CN115160212A - 一种有机发光材料及其制备方法和应用 - Google Patents

一种有机发光材料及其制备方法和应用 Download PDF

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CN115160212A
CN115160212A CN202210834268.XA CN202210834268A CN115160212A CN 115160212 A CN115160212 A CN 115160212A CN 202210834268 A CN202210834268 A CN 202210834268A CN 115160212 A CN115160212 A CN 115160212A
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王辉
陈剑锋
尹健
栾兰
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Jilin Optical and Electronic Materials Co Ltd
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Abstract

本发明公开了一种有机发光材料及其制备方法和应用，属于有机光电材料领域，所述其分子结构通式由通式I表示：
Figure DDA0003746903530000011
其中，所述通式I中，R为单取代基，选自氢、氘、卤素、氰基、取代或非取代的C1‑C6烷基；T为单取代基，独立位于Ar1、Ar2、Ar3、Ar4环上，T为取代或未取代的三芳胺类电子传输基团等。本发明的有机电致发光化合物作为空穴传输材料，与常规有机电致发光化合物相比，有机电致发光器件的效率和寿命显著改善。

Description

一种有机发光材料及其制备方法和应用
技术领域
本发明属于有机光电材料领域，更具体的说是涉及一种有机发光材料及其制备方法和应用。
背景技术
有机电致发光二极管以下简称(OLED)具有自发光、广视角、对比度高、响应时间短、驱动电压低、温度适应的范围大、可制作成软性等特性，并可通过三种有机电致发光材料(红色，绿色和蓝色)来实现全色OLED显示器，是新一代平板显示技术,可用于平板显示器和照明光源,目前商品化的平板显示器已批量投入市场应用在高端电子产品上。
有机电致发光元件是利用了如下原理的自发光元件：通过施加电场，利用由阳极注入的空穴与由阴极注入的电子的复合能使荧光性物质发光。它具有如下结构：阳极、阴极以及介于两者之间的有机材料层。为了提高有机电致发光元件的效率和稳定性，有机材料层通常包括具有不同材料的多层，例如空穴注入层HIL)、空穴传输层HTL)、发光层、电子传输层ETL)和电子注入层EIL)。在这种有机发光元件中，当在阳极和阴极之间施加电压时，来自阳极的空穴和来自阴极的电子注入有机材料层，产生的激子在迁移至基态时产生具有特定波长的光。其中空穴传输层可改变空穴到发光层的空穴传输效率、发光效率、寿命等。
目前使用4,4′-双[N-1-萘基-N-苯基氨基]联苯NPB、N,N′-二苯基-N，N′-双3-甲基苯基-1,1′-联苯-4,4′-二胺TPD等作为空穴传输材料。使用这些材料的有机电致发光元件虽然在空穴传输效率、发光效率、寿命等方面有所提高；但是，在使用寿命方面仍然不是很理想。
因此，需要开发新型结构的空穴传输材料来改善电致发光器件使用寿命长是本领域技术人员重点解决的问题。
发明内容
有鉴于此，本发明的发明目的在于提供一种具有成膜性好、效率高、驱动电压低、使用寿命长的有机电致发光材料。
为了实现上述目的，本发明采用如下技术方案：
一种有机发光材料，其分子结构通式由通式I表示：
Figure BDA0003746903520000021
其中，所述通式I中，R为单取代基，选自氢、氘、卤素、氰基、取代或非取代的C1-C6烷基；
T为单取代基，独立位于Ar1、Ar2、Ar3、Ar4环上，T为取代或未取代的三芳胺类电子传输基团，其中取代基为C1-C6烷基、取代或非取代的C6-C18芳基、取代或非取代的C4-C12芳族杂环基、取代或非取代的C8-C16的稠环基。
优选的，所述T的取代位置为所在环的任意位置。
优选的，所述烷基为直链烷基、支链烷基、环烷基、含1个或几个取代基取代的直链烷基、含1个或几个取代基取代的支链烷基或含1个或几个取代基取代的环烷基；其中，所述取代基独立的选自卤素、氘、氰基、羟基中的一种或几种；所述L1选自连接键、氢或苯基。
优选的，所述烷基优选为甲基。
优选的，所述芳基选自未取代的芳基或含1个或几个取代基取代的芳基；其中，所述取代基独立地选自卤素、氘、氨基、氰基、硝基、羟基。
优选的，所述芳族杂环基选自未取代的杂芳基或含1个或几个取代基取代的芳族杂环基；其中，杂芳基中的杂原子为氮、硫或氧；所述取代基独立地选自卤素、氘、氨基、氰基、硝基、羟基，所述芳族杂环基含有1个或几个选自B、N、O、S、Si以及P的杂原子。
优选的，所述T包括但不限于以下结构式所示基团：
Figure BDA0003746903520000031
优选的，所述有机发光材料的分子结构通式包括但不限于以下结构来表示：
Figure BDA0003746903520000041
优选的，所述有机发光材料的具体结构式还可以下述结构表示：
Figure BDA0003746903520000042
Figure BDA0003746903520000051
Figure BDA0003746903520000061
Figure BDA0003746903520000071
Figure BDA0003746903520000081
Figure BDA0003746903520000091
Figure BDA0003746903520000101
一种有机发光材料的制备方法，制备的合成路线如下：
Figure BDA0003746903520000102
Figure BDA0003746903520000111
本发明提供了一种制备有机发光材料的方法，还包括原料B(B1-B4)合成方法，其具体步骤为：
Figure BDA0003746903520000121
Figure BDA0003746903520000131
一种有机发光材料在有机电致发光器件中的应用，所述有机电致发光器件包括阳极、阴极以及设置在所述阳极和阴极之间的有机物层，所述有机物层包括发光层，所述发光层的原料包括掺杂材料和权利要求1-6任一项所述的有机发光材料。
优选的，所述有机发光材料和掺杂材料的质量比为(90-99.5):(0.5-10)。
优选的，所述有机物层还包括空穴注入层、空穴传输层、电子阻挡层、空穴阻挡层、电子传输层和电子注入层。
经由上述的技术方案可知，与现有技术相比，本发明的有益效果如下：
本发明实施例提供的空穴传输化合物由于具有多元环和螺环组成的刚性环结构，有利于分子间的电荷跃迁能力，同时，通过化合物结构式的Ar1-Ar4位置上连有取代基，分子间不易结晶、不易聚集，使材料具有较高的光热稳定性。因此，在发光层中使用本发明的有机电致发光化合物作为空穴传输材料，我们通过研究发现，这个母核不同位置的三芳胺取代，实现的效果是不一样的，这可能是最高占据分子轨道(HOMO)与阳极材料的功函数关系变化的原因。经测试，本发明限定的特定位置，有机电致发光器件的效率与寿命效果更好。使用本发明的有机电致发光化合物作为空穴传输材料，与常规有机电致发光化合物相比，有机电致发光器件的效率和寿命显著改善。
具体实施方式
下面对本发明实施例中的技术方案进行清楚、完整地描述，显然，所描述的实施例仅仅是本发明一部分实施例，而不是全部的实施例。基于本发明中的实施例，本领域普通技术人员在没有做出创造性劳动前提下所获得的所有其他实施例，都属于本发明保护的范围。
中间体B1合成
Figure BDA0003746903520000141
步骤1：将1-溴-2-萘苯甲酸甲酯(200mmol)、邻溴苯硼酸(200mmol)、四(三苯基膦)钯(2mmol)、碳酸钾(300mmol)纯净水100ml、四氢呋喃300ml加入三口反应瓶中，在氮气保护下加热到80℃反应8h，反应完毕后使用二氯甲烷萃取，浓缩有机相的到中间体B1-1。
步骤2：将B1-1(100mmol)、2-氨基苯硼酸频哪醇酯(100mmol)、四(三苯基膦)钯(1mmol)碳酸钾(150mmol)纯净水50ml、二氧六环300ml加入三口反应瓶中，在氮气保护下加热到120℃反应10h，反应完毕后二氯甲烷萃取，浓缩住层析(PE/EA＝5/1)得到中间体B1-2。
步骤3：将B1-2(40mmol)乙酸100ml、硫酸15ml加入到三口反应瓶中降温至0℃，缓慢滴加亚硝酸钠(50mmol)的水溶液，反应完毕后将反应液缓慢倒入水中，过滤，滤饼柱层析纯化得到中间体B1-3。
步骤4：将B1-3(60mmol)加入至THF(400ml)中，0℃滴加1mol/L的甲基溴化镁(180ml)，滴加完毕后室温反应6h，TLC监控反应完全，加入稀盐酸淬灭后，采用二氯甲烷萃取有机相浓缩得到中间体B1-4。
步骤5：将B1-4(25mmol)、二氯甲烷100ml加入反应瓶中，降温至0℃，滴加甲基磺酸(30mmol)，滴加完毕室温反应2h反应完全，加水用二氯甲烷萃取浓缩得到B1-5；
步骤6，将B1-5(40mmol)加入DMF中，降温至0℃后滴加NBS(48mmol)的DMF溶液，滴加完保温反应2h，TLC监控反应完全，将最终的反应液缓慢倒入水中，过滤，滤饼用乙醇洗涤干燥后得到中间体B1。核磁数据：1H-NMR(500MHz,Chloroform-d)δ8.09(t,J＝2.9Hz,1H),8.07(d,J＝3.5Hz,1H),7.83–7.78(m,3H),7.73(d,J＝1.6Hz,0H),7.72–7.70(m,1H),7.69(s,0H),7.60(d,J＝7.5Hz,1H),7.57(d,J＝2.2Hz,1H),7.56(d,J＝1.5Hz,1H),7.51(dd,J＝7.5,1.7Hz,1H),7.47(s,0H),7.46(d,J＝1.6Hz,1H),7.45(d,J＝3.2Hz,1H),7.43(d,J＝1.6Hz,1H),7.42(d,J＝1.6Hz,1H),2.17(s,3H).
中间体B2的合成:
Figure BDA0003746903520000151
只需将合成步骤4中苯甲基溴化镁替换为4-溴苯甲基溴化镁，其余步骤同上。
核磁数据：1H-NMR(500MHz,Chloroform-d)δ8.09(t,J＝2.9Hz,1H),8.07(d,J＝3.5Hz,1H),7.83–7.78(m,3H),7.73(d,J＝1.6Hz,0H),7.72–7.70(m,1H),7.69(s,0H),7.60(d,J＝7.5Hz,1H),7.57(d,J＝2.2Hz,1H),7.56(d,J＝1.5Hz,1H),7.51(dd,J＝7.5,1.7Hz,1H),7.47(s,0H),7.46(d,J＝1.6Hz,1H),7.45(d,J＝3.2Hz,1H),7.43(d,J＝1.6Hz,1H),7.42(d,J＝1.6Hz,1H),2.17(s,3H).
中间体B3的合成：
Figure BDA0003746903520000161
只需将合成步骤1中的邻溴苯硼酸替换为2，4-二溴苯硼酸，其余步骤同上。
核磁数据：1H-NMR(500MHz,Chloroform-d)δ8.11–8.09(m,1H),8.09–8.05(m,1H),7.93(d,J＝1.7Hz,1H),7.81(d,J＝8.1Hz,2H),7.79(d,J＝1.3Hz,1H),7.71(d,J＝7.6Hz,1H),7.65(d,J＝1.5Hz,1H),7.59(t,J＝7.5Hz,1H),7.54(d,J＝2.1Hz,1H),7.52(d,J＝2.1Hz,1H),7.47(d,J＝3.9Hz,1H),7.46(d,J＝4.3Hz,1H),7.35(d,J＝7.4Hz,1H),7.33(d,J＝1.5Hz,1H),7.26–7.20(m,1H),2.18(s,3H).
中间体B4的合成：
Figure BDA0003746903520000162
只需将合成步骤2中的2-氨基苯硼酸频哪醇酯替换为2-氨基-4-溴苯硼酸频哪醇酯，其余步骤同上。核磁数据：1H-NMR(500MHz,Chloroform-d)δ7.95(d,J＝1.9Hz,1H),7.81(q,J＝1.5Hz,1H),7.80–7.78(m,1H),7.77(d,J＝1.4Hz,1H),7.74–7.72(m,1H),7.71(d,J＝8.0Hz,1H),7.63(d,J＝7.5Hz,1H),7.59(t,J＝7.7Hz,1H),7.55(d,J＝2.0Hz,1H),7.54(d,J＝2.0Hz,1H),7.52(d,J＝1.8Hz,1H),7.51(d,J＝1.5Hz,1H),7.45(t,J＝7.4Hz,1H),7.36–7.30(m,2H),7.24(d,J＝7.5Hz,1H),2.17(s,3H).
实施例1：制备化合物H01
Figure BDA0003746903520000171
在氮气保护体系下，称取式B1(10.88mmol,5g),2-苯基氨(10.88mmol,1.84g)，叔丁醇钠(32.65mmol,3.14g)放入反应体系中,加入150ml甲苯，氮气保护下催化剂Pd2(dba)3(0.217mmol,0.125g)和(50％)P(t-Bu)3(0.435mmol，0.88g)，氮气保护下110℃回流18h，然后冷却到25℃，加入250mL纯净水，搅拌30min后静置分层，分液，将有机相过50g的硅胶漏斗，将有机相滤液旋至无液体流出，加入石油醚搅拌20min，抽滤，滤饼用石油醚淋洗，将滤饼真空烘干，得到所示化合物式H01(4.6g，产率为77.17％),其HPLC纯度大于99.5％。
质谱：计算值为547.23；测试值为547.68。元素分析：计算值为C：92.11％；H：5.34％；N：2.56％；测试值为C：92.12％；H：5.35％；N：2.54％；核磁数据：1H-NMR(500MHz,Chloroform-d)δ8.32(dd,J＝7.4,1.6Hz,1H),8.12–8.03(m,2H),8.06–7.97(m,1H),7.88(t,J＝7.5Hz,1H),7.71(dd,J＝7.4,1.6Hz,1H),7.55(s,1H),7.50(dd,J＝7.5,1.7Hz,1H),7.50–7.38(m,5H),7.34(t,J＝7.4Hz,2H),7.28–7.16(m,9H),7.05–6.95(m,2H),2.24(s,3H).
实施例2：制备化合物H02
Figure BDA0003746903520000172
在氮气保护体系下，称取式B1(10.88mmol,5g),N-苯基联苯-4-胺(10.88mmol,2.67g)，叔丁醇钠(32.65mmol,3.14g)放入反应体系中,加入150ml甲苯，氮气保护下催化剂Pd2(dba)3(0.217mmol,0.125g)和(50％)P(t-Bu)3(0.435mmol，0.88g)，氮气保护下110℃回流18h，然后冷却到25℃，加入250mL纯净水，搅拌30min后静置分层，分液，将有机相过50g的硅胶漏斗，将有机相滤液旋至无液体流出，加入石油醚搅拌20min，抽滤，滤饼用石油醚淋洗，将滤饼真空烘干，得到所示化合物式H02(5.1g，产率为75.12％),其HPLC纯度大于99.5％。质谱：计算值为623.26；测试值为623.78。元素分析：计算值为C：92.42％；H：5.33％；N：2.25％；测试值为C：92.42％；H：5.34％；N：2.26％；核磁数据：1H-NMR(500MHz,Chloroform-d)δ8.35(dd,J＝7.5,1.5Hz,1H),8.13–7.99(m,3H),7.90(t,J＝7.5Hz,1H),7.72(dd,J＝7.3,1.6Hz,1H),7.62–7.54(m,3H),7.51(dd,J＝7.5,1.7Hz,1H),7.50–7.41(m,8H),7.45–7.33(m,4H),7.33(dtd,J＝7.4,3.9,2.0Hz,3H),7.28–7.18(m,5H),7.00(tt,J＝7.0,2.3Hz,1H),2.25(s,3H).
实施例3：制备化合物H03
Figure BDA0003746903520000181
在氮气保护体系下，称取式B1(10.88mmol,5g),N-苯基二苯并[b,d]噻吩-3-胺(10.88mmol,3g)，叔丁醇钠(32.65mmol,3.14g)放入反应体系中,加入150ml甲苯，氮气保护下催化剂Pd2(dba)3(0.217mmol,0.125g)和(50％)P(t-Bu)3(0.435mmol，0.88g)，氮气保护下110℃回流18h，然后冷却到25℃，加入250mL纯净水，搅拌30min后静置分层，分液，将有机相过50g的硅胶漏斗，将有机相滤液旋至无液体流出，加入石油醚搅拌20min，抽滤，滤饼用石油醚淋洗，将滤饼真空烘干，得到所示化合物式H03(5.2g，产率为73.07％),其HPLC纯度大于99.5％。
质谱：计算值为623.26；测试值为623.78。元素分析：计算值为C：88.17％；H：4.78％；N：2.14％；S：2.14％；测试值为C：88.16％；H：4.78％；N：2.15％；S：2.13％；核磁数据：1H-NMR(500MHz,Chloroform-d)δ8.42(ddd,J＝10.5,7.4,1.5Hz,2H),8.13–7.98(m,6H),7.91(t,J＝7.4Hz,1H),7.72(dd,J＝7.4,1.6Hz,1H),7.61–7.48(m,3H),7.50–7.39(m,5H),7.35(d,J＝7.4Hz,2H),7.35–7.24(m,3H),7.28–7.19(m,5H),7.00(tt,J＝7.0,2.4Hz,1H),2.26(s,3H).
实施例4：制备化合物H04
Figure BDA0003746903520000191
在氮气保护体系下，称取式B1(10.88mmol,5g),N-(联苯-4-基)萘-2-胺(10.88mmol,3.21g)，叔丁醇钠(32.65mmol,3.14g)放入反应体系中,加入150ml甲苯，氮气保护下催化剂Pd2(dba)3(0.217mmol,0.125g)和(50％)P(t-Bu)3(0.435mmol，0.88g)，氮气保护下110℃回流18h，然后冷却到25℃，加入250mL纯净水，搅拌30min后静置分层，分液，将有机相过50g的硅胶漏斗，将有机相滤液旋至无液体流出，加入石油醚搅拌20min，抽滤，滤饼用石油醚淋洗，将滤饼真空烘干，得到所示化合物式H03(5.2g，产率为73.07％),其HPLC纯度大于99.5％。
质谱：计算值为673.27；测试值为673.84。元素分析：计算值为C：92.69％；H：5.24％；N：2.08％；测试值为C：92.70％；H：5.23％；N：2.08％；核磁数据：1H-NMR(500MHz,Chloroform-d)δ8.38(dd,J＝7.5,1.4Hz,1H),8.11(dd,J＝7.5,1.5Hz,1H),8.07(dd,J＝5.7,3.9Hz,1H),8.03(dd,J＝5.6,3.9Hz,1H),7.90(t,J＝7.4Hz,1H),7.72(dd,J＝7.4,1.6Hz,3H),7.60(dt,J＝5.7,1.6Hz,3H),7.59–7.56(m,2H),7.51(dd,J＝7.5,1.5Hz,1H),7.49–7.45(m,6H),7.45–7.40(m,5H),7.38–7.33(m,3H),7.33–7.24(m,3H),7.24–7.18(m,1H),2.25(s,3H).
实施例5：制备化合物H10
Figure BDA0003746903520000201
在氮气保护体系下，称取式B1(10.88mmol,5g),N-苯基二苯并[b,d]呋喃-3-胺(10.88mmol,2.82g)，叔丁醇钠(32.65mmol,3.14g)放入反应体系中,加入150ml甲苯，氮气保护下催化剂Pd2(dba)3(0.217mmol,0.125g)和(50％)P(t-Bu)3(0.435mmol，0.88g)，氮气保护下110℃回流18h，然后冷却到25℃，加入250mL纯净水，搅拌30min后静置分层，分液，将有机相过50g的硅胶漏斗，将有机相滤液旋至无液体流出，加入石油醚搅拌20min，抽滤，滤饼用石油醚淋洗，将滤饼真空烘干，得到所示化合物式H10(5.1g，产率为73.47％),其HPLC纯度大于99.5％。
质谱：计算值为637.24；测试值为637.76。元素分析：计算值为C：90.40％；H：4.90％；N：2.20％；O：2.51％；测试值为C：90.41％；H：4.89％；N：2.21％；O：2.52％；核磁数据：1H-NMR(500MHz,Chloroform-d)δ8.38(dd,J＝7.5,1.4Hz,1H),8.12–7.98(m,3H),7.96(dd,J＝7.4,1.6Hz,1H),7.89(t,J＝7.5Hz,1H),7.72(dd,J＝7.4,1.6Hz,1H),7.64(d,J＝7.5Hz,1H),7.61–7.53(m,1H),7.55–7.44(m,4H),7.47–7.39(m,4H),7.39–7.30(m,3H),7.27–7.19(m,5H),7.09(dd,J＝7.5,1.5Hz,1H),7.00(ddd,J＝9.5,5.3,4.1Hz,1H),2.26(s,3H).
实施例6：制备化合物H17
Figure BDA0003746903520000202
在氮气保护体系下，称取式B1(10.88mmol,5g),N-(联苯-4-基)-9,9-二甲基-9H-芴-2-胺(10.88mmol,3.93g)，叔丁醇钠(32.65mmol,3.14g)放入反应体系中,加入150ml甲苯，氮气保护下催化剂Pd2(dba)3(0.217mmol,0.125g)和(50％)P(t-Bu)3(0.435mmol，0.88g)，氮气保护下110℃回流18h，然后冷却到25℃，加入250mL纯净水，搅拌30min后静置分层，分液，将有机相过50g的硅胶漏斗，将有机相滤液旋至无液体流出，加入石油醚搅拌20min，抽滤，滤饼用石油醚淋洗，将滤饼真空烘干，得到所示化合物式H17(5.8g，产率为72.02％),其HPLC纯度大于99.5％。
质谱：计算值为739.32；测试值为739.94。元素分析：计算值为C：92.52％；H：5.58％；N：1.89％；测试值为C：92.53％；H：5.59％；N：1.88％；核磁数据：1H-NMR(500MHz,Chloroform-d)δ8.36(dd,J＝7.4,1.5Hz,1H),8.12–8.06(m,3H),8.04–7.99(m,2H),7.89(t,J＝7.5Hz,1H),7.80(dd,J＝7.7,1.4Hz,2H),7.77(d,J＝7.5Hz,1H),7.73(dd,J＝7.4,1.6Hz,2H),7.61–7.55(m,5H),7.53(dt,J＝5.4,1.5Hz,2H),7.52–7.49(m,2H),7.48(d,J＝1.5Hz,1H),7.47(d,J＝2.2Hz,1H),7.46–7.45(m,2H),7.44(d,J＝1.6Hz,2H),7.42(d,J＝3.2Hz,1H),7.40(dd,J＝6.1,1.5Hz,2H),7.37–7.30(m,3H),2.22(s,3H),1.60(d,J＝1.5Hz,6H).
其他实施例测试数据见表1
表1
Figure BDA0003746903520000211
Figure BDA0003746903520000221
本实施例提供一种有机电致发光器件，其包括第一电极，以及依次设置于第一电极上的空穴注入层、空穴传输层、发光层、电子阻挡层、空穴阻挡层、电子传输层、电子注入层和第二电极。其中，第一电极为ITO阳极；第二电极为阴极；
器件实施例1：利用本发明的空穴传输材料制备红光磷光掺杂有机电致发光器件(OLED)
所制备OLED器件的结构为：ITO阳极/HIL/HTL/EML/ETL/EIL/阴极
a、ITO阳极：将涂层厚度为
Figure BDA0003746903520000222
的ITO(氧化铟锡)-Ag-ITO(氧化铟锡)玻璃基板在蒸馏水中清洗2次，超声波洗涤30min，再用蒸馏水反复清洗2次，超声波洗涤10min，洗涤结束后，用甲醇、丙酮、异丙醇依次超声波洗涤(每次洗涤5min)，干燥，然后转移至等离子体清洗机内洗涤5min，再送至蒸镀机中，以该基板为阳极，在其上依次蒸镀其它功能层。
b、HIL(空穴注入层)：蒸镀2-TNATA(即N1-(2-萘基)-N4,N4-二(4-(2-萘基(苯基)氨基)苯基)-N1-苯基苯-1,4-二胺)10nm，形成空穴注入层。
c、HTL(空穴传输层)：蒸镀上述实施例1制备的化合物A115nm，形成空穴传输层。
d、EML(发光层)：主体材料EMH-1和掺杂材料EMD-1，以重量比97∶3混合蒸镀40nm，形成发光层。其中主体材料EMH-1和掺杂材料EMD-1的结构式如下；
f、ETL(电子传输层)：蒸镀ET-1和Liq 40nm，形成电子传输层。其中ET-1和Liq的重量比为60:40，其中ET-1的结构式如下
g、EIL(电子注入层)：蒸镀Yb 1.0nm，形成电子注入层。
h、阴极：蒸镀镁和银18nm，其重量比为1:9，得到OLED器件。
Figure BDA0003746903520000231
参照上述器件实施例1提供的方法，分别选用本发明实施例中的化合物H01、H02、H03、H04、H10、H17、H29、H30、H31、H32、H57、H58、H59、H60、H74、H84、H85、H86、H87、H88替代化合物A1，进行空穴传输层的蒸镀，并制备得到相应的有机电致发光器件。
器件对比例1：
该对比例提供了一种有机电致发光器件，该有机电致发光器件的制备方法与器件实施例1的唯一区别在于，该有机电致发光器件是采用现有的对比化合物NPB替代上述器件实施例1中的空穴传输材料(化合物A1)进行蒸镀，制备得到相应的有机电致发光器件，记为器件对比例1。其中，对比化合物NPB的化学结构式为：
Figure BDA0003746903520000232
器件对比例2：
将对比例1中化合物NPB替代P87进行蒸镀，制备得到相应的有机电致发光器件,对比化合物P87的化学结构式为：
Figure BDA0003746903520000233
器件对比例3：
将对比例1中化合物NPB替代P88进行蒸镀，制备得到相应的有机电致发光器件,对比化合物P88的化学结构式为：
Figure BDA0003746903520000241
性能检测
在6000(nits)亮度下对上述实施例1-20以及对比例1、2、3得到的有机电致发光器件的驱动电压、发光效率以及寿命进行表征，测试结果如下表2。
表2
Figure BDA0003746903520000242
Figure BDA0003746903520000251
由表2可以看出，与对比例1、2、3相比，本发明实践例1-20提供的有机电致发光器件的驱动电压为3.3V～3.6V，明显小于对比例1、2、3的驱动电压，同时发光效率远远高于对比例1、2、3的发光效率，寿命是对比例1、2、3的1.2倍左右，由此可知，使用本发明提供的有机电致发光化合物作为空穴传输材料所制备的有机电致发光器件与使用对比例化合物作为空穴传输材料所制备的有机电致发光器件相比，驱动电明显降低，发光效率以及寿命得到显著提高。
本领域的技术人员将明显看到，在不脱离本发明的精神和范围下，本发明可以有许多修改和变化。因此可以预期到，本发明覆盖在附带权利要求的范围及其相当范围内提供的本发明修改和变化。
本说明书中各个实施例采用递进的方式描述，每个实施例重点说明的都是与其他实施例的不同之处，各个实施例之间相同相似部分互相参见即可。
对所公开的实施例的上述说明，使本领域专业技术人员能够实现或使用本发明。对这些实施例的多种修改对本领域的专业技术人员来说将是显而易见的，本文中所定义的一般原理可以在不脱离本发明的精神或范围的情况下，在其它实施例中实现。因此，本发明将不会被限制于本文所示的这些实施例，而是要符合与本文所公开的原理和新颖特点相一致的最宽的范围。

Claims (10)

1.一种有机发光材料，其特征在于，其分子结构通式由通式I表示：
Figure FDA0003746903510000011
其中，所述通式I中，R为单取代基，选自氢、氘、卤素、氰基、取代或非取代的C1-C6烷基；
T为单取代基，独立位于Ar1、Ar2、Ar3、Ar4环上，T为取代或未取代的三芳胺类电子传输基团，其中取代基为C1-C6烷基、取代或非取代的C6-C18芳基、取代或非取代的C4-C12芳族杂环基、取代或非取代的C8-C16的稠环基。
2.根据权利要求1所述的一种有机发光材料，其特征在于，所述烷基为直链烷基、支链烷基、环烷基、含1个或几个取代基取代的直链烷基、含1个或几个取代基取代的支链烷基或含1个或几个取代基取代的环烷基；其中，所述取代基独立的选自卤素、氘、氰基、羟基中的一种或几种；所述L1选自连接键、氢或苯基。
3.根据权利要求1所述的一种有机发光材料，其特征在于，所述芳基选自未取代的芳基或含1个或几个取代基取代的芳基；其中，所述取代基独立地选自卤素、氘、氨基、氰基、硝基、羟基。
4.根据权利要求1所述的一种有机发光材料，其特征在于，所述芳族杂环基选自未取代的杂芳基或含1个或几个取代基取代的芳族杂环基；其中，杂芳基中的杂原子为氮、硫或氧；所述取代基独立地选自卤素、氘、氨基、氰基、硝基、羟基，所述芳族杂环基含有1个或几个选自B、N、O、S、Si以及P的杂原子。
5.根据权利要求1所述的一种有机发光材料，其特征在于，所述T包括但不限于以下结构式所示基团：
Figure FDA0003746903510000021
6.根据权利要求1所述的一种有机发光材料，其特征在于，所述有机发光材料的分子结构通式包括但不限于以下结构来表示：
Figure FDA0003746903510000031
7.一种权利要求6所述的有机发光材料的制备方法，其特征在于，制备的合成路线如下：
Figure FDA0003746903510000032
Figure FDA0003746903510000041
8.一种有机发光材料在有机电致发光器件中的应用，其特征在于，所述有机电致发光器件包括阳极、阴极以及设置在所述阳极和阴极之间的有机物层，所述有机物层包括发光层，所述发光层的原料包括掺杂材料和权利要求1-6任一项所述的有机发光材料。
9.一种有机发光材料在有机电致发光器件中的应用，其特征在于，所述有机发光材料和掺杂材料的质量比为(90-99.5):(0.5-10)。
10.一种有机发光材料在有机电致发光器件中的应用，其特征在于，所述有机物层还包括空穴注入层、空穴传输层、电子阻挡层、空穴阻挡层、电子传输层和电子注入层。
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