CN112812106B - 一种化合物及有机电致发光器件 - Google Patents

一种化合物及有机电致发光器件 Download PDF

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CN112812106B
CN112812106B CN202110416762.XA CN202110416762A CN112812106B CN 112812106 B CN112812106 B CN 112812106B CN 202110416762 A CN202110416762 A CN 202110416762A CN 112812106 B CN112812106 B CN 112812106B
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钱超
许军
朱东林
黄明辉
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Nanjing Topto Materials Co Ltd
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Abstract

本发明公开了一种化合物及有机电致发光器件,涉及有机电致发光技术领域,其结构式如下式1所示基团:
Figure 555359DEST_PATH_IMAGE001
其中,Y为O或S;Ar为经取代或未经取代的C6‑C20的芳基;R4、R5、R6、R7、R8各自为氢或氘,R1、R2、R3、R9、R10、R11相同或不同,各自独立的为氢、氘、经取代或未经取代的C6‑C20的芳基、经取代或未经取代的C5‑C20的杂芳基;本发明化合物应用于有机电致发光器件中,在相同电流密度下,器件的发光效率得到了较大幅度的提升,启动电压有所下降,功耗相对降低,寿命相应提高。

Description

一种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,具体涉及一种化合物及有机电致发光器件。
背景技术
有机电致发光器件(Organic Light-emitting Devices, OLED)是利用如下原理的自发性发光器件:当施加电场时,荧光物质通过正极注入的空穴和负极注入的电子的重新结合而发光。这种自发光器件,具有电压低、亮度高、视角宽、响应快、温度适应性好等特性,并且超薄,能制作在柔性面板上等优点,广泛应用于手机、平板电脑、电视、照明等领域。
OLED作为一种利用多层有机薄膜结构产生电致发光的器件,它很容易制作,而且只需要低的驱动电压,这些主要的特征使得OLED在满足平面显示器的应用上显得非常突出。OLED显示屏比LCD更轻薄、亮度高、功耗低、响应快、清晰度高、柔性好、发光效率高,能满足消费者对显示技术的新需求。全球越来越多的显示器厂家纷纷投入研发,大大的推动了OLED的产业化进程。
对于有机电致发光器件提高性能的研究,目前主要集中在如何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方向。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。
目前,就当前有机电致发光产业的实际需求而言,有机电致发光材料的发展还远远不够,落后于面板制造企业的要求,需要继续提高发光器件的发光效率及寿命,推进OLED材料的国产化。
发明内容
发明目的:针对上述技术问题,本发明提供了一种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:
一种化合物,其结构式如下式1所示基团:
Figure 511836DEST_PATH_IMAGE001
其中,Y为O或S;Ar为经取代或未经取代的C6-C20的芳基;
R1、R2、R3、R9、R10、R11 相同或不同,各自独立的为氢、氘、经取代或未经取代的C6-C20的芳基、经取代或未经取代的C5-C20的杂芳基;
R4、R5、R6、R7、R8各自为氢或氘。
优选的,R1、R2、R3、R9、R10、R11相同或不同,各自独立的选自氢、氘、苯基、氘代苯基、联苯基、氘代联苯基、三联苯基、氘代三联苯基;Ar为经氘取代或未经氘取代的苯基、经氘取代或未经氘取代的联苯基、经氘取代或未经氘取代的三联苯基;R4、R5、R6、R7、R8同时为氢或氘。
优选的,R1、R2、R3、R9、R10、R11各自独立的选自氢、苯基、氘代苯基;
Ar为经氘代或未经氘代的苯基、经氘代或未经氘代的联苯基。
进一步地,R9、R10、R11均为氢。
进一步地,其为以下化合物的任意一种:
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Figure 586769DEST_PATH_IMAGE003
Figure 978961DEST_PATH_IMAGE004
Figure 339404DEST_PATH_IMAGE005
Figure 474719DEST_PATH_IMAGE006
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Figure 356698DEST_PATH_IMAGE019
Figure 367249DEST_PATH_IMAGE020
Figure 351910DEST_PATH_IMAGE021
Figure 29885DEST_PATH_IMAGE022
Figure 868396DEST_PATH_IMAGE023
Figure 566575DEST_PATH_IMAGE024
Figure 273369DEST_PATH_IMAGE025
Figure 949726DEST_PATH_IMAGE026
Figure 896822DEST_PATH_IMAGE027
Figure 554068DEST_PATH_IMAGE028
Figure 877602DEST_PATH_IMAGE029
Figure 668185DEST_PATH_IMAGE030
Figure 520603DEST_PATH_IMAGE031
Figure 665146DEST_PATH_IMAGE032
Figure 592038DEST_PATH_IMAGE033
Figure 505636DEST_PATH_IMAGE034
Figure 794535DEST_PATH_IMAGE035
Figure 160794DEST_PATH_IMAGE036
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Figure 349164DEST_PATH_IMAGE038
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Figure 276495DEST_PATH_IMAGE055
Figure 347743DEST_PATH_IMAGE056
Figure 500376DEST_PATH_IMAGE057
Figure 603330DEST_PATH_IMAGE058
Figure 917637DEST_PATH_IMAGE059
Figure 673585DEST_PATH_IMAGE060
Figure 161067DEST_PATH_IMAGE061
Figure 587369DEST_PATH_IMAGE062
Figure 338156DEST_PATH_IMAGE063
Figure 790521DEST_PATH_IMAGE064
Figure 284957DEST_PATH_IMAGE065
Figure 362503DEST_PATH_IMAGE066
Figure 18612DEST_PATH_IMAGE067
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化合物。
进一步地,所述发光层中含有上述的化合物。
更进一步,所述发光层中还含有以下化合物G1-G48中的至少一种:
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Figure 336295DEST_PATH_IMAGE069
Figure 268348DEST_PATH_IMAGE070
Figure 98288DEST_PATH_IMAGE071
Figure 319054DEST_PATH_IMAGE072
Figure 420871DEST_PATH_IMAGE073
Figure 410693DEST_PATH_IMAGE074
Figure 405675DEST_PATH_IMAGE075
Figure 910474DEST_PATH_IMAGE076
Figure 284824DEST_PATH_IMAGE077
Figure 129152DEST_PATH_IMAGE078
Figure 363212DEST_PATH_IMAGE079
Figure 558570DEST_PATH_IMAGE080
Figure 939873DEST_PATH_IMAGE081
Figure 701024DEST_PATH_IMAGE082
Figure 975492DEST_PATH_IMAGE083
Figure 658146DEST_PATH_IMAGE084
Figure 374298DEST_PATH_IMAGE085
Figure 255535DEST_PATH_IMAGE086
Figure 362556DEST_PATH_IMAGE087
Figure 266927DEST_PATH_IMAGE088
Figure 786770DEST_PATH_IMAGE089
Figure 722846DEST_PATH_IMAGE090
Figure 669943DEST_PATH_IMAGE091
Figure 61610DEST_PATH_IMAGE092
Figure 385144DEST_PATH_IMAGE093
Figure 181586DEST_PATH_IMAGE094
Figure 299584DEST_PATH_IMAGE095
Figure 240864DEST_PATH_IMAGE096
Figure 102509DEST_PATH_IMAGE097
Figure 583536DEST_PATH_IMAGE098
Figure 138014DEST_PATH_IMAGE099
Figure 566590DEST_PATH_IMAGE100
Figure 969277DEST_PATH_IMAGE101
Figure 737382DEST_PATH_IMAGE102
Figure 197182DEST_PATH_IMAGE103
Figure 50738DEST_PATH_IMAGE104
Figure 313573DEST_PATH_IMAGE105
Figure 873867DEST_PATH_IMAGE106
Figure 770148DEST_PATH_IMAGE107
Figure 845420DEST_PATH_IMAGE108
Figure 855489DEST_PATH_IMAGE109
Figure 736202DEST_PATH_IMAGE110
Figure 600122DEST_PATH_IMAGE111
一种含有上述有机电致发光器件的电子显示设备。
一种含有上述有机电致发光器件的OLED照明设备。
本发明所述室温均为25±5℃。
本发明的有益效果:
本发明设计了一款应用于OLED有机电致发光材料,本发明的有机电致发光化合物是以富电子基团-咔唑及咔唑衍生物、吸电子基团-三嗪、及增加寿命的二苯并呋喃及其衍生物以特定的方式连接而成的化合物;
一方面,在式1所示基团中将二苯并呋喃及其衍生物的4-号位与三嗪基团连接,该连接方式有三个好处:1、将二苯并呋喃的4-号活泼位置保护起来,增加该类化合物的热稳定性及化学稳定性;2、该种连接方式能够增加化合物的扭矩,提高该类化合物的三线态能级,避免能量由掺杂材料向主体材料的反向传递;3、该种连接方式在增加化合物扭矩的同时,增加了材料的溶解性,增加了该类材料的量产性、降低了制备成本。
另一方面,式1中咔唑及其衍生物与三嗪基团直接连接即D-A结构,而非通过苯环等方式进行桥连即D-π-A的结构,该种连接方式能够导致该类化合物HOMO、LUMO的分离,进而减小该类材料的单线态与三线态之间的能极差即较小∆Est的值。∆Est数值的较小,有利于该类化合物的三线态向单线态的反向系间窜跃,使该类材料具备了成为TADF材料的可能性。进而提高了器件的发光效率及寿命。
经过器件验证,使用本发明设计的化合物与相应的P-type材料搭配制备的有机电致发光器件,其发光效率及寿命均有显著的提高。
附图说明
图1为本发明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-第一空穴传输层、4-第二空穴传输层、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中所制备的化合物1的HPLC图。
图3为本发明实施例1中所制备的化合物1的DSC图谱,由图3可知,化合物1的Tm值为277.33℃。
图4为本发明实施例1中所制备的化合物1的TGA图谱,由图4可知,热失重温度Td值为447.47℃。
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564h和436h。
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,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C20烷基、C2至C20烯基、C2至C20炔基、C6至C20芳基、C5至C20杂芳基、C1至C20烷氨基、C6至C20芳氨基、C6至C20杂芳氨基、C6至C20芳基杂芳氨基等,但不限于此。
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 693848DEST_PATH_IMAGE112
化合物1的合成方法如下:
Figure 239099DEST_PATH_IMAGE113
Figure 833373DEST_PATH_IMAGE114
氮气保护下,将化合物1-A(10g,370.25g/mol,27.01mmol)、化合物1-B(1.1eq,10.6g,356.81g/mol,29.71mmol)和碳酸钠(2eq,5.72g,105.99g/mol,54.02mmol)加入到乙二醇二胺醚(200g,化合物1-A的20倍质量)和水(200g,化合物1-A的20倍质量)中,搅拌混匀后再依次加入三(邻甲苯基)膦(0.05eq,0.41g,304.37g/mol,1.35mmol)和乙酸钯(II)(0.01eq,0.06g,224.51g/mol,0.27mmol),升温至回流反应15h后,将有机相分出,水洗后减压浓缩,得到粗品,粗品再经过柱层析后得到化合物1(7.89,收率51.8%),ESI-MS(m/z)(M+):理论值564.63,实测值564.78,元素分析结果(分子式C39H24N4O):理论值 C, 82.96;H, 4.28; N, 9.92; O, 2.83;实测值 C, 82.92; H, 4.31; N, 9.93; O, 2.84。
实施例2:
Figure 805877DEST_PATH_IMAGE115
化合物2的合成方法如下:
Figure 121321DEST_PATH_IMAGE116
Figure 204683DEST_PATH_IMAGE117
Figure 783957DEST_PATH_IMAGE118
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2-a,收率54.0%,ESI-MS(m/z)(M+):理论值569.66,实测值570.20,元素分析结果(分子式C39H19D5N4O):理论值 C,82.23; H, 5.13; N, 9.84; O, 2.81;实测值 C,82.20; H,5.15; N, 9.86; O, 2.79。
实施例3:
Figure 51996DEST_PATH_IMAGE119
化合物3的合成方法如下:
Figure 406402DEST_PATH_IMAGE120
Figure 90193DEST_PATH_IMAGE121
Figure 396409DEST_PATH_IMAGE122
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3-a,收率53.7%,ESI-MS(m/z)(M+):理论值640.73,实测值640.65,元素分析结果(分子式C45H28N4O):理论值 C,84.35; H, 4.40; N, 8.74; O, 2.50;实测值C,84.31; H, 4.42;N, 8.76; O, 2.51。
实施例4:
Figure 979225DEST_PATH_IMAGE123
化合物21的合成方法如下:
Figure 800419DEST_PATH_IMAGE124
Figure 491164DEST_PATH_IMAGE125
Figure 445695DEST_PATH_IMAGE126
制备方法与实施例1基本相同,区别在于,将化合物1-B替换为化合物4-b,收率50.5%,ESI-MS(m/z)(M+):理论值640.73,实测值640.30,元素分析结果(分子式C45H28N4O):理论值C, 84.35; H, 4.40; N, 8.74; O, 2.50;实测值C, 84.40; H, 4.37;N, 8.72; O, 2.51。
实施例5:
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化合物22的合成方法如下:
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Figure 530566DEST_PATH_IMAGE129
Figure 79884DEST_PATH_IMAGE130
制备方法与实施例1基本相同,区别在于,将化合物1-A、1-B替换为化合物5-a、5-b,收率53.2%,ESI-MS(m/z)(M+):理论值645.76,实测值646.49,元素分析结果(分子式C45H23D5N4O):理论值C, 83.70; H, 5.15; N, 8.68; O, 2.48;实测值C, 83.60; H,5.20; N, 8.73; O, 2.47。
实施例6:
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化合物41的合成方法如下:
Figure 469462DEST_PATH_IMAGE132
Figure 764659DEST_PATH_IMAGE133
Figure 899974DEST_PATH_IMAGE134
制备方法与实施例1基本相同,区别在于,将化合物1-B替换为化合物6-b,收率54.2%,ESI-MS(m/z)(M+):理论值644.75,实测值644.08,元素分析结果(分子式C45H24D4N4O):理论值C,83.83; H, 5.00; N, 8.69; O, 2.48;实测值C,83.88; H, 5.02;N, 8.65; O, 2.45。
实施例7:
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化合物53的合成方法如下:
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Figure 52497DEST_PATH_IMAGE137
制备方法与实施例1基本相同,区别在于,分别将化合物1-B替换为化合物7-b,收率53.6%,ESI-MS(m/z)(M+):理论值 640.73,实测值 640.52,元素分析结果(分子式C45H28N4O):理论值C,84.35; H, 4.40; N, 8.74; O, 2.50;实测值C,84.31; H, 4.42;N, 8.80; O, 2.47。
实施例8:
Figure 307898DEST_PATH_IMAGE138
化合物77的合成方法如下:
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Figure 341768DEST_PATH_IMAGE140
Figure 775505DEST_PATH_IMAGE141
制备方法与实施例1基本相同,区别在于,将化合物1-B替换为化合物8-b,收率50.7%,ESI-MS(m/z)(M+):理论值569.66,实测值570.28,元素分析结果(分子式C39H19D5N4O):理论值C,82.23; H, 5.13; N, 9.84; O, 2.81;实测值C,82.28; H, 5.12;N, 9.82; O, 2.78。
实施例9:
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化合物133的合成方法如下:
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Figure 580409DEST_PATH_IMAGE144
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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-B替换为化合物9-b,收率55.4%,ESI-MS(m/z)(M+):理论值640.73,实测值640.32,元素分析结果(分子式C45H28N4O):理论值C, 84.35; H, 4.40; N, 8.74; O, 2.50;实测值C, 84.37; H, 4.42;N, 8.72; O, 2.49。
实施例10:
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化合物134的合成方法如下:
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Figure 890373DEST_PATH_IMAGE148
Figure 872105DEST_PATH_IMAGE149
制备方法与实施例1基本相同,区别在于,分别将化合物1-A、1-B替换为化合物10-a、10-b,收率51.0%,ESI-MS(m/z)(M+):理论值 645.76,实测值 646.03,元素分析结果(分子式C45H23D5N4O):理论值C,83.70; H, 5.15; N, 8.68; O, 2.48;实测值C,83.66; H,5.18; N, 8.64; O, 2.52。
实施例11:
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化合物148的合成方法如下:
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Figure 222260DEST_PATH_IMAGE153
制备方法与实施例1基本相同,区别在于,将化合物1-B替换为化合物11-b,收率48.87%,ESI-MS(m/z)(M+):理论值716.83,实测值716.62,元素分析结果(分子式C51H32N4O):理论值C, 85.45; H, 4.50; N, 7.82; O, 2.23;实测值C, 85.39; H, 4.48;N, 7.86; O, 2.27。
实施例12:
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化合物156的合成方法如下:
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Figure 882950DEST_PATH_IMAGE157
制备方法与实施例1基本相同,区别在于,将化合物1-A、1-B替换为化合物12-a、12-b,收率55.4%,ESI-MS(m/z)(M+):理论值721.86,实测值722.01,元素分析结果(分子式C51H27D5N4O):理论值C, 84.86; H, 5.17; N, 7.76; O, 2.22;实测值C, 84.87; H,5.15; N, 7.73; O, 2.25。
实施例13:
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化合物162的合成方法如下:
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Figure 922691DEST_PATH_IMAGE160
Figure 846654DEST_PATH_IMAGE161
制备方法与实施例1基本相同,区别在于,分别将化合物1-B替换为化合物13-b,收率51.0%,ESI-MS(m/z)(M+):理论值 716.83,实测值 716.24,元素分析结果(分子式C51H32N4O):理论值C,85.45; H, 4.50; N, 7.82; O, 2.23;实测值C,85.56; H, 4.40;N, 7.80; O, 2.24。
实施例14:
Figure 494673DEST_PATH_IMAGE162
化合物181的合成方法如下:
Figure 114397DEST_PATH_IMAGE163
Figure 215077DEST_PATH_IMAGE164
Figure 880414DEST_PATH_IMAGE165
制备方法与实施例1基本相同,区别在于,将化合物1-B替换为化合物14-b,收率53.1%,ESI-MS(m/z)(M+):理论值640.73,实测值640.59,元素分析结果(分子式C45H28N4O):理论值C, 84.35; H, 4.40; N, 8.74; O, 2.50;实测值C, 84.38; H, 4.39;N, 8.71; O, 2.52。
实施例15:
Figure 648519DEST_PATH_IMAGE166
化合物182的合成方法如下:
Figure 167706DEST_PATH_IMAGE167
Figure 83578DEST_PATH_IMAGE168
Figure 224710DEST_PATH_IMAGE169
制备方法与实施例1基本相同,区别在于,分别将化合物1-A、1-B替换为化合物15-a、15-b,收率51.5%,ESI-MS(m/z)(M+):理论值 645.76,实测值 646.12,元素分析结果(分子式C45H23D5N4O):理论值C,83.70; H, 5.15; N, 8.68; O, 2.48;实测值C,83.76; H,5.12; N, 8.64; O, 2.48。
实施例16:
Figure 850251DEST_PATH_IMAGE170
化合物201的合成方法如下:
Figure 480952DEST_PATH_IMAGE171
Figure 821804DEST_PATH_IMAGE172
制备方法与实施例1基本相同,区别在于,将化合物1-B替换为化合物16-b,收率50.7%,ESI-MS(m/z)(M+):理论值716.83,实测值716.37,元素分析结果(分子式C51H32N4O):理论值C, 85.45; H, 4.50; N, 7.82; O, 2.23;实测值C, 85.48; H, 4.52;N, 7.81; O, 2.19。
实施例17:
Figure 828943DEST_PATH_IMAGE173
化合物207的合成方法如下:
Figure 326568DEST_PATH_IMAGE174
Figure 393750DEST_PATH_IMAGE175
Figure 956319DEST_PATH_IMAGE176
制备方法与实施例1基本相同,区别在于,将化合物1-B替换为化合物17-b,收率51.2%,ESI-MS(m/z)(M+):理论值720.85,实测值720.46,元素分析结果(分子式C51H28D4N4O):理论值C, 84.98; H, 5.03; N, 7.77; O, 2.22;实测值C, 84.93; H,5.04; N, 7.79; O, 2.24。
实施例18:
Figure 439253DEST_PATH_IMAGE177
化合物245的合成方法如下:
Figure 36456DEST_PATH_IMAGE178
Figure 11890DEST_PATH_IMAGE179
Figure 61754DEST_PATH_IMAGE180
制备方法与实施例1基本相同,区别在于,将化合物1-B替换为化合物18-b,收率57.2%,ESI-MS(m/z)(M+):理论值716.83,实测值716.52,元素分析结果(分子式C51H32N4O):理论值C, 85.45; H,4.50; N, 7.82; O, 2.23;实测值C, 85.42; H,4.52;N, 7.84; O, 2.22。
实施例19:
Figure 410696DEST_PATH_IMAGE181
化合物273的合成方法如下:
Figure 921793DEST_PATH_IMAGE182
Figure 330778DEST_PATH_IMAGE183
Figure 930255DEST_PATH_IMAGE184
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19-a,收率51.5%,ESI-MS(m/z)(M+):理论值580.70,实测值580.33,元素分析结果(分子式C39H24N4S):理论值C, 80.66; H, 4.17; N, 9.65; S, 5.52;实测值C, 80.58; H, 4.22;N, 9.70; S, 5.50。
实施例20:
Figure 882555DEST_PATH_IMAGE185
化合物278的合成方法如下:
Figure 188772DEST_PATH_IMAGE186
Figure 768658DEST_PATH_IMAGE187
Figure 793114DEST_PATH_IMAGE188
制备方法与实施例1基本相同,区别在于,分别将化合物1-B替换为化合物20-b,收率54.2%,ESI-MS(m/z)(M+):理论值 645.76,实测值646.13,元素分析结果(分子式C45H23D5N4O):理论值C,83.70; H, 5.15; N,8.68; O, 2.48;实测值C, 83.66; H,5.17;N, 8.66; O, 2.51。
材料性质测试:
测试本发明化合物1、2、3、21、22、41、53、77、133、134、148、156、162、181、182、201、207、245、273、278的热失重温度Td和熔点Tm,测试结果如下表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,熔点Tm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 480929DEST_PATH_IMAGE189
由上述数据可知,本发明所合成的化合物的热稳定性优良,说明符合本发明结构通式的化合物都具有优良的热稳定性,可以满足有机电致发光材料使用的要求。
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10nm掺杂有5% HAT-CN的HT-1,形成空穴注入层(HIL);
在空穴注入层(HIL)上方蒸镀100nm的HT-1形成第一空穴传输层(HTL);
在第一空穴传输层(HTL)上方真空蒸镀GP,形成厚度为30nm的第二空穴传输层(GPL);
将本发明设计的化合物1与G1按照5:5的质量比例作为绿色主体材料进行共同蒸镀,GD-1作为掺杂材料(GD-1用量为GH-1与G1总质量的8%)蒸镀在第二空穴传输层(GPL)上形成厚度为30nm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与LiQ按照5:5的比例进行共同蒸镀到空穴阻挡层(HBL)上得到厚度为30nm的电子传输层(ETL);
将镁(Mg)和银(Ag)以9:1的比例混合蒸镀到电子传输层(ETL)上方,形成厚度为50nm的电子注入层(EIL);
此后将银(Ag)蒸镀到电子注入层上方,形成厚度为100nm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 330122DEST_PATH_IMAGE191
Figure 841875DEST_PATH_IMAGE192
Figure 70731DEST_PATH_IMAGE193
Figure 354469DEST_PATH_IMAGE194
Figure 276158DEST_PATH_IMAGE195
Figure 9627DEST_PATH_IMAGE196
Figure 307754DEST_PATH_IMAGE197
Figure 440139DEST_PATH_IMAGE198
Figure 532729DEST_PATH_IMAGE199
Figure 753495DEST_PATH_IMAGE200
Figure 261836DEST_PATH_IMAGE201
Figure 520167DEST_PATH_IMAGE202
应用例2-20
分别以本发明实施例2-20中的化合物2、3、21、22、41、53、77、133、134、148、156、162、181、182、201、207、245、273、278作为绿光主体材料,其他部分与应用例1一致,据此制作出应用例2-20的有机电致发光器件。
对照例1-4:
与应用例1的区别在于,分别用CN110540536A中的GH-1、GH-2、GH-3、GH-4代替化合物1作为绿光主体材料,其余与应用例1相同。
上述应用例制造的有机电致发光器件及对照例制造的有机电致发光器件的特性是在电流密度为10mA/cm2的条件下测定的,结果如表2所示。
表2:
Figure 783658DEST_PATH_IMAGE203
由如上表2可知,本发明化合物应用于有机电致发光器件中,在相同电流密度下,发光效率得到了较大幅度的提升,器件的启动电压有所下降,器件的功耗相对降低,使得器件的寿命相应提高。
分别将对照例1-4、应用例1-20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 491720DEST_PATH_IMAGE204
由上表3可知,将本发明化合物应用于有机电致发光器件中,在相同电流密度下,使用寿命得到较大程度提升,具有广阔的应用前景。

Claims (7)

1.一种化合物,其特征在于,其为以下结构中的任意一种:
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2.一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中所述的化合物。
3.如权利要求2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权利要求1中所述的化合物。
4.如权利要求3所述的有机电致发光器件,其特征在于,所述发光层中含有如权利要求1中所述的化合物。
5.如权利要求4所述的有机电致发光器件,其特征在于,所述发光层中还含有以下化合物G1-G48中的至少一种:
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6.一种电子显示设备,其特征在于,含有如权利要求4所述的有机电致发光器件。
7.一种OLED照明设备,其特征在于,含有如权利要求4所述的有机电致发光器件。
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