CN108912151B - 一类用作电致发光材料的多芳香环化合物及其发光装置 - Google Patents
一类用作电致发光材料的多芳香环化合物及其发光装置 Download PDFInfo
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- CN108912151B CN108912151B CN201810671304.9A CN201810671304A CN108912151B CN 108912151 B CN108912151 B CN 108912151B CN 201810671304 A CN201810671304 A CN 201810671304A CN 108912151 B CN108912151 B CN 108912151B
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Abstract
本发明属于有机光电材料技术领域，涉及一类用作电致发光材料的多芳香环化合物及应用，所述多芳香环化合物具有如式(1)所示的分子结构：
Description
技术领域
本发明属于有机光电材料技术领域，尤其涉及一类多环芳香族化合物及其发光装置。
背景技术
有机电致发光技术作为新兴显示技术，具有高亮度、驱动电压低、发光效率高、结构简单、视角大等优点，具有十分广泛的应用前景。目前，在用于制备全色有机发光二极管的红、绿、蓝三基色材料中，红光材料和绿光材料已基本达到工业化要求，而蓝光材料在荧光效率、色纯度、寿命、亮度等方面距离工业化应用仍有较大距离，成为该行业的技术难题。
目前，蓝光材料主要以咔唑、蒽、篦、苝、芴、苯乙烯等作为核心结构。寻找一个新的蓝光材料核心结构，进一步设计新型蓝色发光材料，这对于改善和提高蓝光OLED材料的性能有着重要的意义。
作为蓝光材料，其最高占据轨道(HOMO)与最低空轨道(LUMO)的能量差要足够大，才能发出高能量的蓝光。共轭小的芳香环体系具有很大的HOMO-LUMO能差，但是其氧化还原稳定性不够好，发射光谱多有较大的肩峰，容易造成色纯度不够好；而大共轭环的芳香体系具有较好的氧化还原稳定性，但是容易产生比较小的HOMO-LUMO能差，同时也容易产生低能量的三重激发态，不适合作为蓝光发光材料。
发明内容
本发明针对现有蓝光材料存在的不足，设计合成了一系列的多芳香环化合物，这类材料通过将多个小芳香环结构连接构成多芳香环化合物，既能保持较大的HOMO-LUMO能级，同时也扩大了共轭度以增强其氧化还原稳定性。进一步，通过改变芳香环的结构、共轭度和取代基，可以调节HOMO-LUMO能级差，使发射光从深蓝光变成蓝光和天蓝光。
本发明解决上述技术问题的技术方案如下：
一类用作电致发光材料的多芳香环化合物，具有如式(1)所示的分子结构：
其中，A环和B环各自独立的为取代或未取代的芳族环系、取代或未取代的杂芳族环系中的一种；
X1、X2和X3各自独立的选自B、C或N；
Y1和Y2各自独立地选自N、O、S、NR1或CR1；
Z1为B、P、P＝O、P＝S、Al、Ga或As；
Z2选自O、S或Se；
其中R1各自独立的选自氢、氘、卤素、C(＝O)RX、CN、Si(RX)3、P(＝O)(RX)、ORX、SRX、S(＝O)RX、S(＝O)2RX、羰基、N(RX)2、具有1-50个碳原子的烷基或烷氧基、具有3-50个碳原子的环烷基、具有2-50个碳原子的烯基或炔基、具有6-50个芳族环原子的芳族环系或具有5-50个芳族环原子的杂芳族环系；所述烷基、烷氧基、烯基、炔基、芳族环系和杂芳族环系包含各自被一个或者多个RX基团取代后所得基团；所述的烷基、烷氧基、烯基和炔基还包括一个或者多个CH2基团被-RXC＝CRX-、-C≡C-、Si(RX)2、C＝O、C＝NRX、-C(＝O)O-、-C(＝O)NRX-、P(＝O))(RX)、-O-、-S-、SO、或者SO2代替后所得基团；
所述RX各自独立的选自氢、氘、卤素、CN、具有1-50个碳原子的烷基、具有6-50个芳族环原子的芳族环系和具有5-50个芳族环原子的杂芳族环系中的任意一种；RX中所述的烷基、芳族环系和杂芳族环系还包含各自被卤素或CN取代后所得基团。
进一步，所述Y1与A环，Y2与B环，Y1与Y2各自独立的连接形成环状基团，环状基团不含杂原子或包含一个或多个杂原子，其中杂原子优选为B、N、S、O和/或Se。
进一步，所述A环和B环各自独立的选自取代或未取代的芳族单环、取代或未取代的杂芳族单环、取代或未取代的含两个或三个环结构的稠合芳族环、取代或未取代的含两个或三个环结构的稠合杂芳族环中的一种，例如取代或未取代的苯、萘、蒽、菲、吡啶、吡咯、呋喃、噻吩、喹啉、异奎林、吲哚、异吲哚、二苯并呋喃、二苯并噻吩和咔唑等。
进一步，上述的多芳香环化合物，其结构式分别为：
本发明还要求保护由两个以上上述的多芳香环化合物连接形成的多聚体。
进一步，所述多芳香环化合物彼此之间通过共价键或-(W)x-的桥基连接形成多聚体，所述W为B、C、N、O、S、Se、Si、P、C(RY)、N(RY)、A(RY)2、C(＝O)RY、CN、P(＝O)(RY)、S(＝O)、S(＝O)2、羰基、具有1-50个碳原子的烷基或烷氧基、具有3-50个碳原子的环烷基、具有2-50个碳原子的烯基或炔基、具有6-50个芳族环原子的芳族环系或具有5至50个芳族环原子的杂芳族环系；其中所述烷基、烷氧基、烯基、炔基、芳族环系和杂芳族环系包含各自被一个或者多个RY基团取代后所得的基团；并且所述烷基、烷氧基、烯基和炔基还包含一个或者多个CH2基团被-RYC＝CRY-、-C≡C-、Si(RY)2、C＝O、C＝NRY、-C(＝O)O-、-C(＝O)NRY-、P(＝O)(RY)、-O-、-S-、SO、或者SO2代替所得的基团；
其中，A为C、Si或Ge；RY各自独立的选自氢、氘、卤素、CN、具有1-50个碳原子的烷基、具有6-50个芳族环原子的芳族环系和具有5-50个芳族环原子的杂芳族环系；并且RY中提到的所述烷基、芳族环系和杂芳族环系还包含各自被卤素或CN取代所得的基团；x≥1，且为整数，x个W相互独立。
进一步，所述多聚体的具体结构如下：
本发明提供的多芳香环化合物及其多聚体的有益效果是：
本发明提供的多芳香环化合物通过硼和磷氧等元素或基团将小共轭芳香环连接成多芳香环化合物，采用非碳的桥基团来连接小共轭环体系，可以降低多环之间的强共轭相互作用，从而抑制了HOMO和LUMO的离域化程度，使HOMO-LUMO的能差不会变得太小，同时T1能级亦不会太低，因此这类化合物具有较大的HOMO-LUMO能差，可发出高质量的蓝色、天蓝色和深蓝色的光。
在本发明上下文中所述的芳族环系是指不包含任何杂原子作为芳族环原子的芳香族环。因此，在本发明上下文中的芳族环系不包含任何杂芳基基团。在本发明上下文中的芳族环系指的是体系，其不必仅含有芳基基团，还可以是多个芳基基团通过单键或非芳族单元键合而成的体系。例如，两个或更多芳族基团通过直链烷基、环烷基、烯基、炔基或甲硅烷基、B、C、Si、N、O或S原子等连接的体系，如9’9-螺二芴、9’9-二芳基芴、三芳基胺、二芳基醚、二苯乙烯、三苯基硅烷的体系同样被认为是包含在本发明上下文中的芳族环系之中。此外，其中两个或更多个芳基基团通过单键彼此连接的体系也被认为是包含在本发明上下文中的芳族环系内，例如，诸如联苯、三联苯、苯连萘的体系。
在本发明的上下文中的杂芳族环系是指芳族环原子中至少一个是杂原子的芳族环系。杂芳族环系的杂原子优选B、N、O或S。因此杂芳族环系符合上述芳族环系的定义，但具有至少一个杂原子作为芳族环原子之一。以此种方式，其不同于在本申请定义的意义上的芳族环系，根据该定义，芳族环系不能含有任何杂原子作为芳族环原子。
同理，本发明上下文中的芳族单环是指不包含任何杂原子作为环原子的芳香族单环，杂芳族单环是指环原子中至少一个是杂原子的芳香族单环，稠合芳族环是指不包含任何杂原子作为环原子的稠合芳香环，稠合杂芳族环是指环原子中至少一个是杂原子的稠合芳香环，杂原子优选B、N、O或S。
在本发明上下文中的芳基基团是指含有6-50个芳族环原子，其都不是杂原子的基团。在本发明上下文中的芳基基团是指简单的芳族环，即苯，或稠合芳族环，如萘、菲或者蒽等。在本申请上下文中的稠合芳族环由彼此稠合的两个或者更多个简单芳族环组成。环之间稠合在这里是指所述环彼此公用至少一个边。
本发明上下文中的杂芳基基团是指含有5～40个芳族环原子，其中至少有一个是杂原子的基团。杂芳基基团的杂原子有选选自B、N、O和或S。在本发明上下文中的杂芳基基团狮子简单的杂芳族环，例如吡啶、呋喃、噻吩、嘧啶等，或稠合杂芳族多环，例如喹啉、咔唑、苯并呋喃、二苯并噻吩等。在本申请上下文中的稠合杂芳族多环由彼此稠合的两个或更多个简单的杂芳族环,或一个或多个简单的杂芳族环和一个或多个简单芳族环组成。环之间稠合是指所述环彼此共用至少一个边。
具有6-50个芳族环原子的芳族环系或者具有5-40个芳族环原子的杂芳族环系是指衍生自以下的基团：上文在芳基基团和杂芳基基团中提及的基团，以及联苯、三联苯、四联苯、芴、螺二芴、二氢菲、二氢芘、四氢芘、茚并芴、三聚茚、异三聚茚、螺三聚茚、螺异三聚茚、茚并咔唑，或这基团的组合。
各自可被上述基团取代并且可经由任何希望的位置与芳族或杂芳族体系连接的芳基或者杂芳基基团，可以理解为是指衍生自如下物质的基团：苯、萘、蒽、菲、芘、二氢芘、
三亚苯、荧蒽、苯并蒽、苯并菲、并四苯、并五苯、苯并芘、呋喃、苯并呋喃、异苯并呋喃、二苯并呋喃、噻吩、苯并噻吩、异苯并噻吩、二苯并噻吩、吡咯、吲哚、异吲哚、咔唑、吡啶、喹啉、异奎琳、吖啶、菲碇。
本发明的上下文中具有2至50个碳原子的烷基、3-50个碳原子的环烷基和具有2-50个碳原子的烯基或炔基基团优选地被理解为甲基、乙基、正丙基、异丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、2-甲基丁基、正戊基、仲戊基、环戊基、新戊基、正己基、环己基、新己基、正庚基、环庚基、正辛基、环辛基、2-乙基己基、三氟甲基、五氟乙基、2,2,2-三氟乙基、乙烯基、丙烯基、丁烯基、戊烯基、环戊烯基、己烯基、环己烯基、庚烯基、环庚烯基、辛烯基、环辛烯基、乙炔基、丙炔基、丁炔基、戊炔基、己炔基或辛炔基基团，各个基团中单独的氢原子或者CH2基团也可被上述基团所取代。
本发明的上下文中具有1至50个碳原子的烷氧基或硫代烷基基团优选被理解为是指甲氧基、三氟甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基、叔丁氧基、正戊氧基、仲戊氧基、2-甲基丁氧基、正己氧基、环己氧基、正庚氧基、环庚氧基、正辛氧基、环辛氧基、2-乙基己氧基、五氟乙氧基、2,2,2-三氟乙氧基、甲硫基、乙硫基、正丙硫基、异丙硫基、正丁硫基、异丁硫基、仲丁硫基、叔丁硫基、正戊硫基、仲戊硫基、正己硫基、环己硫基、正庚硫基、环庚硫基、正辛硫基、环辛硫基、2-乙基己硫基、三氟甲硫基、五氟乙硫基、2,2,2-三氟乙硫基、乙烯硫基、丙烯硫基、丁烯硫基、戊烯硫基、环戊烯硫基、己烯硫基、环己烯硫基、庚烯硫基、环庚烯硫基、辛烯硫基、环辛烯硫基、乙炔硫基、丙炔硫基、丁炔硫基、戊炔硫基、己炔硫基、庚炔硫基或辛炔硫基，各个基团中单独的氢原子或者CH2基团也可被上述基团所取代。
在本申请的上下文中，两个或更多个基团一起可形成环的措词应理解为两个基团通过化学键彼此连接。上述措词也应理解为是指，如果两个基团之一是氢，则第二基团结合于氢原子所键合的位置，从而成环。
本发明的第二个目的在于提供使用上述多芳香环化合物及其多聚体作为电致发光材料的有机电致发光器件，包括阳极层、阴极层和位于阳极层、阴极层之间的功能层，所述功能层中包含前述的多芳香环化合物或多芳香环化合物的多聚体。
进一步，所述功能层是指发光层，前述的多芳香环化合物或多芳香环化合物的多聚体在发光层中作为客体发光材料。
本发明提供的有机电致发光器件的有益效果是：启动电压低，最大电流效率为3.1-4.9cd/A，发出蓝色、天蓝色或深蓝色的光，性能优异。
附图说明
图1为有机电致发光材料的OLED结构示意图；
图1中，LY1、玻璃衬底；LY2、阳极层；LY3、空穴注入层；LY4、空穴传输层；LY5、发光层；LY6、电子传输层；LY7、电子注入层；LY8、阴极层。
具体实施方式
以下对本发明的原理和特征进行描述，所举实例只用于解释本发明，并非用于限定本发明的范围。
一、化合物的合成实施例
合成实施例中使用的原料结构式如下：
实施例1：
化合物1的合成，反应方程式如下：
(1)
(2)
(3)
(4)
具体合成过程如下：
(1)将邻羟基溴苯RA1(5.16g，30mmol)溶解在120ml的乙醇中，再加入苄基氯(BnCl，3.79g，30mmol)，碘化钾(KI，0.175g，1mmol)和碳酸钾(K2CO3，2.48g，18mmol)，搅拌，加热至85℃，回流5小时；冷却至室温，乙醚萃取3次(15ml)，合并有机层，无水硫酸镁干燥，浓缩，残余物柱层析得淡黄色液体INT1A17.07g；
(2)将上一步得到的INT1A1(7.07g)、RC13.47g(10mmol)、碳酸钾3.4g(25mmol)、甲苯120ml、乙醇15ml和去离子水15ml加入到250ml烧瓶中，氮气保护条件下向其中加入四三苯基膦钯Pd(PPh3)40.24g(0.02mmol)，缓慢升温到65℃，搅拌回流18小时，停止反应，降至室温，分液，收集有机相，脱去溶剂，得到中间体INT2A13.76g(8.2mmol)；
(3)将上一步得到的INT2A1(3.76g)溶解到100ml乙醇中，滴加1mol/L的盐酸5ml，10％的钯/炭催化剂(7.5mg)，反应通入氢气，压力3.4MPa,反应24小时；浓缩，残余物柱层析得淡黄色液体INT3A1(2.09g)；
(4)在氮气保护条件下，且在0℃下将中间体INT3A12.09g加入到120ml邻二甲苯中，然后滴加2.5mol/L的正丁基锂己烷溶液2.9ml，滴加结束后，升温至70℃，搅拌4小时，然后升温至100℃后将己烷蒸馏除去。冷却至-50℃后，再添加三溴化硼2.1g(8.4mmol)，然后升温至70℃并搅拌2小时。再次冷却至0℃，加入三乙基胺1.40g(13.8mmol)，在室温下搅拌20分钟后，升温至120℃搅拌2小时。将反应液冷却至室温，加入乙醇析出白色固体(产物PA1，即化合物1)，然后抽滤得到析出物，用正己烷对粗产物进行清洗。
实施例2：
参照实施例1的方法合成化合物2，不同之处在于步骤(2)中采用RC2代替RC1，经同样的反应得到化合物2。
实施例3：
参照实施例1的方法合成化合物13，不同之处在于步骤(1)中采用RA2代替配体RA1，步骤(2)中采用RC2代替配体RC1，经同样的反应得到化合物13。
实施例4：
参照实施例1的方法合成化合物19，不同之处在于步骤(1)中采用RA3代替配体RA1，步骤(2)中采用RC2代替配体RC1，经同样的反应得到化合物19。
实施例5：
参照实施例1的方法合成化合物28，不同之处在于步骤(1)中采用RA4代替配体RA1，步骤(2)中采用RC2代替配体RC1，经同样的反应得到化合物28。
实施例6：
合成化合物75和69，参照实施例2的(1)-(3)三个步骤先合成中间体INT3A2；然后经过以下反应步骤(4)和(5)分别得到化合物75和69。具体合成方法如下：
(4)
(5)
(4)在氮气保护条件下，且在0℃下将中间体INTA315.86g(30mmol)和苯200ml加入到500ml三口烧瓶中，然后滴加1.64mol/L的正丁基锂的己烷溶液18.4ml，滴加结束后，搅拌2小时，在0℃下添加三氯化磷2.87ml(33mmol)，然后升温至80℃，并在该温度下搅拌1小时。在减压脱掉溶剂后添加硫1.16g(36mmol)及邻二氯苯(300ml)，并在80℃下搅拌1h，冷却至-95℃后，再添加三氯化铝27.9g(210mmol)并在0℃下添加N,N-二异丙基乙胺12.3g(72mmol)，升温至100℃搅拌16小时。将反应液冷却至室温后加入到1，4-二氮杂双环[2.2.2]辛烷的二氯甲烷溶液中。析出固体产物PA6-1(化合物63)，然后抽滤得到析出物，用乙腈及正己烷对粗产物进行清洗；(5)0℃条件下，向步骤(4)中的产物PA6-19.3g(20mmol)及230ml二氯甲烷中添加间氯过苯甲酸5.2g(30mmol)，升至室温并搅拌16小时后添加亚硫酸钠饱和溶液15ml及水60ml搅拌并过滤去除不溶物，用二氯甲烷萃取后合并有机相，浓缩后加入体积比为1：1的二氯甲烷和乙酸乙酯溶液作为洗脱剂过柱，减压脱溶剂，用甲醇对粗产品进行清洗，得到产物PA6-2(化合物57)。
由于Al、Ga与B为同族元素，当通式(1)中Z为Al或Ga时化合物的合成方法可参照实施例1的合成过程，不同之处在于步骤(4)中采用AlCl3或GaCl3代替溴化硼，磷与砷(As)为同族元素，当通式(1)中Z为As时化合物的合成方法可参照实施例6的合成过程，不同之处在于步骤(4)中使用AsCl3代替PCl3，搅拌反应后减压脱掉溶剂后经后处理即可得到产物。
二、有机电致发光器件应用例
应用例中有机电致发光器件的结构如图1所示，有机电致发光器件(OLED)的结构包括依次层叠结合的玻璃衬底LY1、阳极层LY2、空穴注入层LY3、空穴传输层LY4、发光层LY5、电子传输层LY6、电子注入层LY7和阴极层LY8。
应用例中有机电致发光器件的制备方法如下：
1)在玻璃底衬LY1上沉积一层厚度为100nm的氧化铟锡(ITO)作为透明阳极层LY2；
2)在透明阳极层LY2上真空蒸镀厚度为10nm的NPB(N,N’-二(1-萘基)-N,N’-二苯基-1,1’-联苯-4-4’-二胺)空穴传输材料作为空穴注入层LY3，其中掺杂质量比3％的F4-TCNQ(2,3,5,6-四氟-7,7',8,8'-四氰二甲基对苯醌)；
3)空穴注入层LY3上为一层厚度为100nm的spiro-TAD(2,2',7,7'-四(二苯基氨基)-9,9'-螺双芴)作为空穴传输层LY4；
4)在空穴传输层LY4上真空蒸镀一层厚度为30nm的发光层LY5，发光层中主体发光材料为CDBP(4,4’-N,N’-二咔唑-2,2’-二甲基联苯)，其中掺杂有4wt％的本发明提供的化合物作为客体发光材料，应用例1～7中掺杂的分别为本发明的化合物1、2、13、19、26、57和63；
5)发光层LY5上真空蒸镀一层厚度为30nm的TPQ(2,3,5,8-四苯基喹喔啉)作为电子传输层LY6；
6)在电子传输层LY6上真空蒸镀一层厚度为1nm的Liq作为电子注入层LY7；
7)最后在电子注入层LY7上采用真空蒸镀膜沉积技术沉积厚度为100nm的金属铝(Al)作为器件的阴极层LY8。
应用例中所用到的化合物的结构式如下：
经测试，应用例1～7的有机电致发光器件的性能测试结果如表1所示。
表1：应用例1～7的有机电致发光器件性能测试结果
从表1中的数据可以看出，以本发明提供的材料作为发光层中的掺杂材料，发光器件的最大电流效率为3.1-4.9cd/A，器件发出的光为深蓝色、蓝光或天蓝光，表明本发明所提供的材料适合于OLED发光材料，尤其是蓝光材料。
以上所述仅为本发明的较佳实施例，并不用以限制本发明，凡在本发明的精神和原则之内，所作的任何修改、等同替换、改进等，均应包含在本发明的保护范围之内。
Claims (4)
1.一类用作电致发光材料的多芳香环化合物，其特征在于，具有如下所示的分子结构：
2.一种有机电致发光器件，包括阳极层、阴极层和位于阳极层、阴极层之间的功能层，所述功能层中包含权利要求1所述的任一多芳香环化合物。
3.根据权利要求2所述的有机电致发光器件，其特征在于，所述功能层具体是指发光层。
4.根据权利要求3所述的有机电致发光器件，其特征在于，权利要求1所述的任一多芳香环化合物在发光层中作为客体发光材料。
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| WO2012085169A1 (en) * | 2010-12-22 | 2012-06-28 | Haag Benjamin | Metallic amidoborates for functionalizing organic compounds |
| CN103183691A (zh) * | 2011-12-29 | 2013-07-03 | 昆山维信诺显示技术有限公司 | 含有取代或非取代咔唑基的6-均三甲苯基-6H-6-硼杂苯并[cd]芘衍生物及制备方法及应用及含其的发光器件 |
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| WO2012085169A1 (en) * | 2010-12-22 | 2012-06-28 | Haag Benjamin | Metallic amidoborates for functionalizing organic compounds |
| CN103183691A (zh) * | 2011-12-29 | 2013-07-03 | 昆山维信诺显示技术有限公司 | 含有取代或非取代咔唑基的6-均三甲苯基-6H-6-硼杂苯并[cd]芘衍生物及制备方法及应用及含其的发光器件 |
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