CN108623430A - 联萘衍生物、包含该联萘衍生物的材料和有机电致发光器件 - Google Patents

联萘衍生物、包含该联萘衍生物的材料和有机电致发光器件 Download PDF

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CN108623430A
CN108623430A CN201810796753.6A CN201810796753A CN108623430A CN 108623430 A CN108623430 A CN 108623430A CN 201810796753 A CN201810796753 A CN 201810796753A CN 108623430 A CN108623430 A CN 108623430A
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aryl
bases
substituted
phenyl
formulas
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曹建华
王士波
董梁
张建川
隋岩
唐永顺
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Shijiazhuang Chengzhi Yonghua Display Material Co Ltd
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Shijiazhuang Chengzhi Yonghua Display Material Co Ltd
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Abstract

本发明公开了一种联萘衍生物、包含该联萘衍生物的材料和有机电致发光器件。所述联萘衍生物的结构式如下式I所示：本发明提供的式I所示联萘衍生物，具有深蓝荧光性能，克服了荧光材料的聚集荧光淬灭效应，具有较高的玻璃化温度、高的热稳定性和优良的发光性能。其合成工艺简单，提纯的方法简单适于大规模生产，并可通过连接不同的基团调节产物的发光性能、热稳定性等，是作为有机电致发光器件有机发光层材料的理想选择。本发明使用上述荧光材料的OLED器件，其发光层的荧光效率高、稳定性好，从而使器件的发光效率和寿命都能达到实用化的要求。

Description

联萘衍生物、包含该联萘衍生物的材料和有机电致发光器件
技术领域
本发明涉及有机电致发光技术领域。更具体地，涉及一种联萘衍生物、包含该联萘衍生物的材料和有机电致发光器件。
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，有机发光(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，但是金属配合物的特殊电子结构特征，导致其蓝光材料无法达到使用要求。一方面，蓝光是三基色之一；另一方面，蓝光材料常作为母体材料，通过能量转移方式得到绿光或者红光。然而，由于自身的宽带隙，蓝光/深蓝光OLEDs的性能往往劣于绿光或红光OLEDs。目前，达到欧洲广播联盟(EBU)的蓝光标准(CIE坐标为(0.15,0.06))的高效深蓝光材料仍然很少。
迄今为止，已有许多蓝光材料在文献中进行了报道，这些材料结构大致可归类为蒽类衍生物、二苯乙烯芳香族衍生物、芘衍生物、芴和螺芴等类，而其中蒽类衍生物是应用于有机电发光组件的始祖材料，如9,10-二苯基蒽(DPA)和9,10-二(2-萘基)蒽(ADN)，虽然具有荧光量子效率高和稳定性好等优点，但其不稳定的薄膜却是加速器件衰退、造成器件寿命不佳的重要原因之一。
因此，本发明提供了一种热稳定性好且高效的联萘衍生物，以及包含该联萘衍生物的材料和有机电致发光器件。
发明内容
本发明的第一个目的在于提供一种联萘衍生物。本发明的联萘衍生物因其非平面结构，不同的稳定基团的引入形成较大的共轭体系，有效地避免分子聚集，从而得到热稳定性好的、高效的深蓝光材料。
本发明的第二个目的在于提供一种包含该联萘衍生物的材料。
本发明的第三个目的在于提供一种有机电致发光器件。
为达到上述第一个目的，本发明采用下述技术方案：
一种联萘衍生物，其结构式如下式I所示：
所述式I中：
R1和R2各自独立地选自取代的或未取代的C6-C60芳基、取代的或未取代的C6-C60含氧芳基、取代的或未取代的C2-C60杂环芳基中的任意一种；
R3和R4各自独立地选自氢原子、取代的或未取代的C6-C60芳基、取代的或未取代的C6-C60含氧芳基、取代的或未取代的C2-C60杂环芳基中的任意一种，且R3和R4不同时为氢；
R5和R6各自独立地选自氢原子、氘原子或C1-C20烷基中的任意一种。
优选地，所述C2-C60杂环芳基选自如下式II-1至式II-22所示基团中的任意一种：
所述式II-1～II-22中，表示取代位；取代基的与主体结构的连接键跨过多个环，表示该取代基可在多个环的任意取代位；
Z1、Z2和Z3各自独立地选自氢原子、氘原子、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含氧芳基、取代的或未取代的C6-C60含硫芳基、取代的或未取代的C6-C60含硼芳基、取代的或未取代的C6-C60含硅芳基、取代的或未取代的C6-C60含磷芳基中的任意一种；
x1为1～4的整数；
x2为1～3的整数；
x3为1～2的整数；
x4为1～6的整数；
x5为1～5的整数；
T1为氧或硫原子。
优选地，所述C6-C60芳基选自苯基、萘基、联苯基、蒽基、联蒽基、芘基、并四苯基、菲基、苯并菲基、苯并蒽基、苯并芘基、芴基、螺芴基中的任意一种。
优选地，所述C6-C60含氧芳基选自二苯并[b,d]呋喃-2-基、二苯并[b,d]呋喃-4-基、苯并呋喃-2-基、苯并呋喃-5-基、苯并呋喃-7-基、9,9-二甲基氧杂蒽-4-基、9,9-二甲基氧杂蒽-2-基、螺[芴-9,9’-氧杂蒽]-2’-基、螺[芴-9,9’-氧杂蒽]-2-基中的任意一种。
优选地，所述C6-C60含硫芳基选自二苯并[b,d]噻吩-2-基、二苯并[b,d]噻吩-4-基、4-苯亚砜基苯基、4-苯砜基苯基、苯并噻吩-2-基、苯并噻吩-5-基、苯并噻吩-7-基、9,9-二甲基硫杂蒽-4-基、9,9-二甲基硫杂蒽-2-基、螺[芴-9,9’-硫杂蒽]-2’-基、螺[芴-9,9’-硫杂蒽]-2-基中的任意一种。
优选地，所述C6-C60含膦芳基选自4-(二苯基氧膦基)苯基、3-(二苯基氧膦基)苯基、二苯并[b]氧膦-5-(4-苯基)-4-基中的任意一种。
优选地，所述C6-C60含硅芳基选自4-(三苯基硅基)苯基、4-(二苯基甲基硅基)苯基、3-(三苯基硅基)苯基、3-(二苯基甲基硅基)苯基中的任意一种。
优选地，所述C6-C60含硼芳基选自4-(二(2,4,6-三甲基)苯基)-硼烷苯基、二苯并[b,d]硼烷-5-苯基-4-基、三苯基硼基中的任意一种。
优选地，所述取代的C6-C60芳基、取代的C6-C60含氧芳基、取代的C2-C60杂环芳基、取代的C6-C60含硫芳基、取代的C6-C60含膦芳基、取代的C6-C60含硅芳基、取代的C6-C60含硼芳基和取代的C2-C60杂环芳基中的取代基各自独立地选自氢、氘、卤原子、C1-C20烷基、C2-C20烯基、C2-C20炔基、C1-C20烷氧基、C3-C20环烷烃基和C3-C20环烯烃基中的一种或多种。
优选地，所述取代的C6-C60含氧芳基、取代的C6-C60含硫芳基、取代的C6-C60含硼芳基、取代的C6-C60含硅芳基和取代的C6-C60含磷芳基中的取代基选自氘原子、卤原子和含有1～8个碳原子的脂肪烃基中的一种或多种。
优选地，所述结构式为式I的联萘衍生物的结构式具体如下式DN-01～DN-185中的任一种所示：
为达到上述第二个目的，本发明还提供一种材料，该材料的原料包含一种或多种上述联萘衍生物。
优选地，所述材料为有机电致发光材料。
优选地，所述有机电致发光材料为有机发光二极管材料。
另外，上述联萘衍生物在制备有机电致发光材料中的应用，也属于本发明的保护范围。
为达到上述第三个目的，本发明还提供一种有机电致发光器件，该有机电致发光器件的材料包含上述联萘衍生物中的一种或多种。
优选地，所述有机电致发光器件为有机发光二极管。
优选地，所述有机电致发光器件的有机发光层的材料包含上述联萘衍生物中的一种或多种。
优选地，所述有机电致发光器件具体可为如下结构：由下至上依次包括透明基片、阳极层、空穴传输层、有机发光层、电子传输层和阴极层。
优选地，所述有机电致发光器件包括透明基片、设于透明基片上的阳极层、设于阳极层上的空穴传输层、设于空穴传输层上的有机发光层、设于有机发光层上的电子传输层、设于电子传输层上的阴极层。
优选地，所述有机电致发光器件中阳极层和空穴传输层之间还设有空穴注入层。
优选地，构成所述透明基片的材料为玻璃或柔性基片。
优选地，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。
优选地，构成所述空穴注入层的材料为TDATA、m-MTDATA或2-TNATA；其中，所述TDATA、m-MTDATA、2-TNATA的结构式如下：
优选地，构成所述空穴传输层的材料为NPB或TPD；其中，所述NPB的结构式为
所述TPD的结构式为
优选地，构成所述有机发光层的材料为式I所示化合物、由式I所示化合物与主体材料组成的混合物、或由式I所示化合物与掺杂材料组成的混合物；当构成所述有机发光层的材料为式I所示化合物与主体材料组成的混合物时，所述式I所示化合物和主体材料的质量比为1～10:90；当构成所述有机发光层的材料为式I所示化合物与掺杂材料组成的混合物时，所述式I所示化合物和掺杂材料的质量比为90:1～10。
优选地，所述主体材料选自PVK、DPEPO、DPTPO、TBADN、E3、ADN、α,β-ADN、NPA、PNA或APBN中的任意一种：
优选地，所述掺杂材料选自BD01、BD02、BD03、BD04、BD05、BD06、BD07、BD08、BD09、BD10、BD11、BD12或BD13中的任意一种：
优选地，构成所述电子传输层的材料选自Liq、Alq3、Gaq3和BAlq所示化合物中的任意一种：
优选地，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。
优选地，所述空穴注入层的厚度为30-50nm，可更优选为40nm。
优选地，所述空穴传输层的厚度为5-15nm，可更优选为10nm。
优选地，所述有机发光层的厚度为10-100nm，可更优选为40nm。
优选地，所述电子传输层的厚度为10-30nm，可更优选为20nm。
优选地，所述阴极层的厚度为90-110nm，可更优选为100nm。
另外，上述联萘衍生物作为有机发光层材料在制备有机电致发光器件中的应用，也属于本发明的保护范围。
本发明的有益效果如下：
本发明提供的式I所示联萘衍生物，具有深蓝荧光性能，克服了荧光材料的聚集荧光淬灭效应，具有较高的玻璃化温度、高的热稳定性和优良的发光性能。其合成工艺简单，提纯的方法简单适于大规模生产，并可通过连接不同的基团调节产物的发光性能、热稳定性等，是作为有机电致发光器件有机发光层材料的理想选择。本发明使用上述荧光材料的OLED器件，其发光层的荧光效率高、稳定性好，从而使器件的发光效率和寿命都能达到实用化的要求。
附图说明
下面结合附图对本发明的具体实施方式作进一步详细的说明。
图1示出本发明式I所示化合物应用在OLED器件的结构图。
附图标记说明：1-透明基片、2-阳极层、3-空穴注入层、4-空穴传输层、5-有机发光层、6-电子传输层、7-阴极层。
具体实施方式
为了更清楚地说明本发明，下面结合优选实施例和附图对本发明做进一步的说明。附图中相似的部件以相同的附图标记进行表示。本领域技术人员应当理解，下面所具体描述的内容是说明性的而非限制性的，不应以此限制本发明的保护范围。
本发明中，制备方法如无特殊说明则均为常规方法。所用的原料如无特别说明均可从公开的商业途径获得。
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。
实施例1、化合物式DN-01的制备
第一步、中间体Int.-1的制备，制备路线如下：
制备的具体操作流程：
20.0g(69.93mol)的原料SM-0溶解在300ml无水二氯甲烷中，加入27.5g(0.35mol)的吡啶和1.5g的DMAP，缓慢滴加入43.4g(0.15mol)的三氟甲烷磺酸酐溶于二氯甲烷的溶液，室温搅拌反应8小时，加入300ml水搅拌30分钟，收集有机相减压浓缩干，用硅胶柱分离纯化，减压浓缩干，得36.5g白色固体，收率95％。
第二步、中间体Int.-2的制备，制备路线如下：
制备的具体操作流程：
将20.0g(36.3mmol)的上步中间体Int.-1用100ml甲苯溶解，加入10.6g(87.2mmol)的苯硼酸，加入20.0g(0.14mol)无水碳酸钾和50ml水以及50ml的乙醇，再加入0.42g(0.36mmol)钯催化剂Pd(PPh3)4，升温回流搅拌反应16小时，冷却到室温，减压浓缩干，用二氯甲烷和水萃取，收集有机相，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，减压浓缩干，得12.2g白色固体，收率82％。
第三步、中间体Int.-3的制备，制备路线如下：
制备的具体操作流程：
将10.0g(24.6mmol)的上步中间体Int.-2用200ml二氯甲烷溶解，冰盐浴降温至0℃，缓慢滴加入8.2g(51.6mmol)的溴素溶于20ml的二氯甲烷的溶液，搅拌反应6小时，加入20ml的饱和亚硫酸氢钠水溶液，搅拌反应10分钟，收集有机相，减压浓缩干，用硅胶柱分离纯化，减压浓缩干，得12.8g白色固体，收率92％。
第四步、化合物DN-01的制备，制备路线如下：
制备的具体操作流程：
将10.0g(17.73mmol)的上步中间体Int.-3用200ml甲苯溶解，加入5.2g(42.5mmol)的苯硼酸，加入7.5g(70.7mmol)无水碳酸钠和50ml水以及50ml的乙醇，再加入0.2g(0.17mmol)钯催化剂Pd(PPh3)4，升温回流搅拌反应16小时，冷却到室温，分出有机相，水相用二氯甲烷萃取，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，减压浓缩干，得8.7g白色固体，收率88％。
实验数据：
(1)1HNMR(δ、CDCl3)：8.164～8.184(d,2H),8.067～8.087(d,2H),7.744～7.827(m,4H),7.615～7.666(m,4H),7.455～7.542(m,6H),7.309～7.390(m,8H),7.190～7.259(m,4H)。
(2)HRMS：C44H30，标准分子量558.2348，测试结果559.2316[M+H]。
实施例2、化合物式DN-02，DN-04，DN-16，DN-49，DN-57，DN-60，DN-66，DN-80，DN-99，DN-100，DN-101，DN-109的制备
参照实施例1的合成方法，制备化合物DN-02，DN-04，DN-16，DN-49，DN-57，DN-60，DN-66，DN-80，DN-99，DN-100，DN-101，DN-109，即方法步骤同实施例1，不同之处仅在于根据所需产物不同，根据实际需要采用不同的反应物替换实施例1第二步的苯硼酸，替换实施例1第四步的苯硼酸；并根据摩尔量更改该化合物的质量用量。
实施例3、化合物式DN-36的制备
第一步、中间体Int.-4的制备，制备路线如下：
制备的具体操作流程：
将10.0g(24.6mmol)实施例1第二步的中间体Int.-2用200ml二氯甲烷溶解，冰盐浴降温至0℃，缓慢滴加入3.9g(24.6mmol)的溴素溶于10ml的二氯甲烷的溶液，搅拌反应6小时，加入20ml的饱和亚硫酸氢钠水溶液，搅拌反应10分钟，收集有机相，减压浓缩干，用硅胶柱分离纯化，减压浓缩干，得10.2g白色固体，收率86％。
第二步、化合物式DN-36的制备，制备路线如下：
制备的具体操作流程：
10g(20.6mmol)的上步中间体Int.-4、6.1g(24.7mmol)的4-(2-萘基)苯硼酸、0.24g(0.2mmol)的钯催化剂Pd(PPh3)4以及8.7g(82.4mmol)的碳酸钠，再加入60ml的甲苯、20ml的乙醇以及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，石油醚-乙酸乙酯洗脱，得11.0g白色固体，收率87％。
实验数据：
(1)1HNMR(δ、CDCl3)：7.918(s,1H),7.833～7.862(m,3H),7.778～7.814(m,2H),7.588～7.628(m,3H),7.534～7.572(m,8H),7.322～7.505(m,11H),7.203～7.271(m,4H)。
(2)HRMS：C48H32，标准分子量608.2504，测试结果609.2347[M+H]。
实施例4、化合物式DN-22，DN-24，DN-31～DN-35，DN-37～DN-40，DN-44，DN-48，DN-50，DN-51，DN-76，DN-77，DN-95，DN-108，DN-138，DN-139的制备
参照实施例3的合成方法，制备化合物DN-22，DN-24，DN-31～DN-35，DN-37～DN-40，DN-44，DN-48，DN-50，DN-51，DN-76，DN-77，DN-95，DN-108，DN-138，DN-139，即方法步骤同实施例3，不同之处仅在于根据所需产物不同，根据实际需要采用不同的反应物替换实施例3第二步的4-(2-萘基)苯硼酸，并根据摩尔量更改该化合物的质量用量。
实施例5、化合物式DN-140的制备
第一步、中间体Int.-6的制备，制备路线如下：
制备的具体操作流程：
参照实施例3第一步的方法，将实施例3第一步的Int.-2替换为DN-138，得到中间体Int.-5，白色固体，收率92％。
第二步、化合物式DN-140的制备，制备路线如下：
制备的具体操作流程：
10g(13.3mmol)的上步中间体Int.-5、2.0g(16.0mmol)的苯硼酸、0.15g(0.12mmol)的钯催化剂Pd(PPh3)4以及5.7g(53.4mmol)的碳酸钠，再加入60ml的甲苯、20ml的乙醇以及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，石油醚-乙酸乙酯洗脱，得8.8g白色固体，收率89％。
实验数据：
(1)1HNMR(δ、CDCl3)：8.288～8.307(m,2H),8.061～8.082(m,2H),7.899～7.920(m,2H),7.802～7.822(m,2H),7.739～7.761(m,4H),7.449～7.661(m,15H),7.304～7.386(m,5H),7.185～7.253(m,6H)。
(2)HRMS：C58H28D10，标准分子量744.3601，测试结果745.3455[M+H]。
实施例6、化合物式DN-03，DN-05～DN-15，DN-17～DN-21，DN-23，DN-25～DN-30，DN-41～DN-43，DN-45～DN-47，DN-52～DN-56，DN-58，DN-59，DN-61～DN-65，DN-67～DN-75，DN-78，DN-79，DN-81～DN-98，DN-102～DN-107，DN-110～DN-137的制备
参照实施例5的合成方法，制备化合物DN-03，DN-05～DN-15，DN-17～DN-21，DN-23，DN-25～DN-30，DN-41～DN-43，DN-45～DN-47，DN-52～DN-56，DN-58，DN-59，DN-61～DN-65，DN-67～DN-75，DN-78，DN-79，DN-81～DN-98，DN-102～DN-107，DN-110～DN-137，即方法步骤同实施例5，不同之处仅在于根据所需产物不同，根据实际需要采用不同的反应物替换实施例5第二步的苯硼酸，并根据摩尔量更改该化合物的质量用量。
实施例7、化合物式DN-147的制备
制备路线如下：
制备的具体操作流程：
将5.0g(8.86mmol)的实施例1制备的中间体Int.-3用80ml的甲苯溶解，加入5.0g(19.5mmol)的N-苯基-二苯并[b,d]呋喃-4-胺和2.1g(22.2mmol)的叔丁醇钠，在氮气保护下，加入62mg(0.06mmol)的钯催化剂Pd2(dba)3CHCl3以及10uL的三叔丁基磷90％甲苯溶液，升温至90℃搅拌反应16小时，冷却到室温，加入50ml水，搅拌30分钟，过滤，滤饼用乙醇洗，干燥，再用二氯甲烷-四氢呋喃重结晶，得6.7g黄色固体，收率82％。
实验数据：
(1)1HNMR(δ、CDCl3)：8.282～8.384(m,2H)，8.258～8.279(m,2H)，8.128～8.147(m,2H)，7.936～7.954(m,4H)，7.302～7.424(m,18H)，7.099～7.183(m,8H)，7.003～7.024(m,4H)，6.746～6.765(m,4H)。
(2)HRMS：C68H44N2O2，标准分子量920.3403，测试结果921.3342[M+H]。
实施例8、化合物式DN-141～DN-146，DN-148～DN-185的制备
参照实施例7的合成方法，制备结构式为DN-141～DN-146和DN-148～DN-185的化合物，即方法步骤同实施例7，不同之处仅在于根据所需产物不同，根据实际需要采用不同的反应物替换实施例7中的N-苯基-二苯并[b,d]呋喃-4-胺，并根据摩尔量更改该化合物的质量用量。
实施例9、制备器件OLED-1～OLED-5
一种有机电致发光器件，其结构如图1所示，包括透明基片1、设于透明基片1上的阳极层2、设于阳极层2上的空穴注入层3、设于空穴注入层3上的空穴传输层4、设于空穴传输层4上的有机发光层5、设于有机发光层5上的电子传输层6、设于电子传输层6上的阴极层7，其制备包括如下步骤：
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1×10-5～9×10-4Pa，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本发明化合物式I为主体材料，BD05作为掺杂材料，化合物式I：BD05的质量比为90:10，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Liq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4)中的化合物式I替换为实施例1制得的化合物DN-01，得到本发明提供的OLED-1；
按照与上相同的步骤，将步骤4)中的化合物式I替换为实施例3制得的化合物DN-36，得到本发明提供的OLED-2；
按照与上相同的步骤，将步骤4)中的化合物式I替换为实施例6制得的化合物DN-64，得到本发明提供的OLED-3；
按照与上相同的步骤，将步骤4)中的化合物式I替换为实施例2制得的化合物DN-109，得到本发明提供的OLED-4；
按照与上相同的步骤，将步骤4)中的化合物式I替换为化合物±,2-ADN，得到本发明提供的OLED-5作为对照器件；
所得器件OLED-1至OLED-5的性能检测结果如表2所示。
表2、OLED-1至OLED-5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，亮度电流密度在10mA/cm2条件下，器件的亮度均超过的参比器件OLED-5的820Cd/m2，而且器件的T95寿命均超过了参比器件。
实施例10、制备器件OLED-6～OLED-9
一种有机电致发光器件，其结构同实施例9，其制备包括如下步骤：
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1×10-5～9×10-4Pa，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本发明的化合物式I作为掺杂材料，±,2-ADN作为主体材料，α,β-ADN：化合物式I的质量比为92:8，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Liq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4)中的化合物I替换为实施例8制得的化合物DN-142，得到本发明提供的OLED-6；
按照与上相同的步骤，将步骤4)中的化合物I替换为实施例7制得的化合物DN-147，得到本发明提供的OLED-7；
按照与上相同的步骤，将步骤4)中的化合物I替换为实施例8制得的化合物DN-157，得到本发明提供的OLED-8；
按照与上相同的步骤，将步骤4)中的化合物I替换为化合物BD01，得到本发明提供的OLED-9作为对照器件；
所得器件OLED-6至OLED-9的性能检测结果如表3所示。
表3、OLED-6至OLED-9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，亮度电流密度在100mA/cm2条件下，器件的亮度均超过的参比器件OLED-9的1921Cd/m2，而且器件的T95寿命均超过了参比器件。
显然，本发明的上述实施例仅仅是为清楚地说明本发明所作的举例，而并非是对本发明的实施方式的限定，对于所属领域的普通技术人员来说，在上述说明的基础上还可以做出其它不同形式的变化或变动，这里无法对所有的实施方式予以穷举，凡是属于本发明的技术方案所引伸出的显而易见的变化或变动仍处于本发明的保护范围之列。

Claims (10)

1.一种联萘衍生物，其特征在于，所述联萘衍生物的结构式如下式I所示：
所述式I中：
R1和R2各自独立地选自取代的或未取代的C6-C60芳基、取代的或未取代的C6-C60含氧芳基、取代的或未取代的C2-C60杂环芳基中的任意一种；
R3和R4各自独立地选自氢原子、取代的或未取代的C6-C60芳基、取代的或未取代的C6-C60含氧芳基、取代的或未取代的C2-C60杂环芳基中的任意一种，且R3和R4不同时为氢；
R5和R6各自独立地选自氢原子、氘原子或C1-C20烷基中的任意一种。
2.根据权利要求1所述的联萘衍生物，其特征在于，所述C2-C60杂环芳基选自如下式II-1至式II-22所示基团中的任意一种：
所述式II-1～II-22中，表示取代位；
Z1、Z2和Z3各自独立地选自氢原子、氘原子、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含氧芳基、取代的或未取代的C6-C60含硫芳基、取代的或未取代的C6-C60含硼芳基、取代的或未取代的C6-C60含硅芳基、取代的或未取代的C6-C60含磷芳基中的任意一种；
x1为1～4的整数；
x2为1～3的整数；
x3为1～2的整数；
x4为1～6的整数；
x5为1～5的整数；
T1为氧或硫原子。
3.根据权利要求1或2所述的联萘衍生物，其特征在于，所述C6-C60芳基选自苯基、萘基、联苯基、蒽基、联蒽基、芘基、并四苯基、菲基、苯并菲基、苯并蒽基、苯并芘基、芴基、螺芴基中的任意一种；
所述C6-C60含氧芳基选自二苯并[b,d]呋喃-2-基、二苯并[b,d]呋喃-4-基、苯并呋喃-2-基、苯并呋喃-5-基、苯并呋喃-7-基、9,9-二甲基氧杂蒽-4-基、9,9-二甲基氧杂蒽-2-基、螺[芴-9,9’-氧杂蒽]-2’-基、螺[芴-9,9’-氧杂蒽]-2-基中的任意一种；
所述C6-C60含硫芳基选自二苯并[b,d]噻吩-2-基、二苯并[b,d]噻吩-4-基、4-苯亚砜基苯基、4-苯砜基苯基、苯并噻吩-2-基、苯并噻吩-5-基、苯并噻吩-7-基、9,9-二甲基硫杂蒽-4-基、9,9-二甲基硫杂蒽-2-基、螺[芴-9,9’-硫杂蒽]-2’-基、螺[芴-9,9’-硫杂蒽]-2-基中的任意一种；
所述C6-C60含膦芳基选自4-(二苯基氧膦基)苯基、3-(二苯基氧膦基)苯基、二苯并[b]氧膦-5-(4-苯基)-4-基中的任意一种；
所述C6-C60含硅芳基选自4-(三苯基硅基)苯基、4-(二苯基甲基硅基)苯基、3-(三苯基硅基)苯基、3-(二苯基甲基硅基)苯基中的任意一种；
所述C6-C60含硼芳基选自4-(二(2,4,6-三甲基)苯基)-硼烷苯基、二苯并[b,d]硼烷-5-苯基-4-基、三苯基硼基中的任意一种。
4.根据权利要求1或2所述的联萘衍生物，其特征在于，所述取代的C6-C60芳基、取代的C6-C60含氧芳基、取代的C2-C60杂环芳基、取代的C6-C60含硫芳基、取代的C6-C60含膦芳基、取代的C6-C60含硅芳基、取代的C6-C60含硼芳基和取代的C2-C60杂环芳基中的取代基各自独立地选自氘、卤原子、C1-C20烷基、C2-C20烯基、C2-C20炔基、C1-C20烷氧基、C3-C20环烷烃基和C3-C20环烯烃基中的一种或多种。
5.根据权利要求1所述的联萘衍生物，其特征在于，所述结构式为式I的联萘衍生物的结构式具体如下式DN-01～DN-185中的任一种所示：
6.一种材料，其特征在于，所述材料的原料包含权利要求1-5任一项权利要求所述的联萘衍生物。
7.一种有机电致发光器件，其特征在于，该有机电致发光器件的材料包含权利要求1-5任一项所述的联萘衍生物。
8.根据权利要求7所述的有机电致发光器件，其特征在于，该电致发光器件的有机发光层包含有所述联萘衍生物。
9.根据权利要求8所述的有机电致发光器件，其特征在于，构成所述有机发光层的材料为式I所示化合物、由式I所示化合物与主体材料组成的混合物、或由式I所示化合物与掺杂材料组成的混合物。
10.根据权利要求9所述的有机电致发光器件，其特征在于，当构成所述有机发光层的材料为式I所示化合物与主体材料组成的混合物时，所述式I所示化合物和主体材料的质量比为1～10:90；当构成所述有机发光层的材料为式I所示化合物与掺杂材料组成的混合物时，所述式I所示化合物和掺杂材料的质量比为90:1～10；
所述主体材料选自PVK、DPEPO、DPTPO、TBADN、E3、ADN、α,β-ADN、NPA、PNA或APBN中的任意一种；所述掺杂材料选自BD01、BD02、BD03、BD04、BD05、BD06、BD07、BD08、BD09、BD10、BD11、BD12或BD13中的任意一种。
CN201810796753.6A 2018-07-19 2018-07-19 联萘衍生物、包含该联萘衍生物的材料和有机电致发光器件 Pending CN108623430A (zh)

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