CN106831313A - 一种具有三芳基萘的化合物及其有机电致发光器件 - Google Patents

一种具有三芳基萘的化合物及其有机电致发光器件 Download PDF

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CN106831313A
CN106831313A CN201710055510.2A CN201710055510A CN106831313A CN 106831313 A CN106831313 A CN 106831313A CN 201710055510 A CN201710055510 A CN 201710055510A CN 106831313 A CN106831313 A CN 106831313A
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layer
compound
organic
naphthalene
triaryl
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黄锦海
苏建华
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Shanghai Taoe Chemical Technology Co Ltd
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Shanghai Taoe Chemical Technology Co Ltd
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Abstract

本发明提供了一种具有三芳基萘的有机电致发光化合物，该化合物具有较好热稳定性、高发光效率、高发光纯度，可以用于制作有机电致发光器件，应用于有机太阳能电池、有机薄膜晶体管或有机光感受器领域。本发明还提供了一种有机电致发光器件，其包括阳极、阴极和有机层，有机层包含发光层、空穴注入层、空穴传输层、空穴阻挡层、电子注入层、电子传输层中的至少一层，有机层中至少一层包含有如结构式I的化合物。

Description

一种具有三芳基萘的化合物及其有机电致发光器件
技术领域
本发明涉及有机电致发光材料领域，具体涉及一种具有三芳基萘的有机电致发光化合物及其有机电致发光器件，属于有机电致发光器件显示技术领域。
背景技术
有机电致发光器件(OLEDs)为在两个金属电极之间通过旋涂或者真空蒸镀沉积一层有机材料制备而成的器件，一个经典的三层有机电致发光器件包含空穴传输层、发光层和电子传输层。由阳极产生的空穴经空穴传输层跟由阴极产生的电子经电子传输层结合在发光层形成激子，而后发光。有机电致发光器件可以根据需要通过改变发光层的材料来调节发射各种需要的光。
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，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。
自从20世纪80年代底发明以来，有机电致发光器件已经在产业上有所应用，比如作为相机和手机等屏幕，但是目前的OLED器件由于效率低，使用寿命短等因素制约其更广泛的应用，特别是大屏幕显示器，因此需要提高器件的效率。而制约其中的一个重要因素就是有机电致发光器件中的有机电致发光材料的性能。另外由于OLED器件在施加电压运行的时候，会产生焦耳热，使得有机材料容易发生结晶，影响了器件的寿命和效率，因此，也需要开发稳定高效的有机电致发光材料。
在有机电致发光器件中，空穴传输材料和注入材料的引入，可以有效地降低正电荷从正极传输到发光层的能力，提高器件的效率和热稳定。传统的空穴注入材料，如copperphthalocyanine(CuPc)，降解慢，制备耗能高，不利于环境保护，而且其会吸收光，影响器件的效率。NPB等原始的空穴传输材料，热稳定性比较差，也很大程度影响器件寿命。因而，需要开发高效稳定的有机电致发光材料。
在三原色(红，蓝，绿)当中，红光和绿光材料最近已经取得了很大的发展，也符合面板的市场需求。对于稳定且高效的蓝光材料还是很少，由于蓝光的高能隙，使得对于材料的要求更高，又由于蓝色磷光材料的稳定性和光纯度存在的问题，因此开发高效稳定的蓝色荧光材料尤为重要。
发明内容
本发明首先提供一种具有三芳基萘的有机电致发光化合物，其为具有如下结构式I的化合物：
其中，R1-R4分别独立地选自氢、氘、卤素、氰基、硝基、C1-C8烷基、C1-C8烷氧基、C6-C30的取代或者未取代的芳基、C3-C30的取代或者未取代的含有一个或者多个的杂原子芳基；Ar1-Ar3分别独立地选自C6-C30的取代或者未取代的芳基、C3-C30的取代或者未取代的含有一个或者多个的杂原子芳基；L选自苯基和联苯基。
优选地，R1-R4分别独立地选自氢、氘、氟、甲基、苯基、吡啶基。
优选地，Ar1和Ar2分别独立地选自苯基、萘基、联苯基、吡啶基。
优选地，Ar3选自苯基、萘基、N-芳基(C6-C30)或者C1-C4的烷基取代的咔唑基、蒽基、菲基、芘基、苝基、荧蒽基、(9,9-二烷基)芴基、(9,9-二取代或者未取代的芳基)芴基、9,9-螺芴基、三芳香(C6-C60)胺基、二苯并噻吩基、二苯并呋喃基、吡啶基、嘧啶基、哒嗪基、三嗪基、咪唑基、噁唑基、噻唑基、噻二唑基、喹啉基、异喹啉基、喹唑啉基、喹喔啉基、氮杂二苯并呋基、氮杂二苯并噻吩基、苯并咪唑基、苯并噻唑基、苯并恶唑基、喹啉基、喹喔啉基，以上芳基和杂芳基可以被C1-C12的烷基取代。
更优选地，R1-R4独立地选自氢、氘；Ar1和Ar2为苯基。
进一步优选地，本发明的具有三芳基萘的有机电致发光化合物为下列结构式1-82的化合物：
本发明的一种具有三芳基萘结构的有机电致发光化合物可以应用在有机电致发光器件、有机太阳能电池、有机薄膜晶体管或有机光感受器领域。
本发明还提供了一种有机电致发光器件，该器件包含阳极、阴极和有机层，有机层包含发光层、空穴注入层、空穴传输层、空穴阻挡层、电子注入层、电子传输层中的至少一层，其中所述有机层中至少有一层含有如结构式I所述的有机电致发光化合物：
其中R1-R4、Ar1-Ar3和L的定义如前所述。
其中有机层为发光层；
或者有机层为发光层和电子传输层；
或者有机层为发光层、电子传输层和电子注入层；
或者有机层为空穴传输层和发光层；
或者有机层为空穴注入层、空穴传输层和发光层；
或者有机层为空穴传输层、发光层和电子传输层；
或者有机层为空穴注入层、空穴传输层、发光层和电子传输层；
或者有机层为空穴注入层、空穴传输层、发光层、电子传输层和电子注入层；
或者有机层为空穴注入层、空穴传输层、阻挡层、发光层、电子传输层和电子注入层；
或者有机层为空穴传输层、发光层、电子传输层、电子注入层和空穴阻挡层；
或者有机层为空穴传输层、发光层、电子注入层和空穴阻挡层。
优选地，其中如结构式I所述的合物所在的层为发光层、空穴传输层、空穴注入层、电子传输层、电子注入层。
优选地，其中结构式I所述的化合物为结构式1-82的化合物。
如结构式I所述的具有三芳基萘的有机电致发光化合物用于发光器件制备时，可以单独使用，也可以和其它化合物混合使用；如结构式I所述的具有三芳基萘的有机电致发光化合物可以单独使用其中的一种化合物，也可以同时使用结构式I中的两种以上的化合物。
本发明的有机电致发光器件，进一步优选的方式为，该有机电致发光器件包含阳极、空穴注入层、空穴传输层、发光层、电子传输层、电子注入层和阴极，其中发光层中含有一种以上的结构式I的化合物；进一步优选地，发光层中含有一种以上的结构式1-82的化合物。
有机电致发光器件的发光层含有发光客体材料和具有结构式I的化合物作为主体材料，其中结构式I化合物作为主体材料，其浓度为整个发光层重量的20-99.9％，优选80-99％，更优选为90-99％。
本发明的有机电致发光器件有机层的总厚度为1-1000nm，优选50-500nm。
本发明的有机电致发光器件在使用本发明具有结构式I的化合物时，可以搭配使用其它材料，如在空穴注入层、空穴传输层、发光层、电子传输层、电子注入层和阻挡层中等，而获得蓝光、绿光、黄光、红光或者白光。
本发明有机电致发光器件的空穴传输层和空穴注入层，所需材料具有很好的空穴传输性能，能够有效地把空穴从阳极传输到发光层上。除了可以使用具有本发明I的化合物外，还可以包括其它小分子和高分子有机化合物，包括但不限于咔唑类化合物、三芳香胺化合物、联苯二胺化合物、芴类化合物、酞菁类化合物、六氰基六杂三苯(hexanitrilehexaazatriphenylene)、2,3,5,6-四氟-7,7',8,8'-四氰二甲基对苯醌(F4-TCNQ)、聚乙烯基咔唑、聚噻吩、聚乙烯或聚苯磺酸。
本发明的有机电致发光器件的发光层，具有很好的发光特性，可以根据需要调节可见光的范围。除本发明的具有结构式I化合物外，还可以含有如下化合物，但是不限于此，萘类化合物、芘类化合物、芴类化合物、菲类化合物、屈类化合物、荧蒽类化合物、蒽类化合物、并五苯类化合物、苝类化合物、二芳乙烯类化合物、三苯胺乙烯类化合物、胺类化合物、苯并咪唑类化合物、呋喃类化合物、有机金属螯合物。
本发明有机电致发光器件的有机电子传输材料要求具有很好的电子传输性能，能够有效地把电子从阴极传输到发光层中，具有很大的电子迁移率。除了可以为本发明的化合物外，还可以选择如下化合物，但是不限于此：氧杂恶唑、噻唑类化合物、三氮唑类化合物、三氮嗪类化合物、三氮杂苯类化合物、喔啉类化合物、二氮蒽类化合物、含硅杂环类化合物、喹啉类化合物、菲啰啉类化合物、金属螯合物(如Alq3)、氟取代苯类化合物、苯并咪唑类化合物。
本发明有机电致发光器件的电子注入层，可以有效地把电子从阴极注入到有机层中，主要选自碱金属或者碱金属的化合物，或选自碱土金属或者碱土金属的化合物或者碱金属络合物，可以选择如下化合物，但是不限于此：碱金属、碱土金属、稀土金属、碱金属的氧化物或者卤化物、碱土金属的氧化物或者卤化物、稀土金属的氧化物或者卤化物、碱金属或者碱土金属的有机络合物；优选为锂、氟化锂、氧化锂、氮化锂、8-羟基喹啉锂、铯、碳酸铯、8-羟基喹啉铯、钙、氟化钙、氧化钙、镁、氟化镁、碳酸镁、氧化镁，这些化合物可以单独使用也可以混合物使用，也可以跟其他有机电致发光材料配合使用。
本发明的有机电致发光器件中有机层的每一层，可以通过真空蒸镀法、分子束蒸镀法、溶于溶剂的浸涂法、旋涂法、棒涂法或者喷墨打印等方式制备。对于金属电机可以使用蒸镀法或者溅射法进行制备。
器件实验表明，本发明如结构式I所述的具有三芳基萘的有机电致发光化合物，具有较好热稳定性、高发光效率、高发光纯度。采用该具有三芳基萘的有机电致发光化合物制作的有机电致发光器件具有电致发光效率良好和色纯度优异以及寿命长的优点。
附图说明
图1为本发明的一种有机电致发光器件结构示意图；
其中，110代表为玻璃基板，120代表为阳极，130代表为空穴传输层，140代表为发光层，150代表为电子传输层，160代表为电子注入层，170代表为阴极。
具体实施方式
为了更详细叙述本发明，特举以下例子，但是不限于此。
2-(4-溴苯基萘)-1,4-二苯基萘的合成
在烧瓶中，加入1,3-二苯基异苯并呋喃(10g,37mmol)、对溴苯乙炔(6.7g,37mmol)和均三甲苯(100ml)，在氮气保护下加热回流10小时，冷却，除去溶剂，粗产品经柱层析纯化得到5.6g，产率35％。
2-(3-溴苯基萘)-1,4-二苯基萘的合成
合成方法跟2-(4-溴苯基萘)-1,4-二苯基萘一样，除了用间溴苯乙炔代替对溴苯乙炔外，产率43％。
实施例1
化合物4的合成
在烧瓶中，加入2-(4-溴苯基萘)-1,4-二苯基萘(1.4g,3.2mmol)、9-(1-萘基)-10-蒽硼酸(1.1g,3.2mmol)、碳酸钾(0.9g,6.5mmol)、四三苯基膦钯(0.2g)、四氢呋喃(20mL)和水(10ml)，在氮气保护下加热回流10小时，冷却，除去四氢呋喃，过滤，滤饼用四氢呋喃和乙醇重结晶，得到1.6g，产率76％。
实施例2
化合物5的合成
合成方法跟化合物4的一样，除了用9-(2-萘)-10-蒽硼酸代替9-(1-萘基)-10-蒽硼酸外，产率70％。
实施例3
化合物17的合成
合成方法跟化合物5一样，除了用2-(3-溴苯基)-1,4-二苯基萘代替2-(4-溴苯基)-1,4-二苯基萘代替外，产率80％。
实施例4
化合物29的合成
在烧瓶中，加入2-(4-溴苯基萘)-1,4-二苯基萘(2g,4.6mmol)、N-[1,1’-联苯-4-基]-9,9-二甲基-9H-芴-2-胺(1.7g,4.6mmol)、叔丁醇钠(0.9g,9.2mmol)和醋酸钯(0.15g)、X-phos(0.3g)和30ml的邻二甲苯，加热回流10小时，冷却，除去溶剂，粗产品经柱层析纯化得到2.1g，产率63％。
实施例5
化合物41的合成
合成方法跟化合物29的一样，所用的原料为2-(3-溴苯基)-1,4-二苯基萘和二(4-联苯)胺，产率55％。
实施例6
化合物42的合成
合成方法跟化合物41的一样，所用原料为2-(3-溴苯基)-1,4-二苯基萘和N-[1,1’-联苯-4-基]-9,9-二甲基-9H-芴-2-胺，产率73％。
实施例7
化合物56的合成
中间体56-1的合成
在烧瓶中，加入2-(4-溴苯基萘)-1,4-二苯基萘(5g,11.5mmol)、联硼酸频那醇酯(3.5g,14mmol)、乙酸钾(2.25g,23mmol)、二氯三苯基膦钯(0.3g)、二氧六环(50ml)，在氮气保护下加热回流10小时，冷却，除去溶剂，加入二氯甲烷和水，分液，干燥，浓缩，粗品经柱层析纯化得到4.8g，产率87％。
化合物56的合成
在烧瓶中，加入中间体56-1(2g,4.1mmol)、2-氯-4,6-二苯基-1,3,5-三嗪(1.2g,4.6mmol、碳酸钾(1.1g,8.2mmol)、四三苯基膦钯(0.2g)、四氢呋喃(30ml)和水(10ml)，在氮气保护下加热回流10小时，冷却，用二氯甲烷萃取，干燥浓缩，粗产品经柱层析纯化得到1.4g，产率58％。
实施例8
化合物68的合成
合成方法跟化合物56的一样，除了用2-(4-溴苯基)-4,6-三嗪代替2-氯-4,6-二苯基-1,3,5-三嗪外，产率84％。
实施例9
化合物70的合成
合成方法跟化合物56的合成一样，除了用2-(3-溴苯基)-4,6-三嗪代替2-氯-4,6-二苯基-1,3,5-三嗪外，产率78％。
实施例10
化合物73的合成
中间体73-1的合成
合成方法跟中间体56-1一样，除了用2-(3-溴苯基)-1,4-二苯基萘代替2-(4-溴苯基)-1,4-二苯基萘外，产率80％。
化合物73的合成
合成方法跟化合物70的一样，除了用中间体73-1代替中间体56-1外，产率91％。
实施例11
化合物74的合成
在烧瓶中，加入2-(4-溴苯基)-1,4-二苯基萘(2.3g,5.3mmol)、B-[4-(1-苯基-1H-苯并咪唑-2-基)苯基]-硼酸(1.8g,5.8mmol)、碳酸钾(1.5g,11mmol)、四三苯基膦钯(0.2g)、四氢呋喃(20ml)和水(10ml)，在氮气保护下加热回流10小时，冷却，除去溶剂，用二氯甲烷萃取，干燥，浓缩，粗产品经柱层析纯化得到2.4g，产率73％。
实施例12-14
有机电致发光器件的制备
使用实施例的化合物制备OLED。
首先，将透明导电ITO玻璃基板110(上面带有阳极120)(中国南玻集团股份有限公司)依次经：去离子水，乙醇，丙酮和去离子水洗净，再用氧等离子处理30秒。
然后，蒸镀化合物NPB，形成60nm厚的空穴传输层130。
然后，在空穴传输层上蒸镀40nm厚的发光层140。其中，本发明化合物和MADN分别为主体发光材料，而以3％重量比的BUBD-1作为掺杂客体材料。
然后，在发光层上蒸镀20nm厚的Alq3作为电子传输层150。
最后，蒸镀1nm LiF为电子注入层160和100nm Al作为器件阴极170。
所制备的器件(结构如图1)用Photo Research PR650光谱仪测得在1000cd/m2的亮度下的电压为如下表1。
比较例1
除了发光层用MADN代替本发明化合物外，其他的跟实施例8一样。所制备的器件用Photo Research PR650光谱仪测得在1000cd/m2的亮度下的电压如下表1。
表1在1000cd/m2亮度下的电压
实施例 化合物 驱动电压(V) 光谱
12 4 6 蓝光
13 5 5.8 蓝光
14 17 5.9 蓝光
比较例1 MADN 6.5 蓝光
从上结果可以看出，应用本发明的化合物制备的有机电致发光器件在相同的亮度条件下，器件的驱动电压低于比较例。
器件中所述化合物的结构式如下：
实施例15-17
有机电致发光器件的制备
首先，将透明导电ITO玻璃基板110(上面带有阳极120)(中国南玻集团股份有限公司)依次经：去离子水、乙醇、丙酮和去离子水洗净，再用氧等离子处理30秒。
然后，蒸镀本发明化合物，形成60nm厚的空穴传输层130。
然后，在空穴传输层上蒸镀30nm厚的化合物Alq3作为发光层140。
然后，在发光层上蒸镀20nm厚的Alq3作为电子传输层150。最后，蒸镀1nmLiF为电子注入层160和100nm Al作为器件阴极170。
所制备的器件(结构如图1)用Photo Research PR650光谱仪测得在150mA/cm2的电流密度下的电流效率为如下表2。
比较例2
器件的制备方法跟实施例15-17一样，除了用化合物NPB代替本发明化合物外，测得的在150mA/cm2的电流密度下的电流效率如表2。
表2在150mA/cm2的电流密度下的电流效率
实施例 化合物 电流效率(cd/A) 光谱
15 29 1.8 绿光
16 41 1.9 绿光
17 42 1.7 绿光
比较例2 NPB 1.2 绿光
在相同的条件下，应用本发明的有机电致发光化合物制备的有机电致发光器件的电流效率高于比较例。如上所述，本发明的化合物具有高的稳定性，本发明制备的有机电致发光器件具有低驱动电压，高的效率和光纯度。
实施例18-22
有机电致发光器件的制备
使用本发明的化合物制备OLED。
首先，将透明导电ITO玻璃基板110(上面带有阳极120)(中国南玻集团股份有限公司)依次经：去离子水，乙醇，丙酮和去离子水洗净，再用氧等离子处理30秒。
然后，蒸镀NPB，形成60nm厚的空穴传输层130。
然后，在空穴传输层上蒸镀37.5nm厚的Alq3掺杂1％C545T作为发光层140。
然后，在发光层上蒸镀37.5nm厚作为电子传输层150，包含75％本发明化合物和25％的LiQ。
最后，蒸镀1nm LiF为电子注入层160和100nm Al作为器件阴极170。
比较例3
除了电子传输层用Alq3代替本发明化合物外，其他的跟实施例18-22一样。
所制备的器件(结构示意图见图1)在6000cd/m2亮度下工作24小时后的寿命如表3。
表3在6000cd/m2亮度下工作24小时后的寿命
实施例 化合物 寿命 颜色
18 56 81％ 绿光
19 68 84％ 绿光
20 70 85％ 绿光
21 73 83％ 绿光
22 74 82％ 绿光
比较例3 75％ 绿光
在相同的条件下，应用本发明的有机电致发光电子传输材料制备的有机电致发光器件的寿命高于比较例，如上所述，本发明的化合物具有高的稳定性，本发明制备的有机电致发光器件具有高的寿命和光纯度。
器件中所述结构式
以上详细描述了本发明的较佳具体实施例。应当理解，本领域的普通技术人员无需创造性劳动就可以根据本发明的构思作出诸多修改和变化。因此，凡本技术领域中技术人员依本发明的构思在现有技术的基础上通过逻辑分析、推理或者有限的实验可以得到的技术方案，皆应在由权利要求书所确定的保护范围内。

Claims (10)

1.一种具有三芳基萘的有机电致发光化合物，其特征在于其为具有如下结构式I的化合物：
其中，R1-R4分别独立地选自氢、氘、卤素、氰基、硝基、C1-C8烷基、C1-C8烷氧基、C6-C30的取代或者未取代的芳基、C3-C30的取代或者未取代的含有一个或者多个的杂原子芳基；Ar1-Ar3分别独立地选自C6-C30的取代或者未取代的芳基、C3-C30的取代或者未取代的含有一个或者多个的杂原子芳基；L选自苯基和联苯基。
2.根据权利要求1所述的具有三芳基萘的有机电致发光化合物，其特征在于R1-R4分别独立地选自氢、氘、氟、甲基、苯基、吡啶基，Ar1和Ar2分别独立地选自苯基、萘基、联苯基、吡啶基。
3.根据权利要求1所述的具有三芳基萘的有机电致发光化合物，其特征在于Ar3选自苯基、萘基、N-芳基(C6-C30)或者C1-C4的烷基取代的咔唑基、蒽基、菲基、芘基、苝基、荧蒽基、(9,9-二烷基)芴基、(9,9-二取代或者未取代的芳基)芴基、9,9-螺芴基、三芳香(C6-C60)胺基、二苯并噻吩基、二苯并呋喃基、吡啶基、嘧啶基、哒嗪基、三嗪基、咪唑基、噁唑基、噻唑基、噻二唑基、喹啉基、异喹啉基、喹唑啉基、喹喔啉基、氮杂二苯并呋基、氮杂二苯并噻吩基、苯并咪唑基、苯并噻唑基、苯并恶唑基、喹啉基、喹喔啉基，或以上芳基和杂芳基被C1-C12的烷基取代。
4.根据权利要求1所述的具有三芳基萘的有机电致发光化合物，其特征在于R1-R4独立地选自氢、氘；Ar1和Ar2为苯基。
5.根据权利要求1所述的具有三芳基萘的有机电致发光化合物，其特征在于其为下列结构式1-82的化合物：
6.一种有机电致发光器件，其包括阳极、阴极和有机层，有机层包含发光层、空穴注入层、空穴传输层、空穴阻挡层、电子注入层、电子传输层中的至少一层，其特征在于所述有机层中至少有一层含有如权利要求1所述的具有三芳基萘的有机电致发光化合物。
7.根据权利要求6所述的有机电致发光器件，其特征在于如结构式I所述的具有三芳基萘的有机电致发光化合物所在层为发光层、空穴传输层、空穴注入层、电子传输层、电子注入层中的至少一层。
8.根据权利要求6所述的有机电致发光器件，其特征在于如结构式I所述的具有三芳基萘的有机电致发光化合物为结构式1-82的化合物。
9.根据权利要求6所述的有机电致发光器件，其特征在于如结构式I所述的具有三芳基萘的有机电致发光化合物单独使用，或和其它化合物混合使用。
10.根据权利要求6所述的有机电致发光器件，其特征在于如结构式I所述的具有三芳基萘的有机电致发光化合物单独使用其中的一种化合物，或同时使用结构式I中的两种以上的化合物。
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