CN113387875A - 一种多元稠环有机化合物、有机电致发光器件和显示面板 - Google Patents
一种多元稠环有机化合物、有机电致发光器件和显示面板 Download PDFInfo
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- CN113387875A CN113387875A CN202110742198.0A CN202110742198A CN113387875A CN 113387875 A CN113387875 A CN 113387875A CN 202110742198 A CN202110742198 A CN 202110742198A CN 113387875 A CN113387875 A CN 113387875A
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- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
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- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
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- C07C49/657—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings
- C07C49/683—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings having unsaturation outside the aromatic rings
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
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- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
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- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
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- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
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- C07D335/10—Dibenzothiopyrans; Hydrogenated dibenzothiopyrans
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
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- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
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- C—CHEMISTRY; METALLURGY
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
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- C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
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- C—CHEMISTRY; METALLURGY
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- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
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- C07D471/04—Ortho-condensed systems
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Abstract
Description
技术领域
本发明涉及一种多元稠环有机化合物、有机电致发光器件和显示面板,属于半导体技术领域。
背景技术
当前,有机发光二极管(Organic Light-Emitting Diode,OLED)显示技术已经在智能手机,平板电脑等领域获得应用,进一步还将向电视等大尺寸应用领域扩展,但是,和实际的产品应用要求相比,OLED器件的发光效率和使用寿命等性能还需要进一步提升。目前对OLED发光器件提高性能的研究包括:降低器件的驱动电压、提高器件的发光效率、提高器件的使用寿命等。为了实现OLED器件的性能的不断提升,不但需要从OLED器件结构和制作工艺的创新,更需要OLED光电功能材料不断研究和创新,创制出更高性能的OLED功能材料。
因此,针对当前OLED器件的产业应用要求以及OLED器件的光电特性需求,必须选择更适合、性能更高的OLED功能材料或材料组合,才能实现器件的高效率、长寿命和低电压的综合特性。
发明内容
针对现有技术存在的上述问题,本发明提供了一种多元稠环有机化合物、有机电致发光器件和显示面板。该多元稠环有机化合物应用于有机电致发光器件后,可有效提升有机电致发光器件的光电性能以及寿命。
为达此目的,本发明采用如下技术方案:
本发明目的之一在于提供一种由杂蒽酮或氮杂苯修饰的多元稠环有机化合物,具有如下通式(1)所示的结构:
通式(1)中,虚线表示通过单键连接或者不连接;
m表示为0、1、2、3、4、5或6;n表示为0、1、2、3或4;
所述R1、R2分别独立地表示为氢原子、氰基、卤素、C1-10烷基、取代或未取代的C6-30芳基、通式(2)、通式(3)或通式(4)所示结构,R1每次出现相同或不同,R2每次出现相同或不同;
通式(2)中,所述X表示为-O-、-S-、-C(R13)(R14)-或-N(R15)-;
i表示为0、1;
所述Z1每次出现相同或不同地表示为N、C或C-R16;
所述Ar1表示为单键、取代或未取代的C6-30亚芳基、取代或未取代的C2-30亚杂芳基;
所述R13-R15分别独立地表示为C1-10的烷基、取代或未取代的C6-30的芳基、取代或未取代的C2-30杂芳基;
通式(3)中,所述Z2、Z3、Z4表示为N或C-R17,且Z2、Z3、Z4中至少有一个表示为N,
所述R11-R12分别独立地表示为取代或未取代的C6-30的芳基、取代或未取代的C2-30杂芳基;
所述Ar2表示为单键、取代或未取代的C6-30亚芳基、取代或未取代的C2-30亚杂芳基;
通式(2)和通式(3)中,所述R16、R17分别独立地表示为氢原子、氰基、卤素、C1-10烷基、取代或未取代的C6-30芳基、取代或未取代的C2-30杂芳基;
通式(4)中,所述Y每次出现相同或不同表示为N或C-R0;
所述R0表示为氢原子、氰基、卤素、C1-10烷基、取代或未取代的C6-30芳基、通式(2)或通式(3)所示结构;
所述通式(4)以并环方式与通式(1)中*号所示相邻位置稠合连接;
通式(1)中,R3-R10分别独立的表示为氢原子、氰基、卤素、C1-10烷基、取代或未取代的C6-30芳基、通式(2)或通式(3)所示结构;
R0-R10中至少有一个表示为通式(2)或通式(3)所示结构;
可取代基团的取代基任选自氰基、卤素、C1-10烷基、C6-30芳基、C2-30杂芳基中的一种或几种;
所述杂芳基或亚杂芳基中杂原子任选自氧原子、硫原子或氮原子。
可选地,所述多元稠环有机化合物的结构通过通式(1-1)-(1-8)中的任一种表示,
通式(1-1)中,所述R1表示为通式(2)或通式(3)所示结构;
通式(1-2)中,所述R2表示为通式(2)或通式(3)所示结构;
通式(1-3)中,所述R3-R10中的一个表示为通式(2)或通式(3)所示结构;
通式(1-4)-通式(1-8)中,所述R1-R10中的一个表示为通式(2)或通式(3)所示结构。
可选地,所述通式(2)中,至少有一个Z1表示为N。
可选地,所述C6-30芳基为苯基、萘基、蒽基、菲基、芘基、二联苯基、三联苯基、二甲基芴基或二苯基芴基;
所述C2-30杂芳基为吡啶基、萘啶基、二苯并呋喃基、二苯并噻吩基、咔唑基、N-苯基咔唑基或氮杂咔唑基;
所述C6-30亚芳基为亚苯基、亚萘基、亚蒽基、亚菲基、亚芘基、亚二联苯基、亚三联苯基、亚二甲基芴基或亚二苯基芴基;
所述C2-30亚杂芳基为亚吡啶基、亚萘啶基、亚二苯并呋喃基、亚二苯并噻吩基、亚咔唑基亚N-苯基咔唑基或亚氮杂咔唑基;
所述C1-10烷基为甲基、乙基、丙基、异丙基或叔丁基。
可选地,所述Ar1、Ar2各自独立地表示为单键、取代或未取代的亚苯基、取代或未取代的亚萘基、取代或未取代的亚联苯基、取代或未取代的亚三联苯基、取代或未取代的亚吡啶基、取代或未取代的亚呋喃基、取代或未取代的亚萘啶基、取代或未取代的亚二苯并呋喃基、取代或未取代的亚二苯并噻吩基、取代或未取代的亚二甲基芴基、取代或未取代的亚咔唑基中的任一种;
所述R11、R12分别独立地表示为取代或未取代的苯基、取代或未取代的萘基、取代或未取代的萘啶基、取代或未取代的吡啶基、取代或未取代的二联苯基、取代或未取代的三联苯基、取代或未取代的二甲基芴基、取代或未取代的二苯基芴基、取代或未取代的咔唑基、取代或未取代的二苯并呋喃基、取代或未取代的二苯并噻吩基、取代或未取代的氮杂咔唑基中的任一种;
所述R13-R15分别独立地表示为氢原子、甲基、乙基、丙基、异丙基、叔丁基、戊基、取代或未取代的苯基、取代或未取代的萘基、取代或未取代的萘啶基、取代或未取代的吡啶基、取代或未取代的二联苯基、取代或未取代的三联苯基、取代或未取代的二甲基芴基、取代或未取代的二苯基芴基、取代或未取代的咔唑基、取代或未取代的二苯并呋喃基、取代或未取代的二苯并噻吩基、取代或未取代的氮杂咔唑基中的任一种;
所述R16-R17分别独立地表示为取代或未取代的苯基、取代或未取代的萘基、取代或未取代的萘啶基、取代或未取代的吡啶基、取代或未取代的二联苯基、取代或未取代的三联苯基、取代或未取代的二甲基芴基、取代或未取代的二苯基芴基、取代或未取代的咔唑基、取代或未取代的二苯并呋喃基、取代或未取代的二苯并噻吩基、取代或未取代的氮杂咔唑基中的任一种。
可选地,所述可取代基团的取代基任选自甲基、乙基、丙基、异丙基、叔丁基、戊基、苯基、萘基、萘啶基、二联苯基、三联苯基、呋喃基、二苯并呋喃基、咔唑基或吡啶基中的一种或几种。
可选地,所述多元稠环有机化合物选自如式(1)-式(265)所示的化合物。
本发明目的之二在于提供一种有机电致发光器件,包括层叠设置的阳极、阴极和至少一层有机功能层,所述至少一层有机功能层位于所述阴极和所述阳极之间,所述至少一层有机功能层中的至少一层包括如上述任一项所述的由杂蒽酮或氮杂苯修饰的多元稠环有机化合物。
可选地,所述有机功能层选自发光层、空穴阻挡层或者电子传输层。
本发明的目的之三在于提供一种显示面板,包括上述任一项所述的有机电致发光器件。
本发明的有益效果在于:
1.本发明的化合物均以多元稠环为核心,与杂蒽酮或氮杂苯支链相连,结构刚性较强,空间位阻大,不易转动,使得本发明的有机化合物材料的立体结构更加稳定。本发明的多元稠环有机化合物在母核上进一步增加杂蒽酮或氮杂苯取代基团后,该化合物的玻璃化转变温度(Tg)温度升高,提高了材料的稳定性。更进一步地,取代基团的加入使得多元稠环有机化合物的分子量增加,同时该化合物具有较低的蒸镀温度,使得材料加工温度和分解温度之间的温度区间变宽,提高了材料的使用加工窗口。
2.本发明的多元稠环有机化合物作为有机电致发光器件的空穴阻挡层或者电子传输层使用时,合适的LUMO能级能够有效地实现电子传输,提升激子在发光层中的复合效率,减少了能量损失,使发光层主体材料能量充分传递至掺杂材料,从而提升材料应用于器件后的发光效率。
3.本发明的多元稠环有机化合物作为发光层主体材料使用时,使得电子和空穴在发光层的分布更加平衡,提升了空穴注入和传输性能;有效提高激子利用率和高荧光辐射效率,降低高电流密度下的效率滚降,降低器件电压,提高器件的电流效率和寿命。
4.本发明的化合物在应用于有机电致发光器件时,通过器件结构优化,可保持高的膜层稳定性,可有效提升器件的光电性能以及器件的寿命,具有良好的应用效果和产业化前景。
附图说明
图1为本发明的有机电致发光器件的结构示意图。
附图标记:
1为透明基板层,2为阳极层,3为空穴注入层,4为空穴传输层,5为电子阻挡层,6为发光层,7为空穴阻挡层,8为电子传输层,9为电子注入层,10为阴极层。
具体实施方式
为使本发明的目的、技术方案和优点更加清楚,下面将结合本发明的实施例,对本发明实施例中的技术方案进行清楚、完整地描述,显然,所描述的实施例是本发明一部分实施例,而不是全部的实施例。基于本发明中的实施例,本领域普通技术人员在没有做出创造性劳动前提下所获得的所有其他实施例,都属于本发明保护的范围。
本发明的第一方面提供了一种由杂蒽酮或氮杂苯修饰的多元稠环有机化合物,其特征在于,具有如下通式(1)所示的结构:
通式(1)中,虚线表示通过单键连接或者不连接;
m表示为0、1、2、3、4、5或6;n表示为0、1、2、3或4;
所述R1、R2分别独立地表示为氢原子、氰基、卤素、C1-10烷基、取代或未取代的C6-30芳基、通式(2)、通式(3)或通式(4)所示结构,R1每次出现相同或不同,R2每次出现相同或不同;
通式(2)中,所述X表示为-O-、-S-、-C(R13)(R14)-或-N(R15)-;
i表示为0、1;
所述Z1每次出现相同或不同地表示为N、C或C-R16;
所述Ar1表示为单键、取代或未取代的C6-30亚芳基、取代或未取代的C2-30亚杂芳基;
所述R13-R15分别独立地表示为C1-10的烷基、取代或未取代的C6-30的芳基、取代或未取代的C2-30杂芳基;
通式(3)中,所述Z2、Z3、Z4表示为N或C-R17,且Z2、Z3、Z4中至少有一个表示为N,
所述R11-R12分别独立地表示为取代或未取代的C6-30的芳基、取代或未取代的C2-30杂芳基;
所述Ar2表示为单键、取代或未取代的C6-30亚芳基、取代或未取代的C2-30亚杂芳基;
通式(2)和通式(3)中,所述R16、R17分别独立地表示为氢原子、氰基、卤素、C1-10烷基、取代或未取代的C6-30芳基、取代或未取代的C2-30杂芳基;
通式(4)中,所述Y每次出现相同或不同表示为N或C-R0;
所述R0表示为氢原子、氰基、卤素、C1-10烷基、取代或未取代的C6-30芳基、通式(2)或通式(3)所示结构;
所述通式(4)以并环方式与通式(1)中*号所示相邻位置稠合连接;
通式(1)中,R3-R10分别独立的表示为氢原子、氰基、卤素、C1-10烷基、取代或未取代的C6-30芳基、通式(2)或通式(3)所示结构;
R0-R10中至少有一个表示为通式(2)或通式(3)所示结构;
可取代基团的取代基任选自氰基、卤素、C1-10烷基、C6-30芳基、C2-30杂芳基中的一种或几种;
所述杂芳基或亚杂芳基中杂原子任选自氧原子、硫原子或氮原子。
在一种可选地实施方式中,所述多元稠环有机化合物结构通过通式(1-1)-(1-8)中的任一种表示:
通式(1-1)中,所述R1表示为通式(2)或通式(3)所示结构;
通式(1-2)中,所述R2表示为通式(2)或通式(3)所示结构;
通式(1-3)中,所述R3-R10中的一个表示为通式(2)或通式(3)所示结构;
通式(1-4)-通式(1-8)中,所述R1-R10中的一个表示为通式(2)或通式(3)所示结构。
在一种可选地实施方式中,所述通式(2)中,至少有一个Z1表示为N。
在一种可选地实施方式中,所述C6-30芳基为苯基、萘基、蒽基、菲基、芘基、二联苯基、三联苯基、二甲基芴基或二苯基芴基;
所述C2-30杂芳基为吡啶基、萘啶基、二苯并呋喃基、二苯并噻吩基、咔唑基、N-苯基咔唑基或氮杂咔唑基;
所述C6-30亚芳基为亚苯基、亚萘基、亚蒽基、亚菲基、亚芘基、亚二联苯基、亚三联苯基、亚二甲基芴基或亚二苯基芴基;
所述C2-30亚杂芳基为亚吡啶基、亚萘啶基、亚二苯并呋喃基、亚二苯并噻吩基、亚咔唑基亚N-苯基咔唑基或亚氮杂咔唑基;
所述C1-10烷基为甲基、乙基、丙基、异丙基或叔丁基。
在一种可选地实施方式中,所述Ar1、Ar2各自独立地表示为单键、取代或未取代的亚苯基、取代或未取代的亚萘基、取代或未取代的亚联苯基、取代或未取代的亚三联苯基、取代或未取代的亚吡啶基、取代或未取代的亚呋喃基、取代或未取代的亚萘啶基、取代或未取代的亚二苯并呋喃基、取代或未取代的亚二苯并噻吩基、取代或未取代的亚二甲基芴基、取代或未取代的亚咔唑基中的任一种;
所述R11、R12分别独立地表示为取代或未取代的苯基、取代或未取代的萘基、取代或未取代的萘啶基、取代或未取代的吡啶基、取代或未取代的二联苯基、取代或未取代的三联苯基、取代或未取代的二甲基芴基、取代或未取代的二苯基芴基、取代或未取代的咔唑基、取代或未取代的二苯并呋喃基、取代或未取代的二苯并噻吩基、取代或未取代的氮杂咔唑基中的任一种;
所述R13-R15分别独立地表示为氢原子、甲基、乙基、丙基、异丙基、叔丁基、戊基、取代或未取代的苯基、取代或未取代的萘基、取代或未取代的萘啶基、取代或未取代的吡啶基、取代或未取代的二联苯基、取代或未取代的三联苯基、取代或未取代的二甲基芴基、取代或未取代的二苯基芴基、取代或未取代的咔唑基、取代或未取代的二苯并呋喃基、取代或未取代的二苯并噻吩基、取代或未取代的氮杂咔唑基中的任一种;
所述R16-R17分别独立地表示为取代或未取代的苯基、取代或未取代的萘基、取代或未取代的萘啶基、取代或未取代的吡啶基、取代或未取代的二联苯基、取代或未取代的三联苯基、取代或未取代的二甲基芴基、取代或未取代的二苯基芴基、取代或未取代的咔唑基、取代或未取代的二苯并呋喃基、取代或未取代的二苯并噻吩基、取代或未取代的氮杂咔唑基中的任一种。
在一种可选地实施方式中,所述可取代基团的取代基任选自甲基、乙基、丙基、异丙基、叔丁基、戊基、苯基、萘基、萘啶基、二联苯基、三联苯基、呋喃基、二苯并呋喃基、咔唑基或吡啶基中的一种或几种。
在一种可选地实施方式中,具体地,所述多元稠环有机化合物的具体结构为以下结构中的任一种:
本发明的第二方面提供了一种有机电致发光器件,包括层叠设置的阳极、阴极和至少一层有机功能层,所述至少一层有机功能层位于所述阴极和所述阳极之间,所述至少一层有机功能层中的至少一层包括上述任一项所述的多元稠环有机化合物。
在一种可选地实施方式中,优选地,所述有机功能层选自发光层、空穴阻挡层或者电子传输层。
本发明的第三方面提供了一种显示面板,包括上述有机电致发光器件。
以下结合附图和实施例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。
中间体M的制备:
中间体M-1制备过程:
将0.5mmol原料A-1溶解在10mL四氢呋喃中,并将溶液冷却至-78℃(干冰/丙酮)。然后,用少量三甲基硅重氮甲烷(2M,0.5mL,0.5mmol)的醚溶液处理混合物,直至原料A-1的颜色消失,使混合物缓慢升温至-45℃,然后加入0.5mmol原料B-1,使用冰浴(0℃)放置10分钟,向溶液中加入四丁基氟化铵(1M的四氢呋喃溶液,2mL,1mmol)的混合物溶液,在真空下除去溶剂后,通过柱色谱法纯化粗产物得到中间体M-1。
中间体M-4制备过程:
在氮气气氛下,向250ml三口烧瓶中加入5mmol原料C-1、5mmol原料D-1溶解到40ml四氢呋喃中,加入15mmol碳酸钾和0.25mmol Pd(PPh3)4,将反应混合物加热至65℃,回流18小时,利用TLC观察反应,直至反应完全,自然冷却至室温,用***进行萃取,收集有机层,用无水硫酸镁干燥,旋蒸除去溶剂。所得物质通过硅胶柱(石油醚作为洗脱剂)纯化,得到目标产物中间体E-1。
准备250ml三口烧瓶,将6.68mol中间体E-1溶解在50ml的二甲基甲酰胺中,加入6.90mol的氧化银,0.34mol的醋酸钯,5.89mol的三氟乙酸酐,将反应混合物加热至130℃,回流36小时,反应完全,将反应混合物自然冷却至室温,加水将反应猝灭,用乙酸乙酯萃取,收集有几层,用无水硫酸镁干燥,旋蒸除去溶剂,所得物质通过硅胶柱(石油醚作为洗脱剂)纯化,得到目标产物中间体F-1。
在惰性气体保护下,将1mol中间体F-1与1.5mol劳森试剂溶解于20ml干燥的甲苯溶液中,搅拌回流20小时,反应完全,减压蒸馏,所得物质通过硅胶柱(环己烷作为洗脱剂)纯化,得到目标产物中间体G-1。
将0.5mmol中间体G-1溶解在10mL四氢呋喃中,并将溶液冷却至-78℃(干冰/丙酮)。然后,用少量三甲基硅重氮甲烷(2M,0.5mL,0.5mmol)的醚溶液处理混合物,使混合物缓慢升温至-45℃,然后加入0.5mmol原料H-1,使用冰浴(0℃)放置10分钟,向溶液中加入四丁基氟化铵(1M的四氢呋喃溶液,2mL,1mmol)的混合物溶液,在真空下除去溶剂后,通过柱色谱法纯化粗产物得到中间体M-4。
中间体M-5至中间体M-18的制备方法与中间体M-4的制备方法相同,涉及的原料和反应方程式如下:
所制备的中间体M的结构表征如表1所示:
表1
中间体 | 结构表征 | 中间体 | 结构表征 |
中间体1 | LC-MS(m/z):456.04 | 中间体2 | LC-MS(m/z):458.06 |
中间体3 | LC-MS(m/z):456.05 | 中间体4 | LC-MS(m/z):532.06 |
中间体5 | LC-MS(m/z):512.13 | 中间体6 | LC-MS(m/z):508.05 |
中间体7 | LC-MS(m/z):507.05 | 中间体8 | LC-MS(m/z):509.05 |
中间体9 | LC-MS(m/z):458.04 | 中间体10 | LC-MS(m/z):458.07 |
中间体11 | LC-MS(m/z):458.08 | 中间体12 | LC-MS(m/z):508.06 |
中间体13 | LC-MS(m/z):506.04 | 中间体14 | LC-MS(m/z):506.05 |
中间体15 | LC-MS(m/z):508.09 | 中间体16 | LC-MS(m/z):506.07 |
中间体17 | LC-MS(m/z):458.05 | 中间体18 | LC-MS(m/z):456.05 |
制备实施例1:
在250mL三口瓶中,通入氮气,加入0.02mol中间体M-1,150mlDMF,0.022mol原料N-1,0.0002mol醋酸钯,搅拌均匀,然后加入3mL0.01mol/mLK3PO4水溶液,150℃下加热回流反应18小时,取样点板,反应完全,自然冷却,加入100mL水,将混合物过滤并取滤饼在真空干燥箱中干燥,所得残余物过硅胶柱(石油醚:乙酸乙酯=3:1作为洗脱剂)纯化,得到化合物206。
制备实施例2:
化合物208的制备方法同制备实施例1,不同之处在于用中间体M-2替换中间体M-1,用原料N-2替换原料N-1。
制备实施例3:
化合物214的制备方法同制备实施例1,不同之处在于用中间体M-11替换中间体M-1,用原料N-3替换原料N-1。
制备实施例4:
化合物215的制备方法同制备实施例1,不同之处在于用中间体M-3替换中间体M-1,用原料N-4替换原料N-1。
制备实施例5:
化合物216的制备方法同制备实施例1,不同之处在于用中间体M-10替换中间体M-1,用原料N-5替换原料N-1。
制备实施例6:
化合物218的制备方法同制备实施例1,不同之处在于用中间体M-9替换中间体M-1,用原料N-6替换原料N-1。
制备实施例7:
化合物223的制备方法同制备实施例1,不同之处在于用中间体M-14替换中间体M-1,用原料N-7替换原料N-1。
制备实施例8:
化合物226的制备方法同制备实施例1,不同之处在于用中间体M-12替换中间体M-1,用原料N-8替换原料N-1。
制备实施例9:
化合物230的制备方法同制备实施例1,不同之处在于用中间体M-16替换中间体M-1,用原料N-9替换原料N-1。
制备实施例10:
化合物234的制备方法同制备实施例1,不同之处在于用中间体M-15替换中间体M-1,用原料N-10替换原料N-1。
制备实施例11:
化合物236的制备方法同制备实施例1,不同之处在于用中间体M-8替换中间体M-1,用原料N-11替换原料N-1。
制备实施例12:
化合物239的制备方法同制备实施例1,不同之处在于用中间体M-7替换中间体M-1,用原料N-12替换原料N-1。
制备实施例13:
化合物241的制备方法同制备实施例1,不同之处在于用中间体M-6替换中间体M-1,用原料N-13替换原料N-1。
制备实施例14:
化合物245的制备方法同制备实施例1,不同之处在于用中间体M-16替换中间体M-1,用原料N-14替换原料N-1。
制备实施例15:
化合物252的制备方法同制备实施例1,不同之处在于用中间体M-5替换中间体M-1,用原料N-15替换原料N-1。
制备实施例16:
化合物254的制备方法同制备实施例1,不同之处在于用中间体M-4替换中间体M-1,用原料N-16替换原料N-1。
制备实施例17:
化合物258的制备方法同制备实施例1,不同之处在于用中间体M-10替换中间体M-1,用原料N-17替换原料N-1。
制备实施例18:
化合物256的制备方法同制备实施例1,不同之处在于用中间体M-11替换中间体M-1,用原料N-18替换原料N-1。
制备实施例19:
化合物261的制备方法同制备实施例1,不同之处在于用中间体M-2替换中间体M-1,用原料N-19替换原料N-1。
制备实施例20:
化合物262的制备方法同制备实施例1,不同之处在于用中间体M-13替换中间体M-1,用原料N-20替换原料N-1。
制备实施例21-60制备的化合物所涉及到的反应类型同制备实施例1-20。
制备实施例得到的化合物的结构表征如表2a和表2b所示:
表2a
表2b
本发明多元稠环有机化合物,尤其是通过杂蒽酮或氮杂苯修饰后,具有高的玻璃化转变温度(Tg)和三线态能级(T1),合适的HOMO、LUMO能级,可作为发光层、空穴阻挡层或电子传输层材料使用。对本发明上述实施例制备的化合物分别进行热性能、T1能级以及HOMO能级测试,结果如表3所示。
表3
其中,三线态能级T1是由Horiba的Fluorolog-3系列荧光光谱仪测试,材料的测试条件为2*10-5mol/L的甲苯溶液;玻璃化转变温度Tg由示差扫描量热法(DSC,德国耐驰公司DSC204F1示差扫描量热仪)测定,升温速率10℃/min;最高占据分子轨道HOMO能级是由电离能量测试***(IPS-3)测试,测试为大气环境;Eg通过双光束紫外可见分光光度计(型号:TU-1901)进行测试,LUMO=HOMO+Eg。
由上表数据可知,本发明的有机化合物具有高的玻璃化转变温度,可应用于提高材料膜相态稳定性,进一步提高器件使用寿命;本发明的多元稠环有机化合物具有合适的HOMO和LUMO能级,可以解决载流子的注入问题,能够有利于降低器件驱动电压。本发明的有机化合物具有较高的T1能级,作为主体材料使用时可以保证主客体之间的能量传递效率;作为空穴阻挡层材料使用时可以有效地抑制能量损失。因此,本发明的有机材料在应用于OLED器件的不同功能层后,可有效降低器件驱动电压以及提高器件使用寿命。
下面将通过器件实施例说明本发明的化合物在OLED器件中的应用效果,器件实施例2-60、器件比较例1与器件实施例1相比,制作工艺完全相同,并且其中透明基板层1、ITO阳极层2、空穴注入层3、空穴传输层4、电子阻挡层5、电子注入层8、阴极层9采用了相同的材料,各层的膜厚也保持一致,所不同的是器件中发光层或空穴阻挡或电子传输层材料发生了改变,器件实施例2-60、器件比较例1中发光层、空穴阻挡层、电子传输层材料如表4所示,各器件的性能测试结果如表5和表6所示。
器件实施例1
如图1所示,透明基板层1为透明PI膜,对ITO阳极层2(膜厚为150nm)进行洗涤,即依次进行清洗剂(Semiclean M-L20)洗涤、纯水洗涤、干燥,再进行紫外线-臭氧洗涤以清除透明ITO表面的有机残留物。在进行了上述洗涤之后的ITO阳极层2上,利用真空蒸镀装置,蒸镀膜厚为10nm的HT-1和P-1作为空穴注入层3,HT-1和P-1的质量比为97:3。接着蒸镀60nm厚度的HT-1作为空穴传输层4。随后蒸镀40nm厚度的EB-1作为电子阻挡层5。上述电子阻挡材料蒸镀结束后,制作OLED发光器件的发光层6,其结构包括OLED发光层6所使用化合物206和GH-2作为主体材料,GD-1作为掺杂材料,化合物206、GH-2和GD-1质量比为47:47:6,发光层膜厚为40nm。在上述发光层6之后,继续真空蒸镀HB-1,膜厚为5nm,此层为空穴阻挡层7。在上述空穴阻挡层7之后,继续真空蒸镀ET-1和Liq,ET-1和Liq质量比为1:1,膜厚为35nm,此层为电子传输层8。在电子传输层8上,通过真空蒸镀装置,制作膜厚为1nm的Liq层,此层为电子注入层9。在电子注入层9上,通过真空蒸镀装置,制作膜厚为80nm的Mg:Ag电极层,Mg、Ag质量比为1:9,此层为阴极层10使用。相关材料的分子结构式如下所示:
表4
表5
由表5结果可以看出,本发明提供多元稠环有机化合物可应用于OLED发光器件制作。器件实施例1-60与器件比较例1相比,无论是器件效率还是器件寿命均获得较大改观,特别是器件的寿命衰减获得较大的提升。
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 (10)
1.一种多元稠环有机化合物,其特征在于,具有如下通式(1)所示的结构:
通式(1)中,虚线表示通过单键连接或者不连接;
m表示为0、1、2、3、4、5或6;n表示为0、1、2、3或4;
所述R1、R2分别独立地表示为氢原子、氰基、卤素、C1-10烷基、取代或未取代的C6-30芳基、通式(2)、通式(3)或通式(4)所示结构,R1每次出现相同或不同,R2每次出现相同或不同;
通式(2)中,所述X表示为-O-、-S-、-C(R13)(R14)-或-N(R15)-;
i表示为0、1;
所述Z1每次出现相同或不同地表示为N、C或C-R16;
所述Ar1表示为单键、取代或未取代的C6-30亚芳基、取代或未取代的C2-30亚杂芳基;
所述R13-R15分别独立地表示为C1-10的烷基、取代或未取代的C6-30的芳基、取代或未取代的C2-30杂芳基;
通式(3)中,所述Z2、Z3、Z4表示为N或C-R17,且Z2、Z3、Z4中至少有一个表示为N,
所述R11-R12分别独立地表示为取代或未取代的C6-30的芳基、取代或未取代的C2-30杂芳基;
所述Ar2表示为单键、取代或未取代的C6-30亚芳基、取代或未取代的C2-30亚杂芳基;
通式(2)和通式(3)中,所述R16、R17分别独立地表示为氢原子、氰基、卤素、C1-10烷基、取代或未取代的C6-30芳基、取代或未取代的C2-30杂芳基;
通式(4)中,所述Y每次出现相同或不同表示为N或C-R0;
所述R0表示为氢原子、氰基、卤素、C1-10烷基、取代或未取代的C6-30芳基、通式(2)或通式(3)所示结构;
所述通式(4)以并环方式与通式(1)中*号所示相邻位置稠合连接;
通式(1)中,R3-R10分别独立的表示为氢原子、氰基、卤素、C1-10烷基、取代或未取代的C6-30芳基、通式(2)或通式(3)所示结构;
R0-R10中至少有一个表示为通式(2)或通式(3)所示结构;
可取代基团的取代基任选自氰基、卤素、C1-10烷基、C6-30芳基、C2-30杂芳基中的一种或几种;
所述杂芳基或亚杂芳基中杂原子任选自氧原子、硫原子或氮原子。
3.根据权利要求1所述的多元稠环有机化合物,其特征在于,所述通式(2)中,至少有一个Z1表示为N。
4.根据权利要求1所述的多元稠环有机化合物,其特征在于,所述C6-30芳基为苯基、萘基、蒽基、菲基、芘基、二联苯基、三联苯基、二甲基芴基或二苯基芴基;
所述C2-30杂芳基为吡啶基、萘啶基、二苯并呋喃基、二苯并噻吩基、咔唑基、N-苯基咔唑基或氮杂咔唑基;
所述C6-30亚芳基为亚苯基、亚萘基、亚蒽基、亚菲基、亚芘基、亚二联苯基、亚三联苯基、亚二甲基芴基或亚二苯基芴基;
所述C2-30亚杂芳基为亚吡啶基、亚萘啶基、亚二苯并呋喃基、亚二苯并噻吩基、亚咔唑基亚N-苯基咔唑基或亚氮杂咔唑基;
所述C1-10烷基为甲基、乙基、丙基、异丙基或叔丁基。
5.根据权利要求1所述的多元稠环有机化合物,其特征在于,所述Ar1、Ar2各自独立地表示为单键、取代或未取代的亚苯基、取代或未取代的亚萘基、取代或未取代的亚联苯基、取代或未取代的亚三联苯基、取代或未取代的亚吡啶基、取代或未取代的亚呋喃基、取代或未取代的亚萘啶基、取代或未取代的亚二苯并呋喃基、取代或未取代的亚二苯并噻吩基、取代或未取代的亚二甲基芴基、取代或未取代的亚咔唑基中的任一种;
所述R11、R12分别独立地表示为取代或未取代的苯基、取代或未取代的萘基、取代或未取代的萘啶基、取代或未取代的吡啶基、取代或未取代的二联苯基、取代或未取代的三联苯基、取代或未取代的二甲基芴基、取代或未取代的二苯基芴基、取代或未取代的咔唑基、取代或未取代的二苯并呋喃基、取代或未取代的二苯并噻吩基、取代或未取代的氮杂咔唑基中的任一种;
所述R13-R15分别独立地表示为氢原子、甲基、乙基、丙基、异丙基、叔丁基、戊基、取代或未取代的苯基、取代或未取代的萘基、取代或未取代的萘啶基、取代或未取代的吡啶基、取代或未取代的二联苯基、取代或未取代的三联苯基、取代或未取代的二甲基芴基、取代或未取代的二苯基芴基、取代或未取代的咔唑基、取代或未取代的二苯并呋喃基、取代或未取代的二苯并噻吩基、取代或未取代的氮杂咔唑基中的任一种;
所述R16-R17分别独立地表示为取代或未取代的苯基、取代或未取代的萘基、取代或未取代的萘啶基、取代或未取代的吡啶基、取代或未取代的二联苯基、取代或未取代的三联苯基、取代或未取代的二甲基芴基、取代或未取代的二苯基芴基、取代或未取代的咔唑基、取代或未取代的二苯并呋喃基、取代或未取代的二苯并噻吩基、取代或未取代的氮杂咔唑基中的任一种。
6.根据权利要求1-5任一项所述的多元稠环有机化合物,其特征在于,所述可取代基团的取代基任选自甲基、乙基、丙基、异丙基、叔丁基、戊基、苯基、萘基、萘啶基、二联苯基、三联苯基、呋喃基、二苯并呋喃基、咔唑基或吡啶基中的一种或几种。
8.一种有机电致发光器件,其特征在于,包括层叠设置的阳极、阴极和至少一层有机功能层,所述至少一层有机功能层位于所述阴极和所述阳极之间,所述至少一层有机功能层中的至少一层包括如权利要求1-7任一项所述的多元稠环有机化合物。
9.根据权利要求8所述的有机电致发光器件,其特征在于,所述有机功能层包括发光层、空穴阻挡层或者电子传输层。
10.一种显示面板,其特征在于,包括如权利要求8或9所述的有机电致发光器件。
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