CN111635411A - 一种有机化合物、电致发光材料及其应用 - Google Patents
一种有机化合物、电致发光材料及其应用 Download PDFInfo
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- CN111635411A CN111635411A CN202010629525.7A CN202010629525A CN111635411A CN 111635411 A CN111635411 A CN 111635411A CN 202010629525 A CN202010629525 A CN 202010629525A CN 111635411 A CN111635411 A CN 111635411A
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 24
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- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
- C07F9/65616—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings containing the ring system having three or more than three double bonds between ring members or between ring members and non-ring members, e.g. purine or analogs
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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Abstract
本发明提供一种有机化合物、电致发光材料及其应用,所述有机化合物具有如式I所示结构,是一种新型的枝化苯并咪唑小分子,所述有机化合物通过星形多臂结构的设计,能够改善材料的无定型性和抗结晶性,避免共轭平面的直接堆积,从而提高了发光效率。所述有机化合物具有TADF特性和聚集诱导发光性能,能够显著提高两种载流子的传输能力和改善载流子平衡,改善荧光量子效率和器件综合性能。所述有机化合物作为OLED器件的发光层材料,尤其适用于掺杂体系中的客体材料或非掺杂体系中的发光材料,能够降低器件的启亮电压,提升器件的发光效率和工作寿命。
Description
技术领域
本发明属于有机电致发光材料技术领域,具体涉及一种有机化合物、电致发光材料及其应用。
背景技术
有机电致发光(Organic Light Emitting Display,OLED)是一种新型的有机显示技术和半导体照明技术,与传统的液晶显示技术相比,OLED具有高效、响应速度快、能耗低、主动性发光、环境适应性强、轻薄、宽视角、发光颜色连续可调、生产工艺简单以及可柔性显示等优点,已广泛应用于平板显示、柔性显示、固态照明和车载显示等行业。
OLED器件通常具有类三明治的结构,包括阳极、阴极以及夹在阴阳极之间的有机层,向器件的电极施加电压时,电荷在电场作用下在有机层中迁移复合而发光。有机层包括发光层,以及电子传输层、空穴传输层、电子阻挡层、空穴阻挡层、空穴注入层和电子注入层等其他辅助传输的功能层;其中,发光层的材料结构及性质对于OLED器件的发光效率具有很大影响。
研究表明,OLED的发光层材料可根据其发光机制主要分为以下四种:荧光材料、磷光材料、三线态-三线态湮灭(TTA)材料和热激活延迟荧光(TADF)材料。其中,荧光材料的单线激发态S1通过辐射跃迁回到基态S0,根据自旋统计,激子中单线态和三线态激子的比例为1:3,所以荧光材料最大内量子产率不大于25%;依据朗伯发光模式,光取出效率为20%左右,因此,基于荧光材料的OLED器件的外量子效率EQE一般不超过5%。磷光材料的三线激发态T1直接辐射衰减到基态S0,由于重原子效应,可以通过自旋偶合作用加强分子内部系间窜越,可以直接利用75%的三线态激子,从而实现在室温下S1和T1共同参与的发射,理论最大内量子产率可达100%。依据朗伯发光模式,光取出效率约为20%,因此,基于磷光材料的OLED器件的EQE可以达到20%。但是磷光材料通常为Ir、Pt、Os、Re、Ru等重金属配合物,生产成本较高,不利于大规模生产。而且,在高电流密度下,磷光材料存在严重的效率滚降现象,同时磷光OLED器件的稳定性并不好。TTA材料中,两个三线态激子相互作用产生一个单线态激子,通过辐射跃迁回到基态S0。相邻的2个三线态激子复合生成一个更高能级的单线激发态分子和一个基态分子,但是2个三线态激子产生1个单线态激子,故其理论最大内量子产率只能达到62.5%。为了防止产生较大的效率滚降现象,在这个过程中三线态激子的浓度需要调控。
TADF材料中,当S1态和T1态的能级差较小且T1态激子寿命较长时,在一定温度条件下,分子内部发生逆向系间窜越(RISC),T1态激子通过吸收环境热量转换到S1态,再由S1态辐射衰减至基态S0。因此,TADF材料可同时利用75%的三线态激子和25%的单线态激子,理论最大内量子产率可达100%。与磷光材料相比,TADF材料主要为有机化合物,不需要稀有金属元素,生产成本低,可通过多种方法进行化学修饰,使其性能更加丰富且可控。
目前,OLED器件领域对于TADF材料的研究较少,已经公开的TADF材料性能难以满足人们对高性能器件的要求,TADF材料在稳定性和发光性能等方面还有很大的改善空间。
因此,开发更多种类、更高性能的电致发光材料,以满足OLED器件的高性能需求,是本领域的研究重点。
发明内容
为了开发更多种类、更高性能的电致发光材料,本发明的目的之一在于提供一种有机化合物,所述有机化合物具有如式I所示结构:
式I中,R1、R2、R3各自独立地选自取代或未取代的C6~C30芳基、取代或未取代的C2~C30杂芳基、取代或未取代的C6~C30芳胺基中的任意一种。
式I中,R4、R5、R6为吸电子基团,且各自独立地选自取代或未取代的C2~C30杂芳基、氰基取代的C6~C30芳基、含氟取代基取代的C6~C30芳基、取代或未取代的C6~C30芳基酮基、取代或未取代的C4~C30杂芳基酮基、取代或未取代的C6~C30芳基砜基、取代或未取代的C6~C30芳基膦氧基中的任意一种。
本发明中,所述“吸电子基团”意指能够降低苯环上电子云密度的基团,示例性地包括但不限于:氰基、氰基取代的芳基或杂芳基、杂芳基、含氟取代基、含氟取代基取代的芳基或杂芳基、芳基酮基、杂芳基酮基、芳基砜基或芳基膦氧基等。
本发明中,所述“含氟取代基”包括氟或含有氟原子的其他基团,例如氟取代的直链或支链烷基。
所述C6~C30可以为C6、C8、C10、C12、C13、C14、C15、C16、C18、C20、C22、C24、C26或C28等。
所述C2~C30可以为C3、C4、C5、C6、C8、C10、C12、C13、C14、C15、C16、C18、C20、C22、C24、C26或C28等。
所述C4~C30可以为C4、C5、C6、C8、C10、C12、C13、C14、C15、C16、C18、C20、C22、C24、C26或C28等。
本发明的目的之二在于提供一种电致发光材料,所述电致发光材料包括如目的之一所述的有机化合物。
本发明的目的之三在于提供一种显示面板,所述显示面板包括OLED器件,所述OLED器件包括阳极、阴极以及位于所述阳极和阴极之间的有机薄膜层,所述有机薄膜层包括发光层;所述发光层的材料包括如目的之二所述的电致发光材料。
本发明的目的之四在于提供一种电子设备,所述电子设备包括如目的之三所述的显示面板。
相对于现有技术,本发明具有以下有益效果:
本发明提供的有机化合物是一种新型的枝化苯并咪唑小分子,所述有机化合物通过星形多臂结构的设计,能够改善材料的无定型性和抗结晶性,避免共轭平面的直接堆积形成π聚集或激基缔合物,从而提高了发光效率。所述有机化合物具有TADF特性,分子结构具有大的刚性扭曲,降低了HOMO和LUMO之间的重叠,使得三重态和单重态之间的能级差可以降低到0.29eV以下,满足三线态能量向单线态的逆向窜越,提高器件效率。而且,所述有机化合物具有聚集诱导发光性能,其本身具有双极特性,作为发光层材料能够显著提高两种载流子的传输能力和改善载流子平衡,改善荧光量子效率和器件综合性能。所述有机化合物作为OLED器件的发光层材料,尤其适用于掺杂体系中的客体材料或非掺杂体系中的发光材料,能够降低器件的启亮电压,提升器件的发光效率和工作寿命。
附图说明
图1为本发明提供的OLED器件的结构示意图,其中101为阳极,102为阴极,103为发光层,104为第一有机薄膜层,105为第二有机薄膜层;
图2为实施例1提供的有机化合物M1的HOMO和LUMO轨道排布图。
具体实施方式
下面通过具体实施方式来进一步说明本发明的技术方案。本领域技术人员应该明了,所述实施例仅仅是帮助理解本发明,不应视为对本发明的具体限制。
本发明的目的之一在于提供一种有机化合物,所述有机化合物具有如式I所示结构:
式I中,R1、R2、R3各自独立地选自取代或未取代的C6~C30芳基、取代或未取代的C2~C30杂芳基、取代或未取代的C6~C30芳胺基中的任意一种。
式I中,R4、R5、R6为吸电子基团,且各自独立地选自取代或未取代的C2~C30杂芳基、氰基取代的C6~C30芳基、含氟取代基取代的C6~C30芳基、取代或未取代的C6~C30芳基酮基、取代或未取代的C4~C30杂芳基酮基、取代或未取代的C6~C30芳基砜基、取代或未取代的C6~C30芳基膦氧基中的任意一种。
本发明中,所述“吸电子基团”意指能够降低苯环上电子云密度的基团,示例性地包括但不限于:氰基、氰基取代的芳基或杂芳基、杂芳基、含氟取代基、含氟取代基取代的芳基或杂芳基、芳基酮基、杂芳基酮基、芳基砜基或芳基膦氧基等。
本发明中,所述“含氟取代基”包括氟或含有氟原子的其他基团,例如氟取代的直链或支链烷基。
所述C6~C30可以为C6、C8、C10、C12、C13、C14、C15、C16、C18、C20、C22、C24、C26或C28等。
所述C2~C30可以为C3、C4、C5、C6、C8、C10、C12、C13、C14、C15、C16、C18、C20、C22、C24、C26或C28等。
所述C4~C30可以为C4、C5、C6、C8、C10、C12、C13、C14、C15、C16、C18、C20、C22、C24、C26或C28等。
本发明提供的有机化合物是一种包含树枝化苯并咪唑单元的有机小分子化合物,所述有机化合物通过星形多臂结构的特殊设计,能够改善材料的无定型性和抗结晶性,避免共轭平面的直接堆积形成π聚集或激基缔合物,从而提高了发光效率。所述有机化合物中的R4、R5、R6为吸电子基团,其通过羰基与苯并咪唑的稠合结构相连,R1、R2、R3为芳基或给电子基团,取代基与母核结构相互协同,赋予了所述有机化合物TADF特性以及分子结构中大的刚性扭曲,降低了HOMO和LUMO之间的重叠,使得三重态和单重态之间的能级差可以降低到0.20~0.29eV,满足三线态能量向单线态的逆向窜越,可以利用传统荧光分子跃迁禁阻得三线态激子来发光,提高器件效率。更为重要的是,所述有机化合物具有聚集诱导发光(Aggregation-induced emission,AIE)性能,其本身具有双极特性,作为发光层必将大大提高两种载流子的传输能力和改善载流子平衡,提高荧光量子效率和器件综合性能。
本发明提供的具有式I所示结构的有机化合物作为电致发光材料,具有AIE特性和TADF特性,能够用于OLED器件的发光层中,作为非掺杂型发光层材料,或掺杂型发光层的主体或客体材料使用,可以显著提升器件的发光性能和工作寿命,同时降低启亮低压和能耗。
本发明中,所述“给电子基团”意指能够提高苯环上电子云密度的基团,示例性地包括但不限于:芳胺基、咔唑基、N-苯基咔唑基、噻吩基、呋喃基、二苯并噻吩基、二苯呋喃基、吩噻嗪基、吩恶嗪基或吖啶类取代基等。
在一个实施方式中,所述取代的芳基、取代的杂芳基、取代的芳胺基、取代的芳基酮基、取代的芳基酮基、取代的芳基砜基、取代的芳基膦氧基中的取代基各自独立地选自未取代或R'取代的C1~C10(例如C2、C3、C4、C5、C6、C7、C8或C9)直链或支链烷基、未取代或R'取代的C6~C18(例如C6、C9、C10、C12、C14、C16或C18等)芳基、未取代或R'取代的C2~C18(例如C3、C4、C5、C6、C8、C10、C12、C14、C16或C18等)杂芳基、C6~C18(例如C6、C9、C10、C12、C14、C16或C18等)芳胺基、C1~C10(例如C2、C3、C4、C5、C6、C7、C8或C9)烷氧基、C1~C10(例如C2、C3、C4、C5、C6、C7、C8或C9)烷硫基、氰基或卤素中的至少一种;所述R'选自氰基或卤素。
本发明中,所述卤素可以为氟、氯、溴或碘。
在一个实施方式中,所述R1、R2、R3各自独立地选自如下基团中的任意一种:
其中,虚线表示基团的连接位点。
X1、X2各自独立地选自O、S、N-RN1或CRC1RC2。
RN1、RC1、RC2、RN各自独立地选自氢、C1~C10(例如C2、C3、C4、C5、C6、C7、C8或C9)直链或支链烷基、C6~C18(例如C6、C9、C10、C12、C14、C16或C18等)芳基、C2~C18(例如C3、C4、C5、C6、C8、C10、C12、C14、C16或C18等)杂芳基、C6~C18(例如C6、C9、C10、C12、C14、C16或C18等)芳胺基、C1~C10(例如C2、C3、C4、C5、C6、C7、C8或C9)烷氧基、C1~C10(例如C2、C3、C4、C5、C6、C7、C8或C9)烷硫基或卤素。
R11、R12、R13各自独立地选自C1~C10(例如C2、C3、C4、C5、C6、C7、C8或C9)直链或支链烷基、C6~C18(例如C6、C9、C10、C12、C14、C16或C18等)芳基、C2~C18(例如C3、C4、C5、C6、C8、C10、C12、C14、C16或C18等)杂芳基、C6~C18(例如C6、C9、C10、C12、C14、C16或C18等)芳胺基、C1~C10(例如C2、C3、C4、C5、C6、C7、C8或C9)烷氧基、C1~C10(例如C2、C3、C4、C5、C6、C7、C8或C9)烷硫基或卤素。
m1、m8各自独立地选自0~5的整数,例如0、1、2、3、4或5。
m2选自0~7的整数,例如0、1、2、3、4、5、6或7。
m3选自0~9的整数,例如0、1、2、3、4、5、6、7、8或9。
m4、m6、m7各自独立地选自0~4的整数,例如0、1、2、3或4。
m5选自0~3的整数,例如0、1、2或3。
在一个实施方式中,所述R1、R2、R3各自独立地选自如下基团中的任意一种,或被取代基取代的如下基团中的任意一种:
其中,虚线表示基团的连接位点。
所述取代基选自C1~C10(例如C2、C3、C4、C5、C6、C7、C8或C9)直链或支链烷基、C6~C18(例如C6、C9、C10、C12、C14、C16或C18等)芳基、C2~C18(例如C3、C4、C5、C6、C8、C10、C12、C14、C16或C18等)杂芳基、C6~C18(例如C6、C9、C10、C12、C14、C16或C18等)芳胺基、C1~C10(例如C2、C3、C4、C5、C6、C7、C8或C9)烷氧基、C1~C10(例如C2、C3、C4、C5、C6、C7、C8或C9)烷硫基或卤素。
在一个实施方式中,所述R1、R2、R3为相同的取代基。
在一个实施方式中,所述R4、R5、R6各自独立地选自如下基团中的任意一种:
其中,虚线表示基团的连接位点。
Y1选自O、S或N-RN2。
RN2、R22各自独立地选自氢、未取代或R'取代的C1~C10(例如C2、C3、C4、C5、C6、C7、C8或C9)直链或支链烷基、未取代或R'取代的C6~C18(例如C6、C9、C10、C12、C14、C16或C18等)芳基、未取代或R'取代的C2~C18(例如C3、C4、C5、C6、C8、C10、C12、C14、C16或C18等)杂芳基、C1~C10(例如C2、C3、C4、C5、C6、C7、C8或C9)烷氧基、C1~C10(例如C2、C3、C4、C5、C6、C7、C8或C9)烷硫基、氰基或卤素。
R21、R31各自独立地选自未取代或R'取代的C1~C10(例如C2、C3、C4、C5、C6、C7、C8或C9)直链或支链烷基、未取代或R'取代的C6~C18(例如C6、C9、C10、C12、C14、C16或C18等)芳基、未取代或R'取代的C2~C18(例如C3、C4、C5、C6、C8、C10、C12、C14、C16或C18等)杂芳基、C1~C10(例如C2、C3、C4、C5、C6、C7、C8或C9)烷氧基、C1~C10(例如C2、C3、C4、C5、C6、C7、C8或C9)烷硫基、氰基或卤素。
R'选自氰基或卤素。
n1选自0~2的整数,例如0、1或2。
n2选自0~3的整数,例如0、1、2或3。
n3选自0~6的整数,例如0、1、2、3、4、5或6。
n4选自0~5的整数,例如0、1、2、3、4或5。
n5、t1各自独立地选自0~4的整数,例如0、1、2、3或4;t2选自1~4的整数,例如1、2、3或4;且t1+t2≤5。
t3选自0~6的整数,例如0、1、2、3、4、5或6;t4选自1~6的整数,例如1、2、3、4、5或6;且t3+t4≤7。
在一个实施方式中,所述R4、R5、R6各自独立地选自如下基团中的任意一种,或被取代基取代的如下基团中的任意一种:
其中,虚线表示基团的连接位点。
所述取代基选自未取代或R'取代的C1~C10(例如C2、C3、C4、C5、C6、C7、C8或C9)直链或支链烷基、未取代或R'取代的C6~C18(例如C6、C9、C10、C12、C14、C16或C18等)芳基、未取代或R'取代的C2~C18(例如C3、C4、C5、C6、C8、C10、C12、C14、C16或C18等)杂芳基、C1~C10(例如C2、C3、C4、C5、C6、C7、C8或C9)烷氧基、C1~C10(例如C2、C3、C4、C5、C6、C7、C8或C9)烷硫基、氰基或卤素。
R'选自氰基或卤素。
在一个实施方式中,所述R4、R5、R6为相同的取代基。
在一个实施方式中,所述有机化合物选自如下化合物M1~M28中的任意一种:
本发明提供的具有如式I所示结构的有机化合物示例性的通过如下合成路线制备得到:
其中,R1、R2、R3、R4、R5、R6各自独立地具有与式I中相同的限定范围。
本发明的目的之二在于提供一种电致发光材料,所述电致发光材料包括如目的之一所述的有机化合物。
本发明的目的之三在于提供一种显示面板,所述显示面板包括OLED器件,所述OLED器件包括阳极、阴极以及位于所述阳极和阴极之间的有机薄膜层,所述有机薄膜层包括发光层;所述发光层的材料包括如目的之二所述的电致发光材料。
在一个实施方式中,所述电致发光材料用作发光层材料、发光层主体材料、发光层掺杂材料或发光层共同掺杂材料中的任意一种。
在一个实施方式中,所述有机薄膜层还包括空穴传输层、空穴注入层、电子阻挡层、空穴阻挡层、电子传输层或电子注入层中的任意一种或至少两种的组合。
本发明所述OLED器件中,阳极材料可以为金属、金属氧化物或导电性聚合物;其中,所述金属包括铜、金、银、铁、铬、镍、锰、钯、铂等及它们的合金,所述金属氧化物包括氧化铟锡(ITO)、氧化铟锌(IZO)、氧化锌、氧化铟镓锌(IGZO)等,所述导电性聚合物包括聚苯胺、聚吡咯、聚(3-甲基噻吩)等。除以上有助于空穴注入的材料及其组合,还包括已知的适合做阳极的材料。
所述OLED器件中,阴极材料可以为金属或多层金属材料;其中,所述金属包括铝、镁、银、铟、锡、钛等及它们的合金,所述多层金属材料包括LiF/Al、LiO2/Al、BaF2/Al等。除以上有助于电子注入的材料及其组合,还包括已知的适合做阴极的材料。
所述OLED器件中,有机薄膜层包括至少一层发光层(EML)和设置于发光层两侧的空穴传输层(HTL)、空穴注入层(HIL)、电子阻挡层(EBL)、空穴阻挡层(HBL)、电子传输层(ETL)、电子注入层(EIL)中的任意一种或至少两种的组合,其中空穴/电子注入及传输层可以为咔唑类化合物、芳胺类化合物、苯并咪唑类化合物及金属化合物等。所述OLED器件的阴极上(远离阳极的一侧)还可以任选地设置盖帽层(CPL)。
所述OLED器件的示意图如图1所示,包括阳极101和阴极102,设置于所述阳极101和阴极102之间的发光层103,在发光层103的两侧设置有第一有机薄膜层104和第二有机薄膜层105,所述第一有机薄膜层104为空穴传输层(HTL)、空穴注入层(HIL)或电子阻挡层(EBL)中的任意1种或至少2种的组合,所述第二有机薄膜层105包括电子传输层(ETL)、空穴阻挡层(HBL)或电子注入层(EIL)中的任意1种或至少2种的组合;所述阴极102上(远离105的一侧)还可以任选的设置盖帽层(CPL)。
所述OLED器件可以通过以下方法制备:在透明或不透明的光滑的基板上形成阳极,在阳极上形成有机薄层,在有机薄层上形成阴极。其中,形成有机薄层可采用如蒸镀、溅射、旋涂、浸渍、离子镀等已知的成膜方法。
本发明的目的之四在于提供一种电子设备,所述电子设备包括如目的之三所述的显示面板。
以下示例性地列举几种本发明所述有机化合物的实施例:
实施例1
本实施例提供一种有机化合物,结构如下:
该有机化合物M1的制备方法包括如下步骤:
在100mL微波耐热管中加入化合物A(3.36g,20mmol)、化合物B(7.33g,60mmol)、催化剂四丁基氯化铵(TBACl,1.67g,6mmol)、30mL甲苯和30mL去离子水,在微波中加热至160℃,反应10min,由薄层色谱法(TLC)监测反应完成。将混合物冷却至室温,并加入三乙胺到反应混合物中使其呈碱性(pH为9),然后用乙酸乙酯(25mL×2)萃取有机相,分离的有机相用无水Na2SO4干燥。收集有机相旋蒸,以柱层析方法(流动相为体积比为3:1的正己烷/二氯甲烷混合溶剂)纯化产物,得到固体化合物C。
化合物C的表征结果:
1H-NMR(400MHz,CDCl3):δ8.35(s,6H),7.80(s,3H),7.50(s,9H);
13C-NMR(100MHz,CDCl3):δ150.17(s),131.62(s),130.73(s),129.14(s),127.90(s),127.18(s),118.52(s)。
在250mL圆底烧瓶中依次加入步骤(1)得到的化合物C(8.51g,20mmol)、化合物D(9.82g,90mmol)、KI(1.99g,12mmol)、75mL二氯乙烷(DCE)和180mmol过氧化氢叔丁醇(TBHP,70%水溶液);将反应混合物在100℃下搅拌12h,冷却至室温,倒入盐水中,用乙酸乙酯(EtOAc)萃取,合并的萃取物用MgSO4干燥,过滤并蒸发。残余物通过柱色谱法纯化(流动相为石油醚/EtOAc的混合溶剂),得到目标产物M1。
所述有机化合物M1的表征结果:
1H-NMR(400MHz,CDCl3):δ8.49(s,6H),8.28(s,6H),7.50(s,9H);
13C-NMR(100MHz,CDCl3):δ167.16(d,J=18.4Hz),155.72(s),149.63(s),130.61(s),130.02(s),128.75(d,J=2.6Hz),126.42(s),125.51(s)。
实施例2
本实施例提供一种有机化合物,结构如下:
该有机化合物M2的制备方法包括如下步骤:
在100mL微波耐热管中加入化合物A(3.36g,20mmol)、化合物B-2(11.88g,60mmol)、催化剂TBACl(1.67g,6mmol)、30mL甲苯和30mL去离子水,在微波中加热至160℃,反应10min,由TLC监测反应完成。将混合物冷却至室温,并加入三乙胺到反应混合物中使其呈碱性(pH为9),然后用乙酸乙酯(25mL×2)萃取有机相,分离的有机相用无水Na2SO4干燥。收集有机相旋蒸,以柱层析方法(流动相为体积比为3:1的正己烷/二氯甲烷混合溶剂)纯化产物,得到固体化合物C-2。
化合物C-2的表征结果:
1H-NMR(400MHz,CDCl3):δ7.77-7.71(m,6H),7.59(dd,J=7.5,1.8Hz,15H),7.46-7.39(m,6H),7.39-7.31(m,3H);
13C-NMR(100MHz,CDCl3):δ151.14,145.06,139.45,139.03,133.11,132.04,128.97,128.79,128.72,127.44,126.99。
在250mL圆底烧瓶中依次加入步骤(1)得到的化合物C-2(13.08g,20mmol)、化合物D(9.82g,90mmol)、KI(1.99g,12mmol)、75mL DCE和TBHP(180mmol,70%水溶液);将反应混合物在100℃下搅拌12h,冷却至室温,倒入盐水中,用EtOAc萃取,合并的萃取物用MgSO4干燥,过滤并蒸发。残余物通过柱色谱法纯化(流动相为石油醚/EtOAc的混合溶剂),得到目标产物M2。
所述有机化合物M2的表征结果:
1H-NMR(400MHz,CDCl3):δ8.47(s,2H),7.74-7.65(m,10H),7.62-7.56(m,9H),7.45-7.39(m,6H),7.42-7.35(m,3H),7.38-7.32(m,3H);
13C-NMR(100MHz,CDCl3):δ164.30,161.10,159.65,147.41,145.10,138.81,134.69,133.56,129.11,128.83,128.41,128.27,127.01,122.31。
实施例3
本实施例提供一种有机化合物,结构如下:
该有机化合物M3的制备方法包括如下步骤:
在100mL微波耐热管中加入化合物A(3.36g,20mmol)、化合物B-3(10.32g,60mmol)、催化剂TBACl(1.67g,6mmol)、30mL甲苯和30mL去离子水,在微波中加热至160℃,反应10min,由TLC监测反应完成。将混合物冷却至室温,并加入三乙胺到反应混合物中使其呈碱性(pH为9),然后用乙酸乙酯(25mL×2)萃取有机相,分离的有机相用无水Na2SO4干燥。收集有机相旋蒸,以柱层析方法(流动相为体积比为3:1的正己烷/二氯甲烷混合溶剂)纯化产物,得到固体化合物C-3。
化合物C-3的表征结果:
1H-NMR(400MHz,CDCl3):δ7.96-7.90(m,9H),7.93-7.86(m,3H),7.64(t,J=7.6Hz,3H),7.52(td,J=7.6,1.6Hz,6H),7.45(td,J=7.4,1.5Hz,3H);
13C-NMR(100MHz,CDCl3):δ143.20,139.75,132.82,132.43,130.16,128.57,128.17,127.64,127.39,127.21,126.87,125.84。
在250mL圆底烧瓶中依次加入步骤(1)得到的化合物C-3(11.52g,20mmol)、化合物D-3(14.04g,90mmol)、KI(1.99g,12mmol)、75mL DCE和TBHP(180mmol,70%水溶液);将反应混合物在100℃下搅拌12h,冷却至室温,倒入盐水中,用EtOAc萃取,合并的萃取物用MgSO4干燥,过滤并蒸发。残余物通过柱色谱法纯化(流动相为石油醚/EtOAc的混合溶剂),得到目标产物M3。
所述有机化合物M3的表征结果:
1H-NMR(400MHz,CDCl3):δ8.37(d,J=1.5Hz,6H),8.10(t,J=1.5Hz,3H),7.96-7.89(m,9H),7.83-7.77(m,3H),7.64(dd,J=8.0,7.3Hz,3H),7.52(td,J=7.7,1.6Hz,6H),7.41(td,J=7.5,1.5Hz,3H);
13C-NMR(100MHz,CDCl3):δ168.68,139.74,135.49,134.48,133.50,132.32,131.67,130.65,128.61,128.57,128.20,127.98,127.87,127.39,127.04,125.30,120.98,119.29,117.80。
实施例4
本实施例提供一种有机化合物,结构如下:
该有机化合物M4的制备方法包括如下步骤:
在100mL微波耐热管中加入化合物A(3.36g,20mmol)、化合物B-4(12.72g,60mmol)、催化剂TBACl(1.67g,6mmol)、30mL甲苯和30mL去离子水,在微波中加热至160℃,反应10min,由TLC监测反应完成。将混合物冷却至室温,并加入三乙胺到反应混合物中使其呈碱性(pH为9),然后用乙酸乙酯(25mL×2)萃取有机相,分离的有机相用无水Na2SO4干燥。收集有机相旋蒸,以柱层析方法(流动相为体积比为3:1的正己烷/二氯甲烷混合溶剂)纯化产物,得到固体化合物C-4。
化合物C-4的表征结果:
1H-NMR(400MHz,CDCl3):δ8.03(dd,J=7.4,1.5Hz,3H),8.00-7.96(m,3H),7.88(dd,J=7.5,1.5Hz,3H),7.55(dd,J=7.4,1.5Hz,3H),7.52-7.43(m,9H),7.38(td,J=7.4,1.6Hz,3H);
13C-NMR(100MHz,CDCl3):δ156.52,156.15,150.62,139.45,133.11,129.56,129.20,127.40,124.45,124.34,124.03,123.90,123.68,111.63,110.32。
在250mL圆底烧瓶中依次加入步骤(1)得到的化合物C-4(13.92g,20mmol)、化合物D-4(20.34g,90mmol)、KI(1.99g,12mmol)、75mL DCE和TBHP(180mmol,70%水溶液);将反应混合物在100℃下搅拌12h,冷却至室温,倒入盐水中,用EtOAc萃取,合并的萃取物用MgSO4干燥,过滤并蒸发。残余物通过柱色谱法纯化(流动相为石油醚/EtOAc的混合溶剂),得到目标产物M4。
所述有机化合物M4的表征结果:
1H-NMR(400MHz,CDCl3):δ9.34(d,J=7.5Hz,3H),8.84(d,J=7.5Hz,3H),8.14(dd,J=7.5,1.5Hz,3H),8.04(dd,J=7.5,1.5Hz,3H),8.02-7.95(m,6H),7.86(t,J=7.5Hz,3H),7.81(dd,J=7.5,1.5Hz,3H),7.54(dd,J=7.6,1.6Hz,3H),7.52-7.43(m,6H),7.38(td,J=7.4,1.5Hz,3H);
13C-NMR(100MHz,CDCl3):δ166.95,163.19,156.53,156.22,148.83,147.60,146.01,145.97,143.16,141.11,134.71,132.06,128.18,128.15,128.11,128.01,127.51,127.28,126.10,124.59,124.26,123.17,122.40,119.96,114.51,112.16。
以下列举几种本发明所述有机化合物应用于OLED器件中的应用例:
应用例1
本应用例提供一种OLED器件,所述OLED器件依次包括:基板、氧化铟锡(ITO)阳极15nm、空穴注入层10nm、空穴传输层110nm、发光层30nm、第一电子传输层30nm、第二电子传输层5nm、阴极15nm(镁银电极,镁银质量比为1:9)、盖帽层100nm。
OLED器件的制备步骤如下:
(1)将玻璃基板切成50mm×50mm×0.7mm的大小,分别在异丙醇和去离子水中超声处理30min,然后暴露在臭氧下清洁10min,得到基板;将所得的具有厚度为15nm的ITO阳极的玻璃基板安装到真空沉积设备上;
(2)在真空度为2×10-6Pa下,在ITO阳极层上真空蒸镀上化合物HAT-CN,厚度为10nm,作为空穴注入层;
(3)在空穴注入层上真空蒸镀化合物TAPC作为空穴传输层,厚度为110nm;
(4)在空穴传输层上真空蒸镀本发明实施例1提供的有机化合物M1作为发光层,厚度为30nm;
(5)在发光层上真空蒸镀化合物TPBi作为第一电子传输层,厚度为30nm;
(6)在第一电子传输层上真空蒸镀化合物Alq3作为第二电子传输层,厚度为5nm;
(7)在第二电子传输层上真空蒸镀镁银电极作为阴极,厚度为15nm;
(8)在阴极上真空蒸镀CBP作为阴极覆盖层(盖帽层),厚度为100nm。
所述OLED器件中用到的化合物结构如下:
应用例2
本应用例与应用例1的区别仅在于,将步骤(4)中的有机化合物M1用等量的有机化合物M2替换;其它制备步骤均相同。
应用例3
本应用例与应用例1的区别仅在于,将步骤(4)中的有机化合物M1用等量的有机化合物M3替换;其它制备步骤均相同。
应用例4
本应用例与应用例1的区别仅在于,将步骤(4)中的有机化合物M1用等量的有机化合物M4替换;其它制备步骤均相同。
对比例1
对比例2
性能测试:
(1)化合物的模拟计算:
有机化合物的单线态和三线态的能级差可以通过Guassian 09软件(GuassianInc.)完成,能级差ΔEST具体的模拟方法可参照文献(J.Chem.Theory Comput.,2013,DOI:10.1021/ct400415r)进行,分子结构优化和激发均可用TD-DFT方法“B3LYP”和基组“6-31g(d)”完成;按照上述方法模拟本发明提供的有机化合物M1、M2、M3和M4,结果如表1所示。
(2)化合物的轨道排布模拟:
按照现有技术中的方法模拟本发明提供的有机化合物的轨道排布图,例如参考Furche F,Ahlrichs R.Adiabatic time-dependent density functional methods forexcited state properties[J].Journal of Chemical Physics,2002,117(16):7433。
图2为本发明提供的有机化合物M1的HOMO和LUMO轨道排布图,从图2中可知,本发明提供的有机化合物的分子HOMO和LUMO分别排布在不同的区域上,实现了比较完全的分离,有助于减小隙间能差ΔEST,从而提高逆隙间窜越能力。
表1
从表1的数据可知,本发明提供的有机化合物通过分子结构的特殊设计,其ΔEST均降低到0.20~0.29eV,实现了较小的单线态和三线态能级差,利于反向隙间窜越。
(3)OLED器件的性能评价:
用Keithley 2365A数字纳伏表测试OLED器件在不同电压下的电流,然后用电流除以发光面积得到OLED器件的在不同电压下的电流密度;用Konicaminolta CS-2000分光辐射亮度计测试OLED器件在不同电压下的亮度和辐射能流密度;根据OLED器件在不同电压下的电流密度和亮度,得到在相同电流密度下(10mA/cm2)的工作电压和电流效率(Cd/A),Von为亮度1Cd/m2下的启亮电压;通过测量OLED器件的亮度达到初始亮度的95%时的时间而获得寿命LT95(在50mA/cm2测试条件下);具体数据如表2所示。
表2
器件编号 | 发光层材料 | V<sub>on</sub>(V) | CE(Cd/A) | LT95(h) |
应用例1 | M1 | 4.11 | 16.07 | 55 |
应用例2 | M2 | 4.05 | 18.26 | 58 |
应用例3 | M3 | 4.19 | 14.65 | 52 |
应用例4 | M4 | 4.27 | 13.36 | 49 |
对比例1 | DPAVB | 4.47 | 6.59 | 42 |
对比例2 | TBD | 4.35 | 6.82 | 45 |
从表2的数据可得,以本发明所述的有机化合物作为非掺杂型的发光材料,制备的OLED器件具有更低的启亮电压,更高的电流效率和工作寿命,其启亮电压降低至4.05~4.27V,电流效率达到13.36~18.26Cd/A,LT95寿命延长至49~58h。
申请人声明,本发明通过上述实施例来说明本发明的有机化合物、电致发光材料及其应用,但本发明并不局限于上述工艺步骤,即不意味着本发明必须依赖上述工艺步骤才能实施。所属技术领域的技术人员应该明了,对本发明的任何改进,对本发明所选用原料的等效替换及辅助成分的添加、具体方式的选择等,均落在本发明的保护范围和公开范围之内。
Claims (13)
2.根据权利要求1所述的有机化合物,其特征在于,所述取代的芳基、取代的杂芳基、取代的芳胺基、取代的芳基酮基、取代的芳基酮基、取代的芳基砜基、取代的芳基膦氧基中的取代基各自独立地选自未取代或R'取代的C1~C10直链或支链烷基、未取代或R'取代的C6~C18芳基、未取代或R'取代的C2~C18杂芳基、C6~C18芳胺基、C1~C10烷氧基、C1~C10烷硫基、氰基或卤素中的至少一种;所述R'选自氰基或卤素。
3.根据权利要求1或2所述的有机化合物,其特征在于,所述R1、R2、R3各自独立地选自如下基团中的任意一种:
其中,虚线表示基团的连接位点;
X1、X2各自独立地选自O、S、N-RN1或CRC1RC2;
RN1、RC1、RC2、RN各自独立地选自氢、C1~C10直链或支链烷基、C6~C18芳基、C2~C18杂芳基、C6~C18芳胺基、C1~C10烷氧基、C1~C10烷硫基或卤素;
R11、R12、R13各自独立地选自C1~C10直链或支链烷基、C6~C18芳基、C2~C18杂芳基、C6~C18芳胺基、C1~C10烷氧基、C1~C10烷硫基或卤素;
m1、m8各自独立地选自0~5的整数;
m2选自0~7的整数;
m3选自0~9的整数;
m4、m6、m7各自独立地选自0~4的整数;
m5选自0~3的整数。
5.根据权利要求1所述的有机化合物,其特征在于,所述R1、R2、R3为相同的取代基。
6.根据权利要求1或2所述的有机化合物,其特征在于,所述R4、R5、R6各自独立地选自如下基团中的任意一种:
其中,虚线表示基团的连接位点;
Y1选自O、S或N-RN2;
RN2、R22各自独立地选自氢、未取代或R'取代的C1~C10直链或支链烷基、未取代或R'取代的C6~C18芳基、未取代或R'取代的C2~C18杂芳基、C1~C10烷氧基、C1~C10烷硫基、氰基或卤素;
R21、R31各自独立地选自未取代或R'取代的C1~C10直链或支链烷基、未取代或R'取代的C6~C18芳基、未取代或R'取代的C2~C18杂芳基、C1~C10烷氧基、C1~C10烷硫基、氰基或卤素;
R'选自氰基或卤素;
n1选自0~2的整数;
n2选自0~3的整数;
n3选自0~6的整数;
n4选自0~5的整数;
n5、t1各自独立地选自0~4的整数,t2选自1~4的整数,且t1+t2≤5;
t3选自0~6的整数,t4选自1~6的整数,且t3+t4≤7。
8.根据权利要求1所述的有机化合物,其特征在于,所述R4、R5、R6为相同的取代基。
10.一种电致发光材料,其特征在于,所述电致发光材料包括如权利要求1~9任一项所述的有机化合物。
11.一种显示面板,其特征在于,所述显示面板包括OLED器件,所述OLED器件包括阳极、阴极以及位于所述阳极和阴极之间的有机薄膜层,所述有机薄膜层包括发光层;
所述发光层的材料包括如权利要求10所述的电致发光材料。
12.根据权利要求11所述的显示面板,其特征在于,所述电致发光材料用作发光层材料、发光层主体材料、发光层掺杂材料或发光层共同掺杂材料中的任意一种。
13.一种电子设备,其特征在于,所述电子设备包括如权利要求11或12所述的显示面板。
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