L a775
L b43
318
L a782
L b43
319
L a836
L b43
320
L a838
L b43
321
L a9
L b44
322
L a10
L b44
323
L a11
L b44
324
L a12
L b44
325
L a13
L b44
326
L a14
L b44
327
L a15
L b44
328
L a16
L b44
329
L a17
L b44
330
L a18
L b44
331
L a33
L b44
332
L a34
L b44
333
L a37
L b44
334
L a38
L b44
335
L a41
L b44
336
L a42
L b44
337
L a45
L b44
338
L a46
L b44
339
L a49
L b44
340
L a50
L b44
341
L a53
L b44
342
L a54
L b44
343
L a61
L b44
344
L a62
L b44
345
L a65
L b44
346
L a66
L b44
347
L a73
L b44
348
L a74
L b44
349
L a77
L b44
350
L a78
L b44
351
L a85
L b44
352
L a105
L b44
353
L a133
L b44
354
L a145
L b44
355
L a157
L b44
356
L a181
L b44
357
L a201
L b44
358
L a217
L b44
359
L a297
L b44
360
L a305
L b44
361
L a321
L b44
362
L a345
L b44
363
L a357
L b44
364
L a361
L b44
365
L a369
L b44
366
L a373
L b44
367
L a377
L b44
368
L a393
L b44
369
L a413
L b44
370
L a425
L b44
371
L a505
L b44
372
L a510
L b44
373
L a513
L b44
374
L a515
L b44
375
L a534
L b44
376
L a537
L b44
377
L a629
L b44
378
L a653
L b44
379
L a661
L b44
380
L a665
L b44
381
L a775
L b44
382
L a782
L b44
383
L a836
L b44
384
L a838
L b44
385
L a9
L b60
386
L a10
L b60
387
L a11
L b60
388
L a12
L b60
389
L a13
L b60
390
L a14
L b60
391
L a15
L b60
392
L a16
L b60
393
L a17
L b60
394
L a18
L b60
395
L a33
L b60
396
L a34
L b60
397
L a37
L b60
398
L a38
L b60
399
L a41
L b60
400
L a42
L b60
401
L a45
L b60
402
L a46
L b60
403
L a49
L b60
404
L a50
L b60
405
L a53
L b60
406
L a54
L b60
407
L a61
L b60
408
L a62
L b60
409
L a65
L b60
410
L a66
L b60
411
L a73
L b60
412
L a74
L b60
413
L a77
L b60
414
L a78
L b60
415
L a85
L b60
416
L a105
L b60
417
L a133
L b60
418
L a145
L b60
419
L a157
L b60
420
L a181
L b60
421
L a201
L b60
422
L a217
L b60
423
L a297
L b60
424
L a305
L b60
425
L a321
L b60
426
L a345
L b60
427
L a357
L b60
428
L a361
L b60
429
L a369
L b60
430
L a373
L b60
431
L a377
L b60
432
L a393
L b60
433
L a413
L b60
434
L a425
L b60
435
L a505
L b60
436
L a510
L b60
437
L a513
L b60
438
L a515
L b60
439
L a534
L b60
440
L a537
L b60
441
L a629
L b60
442
L a653
L b60
443
L a661
L b60
444
L a665
L b60
445
L a775
L b60
446
L a782
L b60
447
L a836
L b60
448
L a838
L b60
513
L a9
L b79
514
L a10
L b79
515
L a11
L b79
516
L a12
L b79
517
L a13
L b79
518
L a14
L b79
519
L a15
L b79
520
L a16
L b79
521
L a17
L b79
522
L a18
L b79
523
L a297
L b79
524
L a305
L b79
525
L a321
L b79
526
L a345
L b79
527
L a357
L b79
528
L a361
L b79
529
L a369
L b79
530
L a373
L b79
wherein metal complex 449 to metal complex 512 have the structure of Ir(L a ) 2 L c , wherein two L a are the same, and L a and L c separately correspond to structures listed in a following table:
Metal
Metal
Complex
L a
L c
Complex
L a
L c
449
L a9
L c1
450
L a10
L c1
451
L a11
L c1
452
L a12
L c1
453
L a13
L c1
454
L a14
L c1
455
L a15
L c1
456
L a16
L c1
457
L a21
L c1
458
L a22
L c1
459
L a33
L c1
460
L a34
L c1
461
L a37
L c1
462
L a38
L c1
463
L a41
L c1
464
L a42
L c1
465
L a45
L c1
466
L a46
L c1
467
L a49
L c1
468
L a50
L c1
469
L a53
L c1
470
L a54
L c1
471
L a61
L c1
472
L a62
L c1
473
L a65
L c1
474
L a66
L c1
475
L a73
L c1
476
L a74
L c1
477
L a77
L c1
478
L a78
L c1
479
L a85
L c1
480
L a105
L c1
481
L a133
L c1
482
L a145
L c1
483
L a157
L c1
484
L a181
L c1
485
L a201
L c1
486
L a217
L c1
487
L a297
L c1
488
L a305
L c1
489
L a321
L c31
490
L a345
L c31
491
L a357
L c31
492
L a361
L c31
493
L a369
L c31
494
L a373
L c31
495
L a377
L c31
496
L a393
L c31
497
L a413
L c31
498
L a425
L c31
499
L a505
L c31
500
L a510
L c31
501
L a513
L c31
502
L a515
L c31
503
L a534
L c31
504
L a537
L c31
505
L a629
L c31
506
L a653
L c31
507
L a661
L c31
508
L a665
L c31
509
L a775
L c31
510
L a782
L c31
511
L a836
L c31
512
L a838
L c31 .
6. The metal complex of claim 1 , wherein L a has a structure represented by any one of Formula 1a to Formula 1d:
wherein Z, X 1 to X 8 , and Y 1 to Y 4 have same definitions and scopes as those in claim 1 .
7. The metal complex of claim 6 , a general formula of Ir(L a ) m (L b ) 3-m and a structure represented by Formula 2:
wherein,
m is selected from 1 or 2; wherein when m is equal to 2, the two L a are the same or different;
when m is equal to 1, the two L b are the same or different;
Z is selected from the group consisting of O, S, Se, wherein when two R are present, the two R are the same or different;
X 3 to X 8 are, at each occurrence identically or differently, selected from CR x or N;
Y 1 to Y 4 are, at each occurrence identically or differently, selected from CR y or N;
at least one of X 3 to X 8 is selected from CR x , and the R x is cyano;
at least two of Y 1 to Y 4 are selected from CR y , and wherein at least one of the R y is deuterium, and at least one of the R y has a structure of -L-R d ;
L is, at each occurrence identically or differently, selected from a single bond, substituted or unsubstituted alkylene having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkylene having 3 to 20 carbon atoms, substituted or unsubstituted arylene having 6 to 20 carbon atoms, substituted or unsubstituted heteroarylene having 3 to 20 carbon atoms, or combinations thereof,
R d is, at each occurrence identically or differently, selected from substituted alkyl having 1 to 20 carbon atoms, substituted cycloalkyl having 3 to 20 ring carbon atoms, substituted heteroalkyl having 1 to 20 carbon atoms, a substituted heterocyclic group having 3 to 20 ring atoms, substituted arylalkyl having 7 to 30 carbon atoms, substituted alkoxy having 1 to 20 carbon atoms, substituted aryloxy having 6 to 30 carbon atoms, substituted alkenyl having 2 to 20 carbon atoms, substituted aryl having 6 to 30 carbon atoms, substituted heteroaryl having 3 to 30 carbon atoms, substituted alkylsilyl having 3 to 20 carbon atoms, substituted arylsilyl having 6 to 20 carbon atoms, substituted amino having 0 to 20 carbon atoms, or combinations thereof, the substitution in the above-mentioned group of R d contains at least one deuterium atom;
R, R x , R y , and R 1 to R 8 are, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof, and
adjacent substituents R, R x , R y , R 1 to R 8 , L, and R d can be optionally joined to form a ring.
8. The metal complex of claim 7 , R d is, at each occurrence identically or differently, selected from the group consisting of: substituted alkyl having 1 to 20 carbon atoms, substituted cycloalkyl having 3 to 20 ring carbon atoms, substituted aryl having 6 to 30 carbon atoms, substituted heteroaryl having 3 to 30 carbon atoms, and combinations thereof; and at least one substitution in the above groups of R d is a deuterium atom.
9. The metal complex of claim 8 , when the carbon atom at a benzylic position in the deuterated group is a primary carbon atom, a secondary carbon atom, or a tertiary carbon atom, the benzylic position in the deuterated group is fully deuterated.
10. The metal complex of claim 4 , R d is, at each occurrence identically or differently, selected from the group consisting of: CD 3 , CD 2 CH 3 , CD 2 CD 3 , CD(CH 3 ) 2 , CD(CD 3 ) 2 , CD 2 CH(CH 3 ) 2 , CD 2 C(CH 3 ) 3 ,
and combinations thereof.
11. The metal complex of claim 7 , wherein Z is O.
12. The metal complex of claim 7 , wherein X 3 to X 8 are, at each occurrence identically or differently, selected from CR x .
13. The metal complex of claim 7 , wherein X 3 to X 8 are, at each occurrence identically or differently, selected from CR x or N, and at least one of X 3 to X 8 is N.
14. The metal complex of claim 7 , wherein at least two of X 3 to X 8 are selected from CR x , and wherein at least one of the R x is cyano, and at least one of the R x is, at each occurrence identically or differently, selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof.
15. The metal complex of claim 7 , wherein at least one of X 5 to X 8 is selected from CR x , and the R x is cyano.
16. The metal complex of claim 7 , wherein Y 1 to Y 4 are, at each occurrence identically or differently, selected from CR y .
17. The metal complex of claim 7 , wherein Y 1 to Y 4 are, at each occurrence identically or differently, selected from CR y or N, and at least one of Y 1 to Y 4 is N.
18. The metal complex of claim 7 , wherein at least one of Y 2 to Y 4 is selected from CR y , and the R y has a structure of -L-R d .
19. The metal complex of claim 7 , wherein L is, at each occurrence identically or differently, selected from a single bond, substituted or unsubstituted alkylene having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkylene having 3 to 20 carbon atoms, or combinations thereof.
20. The metal complex of claim 8 , wherein R d is, at each occurrence identically or differently, selected from the group consisting of: partially or fully deuterated alkyl having 1 to 20 carbon atoms, partially or fully deuterated cycloalkyl having 3 to 20 ring carbon atoms, and combinations thereof; and when a carbon atom at a benzylic position in the deuterated group is a primary carbon atom, a secondary carbon atom, or a tertiary carbon atom, the carbon atom at the benzylic position in the deuterated group is joined to at least one deuterium atom.
21. The metal complex of claim 7 , wherein Y 1 to Y 4 are each independently selected from CR y or N, and the R y is, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, a cyano group, a hydroxyl group, a sulfanyl group, and combinations thereof.
22. The metal complex of claim 7 , wherein X 3 to X 8 are, at each occurrence identically or differently, selected from CR x or N, and the R x is, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof, and when the R x is selected from substituted alkyl having 1 to 20 carbon atoms or substituted cycloalkyl having 3 to 20 ring carbon atoms, the substituent in the alkyl and cycloalkyl is selected from the group consisting of: unsubstituted alkyl having 1 to 20 carbon atoms, unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, unsubstituted heteroalkyl having 1 to 20 carbon atoms, an unsubstituted heterocyclic group having 3 to 20 ring atoms, unsubstituted arylalkyl having 7 to 30 carbon atoms, unsubstituted alkoxy having 1 to 20 carbon atoms, unsubstituted aryloxy having 6 to 30 carbon atoms, unsubstituted alkenyl having 2 to 20 carbon atoms, unsubstituted alkynyl having 2 to 20 carbon atoms, unsubstituted aryl having 6 to 30 carbon atoms, unsubstituted heteroaryl having 3 to 30 carbon atoms, unsubstituted amino having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof, and
adjacent substituents R x are not joined to form a ring.
23. The metal complex of claim 7 , wherein at least one or two of R 1 to R 8 is(are), at each occurrence identically or differently, selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof.
24. The metal complex of claim 7 , wherein one, two, three, or all of R 2 , R 3 , R 6 , and R 7 is(are), at each occurrence identically or differently, selected from the group consisting of: deuterium, fluorine, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, and combinations thereof.
25. The metal complex of claim 7 , wherein X 8 is N.
26. The metal complex of claim 7 , wherein at least two of X 3 to X 8 are selected from CR x , and wherein at least one of the R x is cyano, and at least one of the R x is, at each occurrence identically or differently, selected from the group consisting of: deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, and combinations thereof.
27. The metal complex of claim 7 , wherein at least one of X 6 to X 8 is selected from CR x , and the R x is cyano.
28. The metal complex of claim 7 , wherein X 7 or X 8 is selected from CR x , and the R x is cyano.
29. The metal complex of claim 7 , wherein Y 3 is N.
30. The metal complex of claim 7 , wherein Y 2 and/or Y 3 are(is) selected from CR y , and the R y has a structure of -L-R d .
31. The metal complex of claim 7 , wherein Y 2 and/or Y 3 are(is) selected from CR y , and the R y has a structure of -L-R d ;
and Y 1 and/or Y 4 are(is) selected from CR y , and the R y is deuterium.
32. The metal complex of claim 7 , wherein R d is, at each occurrence identically or differently, selected from the group consisting of: partially or fully deuterated alkyl having 1 to 20 carbon atoms, partially or fully deuterated cycloalkyl having 3 to 20 ring carbon atoms, and combinations thereof.
33. The metal complex of claim 7 , at least one of Y 1 to Y 2 is selected from CR y , and the R y is, at each occurrence identically or differently, selected from the group consisting of: hydrogen, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, a cyano group, a hydroxyl group, a sulfanyl group, and combinations thereof.
34. The metal complex of claim 7 , two, three, or all of R 2 , R 3 , R 6 , and R 7 is(are), at each occurrence identically or differently, selected from the group consisting of: deuterium, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, t-butyl, cyclopentyl, cyclohexyl, and combinations thereof, optionally, hydrogen in the above groups can be partially or fully deuterated.
35. An electroluminescent device, comprising:
an anode,
a cathode, and
an organic layer disposed between the anode and the cathode, wherein the organic layer comprises the metal complex of claim 1 .
36. The electroluminescent device of claim 35 , wherein the organic layer is a light-emitting layer, and the metal complex is a light-emitting material.
37. The electroluminescent device of claim 36 , wherein the light-emitting layer further comprises at least one host compound.
38. The metal complex of claim 1 , wherein
M is, at each occurrence identically or differently, selected from Pt or Ir;
L b and L c are, at each occurrence identically or differently selected from the group consisting of:
wherein,
R a and R b are, at each occurrence identically or differently, represent mono-substitution, multi-substitution, or non-substitution;
R a and R b are, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 20 ring atoms, substituted or unsubstituted arylalkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, substituted or unsubstituted amino having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof, and
in structures of L b and L c , adjacent substituents R a and R b can be optionally joined to form a ring.
39. A compound formulation, comprising the metal complex of claim 1 .