CN110256358B - 一种胺类衍生物及其有机电致发光器件 - Google Patents
一种胺类衍生物及其有机电致发光器件 Download PDFInfo
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- CN110256358B CN110256358B CN201910631205.2A CN201910631205A CN110256358B CN 110256358 B CN110256358 B CN 110256358B CN 201910631205 A CN201910631205 A CN 201910631205A CN 110256358 B CN110256358 B CN 110256358B
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- 239000010410 layer Substances 0.000 claims abstract description 129
- 238000000605 extraction Methods 0.000 claims abstract description 38
- 125000001424 substituent group Chemical group 0.000 claims abstract description 33
- 239000012044 organic layer Substances 0.000 claims abstract description 13
- 125000003118 aryl group Chemical group 0.000 claims description 54
- -1 ethylphenyl Chemical group 0.000 claims description 39
- 229910052757 nitrogen Inorganic materials 0.000 claims description 28
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 20
- 230000005525 hole transport Effects 0.000 claims description 16
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 13
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 13
- 235000010290 biphenyl Nutrition 0.000 claims description 10
- 125000006732 (C1-C15) alkyl group Chemical group 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
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- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 5
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000004957 naphthylene group Chemical group 0.000 claims description 5
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- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 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 claims description 4
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- ZYZCALPXKGUGJI-DDVDASKDSA-M (e,3r,5s)-7-[3-(4-fluorophenyl)-2-phenyl-5-propan-2-ylimidazol-4-yl]-3,5-dihydroxyhept-6-enoate Chemical compound C=1C=C(F)C=CC=1N1C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)=C(C(C)C)N=C1C1=CC=CC=C1 ZYZCALPXKGUGJI-DDVDASKDSA-M 0.000 description 7
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- WFOVEDJTASPCIR-UHFFFAOYSA-N 3-[(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)methylamino]-n-[[2-(trifluoromethyl)phenyl]methyl]benzamide Chemical compound N=1N=C(C=2C=CN=CC=2)N(C)C=1CNC(C=1)=CC=CC=1C(=O)NCC1=CC=CC=C1C(F)(F)F WFOVEDJTASPCIR-UHFFFAOYSA-N 0.000 description 7
- IJRKLHTZAIFUTB-UHFFFAOYSA-N 5-nitro-2-(2-phenylethylamino)benzoic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC=C1NCCC1=CC=CC=C1 IJRKLHTZAIFUTB-UHFFFAOYSA-N 0.000 description 7
- MXZNUGFCDVAXLG-CHWSQXEVSA-N [(2S)-1-[(2R)-3-methyl-2-(pyridine-4-carbonylamino)butanoyl]pyrrolidin-2-yl]boronic acid Chemical compound CC(C)[C@@H](NC(=O)c1ccncc1)C(=O)N1CCC[C@@H]1B(O)O MXZNUGFCDVAXLG-CHWSQXEVSA-N 0.000 description 7
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- 238000005401 electroluminescence Methods 0.000 description 6
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- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 6
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 6
- PKJBWOWQJHHAHG-UHFFFAOYSA-N 1-bromo-4-phenylbenzene Chemical group C1=CC(Br)=CC=C1C1=CC=CC=C1 PKJBWOWQJHHAHG-UHFFFAOYSA-N 0.000 description 5
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- PYRKKGOKRMZEIT-UHFFFAOYSA-N 2-[6-(2-cyclopropylethoxy)-9-(2-hydroxy-2-methylpropyl)-1h-phenanthro[9,10-d]imidazol-2-yl]-5-fluorobenzene-1,3-dicarbonitrile Chemical compound C1=C2C3=CC(CC(C)(O)C)=CC=C3C=3NC(C=4C(=CC(F)=CC=4C#N)C#N)=NC=3C2=CC=C1OCCC1CC1 PYRKKGOKRMZEIT-UHFFFAOYSA-N 0.000 description 5
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- ZJFKMIYGRJGWIB-UHFFFAOYSA-N n-[3-methyl-4-[2-methyl-4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound CC1=CC(N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)=CC=C1C(C(=C1)C)=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=CC=C1 ZJFKMIYGRJGWIB-UHFFFAOYSA-N 0.000 description 1
- ZTLUNQYQSIQSFK-UHFFFAOYSA-N n-[4-(4-aminophenyl)phenyl]naphthalen-1-amine Chemical compound C1=CC(N)=CC=C1C(C=C1)=CC=C1NC1=CC=CC2=CC=CC=C12 ZTLUNQYQSIQSFK-UHFFFAOYSA-N 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000000643 oven drying Methods 0.000 description 1
- 150000007978 oxazole derivatives Chemical class 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 125000002080 perylenyl group Chemical class C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 108091008695 photoreceptors Proteins 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 229920000078 poly(4-vinyltriphenylamine) Polymers 0.000 description 1
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
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- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920002620 polyvinyl fluoride Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 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
- 238000005036 potential barrier Methods 0.000 description 1
- 238000011085 pressure filtration Methods 0.000 description 1
- LYKXFSYCKWNWEZ-UHFFFAOYSA-N pyrazino[2,3-f][1,10]phenanthroline-2,3-dicarbonitrile Chemical compound N1=CC=CC2=C(N=C(C(C#N)=N3)C#N)C3=C(C=CC=N3)C3=C21 LYKXFSYCKWNWEZ-UHFFFAOYSA-N 0.000 description 1
- VLRICFVOGGIMKK-UHFFFAOYSA-N pyrazol-1-yloxyboronic acid Chemical compound OB(O)ON1C=CC=N1 VLRICFVOGGIMKK-UHFFFAOYSA-N 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- OWJJRQSAIMYXQJ-UHFFFAOYSA-N pyrene-1,6-diamine Chemical compound C1=C2C(N)=CC=C(C=C3)C2=C2C3=C(N)C=CC2=C1 OWJJRQSAIMYXQJ-UHFFFAOYSA-N 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000005548 pyrenylene group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000005551 pyridylene group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- DLJHXMRDIWMMGO-UHFFFAOYSA-N quinolin-8-ol;zinc Chemical compound [Zn].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 DLJHXMRDIWMMGO-UHFFFAOYSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- FOGKDYADEBOSPL-UHFFFAOYSA-M rubidium(1+);acetate Chemical compound [Rb+].CC([O-])=O FOGKDYADEBOSPL-UHFFFAOYSA-M 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000005361 soda-lime glass Substances 0.000 description 1
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- 239000011734 sodium Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000011775 sodium fluoride Substances 0.000 description 1
- 235000013024 sodium fluoride Nutrition 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000005649 substituted arylene group Chemical group 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- TXEYQDLBPFQVAA-UHFFFAOYSA-N tetrafluoromethane Chemical compound FC(F)(F)F TXEYQDLBPFQVAA-UHFFFAOYSA-N 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- GVIJJXMXTUZIOD-UHFFFAOYSA-N thianthrene Chemical group C1=CC=C2SC3=CC=CC=C3SC2=C1 GVIJJXMXTUZIOD-UHFFFAOYSA-N 0.000 description 1
- 125000004627 thianthrenyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3SC12)* 0.000 description 1
- 125000005730 thiophenylene group Chemical group 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 108010086502 tumor-derived adhesion factor Proteins 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 125000002948 undecyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 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
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
- HTPBWAPZAJWXKY-UHFFFAOYSA-N zinc;quinolin-8-ol Chemical compound [Zn+2].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-N 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
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Abstract
本发明公开了一种胺类衍生物及其有机电致发光器件,涉及有机光电材料技术领域。本发明所要解决的技术问题是,目前光取出材料热稳定性差以及有机电致发光器件使用寿命短的问题。本发明的胺类衍生物为桥连基团含有芴基或者螺芴基的二胺,并且N上的取代基团至少含有一个苯并恶唑基、苯并噻唑基或者苯并咪唑基。本发明的有机电致发光器件,包括阳极、有机物层、阴极和光取出层,有机物层位于阳极和阴极之间,光取出层含有本发明式I的胺类衍生物。本发明的胺类衍生物的玻璃转化温度较高,具有较好的热稳定性,将其用作有机电致发光器件的光取出材料时,有机电致发光器件表现出较长的使用寿命。
Description
技术领域
本发明涉及有机光电材料技术领域,具体涉及一种胺类衍生物及其有机电致发光器件。
背景技术
有机电致发光就是指有机材料在电流或电场的激发作用下发光的现象。由于它在应用上的重要性,电致发光现象的研究和探索一直都是令人极感兴趣的一门科学,电致发光曾经被誉为是一种可以产生“冷光”的现象。根据所使用有机电致发光材料的不同,人们将利用有机小分子为发光材料制成的器件称为有机电致发光器件,简称OLED;而将利用高分子作为电致发光材料制成的器件称为高分子电致发光器件,简称PLED。但通常将两者笼统地称为有机电致发光器件,也简称为OLED。
有机电致发光比起发展较早的无机电致发光而言,具有材料选择范围宽、可实现由蓝光区到红光区的全彩色显示、驱动电压低、发光亮度和发光效率高、视角宽、响应速度快、制作过程相对简单、费用低,并可实现柔性显示等诸多优点,有机电致发光器件被普遍认为将是下一代显示器件的主流。
有机电致发光器件多采用夹层式的三明治结构,即有机功能层被夹在器件两侧的阳极和阴极之间,通常采用具有较高功函数的金属或者金属氧化物作为阳极,具有较低功函数的金属作为阴极。在器件两端施加一定的电压后,从阳极和阴极产生的空穴和电子分别沿材料的HOMO能级和LUMO能级向对方移动。当两者在发光层相遇时,会形成紧密结合的空穴电子对,即激子。由于激子并不稳定,会向低能级跃迁,回到稳定状态。在跃迁过程中,一部分能量变为热能散失掉,而另一部分则以光能的形式散发出去。
根据有机电致发光器件中有机功能层数的多少,器件结构大致可以分为单层、双层、三层和多层四种。根据光传出的路径不同,器件又分为顶发射器件和底发射器件两类。有机电致发光从最初的单层器件发展到今天,出现了各种复杂的器件结构,发光性能也有了质的飞跃。
底发射器件的光从阳极经过衬底传播到器件外部,顶发射器件的光通过阴极传播到器件外部。无论是底发射器件还是顶发射器件,对于出光侧的电极都要求具有较高的透过率和良好的载流子注入特性。底发射器件光从阳极传出,一般选用透过率极佳的ITO作为阳极材料。顶发射器件的光从阴极传出,要求阴极既具有较高的透过率,其功函数又要满足电子注入特性,目前常用的阴极材料通常是金属复合膜,一般由一种吸收较少的金属,例如Ag等,搭配一种功函数较低的金属,例如Mg、Al等。
顶发射器件的概念从提出至今,无论是理论还是工艺都在飞速发展,顶发射器件以其宽色域、高亮度迅速打入商业市场。顶发射器件由于复合金属阴极的存在,导致器件受到等离子损耗和波导模式的影响,其外部光耦合效率受到较大的损失,通常的改进方法是在阴极的表面沉积一层光取出层来进一步提高器件的发光效率,但是目前所使用的光取出材料的热稳定性大多较差,导致器件的使用寿命较短,因此如何提高光取出材料的热稳定性来获得寿命更高的有机电致发光器件成为了目前研究者重点关注的问题之一。
发明内容
为了解决目前光取出材料热稳定性差以及有机电致发光器件使用寿命短的问题,本发明提供了一种胺类衍生物及其有机电致发光器件。
本发明通过使用下述式I所示的胺类衍生物作为有机电致发光器件的光取出材料,可以实现上述目的,从而完成了本发明。
本发明提供了一种胺类衍生物,所述胺类衍生物由式I表示,
其中,所述Ar1、Ar2独立的选自取代或未取代的C6~C30的芳基、取代或未取代的C3~C30的杂芳基中的一种,并且Ar1、Ar2中的至少一个选自式II所示的基团,
所述L1选自单键、取代或未取代的C6~C18的亚芳基、取代或未取代的C3~C18的亚杂芳基中的一种;所述a选自0~4中的整数,所述R1选自取代或未取代的C1~C15的烷基、取代或未取代的C6~C18的芳基中的一种,当a大于1时,每个R1相同或者不同,所述X选自O、S或者N(Rx),所述Rx选自取代或未取代的C1~C15的烷基、取代或未取代的C6~C18的芳基中的一种;
所述Ar3、Ar4独立的选自取代或未取代的C6~C30的芳基、取代或未取代的C3~C30的杂芳基中的一种;
所述L选自如下所示基团中的一种,
所述R选自氢、取代或未取代的C1~C15的烷基、取代或未取代的C6~C18的芳基、取代或未取代的C3~C18的杂芳基中的一种;
所述L11、L12独立的选自单键、取代或未取代的C6~C18的亚芳基、取代或未取代的C3~C18的亚杂芳基中的一种。
另外,本发明还提供了一种有机电致发光器件,包括阳极、有机物层、阴极和光取出层,所述有机物层位于阳极和阴极之间,所述有机物层包含空穴传输层、发光层、电子传输层,所述空穴传输层位于阳极和发光层之间,所述电子传输层位于发光层和阴极之间,所述光取出层位于阴极远离阳极的一侧,所述光取出层含有上述本发明式I所示的胺类衍生物。
有益效果:本发明的胺类衍生物的玻璃转化温度较高,具有较好的热稳定性,因此本发明的胺类衍生物是一种更加稳定的光学材料,将其用作有机电致发光器件的光取出材料时,有机电致发光器件表现出较长的使用寿命。
另外本发明的胺类衍生物对光的折射率较高,当其用作有机电致发光器件的光取出层时,能够减弱表面等离子损耗以及波导模式带来的不利影响,增加了光学耦合输出效率,从而使有机电致发光器件的发光效率得到了有效的提高。
附图说明
图1为本发明的化合物1的1H NMR图;图2为本发明的化合物22的1H NMR图;
图3为本发明的化合物26的1H NMR图;图4为本发明的化合物35的1H NMR图;
图5为本发明的化合物41的1H NMR图;图6为本发明的化合物73的1H NMR图;
图7为本发明的化合物101的1H NMR图;图8为本发明的化合物121的1H NMR图;
图9为本发明的化合物143的1H NMR图;图10为本发明的化合物146的1H NMR图;
图11为本发明的化合物1的DSC曲线图;图12为本发明的化合物22的DSC曲线图;
图13为本发明的化合物26的DSC曲线图;图14为本发明的化合物35的DSC曲线图;
图15为本发明的化合物41的DSC曲线图;图16为本发明的化合物73的DSC曲线图;
图17为本发明的化合物101的DSC曲线图;图18为本发明的化合物121的DSC曲线图;
图19为本发明的化合物143的DSC曲线图;图20为本发明的化合物146的DSC曲线图。
具体实施方式
下面结合具体实施例,进一步阐明本发明,应理解这些实施例仅用于说明本发明而不用于限制本发明的范围,在阅读了本发明之后,本领域技术人员对本发明的各种等价形式的修改均落于本申请所要求保护的范围内。
本发明所述的“取代或未取代的C6~C30的芳基”中的“C6~C30”是指未取代的芳基中含有的碳原子数,取代基的碳原子数不包括在内;“取代或未取代的C3~C30的杂芳基”中的“C3~C30”是指未取代的杂芳基中含有的碳原子数,取代基的碳原子数不包括在内;“取代或未取代的C6~C18的亚芳基”中的“C6~C18”是指未取代的亚芳基中含有的碳原子数,取代基的碳原子数不包括在内;“取代或未取代的C3~C18的亚杂芳基”中的“C3~C18”是指未取代的亚杂芳基中含有的碳原子数,取代基的碳原子数不包括在内;“取代或未取代的C1~C15的烷基”中的“C1~C15”是指未取代的烷基中含有的碳原子数,取代基的碳原子数不包括在内。以此类推。
本发明所述的丙基、丁基、戊基等碳原子数大于二的链状烷基包括它们的异构体,如异丙基,异丁基、仲丁基、叔丁基,异戊基、新戊基、叔戊基等,但不限于此。
本发明所述的烷基是指烷烃分子中少掉一个氢原子而成的烃基,其可以为直链烷基、支链烷基或者环烷基。所述直链烷基包括甲基、乙基、正丙基、正丁基、正戊基、正己基、正庚基、正辛基、正壬基、正癸基、十一烷基、十二烷基等,但不限于此;所述支链烷基包括异丙基、异丁基、仲丁基、叔丁基、正戊基的异构基团、正己基的异构基团、正庚基的异构基团、正辛基的异构基团、正壬基的异构基团、正癸基的异构基团等,但不限于此;所述环烷基包括环丙基、环丁基、环戊基、环己基等,但不限于此。上述烷基优选为甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基和叔丁基。
本发明所述的芳基是指芳香族化合物分子的芳核碳上去掉一个氢原子后,剩下一价基团的总称,其可以为单环芳基、多环芳基或者稠环芳基。所述单环芳基是指分子中只有一个芳香环的芳基,例如,苯基等,但不限于此;所述多环芳基是指分子中含有两个或者两个以上独立芳香环的芳基,例如,联苯基、三联苯基等,但不限于此;所述稠环芳基是指分子中含有两个或者多个芳香环且彼此间通过共用两个相邻碳原子稠合而成的芳基,例如,萘基、蒽基、菲基、芴基、苯并芴基、芘基、三亚苯基、荧蒽基、螺二芴基等,但不限于此。上述芳基优选为苯基、联苯基、三联苯基、萘基、菲基、芴基、苯并芴基、三亚苯基、螺二芴基。
本发明所述的杂芳基是指芳基中的一个或多个芳核碳原子被杂原子替代得到的基团的总称,所述杂原子包括但不限于氧、硫、氮或者磷原子,所述杂芳基的连接位点可以位于成环碳原子上,也可以位于成环氮原子上,所述杂芳基可以为单环杂芳基、多环杂芳基或者稠环杂芳基。所述单环杂芳基包括吡啶基、嘧啶基、三嗪基、呋喃基、噻吩基、吡咯基、咪唑基等,但不限于此;所述多环杂芳基包括联吡啶基、联嘧啶基、苯基吡啶基等,但不限于此;所述稠环杂芳基包括喹啉基、异喹啉基、吲哚基、邻菲罗啉基、二苯并呋喃基、苯并二苯并呋喃基、二苯并噻吩基、苯并二苯并噻吩基、咔唑基、苯并咔唑基、吖啶基、9,10-二氢吖啶基、吩恶嗪、氧杂蒽基、硫杂蒽基等,但不限于此。上述杂芳基优选为呋喃基、噻吩基、二苯并呋喃基、苯并二苯并呋喃基、二苯并噻吩基、苯并二苯并噻吩基、咔唑基、苯并咔唑基、吖啶基、9,10-二氢吖啶基、吩恶嗪基、氧杂蒽基、硫杂蒽。
本发明所述的亚芳基是指取代或未取代的芳香族化合物分子的芳核碳上去掉两个氢原子后,剩下二价基团的总称,其可以为单环亚芳基、多环亚芳基或者稠环亚芳基。所述单环亚芳基包括亚苯基等,但不限于此;所述多环亚芳基包括亚联苯基、亚三联苯基等,但不限于此;所述稠环亚芳基包括亚萘基、亚蒽基、亚菲基、亚芴基、亚芘基、亚三亚苯基、亚荧蒽基、亚苯基芴基等,但不限于此。上述亚芳基优选为亚苯基、亚联苯基、亚三联苯基、亚萘基、亚芴基、亚苯基芴基。
本发明所述的亚杂芳基是指亚芳基中的一个或多个芳核碳被杂原子替代得到的基团的总称,所述杂原子包括但不限于氧、硫、氮或者磷原子,所述亚杂芳基可以为单环亚杂芳基、多环亚杂芳基或者稠环亚杂芳基。所述单环亚杂芳基包括亚吡啶基、亚嘧啶基、亚呋喃基、亚噻吩基等,但不限于此;所述多环亚杂芳基包括亚联吡啶基、亚联嘧啶基、亚苯基吡啶基等,但不限于此;所述稠环亚杂芳基包括亚喹啉基、亚异喹啉基、亚邻菲罗啉基、亚二苯并呋喃基、亚二苯并噻吩基、亚咔唑基等,但不限于此。上述亚杂芳基优选为亚邻菲罗啉基、亚二苯并呋喃基、亚二苯并噻吩基。
本发明所述的取代的烷基是指烷基上的氢被取代基团替代得到的基团的总称,所述取代基团可以为单个或者多个,当取代基团为多个取代基团时,所述多个取代基团可以相同或者不同,所述取代基团包括氘、卤素、氰基、硝基、羟基、羰基、取代或未取代的C6~C30的芳基、取代或未取代的C3~C30的杂芳基,所述芳基、杂芳基如上述定义。
本发明所述的取代的芳基是指芳基上的氢被取代基团替代得到的基团的总称,所述取代基团可以为单个或者多个,当取代基团为多个取代基团时,所述多个取代基团可以相同或者不同,所述取代基团包括氘、卤素、氰基、硝基、羟基、羰基、取代或未取代的C1~C15的烷基、取代或未取代的C6~C30的芳基、取代或未取代的C3~C30的杂芳基,所述烷基、芳基、杂芳基如上述定义。
本发明所述的取代的杂芳基是指杂芳基上的氢被取代基团替代得到的基团的总称,所述取代基团可以为单个或者多个,当取代基团为多个取代基团时,所述多个取代基团可以相同或者不同,所述取代基团包括氘、卤素、氰基、硝基、羟基、羰基、取代或未取代的C1~C15的烷基、取代或未取代的C6~C30的芳基、取代或未取代的C3~C30的杂芳基,所述烷基、芳基、杂芳基如上述定义。
本发明所述的取代的亚芳基是指亚芳基上的氢被取代基团替代得到的基团的总称,所述取代基团可以为单个或者多个,当取代基团为多个取代基团时,所述多个取代基团可以相同或者不同,所述取代基团包括氘、卤素、氰基、硝基、羟基、羰基、取代或未取代的C1~C15的烷基、取代或未取代的C6~C30的芳基、取代或未取代的C3~C30的杂芳基,所述烷基、芳基、杂芳基如上述定义。
本发明所述的取代的亚杂芳基是指亚杂芳基上的氢被取代基团替代得到的基团的总称,所述取代基团可以为单个或者多个,当取代基团为多个取代基团时,所述多个取代基团可以相同或者不同,所述取代基团包括氘、卤素、氰基、硝基、羟基、羰基、取代或未取代的C1~C15的烷基、取代或未取代的C6~C30的芳基、取代或未取代的C3~C30的杂芳基,所述烷基、芳基、杂芳基如上述定义。
本发明提供了一种胺类衍生物,所述胺类衍生物由式I表示,
其中,所述Ar1、Ar2独立的选自取代或未取代的C6~C30的芳基、取代或未取代的C3~C30的杂芳基中的一种,并且Ar1、Ar2中的至少一个选自式II所示的基团,
所述L1选自单键、取代或未取代的C6~C18的亚芳基、取代或未取代的C3~C18的亚杂芳基中的一种;所述a选自0~4中的整数,所述R1选自取代或未取代的C1~C15的烷基、取代或未取代的C6~C18的芳基中的一种,当a大于1时,每个R1相同或者不同,所述X选自O、S或者N(Rx),所述Rx选自取代或未取代的C1~C15的烷基、取代或未取代的C6~C18的芳基中的一种;
所述Ar3、Ar4独立的选自取代或未取代的C6~C30的芳基、取代或未取代的C3~C30的杂芳基中的一种;
所述L选自如下所示基团中的一种,
所述R选自氢、取代或未取代的C1~C15的烷基、取代或未取代的C6~C18的芳基、取代或未取代的C3~C18的杂芳基中的一种;
所述L11、L12独立的选自单键、取代或未取代的C6~C18的亚芳基、取代或未取代的C3~C18的亚杂芳基中的一种。
优选的,所述式II选自如下所示基团中的一种,
其中,所述b选自0~4中的整数,所述R2选自取代或未取代的C1~C10的烷基、取代或未取代的C6~C18的芳基中的一种,当b大于1时,每个R2相同或者不同;
所述c选自0~4中的整数,所述R3选自取代或未取代的C1~C10的烷基、取代或未取代的C6~C18的芳基中的一种,当c大于1时,每个R3相同或者不同。
优选的,所述胺类衍生物如式I-1所示,
所述Ar2选自取代或未取代的C6~C30的芳基、取代或未取代的C3~C30的杂芳基中的一种,并且Ar2不为式II;
所述Ar3、Ar4独立的选自取代或未取代的C6~C30的芳基、取代或未取代的C3~C30的杂芳基中的一种。
优选的,所述Ar2、Ar4选自相同的取代基。
优选的,所述胺类衍生物如式I-2所示,
所述Ar3、Ar4独立的选自取代或未取代的C6~C30的芳基、取代或未取代的C3~C30的杂芳基中的一种。
优选的,所述Ar3、Ar4独立的选自如下所示基团中的一种,
其中,所述d选自0~5的整数,所述R4选自取代或未取代的C1~C10的烷基,当d大于1时,每个R4相同或者不同;
所述e选自0~4的整数,所述R5选自取代或未取代的C1~C10的烷基、取代或未取代的C6~C18的芳基中的一种,当e大于1时,每个R5相同或者不同;
所述f选自0~4的整数,所述R6选自取代或未取代的C1~C10的烷基、取代或未取代的C6~C18的芳基中的一种,当f大于1时,每个R6相同或者不同;
所述g选自0~5的整数,所述R7选自取代或未取代的C1~C10的烷基、取代或未取代的C6~C18的芳基中的一种,当g大于1时,每个R7相同或者不同;
所述R0选自取代或未取代的C1~C10的烷基、取代或未取代的C6~C18的芳基中的一种;
所述L2选自单键、取代或未取代的C6~C18的亚芳基、取代或未取代的C3~C18的亚杂芳基中的一种。
优选的,所述Ar3、Ar4独立的选自如下所示基团中的一种,
其中,所述R4选自甲基、乙基、丙基、丁基、戊基、己基、庚基、辛基中的一种,并且每个R4相同或者不同;
所述R5选自甲基、乙基、丙基、丁基中的一种,并且每个R5相同或者不同;
所述R7选自甲基、乙基、丙基、丁基、苯基、甲苯基、乙苯基中的一种,并且每个R7相同或者不同。
优选的,所述式II选自如下所示基团中的一种,
其中,所述R1选自甲基、乙基、丙基、丁基、戊基、己基、庚基、辛基中的一种,并且每个R1相同或者不同;
所述R2选自甲基、乙基、丙基、丁基中的一种,并且每个R2相同或者不同;
所述R3选自甲基、乙基、丙基、丁基中的一种。
进一步的,所述胺类衍生物选自如下所示结构中的一种,
以上列举了本发明所述的式I所示的胺类衍生物的一些具体化学结构,但本发明并不局限于所列的这些化学结构,凡是以式I所示结构为基础,取代基为如上所限定的基团都应包含在内。
本发明的有机电致发光器件,包括阳极、有机物层、阴极和光取出层,所述有机物层位于阳极和阴极之间,所述光取出层位于阴极远离阳极的一侧。
本发明的有机电致发光器件的光取出层可以具有单层结构,或者具有两层以上的多层结构,本发明的光取出层包含本发明的胺类衍生物,所述胺类衍生物的含量没有特殊限制,可以根据需要适当调整。本发明的有机电致发光器件的有机物层可以包含空穴注入层、空穴传输层、电子阻挡层、发光层、空穴阻挡层、电子传输层、电子注入层或者置于阳极和空穴注入层之间的缓冲层中的任意一层或者任意多层。各层的膜厚没有特别限制,一般而言如果膜厚太薄,则薄膜容易产生针孔等缺陷,如果膜厚太厚则会导致有机电致发光器件的驱动电压升高、发光效率降低,因此膜厚优选为0.1nm~10μm,更优选为0.5nm~0.5μm。
本发明的有机电致发光器件的器件结构优选为:
基板/阳极/空穴传输层/发光层/电子传输层/金属阴极/光取出层;或者,
基板/阳极/空穴传输层/发光层/电子传输层/电子注入层/金属阴极/光取出层;或者,
基板/阳极/空穴传输层/发光层/空穴阻挡层/电子传输层/金属阴极/光取出层;或者,
基板/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/金属阴极/光取出层;或者,
基板/阳极/空穴注入层/空穴传输层/发光层/空穴阻挡层/电子传输层/电子注入层/金属阴极/光取出层。
本发明的有机电致发光器件可以使用已知材料通过已知方法制备,然而,有机电致发光器件的结构不限于此。
本发明所述的基板优选玻璃板、石英板、聚合物板等,但不限于此。所述玻璃包括钠钙玻璃、铅玻璃、铝硅酸盐玻璃、硼硅酸盐玻璃、钡硼硅酸盐玻璃等。所述聚合物包括聚碳酸酯、聚芳酯、聚醚砜、聚丙烯、聚氟乙烯、聚氯乙烯等。
本发明所述的阳极具有将空穴注入到空穴传输层中的功能,阳极材料需要具有较高的功函数,一般而言功函数在4.5eV以上的材料是有效的。由于本发明的有机电致发光器件为顶发射器件,因此又需要阳极材料要在可见光的范围内具有较高的反射率以及较低的吸收率。本发明的阳极材料可以选择如下所述材料中的一种或者多种,金属氧化物、金属、金属合金、聚合物等。具体为,氧化铟锡(简称:ITO)、氧化铟锌(简称:IZO)、氧化铝锌(简称:AZO)、氧化铟、氧化锌、Ag、Au、Al、Cu、Ni、Mo、Ti、Zn、Pd、Pt、聚吡咯等,但不限于此。阳极的膜厚根据材料而有所不同,通常选择10nm~1μm,优选10nm~200nm的范围。本发明的阳极可以是单层结构,也可以是两层以上的多层结构,每一层所包含的阳极材料可以是单一材料,也可以是混合材料。
本发明的缓冲层是指在阳极上蒸镀一层非常薄的绝缘物质层,可以改进空穴注入效率、降低驱动电压。所述缓冲层具体可以选择如下材料,二氧化硅、四氟化碳、氟化锂等,但不限于此。
本发明的空穴注入层具有降低有机电致发光器件中空穴传输层与阳极界面的势垒,提高空穴注入效率,延长器件寿命的功能。本发明的空穴注入材料优选具有较好的空穴注入性能的材料,可以选择如下材料中的一种或者多种,钼氧化物、银氧化物、钒氧化物、钨氧化物、钌氧化物、镍氧化物、铜氧化物、钛氧化物、铝氧化物等金属氧化物,酞菁类化合物、芳香族胺类衍生物、含有多氰基的共轭有机材料等低分子有机化合物,聚合物等,但不限于此。具体为,三氧化钼、氧化银、五氧化二钒、三氧化钨、氧化钌、氧化镍、氧化铜、二氧化钛、三氧化二铝,酞菁铜(II)(简称:CuPc)、氧钛酞菁(简称:TiOPC)、N,N'-二(N,N'-二苯基-4-氨基苯基)-N,N'-二苯基-4,4'-二氨基-1,1'-联苯、N4,N4,N4',N4'-四([1,1'-联苯]-4-基)-[1,1'-联苯]-4,4'-二胺、4,4'4"-三(N,N-二苯基氨基)三苯基胺(简称:NATA)、4,4',4”-三(N-(萘-1-基)-N-苯基-氨基)三苯胺(简称:1T-NATA)、4,4',4”-三[2-萘基苯基氨基]三苯基胺(简称:2T-NATA)、4,4',4”-三(N-3-甲基苯基-N-苯基氨基)三苯胺(简称:m-MTDATA)、N4,N4,N4',N4'-四(4-甲氧基苯基)-[1,1'-联苯]-4,4'-二胺(简称:MeO-TPD)、2,7-二[N,N-二(4-甲氧基苯基)氨]-9,9-螺二[9H-芴](简称:MeO-Spiro-TPD)、N,N'-二[4-二(间甲苯基)氨基苯基]-N,N'-二苯基联苯胺(简称:DNTPD)、7,7,8,8-四氰基对苯二醌二甲烷(简称:TCNQ)、2,3,5,6-四氟-7,7',8,8'-四氰二甲基对苯醌(简称:F4-TCNQ)、吡唑并[2,3-F][1,10]菲啰啉-2,3-二腈(简称:PPDN)、1,4,5,8,9,11-六氮杂苯甲腈(简称:HAT-CN),聚(N-乙烯基咔唑)(简称:PVK)、聚(4-乙烯基三苯胺)(简称:PVTPA)、聚[N,N’-二(4-丁基苯基)-N,N’-二(苯基)联苯胺](简称:Poly-TPD)、聚(3,4-亚乙二氧基噻吩)/聚(苯乙烯磺酸)(简称:PEDOT/PSS)等,但不限于此。本发明的空穴注入层可以是单层结构,也可以是两层以上的多层结构,每一层所包含的空穴注入材料可以是单一材料,也可以是混合材料。
本发明的空穴传输层具有提高空穴在器件中的传输效率并将电子阻挡在发光层内的作用。本发明的空穴传输材料优选具有较好的空穴传输性能的材料,可以选择如下材料中的一种或者多种,芳香族胺类衍生物、吡唑啉类化合物、咔唑衍生物、腙类化合物、苯乙烯类化合物、丁二烯类化合物等小分子材料以及聚合物材料,但不限于此。具体为,N4,N4,N4',N4'-四([1,1'-联苯]-4-基)-[1,1'-联苯]-4,4'-二胺、4,4',4”-三(N,N-二苯基氨基)三苯胺(简称:TDATA)、4,4',4”-三[N-(3-甲基苯基)-N-苯基氨基]三苯胺(简称:MTDATA)、N,N'-二苯基-N,N'-二菲-9-基-4,4'-联苯二胺(简称:PPD)、N,N'-二(萘-1-基)-N,N'-二(苯基)-2,2'-二甲基联苯胺(简称:α-NPD)、N,N'-二苯基-N,N'-(1-萘基)-1,1'-联苯-4,4'-二胺(简称:NPB)、N,N'-二(萘-2-基)-N,N'-二(苯基)联苯-4,4'-二胺(简称:β-NPB)、N,N'-二苯基-N,N'-二(α-萘基)-1,1'-联萘-4,4'-二胺(简称:α-NPN)、4,4'-环己基二[N,N-二(4-甲基苯基)苯胺](简称:TAPC)、N,N'-二苯基-N,N'-二(3-甲基苯基)-1,1'-联苯-4,4'-二胺(简称:TPD)、2,2,7,7-四(二苯基氨基)-9,9-螺二芴(简称:Spiro-TAD),3,3'-(1,4-亚苯基)二(1,5-二苯基-4,5-二氢-1H-吡唑)(简称:PYR-D1),4,4',4”-三(咔唑-9-基)三苯胺(简称:TCTA);聚(N-乙烯基咔唑)(简称:PVK),4-(N,N-二对甲基苯基)氨基苯甲醛-1,1-二苯基腙,1,4-二[4-(N,N-二对甲基苯基氨基)苯乙烯基]苯(简称:DPD)等,但不限于此。本发明的空穴传输层可以是单层结构,也可以是两层以上的多层结构,每一层所包含的空穴传输材料可以是单一材料,也可以是混合材料。
本发明的发光层是指能够发射光子的有机物层。本发明的发光层可以包含一种材料,也可以包含两种以上的混合材料,所述发光材料分为蓝色发光材料、绿色发光材料以及红色发光材料。
上述蓝色发光材料选自如下所述材料中的一种或者多种,芘衍生物、蒽衍生物、芴衍生物、苝衍生物、苯乙烯基胺衍生物、金属配合物等,但不限于此。具体为,N1,N6-二([1,1'-联苯]-2-基)-N1,N6-二([1,1'-联苯]-4-基)芘-1,6-二胺、9,10-二-(2-萘基)蒽(简称:ADN)、2-甲基-9,10-二-2-萘基蒽(简称:MADN)、2,7-二(4-二苯胺基苯基)-9,9-二(4-二苯胺基苯基)芴(简称:XB10)、2,5,8,11-四叔丁基苝(简称:TBPe)、4,4'-二[4-(二苯氨基)苯乙烯基]联苯(简称:BDAVBi)、4,4'-二[4-(二对甲苯基氨基)苯乙烯基]联苯(简称:DPAVBi)、1,4-二[4-(N,N-二苯基)氨基]苯乙烯(简称:DSA-Ph)、三[1-(2,6-二异丙基苯基)-2-苯基-1H-咪唑]合铱(简称:fac-Ir(iprpmi)3)、二(2-羟基苯基吡啶)合铍(简称:Bepp2)、二(4,6-二氟苯基吡啶-C2,N)吡啶甲酰合铱(简称:FIrpic)、二(2,4-二氟苯基吡啶)-四(1-吡唑基)硼酸铱(III)(简称:Fir6)等,但不限于此。
上述绿色发光材料选自如下所述材料中的一种或者多种,香豆素染料、喹吖啶铜类衍生物、多环芳香烃、二胺蒽类衍生物、咔唑衍生物、金属配合物等,但不限于此。具体为,香豆素6(简称:C-6)、香豆素545T(简称:C-525T)、喹吖啶铜(简称:QA)、N,N'-二甲基喹吖啶酮(简称:DMQA)、5,12-二苯基萘并萘(简称:DPT)、N10,N10,N10',N10'-四苯基-9,9'-二蒽-10,10'-二胺(简称:BA-TAD)、N10,N10'-二苯基-N10,N10'-二苯二甲酰-9,9'-二蒽-10,10'-二胺(简称:BA-NPB)、9,9',9”-(5-(4,6-二苯基-1,3,5-三嗪-2-基)苯-1,2,3-三基)三(3,6-二甲基-9H-咔唑)(简称:TmCzTrz)、三(8-羟基喹啉)合铝(III)(简称:Alq3)、三(2-苯基吡啶)合铱(简称:Ir(ppy)3)、乙酰丙酮酸二(2-苯基吡啶)铱(简称:Ir(ppy)2(acac))、三[2-(对甲苯基)吡啶-C2,N]合铱(III)(简称:Ir(mppy)3)、三[2-(3-甲基-2-吡啶基)苯基]铱(简称:Ir(3mppy)3)、二[2-(2-苯并噻唑基)苯酚]锌(简称:Zn(BTZ)2)等,但不限于此。
上述红色发光材料选自如下所述材料中的一种或者多种,DCM系列材料、金属配合物等,但不限于此。具体为,4-(二氰基亚甲基)-2-甲基-6-(4-二甲基氨基苯乙烯基)-4H-吡喃(简称:DCM)、4-(二氰基甲撑)-2-叔丁基-6-(1,1,7,7-四甲基久洛尼啶-9-烯基)-4H-吡喃(简称:DCJTB),二(1-苯基异喹啉)(乙酰丙酮)铱(III)(简称:Ir(piq)2(acac))、八乙基卟啉铂(简称:PtOEP)、二(2-(2'-苯并噻吩基)吡啶-N,C3')(乙酰丙酮)合铱(简称:Ir(btp)2(acac)、二[1-(9,9-二甲基-9H-芴-2-基)-异喹啉](乙酰丙酮)铱(III)(简称:Ir(fliq)2(acac))、二[2-(9,9-二甲基-9H-芴-2-基)-喹啉](乙酰丙酮)铱(III)(简称:Ir(flq)2(acac))、三(二苯甲酰基甲烷)单(菲罗啉)铕(III)(简称:Eu(dbm)3(Phen))等,但不限于此。
当上述发光材料用作客体材料时,需要选择合适的主体材料与之匹配,所述主体材料优选与客体材料相比最低未占轨道能级高、最高已占轨道能级低的材料。上述主体材料包括铝配合物、锌配合物等金属配合物,芴衍生物,蒽衍生物,咔唑衍生物等,但不限于此。具体为,三(8-羟基喹啉)合铝(III)(简称:Alq3)、8-羟基喹啉锌(简称:Znq2)、2,7-二[9,9-二(4-甲基苯基)-芴-2-基]-9,9-二(4-甲基苯基)芴(简称:TDAF)、9,10-二(2-萘基)蒽(简称:ADN)、9-(1-萘基)-10-[4-(2-萘基)苯基]蒽、1,3,5-三(9-咔唑基)苯(简称:TCP)、9,9'-(1,3-苯基)二-9H-咔唑(简称:MCP)、4,4'-二(9-咔唑)联苯(简称:CBP)、4,4',4”-三(咔唑-9-基)三苯胺(简称:TCTA)等,但不限于此。
本发明的空穴阻挡层具有防止空穴从发光层泄漏至电子传输层的作用。本发明的空穴阻挡材料优选具有较好的空穴阻挡性能的材料,可以选择如下所述材料中的一种或者多种,菲啰啉衍生物、铝配合物、苯并咪唑衍生物、芳香化合物、有机硼化合物等,但不限于此。具体为,4,7-二苯基-1,10-菲罗啉(简称:Bphen)、2,9-二(萘-2-基)-4,7-二苯基-1,10-菲罗啉(简称:NBphen)、2,9-二甲基-4,7-二苯基-1,10-菲啰啉(简称:BCP)、二(8-羟基-2-甲基喹啉)-(4-苯基苯氧基)铝(简称:BAlq)、1,3,5-三(N-苯基-2-苯并咪唑)苯(简称:TPBi)、(1,3,5-三联苯基)苯(简称:TBB)、1,3,5-三(9,9-二甲基-9H-芴-2-基)苯(简称:TFB)、三异丙叉丙酮基硼烷(简称:TPhB)等,但不限于此。本发明的空穴阻挡层可以是单层结构,也可以是两层以上的多层结构,每一层所包含的空穴阻挡材料可以是单一材料,也可以是混合材料。
本发明的电子传输层具有提高电子在器件中的传输效率并将空穴阻挡在发光层内的作用。本发明的电子传输材料,优选具有较好的电子传输性能的材料,可以选择如下所述材料中的一种或者多种,铝配合物、铍配合物、锌配合物等金属配合物,恶唑衍生物、咪唑衍生物、***类化合物、菲啰啉衍生物、吡啶衍生物芳香族杂环化合物,聚合物等,但不限于此。具体为,三(8-羟基喹啉)合铝(III)(简称:Alq3)、三(4-甲基-8-羟基喹啉)合铝(简称:Almq3)、二(10-羟基苯并[h]喹啉)铍(简称:Bepq2)、二(2-甲基-8-羟基喹啉)(4-苯基苯酚)合铝(III)(简称:BAlq)、二(8-羟基喹啉)合锌(II)(简称:Znq),2,5-二-(4-萘基)-1,3,4-恶二唑(简称:BND)、2-(4-联苯基)-5-(4-叔丁基苯基)-1,3,4-恶二唑(简称:PBD)、2-(4-(9,10-二(萘-2-基)蒽-2-基)苯基)-1-苯基-1H-苯并[d]咪唑、1,3,5-三(N-苯基-2-苯并咪唑)苯(简称:TPBi)、4,7-二苯基-1,10-菲罗啉(简称:Bphen)、2,9-二甲基-4,7-二苯基-1,10-菲啰啉(简称:BCP)、2,9-二(萘-2-基)-4,7-二苯基-1,10-菲罗啉(简称:NBphen)、3,3'-[5'-[3-(3-吡啶基)苯基](简称:TmPyPB)、1,3,5-三(4-吡啶-3-基苯基)苯(简称:TpPyPB)、1,3,5-三(6-(3-(3-吡啶基)苯基)吡啶-2-基)苯(简称:Tm3PyP26PyB)、2,4,6-三(3-(3-吡啶基)-(1,1'-联苯基)-3-基)-1,3,5-三嗪(简称:TmPPPyTz),聚[9,9-二[6'-(N,N,N-三甲基铵)己基]芴-alt-co-1,4-亚苯基]溴化物(简称:FPQ-Br)等,但不限于此。本发明的电子传输层还可以是由上述电子传输材料和下述电子注入材料相互掺杂形成的混合材料,例如Alq3/LiF、Alq3/Liq、BAlq/LiF、BAlq/Liq等,但不限于此。本发明的电子传输层可以是单层结构,也可以是两层以上的多层结构,每一层所包含的电子传输材料可以是单一材料,也可以是混合材料。
本发明的电子注入层的作用是提高电子从阴极注入电子传输层和发光层的效率。本发明的电子注入材料优选具有较好的电子注入性能的材料,本发明的电子注入材料可以选择如下材料中的一种或者多种,碱金属、碱土金属或者含有碱金属、碱土金属的化合物等,但不限于此。具体为,Li、Na、K、Rb、Cs、Be、Mg、Ca、Sr、Ba,氟化锂、氟化钠、氟化钾、氟化铷、氟化铯、氟化镁、氟化钙、氧化锂、碳酸铯、偏硼酸锂、硅酸钾、醋酸锂、醋酸钠、醋酸铷、醋酸钾、醋酸铯、四(8-羟基喹啉)硼锂、8-羟基喹啉锂等,但不限于此。本发明的电子注入层可以是单层结构,也可以是两层以上的多层结构,每一层所包含的电子注入材料可以是单一材料,也可以是混合材料。
本发明所述的阴极具有将电子注入到电子传输层中的功能,阴极材料需要具有较低的功函数,由于顶发射器件的光从阴极传出,又要求阴极具有较高的透过率。本发明的阴极材料可以选择如下所述材料中的一种或者多种,主族金属、碱金属、碱土金属、过渡金属、镧系金属等金属或者合金,但不限于此。具体为,Al、In、Li、Mg、Ca、Ag、Ti、Sm,Mg/Ag、Li/Al等,但不限于此。阴极的膜厚根据材料而有所不同,通常选择10nm~1μm,优选10nm~300nm的范围。本发明的阴极可以是单层结构,也可以是两层以上的多层结构,每一层所包含的阴极材料可以是单一材料,也可以是混合材料。
本发明所述的光取出层可以选择如下所述材料中的一种或者多种,金属化合物、芳香族胺类衍生物、咔唑衍生物或者本发明所述的胺类衍生物等,但不限于此。具体为,三(8-羟基喹啉)合铝(III)(简称:Alq3)、氧化镁、硒化锌、硫化锌、氧化锡、氧化钼、氧化碲,N,N′-二(萘-1-基)-N,N′-二(苯基)-2,2′-二甲基联苯胺(简称:α-NPD)、N,N′-二苯基-N,N′-(1-萘基)-1,1′-联苯-4,4′-二胺(简称:NPB)、N4,N4,N4′,N4′-四(4-甲氧基苯基)-[1,1′-联苯]-4,4′-二胺(简称:MeO-TPD),4,4′-二(9-咔唑)联苯(简称:CBP)等,但不限于此。优选为本发明所述的胺类衍生物。本发明的光取出材料可以是单层结构,也可以是两层以上的多层结构,每一层所包含的光取出材料可以是单一材料,也可以是混合材料。
对本发明的有机电致发光器件的各层的形成方法,没有特别限制,可以采用干式成膜法、湿式成膜法等公知的方法。干式成膜法包括真空蒸镀法、溅射法、等离子法等。湿式成膜法包括旋涂法、浸渍法、喷墨法等,但不限于此。
本发明的有机电致发光器件可广泛应用于平板显示、固体照明、有机感光体或有机薄膜晶体管等领域。
本发明式I所示的胺类衍生物的合成路线如下
步骤一:
步骤二:
步骤三:
本发明对以下实施例中所采用的原料没有特别的限制,可以为市售产品或采用本领域技术人员所熟知的制备方法制备得到。
化合物的制备及表征
原料、试剂以及表征设备的说明:
本发明所用的原料及试剂均为试剂纯;
质谱使用岛津集团英国Kratos Analytical公司的AXIMA-CFR plus基质辅助激光解吸电离飞行质谱仪,氯仿为溶剂;
元素分析使用德国Elementar公司的Vario EL cube型有机元素分析仪,样品质量为5~10mg;
核磁共振(1HNMR)使用Bruker-510型核磁共振谱仪(德国Bruker公司),600MHz,CDCl3为溶剂,TMS为内标。
合成例1:化合物1的合成
中间体I-1的合成
向1L反应瓶中加入脱气过的甲苯溶剂(400mL),然后依次加入原料4-(2-苯并恶唑基)苯胺(37.8g,0.18mol)、溴苯(19.0ml,0.18mol)及叔丁醇钠(22.8g,0.234mol)。氮气置换三次后,加入醋酸钯(0.4g,0.0018mol)。再进行氮气置换三次后,加入三叔丁基膦(7.2mL的1.0M的甲苯溶液,0.0072mol)。再重复氮气置换步骤三次后,将该混合物在氮气环境下回流2小时。反应停止后,将混合物冷却至室温,经硅藻土过滤得滤液。浓缩滤液,加入少量甲醇后,静置重结晶,一段时间后,有固体产生,抽滤并用甲醇淋洗得重结晶固体,即为中间体I-1(46.3g,产率约为90%),HPLC检测固体纯度≧98.1%。
化合物1的合成
向250mL反应瓶中加入脱气过的甲苯溶剂(100mL),然后依次加入原料中间体I-1(17.6g,0.062mol)、2,7-二溴-9,9-二甲基芴(9.8g,0.028mol)及叔丁醇钠(8.0g,0.084mol)。氮气置换三次后,加入醋酸钯(0.12g,0.00056mol)。再进行氮气置换三次后,加入三叔丁基膦(2.24mL的1.0M的甲苯溶液,0.00224mol)。再重复氮气置换步骤三次后,将该混合物在氮气环境下回流2小时。反应停止后,将混合物冷却至室温,经硅藻土过滤得滤液。浓缩滤液,将滤液加热至60℃后,加入少量乙醇,静置至室温重结晶,一段时间后,有固体产生,抽滤并用乙醇淋洗得重结晶固体,得到淡黄色固体化合物1(18.1g,产率约为85%),HPLC检测固体纯度≧99.9%。
质谱m/z:762.85(计算值:762.91)。理论元素含量(%)C53H38N4O2:C,83.44;H,5.02;N,7.34;O,4.19实测元素含量(%):C,83.52;H,5.02;N,7.35;O,4.11。1H NMR(600MHz,CDCl3)(δ,ppm):8.10(d,J=8.6Hz,4H),7.82–7.67(m,2H),7.67–7.50(m,4H),7.40–7.28(m,8H),7.23(d,J=8.5Hz,6H),7.20–6.99(m,8H),1.40(s,6H)。上述结果证实获得产物为目标产品。
合成例2:化合物10的合成
将合成例1中的溴苯换成等摩尔的4-溴联苯,其他步骤相同,得到黄色固体化合物10(22.5g,产率约为88%)。质谱m/z:914.41(计算值:915.11)。理论元素含量(%)C65H46N4O2:C,85.31;H,5.07;N,6.12;O,3.50实测元素含量(%):C,85.28;H,4.95N,6.08;O,3.55。上述结果证实获得产物为目标产品。
合成例3:化合物22的合成
将合成例1中的溴苯换成等摩尔的2-溴-9,9-二甲基芴,其他步骤相同,得到黄色固体化合物22(20.0g,产率约为72%)。质谱m/z:995.32(计算值:995.24)。理论元素含量(%)C71H54N4O2:C,85.69;H,5.47;N,5.63;O,3.22实测元素含量(%):C,85.77;H,5.48;N,5.62;O,3.12。1H NMR(600MHz,CDCl3)(δ,ppm):7.92(d,J=3.3Hz,1H),7.89(d,J=3.2Hz,1H),7.88(s,2H),7.85(s,2H),7.79–7.70(m,8H),7.56(d,J=3.2Hz,1H),7.53(dd,J=2.8,1.3Hz,5H),7.42–7.33(m,9H),7.31(dd,J=5.3,2.3Hz,3H),7.28(dd,J=6.6,3.3Hz,3H),7.24(d,J=3.2Hz,1H),1.47(d,J=30.9Hz,12H),1.39(s,6H).。上述结果证实获得产物为目标产品。
合成例4:化合物26的合成
将合成例1中的溴苯换成等摩尔的2-溴-11,11-二甲基-苯并[b]芴,其他步骤相同,得到黄色固体,化合物26(20.8g,产率约为68%)。质谱m/z:1095.44(计算值:1095.36)。理论元素含量(%)C79H58N4O2:C,86.63;H,5.34;N,5.12;O,2.92实测元素含量(%):C,86.71;H,5.32;N,5.12;O,2.87。1H NMR(600MHz,CDCl3)(δ,ppm):8.15(d,J=8.6Hz,4H),8.02(s,2H),7.86(dt,J=6.8,2.1Hz,6H),7.79–7.74(m,2H),7.73(s,2H),7.65(d,J=8.1Hz,2H),7.60–7.53(m,2H),7.49–7.39(m,6H),7.34(dd,J=9.5,4.0Hz,6H),7.25(s,2H),7.23–7.16(m,4H),1.63(s,12H),1.45(s,6H)。上述结果证实获得产物为目标产品。
合成例5:化合物27的合成
将合成例1中的溴苯换成等摩尔的9-溴-11,11-二甲基-11H-苯并[A]芴,其他步骤相同,得到黄色固体,化合物27(20.24g,产率约为66%)。质谱m/z:1094.48(计算值:1095.36)。理论元素含量(%)C79H58N4O2:C,86.63;H,5.34;N,5.12;O,2.92实测元素含量(%):C,86.56;H,5.30;N,5.16;O,2.88。上述结果证实获得产物为目标产品。
合成例6:化合物35的合成
将合成例1中的溴苯换成等摩尔的3-溴二苯并[b,d]呋喃,其他步骤相同,得到黄色固体化合物35(19.5g,产率约为74%)。质谱m/z:943.31(计算值:943.08)。理论元素含量(%)C65H42N4O4:C,82.78;H,4.49;N,5.94;O,6.79实测元素含量(%):C,82.83;H,4.50;N,5.92;O,6.75。1H NMR(600MHz,CDCl3)(δ,ppm):8.12–8.08(m,4H),7.88–7.81(m,4H),7.76–7.71(m,2H),7.62–7.53(m,8H),7.47(d,J=1.0Hz,2H),7.38–7.30(m,8H),7.28(s,2H),7.18–7.15(m,6H),1.39(s,6H)。上述结果证实获得产物为目标产品。
合成例7:化合物41的合成
将合成例1中的2,7-二溴-9,9-二甲基芴换成等摩尔的2,7-二溴-9,9-二苯基芴其他步骤相同,得到淡黄色固体化合物41(20.6g,产率约为83%)。质谱m/z:887.31(计算值:887.06)。理论元素含量(%)C63H42N4O2:C,85.30;H,4.77;N,6.32;O,3.61实测元素含量(%):C,85.38;H,4.85;N,6.38;O,3.70。1H NMR(600MHz,CDCl3)(δ,ppm):8.06(d,J=7.9Hz,4H),7.80–7.69(m,2H),7.62(d,J=6.6Hz,2H),7.58–7.53(m,6H),7.51(t,J=9.5Hz,4H),7.43(t,J=7.7Hz,4H),7.37–7.30(m,6H),7.22–7.18(m,8H),7.14–7.10(m,6H)。上述结果证实获得产物为目标产品。
合成例8:化合物44的合成
将合成例1中的溴苯换成等摩尔的4-溴联苯,2,7-二溴-9,9-二甲基芴换成等摩尔的2,7-二溴-9,9-二苯基芴其他步骤相同,得到淡黄色固体化合物44(23.6g,产率约为81%)。质谱m/z:1038.43(计算值:1039.25)。理论元素含量(%)C75H50N4O2:C,86.68;H,4.85;N,5.39;O,3.08实测元素含量(%):C,86.56;H,4.82;N,5.49;O,3.08。上述结果证实获得产物为目标产品。
合成例9:化合物73的合成
中间体a的合成
向1L反应瓶中依次加入固体原料2-溴-7-碘芴(37.1g,0.1mol)、对溴苯硼酸(22.1g,0.11mol),然后加入超声脱气的甲苯(250mL)、乙醇(100mL)和碳酸钾(41.4g,0.3mol)的150mL水溶液。抽真空充氮气三次,氮气氛围下加入催化剂四三苯基膦钯(1.15g,0.001mol),继续抽真空充氮气三次,80℃回流搅拌反应4个小时后停止加热,向混合物中加入150mL水,搅拌30分钟,降温至40℃左右减压过滤,依次使用热水(100mL)和丙酮(150mL)冲洗滤饼,确保滤液pH值约为7。使用1L氯仿溶解滤饼,溶液过硅胶漏斗,浓缩滤液至500mL后加入少量甲醇(25mL左右)重结晶,减压过滤得到固体(36.0g,产率约为90%),HPLC检测固体纯度≧98.6%。
将上述固体(20g,0.05mol)溶解于700mL甲苯中,氮气氛围下加入碘甲烷(6.2mL,0.1mol)和叔丁醇钾(16.8g,0.15mol),之后加入配体3-环己基苯酚(1.41g,0.008mol)和催化剂醋酸钯(1.12g,0.005mol),氮气置换三次后,回流反应过夜。反应结束时,降温至室温,过硅胶漏斗后,将滤液倒入400mL水中,搅拌半小时后甲苯萃取,合并有机相,干燥浓缩至500mL,加入200mL甲醇重结晶,一段时间后,有固体生成,即为中间体a(19.3g,产率约为90%),HPLC检测固体纯度≧99.2%
化合物73的合成
将合成例1中的2,7-二溴-9,9-二甲基芴换成等摩尔的中间体a,其他步骤相同,得到淡黄色固体化合物73(18.3g,产率约为78%)。质谱m/z:839.29(计算值:839.01)。理论元素含量(%)C59H42N4O2:C,84.46;H,5.05;N,6.68;O,3.81实测元素含量(%):C,84.54;H,5.05;N,6.66;O,3.75。1H NMR(600MHz,CDCl3)(δ,ppm):8.19–8.05(m,4H),7.74(ddd,J=14.1,8.0,4.9Hz,3H),7.67(d,J=8.1Hz,1H),7.63(dd,J=5.0,3.5Hz,3H),7.60–7.52(m,3H),7.39–7.29(m,8H),7.29–7.26(m,2H),7.26–7.21(m,5H),7.21–7.10(m,7H),1.49(s,6H)。上述结果证实获得产物为目标产品。
合成例10:化合物75的合成
将合成例9中的溴苯换成等摩尔的4-叔丁基溴苯,其他步骤相同,得到淡黄色固体化合物75(21.0g,产率约为79%)。质谱m/z:950.51(计算值:951.23)。理论元素含量(%)C67H58N4O2:C,84.60;H,6.15;N,5.89;O,3.36实测元素含量(%):C,84.56;H,6.18;N,5.83;O,3.43。上述结果证实获得产物为目标产品。
合成例11:化合物78的合成
将合成例9中的溴苯换成等摩尔的4-溴联苯,其他步骤相同,得到淡黄色固体化合物78(20.8g,产率约为75%)。质谱m/z:990.40(计算值:991.21)。理论元素含量(%)C71H50N4O2:C,86.03;H,5.08;N,5.65;O,3.23实测元素含量(%):C,86.11;H,5.04;N,5.69;O,3.20。上述结果证实获得产物为目标产品。
合成例12:化合物89的合成
将合成例9中的溴苯换成等摩尔的4-溴联苯,其他步骤相同,得到淡黄色固体化合物89(21.9g,产率约为73%)。质谱m/z:1070.49(计算值:1071.34)。理论元素含量(%)C77H58N4O2:C,86.33;H,5.46;N,5.23;O,2.99实测元素含量(%):C,86.27;H,5.41;N,5.29;O,2.88。上述结果证实获得产物为目标产品。
合成例13:化合物101的合成
将合成例1中的4-(2-苯并恶唑基)苯胺换成等摩尔的4-(2-苯并噻唑基)苯胺,其他步骤相同,得到亮黄色固体化合物101(18.5g,产率约为83%)。质谱m/z:795.19(计算值:795.04)。理论元素含量(%)C53H38N4S2:C,80.07;H,4.82;N,7.05;S,8.07实测元素含量(%):C,80.13;H,4.80;N,7.04;S,8.03。1H NMR(600MHz,CDCl3)(δ,ppm):8.18(dd,J=6.9,2.0Hz,2H),8.02(dd,J=6.8,2.1Hz,2H),7.86(dd,J=7.5,5.0Hz,6H),7.58–7.47(m,6H),7.37(d,J=7.5Hz,4H),7.31–7.21(m,6H),7.08(dd,J=7.5,1.4Hz,4H),7.04–6.96(m,2H),1.69(s,6H)。上述结果证实获得产物为目标产品。
合成例14:化合物121的合成
将合成例9中的4-(2-苯并恶唑基)苯胺换成等摩尔的换成等摩尔的4-(2-苯并噻唑基)苯胺,其他步骤相同,得到亮黄色固体,化合物121(18.0g,产率约为74%)。质谱m/z:870.25(计算值:871.13)。理论元素含量(%)C59H42N4O2:C,81.35;H,4.86;N,6.43;S,7.36实测元素含量(%):C,81.32;H,4.85;N,6.45;S,7.37。1H NMR(600MHz,CDCl3)(δ,ppm):8.22–8.14(m,2H),8.08(t,J=10.0Hz,1H),8.05–7.98(m,3H),7.89–7.82(m,5H),7.78(dd,J=15.0,2.9Hz,1H),7.60–7.46(m,7H),7.42–7.33(m,6H),7.33–7.19(m,5H),7.12–7.05(m,4H),7.04–6.95(m,2H),1.69(s,6H)。上述结果证实获得产物为目标产品。
合成例15:化合物125的合成
将合成例9中的溴苯换成等摩尔的4-溴联苯,4-(2-苯并恶唑基)苯胺换成等摩尔的换成等摩尔的4-(2-苯并噻唑基)苯胺,其他步骤相同,得到亮黄色固体,化合物125(20.9g,产率约为73%)。质谱m/z:1022.38(计算值:1023.33)。理论元素含量(%)C71H50N4S2:C,83.33;H,4.93;N,5.48;S,6.27实测元素含量(%):C,83.24;H,4.97;N,5.51;S,6.24。上述结果证实获得产物为目标产品。
合成例16:化合物143的合成
将合成例1中的4-(2-苯并恶唑基)苯胺换成等摩尔的4-(1-苯基苯并咪唑-2-基)苯胺,2,7-二溴-9,9-二甲基芴换成等摩尔的2,7-二溴-9,9'-螺二芴,其他步骤相同,得到黄色固体,化合物143(20.58g,产率约为71%)。质谱m/z:1034.35(计算值:1035.27)。理论元素含量(%)C59H42N4O2:C,87.01;H,4.87;N,8.12;实测元素含量(%):C,86.98;H,4.91;N,8.11。1H NMR(600MHz,CDCl3)(δ,ppm):1H NMR(600MHz,CDCl3)(δ,ppm)7.85(d,J=7.2Hz,2H),7.70(d,J=7.6Hz,2H),7.61(d,J=8.2Hz,2H),7.48(d,J=6.9Hz,6H),7.40–7.27(m,12H),7.25–7.20(m,2H),7.20–7.10(m,8H),7.06–6.86(m,8H),6.83(d,J=7.6Hz,2H),6.77(d,J=8.7Hz,4H),6.50(d,J=1.7Hz,2H)。上述结果证实获得产物为目标产品。
合成例17:化合物144的合成
将合成例9中的4-(2-苯并恶唑基)苯胺换成等摩尔的换成等摩尔的4-(1-苯基苯并咪唑-2-基)苯胺,其他步骤相同,得到黄色固体,化合物144(19.4g,产率约为70%)。质谱m/z:988.49(计算值:989.24)。理论元素含量(%)C71H52N6:C,86.21;H,5.30;N,8.50实测元素含量(%):C,86.32;H,5.24;N,8.56。上述结果证实获得产物为目标产品。
合成例18:化合物146的合成
向250mL反应瓶中加入脱气过的甲苯溶剂(100mL),然后依次加入原料中间体I-2(17.6g,0.028mol)、N,N-二([1,1'-联苯基]-4-基)-7-溴-9,9-二甲基-9H-芴-2-胺(9.8g,0.028mol)及叔丁醇钠(4.0g,0.042mol)。氮气置换三次后,加入醋酸钯(0.06g,0.00028mol)。再进行氮气置换三次后,加入三叔丁基膦(1.12mL的1.0M的甲苯溶液,0.00112mol)。再重复氮气置换步骤三次后,将该混合物在氮气环境下回流2小时。反应停止后,将混合物冷却至室温,经硅藻土过滤得滤液。浓缩滤液,将滤液加热至60℃后,加入少量乙醇,静置至室温重结晶,一段时间后,有固体产生,抽滤并用乙醇淋洗得重结晶固体,得到淡黄色固体化合物146(21.8g,产率约为89%),HPLC检测固体纯度≧99.9%。
质谱m/z:873.35(计算值:874.10)。理论元素含量(%)C64H47N3O:C,87.94;H,5.42;N,4.81;O,1.83实测元素含量(%):C,87.85;H,5.54;N,4.84;O,1.99。1H NMR(600MHz,CDCl3)(δ,ppm):7.88(s,1H),7.85(s,1H),7.77–7.75(m,3H),7.75–7.73(m,5H),7.72(t,J=3.5Hz,2H),7.56(d,J=2.3Hz,2H),7.55–7.51(m,7H),7.49(dd,J=3.9,3.0Hz,3H),7.48–7.45(m,2H),7.43(dd,J=7.7,4.4Hz,2H),7.41–7.39(m,2H),7.39–7.37(m,5H),7.37–7.34(m,4H),7.32(d,J=2.9Hz,1H),7.29(d,J=2.9Hz,1H),1.69(s,6H).上述结果证实获得产物为目标产品。
合成例19:化合物153的合成
将合成例18中的中间体I-2换成等摩尔的中间体II-2,其他步骤相同,得到亮黄色固体,化合物153(22.7g,产率约为91%)。质谱m/z:889.37(计算值:890.16)。理论元素含量(%)C64H47N3S:C,86.36;H,5.32;N,4.72;S,3.60实测元素含量(%):C,86.26;H,5.25;N,4.87;S,3.55。上述结果证实获得产物为目标产品。
化合物的光物理性质
化合物的玻璃转化温度(Tg)的测定:测量仪器为美国TA公司的DSC 25型差示扫描量热仪;测试气氛为氮气,氮气的流速为50ml/min;升温速率为为10℃/min,温度范围为50~350℃;化合物样品的质量为1~6mg;坩埚类型为铝制坩埚。所测得的玻璃转化温度(Tg)如表1所示。
表1化合物的玻璃转化温度(Tg)
化合物 | 玻璃转化温度(℃) | 化合物 | 玻璃转化温度(℃) |
化合物1 | 130 | 化合物89 | 140 |
化合物10 | 133 | 化合物101 | 129 |
化合物22 | 139 | 化合物121 | 132 |
化合物26 | 140 | 化合物125 | 135 |
化合物27 | 140 | 化合物143 | 131 |
化合物35 | 137 | 化合物144 | 129 |
化合物41 | 132 | 化合物146 | 131 |
化合物44 | 135 | 化合物153 | 132 |
化合物73 | 132 | CPM-1 | 125 |
化合物75 | 131 | CPM-2 | 128 |
化合物78 | 134 |
从表1中可以看出本发明的胺类衍生物的玻璃转化温度高于CPM-1和CPM-2的玻璃转化温度,因此本发明的胺类衍生物的热稳定性更加的优越,是一种性能更加稳定的材料。
化合物的折射率(n)的测定:测量仪器为美国J.A.Woollam公司的M-2000光谱型椭偏仪;仪器扫描范围为245~1000nm;玻璃基板大小为200×200mm,材料薄膜厚度为20~60nm。所测得的在450nm下的折射率(n)如表2所示。
表2化合物的折射率(n)
化合物 | 折射率 | 化合物 | 折射率 |
化合物1 | 2.07 | 化合物89 | 2.12 |
化合物10 | 2.11 | 化合物101 | 2.07 |
化合物22 | 2.09 | 化合物121 | 2.05 |
化合物26 | 2.10 | 化合物125 | 2.09 |
化合物27 | 2.10 | 化合物143 | 2.04 |
化合物35 | 2.12 | 化合物144 | 2.07 |
化合物41 | 2.08 | 化合物146 | 2.14 |
化合物44 | 2.12 | 化合物153 | 2.13 |
化合物73 | 2.06 | CPM-1 | 2.10 |
化合物75 | 2.05 | CPM-2 | 2.15 |
化合物78 | 2.10 |
从表2中可以看出,本发明的胺类衍生物的折射率和化合物CPM-1以及CPM-2的折射率相当,说明本发明的胺类衍生物用作光取出材料时可以有效的将器件中的光耦合出来,提高有机电致发光器件的发光效率。
器件的制备与性能
在本发明中,有机材料都是经过升华,纯度都在99.99%以上。实验中用到的ITO玻璃基板是从深圳南玻显示器件科技有限公司购买。ITO玻璃基板由5%的玻璃清洗液超声清洗2次,每次20分钟,再由去离子水超声清洗2次,每次10分钟。依次使用丙酮和异丙酮超声清洗20分钟,120℃烘干。
器件的制备采用真空蒸镀***,在真空不间断条件下连续蒸发制备完成。所用材料分别在不同的蒸发源石英坩埚中,蒸发源的温度可以单独控制。有机材料或掺杂母体有机材料的热蒸发速率一般定在0.1nm/s,掺杂材料蒸发速率调节按掺杂比率进行;电极金属蒸发速率在0.4~0.6nm/s。将处理好的玻璃基板放置到OLED真空镀膜机中,在薄膜制作过程中,***真空度应该维持在5×10-5Pa以下,通过更换掩膜板分别来蒸镀有机层和金属电极,用Inficon的SQM160石英晶体膜厚检测仪检测蒸镀速度,用石英晶体振荡器检测薄膜厚度。将测试软件、计算机、美国Keithley公司生产的K2400数字源表和美国Photo Research公司的PR788光谱扫描亮度计组成一个联合IVL测试***来测试有机电致发光器件的驱动电压、发光效率、CIE色坐标。寿命的测试采用McScience公司的M6000 OLED寿命测试***。测试的环境为大气环境,温度为室温。
实施例1:有机电致发光器件1的制备
在玻璃基板上以ITO/Ag/ITO作为阳极;在阳极上真空蒸镀HIM-1作为第一空穴注入层,蒸镀厚度为60nm;在第一空穴注入层上真空蒸镀HAT-CN作为第二空穴注入层,蒸镀厚度为5nm;在第二空穴注入层上真空蒸镀NPB作为空穴传输层,蒸镀厚度为60nm;在空穴传输层上真空蒸镀BH-1与3%BD-1作为发光层,蒸镀厚度为25nm;在发光层上真空蒸镀Alq3:Liq(1:1)作为电子传输层,蒸镀厚度为30nm;在电子传输层上真空蒸镀LiF作为电子注入层,蒸镀厚度为1nm;在电子注入层上真空蒸镀Mg/Ag(9:1)作为阴极,蒸镀厚度为15nm;在阴极上真空蒸镀本发明的化合物1作为光取出层,蒸镀厚度为60nm。
实施例2~19:将实施例1中光取出层中的化合物1分别换成化合物10、化合物22、化合物26、化合物27、化合物35、化合物41、化合物44、化合物73、化合物75、化合物78、化合物89、化合物101、化合物121、化合物125、化合物143、化合物144、化合物146、化合物153,其他步骤相同,得到有机电致发光器件2~19。
对比例1:将实施例1中光取出层中的化合物1换成化合物CPM-1,其他步骤相同,得到对比有机电致发光器件1。
对比例2:将实施例1中光取出层中的化合物1换成化合物CPM-2,其他步骤相同,得到对比有机电致发光器件2。
对比例3:参照实施例1的步骤制备有机电致发光器件,但不形成光取出层,得到对比有机电致发光器件3。
本发明实施例1~19以及对比例1~3制备的有机电致发光器件的发光特性测试结果如表3所示。
表3有机电致发光器件的发光特性测试数据
从表3中可以看出,与对比例1和对比例2相比,采用本发明的胺类衍生物作为光取出材料的有机电致发光器件的使用寿命更长。与对比例3相比,采用本发明的胺类衍生物作为光取出材料的有机电致发光器件的发光效率较高、使用寿命较长。因此,本发明的胺类衍生物是一种性能更好的光取出材料。
Claims (9)
1.一种胺类衍生物,其特征在于,所述胺类衍生物由式I表示,
其中,Ar1、Ar2中的至少一个选自式II所示的基团,
当Ar1或Ar2不为式II所示的基团时,其选自苯基、联苯基或萘基中的一种;
所述L1选自单键、亚苯基、亚联苯基、亚萘基中的一种;所述a选自0~4中的整数,所述R1选自C1~C15的烷基、C6~C18的芳基中的一种,当a大于1时,每个R1相同或者不同,所述X选自O、S或者N(Rx),所述Rx选自C6~C18的芳基中的一种;
所述Ar3、Ar4独立的选自如下所示基团中的一种:
其中,所述d选自0~5的整数,所述R4选自C1~C10的烷基,当d大于1时,每个R4相同或者不同;
所述e选自0~4的整数,所述R5选自C1~C10的烷基、C6~C18的芳基中的一种,当e大于1时,每个R5相同或者不同;
所述f选自0~4的整数,所述R6选自C1~C10的烷基、C6~C18的芳基中的一种,当f大于1时,每个R6相同或者不同;
所述g选自0~5的整数,所述R7选自C1~C10的烷基、C6~C18的芳基中的一种,当g大于1时,每个R7相同或者不同;
所述R0选自C1~C10的烷基、C6~C18的芳基中的一种;
所述L2选自单键、亚苯基、亚联苯基、亚萘基中的一种;
所述L选自如下所示基团中的一种,
所述R选自氢、C1~C15的烷基、C6~C18的芳基中的一种;
所述L11、L12独立的选自单键、亚苯基、亚联苯基、亚萘基中的一种。
4.根据权利要求3所述的胺类衍生物,其特征在于,所述Ar2、Ar4选自相同的取代基。
9.一种有机电致发光器件,其特征在于,包括阳极、有机物层、阴极和光取出层,所述有机物层位于阳极和阴极之间,所述有机物层包含空穴传输层、发光层、电子传输层,所述空穴传输层位于阳极和发光层之间,所述电子传输层位于发光层和阴极之间,所述光取出层位于阴极远离阳极的一侧,所述光取出层含有权利要求1~8任一项所述的胺类衍生物。
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CN201910631205.2A CN110256358B (zh) | 2019-07-12 | 2019-07-12 | 一种胺类衍生物及其有机电致发光器件 |
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EP20166566.8A EP3763707B1 (en) | 2019-07-12 | 2020-03-30 | Amine derivative and an organic electroluminescent device thereof |
ES20166566T ES2949041T3 (es) | 2019-07-12 | 2020-03-30 | Derivado de amina y un dispositivo electroluminiscente orgánico del mismo |
PL20166566.8T PL3763707T3 (pl) | 2019-07-12 | 2020-03-30 | Pochodna aminy i jej organiczne urządzenie elektroluminescencyjne |
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CN110669025A (zh) * | 2019-09-26 | 2020-01-10 | 吉林奥来德光电材料股份有限公司 | 芳胺类化合物及其制备方法和包含该化合物的有机发光器件 |
CN110964002A (zh) * | 2019-12-13 | 2020-04-07 | 长春海谱润斯科技有限公司 | 一种芳胺类衍生物及其有机发光器件 |
CN111205237B (zh) * | 2020-01-13 | 2020-12-29 | 长春海谱润斯科技股份有限公司 | 一种三胺衍生物及其有机电致发光器件 |
CN111785849B (zh) * | 2020-07-14 | 2021-02-02 | 长春海谱润斯科技股份有限公司 | 一种含有覆盖层的顶发射有机电致发光器件 |
CN111892586B (zh) * | 2020-09-08 | 2021-08-24 | 长春海谱润斯科技股份有限公司 | 一种苯并五元含n杂环杂芳基胺化合物及其有机电致发光器件 |
CN111978329B (zh) * | 2020-09-09 | 2023-04-07 | 烟台显华化工科技有限公司 | 一种化合物、空穴传输材料、有机电致发光器件和显示装置 |
WO2022100099A1 (zh) * | 2020-11-13 | 2022-05-19 | 广州华睿光电材料有限公司 | 一种用于有机电致发光器件的化合物 |
CN113582938A (zh) * | 2021-07-30 | 2021-11-02 | 上海天马有机发光显示技术有限公司 | 一种有机化合物及其应用 |
WO2023039010A1 (en) * | 2021-09-08 | 2023-03-16 | Academia Sinica | Compounds and their uses for treating neurodegenerative disease |
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Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4769292A (en) * | 1987-03-02 | 1988-09-06 | Eastman Kodak Company | Electroluminescent device with modified thin film luminescent zone |
EP0879868B1 (en) * | 1997-05-19 | 2002-04-03 | Canon Kabushiki Kaisha | Organic compound and electroluminescent device using the same |
JP3508984B2 (ja) * | 1997-05-19 | 2004-03-22 | キヤノン株式会社 | 有機化合物及び該有機化合物を用いた発光素子 |
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US9051274B2 (en) | 2011-06-24 | 2015-06-09 | Semiconductor Energy Laboratory Co., Ltd. | Triarylamine compound, light-emitting element, light-emitting device, electronic device, and lighting device |
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JP6060530B2 (ja) * | 2012-06-12 | 2017-01-18 | ソニー株式会社 | 有機電界発光素子及び表示装置 |
JP5749870B1 (ja) | 2013-07-03 | 2015-07-15 | 保土谷化学工業株式会社 | 有機エレクトロルミネッセンス素子 |
CN108047130A (zh) | 2017-12-05 | 2018-05-18 | 李现伟 | 苯并蒽类有机电致发光材料、发光器件及显示器 |
CN108203406A (zh) | 2017-12-05 | 2018-06-26 | 李现伟 | 苯并芴类有机电致发光材料、发光器件及显示器 |
CN108191744A (zh) | 2017-12-05 | 2018-06-22 | 李现伟 | 苯并芴类有机电致发光材料、发光器件及显示器 |
CN107936955A (zh) | 2017-12-05 | 2018-04-20 | 李现伟 | 7H‑苯并[de]蒽类有机电致发光材料、发光器件及显示器 |
CN109574857A (zh) | 2018-11-29 | 2019-04-05 | 长春海谱润斯科技有限公司 | 一种有机电致发光器件用芳香胺化合物及其有机电致发光器件 |
CN109535012A (zh) * | 2018-12-17 | 2019-03-29 | 长春海谱润斯科技有限公司 | 一种有机电致发光器件 |
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CN110669025A (zh) * | 2019-09-26 | 2020-01-10 | 吉林奥来德光电材料股份有限公司 | 芳胺类化合物及其制备方法和包含该化合物的有机发光器件 |
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