TW202122398A - 一種咪唑並吡啶的芳胺類化合物及其應用 - Google Patents

一種咪唑並吡啶的芳胺類化合物及其應用 Download PDF

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TW202122398A
TW202122398A TW109134367A TW109134367A TW202122398A TW 202122398 A TW202122398 A TW 202122398A TW 109134367 A TW109134367 A TW 109134367A TW 109134367 A TW109134367 A TW 109134367A TW 202122398 A TW202122398 A TW 202122398A
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陳少福
鄢亮亮
戴雷
蔡麗菲
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大陸商廣東阿格蕾雅光電材料有限公司
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Abstract

本發明涉及一種咪唑並吡啶的芳胺類化合物及其應用。所述化合物具有式（I）結構。本發明化合物具有昇華溫度低，熱穩定性好，折射率高、可見光區折射率差異小等優點，可做為光提取層材料，應用於有機發光器件中。

Description

一種咪唑並吡啶的芳胺類化合物及其應用
本發明涉及有機電致發光材料領域，特別涉及咪唑並吡啶的芳胺類化合物及其在有機電致發光器件上的應用。
目前，作為新一代顯示技術的有機電致發光器件（OLED）在顯示和照明技術方面都獲得了越來越多的關注，應用前景十分廣泛。但是，和市場應用要求相比，OLED器件的發光效率、驅動電壓、使用壽命等性能還需要繼續加強和改進。
一般來說，OLED器件基本結構為在金屬電極中間夾雜各種不同功能的有機功能材料薄膜，猶如一個三明治的結構，在電流的驅動下，從陰陽兩極分別注入空穴和電子，空穴和電子在移動一段距離後，在發光層得到複合，並以光或熱的形式進行釋放，從而產生了OLED的發光。然而，有機功能材料是有機電致發光器件的核心組成部分，材料的熱穩定性、光化學穩定性、電化學穩定性、量子產率、成膜穩定性、結晶性、色飽和度等都是影響器件性能表現的主要因素。
一方面，如何縮小OLED器件內外量子效率之間的巨大差距，如何減少器件中的全發射效應、提高光耦合提取比例引起人們的廣泛關注。現行的光提取層的材料的折射率都比較低，尤其是在紅光波段，通常折射率小於1.85，極少數大於1.90，更少數大於2.0。另外，現有的光提取材料在紅綠藍光波段區域的折射率差別較大，造成三種顏色光的最佳厚度差別大，未能充分體現光提取材料的性能。對於頂發射器件來說，光提取層材料的折射率越大，相應的外量子效率就越高，器件的發光效率就越高。所以，開發高折射率的光提取層材料尤為重要。CN103828485和TW201506128公開了以多聯苯二胺為核心的光提取層材料，但是折射率還是稍微偏低，尤其是在紅光方面更需要進一步提升。
針對上述領域中的缺陷，本發明提供一種咪唑並吡啶的芳胺類化合物，該類化合物具有昇華溫度低，熱穩定性好，折射率高、可見光區折射率差異小等優點，可用於有機發光器件中。
一種咪唑並吡啶的芳胺類化合物，其結構式為式I所示：
Figure 02_image001
（I） 其中n為1或2； X1、X2、X3、X4獨立的表示為CR0 或者N，R0 獨立的選自氫、氘、鹵素、C1-C8烷基、C1-C8雜烷基、芳烷基、氨基、矽烷基、取代或未取代的C6-C60的芳基、取代或未取代的C1-C60的雜芳基、腈、異腈，且相鄰的R0 能鍵接成並環； 其中R1 為單鍵、C1-C30亞烷基、C1-C30亞雜烷基、C3-C30亞環烷基、取代或未取代的C6-C30的亞芳基、取代或未取代的C2-C28的亞雜芳基； 其中R2獨立的選自氫、氘、鹵素、C1-C30烷基、C1-C30雜烷基、C3-C30環烷基、C1-C30烷氧基、C6-C60芳氧基、氨基、矽烷基、腈基、異腈基、膦基、取代或未取代的C6-C60的芳基、取代或未取代的C1-C60的雜芳基； 其中Ar1 為取代或未取代的C6-C60的芳基、取代或未取代的C6-C60的雜芳基、經取代或未經取代C3-C60環烷基、取代或未取代的C6-C60的芳胺基； 其中B為取代或未取代的C6-C60的芳基或亞芳基、取代或未取代的C6-C60的雜芳基或亞雜芳基、經取代或未經取代的C3-C60環烷基或亞環烷基、取代或未取代的C6-C60的芳胺基或亞芳胺基； 其中雜烷基或雜芳基中的一個或多個碳原子由選自O、S、N、Se、Si、Ge中的至少一個雜原子替換；所述取代為被氘、鹵素、C1-C30烷基、苯基、萘基或聯苯基取代。
優選：其結構式如式II所示
Figure 02_image004
（II） 其中R1 為單鍵、C1-C10亞烷基、C1-C10亞雜烷基、C3-C10亞環烷基、取代或未取代的C6-C30的亞芳基、取代或未取代的C2-C28的亞雜芳基； 其中R2獨立的選自氫、氘、鹵素、C1-C10烷基、C1-C10雜烷基、C1-C10烷氧基、C3-C30環烷基、C6-C30芳氧基、氨基、矽烷基、腈、異腈、膦基、取代或未取代的C6-C30的芳基、取代或未取代的C1-C30的雜芳基； 其中Ar1 、Ar2 為取代或未取代的C6-C30的芳基、取代或未取代的C6-C30的雜芳基、經取代或未經取代的單環或多環C3-C30脂肪族環或芳香族環、取代或未取代的C6-C30的芳胺基； 其中雜烷基或雜芳基中的一個或多個碳原子由選自O、S、N、Si中的至少一個雜原子替換；所述取代為被氘、鹵素、C1-C8烷基、苯基、萘基或聯苯基取代。
優選：其中R1 為C1-C8烷基取代或未取代的C6-C20的亞芳基、C1-C8烷基取代或未取代的C2-C18的亞雜芳基；其中R2 為C1-C8烷基、C1-C8烷基取代或未取代的C6-C20的芳基、C1-C8烷基取代或未取代的C1-C20的雜芳基；其中Ar1 、Ar2 為取代或未取代的C6-C20的芳基、取代或未取代的C6-C20的雜芳基、經取代或未經取代的單環或多環C3-C20脂肪族環或芳香族環、取代或未取代的C6-C20的芳胺基；其中雜烷基或雜芳基中的一個或多個碳原子由選自O、S、N中的至少一個雜原子替換；所述取代為被氘、C1-C8烷基、苯基、萘基或聯苯基取代。
更優選：其中R1 為C1-C4烷基取代或未取代的C6-C10的亞芳基、C1-C4烷基取代或未取代的C2-C8的亞雜芳基；其中Ar1 、R2 為C1-C4烷基取代或未取代的C6-C10的芳基、C1-C4烷基取代或未取代的C1-C8的雜芳基；其中Ar2 為取代或未取代的C6-C20的芳基、取代或未取代的C6-C20的雜芳基、經取代或未經取代的單環或多環C3-C20脂肪族環或芳香族環、取代或未取代的C6-C20的芳胺基；其中雜烷基或雜芳基中的一個或多個碳原子由選自O、S、N中的至少一個雜原子替換；所述取代為被氘、C1-C4烷基、苯基、萘基或聯苯基取代。
作為優選的化合物，Ar1或Ar2至少之一含有以下結構式（III），其中R1 為單鍵、C1-C8亞烷基、C1-C8亞雜烷基、C3-C8亞環烷基、C1-C8烷基取代或未取代的C6-C30的亞芳基、C1-C8烷基取代或未取代的C2-C28的亞雜芳基；其中R2 為氫、氘、鹵素、C1-C8烷基、C1-C8雜烷基、C3-C8環烷基、C1-C8烷基取代或未取代的C6-C30的芳基、C1-C8烷基取代或未取代的C1-C30的雜芳基。
Figure 02_image006
（III）
作為優選的化合物，可為以下式（IV）結構，其中R1 為單鍵、C1-C8亞烷基、C1-C8亞雜烷基、C3-C8亞環烷基、C1-C8烷基取代或未取代的C6-C30的亞芳基、C1-C8烷基取代或未取代的C2-C28的亞雜芳基；其中R2 為氫、氘、鹵素、C1-C8烷基、C1-C8雜烷基、C3-C8環烷基、C1-C8烷基取代或未取代的C6-C30的芳基、C1-C8烷基取代或未取代的C1-C30的雜芳基；其中Ar1 為取代或未取代的C6-C30的芳基、取代或未取代的C6-C30的雜芳基、經取代或未經取代的單環或多環C3-C30脂肪族環或芳香族環，A為取代或未取代的C6-C30的亞芳基、取代或未取代的C6-C30的亞雜芳基；其中雜烷基或雜芳基中的一個或多個碳原子由選自O、S、N、Si中的至少一個雜原子替換；所述取代為被氘、鹵素、C1-C8烷基、苯基、萘基或聯苯基取代。
Figure 02_image008
（IV）
優選：其中R1 為C1-C8烷基取代或未取代的C6-C20的亞芳基、C1-C8烷基取代或未取代的C2-C18的亞雜芳基；其中R2 為C1-C8烷基、C1-C8烷基取代或未取代的C6-C20的芳基、C1-C8烷基取代或未取代的C1-C20的雜芳基；其中Ar1 為取代或未取代的C6-C20的芳基、取代或未取代的C6-C20的雜芳基、經取代或未經取代的單環或多環C3-C20脂肪族環或芳香族環，A為取代或未取代的C6-C20的亞芳基、取代或未取代的C6-C20的亞雜芳基；其中雜烷基或雜芳基中的一個或多個碳原子由選自O、S、N中的至少一個雜原子替換；所述取代為被氘、C1-C8烷基、苯基、萘基或聯苯基取代。
優選：X1、X2、X3、X4獨立的表示為CR0 ，R0 獨立的選自氫、C1-C8烷基。
作為優選的化合物為以下化合物：
A 1 A 2 A 3
Figure 02_image010
Figure 02_image012
Figure 02_image014
A 4 A 5 A 6
Figure 02_image016
Figure 02_image018
Figure 02_image020
A 7 A 8 A 9
Figure 02_image022
Figure 02_image024
Figure 02_image026
A 10 A 11 A 12
Figure 02_image028
Figure 02_image030
Figure 02_image032
A 13 A 14 A 15
Figure 02_image034
Figure 02_image036
Figure 02_image038
A 16 A 17 A 18
Figure 02_image040
Figure 02_image042
Figure 02_image044
A 19 A 20 A 21
Figure 02_image046
Figure 02_image048
Figure 02_image050
A 22 A 23 A 24
Figure 02_image052
Figure 02_image054
Figure 02_image056
A 25 A 26 A 27
Figure 02_image058
Figure 02_image060
Figure 02_image062
A 28 A 29 A 30
Figure 02_image064
Figure 02_image066
Figure 02_image068
A 31 A 32 A 33
Figure 02_image070
Figure 02_image072
Figure 02_image074
A 34 A 35 A 36
Figure 02_image076
Figure 02_image078
Figure 02_image080
A 37 A 38 A 39
Figure 02_image082
Figure 02_image084
Figure 02_image086
A 40 A 41 A 42
Figure 02_image088
Figure 02_image090
Figure 02_image092
A 43 A 44 A 45
Figure 02_image094
Figure 02_image096
Figure 02_image098
A 46 A 47 A 48
Figure 02_image100
Figure 02_image102
Figure 02_image104
A 49 A 50 A 51
Figure 02_image106
Figure 02_image108
Figure 02_image110
A 52 A 53 A 54
Figure 02_image112
Figure 02_image114
Figure 02_image116
A 55 A 56 A 57
Figure 02_image118
Figure 02_image120
Figure 02_image122
A 58 A 59 A 60
Figure 02_image124
Figure 02_image126
Figure 02_image128
A 61 A 62 A 63
Figure 02_image130
Figure 02_image132
Figure 02_image134
A 64 A 65 A 66
Figure 02_image136
Figure 02_image138
Figure 02_image140
A 67 A 68 A 69
Figure 02_image142
Figure 02_image144
Figure 02_image146
A 70 A 71 A 72
Figure 02_image148
Figure 02_image150
Figure 02_image152
A 73 A 74 A 75
Figure 02_image154
Figure 02_image156
Figure 02_image158
A 76 A 77 A 78
Figure 02_image160
Figure 02_image162
Figure 02_image164
A 79 A 80 A 81
Figure 02_image166
Figure 02_image168
Figure 02_image170
A 82 A 83 A 84
Figure 02_image172
Figure 02_image174
Figure 02_image176
作為優選的化合物為以下化合物：
B 1 B 2 B 3
Figure 02_image178
Figure 02_image180
Figure 02_image182
B 4 B 5 B 6
Figure 02_image184
Figure 02_image186
Figure 02_image188
B 7 B 8 B 9
Figure 02_image190
Figure 02_image192
Figure 02_image194
B 10 B 11 B 12
Figure 02_image196
Figure 02_image198
Figure 02_image200
B 13 B 14 B 15
Figure 02_image202
Figure 02_image204
Figure 02_image206
B 16 B 17 B 18
Figure 02_image208
Figure 02_image210
Figure 02_image212
B 19 B 20 B 21
Figure 02_image214
Figure 02_image216
Figure 02_image218
B 22 B 23 B 24
Figure 02_image220
Figure 02_image222
Figure 02_image224
B 25 B 26 B 27
Figure 02_image226
Figure 02_image228
Figure 02_image230
B 28 B 29 B 30
Figure 02_image232
Figure 02_image234
Figure 02_image236
B 31 B 32 B 33
Figure 02_image238
Figure 02_image240
Figure 02_image242
B 34 B 35 B 36
Figure 02_image244
Figure 02_image246
Figure 02_image248
B 37 B 38 B 39
Figure 02_image250
Figure 02_image252
Figure 02_image254
B 40 B 41 B 42
Figure 02_image256
Figure 02_image258
Figure 02_image260
B 43 B 44 B 45
Figure 02_image262
Figure 02_image264
Figure 02_image266
B 46 B 47 B 48
Figure 02_image268
Figure 02_image270
Figure 02_image272
B 49 B 50 B 51
Figure 02_image274
Figure 02_image276
Figure 02_image278
B 52 B 53 B 54
Figure 02_image280
Figure 02_image282
Figure 02_image284
B 55 B 56 B 57
Figure 02_image286
Figure 02_image288
Figure 02_image290
B 58 B 59 B 60
Figure 02_image292
Figure 02_image294
Figure 02_image296
B 61 B 62 B 63
Figure 02_image298
Figure 02_image300
Figure 02_image302
B 64 B 65 B 66
Figure 02_image304
Figure 02_image306
Figure 02_image308
B 67 B 68 B 69
Figure 02_image310
Figure 02_image312
Figure 02_image314
B 70 B 71 B 72
Figure 02_image316
Figure 02_image318
Figure 02_image320
B 73 B 74 B 75
Figure 02_image322
Figure 02_image324
Figure 02_image326
B 76 B 77 B 78
Figure 02_image328
Figure 02_image330
Figure 02_image332
B 79 B 80 B 81
Figure 02_image334
Figure 02_image336
Figure 02_image338
B 82 B 83 B 84
Figure 02_image340
Figure 02_image342
Figure 02_image344
B 85 B 86 B 87
Figure 02_image346
Figure 02_image348
Figure 02_image350
B 88 B 89 B 90
Figure 02_image352
Figure 02_image354
Figure 02_image356
B 91 B 92 B 93
Figure 02_image358
Figure 02_image360
Figure 02_image362
B 94 B 95 B 96
Figure 02_image364
Figure 02_image366
Figure 02_image368
B 97 B 98 B 99
Figure 02_image370
Figure 02_image372
Figure 02_image374
B 100 B 101 B 102
Figure 02_image376
Figure 02_image378
Figure 02_image380
B 103 B 104 B 105
Figure 02_image382
Figure 02_image384
Figure 02_image386
B 106 B 107 B 108
Figure 02_image388
Figure 02_image390
Figure 02_image392
B 109 B 110 B 111
Figure 02_image394
Figure 02_image396
Figure 02_image398
B 112 B 113 B 114
Figure 02_image400
Figure 02_image402
Figure 02_image404
B 115 B 116 B 117
Figure 02_image406
Figure 02_image408
Figure 02_image410
B 118 B 119 B 120
Figure 02_image412
Figure 02_image414
Figure 02_image416
B 121 B 122 B 123
Figure 02_image418
Figure 02_image420
Figure 02_image422
B 124 B 125 B 126
Figure 02_image424
Figure 02_image426
Figure 02_image428
B 127 B 128 B 129
Figure 02_image430
Figure 02_image432
Figure 02_image434
B 130 B 131 B 132
Figure 02_image436
Figure 02_image438
Figure 02_image440
B 133 B 134 B 135
Figure 02_image442
Figure 02_image444
Figure 02_image446
B 136 B 137 B 138
Figure 02_image448
Figure 02_image450
Figure 02_image452
B 139 B 140 B 141
Figure 02_image454
Figure 02_image456
Figure 02_image458
B 142 B 143 B 144
Figure 02_image460
Figure 02_image462
Figure 02_image464
B 145 B 146 B 147
Figure 02_image466
Figure 02_image468
Figure 02_image470
B 148 B 149 B 150
Figure 02_image472
Figure 02_image474
Figure 02_image476
B 151 B 152 B 153
Figure 02_image478
Figure 02_image480
Figure 02_image482
B 154 B 155 B 156
Figure 02_image484
Figure 02_image486
Figure 02_image488
B 157 B 158 B 159
Figure 02_image490
Figure 02_image492
Figure 02_image494
B 160 B 161 B 162
Figure 02_image496
Figure 02_image498
Figure 02_image500
B 163 B 164 B 165
Figure 02_image502
Figure 02_image504
Figure 02_image506
B 166 B 167 B 168
Figure 02_image508
Figure 02_image510
Figure 02_image512
B 169 B 170 B 171
Figure 02_image514
Figure 02_image516
Figure 02_image518
B 172 B 173 B 174
Figure 02_image520
Figure 02_image522
Figure 02_image524
B 175 B 176 B 177
Figure 02_image526
Figure 02_image528
Figure 02_image530
B 178 B 179 B 180
Figure 02_image532
Figure 02_image534
Figure 02_image536
B 181 B 182 B 183
Figure 02_image538
Figure 02_image540
Figure 02_image542
B 184 B 185 B 186
Figure 02_image544
Figure 02_image546
Figure 02_image548
B 187 B 188 B 189
Figure 02_image550
Figure 02_image552
Figure 02_image554
B 190 B 191 B 192
Figure 02_image556
Figure 02_image558
Figure 02_image560
B 193 B 194 B 195
Figure 02_image562
Figure 02_image564
Figure 02_image566
B 196 B 197 B 198
Figure 02_image568
Figure 02_image570
Figure 02_image572
所述應用為化合物作為OLED器件的光提取層材料。
本發明的咪唑並吡啶的芳胺類化合物材料具有昇華溫度低，熱穩定性好，發光效率高，折射率高、可見光區折射率差異小等優點，可用於有機發光器件中。作為光提取層材料，該器件具有發光效率高、長時間熱穩定性好的優點，具有應用於AMOLED產業的可能。
下述實施例僅為了便於理解技術發明，不應視為本發明的具體限製。
本發明中的化合物合成中涉及的原物料和溶劑等均購自於Alfa、Acros等本領域技術人員熟知的供應商。
實施例1： （1）化合物A1的合成：
Figure 02_image574
Figure 02_image576
化合物03的合成：向一個2L三口瓶，依次將化合物01（80g，256.4mmol，1.0eq）、化合物02（71.64g，769.2mmol，3.0eq），t-BuONa（49.2g，512.8mmol，2.0eq）、Pd2 (dba)3 （2.35g，2.56mmol，0.01eq）, X-phos（2.44g，5.13mmol，0.02eq）,分子篩乾燥的甲苯（800ml）投入到燒瓶中，真空、氮氣置換3次，油浴加熱到108度左右，保溫攪拌回流2h，取樣點板01原料反應完。反應液降溫至80℃，滴加甲醇（800ml）攪拌1h，降至室溫後抽濾，得到固體加入THF（900ml）和正己烷（600ml）熱打漿2h，抽濾，烘乾得到71.5g類白色固體，收率82.8%。質譜：337.4（M+H）。
化合物06的合成：向一個2L單口瓶，依次將化合物04（76g，214.6mmol，1.0eq）、化合物05（50.5g，536.6mmol，2.5q），NaHCO3 （27.05g，322mmol，1.5eq）、異丙醇（700ml）投入到燒瓶中，油浴加熱到80度左右，保溫攪拌回流7h，取樣點板原料反應完。降溫，滴加去離子水，攪拌2h左右，抽濾。固體用乙酸乙酯打漿，抽濾烘乾。得到54.5g白色固體化合物06，收率72.7%。質譜：349.2（M+H）。
化合物A1的合成：向一個2L三口瓶，依次將化合物06（45.7，130.8mmol，2.2eq）、化合物03（20g，59.4mmol，1eq），t-BuONa（17.1g，178.3mmol，3.0eq）、Pd2 (dba)3 （1.09g，1.19mmol，0.02eq）, X-phos（1.13g，2.38mmol，0.04eq）,分子篩乾燥的甲苯（600ml）投入到燒瓶中，真空、氮氣置換3次，油浴加熱到108度左右，保溫攪拌回流16h，取樣點板06原料反應完。反應液降溫至80℃，滴加正己烷（800ml）攪拌1h，降至室溫後抽濾，得到固體加入二氯甲烷（1.6L）溶解完全，去離子水洗四次（500ml*4），分液後有機相用矽膠過濾，少量二氯甲烷沖洗矽膠，濃縮有機相得到固體，採用四氫呋喃/甲醇（250ml/300ml）進行重結晶2次，烘乾得到32g淡黃色固體，收率61.6%。得到的合成品經過昇華純化得到21.2克淡黃色固體化合物A1，收率66.2%。質譜：874.1（M+H）。1 HNMR(400MHz,CDCl3 )δ8.01(d,J=6.8Hz,2H),7.72(d,J=8.0Hz,3H),7.64(d,J=9.0Hz, 2H), 7.51(d,J=8.3Hz ,4H), 7.40–7.13(m,23H), 7.10(d,J=7.2Hz, 2H), 6.74(d,J=6.8Hz, 2H)。
（2）化合物A16的合成：
Figure 02_image578
化合物08的合成：選取對應的材料，參照化合物03的合成方式和處理方法，只需要將對應的原物料變更即可。質譜：412.5（M+H）。
化合物A16的合成：選取對應的材料，參照化合物A1的合成、昇華得到黃色固體化合物A16。質譜：949.1（M+H）。1 HNMR(400MHz,CDCl3 )δ8.48(d,2H),7.73(dd,4H),7.58–7.44(m,12H), 7.37(m, 8H), 7.33–7.17(m,14H), 7.08(d,4H), 7.00(d,2H),6.86(d,2H)。
（3）化合物A17的合成：
Figure 02_image580
化合物10的合成：選取對應的材料，參照化合物03的合成方式和處理方法，只需要將對應的原物料變更即可。質譜：377.5（M+H）
化合物A17的合成：選取對應的材料，參照化合物A1的合成、昇華得到黃色固體化合物A17。質譜：913.1（M+H）。1 HNMR (400MHz,CDCl3 )δ8.48(d,2H), 7.86(d,2H), 7.73(dd,4H), 7.49(dd, J=14.4,9.4Hz,10H),7.37(m,4H),7.25(dd,J=28.1,8.1Hz,12H),7.08(m,4H),7.00(d,2H),6.86(d,2H),1.69(s,6H)。
（4）化合物A22的合成：
Figure 02_image582
化合物12的合成：選取對應的材料，參照化合物06的合成方式和處理方法，只需要將對應的原物料變更即可。質譜：349.03（M+H）。
化合物A22的合成：選取對應的材料，參照化合物A1的合成、昇華得到黃色固體化合物A22。質譜：873.1（M+H）。1 HNMR(400MHz,CDCl3 )δ8.48(d,2H),7.73(dd,4H),7.60–7.42(m,12H), 7.37(m, 8H),7.33–7.16(m,10H),7.04(d,J=40.0Hz,6H),6.86(d,2H)
（5）化合物B86的合成：
Figure 02_image584
Figure 02_image586
化合物14的合成：選取對應的材料，參照化合物06的合成方式和處理方法，只需要將對應的原物料變更即可。質譜：397.30（M+H）。
化合物15的合成：選取對應的材料，參照化合物03的合成方式和處理方法，只需要將對應的原物料變更即可。質譜：361.4（M+H）。
化合物17的合成：向一個2L三口瓶，依次將化合物15（45g，124.5mmol，1.0eq）、化合物16（36.98g，130.7mmol，1.05eq），CuI（2.37g，12.45mmol，2eq）、1,10-菲羅啉（4.49g，24.9mmol，0.2eq）,K2 CO3 （34.41g，2.49mmol，0.04eq）,DMF（450ml）投入到燒瓶中，真空、氮氣置換3次，油浴加熱到120度左右，保溫攪拌8h，取樣點板15原料反應完。反應液降溫至40℃，滴加去離子水（800ml）攪拌1h，降至室溫後過濾，得到固體加入甲苯（400ml）溶解完全，去離子水洗（100ml*3），分液後有機相用矽膠過濾，少量甲苯沖洗矽膠，濃縮有機相至剩餘250ml，再滴加甲醇（300ml）進行析晶，過濾烘乾得到50.34g米白色固體化合物17，收率78.3%。質譜：516.4（M+H）。
化合物18的合成：向一個1L單口瓶，依次將化合物17（32.5g，62.9mmol，1.0eq）、聯硼酸頻那醇酯（19.18g，75.52mmol，1.2eq），Pd (dppf) Cl2 （0.92g，1.26mmol，0.02eq）、醋酸鉀（12.35g，125.8mmol，2eq）,二氧六環（350ml）投入到燒瓶中，油浴加熱到100度左右，保溫攪拌6h，取樣點板17原料反應完。反應液降溫至40℃，反應液減壓濃縮至200ml，加入甲醇（400ml）室溫下攪拌2h，過濾，得到固體加入正己烷（400ml）在50℃時打漿2h，過濾烘乾得到30.35g米白色固體化合物18，收率86.1%。質譜：563.5（M+H）。
化合物B86的合成：向一個1L三口瓶，依次將化合物18（28.0g49.69mmol，1.0eq）、化合物19（23.67g，49.69mmol，1.0eq），K2 CO3 （13.73g，99.38mmol，2.0eq）、Pd132 （0.35g，0.49mmol，0.01eq）,甲苯（280ml）,乙醇（56ml）去離子水（56ml）投入到燒瓶中，真空、氮氣置換3次，油浴加熱到75度左右，保溫攪拌回流16h，取樣點板18原料反應完。反應液降溫至60度，加入甲苯（200ml），去離子水（100ml），攪拌1h，分液，分液後有機相用矽膠過濾，少量甲苯沖洗矽膠，濃縮有機相得到固體，採用甲苯/甲醇（220ml/250ml）進行重結晶3次，烘乾得到29.47g淡黃色固體，收率71.2%。得到的合成品經過昇華純化得到22.3克淡黃色固體化合物B86，收率75.6%。質譜：833.1（M+H）。1 HNMR(400MHz,CDCl3 )δ8.48(d,1H),7.75(dd,4H),7.62–7.42(m,19H), 7.39(m, J=20.0Hz,9H),7.33–7.14(m,7H),7.08(d,2H),7.00(d,1H),6.86(d,1H)。
（6）化合物B111的合成：
Figure 02_image588
化合物B111的合成：選取對應的材料，參照化合物B86的合成方式和處理方法，只需要將對應的原物料變更即可。質譜：897.1（M+H）。1 HNMR(400MHz,CDCl3 )δ8.48(d,1H),7.96(m,6H),7.75(m,4H),7.60–7.34(m, 16H), 7.33-7.15(m,13H),7.08(d,2H),7.00(d,1H),6.86(d,1H)。
（7）化合物B130的合成：
Figure 02_image590
Figure 02_image592
化合物B130的合成：選取對應的材料，參照化合物B86的合成方式和處理方法，只需要將對應的原物料變更即可。質譜：913.2（M+H）。1 HNMR(400MHz,CDCl3 )δ8.48(d,1H),7.95–7.79(m,6H),7.60–7.44(m,14H), 7.36(m,J=13.6Hz,7H), 7.30–7.15(m,8H), 7.08(d,2H), 7.00(d,1H), 6.86(d,1H), 1.69(s,12H)
（8）化合物B137的合成：
Figure 02_image594
化合物B137的合成：選取對應的材料，參照化合物B86的合成方式和處理方法，只需要將對應的原物料變更即可。質譜：679.8（M+H）。1 HNMR(400MHz,CDCl3 )8.48(d,1H),8.13–7.94(m,3H),7.84(d,2H),7.63–7.46(m, 9H),7.45–7.29(m,5H),7.29–7.13(m,9H),7.04(d,J=40.0Hz,3H),6.86(d,1H)。
應用例： （1）化合物性能對比：本發明的化合物在OLED器件中可作為光提取層材料，具有較高的玻璃化轉變溫度、較高的折射率、可見光區較小的折射率差值。基本性能列於下表1 表1：折射率對比：
  玻璃化溫度（℃） 昇華溫度（℃） 折射率 折射率差值
@450nm @520nm @630nm ΔB-G ΔB-R ΔG-R
化合物A1 150 370 2.09 2.03 1.97 0.03 0.12 0.06
化合物A16 152 378 2.04 1.99 1.95 0.06 0.09 0.04
化合物A17 141 365 2.11 2.06 1.99 0.05 0.12 0.07
化合物A22 134 365 2.10 2.01 1.97 0.09 0.13 0.06
化合物B86 149 370 2.15 2.07 2.03 0.08 0.12 0.04
化合物B111 154 380 2.05 1.98 1.95 0.07 0.10 0.04
化合物B130 152 378 2.15 2.09 2.04 0.06 0.11 0.05
化合物B137 124 363 2.07 1.99 1.96 0.08 0.11 0.03
HTM1 134 385 1.99 1.91 1.85 0.08 0.14 0.06
（2）有機電致發光器件的製作 將50mm*50mm*1.0mm的具有ITO（100nm）透明電極的玻璃基板在乙醇中超聲清洗10分鐘，再150度烘乾後經過N2 Plasma處理30分鐘。將洗滌後的玻璃基板安裝在真空蒸鍍裝置的基板支架上，首先在有透明電極線一側的面上按照覆蓋透明電極的方式蒸鍍化合物HATCN，形成膜厚為5nm的薄膜，緊接著蒸鍍一層HTM1形成膜厚為60nm的薄膜，再在HTM1薄膜上蒸鍍一層HTM2形成膜厚為10nm的薄膜，然後，在HTM2膜層上再採用共蒸鍍的模式蒸鍍主體材料CBP和摻雜材料，膜厚為30nm，主體材料和摻雜材料比例為90%：10%。在發光層上再依次按照下表的搭配蒸鍍BCP（5nm）作為空穴阻隔層材料、Alq3 （30nm）作為電子傳輸材料，接著在電子傳輸材料層之上蒸鍍LiF(1nm) 作為電子注入材料，接著再採用共蒸鍍的模式蒸鍍Mg/Ag（18nm,1:9）作為陰極材料,最後在陰極材料之上按照下表的搭配蒸鍍CPL（50nm）作為光提取層材料。
Figure 02_image596
Figure 02_image598
器件性能評價 將上述器件進行器件性能測試，在各實施例和比較例中，使用恒定電流電源（Keithley2400）,使用固定的電流密度流過發光元件，使用分光輻射倆都系（CS2000）測試發光波譜，同時測定器件的發光效率。結果如下表2： 表2：
器件 CPL 電流效率Cd/A @3000nits
實施例1 化合物A1 52
實施例2 化合物A16 52
實施例3 化合物A17 53
實施例4 化合物A22 51
實施例5 化合物B86 50
實施例6 化合物B111 49
實施例7 化合物B130 52
實施例8 化合物B137 51
對比例1 HTM1 48
對比上述表2中的資料可知，使用本發明的化合物應用於有機電致發光器件的光提取層材料，相較於對比化合物發光效率表現出更加優越的性能。
如上所示，含有本發明結構的咪唑並吡啶的芳胺類化合物具有昇華溫度低，熱穩定性好，折射率高、可見光區折射率差異小等優點，能夠大幅改善光的取出效率、薄膜狀態的穩定性。通過使用該系列化合物製備的OLED器件，能夠得到較高的效率，並且改善其耐用性。綜上所述，該類化合物作為光提取層材料，具有應用於AMOLED產業的可能。
Figure 109134367-A0101-11-0002-3

Claims (10)

  1. 一種咪唑並吡啶的芳胺類化合物，其結構式如式（I）所示：
    Figure 03_image001
    （I） 其中n為1或2； 其中X1、X2、X3、X4獨立的表示為CR0 或者N，R0 獨立的選自氫、氘、鹵素、C1-C8烷基、C1-C8雜烷基、芳烷基、氨基、矽烷基、取代或未取代的C6-C60的芳基、取代或未取代的C1-C60的雜芳基、腈、異腈，且相鄰的R0 能鍵接成並環； 其中R1 為單鍵、C1-C30亞烷基、C1-C30亞雜烷基、C3-C30亞環烷基、取代或未取代的C6-C30的亞芳基、取代或未取代的C2-C28的亞雜芳基； 其中R2獨立的選自氫、氘、鹵素、C1-C30烷基、C1-C30雜烷基、C3-C30環烷基、C1-C30烷氧基、C6-C60芳氧基、氨基、矽烷基、腈基、異腈基、膦基、取代或未取代的C6-C60的芳基、取代或未取代的C1-C60的雜芳基； 其中Ar1 為取代或未取代的C6-C60的芳基、取代或未取代的C6-C60的雜芳基、C3-C60環烷基、取代或未取代的C6-C60的芳胺基； 其中B為取代或未取代的C6-C60的芳基或亞芳基、取代或未取代的C6-C60的雜芳基或亞雜芳基、C3-C60環烷基、取代或未取代的C6-C60的芳胺基或亞芳胺基； 其中雜烷基或雜芳基中的一個或多個碳原子由選自O、S、N、Se、Si、Ge中的至少一個雜原子替換；所述取代為被氘、鹵素、C1-C30烷基、苯基、萘基或聯苯基取代。
  2. 如請求項1所述的化合物，其結構式如式（II）所示：
    Figure 03_image004
    （II） 其中R1 為單鍵、C1-C10亞烷基、C1-C10亞雜烷基、C3-C10亞環烷基、取代或未取代的C6-C30的亞芳基、取代或未取代的C2-C28的亞雜芳基； 其中R2獨立的選自氫、氘、鹵素、C1-C10烷基、C1-C10雜烷基、C1-C10烷氧基、C3-C30環烷基、、C6-C30芳氧基、氨基、矽烷基、腈、異腈、膦基、取代或未取代的C6-C30的芳基、取代或未取代的C1-C30的雜芳基； 其中Ar1 、Ar2 為取代或未取代的C6-C30的芳基、取代或未取代的C6-C30的雜芳基、經取代或未經取代的單環或多環C3-C30脂肪族環或芳香族環、取代或未取代的C6-C30的芳胺基； 其中雜烷基或雜芳基中的一個或多個碳原子由選自O、S、N、Si中的至少一個雜原子替換；所述取代為被氘、鹵素、C1-C8烷基、苯基、萘基或聯苯基取代。
  3. 如請求項2所述的化合物，其中，R1 為C1-C8烷基取代或未取代的C6-C20的亞芳基、C1-C8烷基取代或未取代的C2-C18的亞雜芳基；其中R2 為C1-C8烷基、C1-C8烷基取代或未取代的C6-C20的芳基、C1-C8烷基取代或未取代的C1-C20的雜芳基；其中Ar1 、Ar2 為取代或未取代的C6-C20的芳基、取代或未取代的C6-C20的雜芳基、經取代或未經取代的單環或多環C3-C20脂肪族環或芳香族環、取代或未取代的C6-C20的芳胺基；其中雜烷基或雜芳基中的一個或多個碳原子由選自O、S、N中的至少一個雜原子替換；所述取代為被氘、C1-C8烷基、苯基、萘基或聯苯基取代。
  4. 如請求項3所述的化合物，其中，R1 為C1-C4烷基取代或未取代的C6-C10的亞芳基、C1-C4烷基取代或未取代的C2-C8的亞雜芳基；其中Ar1 、R2 為C1-C4烷基取代或未取代的C6-C10的芳基、C1-C4烷基取代或未取代的C1-C8的雜芳基；其中Ar2 為取代或未取代的C6-C20的芳基、取代或未取代的C6-C20的雜芳基、經取代或未經取代的單環或多環C3-C20脂肪族環或芳香族環、取代或未取代的C6-C20的芳胺基；其中雜烷基或雜芳基中的一個或多個碳原子由選自O、S、N中的至少一個雜原子替換；所述取代為被氘、C1-C4烷基、苯基、萘基或聯苯基取代。
  5. 如請求項2所述的化合物，其中，Ar1或Ar2至少之一含有以下結構式（III），
    Figure 03_image006
    （III） 其中R1 為單鍵、C1-C8亞烷基、C1-C8亞雜烷基、C3-C8亞環烷基、C1-C8烷基取代或未取代的C6-C30的亞芳基、C1-C8烷基取代或未取代的C2-C28的亞雜芳基；其中R2 為氫、氘、鹵素、C1-C8烷基、C1-C8雜烷基、C3-C8環烷基、C1-C8烷基取代或未取代的C6-C30的芳基、C1-C8烷基取代或未取代的C1-C30的雜芳基。
  6. 如請求項1所述的化合物，其結構式如式（IV）所示：
    Figure 03_image008
    （IV） 其中R1 為單鍵、C1-C8亞烷基、C1-C8亞雜烷基、C3-C8亞環烷基、C1-C8烷基取代或未取代的C6-C30的亞芳基、C1-C8烷基取代或未取代的C2-C28的亞雜芳基；其中R2 為氫、氘、鹵素、C1-C8烷基、C1-C8雜烷基、C3-C8環烷基、C1-C8烷基取代或未取代的C6-C30的芳基、C1-C8烷基取代或未取代的C1-C30的雜芳基；其中Ar1 為取代或未取代的C6-C30的芳基、取代或未取代的C6-C30的雜芳基、經取代或未經取代的單環或多環C3-C30脂肪族環或芳香族環，A為取代或未取代的C6-C30的亞芳基、取代或未取代的C6-C30的亞雜芳基；其中雜烷基或雜芳基中的一個或多個碳原子由選自O、S、N、Si中的至少一個雜原子替換；所述取代為被氘、鹵素、C1-C8烷基、苯基、萘基或聯苯基取代。
  7. 如請求項6所述的化合物，其中，R1 為C1-C8烷基取代或未取代的C6-C20的亞芳基、C1-C8烷基取代或未取代的C2-C18的亞雜芳基；其中R2 為C1-C8烷基、C1-C8烷基取代或未取代的C6-C20的芳基、C1-C8烷基取代或未取代的C1-C20的雜芳基；其中Ar1 為取代或未取代的C6-C20的芳基、取代或未取代的C6-C20的雜芳基、經取代或未經取代的單環或多環C3-C20脂肪族環或芳香族環，A為取代或未取代的C6-C20的亞芳基、取代或未取代的C6-C20的亞雜芳基；其中雜烷基或雜芳基中的一個或多個碳原子由選自O、S、N中的至少一個雜原子替換；所述取代為被氘、C1-C8烷基、苯基、萘基或聯苯基取代。
  8. 如請求項1至7中任一項所述的化合物，其中，X1、X2、X3、X4獨立的表示為CR0 ，R0 獨立的選自氫、C1-C8烷基。
  9. 如請求項1所述的化合物，其結構式如下式之一所示： A 1 A 2 A 3  
    Figure 03_image010
    Figure 03_image012
    Figure 03_image014
         A 4 A 5 A 6
    Figure 03_image016
    Figure 03_image018
    Figure 03_image020
         A 7 A 8 A 9
    Figure 03_image022
    Figure 03_image024
    Figure 03_image026
         A 10 A 11 A 12
    Figure 03_image028
    Figure 03_image030
    Figure 03_image032
         A 13 A 14 A 15
    Figure 03_image034
    Figure 03_image036
    Figure 03_image038
         A 16 A 17 A 18
    Figure 03_image040
    Figure 03_image042
    Figure 03_image044
         A 19 A 20 A 21
    Figure 03_image046
    Figure 03_image048
    Figure 03_image050
         A 22 A 23 A 24
    Figure 03_image052
    Figure 03_image054
    Figure 03_image056
         A 25 A 26 A 27
    Figure 03_image058
    Figure 03_image060
    Figure 03_image062
         A 28 A 29 A 30
    Figure 03_image064
    Figure 03_image066
    Figure 03_image068
         A 31 A 32 A 33
    Figure 03_image070
    Figure 03_image072
    Figure 03_image074
         A 34 A 35 A 36
    Figure 03_image076
    Figure 03_image078
    Figure 03_image080
         A 37 A 38 A 39
    Figure 03_image082
    Figure 03_image084
    Figure 03_image086
         A 40 A 41 A 42
    Figure 03_image088
    Figure 03_image090
    Figure 03_image092
         A 43 A 44 A 45
    Figure 03_image094
    Figure 03_image096
    Figure 03_image098
         A 46 A 47 A 48
    Figure 03_image100
    Figure 03_image102
    Figure 03_image104
         A 49 A 50 A 51
    Figure 03_image106
    Figure 03_image108
    Figure 03_image110
         A 52 A 53 A 54
    Figure 03_image112
    Figure 03_image114
    Figure 03_image116
         A 55 A 56 A 57
    Figure 03_image118
    Figure 03_image120
    Figure 03_image122
         A 58 A 59 A 60
    Figure 03_image124
    Figure 03_image126
    Figure 03_image128
         A 61 A 62 A 63
    Figure 03_image130
    Figure 03_image132
    Figure 03_image134
         A 64 A 65 A 66
    Figure 03_image136
    Figure 03_image138
    Figure 03_image140
         A 67 A 68 A 69
    Figure 03_image142
    Figure 03_image144
    Figure 03_image146
         A 70 A 71 A 72
    Figure 03_image148
    Figure 03_image150
    Figure 03_image152
         A 73 A 74 A 75
    Figure 03_image154
    Figure 03_image156
    Figure 03_image158
         A 76 A 77 A 78
    Figure 03_image160
    Figure 03_image162
    Figure 03_image164
         A 79 A 80 A 81
    Figure 03_image166
    Figure 03_image168
    Figure 03_image170
         A 82 A 83 A 84
    Figure 03_image172
    Figure 03_image174
    Figure 03_image176
         B 1 B 2 B 3
    Figure 03_image178
    Figure 03_image180
    Figure 03_image182
         B 4 B 5 B 6
    Figure 03_image184
    Figure 03_image186
    Figure 03_image188
         B 7 B 8 B 9
    Figure 03_image190
    Figure 03_image192
    Figure 03_image194
         B 10 B 11 B 12
    Figure 03_image196
    Figure 03_image198
    Figure 03_image200
         B 13 B 14 B 15
    Figure 03_image202
    Figure 03_image204
    Figure 03_image206
         B 16 B 17 B 18
    Figure 03_image208
    Figure 03_image210
    Figure 03_image212
         B 19 B 20 B 21
    Figure 03_image214
    Figure 03_image216
    Figure 03_image218
         B 22 B 23 B 24
    Figure 03_image220
    Figure 03_image222
    Figure 03_image224
         B 25 B 26 B 27
    Figure 03_image226
    Figure 03_image228
    Figure 03_image230
         B 28 B 29 B 30
    Figure 03_image232
    Figure 03_image234
    Figure 03_image236
         B 31 B 32 B 33
    Figure 03_image238
    Figure 03_image240
    Figure 03_image242
         B 34 B 35 B 36
    Figure 03_image244
    Figure 03_image246
    Figure 03_image248
         B 37 B 38 B 39
    Figure 03_image250
    Figure 03_image252
    Figure 03_image254
         B 40 B 41 B 42
    Figure 03_image256
    Figure 03_image258
    Figure 03_image260
         B 43 B 44 B 45
    Figure 03_image262
    Figure 03_image264
    Figure 03_image266
         B 46 B 47 B 48
    Figure 03_image268
    Figure 03_image270
    Figure 03_image272
         B 49 B 50 B 51
    Figure 03_image274
    Figure 03_image276
    Figure 03_image278
         B 52 B 53 B 54
    Figure 03_image280
    Figure 03_image282
    Figure 03_image284
         B 55 B 56 B 57
    Figure 03_image286
    Figure 03_image288
    Figure 03_image290
         B 58 B 59 B 60
    Figure 03_image292
    Figure 03_image294
    Figure 03_image296
         B 61 B 62 B 63
    Figure 03_image298
    Figure 03_image300
    Figure 03_image302
         B 64 B 65 B 66
    Figure 03_image304
    Figure 03_image306
    Figure 03_image308
         B 67 B 68 B 69
    Figure 03_image310
    Figure 03_image312
    Figure 03_image314
         B 70 B 71 B 72
    Figure 03_image316
    Figure 03_image318
    Figure 03_image320
         B 73 B 74 B 75
    Figure 03_image322
    Figure 03_image324
    Figure 03_image326
         B 76 B 77 B 78
    Figure 03_image328
    Figure 03_image330
    Figure 03_image332
         B 79 B 80 B 81
    Figure 03_image334
    Figure 03_image336
    Figure 03_image338
         B 82 B 83 B 84
    Figure 03_image340
    Figure 03_image342
    Figure 03_image344
         B 85 B 86 B 87
    Figure 03_image346
    Figure 03_image348
    Figure 03_image350
         B 88 B 89 B 90
    Figure 03_image352
    Figure 03_image354
    Figure 03_image356
         B 91 B 92 B 93
    Figure 03_image358
    Figure 03_image360
    Figure 03_image362
         B 94 B 95 B 96
    Figure 03_image364
    Figure 03_image366
    Figure 03_image368
         B 97 B 98 B 99
    Figure 03_image370
    Figure 03_image372
    Figure 03_image374
         B 100 B 101 B 102
    Figure 03_image376
    Figure 03_image378
    Figure 03_image380
         B 103 B 104 B 105
    Figure 03_image382
    Figure 03_image384
    Figure 03_image386
         B 106 B 107 B 108
    Figure 03_image388
    Figure 03_image390
    Figure 03_image392
         B 109 B 110 B 111
    Figure 03_image394
    Figure 03_image396
    Figure 03_image398
         B 112 B 113 B 114
    Figure 03_image400
    Figure 03_image402
    Figure 03_image404
         B 115 B 116 B 117
    Figure 03_image406
    Figure 03_image408
    Figure 03_image410
         B 118 B 119 B 120
    Figure 03_image412
    Figure 03_image414
    Figure 03_image416
         B 121 B 122 B 123
    Figure 03_image418
    Figure 03_image420
    Figure 03_image422
         B 124 B 125 B 126
    Figure 03_image424
    Figure 03_image426
    Figure 03_image428
         B 127 B 128 B 129
    Figure 03_image430
    Figure 03_image432
    Figure 03_image434
         B 130 B 131 B 132
    Figure 03_image436
    Figure 03_image438
    Figure 03_image440
         B 133 B 134 B 135
    Figure 03_image442
    Figure 03_image444
    Figure 03_image446
         B 136 B 137 B 138
    Figure 03_image448
    Figure 03_image450
    Figure 03_image452
         B 139 B 140 B 141
    Figure 03_image454
    Figure 03_image456
    Figure 03_image458
         B 142 B 143 B 144
    Figure 03_image460
    Figure 03_image462
    Figure 03_image464
         B 145 B 146 B 147
    Figure 03_image466
    Figure 03_image468
    Figure 03_image470
         B 148 B 149 B 150
    Figure 03_image472
    Figure 03_image474
    Figure 03_image476
         B 151 B 152 B 153
    Figure 03_image478
    Figure 03_image480
    Figure 03_image482
         B 154 B 155 B 156
    Figure 03_image484
    Figure 03_image486
    Figure 03_image488
         B 157 B 158 B 159
    Figure 03_image490
    Figure 03_image492
    Figure 03_image494
         B 160 B 161 B 162
    Figure 03_image496
    Figure 03_image498
    Figure 03_image500
         B 163 B 164 B 165
    Figure 03_image502
    Figure 03_image504
    Figure 03_image506
         B 166 B 167 B 168
    Figure 03_image508
    Figure 03_image510
    Figure 03_image512
         B 169 B 170 B 171
    Figure 03_image514
    Figure 03_image516
    Figure 03_image518
         B 172 B 173 B 174
    Figure 03_image520
    Figure 03_image522
    Figure 03_image524
         B 175 B 176 B 177
    Figure 03_image526
    Figure 03_image528
    Figure 03_image530
         B 178 B 179 B 180
    Figure 03_image532
    Figure 03_image534
    Figure 03_image536
         B 181 B 182 B 183
    Figure 03_image538
    Figure 03_image540
    Figure 03_image542
         B 184 B 185 B 186
    Figure 03_image544
    Figure 03_image546
    Figure 03_image548
         B 187 B 188 B 189
    Figure 03_image550
    Figure 03_image552
    Figure 03_image554
         B 190 B 191 B 192
    Figure 03_image556
    Figure 03_image558
    Figure 03_image560
         B 193 B 194 B 195
    Figure 03_image562
    Figure 03_image564
    Figure 03_image566
         B 196 B 197 B 198
    Figure 03_image568
    Figure 03_image570
    Figure 03_image572
       。
  10. 一種如請求項1至9中任一項所述的化合物在OLED器件中的應用，所述的應用為請求項1至9中任一項所述的化合物作為OLED器件的光提取層材料。
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