CN107915737A - 一种含有咪唑结构的衍生物及其制备方法和有机电致发光器件 - Google Patents
一种含有咪唑结构的衍生物及其制备方法和有机电致发光器件 Download PDFInfo
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- CN107915737A CN107915737A CN201711123522.0A CN201711123522A CN107915737A CN 107915737 A CN107915737 A CN 107915737A CN 201711123522 A CN201711123522 A CN 201711123522A CN 107915737 A CN107915737 A CN 107915737A
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- 0 CC(C)(c1c-2cccc1)[n]1*-2nc2ccc(C3C=CC=CC3)cc12 Chemical compound CC(C)(c1c-2cccc1)[n]1*-2nc2ccc(C3C=CC=CC3)cc12 0.000 description 13
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- QEYFRCKSOHLENP-UHFFFAOYSA-N CC(c1ccccc1-1)(c2ccc(cc3)c4c2C=CC2c4c3C=CC2)[n]2c-1nc(cc1)c2cc1C1=CC=CCC1 Chemical compound CC(c1ccccc1-1)(c2ccc(cc3)c4c2C=CC2c4c3C=CC2)[n]2c-1nc(cc1)c2cc1C1=CC=CCC1 QEYFRCKSOHLENP-UHFFFAOYSA-N 0.000 description 1
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- FKLDTGIVUGJYAC-UHFFFAOYSA-N CC1(N2c3cc(-c4ccccc4)ccc3NC2c2c1cccc2)[n]1c2ccccc2c2ccccc12 Chemical compound CC1(N2c3cc(-c4ccccc4)ccc3NC2c2c1cccc2)[n]1c2ccccc2c2ccccc12 FKLDTGIVUGJYAC-UHFFFAOYSA-N 0.000 description 1
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- NEGAIVRTASMPCY-UHFFFAOYSA-N CC1NC=CC2C1=CC=CC2C(C)(c1c-2cccc1)[n]1c-2nc(cc2)c1cc2-c1ccccc1 Chemical compound CC1NC=CC2C1=CC=CC2C(C)(c1c-2cccc1)[n]1c-2nc(cc2)c1cc2-c1ccccc1 NEGAIVRTASMPCY-UHFFFAOYSA-N 0.000 description 1
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- XEQIQHHSUTWKQZ-UHFFFAOYSA-N Cc1ccc(C(c2c-3cccc2)(C2=CC=C4C=NC=CC4C2)[n]2c-3nc3c2cccc3)cc1 Chemical compound Cc1ccc(C(c2c-3cccc2)(C2=CC=C4C=NC=CC4C2)[n]2c-3nc3c2cccc3)cc1 XEQIQHHSUTWKQZ-UHFFFAOYSA-N 0.000 description 1
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- GCRHEEYIKRGGQL-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)ccc1-c1ccc(C(c2ccccc2-2)(c(cc3)cc4c3cncc4)[n]3c-2nc2ccccc32)cc1 Chemical compound c(cc1)ccc1-c(cc1)ccc1-c1ccc(C(c2ccccc2-2)(c(cc3)cc4c3cncc4)[n]3c-2nc2ccccc32)cc1 GCRHEEYIKRGGQL-UHFFFAOYSA-N 0.000 description 1
- RZUNXMAWADDDGN-UHFFFAOYSA-N c(cc1)ccc1-c1ccc(C(c2c-3cccc2)(c(cc2)cc4c2cncc4)[n]2c-3nc3c2cccc3)cc1 Chemical compound c(cc1)ccc1-c1ccc(C(c2c-3cccc2)(c(cc2)cc4c2cncc4)[n]2c-3nc3c2cccc3)cc1 RZUNXMAWADDDGN-UHFFFAOYSA-N 0.000 description 1
- MEZRPBKVFRLRIY-UHFFFAOYSA-N c1ccc(C(c2c-3cccc2)(c(cc2)cc4c2nccc4)[n]2c-3nc3c2cccc3)cc1 Chemical compound c1ccc(C(c2c-3cccc2)(c(cc2)cc4c2nccc4)[n]2c-3nc3c2cccc3)cc1 MEZRPBKVFRLRIY-UHFFFAOYSA-N 0.000 description 1
- IFQGTRZDBJUZPA-UHFFFAOYSA-N c1ccc(C(c2c-3cccc2)(c2cc4ccccc4cc2)[n]2c-3nc3c2cccc3)cc1 Chemical compound c1ccc(C(c2c-3cccc2)(c2cc4ccccc4cc2)[n]2c-3nc3c2cccc3)cc1 IFQGTRZDBJUZPA-UHFFFAOYSA-N 0.000 description 1
- SEAUIHUSMHHMJI-UHFFFAOYSA-N c1ccc(C(c2c-3cccc2)(c2ccccc2)[n]2c-3nc3c2cccc3)cc1 Chemical compound c1ccc(C(c2c-3cccc2)(c2ccccc2)[n]2c-3nc3c2cccc3)cc1 SEAUIHUSMHHMJI-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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Abstract
本发明提供一种含有咪唑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。本发明提供的含有咪唑结构的衍生物具有式(Ⅰ)所示结构,
Description
技术领域
本发明涉及有机光电材料技术领域,具体涉及一种含有咪唑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。
有机电致发光材料在近些年内不断实现突破,取得了令人瞩目的进展,对传统的显示材料构成了强有力的挑战。柔性OLED商业化以后,目前世界上与之相关的科研及商业力量都在不遗余力的开展这方面的工作。虽然有机电致发光材料研究已经取得巨大的成果,但是OLED在商业化的过程中还有一些亟待解决的问题。
电子传输材料在分子结构上表现为缺电子体系,具有较强的电子接受能力,电子传输材料还应具有较好的可逆还原过程。常用的电子传输材料主要包括四氰基苯醌二甲烷(TCNQ)、三硝基芴酮(TNF)、(8-羟基喹啉)铝(Alq3)、噫二唑(Oxadiazole)、三氮唑(Triazole)、萘酐、花酐、C60及其衍生物等。
但是目前公开的电子传输材料在效率和寿命都有待提高,所以开发稳定高效的电子传输材料,提高器件效率,延长器件寿命,具有很重要的实际应用价值。
发明内容
本发明的目的是提供一种含有咪唑结构的衍生物及其制备方法和有机电致发光器件,本发明提供的化合物稳定性好,电子迁移率高,玻璃化温度高,成膜性好,合成方法简单易操作,使用该衍生物制备的有机电致发光器件具有良好的发光效率和寿命表现。
本发明首先提供一种含有咪唑结构的衍生物,结构式为:
其中,R1、R2、R3、R4独立的选自氢、取代或未取代的C1-C60烷基、取代或未取代的C6-C60的芳基、取代或未取代的C3~C60的杂环基中的一种。
优选的,所述的R1、R2、R3、R4独立的选自氢、取代或未取代的C1-C30烷基、取代或未取代的C6-C30的芳基、取代或未取代的C3~C30的杂环基中的一种。
优选的,所述的R1、R2、R3、R4独立的选自氢、C1~C4烷基或取代或未取代的如下基团:苯基、萘基、蒽基、菲基、芴基、螺二芴基、咔唑基、二苯并噻吩基、二苯并呋喃基、三嗪基、喹啉基或异喹啉基。
优选的,所述的含有咪唑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咪唑结构的衍生物的制备方法,制备路线如下:
其中,R1、R2、R3、R4独立的选自氢、取代或未取代的C1-C60烷基、取代或未取代的C6-C60的芳基、取代或未取代的C3~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咪唑结构的衍生物。
优选的,所述有机物层包括电子传输层,所述电子传输层中含有所述的含有咪唑结构的衍生物。
本发明的有益效果:
本发明首先提供一种含有咪唑结构的衍生物,该衍生物具有式(I)所示结构,由于咪唑基团的存在,材料具有优异的电子传输能力,电子迁移率高;共轭体系存在,稳定性好,玻璃化温度高;成膜性好,能够防止结晶的作用;合成方法简单易操作,使用该衍生物制备的有机电致发光器件具有良好的发光效率和寿命表现。
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咪唑结构的化合物,结构式为:
其中,R1、R2、R3、R4独立的选自氢、取代或未取代的C1-C60烷基、取代或未取代的C6-C60的芳基、取代或未取代的C3~C60的杂环基中的一种。
优选的,R1、R2、R3、R4独立的选自氢、取代或未取代的C1-C30烷基、取代或未取代的C6-C30的芳基、取代或未取代的C3~C30的杂环基中的一种。
优选的,R1、R2、R3、R4独立的选自氢、C1~C4烷基或取代或未取代的如下基团:苯基、萘基、蒽基、菲基、芴基、螺二芴基、咔唑基、二苯并噻吩基、二苯并呋喃基、三嗪基、喹啉基或异喹啉基。
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,所述含有咪唑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咪唑结构的衍生物的制备方法,制备路线如下:
其中,R1、R2、R3、R4独立的选自氢、取代或未取代的C1-C60烷基、取代或未取代的C6-C60的芳基、取代或未取代的C3~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咪唑结构的衍生物。
优选的,所述有机物层包括电子传输层,所述电子传输层中含有所述的含有咪唑结构的衍生物。
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
在氩气的保护下,将二氯甲烷(45%,200ml)添加到1-1(22.02g,100.00mmol)和催化剂1-2(9.54g,100.00mmol)中,室温下搅拌24h。用饱和硫代硫酸钠溶液洗涤产物,并用乙酸乙酯萃取。有几层用饱和盐水洗涤,并且用无水硫酸钠干燥。对有机提取物进行减压抽滤,重结晶得到1 19.46g,产率为83.04%。质谱m/z:234.30(计算值:234.31)。理论元素含量(%)C16H14N2:C,82.02;H,6.02;N,11.96。实测元素含量(%):C,82.03;H,6.03;N,11.98。上述证实获得产物为目标产物1。
实施例2
化合物12的制备
将实施例1中的R1、R2、R3、R4基团替换为如上所示R1、R2、R3、R4基团,得到化合物12。质谱m/z:420.16(计算值:420.15)。理论元素含量(%)C31H20N2:C,88.54;H,4.79;N,6.66。实测元素含量(%):C,88.53;H,4.78;N,6.65。上述证实获得产物为目标产物12。
实施例3
化合物19的制备
将实施例1中的R1、R2、R3、R4基团替换为如上所示R1、R2、R3、R4基团,得到化合物19。质谱m/z:461.57(计算值:461.58)。理论元素含量(%)C33H23N3:C,85.57;H,5.02;N,9.10。实测元素含量(%):C,85.56;H,5.03;N,9.12。上述证实获得产物为目标产物19。
实施例4
化合物28的制备
将实施例1中的R1、R2、R3、R4基团替换为如上所示R1、R2、R3、R4基团,得到化合物28。质谱m/z:470.66(计算值:470.65)。理论元素含量(%)C34H34N2:C,86.77;H,7.28;N,5.95。实测元素含量(%):C,86.78;H,7.29;N,5.96。上述证实获得产物为目标产物28。
实施例5
化合物33的制备
将实施例1中的R1、R2、R3、R4基团替换为如上所示R1、R2、R3、R4基团,得到化合物33。质谱m/z:409.49(计算值:409.50)。理论元素含量(%)C29H19N3:C,85.06;H,4.68;N,10.26。实测元素含量(%):C,85.07;H,4.64;N,10.25。上述证实获得产物为目标产物33。
实施例6
化合物48的制备
将实施例1中的R1、R2、R3、R4基团替换为如上所示R1、R2、R3、R4基团,得到化合物48。质谱m/z:474.62(计算值:474.61)。理论元素含量(%)C35H26N2:C,88.58;H,5.52;N,5.90。实测元素含量(%):C,88.59;H,5.53;N,5.91。上述证实获得产物为目标产物48。
实施例7
化合物58的制备
将实施例1中的R1、R2、R3、R4基团替换为如上所示R1、R2、R3、R4基团,得到化合物58。质谱m/z:361.45(计算值:361.46)。理论元素含量(%)C25H19N3:C,83.08;H,5.30;N,11.63。实测元素含量(%):C,83.09;H,5.31;N,11.64。上述证实获得产物为目标产物58。
实施例8
化合物68的制备
将实施例1中的R1、R2、R3、R4基团替换为如上所示R1、R2、R3、R4基团,得到化合物68。质谱m/z:475.60(计算值:475.61)。理论元素含量(%)C34H25N3:C,85.87;H,5.30;N,8.84。实测元素含量(%):C,85.86;H,5.31;N,8.85。上述证实获得产物为目标产物68。
实施例9
化合物72的制备
将实施例1中的R1、R2、R3、R4基团替换为如上所示R1、R2、R3、R4基团,得到化合物72。质谱m/z:399.50(计算值:399.51)。理论元素含量(%)C28H21N3:C,84.18;H,5.30;N,10.52。实测元素含量(%):C,84.19;H,5.31;N,10.53。上述证实获得产物为目标产物72。
实施例10
化合物80的制备
将实施例1中的R1、R2、R3、R4基团替换为如上所示R1、R2、R3、R4基团,得到化合物80。质谱m/z:428.58(计算值:428.56)。理论元素含量(%)C31H28N2:C,86.88;H,6.59;N,6.54。实测元素含量(%):C,86.87;H,6.58;N,6.55。上述证实获得产物为目标产物80。
实施例11
化合物82的制备
将实施例1中的R1、R2、R3、R4基团替换为如上所示R1、R2、R3、R4基团,得到化合物82。质谱m/z:423.52(计算值:423.53)。理论元素含量(%)C30H21N3:C,85.08;H,5.00;N,9.92。实测元素含量(%):C,85.09;H,4.98;N,9.93。上述证实获得产物为目标产物82。
实施例12
化合物98的制备
将实施例1中的R1、R2、R3、R4基团替换为如上所示R1、R2、R3、R4基团,得到化合物98。质谱m/z:310.40(计算值:310.41)。理论元素含量(%)C22H18N2:C,85.13;H,5.85;N,9.03。实测元素含量(%):C,85.14;H,5.86;N,9.04。上述证实获得产物为目标产物98。
实施例12
化合物120的制备
将实施例1中的R1、R2、R3、R4基团替换为如上所示R1、R2、R3、R4基团111。质谱m/z:441.58(计算值:441.56)。理论元素含量(%)C31H27N3:C,84.32;H,6.16;N,9.52。实测元素含量(%):C,84.33;H,6.18;N,9.53。上述证实获得产物为目标产物120。
实施例12
化合物135的制备
将实施例1中的R1、R2、R3、R4基团替换为如上所示R1、R2、R3、R4基团111。质谱m/z:610.76(计算值:610.75)。理论元素含量(%)C46H30N2:C,90.45;H,4.96;N,4.58。实测元素含量(%):C,90.46;H,4.95;N,4.59。上述证实获得产物为目标产物135。
[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HAT-CN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TPBi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1-10]
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HAT-CN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的本发明含有咪唑结构的衍生物作为电子传输层,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电致发光器件的电子发光特性在下表中表示:
以上结果表明,本发明的含有咪唑结构的衍生物作为电子传输材料,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 (7)
1.一种含有咪唑结构的衍生物,其特征在于,具有如下通式(Ⅰ)所示结构:
其中,R1、R2、R3、R4独立的选自氢、取代或未取代的C1-C60烷基、取代或未取代的C6-C60的芳基、取代或未取代的C3~C60的杂环基中的一种。
2.根据权利要求1所述含有咪唑结构的衍生物,其特征在于,R1、R2、R3、R4独立的选自氢、取代或未取代的C1-C30烷基、取代或未取代的C6-C30的芳基、取代或未取代的C3~C30的杂环基中的一种。
3.根据权利要求1所述含有咪唑结构的衍生物,其特征在于,R1、R2、R3、R4独立的选自氢、C1~C4烷基或取代或未取代的如下基团:苯基、萘基、蒽基、菲基、芴基、螺二芴基、咔唑基、二苯并噻吩基、二苯并呋喃基、三嗪基、喹啉基或异喹啉基。
4.根据权利要求1所述含有咪唑结构的衍生物,其特征在于,选自如下所示结构中的任意一种:
5.权利要求1所述的含有咪唑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独立的选自氢、取代或未取代的C1-C60烷基、取代或未取代的C6-C60的芳基、取代或未取代的C3~C60的杂环基中的一种。
6.一种有机电致发光器件,其特征在于,包括阳极、阴极、有机物层;所述有机物层含有权利要求1-4任一项所述的含有咪唑结构的衍生物。
7.根据权利要求6所述的有机电致发光器件,其特征在于,所述有机物层包括电子传输层,所述电子传输层中含有权利要求1-4任一项所述的含有咪唑结构的衍生物。
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CN107915731A (zh) * | 2017-11-14 | 2018-04-17 | 长春海谱润斯科技有限公司 | 一种稠环衍生物及其合成方法和有机发光器件 |
CN110746442A (zh) * | 2018-12-10 | 2020-02-04 | 广州华睿光电材料有限公司 | 含咪唑螺环的化合物及其应用 |
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CN107915731A (zh) * | 2017-11-14 | 2018-04-17 | 长春海谱润斯科技有限公司 | 一种稠环衍生物及其合成方法和有机发光器件 |
CN110746442A (zh) * | 2018-12-10 | 2020-02-04 | 广州华睿光电材料有限公司 | 含咪唑螺环的化合物及其应用 |
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