CN113528122A - 一种二元组合物、制剂、有机发光器件及显示或照明装置 - Google Patents

一种二元组合物、制剂、有机发光器件及显示或照明装置 Download PDF

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CN113528122A
CN113528122A CN202111077553.3A CN202111077553A CN113528122A CN 113528122 A CN113528122 A CN 113528122A CN 202111077553 A CN202111077553 A CN 202111077553A CN 113528122 A CN113528122 A CN 113528122A
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CN113528122B (zh
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王子兴
张迪
王朋超
吴空物
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Zhejiang Huadisplay Optoelectronics Co Ltd
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Abstract

一种二元组合物以及包含其的制剂、有机发光器件及显示或照明装置，化学式(I)作为第一化合物，化学式(II)作为第二化合物：
Figure DEST_PATH_IMAGE002

Description

一种二元组合物、制剂、有机发光器件及显示或照明装置
技术领域
本发明涉及一种二元组合物，尤其涉及一种二元组合物、制剂、有机发光器件及显示或照明装置，属于有机半导体领域。
背景技术
随着多媒体技术的发展及信息化要求的提高，对面板显示器性能的要求越来越高。其中有机发光器件（例如OLED）具有自主发光、低电压直流驱动、全固化、视角宽、颜色丰富等一系列的优点，在显示器和照明中的潜在应用而引起广泛注意，具有一定的应用价值。OLED发光的机理是在外加电场作用下，电子和空穴分别从正负两极注入后在有机材料中迁移、复合并衰减而产生发光。OLED的典型结构包括阴极层、阳极层、电子注入层、电子传输层、空穴阻挡层、空穴传输层、空穴注入层和有机发光层中的一种或多种功能层。
有机发光器件(例如OLED)具有独特的发光特性和低电压驱动能力。与显示器件液晶显示器(LCD)相比，OLED具有更好的可视角度、对比度和不必要的背光，在功耗方面具有优势。然而，目前有机发光器件的主要问题是需要提升发光效率、延长使用寿命及降低操作电压。
因此，有必要开发一种新颖的发光层主体材料，用于提升OLED器件的发光效率、延长使用寿命及降低操作电压。
发明内容
为了克服现有技术中存在的上述缺陷，本发明的目的是提供了一种新颖的二元组合物以及它们在显示和照明中应用，且将该二元组合物用于制作有机发光器件（红光器件）时，提高了该有机发光器件的发光效率、延长其使用寿命及降低其操作电压。
为了实现本发明的目的，本发明的技术方案如下：
本发明提供了一种二元组合物，其包括下列式(I)所示的第一化合物和式(II)所示的第二化合物，
Figure 602444DEST_PATH_IMAGE001
其中，A、B和Ar各自独立地选自取代或未取代的C6~C30芳基或取代或未取代的C3~C30的杂芳基；
Figure 457267DEST_PATH_IMAGE002
其中，X为O或S原子；
Y为单键、取代或未取代的C6~C30芳基或取代或未取代的C3~C30杂芳基；
Ar1和Ar2各自独立地选自取代或未取代的C6~C30芳基或取代或未取代的C3~C30杂芳基。
优选地，式（I）选自以下结构中任一者：
Figure DEST_PATH_IMAGE003
Figure 351186DEST_PATH_IMAGE004
其中，Ar和Ar1各自独立地选自取代或未取代的C6~C30芳基或取代或未取代的C3~C30杂芳基；
R为氢原子、氘原子、卤素原子、取代或未取代的C1~C30的烷基、取代或未取代的C6~C30的芳基或取代或未取代的C3~C30的杂芳基；n为0到8的整数。
优选地，式（II）中的
Figure DEST_PATH_IMAGE005
为以下结构中任一者：
Figure 526821DEST_PATH_IMAGE006
Figure 544456DEST_PATH_IMAGE007
Figure DEST_PATH_IMAGE008
Figure 242285DEST_PATH_IMAGE009
Figure 679957DEST_PATH_IMAGE010
Figure 816540DEST_PATH_IMAGE011
更优选地，式(I)和式(II)中的Ar、Ar1和Ar2各自独立地选自以下结构中任一者：
Figure 423102DEST_PATH_IMAGE012
Figure 619728DEST_PATH_IMAGE013
Figure 810276DEST_PATH_IMAGE014
Figure 484971DEST_PATH_IMAGE015
Figure 946039DEST_PATH_IMAGE016
Figure 47987DEST_PATH_IMAGE017
Figure 719972DEST_PATH_IMAGE018
Figure 198358DEST_PATH_IMAGE019
Figure 513932DEST_PATH_IMAGE020
Figure 786782DEST_PATH_IMAGE021
Figure 951922DEST_PATH_IMAGE022
Figure 765157DEST_PATH_IMAGE023
Figure 200818DEST_PATH_IMAGE024
Figure 910148DEST_PATH_IMAGE025
Figure 297004DEST_PATH_IMAGE026
Figure 117193DEST_PATH_IMAGE027
Figure 407360DEST_PATH_IMAGE028
Figure 287591DEST_PATH_IMAGE029
Figure 161744DEST_PATH_IMAGE030
Figure 520044DEST_PATH_IMAGE031
Figure 930297DEST_PATH_IMAGE032
Figure 981429DEST_PATH_IMAGE033
Figure 83159DEST_PATH_IMAGE034
Figure 917253DEST_PATH_IMAGE035
Figure 916434DEST_PATH_IMAGE036
Figure 637003DEST_PATH_IMAGE037
Figure 987212DEST_PATH_IMAGE038
Figure 952894DEST_PATH_IMAGE039
Figure 72160DEST_PATH_IMAGE040
Figure 698051DEST_PATH_IMAGE041
Figure 535557DEST_PATH_IMAGE042
Figure 39351DEST_PATH_IMAGE043
Figure 278702DEST_PATH_IMAGE044
Figure 75495DEST_PATH_IMAGE045
Figure 400297DEST_PATH_IMAGE046
Figure 707782DEST_PATH_IMAGE047
Figure 270481DEST_PATH_IMAGE048
Figure 521332DEST_PATH_IMAGE049
*表示与相邻原子相连的位置
更优选地，所述第一化合物为以下结构中任一者：
Figure 67851DEST_PATH_IMAGE050
Figure 179027DEST_PATH_IMAGE051
Figure 127391DEST_PATH_IMAGE052
Figure 797145DEST_PATH_IMAGE053
Figure 565380DEST_PATH_IMAGE054
Figure 214668DEST_PATH_IMAGE055
Figure 17538DEST_PATH_IMAGE056
Figure 592614DEST_PATH_IMAGE057
Figure 113725DEST_PATH_IMAGE058
Figure 301124DEST_PATH_IMAGE059
Figure 224081DEST_PATH_IMAGE060
Figure 766795DEST_PATH_IMAGE061
Figure 775203DEST_PATH_IMAGE062
Figure 766292DEST_PATH_IMAGE063
Figure 543755DEST_PATH_IMAGE064
Figure 466493DEST_PATH_IMAGE065
Figure 696617DEST_PATH_IMAGE066
Figure 491398DEST_PATH_IMAGE067
Figure 326630DEST_PATH_IMAGE068
Figure 414409DEST_PATH_IMAGE069
Figure 397409DEST_PATH_IMAGE070
Figure 730301DEST_PATH_IMAGE071
Figure 482356DEST_PATH_IMAGE072
Figure 741037DEST_PATH_IMAGE073
Figure 742491DEST_PATH_IMAGE074
Figure 879075DEST_PATH_IMAGE075
Figure 220057DEST_PATH_IMAGE076
Figure 118481DEST_PATH_IMAGE077
Figure 810493DEST_PATH_IMAGE078
Figure 485188DEST_PATH_IMAGE079
Figure 477415DEST_PATH_IMAGE080
Figure 337618DEST_PATH_IMAGE081
Figure 251348DEST_PATH_IMAGE082
Figure 995313DEST_PATH_IMAGE083
Figure 310888DEST_PATH_IMAGE084
Figure 347851DEST_PATH_IMAGE085
Figure 748877DEST_PATH_IMAGE086
Figure DEST_PATH_IMAGE087
Figure 703058DEST_PATH_IMAGE088
Figure DEST_PATH_IMAGE089
Figure 840516DEST_PATH_IMAGE090
Figure DEST_PATH_IMAGE091
Figure 221949DEST_PATH_IMAGE092
Figure DEST_PATH_IMAGE093
Figure 812069DEST_PATH_IMAGE094
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更优选地，所述第二化合物为以下结构中任一者：
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。
本发明还提供了一种制剂，其包含该二元组合物和至少一种溶剂，该溶剂可以是本领域技术人员公知的不饱和烃溶剂（例如甲苯、二甲苯、均三甲苯、四氢化萘、十氢萘、双环己烷、正丁基苯、仲丁基苯、叔丁基苯等）、卤化饱和烃溶剂（例如四氯化碳、氯仿、二氯甲烷、二氯乙烷、氯丁烷、溴丁烷、氯戊烷、溴戊烷、氯己烷、溴己烷、氯环己烷、溴环己烷等）、卤化不饱和烃溶剂（例如氯苯、二氯苯、三氯苯等）、醚类溶剂（例如四氢呋喃、四氢吡喃等）或酯类溶剂（例如苯甲酸烷基酯等）。
本发明又提供了有机发光器件，其包括阴极层、阳极层和有机功能层，该有机功能层为空穴注入层、空穴传输层、发光层、电子传输层和电子注入层中至少一层，其中，该有机功能层包含该二元组合物或制剂。
优选地，该有机功能层为发光层，该发光层中还包含客体化合物，其中该客体化合物为荧光材料或磷光材料。
更优选地，该二元组合物与该掺杂剂的体积比为1：99至99：1。
更优选地，该二元组合物中该第一化合物和该第二化合物的体积比为2：8至8：2。
本发明进一步提供了显示或照明装置，其包括该有机发光器件。
具体实施方式
为了使本发明的目的、技术方案及优点更加清楚明白，以下结合具体实施例，对本发明进行进一步详细说明。应当理解，此处所描述的具体实施例仅仅用以解释本发明，并不用于限定本发明。
本发明的OLED器件包括空穴传输层，且空穴传输材料可以优选地选自本领域公知的材料，特别优选地选自以下结构，但并不代表本发明限于以下结构：
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本发明的有机发光器件中空穴传输层包含一种或多种p型掺杂剂。本发明优选的p型掺杂剂为以下结构中任一者，但并不代表本发明限于以下结构：
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Figure 254745DEST_PATH_IMAGE213
本发明的电子传输层可以选自化合物ET-1至化合物ET-13中至少一者，但并不代表本发明限于以下结构：
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电子传输层可以通过有机材料与一种或多种n型掺杂剂（如LiQ）共同形成。
本发明的二元组合物同样可以应用于照明的OLED、柔性OLED等。并且本发明的有机发光器件可以归类为顶发射、底发射或双面发射。
本发明提供了一种二元组合物，用它作为主体材料构筑有机发光器件，可以降低该器件的驱动电压，提高该器件的发光效率及延长该器件的使用寿命。
实施例
本发明不限于以下反应方案。下面通过反应方案和对比实例对本发明进行详细说明。
下列实施例中的中间体1至中间体8均通过本领域公知的方法制备得到。
实施例1
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在氮气保护下，将中间体1 (5g)、中间体2(4g)、Pd2(dba)3(0.4g)、P(t-Bu)3(0.19g)、NaOt-Bu(4.5g)和甲苯(200mL)加入烧瓶中回流搅拌过夜。反应完成后，分离有机层，用硫酸镁除湿，减压浓缩溶液。通过二氯甲烷过柱层析，THF重结晶得到化合物666(6.4g，收率：75%)。LC-MS: M/Z 实测539.1 (M+)，理论539.13。
实施例2
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在氮气保护下，将中间体3(5g)、中间体4(5.1g)、Pd2(dba)3(0.45g)、P(t-Bu)3(0.2g)、Naot-Bu(4.8g)和甲苯200 ml回流搅拌过夜。反应完成后，分离有机层，用硫酸镁干燥，减压浓缩溶液。通过二氯甲烷过柱层析，THF重结晶得到化合物667(6.6g，收率：70%)。LC-MS: M/Z 实测573.2 (M+)，理论573.17。
实施例3
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在氮气保护下，将中间体5(5g)、中间体6(5.2g)、Pd2(dba)3(0.3g)、x-Phos(0.23g)、K2CO3(5g)、二氧六环/水(3：1)200 ml加入烧瓶中回流搅拌过夜。反应完成后，分离有机层，用硫酸镁除湿，减压浓缩溶液。通过二氯甲烷过柱层析，THF重结晶得到化合物668(7.1g，收率：89%)。LC-MS: M/Z 实测671.2 (M+)，理论671.15。
实施例4
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在氮气保护下，将中间体7(5g)、中间体8 (4.4g)、Pd2(dba)3(0.35g)、x-Phos(0.25g)、K2CO3(5.4g)、二氧六环/水(3：1)200 ml加入烧瓶中回流搅拌过夜。反应完成后，分离有机层，用硫酸镁干燥，减压浓缩溶液。通过二氯甲烷过柱层析，THF重结晶得到化合物669(6.88g，收率：92%)。LC-MS: M/Z 实测575.2 (M+)，理论575.20。
化合物670-674通过以上类似的步骤反应得到：
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OLED器件实施例：
具体实施底发射OLED器件的结构为在含有ITO的玻璃上，空穴注入层（HIL）为HT-1:P-3 (95:5 v/v%)，厚度为10纳米；空穴传输层（HTL）为HT-1，厚度为100纳米；电子阻挡层（EBL）为HT-12，厚度为10纳米，发光层（EML）为[A:B或本发明的二元组合物]:RD-1 (97:3v/v%)，厚度为35纳米，电子传输层（ETL）为ET-11：LiQ (50:50 v/v%)，厚度为25纳米，然后蒸镀LiQ，厚度为1纳米，和Al，厚度为60纳米。其中，化合物A和B作为对比化合物。
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对比器件1-3和器件例1-19中的器件均是采用本领域公知的标准方法测定的。
依据上述器件实施例，OLED器件的电流效率、操作电压、寿命等特性显示在下表1所示。
表1
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附注：上述表格中的比例是指体积比。
从表1中可以看出，用本发明的二元组合物作为红光主体用于发光层，可以显著提升OLED器件的发光效率，延长使用寿命，同时不同程度地降低电压。
以上所述，仅为本发明较佳的具体实施方式，但本发明的保护范围并不局限于此，任何熟悉本技术领域的技术人员在本发明揭露的技术范围内，根据本发明的技术方案及其发明构思加以等同替换或改变，都应涵盖在本发明的保护范围之内。

Claims (12)

1.一种二元组合物，其包括下列式(I)所示的第一化合物和式(II)所示的第二化合物，
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其中，A、B和Ar各自独立地选自取代或未取代的C6~C30芳基或取代或未取代的C3~C30的杂芳基；
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其中，X为O或S原子；
Y为单键、取代或未取代的C6~C30芳基或取代或未取代的C3~C30的杂芳基；
Ar1和Ar2各自独立地选自取代或未取代的C6~C30芳基或取代或未取代的C3~C30的杂芳基。
2.根据权利要求1所述的二元组合物，其中式（I）选自以下结构中的任一者：
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其中，Ar和Ar1各自独立地选自取代或未取代的C6~C30芳基或取代或未取代的C3~C30杂芳基；
R为氢原子、氘原子、卤素原子、取代或未取代的C1~C30烷基，取代或未取代的C6~C30芳基或取代或未取代的C3~C30的杂芳基；
n为0到8的整数。
3.根据权利要求1所述的二元组合物，其中式（II）中的
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为以下结构中任一者：
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。
4.根据权利要求1-3中任一项所述的二元组合物，其中式(I)和式(II)中的Ar、Ar1和Ar2各自独立地选自以下结构中任一者：
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*表示与相邻原子相连的位置。
5.根据权利要求1-3中任一项所述的二元组合物，其中所述第一化合物为以下结构中任一者：
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。
6.根据权利要求1-3中任一项所述的二元组合物，其中所述第二化合物为以下结构中任一者：
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。
7.制剂，其包含权利要求1-3中任一项所述的二元组合物和至少一种溶剂，其中所述溶剂为不饱和烃溶剂、饱和烃溶剂、醚类溶剂或酯类溶剂。
8.有机发光器件，其包括阴极层、阳极层和有机功能层，所述有机功能层为空穴注入层、空穴传输层、发光层、电子传输层和电子注入层中至少一层，其中所述有机功能层包含权利要求1-3中任一项所述的二元组合物。
9.根据权利要求8所述的有机发光器件，其中，所述有机功能层为发光层，所述发光层中还包含掺杂剂，其中所述掺杂剂为荧光材料或磷光材料。
10.根据权利要求9所述的有机发光器件，其中所述二元组合物与所述掺杂剂的体积比为1：99至99：1。
11.根据权利要求10所述的有机发光器件，其中所述二元组合物中所述第一化合物和所述第二化合物的体积比为2：8至8：2。
12.显示或照明装置，其包括根据权利要求8所述的有机发光器件。
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