CN105601558B - 一种电子传输型发光材料及其应用 - Google Patents

一种电子传输型发光材料及其应用 Download PDF

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CN105601558B
CN105601558B CN201610076386.3A CN201610076386A CN105601558B CN 105601558 B CN105601558 B CN 105601558B CN 201610076386 A CN201610076386 A CN 201610076386A CN 105601558 B CN105601558 B CN 105601558B
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王元勋
盛磊
雷桂平
肖立新
陈志坚
龚旗煌
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Abstract

本发明涉及一种电子传输型发光材料及其应用,本电子传输型发光材料以螺芴为母核，连接一个或者两个三联吡啶基团。螺芴是一种重要的蓝色荧光母核，其分子呈扭曲的非共平面结构，分子内共轭程度变小，引进发光波长蓝移，有效提高了器件的色纯度。同时其扭曲的结构也可以避免分子内聚集，提高发光效率。螺芴的刚性结构也极大地提高了分子的热稳定性。吡啶是一个缺电子的分子结构，是一种在OLED中被广泛应用作电子传输层的化合物。所述材料兼具两者优点，既可以用作蓝色发光材料，也可以作为电子传输材料，也可以作为电子传输兼发光材料。

Description

一种电子传输型发光材料及其应用
技术领域
本发明涉及一种电子传输型发光材料及其应用,属于有机光电材料技术领域。
背景技术
近年来，有机发光二极管(organic light emitting diode，OLED)是21世纪非常热门的新兴技术。由于其自身的优点，如可自发光、可视角度大、驱动电压低、发光亮度高、超薄、可实现柔性显示等，使其有望成为替代液晶的下一代主流显示器。由于各界的投入和努力，OLED已经取得了很大的发展。现在全世界有许多研究机构和公司投入了大量的精力去研究和开发有机电致发光器件，但是尚有许多关键问题没有得到真正解决，如蓝光的色纯度，发光器件的寿命短，效率较低等问题。
目前OLED材料中，红光和绿光材料的性能已经能够满足商业化的要求，但作为三原色之一的蓝光材料的发展却相对薄弱，这成为制约OLED全彩显示的瓶颈。由于蓝光材料能隙较宽，很难满足蓝光材料对高效率和高色纯度的要求。做好这两方面的平衡，是开发好的蓝光材料的关键。
为了提升OLED发光器件的效率，开发传输性好的电子传输材料十分重要。选择电子传输材料必须满足以下几个要求：1、有可逆的电化学还原和足够的还原电位，这是因为电子在有机薄膜中传导的过程是一连串的氧化还原反应；2、有合适的HOMO和LUMO值，这是为了使电子有最小的注入能障，减少超始/工作电压，而且最好具有空穴阻挡能力；3、有较高的电子移动率，这样才能将电荷再结合区域移至远离阴极的地方并提高电激子产生速率；4、必须具备高玻璃转移温度(Tg)和热稳定性；5、良好的光稳定性。
发明内容
本申请发明人发现，化合物螺芴是很好的蓝光母体，具有很好的热稳定性和成膜性；而吡啶为缺电子杂环，具有一定的电子传输能力，这两者结合将有希望获得一种电子传输型蓝光材料。
本发明所要解决的技术问题是提供一种电子传输型发光材料及其应用,本材料作为电子传输材料用于有机电致发光器件中，能显著提高器件的效率。作为发光材料，可以得到高效蓝光发光器件。
本发明解决上述技术问题的技术方案如下：一种电子传输型发光材料，结构式如下所示：
式中，A1和A2分别为下列结构中的一种，A1和A2相同或不同:
本发明还提供了一种上述电子传输型发光材料的制备方法，该制备方法是依照下述合成路线实现的：
通过溴代三联吡啶与2,7或2,2′螺芴二硼酸或二硼酸酯进行Suzuki偶联反应，得到目标化合物。在上述步骤中，Suzuki偶联反应在氮气保护下进行，催化剂为Pd(PPh3)4或醋酸钯，反应温度60～100℃，反应时间12～36小时。
通过上述方法，制备电子传输型发光材料C01(式3)和C21(式4)的反应流程如下：
以下所列化合物C01-C40，是符合本发明精神和原则的代表结构，应当理解，列出以下化合物结构，只是为了更好地解释本发明，并非是对本发明的限制。
本发明还提供一种电子传输型发光材料的应用，在有机电致发光器件中，发光层和/或电子传输层含有权利要求1所述的电子传输型发光材料。
在上述技术方案的基础上，本发明还可以做如下改进。
进一步，所述电子传输型发光材料作为发光层的发光材料时，单独使用或作为主体材料使用。
本发明还提供一种有机电致发光器件，包括依次叠加的ITO(氧化铟锡)导电玻璃衬底(阳极)、空穴传输层(NPB)，发光层(MADN)、电子传输层、电子注入层(LiF)和阴极层(Al)。所有功能层均可采用真空蒸镀或者溶液成膜工艺。该器件中所用到的一些有机化合物的分子结构式如下所示：
当然，本发明器件的功能层并不限于使用上述材料，这些材料可以用其他材料代替，比如空穴传输层可以用TPD等代替。这些材料的分子结构式如下所示：
本发明的有益效果是：
本发明的电子传输型发光材料应用于有机电致发光中，显著提高了器件的效率，其在有机电致发光器件的应用上有着诱人的前景。该材料的主要优点在于:
1、该材料的采用螺芴为核，两边连接三联吡啶基团，较高的位阻使芳环之间相互扭曲排列，整个分子成非平面结构，避免分子间聚集和相互作用，而且具有较高的能带；
2、具有较好的电子传输性能。用该材料制备的器件最大电流效率可达到1.1-1.34cd/A；
3、用该材料制备发光兼电子传输层制备的蓝光器件，CIE坐标(0.14-0.15，0.10-0.16)。
具体实施方式
以下对本发明的原理和特征进行描述，所举实例只用于解释本发明，并非用于限定本发明的范围。
实施例1 电子兼发光材料C01的制备
在氮气保护下，投入2,2'-二硼酸酯基螺芴(1.137g，2mmol)，4'-溴-2，2':6',2”-三溴吡啶(1.374g，4.4mmol)，碳酸钾的水溶液(80mL,0.1mol/L)，甲苯(200mL)，最后投入催化剂Pd(PPh3)4(300mg，0.26mmol)，将体系升温至90-100℃保温反应36小时。加入50mL去离子水中止反应。收集有机相,脱干后得到粗品，硅胶柱层析，淋洗剂用V乙酸乙酯：V正己烷＝1:20提纯分离，得到一白色固体,即为目标化合物C01的粗品。
将粗品采用化学气相沉积系统进一步升华提纯，升华温度为320℃，得到化合物C01，收率82％。
高分辨质谱，ESI源，正离子模式[M+1]，分子式C55H35N6，理论值779.2923，测试值779.2925。元素分析(C55H34N6)，理论值C：84.70，H：4.52，N：10.78，实测值C：84.71，H：4.53，N：10.76。
1HNMR(500MHz,CDCl3)δ:8.643-8.653(d,4H),8.539-8.570(m,8H),8.01-8.026(d,2H),7.959-7.975(d,2H),7.922-7.937(d,2H),7.792-7.822(t,4H),7.388-7.418(t,2H),7.256-7.298(m,6H),7.130-7.160(t,2H),6.75-6.765(d,2H)。
实施例2 电子兼发光材料C21的制备
在氮气保护下，投入2,7-二硼酸酯基螺芴(1.257g，2.2mmol)，4'-溴-2，2':6',2”-三溴吡啶(1.520g，4.8mmol)，碳酸钾的水溶液(88mL,0.1mol/L)，甲苯(200mL)，最后投入催化剂Pd(PPh3)4(300mg，0.26mmol)，将体系升温至90-100℃保温反应36小时。加入50mL去离子水中止反应。收集有机相,脱干后得到粗品，硅胶柱层析,淋洗剂用V1,2-二氯乙烷：V正己烷＝1:25提纯分离，得到一白色固体,即为目标化合物C21的粗品。
将粗品采用化学气相沉积系统进一步升华提纯,升华温度为315℃，得到化合物C21，收率86％。
高分辨质谱，ESI源，正离子模式[M+1]，分子式C55H35N6，理论值779.2923，测试值779.2926。元素分析(C55H34N6)，理论值C：84.70，H：4.52，N：10.78，实测值C：84.72，H：4.50，N：10.78。
1HNMR(500MHz,CDCl 3)δ:8.668-8.678(d,4H),8.579-8.594(d,4H),8.519(s,4H),8.032-8.048(d,2H),7.944-7.960(d,2H),7.891-7.906(d,2H),7.820-7.851(m,4H),7.380-7.41(m,2H),7.301-7.325(m,4H),7.210(s,2H),7.13-7.16(m,2H),6.806-6.821(d,2H)。
有机电致发光器件实施例：
本发明选取实施例1制备的化合物C01、实施例2制备的化合物C21制作有机电致发光器件，应当理解，器件实施过程与结果，只是为了更好地解释本发明，并非对本发明的限制。
实施例3 发光兼电子传输材料C01在有机电致发光器件中的应用
本实施例按照下述方法制备有机电致发光器件：
a)清洗ITO(氧化铟锡)导电玻璃：分别用去离子水、丙酮、无水乙醇超声清洗ITO玻璃各15分钟，然后在等离子体清洗器中处理2分钟；
b)在阳极ITO玻璃上真空蒸镀或者溶液成膜空穴传输层NPB，厚度为50nm；
c)在空穴传输层NPB之上，真空蒸镀发光兼电子传输层C01，厚度为60nm；
d)在C01之上，真空蒸镀电子注入层LiF，厚度1nm；
e)在电子注入层LiF之上，真空蒸镀阴极Al，厚度为100nm。
器件一的启亮电压、最大电流效率、色纯度等光电数据列于后文表1中。
实施例4 化合物C21在有机电致发光器件中的应用
以化合物C21代替化合物C01，按照实施例3所述方法，制备有机电致发光器件二，结构为ITO/NPB(50nm)/化合物C21(60nm)/LiF(1nm)/Al(100nm)，器件二的启亮电压、最大电流效率、色纯度等光电数据列于后文表1中。
表1 器件一和器件二光电数据表
实施例5 电子传输材料C01在有机电致发光器件中的应用
a)清洗ITO(氧化铟锡)导电玻璃：分别用去离子水、丙酮、无水乙醇超声清洗ITO玻璃各15分钟，然后在等离子体清洗器中处理2分钟；
b)在阳极ITO玻璃上真空蒸镀或者溶液成膜空穴传输层NPB，厚度为50nm；
c)在空穴传输层NPB之上，真空蒸镀发光Alq3，厚度为30nm；
d)在Alq3之上，真空蒸镀电子传输层C01，厚度30nm；
e)在C01之上，真空蒸镀电子注入层LiF，厚度1nm；
f)在电子注入层LiF之上，真空蒸镀阴极Al，厚度为100nm。
器件三的启亮电压、最大电流效率、色纯度等光电数据列于后文表2中。
实施例6 电子传输材料C21在有机电致发光器件中的应用
a)清洗ITO(氧化铟锡)导电玻璃：分别用去离子水、丙酮、无水乙醇超声清洗ITO玻璃各15分钟，然后在等离子体清洗器中处理2分钟；
b)在阳极ITO玻璃上真空蒸镀或者溶液成膜空穴传输层NPB，厚度为50nm；
c)在空穴传输层NPB之上，真空蒸镀发光Alq3，厚度为30nm；
d)在Alq3之上，真空蒸镀电子传输层C21，厚度30nm；
e)在C21之上，真空蒸镀电子注入层LiF，厚度1nm；
f)在电子注入层LiF之上，真空蒸镀阴极Al，厚度为100nm。
器件四的启亮电压、最大电流效率、色纯度等光电数据列于后文表2中。
表2 器件三和器件四光电数据表
以上所述仅为本发明的较佳实施例，并不用以限制本发明，凡在本发明的精神和原则之内，所作的任何修改、等同替换、改进等，均应包含在本发明的保护范围之内。

Claims (4)

1.一种电子传输型发光材料，其特征在于，结构式如下所示：
2.一种电子传输型发光材料，其特征在于，结构式如下所示：
3.一种电子传输型发光材料的应用，其特征在于，在有机电致发光器件中，发光层和/或电子传输层含有权利要求1-2任一所述的电子传输型发光材料。
4.根据权利要求3所述的应用，其特征在于，所述电子传输型发光材料作为发光层的发光材料时，单独使用或作为主体材料使用。
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