Heterocyclic compound and organic light-emitting device comprising same
The present specification provides a hetero-cyclic compound and an organic light emitting device comprising the same.
1. A compound of any one of Formulae 3 to 6:
wherein in Formula 3 to 6:
Ar1 and Ar2 are different from each other, and each independently is a phenyl group, a naphthyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, a phenanthryl group, or a chrysenyl group, which is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a phenyl group, a naphthyl group, a terphenyl group and a phenanthryl group;
R1 is hydrogen or deuterium, or two or more adjacent R1s combine with each other to form a benzene ring;
R2 is hydrogen, deuterium, a C1 to C6 alkyl group, a phenyl group, a naphthyl group, or a biphenyl group, or two or more adjacent R2s combine with each other to form a benzene ring;
R3 and R4 are the same as or different from each other, and each independently is hydrogen, deuterium, a C1 to C6 alkyl group, a phenyl group, a naphthyl group, or a biphenyl group, which is unsubstituted or substituted with deuterium or an C1-C6 alkyl group;
L is a direct bond, a phenylene, a biphenylene, a naphthylene, or a phenanthrylene, which is unsubstituted or substituted with deuterium;
n is an integer of 0 to 3;
m is an integer of 0 to 4;
s is an integer of 1 to 5; and
when n is 2 or more, the R1's are the same as or different from each other, and
when m is 2 or more, the R2's are the same as or different from each other, and
when s is 2 or more, the L's are the same as or different from each other.
2. A compound of Formula 7 or 8:
wherein in Formulae 7 and 8:
Ar1 and Ar2 are different from each other, and each independently is a phenyl group, a naphthyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, a phenanthryl group, or a chrysenyl group, which is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a phenyl group, a naphthyl group, a terphenyl group and a phenanthryl group;
R1 is hydrogen or deuterium, or two or more adjacent R1s combine with each other to form a benzene ring;
R2 is hydrogen, deuterium, a C1 to C6 alkyl group, a phenyl group, a naphthyl group, or a biphenyl group, or two or more adjacent R2s combine with each other to form a benzene ring;
L is a direct bond, a phenylene, a biphenylene, a naphthylene, or a phenanthrylene, which is unsubstituted or substituted with deuterium;
R11 and R12 are the same as or different from each other, and each independently is hydrogen, deuterium, or a C1-C6 alkyl group, or two or more adjacent groups combine with each other to form a benzene ring,
A1 and A2 are the same as or different from each other, and each independently is hydrogen, deuterium, or a C1-C6 alkyl group,
a and b are the same as or different from each other, and each independently is 0 or 1; and
n is an integer of 0 to 3;
m is an integer of 0 to 4; and
s is an integer of 1 to 5;
when n is 2 or more, the R1's are the same as or different from each other, and
when m is 2 or more, the R2's are the same as or different from each other, and
when s is 2 or more, the L's are the same as or different from each other, and
when a is 2 or more, the R11's are the same as or different from each other, and
when b is 2 or more, the R12's are the same as or different from each other.
3. The compound of claim 1 , wherein L is a direct bond, or any one structure selected from the following structures:
wherein the structures are unsubstituted or substituted with deuterium.
4. A compound of Formula 24:
wherein in Formula 24:
Ar1 and Ar2 are different from each other, and each independently is a phenyl group, a naphthyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, a phenanthryl group, or a chrysenyl group, which is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a phenyl group, a naphthyl group, a terphenyl group and a phenanthryl group;
R1 is hydrogen or deuterium, or two or more adjacent R1s combine with each other to form a benzene ring;
R2 is hydrogen, deuterium, a C1 to C6 alkyl group, a phenyl group, a naphthyl group, or a biphenyl group, or two or more adjacent R2s combine with each other to form a benzene ring;
R3 and R4 are the same as or different from each other, and each independently is hydrogen, deuterium, a C1 to C6 alkyl group, a phenyl group, a naphthyl group, or a biphenyl group, which is unsubstituted or substituted with deuterium or an C1-C6 alkyl group;
T is hydrogen, or deuterium;
s is an integer of 1 to 5;
u is an integer of 0 to 4; and
when u is 2 or more, T's are the same as or different from each other.
5. A compound of Formula 26:
wherein in Formula 26:
Ar1 is a phenyl group, a naphthyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, a phenanthryl group, or a chrysenyl group, which is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a phenyl group, a naphthyl group, a terphenyl group and a phenanthryl group;
R1 is hydrogen or deuterium, or two or more adjacent R1s combine with each other to form a benzene ring;
R2 is hydrogen, deuterium, a C1 to C6 alkyl group, a phenyl group, a naphthyl group, or a biphenyl group, or two or more adjacent R2s combine with each other to form a benzene ring;
R3 and R4 are the same as or different from each other, and each independently is hydrogen, deuterium, a C1 to C6 alkyl group, a phenyl group, a naphthyl group, or a biphenyl group, which is unsubstituted or substituted with deuterium or an C1-C6 alkyl group;
X1 and X2 are the same as or different from each other, and each independently is hydrogen, deuterium, a phenyl group, a naphthyl group, a terphenyl group, or a phenanthryl group;
and Ar1 are different from each other;
x1 is an integer of 0 to 5;
x2 is an integer of 0 to 4;
n is an integer of 1 to 3;
m is an integer of 1 to 4;
s is an integer of 1 to 5; and
when n is 2 or more, the R1's are the same as or different from each other; and
when m is 2 or more, the R2's are the same as or different from each other; and
when s is 2 or more, the L's are the same as or different from each other; and
when x1 is 2 or more, the X's are the same as or different from each other; and
when x2 is 2 or more, the X2's are the same as or different from each other.
6. The compound of claim 1 , wherein Ar1 is a phenyl group, a biphenyl group, a naphthyl group, or a phenanthryl group, which is unsubstituted or substituted with a phenyl group, a naphthyl group, a terphenyl group or a phenanthryl group; and
Ar2 is a phenyl group, a biphenyl group, a terphenyl group, quaterphenyl group, a naphthyl group, or a phenanthryl group, which is unsubstituted or substituted with a phenyl group, a naphthyl group, a terphenyl group or a phenanthryl group.
7. The compound of claim 1 , wherein the compound of any one of Formulae 3 to 6 is a compound of Formula 1:
that is any one selected from the following compounds:
Com-
pound
- - - Ar1
- - - Ar2
- - - Ar3
1-1
1-2
1-3
1-4
1-5
1-6
1-7
1-8
1-9
1-10
1-11
1-12
1-13
1-14
1-15
1-16
1-17
1-18
1-19
1-20
1-21
1-22
1-23
1-24
1-25
1-26
1-27
1-28
1-29
1-30
1-32
1-33
1-34
1-35
1-36
1-37
1-38
1-39
1-40
1-41
1-42
1-43
1-44
1-45
1-46
1-47
1-48
1-49
1-50
1-51
1-52
1-53
1-54
1-55
1-56
1-57
1-58
1-59
1-60
1-61
1-62
1-63
1-64
1-66
1-67
1-68
1-69
1-70
1-71
1-72
1-73
1-74
1-75
1-76
1-77
1-78
1-79
1-80
1-81
1-82
1-83
1-84
1-85
1-86
1-87
1-88
1-89
1-90
1-91
1-92
1-93
1-94
1-95
1-96
1-97
1-98
1-99
1-100
1-101
1-102
1-103
1-104
1-105
1-106
1-107
1-108
1-109
1-110
1-112
1-113
1-114
1-115
1-116
1-117
1-118
1-119
1-120
1-121
1-122
1-123
1-124
1-125
1-126
1-128
1-129
1-130
1-131
1-132
1-134
1-135
1-136
1-137
1-138
1-139
1-140
1-141
1-142
1-143
1-144
1-145
1-146
1-147
1-148
1-149
1-150
1-151
1-152
1-153
1-154
1-155
1-156
1-157
1-158
1-159
1-160
1-161
1-162
1-163
1-164
1-165
1-166
1-167
1-168
1-169
1-170
1-172
1-173
1-174
1-175
1-176
1-178
1-179
1-180
1-181
1-182
1-183
1-184
1-185
1-186
1-187
1-188
1-189
1-190
1-191
1-192
1-193
1-194
1-195
1-196
1-197
1-198
1-199
1-200
1-201
1-202
1-203
1-204
1-205
1-206
1-208
1-209
1-210
1-211
1-212
1-213
1-214
1-215
1-216
1-217
1-218
1-219
1-220
1-221
1-222
1-223
1-224
1-225
1-226
1-227
1-228
1-229
1-230
1-231
1-232
1-233
1-234
1-235
1-236
1-237
1-238
1-239
1-240
1-241
1-242
1-243
1-244
1-245
1-246
1-247
1-248
1-249
1-250
1-251
1-252
1-253
1-254
1-255
1-256
1-258
1-259
1-260
1-261
1-262
1-263
1-264
1-265
1-266
1-267
1-268
1-269
1-270
1-271
1-272
1-273
1-274
1-275
1-276
1-278
1-279
1-280
1-281
1-282
1-283
1-284
1-285
1-286
1-287
1-288
1-289
1-290
1-292
1-293
1-294
1-295
1-296
1-297
1-298
1-299
1-300
1-301
1-302
1-303
1-304
1-305
1-306
1-307
1-308
1-309
1-310
1-311
1-312
1-313
1-314
1-315
1-316
1-317
1-318
1-319
1-319
1-320
1-321
1-322
1-323
1-324
1-325
1-326
1-327
1-328
1-329
1-330
1-331
1-332
1-333
1-334
1-335
1-336
1-337
1-338
1-339
1-340
1-341
1-342
1-343
1-344
1-345
1-346
1-347
1-348
1-350
1-351
1-352
1-353
1-354
1-355
1-356
1-357
1-358
1-360
1-361
1-362
1-363
1-364
1-365
1-366
1-367
1-368
1-369
1-370
1-371
1-372
1-373
1-374
1-375
1-376
1-377
1-378
1-379
1-380
1-382
1-383
1-384
1-385
1-386
1-387
1-388
1-389
1-390
1-391
1-392
1-393
1-394
1-395
1-396
1-397
1-398
1-399
1-400
1-401
1-402
1-403
1-404
1-405
1-406
1-407
1-408
1-409
1-410
1-411
1-412
1-413
1-414
1-415
1-416
1-417
1-418
1-420
1-421
1-422
1-423
1-424
1-425
1-426
1-427
1-428
1-429
1-430
1-431
1-432
1-433
1-434
1-435
1-436
1-437
1-438
1-439
1-440
1-441
1-442
1-443
1-444
1-445
1-446
1-447
1-448
1-449
1-450
1-451
1-452
1-453
1-454
1-455
1-456
1-457
1-459
1-460
1-461
1-462
1-463
1-464
1-465
1-466
1-467
1-468
1-469
1-470
1-471
1-472
1-474
1-475
1-476
1-477
1-478
1-479
1-480
1-481
1-482
1-484
1-485
1-486
1-487
1-488
1-489
1-490
1-491
1-492
1-493
1-494
1-495
1-496
1-497
1-498
1-499
1-500
1-501
1-502
1-503
1-504
1-505
1-506
1-507
1-508
1-509
1-510
1-511
1-512
1-513
1-514
1-516
1-517
1-518
1-519
1-520
1-522
1-523
1-524
1-525
1-526
1-527
1-528
1-529
1-530
1-531
1-532
1-533
1-534
1-535
1-536
1-537
1-538
1-539
1-540
1-541
1-542
1-543
1-544
1-545
1-546
1-547
1-548
1-549
1-550
1-551
1-552
1-553
1-554
1-555
1-556
1-557
1-558
1-559
1-560
1-561
1-562
1-564
1-565
1-566
1-567
1-568
1-569
1-570
1-571
1-572
1-573
1-574
1-575
1-576
1-577
1-578
1-579
1-580
1-581
1-582
1-583
1-584
1-585
1-586
1-587
1-588
1-589
1-590
1-591
1-592
1-593
1-594
1-595
1-596
1-597
1-598
1-599
1-600
1-601
1-602
1-603
1-604
1-605
1-606
1-607
1-608
1-609
1-610
1-611
1-612
1-613
1-614
1-615
1-616
1-617
1-618
1-619
1-620
1-622
1-623
1-624
1-625
1-626
1-627
8. A compound of Formula 1:
that is any one selected from the following compounds:
Com-
pound
- - - -Ar1
- - - -Ar2
- - - -Ar3
2-1
2-2
2-3
2-4
2-5
2-6
2-7
2-8
2-9
2-10
2-11
2-12
2-13
2-14
2-15
2-16
2-17
2-18
2-19
2-20
2-21
2-22
2-23
2-24
2-25
2-26
2-27
2-28
2-29
2-30
2-31
2-32
2-33
2-34
2-35
2-36
2-37
2-38
2-39
2-40
2-41
2-42
2-43
2-44
2-45
2-46
2-47
2-48
2-49
2-50
2-51
2-52
2-53
2-54
2-55
2-56
2-57
2-58
2-59
2-60
2-61
2-62
2-63
2-64
2-65
2-66
2-67
2-68
2-69
2-70
2-71
2-72
2-73
2-74
2-75
2-76
2-77
2-78
2-79
2-80
2-81
2-82
2-83
2-84
2-85
2-86
2-87
2-88
2-89
2-90
2-91
2-92
2-93
2-94
2-95
2-96
2-97
2-98
2-99
2-100
2-101
2-102
2-103
2-104
2-105
2-106
2-107
2-108
2-109
2-110
2-111
2-112
2-113
2-114
2-115
2-116
2-117
2-118
2-119
2-120
2-121
2-122
2-123
2-124
2-125
2-126
2-127
2-128
2-129
2-130
2-131
2-132
2-133
2-134
2-135
2-136
2-137
2-138
2-139
2-140
2-141
2-142
2-143
2-144
2-145
2-146
2-147
2-148
2-149
2-150
2-151
2-152
2-153
2-154
2-155
2-156
2-157
2-158
2-159
2-160
2-161
2-162
2-163
2-164
2-165
2-166
2-167
2-168
2-169
2-170
2-171
2-172
2-173
2-174
2-175
2-176
2-177
2-178
2-179
2-180
2-181
2-182
2-183
2-184
2-185
2-186
2-187
2-188
2-189
2-190
2-191
2-192
2-193
2-194
2-195
2-196
2-197
2-198
2-199
2-200
2-201
2-202
2-203
2-204
2-205
2-206
2-207
2-209
2-210
2-211
2-212
2-213
2-214
2-215
2-216
2-217
2-218
2-219
2-220
2-221
2-222
2-223
2-224
2-225
2-226
2-227
2-228
2-229
2-230
2-231
2-232
2-233
2-234
2-235
2-236
2-237
2-238
2-239
2-240
2-241
2-242
2-243
2-244
2-245
2-246
2-248
2-249
2-250
2-251
2-252
2-253
2-254
2-255
2-256
2-257
2-258
2-259
2-260
2-261
2-262
2-263
2-264
2-265
2-266
2-267
2-268
2-269
2-270
2-271
2-273
2-274
2-275
2-276
2-277
2-278
2-279
2-280
2-281
2-282
2-283
2-284
2-285
2-286
2-287
2-288
2-289
2-290
2-291
2-292
2-293
2-294
2-295
2-296
2-297
2-298
2-299
2-300
2-301
2-302
2-303
2-304
2-305
2-306
2-307
2-308
2-309
2-310
2-311
2-312
2-313
2-314
2-315
2-316
2-317
2-318
2-319
2-320
2-321
2-322
2-323
2-324
2-325
2-326
2-327
2-328
2-329
2-330
2-331
2-332
2-333
2-334
2-335
2-336
2-337
2-338
2-339
2-340
2-341
2-342
2-343
2-344
2-345
2-346
2-347
2-348
2-349
2-350
2-351
2-353
2-354
2-355
2-356
2-357
2-358
2-359
2-360
2-361
2-362
2-363
I-7
I-9
I-14
I-18
I-22
I-23
I-26
I-30
I-33
I-34
I-38
I-42
I-45
I-46
I-50
I-54
I-57
I-58
I-62
I-66
I-69
I-70
I-74
I-78
I-82
I-86
I-90
I-94
I-98
I-102
I-105
I-106
I-110
I-114
I-118
I-119
I-122
I-126
I-130
I-134
I-138
I-142
I-143
I-146
I-149
I-150
I-153
I-154
I-158
I-162
I-166
I-167
I-170
I-174
I-178
I-179
I-182
I-186
I-190
I-194
I-198
I-202
I-206
I-210
I-214
I-218
I-222
I-226
I-227
I-230
I-234
I-237
I-238
I-242
I-246
I-247
I-249
I-250
I-254
I-258
I-261
I-262
I-266
I-270
I-273
I-274
I-278
I-282
I-286
I-290
I-294
I-297
I-298
I-302
I-306
I-310
I-314
I-318
I-321
I-322
I-326
I-330
I-334
I-335
I-338
I-342
I-345
I-346
I-350
I-354
I-358
I-362
I-366
I-370
I-374
I-378
I-382
I-386
I-389
I-390
I-394
I-398
I-401
I-402
I-403
I-406
I-410
I-414
I-418
I-422
I-426
I-429
I-430
I-434
I-438
I-442
I-446
I-449
I-450
I-454
I-462
I-463
I-466
I-470
I-474
I-478
I-482
I-486
I-489
I-490
I-494
I-497
I-498
I-502
I-503
I-506
I-507
I-510
I-514
I-518
I-522
I-526
I-527
I-530
I-534
I-538
I-542
I-546
I-550
I-554
I-558
I-561
I-562
I-566
I-569
I-570
I-574
I-578
I-582
I-586
I-590
I-594
I-597
I-598
I-599
I-602
I-606
I-609
I-610
I-611
I-614
I-618
I-622
I-623
I-625
I-627
9. An organic light emitting device comprising:
an anode;
a cathode; and
one or more organic material layers provided between the anode and the cathode,
wherein one or more layers of the organic material layers comprise the compound of claim 1 .
10. The organic light emitting device of claim 9 , wherein the organic material layer comprising the compound is one or two or more organic material layers selected from the group consisting of an electron transporting layer, an electron injection layer, a layer which simultaneously injects or transports electrons, and an electron controlling layer.
11. The organic light emitting device of claim 9 , wherein the organic material layer comprising the compound comprises the compound as a host and an n-type dopant as a dopant.
12. The organic light emitting device of claim 11 , wherein the n-type dopant comprises an alkali metal, an alkali metal compound, an alkaline earth metal, an alkaline earth metal compound, or a combination thereof.
13. The organic light emitting device of claim 11 , wherein as the n-type dopant, one or two or more are selected from the group consisting of Li, Na, K, Rb, Cs, Mg, Ca, Sr, Ba, La, Nd, Sm, Eu, Tb, Yb, LiF, Li 2 O, CsF, or the following compounds:
14. An organic light emitting device comprising:
an anode;
a cathode; and
two or more organic material layers provided between the anode and the cathode,
wherein the organic material layer comprises an electron transporting layer and an electron controlling layer,
the electron transporting layer comprises the compound of claim 1 as a host and an n-type dopant as a dopant, and
the electron controlling layer is different from the electron transporting layer.
15. An organic light emitting device comprising:
an anode;
a cathode; and
two or more organic material layers provided between the anode and the cathode,
wherein the organic material layer comprises an electron transporting layer and an electron controlling layer,
the electron controlling layer comprises the compound of claim 1 as a host and an n-type dopant as a dopant, and
the electron transporting layer is different from the electron controlling layer.
16. The organic light emitting device of claim 9 , wherein the organic light emitting device comprises:
a light emitting layer provided between the anode and the cathode;
an electron transporting layer provided between the light emitting layer and the cathode; and
an electron controlling layer provided between the electron transporting layer and the light emitting layer, and
the electron controlling layer comprises a compound of Formula 3-1:
wherein in Formula 3-1:
Ar1 and Ar12 are different from each other, and each independently is a phenyl group, a naphthyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, a phenanthryl group, or a chrysenyl group, which is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a phenyl group, a naphthyl group, a terphenyl group and a phenanthryl group;
L1 is a direct bond, a phenylene, a biphenylene, a naphthylene, or a phenanthrylene, which is unsubstituted or substituted with deuterium;
R32 is hydrogen or deuterium, or two or more adjacent R32s combine with each other to form a benzene ring;
R42 is hydrogen, deuterium, a C1 to C6 alkyl group, a phenyl group, a naphthyl group, or a biphenyl group, or two or more adjacent R42s combine with each other to form a benzene ring;
R31 and R41 are the same as or different from each other, and each independently is hydrogen, deuterium, a C1 to C6 alkyl group, a phenyl group, a naphthyl group, or a biphenyl group, which is unsubstituted or substituted with deuterium or a C1-C6 alkyl group;
n32 is an integer of 0 to 3 and m42 is an integer of 0 to 4; and
s1 is an integer of 1 to 5; and
when n32 is 2 or more, the R32's are the same as or different from each other; and
when n42 is 2 or more, the R42's are the same as or different from each other; and
when s1 is 2 or more, the L1's are the same as or different from each other.
17. An organic light emitting device comprising:
an anode;
a cathode;
two or more organic material layers provided between the anode and the cathode, wherein at least one organic material layer is an electron transporting layer and at least one organic material layer is an electron controlling layer; and
a light emitting layer provided between the anode and the cathode;
wherein:
the electron transporting layer is provided between the light emitting layer and the cathode;
the electron controlling layer is provided between the electron transporting layer and the light emitting layer; and
the electron transporting layer comprises a compound of Formula 6-1:
wherein in Formula 6-1:
Ar2 and Ar22 are different from each other, and each independently is a phenyl group, a naphthyl group, biphenyl group, a terphenyl group, a quaterphenyl group, a phenanthryl group, or a chrysenyl group, which is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a phenyl group, a naphthyl group, a terphenyl group, and a phenanthryl group;
L2 is a direct bond, a phenylene, a biphenylene, a naphthylene, or a phenanthrylene, which is unsubstituted or substituted with deuterium;
R52 is hydrogen or deuterium, or two or more adjacent R52s combine with each other to a benzene ring;
R62 is hydrogen, deuterium, a C1 to C6 alkyl group, a phenyl group, a naphthyl group, or a biphenyl group, or two or more adjacent R62s combine with each other to form a benzene ring;
R51 and R61 are the same as or different from each other, and each independently is hydrogen, deuterium, a substituted or unsubstituted C1 to C6 alkyl group, a phenyl group, a naphthyl group, or a biphenyl group, which is unsubstituted or substituted with deuterium or a C1-C6 alkyl group;
n52 is an integer of 0 to 3;
m62 is an integer of 0 to 4; and
s2 is an integer of 1 to 5; and
when n52 is each 2 or more, the R52's are the same as or different from each other; and
when m62 is each 2 or more, the R62's are the same as or different from each other; and
when s is each 2 or more, the L2's are the same as or different from each other.
18. An organic light emitting device comprising:
an anode;
a cathode;
a light emitting layer provided between the anode and the cathode; and
an electron transporting layer provided between the light emitting layer and the cathode,
wherein the light emitting layer comprises a host, and
the electron transporting layer comprises the compound of claim 1 , which is different from the host and has a HOMO energy level of 6 eV to 7 eV.
19. An organic light emitting device comprising:
an anode;
a cathode;
a light emitting layer provided between the anode and the cathode; and
an electron transporting layer provided between the light emitting layer and the cathode,
wherein the light emitting layer comprises a host, and
the electron transporting layer comprises the compound of claim 1 , which is different from the host and has a triplet energy (ET) of 2.2 eV or more.