CN103468243A - 有机电子材料和有机电致发光器件 - Google Patents

有机电子材料和有机电致发光器件 Download PDF

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CN103468243A
CN103468243A CN201310219268XA CN201310219268A CN103468243A CN 103468243 A CN103468243 A CN 103468243A CN 201310219268X A CN201310219268X A CN 201310219268XA CN 201310219268 A CN201310219268 A CN 201310219268A CN 103468243 A CN103468243 A CN 103468243A
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organic
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CN103468243B (zh
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黄锦海
戴雷
陈金鑫
蔡丽菲
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Beijing Aglaia Technology Development Co Ltd
Guangdong Aglaia Optoelectronic Materials Co Ltd
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Beijing Aglaia Technology Development Co Ltd
Guangdong Aglaia Optoelectronic Materials Co Ltd
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Abstract

本发明涉及“有机电子材料和有机电致发光器件”，具有如下式（I）或（II）所述的结构。本发明的有机电致发光器件采用了含有荧蒽基团的化合物作为电子传输材料，具有较高的电子传输和注入能力，也由于其具有很好的热稳定性和良好的成膜性能，在提高有机电致发光器件效率的同时，也提高了器件的使用寿命；同时，本发明的有机电致命发光器件采用了含有荧蒽基团的化合物作为磷光的主体材料，由于其不但具有较高的三线态能级，而且具有很好的电子传输性能，能有效的提高发光层中电子的数量，提高器件的效率。

Description

有机电子材料和有机电致发光器件
技术领域
本发明涉及新型的有机电子材料，通过真空蒸渡沉积成薄膜，作为电子传输材料和磷光主体材料应用在有机电致发光二极管上，属于有机电致发光器件显示技术领域。
技术背景
有机电致发光器件作为一种新型的显示技术，具有自发光、宽视角、低能耗、效率高、薄、色彩丰富、响应速度快、适用温度范围广、低驱动电压、可制作柔性可弯曲与透明的显示面板以及环境友好等独特优点，因此，有机电致发光器件技术可以应用在平板显示器和新一代照明上，也可以作为LCD的背光源。自1987年柯达公司的Tang等利用真空薄膜蒸镀技术，用8-羟基喹啉铝（Alq3)作为发光层，三苯胺衍生物作为空穴传输层做出的夹心式双层器件，在10V的驱动电压下，发光亮度达1000cd/m2（Tang C.W.,Vanslyke S.A.Appl.Phys.Lett.1987,51,913-916)。这一突破性进展，引起了科技界和产业界的广泛关注，掀起了人们对有机电致发光研究和应用的热潮。随后，于1989年，主客体技术的发明，更是极大提高了有机电致发光器件的发光效率和工作寿命。1998年，Forrest等发现了电致磷光现象，突破了有机电致发光量子效率低于25%的理论限制，提升到100%(Baldo M.A.,Forrest S.R.Et al，Nature,1998,395,151-154)，使得有机电子发光的研究进入了一个新时期，拓宽了其研究领域。
一个经典的三层有机电致发光器件包含有空穴传输层，发光层和电子传输层。其中器件的电子传输层，传统使用的是Alq3，具有良好的成膜性和热稳定性，但是其发很强的绿光和较低的电子迁移率，影响了它的产业化应用。随后，一些具有优越性能的电子传输材料如TPBI,BCP，Bphen等也广泛应用在有机电致发光器件上。而现有发光层材料基本可以分为两类，分别为荧光发光材料和磷光发光材料，往往采用的是主客体掺杂技术。CBP(4,4′-bis(9-carbazolyl)-biphenyl)是一个具有高效和高三线态能级的磷光主体材料，当CBP作为主体材料时，三线态能量能够顺利地转移到磷光发光材料，从而产生高效的红光和绿光材料。但是这些具有代表性的主体材料，往往由于其的热稳定性和制备得到的器件寿命短而限制它们的应用。
尽管经过20年的发展，有机电致发光器件已经取得了长足的进步和发展，有机材料也随之不断的发展进行中，但是，符合市场化需求的且具有良好的器件效率和寿命，以及很好性能和稳定性的材料还是很少。
荧蒽作为电致发光材料，应用广泛，可以作为电子传输材料，空穴传输材料，发光材料，但是报道的文献要么没有详细描述器件性能，要么器件的效率比较低以及较低的器件稳定性，本发明就是在荧蒽的基础上发明一系列新型化合物，并且应用在有机电致发光器件上。
发明内容
本发明的目的是一种高效的新型有机电子传输和磷光主体材料的合成，以及在器件上的应用，提供高性能的有机电致发光器件和制备方法。
本发明所述的有机电子材料具有化学式(I)或者化学式(II)的化学结构式：
其中，
R1-R5中任意四个为氢，另一个为C1-C6烷基、C7-C24的芳基、含有一个或多个选自N、O、S的取代或未取代的杂芳环基、三芳香甲硅烷基、二芳胺基、二芳香氧磷基、芳香羰基、芳硫基；或者
R1、R3、R5为氢，R2、R4分别独立为C1-C6烷基、C6-C24的芳基、含有一个或多个选自N、O、S的杂芳环、三芳香甲硅烷基、二芳胺基、二芳香氧磷基、芳香羰基、芳硫基；
A独立地表示为C(R6)2、N(R7)、S、O、P(R8)、S(O)2或者B(R9)，R6-R9独立地表示为氢、氘、C1-C6烷基、苯基、C1-C6烷基苯基、含有一个或多个选自N、O、S的杂芳基，或两个R6与C之间形成环状结构。
优选，R1-R5优选为芴基、C1-C4烷基或苯基或萘基取代的五元或六元杂芳环基、二苯基胺基、苯萘胺基、三苯基甲硅烷基、二苯基氧磷、苯基羰基、苯基硫基。
其中所述五元或六元杂环芳烃基为咔唑基、嘧啶基、吡啶基、噻唑基，三氮唑基，三嗪基。
所述芴基为9，9-二甲基芴基、9，9-二苯基芴基、9，9-二甲苯基芴基或螺芴基。
所述R1、R2、R4、R5为氢。
A优选C(R6)2、N(R7)、S、O、S(O)2，R6-R7优选氢、甲基，苯基或甲基苯基，或两个R6与C之间形成五元环状结构。
本发明优选的化合物如下，但是并没有限制在这些里面
Figure BDA00003302917900031
Figure BDA00003302917900051
Figure BDA00003302917900061
本发明的有机电致发光器件包括基板，于基板上形成的阳极层，于阳极层上依次蒸镀空穴注入层，空穴传输层，发光层，电子传输层以及电子注入层和阴极阳极。
发光层可分为荧光发光层或者为磷光发光层。
本发明中的有机电子发光器件一个实施方式，利用本发明的化合物作为电子传输材料；
本发明的有机电致发光器件的另外一个实施方式为，利用以上化合物作为磷光主体材料，客体材料优选为有机铱化合物和有机铂化合物；
本发明的有机电致发光器件中，利用以上化合物作为磷光主体材料，并利用以上化合作为电子传输层。
本发明的有机电致发光器件采用了含有荧蒽基团的化合物作为电子传输材料，具有较高的电子传输和注入能力，也由于其具有很好的热稳定性和良好的成膜性能，在提高有机电致发光器件效率的同时，也提高了器件的使用寿命；同时，本发明的有机电致命发光器件采用了含有荧蒽基团的化合物作为磷光的主体材料，由于其不但具有较高的三线态能级，而且具有很好的电子传输性能，能有效的提高发光层中电子的数量，提高器件的效率。
附图说明
图1为本发明的器件结构图，其中10代表为玻璃基板，20代表为阳极，30代表为空穴注入层，40代表为空穴传输层，50代表为发光层，60代表为电子传输层，70代表为电子注入层，80代表为阴极。
图2为化合物46的1H NMR图。
图3为化合物36的1H NMR图。
图4为化合物46的DSC图。
具体实施方式
下面结合实施例对本发明作进一步的详细说明。
实施例1：化合物43合成
中间体1-1的合成
向烧瓶中加入7.5g2-溴-9,9-二甲基-芴，0.15g碘化亚铜，0.3g四三苯基磷钯，然后加入三乙胺通氮气，开始搅拌，使充分溶解，然后加入10ml三甲基硅乙炔，过夜回流反应12小时。减压除去溶剂。加入水，用乙醚萃取三次，合并有机相，用饱和食盐水洗三次，干燥，抽滤，浓缩，得到6.8g产品，产率85%。
中间体1-2的合成
向烧瓶中加入45ml甲醇，50ml二氯甲烷，5g氢氧化钾，6.8g中间体1-1，通氮气，搅拌反应1小时。过滤除去无机盐，除去有机溶剂，滤饼用甲醇重结晶，得到4.2g，产率为82%。
中间体1-3的合成
将84g苊醌，72.8g1,3-二苯基丙酮，600ml乙醇,56g氢氧化钾，加入四口烧瓶，开始搅拌，通氮气，回流2小时。冷却室温，过滤，滤饼用乙醇淋洗2次，得到130g黑色固体，产率为91%。
化合物43的合成
将4.2g中间体1-2和6.3g中间体1-3，还60ml二苯醚加入到四口烧瓶中，开始搅拌，通氮气10分钟，开始加热回流12小时，冷却，过滤，滤饼用乙酸乙酯加热回流，冷却，过滤得到6.5g淡黄色固体，产率为66%。1H NMR(400MHz,CD2Cl2,δ)：7.56-7.74(m,9H),7.21-7.44(m,14H),7.76-7.70(m,1H),1.27(s,6H).MALDI-TOF-MS m/s计算值C43H30：546.2，实测值[M+]:546.5。
实施例2：化合物46合成
Figure BDA00003302917900081
中间体2-1的合成
向烧瓶中加入8.0g中间体2-0，0.15g碘化亚铜，0.3g四三苯基磷钯，然后加入三乙胺通氮气，开始搅拌，使充分溶解，然后加入10ml三甲基硅乙炔，过夜回流反应12小时。减压除去溶剂。加入水，用乙醚萃取三次，合并有机相，用饱和食盐水洗三次，干燥，抽滤，浓缩，得到6.8g产品，产率83%。
中间体2-2的合成
向烧瓶中加入45ml甲醇，50ml二氯甲烷，5g氢氧化钾，7g中间体2-1，通氮气，搅拌反应1小时。过滤除去无机盐，除去有机溶剂，滤饼用甲醇重结晶，得到4.0g，产率为70%。
化合物46的合成
将4.0g中间体2-2和4.2g中间体1-3，60ml二苯醚加入到四口烧瓶中，开始搅拌，通氮气10分钟，开始加热回流12小时，冷却，过滤，滤饼用乙酸乙酯加热回流，冷却，过滤得到7.0g淡黄色固体，产率为89%。1H NMR(400MHz,CDCl3,δ)：7.61-7,79（m,8H),7.47-7.52(m,3H),7.32-7.36(m,5H),7.20-7.24(m,3H),7.02-7.14(m,8H),6.56-6.65(m,4H),6.49(s,1H)。如图2。MALDI-TOF-MS m/s计算值C53H32：668.3，实测值[M+]:668.5。
实施例3：化合物35合成
中间体3-1的合成
向烧瓶中加入7.7g中间体3-0，0.15g碘化亚铜，0.3g四三苯基磷钯，然后加入三乙胺通氮气，开始搅拌，使充分溶解，然后加入10ml三甲基硅乙炔，过夜回流反应12小时。减压除去溶剂。加入水，用乙醚萃取三次，合并有机相，用饱和食盐水洗三次，干燥，抽滤，浓缩，得到6.8g产品，产率67%。
中间体3-2的合成
向烧瓶中加入45ml甲醇，50ml二氯甲烷，5g氢氧化钾，5.5g中间体3-1，通氮气，搅拌反应1小时。过滤除去无机盐，除去有机溶剂，滤饼用甲醇重结晶，得到4.11g，产率为95%。
化合物35的合成
将4.0g中间体3-2和5.5g中间体1-3，60ml二苯醚加入到四口烧瓶中，开始搅拌，通氮气10分钟，开始加热回流12小时，冷却，过滤，滤饼用乙酸乙酯加热回流，冷却，过滤得到4.5g淡黄色固体，产率为49%。1H NMR(400MHz,CD2Cl2,δ)：8.12-8.13（d,J=7.6Hz,2H),7.74-7.77(m,4H),7.52-7.60(m,3H),7.25-7.45(m,19H),6.69-6.81(d,J=7.2Hz,1H).MALDI-TOF-MS m/s计算值C46H29N：595.2，实测值[M+]:595.4。
实施例4：化合物26合成
Figure BDA00003302917900101
合成工艺跟实施例1一样
实施例5：化合物36合成
Figure BDA00003302917900111
中间体5-1的合成
向烧瓶中加入9.1g化合物5-0，0.15g碘化亚铜，0.24g四三苯基磷钯，然后加入100ml三乙胺通氮气，开始搅拌，使充分溶解，然后加入10ml三甲基硅乙炔，过夜回流反应12小时。减压除去溶剂。加入水，用乙醚萃取三次，合并有机相，用饱和食盐水洗三次，干燥，抽滤，浓缩，得到6.8g产品，产率74%。
中间体5-2的合成
向烧瓶中加入45ml甲醇，50ml二氯甲烷，5g氢氧化钾，7g中间体2-1，通氮气，搅拌反应1小时。过滤除去无机盐，除去有机溶剂，滤饼用甲醇重结晶，得到5.0g，产率为83%。
化合物36的合成
将4.8g中间体6-2和3.9g中间体1-3，60ml二苯醚加入到四口烧瓶中，开始搅拌，通氮气10分钟，开始加热回流12小时，冷却，过滤,l滤饼用乙酸乙酯加热回流，冷却，过滤得到5.5g淡黄色固体，产率为65%。1H NMR(400MHz,CD2Cl2,δ)：8.14-8.16（d,J=8.4Hz,4H),7.72-7.80(m,4H),7.54-7.69(m,11H),7.27-7.50(m,16H),6.74-6.76(d,J=6.8Hz,1H).如图3。MALDI-TOF-MS m/s计算值C59H36N2：760.3，实测值[M+]:760.5。
实施例6
在氮气保护下，以20℃/min的加热和冷却速度用DSC方法测试化合物26的玻璃化温度。测得的化合物26的玻璃化转变温度Tg为140℃。用相同的方法测试化合物35，化合物36，化合物43,和化合物46的玻璃化温度，所得结果列于表1中。
比较例1
跟实施例1一样的条件，测得化合物mCP和BCP的玻璃化转变温度，所得结果也列于表1中。
Figure BDA00003302917900121
Figure BDA00003302917900122
从表1中，可以看出本发明的化合物比常规的市场化的主体材料具有更高的玻璃化转变温度，本发明改善了电致发光材料的热稳定性。
实施7
使用本发明的有机电致发光材料制备OLED，器件结构如图1
首先，将透明导电ITO玻璃（带有阳极20的玻璃基板10）依次经：洗涤剂溶液和去离子水，乙醇，丙酮，去离子水洗净。再用氧等离子处理30秒，接着用等离子处理的CFx处理。
然后，在ITO上蒸渡5nm厚的MoO3空穴注入层30。
然后，蒸渡TAPC形成50nm厚的空穴传输层40。
然后，在空穴传输层上蒸渡10nm厚发光层50，其中，化合物35为主体发光材料，而以10%FIrpic作为作为蓝色磷光材料。
然后，在发光层上蒸渡50nm厚的TmPyPb作为电子传输层60。
最后，蒸渡1.2nm LiF作为电子注入层70和150nm Al阴极。
本发明所制备的有机电致发光器件在4V的驱动电压下的电流密度为0.28mA/cm2，发射蓝光。
Figure BDA00003302917900131
比较例2
器件结构跟实施例7一样，除了用CBP代替化合物35。
此比较例制备的有机电致发光器件在4V的驱动电压下的电流密度为0.17mA/cm2，发射蓝光。
因此，本发明相比较常规的材料，在相同的驱动电压下具有跟高的电流密度，改善了电致发光性质。

Claims (14)

1.一种有机电子材料，具有如下式（I）或（II）所述的结构，
Figure FDA00003302917800011
其中，
R1-R5中任意四个为氢，另一个为C1-C6烷基、C7-C24的芳基、含有一个或多个选自N、O、S的取代或未取代的杂芳环、三芳香甲硅烷基、二芳胺基、二芳香氧磷基、芳香羰基、芳硫基；或者
R1、R3、R5为氢，R2、R4分别独立为C1-C6烷基、C6-C24的芳基、含有一个或多个选自N、O、S的杂芳环、三芳香甲硅烷基、二芳胺基、二芳香氧磷基、芳香羰基、芳硫基；
A独立地表示为C(R6)2、N(R7)、S、O、P(R8)、S(O)2或者B(R9)，R6-R9独立地表示为氢、氘、烷基、苯基、烷基苯基、含有一个或多个选自N、O、S的杂芳基，或两个R6与C之间形成环状结构。
2.根据权利要求1所述的有机电子材料，其中R1-R5中任意四个为氢，另一个为芴基、烷基或苯基或萘基取代的五元或六元杂芳环基、二苯基胺基、苯萘胺基、三苯基甲硅烷基、二苯基氧磷、苯基羰基或苯基硫基。
3.根据权利要求2所述的有机电子材料，其中所述五元或六元杂芳环基为咔唑基、嘧啶基、吡啶基、噻唑基、三氮唑基或三嗪基。
4.根据权利要求2所述的有机电子材料，其中所述芴基为9，9-二甲基芴基、9，9-二苯基芴基、9，9-二甲苯基芴基或螺芴基。
5.根据权利要求2-4任一所述的有机电子材料，其中R1、R2、R4、R5为氢。
6.根据权利要求1所述的有机电致发光材料，其中A为C(R6)2、N(R7)、S、O、S(O)2，R6、R7独立为氢、甲基、苯基或甲基苯基，或两个R6与C之间形成五元环状结构。
7.权利要求1所述的有机电子材料，其结构如下：
Figure FDA00003302917800021
Figure FDA00003302917800051
8.权利要求1所述的有机电子材料，其结构式为：
9.一种含有权利要求1-8任一所述的有机电子材料的有机电致发光器件。
10.根据权利要求9所述的有机电致发光器件，包括空穴注入层，空穴传输层，发光层，电子传输层或/和电子注入层，其中权利要求1-8任一所述的有机电子材料作为空穴注入层，空穴传输层，发光层，电子传输层或/和电子注入层中的任一层或多层中的材料。
11.根据权利要求10所述的有机电致发光器件，权利要求1-8任一所述的有机电子材料作为电子传输层的材料。
12.根据权利要求10所述的有机电致发光器件，所述发光层中包括主体材料和客体材料，其中权利要求1-8任一所述的有机电子材料为发光层中红色磷光的主体材料。
13.根据权利要求12所述的有机电致发光器件，其中客体材料为有机铱化合物或有机铂化合物。
14.根据权利要求12或13所述的有机电致发光器件，权利要求1-8任一所述的有机电子材料作为电子传输层的材料。
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