CN111423390A - 一种新型结构化合物及其应用 - Google Patents
一种新型结构化合物及其应用 Download PDFInfo
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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,该类材料具有高的电子迁移率,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,作为电子传输材料使用。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
技术领域
本发明属于有机电致发光显示技术领域,具体地,涉及一种新型结构化合物及其应用。
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
本发明的目的在于提供一种新型结构化合物,其母核具有茚并荧蒽结构单元,且与含有氮杂六元环的芳香基团相连,可以作为电子传输材料使用,以降低有机电致发光器件的驱动电压,同时提高有机电致发光器件的发光效率。
具体而言,本发明提供一种新型结构化合物,具有如通式(Ⅰ)所示的结构:
所述R1~R8中,至少有一个基团为取代或未被取代的含有氮杂六元环的芳香基团,其通过C原子与通式(Ⅰ)所示的母核相连。
所述取代或未被取代的含有氮杂六元环的芳香基团可以是单环芳烃,也可以是多环芳烃;所述多环芳烃可以是多苯代脂烃、联苯型多环芳烃或稠环芳烃。
所述取代或未被取代的含有氮杂六元环的芳香基团中,所述氮杂六元环可以是含有一个氮杂原子的苯环,含有两个氮杂原子的苯环或者含有三个氮杂原子的苯环。所述氮杂六元环还可以进一步代表含有一个氮杂原子的萘环,含有两个氮杂原子的萘环或者含有三个氮杂原子的萘环。
作为本发明的优选方案,所述取代或未被取代的含有氮杂六元环的芳香基团选自:一个或多个三嗪基取代的含有至少一个苯环的芳香基、取代或未被取代的哒嗪基、取代或未被取代的嘧啶基、取代或未被取代的吡嗪基、取代或未被取代的三嗪基、取代或未被取代的喹啉基、取代或未被取代的异喹啉基。
作为本发明的优选方案,所述取代的含有氮杂六元环的芳香基团中,取代采用的取代基可以任意选自:烷基、苯基、烷基苯基、萘基、联苯基、苯并基、烷基苯并基、萘并基、吡啶基、喹啉基、异喹啉基、芴基、氧芴基、硫芴基、咔唑基;取代基的个数选自1~5的整数、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有氮杂六元环的芳香基团选自:
所述基团中“---”表示取代位。
优选地,所述取代或未被取代的含有氮杂六元环的芳香基团选自:
更优选地,所述取代或未被取代的含有氮杂六元环的芳香基团选自:
所述通式(I)中,所述R1~R8中,除了代表取代或未被取代的含有氮杂六元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(所述芳香基团可以是单环芳烃,也可以是多环芳烃;所述多环芳烃可以是多苯代脂烃、联苯型多环芳烃或稠环芳烃)。所述其余基团可以独立存在,也可以与相邻的基团成环。
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有氮杂六元环的芳香基团。
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有氮杂六元环的芳香基团;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有氮杂六元环的芳香基团;且所述R5~R8中,任意一个基团为取代或未被取代的含有氮杂六元环的芳香基团;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R6、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R6、或者R4和R7、或者R4和R8为取代或未被取代的含有氮杂六元环的芳香基团,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有氮杂六元环的芳香基团外,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(所述芳香基团可以是单环芳烃,也可以是多环芳烃;所述多环芳烃可以是多苯代脂烃、联苯型多环芳烃或稠环芳烃);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。
作为本发明的优选实施方案,所述新型结构化合物选自:
第二方面,本发明提供了所述新型结构化合物在制备有机电致发光器件中的应用;优选地,所述新型结构化合物在制备有机电致发光器件中作为电子传输层的电子传输材料的应用。
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新型结构化合物的电子传输层;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、空穴传输层、电致发光层、含有所述新型结构化合物的电子传输层、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结构化合物,该材料以茚并荧蒽结构为母核,以芳香化合物为端基,通过在母体结构中引入含有氮杂六元环的芳香基团,获得了一类新的有机材料。该类材料具有较高的电子迁移率,较好的薄膜稳定性和适合的分子能级可以被应用在有机电致发光领域,作为电子传输材料使用。本发明提供的新型结构化合物能够很好地应用于有机电致发光器件中,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
下面通过实施例对本发明作进一步说明,应该理解的是,本发明的实施例仅仅是用于说明本发明,而不是本发明的限制,在本发明的构思前提下对本发明的简单改进都属于本发明要求保护的范围。
实施例1
合成路线如下:
包括如下具体步骤:化合物I-3的合成
在1L的三口瓶中,加入M1(43.4g,0.1mol,纯度99%),(4,6-二苯基-1,3,5-三嗪-2-基)硼酸(55.4g,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57.6g浅黄色固体,收率约78%。
产物MS(m/e):738.25;元素分析(C52H30N6):理论值C:84.53%,H:4.09%,N:11.37%;实测值C:84.52%,H:4.09%,N:11.38%。
实施例2
合成路线如下:
化合物I-12的合成
用(4,6-二(萘-2-基)-1,3,5-三嗪-2-基)硼酸和M2,分别等当量代替实施例1所述的(4,6-二苯基-1,3,5-三嗪-2-基)硼酸和M1,其他反应条件和操作均和实施例1相同,得67.5g浅黄色固体,收率约72%。
产物MS(m/e):938.32;元素分析(C68H38N6):理论值C:86.97%,H:4.08%,N:8.95%;实测值C:86.98%,H:4.07%,N:8.95%。
实施例3
合成路线如下:
包括如下具体步骤:化合物I-37的合成
用(4-([[1,1'-联苯]-4-基)-6-苯基-1,3,5-三嗪-2-基)硼酸和M3,分别等当量代替实施例1所述的(4,6-二苯基-1,3,5-三嗪-2-基)硼酸和M1,其他反应条件和操作均和实施例1相同,得66.8g浅黄色固体,收率约75%。
产物MS(m/e):890.32;元素分析(C64H38N6):理论值C:86.27%,H:4.30%,N:9.43%;实测值C:86.26%,H:4.31%,N:9.43%。
实施例4
合成路线如下:
化合物I-46的合成
用(4-(4,6-二苯基-1,3,5-三嗪-2-基)苯基)硼酸和M4,分别等当量代替实施例1所述的(4,6-二苯基-1,3,5-三嗪-2-基)硼酸和M1,其他反应条件和操作均和实施例1相同,得71.2g浅黄色固体,收率约80%。
产物MS(m/e):890.32;元素分析(C64H38N6):理论值C:86.27%,H:4.30%,N:9.43%;实测值C:86.26%,H:4.31%,N:9.43%。
实施例5
合成路线如下:
包括如下具体步骤:化合物I-57的合成
用(4,6-双(9,9-二甲基-9H-芴-2-基)-1,3,5-三嗪-2-基)硼酸和M5,按摩尔比1.05:1代替实施例1所述的(4,6-二苯基-1,3,5-三嗪-2-基)硼酸和M1,其他反应条件和操作均和实施例1相同,得56.9g浅黄色固体,收率约77%。
产物MS(m/e):739.30;元素分析(C55H37N3):理论值C:89.28%,H:5.04%,N:5.68%;实测值C:89.27%,H:5.05%,N:5.68%。
实施例6
合成路线如下:
包括如下具体步骤:化合物I-66的合成
用(4,6-双(二苯并[b,d]噻吩-3-基)-1,3,5-三嗪-2-基)硼酸和M6,按摩尔比1.05:1代替实施例1所述的(4,6-二苯基-1,3,5-三嗪-2-基)硼酸和M1,其他反应条件和操作均和实施例1相同,得56.1g浅黄色固体,收率约78%。
产物MS(m/e):719.15;元素分析(C49H25N3S2):理论值C:81.76%,H:3.50%,N:5.84%;实测值C:81.75%,H:3.50%,N:5.83%。
实施例7
合成路线如下:
包括如下具体步骤:化合物I-80的合成
用(4-(二苯并[b,d]呋喃-3-基)-6-苯基-1,3,5-三嗪-2-基)硼酸和M7,分别等当量代替实施例1所述的(4,6-二苯基-1,3,5-三嗪-2-基)硼酸和M1,其他反应条件和操作均和实施例1相同,得69.8g浅黄色固体,收率约76%。
产物MS(m/e):918.27;元素分析(C64H34N6O2):理论值C:83.64%,H:3.73%,N:9.14%;实测值C:83.63%,H:3.74%,N:9.15%。
实施例8
合成路线如下:
包括如下具体步骤:化合物I-111的合成
用(6-异丙基喹啉-2-基)硼酸和M8,分别等当量代替实施例1所述的(4,6-二苯基-1,3,5-三嗪-2-基)硼酸和M1,其他反应条件和操作均和实施例1相同,得51.6g浅黄色固体,收率约84%。
产物MS(m/e):614.27;元素分析(C46H34N2):理论值C:89.87%,H:5.57%,N:4.56%;实测值C:89.86%,H:5.58%,N:4.56%。
实施例9
合成路线如下:
包括如下具体步骤:化合物I-129的合成
在1L的三口瓶中,加入M9(48.1g,0.1mol,纯度99%),(4,6-二(萘-2-基)-1,3,5-三嗪-2-基)硼酸(37.7g,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53.4g浅黄色固体I-129-1,收率约78%。
在1L的三口瓶中,加入I-129-1(68.5g,0.1mol,纯度99%),(4,6-二苯基-1,3,5-三嗪-2-基)硼酸(27.7g,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62.9g浅黄色固体I-129,收率约75%。
产物MS(m/e):838.28;元素分析(C60H34N6):理论值C:85.90%,H:4.08%,N:10.02%;实测值C:85.91%,H:4.07%,N:10.02%。
实施例10
合成路线如下:
包括如下具体步骤:化合物I-135的合成
用(4,6-二(喹啉-3-基)-1,3,5-三嗪-2-基)硼酸和M10,(4-([[1,1'-联苯]-3-基)-6-苯基-1,3,5-三嗪-2-基)硼酸和I-135-1,分别等当量代替实施例9所述的(4,6-二(萘-2-基)-1,3,5-三嗪-2-基)硼酸和M9,(4,6-二苯基-1,3,5-三嗪-2-基)硼酸和I-129-1,其他反应条件和操作均和实施例9相同,得68.7g浅黄色固体I-135,收率约75%。
产物MS(m/e):916.31;元素分析(C64H36N8):理论值C:83.82%,H:3.96%,N:12.22%;实测值C:83.83%,H:3.95%,N:12.22%。
试验过程中所用中间体M1~M10等均可从北京燕化集联光电技术有限公司购买所得。
依据实施例1~实施例10的技术方案,只需要简单替换对应的原料,不改变任何实质性操作,可以合成I-1~I-148的其他化合物。
实施例11
本实施例制作了一组OLED红光器件。该器件的结构为:
ITO/HATCN(1nm)/HT01(40nm)/NPB(20nm)/EML(30nm)/I-3(40nm)/LiF(1nm)/Al。
各功能层材料分子结构如下:
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分,用紫外光和臭氧清洗,并用低能阳离子束轰击表面。
(2)把上述带有阳极的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NPB,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)用化合物I-3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。
按照与上相同的步骤,仅将步骤(4)中的化合物I-3分别替换为化合物I-12、I-37、I-46、I-57、I-66、I-80、I-111、I-129以及I-135,分别得到本发明提供的OLED-2~OLED-10。
按照与上相同的步骤,仅将步骤(4)中的I-3替换为Bphen(对比化合物),得到本发明提供的对比例OLED-11。Bphen的结构具体为:
本发明对上述所得器件OLED-1~OLED-11的性能进行检测,检测结果如表1所示。
表1:OLED器件性能检测结果
由上结果可知,利用本发明提供的通式(Ⅰ)所示结构的有机电致发光材料制备成的器件OLED-1~OLED-10的电流效率偏高,且在亮度相同的条件下,工作电压明显比Bphen作为电子传输材料的器件OLED-11偏低。本发明提供的有机电致发光材料是性能良好的电子传输材料。
以上详细描述了本发明的优选实施方式,但是,本发明并不限于上述实施方式中的具体细节,在本发明的技术构思范围内,可以对本发明的技术方案进行多种简单变型,这些简单变型均属于本发明的保护范围。
另外需要说明的是,在上述具体实施方式中所描述的各个具体技术特征,在不矛盾的情况下,可以通过任何合适的方式进行组合,为了避免不必要的重复,本发明对各种可能的组合方式不再另行说明。
此外,本发明的各种不同的实施方式之间也可以进行任意组合,只要其不违背本发明的思想,其同样应当视为本发明所公开的内容。
Claims (10)
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有氮杂六元环的芳香基团;
或者,所述R1~R8中,任意两个基团为取代或未被取代的含有氮杂六元环的芳香基团;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有氮杂六元环的芳香基团;且所述R5~R8中,任意一个基团为取代或未被取代的含有氮杂六元环的芳香基团;上述两个基团可以相同,也可以不同。
3.根据权利要求1所述的化合物,其特征在于,所述R1~R8中,除了代表取代或未被取代的含有氮杂六元环的芳香基团的一个、两个或多个基团外,其余基团均代表氢原子。
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有氮杂六元环的芳香基团选自:一个或多个三嗪基取代的含有至少一个苯环的芳香基、取代或未被取代的哒嗪基、取代或未被取代的嘧啶基、取代或未被取代的吡嗪基、取代或未被取代的三嗪基、取代或未被取代的喹啉基、取代或未被取代的异喹啉基;
优选地,所述取代的含有氮杂六元环的芳香基团中,取代采用的取代基可以任意选自:烷基、苯基、烷基苯基、萘基、联苯基、苯并基、烷基苯并基、萘并基、吡啶基、喹啉基、异喹啉基、芴基、氧芴基、硫芴基、咔唑基;取代基的个数选自1~5的整数。
7.权利要求1~6任意一项所述新型结构化合物在制备有机电致发光器件中的应用;
优选地,所述新型结构化合物在有机电致发光器件中用作电子传输层的电子传输材料。
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电子传输层中含有权利要求1~6任意一项所述的新型结构化合物;
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、空穴传输层、电致发光层、含有权利要求1~6任意一项所述新型结构化合物的电子传输层、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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CN112724158B (zh) * | 2020-12-22 | 2022-05-27 | 上海和辉光电股份有限公司 | 一种用于有机发光的化合物及其应用 |
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