CN115160241A - 一种三嗪类电子传输材料及其制备方法与应用、包含其的有机电致发光器件 - Google Patents
一种三嗪类电子传输材料及其制备方法与应用、包含其的有机电致发光器件 Download PDFInfo
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- CN115160241A CN115160241A CN202210922210.0A CN202210922210A CN115160241A CN 115160241 A CN115160241 A CN 115160241A CN 202210922210 A CN202210922210 A CN 202210922210A CN 115160241 A CN115160241 A CN 115160241A
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- 239000000463 material Substances 0.000 title claims abstract description 83
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 title claims abstract description 27
- 238000002360 preparation method Methods 0.000 title claims abstract description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 142
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 138
- 239000010410 layer Substances 0.000 claims description 124
- 238000006243 chemical reaction Methods 0.000 claims description 101
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 96
- 229910052757 nitrogen Inorganic materials 0.000 claims description 71
- 239000000243 solution Substances 0.000 claims description 58
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 54
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 51
- 239000003208 petroleum Substances 0.000 claims description 48
- 239000007787 solid Substances 0.000 claims description 45
- 238000001035 drying Methods 0.000 claims description 43
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 42
- 239000012044 organic layer Substances 0.000 claims description 41
- 229910052760 oxygen Inorganic materials 0.000 claims description 41
- 229910052717 sulfur Inorganic materials 0.000 claims description 40
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 38
- 125000005842 heteroatom Chemical group 0.000 claims description 38
- 239000001301 oxygen Substances 0.000 claims description 38
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 37
- 239000011593 sulfur Substances 0.000 claims description 37
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 35
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 34
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- 238000003756 stirring Methods 0.000 claims description 28
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- 239000000126 substance Substances 0.000 claims description 25
- 239000005416 organic matter Substances 0.000 claims description 22
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 21
- 239000011259 mixed solution Substances 0.000 claims description 21
- 239000002994 raw material Substances 0.000 claims description 19
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- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 17
- 239000000047 product Substances 0.000 claims description 17
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 16
- 238000004440 column chromatography Methods 0.000 claims description 16
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- 230000005525 hole transport Effects 0.000 claims description 15
- 238000005406 washing Methods 0.000 claims description 15
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 12
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- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims description 12
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 11
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- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 10
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 10
- 238000002386 leaching Methods 0.000 claims description 10
- 230000000903 blocking effect Effects 0.000 claims description 9
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- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 235000019441 ethanol Nutrition 0.000 claims description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 8
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- -1 cyano, carboxyl Chemical group 0.000 claims description 7
- 239000000284 extract Substances 0.000 claims description 7
- UQPUONNXJVWHRM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 UQPUONNXJVWHRM-UHFFFAOYSA-N 0.000 claims description 7
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 claims description 6
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000008346 aqueous phase Substances 0.000 claims description 6
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 229910052710 silicon Inorganic materials 0.000 claims description 6
- 239000010703 silicon Substances 0.000 claims description 6
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 5
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims description 5
- 229910000024 caesium carbonate Inorganic materials 0.000 claims description 5
- 229910052805 deuterium Inorganic materials 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 239000003446 ligand Substances 0.000 claims description 5
- 239000002244 precipitate Substances 0.000 claims description 5
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- 150000004982 aromatic amines Chemical class 0.000 claims description 4
- 125000005549 heteroarylene group Chemical group 0.000 claims description 4
- 150000002431 hydrogen Chemical group 0.000 claims description 4
- 230000001376 precipitating effect Effects 0.000 claims description 4
- 239000010409 thin film Substances 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000000707 boryl group Chemical group B* 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 108091008695 photoreceptors Proteins 0.000 claims description 3
- 238000009987 spinning Methods 0.000 claims description 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 2
- 125000006584 (C3-C10) heterocycloalkyl group Chemical group 0.000 claims description 2
- 125000006835 (C6-C20) arylene group Chemical group 0.000 claims description 2
- 125000006751 (C6-C60) aryloxy group Chemical group 0.000 claims description 2
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 2
- 125000002723 alicyclic group Chemical group 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 125000000732 arylene group Chemical group 0.000 claims description 2
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 claims description 2
- 125000003367 polycyclic group Chemical group 0.000 claims description 2
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims 1
- 125000000524 functional group Chemical group 0.000 abstract description 6
- 230000032258 transport Effects 0.000 description 42
- 150000001875 compounds Chemical class 0.000 description 33
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- 230000008020 evaporation Effects 0.000 description 12
- 239000002019 doping agent Substances 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 9
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 8
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- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 4
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- 101150003085 Pdcl gene Proteins 0.000 description 4
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- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
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- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 238000005036 potential barrier Methods 0.000 description 1
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- 230000000750 progressive effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
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- 230000006798 recombination Effects 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
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- 238000001308 synthesis method Methods 0.000 description 1
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- 150000003852 triazoles Chemical class 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 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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Abstract
Description
技术领域
本发明属于有机光电材料领域,具体涉及一种三嗪类电子传输材料及其制备方法与应用、包含其的有机电致发光器件。
背景技术
目前,作为新一代显示技术的有机电致发光器件(OLED)在显示和照明技术方面都获得了越来越多的关注,应用前景十分广泛。
有机发光二极管(OLED:Organic Light Emitting Diode)作为一种新型和有前途的显示技术逐渐进入人们的视野。OLED是一种由多层有机薄膜结构形成的电致发光器件。有机电致发光器件是利用了如下原理的自发光元件:通过施加电场,利用由阳极注入的空穴与由阴极注入的电子的复合能使荧光性物质发光。
它具有如下结构:阳极、阴极以及介于两者之间的有机材料层。为了提高有机电致发光器件的效率和稳定性,有机材料层通常包括具有不同材料的多层,例如空穴注入层(HIL)、空穴传输层(HTL)、发光层、电子传输层(ETL)和电子注入层(EIL)。这种有机发光元件中,当在阳极和阴极之间施加电压时,来自阳极的空穴和来自阴极的电子注入有机材料层,产生的激子在迁移至基态时产生具有特定波长的光。
电子传输层是OLED结构中的一个关键组成部分,目前作为电子传输层所用到的电子传输型材料的电子迁移率低,而空穴迁移率较高,使发光器件内部的电子-空穴不平衡,从而导致器件效率降低,稳定性差,寿命短等问题。
因此,研发一种具有高迁移率电子传输材料使其制备而成的有机电致发光器件具有低驱动电压,高效率,长寿命的性能优点是本领域人员亟需解决的技术问题。
发明内容
有鉴于此,本发明提供一种电子传输材料,旨在解决现有的发光器件效率降低,稳定性差,寿命短等问题。
为了实现上述目的,本发明的第一个目的在于提供一种三嗪类电子传输材料。采用如下技术方案:
一种三嗪类电子传输材料,具有如下结构通式:
其中,
X、Y分别独立选自C-R4/R5、N-R6、O或S;
m、n分别选自0或1的整数,且m和n不同时为0;
L1、L2表示为连接键、经取代或未经取代的C6-C30亚芳基、经取代或未经取代的3元-20元亚杂芳基,其杂原子选自氧、氮或硫;
环A表示取代或未经取代的C3-C30环烷基、取代或未经取代的3元-30元杂环烷基,其杂原子选自氧、氮或硫;经取代或未经取代的C6-C30芳基、经取代或未经取代的3元-20元杂芳基,其杂原子选自氧、氮或硫;经取代或未经取代的3元-25元杂芳基胺基,其杂原子选自氧、氮或硫;经取代或未经取代的C6~C60芳基胺基;
R1、R2、R3各自独立地为氢、氘、卤素、氰基、羧基、硝基、羟基、氨基、磺酸基、磺酰基、磷酸基、磷酰基、硅基或硼烷基;取代或未经取代的C1-C30烷基、取代或未经取代的C2-C30烯基、取代或未经取代的C2-C30炔基、取代或未经取代的C3-C30环烷基、取代或未经取代的3元-30元杂环烷基,其杂原子选自氧、氮或硫;经取代或未经取代的C6-C30芳基、经取代或未经取代的3元-20元杂芳基,其杂原子选自氧、氮或硫;经取代或未经取代的3元-25元杂芳基胺基,其杂原子选自氧、氮或硫;经取代或未经取代的C6~C60芳基胺基、经取代或未经取代的C1-C30烷氧基、经取代或未经取代的C6-C60芳氧基;
R4~R6各自独立地表示经取代或未经取代的C1-C30烷基、经取代或未经取代C6-C30芳基、经取代或未经取代的3元-30元杂芳基,其杂原子选自氧、氮或硫;或与相邻取代基连接形成单环或多环C3-C30脂环族环或C3-C30芳香族环,其碳原子可置换为至少一个选自氮、氧或硫的杂原子;
Ar1-Ar4各自独立地表示经取代或未经取代的C1-C30烷基、取代或未经取代的C3-C30环烷基、取代或未经取代的3元-20元杂环烷基,其杂原子选自氧、氮或硫;经取代或未经取代的C6-C30芳基或经取代或未经取代的3元-30元杂芳基,其杂原子选自氧、氮或硫;经取代或未经取代的3元-15元杂芳基胺基,其杂原子选自氧、氮或硫;经取代或未经取代的C6~C60芳基胺基。
值得说明的是,环A为稠合在苯环上的取代基,环A可稠合在苯环的任意位置。
本发明公开的电子传输材料中的三嗪类结构是吸电子能力强的官能团,所采用的吸电子能力强的官能团基团能有效提高电子传输材料的电子迁移率。改善有机电致发光器件内部电子-空穴不平衡的问题,提高发光效率,进一步提高电子传输材料的电子迁移率的同时,平面分子结构能使核心结构的π-共轭体系不被延续,保证高三线态能级(ET),宽带隙。进一步提高发光效率,并改善器件各层能级匹配程度,降低驱动电压,延长器件寿命。
进一步的,所述L1、L2表示为连接键、经取代或未经取代的C6-C20亚芳基、经取代或未经取代的3元-18元亚杂芳基,其杂原子选自氧、氮或硫;
环A表示经取代或未经取代的C6-C30芳基、经取代或未经取代的3元-20元杂芳基,其杂原子选自氧、氮或硫;
R1、R2、R3彼此相同或不同,并且各自独立地为氢、氘、卤素、氰基;取代或未经取代的C1-C10烷基、取代或未经取代的C3-C10环烷基、取代或未经取代的3元-10元杂环烷基,其杂原子选自氧、氮或硫;经取代或未经取代的C6-C20芳基、经取代或未经取代的3元-10元杂芳基,其杂原子选自氧、氮或硫;经取代或未经取代的3元-15元杂芳基胺基,其杂原子选自氧、氮或硫;经取代或未经取代的C6~C20芳基胺基;
Ar1-Ar4各自独立地表示取代或未经取代的C6-C20芳基、经取代或未经取代的3元-15元杂芳基,其杂原子选自氧、氮或硫;经取代或未经取代的3元-15元杂芳基胺基,其杂原子选自氧、氮或硫;经取代或未经取代的C6~C30芳基胺基。
上述术语中,“取代”意指与化合物的碳原子键合的氢原子变成另外的取代基,并且取代的位置没有限制,只要该位置为氢原子被取代的位置(即,取代基可以取代的位置)即可,并且当两个或更多个取代基取代时,两个或更多个取代基可以彼此相同或不同
即上述的“取代或未经取代”中的“取代”,可优选的取代基为氘、氰基、卤素、硝基、羟基、磷酸基、硼烷基、硅基、C1~C8烷基、C2~C15烯基、C2~C10炔基、C6~C20芳基、C3~C10杂芳基、C1~C10烷氧基、C6~C20芳基氨基中的一种或多种。
更进一步的,所述通式1由以下式(1)-(92)中的任一表示:
本发明的第二个目的在于提供一种如上所述的三嗪类电子传输材料的制备方法,采用如下技术方案:
一种三嗪类电子传输材料的制备方法,L为非连接键,包括如下反应步骤:
(1)将原料A(1.1eq)和原料B(1.0eq)加入到三口反应瓶中,分别加入四(三苯基膦钯)(0.01eq)和碳酸钾(2.0eq),再加入甲苯:乙醇:水=2:1:1混合液,氮气保护,升温到90℃回流过夜,反应完毕后,反应液降温到40-50℃,分去水层,用无水硫酸钠干燥有机层,旋干有机层得到固体有机物,使用少量的二氯甲烷将固体有机物完全溶解,然后缓慢滴加到石油醚溶液中,搅拌均匀,有沉淀析出,抽滤得固体,依次用无水乙醇、石油醚淋洗,烘干,获得中间体1;
(2)将中间体1(1.0eq)加入到反应瓶中,再加入(1.1eq)的碳酸钾,加入溶剂DMSO,氮气保护下,升温到160℃反应24小时。将反应液降到室温,加入水搅拌,再加入乙酸乙酯萃取反应液,得到的萃取液再用水洗涤一次,无水硫酸镁干燥,旋干得到油状物,利用二氯甲烷和石油醚(v:v=10:4)的混合溶液,通过柱色谱法纯化剩余物质从而获得中间体2;
(3)将中间体2(1.0eq)和原料C(1.1eq)加入到反应瓶中,再分别加入Pd(oAc)2(0.05eq)、碳酸铯(2.0eq)、配体X-PHOS(0.11eq),加入乙二醇二甲醚DME:水=2:1的混合溶液,氮气保护,升温回流反应16小时。处理过程:反应完毕后,反应液降温到40-50℃,分去水层,用无水硫酸钠干燥有机层,旋干有机层得到黑色状物,用二氯甲烷:石油醚=1:1过柱子,收集产品点,从而获得中间体3;
(4)将中间体3(1.0eq)和原料D(1.1eq)加入到反应瓶中,再分别加入Pd(oAc)2(0.05eq)、碳酸铯(2.0eq)、配体X-PHOS(0.11eq),加入乙二醇二甲醚DME:水=2:1的混合溶液,氮气保护,升温回流反应16小时。处理过程:反应完毕后,反应液降温到40-50℃,分去水层,用无水硫酸钠干燥有机层,旋干有机层得到黑色状物,利用二氯甲烷和石油醚(v:v=10:4)的混合溶液,通过柱色谱法纯化剩余物质从而获得通式1;且,
具体合成路线如反应式I所示:
式中A、X、Y、R1~R3、L1、L2、Ar1~Ar4具有如上所给定义。
一种三嗪类电子传输材料的制备方法,L为连接键,包括如下反应步骤:
(1)将原料A(1.1eq)和原料B(1.0eq)加入到三口反应瓶中,分别加入四(三苯基膦钯)(0.01eq)和碳酸钾(2.0eq),再加入甲苯:乙醇:水=2:1:1混合液,氮气保护,升温到90℃回流过夜。反应完毕后,反应液降温到40-50℃,分去水层,用无水硫酸钠干燥有机层,旋干有机层得到固体有机物,使用少量的二氯甲烷将固体有机物完全溶解,然后缓慢滴加到石油醚溶液中,搅拌均匀,有沉淀析出,抽滤得固体,依次用无水乙醇、石油醚淋洗,烘干,获得中间体1;
(2)将中间体1(1.0eq)加入到反应瓶中,再加入(1.1eq)的碳酸钾,加入溶剂DMSO,氮气保护下,升温到160℃反应24小时。将反应液降到室温,加入水搅拌,再加入乙酸乙酯萃取反应液,得到的萃取液再用水洗涤一次,无水硫酸镁干燥,旋干得到油状物,利用二氯甲烷和石油醚(v:v=10:4)的混合溶液,通过柱色谱法纯化剩余物质从而获得中间体2;
(3)氮气保护下,将中间体2(1.0eq)和原料C(1.1eq)溶于甲苯溶液中,加入三(二亚苄基丙酮)二钯(0.01eq),三叔丁基膦(0.05eq)及叔丁醇钠(2.0eq),搅拌均匀,升温至回流,反应5h;反应结束后,稍降温度,使用硅藻土进行过滤,除去盐以及催化剂,滤液冷却至室温后,水洗三遍,保留有机相,接着用乙酸乙酯萃取水相;合并有机相后,使用无水硫酸镁进行干燥,并且使用旋转式蒸发器去除溶剂;使用少量的二氯甲烷将固体有机物完全溶解,然后缓慢滴加到石油醚溶液中,搅拌均匀,有沉淀析出,抽滤得固体,依次用无水乙醇、石油醚淋洗,烘干,从而获得中间体3;
(4)氮气保护下,将中间体3(1.0eq)和原料D(1.1eq)溶于甲苯溶液中,加入三(二亚苄基丙酮)二钯(0.01eq),三叔丁基膦(0.05eq)及叔丁醇钠(2.0eq),搅拌均匀,升温至回流,反应5h;反应结束后,稍降温度,使用硅藻土进行过滤,除去盐以及催化剂,滤液冷却至室温后,水洗三遍,保留有机相,接着用乙酸乙酯萃取水相;合并有机相后,使用无水硫酸镁进行干燥,并且使用旋转式蒸发器去除溶剂;利用二氯甲烷和石油醚(v:v=10:4)的混合溶液,通过柱色谱法纯化剩余物质从而获得通式1;且,
具体合成路线如反应式II所示:
式中A、X、Y、R1~R3、L1、L2、Ar1~Ar4具有如上所给定义。
值得说明的是,考虑到本发明的完整实现,现提供一种原料A的制备方法。应当理解,此制备方法不是对本发明技术实现的限定,任何通过现有技术或不经创造性劳动获得原料A的技术手段都应当视为本发明获得原料A的合理途径。
一种原料A的制备方法,包括如下反应步骤:
1)当X为O、S时:
将A(1eq)加入到三口瓶中,再依次加入Pd(pph3)2约(0.1eq),CuI(2eq),Et3N(2eq)和干燥的DMF 200mL,最后加入B(2eq)。在氮气的保护下,将反应物升温到80℃反应48h。冷却到室温,除去不溶物,将反应液倒入约1000mL水中,有固体析出,过滤干燥,过硅胶柱分离(石油醚:乙酸乙酯=10:1)出纯品C。
将C(1eq)溶于200mL二氯甲烷中,室温下逐量加入NBS(1.1eq),过程持继10min左右,反应16h。过滤除去不溶物,旋干滤液得固体,加入石油醚200mL、甲醇50mL和水100mL搅拌24h,抽滤得到固体D。
将D(1eq)加入到反应瓶中,分别加入PdCl2(dppf)(0.03eq)、醋酸钾(2eq)和1,4-二氧六环200mL,氮气保护下升温到90℃反应6h。反应完毕后,降到室温,过滤,除去不溶物,旋干滤液,得到黑色油状物。过硅胶柱分离产物(二氯甲烷:石油醚=1:4),得到目标产物原料A。
2)当X为C时:
将A3(1eq)溶解在100mL的二氯甲烷中备用。然后在80mL的二氯甲烷中,加入TiCl4(6eq)并搅拌,氮气保护下降温到-50℃保持30min,注入二甲基锌(6eq),溶液由无色变为橙棕色,-50℃搅拌1h。再滴加A3的二氯甲烷溶液-50℃反应2h。升温到-10℃加入冷的饱和氯化铵溶液搅拌30min,静止分液,有机层用盐水洗,无水硫酸钠干燥,浓缩得到油状物。过柱纯化,二氯甲烷:石油醚=1:10洗脱,得到无色油状物B3。
将化合物C3(1eq)溶解在200mL无水乙醇中,分别加入DDQ(1.1eq)和钯碳催化剂3g,升温回流反应4h。降温过滤除去催化剂,浓缩得到产物C3。
将化合物C3(1eq)溶解在100mL二氯甲烷中,分批加入NBS(1eq),室温下反应过24h。过滤除去不溶物,浓缩加入甲醇析出固体,再用水和甲醇冲洗滤饼,干燥得化合物D3。
将化合物D3(1eq)和原料E3(1.1eq)加入到反应瓶中,加入四三苯基膦钯(0.01eq)和碳酸钾(2eq),再加入甲苯、乙醇和水的2:1:1的混合液400mL,升温到90℃反应16h。降温,分液,水洗一次甲苯层,无水硫酸钠干燥,浓缩得到油状物,过硅柱,二氯甲烷:石油醚=1:4淋洗,得到白色固体F3。
将化合物F30.077 mol溶解在100mL DMF中,分批加入NBS 0.093mol,升温到100℃反应过24h。将反应液倒入300mL冷水中,搅拌有大量的固体析出,过滤得到深色产品,过硅柱,二氯甲烷:石油醚=1:4淋洗,得到白色固体G2。
将G3(1eq)加入到反应瓶中,分别加入PdCl2(dppf)(0.03eq)、醋酸钾(2eq)和1,4-二氧六环200mL,氮气保护下升温到90℃反应6h。反应完毕后,降到室温,过滤,除去不溶物,旋干滤液,得到黑色油状物。过硅胶柱分离产物(二氯甲烷:石油醚=1:4),得到目标产物原料A。
3)当X为N时:
将A2(1eq)溶于200mL二氯甲烷中,室温下逐量加入NBS(1eq),过程持继10min左右,反应16h。过滤除去不溶物,旋干滤液得固体,加入石油醚300mL、甲醇50mL和水100mL搅拌24h,抽滤得到固体D2。
将B2(1eq)、原料C2(1.1eq)、催化剂(0.01eq)和碳酸钾(2eq)依次加入到反应瓶中,氮气保护,加入甲苯:乙醇:水=2:1:1的混合物约400mL,升温到90℃反应18h。反应完毕后,降温分液,无水硫酸镁干燥,旋干甲苯层,得到黑色油状物,过硅胶柱,二氯甲烷:石油醚=1:2淋洗,收集目标产品D2。
将干燥后的D2(1eq)加入到100mL的DMF中并滴入几滴乙酸,再加分批逐量加入NBS(1.1eq)升温到100℃反应过夜。待反应完毕后降温,将反应液倒入500mL水中,有大量固体析出,抽滤干燥得E2。
将E2(1eq)加入到反应瓶中,分别加入PdCl2(dppf)(0.03eq)、醋酸钾(2eq)和1,4-二氧六环200mL,氮气保护下升温到90℃反应6h。反应完毕后,降到室温,过滤,除去不溶物,旋干滤液,得到黑色油状物。过硅胶柱分离产物(二氯甲烷:石油醚=1:4),得到目标产物原料A。
本发明的第三个目的在于提供一种如上所述的三嗪类电子传输材料在制备有机发光器件、有机太阳电池、电子纸、有机感光体或有机薄膜晶体管中的应用。
本发明的第四个目的在于提供一种有机电致发光器件,包括第一电极,第二电极,置于所述第一电极和所述第二电极之间的一个或多个有机物层;且
所述有机物层至少包括空穴注入层、空穴传输层、电子阻挡层、发光辅助层、发光层、空穴阻挡层、电子传输层、电子注入层及盖帽层中的一种;且,
所述电子传输层或电子注入层包含一种或多种如权利要求1~3任一所述的三嗪类电子传输材料。
本发明对所述有机电致发光器件的制备方法并无限定,优选利用薄膜蒸镀、电子束蒸发或物理气相沉积等方法在基板上蒸镀金属及具有导电性的氧化物及它们的合金形成阳极,然后在其上形成有机物层及蒸镀阴极,得到有机电致发光器件。
与现有技术相比,本发明公开的电子传输材料中的三嗪类结构是吸电子能力强的官能团,所采用的吸电子能力强的官能团基团能有效提高电子传输材料的电子迁移率。改善有机电致发光器件内部电子-空穴不平衡的问题,提高发光效率,进一步提高电子传输材料的电子迁移率的同时,平面分子结构能使核心结构的π-共轭体系不被延续,保证高三线态能级(ET),宽带隙。进一步提高发光效率,并改善器件各层能级匹配程度,降低驱动电压,延长器件寿命。
附图说明
为了更清楚地说明本发明实施例或现有技术中的技术方案,下面将对实施例或现有技术描述中所需要使用的附图作简单地介绍,显而易见地,下面描述中的附图仅仅是本发明的实施例,对于本领域普通技术人员来讲,在不付出创造性劳动的前提下,还可以根据提供的附图获得其他的附图。
图1为本发明实施例1化合物HT-1核磁共振氢谱图。
图2为本发明实施例3化合物HT-81核磁共振氢谱图。
具体实施方式
下面将结合附图对本发明实施例中的技术方案进行清楚、完整地描述,显然,所描述的实施例仅仅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。
本说明书中各个实施例采用递进的方式描述,每个实施例重点说明的都是与其他实施例的不同之处,各个实施例之间相同相似部分互相参见即可。对于实施例公开的装置而言,由于其与实施例公开的方法相对应,所以描述的比较简单,相关之处参见方法部分说明即可。
值得说明的是,考虑到技术的完整实现,本发明提供一种原料A的制备方法。但应当明确,此方法不可理解为对原料A获得方法及途径的限定,任何基于现有技术或不经创造性劳动获得原料A的方法均应当视为本发明的保护范围。
一种原料A的制备方法,反应途径如下:
将100mmol的A1溶解在100mL的二氯甲烷中备用。然后在80mL的二氯甲烷中,加入600mmol的TiCl4并搅拌,氮气保护下降温到-50℃保持30min,注入二甲基锌600mmol,溶液由无色变为橙棕色,-50℃搅拌1h。再滴加A1的二氯甲烷溶液-50℃反应2h。升温到-10℃加入冷的饱和氯化铵溶液搅拌30min,静止分液,有机层用盐水洗,无水硫酸钠干燥,浓缩得到油状物。过柱纯化,二氯甲烷:石油醚=1:10洗脱,得到无色油状物B1(98.0%,21.0g,MW:214.20)。
将95mmol的化合物B1溶解在200mL无水乙醇中,分别加入105mmol的DDQ和3g的钯碳催化剂,升温回流反应4h。降温过滤除去催化剂,浓缩得到产物C1(95.0%,19.2g,MW:212.25)。
将90mmol的化合物C1溶解于100mL二氯甲烷中,分批加入90mmol的NBS,室温下反应过24h。过滤除去不溶物,浓缩加入甲醇析出固体,再用水和甲醇冲洗滤饼,干燥得化合物D1(95.3%,25.02g,MW:291.19)。
将80mmol的化合物D1和80mmol的原料E1加入到反应瓶中,加入四三苯基膦钯(0.8mmol)和碳酸钾(160mmol),再加入甲苯、乙醇和水的2:1:1的混合液400mL,升温到90℃反应16h。降温,分液,水洗一次甲苯层,无水硫酸钠干燥,浓缩得到油状物,过硅柱,二氯甲烷:石油醚=1:4淋洗,得到白色固体F1(95.0%,19.2g,MW:212.25)。
将0.077mol的化合物F1溶解在100mL DMF中,分批加入0.093mol的NBS,升温到100℃反应过24h。将反应液倒入300mL冷水中,搅拌有大量的固体析出,过滤得到深色产品,过硅柱,二氯甲烷:石油醚=1:4淋洗,得到白色固体G1(90.3%,25.6g,MW:367.28)。
将60mmol的G1加入到反应瓶中,分别加入PdCl2(dppf)1.8mmol、醋酸钾120mmol和1,4-二氧六环200mL,氮气保护下升温到90℃反应6h。反应完毕后,降到室温,过滤,除去不溶物,旋干滤液,得到黑色油状物。过硅胶柱分离产物(二氯甲烷:石油醚=1:4),得到目标产物原料A(91.5%,22.8g,MW:414.39)。
实施例1:化合物HT-1的合成
将原料A(55mmol)和原料B(50mmol)加入到三口反应瓶中,分别加入四(三苯基膦钯)(0.50mmol)和碳酸钾(100mmol),再加入120.00mL甲苯:乙醇:水=2:1:1混合液,氮气保护,升温到90℃回流过夜。反应完毕后,反应液降温到40-50℃,分去水层,用无水硫酸钠干燥有机层,旋干有机层得到固体有机物,使用少量的二氯甲烷将固体有机物完全溶解,然后缓慢滴加到石油醚溶液中,搅拌均匀,有沉淀析出,抽滤得固体,依次用无水乙醇、石油醚淋洗,烘干,获得中间体1(13.8g,产率:75.8%,MW:364.75)。
将中间体1(30mmol)加入到反应瓶中,再加入(33mmol)的碳酸钾,加入80.00mL的DMSO溶剂,氮气保护下,升温到160℃反应24h。将反应液降到室温,加入水搅拌,再加入乙酸乙酯萃取反应液,得到的萃取液再用水洗涤一次,无水硫酸镁干燥,旋干得到油状物,利用二氯甲烷和石油醚(v:v=10:4)的混合溶液,通过柱色谱法纯化剩余物质从而获得中间体2(7.0g,产率:67.5%,MW:344.82)。
氮气保护下,将中间体2(15mmol)和原料C(16.5mmol)溶于90.00mL甲苯溶液中,加入三(二亚苄基丙酮)二钯(0.15mmol),三叔丁基膦(0.75mmol)及叔丁醇钠(30mmol),搅拌均匀,升温至回流,反应5h;反应结束后,稍降温度,使用硅藻土进行过滤,除去盐以及催化剂,滤液冷却至室温后,水洗三遍,保留有机相,接着用乙酸乙酯萃取水相;合并有机相后,使用无水硫酸镁进行干燥,并且使用旋转式蒸发器去除溶剂;利用二氯甲烷和石油醚(v:v=10:4)的混合溶液,通过柱色谱法纯化剩余物质从而获得化合物HT-1(4.6g,产率:56.9%,Mw:541.79)。
HPLC纯度:>99.5%。
元素分析:
计算值为:C,86.47;H,5.77;N,7.76。
测试值为:C,86.52;H,5.85;N,7.83。
实施例2:化合物HT-17的合成
将原料A(55mmol)和原料B(50mmol)加入到三口反应瓶中,分别加入四(三苯基膦钯)(0.50mmol)和碳酸钾(100mmol),再加入120.00mL甲苯:乙醇:水=2:1:1混合液,氮气保护,升温到90℃回流过夜。反应完毕后,反应液降温到40-50℃,分去水层,用无水硫酸钠干燥有机层,旋干有机层得到固体有机物,使用少量的二氯甲烷将固体有机物完全溶解,然后缓慢滴加到石油醚溶液中,搅拌均匀,有沉淀析出,抽滤得固体,依次用无水乙醇、石油醚淋洗,烘干,获得中间体1(13.9g,产率:76.2%,MW:364.79)。
将中间体1(30mmol)加入到反应瓶中,再加入(33mmol)的碳酸钾,加入80.00ml的DMSO溶剂,氮气保护下,升温到160℃反应24h。将反应液降到室温,加入水搅拌,再加入乙酸乙酯萃取反应液,得到的萃取液再用水洗涤一次,无水硫酸镁干燥,旋干得到油状物,利用二氯甲烷和石油醚(v:v=10:4)的混合溶液,通过柱色谱法纯化剩余物质从而获得中间体2(6.9g,产率:66.9%,MW:344.81)。
氮气保护下,将中间体2(15mmol)和原料C(16.5mmol)溶于90.00mL甲苯溶液中,加入三(二亚苄基丙酮)二钯(0.15mmol),三叔丁基膦(0.75mmol)及叔丁醇钠(30mmol),搅拌均匀,升温至回流,反应5h;反应结束后,稍降温度,使用硅藻土进行过滤,除去盐以及催化剂,滤液冷却至室温后,水洗三遍,保留有机相,接着用乙酸乙酯萃取水相;合并有机相后,使用无水硫酸镁进行干燥,并且使用旋转式蒸发器去除溶剂;利用二氯甲烷和石油醚(v:v=10:4)的混合溶液,通过柱色谱法纯化剩余物质从而获得化合物HT-17(6.2g,产率:53.5%,Mw:774.09)。
HPLC纯度:>99.5%。
元素分析:
计算值为:C,88.45;H,6.12;N,5.43。
测试值为:C,88.51;H,6.27;N,5.50。
实施例3:化合物HT-81的合成
将原料A(55mmol)和原料B(50mmol)加入到三口反应瓶中,分别加入四(三苯基膦钯)(0.5mmol)和碳酸钾(100mmol),再加入120.00mL甲苯:乙醇:水=2:1:1混合液,氮气保护,升温到90℃回流过夜。反应完毕后,反应液降温到40-50℃,分去水层,用无水硫酸钠干燥有机层,旋干有机层得到固体有机物,使用少量的二氯甲烷将固体有机物完全溶解,然后缓慢滴加到石油醚溶液中,搅拌均匀,有沉淀析出,抽滤得固体,依次用无水乙醇、石油醚淋洗,烘干,获得中间体1(13.6g,产率:74.9%,MW:364.93)。
将中间体1(30mmol)加入到反应瓶中,再加入33mmol的碳酸钾,加入80.00mL的DMSO溶剂,氮气保护下,升温到160℃反应24h。将反应液降到室温,加入水搅拌,再加入乙酸乙酯萃取反应液,得到的萃取液再用水洗涤一次,无水硫酸镁干燥,旋干得到油状物,利用二氯甲烷和石油醚(v:v=10:4)的混合溶液,通过柱色谱法纯化剩余物质从而获得中间体2(7.0g,产率:68.3%,MW:344.85)。
将中间体2(15mmol)和原料C(16.5mmol)加入到反应瓶中,再分别加入Pd(oAc)2(0.75mmol)、碳酸铯(30mmol)、配体X-PHOS(1.20mmol),加入100.00mL乙二醇二甲醚(DME):水=2:1的混合溶液,氮气保护,升温回流反应16h。反应完毕后,反应液降温到40-50℃,分去水层,用无水硫酸钠干燥有机层,旋干有机层得到黑色状物,利用二氯甲烷和石油醚(v:v=10:4)的混合溶液,通过柱色谱法纯化剩余物质从而获得化合物HT-81(4.4g,产率:48.9%,Mw:617.85)。
HPLC纯度:>99.5%。
元素分析:
计算值为:C,87.49;H,5.71;N,6.80。
测试值为:C,87.55;H,5.83;N,6.86。
实施例4~30
参照实施例1~3的合成方法完成对如下化合物的合成,其分子式和质谱如下表1所示:
表1实施例4~30产物的结构及表征数据
另外,需要说明,本申请其他化合物参照上述所列举的实施例的合成方法即可获得,所以在此不再赘述。
进一步的,本发明还提供了一种有机电致发光器件,包括第一电极、与上述第一电极对置而具备的第二电极、以及具备在上述第一电极与第二电极之间的1层以上的有机物层,上述有机物层中的至少1层包含本发明制备的式I所示化合物。
本发明的有机发光器件可以具有包含空穴注入层、空穴传输层、电子阻挡层、发光辅助层、发光层、空穴阻挡层、电子传输层、电子注入层、盖帽层等作为有机物层的结构。但是,发光器件的结构并不限于此,可以包含数量更少或更多的有机层。
根据本申请说明书的一个实施方式,上述有机物层具有电子传输层,本申请制备的通式1所示化合物作为电子传输层材料。
在上述有机发光元件包含多个有机物层的情况下,上述有机物层可以由相同物质或不同物质形成。
关于上述通式1所表示的化合物,在制造发光器件时,可以利用真空蒸镀法,也可以利用溶液涂布法来形成有机物层。其中,所谓溶液涂布法是指,旋涂法、浸涂法、刮涂法、喷墨印刷法、丝网印刷法、喷雾法、辊涂法等,但并非仅限于此。
本申请的发光器件根据所使用的材料,可以为顶部发光型、底部发光型或双向发光型。
本申请所述的器件可以用于有机发光器件、有机太阳电池、电子纸、有机感光体或有机薄膜晶体管。
作为阳极物质,通常为了使空穴能够顺利地向有机物层注入,优选为功函数大的物质。作为本申请中可使用的阳极物质的具体例,有钒、铬、铜、锌、金等金属或它们的合金;氧化锌、氧化铟、氧化铟锡(ITO)、氧化铟锌(IZO)等金属氧化物;ZnO:A1或SnO2:Sb等金属与氧化物的组合;聚吡咯及聚苯胺等导电性高分子等。
空穴注入层优选为p掺杂的空穴注入层,p掺杂的空穴注入层意指掺杂有p掺杂剂的空穴注入层。p掺杂剂是能够赋予p型半导体特性的材料。p型半导体特性意指在HOMO能级下注入空穴或传输空穴的特性,即具有高空穴传导率的材料的特性。
空穴传输材料是能够接收来自阳极或空穴注入层的空穴并将空穴传输至发光层的材料,并且具有高空穴迁移率的材料。空穴传输材料,可以选自芳基胺系衍生物、导电性高分子、以及同时存在共轭部分和非共轭部分的嵌段共聚物等。
空穴输送层和发光层之间加入发光辅助层(多层空穴输送层)。发光辅助层主要起到辅助空穴传输层的作用,因此有时也称为第二空穴传输层。发光辅助层使得从阳极转移的空穴能够平稳地移动到发光层,并且可以阻挡从阴极转移的电子,以将电子限制在发光层内,减少空穴传输层与发光层之间的势垒,降低有机电致发光器件的驱动电压,进一步增加空穴的利用率,从而改善器件的发光效率和寿命。
发光层的发光物质,是能够分别接收来自空穴传输层和电子传输层的空穴和电子并使其结合而发出可见光区域的光的物质,优选为对于荧光或磷光的量子效率高的物质。
发光层可以包含主体材料和掺杂剂材料。
主体材料和掺杂材料的质量比为90-99.5:0.5-10。
主体材料有芳香族稠环衍生物或含杂环化合物等。具体而言,作为芳香族稠环衍生物,有蒽衍生物、芘衍生物、萘衍生物、并五苯衍生物、菲化合物、荧蒽化合物等,作为含杂环化合物,有咔唑衍生物、二苯并呋喃衍生物、嘧啶衍生物等。
本申请掺杂剂材料包括荧光掺杂和磷光掺杂。可以选自芳香族胺衍生物、苯乙烯基胺化合物、硼配合物、荧蒽化合物、金属配合物等。
电子传输层可以起到促进电子传输的作用。电子传输材料是有利地接收来自阴极的电子并将电子传输至发光层的材料,优选具有高电子迁移率的材料。电子传输层可以包括电子缓冲层、空穴阻挡层、电子传输层和电子注入层中的至少一个,并且优选电子传输层和电子注入层中的至少一个。本申请电子传输层材料为通式1所示化合物。
电子注入层可以起到促进电子注入的作用。具有传输电子的能力,防止发光层中产生的激子迁移至空穴注入层。电子注入层的材料包括噁唑、噁二唑、三唑、咪唑、苝四羧酸、亚芴基甲烷、蒽酮以及它们的衍生物、镁、钙、钠、钾、钛、铟、钇、锂、钆、铝、银、锡、镱等金属或它们的合金,金属配合物或含氮5元环衍生物等,但并不限于此。
阴极通常优选具有小功函数的材料使得电子顺利注入有机材料层,该层的层厚度优选在0.5和5nm之间。阴极物质,通常为了使电子容易地向有机物层注入,优选为功函数小的物质。作为阴极物质的具体例,有镁、钙、钠、钾、钛、铟、钇、锂、钆、铝、银、锡及铅等金属或它们的合金:LiF/Al或LiO2/Al,Mg/Ag等多层结构物质等。
除本申请所公开的电子传输层中包含通式1,OLED器件中对于其他层材料并无特殊限制。可以使用现有的空穴注入材料、空穴输送材料、空穴传输辅助材料,掺杂剂材料、空穴阻挡层材料、电子传输层材料和电子注入材料。
以下结合具体实施例对本申请提供的一种有机电致发光组合物和有机电致发光器件进行具体说明。
器件实施例1有机电致发光器件的制备
a、ITO阳极:将涂层厚度为150nm的ITO(氧化铟锡)-Ag-ITO(氧化铟锡)玻璃基板在蒸馏水中清洗2次,超声波洗涤30min,再用蒸馏水反复清洗2次,超声波洗涤10min,洗涤结束后,然后转移至等甩干机内进行甩干,最后用真空烘箱220℃烘烤2小时,烘烤结束后降温即可使用。以该基板为阳极,使用蒸镀机进行蒸镀器件工艺,在其上依次蒸镀其它功能层。
e、EML(发光层):然后在上述发光辅助层上,以的蒸镀速率,真空蒸镀厚度为25nm的主体材料(Host)和掺杂材料(Dopant)作为发光层,其Host和Dopant的化学式如下所示。其中Host和Dopant的蒸镀速率比为97:3。
k、将蒸镀完成的基板进行封装。首先采用涂胶设备将清洗后盖板用UV胶进行涂覆工艺,然后将涂覆完成的盖板移至压合工段,将蒸镀完成的基板置于盖板上端,最后将基板和盖板在贴合设备作用下进行贴合,同时完成对UV胶光照固化。
器件结构:
ITO/Ag/ITO/HT:P-dopant(10nm,2%)/HT(120nm)/prime(10nm)/Host:Dopant(25nm,3%)/HB(5nm)/ET:Liq(35nm,50%)/Yb(1nm)/Mg:Ag(18nm,1:9)/CPL(70nm)。
所述有机电致发光器件制备过程中使用的化合物结构如下所示:
器件实施例2~30
按照上述有机电致发光器件的制备方法制备器件实施例2-30的有机电致发光器件,区别在于将器件实施例1中的化合物HT-1分别替换为化合物HT-3,HT-5,HT-8,HT-10,HT-12,HT-13,HT-17,HT-20,HT-21,HT-26,HT-28,HT-33,HT-36,HT-38,HT-41,HT-43,HT-46,HT-49,HT-52,HT-55,HT-58,HT-61,HT-65,HT-66,HT-69,HT-71,HT-76,HT-81,HT-88,制成器件实施例2~30。
为了进一步证明本发明的有益效果以更好地理解本发明,下面通过以下对比实施例进一步阐明本发明所述三嗪类电子传输材料及包含其的器件具有的性质及应用性能,但不可理解为对本发明的限定,对于本领域的技术人员根据上述发明内容所作的其他测定实验得到的产品性质及根据上述性质进行的应用,也视为落在本发明的保护范围内。
对比例1
按照上述有机电致发光器件的制备方法制备有机电致发光器件,区别在于将器件实施例1中的化合物HT-1替换为对比化合物1,其中对比化合物1的结构式如下:
器件对比例2
按照上述有机电致发光器件的制备方法制备有机电致发光器件,区别在于将器件实施例1中的化合物HT-1替换为对比化合物2,其中对比化合物2的结构式如下:
在1000(nits)亮度下对器件实施例2~30以及对比例1~2得到的机电致发光器件的驱动电压、发光效率、BI值以及寿命进行表征,测试结果如下表2。
表2有机电致发光器件的发光特性测试结果(亮度值为1000nits)
由表2可知,使用本申请提供的电子传输材料制备的有机电致发光器件实施例2~30与器件对比例1~2提供的现有的有机电致发光器件相比较而言,在驱动电压,发光效率、BI和寿命得到提高。
对所公开的实施例的上述说明,使本领域专业技术人员能够实现或使用本发明。对这些实施例的多种修改对本领域的专业技术人员来说将是显而易见的,本文中所定义的一般原理可以在不脱离本发明的精神或范围的情况下,在其它实施例中实现。因此,本发明将不会被限制于本文所示的这些实施例,而是要符合与本文所公开的原理和新颖特点相一致的最宽的范围。
Claims (7)
1.一种三嗪类电子传输材料,其特征在于,具有如下结构通式:
其中,
X、Y分别独立选自C-R4/R5、N-R6、O或S;
m、n分别选自0或1的整数,且m和n不同时为0;
L1、L2表示为连接键、经取代或未经取代的C6-C30亚芳基、经取代或未经取代的3元-20元亚杂芳基,其杂原子选自氧、氮或硫;
环A表示取代或未经取代的C3-C30环烷基、取代或未经取代的3元-30元杂环烷基,其杂原子选自氧、氮或硫;经取代或未经取代的C6-C30芳基、经取代或未经取代的3元-20元杂芳基,其杂原子选自氧、氮或硫;经取代或未经取代的3元-25元杂芳基胺基,其杂原子选自氧、氮或硫;经取代或未经取代的C6~C60芳基胺基;
R1、R2、R3各自独立地为氢、氘、卤素、氰基、羧基、硝基、羟基、氨基、磺酸基、磺酰基、磷酸基、磷酰基、硅基或硼烷基;取代或未经取代的C1-C30烷基、取代或未经取代的C2-C30烯基、取代或未经取代的C2-C30炔基、取代或未经取代的C3-C30环烷基、取代或未经取代的3元-30元杂环烷基,其杂原子选自氧、氮或硫;经取代或未经取代的C6-C30芳基、经取代或未经取代的3元-20元杂芳基,其杂原子选自氧、氮或硫;经取代或未经取代的3元-25元杂芳基胺基,其杂原子选自氧、氮或硫;经取代或未经取代的C6~C60芳基胺基、经取代或未经取代的C1-C30烷氧基、经取代或未经取代的C6-C60芳氧基;
R4~R6各自独立地表示经取代或未经取代的C1-C30烷基、经取代或未经取代C6-C30芳基、经取代或未经取代的3元-30元杂芳基,其杂原子选自氧、氮或硫;或与相邻取代基连接形成单环或多环C3-C30脂环族环或C3-C30芳香族环,其碳原子可置换为至少一个选自氮、氧或硫的杂原子;
Ar1-Ar4各自独立地表示经取代或未经取代的C1-C30烷基、取代或未经取代的C3-C30环烷基、取代或未经取代的3元-20元杂环烷基,其杂原子选自氧、氮或硫;经取代或未经取代的C6-C30芳基或经取代或未经取代的3元-30元杂芳基,其杂原子选自氧、氮或硫;经取代或未经取代的3元-15元杂芳基胺基,其杂原子选自氧、氮或硫;经取代或未经取代的C6~C60芳基胺基。
2.根据权利要求1所述的三嗪类电子传输材料,其特征在于,所述L1、L2表示为连接键、经取代或未经取代的C6-C20亚芳基、经取代或未经取代的3元-18元亚杂芳基,其杂原子选自氧、氮或硫;
环A表示经取代或未经取代的C6-C30芳基、经取代或未经取代的3元-20元杂芳基,其杂原子选自氧、氮或硫;
R1、R2、R3彼此相同或不同,并且各自独立地为氢、氘、卤素、氰基;取代或未经取代的C1-C10烷基、取代或未经取代的C3-C10环烷基、取代或未经取代的3元-10元杂环烷基,其杂原子选自氧、氮或硫;经取代或未经取代的C6-C20芳基、经取代或未经取代的3元-10元杂芳基,其杂原子选自氧、氮或硫;经取代或未经取代的3元-15元杂芳基胺基,其杂原子选自氧、氮或硫;经取代或未经取代的C6~C20芳基胺基;
Ar1-Ar4各自独立地表示取代或未经取代的C6-C20芳基、经取代或未经取代的3元-15元杂芳基,其杂原子选自氧、氮或硫;经取代或未经取代的3元-15元杂芳基胺基,其杂原子选自氧、氮或硫;经取代或未经取代的C6~C30芳基胺基。
4.一种如权利要求1~3任一项所述的三嗪类电子传输材料的制备方法,其特征在于,L为非连接键,包括如下反应步骤:
(1)将原料A(1.1eq)和原料B(1.0eq)加入到三口反应瓶中,分别加入四(三苯基膦钯)(0.01eq)和碳酸钾(2.0eq),再加入甲苯:乙醇:水=2:1:1混合液,氮气保护,升温到90℃回流过夜,反应完毕后,反应液降温到40-50℃,分去水层,用无水硫酸钠干燥有机层,旋干有机层得到固体有机物,使用少量的二氯甲烷将固体有机物完全溶解,然后缓慢滴加到石油醚溶液中,搅拌均匀,有沉淀析出,抽滤得固体,依次用无水乙醇、石油醚淋洗,烘干,获得中间体1;
(2)将中间体1(1.0eq)加入到反应瓶中,再加入(1.1eq)的碳酸钾,加入溶剂DMSO,氮气保护下,升温到160℃反应24小时。将反应液降到室温,加入水搅拌,再加入乙酸乙酯萃取反应液,得到的萃取液再用水洗涤一次,无水硫酸镁干燥,旋干得到油状物,利用二氯甲烷和石油醚(v:v=10:4)的混合溶液,通过柱色谱法纯化剩余物质从而获得中间体2;
(3)将中间体2(1.0eq)和原料C(1.1eq)加入到反应瓶中,再分别加入Pd(oAc)2(0.05eq)、碳酸铯(2.0eq)、配体X-PHOS(0.11eq),加入乙二醇二甲醚DME:水=2:1的混合溶液,氮气保护,升温回流反应16小时。处理过程:反应完毕后,反应液降温到40-50℃,分去水层,用无水硫酸钠干燥有机层,旋干有机层得到黑色状物,用二氯甲烷:石油醚=1:1过柱子,收集产品点,从而获得中间体3;
(4)将中间体3(1.0eq)和原料D(1.1eq)加入到反应瓶中,再分别加入Pd(oAc)2(0.05eq)、碳酸铯(2.0eq)、配体X-PHOS(0.11eq),加入乙二醇二甲醚DME:水=2:1的混合溶液,氮气保护,升温回流反应16小时。处理过程:反应完毕后,反应液降温到40-50℃,分去水层,用无水硫酸钠干燥有机层,旋干有机层得到黑色状物,利用二氯甲烷和石油醚(v:v=10:4)的混合溶液,通过柱色谱法纯化剩余物质从而获得通式1;且,
具体合成路线如反应式I所示:
式中A、X、Y、R1~R3、L1、L2、Ar1~Ar4具有权利要求1中所给定义。
5.一种如权利要求1~3任一项所述的三嗪类电子传输材料的制备方法,其特征在于,L为连接键,包括如下反应步骤:
(1)将原料A(1.1eq)和原料B(1.0eq)加入到三口反应瓶中,分别加入四(三苯基膦钯)(0.01eq)和碳酸钾(2.0eq),再加入甲苯:乙醇:水=2:1:1混合液,氮气保护,升温到90℃回流过夜,反应完毕后,反应液降温到40-50℃,分去水层,用无水硫酸钠干燥有机层,旋干有机层得到固体有机物,使用少量的二氯甲烷将固体有机物完全溶解,然后缓慢滴加到石油醚溶液中,搅拌均匀,有沉淀析出,抽滤得固体,依次用无水乙醇、石油醚淋洗,烘干,获得中间体1;
(2)将中间体1(1.0eq)加入到反应瓶中,再加入(1.1eq)的碳酸钾,加入溶剂DMSO,氮气保护下,升温到160℃反应24小时。将反应液降到室温,加入水搅拌,再加入乙酸乙酯萃取反应液,得到的萃取液再用水洗涤一次,无水硫酸镁干燥,旋干得到油状物,利用二氯甲烷和石油醚(v:v=10:4)的混合溶液,通过柱色谱法纯化剩余物质从而获得中间体2;
(3)氮气保护下,将中间体2(1.0eq)和原料C(1.1eq)溶于甲苯溶液中,加入三(二亚苄基丙酮)二钯(0.01eq),三叔丁基膦(0.05eq)及叔丁醇钠(2.0eq),搅拌均匀,升温至回流,反应5h;反应结束后,稍降温度,使用硅藻土进行过滤,除去盐以及催化剂,滤液冷却至室温后,水洗三遍,保留有机相,接着用乙酸乙酯萃取水相;合并有机相后,使用无水硫酸镁进行干燥,并且使用旋转式蒸发器去除溶剂;使用少量的二氯甲烷将固体有机物完全溶解,然后缓慢滴加到石油醚溶液中,搅拌均匀,有沉淀析出,抽滤得固体,依次用无水乙醇、石油醚淋洗,烘干,从而获得中间体3;
(4)氮气保护下,将中间体3(1.0eq)和原料D(1.1eq)溶于甲苯溶液中,加入三(二亚苄基丙酮)二钯(0.01eq),三叔丁基膦(0.05eq)及叔丁醇钠(2.0eq),搅拌均匀,升温至回流,反应5h;反应结束后,稍降温度,使用硅藻土进行过滤,除去盐以及催化剂,滤液冷却至室温后,水洗三遍,保留有机相,接着用乙酸乙酯萃取水相;合并有机相后,使用无水硫酸镁进行干燥,并且使用旋转式蒸发器去除溶剂;利用二氯甲烷和石油醚(v:v=10:4)的混合溶液,通过柱色谱法纯化剩余物质从而获得通式1;且,
具体合成路线如反应式II所示:
式中A、X、Y、R1~R3、L1、L2、Ar1~Ar4具有权利要求1中所给定义。
6.一种如权利要求1~3任一项所述的三嗪类电子传输材料的应用,其特征在于,所述三嗪类电子传输材料在制备有机发光器件、有机太阳电池、电子纸、有机感光体或有机薄膜晶体管中的应用。
7.一种有机电致发光器件,其特征在于,包括第一电极,第二电极,置于所述第一电极和所述第二电极之间的一个或多个有机物层;且,
所述有机物层至少包括空穴注入层、空穴传输层、电子阻挡层、发光辅助层、发光层、空穴阻挡层、电子传输层、电子注入层及盖帽层中的一种;且,
所述电子传输层或电子注入层包含一种或多种如权利要求1~3任一所述的三嗪类电子传输材料。
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