CN111732578A - 一种有机电致发光化合物及有机电致发光器件 - Google Patents

一种有机电致发光化合物及有机电致发光器件 Download PDF

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CN111732578A
CN111732578A CN202010786018.4A CN202010786018A CN111732578A CN 111732578 A CN111732578 A CN 111732578A CN 202010786018 A CN202010786018 A CN 202010786018A CN 111732578 A CN111732578 A CN 111732578A
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CN111732578B (zh
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钱超
许军
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Nanjing Topto Materials Co Ltd
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Abstract

本发明公开了一种有机电致发光化合物及有机电致发光器件，其结构式如下式1所示：
Figure 560842DEST_PATH_IMAGE001
，其中，R1、R2各自独立的为氢、苯基、联苯基、三联苯基、萘基；所述苯基、联苯基、三联苯基、萘基为未取代的或是其中至少一个氢被氘、碳原子数1‑4的烷基、碳原子数1‑4的氘代烷基、氰基取代而成的基团；R3、R4、R5、R6、R7各自独立的为氢、苯基、联苯基、萘基；所述苯基、联苯基、萘基为未取代的或是其中至少一个氢被氘、碳原子数1‑4的烷基、碳原子数1‑4的氘代烷基、氰基取代而成的基团；将其应用于有机电致发光器件中，作为有机电致发光材料使用，可以使有机电致发光器件的发光效率得到较大幅度提升，而且启动电压下降，功耗相对降低，使用寿命得到很大程度提升。

Description

一种有机电致发光化合物及有机电致发光器件
技术领域
本发明涉及有机电致发光技术领域，具体涉及一种有机电致发光化合物及有机电致发光器件。
背景技术
通常情况下，有机发光现象是指利用有机物质将电能转换为光能的现象。利用有机发光现象的有机电致发光器件具有宽视角、优异的对比度、快速响应时间，亮度、驱动电压和响应速度特性优异，是目前国内外研究的重点。
对于有机电致发光器件提高性能的研究包括：降低器件的驱动电压，提高器件的发光效率，提高器件的使用寿命等。为了实现有机电致发光器件性能的不断提升，不但需要有机电致发光器件的结构和制作工艺的创新，更需要有机电致光电功能材料的不断研究和创新，创制出更高性能的有机电致功能材料。
就当前有机电致发光产业的实际需求而言，目前有机电致发光材料的发展还远远不够，远远落后于面板制造企业的要求，而且国内企业的研究步伐也远远落后于美日韩企业，所以研发出提供更多可选择的有机电致发光材料是目前国内面板企业的重中之重。
发明内容
发明目的：针对上述技术问题，本发明提供了一种有机电致发光化合物及有机电致发光器件。
为了达到上述发明目的，本发明所采用的技术方案如下：
一种有机电致发光化合物，其结构式如下式1所示：
Figure 930020DEST_PATH_IMAGE001
其中，R1、R2各自独立的为氢、苯基、联苯基、三联苯基、萘基；
所述苯基、联苯基、三联苯基、萘基为未取代的或是其中至少一个氢被氘、碳原子数1-4的烷基、碳原子数1-4的氘代烷基、氰基取代而成的基团；
R3、R4、R5、R6、R7各自独立的为氢、苯基、联苯基、萘基；
所述苯基、联苯基、萘基为未取代的或是其中至少一个氢被氘、碳原子数1-4的烷基、碳原子数1-4的氘代烷基、氰基取代而成的基团；
R3、R4、R5、R6、R7不同时为氢；
R8为氢或苯基；
Ar为如下式2-a或式2-b所示基团；
Figure 909477DEST_PATH_IMAGE002
,
其中，A、B相同或不同，各自独立的为苯基或萘基；
X为O或S。
进一步地，其结构式如下式3-式5所示：
Figure 689214DEST_PATH_IMAGE003
。
进一步地，Ar为如下式6-式19所示基团：
Figure 84423DEST_PATH_IMAGE004
Figure 961112DEST_PATH_IMAGE005
Figure 783575DEST_PATH_IMAGE006
Figure 112925DEST_PATH_IMAGE007
Figure 374142DEST_PATH_IMAGE008
Figure 43021DEST_PATH_IMAGE009
Figure 98702DEST_PATH_IMAGE010
Figure 853031DEST_PATH_IMAGE011
Figure 652360DEST_PATH_IMAGE012
。
进一步地，R1、R2各自独立的为氢或苯基。
进一步地，R3、R4、R5、R6、R7各自独立的为氢、苯基、联苯基、萘基。
进一步地，所述有机电致发光化合物为以下化合物中的任意一种：
Figure 175745DEST_PATH_IMAGE013
Figure 605589DEST_PATH_IMAGE014
Figure 909532DEST_PATH_IMAGE015
Figure 184655DEST_PATH_IMAGE016
Figure 828126DEST_PATH_IMAGE017
Figure 225609DEST_PATH_IMAGE018
Figure 954531DEST_PATH_IMAGE019
Figure 33345DEST_PATH_IMAGE020
Figure 593640DEST_PATH_IMAGE021
Figure 365287DEST_PATH_IMAGE022
Figure 315925DEST_PATH_IMAGE023
Figure 198431DEST_PATH_IMAGE024
Figure 613231DEST_PATH_IMAGE025
Figure 555780DEST_PATH_IMAGE026
Figure 993714DEST_PATH_IMAGE027
Figure 414331DEST_PATH_IMAGE028
Figure 949218DEST_PATH_IMAGE029
Figure 62667DEST_PATH_IMAGE030
Figure 987898DEST_PATH_IMAGE031
Figure 212206DEST_PATH_IMAGE032
Figure 336020DEST_PATH_IMAGE033
Figure 620371DEST_PATH_IMAGE034
Figure 32897DEST_PATH_IMAGE035
Figure 123213DEST_PATH_IMAGE036
Figure 304796DEST_PATH_IMAGE037
Figure 494469DEST_PATH_IMAGE038
Figure 394291DEST_PATH_IMAGE039
Figure 22719DEST_PATH_IMAGE040
Figure 324387DEST_PATH_IMAGE041
Figure 684961DEST_PATH_IMAGE042
Figure 72080DEST_PATH_IMAGE043
Figure 504199DEST_PATH_IMAGE044
Figure 394794DEST_PATH_IMAGE045
Figure 191849DEST_PATH_IMAGE046
Figure 863002DEST_PATH_IMAGE047
Figure 36494DEST_PATH_IMAGE048
Figure 47176DEST_PATH_IMAGE049
Figure 15132DEST_PATH_IMAGE050
Figure 173580DEST_PATH_IMAGE051
Figure 885185DEST_PATH_IMAGE052
Figure 750372DEST_PATH_IMAGE053
Figure 951547DEST_PATH_IMAGE054
Figure 534975DEST_PATH_IMAGE055
Figure 784690DEST_PATH_IMAGE056
Figure 769964DEST_PATH_IMAGE057
Figure 142039DEST_PATH_IMAGE058
Figure 212764DEST_PATH_IMAGE059
Figure 266170DEST_PATH_IMAGE060
Figure 105950DEST_PATH_IMAGE061
Figure 648927DEST_PATH_IMAGE062
Figure 941368DEST_PATH_IMAGE063
Figure 798466DEST_PATH_IMAGE064
Figure 555069DEST_PATH_IMAGE065
Figure 206630DEST_PATH_IMAGE066
Figure 251947DEST_PATH_IMAGE067
Figure 647156DEST_PATH_IMAGE068
Figure 258266DEST_PATH_IMAGE069
Figure 346308DEST_PATH_IMAGE070
Figure 613341DEST_PATH_IMAGE071
Figure 812241DEST_PATH_IMAGE072
Figure 277857DEST_PATH_IMAGE073
Figure 536801DEST_PATH_IMAGE074
Figure 291130DEST_PATH_IMAGE075
Figure 28142DEST_PATH_IMAGE076
Figure 613844DEST_PATH_IMAGE077
Figure 43688DEST_PATH_IMAGE078
Figure 19734DEST_PATH_IMAGE079
Figure 622754DEST_PATH_IMAGE080
Figure 266225DEST_PATH_IMAGE081
Figure 601391DEST_PATH_IMAGE082
Figure 330313DEST_PATH_IMAGE083
Figure 471444DEST_PATH_IMAGE084
Figure 969422DEST_PATH_IMAGE085
Figure 475489DEST_PATH_IMAGE086
Figure 691707DEST_PATH_IMAGE087
Figure 636529DEST_PATH_IMAGE088
Figure 989013DEST_PATH_IMAGE089
Figure 931562DEST_PATH_IMAGE090
Figure 431813DEST_PATH_IMAGE091
Figure 852430DEST_PATH_IMAGE092
Figure 325000DEST_PATH_IMAGE093
Figure 172870DEST_PATH_IMAGE094
Figure 160418DEST_PATH_IMAGE095
Figure 384726DEST_PATH_IMAGE096
Figure 711802DEST_PATH_IMAGE097
Figure 58469DEST_PATH_IMAGE098
Figure 470996DEST_PATH_IMAGE099
Figure 233416DEST_PATH_IMAGE100
Figure 414998DEST_PATH_IMAGE101
Figure 932567DEST_PATH_IMAGE102
Figure 832390DEST_PATH_IMAGE103
Figure 398501DEST_PATH_IMAGE104
Figure 434590DEST_PATH_IMAGE105
Figure 958998DEST_PATH_IMAGE106
Figure 346117DEST_PATH_IMAGE107
Figure 450339DEST_PATH_IMAGE108
Figure 668831DEST_PATH_IMAGE109
Figure 465886DEST_PATH_IMAGE110
Figure 74721DEST_PATH_IMAGE111
Figure 248214DEST_PATH_IMAGE112
Figure 321212DEST_PATH_IMAGE113
Figure 289168DEST_PATH_IMAGE114
Figure 385300DEST_PATH_IMAGE115
Figure 831325DEST_PATH_IMAGE116
Figure 24409DEST_PATH_IMAGE117
Figure 163266DEST_PATH_IMAGE118
Figure 746694DEST_PATH_IMAGE119
Figure 996410DEST_PATH_IMAGE120
Figure 44000DEST_PATH_IMAGE121
Figure 353759DEST_PATH_IMAGE122
Figure 424483DEST_PATH_IMAGE123
Figure 540207DEST_PATH_IMAGE124
Figure 379987DEST_PATH_IMAGE125
Figure 860647DEST_PATH_IMAGE126
Figure 153088DEST_PATH_IMAGE127
Figure 72502DEST_PATH_IMAGE128
Figure 766789DEST_PATH_IMAGE129
Figure 418350DEST_PATH_IMAGE130
Figure 463666DEST_PATH_IMAGE131
Figure 921192DEST_PATH_IMAGE132
Figure 469985DEST_PATH_IMAGE133
Figure 558027DEST_PATH_IMAGE134
Figure 825060DEST_PATH_IMAGE135
Figure 820698DEST_PATH_IMAGE136
Figure 489577DEST_PATH_IMAGE137
Figure 748520DEST_PATH_IMAGE138
Figure 299587DEST_PATH_IMAGE139
Figure 302178DEST_PATH_IMAGE140
Figure 825563DEST_PATH_IMAGE141
Figure 989828DEST_PATH_IMAGE142
Figure 293771DEST_PATH_IMAGE143
Figure 834474DEST_PATH_IMAGE144
Figure 212365DEST_PATH_IMAGE145
Figure 813111DEST_PATH_IMAGE146
Figure 338770DEST_PATH_IMAGE147
Figure 683164DEST_PATH_IMAGE148
Figure 305775DEST_PATH_IMAGE149
Figure 874160DEST_PATH_IMAGE150
Figure 90377DEST_PATH_IMAGE151
Figure 972883DEST_PATH_IMAGE152
Figure 325367DEST_PATH_IMAGE153
Figure 64653DEST_PATH_IMAGE154
Figure 502587DEST_PATH_IMAGE155
Figure 188783DEST_PATH_IMAGE156
Figure 458091DEST_PATH_IMAGE157
Figure 571540DEST_PATH_IMAGE158
Figure 496771DEST_PATH_IMAGE159
Figure 721079DEST_PATH_IMAGE160
Figure 110472DEST_PATH_IMAGE161
Figure 394823DEST_PATH_IMAGE162
Figure 541770DEST_PATH_IMAGE163
Figure 632086DEST_PATH_IMAGE164
Figure 813669DEST_PATH_IMAGE165
Figure 268921DEST_PATH_IMAGE166
Figure 168744DEST_PATH_IMAGE167
Figure 797171DEST_PATH_IMAGE168
Figure 833260DEST_PATH_IMAGE169
Figure 459414DEST_PATH_IMAGE170
Figure 580953DEST_PATH_IMAGE171
Figure 13072DEST_PATH_IMAGE172
Figure 169247DEST_PATH_IMAGE173
Figure 28618DEST_PATH_IMAGE174
Figure 637454DEST_PATH_IMAGE175
Figure 545367DEST_PATH_IMAGE176
Figure 556049DEST_PATH_IMAGE177
Figure 586321DEST_PATH_IMAGE178
Figure 682453DEST_PATH_IMAGE179
Figure 394058DEST_PATH_IMAGE180
Figure 524825DEST_PATH_IMAGE181
Figure 725999DEST_PATH_IMAGE182
Figure 43848DEST_PATH_IMAGE183
Figure 559143DEST_PATH_IMAGE184
Figure 544416DEST_PATH_IMAGE185
Figure 916492DEST_PATH_IMAGE186
Figure 721637DEST_PATH_IMAGE187
。
本发明还公开了一种有机电致发光器件，包括第一电极、第二电极以及在所述第一电极和所述第二电极之间形成的有机层，所述有机层中含有上述有机电致发光化合物。
进一步地，所述有机层包含空穴注入层、空穴传输层、电子阻挡层、发光层、空穴阻挡层、电子传输层、电子注入层；所述空穴注入层、空穴传输层、电子阻挡层、发光层、空穴阻挡层、电子传输层、电子注入层中的至少一层含有上述的有机电致发光化合物。
进一步地，所述电子阻挡层中含有上述的有机电致发光化合物。
本发明所述室温均为25±5℃。
本发明的有益效果：
本发明设计了一种有机电致发光化合物及含有该化合物的有机电致发光器件，本发明在化合物分子式中引入特定位置受苯基保护的二苯并五元杂环结构，能够有效提高化合物分子的热稳定性和化学稳定性，进而提高了使用该类化合物制备的器件的寿命及效率。同时，二苯并五元杂环结构直接与三芳胺结构进行连接，增大了化合物分子的空间位阻及扭矩，有效阻挡了能量从发光层向空穴传输层的反向传递，进一步提高了器件的发光效率及寿命。
附图说明
图1为本发明提供的有机电致发光器件的结构示意图；
图中标号分别代表：
1-阳极、2-空穴注入层、3-空穴传输层、4-电子阻挡层、5-发光层、6-空穴阻挡层、7-电子传输层、8-电子注入层、9-阴极。
图2为本发明实施例1中所制备的有机电致发光化合物1的核磁氢谱图；
图3为本发明实施例1中所制备的有机电致发光化合物1的TGA图谱，由图3可知，有机电致发光化合物1的Td为510.21℃。
图4为本发明实施例1中所制备的有机电致发光化合物1的HOMO图谱，由图4可知，有机电致发光化合物1的HOMO值为5.65eV。
图5为本发明应用例1和对照例1中有机电致发光器件的寿命图；
由图5可知，本发明应用例1和对照例1所制备的有机电致发光器件的T97%寿命分别为158h和96h。
具体实施方式
以下进一步说明和描述了各个方面的实施例。应当理解，本文的描述并非旨在将权利要求书限制于所描述的特定方面。相反，旨在覆盖可包括在由所附权利要求书限定的本公开的精神和范围内的替代、修改和等同物。
如本文所用，“Ca至Cb”烃基被限定为具有碳数为“a”(包含在内)至“b”(包含在内)
的烃基。如本文所用，“a和/或b”表示“a”或“b”或“a和b”。
如本文所用，在“取代的”或“未取代的”中，术语“取代的”是指该基团中的至少一个氢与氘、烃基、烃衍生物基、卤素或氰基(-CN)重新配位。术语“未取代的”是指该基团中的至少一个氢不与氘、烃基、烃衍生物基、卤素或氰基(-CN)重新配位。烃基或烃衍生物基团的实例可包括C1至C30烷基、C2至C30烯基、C2至C30炔基、C6至C30芳基、C5至C30杂芳基、C1至C30烷氨基、C6至C30芳氨基、C6至C30杂芳氨基、C6至C30芳基杂芳氨基等，但不限于此。
如本文所用，碳原子数1～4的烷基是指甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基；
如本文所用，碳原子数1～4的氘代烷基是指甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基中的至少一个氢被氘取代所得到的基团；
实施例中未注明具体条件者，按照常规条件或制造商建议的条件进行。所用试剂或仪器未注明生产厂商者，均为可以通过市售购买获得的常规产品。
实施例1：
Figure 775043DEST_PATH_IMAGE188
有机电致发光化合物1的制备方法如下所示：
Figure 614823DEST_PATH_IMAGE189
S1：氮气保护下，将化合物1-a（10g，281.53g/mol，35.52mmol）、化合物1-b（1.1eq，4.76g，121.93g/mol，39.07mmol）和碳酸钠（2eq，7.53g，105.99g/mol，71.04mmol）加入到甲苯（200ml）、乙醇（50ml）、水（50ml）中，搅拌混匀后再加入四三苯基膦钯（0.05eq，2.05g，1155.58g/mol，1.78mmol），升温至回流反应10h后，冷却至室温加入水（150ml），搅拌分出水相，水相用二氯甲烷萃取后，合并有机相，有机相用无水硫酸钠干燥后硅胶拌样柱层析提纯，得到化合物1-c（9.44g，收率95.3%），ESI-MS(m/z)（M+）：理论值278.73，实测值278.80，元素分析结果（分子式C18H11ClO）：理论值C, 77.56; H, 3.98; Cl, 12.72; O, 5.74；实测值C, 77.56; H, 3.98; Cl, 12.72; O, 5.75。
S2：氮气保护下，将化合物1-c（8g，278.73g/mol，28.70mmol），化合物1-d（1.1eq，15.36g，486.61g/mol，31.57mmol）、叔丁醇钠（1.1eq，3.03g，96.1g/mol，31.57mmol）、三(二亚苄基丙酮)二钯（0.05eq，1.31g，915g/mol，1.44mmol）、三叔丁基膦（0.05eq，0.29g，202.32g/mol，1.44mmol）、甲苯（160ml）加入反应瓶中，加料完毕后升温至回流反应5h，反应完毕后降至室温后加入水（160ml）搅拌15min后过滤得滤液，滤液经由硅藻土过滤后分液得有机相，有机相使用无水硫酸镁干燥后旋干，经过柱层析提纯后得到有机电致发光化合物1（13.83g，收率66.1%），ESI-MS(m/z)（M+）：理论值728.88，实测值728.68，元素分析结果（分子式C54H36N2O）：理论值C, 88.98; H, 4.98; N, 3.84; O, 2.20；实测值C, 88.98; H,4.98; N, 3.85; O, 2.20。
实施例2：
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有机电致发光化合物5的制备方法如下所示：
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制备方法与实施例1基本相同，区别在于，将化合物1-d替换为化合物2-d，收率66.1%，ESI-MS(m/z)（M+）：理论值728.88，实测值728.67，元素分析结果（分子式C54H36N2O）：理论值C, 88.98; H, 4.98; N, 3.84; O, 2.20；实测值C, 88.98; H, 4.98; N, 3.84; O,2.20。
实施例3：
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有机电致发光化合物9的制备方法如下所示：
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制备方法与实施例1基本相同，区别在于，将化合物1-d替换为化合物3-d，收率63.7%，ESI-MS(m/z)（M+）：理论值728.88，实测值728.86，元素分析结果（分子式C54H36N2O）：理论值C, 88.98; H, 4.98; N, 3.84; O, 2.20；实测值C, 88.98; H, 4.98; N, 3.84; O,2.21。
实施例4：
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有机电致发光化合物17的制备方法如下所示：
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制备方法与实施例1基本相同，区别在于，将化合物1-d替换为化合物4-d，收率62.7%，ESI-MS(m/z)（M+）：理论值728.88，实测值728.47，元素分析结果（分子式C54H36N2O）：理论值C, 88.98; H, 4.98; N, 3.84; O, 2.20；实测值C, 88.98; H, 4.98; N, 3.84; O,2.20。
实施例5：
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有机电致发光化合物21的制备方法如下所示：
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制备方法与实施例1基本相同，区别在于，将化合物1-d替换为化合物5-d，收率62.2%，ESI-MS(m/z)（M+）：理论值728.88，实测值728.68，元素分析结果（分子式C54H36N2O）：理论值C, 88.98; H, 4.98; N, 3.84; O, 2.20；实测值C, 88.99; H, 4.98; N, 3.84; O,2.20。
实施例6：
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有机电致发光化合物26的制备方法如下所示：
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制备方法与实施例1基本相同，区别在于，将化合物1-d替换为化合物6-d，收率61.6%，ESI-MS(m/z)（M+）：理论值728.88，实测值728.82，元素分析结果（分子式C54H36N2O）：理论值C, 88.98; H, 4.98; N, 3.84; O, 2.20；实测值C, 88.98; H, 4.98; N, 3.84; O,2.21。
实施例7：
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有机电致发光化合物27的制备方法如下所示：
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制备方法与实施例1基本相同，区别在于，将化合物1-d替换为化合物7-d，收率62.4%，ESI-MS(m/z)（M+）：理论值728.88，实测值728.98，元素分析结果（分子式C54H36N2O）：理论值C, 88.98; H, 4.98; N, 3.84; O, 2.20；实测值C, 88.98; H, 4.98; N, 3.84; O,2.20。
实施例8：
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有机电致发光化合物34的制备方法如下所示：
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制备方法与实施例1基本相同，区别在于，将化合物1-d替换为化合物8-d，收率62.2%，ESI-MS(m/z)（M+）：理论值828.99，实测值828.96，元素分析结果（分子式C62H40N2O）：理论值C, 89.83; H, 4.86; N, 3.38; O, 1.93；实测值C, 89.83; H, 4.85; N, 3.38; O,1.93。
实施例9：
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有机电致发光化合物37的制备方法如下所示：
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制备方法与实施例1基本相同，区别在于，将化合物1-a、1-d替换为化合物9-a、9-d，收率57.3%，ESI-MS(m/z)（M+）：理论值905.09，实测值906.44，元素分析结果（分子式C68H44N2O）：理论值C, 90.24; H, 4.90; N, 3.10; O, 1.77；实测值C, 90.25; H, 4.90;N, 3.10; O, 1.77。
实施例10：
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有机电致发光化合物61的制备方法如下所示：
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制备方法与实施例1基本相同，区别在于，将化合物1-d替换为化合物10-d，收率62.3%，ESI-MS(m/z)（M+）：理论值762.97，实测值762.52，元素分析结果（分子式C56H34D6N2O）：理论值C, 88.16; H, 6.08; N, 3.67; O, 2.10；实测值C, 88.16; H, 6.08; N, 3.67; O,2.10。
实施例11：
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有机电致发光化合物66的制备方法如下所示：
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制备方法与实施例1基本相同，区别在于，将化合物1-a替换为化合物11-a，收率65.5%，ESI-MS(m/z)（M+）：理论值744.94，实测值744.81，元素分析结果（分子式C54H36N2S）：理论值C, 87.06; H, 4.87; N, 3.76; S, 4.30；实测值C, 87.06; H, 4.87; N, 3.76; S,4.30。
实施例12：
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有机电致发光化合物95的制备方法如下所示：
Figure 839186DEST_PATH_IMAGE211
制备方法与实施例1基本相同，区别在于，将化合物1-a、1-d替换为化合物12-a、12-d，收率61.8%，ESI-MS(m/z)（M+）：理论值821.04，实测值822.16，元素分析结果（分子式C60H40N2S）：理论值C, 87.77; H, 4.91; N, 3.41; S, 3.91；实测值C, 87.77; H, 4.91;N, 3.41; S, 3.92。
实施例13：
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有机电致发光化合物102的制备方法如下所示：
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制备方法与实施例1基本相同，区别在于，将化合物1-a、1-d替换为化合物13-a、13-d，收率61.1%，ESI-MS(m/z)（M+）：理论值845.06，实测值846.28，元素分析结果（分子式C62H40N2S）：理论值C, 88.12; H, 4.77; N, 3.31; S, 3.79；实测值C, 88.12; H, 4.77;N, 3.31; S, 3.80。
实施例14：
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有机电致发光化合物109的制备方法如下所示：
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制备方法与实施例1基本相同，区别在于，将化合物1-a、1-d替换为化合物14-a、14-d，收率59.5%，ESI-MS(m/z)（M+）：理论值845.06，实测值846.10，元素分析结果（分子式C62H40N2S）：理论值C, 88.12; H, 4.77; N, 3.31; S, 3.79；实测值C, 88.12; H, 4.77;N, 3.31; S, 3.79。
实施例15：
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有机电致发光化合物128的制备方法如下所示：
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制备方法与实施例1基本相同，区别在于，将化合物1-a、1-d替换为化合物15-a、15-d，收率60.2%，ESI-MS(m/z)（M+）：理论值801.05，实测值802.37，元素分析结果（分子式C58H44N2S）：理论值C, 86.96; H, 5.54; N, 3.50; S, 4.00；实测值C, 86.96; H, 5.55;N, 3.50; S, 4.00。
实施例16：
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有机电致发光化合物136的制备方法如下所示：
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制备方法与实施例1基本相同，区别在于，将化合物1-d替换为化合物16-d，收率63.1%，ESI-MS(m/z)（M+）：理论值728.88，实测值728.90，元素分析结果（分子式C54H36N2O）：理论值C, 88.98; H, 4.98; N, 3.84; O, 2.20；实测值C, 88.98; H, 4.97; N, 3.84; O,2.20。
实施例17：
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有机电致发光化合物137的制备方法如下所示：
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制备方法与实施例1基本相同，区别在于，将化合物1-a、1-d替换为化合物17-a、17-d，收率63.6%，ESI-MS(m/z)（M+）：理论值728.88，实测值728.62，元素分析结果（分子式C54H36N2O）：理论值C, 88.98; H, 4.98; N, 3.84; O, 2.20；实测值C, 88.98; H, 4.98;N, 3.84; O, 2.20。
实施例18：
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有机电致发光化合物147的制备方法如下所示：
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制备方法与实施例9基本相同，区别在于，将化合物9-d替换为化合物18-d，收率65.7%，ESI-MS(m/z)（M+）：理论值804.97，实测值804.80，元素分析结果（分子式C60H40N2O）：理论值C, 89.52; H, 5.01; N, 3.48; O, 1.99；实测值C, 89.52; H, 5.01; N, 3.48; O,1.99。
实施例19：
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有机电致发光化合物151的制备方法如下所示：
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制备方法与实施例15基本相同，区别在于，将化合物15-a、15-d替换为化合物19-a、19-d，收率64.3%，ESI-MS(m/z)（M+）：理论值744.94，实测值744.59，元素分析结果（分子式C54H36N2S）：理论值C, 87.06; H, 4.87; N, 3.76; S, 4.30；实测值C, 87.06; H, 4.87;N, 3.76; S, 4.30。
实施例20：
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有机电致发光化合物166的制备方法如下所示：
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制备方法与实施例1基本相同，区别在于，将化合物1-d替换为化合物20-d，收率63.0%，ESI-MS(m/z)（M+）：理论值804.97，实测值804.68，元素分析结果（分子式C60H40N2O）：理论值C, 89.52; H, 5.01; N, 3.48; O, 1.99；实测值C, 89.52; H, 5.01; N, 3.48; O,1.99。
实施例21：
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有机电致发光化合物176的制备方法如下所示：
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制备方法与实施例1基本相同，区别在于，将化合物1-d替换为化合物21-d，收率61.7%，ESI-MS(m/z)（M+）：理论值728.88，实测值728.97，元素分析结果（分子式C54H36N2O）：理论值C, 88.98; H, 4.98; N, 3.84; O, 2.20；实测值C, 88.98; H, 4.98; N, 3.84; O,2.20。
器件性能测试：
测试本发明实施例1-21中的有机电致发光化合物1、5、9、17、21、26、27、34、37、61、66、95、102、109、128、136、137、147、151、166、176的玻璃化温度Tg、热失重温度Td、HOMO值和LOMO值，结果如表1所示：
注：热失重温度Td是在氮气气氛中失重5％的温度，在TGA N-1000热重分析仪上进行测定，测定时氮气流量为10mL/min，玻璃化温度Tg由示差扫描量热法(DSC，新科DSC N-650)测定，升温速率10℃/min。
表1：
Figure 644703DEST_PATH_IMAGE230
由上表1可知，本发明有机电致发光化合物具有较高的Tg值、Tm值和Td值，说明其具有优良的热稳定性，而且具有合适的HOMO、LOMO值将其应用于有机电致发光器件中，可以有效延长有机电致发光器件的使用寿命，且可以获得更佳的使用效果。
器件性能测试：
应用例1:
采用ITO作为反射层阳极基板材料，并依次用水、丙酮、N2等离子对其进行表面处理；
在ITO阳极基板上方，沉积厚度为10nm的HAT-CN形成空穴注入层(HIL)；
在空穴注入层(HIL)上方蒸镀100nm的HT-1形成空穴传输层(HTL)；
在空穴传输层(HTL)上方真空蒸镀本发明实施例1制备的有机电致发光化合物1，形成厚度为10nm的电子阻挡层（EBL）；
将BH-1作为蓝光主体材料、BD-1作为蓝光掺杂材料（BD-1用量为ADN重量的5%）以不同速率蒸发在空穴传输层(HTL)上形成厚度为20nm的发光层；
将HB-1蒸镀到发光层上得到厚度为20nm的空穴阻挡层（HBL）；
将ET-1作为电子传输层材料（ET）蒸镀到空穴阻挡层（HBL）上得到厚度为30nm的电子传输层(ETL)，在电子传输层(ETL)上方蒸镀厚度为2nm的LiQ形成电子注入层(EIL)；
此后将镁（Mg）和银（Ag）以9:1的比例混合蒸镀得到厚度为15nm的阴极，在上述阴极封口层上沉积50nm厚度的DNTPD，此外，在阴极表面以UV硬化胶合剂和含有除湿剂的封装薄膜(seal cap)进行密封，以保护有机电致发光器件不被大气中的氧气或水分所影响至此制备获得有机电致发光器件。
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Figure 907374DEST_PATH_IMAGE232
Figure 209042DEST_PATH_IMAGE233
Figure 835196DEST_PATH_IMAGE234
Figure 956735DEST_PATH_IMAGE235
Figure 388854DEST_PATH_IMAGE236
Figure 545029DEST_PATH_IMAGE237
Figure 342083DEST_PATH_IMAGE238
Figure 950919DEST_PATH_IMAGE239
Figure 921149DEST_PATH_IMAGE240
Figure 931831DEST_PATH_IMAGE241
Figure 899787DEST_PATH_IMAGE242
。
其中，EB-1是本领域目前常用到的电子阻挡层材料；
EB-2、EB-3、EB-4是现有专利（WO2017099471A1）所公开的化合物。
应用例2-21
分别用本发明实施例2-21中的有机电致发光化合物有机电致发光化合物5、9、17、21、26、27、34、37、61、66、95、102、109、128、136、137、147、151、166、176替代应用例1中的有机电致发光化合物1，其他部分与应用例1一致，据此制作出应用例2-21的有机电致发光器件。
对照例1-4
对照例1-4和与应用例1的区别在于，分别使用EB-1、EB-2、EB-3、EB-4替代应用例1中的有机电致发光化合物1，其余与应用例1相同。
分别测试应用例1-26及对照例制备的有机电致发光器件，测试结果如表2所示。
表2:
Figure 995919DEST_PATH_IMAGE243
由上表2可知，将本发明有机电致发光化合物应用于有机电致发光器件中，作为电子阻挡层（EBL）使用，可以使有机电致发光器件的发光效率得到较大幅度提升，而且启动电压下降，功耗相对降低。
将对照例1-4及应用例1-6所制备的有机电致发光器件进行发光寿命测试，得到发光寿命T97%数据（发光亮度降低至初始亮度97%的时间），测试设备为TEO发光器件寿命测试系统。结果如表3所示：
表3：
Figure 769840DEST_PATH_IMAGE244
由上表3可知，将本发明有机电致发光化合物作为电子阻挡层（EBL）使用应用于有机电致发光器件中，所制备的有机电致发光器件使用寿命得到很大程度提升，所以具有很广阔的应用前景。

Claims (9)

1.一种有机电致发光化合物，其特征在于，其结构式如下式1所示：
Figure 297839DEST_PATH_IMAGE001
，
其中，R1、R2各自独立的为氢、苯基、联苯基、三联苯基、萘基；
所述苯基、联苯基、三联苯基、萘基为未取代的或是其中至少一个氢被氘、碳原子数1-4的烷基、碳原子数1-4的氘代烷基、氰基取代而成的基团；
R3、R4、R5、R6、R7各自独立的为氢、苯基、联苯基、萘基；
所述苯基、联苯基、萘基为未取代的或是其中至少一个氢被氘、碳原子数1-4的烷基、碳原子数1-4的氘代烷基、氰基取代而成的基团；
R3、R4、R5、R6、R7不同时为氢；
R8为氢或苯基；
Ar为如下式2-a或式2-b所示基团；
Figure 436696DEST_PATH_IMAGE002
其中，A、B相同或不同，各自独立的为苯基或萘基；
X为O或S。
2.如权利要求1所述的有机电致发光化合物，其特征在于，其结构式如下式3-式5所示：
Figure 20124DEST_PATH_IMAGE003
。
3.如权利要求1所述的有机电致发光化合物，其特征在于，Ar为如下式6-式19所示基团：
Figure 597736DEST_PATH_IMAGE004
Figure 317430DEST_PATH_IMAGE005
Figure 627189DEST_PATH_IMAGE006
Figure 760230DEST_PATH_IMAGE007
Figure 813637DEST_PATH_IMAGE008
Figure 653417DEST_PATH_IMAGE009
Figure 196393DEST_PATH_IMAGE010
Figure 754414DEST_PATH_IMAGE011
Figure 345932DEST_PATH_IMAGE012
。
4.如权利要求1所述的有机电致发光化合物，其特征在于，R1、R2各自独立的为氢或苯基。
5.如权利要求1所述的有机电致发光化合物，其特征在于，R3、R4、R5、R6、R7各自独立的为氢、苯基、联苯基、萘基。
6.如权利要求1所述的有机电致发光化合物，其特征在于，所述有机电致发光化合物为以下化合物中的任意一种：
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Figure 223124DEST_PATH_IMAGE019
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Figure 223627DEST_PATH_IMAGE025
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Figure 957414DEST_PATH_IMAGE027
Figure 232537DEST_PATH_IMAGE028
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Figure 910884DEST_PATH_IMAGE059
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Figure 221463DEST_PATH_IMAGE063
Figure 933067DEST_PATH_IMAGE064
Figure 798254DEST_PATH_IMAGE065
Figure 999429DEST_PATH_IMAGE066
Figure 582857DEST_PATH_IMAGE067
Figure 894889DEST_PATH_IMAGE068
Figure 880163DEST_PATH_IMAGE069
Figure 189921DEST_PATH_IMAGE070
Figure 322963DEST_PATH_IMAGE071
Figure 376369DEST_PATH_IMAGE072
Figure 216149DEST_PATH_IMAGE073
Figure 759126DEST_PATH_IMAGE074
Figure 51567DEST_PATH_IMAGE075
Figure 908665DEST_PATH_IMAGE076
Figure 665268DEST_PATH_IMAGE077
Figure 316829DEST_PATH_IMAGE078
Figure 362146DEST_PATH_IMAGE079
Figure 757355DEST_PATH_IMAGE080
Figure 368465DEST_PATH_IMAGE081
Figure 456507DEST_PATH_IMAGE082
Figure 723540DEST_PATH_IMAGE083
Figure 984757DEST_PATH_IMAGE084
Figure 388056DEST_PATH_IMAGE085
Figure 646999DEST_PATH_IMAGE086
Figure 401329DEST_PATH_IMAGE087
Figure 200658DEST_PATH_IMAGE088
Figure 724043DEST_PATH_IMAGE089
Figure 153887DEST_PATH_IMAGE090
Figure 192250DEST_PATH_IMAGE091
Figure 732953DEST_PATH_IMAGE092
Figure 376424DEST_PATH_IMAGE093
Figure 711590DEST_PATH_IMAGE094
Figure 502829DEST_PATH_IMAGE095
Figure 581643DEST_PATH_IMAGE096
Figure 79621DEST_PATH_IMAGE097
Figure 648005DEST_PATH_IMAGE098
Figure 864223DEST_PATH_IMAGE099
Figure 746728DEST_PATH_IMAGE100
Figure 99212DEST_PATH_IMAGE101
Figure 104077DEST_PATH_IMAGE102
Figure 542012DEST_PATH_IMAGE103
Figure 962629DEST_PATH_IMAGE104
Figure 497516DEST_PATH_IMAGE105
Figure 345386DEST_PATH_IMAGE106
Figure 270617DEST_PATH_IMAGE107
Figure 494925DEST_PATH_IMAGE108
Figure 884318DEST_PATH_IMAGE109
Figure 168668DEST_PATH_IMAGE110
Figure 581195DEST_PATH_IMAGE111
Figure 405932DEST_PATH_IMAGE112
Figure 587514DEST_PATH_IMAGE113
Figure 42766DEST_PATH_IMAGE114
Figure 4906DEST_PATH_IMAGE115
Figure 571017DEST_PATH_IMAGE116
Figure 607106DEST_PATH_IMAGE117
Figure 295576DEST_PATH_IMAGE118
Figure 682695DEST_PATH_IMAGE119
Figure 786917DEST_PATH_IMAGE120
Figure 943092DEST_PATH_IMAGE121
Figure 802464DEST_PATH_IMAGE122
Figure 411300DEST_PATH_IMAGE123
Figure 584792DEST_PATH_IMAGE124
Figure 657790DEST_PATH_IMAGE125
Figure 625746DEST_PATH_IMAGE126
Figure 721878DEST_PATH_IMAGE127
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Figure 713775DEST_PATH_IMAGE134
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Figure 126805DEST_PATH_IMAGE141
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Figure 823682DEST_PATH_IMAGE143
Figure 281208DEST_PATH_IMAGE144
Figure 830001DEST_PATH_IMAGE145
Figure 918043DEST_PATH_IMAGE146
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Figure 180714DEST_PATH_IMAGE148
Figure 849593DEST_PATH_IMAGE149
Figure 108536DEST_PATH_IMAGE150
Figure 659603DEST_PATH_IMAGE151
Figure 662194DEST_PATH_IMAGE152
Figure 185579DEST_PATH_IMAGE153
Figure 412161DEST_PATH_IMAGE154
Figure 653787DEST_PATH_IMAGE155
Figure 194489DEST_PATH_IMAGE156
Figure 572381DEST_PATH_IMAGE157
Figure 235444DEST_PATH_IMAGE158
Figure 698786DEST_PATH_IMAGE159
Figure 43180DEST_PATH_IMAGE160
Figure 541157DEST_PATH_IMAGE161
Figure 109542DEST_PATH_IMAGE162
Figure 325759DEST_PATH_IMAGE163
Figure 208265DEST_PATH_IMAGE164
Figure 623066DEST_PATH_IMAGE165
Figure 300035DEST_PATH_IMAGE166
Figure 737969DEST_PATH_IMAGE167
Figure 486482DEST_PATH_IMAGE168
Figure 693473DEST_PATH_IMAGE169
Figure 806922DEST_PATH_IMAGE170
Figure 794470DEST_PATH_IMAGE171
Figure 18778DEST_PATH_IMAGE172
Figure 345854DEST_PATH_IMAGE173
Figure 630205DEST_PATH_IMAGE174
Figure 839469DEST_PATH_IMAGE175
Figure 867468DEST_PATH_IMAGE176
Figure 49051DEST_PATH_IMAGE177
Figure 566620DEST_PATH_IMAGE178
Figure 466443DEST_PATH_IMAGE179
Figure 32553DEST_PATH_IMAGE180
Figure 68642DEST_PATH_IMAGE181
Figure 757113DEST_PATH_IMAGE182
Figure 878652DEST_PATH_IMAGE183
Figure 248454DEST_PATH_IMAGE184
Figure 466946DEST_PATH_IMAGE185
Figure 264000DEST_PATH_IMAGE186
Figure 872836DEST_PATH_IMAGE187
。
7.一种有机电致发光器件，其特征在于，包括第一电极、第二电极以及在所述第一电极和所述第二电极之间形成的有机层，所述有机层中含有如权利要求1-6中任一项所述的有机电致发光化合物。
8.根据权利要求7所述的有机电致发光器件，其特征在于，所述有机层包含空穴注入层、空穴传输层、电子阻挡层、发光层、空穴阻挡层、电子传输层、电子注入层；所述空穴注入层、空穴传输层、电子阻挡层、发光层、空穴阻挡层、电子传输层、电子注入层中的至少一层含有如权利要求1-6中任一项所述的有机电致发光化合物。
9.根据权利要求8所述的有机电致发光器件，其特征在于，所述电子阻挡层中含有如权利要求1-6中任一项所述的有机电致发光化合物。
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