CN113817462A - 主体材料、有机光电器件及显示或照明装置 - Google Patents
主体材料、有机光电器件及显示或照明装置 Download PDFInfo
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- CN113817462A CN113817462A CN202111132490.7A CN202111132490A CN113817462A CN 113817462 A CN113817462 A CN 113817462A CN 202111132490 A CN202111132490 A CN 202111132490A CN 113817462 A CN113817462 A CN 113817462A
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- 238000007125 Buchwald synthesis reaction Methods 0.000 description 1
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- 238000005481 NMR spectroscopy Methods 0.000 description 1
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- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
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- 239000000292 calcium oxide Substances 0.000 description 1
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- RWWUBXBYBPQIJI-UHFFFAOYSA-N cesium;quinolin-8-ol Chemical compound [Cs].C1=CN=C2C(O)=CC=CC2=C1 RWWUBXBYBPQIJI-UHFFFAOYSA-N 0.000 description 1
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- 239000012153 distilled water Substances 0.000 description 1
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- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
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- FUJCRWPEOMXPAD-UHFFFAOYSA-N lithium oxide Chemical compound [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
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- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- ORUIBWPALBXDOA-UHFFFAOYSA-L magnesium fluoride Chemical compound [F-].[F-].[Mg+2] ORUIBWPALBXDOA-UHFFFAOYSA-L 0.000 description 1
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- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
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- 230000004048 modification Effects 0.000 description 1
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- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
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- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 150000003057 platinum Chemical class 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920005596 polymer binder Polymers 0.000 description 1
- 239000002491 polymer binding agent Substances 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- NNHHDJVEYQHLHG-UHFFFAOYSA-N potassium silicate Chemical compound [K+].[K+].[O-][Si]([O-])=O NNHHDJVEYQHLHG-UHFFFAOYSA-N 0.000 description 1
- 229910052913 potassium silicate Inorganic materials 0.000 description 1
- 235000019353 potassium silicate Nutrition 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
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- 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
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- C07D487/22—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 four or more hetero rings
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
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- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C07F7/0816—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring comprising Si as a ring atom
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Abstract
本发明提供了一种主体材料,该主体材料包含至少一种第一主体化合物和至少一种第二主体化合物,其中所述第一主体化合物由通式Ⅰ表示并且所述第二主体化合物由通式Ⅱ表示:
Description
技术领域
本发明涉及一种主体材料。更特别地,涉及一种主体材料、有机光电器件及显示或照明装置。
背景技术
有机电致发光器件(Organic Light-Emitting Diode,简称为OLED)具有薄型且能在低驱动电压下高亮度发光以及能通过选择发光材料而进行多色发光的特征,因此倍受关注。
有机光电器件(例如有机电致发光器件)通过在器件两端施加电压,将电能转换成光。有机电致发光器件包括阳极、阴极和在阳极与阴极之间的有机层,该有机层可以包括空穴注入层、空穴传输层、电子阻挡层、发光层(包含主体材料和掺杂材料)、电子缓冲层、空穴阻挡层、电子传输层和电子注入层等。根据材料功能的不同,组成有机层的材料可以分为空穴注入材料、空穴传输材料、电子阻挡材料、发光材料、电子缓冲材料、空穴阻挡材料、电子传输材料、空穴阻挡材料等。当施加偏压于器件,空穴从阳极注入至发光层,电子从阴极注入至发光层,空穴和电子相遇形成激子,激子复合发光,其中发光层对有机发光器件的性能的影响最为关键。发光层材料需要具有高的量子效率、高电子迁移率和高空穴迁移率等特性,发光层材料可以使用主体材料和掺杂材料的组合来提高颜色纯度、发光效率和稳定性。为了获得具有更高效率和更长的使用寿命等的有机光电器件,选择合适的主体材料和掺杂材料的匹配组合十分重要。日本专利申请公开号2001-23777公开了含氮的5元杂芳基缩合在菲骨架的中间苯环化合物作为主体材料的有机电致发光器件,其中公开的包含上述化合物的有机电致发光器件具有优异的蓝色的颜色纯度特性。然而,上述化合物在驱动电压、电流效率以及驱动寿命方面仍需要改进。
发明内容
为了克服现有技术中存在的缺陷,本发明提供一种主体材料、有机光电器件及显示或照明装置。本发明的有机光电器件具有高电流效率及长使用寿命。
为了实现本发明的目的,本发明的技术方案如下:
本发明提供了一种主体材料,所述主体材料包含至少一种第一主体化合物和至少一种第二主体化合物,其中所述第一主体化合物由通式Ⅰ表示并且所述第二主体化合物由通式Ⅱ表示:
其中,X1-X8各自独立地选自CR或N原子,其中R选自氢、氘、卤素、氰基、取代或未取代的烷基、环烷基、杂烷基、杂环烷基、芳基或杂芳基;
X1-X8彼此相同或不同;
L1、L2和L3各自独立地选自单键或取代或未取代的芳基;
R1、R2和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C4~C30杂芳基或与邻近的原子键合成环,其中R1、R2和R3中至少一者选自如下取代或未取代的基团:
其中,R4-R10各自独立地选自氢、取代或未取代的C1-C15烷基、取代或未取代的C6~C30芳基或取代或未取代的C4~C30杂芳基;
当X1-X8均不为N原子时,R1、R2和R3不全相同或全部不相同;
其中,Ar1、Ar2和Ar3各自独立地选自取代或未取代的C6~C30芳基或取代或未取代的C3~C30杂芳基;
Z1、Z2和Z3各自独立地选自碳或氮;
Y1和Y2各自独立地选自NR1或氧,其中R1为取代或未取代的C1~C20烷基、取代或未取代的C6~30芳基或取代或未取代的C3~C30杂芳基;
R11为氢、取代或未取代的C1-C15烷基、取代或未取代的C6~C30芳基或取代或未取代的C4~C30杂芳基。
优选地,其中,由通式Ⅰ表示的化合物选自由以下各项组成的组合:
优选地,式Ⅱ选自以下化合物:
其中,Ar1、Ar2和Ar3各自独立地选自取代或未取代的C6~C30芳基或取代或未取代的C3~C30杂芳基;
Z1、Z2和Z3各自独立地选自碳或氮;
R11为氢、取代或未取代的C1-C15烷基、取代或未取代的C6~C30芳基或取代或未取代的C4~C30杂芳基。更优选地,其中,由式Ⅱ表示的化合物选自由以下各项组成的群组:
本发明又提供了一种有机光电器件,其包括阴极层、阳极层和有机层,其中,所述有机层为空穴注入层、空穴传输层、发光层、电子注入层或电子传输层中至少一层,其中,所述发光层中含有该主体材料。
优选地,其中所述有机层为发光层,所述发光层还包含掺杂剂,其中所述主体材料与所述掺杂剂的质量比为1:99~99:1。优选地,其中所述第一主体化合物与所述第二主体化合物的质量比为1:99~99:1。
优选地,其中所述有机光电器件为有机光伏器件、有机发光器件、有机太阳电池、电子纸、有机感光体、有机薄膜晶体管或有机内存器件。
本发明进一步提供了一种显示或照明装置,其包括该有机光电器件。
本发明由通式Ⅰ表示的三并咔唑化合物具有较高的三线态能级,因此,具有好的空穴传输能力。本发明由通式Ⅱ表示的菲并噻唑、噁唑、呋喃、噻吩等的衍生化合物固有地具有高电负性和富电子基团,并且两种通式表示的化合物因其中三并咔唑、菲和噁唑、菲和噻唑、菲和呋喃或菲和噻吩等是稠合的结构而具有刚性特性,使得本发明的这两种衍生物促进了分子之间的电荷跃迁。另外,三并咔唑衍生物和菲和噁唑、菲和噻唑、菲和呋喃或菲和噻吩等衍生物具有良好的平面性,能增强此两种分子间堆叠,能更容易实现水平分子取向,从而使得能够实现快速电子电流特征。可以实现具有高效率及长寿命的有机电致发光器件。
具体实施方式
在下文中,将详细描述本发明。然而,以下描述旨在解释本发明,并不意味着以任何方式限制本发明的范围。
本发明提供了上述主体材料在有机光电器件中的应用。
本发明的有机光电器件顺次包括沉积的阳极、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。
本发明的有机光电器件包括阳极、阴极以及位于阳极与阴极之间的若干个有机层,该有机层含有该主体材料。
本发明的有机光电器件是包含有通式Ⅰ和通式Ⅱ作为发光层的多种主体材料的发光器件,该发光器件包含基板、第一电极、有机层、第二电极以及覆盖层,优选的器件可包括基板,位于基板上的第一电极,位于第一电极上的有机层,位于有机层上的第二电极,以及位于第二电极外侧的覆盖层,本发明的第二电极外侧是指背离第一电极的一侧。
本发明的有机层可以包含发光层、空穴注入层、空穴传输层、电子传输层和电子注入层。该有机层可以由单层结构形成,也可以由层叠(包含发光层、空穴注入层、空穴传输层、电子传输层和电子注入层在内的多层结构)形成。同时,该有机层还可以包含一层或多层结构,例如该空穴传输层可以包含第一空穴传输层以及第二空穴传输层。在本发明的发光器件中,除了该发光层包含本发明的多种主体材料外,其它层均可以使用本领域公知的用于层的任何材料。
在本发明的发光器件中,基板材料可选用典型的有机发光器件中使用的任何基板,其可以是钠玻璃、无碱玻璃或者透明柔性基板,也可以是不透明材料如硅或不锈钢的基板,还可以是柔性聚酰亚胺薄膜。不同基板材料具有不同的性能,应用方向不同。作为本发明的空穴传输层,可通过将空穴传输材料的一种或二种以上层叠或混合的方法,或通过使用空穴传输材料和高分子粘合剂的混合物的方法来形成。空穴传输材料需要在施加了电场的电极之间高效率地传输来自正极的空穴,因此希望空穴注入效率高、能够高效率地传输注入的空穴。因此,要求空穴传输材料具有适当电离势,适当的能级并且具有大的空穴迁移率,进一步材料稳定性优异,制造及使用过程中不容易产生会成为陷阱的杂质。对满足这样的条件的物质,没有特别限定,例如可以是咔唑衍生物、三芳胺衍生物、联苯二胺衍生物、芴衍生物、酞菁类化合物、六腈六氮杂苯并菲类化合物、喹吖啶酮类化合物、苝衍生物、蒽醌类化合物、F4-TCNQ、聚苯胺、聚噻吩、聚乙烯咔唑等,但不限于此。
作为本发明的发光层材料,除了包含本发明提供的多种主体材料,也可以使用掺杂材料(也称客体材料),可包含多个掺杂材料。由通式Ⅰ表示的化合物可以作为多种主体材料的第一主体化合物,且由通式Ⅱ表示的化合物可以作为多种主体材料的第二主体化合物。第一主体化合物与第二主体化合物的质量比约1:99至约99:1、优选约1:9至约9:1、更优选约3:7至7:3、甚至更优选约2:3至约3:2、并且更优选约1:1。当发光层包含两种或两种以上材料时,可以用混合蒸镀形成层,或可以同时分别共蒸镀形成层。另外发光层可为单一的发光层,也可为横向或纵向叠加在一起的复合发光层。对于掺杂材料的种类选择,可以为荧光材料,也可以为磷光材料;对于掺杂材料的用量选择,优选0.1~70%质量,更优选为0.1~30质量%、进一步优选为1~30质量%、更进一步优选为1~20质量%、特别优选为1~10质量%。
可用于本发明的荧光掺杂材料包括稠合多环芳族衍生物、苯乙烯基胺衍生物、稠环胺衍生物、含硼化合物、吡咯衍生物、吲哚衍生物、咔唑衍生物等,但不限于此。可用于本发明的磷光掺杂材料可包括重金属配合物、磷光发光性的稀土类金属配合物等,但不限于此。重金属配合物可举出例如铱配合物、铂配合物、锇配合物等;稀土类金属配合物可举出例如铽络合物、铕络合物等,但不限于此。作为本发明的电子传输材料,优选具备良好电子迁移率的物质,同时具备合适的HOMO和LUMO能级。可作为本发明的电子传输材料包括金属配合物、氧杂噻唑衍生物、噁唑衍生物、二氮唑衍生物、氮杂苯衍生物、菲罗啉衍生物、二氮蒽衍生物、含硅杂环类化合物、含硼杂环类化合物、氰基类化合物、喹啉衍生物、苯并咪唑衍生物等,但不限于此。作为本发明的电子注入材料,优选具有传输电子能力的物质,同时具有从阴极注入电子的效应,具有优异的薄膜形成能力。可作为本发明的电子注入材料包括碱金属化合物,例如氧化锂、氟化锂、8-羟基喹啉锂、氧化锂硼、碳酸铯、8-羟基喹啉铯、硅酸钾、氟化钙、氧化钙、氟化镁、氧化镁;芴酮;含氮五元环衍生物,例如,噁唑衍生物、恶二唑衍生物、咪唑衍生物、金属配合物、蒽醌二甲烷、联苯醌、蒽酮衍生物等,但不限于此,这些化合物可以单独使用,也可与其他材料混合使用。作为本发明的阴极材料,优选具有低功函数的材料,以便容易地将电子注入有机层。可用于本发明的阴极材料包括金属,例如镁、钙、钠、钾、钛、铟、钇、锂、铝、银、锡、铅或它们的合金;以及多层材料,例如LiF/Al或LiO2/Al,但不限于此。
本发明所述的有机层材料,它们在使用时,可单独成膜形成单层结构,也可和其他材料一起混合成膜形成单层结构,或形成单独成膜的单层的层叠结构、混合成膜的单层的叠层结构、单独成膜的单层和混合成膜的单层的叠层结构,但不限于此。本发明的有机电致发光器件可以通过依次层叠上述的结构而制造。制造方法可使用干式成膜法、湿式成膜法等公知方法。作为干式成膜法的具体例,可举出真空蒸镀法、溅射法、等离子体法、离子电镀法等;作为湿式成膜法的具体例,可举出旋涂法、浸渍法、流延法、喷墨法等各种涂布法,但不限于此。本发明的有机光电器件可广泛应用于面板显示、照明光源、柔性OLED、电子纸、有机太阳能电池、有机感光体或有机薄膜晶体管、指示牌、信号灯等领域。
实施例
上述通式Ⅰ或通式Ⅱ表示的化合物可以使用本领域公知的方法合成,例如,使用镍、钯等过渡金属的交叉偶合反应。其他合成方法是使用镁或锌等过渡金属的C-C,C-N偶联生成反应。上述反应,限于反应条件温和、各种官能团的选择性优越等特点,优选Suzuki,Buchwald反应。
本发明的多主体材料化合物用以下实施例举例说明,但并不限于这些实施例举例的化合物和合成方法。
本发明的初始原料和溶剂购于国药,部分常用的OLED中间体类等产品购于国内的OLED中间体厂商;各种钯催化剂、配体等购于sigma-Aldrich公司。
1H-NMR数据使用JEOL(400MHz)核磁共振仪来测定;
HPLC数据使用岛津LC-20AD高效液相仪来测定。
实施例1
化合物2的合成
1)中间体2-2的合成
在氩气气氛下,反应容器中加入化合物2-145.1克(100mmol),(2-硝基苯基)硼酸36.7g(220mmol),[1,3-双(2,6-二-异丙基苯基)-4,5-二氢咪唑-2-亚基]氯][3-苯基烯丙基]钯(II)催化剂648毫克,1.5M碳酸钠水液200ml(300mmol)和乙二醇二甲醚1000ml(DME),80℃加热搅拌一晚。冷却至室温,加入800ml水,固体析出,过滤,粗品通过硅胶柱层析法精制(洗脱液:乙酸乙酯/己烷),得到42.3g化合物2-2,收率79%,HPLC纯度99.1%。
2)中间体2-3的合成
在氩气气氛下,反应容器中加入化合物2-253.6克(100mmol),用100ml氯苯溶解,加入7.9克三苯基膦,180℃加热搅拌一晚。冷却至室温,过滤,滤液减压除去溶剂,得到的粗品通过硅胶柱层析法精制(洗脱液:乙酸乙酯/己烷),得到35.4g化合物2-3,收率75%,HPLC纯度98.7%。
3)化合物2的合成
在氩气气氛下,反应容器中加入叔丁醇钾26.9克(240mmol),[1,3-双(2,6-二-异丙基苯基)-4,5-二氢咪唑-2-亚基]氯][3-苯基烯丙基]钯(II)催化剂648毫克(1mmol%)2-溴-3-苯基喹啉62.7g(220mmol),化合物2-347.2克(100mmol)和1000mL乙二醇二甲醚(DME),在80℃加热搅拌15小时。反应混合物冷却到室温,加入500ml水,过滤,粗品通过硅胶柱层析法精制(洗脱液:乙酸乙酯/己烷),得到70.4克化合物2,HPLC纯度99.5%,收率80%.
1HNMR(DMSO):δ8.55(d,2H),8.40(d,4H),8.03(m,3H),7.94(d,2H),7.83(s,1H),7.80(d,4H),7.67(m,4H),7.59~7.57(m,8H),7.47(s,4H),7.35(m,2H),7.16(m,2H).
实施例2
化合物4的合成
1)中间体4-2的合成
除了起始原料更换为4-1以外,其他与实施例1相同
2)中间体4-3的合成
除了起始原料更换为4-2以外,其他与实施例1相同
3)化合物4的合成
除了起始原料更换为化合物4-3和2-溴萘以外,其他与实施例1相同。
1HNMR(DMSO):δ8.55(d,2H),8.40(d,2H),8.03(m,6H),7.94(m,2H),7.83(s,2H),7.80(d,2H),7.67(m,2H),7.59~7.57(m,7H),7.47(s,4H),7.35(m,3H),7.16(m,2H).
实施例3
化合物12的合成
1)中间体12-2的合成
除了起始原料更换为化合物12-1以外,其他与实施例1相同。
2)中间体12-3的合成
除了起始原料更换为化合物12-2以外,其他与实施例1相同。
3)化合物12的合成
除了原料更换为12-3和间溴吡啶以外,其他与实施例1相同
1HNMR(DMSO):δ8.71(s,2H),8.55(d,2H),8.46(m,2H),7.94(d,2H),
7.87(d,2H),7.62(m,2H),7.58(s,1H),7.48(m,2H),7.47(s,4H),7.35(t,2H),7.16(m,2H)..
实施例4
化合物18的合成
1)中间体18-2的合成
与实施例1相同。
2)中间体18-3的合成
与实施例1相同。
3)化合物18的合成
除了起始原料更换为19-3和3-溴-1,2,4-恶二唑以外,其他与实施例1相同。
1HNMR(DMSO):δ8.90(s,2H),8.55(d,2H),8.03(m,3H),7.94(d,2H),7.83(s,1H),7.59(m,2H),7.47(s,4H),7.35(m,3H),7.16(m,2H).
实施例5
化合物22的合成
1)中间体22-2的合成
除了起始原料更换为化合物22-1和(5-(叔丁基)-2-硝基苯基)硼酸以外,其他与实施例1相同。
2)中间体22-3的合成
除了起始原料更换为22-2以外,其他与实施例1相同。
3)化合物22的合成
除了起始原料更换为邻溴吡啶和22-3以外,其他与实施例1相同。
1HNMR(DMSO):δ8.95(s,2H),8.65(d,3H),8.15(m,3H),8.02(d,3H),7.86(d,2H),7.47(s,4H),7.36(m,3H),7.11(d,2H),1.43(s.18H).
实施例6
化合物30的合成
1)中间体30-2的合成
除了起始原料更换为化合物30-1和(5-(叔丁基)-2-硝基苯基)硼酸以外,其他与实施例1相同。
1)中间体30-3的合成
除了起始原料更换为化合物30-2以外,其他与实施例1相同。
2)化合物30的合成
除了起始原料更换为化合物30-3和2-溴苯并噻唑以外,其他与实施例1相同。
1HNMR(DMSO):δ8.95(s,2H),8.18(d,2H),8.02(d,2H),7.86(d,2H),7.72(m,2H),
7.53(m,2H),7.51(m,2H),7.47(s,4H),7.39(d,2H),7.11(d,2H),1.43(s.18H).
实施例7
化合物37的合成
1)中间体37-2的合成
除了起始原料更换为化合物37-1和(3-硝基吡啶-2-基)硼酸以外,其他与实施例1相同。
2)中间体37-3的合成
除了起始原料更换为化合物37-2以外,其他与实施例1相同。
3)化合物37的合成
除了起始原料更换为间溴吡啶和化合物37-3以外,其他与实施例1相同。
1HNMR(DMSO):δ8.71(s,3H),8.46(m,3H),8.43(d,2H),7.97(d,2H),7.87(d,2H),7.55(s,2H),7.48(d,3H),7.40(s,2H),7.22(m,2H)
实施例8
化合物44的合成
1)中间体44-2的合成
除了起始原料更换为化合物41-1和(3-硝基吡啶-2-基)硼酸以外,其他与实施例1相同。
2)中间体44-3的合成
除了起始原料更换为化合物43-2以外,其他与实施例1相同。
3)化合物44的合成
除了起始原料更换为2-溴苯并恶唑和化合物44-3以外,其他与实施例1相同。
1HNMR(DMSO):δ8.43(d,2H),8.18(d,2H),8.02(d,3H),7.97(d,2H),7.55(s,2H),7.53(d,3H),7.51(d,3H),7.40(s,2H),7.22(m,2H).
实施例9
化合物47的合成
1)中间体47-2的合成
除了起始原料更换为化合物47-1和(4-硝基吡啶-3-基)硼酸以外,其他与实施例1相同。
2)中间体47-3的合成
除了起始原料更换为47-2,其他与实施例1相同。
3)化合物47的合成
除了起始原料更换为47-3和3-溴喹啉以外,其他与实施例1相同。
1HNMR(DMSO):δ9.34(s,2H),8.93(s,3H),8.35(d,2H),8.12(s,3H),8.11(d,3H),8.00(d,3H),7.69(m,3H),7.57(m,3H),7.51(d,2H),7.47(s,4H)
实施例10
化合物53的合成
1)中间体53-2的合成
除了起始原料更换为53-1以外,其他与实施例1相同。
2)中间体53-3的合成
除了起始原料更换为53-2以外,其他与实施例1相同。
3)化合物53的合成
除了起始原料更换为53-3以外,其他与实施例1相同。
1HNMR(DMSO):δ9.34(s,2H),9.25(s,3H),8.52(d,2H),8.35(d,2H),8.07(d,3H),7.75(m,3H),7.69(m,3H),7.63(d,3H),7.51(d,2H),7.47(s,4H).
实施例11
化合物67的合成
1)中间体67-2的合成
除了起始原料更换为化合物67-1和(5-氰基-2-硝基苯基)硼酸以外,其他与实施例1相同。
2)中间体67-3的合成
除了起始原料更换为化合物67-2以外,其他与实施例1相同。
3)化合物67的合成
除了起始原料更换为67-3以外,其他与实施例1相同。
1HNMR(DMSO):δ8.71(s,3H),8.46(d,3H),8.12(d,2H),7.87(d,3H),7.80(s,2H),7.48(m,3H),7.47(s,4H),7.33(d,2H).
实施例12
化合物87的合成
1)中间体87-2的合成
除了起始原料更换为化合物87-1和(3-硝基吡啶-2-基)硼酸以外,其他与实施例1相同。
2)中间体87-3的合成
除了起始原料更换为化合物87-2以外,其他与实施例1相同。
3)化合物87的合成
除了起始原料更换为化合物87-3和2-溴吡嗪以外,其他与实施例1相同。
1HNMR(DMSO):δ8.83(d,3H),8.82(d,3H),8.76(m,3H),8.43(d,2H),7.97(d,2H),7.55(s,2H),7.40(s,2H),7.22(m,2H).
实施例13
化合物94的合成
1)中间体94-2的合成
除了起始原料更换为化合物94-1和(3-硝基吡啶-2-基)硼酸以外,其他与实施例1相同。
2)中间体94-3的合成
除了起始原料更换为化合物94-2以外,其他与实施例1相同。
3)化合物94的合成
除了起始原料更换为化合物94-3和3-(4-溴苯基)吡啶以外,其他与实施例1相同。
1HNMR(DMSO):δ9.24(s,3H),8.70(d,3H),8.43(d,2H),8.42(d,3H),7.97(d,2H),7.92(d,6H),7.91(d,6H),7.57(m,3H),7.55(s,2H),7.40(s,2H),7.22(m,2H).
实施例14
化合物146的合成
1)中间体146-2的合成
除了起始原料更换为146-1以外,其他与实施例1相同。
2)中间体146-3的合成
除了起始原料更换为146-2以外,其他与实施例1相同。
3)化合物146的合成
除了起始原料更换为溴苯和146-3和溴苯以外,其他与实施例1相同。
1HNMR(DMSO):δ8.93(s,1H),8.80(d,1H),8.55(d,2H),8.45(d,1H),8.14(d,1H),8.12(s,1H),7.94(d,2H),7.89(d,1H),7.62(m,4H),7.58(m,2H),7.56(m,1H),7.50(m,4H),7.47(s,4H),7.35(m,2H),7.16(m,2H).实施例15
化合物149的合成
1)中间体149-2的合成
除了起始原料更换为化合物149-1和5-甲氧基-2-硝基苯基)硼酸以外,其他与实施例1相同。
2)中间体149-3的合成
除了起始原料更换为化合物149-2以外,其他与实施例1相同。
3)化合物149的合成
除了起始原料更换为化合物149-3和溴苯以外,其他与实施例1相同。
1HNMR(DMSO):δ8.93(s,1H),8.80(d,1H),8.45(d,1H),8.24(s,2H),8.14(d,1H),8.12(s,1H),7.89(d,1H),7.62(m,4H),7.58(m,2H),7.56(m,1H),7.50(m,4H),7.47(s,4H),7.33(m,2H),6.60(m,2H),3.81(s,9H).
实施例16
化合物183的合成
1)中间体183-2的合成
除了起始原料更换为化合物183-1以外,其他与实施例1相同。
2)中间体183-3的合成
除了起始原料更换为化合物183-2以外,其他与实施例1相同。
3)化合物183的合成
除了起始原料更换为化合物183-3和2-溴萘以外,其他与实施例1相同。
1HNMR(DMSO):δ8.82(d,1H),8.55(d,2H),8.44(d,1H),8.21(s,1H),
8.03(m,6H),7.83(s,2H),7.90(d,1H),7.85(m,1H),7.83(s,2H),7.68(m,1H),7.60(m,1H),7.59(m,2H),7.58(m,2H),7.47(s,5H),7.35(m,3H),7.16(m,2H).
实施例17
化合物E-1的合成
氩气气氛围下,将化合物E-1-1(33.0g,100mmol)、(4,6-二苯基-1,3,5-三嗪-2-基)硼酸(38.8g,110mmol)、双二亚苄基丙酮钯(1.15g,2mmol)、三叔丁基膦四氟硼酸盐(1.16g,4mmol)、1.5M碳酸铯(200ml,300mmol)、以及800mL邻二甲苯添加至反应容器中加热回流20小时。反应完成后,将混合物冷却至室温,冷却至室温,固体析出,过滤,粗品通过硅胶柱层析法精制(洗脱液:乙酸乙酯/己烷),得到38.6g化合物E-1,收率64%,HPLC纯度99.2%。
1HNMR(DMSO):δ9.08(d,1H),8.92(d,1H),8.36(d,2H),8.29(m,1H),8.18(d,2H),8.15(d,1H),7.96(d,2H),7.88(d,1H),7.75(d,2H),7.70(s,2H),7.65(d,2H),7.62(m,1H),7.50(m,3H),7.49(m,2H),7.41(m,1H),7.25(d,2H).
实施例18
化合物E-13的合成
除了起始原料更换为化合物E-13-2以外,其他与实施例17相同。
1HNMR(DMSO):δ9.08(d,1H),8.95(d,1H),8.92(d,1H),8.50(d,1H),8.29(m,1H),7.96(d,4H),7.88(d,1H),7.77(m,1H),7.75(d,2H),7.70(s,1H),7.65(m,2H),7.62(m,1H),7.52(m,1H),7.49(m,2H),7.41(m,1H),7.39(m,1H),7.25(d,4H).
实施例19
化合物E-32的合成
除了起始原料更换为化合物E-32-2以外,其他与实施例17相同。
1HNMR(DMSO):δ9.08(d,1H),8.95(d,1H),8.92(d,1H),8.38(d,1H),8.29(m,1H),8.20(d,1H),8.18(d,2H),8.15(d,1H),8.09(d,1H),7.96(d,2H),7.94(s,1H),7.88(d,1H),7.75(d,2H),7.73(m,1H),7.70(s,2H),7.65(m,2H),7.62(m,1H),7.61(d,1H),7.52(m,1H),7.49(m,2H),7.41(m,1H),7.39(m,1H),7.25(d,2H).
实施例20
化合物E-39的合成
除了起始原料更换为化合物E-39-2以外,其他与实施例17相同。
1HNMR(DMSO):δ9.08(d,1H),8.92(d,1H),8.36(d,2H),8.29(m,1H),8.18(d,2H),8.15(d,1H),8.08(d,1H),7.88(d,2H),7.70(s,2H),7.65(m,2H),7.62(m,1H),7.54(d,1H),7.51(m,1H),7.50(m,3H),7.39(m,1H),7.31(m,1H).
实施例21
化合物E-54的合成
除了起始原料更换为化合物E-54-2以外,其他与实施例1相同。
1HNMR(DMSO):δ9.08(d,1H),8.92(d,1H),8.29(m,1H),8.18(d,2H),8.15(m,1H),8.09(d,1H),8.06(d,1H),7.99(d,1H),7.98(d,1H),7.96(d,2H),7.88(d,1H),7.82(d,1H),7.70(s,2H),7.69(d,1H),7.65(m,2H),7.63(m,1H),7.62(m,1H),7.57(m,1H),7.55(s,1H),7.54(d,1H),7.39(m,1H),7.38(d,1H),7.31(m,1H),7.25(d,2H).
实施例22
化合物E-69的合成
除了起始原料更换为化合物E-69-2以外,其他与实施例17相同。
1HNMR(DMSO):δ9.08(d,1H),8.92(d,1H),8.29(m,1H),8.18(d,2H),8.09(d,1H),8.06(d,1H),7.99(d,1H),7.98(d,1H),7.96(d,2H),7.88(d,1H),7.82(d,1H),7.70(s,2H),7.69(d,1H),7.65(m,2H),7.63(m,1H),7.62(m,1H),7.60(m,1H),7.57(m,1H),7.55(s,1H),7.54(d,1H),7.39(m,1H),7.38(d,1H),7.31(m,1H),7.25(d,2H).
实施例23
化合物E-77的合成
除了起始原料更换为化合物E-77-2以外,其他与实施例17相同。
1HNMR(DMSO):δ9.08(d,1H),8.92(d,1H),8.55(d,1H),8.31(d,1H),8.29(m,1H),8.18(d,2H),8.15(m,1H),7.96(d,2H),7.94(d,1H),7.91(d,1H),7.88(d,1H),7.75(d,2H),7.74(s,1H),7.70(s,2H),7.65(m,1H),7.62(m,3H),7.58(m,1H),7.50(d,2H),7.49(m,2H),7.35(m,1H),7.25(d,2H),7.16(m,1H).
实施例24
化合物E-94的合成
除了起始原料更换为化合物E-94-2以外,其他与实施例17相同。
1HNMR(DMSO):δ9.08(d,1H),8.92(d,1H),8.29(m,1H),8.18(d,2H),8.15(d,1H),7.96(d,4H),7.88(m,1H),7.75(d,4H),7.70(s,2H),7.65(m,2H),7.62(m,1H),7.49(m,4H),7.41(m,2H),7.25(d,4H).
实施例25
化合物E-125的合成
除了起始原料更换为化合物E-125-2以外,其他与实施例17相同。
1HNMR(DMSO):δ9.08(d,1H),8.92(d,1H),8.38(d,1H),8.29(m,1H),8.18(d,2H),8.15(d,1H),8.09(d,1H),8.06(d,1H),7.99(d,1H),7.96(d,2H),7.94(s,1H),7.88(d,1H),7.75(d,2H),7.73(m,1H),7.65(m,2H),7.63(m,1H),7.62(m,1H),7.61(d,1H),7.60(m,1H),7.55(s,1H),7.49(m,2H),7.41(m,1H),7.38(d,1H),7.25(d,2H).
实施例26
化合物E-142的合成
除了起始原料更换为化合物E-142-2以外,其他与实施例17相同。
1HNMR(DMSO):δ9.08(d,1H),8.92(d,1H),8.29(d,1H),8.18(d,2H),8.15(d,1H),8.09(d,1H),8.06(d,1H),7.99(d,1H),7.98(d,1H),7.96(d,2H),7.88(d,2H),7.83(s,1H),7.79(d,1H),7.70(s,2H),7.65(m,2H),7.63(m,1H),7.62(m,1H),7.55(s,1H),7.54(d,1H),7.39(m,1H),7.38(d,1H),7.31(m,1H),7.25(d,2H).
实施例27
化合物E-160的合成
除了起始原料更换为化合物E-160-2以外,其他与实施例17相同。
1HNMR(DMSO):δ9.08(d,1H),8.92(d,1H),8.29(m,1H),8.18(d,2H),8.15(d,1H),8.09(d,1H),8.06(d,1H),7.99(d,1H),7.98(d,1H),7.96(d,2H),7.88(d,2H),7.83(s,1H),7.79(d,1H),7.70(s,1H),7.65(m,2H),7.63(m,1H),7.62(m,1H),7.60(m,1H),7.55(s,1H),7.54(d,1H),7.39(m,1H),7.31(m,1H),7.25(d,2H).
实施例28
化合物E-180的合成
除了起始原料更换为化合物E-180-2以外,其他与实施例1相同。
1HNMR(DMSO):δ9.08(d,1H),8.92(d,1H),8.55(d,1H),8.29(m,1H),8.18(d,2H),8.15(d,1H),8.09(d,1H),8.06(d,1H),7.99(d,1H),7.96(d,2H),7.94(d,1H),7.91(d,1H),7.70(s,2H),7.68(d,1H),7.65(m,2H),7.63(m,1H),7.62(m,2H),7.60(m,1H),7.58(m,1H),7.56(m,1H),7.55(s,1H),7.50(d,2H),7.38(d,1H),7.35(m,1H),7.25(d,2H),7.16(m,1H).
实施例29
化合物E-220的合成
除了起始原料更换为化合物E-220-1和E-220-2以外,其他与实施例17相同。
1HNMR(DMSO):δ9.27(s,1H),8.92(d,1H),8.52(d,1H),8.18(d,2H),8.15(d,1H),7.98(d,1H),7.96(d,2H),7.92(m,1H),7.88(d,2H),7.83(d,1H),7.79(d,1H),7.75(d,2H),7.70(d,1H),7.65(m,2H),7.62(m,1H),7.54(d,1H),7.49(d,2H),7.41(m,1H),7.39(m,1H),7.31(m,1H),7.25(d,2H).
实施例30
化合物E-251的合成
除了起始原料更换为化合物E-251和E-251-2以外,其他与实施例17相同
1HNMR(DMSO):δ9.27(s,1H),8.92(d,1H),8.52(d,1H),8.18(d,2H),8.15(d,1H),8.09(d,2H),8.06(d,1H),7.99(d,1H),7.96(d,2H),7.92(d,1H),7.90(d,1H),7.89(d,1H),7.88(d,1H),7.70(s,1H),7.65(m,2H),7.63(m,1H),7.62(m,1H),7.60(m,1H),7.55(d,2H),7.38(m,1H),7.28(m,1H),7.25(d,2H).
实施例31
化合物E-305的合成
除了起始原料更换为化合物E-305-1和E-305-2以外,其他与实施例17相同
1HNMR(DMSO):δ9.27(s,1H),8.92(d,1H),8.52(d,1H),8.38(d,1H),8.18(d,2H),8.15(d,1H),8.09(d,1H),8.06(d,1H),7.99(d,1H),7.96(d,2H),7.94(s,1H),7.92(d,1H),7.75(d,2H),7.73(m,1H),7.70(d,1H),7.65(m,2H),7.63(m,1H),7.62(m,1H),7.61(d,1H),7.60(m,1H),7.55(s,1H),7.49(d,2H),7.41(m,1H),7.25(d,2H).
实施例32
化合物E-350的合成
除了起始原料更换为化合物E-350-1和E-350-2以外,其他与实施例17相同
1HNMR(DMSO):δ9.27(s,1H),9.09(s,1H),8.92(d,1H),8.55(d,1H),8.52(d,1H),8.49(d,1H),8.31(d,1H),8.18(d,2H),8.16(d,1H),8.15(d,1H),8.08(d,1H),7.94(d,1H),7.92(d,1H),7.91(d,1H),7.88(d,1H),7.74(d,1H),7.70(d,1H),7.65(m,2H),7.62(m,2H),7.61(m,1H),7.59(m,1H),7.50(m,2H),7.35(m,1H),7.16(m,1H).
器件实施方案
有机光电器件的评价
器件实施例中所用的各有机层化合物如下所示:
实施例33
有机光电器件的基本结构模型为:ITO/HAT-CN(10nm)/TAPC(40nm)/TCTA(10nm)/EML(本发明的主体材料:RD(Ir配合物))(40nm)=98:2/ETL(30nm)/LiF(1nm)/Al(80nm)
本发明有机光电器件的制造方法:
(1)依次用丙酮、乙醇和蒸馏水对透明阳极氧化铟锡(ITO)20(10Ω/sq)玻璃基板进行超声清洗,再用臭氧等离子处理15分钟;
(2)在真空气相蒸镀设备的衬底固定器上安装ITO衬底后,控制体系压力在10-6托,接着向ITO衬底上依次蒸镀厚度为10nm的HAT-CN,40nm的TAPC和10nm的TCTA;
(3)蒸镀厚度为40nm的发光层(EML)(其中,本发明主体材料与RD的质量比为98:2,第一主体化合物与第二主体化合物的质量比为2:3);
(4)蒸镀厚度为30nm的电子传输层(ETL)材料;
(5)蒸镀厚度为1nm的LiF作为电子注入层;
(6)最后蒸镀厚度为80nm的Al作为阴极,且利用玻璃封装盖对器件进行封装。
本发明的有机光电器件测试结果见表1。
实施例34
除了EML材料更换为化合物4和E-13以外,其余与实施例33作成相同的器件进行评价,测试结果见表1。
实施例35
除了EML材料为化合物12和E-32以外,其余与实施例33作成相同的器件进行评价,测试结果见表1。
实施例36
除了EML材料为化合物18和E-39以外,其余与实施例33作成相同的器件进行评价,测试结果见表1。
实施例37
除了EML材料为化合物22和E-54以外,其余与实施例33作成相同的器件进行评价,测试结果见表1。
实施例38
除了EML材料为化合物30和E-69以外,其余与实施例33作成相同的器件进行评价,测试结果见表1。
实施例39
除了EML材料为化合物37和E-77以外,其余与实施例33作成相同的器件进行评价,测试结果见表1。
实施例40
除了EML材料为化合物44和E-94以外,其余与实施例33作成相同的器件进行评价,测试结果见表1。
实施例41
除了EML材料为化合物47和E-125以外,其余与实施例33作成相同的器件进行评价,测试结果见表1。
实施例42
除了EML材料为化合物53和E-142以外,其余与实施例33作成相同的器件进行评价,测试结果见表1。
实施例43
除了EML材料为化合物67和E-160以外,其余与实施例33作成相同的器件进行评价,测试结果见表1。
实施例44
除了EML材料为化合物87和E-180以外,其余与实施例33作成相同的器件进行评价,测试结果见表1。
实施例45
除了EML材料为化合物94和E-220以外,其余与实施例33作成相同的器件进行评价,测试结果见表1。
实施例46
除了EML材料为化合物146和E-251以外,其余与实施例33作成相同的器件进行评价,测试结果见表1。
实施例47
除了EML材料为化合物149和E-305以外,其余与实施例33作成相同的器件进行评价,测试结果见表1。
实施例48
除了EML材料为化合物183和E-350以外,其余与实施例33作成相同的器件进行评价,测试结果见表1。
对比例1
除了EML材料为化合物CBP以外,其余与实施例33作成相同的器件进行评价,测试结果见表1。
对比例2
除了EML材料为化合物Ref-1和Ref-2以外,其余与实施例33作成相同的器件进行评价,测试结果见表1。
表1
从表1可以看出,有机光电器件结构除了发光层不同外,其它均一致,基于对比例1和对比例2的器件性能为参考,本发明的主体材料应用于发光层后的器件的电流效率有了显著提升,同时器件寿命也有所提升。因此,本发明的主体材料在有机光电器件(例如有机发光二极管)上具有有较大的应用价值。
以上描述了本发明的基本原理、主要特征和本发明的优点。本行业的技术人员应该了解,本发明不受上述实施例的限制,上述实施例和说明书中描述的只是说明本发明的原理,在不脱离本发明精神和范围的前提下本发明还会有各种变化和改进,这些变化和改进都落入要求保护的本发明范围内。本发明要求保护范围由所附的权利要求书及其等同物界定。
Claims (9)
1.主体材料,所述主体材料包含至少一种第一主体化合物和至少一种第二主体化合物,其中所述第一主体化合物由通式Ⅰ表示并且所述第二主体化合物由通式Ⅱ表示:
其中,X1-X8各自独立地选自CR或N原子,其中R选自氢、氘、卤素、氰基、取代或未取代的烷基、环烷基、杂烷基、杂环烷基、芳基或杂芳基;
X1-X8彼此相同或不同;
L1、L2和L3各自独立地选自单键或取代或未取代的芳基;
R1、R2和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C4~C30杂芳基或与邻近的原子键合成环,其中R1、R2和R3中至少一者选自如下取代或未取代的基团:
其中,R4-R10各自独立地选自氢、取代或未取代的C1-C15烷基、取代或未取代的C6~C30芳基或取代或未取代的C4~C30杂芳基;
当X1-X8均不为N原子时,R1、R2和R3不全相同或全部不相同;
其中,Ar1、Ar2和Ar3各自独立地选自取代或未取代的C6~C30芳基或取代或未取代的C3~C30杂芳基;
Z1、Z2和Z3各自独立地选自碳或氮;
Y1和Y2各自独立地选自NR1或氧,其中R1为取代或未取代的C1~C20烷基、取代或未取代的C6~30芳基或取代或未取代的C3~C30杂芳基;
R11为氢、取代或未取代的C1-C15烷基、取代或未取代的C6~C30芳基或取代或未取代的C4~C30杂芳基。
5.有机光电器件,其包括阴极层、阳极层和有机层,其中,所述有机层为空穴注入层、空穴传输层、发光层、电子注入层或电子传输层中至少一层,其中,所述发光层中含有权利要求1-4中任一项所述的主体材料。
6.根据权利要求5所述的有机光电器件,其中所述有机层为发光层,所述发光层还包含掺杂剂,其中所述主体材料与所述掺杂剂的质量比为1:99~99:1。
7.根据权利要求6所述的有机光电器件,其中所述第一主体化合物与所述第二主体化合物的质量比为1:99~99:1。
8.根据权利要求5所述的有机光电器件,其中所述有机光电器件为有机光伏器件、有机发光器件、有机太阳电池、电子纸、有机感光体、有机薄膜晶体管或有机内存器件。
9.显示或照明装置,其包括权利要求5所述的有机光电器件。
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CN106467522A (zh) * | 2016-07-25 | 2017-03-01 | 江苏三月光电科技有限公司 | 一种含有三嗪类化合物的有机电致发光器件及其应用 |
CN106397398A (zh) * | 2016-08-31 | 2017-02-15 | 北京绿人科技有限责任公司 | 一种有机化合物及其在有机电致发光器件中的应用 |
CN112313811A (zh) * | 2018-06-22 | 2021-02-02 | 罗门哈斯电子材料韩国有限公司 | 多种主体材料及包含其的有机电致发光装置 |
CN113410415A (zh) * | 2020-03-17 | 2021-09-17 | 罗门哈斯电子材料韩国有限公司 | 多种主体材料和包含其的有机电致发光装置 |
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WO2023200315A1 (ko) * | 2022-04-15 | 2023-10-19 | 주식회사 엘지화학 | 신규한 화합물 및 이를 이용한 유기 발광 소자 |
CN117430594A (zh) * | 2023-08-03 | 2024-01-23 | 陕西莱特光电材料股份有限公司 | 有机化合物、电子元件和电子装置 |
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