CN108409720A - 有机发光材料、有机发光材料的应用及有机电致发光器件 - Google Patents

有机发光材料、有机发光材料的应用及有机电致发光器件 Download PDF

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CN108409720A
CN108409720A CN201810315618.5A CN201810315618A CN108409720A CN 108409720 A CN108409720 A CN 108409720A CN 201810315618 A CN201810315618 A CN 201810315618A CN 108409720 A CN108409720 A CN 108409720A
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廖良生
袁熠
蒋佐权
胡云
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Abstract

本发明涉及一种有机发光材料、有机发光材料的应用及有机电致发光器件，该有机发光材料为包含以下通式(1)表示的化合物：通式(1)中，Y1和Y2分别选自氢基或氰基中的一种；X1和X2分别选自CH或N中的一种；L1连接一个或两个R1，L2连接一个或两个R2，且L1和L2分别选自氢基或单键，和/或，环原子数为6～18的芳基/杂芳族环；R1和R2分别选自环原子数为10～40的芳胺基。该有机发光材料以苊并吡嗪衍生物为结构通式，并通过修饰其他不同化学基团，使该有机发光材料具有优异的发光特性、稳定的结构以及较高的色纯度，同时，其制备成本较低。

Description

有机发光材料、有机发光材料的应用及有机电致发光器件
技术领域
本发明涉及一种有机发光材料、有机发光材料的应用及有机电致发光器件。
背景技术
自1987年C.W.Tang发明多层结构以来，有机电致发光器件在可见光范围内取得了长足的进展，并且已经广泛应用于平板显示、固态照明等领域。相较而言，深红光特别是近红外放光材料的发展相对落后。但深红/近红外发光材料在安全显示、夜视仪、信息安全存储、光学通信等新兴领域有不可替代的作用。因此，近几年研发新型高效深红/近红外发光材料成为了有机光电领域研究的热点和难点。
目前，深红/近红外发光材料主要分为两大类：过渡金属配合物和具有给体受体结构的纯有机共轭材料。其中，铱、铂等贵金属的配合物能利用三重态的激子发光而受到了更多的关注。但由于此类材料具有很长的三重态寿命，所以大部分近红外磷光器件在高亮度时具有较大的效率滚降。此外，深红/近红外金属配合物需要有很大的共轭，但同时为了可以蒸镀分子量又不能太大，因此，分子设计上具有一定的局限性。作为另一大类深红/近红外发光材料，传统荧光材料也得到了广泛的研究，因为相较于磷光材料其更具有成本优势以及容易调节的光谱。但这类有给体-受体(D-A)构型的近红外传统荧光材料通常有如下缺点：
(1)根据带隙定律，当光谱扩展到近红外区时，非辐射跃迁效率会增大；
(2)只能利用25％的单重态激子。
因此，要实现高效的深红/近红外荧光器件仍然有很大的挑战。尽管近几年，在深红/近红外有机电致发光器件领域取得了很大的进展，但其效率仍然远低于可见光范围的电致发光器件。另外，目前大部分高效的深红/近红外发光器件光谱峰值小于650nm，还没达到真正的深红/近红外区域。而研究表明，苊并吡嗪具有强的吸电子能力，当接上不同的强给电子基团，由于强的分子内电荷转移使得分子具有小的带隙，具有深红/近红外发射；苊并吡嗪具有刚性的平面构型，能有效地的降低分子的振动和转动而达到高的辐射跃迁速率；热活化延迟荧光材料不需要使用铂铱等贵金属，并且其能通过高效的反向系间窜跃过程从而达到理论上100％的机子利用率。
基于上述情况，特提出本发明。
发明内容
本发明的目的在于提供一种有机发光材料、有机发光材料的应用及有机电致发光器件，能降低制造成本，提高既有发光材料的色纯度以及其在电致发光器件中的效率。
为达到上述目的，本发明提供如下技术方案：一种有机发光材料，为包含以下通式(1)表示的化合物的材料：
通式(1)中，Y1和Y2分别选自氢基或氰基中的一种；X1和X2分别选自CH或N中的一种；L1连接一个或两个R1，L2连接一个或两个R2，且L1和L2分别选自氢基或单键，和/或，环原子数为6～18的芳基/杂芳族环；R1和R2分别选自环原子数为10～40的芳胺基。
进一步地，在R1和R2所表示的芳胺基中，与苯环碳原子连接的氢基可以被R1取代，各位点的R1分别选自卤基、氰基、碳原子为1～10个的直链烷基/环状烷基/烷氧基/烷硫基或环原子数为6～30个的芳环中的任一种。
进一步地，所述直链烷基或环状烷基可以存在卤族取代基。
进一步地，R1和R2分别选自包括式Ar-1至Ar-19结构中的一种或多种：
其中，虚线表示与L1或L2相连接的键。
进一步地，L1、L2分别优选为氢、单键、苯基、联苯基或反式二苯乙烯基。
进一步地，R1、R2分别优选为以下芳胺：咔唑、二苯胺、9,9-二甲基-9,10-二氢吖啶、吩恶嗪、吩噻嗪、9,9-二甲基-10-苯基-9,10-二氢吖啶、5—苯基-5,10-二氢吩嗪、10-苯基吩恶嗪、10-苯基吩噻嗪、螺芴吖啶、双二甲基碳闭环三苯胺、二氧杂闭环三苯胺、二硫杂闭环三苯胺、三二甲基碳闭环三苯胺、三氧杂闭环三苯胺、三硫杂闭环三苯胺。
进一步地，各位点的R1分别优选为：氢、1至4个碳原子的烷基或烷氧基、1至2个碳原子的烷基或烷氧基取代的二芳基胺基。
进一步地，所述有机发光材料优选为以下式1-1至1-170、2-1至2-170、3-1至3-170、4-1至4-170、5-1至5-170以及6-1至6-170的化合物：
其中，2-1至2-170、3-1至3-170、4-1至4-170、5-1至5-170和6-1至6-170的结构式是相应的把吸电子基团由依次替换为 其余基团不变。
为达到上述目的，本发明还提供了根据所述的有机发光材料在用于制备深红/近红外电致发光器件中的应用。
为达到上述目的，本发明又提供了一种有机电致发光器件，包括阴极、阳极以及有机薄膜层，所述有机薄膜层设置在所述阴极和阳极之间，所述有机薄膜层包括至少一层有机发光层，所述有机薄膜层含有所述的有机发光材料。
进一步地，所述有机发光层包含所述有机发光材料。
进一步地，所述有机薄膜层还包括空穴注入层、空穴传输层、电子阻挡层、以及电子传输层，所述有机电致发光器件从高度方向上依次设有所述阳极、空穴注入层、空穴传输层、电子阻挡层、有机发光层、电子传输层以及阴极。
进一步地，所述有机电致发光器件为深红/近红外电致发光器件
与现有技术相比，本发明的有益效果在于：本发明的有机发光材料以苊并吡嗪衍生物为结构通式(1)，在苊并吡嗪上在并入不同的六元环增加电子的离域区域，并通过修饰其他不同化学基团，使该有机发光材料具有优异的发光特性、稳定的结构以及较高的色纯度，同时，其制备成本较低。并且，采用该有机发光材料的深红/近红外有机电致发光器件具有较高的发光效率和优异的性能。
上述说明仅是本发明技术方案的概述，为了能够更清楚了解本发明的技术手段，并可依照说明书的内容予以实施，以下以本发明的较佳实施例并配合附图详细说明如后。
附图说明
图1为本发明实施例11所示的化合物1-144的1H-NMR光谱图；
图2为本发明实施例11所示的化合物1-144的紫外-可见吸收光谱和荧光光谱图；
图3为本发明实施例20所示的OLED8的外量子效率-电流密度曲线和电致发光光谱图；
图4为本发明实施例18和实施例19所示的OLED6和OLED7在TPBi中的掺杂器件的外量子效率-电流密度曲线和电致发光光谱图；
图5为本发明实施例20所示的OLED11在TPBi中的掺杂器件的外量子效率-电流密度曲线和电致发光光谱图。
具体实施方式
下面结合相关通式、表格和实施例，对本发明的具体实施方式作进一步详细描述。以下实施例用于说明本发明，但不用来限制本发明的范围。
本发明的有机发光材料具有由下述通式(1)表示的结构：
其中，L1、L2分别连接一个或两个R1或R2基团，-L1-R1和/或-L2-R2以碳原子连接到苊并吡嗪母核的3和/或4号位；L1、L2分别独立地选自单键和/或苯、联苯等具有6至18个环原子的芳族或杂芳族环；R1、R2分别为具有10至40个环原子的芳胺，且所述芳环系可任选地被一个或者多个R1取代。各位点的R1可任意地选自：氢、卤素、氰基；具有1至10个碳原子的直链、直链或环状烷基、烷氧基或烷硫基基团，且所述直链烷基或直链烷基可任选地被卤素取代；具有6至30个环原子的芳环。
其中，L1、L2分别优选为氢、单键、苯基、联苯基或反式二苯乙烯基。各位点的R1分别优选为：氢、1至4个碳原子的烷基或烷氧基、1至2个碳原子的烷基或烷氧基取代的二芳基胺基中的任一种。R1、R2分别优选为以下芳胺中的一种或多种：
更优的，选为咔唑、二苯胺、9,9-二甲基-9,10-二氢吖啶、吩恶嗪、吩噻嗪、9,9-二甲基-10-苯基-9,10-二氢吖啶、5-苯基-5,10-二氢吩嗪、10-苯基吩恶嗪、10-苯基吩噻嗪、螺芴吖啶、双二甲基碳闭环三苯胺、二氧杂闭环三苯胺、二硫杂闭环三苯胺、三二甲基碳闭环三苯胺、三氧杂闭环三苯胺或三硫杂闭环三苯胺中的任一种或多种。
实施例1至10，中间体1～10的合成
实施例1，中间体1的合成：
其中，原料A(5-溴苊醌)的制备方法为：在250mL两口烧瓶中，加入21.86g(120mmol)苊醌和27mL(480mmol)液溴，搅拌并升温至70℃，2h后停止反应，加入饱和亚硫酸氢钠水溶液，至反应液为无色。加水稀释后减压抽滤，并用大量水洗涤至滤液呈中性。滤饼干燥后用二氯甲烷：石油醚＝2：1(体积比)的洗脱剂在硅胶柱上进行分离提纯，得到黄棕色的5-溴苊醌27.6g，收率88.12％。MS(EI):m/z 259.95[M+]。
中间体1的制备方法为：在250mL两口烧瓶中，依次加入5-溴苊醌7.83g(30.0mmol)、4,5-二氨基邻二苯腈4.74g(30.0mmol)、乙酸150mL，升高温度到120℃，回流搅拌24小时，反应完全后，冷却降到室温，倒入水中，减压抽滤并用大量水洗涤，滤渣干燥后用二氯甲烷：石油醚＝4：1(体积比)的洗脱剂在硅胶柱上进行分离提纯(注：产物溶解度差，必须以少量多次的方式进行分离提纯)，最终得到橙黄色固体9.95g，产率为77.82％。MS(EI):m/z 381.89[M+]。
实施例2至10，中间体的合成
中间体2的合成：
其中，化合物C(4,5-二溴苊)的制备方法为：在500mL的两口烧瓶中，加入37.01g(240mL)苊和200mLDMF，将温度维持在13℃并搅拌。将103.23g(580mL)NBS溶于200mLDMF中，然后缓慢滴加到苊的DMF溶液中，大约5小时滴完，恒温搅拌过夜。反应完全后，减压抽滤，然后将的到的滤渣用100mL乙醇回流10小时，冷却到室温后，抽滤得到灰白色固体24.3g，收率32.45％。MS(EI):m/z 319.90[M+]。
原料A(4,5-二溴苊醌)的制备方法为：在1000mL的两口烧瓶中，加入18.72g(60mmol)4,5-二溴苊和500mL乙酸酐，搅拌并升温至110℃，大约两小时缓慢滴加三氧化铬的乙酸酐溶液(46.4g三氧化铬溶于300mL乙酸酐中)。滴加完毕后，将温度升高到160℃继续反应30分钟，反应完全后将反应液倒入盛有1000g碎冰的烧杯中，并且搅拌散热，然后缓慢滴加20mL浓盐酸，减压抽滤得到黄色固体，然后将滤渣在乙酸酐中重结晶，冷却抽滤得到深黄棕色固体5.21g，收率25.54％。MS(EI):m/z 339.86[M+]。
中间体2～10的合成均按照与中间体1相同或类似的方法进行醌和二胺的关环反应，区别在于所使用的原料底物不同，所用的原料和中间体化合物的结构、收率以及质谱检测数据如表1所示。
表1
实施例11，化合物1-144的合成：
具体合成方法为：先按实施例2制备得到中间体2(3,4-二溴-苊并[1,2-b]喹喔啉-9,10-二腈)，然后在250mL圆底烧瓶中，加入1.39g(3mmol)的中间体2，2.02g(7.0mmol)的4-硼酸三苯胺和120mL的四氢呋喃，将反应体系除气，再用氩气保护。升温至50℃搅拌反应10分钟，然后加入30mL用氮气鼓泡30分钟的2mol/L的碳酸钠溶液，升高温度至66℃反应过夜，反应完全后冷却至室温，反应的混合物用二氯甲烷和水萃取分液，旋干有机相，得到的粗产品用二氯甲烷：石油醚＝3：1(体积比)的洗脱剂在硅胶柱上进行分离提纯，得到红褐色红色固体，在制备器件前再用气相沉积对产物进一步升华提纯，最终得到产物1.34g，收率56.3％。MS(EI):m/z 790.89[M+]。
请参见图1，分析并计算可知，元素分析计算值C56H34N6(％):C 85.04，H 4.33，N10.63；实测值：C 85.07，H 4.30，N 10.63。故，说明制备得到式1-144所示的化合物。
请参见图2，由图可知，式1-144所示的化合物吸光光谱峰值约为350nm，发光光谱峰值约为590nm。
本发明所涉及的芳胺通过苯或其他芳环以碳碳键链接到苊并吡嗪的3和/或4号位的所有化合物均按照此方法合成。
实施例12，结构式1-4的化合物的合成路线如下：
具体合成方法为：先按实施例1制备得到中间体1(3-溴-苊并[1,2-b]喹喔啉-9,10-二腈)，然后在100mL圆底烧瓶中，加入1.15g(3mmol)的中间体1，0.59g(3.5mmol)的二苯胺和1.95g(6mmol)的碳酸铯，将反应体系除气，再用氩气保护，用注射器加入50mL超干邻二甲苯和三叔顶基磷(0.1g/mL的甲苯溶液)0.3mL(0.15mmol)，将体系升温至120℃反应12小时。反应完全后冷却至室温，反应的混合物用二氯甲烷和水萃取分液，旋干有机相，得到的粗产品用二氯甲烷：石油醚＝2：1(体积比)的洗脱剂在硅胶柱上进行分离提纯，得到深红色的固体，在制备器件前再用气相沉积对产物进一步升华提纯，最终得到产物0.74g，收率52.4％。MS(EI):m/z 471.48[M+]。元素分析计算值C28H15N5(％):C 81.51，H 3.63，N14.85；实测值：C 81.52，H 3.61，N 14.87。
本发明所涉及的芳胺以氮原子通过碳氮键直接链接到苊并吡嗪衍生基元的3和/或4号位的所有化合物均按照此方法合成。
由于苊中的五元环具有形成6个π电子的环戊二烯结构的趋势，相较于萘、蒽、菲等稠环芳烃其具有更强的拉电子能力。苊并吡嗪基元中由于吡嗪的引入使得整个基元的拉电子能力相较于苊得到进一步加强，此外苊并吡嗪具有大的共轭平面，利于电子的离域，进而得到较高的荧光量子产率，因此，当在苊并吡嗪基元上引入合适的给电子基元后，容易的到高效的长波长发射。本发明的有机发光材料为基于苊并吡嗪衍生物的热活化延迟荧光材料，能有效地的降低分子的振动和转动而达到高的辐射跃迁速率，满足其在深红/近红外有机电致发光器件领域的应用。
本发明还提供了基于上述有机发光材料所制备的有机电致发光器件，包括阴极、阳极以及有机薄膜层，所述有机薄膜层设置在所述阴极和阳极之间，所述有机薄膜层包括至少一层有机发光层，所述有机薄膜层含有上述的有机发光材料，优选为采用上述有机发光材料制成的有机发光层。
其中，所述有机薄膜层还包括空穴注入层、空穴传输层、电子阻挡层、以及电子传输层，所述有机电致发光器件从高度方向上依次设有所述阳极、空穴注入层、空穴传输层、电子阻挡层、有机发光层、电子传输层以及阴极。
下面，对本发明的有机电致发光器件进行说明。
将涂布ITO透明导电层的玻璃板在商用清洗剂中超声处理，去离子水中冲洗，在丙酮和乙醇中各清洗三次，在洁净的环境下烘烤至完全除去水分，用紫外光和臭氧清洗，并用低能阳离子束轰击表面。把ITO导电玻璃置入真空腔内，抽真空至低于5×10-4Pa。以ITO导电玻璃为阳极，在其上依次蒸镀空穴注入层(HIL)、空穴传输层(HIL)、电子阻挡层(EBL)、有机发光层(EML)、电子传输层(ETL)以及阴极；其中，有机材料的蒸镀速率为0.2nm/s，金属电极的蒸镀速率为0.5nm/s。
使用光子多道分析仪PMA-12(Hamamatsu C10027-01)收集电致发光光谱，其可以在200-950nm的光谱区域中检测。通过使用积分球(Hamamatsu A10094)测量正向光强度得到器件的外量子效率。所有测量均在室温下在大气环境下进行。
本发明的有机电致发光器件中各结构层的形成方法没有特别限定，可以使用包括但不限于现有的真空蒸镀法、旋转涂覆法等。
实施例13至23
下面将结合实施例13至23来对OLED1-10以及基于参照材料ref的器件OLED11来进行说明，其中，OLED1-5所采用的材料为本发明所示的化合物式1-24，OLED6-10所采用的材料为本发明所示的化合物式1-144，各OLED器件结构和各层的膜厚厚度如下：
OLEDl：
ITO/HAT-CN(5nm)/NPB(70nm)/TCTA(5nm)/10wt％1-24:TPBi(20nm)/TPBi(60nm)/Liq(2nm)/Al(100nm)
OLED2：
ITO/HAT-CN(5nm)/NPB(70nm)/TCTA(5nm)/20wt％1-24:TPBi(20nm)/TPBi(60nm)/Liq(2nm)/Al(100nm)
OLED3：
ITO/HAT-CN(5nm)/NPB(70nm)/TCTA(5nm)/1-24(20nm)/TPBi(60nm)/Liq(2nm)/Al(100nm)
OLED4：
ITO/HAT-CN(5nm)/NPB(70nm)/TCTA(5nm)/10wt％1-24:Zn(BTZ)2(20nm)/TPBi(60nm)/Liq(2nm)/Al(100nm)
OLED5：
ITO/HAT-CN(5nm)/NPB(70nm)/TCTA(5nm)/20wt％1-24:Zn(BTZ)2(20nm)/TPBi(60nm)/Liq(2nm)/Al(100nm)
OLED6：
ITO/HAT-CN(5nm)/NPB(70nm)/TCTA(5nm)/10wt％1-84:TPBi(20nm)/TPBi(60nm)/Liq(2nm)/Al(100nm)
OLED7：
ITO/HAT-CN(5nm)/NPB(70nm)/TCTA(5nm)/20wt％1-84:TPBi(20nm)/TPBi(60nm)/Liq(2nm)/Al(100nm)
OLED8：
ITO/HAT-CN(5nm)/NPB(70nm)/TCTA(5nm)/1-84(20nm)/TPBi(60nm)/Liq(2nm)/Al(100nm)
OLED9：
ITO/HAT-CN(5nm)/NPB(70nm)/TCTA(5nm)/10wt％1-84:Zn(BTZ)2(20nm)/TPBi(60nm)/Liq(2nm)/Al(100nm)
OLED10：
ITO/HAT-CN(5nm)/NPB(70nm)/TCTA(5nm)/20wt％1-84:Zn(BTZ)2(20nm)/TPBi(60nm)/Liq(2nm)/Al(100nm)
OLED11：
ITO/HAT-CN(5nm)/NPB(70nm)/TCTA(5nm)/10wt％ref-1:TPBi(20nm)/TPBi(60nm)/Liq(2nm)/Al(100nm)
器件的性能数据如表2所示：
表2
请参见图3至图5，由图可知，实施例20所示的器件OLED8的最大外量子效率为3.30％，其在外加电压为5V时，发光光谱峰值为726nm。实施例18所示的器件OLED6的最大外量子效率为13.84％，其在外加电压为5V时，发光光谱峰值为635nm。实施例19所示的器件OLED7的最大外量子效率为11.14％，其在外加电压为5V时，发光光谱峰值为651nm。器件10的最大外量子效率为10.94，其在外加电压为5V时，发光光谱峰值为639nm。
由上述表2的结果，可以得知，本发明所提供的有机光电材料可以应用于高效的深红/近红外电致发光器件中。
实施例13至23所涉及的化合物结构如下：
综上所述：本发明的有机发光材料以苊并吡嗪衍生物为结构通式，并通过修饰其他不同化学基团，使该有机发光材料具有优异的发光特性、稳定的结构以及较高的色纯度，同时，其制备成本较低。并且，采用该有机发光材料的深红/近红外有机电致发光器件具有较高的发光效率和优异的性能。
以上所述实施例的各技术特征可以进行任意的组合，为使描述简洁，未对上述实施例中的各个技术特征所有可能的组合都进行描述，然而，只要这些技术特征的组合不存在矛盾，都应当认为是本说明书记载的范围。
以上所述实施例仅表达了本发明的几种实施方式，其描述较为具体和详细，但并不能因此而理解为对发明专利范围的限制。应当指出的是，对于本领域的普通技术人员来说，在不脱离本发明构思的前提下，还可以做出若干变形和改进，这些都属于本发明的保护范围。因此，本发明专利的保护范围应以所附权利要求为准。

Claims (10)

1.一种有机发光材料，其特征在于，为包含以下通式(1)表示的化合物：
通式(1)中，Y1和Y2分别选自氢基或氰基中的一种；X1和X2分别选自CH或N中的一种；L1连接一个或两个R1，L2连接一个或两个R2，且L1和L2分别选自氢基或单键，和/或，环原子数为6～18的芳基/杂芳族环；R1和R2分别选自环原子数为10～40的芳胺基。
2.如权利要求1所述的有机发光材料，其特征在于，在R1和R2所表示的芳胺基中，与苯环碳原子连接的氢基可以被R1取代，各位点的R1分别选自卤基、氰基、碳原子为1～10个的直链烷基/环状烷基/烷氧基/烷硫基或环原子数为6～30个的芳环中的任一种。
3.如权利要求2所示的有机发光材料，其特征在于，所述直链烷基或环状烷基可以存在卤族取代基。
4.如权利要求2或3所述的有机发光材料，其特征在于，R1和R2分别选自包括式Ar-1至Ar-19结构中的一种或多种：
其中，虚线表示与L1或L2相连接的键。
5.如权利要求4所述的有机发光材料，其特征在于，R1和R2分别选自包括咔唑、二苯胺、9,9-二甲基-9,10-二氢吖啶、吩恶嗪、吩噻嗪、9,9-二甲基-10-苯基-9,10-二氢吖啶、5—苯基-5,10-二氢吩嗪、10-苯基吩恶嗪、10-苯基吩噻嗪、螺芴吖啶、双二甲基碳闭环三苯胺、二氧杂闭环三苯胺、二硫杂闭环三苯胺、三二甲基碳闭环三苯胺、三氧杂闭环三苯胺或三硫杂闭环三苯胺中的任一种。
6.根据权利要求1至5中任一项所述的有机发光材料在用于制备深红/近红外电致发光器件中的应用。
7.一种有机电致发光器件，其特征在于，包括阴极、阳极以及有机薄膜层，所述有机薄膜层设置在所述阴极和阳极之间，所述有机薄膜层包括至少一层有机发光层，所述有机薄膜层含有如权利要求1至5中任一项所述的有机发光材料。
8.如权利要求7所述的有机电致发光器件，其特征在于，所述有机发光层包含所述有机发光材料。
9.如权利要求7所述的有机电致发光器件，其特征在于，所述有机薄膜层还包括空穴注入层、空穴传输层、电子阻挡层、以及电子传输层，所述有机电致发光器件从高度方向上依次设有所述阳极、空穴注入层、空穴传输层、电子阻挡层、有机发光层、电子传输层以及阴极。
10.如权利要求7至9中任一项所述的有机电致发光器件，其特征在于，所述有机电致发光器件为深红/近红外电致发光器件。
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