CN111349055B - 一类用作电致发光材料的多环化合物及应用 - Google Patents

一类用作电致发光材料的多环化合物及应用 Download PDF

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CN111349055B
CN111349055B CN201811582802.2A CN201811582802A CN111349055B CN 111349055 B CN111349055 B CN 111349055B CN 201811582802 A CN201811582802 A CN 201811582802A CN 111349055 B CN111349055 B CN 111349055B
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rings
aromatic ring
layer
groups
aromatic
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CN111349055A (zh
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陈跃
丰佩川
单宏斌
胡灵峰
杨阳
孙伟
王培祥
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Yantai Xianhua Photoelectric Material Research Institute Co ltd
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Abstract

本发明属于有机光电材料技术领域，尤其涉及一类用作电致发光材料的多环化合物及应用。本发明提供的化合物通过四元环将萘与其芳族环或杂芳族环等环状基团连接，形成大共轭不饱和环状化合物；这种四元环的连接方式，不同于直接稠合连接，它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，从而易于调节体系的HOMO‑LUMO能差，可发出高质量的蓝色、天蓝色和深蓝色的光，最大电流效率为3.1‑4.9cd/A。

Description

一类用作电致发光材料的多环化合物及应用
技术领域
本发明属于有机光电材料技术领域，尤其涉及一类用作电致发光材料的多环化合物及应用。
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。比如，苯并萘形成的蒽，其发生光在紫外到深蓝区，而萘并萘形成的并四苯，其发生光为绿光。这种直接稠合形成的大共轭体系，其发射光能量主要通过取代基进行调节，且可调整幅度较小。
发明内容
本发明针对上述现有技术存在的不足，提供一类用作电致发光材料的多环化合物及应用。
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环化合物，其结构式如下：
Figure BDA0001918316330000021
其中，A环为取代或未取代的芳族环系、取代或未取代的杂芳族环系、或含有羰基的不饱和环；
R1、R2、R3、R4、R5和R6各自独立的为氢、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RX为氢、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；
m＝1、2或3。
进一步，R1、R2、R3、R4、R5和R6中邻近的基团可以连接形成环状结构。
进一步，所述A环为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、由取代或未取代的芳族环和杂族芳环构成的多环、或取代或未取代的含有羰基的多环中的一种。
更进一步，A环为由两个苯环通过X和Y连接形成三元环，通式如下：
Figure BDA0001918316330000031
其中，n＝0或1，0≤n1<5,0≤n2<5，且n1、n2为整数；
X为CR7、N、O、S、Se、B(R7)、N(R7)、CR7R8或羰基；
Y为CR9、N、O、S、Se、B(R8)或N(R8)；
其中，R7、R8、R9、Ra、Rb各自独立的为氢、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RX为氢、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、或具有5-50个芳族环原子的杂芳族环系中的任意一种；
多个Ra之间或多个Rb之间形成环状结构。
进一步，R1、R2、R3、R4、R5、R6、R7、R8、R9、Ra、Rb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RX基团取代后所得基团；RX中所述的烷基、芳族环系和杂芳族环系包含各自被卤素或CN取代后所得基团。
进一步，R1、R2、R3、R4、R5、R6、R7、R8、Ra、Rb中，所述的烷基、烷氧基、烯基和炔基包括一个或者多个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；RX中所述的烷基、芳族环系和杂芳族环系包含各自被卤素或CN取代后所得基团。
优选地，上述多环化合物的结构式为：
Figure BDA0001918316330000041
Figure BDA0001918316330000051
Figure BDA0001918316330000061
Figure BDA0001918316330000071
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、9’9-二烷基芴、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，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、或者基团的组合。
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、
Figure BDA0001918316330000081
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、异喹啉、吖啶、菲啶。
由芳族环和杂族芳环构成的多环是指两个或多个芳基基团和杂芳基基团通过单键或非芳族单元键合而成的体系。比如苯连吡啶、萘连吡啶、苯连喹啉、苯连异喹啉、萘连喹啉、萘连异喹啉、5,5-二甲基-5H-茚[1,2-c]吡啶、螺[芴-9,5'-茚[1,2-c]吡啶]、12,12-二甲基-12H-芴[1,2-b]苯并呋喃、12,12-二甲基-12H-芴[1,2-b]苯并噻吩、12,12-二甲基-12H-芴[1,2-b]苯并吡咯、14,14-二甲基-14H-苯[5,6]芴[1,2-b]苯并呋喃等。
本发明的上下文中具有2-50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、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1-50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上述多环化合物作为电致发光材料，在有机电致发光器件中的应用。
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，所述功能层中包含上述渡金属配合物，所述功能层是指发光层；上述多环化合物在发光层中作为主体发光材料或客体发光材料。
本发明的有益效果是：本发明提供的化合物通过四元环将萘与其芳族环或杂芳族环等环状基团连接，形成大共轭不饱和环状化合物；这种四元环的连接方式，不同于直接稠合连接，它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，从而易于调节体系的HOMO-LUMO能差，可发出高质量的蓝色、天蓝色和深蓝色的光，最大电流效率为3.1-4.9cd/A。
附图说明
图1为有机电致发光材料的OLED结构示意图；
图中，1、玻璃衬底；2、阳极层；3、空穴注入层；4、空穴传输层；5、发光层；6、电子传输层；7、电子注入层；8、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：
Figure BDA0001918316330000111
实施例1
化合物3的合成，反应方程式如下：
(1)
Figure BDA0001918316330000112
(2)
Figure BDA0001918316330000113
具体合成过程如下：
(1)向15mL经火焰干燥的压力管中加入RA1(0.125mmol)、RB1(0.25mmol)、Pd(OAc)2(0.0125mmol)和(2-联苯基)二叔丁基膦配体(0.025mmol)后，将该压力管移至手套式操作箱，并加入Cs2CO3(0.25mmol)及15mL的1,4-二氧六环；密封该压力管并移出手套式操作箱，室温条件下，搅拌5min后升温至150℃，反应24h后降至室温，用硅藻土过滤除去反应体系中的无机盐，真空脱溶剂并过柱(1:3EA/Hex)得中间体INT1；
(2)将中间体INT1(0.21mmol)溶于由异丙醇(0.6mL)、三氯甲烷(0.15mL)、HCl(0.1mL，37％)，升温至80℃并保温24h后冷却该反应体系，用NaHCO3溶液洗涤后再用DCM萃取，合并有机相，Na2SO4干燥有机相，脱溶剂，所得固体用甲醇洗涤，过滤收集固相，并用低温甲醇洗涤得化合物3。
实施例2
参照实施例1的方法合成化合物4，不同之处在于步骤(1)中采用RA2代替RA1，经同样的反应得到化合物4。
实施例3
参照实施例1的方法合成化合物14，不同之处在于步骤(1)中采用RA4代替RA1，RB2代替RB1，经同样的反应得到化合物14。
实施例4
参照实施例1的方法合成化合物13，不同之处在于步骤(1)中采用采用RA5代替RA1，经同样的反应得到化合物13。
实施例5
参照实施例1的方法合成化合物21，不同之处在于步骤(1)中采用RA3代替RA1，经同样的反应得到化合物21。
实施例6
参照实施例1的方法合成化合物29，不同之处在于步骤(1)中采用RA6代替RA1，采用RB2代替RB1，经同样的反应得到化合物29。
二、有机电致发光器件应用例
应用例1-6的有机电致发光器件的制备过程如下：
(1)在玻璃底衬1上沉积一层厚度为100nm的氧化铟锡(ITO)作为透明阳极层2；
(2)在透明阳极层2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3，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3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4；
(4)在空穴传输层4上真空蒸镀一层厚度为30nm的发光层5；
应用例1-4中，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)，分别掺杂有4wt％的本发明提供的化合物3、4、14和13作为客体发光材料；
应用例5-6中，使用本发明提供的化合物21、29作为主体发光材料，掺杂4％荧光材料(例如TPPDA：N1,N1,N6,N6-四苯基芘-1,6-二胺)作为客体材料；
(5)再在发光层5上依次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6；
(6)在电子传输层6上真空蒸镀厚度为1nm的Liq作为电子注入层7；
(7)最后在电子注入层7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8。
应用例中所用到的化合物的结构式如下：
Figure BDA0001918316330000141
经测试，应用例1-6的有机电致发光器件的性能测试结果如表1所示。
表1
Figure BDA0001918316330000142
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主体或掺杂材料，发光器件的1000nits下的电流效率为3.4-4.4cd/A，器件发出的光为深蓝色、蓝光，表明本发明所提供的材料适合于OLED发光掺杂材料和主体材料，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 (3)

1.一类用作电致发光材料的多环化合物，其特征在于，其结构式如下：
Figure QLYQS_1
。
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，其特征在于，所述功能层中包含权利要求1所述的多环化合物。
3.根据权利要求2所述的有机电致发光器件，其特征在于，所述功能层是指发光层；权利要求1所述多环化合物在发光层中作为主体发光材料。
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