US2018002256A1PendingUtilityA1
Double-spiro type compound and organic light-emitting device containing same
Est. expiryFeb 16, 2035(~8.6 yrs left)· nominal 20-yr term from priority
C09K 11/06C07C 211/61C07D 213/16C09K 2211/1059C07D 239/26C09K 2211/1014C07D 251/12C09K 2211/1044C07D 239/24C09K 2211/1029C07D 333/76C07D 209/86C07D 263/56C07D 209/88C09K 2211/1037C07D 307/91C07C 13/72C07C 2603/97C09K 2211/1033C07D 251/24C07C 211/54C09K 2211/1092C09K 2211/1088C07D 277/66C07D 209/80C07C 2603/26C07B 2200/05C07D 263/57C07C 2603/18C07D 235/18C07C 2603/94C09K 2211/1011H01L 51/50H10K 85/636H10K 85/6576H10K 85/654H10K 85/631H10K 85/633H10K 85/6572H10K 85/625H10K 50/00H10K 85/615H10K 85/657H10K 85/6574H10K 50/11
55
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Claims
Abstract
The present specification relates to a double spiro structure compound, and an organic light emitting device comprising the same.
Claims
exact text as granted — not AI-modified1 . A double spiro structure compound represented by the following Chemical Formula 1:
wherein, in Chemical Formula 1,
R 1 is represented by any one of the following Chemical Formula A to Chemical Formula C,
wherein, in Chemical Formula A to Chemical Formula C,
X 1 to X 3 are the same as or different from each other, and each independently CH or N;
at least one of X 1 to X 3 is N;
X 4 is O, S or NAr 5 ;
L 1 to L 3 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted monocyclic or multicyclic arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms;
Ar 1 to Ar 5 are the same as or different from each other, and each independently selected from the group consisting of a substituted or unsubstituted arylamine group; a substituted or unsubstituted monocyclic or multicyclic aryl group having 6 to 30 carbon atoms; and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; and
Cy1 is a substituted or unsubstituted monocyclic or multicyclic hydrocarbon ring having 3 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or multicyclic heteroring having 2 to 30 carbon atoms.
2 . The double spiro structure compound of claim 1 , wherein the double spiro structure compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formulae 1-1 to 1-3:
wherein, in Chemical Formula 1-1 to Chemical Formula 1-3,
a definition of R 1 is the same as in Chemical Formula 1.
3 . The double spiro structure compound of claim 1 , wherein Cy1 is a substituted or unsubstituted benzene ring.
4 . The double spiro structure compound of claim 1 , wherein L 1 to L 3 are the same as or different from each other and each independently a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted biphenylylene group.
5 . The double spiro structure compound of claim 1 , wherein Ar 1 to Ar 5 are the same as or different from each other, and each independently selected from the group consisting of a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenylyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted quaterphenyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted terphenylenyl group; a substituted or unsubstituted dibenzothiophene group; and a substituted or unsubstituted dibenzofuran group.
6 . The double spiro structure compound of claim 1 , wherein Ar 1 to Ar 5 are the same as or different from each other, and each independently selected as any one among the following structural formulae:
wherein, in the structural formulae, means a site linking to other substituents.
7 . The double spiro structure compound of claim 1 , wherein the double spiro structure compound represented by Chemical Formula 1 is represented by the following Chemical Formula 2, and in the following Chemical Formula 2, L 1 , Ar 1 and Ar 2 are any one selected from among 2-1-1 to 2-1-334 of the following Table 1:
TABLE 1
− − −L 1 − − −
− − −Ar 1
− − −Ar 2
2-1- 1
Direct bond
2-1- 2
Direct bond
2-1- 3
Direct bond
2-1- 4
Direct bond
2-1- 5
Direct bond
2-1- 6
Direct bond
2-1- 7
Direct bond
2-1- 8
Direct bond
2-1- 9
Direct bond
2-1- 10
Direct bond
2-1- 11
Direct bond
2-1- 12
Direct bond
2-1- 13
Direct bond
2-1- 14
Direct bond
2-1- 15
Direct bond
2-1- 16
Direct bond
2-1- 17
Direct bond
2-1- 18
Direct bond
2-1- 19
Direct bond
2-1- 20
Direct bond
2-1- 21
Direct bond
2-1- 22
Direct bond
2-1- 23
Direct bond
2-1- 24
Direct bond
2-1- 25
Direct bond
2-1- 26
Direct bond
2-1- 27
Direct bond
2-1- 28
Direct bond
2-1- 29
Direct bond
2-1- 30
Direct bond
2-1- 31
Direct bond
2-1- 32
Direct bond
2-1- 33
Direct bond
2-1- 34
Direct bond
2-1- 35
Direct bond
2-1- 36
Direct bond
2-1- 37
Direct bond
2-1- 38
Direct bond
2-1- 39
Direct bond
2-1- 40
Direct bond
2-1- 41
Direct bond
2-1- 42
Direct bond
2-1- 43
Direct bond
2-1- 44
Direct bond
2-1- 45
Direct bond
2-1- 46
Direct bond
2-1- 47
Direct bond
2-1- 48
Direct bond
2-1- 49
Direct bond
2-1- 50
Direct bond
2-1- 51
Direct bond
2-1- 52
Direct bond
2-1- 53
Direct bond
2-1- 54
Direct bond
2-1- 55
Direct bond
2-1- 56
Direct bond
2-1- 57
Direct bond
2-1- 58
Direct bond
2-1- 59
Direct bond
2-1- 60
Direct bond
2-1- 61
Direct bond
2-1- 62
Direct bond
2-1- 63
Direct bond
2-1- 64
2-1- 65
2-1- 66
2-1- 67
2-1- 68
2-1- 69
2-1- 70
2-1- 71
2-1- 72
2-1- 73
2-1- 74
2-1- 75
2-1- 76
2-1- 77
2-1- 78
2-1- 79
2-1- 80
2-1- 81
2-1- 82
2-1- 83
2-1- 84
2-1- 85
2-1- 86
2-1- 87
2-1- 88
2-1- 89
2-1- 90
2-1- 91
2-1- 92
2-1- 93
2-1- 94
2-1- 95
2-1- 96
2-1- 97
2-1- 98
2-1- 99
2-1- 100
2-1- 101
2-1- 102
2-1- 103
2-1- 104
2-1- 105
2-1- 106
2-1- 107
2-1- 108
2-1- 109
2-1- 110
2-1- 111
2-1- 112
2-1- 113
2-1- 114
2-1- 115
2-1- 116
2-1- 117
2-1- 118
2-1- 119
2-1- 120
2-1- 121
2-1- 122
2-1- 123
2-1- 124
2-1- 125
2-1- 126
2-1- 127
2-1- 128
2-1- 129
2-1- 130
2-1- 131
2-1- 132
2-1- 133
2-1- 134
2-1- 135
2-1- 136
2-1- 137
2-1- 138
2-1- 139
2-1- 140
2-1- 141
2-1- 142
2-1- 143
2-1- 144
2-1- 145
2-1- 146
2-1- 147
2-1- 148
2-1- 149
2-1- 150
2-1- 151
2-1- 152
2-1- 153
2-1- 154
2-1- 155
2-1- 156
2-1- 157
2-1- 158
2-1- 159
2-1- 160
2-1- 161
2-1- 162
2-1- 163
2-1- 164
2-1- 165
2-1- 166
2-1- 167
2-1- 168
2-1- 169
2-1- 170
2-1- 171
2-1- 172
2-1- 173
2-1- 174
2-1- 175
2-1- 176
2-1- 177
2-1- 178
2-1- 179
2-1- 180
2-1- 181
2-1- 182
2-1- 183
2-1- 184
2-1- 185
2-1- 186
2-1- 187
2-1- 188
2-1- 189
2-1- 190
2-1- 191
2-1- 192
2-1- 193
2-1- 194
2-1- 195
2-1- 196
2-1- 197
2-1- 198
2-1- 199
2-1- 200
2-1- 201
2-1- 202
2-1- 203
2-1- 204
2-1- 205
2-1- 206
2-1- 207
2-1- 208
2-1- 209
2-1- 210
2-1- 211
2-1- 212
2-1- 213
2-1- 214
2-1- 215
2-1- 216
2-1- 217
2-1- 218
2-1- 219
2-1- 220
2-1- 221
2-1- 222
2-1- 223
2-1- 224
2-1- 225
2-1- 226
2-1- 227
2-1- 228
2-1- 229
2-1- 230
2-1- 231
2-1- 232
2-1- 233
2-1- 234
2-1- 235
2-1- 236
2-1- 237
2-1- 238
2-1- 239
2-1- 240
2-1- 241
2-1- 242
2-1- 243
2-1- 244
2-1- 245
2-1- 246
2-1- 247
2-1- 248
2-1- 249
2-1- 250
2-1- 251
2-1- 252
2-1- 253
2-1- 254
2-1- 255
2-1- 256
2-1- 257
2-1- 258
2-1- 259
2-1- 260
2-1- 261
2-1- 262
2-1- 263
2-1- 264
2-1- 265
2-1- 266
2-1- 267
2-1- 268
2-1- 269
2-1- 270
2-1- 271
2-1- 272
2-1- 273
+-
2-1- 274
2-1- 275
2-1- 276
2-1- 277
2-1- 278
2-1- 279
2-1- 280
2-1- 281
2-1- 282
2-1- 283
2-1- 284
2-1- 285
2-1- 286
2-1- 287
2-1- 288
2-1- 289
2-1- 290
2-1- 291
2-1- 292
2-1- 293
2-1- 294
2-1- 295
2-1- 296
2-1- 297
2-1- 298
2-1- 299
2-1- 300
2-1- 301
2-1- 302
2-1- 303
2-1- 304
2-1- 305
2-1- 306
2-1- 307
2-1- 308
2-1- 309
2-1- 310
2-1- 311
2-1- 312
2-1- 313
2-1- 314
2-1- 315
2-1- 316
2-1- 317
2-1- 318
2-1- 319
2-1- 320
2-1- 321
2-1- 322
2-1- 323
2-1- 324
2-1- 325
2-1- 326
2-1- 327
2-1- 328
2-1- 329
2-1- 330
2-1- 331
2-1- 332
2-1- 333
2-1- 334
8 . The double Spiro structure compound of claim 1 , wherein the double spiro structure compound represented by Chemical Formula 1 is represented by the following Chemical Formula 3-1, and in the following Chemical Formula 3-1, L 2 , Ar 3 and Ar 4 are any one selected from among 3-1-1 to 3-1-104 of the following Table 2:
TABLE 2
3-1-1
Direct bond
3-1-2
Direct bond
3-1-3
Direct bond
3-1-4
Direct bond
3-1-5
Direct bond
3-1-6
Direct bond
3-1-7
Direct bond
3-1-8
Direct bond
3-1-9
Direct bond
3-1-10
Direct bond
3-1-11
Direct bond
3-1-12
3-1-13
3-1-14
3-1-15
3-1-16
3-1-17
3-1-18
3-1-19
3-1-20
3-1-21
3-1-22
3-1-23
3-1-24
3-1-25
3-1-26
3-1-27
3-1-28
3-1-29
3-1-30
3-1-31
3-1-32
3-1-33
3-1-34
3-1-35
3-1-36
3-1-37
3-1-38
3-1-39
3-1-40
3-1-41
3-1-42
3-1-43
3-1-44
3-1-45
3-1-46
3-1-47
3-1-48
3-1-49
3-1-50
3-1-51
3-1-52
3-1-53
3-1-54
3-1-55
3-1-56
3-1-57
3-1-58
3-1-59
3-1-60
3-1-61
3-1-62
3-1-63
3-1-64
3-1-65
3-1-66
3-1-67
3-1-68
3-1-69
3-1-70
3-1-71
3-1-72
3-1-73
3-1-74
3-1-75
3-1-76
3-1-77
3-1-78
3-1-79
3-1-80
3-1-81
3-1-82
3-1-83
3-1-84
3-1-85
3-1-86
3-1-87
3-1-88
3-1-89
3-1-90
3-1-91
3-1-92
3-1-93
3-1-94
3-1-95
3-1-96
3-1-97
3-1-98
3-1-99
3-1-100
3-1-101
3-1-102
3-1-103
3-1-104
9 . The double Spiro structure compound of claim 1 , wherein the double spiro structure compound represented by Chemical Formula 1 is represented by the following Chemical Formula 3-2, and in the following Chemical Formula 3-2, L 2 , Ar 3 and Ar 4 are any one selected from among 3-2-1 to 3-2-104 of the following Table 3:
TABLE 3
− − −L 2 − − −
− − −Ar 3
− − −Ar 4 − − −
3-2-1
Direct bond
3-2-2
Direct bond
3-2-3
Direct bond
3-2-4
Direct bond
3-2-5
Direct bond
3-2-6
Direct bond
3-2-7
Direct bond
3-2-8
Direct bond
3-2-9
Direct bond
3-2-10
Direct bond
3-2-11
Direct bond
3-2-12
3-2-13
3-2-14
3-2-15
3-2-16
3-2-17
3-2-18
3-2-19
3-2-20
3-2-21
3-2-22
3-2-23
3-2-24
3-2-25
3-2-26
3-2-27
3-2-28
3-2-29
3-2-30
3-2-31
3-2-32
3-2-33
3-2-34
3-2-35
3-2-36
3-2-37
3-2-38
3-2-39
3-2-40
3-2-41
3-2-42
3-2-43
3-2-44
3-2-45
3-2-46
3-2-47
3-2-48
3-2-49
3-2-50
3-2-51
3-2-52
3-2-53
3-2-54
3-2-55
3-2-56
3-2-57
3-2-58
3-2-59
3-2-60
3-2-61
3-2-62
3-2-63
3-2-64
3-2-65
3-2-66
3-2-67
3-2-68
3-2-69
3-2-70
3-2-71
3-2-72
3-2-73
3-2-74
3-2-75
3-2-76
3-2-77
3-2-78
3-2-79
3-2-80
3-2-81
3-2-82
3-2-83
3-2-84
3-2-85
3-2-86
3-2-87
3-2-88
3-2-89
3-2-90
3-2-91
3-2-92
3-2-93
3-2-94
3-2-95
3-2-96
3-2-97
3-2-98
3-2-99
3-2-100
3-2-101
3-2-102
3-2-103
3-2-104
10 . The double Spiro structure compound of claim 1 , wherein in the double spiro structure compound represented by Chemical Formula 1 is represented by the following Chemical Formula 3-3, and in the following Chemical Formula 3-3, L 2 , Ar 3 and Ar 4 are any one selected from among 3-3-1 to 3-3-104 of the following Table 4:
TABLE 4
− − −L 4 − − −
− − −Ar 3
− − −Ar 4
3-3-1
Direct bond
3-3-2
Direct bond
3-3-3
Direct bond
3-3-4
Direct bond
3-3-5
Direct bond
3-3-6
Direct bond
3-3-7
Direct bond
3-3-8
Direct bond
3-3-9
Direct bond
3-3-10
Direct bond
3-3-11
Direct bond
3-3-12
3-3-13
3-3-14
3-3-15
3-3-16
3-3-17
3-3-18
3-3-19
3-3-20
3-3-21
3-3-22
3-3-23
3-3-24
3-3-25
3-3-26
3-3-27
3-3-28
3-3-29
3-3-30
3-3-31
3-3-32
3-3-33
3-3-34
3-3-35
3-3-36
3-3-37
3-3-38
3-3-39
3-3-40
3-3-41
3-3-42
3-3-43
3-3-44
3-3-45
3-3-46
3-3-47
3-3-48
3-3-49
3-3-50
3-3-51
3-3-52
3-3-53
3-3-54
3-3-55
3-3-56
3-3-57
3-3-58
3-3-59
3-3-60
3-3-61
3-3-62
3-3-63
3-3-64
3-3-65
3-3-66
3-3-67
3-3-68
3-3-69
3-3-70
3-3-71
3-3-72
3-3-73
3-3-74
3-3-75
3-3-76
3-3-77
3-3-78
3-3-79
3-3-80
3-3-81
3-3-82
3-3-83
3-3-84
3-3-85
3-3-86
3-3-87
3-3-88
3-3-89
3-3-90
3-3-91
3-3-92
3-3-93
3-3-94
3-3-95
3-3-96
3-3-97
3-3-98
3-3-99
3-3-100
3-3-101
3-3-102
3-3-103
3-3-104
11 . The double Spiro structure compound of claim 1 , wherein the double spiro structure compound represented by Chemical Formula 1 is represented by the following Chemical Formula 3-4, and in the following Chemical Formula 3-4, L 2 , Ar 3 and Ar 4 are any one selected from among 3-4-1 to 3-4-104 of the following Table 5:
TABLE 5
—L 2—
—Ar 3
—Ar 4
3-4-1
Direct bond
3-4-2
Direct bond
3-4-3
Direct bond
3-4-4
Direct bond
3-4-5
Direct bond
3-4-6
Direct bond
3-4-7
Direct bond
3-4-8
Direct bond
3-4-9
Direct bond
3-4-10
Direct bond
3-4-11
Direct bond
3-4-12
3-4-13
3-4-14
3-4-15
3-4-16
3-4-17
3-4-18
3-4-19
3-4-20
3-4-21
3-4-22
3-4-23
3-4-24
3-4-25
3-4-26
3-4-27
3-4-28
3-4-29
3-4-30
3-4-31
3-4-32
3-4-33
3-4-34
3-4-35
3-4-36
3-4-37
3-4-38
3-4-39
3-4-40
3-4-41
3-4-42
3-4-43
3-4-44
3-4-45
3-4-46
3-4-47
3-4-48
3-4-49
3-4-50
3-4-51
3-4-52
3-4-53
3-4-54
3-4-55
3-4-56
3-4-57
3-4-58
3-4-59
3-4-60
3-4-61
3-4-62
3-4-63
3-4-64
3-4-65
3-4-66
3-4-67
3-4-68
3-4-69
3-4-70
3-4-71
3-4-72
3-4-73
3-4-74
3-4-75
3-4-76
3-4-77
3-4-78
3-4-79
3-4-80
3-4-81
3-4-82
3-4-83
3-4-84
3-4-85
3-4-86
3-4-87
3-4-88
3-4-89
3-4-90
3-4-91
3-4-92
3-4-93
3-4-94
3-4-95
3-4-96
3-4-97
3-4-98
3-4-99
3-4-100
3-4-101
3-4-102
3-4-103
3-4-104
12 . The double Spiro structure compound of claim 1 , wherein the double spiro structure compound represented by Chemical Formula 1 is represented by the following Chemical Formula 4-4, and in the following Chemical Formula 4-4, L 3 and X 4 are any one selected from among 4-4-1 to 4-4-22 of the following Table 6:
TABLE 6
X 4
—L 3 —
4-4-1
O
4-4-2
S
X 4
—L 3 —
—Ar 5
4-4-3
NAr 5
4-4-4
NAr 5
4-4-5
NAr 5
4-4-6
NAr 5
4-4-7
NAr 5
4-4-8
NAr 5
4-4-9
NAr 5
4-4-10
NAr 5
4-4-11
NAr 5
4-4-12
NAr 5
4-4-13
NAr 5
4-4-14
NAr 5
4-4-15
NAr 5
4-4-16
NAr 5
4-4-17
NAr 5
4-4-18
NAr 5
4-4-19
NAr 5
4-4-20
NAr 5
4-4-21
NAr 5
4-4-22
NAr 5
13 . An organic light emitting device comprising:
an anode; a cathode provided opposite to the anode; and a light emitting layer and one or more organic material layers provided between the anode and the cathode, wherein the light emitting layer or one or more layers of the organic material layers comprise the double spiro structure compound of claim 1 .
14 . The organic light emitting device of claim 13 , wherein the organic material layer comprises a hole injection layer or a hole transfer layer, and the hole injection layer or the hole transfer layer comprises the double spiro structure compound.
15 . The organic light emitting device of claim 13 , wherein the organic material layer comprises an electron blocking layer, and the electron blocking layer comprises the double spiro structure compound.
16 . The organic light emitting device of claim 13 , wherein the light emitting layer comprises the double spiro structure compound.
17 . The organic light emitting device of claim 13 , wherein the organic material layer comprises an electron transfer layer, an electron injection layer or a layer carrying out electron transfer and electron injection at the same time, and the electron transfer layer, the electron injection layer or the layer carrying out electron transfer and electron injection at the same time comprises the double spiro structure compound.
18 . The organic light emitting device of claim 13 comprising one or more organic material layers provided between the anode and the light emitting layer, wherein the organic material layer comprises a double spiro structure compound represented by the following Chemical Formula 2:
wherein, in Chemical Formula 2,
L 1 is a direct bond; a substituted or unsubstituted monocyclic or multicyclic arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms; and
Ar 1 and Ar 2 are the same as or different from each other, and each independently selected from the group consisting of hydrogen; a substituted or unsubstituted arylamine group; a substituted or unsubstituted monocyclic or multicyclic aryl group having 6 to 30 carbon atoms; and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
19 . The organic light emitting device of claim 13 comprising one or more organic material layers provided between the cathode and the light emitting layer, wherein the light emitting layer or the organic material layer comprises a double spiro structure compound represented by the following Chemical Formula 3:
wherein, in Chemical Formula 3,
X 1 to X 3 are the same as or different from each other, and each independently CH or N;
at least one of X 1 to X 3 is N;
L 2 is a direct bond; a substituted or unsubstituted monocyclic or multicyclic arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms; and
Ar 3 and Ar 4 are the same as or different from each other, and each independently selected from the group consisting of hydrogen; a substituted or unsubstituted arylamine group; a substituted or unsubstituted monocyclic or multicyclic aryl group having 6 to 30 carbon atoms; and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
20 . The organic light emitting device of claim 13 comprising one or more organic material layers provided between the cathode and the light emitting layer, wherein the organic material layer comprises a double spiro structure compound represented by the following Chemical Formula 4:
wherein, in Chemical Formula 4,
X 4 is O, S or NAr 5 ;
L 3 is a direct bond; a substituted or unsubstituted monocyclic or multicyclic arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms;
Ar 5 is selected from the group consisting of hydrogen; a substituted or unsubstituted arylamine group; a substituted or unsubstituted monocyclic or multicyclic aryl group having 6 to 30 carbon atoms; and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; and
Cy1 is a substituted or unsubstituted monocyclic or multicyclic hydrocarbon ring having 3 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or multicyclic heteroring having 2 to 30 carbon atoms.Join the waitlist — get patent alerts
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