CN111303012A - 一种茚并荧蒽化合物及应用 - Google Patents

一种茚并荧蒽化合物及应用 Download PDF

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CN111303012A
CN111303012A CN202010239758.6A CN202010239758A CN111303012A CN 111303012 A CN111303012 A CN 111303012A CN 202010239758 A CN202010239758 A CN 202010239758A CN 111303012 A CN111303012 A CN 111303012A
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indeno
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梁现丽
段陆萌
范洪涛
李仲庆
杭德余
李继响
班全志
陈婷
曹占广
刘阳
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Beijing Yanhua Jilian Optoelectronic Technology Co ltd
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Abstract

本发明涉及有机电致发光显示技术领域，具体公开了一种新型茚并荧蒽结构的有机材料，同时还公开了其在有机电致发光器件中的应用。本发明提供的新型茚并荧蒽结构化合物如通式(Ⅰ)所示，以茚并荧蒽结构化合物为母核，该类材料具有高的空穴迁移率，较好的薄膜稳定性和适合的分子能级，同时具有良好的热稳定性，可以被应用在有机电致发光领域，作为空穴传输材料使用。本发明提供的该新型茚并荧蒽结构化合物能够很好地应用于OLED器件中，器件表现具有驱动电压低、发光效率高的优点。

Description

一种茚并荧蒽化合物及应用
技术领域
本发明涉及有机电致发光显示技术领域，特别是涉及一种新型茚并荧蒽结构的有机材料，同时还涉及其在有机电致发光器件中的应用。
背景技术
有机电致发光(OLED)材料在信息显示材料、有机光电子材料等领域中的应用具有极大的研究价值和美好的应用前景。随着多媒体信息技术的发展，对平板显示器件性能的要求越来越高。目前主要的显示技术有等离子显示器件、场发射显示器件和有机电致发光显示器件(OLED)。其中，OLED具有自身发光、轻薄省电、全固化、视角宽、颜色丰富等一系列优点，与液晶显示器件相比，OLED不需要背光源，视角更宽，功耗低，其响应速度是液晶显示器件的1000倍，因此，OLED具有更广阔的应用前景。
目前，在显示与照明领域的有机电致发光器件结构中，一般都采用蓝色荧光搭配红、绿色磷光材料使用。常见电致发光器件的发光层主要采用主客体掺杂方式来调节其光色、亮度与效率，进而改善器件性能。
目前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。但是现有的有机电致发光材料在发光性能方面还有很大改进余地，业界亟需开发新的有机电致发光材料。
发明内容
本发明的目的在于开发一种稳定高效的有机空穴传输材料，应用于OLED器件中，可以降低驱动电压，提高器件发光效率。
具体而言，本发明提供一种茚并荧蒽化合物，具有如通式(Ⅰ)所示的结构：
Figure BDA0002432162580000011
所述通式(I)中，R1～R8中至少有一个基团为含五元杂环的芳香基团。所述含五元杂环的芳香基团通过C原子与通式(Ⅰ)所示的母核相连。
所述R1～R8中，至少有一个基团为取代或未被取代的含五元杂环的芳香基团，其余基团各自独立地代表氢原子、卤素、直链或含支链的烷基、环烷基、氨基、烷胺基、取代或未被取代的含有苯环和/或芳杂环的芳香基团；
所述取代或未被取代的含五元杂环的芳香基团通过C原子与通式(Ⅰ)所示的母核相连；
X、Y各自独立地选自氢原子、卤素、直链或含支链的烷基、环烷基、氨基、烷胺基、芳胺基、取代或未被取代的含有苯环和/或芳杂环的芳香基团；
m、n各自独立地代表0、1或者2。
所述取代或未被取代的含五元杂环的芳香基团含有至少一个五元杂环，优选为含有一个、两个或三个五元杂环。所述五元杂环含有至少一个杂原子，优选为含有一个、两个或三个杂原子。所述杂原子任意地选自N原子、S原子和O原子；当所述取代或未被取代的含五元杂环的芳香基团中含有多个杂原子时，各个杂原子可以彼此相同，可以部分相同，也可以各不相同。
作为本发明的优选方案，所述取代或未被取代的含五元杂环的芳香基团选自：取代或未被取代的咔唑基、取代或未被取代的吲哚并吲哚基、取代或未被取代的噻吩基、取代或未被取代的苯并噻吩基、取代或未被取代的苯并呋喃基。
作为本发明的优选方案，所述取代的含五元杂环的芳香基团中，取代采用的取代基可以任意选自：苯基、萘基、联苯基、苯并基、萘并基、菲并基、吲哚并基(如N-苯代吲哚并基)、苯并噻吩并基、苯并呋喃并基。取代基的个数选自1～5、优选为1～3的整数。
作为本发明的优选方案，所述取代或未被取代的含五元杂环的芳香基团选自：
Figure BDA0002432162580000021
Figure BDA0002432162580000031
Figure BDA0002432162580000041
其中“--”表示取代位。
优选地，所述取代或未被取代的含五元杂环的芳香基团选自：
Figure BDA0002432162580000042
Figure BDA0002432162580000051
更优选地，所述取代或未被取代的含五元杂环的芳香基团选自：
Figure BDA0002432162580000052
所述通式(I)中，所述R1～R8中，除了代表取代或未被取代的含五元杂环的芳香基团的一个、两个或多个基团外，其余基团各自独立地代表氢原子、卤素、直链或含支链的烷基(优选为C1-C5)、环烷基、氨基、烷胺基、取代或未被取代的含有苯环和/或芳杂环的芳香基团。
作为本发明的一种优选方案，所述R1～R8中，任意一个基团为取代或未被取代的含五元杂环的芳香基团。
作为本发明的一种优选方案，所述R1～R8中，任意两个基团为取代或未被取代的含五元杂环的芳香基团；上述两个基团可以相同，也可以不同。
作为本发明的一种优选方案，所述R1～R4中，任意一个基团为取代或未被取代的含五元杂环的芳香基团；且所述R5～R8中，任意一个基团为取代或未被取代的含五元杂环的芳香基团；上述两个基团可以相同，也可以不同。具体而言，所述R1和R5、或者R1和R7、或者R1和R8、或者R2和R5、或者R2和R6、或者R2和R7、或者R2和R8、或者R3和R5、或者R3和R6、或者R3和R7、或者R3和R8、或者R4和R5、或者R4和R7、或者R4和R8为取代或未被取代的含五元杂环的芳香基团，上述两个基团可以相同，也可以不同。
作为本发明的一种优选方案，所述R1～R8中，除了任意一个、两个或多个为取代或未被取代的含五元杂环的芳香基团外，其余皆为氢原子。
所述通式(I)中，X、Y各自独立地选自氢原子、卤素、直链或含支链的烷基(优选为C1-C5)、环烷基、氨基、烷胺基(优选为C1-C5)、取代或未被取代的含有苯环和/或芳杂环的芳香基团；m、n各自独立地代表0、1或者2。
作为本发明的一种优选方案，X代表芳胺基，卤素、优选为F原子，或者C1-C5的直链或支链烷基，m为1或2。
作为本发明的一种优选方案，Y代表芳胺基，卤素、优选为F原子，或者C1-C5的直链或支链烷基，n为1或2。
作为本发明的一种优选方案，X、Y均代表芳胺基，卤素、优选为F原子，或者C1-C5的直链或支链烷基，或氢原子。
作为本发明的优选的实施方案，所述茚并荧蒽化合物选自以下结构式所示化合物：
Figure BDA0002432162580000061
Figure BDA0002432162580000071
Figure BDA0002432162580000081
Figure BDA0002432162580000091
Figure BDA0002432162580000101
Figure BDA0002432162580000111
Figure BDA0002432162580000121
Figure BDA0002432162580000131
Figure BDA0002432162580000141
Figure BDA0002432162580000151
Figure BDA0002432162580000161
Figure BDA0002432162580000171
Figure BDA0002432162580000181
Figure BDA0002432162580000191
Figure BDA0002432162580000201
Figure BDA0002432162580000211
第二方面，本发明提供了一种所述的茚并荧蒽化合物在制备有机电致发光器件中的应用；优选地，所述的茚并荧蒽化合物在制备有机电致发光器件中作为空穴传输层的空穴传输材料的应用。
第三方面，本发明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含有所述的茚并荧蒽化合物的空穴传输层；优选地，所述有机电致发光器件由下至上依次包括透明基片、阳极层、含有所述的茚并荧蒽化合物的空穴传输层、电致发光层、电子传输层、电子注入层和阴极层。
第四方面，本发明提供了一种显示装置，包括所述的有机电致发光器件。
第五方面，本发明提供了一种照明装置，包括所述有机电致发光器件。
本发明提供了一种新型的茚并荧蒽结构化合物，该系列化合物以茚并荧蒽结构为母体，该母体结构具有刚性的结构单元，同时具有良好的热稳定性，该结构具有合适的HOMO和LUMO能级和Eg；通过在茚并荧蒽化合物的活泼位置引入具有空穴传输性能的给电子基团，即通过在结构中引入具有较强给电子能力的五元杂环结构，以芳香化合物为端基，获得了一类具有空穴传输性能的新型OLED材料。
本发明提供的该新型茚并荧蒽结构化合物，以茚并荧蒽结构化合物为母核，该类材料具有高的空穴迁移率，具有较好的薄膜稳定性和适合的分子能级，同时具有良好的热稳定性，可以被应用在有机电致发光领域，作为空穴传输材料使用。本发明提供的该新型茚并荧蒽结构化合物能够很好地应用于OLED器件中，器件表现具有驱动电压低、发光效率高的优点。该器件可以应用于显示或者照明领域。
具体实施方式
下面对本发明的技术方案进行详细说明。
根据本发明提供的制备方法，本领域技术人员可采用已知的常见手段来实现，如进一步选择合适的催化剂、溶剂，确定适宜的反应温度、时间等，本发明对此不作特别限定。制备过程中使用的溶剂、催化剂、碱等原料均可以通过公开商业途径或者本领域已知的方法合成得到。
采用本发明提供的制备方法，本发明提供了一系列茚并荧蒽结构化合物。
实施例1
Figure BDA0002432162580000221
合成路线如下：
Figure BDA0002432162580000231
化合物I-6的合成，包括如下具体步骤：在1L的三口瓶中，加入M1(43.4g，0.1mol，纯度99％)，(9-苯基-9H-咔唑-3-基)硼酸(57.4g，0.2mol，纯度99％)，碳酸钠(53g,0.5mol)，甲苯150mL，乙醇150mL，水150mL，反应体系用氮气置换保护后加入Pd(PPh3)4(11.5g，0.01mol)。加热回流反应(体系内温度约78℃)3小时，停止反应。分液，萃取，干燥，过滤，柱层析，旋干溶剂，得59.9g浅黄色固体，收率约79％。
产物MS(m/e)：758.27；元素分析(C58H34N2)：理论值C：91.79％，H：4.52％，N：3.69％；实测值C：91.78％，H：4.53％，N：3.69％。
实施例2
Figure BDA0002432162580000232
合成路线如下：
Figure BDA0002432162580000233
化合物I-20的合成，包括如下具体步骤：
用(9-(萘-2-基)-9H-咔唑-3-基)硼酸和M2，分别等当量代替实施例1所述的(9-苯基-9H-咔唑-3-基)硼酸和M1，其他反应条件和操作均和实施例1相同，得70.4g浅黄色固体，收率约82％。产物MS(m/e)：858.30；元素分析(C66H38N2)：理论值C：92.28％，H：4.46％，N：3.26％；实测值C：92.26％，H：4.47％，N：3.27％。
实施例3
Figure BDA0002432162580000241
合成路线如下：
Figure BDA0002432162580000242
化合物I-29的合成，包括如下具体步骤：用(4'-(9H-咔唑-9-基)-[1,1'-联苯]-4-基)硼酸和M3，分别等当量代替实施例1所述的(9-苯基-9H-咔唑-3-基)硼酸和M1，其他反应条件和操作均和实施例1相同，得72.8g浅黄色固体，收率约80％。产物MS(m/e)：910.33；元素分析(C70H42N2)：理论值C：92.28％，H：4.65％，N：3.07％；实测值C：92.26％，H：4.66％，N：3.08％。
实施例4
Figure BDA0002432162580000243
合成路线如下：
Figure BDA0002432162580000244
化合物I-35的合成，包括如下具体步骤：用(5-苯基-5H-苯并[b]咔唑-2-基)硼酸和M4，分别等当量代替实施例1所述的(9-苯基-9H-咔唑-3-基)硼酸和M1，其他反应条件和操作均和实施例1相同，得67.8g浅黄色固体，收率约79％。产物MS(m/e)：858.30；元素分析(C66H38N2)：理论值C：92.28％，H：4.46％，N：3.26％；实测值C：92.26％，H：4.47％，N：3.27％。
实施例5
Figure BDA0002432162580000251
合成路线如下：
Figure BDA0002432162580000252
化合物I-65的合成，包括如下具体步骤：用(4-(9H-二苯并[a，c]咔唑-9-基)苯基)硼酸和M5，按摩尔比1.05:1代替实施例1所述的(9-苯基-9H-咔唑-3-基)硼酸和M1，其他反应条件和操作均和实施例1相同，得46.3g浅黄色固体，收率约75％。产物MS(m/e)：617.21；元素分析(C48H27N)：理论值C：93.33％，H：4.41％，N：2.26％；实测值C：93.32％，H：4.41％，N：2.27％。
实施例6
Figure BDA0002432162580000253
合成路线如下：
Figure BDA0002432162580000254
化合物I-74的合成，包括如下具体步骤：用(4-(10-苯基吲哚[3,2-b]吲哚-5(10H)-基)苯基)硼酸和M6，按摩尔比1.05:1代替实施例1所述的(9-苯基-9H-咔唑-3-基)硼酸和M1，其他反应条件和操作均和实施例1相同，得51.2g浅黄色固体，收率约81％。产物MS(m/e)：632.23；元素分析(C48H28N2)：理论值C：91.11％，H：4.46％，N：4.43％；实测值C：91.09％，H：4.50％，N：4.41％。
实施例7
Figure BDA0002432162580000261
合成路线如下：
Figure BDA0002432162580000262
化合物I-111的合成，包括如下具体步骤：用(3-苯基苯并[b]噻吩-2-基)硼酸和M7，分别等当量代替实施例1所述的(9-苯基-9H-咔唑-3-基)硼酸和M1，其他反应条件和操作均和实施例1相同，得54.0g浅黄色固体，收率约78％。产物MS(m/e)：692.16；元素分析(C50H28S2)：理论值C：86.67％，H：4.07％；实测值C：86.66％，H：4.09％。
实施例8
Figure BDA0002432162580000263
合成路线如下：
Figure BDA0002432162580000271
化合物I-144的合成，包括如下具体步骤：用二苯并[b，d]呋喃-3-基硼酸和M8，分别等当量代替实施例1所述的(9-苯基-9H-咔唑-3-基)硼酸和M1，其他反应条件和操作均和实施例1相同，得52.3g浅黄色固体，收率约86％。产物MS(m/e)：608.18；元素分析(C46H24O2)：理论值C：90.77％，H：3.97％；实测值C：90.76％，H：3.99％。
实施例9
Figure BDA0002432162580000272
合成路线如下：
Figure BDA0002432162580000273
化合物I-156的合成，包括如下具体步骤：在1L的三口瓶中，加入M9(48.1g，0.1mol，纯度99％)，(4-(7H-二苯并[c，g]咔唑-7-基)苯基)硼酸(38.7g，0.1mol，纯度99％)，碳酸钠(31.8g,0.3mol)，甲苯150mL，乙醇150mL，水150mL，反应体系用氮气置换保护后加入Pd(PPh3)4(11.5g，0.01mol)。加热回流反应(体系内温度约78℃)3小时，停止反应。分液，萃取，干燥，过滤，柱层析，旋干溶剂，得55.6g浅黄色固体I-156-1，收率约80％。
在1L的三口瓶中，加入I-156-1(69.5g，0.1mol，纯度99％)，(4-(3,6-二苯基-9H-咔唑-9-基)苯基)硼酸(43.9g，0.1mol，纯度99％)，碳酸钠(31.8g,0.3mol)，甲苯150mL，乙醇150mL，水150mL，反应体系用氮气置换保护后加入Pd(PPh3)4(11.5g，0.01mol)。加热回流反应(体系内温度约78℃)3小时，停止反应。分液，萃取，干燥，过滤，柱层析，旋干溶剂，得76.8g浅黄色固体I-156，收率约76％。
产物MS(m/e)：1010.37；元素分析(C78H46N2)：理论值C：92.64％，H：4.59％，N：2.77％；实测值C：92.63％，H：4.59％，N：2.78％。
实施例10
Figure BDA0002432162580000281
合成路线如下：
Figure BDA0002432162580000282
化合物I-162的合成，包括如下具体步骤：用苯并[b]菲[9,10-d]噻吩-11-基硼酸和M10，二萘并[2,1-b：1'，2'-d]呋喃-5-基硼酸和I-162-1，分别等当量代替实施例9所述的(4-(7H-二苯并[c，g]咔唑-7-基)苯基)硼酸和M9，(4-(3,6-二苯基-9H-咔唑-9-基)苯基)硼酸和I-156-1，其他反应条件和操作均和实施例9相同，得61.8g浅黄色固体I-162，收率约75％。产物MS(m/e)：824.22；元素分析(C62H32OS)：理论值C：90.26％，H：3.91％；实测值C：90.25％，H：3.96％。
以上实施例中所用中间体M1～M10等均可从北京燕化集联光电技术有限公司购买所得。
依据上述实施例1～实施例10的合成方案，只需要简单替换对应的原料，不改变任何实质性操作，合成了I-1～I-174的其他化合物。
实施例11
本实施例提供了一组OLED红光器件，该OLED-1红光器件的结构为：ITO/HATCN(1nm)/HT01(40nm)/I-6化合物(20nm)/EML(30nm)/Bphen(40nm)/LiF(1nm)/Al。其中1nm、40nm、20nm等均表示功能层的厚度。
各功能层材料分子结构具体如下：
Figure BDA0002432162580000291
具体制备方法如下：
(1)将涂布了ITO透明导电层的玻璃板在商用清洗剂中超声处理，在去离子水中冲洗，在丙酮∶乙醇混合溶剂(体积比1∶1)中超声除油，在洁净环境下烘烤至完全除去水份，用紫外光和臭氧清洗，并用低能阳离子束轰击表面；
(2)把带有阳极的上述玻璃基片置于真空腔内，抽真空至1×10-5～9×10-3Pa，在上述阳极层膜上真空蒸镀HATCN作为第一空穴注入层，蒸镀速率为0.1nm/s，蒸镀总膜厚为1nm；接着蒸镀第二空穴注入层HT01，蒸镀速率为0.1nm/s，厚度为40nm；然后蒸镀空穴传输层，采用实施例1制得的I-6化合物，蒸镀速率为0.1nm/s，蒸镀膜厚为20nm；
(3)在空穴传输层之上真空蒸镀EML作为器件的发光层，EML包括主体材料和染料材料，利用多源共蒸的方法，调节主体材料PRH01蒸镀速率为0.1nm/s，染料材料Ir(piq)2acac的浓度为5％，蒸镀总膜厚为30nm；
(4)用Bphen作为器件电子传输层的电子传输材料，其蒸镀速率为0.1nm/s，蒸镀总膜厚为40nm；
(5)在电子传输层上依次真空蒸镀厚度为1nm的LiF作为电子注入层，厚度为150nm的Al层作为器件的阴极；制得该OLED-1红光器件。
按照与上相同的步骤，仅将步骤(2)中的空穴传输层材料由实施例1制得的I-6化合物分别替换为I-20、I-29、I-35、I-65、I-74、I-111、I-144、I-156、I-162，分别得到本发明提供的OLED-2～OLED-10红光器件。
按照与上相同的步骤，仅将步骤(2)中空穴传输层材料由实施例1制得的I-6化合物替换为NPB(对比化合物)，得到本发明提供的对比例OLED-11。所述NPB的结构具体为：
Figure BDA0002432162580000301
对上述所得器件OLED-1～OLED-11的性能分别进行检测，检测结果如表1所示。
表1
Figure BDA0002432162580000302
由上表可知，利用本发明提供的通式(I)所示的有机材料制备成的器件OLED-1～OLED-10，电流效率高于对比例OLED-11，且在亮度相同的条件下，工作电压明显比NPB作为空穴传输材料的器件OLED-11低。以上说明本发明提供的通式(I)所示的有机材料是一种新型的性能良好的空穴传输材料。
虽然，上文中已经用一般性说明、具体实施方式及试验，对本发明作了详尽的描述，但在本发明基础上，可以对之作一些修改或改进，这对本领域技术人员而言是显而易见的。因此，在不偏离本发明精神的基础上所做的这些修改或改进，均属于本发明要求保护的范围。

Claims (10)

1.一种茚并荧蒽化合物，其特征在于，所述化合物如通式(Ⅰ)所示：
Figure FDA0002432162570000011
所述R1～R8中，至少有一个基团为取代或未被取代的含五元杂环的芳香基团，其余基团各自独立地代表氢原子、卤素、直链或含支链的烷基、环烷基、氨基、烷胺基、取代或未被取代的含有苯环和/或芳杂环的芳香基团；
所述取代或未被取代的含五元杂环的芳香基团通过C原子与通式(Ⅰ)所示的母核相连；
X、Y各自独立地选自氢原子、卤素、直链或含支链的烷基、环烷基、氨基、烷胺基、芳胺基、取代或未被取代的含有苯环和/或芳杂环的芳香基团；
m、n各自独立地代表0、1或者2。
2.根据权利要求1所述的化合物，其特征在于，所述R1～R8中，任意一个基团为取代或未被取代的含五元杂环的芳香基团；
或者，所述R1～R8中，任意两个基团为取代或未被取代的含五元杂环的芳香基团；上述两个基团可以相同，也可以不同；
或者，所述R1～R4中，任意一个基团为取代或未被取代的含五元杂环的芳香基团；且所述R5～R8中，任意一个基团为取代或未被取代的含五元杂环的芳香基团；上述两个基团可以相同，也可以不同。
3.根据权利要求1或2所述的化合物，其特征在于，所述取代或未被取代的含五元杂环的芳香基团含有至少一个五元杂环，所述五元杂环含有至少一个杂原子，所述杂原子任意地选自N原子、S原子和O原子。
4.根据权利要求1～3任意一项所述的化合物，其特征在于，所述取代或未被取代的含五元杂环的芳香基团选自：取代或未被取代的咔唑基、取代或未被取代的吲哚并吲哚基、取代或未被取代的噻吩基、取代或未被取代的苯并噻吩基、取代或未被取代的苯并呋喃基；
优选地，所述取代的含五元杂环的芳香基团中，取代采用的取代基可以任意选自：苯基、萘基、联苯基、苯并基、萘并基、菲并基、吲哚并基、苯并噻吩并基、苯并呋喃并基。
5.根据权利要求1～3任意一项所述的茚并荧蒽化合物，其特征在于，所述取代或未被取代的含五元杂环的芳香基团选自：
Figure FDA0002432162570000021
Figure FDA0002432162570000031
其中“--”表示取代位。
6.根据权利要求1所述的化合物，其特征在于，所述化合物选自以下结构式所示化合物：
Figure FDA0002432162570000032
Figure FDA0002432162570000041
Figure FDA0002432162570000051
Figure FDA0002432162570000061
Figure FDA0002432162570000071
Figure FDA0002432162570000081
Figure FDA0002432162570000091
Figure FDA0002432162570000101
Figure FDA0002432162570000111
Figure FDA0002432162570000121
Figure FDA0002432162570000131
Figure FDA0002432162570000141
Figure FDA0002432162570000151
Figure FDA0002432162570000161
Figure FDA0002432162570000171
Figure FDA0002432162570000181
Figure FDA0002432162570000191
7.权利要求1～6任意一项所述的茚并荧蒽化合物在制备有机电致发光器件中的应用；
优选地，所述的茚并荧蒽化合物在有机电致发光器件中用作空穴传输层的空穴传输材料。
8.一种有机电致发光器件，其特征在于，所述有机电致发光器件的空穴传输层中含有权利要求1～6任意一项所述的茚并荧蒽化合物；
优选地，所述有机电致发光器件由下至上依次包括透明基片、阳极层、含有权利要求1～6任意一项所述的茚并荧蒽化合物的空穴传输层、电致发光层、电子传输层、电子注入层和阴极层。
9.一种显示装置，其特征在于，包括权利要求8所述的有机电致发光器件。
10.一种照明装置，其特征在于，包括权利要求8所述有机电致发光器件。
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JP2003238516A (ja) * 2002-02-19 2003-08-27 Petroleum Energy Center 新規な縮合芳香族化合物及びそれを利用した有機エレクトロルミネッセンス素子

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