CN107827807A - 一种含有咔唑结构的衍生物及其制备方法和有机电致发光器件 - Google Patents
一种含有咔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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- 0 CC(C)CCCC1=C(*c2ccccc2Nc2cccc(-c3ccccc3)c2)CCC=C1c(cc1)ccc1N(c1ccccc1)c1cc2ccccc2cc1 Chemical compound CC(C)CCCC1=C(*c2ccccc2Nc2cccc(-c3ccccc3)c2)CCC=C1c(cc1)ccc1N(c1ccccc1)c1cc2ccccc2cc1 0.000 description 8
- GTMZEDPIOAFSRR-UHFFFAOYSA-N Brc(c1ccc2CCC3Cc4ccccc4)cccc1c2-c1c3cccc1 Chemical compound Brc(c1ccc2CCC3Cc4ccccc4)cccc1c2-c1c3cccc1 GTMZEDPIOAFSRR-UHFFFAOYSA-N 0.000 description 1
- QQLLKOSTACUDJV-UHFFFAOYSA-N Brc(cc1)ccc1-c1cccc(C2)c1C=CC(N1c3ccccc3)=C2C2C1=CC=CC2 Chemical compound Brc(cc1)ccc1-c1cccc(C2)c1C=CC(N1c3ccccc3)=C2C2C1=CC=CC2 QQLLKOSTACUDJV-UHFFFAOYSA-N 0.000 description 1
- UCCUXODGPMAHRL-UHFFFAOYSA-N Brc(cc1)ccc1I Chemical compound Brc(cc1)ccc1I UCCUXODGPMAHRL-UHFFFAOYSA-N 0.000 description 1
- QARVLSVVCXYDNA-UHFFFAOYSA-N Brc1ccccc1 Chemical compound Brc1ccccc1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 1
- HYGVRWRSZIBVBB-UHFFFAOYSA-N C(C(C=C1)N(c(cc2)cc3c2c(cccc2)c2[n]3C2C=CC=CC2)C2=CC=CC=CC2)C=C1c1cccc2c1ccc(N1c3cccc(-c4ccccc4)c3)c2-c2cc1ccc2 Chemical compound C(C(C=C1)N(c(cc2)cc3c2c(cccc2)c2[n]3C2C=CC=CC2)C2=CC=CC=CC2)C=C1c1cccc2c1ccc(N1c3cccc(-c4ccccc4)c3)c2-c2cc1ccc2 HYGVRWRSZIBVBB-UHFFFAOYSA-N 0.000 description 1
- OSBSXTGABLIDRX-UHFFFAOYSA-N C=C1C=CC=CC1 Chemical compound C=C1C=CC=CC1 OSBSXTGABLIDRX-UHFFFAOYSA-N 0.000 description 1
- IEBSDPOHZXTBSL-UHFFFAOYSA-N [O-][N+](c(cccc1)c1-c1cccc2c1cccc2Br)=O Chemical compound [O-][N+](c(cccc1)c1-c1cccc2c1cccc2Br)=O IEBSDPOHZXTBSL-UHFFFAOYSA-N 0.000 description 1
- FQVZHGGNBULOIB-UHFFFAOYSA-N c(cc1)ccc1-[n]1c2cccc(-c3cc(-[n]4c(cccc5)c5c5c4cccc5)ccc3)c2c2c1cccc2 Chemical compound c(cc1)ccc1-[n]1c2cccc(-c3cc(-[n]4c(cccc5)c5c5c4cccc5)ccc3)c2c2c1cccc2 FQVZHGGNBULOIB-UHFFFAOYSA-N 0.000 description 1
- PGJAIEOOBICKJT-UHFFFAOYSA-N c(cc1)ccc1Nc(cc1)ccc1-c1c(ccc2c3c4ccccc4[n]2-c2ccccc2)c3ccc1 Chemical compound c(cc1)ccc1Nc(cc1)ccc1-c1c(ccc2c3c4ccccc4[n]2-c2ccccc2)c3ccc1 PGJAIEOOBICKJT-UHFFFAOYSA-N 0.000 description 1
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Abstract
本发明提供一种含有咔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。该化合物具有式(Ⅰ)所示结构,通过在非对称结构咔唑结构上调整R1、R2和Ar1、Ar2基团来提高空穴移动度,提高空穴传输性能,进而提高器件的发光效率,是性能良好的有机发光材料。
Description
技术领域
本发明涉及有机光电材料技术领域,具体涉及一种含有咔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***、通讯***、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。目前空穴传输材料大多采用具有二苯胺或咔唑结构,含有此类结构的器件缺陷是,发射光线发光度的改进伴随发光效率明显降低,尤其是,在无源驱动的情况下,对于实际应用来说,瞬间需要数千cd/m2或者更高的亮度,并且在高亮度区中发光效率的增加是重要的。然而,由于高亮度区域中三线态失活占优势地位,因此目前实际应用的空穴传输材料的条件下,发光效率的降低不能得到改进。
发明内容
本发明提供一种含有咔唑结构的衍生物及其制备方法和有机电致发光器件,本发明是通过咔唑结构来提高空穴移动度,提供空穴传输及发光效果最大化的化合物,并且将这种含有咔唑结构的衍生物制备成器件,其具有很好的发光效率。
本发明首先提供一种含有咔唑结构的衍生物,结构式为:
其中,R1选自单键、取代或未取代的C6-C60的芳基、取代或未取代的C10~C60的稠环、取代或未取代的C8~C60的稠杂环中的一种;R2选自C1~C10的烷基、取代或未取代的C6-C60的芳基、取代或未取代的C10~C60的稠环中的一种;Ar1、Ar2独立地选自取代或未取代C6~C60芳基、取代或未取代的C10~C60的稠环、取代或未取代的C8~C60的稠杂环中的一种。。
优选的,所述R1选自单键、取代或未取代的C6-C30的芳基、取代或未取代的C10~C30的稠环、取代或未取代的C8~C30的稠杂环中的一种;R2选自C1~C4的烷基、取代或未取代的C6-C30的芳基、取代或未取代的C10~C30的稠环中的一种;Ar1、Ar2独立地选自取代或未取代C6~C30芳基、取代或未取代的C10~C30的稠环、取代或未取代的C8~C30的稠杂环中的一种。
优选的,所述R1选自单键、苯基、萘基、联苯基、喹啉基或异喹啉基;R2选自甲基、乙基、丙基、苯基、萘基、联苯基、喹啉基或异喹啉基;Ar1、Ar2独立地选自苯基、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、喹啉基或异喹啉基。
优选的,所述的含有咔唑结构的化合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咔唑结构的衍生物的制备方法,制备路线如下:
其中,R1选自单键、取代或未取代的C6-C60的芳基、取代或未取代的C10~C60的稠环、取代或未取代的C8~C60的稠杂环中的一种;R2选自C1~C10的烷基、取代或未取代的C6-C60的芳基、取代或未取代的C10~C60的稠环中的一种;Ar1、Ar2独立地选自取代或未取代C6~C60芳基、取代或未取代的C10~C60的稠环、取代或未取代的C8~C60的稠杂环中的一种
本发明还提供一种有机电致发光器件,包括阳极、阴极、置于所述阳极与所述阴极之间的有机物层;所述有机物层含有所述的含有咔唑结构的衍生物。
优选的,所述有机物层中含有空穴传输层,所述空穴传输层中含有所述的含有咔唑结构的衍生物。
本发明的有益效果:
本发明首先提供一种含有咔唑结构的衍生物,该化合物具有式(Ⅰ)所示结构,通过在非对称结构咔唑结构上调整R1、R2和Ar1、Ar2基团来提高空穴移动度,提高空穴传输性能,进而提高器件的发光效率。
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咔唑结构的衍生物,具有如下通式(Ⅰ)所示结构:
其中,R1选自单键、取代或未取代的C6-C60的芳基、取代或未取代的C10~C60的稠环、取代或未取代的C8~C60的稠杂环中的一种;R2选自C1~C10的烷基、取代或未取代的C6-C60的芳基、取代或未取代的C10~C60的稠环中的一种;Ar1、Ar2独立地选自取代或未取代C6~C60芳基、取代或未取代的C10~C60的稠环、取代或未取代的C8~C60的稠杂环中的一种。
优选的,R1选自单键、取代或未取代的C6-C30的芳基、取代或未取代的C10~C30的稠环、取代或未取代的C8~C30的稠杂环中的一种;R2选自C1~C4的烷基、取代或未取代的C6-C30的芳基、取代或未取代的C10~C30的稠环中的一种;Ar1、Ar2独立地选自取代或未取代C6~C30芳基、取代或未取代的C10~C30的稠环、取代或未取代的C8~C30的稠杂环中的一种。
优选的,R1选自单键、苯基、萘基、联苯基、喹啉基或异喹啉基;R2选自甲基、乙基、丙基、苯基、萘基、联苯基、喹啉基或异喹啉基;Ar1、Ar2独立地选自苯基、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、喹啉基或异喹啉基。
具体的,所述含有咔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咔唑结构的衍生物的制备方法,制备路线如下:
其中,R1选自单键、取代或未取代的C6-C60的芳基、取代或未取代的C10~C60的稠环、取代或未取代的C8~C60的稠杂环中的一种;R2选自C1~C10的烷基、取代或未取代的C6-C60的芳基、取代或未取代的C10~C60的稠环中的一种;Ar1、Ar2独立地选自取代或未取代C6~C60芳基、取代或未取代的C10~C60的稠环、取代或未取代的C8~C60的稠杂环中的一种。
本发明还提供一种有机电致发光器件,包括阳极、阴极、置于所述阳极与所述阴极之间的有机物层;所述有机物层含有所述的含有咔唑结构的衍生物。
上述有机物层中至少包括空穴注入层、空穴传输层、电子阻挡层、发光层、空穴阻挡层、电子传输层、电子注入层中的至少一层。优选所述空穴传输层中含有所述的含有咔唑结构的衍生物。
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TM1的制备
1-3的制备
在氮气的保护下,向2L反应釜中加入化合物1-1(6.89g,41.28mmol),1-2(11.80g,41.28mmol),碳酸钾(4.39g,31.75mmol),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1-3 12.89g,产率为80.89%。
1-4的制备
在250ml三口烧瓶中,加入1-3(12.89g,41.28mmol),溶剂邻二氯苯,亚磷酸三乙酯200ml,溶液加热到150℃,保持15h。减压蒸馏除掉溶剂和多余的亚磷酸三乙酯,粗品经过柱层析,得到产品1-4 9.26g,产率为79.57%。
1-6的制备
将三叔丁基膦(3mL的1.0M的甲苯溶液,7.32mmol)、醋酸钯(0.4g,1.83mmol)和叔丁醇钠(1.6g,52mmol)添加至1-4(9.26g,31.27mmol)1-5(6.38g,31.27mmol)在脱气甲苯(200mL)中的溶液,并且将该混合物在回流下加热2小时。将该反应混合物冷却至室温,用甲苯稀释并且经由硅藻土过滤。将该滤液用水稀释,并用甲苯提取,并且合并有机相,将其在真空下进行蒸发。将该残余物经由硅胶进行过滤,重结晶得到1-6 9.52g,产率为81.81%。
1-8的制备
在氮气的保护下,向2L反应釜中加入化合物1-6(9.52g,25.57mmol),1-7(6.49g,25.57mmol),碳酸钾(4.39g,19.72mmol),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1-8 8.14g,产率为75.94%。
1-10的制备
将三叔丁基膦(3mL的1.0M的甲苯溶液,7.32mmol)、醋酸钯(0.4g,1.83mmol)和叔丁醇钠(1.6g,52mmol)添加至1-8(8.14g,19.41mmol)1-9(5.49g,19.41mmol)在脱气甲苯(200mL)中的溶液,并且将该混合物在回流下加热2小时。将该反应混合物冷却至室温,用甲苯稀释并且经由硅藻土过滤。将该滤液用水稀释,并用甲苯提取,并且合并有机相,将其在真空下进行蒸发。将该残余物经由硅胶进行过滤,重结晶得到1-10 6.8g,产率为78.13%。
化合物TM1的制备
向干净的两口烧瓶中加入中间体1-10(7.73g,15.17mmol)和1-11(2.57g,15.17mmol),同时加入三氯化铝(1.44g,14.10mmol)、三氧化二铝(1.44g,14.10mmol)和30ml二甲苯,在氮气保护下,将体系加热到70-80度,连续反应8小时。冷却到室温后,采用***/去离子水萃取,然后采用硅胶柱层分离,同时采用无水硫酸镁进行干燥,获得产物6.38g,产率为78.43%。质谱m/z:536.23(计算值:536.25)。理论元素含量(%)C40H28N2:C,89.52;H,5.26;N,5.22。实测元素含量(%):C,89.53;H,5.25;N,5.23。上述证实获得产物为目标产物TM1。
实施例2
化合物TM7的制备
将实施例1中的R1、R2和Ar1、Ar2基团替换为如上所示R1、R2和Ar1、Ar2基团,其他步骤均与实施例1相同,得到化合物TM3。质谱m/z:587.24(计算值:587.25)。
实施例3
化合物TM12的制备
将实施例1中的R1、R2和Ar1、Ar2基团替换为如上所示R1、R2和Ar1、Ar2基团,其他步骤均与实施例1相同,得到化合物TM12。质谱m/z:642.21(计算值:642.23)。
实施例4
化合物TM14的制备
将实施例1中的R1、R2和Ar1、Ar2基团替换为如上所示R1、R2和Ar1、Ar2基团,其他步骤均与实施例1相同,得到化合物TM14。质谱m/z:626.24(计算值:626.25)。
实施例5
化合物TM15的制备
将实施例1中的R1、R2和Ar1、Ar2基团替换为如上所示R1、R2和Ar1、Ar2基团,其他步骤均与实施例1相同,得到化合物TM15。质谱m/z:701.28(计算值:701.29)。
实施例6
化合物TM18的制备
将实施例1中的R1、R2和Ar1、Ar2基团替换为如上所示R1、R2和Ar1、Ar2基团,其他步骤均与实施例1相同,得到化合物TM18。质谱m/z:774.30(计算值:774.35)。
实施例7
化合物TM26的制备
将实施例1中的R1、R2和Ar1、Ar2基团替换为如上所示R1、R2和Ar1、Ar2基团,其他步骤均与实施例1相同,得到化合物TM26。质谱m/z:511.20(计算值:511.23)。
实施例8
化合物TM36的制备
将实施例1中的R1、R2和Ar1、Ar2基团替换为如上所示R1、R2和Ar1、Ar2基团,其他步骤均与实施例1相同,得到化合物TM36。质谱m/z:698.27(计算值:698.25)。
实施例9
化合物TM44的制备
将实施例1中的R1、R2和Ar1、Ar2基团替换为如上所示R1、R2和Ar1、Ar2基团,其他步骤均与实施例1相同,得到化合物TM44。质谱m/z:612.23(计算值:612.25)。
实施例10
化合物TM50的制备
将实施例1中的R1、R2和Ar1、Ar2基团替换为如上所示R1、R2和Ar1、Ar2基团,其他步骤均与实施例1相同,得到化合物TM50。质谱m/z:790.31(计算值:790.32)。
实施例11
化合物TM68的制备
将实施例1中的R1、R2和Ar1、Ar2基团替换为如上所示R1、R2和Ar1、Ar2基团,其他步骤均与实施例1相同,得到化合物TM68。质谱m/z:702.27(计算值:702.28)。
实施例12
化合物TM80的制备
将实施例1中的R1、R2和Ar1、Ar2基团替换为如上所示R1、R2和Ar1、Ar2基团,其他步骤均与实施例1相同,得到化合物TM80。质谱m/z:613.23(计算值:613.25)。
实施例13
化合物TM126的制备
将实施例1中的R1、R2和Ar1、Ar2基团替换为如上所示R1、R2和Ar1、Ar2基团,其他步骤均与实施例1相同,得到化合物TM126。质谱m/z:1012.38(计算值:1012.39)。
[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2-TNATA作为空穴注入层,蒸镀速率为0.1nm/s,蒸镀厚度为10nm。以同样方法蒸镀一层α-NPD作为空穴传输层。然后是发光层的蒸镀,混合蒸镀所述有机发光材料AND/DPAP-DPPA,作为蓝光掺杂材料,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]
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2-TNATA作为空穴注入层,蒸镀速率为0.1nm/s,蒸镀厚度为10nm。以同样方法蒸镀一层本发明含有咔唑结构的衍生物作为空穴传输层。然后是发光层的蒸镀,混合蒸镀所述有机发光材料AND/DPAP-DPPA,作为蓝光掺杂材料,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。
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,本发明的化合物物作为空穴传输材料,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)
1.一种含有咔唑结构的衍生物,其特征在于,具有如下通式(Ⅰ)所示结构:
其中,R1选自单键、取代或未取代的C6-C60的芳基、取代或未取代的C10~C60的稠环、取代或未取代的C8~C60的稠杂环中的一种;R2选自C1~C10的烷基、取代或未取代的C6-C60的芳基、取代或未取代的C10~C60的稠环中的一种;Ar1、Ar2独立地选自取代或未取代C6~C60芳基、取代或未取代的C10~C60的稠环、取代或未取代的C8~C60的稠杂环中的一种。
2.根据权利要求1所述的含有咔唑结构的衍生物,其特征在于,R1选自单键、取代或未取代的C6-C30的芳基、取代或未取代的C10~C30的稠环、取代或未取代的C8~C30的稠杂环中的一种;R2选自C1~C4的烷基、取代或未取代的C6-C30的芳基、取代或未取代的C10~C30的稠环中的一种;Ar1、Ar2独立地选自取代或未取代C6~C30芳基、取代或未取代的C10~C30的稠环、取代或未取代的C8~C30的稠杂环中的一种。
3.根据权利要求1所述的含有咔唑结构的衍生物,其特征在于,R1选自单键、苯基、萘基、联苯基、喹啉基或异喹啉基;R2选自甲基、乙基、丙基、苯基、萘基、联苯基、喹啉基或异喹啉基;Ar1、Ar2独立地选自苯基、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、喹啉基或异喹啉基。
4.根据权利要求1所述的含有咔唑结构的衍生物,其特征在于,选自如下所示结构中的任意一种:
5.权利要求1-4任一项所述的含有咔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选自单键、取代或未取代的C6-C60的芳基、取代或未取代的C10~C60的稠环、取代或未取代的C8~C60的稠杂环中的一种;R2选自C1~C10的烷基、取代或未取代的C6-C60的芳基、取代或未取代的C10~C60的稠环中的一种;Ar1、Ar2独立地选自取代或未取代C6~C60芳基、取代或未取代的C10~C60的稠环、取代或未取代的C8~C60的稠杂环中的一种。
6.一种有机电致发光器件,其特征在于,包括阳极、阴极、置于所述阳极与所述阴极之间的有机物层;所述有机物层含有权利要求1-4任一项所述的含有咔唑结构的衍生物。
7.根据权利要求6所述的有机电致发光器件,其特征在于,所述有机物层中含有空穴传输层,所述空穴传输层中含有权利要求1-4任一项所述的含有咔唑结构的衍生物。
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