CN107739345A - 一种含有三嗪结构的衍生物及其制备方法和有机电致发光器件 - Google Patents

一种含有三嗪结构的衍生物及其制备方法和有机电致发光器件 Download PDF

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CN107739345A
CN107739345A CN201711054635.XA CN201711054635A CN107739345A CN 107739345 A CN107739345 A CN 107739345A CN 201711054635 A CN201711054635 A CN 201711054635A CN 107739345 A CN107739345 A CN 107739345A
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张弘
蔡辉
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Changchun Haipurunsi Technology Co Ltd
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Abstract

本发明提供一种含有三嗪结构的衍生物及其制备方法和有机电致发光器件，属于有机光电材料技术领域。该化合物具有式(Ⅰ)所示结构。本发明的含有三嗪类结构的衍生物热稳定性能高、玻璃化温度高；制备方法简单、原料易得，采用常规的偶联反应制得成品，能够满足工业化发展的需要；采用本发明的新的三嗪结构的衍生物制造的器件具表现出驱动电压低、发光效率高的优点，是性能优异的有机发光材料。

Description

一种含有三嗪结构的衍生物及其制备方法和有机电致发光 器件
技术领域
本发明涉及有机光电材料技术领域，具体涉及一种含有三嗪结构的衍生物及其制备方法和有机电致发光器件。
背景技术
随着信息产业的进步，传统的显示器已不能满足人们的要求，如：阴极射线管(cathode ray tube,CRT)显示器体积大、驱动电压高；液晶显示器(liquid crystaldisplay,LCD)亮度低、视角窄、工作温度范围小；等离子显示器(plasma display panel,PDP)造价昂贵、分辨率不高、耗电量大。
有机电致发光二极管(organic light-emitting diodes,OLEDs)作为一种全新的显示技术在各个性能上拥有现有显示技术无以伦比的优势，如具有全固态、自主发光、亮度高、高分辨率、视角宽(170度以上)、响应速度快、厚度薄、体积小、重量轻、可使用柔性基板、低电压直流驱动(3-10V)、功耗低、工作温度范围宽等，使得它的应用市场十分广泛，如照明系统、通讯系统、车载显示、便携式电子设备、高清晰度显示甚至是军事领域。
发光材料分为荧光材料和磷光材料，发光层的形成方法是荧光主体材料中掺杂磷光材料(有机金属)的方法和荧光主体材料掺杂荧光(包含氮的有机物)掺杂剂的方法。常用的主体材料概可以分为几种，如空穴传输主体材料、电子传输主体材料、双极主体材料、惰性主体材料、荧光配合物主体材料和磷光配合物主体材料。
在使用磷光材料制备的有机发光器件中，大多使用TPD等含有三苯胺基团材料当作发光层的主体发光材料。然而，这一类材料的热稳定性较差，导致使用磷光材料的有机发光器件的寿命较短，因而降低了此类材料的使用程度。如何设计新的性能更好的材料进行调节，一直是本领域技术人员亟待解决的问题。
发明内容
本发明的目的是提供一种含有三嗪结构的衍生物及其制备方法和有机电致发光器件。本发明提供的含有三嗪类结构的衍生物热稳定性能高、玻璃化温度高、制备方法简单，将该化合物作为发光层中的主体材料使用而制成的有机发光器件，表现出驱动电压低、发光效率高的优点，是性能优良的有机发光材料。
本发明首先提供一种含有三嗪结构的衍生物，结构式为：
其中，R1、R2、R3、R4和R5独立的选自H、C1～C30烷基、取代或未取代C6～C60芳基、取代或未取代的C4～C60的杂环基中的一种。
优选的，R1、R2、R3、R4和R5独立的选自H、C1～C10烷基、取代或未取代C6～C30芳基、取代或未取代的C4～C30的杂环基中的一种。
优选的，所述的R1、R2、R3、R4和R5独立的选自H、甲基、乙基、异丙基、叔丁基或取代或未取代的如下基团中的一种：苯基、萘基、蒽基、菲基、联苯基、三联苯基、芴基、螺二芴基、咔唑基、二苯并噻吩基、二苯并呋喃基、喹啉基、异喹啉基或三嗪基。
优选的，R5选自取代或未取代的芴基、取代或未取代的苯基、取代或未取代的联苯基、取代或未取代的萘基、取代或未取代的蒽基、取代或未取代的喹啉基中的一种。
优选的，所述的含有三嗪结构的衍生物选自如下所示结构中的任意一种：
本发明还提供一种含有三嗪结构的衍生物的制备方法，制备路线如下：
其中，R1、R2、R3、R4和R5独立的选自H、C1～C30烷基、取代或未取代C6～C60芳基、取代或未取代的C4～C60的杂环基中的一种。
本发明还提供一种有机电致发光器件，所述有机电致发光器件包括阳极、阴极、有机物层；所述有机物层含有所述的含有三嗪结构的衍生物。
优选的，所述有机层中含有发光层，所述发光层中含有所述的含有三嗪结构的衍生物。
本发明的有益效果:
本发明首先提供一种含有三嗪结构的衍生物，该化合物具有式(Ⅰ)所示结构，本发明的含有三嗪类结构的衍生物热稳定性能高、玻璃化温度高；制备方法简单、原料易得，采用常规的偶联反应制得成品，能够满足工业化发展的需要；采用本发明的新的三嗪结构的衍生物制造的器件具表现出驱动电压低、发光效率高的优点，是性能优异的有机发光材料。
具体实施方式
为了进一步理解本发明，下面结合实施例对本发明优选实施方案进行描述，但是应当理解，这些描述只是为进一步说明本发明的特征和优点，而不是对本发明权利要求的限制。
本发明首先提供一种含有三嗪结构的化合物，结构式为：
其中，R1、R2、R3、R4和R5独立的选自H、C1～C30烷基、取代或未取代C6～C60芳基、取代或未取代的C4～C60的杂环基中的一种。
优选的，R1、R2、R3、R4和R5独立的选自H、C1～C10烷基、取代或未取代C6～C30芳基、取代或未取代的C4～C30的杂环基中的一种。
优选的，R1、R2、R3、R4和R5独立的选自H、甲基、乙基、异丙基、叔丁基或取代或未取代的如下基团中的一种：苯基、萘基、蒽基、菲基、联苯基、三联苯基、芴基、螺二芴基、咔唑基、二苯并噻吩基、二苯并呋喃基、喹啉基、异喹啉基或三嗪基。
优选的，R5选自取代或未取代的芴基、取代或未取代的苯基、取代或未取代的联苯基、取代或未取代的萘基、取代或未取代的蒽基、取代或未取代的喹啉基中的一。
需要说明的是，本发明提到的取代的各类基团中，所述取代基选自C1～C10的烷基、C6～C30的芳基或C4～C30的杂环基。所述取代基的个数优选为1～3个。
具体的，所述含有三嗪结构的衍生物优选选自如下结构中的任意一种：
本发明还提供一种含有三嗪结构的衍生物的制备方法，制备路线如下：
其中，R1、R2、R3、R4和R5独立的选自H、C1～C30烷基、取代或未取代C6～C60芳基、取代或未取代的C4～C60的杂环基中的一种。
本发明还提供一种有机电致发光器件，包括阳极、阴极、有机物层；所述有机物层含有所述的含有三嗪结构的衍生物。
优选的，所述有机层中含有发光层，所述发光层中含有所述的含有三嗪结构的衍生物。
本发明对以下实施例中所采用的原料没有特别的限制，可以为市售产品或采用本领域技术人员所熟知的制备方法制备得到。
实施例1：
化合物1的制备
中间体1-3的制备
在氮气的保护下，向2L反应釜中加入1-1(16.01g，100.08mmol)，1-2(21.02g，100.08mmol)，碳酸钾(1.24g，9.00mmol)，甲苯200mL搅拌。
反应釜内温度升到70℃，加入Pd(PPh3)4(1.04g，0.90mmol)，蒸馏水100mL搅拌，搅拌回流11h，充分反应。
加入70mL蒸馏水终止反应后，减压过滤，用蒸馏水洗涤固体，然后用丙酮，甲苯，THF来重结晶，得到固体后再升华，甲苯重结晶，得到中间体1-3 23.23g，产率为80.44％。
中间体1-3(1)的制备
在避光的条件下，向2L反应釜中加入1-3(24.53g，100.00mmol)，NBS(29.44g，120.00mmol)，四氯化碳200mL搅拌，过氧化苯甲酰引发，反应釜内温度升到70℃，反应5小时，加入70mL蒸馏水终止反应后，减压过滤，用蒸馏水洗涤固体，然后用丙酮，甲苯，THF来重结晶，得到固体后再升华，甲苯重结晶，得到中间体1-3 26.83g，产率为82.75％。
中间体1-4的制备
将中间体1-3的制备中的1-1替换为1-3(1)，其他步骤均与中间体1-3的制备相同，得到中间体1-4 28.23g，产率为81.78％。
中间体1-4(1)的制备
将中间体1-3(1)的制备中的1-3替换为1-4，其他步骤均与中间体1-3(1)的制备相同，得到中间体1-4(1)27.68g，产率为82.20％。
化合物1的制备
将中间体1-3的制备中的1-1替换为1-4(1)，其他步骤均与中间体1-3的制备相同，得到化合物1 31.89g，产率为83.37％。质谱m/z：573.7(计算值：573.6)。理论元素含量(％)C42H27N3：C，87.93；H，4.74；N，7.32。实测元素含量(％)：C，87.92；H，4.73；N，7.33。
实施例2
化合物7的制备
将实施例1中的R1、R2、R5基团替换为如上所示R1、R2、R5基团，其他步骤均与实施例1相同，得到化合物7。质谱m/z：801.31(计算值：801.32)。理论元素含量(％)C60H39N3：C，89.86；H，4.90；N，5.24。实测元素含量(％)：C，89.87；H，4.89；N，5.23。
实施例3
化合物TM12的制备
将实施例1中的R1、R2、R3、R4、R5基团替换为如上所示R1、R2、R3、R4、R5基团，其他步骤均与实施例1相同，得到化合物7。质谱m/z：953.38(计算值：953.36)。理论元素含量(％)C72H47N3：C，90.63；H，4.97；N，4.40。实测元素含量(％)：C，90.62；H，4.96；N，4.41。
实施例4
化合物14的制备
将实施例1中的R1、R3、R5基团替换为如上所示R1、R3、R5基团，其他步骤均与实施例1相同，得到化合物7。质谱m/z：801.31(计算值：801.32)。理论元素含量(％)C60H39N3：C，89.86；H，4.90；N，5.24。实测元素含量(％)：C，89.87；H，4.89；N，5.23。
实施例5
化合物15的制备
将实施例1中的R1、R3、R4、R5基团替换为如上所示R1、R3、R4、R5基团，其他步骤均与实施例1相同，得到化合物15。质谱m/z：877.35(计算值：877.36)。理论元素含量(％)C66H43N3：C，90.28；H，4.94；N，4.79。实测元素含量(％)：C，90.26；H，4.93；N，4.78。
实施例6
化合物18的制备
将实施例1中的R1、R3、R5基团替换为如上所示R1、R、R5基团，其他步骤均与实施例1相同，得到化合物18。质谱m/z：725.28(计算值：725.29)。理论元素含量(％)C54H35N3：C，89.35；H，4.86；N，5.79。实测元素含量(％)：C，89.34；H，4.87；N，5.78。
实施例7
化合物26的制备
将实施例1中的R1、R4、R5基团替换为如上所示R1、R4、R5基团，其他步骤均与实施例1相同，得到化合物26。质谱m/z：601.25(计算值：601.26)。理论元素含量(％)C44H31N3：C，87.82；H，5.19；N，6.98。实测元素含量(％)：C，87.83；H，5.20；N，6.97。
实施例8
化合物36的制备
将实施例1中的R1、R3、R4、R5基团替换为如上所示R1、R3、R4、R5基团，其他步骤均与实施例1相同，得到化合物36。质谱m/z：629.28(计算值：629.29)。理论元素含量(％)C46H35N3：C，87.73；H，5.60；N，6.67。实测元素含量(％)：C，87.84；H，5.61；N，6.68。
实施例9
化合物44的制备
将实施例1中的R1、R3、R5基团替换为如上所示R1、R3、R5基团，其他步骤均与实施例1相同，得到化合物44。质谱m/z：601.25(计算值：601.28)。理论元素含量(％)C44H31N3：C，87.82；H，5.19；N，6.98。实测元素含量(％)：C，87.84；H，5.20；N，6.97。
实施例10
化合物50的制备
将实施例1中的R1、R2、R5基团替换为如上所示R1、R2、R5基团，其他步骤均与实施例1相同，得到化合物50。质谱m/z：629.28(计算值：629.29)。理论元素含量(％)C46H35N3：C，87.73；H，5.60；N，6.67。实测元素含量(％)：C，87.74；H，5.59；N，6.68。
实施例11
化合物68的制备
将实施例1中的R1、R2、R5基团替换为如上所示R1、R2、R5基团，其他步骤均与实施例1相同，得到化合物68。质谱m/z：827.30(计算值：827.31)。理论元素含量(％)C60H37N5：C，87.04；H，4.50；N，8.46。实测元素含量(％)：C，87.05；H，4.51；N，8.47。
实施例12
化合物80的制备
将实施例1中的R1、R3、R5基团替换为如上所示R1、R3、R5基团，其他步骤均与实施例1相同，得到化合物80。质谱m/z：905.30(计算值：905.31)。理论元素含量(％)C66H39N3O2：C，87.49；H，4.34；N，4.64；O，3.53。实测元素含量(％)：C，87.48；H，4.35；N，4.65；O，3.52。
实施例13
化合物113的制备
将实施例1中的R1、R3、R4、R5基团替换为如上所示R1、R3、R4、R5基团，其他步骤均与实施例1相同，得到化合物113。质谱m/z：789.31(计算值：789.32)。理论元素含量(％)C59H39N3：C，89.70；H，4.98；N，5.32。实测元素含量(％)：C，89.71；H，4.97；N，5.33。
[对比应用实施例]
将透明阳极电极ITO基板分别用去离子水、丙酮、乙醇超声清洗各15分钟，然后在等离子清洗器中清洗2分钟，干燥并且抽真空至5×10-5Pa。随后将处理后的ITO基板进行蒸镀。首先蒸镀一层NPB作为空穴传输层，蒸镀速率为0.1nm/s，蒸镀厚度为10nm。然后是发光层的蒸镀，混合蒸镀所述有机发光材料CBP/Ir(PPy)3，作为绿光磷光掺杂材料，掺杂浓度为5％，蒸镀速率为0.005nm/s，蒸镀厚度为30nm，随后蒸镀50nm的Alq3作为电子传输层，蒸镀速率为0.01nm/s，在电子传输层上真空蒸镀Al层作为阴极，厚度为30nm。
[应用实施例1-9]
将透明阳极电极ITO基板分别用去离子水、丙酮、乙醇超声清洗各15分钟，然后在等离子清洗器中清洗2分钟，干燥并且抽真空至5×10-5Pa。随后将处理后的ITO基板进行蒸镀。首先蒸镀一层NPB作为空穴传输层，蒸镀速率为0.1nm/s，蒸镀厚度为10nm。然后是发光层的蒸镀，混合蒸镀本发明含有三嗪结构的衍生物/Ir(PPy)3，作为绿光磷光掺杂材料，掺杂浓度为5％，蒸镀速率为0.005nm/s，蒸镀厚度为30nm，随后蒸镀50nm的Alq3作为电子传输层，蒸镀速率为0.01nm/s，在电子传输层上真空蒸镀Al层作为阴极，厚度为30nm。
上述方法制造的有机发光器件的电子发光特性在下表中表示：
以上结果表明，本发明的化合物作为发光层的主体材料，应用于有机电致发光器件中，发光效率高，是性能良好的有机发光材料。
虽然本发明用示范性实施方案进行了特别的描述，但应该理解在不偏离权利要求所限定的本发明的精神与范围的情况下，本领域普通技术人员可对其进行各种形式和细节上的改变。

Claims (8)

1.一种含有三嗪结构的衍生物，其特征在于,具有如下通式(Ⅰ)所示结构：
其中，R1、R2、R3、R4和R5独立的选自H、C1～C30烷基、取代或未取代C6～C60芳基、取代或未取代的C4～C60的杂环基中的一种。
2.根据权利要求1所述含有三嗪结构的衍生物，其特征在于，R1、R2、R3、R4和R5独立的选自H、C1～C10烷基、取代或未取代C6～C30芳基、取代或未取代的C4～C30的杂环基中的一种。
3.根据权利要求1所述含有三嗪结构的衍生物，其特征在于，R1、R2、R3、R4和R5独立的选自H、甲基、乙基、异丙基、叔丁基或取代或未取代的如下基团中的一种：苯基、萘基、蒽基、菲基、联苯基、三联苯基、芴基、螺二芴基、咔唑基、二苯并噻吩基、二苯并呋喃基、喹啉基、异喹啉基或三嗪基。
4.根据权利要求1所述含有三嗪结构的衍生物，其特征在于，R5选自取代或未取代的芴基、取代或未取代的苯基、取代或未取代的联苯基、取代或未取代的萘基、取代或未取代的蒽基、取代或未取代的喹啉基中的一种。
5.根据权利要求1所述含有三嗪结构的衍生物，其特征在于，选自如下所示结构中的任意一种：
6.权利要求1-5任一项所述的含有三嗪结构的衍生物的制备方法，其特征在于，通过如下路线合成得到：
其中，R1、R2、R3、R4和R5独立的选自H、C1～C30烷基、取代或未取代C6～C60芳基、取代或未取代的C4～C60的杂环基中的一种。
7.一种有机电致发光器件，其特征在于，所述有机电致发光器件包括阳极、阴极、有机物层；所述有机物层含有权利要求1-5任一项所述的含有三嗪结构的衍生物。
8.根据权利要求7所述的有机电致发光器件，其特征在于，所述有机层中含有发光层，所述发光层中含有权利要求1-5任一项所述的含有三嗪结构的衍生物。
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Publication number Priority date Publication date Assignee Title
CN109273615A (zh) * 2018-09-11 2019-01-25 长春海谱润斯科技有限公司 一种有机发光器件
CN112759578A (zh) * 2019-11-01 2021-05-07 北京夏禾科技有限公司 一种有机化合物、包含其的电致发光器件及其用途
EP3882238A1 (en) * 2020-03-19 2021-09-22 Idemitsu Kosan Co.,Ltd. Compound, material for an organic electroluminescence device and an organic electroluminescence device comprising the compound

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109273615A (zh) * 2018-09-11 2019-01-25 长春海谱润斯科技有限公司 一种有机发光器件
CN109273615B (zh) * 2018-09-11 2020-09-25 长春海谱润斯科技有限公司 一种有机发光器件
CN112759578A (zh) * 2019-11-01 2021-05-07 北京夏禾科技有限公司 一种有机化合物、包含其的电致发光器件及其用途
CN112759578B (zh) * 2019-11-01 2023-09-15 北京夏禾科技有限公司 一种有机化合物、包含其的电致发光器件及其用途
EP3882238A1 (en) * 2020-03-19 2021-09-22 Idemitsu Kosan Co.,Ltd. Compound, material for an organic electroluminescence device and an organic electroluminescence device comprising the compound

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