# US 2021/0280802 A1 · Organic electroluminescent material and device

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- Number: US 2021/0280802 A1
- Document ID: US20210280802A1
- Status: Published application
- Kind: A1
- Application number: 17/248,964
- Filed: 2021-02-16
- Published: 2021-09-09
- Earliest claimed: 2020-02-20
- Assignees: Beijing Summer Sprout Technology Co., Ltd.
- Applicants: Beijing Summer Sprout Technology Co., Ltd.
- Inventors: Tao WANG; Chi Yuen Raymond KWONG; Chuanjun XIA
- Web page: https://patentgrep.com/patent/US20210280802A1

## CPC

- H10K 85/342: {comprising iridium}
- C07F 15/0033: {Iridium compounds}
- C09K 11/06: containing organic luminescent materials
- C09K 2211/1029: containing one nitrogen atom as the heteroatom
- C09K 2211/1033: with oxygen
- C09K 2211/185: of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 2101/10: Triplet emission
- H10K 2101/90: {Multiple hosts in the emissive layer}
- Y02E 10/549: Organic PV cells
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## Abstract

Disclosed is an organic electroluminescent material and device. The organic electroluminescent material is a novel metal complex that comprises a ligand having a fluorene structure and a ligand having a dibenzofuran, dibenzothiophene, or dibenzoselenophene structure, and has a general formula of M(La)m(Lb)n(Lc)q, where the ligand La has a structure represented by Formula IA, the ligand Lb has a structure represented by Formula IB, and the ligand Lc is a monoanionic bidentate ligand. The metal complex may be used as the light-emitting material in the organic electroluminescent device. These novel compounds can greatly improve the device efficiency and provide better device performance. Further provided are an electroluminescent device and a compound formulation.

## Claims

### Claim at position 1

1-30. (canceled)

### Claim 31

A metal complex, having a general formula of M(La)m(Lb)n(Lc)q, wherein La, Lb, and Lc are the first ligand, the second ligand and the third ligand coordinated to the metal M, respectively; wherein Lc is a monoanionic bidentate ligand, and Lc is the same as or different from the La or the Lb; wherein La, Lb, and Lc can be optionally joined to form a tetradentate ligand;
wherein the metal M is selected from a metal with a relative atomic mass greater than 40;
wherein m is 1 or 2, n is 1 or 2, q is 0 or 1, and m+n+q equals to the oxidation state of the metal M; when m is 2, two La can be the same or different; when n is 2, two Lb can be the same or different;
wherein the ligand La has, at each occurrence identically or differently, a structure represented by Formula IA, and the ligand Lb has, at each occurrence identically or differently, a structure represented by Formula IB:
wherein
in Formula IA, W1, W2, W3, and W4 are each independently selected from N or CRw; X1, X2, X3, and X4 are each independently selected from N, C, or CRx; V1, V2, V3, and V4 are each independently selected from N or CRy;
in Formula IB, Y1, Y2, Y3, and Y4 are each independently selected from N or CRy; Z1, Z2, Z3, and Z4 are each independently selected from N, C, or CRz; U1, U2, U3, and U4 are each independently selected from N or CRu;
wherein Q is, at each occurrence identically or differently, selected from O, S, or Se;
wherein Rw, Ry, Ru, Rv, Rx, Rz, and R 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, 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 sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
wherein adjacent substituents Rw, Rv, Rx, and R can be optionally joined to form a ring;
wherein adjacent substituents Ry, Ru, and Rz can be optionally joined to form a ring.

### Claim 32 (depends on 31)

The metal complex according to claim 31, wherein the metal M is selected from the group consisting of Cu, Ag, Au, Ru, Rh, Pd, Os, Ir, and Pt; preferably, the metal M is selected from Pt, Os, or Ir; more preferably, the metal M is selected from Ir.

### Claim 33 (depends on 31)

The metal complex according to claim 31, wherein La is, at each occurrence identically or differently, selected from the group consisting of:
wherein, X1, X3, and X4 are each independently selected from N or CRX; W1, W2, W3, and W4 are each independently selected from N or CRW; V1, V2, V3, and V4 are each independently selected from N or CRx;
preferably, L is, at each occurrence identically or differently, selected from a structure represented by Formula II, Formula III, or Formula IV; more preferably, La, is, at each occurrence identically or differently, selected from a structure represented by Formula IV;
wherein Lb is, at each occurrence identically or differently, selected from the group consisting of:
wherein, Z1, Z3, and Z4 are each independently selected from N or CRz; U1, U2, U3, and U4 are each independently selected from N or CRu; Y1, Y2, Y3, and Y4 are each independently selected from N or CRy; Q is, at each occurrence identically or differently, selected from O, S, or Se;
wherein Rw, Ry, Ru, Rv, Rx, Rz, and R 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, 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 sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
wherein adjacent substituents Rw, Rv, Rx, and R can be optionally joined to form a ring;
wherein adjacent substituents Ry, Ru, and Rz can be optionally joined to form a ring;
preferably, Lb is, at each occurrence identically or differently, selected from a structure represented by Formula VI.

### Claim 34 (depends on 33)

The metal complex according to claim 33, wherein at least one of W1, W2, W3, W4, X1, X3, X4, V1, V2, V3, and V4 is selected from N; preferably, one of W1, W2, W3, W4, X1, X3, X4, V1, V2, V3, and V4 is selected from N; more preferably, one of X1, X3, X4, V1, V2, V3, and V4 is selected from N; most preferably, one of V1, V2, V3, and V4 is selected from N;
and, wherein at least one of Y1, Y2, Y3, Y4, Z1, Z3, Z4, U1, U2, U3, and U4 is selected from N; preferably, one of Y1, Y2, Y3, Y4, Z1, Z3, Z4, U1, U2, U3, and U4 is selected from N; more preferably, one of Z1, Z3, Z4, U1, U2, U3, and U4 is selected from N; most preferably, one of U1, U2, U3, and U4 is selected from N.

### Claim 35 (depends on 33)

The metal complex according to claim 33, wherein W1, W2, W3, and W4 are each independently selected from CRw; X1, X3, and X4 are each independently selected from CRx; V1, V2, V3, and V4 are each independently selected from CRy;
wherein Y1, Y2, Y3, and Y4 are each independently selected from CRy; Z1, Z3, and Z4 are each independently selected from CRz; U1, U2, U3, and U4 are each independently selected from CRu.

### Claim 36 (depends on 31)

The metal complex according to claim 31, wherein Rw and Ry 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 alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 20 carbon atoms, a cyano group, an isocyano group, and combinations thereof;
preferably, Rw and Ry are, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, fluorine, methyl, ethyl, isopropyl, isobutyl, t-butyl, cyano, isocyano, and combinations thereof.

### Claim 37 (depends on 31)

The metal complex according to claim 31, wherein Q is, at each occurrence identically or differently, selected from O or S, and preferably, Q is O.

### Claim 38 (depends on 31)

The metal complex according to claim 31, wherein Ru, Rv, Rx, Rz, and R 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 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, a cyano group, an isocyano group, a sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
preferably, Ru, Rv, Rx, Rz, and R are, at each occurrence identically or differently, selected from the group consisting of: hydrogen, deuterium, fluorine, methyl, ethyl, isopropyl, isobutyl, t-butyl, phenyl, cyano, isocyano, and combinations thereof.

### Claim 39 (depends on 31)

The metal complex according to claim 31, wherein La is, at each occurrence identically or differently, selected from the group consisting of:
wherein Lb is, at each occurrence identically or differently, selected from the group consisting of:

### Claim 40 (depends on 39)

The metal complex according to claim 39, wherein Lc is selected from the group consisting of the following structures:
wherein
Ra, Rb, and Rc can represent mono-substitution, multiple substitutions, or non-substitution;
Xb is, at each occurrence identically or differently, selected from the group consisting of: O, S, Se, NRN1, and CRC1RC2;
Xc and Xd are, at each occurrence identically or differently, selected from the group consisting of: O, S, Se, and NRN2;
Ra, Rb, Rc, RN1, RN2, RC1 and RC2 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, 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 sulfanyl group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof; and
adjacent substituents can be optionally joined to form a ring;
preferably, the ligand Lc is selected from the group consisting of the following structures:

### Claim 41 (depends on 40)

The metal complex according to claim 40, wherein the metal complex is selected from the group consisting of Compound 1 to Compound 939:
wherein Compound 1 to Compound 437 have a structure of Ir(La)2(Lb), wherein two La are the same, and La and Lb are respectively and correspondingly selected from ligands listed in the following table:
Compound No.
La
Lb
1
La-19
Lb-1
2
La-19
Lb-2
3
La-19
Lb-6
4
La-19
Lb-10
5
La-19
Lb-13
6
La-19
Lb-102
7
La-19
Lb-110
8
La-19
Lb-152
9
La-19
Lb-170
10
La-19
Lb-189
11
La-19
Lb-228
12
La-19
Lb-237
13
La-19
Lb-252
14
La-19
Lb-393
15
La-19
Lb-399
16
La-19
Lb-411
17
La-19
Lb-468
18
La-19
Lb-516
19
La-19
Lb-531
20
La-48
Lb-1
21
La-48
Lb-2
22
La-48
Lb-6
23
La-48
Lb-10
24
La-48
Lb-13
25
La-48
Lb-102
26
La-48
Lb-110
27
La-48
Lb-152
28
La-48
Lb-170
29
La-48
Lb-189
30
La-48
Lb-228
31
La-48
Lb-237
32
La-48
Lb-252
33
La-48
Lb-393
34
La-48
Lb-399
35
La-48
Lb-411
36
La-48
Lb-468
37
La-48
Lb-516
38
La-48
Lb-531
39
La-71
Lb-1
40
La-71
Lb-2
41
La-71
Lb-6
42
La-71
Lb-10
43
La-71
Lb-13
44
La-71
Lb-102
45
La-71
Lb-110
46
La-71
Lb-152
47
La-71
Lb-170
48
La-71
Lb-189
49
La-71
Lb-228
50
La-71
Lb-237
51
La-71
Lb-252
52
La-71
Lb-393
53
La-71
Lb-399
54
La-71
Lb-411
55
La-71
Lb-468
56
La-71
Lb-516
57
La-71
Lb-531
58
La-80
Lb-1
59
La-80
Lb-2
60
La-80
Lb-6
61
La-80
Lb-10
62
La-80
Lb-13
63
La-80
Lb-102
64
La-80
Lb-110
65
La-80
Lb-152
66
La-80
Lb-170
67
La-80
Lb-189
68
La-80
Lb-228
69
La-80
Lb-237
70
La-80
Lb-252
71
La-80
Lb-393
72
La-80
Lb-399
73
La-80
Lb-411
74
La-80
Lb-468
75
La-80
Lb-516
76
La-80
Lb-531
77
La-99
Lb-1
78
La-99
Lb-2
79
La-99
Lb-6
80
La-99
Lb-10
81
La-99
Lb-13
82
La-99
Lb-102
83
La-99
Lb-110
84
La-99
Lb-152
85
La-99
Lb-170
86
La-99
Lb-189
87
La-99
Lb-228
88
La-99
Lb-237
89
La-99
Lb-252
90
La-99
Lb-393
91
La-99
Lb-399
92
La-99
Lb-411
93
La-99
Lb-468
94
La-99
Lb-516
95
La-99
Lb-531
96
La-146
Lb-1
97
La-146
Lb-2
98
La-146
Lb-6
99
La-146
Lb-10
100
La-146
Lb-13
101
La-146
Lb-102
102
La-146
Lb-110
103
La-146
Lb-152
104
La-146
Lb-170
105
La-146
Lb-189
106
La-146
Lb-228
107
La-146
Lb-237
108
La-146
Lb-252
109
La-146
Lb-393
110
La-146
Lb-399
111
La-146
Lb-411
112
La-146
Lb-468
113
La-146
Lb-516
114
La-146
Lb-531
115
La-168
Lb-1
116
La-168
Lb-2
117
La-168
Lb-6
118
La-168
Lb-10
119
La-168
Lb-13
120
La-168
Lb-102
121
La-168
Lb-110
122
La-168
Lb-152
123
La-168
Lb-170
124
La-168
Lb-189
125
La-168
Lb-228
126
La-168
Lb-237
127
La-168
Lb-252
128
La-168
Lb-393
129
La-168
Lb-399
130
La-168
Lb-411
131
La-168
Lb-468
132
La-168
Lb-516
133
La-168
Lb-531
134
La-197
Lb-1
135
La-197
Lb-2
136
La-197
Lb-6
137
La-197
Lb-10
138
La-197
Lb-13
139
La-197
Lb-102
140
La-197
Lb-110
141
La-197
Lb-152
142
La-197
Lb-170
143
La-197
Lb-189
144
La-197
Lb-228
145
La-197
Lb-237
146
La-197
Lb-252
147
La-197
Lb-393
148
La-197
Lb-399
149
La-197
Lb-411
150
La-197
Lb-468
151
La-197
Lb-516
152
La-197
Lb-531
153
La-214
Lb-1
154
La-214
Lb-2
155
La-214
Lb-6
156
La-214
Lb-10
157
La-214
Lb-13
158
La-214
Lb-102
159
La-214
Lb-110
160
La-214
Lb-152
161
La-214
Lb-170
162
La-214
Lb-189
163
La-214
Lb-228
164
La-214
Lb-237
165
La-214
Lb-252
166
La-214
Lb-393
167
La-214
Lb-399
168
La-214
Lb-411
169
La-214
Lb-468
170
La-214
Lb-516
171
La-214
Lb-531
172
La-295
Lb-1
173
La-295
Lb-2
174
La-295
Lb-6
175
La-295
Lb-10
176
La-295
Lb-13
177
La-295
Lb-102
178
La-295
Lb-110
179
La-295
Lb-152
180
La-295
Lb-170
181
La-295
Lb-189
182
La-295
Lb-228
183
La-295
Lb-237
184
La-295
Lb-252
185
La-295
Lb-393
186
La-295
Lb-399
187
La-295
Lb-411
188
La-295
Lb-468
189
La-295
Lb-516
190
La-295
Lb-531
191
La-296
Lb-1
192
La-296
Lb-2
193
La-296
Lb-6
194
La-296
Lb-10
195
La-296
Lb-13
196
La-296
Lb-102
197
La-296
Lb-110
198
La-296
Lb-152
199
La-296
Lb-170
200
La-296
Lb-189
201
La-296
Lb-228
202
La-296
Lb-237
203
La-296
Lb-252
204
La-296
Lb-393
205
La-296
Lb-399
206
La-296
Lb-411
207
La-296
Lb-468
208
La-296
Lb-516
209
La-296
Lb-531
210
La-297
Lb-1
211
La-297
Lb-2
212
La-297
Lb-6
213
La-297
Lb-10
214
La-297
Lb-13
215
La-297
Lb-102
216
La-297
Lb-110
217
La-297
Lb-152
218
La-297
Lb-170
219
La-297
Lb-189
220
La-297
Lb-228
221
La-297
Lb-237
222
La-297
Lb-252
223
La-297
Lb-393
224
La-297
Lb-399
225
La-297
Lb-411
226
La-297
Lb-468
227
La-297
Lb-516
228
La-297
Lb-531
229
La-298
Lb-1
230
La-298
Lb-2
231
La-298
Lb-6
232
La-298
Lb-10
233
La-298
Lb-13
234
La-298
Lb-102
235
La-298
Lb-110
236
La-298
Lb-152
237
La-298
Lb-170
238
La-298
Lb-189
239
La-298
Lb-228
240
La-298
Lb-237
241
La-298
Lb-252
242
La-298
Lb-393
243
La-298
Lb-399
244
La-298
Lb-411
245
La-298
Lb-468
246
La-298
Lb-516
247
La-298
Lb-531
248
La-299
Lb-1
249
La-299
Lb-2
250
La-299
Lb-6
251
La-299
Lb-10
252
La-299
Lb-13
253
La-299
Lb-102
254
La-299
Lb-110
255
La-299
Lb-152
256
La-299
Lb-170
257
La-299
Lb-189
258
La-299
Lb-228
259
La-299
Lb-237
260
La-299
Lb-252
261
La-299
Lb-393
262
La-299
Lb-399
263
La-299
Lb-411
264
La-299
Lb-468
265
La-299
Lb-516
266
La-299
Lb-531
267
La-300
Lb-1
268
La-300
Lb-2
269
La-300
Lb-6
270
La-300
Lb-10
271
La-300
Lb-13
272
La-300
Lb-102
273
La-300
Lb-110
274
La-300
Lb-152
275
La-300
Lb-170
276
La-300
Lb-189
277
La-300
Lb-228
278
La-300
Lb-237
279
La-300
Lb-252
280
La-300
Lb-393
281
La-300
Lb-399
282
La-300
Lb-411
283
La-300
Lb-468
284
La-300
Lb-516
285
La-300
Lb-531
286
La-302
Lb-1
287
La-302
Lb-2
288
La-302
Lb-6
289
La-302
Lb-10
290
La-302
Lb-13
291
La-302
Lb-102
292
La-302
Lb-110
293
La-302
Lb-152
294
La-302
Lb-170
295
La-302
Lb-189
296
La-302
Lb-228
297
La-302
Lb-237
298
La-302
Lb-252
299
La-302
Lb-393
300
La-302
Lb-399
301
La-302
Lb-411
302
La-302
Lb-468
303
La-302
Lb-516
304
La-302
Lb-531
305
La-303
Lb-1
306
La-303
Lb-2
307
La-303
Lb-6
308
La-303
Lb-10
309
La-303
Lb-13
310
La-303
Lb-102
311
La-303
Lb-110
312
La-303
Lb-152
313
La-303
Lb-170
314
La-303
Lb-189
315
La-303
Lb-228
316
La-303
Lb-237
317
La-303
Lb-252
318
La-303
Lb-393
319
La-303
Lb-399
320
La-303
Lb-411
321
La-303
Lb-468
322
La-303
Lb-516
323
La-303
Lb-531
324
La-307
Lb-1
325
La-307
Lb-2
326
La-307
Lb-6
327
La-307
Lb-10
328
La-307
Lb-13
329
La-307
Lb-102
330
La-307
Lb-110
331
La-307
Lb-152
332
La-307
Lb-170
333
La-307
Lb-189
334
La-307
Lb-228
335
La-307
Lb-237
336
La-307
Lb-252
337
La-307
Lb-393
338
La-307
Lb-399
339
La-307
Lb-411
340
La-307
Lb-468
341
La-307
Lb-516
342
La-307
Lb-531
343
La-314
Lb-1
344
La-314
Lb-2
345
La-314
Lb-6
346
La-314
Lb-10
347
La-314
Lb-13
348
La-314
Lb-102
349
La-314
Lb-110
350
La-314
Lb-152
351
La-314
Lb-170
352
La-314
Lb-189
353
La-314
Lb-228
354
La-314
Lb-237
355
La-314
Lb-252
356
La-314
Lb-393
357
La-314
Lb-399
358
La-314
Lb-411
359
La-314
Lb-468
360
La-314
Lb-516
361
La-314
Lb-531
362
La-338
Lb-1
363
La-338
Lb-2
364
La-338
Lb-6
365
La-338
Lb-10
366
La-338
Lb-13
367
La-338
Lb-102
368
La-338
Lb-110
369
La-338
Lb-152
370
La-338
Lb-170
371
La-338
Lb-189
372
La-338
Lb-228
373
La-338
Lb-237
374
La-338
Lb-252
375
La-338
Lb-393
376
La-338
Lb-399
377
La-338
Lb-411
378
La-338
Lb-468
379
La-338
Lb-516
380
La-338
Lb-531
381
La-343
Lb-1
382
La-343
Lb-2
383
La-343
Lb-6
384
La-343
Lb-10
385
La-343
Lb-13
386
La-343
Lb-102
387
La-343
Lb-110
388
La-343
Lb-152
389
La-343
Lb-170
390
La-343
Lb-189
391
La-343
Lb-228
392
La-343
Lb-237
393
La-343
Lb-252
394
La-343
Lb-393
395
La-343
Lb-399
396
La-343
Lb-411
397
La-343
Lb-468
398
La-343
Lb-516
399
La-343
Lb-531
400
La-363
Lb-1
401
La-363
Lb-2
402
La-363
Lb-6
403
La-363
Lb-10
404
La-363
Lb-13
405
La-363
Lb-102
406
La-363
Lb-110
407
La-363
Lb-152
408
La-363
Lb-170
409
La-363
Lb-189
410
La-363
Lb-228
411
La-363
Lb-237
412
La-363
Lb-252
413
La-363
Lb-393
414
La-363
Lb-399
415
La-363
Lb-411
416
La-363
Lb-468
417
La-363
Lb-516
418
La-363
Lb-531
419
La-367
Lb-1
420
La-367
Lb-2
421
La-367
Lb-6
422
La-367
Lb-10
423
La-367
Lb-13
424
La-367
Lb-102
425
La-367
Lb-110
426
La-367
Lb-152
427
La-367
Lb-170
428
La-367
Lb-189
429
La-367
Lb-228
430
La-367
Lb-237
431
La-367
Lb-252
432
La-367
Lb-393
433
La-367
Lb-399
434
La-367
Lb-411
435
La-367
Lb-468
436
La-367
Lb-516
437
La-367
Lb-531
wherein Compound 438 to Compound 874 have a structure of Ir(La)(Lb)2, wherein two Lb are the same, and La and Lb are respectively and correspondingly selected from ligands listed in the following table:
Compound No.
La
Lb
438
La-19
Lb-1
439
La-19
Lb-2
440
La-19
Lb-6
441
La-19
Lb-10
442
La-19
Lb-13
443
La-19
Lb-102
444
La-19
Lb-110
445
La-19
Lb-152
446
La-19
Lb-170
447
La-19
Lb-189
448
La-19
Lb-228
449
La-19
Lb-237
450
La-19
Lb-252
451
La-19
Lb-393
452
La-19
Lb-399
453
La-19
Lb-411
454
La-19
Lb-468
455
La-19
Lb-516
456
La-19
Lb-531
457
La-48
Lb-1
458
La-48
Lb-2
459
La-48
Lb-6
460
La-48
Lb-10
461
La-48
Lb-13
462
La-48
Lb-102
463
La-48
Lb-110
464
La-48
Lb-152
465
La-48
Lb-170
466
La-48
Lb-189
467
La-48
Lb-228
468
La-48
Lb-237
469
La-48
Lb-252
470
La-48
Lb-393
471
La-48
Lb-399
472
La-48
Lb-411
473
La-48
Lb-468
474
La-48
Lb-516
475
La-48
Lb-531
476
La-71
Lb-1
477
La-71
Lb-2
478
La-71
Lb-6
479
La-71
Lb-10
480
La-71
Lb-13
481
La-71
Lb-102
482
La-71
Lb-110
483
La-71
Lb-152
484
La-71
Lb-170
485
La-71
Lb-189
486
La-71
Lb-228
487
La-71
Lb-237
488
La-71
Lb-252
489
La-71
Lb-393
490
La-71
Lb-399
491
La-71
Lb-411
492
La-71
Lb-468
493
La-71
Lb-516
494
La-71
Lb-531
495
La-80
Lb-1
496
La-80
Lb-2
497
La-80
Lb-6
498
La-80
Lb-10
499
La-80
Lb-13
500
La-80
Lb-102
501
La-80
Lb-110
502
La-80
Lb-152
503
La-80
Lb-170
504
La-80
Lb-189
505
La-80
Lb-228
506
La-80
Lb-237
507
La-80
Lb-252
508
La-80
Lb-393
509
La-80
Lb-399
510
La-80
Lb-411
511
La-80
Lb-468
512
La-80
Lb-516
513
La-80
Lb-531
514
La-99
Lb-1
515
La-99
Lb-2
516
La-99
Lb-6
517
La-99
Lb-10
518
La-99
Lb-13
519
La-99
Lb-102
520
La-99
Lb-110
521
La-99
Lb-152
522
La-99
Lb-170
523
La-99
Lb-189
524
La-99
Lb-228
525
La-99
Lb-237
526
La-99
Lb-252
527
La-99
Lb-393
528
La-99
Lb-399
529
La-99
Lb-411
530
La-99
Lb-468
531
La-99
Lb-516
532
La-99
Lb-531
533
La-146
Lb-1
534
La-146
Lb-2
535
La-146
Lb-6
536
La-146
Lb-10
537
La-146
Lb-13
538
La-146
Lb-102
539
La-146
Lb-110
540
La-146
Lb-152
541
La-146
Lb-170
542
La-146
Lb-189
543
La-146
Lb-228
544
La-146
Lb-237
545
La-146
Lb-252
546
La-146
Lb-393
547
La-146
Lb-399
548
La-146
Lb-411
549
La-146
Lb-468
550
La-146
Lb-516
551
La-146
Lb-531
552
La-168
Lb-1
553
La-168
Lb-2
554
La-168
Lb-6
555
La-168
Lb-10
556
La-168
Lb-13
557
La-168
Lb-102
558
La-168
Lb-110
559
La-168
Lb-152
560
La-168
Lb-170
561
La-168
Lb-189
562
La-168
Lb-228
563
La-168
Lb-237
564
La-168
Lb-252
565
La-168
Lb-393
566
La-168
Lb-399
567
La-168
Lb-411
568
La-168
Lb-468
569
La-168
Lb-516
570
La-168
Lb-531
571
La-197
Lb-1
572
La-197
Lb-2
573
La-197
Lb-6
574
La-197
Lb-10
575
La-197
Lb-13
576
La-197
Lb-102
577
La-197
Lb-110
578
La-197
Lb-152
579
La-197
Lb-170
580
La-197
Lb-189
581
La-197
Lb-228
582
La-197
Lb-237
583
La-197
Lb-252
584
La-197
Lb-393
585
La-197
Lb-399
586
La-197
Lb-411
587
La-197
Lb-468
588
La-197
Lb-516
589
La-197
Lb-531
590
La-214
Lb-1
591
La-214
Lb-2
592
La-214
Lb-6
593
La-214
Lb-10
594
La-214
Lb-13
595
La-214
Lb-102
596
La-214
Lb-110
597
La-214
Lb-152
598
La-214
Lb-170
599
La-214
Lb-189
600
La-214
Lb-228
601
La-214
Lb-237
602
La-214
Lb-252
603
La-214
Lb-393
604
La-214
Lb-399
605
La-214
Lb-411
606
La-214
Lb-468
607
La-214
Lb-516
608
La-214
Lb-531
609
La-295
Lb-1
610
La-295
Lb-2
611
La-295
Lb-6
612
La-295
Lb-10
613
La-295
Lb-13
614
La-295
Lb-102
615
La-295
Lb-110
616
La-295
Lb-152
617
La-295
Lb-170
618
La-295
Lb-189
619
La-295
Lb-228
620
La-295
Lb-237
621
La-295
Lb-252
622
La-295
Lb-393
623
La-295
Lb-399
624
La-295
Lb-411
625
La-295
Lb-468
626
La-295
Lb-516
627
La-295
Lb-531
628
La-296
Lb-1
629
La-296
Lb-2
630
La-296
Lb-6
631
La-296
Lb-10
632
La-296
Lb-13
633
La-296
Lb-102
634
La-296
Lb-110
635
La-296
Lb-152
636
La-296
Lb-170
637
La-296
Lb-189
638
La-296
Lb-228
639
La-296
Lb-237
640
La-296
Lb-252
641
La-296
Lb-393
642
La-296
Lb-399
643
La-296
Lb-411
644
La-296
Lb-468
645
La-296
Lb-516
646
La-296
Lb-531
647
La-297
Lb-1
648
La-297
Lb-2
649
La-297
Lb-6
650
La-297
Lb-10
651
La-297
Lb-13
652
La-297
Lb-102
653
La-297
Lb-110
654
La-297
Lb-152
655
La-297
Lb-170
656
La-297
Lb-189
657
La-297
Lb-228
658
La-297
Lb-237
659
La-297
Lb-252
660
La-297
Lb-393
661
La-297
Lb-399
662
La-297
Lb-411
663
La-297
Lb-468
664
La-297
Lb-516
665
La-297
Lb-531
666
La-298
Lb-1
667
La-298
Lb-2
668
La-298
Lb-6
669
La-298
Lb-10
670
La-298
Lb-13
671
La-298
Lb-102
672
La-298
Lb-110
673
La-298
Lb-152
674
La-298
Lb-170
675
La-298
Lb-189
676
La-298
Lb-228
677
La-298
Lb-237
678
La-298
Lb-252
679
La-298
Lb-393
680
La-298
Lb-399
681
La-298
Lb-411
682
La-298
Lb-468
683
La-298
Lb-516
684
La-298
Lb-531
685
La-299
Lb-1
686
La-299
Lb-2
687
La-299
Lb-6
688
La-299
Lb-10
689
La-299
Lb-13
690
La-299
Lb-102
691
La-299
Lb-110
692
La-299
Lb-152
693
La-299
Lb-170
694
La-299
Lb-189
695
La-299
Lb-228
696
La-299
Lb-237
697
La-299
Lb-252
698
La-299
Lb-393
699
La-299
Lb-399
700
La-299
Lb-411
701
La-299
Lb-468
702
La-299
Lb-516
703
La-299
Lb-531
704
La-300
Lb-1
705
La-300
Lb-2
706
La-300
Lb-6
707
La-300
Lb-10
708
La-300
Lb-13
709
La-300
Lb-102
710
La-300
Lb-110
711
La-300
Lb-152
712
La-300
Lb-170
713
La-300
Lb-189
714
La-300
Lb-228
715
La-300
Lb-237
716
La-300
Lb-252
717
La-300
Lb-393
718
La-300
Lb-399
719
La-300
Lb-411
720
La-300
Lb-468
721
La-300
Lb-516
722
La-300
Lb-531
723
La-302
Lb-1
724
La-302
Lb-2
725
La-302
Lb-6
726
La-302
Lb-10
727
La-302
Lb-13
728
La-302
Lb-102
729
La-302
Lb-110
730
La-302
Lb-152
731
La-302
Lb-170
732
La-302
Lb-189
733
La-302
Lb-228
734
La-302
Lb-237
735
La-302
Lb-252
736
La-302
Lb-393
737
La-302
Lb-399
738
La-302
Lb-411
739
La-302
Lb-468
740
La-302
Lb-516
741
La-302
Lb-531
742
La-303
Lb-1
743
La-303
Lb-2
744
La-303
Lb-6
745
La-303
Lb-10
746
La-303
Lb-13
747
La-303
Lb-102
748
La-303
Lb-110
749
La-303
Lb-152
750
La-303
Lb-170
751
La-303
Lb-189
752
La-303
Lb-228
753
La-303
Lb-237
754
La-303
Lb-252
755
La-303
Lb-393
756
La-303
Lb-399
757
La-303
Lb-411
758
La-303
Lb-468
759
La-303
Lb-516
760
La-303
Lb-531
761
La-307
Lb-1
762
La-307
Lb-2
763
La-307
Lb-6
764
La-307
Lb-10
765
La-307
Lb-13
766
La-307
Lb-102
767
La-307
Lb-110
768
La-307
Lb-152
769
La-307
Lb-170
770
La-307
Lb-189
771
La-307
Lb-228
772
La-307
Lb-237
773
La-307
Lb-252
774
La-307
Lb-393
775
La-307
Lb-399
776
La-307
Lb-411
777
La-307
Lb-468
778
La-307
Lb-516
779
La-307
Lb-531
780
La-314
Lb-1
781
La-314
Lb-2
782
La-314
Lb-6
783
La-314
Lb-10
784
La-314
Lb-13
785
La-314
Lb-102
786
La-314
Lb-110
787
La-314
Lb-152
788
La-314
Lb-170
789
La-314
Lb-189
790
La-314
Lb-228
791
La-314
Lb-237
792
La-314
Lb-252
793
La-314
Lb-393
794
La-314
Lb-399
795
La-314
Lb-411
796
La-314
Lb-468
797
La-314
Lb-516
798
La-314
Lb-531
799
La-338
Lb-1
800
La-338
Lb-2
801
La-338
Lb-6
802
La-338
Lb-10
803
La-338
Lb-13
804
La-338
Lb-102
805
La-338
Lb-110
806
La-338
Lb-152
807
La-338
Lb-170
808
La-338
Lb-189
809
La-338
Lb-228
810
La-338
Lb-237
811
La-338
Lb-252
812
La-338
Lb-393
813
La-338
Lb-399
814
La-338
Lb-411
815
La-338
Lb-468
816
La-338
Lb-516
817
La-338
Lb-531
818
La-343
Lb-1
819
La-343
Lb-2
820
La-343
Lb-6
821
La-343
Lb-10
822
La-343
Lb-13
823
La-343
Lb-102
824
La-343
Lb-110
825
La-343
Lb-152
826
La-343
Lb-170
827
La-343
Lb-189
828
La-343
Lb-228
829
La-343
Lb-237
830
La-343
Lb-252
831
La-343
Lb-393
832
La-343
Lb-399
833
La-343
Lb-411
834
La-343
Lb-468
835
La-343
Lb-516
836
La-343
Lb-531
837
La-363
Lb-1
838
La-363
Lb-2
839
La-363
Lb-6
840
La-363
Lb-10
841
La-363
Lb-13
842
La-363
Lb-102
843
La-363
Lb-110
844
La-363
Lb-152
845
La-363
Lb-170
846
La-363
Lb-189
847
La-363
Lb-228
848
La-363
Lb-237
849
La-363
Lb-252
850
La-363
Lb-393
851
La-363
Lb-399
852
La-363
Lb-411
853
La-363
Lb-468
854
La-363
Lb-516
855
La-363
Lb-531
856
La-367
Lb-1
857
La-367
Lb-2
858
La-367
Lb-6
859
La-367
Lb-10
860
La-367
Lb-13
861
La-367
Lb-102
862
La-367
Lb-110
863
La-367
Lb-152
864
La-367
Lb-170
865
La-367
Lb-189
866
La-367
Lb-228
867
La-367
Lb-237
868
La-367
Lb-252
869
La-367
Lb-393
870
La-367
Lb-399
871
La-367
Lb-411
872
La-367
Lb-468
873
La-367
Lb-516
874
La-367
Lb-531
wherein Compound 875 to Compound 939 have a structure of Ir(La)(Lb)(Lc), wherein La, Lb, and Lc are respectively and correspondingly selected from ligands listed in the following table:
Compound No.
La
Lb
Lc
875
La-19
Lb-1
Lc-1
876
La-19
Lb-1
Lc-3
878
La-19
Lb-1
Lc-12
879
La-19
Lb-1
Lc-19
880
La-19
Lb-1
Lc-21
881
La-19
Lb-1
Lc-37
882
La-19
Lb-1
Lc-40
883
La-19
Lb-1
Lc-44
884
La-48
Lb-6
Lc-1
885
La-48
Lb-6
Lc-3
886
La-48
Lb-6
Lc-12
887
La-48
Lb-6
Lc-19
888
La-48
Lb-6
Lc-21
889
La-48
Lb-6
Lc-37
890
La-48
Lb-6
Lc-40
891
La-48
Lb-6
Lc-44
892
La-71
Lb-102
Lc-1
893
La-71
Lb-102
Lc-3
894
La-71
Lb-102
Lc-12
895
La-71
Lb-102
Lc-19
896
La-71
Lb-102
Lc-21
897
La-71
Lb-102
Lc-37
898
La-71
Lb-102
Lc-40
899
La-71
Lb-102
Lc-44
900
La-71
Lb-103
Lc-1
901
La-71
Lb-103
Lc-3
902
La-71
Lb-103
Lc-12
903
La-71
Lb-103
Lc-19
904
La-71
Lb-103
Lc-21
905
La-71
Lb-103
Lc-37
906
La-71
Lb-103
Lc-40
907
La-71
Lb-103
Lc-44
908
La-295
Lb-110
Lc-1
909
La-295
Lb-110
Lc-3
910
La-295
Lb-110
Lc-12
911
La-295
Lb-110
Lc-19
912
La-295
Lb-110
Lc-21
913
La-295
Lb-110
Lc-37
914
La-295
Lb-110
Lc-40
915
La-295
Lb-110
Lc-44
916
La-299
Lb-170
Lc-1
917
La-299
Lb-170
Lc-3
918
La-299
Lb-170
Lc-12
919
La-299
Lb-170
Lc-19
920
La-299
Lb-170
Lc-21
921
La-299
Lb-170
Lc-37
922
La-299
Lb-170
Lc-40
923
La-299
Lb-170
Lc-44
924
La-303
Lb-252
Lc-1
925
La-303
Lb-252
Lc-3
926
La-303
Lb-252
Lc-12
927
La-303
Lb-252
Lc-19
928
La-303
Lb-252
Lc-21
929
La-303
Lb-252
Lc-37
930
La-303
Lb-252
Lc-40
931
La-303
Lb-252
Lc-44
932
La-363
Lb-516
Lc-1
933
La-363
Lb-516
Lc-3
934
La-363
Lb-516
Lc-12
935
La-363
Lb-516
Lc-19
936
La-363
Lb-516
Lc-21
937
La-363
Lb-516
Lc-37
938
La-363
Lb-516
Lc-40
939
La-363
Lb-516
Lc-44.

### Claim 42 (depends on 31)

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 according to claim 31.

### Claim 43 (depends on 42)

The electroluminescent device according to claim 42, wherein the organic layer is an emissive layer, and the compound is an emissive material; preferably, the organic layer further comprises a host material; more preferably, the organic layer comprises at least two host materials.

### Claim 44 (depends on 43)

The electroluminescent device according to claim 43, wherein the host material comprises at least one chemical group selected from the group consisting of: benzene, biphenyl, pyridine, pyrimidine, triazine, carbazole, azacarbazole, indolocarbazole, dibenzothiophene, azadibenzothiophene, dibenzofuran, azadibenzofuran, dibenzoselenophene, azadibenzoselenophene, triphenylene, azatriphenylene, fluorene, silafluorene, naphthalene, quinoline, isoquinoline, quinazoline, quinoxaline, phenanthrene, azaphenanthrene, and combinations thereof.

### Claim 45 (depends on 42)

The electroluminescent device according to claim 42, wherein the electroluminescent device is incorporated into a device in the group consisting of: consumer products, electronic element modules, organic light-emitting devices, and lighting panels.

### Claim 46 (depends on 31)

A compound formulation, comprising the metal complex according to claim 31.