CN107400086A - 一种有机化合物及使用该化合物制备的有机电致发光器件 - Google Patents

一种有机化合物及使用该化合物制备的有机电致发光器件 Download PDF

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CN107400086A
CN107400086A CN201710621321.7A CN201710621321A CN107400086A CN 107400086 A CN107400086 A CN 107400086A CN 201710621321 A CN201710621321 A CN 201710621321A CN 107400086 A CN107400086 A CN 107400086A
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蔡辉
董秀芹
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Changchun Haipurunsi Technology Co Ltd
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Abstract

本发明提供一种有机化合物及使用该化合物的有机电致发光器件，属于有机光电材料技术领域。本发明通过在主体结构上连接不同的配体，调节化合物的分子量、π共轭程度及亲电性，从而使化合物的玻璃化转变温度提高，电荷迁移定向性增强，进而提高材料的稳定性及电荷传输能力。该化合物可用于制备有机电致发光器件，尤其可作为有机电致发光器件中的电子传输层材料，可有效解决有机电致发光器件中载流子不平衡的问题，具有发光效率高，寿命长的优点。

Description

一种有机化合物及使用该化合物制备的有机电致发光器件
技术领域
本发明涉及有机光电材料技术领域，尤其涉及一种有机化合物及使用该化合物制备的有机电致发光器件。
背景技术
随着科学技术的发展，有机电致发光(简称OLED)技术及器件取得了长足的进步，在平板显示技术中，OLED凭借其自发光、视角宽、全固化、全彩化、反应速度快、高亮度、低驱动电压、厚度薄、质量轻、可制作大尺寸与弯曲面板、成本低、制备简单等优势，在显示器市场得到了越来越多的应用。因此OLED技术是平面显示器未来发展的趋势，具有广阔的应用前景。
从有机电致发光器件的结构角度划分，有机电致发光材料大致上可以分为三种类型：电极材料及电极修饰材料、载流子传输材料、发光材料。载流子传输材料根据载流子的不同又可分为电子传输材料、空穴传输材料。其中电子传输材料的主要特点有：1、电子亲合能较高，利于电子从阴极注入；2、电子迁移率高，利于电子的传输；3、电离能大，对空穴起到阻挡的作用，避免空穴和电子在电子传输材料区域的复合；4、具有较高的激发能级，高于发光层能级，有效避免发光层激发态的能量传递，有效避免激子在电子传输层的复合；5、成膜性及稳定性好。
随着市场对OLED器件要求的进一步提高，更高发光效率、更长寿命、更低成本成为OLED器件发展的趋势，由于在有机光电材料中空穴传输性能优于电子，电子迁移率比空穴迁移率慢，空穴和电子在发光层内的复合区域会选择性的偏向一边，导致其发光效率和光色的改变，严重的甚至会引起三重态之间的能量淬灭，导致高亮度下的效率滚降严重，因此载流子平衡注入是提高OLED器件发光效率的关键因素。
发明内容
本发明的目的是提供一种有机化合物及使用该化合物的有机电致发光器件，本发明提供的有机化合物成膜型及稳定性好，有较高的电子亲和能，利于电子的定向迁移，制备方法简单，使用该化合物制备的有机电致发光器件具有良好的发光效率及寿命表现。
本发明提供了一种有机化合物，其分子结构通式如化学式1所示：
[化学式1]
其中，R1、R2独立的选自氢、卤素、氰基、取代或未取代的C1～C30的烷基、取代或未取代的C2～C30的烯烃基、取代或未取代的C2～C30的炔烃基、取代或非取代C6～C60的芳基、取代或未取代的C3～C60的杂环基、取代或未取代的C10-C60稠环基中的一种；X1～X4独立的选自C或N；Y选自O或S。
优选的，R1、R2独立的选自氢、氟、Cl、Br、I、氰基、取代或未取代的C1～C10的烷基、取代或未取代的C2～C10的烯烃基、取代或未取代的C2～C10的炔烃基、取代或非取代C6～C24芳基、取代或未取代的C3～C14的杂环基、取代或未取代的C10-C18稠环基中的一种。
优选的，X1～X4中有一个为N，或全为C。
优选的，本发明所述的有机化合物具有化学式2-化学式6所示的结构：
其中，R1、R2独立的选自氢、氟、Cl、Br、I、氰基、取代或未取代的C1～C10的烷基、取代或未取代的C2～C10的烯烃基、取代或未取代的C2～C10的炔烃基、取代或非取代C6～C24芳基、取代或未取代的C3～C14的杂环基、取代或未取代的C10-C18稠环基中的一种；Y选自O或S。
优选的，Y为O。
优选的，本发明所述的有机化合物选自如下所示化学结构中的任意一种：
本发明还提供了一种有机电致发光器件，所述有机电致发光器件包括阴极、阳极和置于所述两电极之间的一个或多个有机物层，所述的有机物层含有本发明所述的有机化合物。
优选的，所述的有机物层包括电子传输层，电子传输层中含有本发明所述的有机化合物。
本发明的有益效果：
本发明提供一种有机化合物及使用该化合物的有机电致发光器件。本发明通过在主体结构上连接不同的配体，调节化合物的分子量、π共轭程度及亲电性，从而使化合物的玻璃化转变温度提高，电荷迁移定向性增强，进而提高材料的稳定性及电荷传输能力。合成方法简单，容易操作。该化合物可用于制备有机电致发光器件，尤其可作为有机电致发光器件中的电子传输层材料，可有效解决有机电致发光器件中载流子不平衡的问题，具有发光效率高，寿命长的优点。
具体实施方式：
下面将结合本发明实施例的技术方案进行清楚、完整地描述，显然，所描述的实施例仅仅是本发明一部分实施例，而不是全部的实施例。基于本发明中的实施例，本领域技术人员在没有做出创造性劳动前提下所获得的所有其他实施例，都属于本发明的保护范围。
本发明提供了一种有机化合物，其分子结构通式如化学式1所示：
[化学式1]
其中，R1、R2独立的选自氢、卤素、氰基、取代或未取代的C1～C30的烷基、取代或未取代的C2～C30的烯烃基、取代或未取代的C2～C30的炔烃基、取代或非取代C6～C60的芳基、取代或未取代的C3～C60的杂环基、取代或未取代的C10-C60稠环基中的一种；X1～X4独立的选自C或N；Y选自O或S。
优选的，R1、R2独立的选自氢、氟、Cl、Br、I、氰基、取代或未取代的C1～C10的烷基、取代或未取代的C2～C10的烯烃基、取代或未取代的C2～C10的炔烃基、取代或非取代C6～C24芳基、取代或未取代的C3～C14的杂环基、取代或未取代的C10-C18稠环基中的一种。
优选的，X1～X4中有一个为N，或全为C。
按照本发明，所述取代的烷基、取代的烯烃基、取代的炔烃基、取代的芳基、取代的杂环基、取代的稠环基中，所述取代基可选自氘、氰基、卤素、硝基、C1-C10烷基、C6-C24芳基、C3-C20的杂环基。所述杂环基中杂原子优选为N、O或S。
优选的，本发明所述的有机化合物具有化学式2-化学式6所示的结构：
其中，R1、R2独立的选自氢、氟、Cl、Br、I、氰基、取代或未取代的C1～C10的烷基、取代或未取代的C2～C10的烯烃基、取代或未取代的C2～C10的炔烃基、取代或非取代C6～C24芳基、取代或未取代的C3～C14的杂环基、取代或未取代的C10-C18稠环基中的一种；Y选自O或S。
优选的，Y选自O。
作为举例，没有特别限定，本发明所述的有机化合物选自如下所示化学结构中的任意一种：
本发明所述有机化合物的合成方法，合成路线如下：
其中，R1、R2独立的选自氢、卤素、氰基、取代或未取代的C1～C30的烷基、取代或未取代的C2～C30的烯烃基、取代或未取代的C2～C30的炔烃基、取代或非取代C6～C60的芳基、取代或未取代的C3～C60的杂环基、取代或未取代的C10-C60稠环基中的一种；X1～X4独立的选自C或N；Y选自O或S。
按照本发明，中间体A所示的化合物按照如下所示方法制备得到：
在氮气保护，K2Cr2O7作为氧化剂，通过氧化反应得到中间体A。
按照本发明，中间体B所示的化合物按照如下所示方法制备得到：
在氮气保护下，中间体A在格式试剂作用下生成中间体B。
按照本发明，目标产物1所示的化合物按照如下所示方法制备得到：
在氮气保护下，中间体B在酸性条件下，在格式试剂作用下生成目标化合物。
按照本发明，目标产物2所示的化合物按照如下所示方法制备得到：
在氮气保护下，目标产物1在劳森试剂作用下生成目标化合物2。
本发明对上述反应没有特殊的限制，采用本领域技术人员所熟知的常规反应即可。
本发明还提供了一种有机电致发光器件，所述有机电致发光器件包括阴极、阳极和置于所述两电极之间的一个或多个有机物层，所述的有机物层含有本发明所述的有机化合物。优选的，所述的有机物层包括电子传输层，电子传输层中含有本发明所述的有机化合物。
本发明所述的的器件结构优选具体为：3Ph-anthracene/Ir(tpy)3用作发光层物质，本发明所述的有机化合物用作电子传输层，用以制造有以下相同构造的有机电致发光器件：ITO/2-TNATA(50nm)/α-NPD(30nm)/3Ph-anthracene(2,9,10-三苯基蒽)：Ir(tpy)3(30nm)/本发明所述的有机化合物(30nm)/LiF(0.5nm)/Al(60nm)。
本发明所述有机电致发光器件可广泛应用于面板显示、照明OLED、柔性OLED、电子纸、有机感光体或有机薄膜晶体管领域。
[实施例1]化合物4的制备
*中间体4-1的合成
氮气保护下，反应器中加入H2SO4/H2O(20mL/60mL)的混合溶液，加入7,8-苯并喹啉(1.79g，10mmol)，控制反应温度90～95℃，搅拌反应4h，后加入K2Cr2O7(10.69g，36.34mmol)，继续反应1.5h，反应完成后加入200mL蒸馏水析出沉淀、过滤、水洗，将析出物中加入60mL乙醇、30mL的Na2S2O5饱和溶液，持续搅拌15nin，加入150mL蒸馏水到反应混合物中，将溶解产物过滤，滤液中加入50mL的Na2CO3溶液析出沉淀，沉淀经过滤、水洗、干燥得到粗产物，再经冰醋酸重结晶得到中间体4-1(1.57g,75％)。
*中间体4-2的合成
氮气保护下，反应器中加入中间体4-1(2.09g，10mmol)、60mL苯、15mL苯甲醚，后缓慢滴加由溴蒽(3.08g，11mmol)/镁(0.26g，10.5mmol)/20mL苯甲醚制备的格式试剂，回流3.5h，后冷却，反应混合物中加入蒸馏水、稀硫酸溶解，后用苯萃取，减压蒸馏，干燥得到粗产物，再经、氯仿、乙醇重结晶得到中间体4-2(2.08g，55％)。
*化合物4的合成
氮气保护下，反应器中加入中间体4-2(3.78g，10mmol)，60mL苯，缓慢加入由碘甲烷(5.81g，35mmol)/镁(2.8g，35mmol)/10mL苯甲醚制备的格式试剂，搅拌反应10h，倒入等体积的碎冰，6M的硫酸，用氯仿萃取，蒸干得到粗产物，粗产物溶解在醋酸中，加入4.5mL的浓度为48％的HBr溶液，回流反应20min,，后用NaOH中和，用苯、氯仿萃取得到粗产物，后干燥，升华提纯得到化合物4(2.6g，67.5％)。
[实施例2]化合物39的制备
按照化合物4的制备方法得到化合物39(2.08g，67％)。
[实施例3]化合物76的制备
按照化合物4的制备方法得到化合物76(2.26g，60％)。
[实施例4]化合物103的制备
按照化合物4的制备方法得到化合物103(1.82g，63％)。
[实施例5]化合物116的制备
按照化合物4的制备方法得到化合物116(3.05g，55％)。
【表1】
实施例 FD-MS
实施例1 m/z＝385.20(C28H19NO＝385.15)
实施例2 m/z＝311.18(C20H13N3O3＝311.11)
实施例3 m/z＝376.22(C25H16N2O2＝376.12)
实施例4 m/z＝288.18(C17H12N4O＝288.10)
实施例5 m/z＝555.13(C38H27N4O＝555.22)
[对比实施例1]器件制备实施例：
将ITO玻璃基板放在蒸馏水中清洗2次，超声波洗涤30分钟，用蒸馏水反复清洗2次，超声波洗涤10分钟，蒸馏水清洗结束后，异丙醇、丙酮、甲醇等溶剂按顺序超声波洗涤以后干燥，转移到等离子体清洗机里，将上述基板洗涤5分钟，送到蒸镀机里。
在已经准备好的ITO透明电极上逐层蒸镀空穴注入层2-TNATA/50nm、蒸镀空穴传输层α-NPD/30nm、蒸镀主体3Ph-anthracene(2,9,10-三苯基蒽)：掺杂Ir(tpy)3 10％混合/30nm、然后蒸镀电子传输层TPBi/30nm、阴极LiF/0.5nm、Al/60nm。
[实施例6]器件制备实施例：
将对比实施例1中的TPBi换成实施例1的化合物4。
[实施例7]器件制备实施例：
将对比实施例1中的TPBi换成实施例2的化合物39。
[实施例8]器件制备实施例：
将对比实施例1中的TPBi换成实施例3的化合物76。
[实施例9]器件制备实施例：
将对比实施例1中的TPBi换成实施例4的化合物103。
[实施例10]器件制备实施例：
将对比实施例1中的TPBi换成实施例5的化合物106。
本发明实施例6-10以及对比实施例1制备的发光器件的发光特性测试结果如表2所示。
[表2]
以上结果表明，本发明的有机化合物应用于有机电致发光器件中，尤其是作为电子传输层，其有机电致发光器件的发光效率有显著提高，本发明的有机化合物是性能良好的有机发光材料。
应当指出，本发明用个别实施方案进行了特别描述，但在不脱离本发明原理的前提下，本领域普通技术人可对本发明进行各种形式或细节上的改进，这些改进也落入本发明的保护范围内。

Claims (8)

1.一种有机化合物，其特征在于，其分子结构通式如化学式1所示：
[化学式1]
其中，R1、R2独立的选自氢、卤素、氰基、取代或未取代的C1～C30的烷基、取代或未取代的C2～C30的烯烃基、取代或未取代的C2～C30的炔烃基、取代或非取代C6～C60的芳基、取代或未取代的C3～C60的杂环基、取代或未取代的C10-C60稠环基中的一种；X1～X4独立的选自C或N；Y选自O或S。
2.根据权利要求1所述的一种有机化合物，其特征在于，R1、R2独立的选自氢、氟、Cl、Br、I、氰基、取代或未取代的C1～C10的烷基、取代或未取代的C2～C10的烯烃基、取代或未取代的C2～C10的炔烃基、取代或非取代C6～C24芳基、取代或未取代的C3～C14的杂环基、取代或未取代的C10-C18稠环基中的一种。
3.根据权利要求1所述的一种有机化合物，其特征在于，X1～X4中有一个为N，或全为C。
4.根据权利要求1所述的一种有机化合物，其特征在于，如下面化学式2-化学式6中的任意一种结构表示：
其中，R1、R2独立的选自氢、氟、Cl、Br、I、氰基、取代或未取代的C1～C10的烷基、取代或未取代的C2～C10的烯烃基、取代或未取代的C2～C10的炔烃基、取代或非取代C6～C24芳基、取代或未取代的C3～C14的杂环基、取代或未取代的C10-C18稠环基中的一种；Y选自O或S。
5.根据权利要求1所述的一种有机化合物，其特征在于，Y为O。
6.根据权利要求1所述的一种有机化合物，其特征在于，选自如下所示化学结构中的任意一种：
7.一种有机电致发光器件，其特征在于，所述有机电致发光器件包括阴极、阳极和置于所述两电极之间的一个或多个有机物层，所述的有机物层含有权利要求1～6任一项所述的有机化合物。
8.根据权利要求7中所述的一种有机电致发光器件，其特征在于，所述有机物层包括电子传输层，电子传输层中含有权利要求1～6任一项所述的有机化合物。
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Cited By (1)

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WO2019160315A1 (ko) * 2018-02-13 2019-08-22 주식회사 엘지화학 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
CN111225905A (zh) * 2018-02-13 2020-06-02 株式会社Lg化学 杂环化合物及包含其的有机发光器件
CN111225905B (zh) * 2018-02-13 2023-09-05 株式会社Lg化学 杂环化合物及包含其的有机发光器件

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