CN107021956A - 苯并恶唑衍生物及其应用 - Google Patents
苯并恶唑衍生物及其应用 Download PDFInfo
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- CN107021956A CN107021956A CN201710291650.XA CN201710291650A CN107021956A CN 107021956 A CN107021956 A CN 107021956A CN 201710291650 A CN201710291650 A CN 201710291650A CN 107021956 A CN107021956 A CN 107021956A
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Abstract
本发明公开了一种苯并恶唑衍生物的制备方法与在有机发光二极管中的应用。该材料的结构如式I所示,该系列材料具有优异的电子传输能力,利用本发明的材料制备的有机电致发光器件可明显降低启动电压、提高发光效率和亮度。这一系列材料有较好的成膜性能,并且材料合成以及提纯的方法简单适于大规模生产等特点,是作为有机电致发光器件电子传输材料的理想选择。该有机电致发光材料作为发光材料或者作为发光层中的主体材料或空穴传输材料的应用也在保护范围内。
Description
技术领域
本发明属于有机电致发光显示技术领域,涉及一系列苯并恶唑衍生物及其在有机电致发光二极管的应用。
背景技术
有机电致发光(简称OLED)及相关的研究早在1963年pope等人首先发现了有机化合物单晶蒽的电致发光现象。1987年美国的柯达公司用蒸镀有机小分子的方法制成了一种非晶膜型器件,将驱动电压降到了20V以内。这类器件由于具有超轻薄、全固化、自发光、亮度高、视角宽、响应速度快、驱动电压低、功耗小、色彩鲜艳、对比度高、工艺过程简单、温度特性好、可实现柔软显示等优点,可广泛应用于平板显示器和面光源,因此得到了广泛地研究、开发和使用。
经过二十几年的发展,有机EL材料已经全面实现了红、蓝、绿色发光,应用领域也从小分子扩展到了高分子以及金属络合物等领域。最近几年有机电发光显示技术己趋于成熟,一些产品已进入市场,但在产业化时程中,仍有许多问题亟待解决,特别是用于制作器件的各种有机材料,其载流子注入、传输性能,材料电发光性能、使用寿命、色纯度、各种材料之间及与各电极之间的匹配等,尚有许多问题还未解决。尤其是发光器件在发光效率和使用寿命还达不到实用化要求,这大限制了OLED技术的发展。而利用三线态发光的金属配合物磷光材料具有高的发光效率,其绿光和红光材料已经达到使用要求,但是金属配合物特殊的电子结构特征,导致其蓝光材料无法达到使用要求。
介于荧光和磷光之间的热激活延迟荧光材料的出现,大大提高了荧光材料的发光效率,几乎达到磷光材料的发光效率,弥补了磷光蓝光材料的不足,同时避免了使用贵重的稀有金属,大大降低了材料成本。但是已经报道的热激活延迟荧光材料由于在固体状态下存在聚集荧光淬灭效应,只能采用掺杂的方式制备OLED器件。因此,开发出具有在固态下聚集诱导发光的热致激活延迟荧光材料是解决上述问题的一个途径。
发明内容
本发明的目的是提供一种高效的荧光材料与在有机电致发光二极管中的应用。
本发明具体提供了式I所示化合物
所述式I中:
Ar1、Ar2各自独立地表示氢、苯基、联苯基、1-萘基、2-萘基、吡啶基、芘基、蒽基、菲基、取代的或未取代的C2-C60杂环芳基中的任意一种;
R1、R2、R3各自独立的表示氢、氘氢、含有C1~C8的直链或带有支链的烷基、含有C1~C8的直链或带有支链的烷氧基、取代的或未取代的C6-C60芳基、取代的或未取代的C2-C60杂环芳基中的任意一种;
L1表示取代的或未取代的亚苯基、取代的或未取代的亚萘基、取代的或未取代的亚芴基、取代的或未取代的亚螺芴基、取代的或未取代的亚蒽基、取代的或未取代的亚吡啶基、取代的或未取代的亚嘧啶基、取代的或未取代的亚喹啉基和/或取代的或未取代的亚咔唑基;
x表示0-5的整数。
所述取代的或未取代的C2-C60杂环芳基,其中包含N、O、S原子中的至少一种的环状结构;
所述Ar1、Ar2、R1、R2、R3表示的基团中,所述C2-C60的杂环芳基优选包含以下II-1~II-15的结构中的一种或多种:
所述式II-1至II-15中,
Z1、Z2、Z3各自独立地表示氢、氘氢、卤原子、羟基、腈基、硝基、氨基、脒基、肼基、腙基、羧基或其羧酸盐、磺酸基或其磺酸盐、磷酸基或其磷酸盐、C1-C60烷基、C2-C60烯基、C2-C60炔基、C1-C60烷氧基、C3-C60环烷烃基、C3-C60环烯烃基、C6-C60芳基、至少含有一个-F、-CN或C1-C10烷基的C6-C60芳基、取代的或未取代的C6-C60芳氧基、取代的或未取代的C6-C60芳硫醚基、取代的或未取代的C2-C60杂环芳基中的任意一种;
x1表示1-4的整数;x2表示1-3的整数;x3表示1或2;x4表示1-6的整数;x5表示1-5的整数;
T1表示氧或硫。
具体的所述L1包含以下III-1~III-16的结构:
所述式III-1~III-16中
Z11和Z12各自独立地表示氢、氘氢、卤原子、羟基、腈基、硝基、氨基、脒基、肼基、腙基、羧基或其羧酸盐、磺酸基或其磺酸盐、磷酸基或其磷酸盐、C1-C60烷基、C2-C60烯基、C2-C60炔基、C1-C60烷氧基、C3-C60环烷烃基、C3-C60环烯烃基、C6-C60芳基、至少含有一个-F、-CN或C1-C10烷基的C6-C60芳基、取代的或未取代的C6-C60芳氧基、取代的或未取代的C6-C60芳硫醚基、取代的或未取代的C2-C60杂环芳基中的任意一种;
Z13表示取代的或未取代的C6-C60芳基、取代的或未取代的C6-C60芳氧基、取代的或未取代的C6-C60芳硫醚基、取代的或未取代的C2-C60杂环芳基中的任意一种;
y1表示1-4的整数;y2表示1-6的整数;y3表示1-3的整数;y4表示1-5的整数。
具体的,所述式I所示化合物为以下POZ-1至POZ-132所示化合物中的任意一种:
本发明还请求保护包含以上化合物的材料、以上化合物在制备有机发光二极管材料中的应用、以上化合物作为发光层材料在制备有机电致发光器件中的应用以及含有以上化合物作为发光层的有机电致发光器件。
本发明还提供一种使用以上苯并恶唑衍生物材料的电致发光OLED器件;
具体的,所述有机电致发光器件如附图2所示,由下至上依次包括透明基片1、阳极2、空穴注入层3、空穴传输层4、有机发光层5、电子传输层6和阴极层7。
其中,构成所述透明基片的材料为玻璃或柔性基片;
构成所述阳极层的材料为无机材料或有机导电聚合物;其中,所述无机材料为氧化铟锡、氧化锌、氧化锡锌、金、银或铜;所述有机导电聚合物选自聚噻吩、聚乙烯基苯磺酸钠和聚苯胺中的至少一种;
构成所述空穴注入层的材料如下,但不限于以下材料:
构成所述空穴传输层的材料如下,但不限于以下材料:
构成所述有机发光层的材料包括主体材料和掺杂材料,主体材料如下,但不限于以下材料:
构成所述电子传输层的材料为本发明所述式I所示化合物,以及其它金属的配合物,结构如下,但不限于以下材料:
构成所述有机发光层的掺杂材料还包括红色、绿色、蓝色掺杂材料,其中蓝色掺杂材料如下,但不限于以下材料:
其中红色掺杂材料如下,但不限于以下材料:
其中绿色掺杂材料如下,但不限于以下材料:
构成所述阴极层的材料选自下述元素中的任意一种或任意两种组成的合金或下述元素的氟化物:锂、镁、银、钙、锶、铝、铟、铜、金和银。
其中,所述空穴注入层的厚度为30-50nm,具体为40nm;
所述空穴传输层的厚度为5-15nm,具体为10nm;
所述有机发光层的厚度为10-100nm,具体为40nm;
所述电子传输层的厚度为10-30nm,具体为50nm;
所述阴极层的厚度为90-110nm,具体为100nm。
本发明提供的式I所示有机电致发光材料,具有优异的电子传输能力,利用本发明的材料制备的有机电致发光器件可降低启动电压、提高发光效率和亮度。这一系列材料有较好的成膜性能,并且材料合成以及提纯的方法简单适于大规模生产等特点,是作为有机电致发光器件电子传输材料的理想选择。该有机电致发光材料作为发光材料或者作为发光层中的主体材料或空穴传输材料的应用也在保护范围内。
具体实施方式
下面结合具体实施例对本发明的特征和技术内容作进一步阐述,但本发明并不限于以下实施例。请参阅以下有关本发明的详细说明与附图,然而附图仅提供参考与说明,并非用来对本发明加以限制。所述原材料如无特别说明均能从公开商业途径而得。
下述实施例对OLED材料及器件进行性能测试的测试仪器及方法如下:
OLED器件性能检测条件:
亮度和色度坐标:使用光谱扫描仪PhotoResearch PR-715测试;
电流密度和起亮电压:使用数字源表Keithley 2420测试;
功率效率:使用NEWPORT 1931-C测试。
附图说明
图1为本发明化合物式I的制备方法流程图;
图2为本发明使用化合物式I的OLED器件结构示意图;
图3为本发明化合物式POZ-9的紫外吸收谱图;
图4为本发明化合物式POZ-9的荧光光谱图;
图5为本发明化合物式POZ-9的低温磷光光谱图。
具体实施方式
下面结合附图,通过对本发明的具体实施方式详细描述,将使本发明的技术方案和其它有益效果显而易见。
以下通过具体的实施例对本发明作进一步的阐述,但本发明并不限于此特定例子。
实施例1
化合物POZ-9的制备
第一步:中间体Int.-2的制备
10g(26.5mmol)的4-(4-溴苯基)-3,5-二苯基-1,2,4-三唑中间体Int.-1溶解在80ml的N,N-二甲基甲酰胺中,在氮气保护下,加入7.4g(29.1mmol)的联硼酸频那醇酯和3.5g的醋酸钾,再加入217mg(0.26mmol)的Pd(dppf)Cl2催化剂,升温至80℃搅拌反应8小时,冷却到室温,将反应液倒入800ml的冰水中,用二氯甲烷萃取,有机相干燥过滤,滤液减压浓缩干,用硅胶柱分离纯化,减压浓缩干,得9.5g黄色固体,收率85%。
第二步:中间体Int.-3的制备
20g(0.106mol)的2-羟基-3-溴苯氨溶解在80ml的二苯醚中,加入13g(0.106mol)的苯甲酸和0.66g的硼酸,升温至180℃搅拌反应8小时,随时分出反应生成的水,冷却到室温,用硅胶柱分离纯化,减压浓缩干,得26.2g白色固体,收率90%。
第三步:化合物式POZ-9的制备
将5g(11.8mmol)上步中间体Int.-2、3.2g(11.6mmol)的中间体Int.-3、2.5g(23.6mmol)的碳酸钠混合,再加入136mg(0.11mmol)的Pd(PPh3)4催化剂和60mL的甲苯,再加入20mL的乙醇和20mL的水,在氮气保护下,升温回流搅拌反应12小时,冷却到室温,用乙酸乙酯萃取,有机相用无水硫酸钠干燥,过滤,滤液减压浓缩干,用硅胶柱分离纯化,再用乙醇重结晶,得5.4g白色固体POZ-9,收率93%。HRMS:C33H22N4O,标准分子量490.18,测试结果491.16,1HNMR(δ、CDCl3):7.12(1H,s);7.17~7.27(6H,m);7.31~7.48(10H,m);7.65~7.67(1H,d);7.88~7.91(2H,d);8.09~8.11(2H,m)。载流子迁移率:4.5×10-4cm2/VS
实施例2
化合物POZ-57的制备
第一步:中间体Int.-5的制备
合成操作参照实施例1的第二步,将实施例1第二步的苯甲酸替换为9,9-二甲基芴-2-甲酸,硅胶柱分离纯化,得到中间体Int.-5,白色的固体,收率86%。
第二步:化合物式POZ-57的制备
将5g(14.3mmol)中间体Int.-4、5.46g(14mmol)的中间体Int.-5、3.0g(28.6mmol)的碳酸钠混合,再加入162mg(0.14mmol)的Pd(PPh3)4催化剂和60mL的甲苯,再加入20mL的乙醇和20mL的水,在氮气保护下,升温回流搅拌反应12小时,冷却到室温,用乙酸乙酯萃取,有机相用无水硫酸钠干燥,过滤,滤液减压浓缩干,用硅胶柱分离纯化,得6.6g黄色固体POZ-57,收率89%。HRMS:C36H25N3O2,标准分子量531.195,测试结果531.193,1HNMR(δ、CDCl3):1.45(6H,s);7.17~7.23(4H,m);7.26~7.34(5H,m);7.36~7.38(3H,m);7.40~7.43(6H,m);7.85(1H,d)。载流子迁移率:4.8×10-3cm2/VS
参照实施例1和2的合成方法,制备下列化合物:
实施例3
化合物式POZ-68的制备
第一步:中间体Int.-20的制备
合成操作参照实施例1的第二步,将实施例1第二步的苯甲酸替换为烟酸,
硅胶柱分离纯化,得到中间体Int.-20,黄色的固体,收率88%。
第二步:中间体Int.-21的制备
7.3g(26.5mmol)的中间体Int.-20溶解在80ml的N,N-二甲基甲酰胺中,在氮气保护下,加入7.4g(29.1mmol)的联硼酸频那醇酯和3.5g的醋酸钾,再加入217mg(0.26mmol)的Pd(dppf)Cl2催化剂,升温至80℃搅拌反应8小时,冷却到室温,将反应液倒入800ml的冰水中,用二氯甲烷萃取,有机相干燥过滤,滤液减压浓缩干,用硅胶柱分离纯化,减压浓缩干,得6.6g黄色油状物,收率77%。
第三步:化合物POZ-68的制备
将5g(15.5mmol)中间体Int.-21、2.4g(7mmol)的中间体(4,4’-二溴)二苯甲酮、6.6g(62mmol)的碳酸钠混合,再加入173mg(0.15mmol)的Pd(PPh3)4催化剂和40mL的甲苯,再加入20mL的乙醇和20mL的水,在氮气保护下,升温回流搅拌反应12小时,冷却到室温,用乙酸乙酯萃取,有机相用无水硫酸钠干燥,过滤,滤液减压浓缩干,用硅胶柱分离纯化,得3.0g白色固体,收率76%。HRMS:C37H22N4O3,标准分子量570.169,测试结果570.199,1HNMR(δ、CDCl3):7.41~7.35(2H,m);7.62~7.48(6H,m);7.59~7.54(8H,m);7.87~7.84(2H,m);8.13~8.10(2H,m);8.24(2H,s)。载流子迁移率:5.7×10-4cm2/VS
参照实施例3的合成方法,制备下列化合物:
序号 | 化合物编号 | 质谱测试结果 | 载流子迁移率(cm2/VS) |
55 | POZ-65 | 568.182 | 4.5×10-4 |
56 | POZ-66 | 668.213 | 5.2×10-4 |
57 | POZ-67 | 668.213 | 5.1×10-4 |
58 | POZ-69 | 570.199 | 5.4×10-4 |
59 | POZ-70 | 748.205 | 4.8×10-4 |
60 | POZ-71 | 780.158 | 4.5×10-4 |
61 | POZ-72 | 472.184 | 3.7×10-4 |
实施例4
化合物式POZ-73的制备
第一步:中间体Int.-6的制备
7.3g(26.5mmol)的中间体Int.-3溶解在80ml的N,N-二甲基甲酰胺中,在氮气保护下,加入7.4g(29.1mmol)的联硼酸频那醇酯和3.5g的醋酸钾,再加入217mg(0.26mmol)的Pd(dppf)Cl2催化剂,升温至80℃搅拌反应8小时,冷却到室温,将反应液倒入800ml的冰水中,用二氯甲烷萃取,有机相干燥过滤,滤液减压浓缩干,用硅胶柱分离纯化,减压浓缩干,得7.2g黄色油状物,收率85%。
第二步:中间体Int.-7的制备
将5g(15.5mmol)中间体Int.-6、2.4g(7mmol)的中间体(4,4’-二溴)二苯硫醚、6.6g(62mmol)的碳酸钠混合,再加入173mg(0.15mmol)的Pd(PPh3)4催化剂和40mL的甲苯,再加入20mL的乙醇和20mL的水,在氮气保护下,升温回流搅拌反应12小时,冷却到室温,用乙酸乙酯萃取,有机相用无水硫酸钠干燥,过滤,滤液减压浓缩干,用硅胶柱分离纯化,得3.3g黄色固体,收率82%。
第三步:化合物POZ-73的制备
将3g(5.2mmol)中间体Int.-7和40mL的醋酸混合,加入10mL的30%过氧化氢,升温回流搅拌反应6小时,冷却到室温,将反应液倒入200mL的冰水中,过滤,滤饼用水洗,再用硅胶柱分离纯化,得3g白色固体POZ-73,收率95%。HRMS:C38H24N2O4S,标准分子量604.146,测试结果604.148,1HNMR(δ、CDCl3):7.43~7.37(2H,m);7.52~7.46(6H,m);7.59~7.55(4H,m);7.68~7.62(4H,m);7.75~7.70(4H,m);7.83~7.78(4H,m)。载流子迁移率:3.8×10-4cm2/VS
参照实施例3的合成方法,制备下列化合物:
实施例4
化合物POZ-129的制备
第一步:中间体Int.-9的制备
将10g(31.8mmol)中间体Int.-8、5.0g(26.5mmol)的原料3-溴-2-羟基苯胺、6.7g(63.6mmol)的碳酸钠混合,再加入30mg(0.13mmol)的醋酸钯催化剂和60mL的N,N-二甲基甲酰胺,升温至80℃搅拌反应2小时,冷却到室温,将反应液倒入600mL的冰水中,过滤,滤饼用水洗,乙醇洗,得9.2g灰白色固体,收率92%。
第二步:中间体Int.-10的制备
8g(21.2mmol)的中间体Int.-9溶解在80ml的二苯醚中,加入4.3g(21.2mmol)的对溴苯甲酸和132mg的硼酸,升温至180℃搅拌反应8小时,随时分出反应生成的水,冷却到室温,用硅胶柱分离纯化,减压浓缩干,得8.7g黄色固体,收率76%。
第三步:中间体Int.-11的制备
8g(14.7mmol)的中间体Int.-10溶解在120ml的干燥四氢呋喃中,在氮气保护下,用液氮降温至-78℃,缓慢滴加入6.5ml的2.5M正丁基锂正己烷溶液,搅拌反应30分钟,缓慢滴加入3.57g(16.2mmol)的二苯基氯化磷溶于四氢呋喃的溶液,搅拌反应30分钟,升至室温搅拌反应1小时,滴加入15ml的饱和氯化铵水溶液,分出有机相,水相用二氯甲烷萃取,有机相减压浓缩干,用硅胶柱分离纯化,得7.7g黄色固体,收率81%。
第四步:化合物POZ-129的制备
5g(7.7mmol)的中间体Int.-11溶解在50ml的二氯甲烷中,加入10ml的30%过氧化氢水溶液,搅拌升温回流反应12小时,冷却到室温,分出有机相,水相用二氯甲烷萃取,有机相减压浓缩干,用硅胶柱分离纯化,得4.8g白色固体,收率93%。HRMS:C44H30N3O2P,标准分子量663.208,测试结果663.212,1HNMR(δ、CDCl3):7.22~7.25(5H,m);7.43~7.30(11H,m);7.52~7.45(7H,m);7.59~7.56(4H,m);7.64~7.61(2H,m);7.83~7.82(1H,m)。载流子迁移率:6.8×10-3cm2/VS
参照实施例4的合成方法,制备下列化合物:
实施例5
制备器件OLED-1~OLED-6
1)将涂布了ITO导电层的玻璃基片在清洗剂中超声处理30分钟,在去离子水中冲洗,在丙酮/乙醇混合溶剂中超声30分钟,在洁净的环境下烘烤至完全干燥,用紫外光清洗机照射10分钟,并用低能阳离子束轰击表面。
2)把上述处理好的ITO玻璃基片置于真空腔内,抽真空至1×10-5~9×10-3Pa,在上述阳极层膜上蒸镀化合物2-TNATA作为空穴注入层,蒸镀速率为0.1nm/s,蒸镀膜厚为40nm;
3)在上述空穴注入层上继续蒸镀NPB为空穴传输层,蒸镀速率为0.1nm/s,蒸镀膜厚为10nm;
4)在空穴传输层上继续蒸镀ADN为主体材料和DPVBi为掺杂材料,ADN:DPVBi=98:2,作为器件的有机发光层,蒸镀速率为0.1nm/s,蒸镀所得有机发光层的膜厚为40nm;
5)在有机发光层上继续蒸镀一层本发明的化合物(式I)为主体材料和LiQ为掺杂材料,化合物(式I):LiQ=90:10,作为器件的电子传输层,蒸镀速率为0.1nm/s,蒸镀膜厚为50nm;
6)在电子传输层之上依次蒸镀镁/银合金层作为器件的阴极层,其中镁/银合金层的蒸镀速率为2.0~3.0nm/s,蒸镀膜厚为100nm,镁和银的质量比为1:9,得到本发明提供的OLED器件。
按照与上相同的步骤,将步骤5)中的化合物(式I)选为POZ-9,得到本发明提供的OLED-1;
按照与上相同的步骤,将步骤5)中的化合物(式I)选为POZ-18,得到本发明提供的OLED-2;
按照与上相同的步骤,将步骤5)中的化合物(式I)选为POZ-57,得到本发明提供的OLED-3;
按照与上相同的步骤,将步骤5)中的化合物(式I)选为POZ-107,得到本发明提供的OLED-4;
按照与上相同的步骤,将步骤5)中的化合物(式I)选为POZ-129,得到本发明提供的OLED-5;
按照与上相同的步骤,将步骤5)中的化合物(式I)替换为Alq3,得到对比器件OLED-6;
所得器件OLED-1至OLED-6的性能检测结果如表1所示。
表1、OLED-1至OLED-6的性能检测结果
由上可知,本专利发明的有机材料制备成的器件起亮电压低,在电流密度相同的条件下,亮度和效率明显比Alq3作为电子传输层的高,而且器件的半衰期要延长很多。
尽管结合优选实施例对本发明进行了说明,但本发明并不局限于上述实施例和附图,应当理解,在本发明构思的引导下,本领域技术人员可进行各种修改和改进,所附权利要求概括了本发明的范围。
Claims (12)
1.式I所示化合物
所述式I中
Ar1、Ar2各自独立地表示氢、苯基、联苯基、1-萘基、2-萘基、吡啶基、芘基、蒽基、菲基、取代的或未取代的C2-C60杂环芳基中的任意一种;
R1、R2、R3各自独立的表示氢、氘氢、含有C1~C8的直链或带有支链的烷基、含有C1~C8的直链或带有支链的烷氧基、取代的或未取代的C6-C60芳基、取代的或未取代的C2-C60杂环芳基中的任意一种;
L1表示取代的或未取代的亚苯基、取代的或未取代的亚萘基、取代的或未取代的亚芴基、取代的或未取代的亚螺芴基、取代的或未取代的亚蒽基、取代的或未取代的亚吡啶基、取代的或未取代的亚嘧啶基、取代的或未取代的亚喹啉基和/或取代的或未取代的亚咔唑基;
x表示0-5的整数。
2.根据权利要求1所述的化合物,其特征在于:所述Ar1、Ar2、R1、R2、R3表示的基团中,所述C2-C60的杂环芳基各自独立地包含以下II-1~II-15的结构中的一种或多种:
所述式II-1至II-15中
Z1、Z2、Z3各自独立地表示氢、氘氢、卤原子、羟基、腈基、硝基、氨基、脒基、肼基、腙基、羧基或其羧酸盐、磺酸基或其磺酸盐、磷酸基或其磷酸盐、C1-C60烷基、C2-C60烯基、C2-C60炔基、C1-C60烷氧基、C3-C60环烷烃基、C3-C60环烯烃基、C6-C60芳基、至少含有一个-F、-CN或C1-C10烷基的C6-C60芳基、取代的或未取代的C6-C60芳氧基、取代的或未取代的C6-C60芳硫醚基、取代的或未取代的C2-C60杂环芳基中的任意一种;
x1表示1-4的整数;x2表示1-3的整数;x3表示1或2;x4表示1-6的整数;x5表示1-5的整数;
T1表示氧或硫。
3.根据权利要求2所述的化合物,其特征在于:所述式I所示化合物为以下POZ-1至POZ-132所示化合物中的任意一种:
4.含有权利要求1-3中任一所述式I所示化合物的材料。
5.权利要求1-3中任一所述式I所示化合物在制备有机发光二极管材料中的应用。
6.权利要求1-3任一所述式I所示化合物作为发光层材料在制备有机电致发光器件中的应用。
7.含有权利要求1-3中任一所述式I所示化合物作为发光层的有机电致发光器件。
8.根据权利要求7所述的有机电致发光器件,其特征在于: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、空穴注入层、空穴传输层、有机发光层、电子传输层和阴极层。
9.根据权利要求8所述的有机电致发光器件,其特征在于:构成所述透明基片的材料为玻璃或柔性基片;
构成所述阳极层的材料为无机材料或有机导电聚合物,所述无机材料为氧化铟锡、氧化锌、氧化锡锌、金、银或铜,所述有机导电聚合物选自聚噻吩、聚乙烯基苯磺酸钠和聚苯胺中的至少一种。
10.根据权利要求9所述的器件,其特征在于:所述空穴注入层含有以下材料中的一种或多种:
所述空穴传输层含有以下材料中的一种或多种:
构成所述有机发光层的材料包括主体材料和掺杂材料,所述主体材料含有以下材料中的一种或多种:
构成所述电子传输层的材料为所述式I所示化合物中以下结构所示化合物中的一种或多种:
构成所述有机发光层的掺杂材料还包括红色、绿色、蓝色掺杂材料,其中蓝色掺杂材料包含以下所述化合物中的一种或多种:
所述红色掺杂材料包含以下化合物中的一种或多种:
所述绿色掺杂材料包含以下化合物中的一种或多种:
构成所述阴极层的材料选自下述元素中的任意一种或任意两种组成的合金或下述元素的氟化物:锂、镁、银、钙、锶、铝、铟、铜、金和银。
11.根据权利要求9或10所述的器件,其特征在于:
其中,所述空穴注入层的厚度为30-50nm;
所述空穴传输层的厚度为5-15nm;
所述有机发光层的厚度为10-100nm;
所述电子传输层的厚度为10-30nm;
所述阴极层的厚度为90-110nm。
12.根据权利要求9或10所述的器件,其特征在于:
其中,所述空穴注入层的厚度为40nm;
所述空穴传输层的厚度为10nm;
所述有机发光层的厚度为40nm;
所述电子传输层的厚度为50nm;
所述阴极层的厚度为100nm。
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