CN114907359A - Organic compound and application thereof in organic electroluminescent device - Google Patents
Organic compound and application thereof in organic electroluminescent device Download PDFInfo
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- CN114907359A CN114907359A CN202210726540.2A CN202210726540A CN114907359A CN 114907359 A CN114907359 A CN 114907359A CN 202210726540 A CN202210726540 A CN 202210726540A CN 114907359 A CN114907359 A CN 114907359A
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- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 51
- 239000000463 material Substances 0.000 claims abstract description 69
- 239000000126 substance Substances 0.000 claims abstract description 12
- 239000010410 layer Substances 0.000 claims description 64
- 150000001875 compounds Chemical class 0.000 claims description 40
- 125000003118 aryl group Chemical group 0.000 claims description 31
- 125000001072 heteroaryl group Chemical group 0.000 claims description 31
- 239000012044 organic layer Substances 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 17
- 229910052805 deuterium Inorganic materials 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- 229910052717 sulfur Inorganic materials 0.000 claims description 15
- 230000015572 biosynthetic process Effects 0.000 claims description 14
- 125000005842 heteroatom Chemical group 0.000 claims description 14
- 150000002431 hydrogen Chemical class 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 230000005525 hole transport Effects 0.000 claims description 13
- 125000006574 non-aromatic ring group Chemical group 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 12
- 238000002347 injection Methods 0.000 claims description 11
- 239000007924 injection Substances 0.000 claims description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 9
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 239000011737 fluorine Substances 0.000 claims description 7
- 125000005549 heteroarylene group Chemical group 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 229910052698 phosphorus Inorganic materials 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 125000006761 (C6-C60) arylene group Chemical group 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 229910052701 rubidium Inorganic materials 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 2
- 229910052796 boron Inorganic materials 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 238000013086 organic photovoltaic Methods 0.000 claims description 2
- 108091008695 photoreceptors Proteins 0.000 claims description 2
- 239000010409 thin film Substances 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims 2
- 238000005401 electroluminescence Methods 0.000 abstract description 2
- -1 1-methylpentyl Chemical group 0.000 description 56
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 45
- 238000000034 method Methods 0.000 description 17
- 125000001424 substituent group Chemical group 0.000 description 16
- 238000001704 evaporation Methods 0.000 description 13
- 238000003786 synthesis reaction Methods 0.000 description 13
- 230000032258 transport Effects 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 8
- 230000008020 evaporation Effects 0.000 description 8
- 125000001931 aliphatic group Chemical group 0.000 description 7
- 150000002500 ions Chemical class 0.000 description 7
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 7
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 239000003086 colorant Substances 0.000 description 5
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- 238000002156 mixing Methods 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 125000002877 alkyl aryl group Chemical group 0.000 description 4
- 125000004414 alkyl thio group Chemical group 0.000 description 4
- 125000001691 aryl alkyl amino group Chemical group 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 4
- 239000007806 chemical reaction intermediate Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 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 description 3
- 125000004062 acenaphthenyl group Chemical group C1(CC2=CC=CC3=CC=CC1=C23)* 0.000 description 3
- 125000003282 alkyl amino group Chemical group 0.000 description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 3
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 3
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 3
- 125000001769 aryl amino group Chemical group 0.000 description 3
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- 125000005110 aryl thio group Chemical group 0.000 description 3
- 125000004104 aryloxy group Chemical group 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 3
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- 239000002019 doping agent Substances 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
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- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
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- 125000002950 monocyclic group Chemical group 0.000 description 3
- 125000003367 polycyclic group Chemical group 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- BWHDROKFUHTORW-UHFFFAOYSA-N tri-tert-butylphosphine Substances CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000005916 2-methylpentyl group Chemical group 0.000 description 2
- 125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 239000010405 anode material Substances 0.000 description 2
- 125000000732 arylene group Chemical group 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 229920001940 conductive polymer Polymers 0.000 description 2
- 230000021615 conjugation Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 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 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 description 2
- 125000005462 imide group Chemical group 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
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- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 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 2
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 2
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 2
- 125000005561 phenanthryl group Chemical group 0.000 description 2
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
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- 125000001725 pyrenyl group Chemical group 0.000 description 2
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- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- 125000006749 (C6-C60) aryl group Chemical group 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
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- 241001391944 Commicarpus scandens Species 0.000 description 1
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- 229910004039 HBF4 Inorganic materials 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
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- 229910021529 ammonia Inorganic materials 0.000 description 1
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- 230000009286 beneficial effect Effects 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
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- 125000000707 boryl group Chemical group B* 0.000 description 1
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- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
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- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
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- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical compound C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 1
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- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 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
- 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
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- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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Abstract
The invention relates to the field of organic electroluminescent materials, in particular to an organic compound and application thereof in an organic electroluminescent device. The chemical structure of the organic compound is shown as formula I:
Description
Technical Field
The invention relates to the field of organic electroluminescent materials, in particular to an organic compound and application thereof in an organic electroluminescent device.
Background
Organic electroluminescent diodes (abbreviated as OLEDs) are widely used in various displays because of their characteristics of self-luminescence, solid state, flexibility, high efficiency, etc. Phosphorescent light emitting materials theoretically have an internal quantum light emitting efficiency of 100%, while ordinary fluorescent materials have a light emitting efficiency of only 25%, and thus are commonly used in OLEDs. The phosphorescent light-emitting material is mainly formed by mixing a light-emitting host material and a light-emitting guest material. Holes and electrons are respectively injected from the anode and the cathode, injected into a host of the light-emitting layer through the hole transport layer and the electron transport layer and are combined to form excitons, and the energy of the excitons is transferred to the light-emitting object from the light-emitting host to emit light. The mass ratio of the luminescent host to the luminescent layer is generally 99% to 85%. The properties of the material of the light emitting host are therefore crucial for the performance of the OLED.
The phosphorescent light-emitting main material is required to have a proper triplet state energy level, well balanced hole and electron mobility and good thermal stability. The existing phosphorescent host material mainly comprises carbazole or carbazole derived varieties, and particularly, a compound containing a plurality of aromatic fused rings is a preferable material for the phosphorescent host, because the compound has a very suitable triplet state energy level and can well regulate and control the energy level. However, the material has strong rigidity and large conjugate area, and the evaporation temperature of the material is generally higher. And the C-N structure of carbazoles is unstable, and C-N bonds are easy to break in a long-term evaporation process, so that the material is cracked. To solve this problem, one method is to reduce the molecular weight and the conjugation area, and the other method is to substitute the hydrogen atom on the aromatic ring with an alkyl group or a heteroalkyl group. However, the energy level is difficult to regulate and control and the triplet state change is very high due to the adoption of the reduction of the molecular weight and the conjugation area, so that the collocation of devices is not facilitated; the hydrogen atoms on the aromatic ring are replaced by alkyl or heteroalkyl, so that the evaporation temperature of the material can be reduced, the service life of the material can be prolonged, but the alkyl can generate a large amount of influences such as rotary vibration, telescopic vibration and the like, the energy can be influenced to be transferred to the luminescent molecules of the doping body, and the efficiency is low.
The OLED display panel is usually composed of red light, green light and blue light in an array manner. When one color is lit while power is applied, the other two colors remain dark if not applied. In reality, two other colors appear, and although the two colors are not energized, the two colors also appear to be slightly bright, so that the colors are not pure. This reduction in color purity is particularly acute when just lit, a condition known as pixel crosstalk. The crosstalk of red light and green light is more serious because the red light and the green light have the lowest theoretical lighting voltage. Currently, panel factories make some effort from device or panel pixel designs, but still have limited success.
Disclosure of Invention
In view of the above-mentioned drawbacks of the prior art, it is an object of the present invention to provide an organic compound and its use in an organic electroluminescent device for solving the problems of the prior art.
To achieve the above and other related objects, the present invention provides, in one aspect, an organic compound having a chemical structure represented by formula i:
at least two adjacent carbon atoms in formula I are connected with other carbon atoms and/or heteroatoms to form a non-aromatic ring, and the heteroatoms are selected from O, S or N;
x is selected from O, S, NR a Or CR a R b Wherein R is a 、R b Each independently selected from hydrogen, deuterium, substituted or unsubstituted straight chain or branched alkyl with C1-C10, substituted or unsubstituted cycloalkyl with C3-C20, substituted or unsubstituted heteroalkyl with C1-C10, substituted or unsubstituted aryl with C6-C60, substituted or unsubstituted heteroaryl with C5-C30, substituted or unsubstituted amine with C6-C30, or Ra and Rb are connected to form substituted or unsubstitutedA ring of (a);
y is selected from substituted or unsubstituted aryl of C6-C60, substituted or unsubstituted heteroaryl of C5-C60,
Wherein R is c To the nitrogen atom in formula I, R c Selected from the group consisting of substituted or unsubstituted C6-C60 arylene, substituted or unsubstituted C5-C30 heteroarylene; r is d 、R e And R f Each independently selected from hydrogen, deuterium, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C5-C30 heteroaryl, substituted or unsubstituted C6-C30 amine, or R c 、R d 、R e And R f Any two of which are linked to form a substituted or unsubstituted ring;
R 1 ～R 3 each independently selected from hydrogen, deuterium, fluorine, carbon trifluoride, cyano, nitro, substituted or unsubstituted C1-C10 linear or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C10 heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl, or wherein two or more adjacent groups are linked to each other to form a substituted or unsubstituted ring;
m is 0-6, n is 0-2, and q is 0-4.
In another aspect, the present invention provides a composition comprising the aforementioned organic compound of the present invention and a second host compound selected from one or more of the following chemical structures:
another aspect of the present invention provides a light-emitting host material, including the organic compound described above, and/or the composition described above.
In another aspect, the invention provides an organic layer comprising the aforementioned light-emitting host material.
In another aspect, the present invention provides the use of the organic compound, the composition, and/or the luminescent host material as described above in an organic electroluminescent device.
In another aspect, the present invention provides an organic electroluminescent device comprising a first electrode, a second electrode and an organic layer, wherein the organic layer is at least one of a hole injection layer, a hole transport layer, a light emitting layer, an electron injection layer or an electron transport layer, and the organic layer comprises the organic compound, the composition and/or the light emitting host material.
In another aspect, the present invention provides a display or lighting device comprising the organic electroluminescent device as described above.
Compared with the prior art, the invention has the beneficial effects that:
the organic compound is applied to the field of organic electroluminescence, can reduce the use temperature, prolong the service life and reduce the problem of luminous crosstalk of a luminous panel.
Drawings
Fig. 1 is a schematic view of one structure of an organic electroluminescent device (top emission device) in the example.
Fig. 2 is another schematic structural view of the organic electroluminescent device in the example (bottom emission device).
In the figure:
101 substrate
102 first electrode
103 hole injection layer
104 first hole transport layer
105 second hole transport layer
106 light emitting layer
107 hole blocking layer
108 electron transport layer
109 second electrode
110 coating
Detailed Description
Hereinafter, embodiments of specifically disclosed organic compounds and their use in organic electroluminescent devices are described in detail. Other advantages and effects of the present invention will be readily apparent to those skilled in the art from the disclosure herein. The invention is capable of other and different embodiments and of being practiced or of being carried out in various ways, and its several details are capable of modification in various respects, all without departing from the spirit and scope of the present invention.
Before the present embodiments are further described, it is to be understood that the scope of the invention is not limited to the particular embodiments described below; it is also to be understood that the terminology used in the examples herein is for the purpose of describing particular embodiments only, and is not intended to limit the scope of the present invention; in the description and claims of the present application, the singular forms "a", "an" and "the" include plural referents unless the context clearly dictates otherwise.
When numerical ranges are given in the examples, it is understood that both endpoints of each of the numerical ranges and any value therebetween can be selected unless the invention otherwise indicated. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. In addition to the specific methods, devices, and materials used in the examples, any methods, devices, and materials similar or equivalent to those described in the examples may be used in the practice of the invention in addition to the specific methods, devices, and materials used in the examples, in keeping with the knowledge of one skilled in the art and with the description of the invention.
The inventor of the invention provides a novel material design scheme through a great deal of research and study, and can perfectly and simultaneously solve the two problems in the prior art. The technical scheme of the invention is to add a non-aromatic ring into a carbazole-derived aromatic polycyclic molecular structure, wherein the non-aromatic ring can be cycloalkyl or heterocycloalkyl, for example. The cycloalkyl or heterocycloalkyl can reduce the evaporation temperature of the material as the alkyl replaces hydrogen atoms, and meanwhile, the molecular rotation and vibration of the cycloalkyl can be limited, so that adverse effects cannot be caused and the luminous efficiency cannot be reduced in the process of transferring the host energy to an object. And the addition of the cycloalkyl or the heterocycloalkyl can effectively improve the dielectric constant of the material, thereby improving the starting voltage and solving the problem of pixel crosstalk to a great extent. On this basis, the present application has been completed.
Phosphorescent light-emitting host materials in order to balance the number of holes and electrons, two methods are generally used, one is to add a hole-transporting light-emitting host and an electron-transporting light-emitting host at the same time. And the other is that a hole transmission group and an electron transmission group are simultaneously introduced into the same molecule. Both of these methods are often found in practical applications. The solution of the present invention is applicable to both of the above two carrier transport balancing methods.
Examples of the substituent in the present invention are described below, but the substituent is not limited thereto:
[ substituted or unsubstituted ] means substituted with one or more substituents selected from: deuterium, a halogen group, a cyano group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amino group, a phosphine oxide group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an alkylsulfonyl group, an arylsulfonyl group, a silyl group, a boryl group, an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, an aralkyl group, an aralkenyl group, an alkylaryl group, an alkylamino group, an aralkylamino group, a heteroarylamino group, an arylamino group, an arylphosphino group, and a heteroaryl group, an acenaphthenyl group, a derivative group of acenaphthenyl group, or unsubstituted; or substituted with a substituent linking two or more of the substituents exemplified above, or unsubstituted. For example, "a substituent linking two or more substituents" may include a biphenyl group, i.e., the biphenyl group may be an aryl group, or a substituent linking two phenyl groups.
[ alkyl ] may be linear or branched, and the number of carbon atoms is not particularly limited. In some embodiments, alkyl includes, but is not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2-dimethylheptyl, 1-ethyl-propyl, 1-dimethyl-propyl, n-butyl, 2-methylpentyl, 4-methyl-2-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propyl, 2-pentyl, 2-dimethylheptyl, 1, 2-propyl, 2-pentyl, and mixtures thereof, Isohexyl, 4-methylhexyl, 5-methylhexyl, and the like.
The above description of alkyl groups also applies to alkyl groups in aralkyl, aralkylamino, alkylaryl, and alkylamino groups.
[ cycloalkyl ] may be cyclic, and the number of carbon atoms is not particularly limited. In some embodiments, cycloalkyl includes, but is not limited to, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2, 3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2, 3-dimethylcyclohexyl, 3, 4, 5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like.
[ heteroalkyl ] may be a linear or branched alkyl group containing a heteroatom, and the number of carbon atoms is not particularly limited. In some embodiments, heteroalkyl groups include, but are not limited to, alkoxy, alkylthio, alkylsulfonyl, and the like. The alkoxy group may include, for example, but not limited to, methoxy, ethoxy, n-propoxy, isopropoxy (isopropoxyxy), isopropoxy (i-propyloxy), n-butoxy, isobutoxy, t-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexoxy, 3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, and the like. Alkylthio groups may include, for example, but are not limited to, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, tert-butylthio, sec-butylthio, n-pentylthio, neopentylthio, isopentylthio, n-hexylthio, 3-dimethylbutylthio, 2-ethylbutylthio, n-octylthio, n-nonylthio, n-decylthio, benzylthio, and the like.
[ heterocycloalkyl ] may be a cycloalkyl group containing a heteroatom, and the number of carbon atoms is not particularly limited. In some embodiments, the heterocycloalkyl group comprisesIncluding but not limited to
And the like.
[ aryl ] is not particularly limited, and the aryl group may be a monocyclic aryl group or a polycyclic aryl group. In some embodiments, monocyclic aryl groups include, but are not limited to, phenyl, biphenyl, terphenyl, quaterphenyl, pentabiphenyl, and the like. Polycyclic aryl groups include, but are not limited to, naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, fluorenyl, and the like. The fluorenyl group can be substituted, such as 9, 9 '-dimethylfluorenyl, 9' -dibenzofluorenyl, and the like. Further, two of the substituents may be combined with each other to form a spiro ring structure, for example, 9' -spirobifluorenyl group and the like.
The above description of aryl groups applies to arylene groups, except that arylene groups are divalent.
The above description of aryl groups applies to aryl groups in aryloxy, arylthio, arylsulfonyl, arylphosphino, aralkyl, aralkylamino, aralkenyl, alkylaryl, arylamino, and arylheteroarylamino groups.
[ heteroaryl ] contains one or more of N, O, P, S, Si and Se as heteroatoms. Heteroaryl groups include, but are not limited to, pyridyl, pyrrolyl, pyrimidinyl, pyridazinyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, dithiazolyl, tetrazolyl, pyranyl, thiopyranyl, pyrazinyl, oxazinyl, thiazinyl, dioxanyl, triazinyl, tetrazinyl, quinolinyl, isoquinolinyl, quinolinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, acridinyl, xanthenyl, phenanthridinyl, naphthyridinyl, triazaindenyl, indolyl, indolinyl, indolizinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, benzothiazolyl, benzoxazolyl, benzimidazolyl, benzothienyl, benzofuranyl, dibenzothienyl, dibenzofuranyl, carbazolyl, benzocarbazolyl, and benzocarbazolyl, Dibenzocarbazolyl, indolocarbazolyl, indenocarbazolyl, phenazinyl, imidazopyridinyl, phenazinyl, phenanthridinyl, phenanthrolinyl, phenothiazinyl, imidazopyridinyl, imidazophenanthridinyl, benzimidazoloquinazolinyl, benzimidazolophhenanthridinyl, spiro [ fluorene-9, 9' -xanthene ], benzidinaphthyl, dinaphthofuranyl, naphthobenzofuranyl, dinaphthothiophenyl, naphthobenzothienyl, triphenylphosphine oxide, triphenylborane, and the like.
The above description of heteroaryl groups applies to heteroaryl groups in heteroarylamino and arylheteroarylamino groups.
The above description of heteroaryl groups can be used for heteroarylenes, except that the heteroarylene group is divalent.
[ AMINO ] AMINO is an organic compound in which the hydrogen atom of ammonia is replaced with an alkyl group. For example, the number of alkyl carbon atoms may be 6 to 30.
[ adjacent groups ] may mean a substituent that replaces an atom directly attached to an atom substituted with the corresponding substituent, a substituent that is located sterically closest to the corresponding substituent, or another substituent that replaces an atom substituted with the corresponding substituent.
[ CONNECTED TO FORM A SUBSTITUTED OR UNSUBSTITUTED RING ] may mean, for example, a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted aliphatic heterocyclic ring.
An aliphatic hydrocarbon ring means a ring formed only of carbon and hydrogen atoms as a non-aromatic ring. The aliphatic hydrocarbon ring includes, but is not limited to, cycloalkylene, and specific examples may include cyclopropylene, cyclobutylene, cyclobutenyl, cyclopentylene, cyclopentenylene, cyclohexylene, cyclohexenylene, 1, 4-cyclohexadienylene, cycloheptenylene, cyclooctenylene, and the like.
The aromatic hydrocarbon ring is an aromatic ring formed only of carbon and hydrogen atoms. Specific examples of the aromatic hydrocarbon ring may include phenyl, naphthyl, anthryl, phenanthryl, perylenyl, anthryl, triphenylenyl, phenalkenyl, pyrenyl, tetracenyl, pentacenyl, fluorenyl, indenyl, acenaphthenyl, benzofluorenyl, spirofluorenyl, and the like, but are not limited thereto.
By aliphatic heterocycle is meant an aliphatic ring containing one or more heteroatoms. Specific examples of the aliphatic heterocyclic ring may include, but are not limited to, oxiranyl, tetrahydrofuryl, 1, 4-dioxaylethyl, pyrrolidinyl, piperidinyl, morpholinyl, oxetanyl, azocyclohexane (azoxane) group, and the like.
The aliphatic hydrocarbon ring may be monocyclic or polycyclic.
In a first aspect, the present invention provides an organic compound having a chemical structure represented by formula i: the chemical structure of the organic compound is shown as formula I:
at least two adjacent carbon atoms in formula I are linked to other carbon atoms and/or heteroatoms selected from O, S, or N to form a non-aromatic ring.
X is selected from O, S, NR a Or CR a R b Wherein R is a 、R b Each independently selected from hydrogen, deuterium, substituted or unsubstituted straight or branched alkyl having C1-C10, substituted or unsubstituted cycloalkyl having C3-C20, substituted or unsubstituted heteroalkyl having C1-C10, substituted or unsubstituted aryl having C6-C60, substituted or unsubstituted heteroaryl having C5-C30, substituted or unsubstituted amine having C6-C30, or Ra and Rb are linked to form a substituted or unsubstituted ring;
y is selected from substituted or unsubstituted aryl of C6-C60, substituted or unsubstituted heteroaryl of C5-C60,
(the foregoing structural formula may be abbreviated as N (R) c R d R e )、C(＝O)R c R d 、Si(R c R d R e R f )、P(＝O)(R c R d R e )、B(R c R d R e )、S(＝O) 2 (R c R d ) Wherein R) is c To the nitrogen atom in formula I, R c A heteroarylene selected from substituted or unsubstituted C6-C60 arylene, substituted or unsubstituted C5-C30; r d 、R e And R f Each independently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted aryl groups of C6-C60, substituted or unsubstituted heteroaryl groups of C5-C30, substituted or unsubstituted amine groups of C6-C30, or R c 、R d 、R e And R f Any two of which are linked to form a substituted or unsubstituted ring;
R 1 ～R 3 each independently selected from hydrogen, deuterium, fluorine, carbon trifluoride, cyano, nitro, substituted or unsubstituted C1-C10 linear or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C10 heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl, or wherein two or more adjacent groups are linked to each other to form a substituted or unsubstituted ring;
m is 0-6, n is 0-2, and q is 0-4.
In some embodiments, m, n, and q are integers, and m can take a value of, for example, 0 to 3, 3 to 6, 0, 1, 2, 3, 4, 5, and 6. The value of n can be, for example, 0 to 1, 1 to 2, 0, 1, or 2. The value of q may be, for example, 0 to 2, 2 to 4, 0, 1, 2, 3, or 4.
For example, C1-C10 means that the number of carbon atoms is 1-10. C6-C30 means that the number of carbon atoms is 6-30. Elsewhere in this text, as explained above.
In the organic compound provided by the invention, the non-aromatic ring is selected from cycloalkyl or heterocycloalkyl. The non-aromatic ring is preferably selected from substituted or unsubstituted C3-C12 cycloalkyl, or substituted or unsubstituted C3-C10 heterocycloalkyl. In some embodiments, the number of cycloalkyl groups can be, for example, 3 to 5, 5 to 10, or 10 to 12, etc. The number of heterocycloalkyl groups may be, for example, 3 to 5, 5 to 8, 8 to 10, or the like.
More preferably, the non-aromatic ring is selected from any of the following groups: the non-aromatic ring is selected from any one of the following groups:
any two adjacent carbon atom positions on the above groups coincide with any two adjacent carbon atom positions in formula i.
At least two adjacent carbon atoms of formula i are bonded to form a non-aromatic ring by:
the position of the asterisked carbon atom on the above-mentioned group coincides with any two adjacent asterisked carbon atom positions in formula I.
In the organic compound provided by the invention, the Y is selected from any one of the following groups or any combination formed by two or more groups:
wherein the content of the first and second substances,
ar is selected from substituted or unsubstituted aryl of C6-C30, or substituted or unsubstituted heteroaryl of C5-C30;
A 1 and A 2 Each independently selected from hydrogen, deuterium, fluorine, carbon trifluoride (-CF) 3 ) Cyano (-CN), nitro (-NO) 2 ) Substituted or unsubstituted aryl of C6-C20, substituted or unsubstituted heteroaryl of C5-C20;
X 1 ～X 7 each independently selected from O, S orCR e R f Wherein R is e 、R f Each independently selected from hydrogen, deuterium, fluorine, carbon trifluoride, cyano, nitro, linear or branched C1-C10 alkyl, and substituted or unsubstituted C3-C20 cycloalkyl;
Z 1 ～Z 8 each is independently selected from C, or N;
any position on the above groups can be used as a connecting site with the nitrogen atom in the formula I.
By way of illustration, in some embodiments,
for example, can be
And the like. Specific choices of other groups can be made with reference to this variation.
In the organic compound provided by the invention, R is a Selected from any one or a combination of two or more of the following groups:
methyl, ethyl,
Any position on the above groups can be used as the attachment site for the adjacent group in formula I. For example, X is selected from NR a In the case where any position on the above groups is defined as being bonded to NR a The attachment site of the upper nitrogen atom. As another example, X is selected from CR a R b In the case where any position on the above-mentioned group is considered to be bonded with CR a R b The attachment site of the upper carbon atom.
By way of example, in some embodiments,
for example, can be
Specific choices of other groups can be made with reference to this variation.
In the organic compound provided by the invention, R is b Selected from methyl, ethyl, or phenyl.
In the organic compound provided by the invention, R is a Or R b Wherein the heteroatoms in the heteroalkyl or heteroaryl group are each independently selected from O, N, S, P, Si, Se, or B.
In the organic compound provided by the invention, R is a Or R b The substituted or unsubstituted heteroaryl of C5-C30 is selected from substituted or unsubstituted carbazolyl of C6-C30.
In the organic compound provided by the invention, the CR a R b In, R a 、R b Connection formation
R a 、R b The ring formed by the connection, in particular, R a 、R b Bonded to CR a R b C in (b) together form a ring.
In the organic compound provided by the invention, R is 1 ～R 3 Each independently selected from hydrogen, deuterium, methyl, ethyl, isopropyl, tert-butyl, fluoro, carbon trifluoride, cyano, nitro, or phenyl.
In the organic compound provided by the invention, R is c Wherein the hetero atom in the heteroarylene group is selected from O, N, S, P, Si, Se or B.
In the organic compound provided by the invention, R is d 、R e And R f Wherein the heteroatoms in the heteroaryl group are each independently selected from O, N, S, P, Si, Se, or B.
In the organic compound provided by the invention, the substituted or unsubstituted C5-C30 heteroaryl is selected from substituted or unsubstituted C6-C30 carbazolyl.
In the organic compound provided by the present invention, the organic compound is selected from any one of the following chemical structures:
specifically, the above structure may be unsubstituted or substituted with one or more substituents selected from the group consisting of the following. For example, deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amine group, a phosphine oxide group, an alkoxy group, an aryloxy group, an alkylthio group, an arylthio group, an alkylsulfonyl group, an arylsulfonyl group, a silyl group, a boron group, an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, an aralkyl group, an aralkenyl group, an alkylaryl group, an alkylamino group, an aralkylamino group, a heteroarylamino group, an arylamino group, an arylheteroarylamino group, an arylphosphino group, a heteroaryl group and the like may be mentioned.
In a second aspect, the present invention provides a composition comprising an organic compound according to the first aspect of the present invention and a second host compound. The second host compound is selected from one or more of the following chemical structures:
the organic compound according to the first aspect of the present invention may be used as a first host compound, and may be used as a light-emitting host material together with a second host compound.
In a third aspect, the present invention provides a light-emitting host material comprising the organic compound of the first aspect of the present invention, and/or the composition of the second aspect of the present invention.
A fourth aspect of the invention provides an organic layer comprising a light-emissive host material according to the first aspect of the invention.
A fifth aspect of the invention provides the use of an organic compound according to the first aspect of the invention, a composition according to the second aspect of the invention, and/or an organic layer according to the third aspect of the invention in an organic electroluminescent device.
A sixth aspect of the present invention provides an organic electroluminescent device, including a first electrode, a second electrode, and one or more organic layers disposed between the first electrode and the second electrode, wherein the organic layers are in a bottom or top light-emitting device structure, and may be in a single-layer structure or a multi-layer tandem structure in which two or more organic layers are laminated, and the organic layers include, for example, at least one layer selected from a hole injection layer, a hole transport layer, a light-emitting layer, an electron injection layer, and an electron transport layer. Can be prepared using common methods and materials for preparing organic electroluminescent devices. The organic layer comprises an organic compound according to the first aspect of the invention, a composition according to the second aspect of the invention, and/or a light-emitting host material according to the third aspect of the invention.
The light-emitting layer comprises the organic compound according to the first aspect of the present invention and/or the composition according to the second aspect of the present invention. The organic electroluminescent device adopts the organic compound and the composition as the luminescent main body material of the organic electroluminescent device.
In the organic electroluminescent device provided by the invention, the first electrode is used as an anode layer, and the anode material can be a material with a large work function, so that holes can be smoothly injected into the organic layer. More examples are metals, metal oxides, combinations of metals and oxides, conductive polymers, and the like. The metal oxide may be, for example, Indium Tin Oxide (ITO), zinc oxide, Indium Zinc Oxide (IZO), or the like.
In the organic electroluminescent device provided by the invention, the second electrode is used as a cathode layer, and the cathode material can be a material with a small work function, so that electrons can be smoothly injected into the organic layer. The cathode material may be, for example, a metal or a multilayer structure material. The metal may be, for example, magnesium, silver, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, tin, and lead, or alloys thereof. The cathode material is preferably selected from magnesium and silver.
In the organic electroluminescent device provided by the present invention, a material of the hole injection layer, preferably a material having a Highest Occupied Molecular Orbital (HOMO) between the work function of the anode material and the HOMO of the surrounding organic layer, is used as a material that advantageously receives holes from the anode at a low voltage.
In the organic electroluminescent device provided by the invention, the material of the hole transport layer is a material having high mobility to holes and is suitable for receiving the holes from the anode or the hole injection layer and transporting the holes to the light emitting layer. Materials for the hole transport layer include, but are not limited to, organic materials of arylamines, conductive polymers, block copolymers having both conjugated and non-conjugated moieties, and the like.
In the organic electroluminescent device provided by the present invention, the material of the light emitting layer may be generally selected from materials having good quantum efficiency for fluorescence or phosphorescence as materials capable of emitting light in the visible light region by receiving holes and electrons from the hole transport layer and from the electron transport layer, respectively, and combining the holes and the electrons.
In the organic electroluminescent device provided by the present invention, the material of the electron transport layer is a material having a high mobility to electrons and suitable as a material that favorably receives electrons from the cathode and transports the electrons to the light emitting layer.
In the organic electroluminescent device provided by the invention, the material of the covering layer generally has a high refractive index, so that the material can contribute to the improvement of the light efficiency of the organic electroluminescent device, and particularly contributes to the improvement of the external light efficiency.
In the organic electroluminescent device provided by the invention, the organic electroluminescent device is an organic photovoltaic device, an organic luminescent device, an organic solar cell, electronic paper, an organic photoreceptor, an organic thin film transistor and the like.
In another aspect, the invention provides a display or lighting device comprising an organic electroluminescent device according to the invention.
The embodiments of the present invention are illustrated below by specific examples.
Synthesis examples:
the synthesis of the compounds of the invention has the following 3 schemes:
general formula 1:
general formula 2:
general formula 3:
the detailed synthetic procedure is as follows:
example 1
Synthesis of compound a 1:
synthesis of intermediate A1-3:
a1-1(30g, 71.2 mmol), A1-2(14.6g, 85.4mmol) and K were added in this order to a three-necked flask 2 CO 3 (29.4g, 213.6mmol), Pd (OAc) palladium acetate 2 (0.16g, 0.7mmol), triphenylphosphine pph 3 (56.0g, 213.6mmol) was added to 300mL of dichlorobenzene, and the reaction mixture was heated to reflux (180 ℃ C.) and stirred for 24 hours. After the reaction solution was cooled, it was concentrated in vacuo, and the remaining solution was subjected to column chromatography 2 times using toluene and petroleum ether as a washing solution. The collected liquid was evaporated to dryness in vacuo and then toluene was recrystallized to give a solid, which was dried to obtain 14g of an intermediate compound A1-3 in 45% yield. LCMS (ESI ion source) M/Z: 436.3.
synthesis of compound a 1:
a1-3(10g, 22.9mmol), A1-4(4.3g, 22.9mmol), tris (dibenzylideneacetone) dipalladium (Pd) were added to a three-necked flask 2 (dba) 3 (0.4g, 0.46mmol), tri-tert-butylphosphine t-Bu 3 P (0.5g, 2.29mmol), sodium t-butoxide NaOBu-t, (6.6g, 68.7mmol) were stirred in toluene solvent (toluene) under nitrogen, the reaction mixture was warmed to 110 ℃ and stirred for reaction for 3 hours. The reaction solution was cooled to room temperature, extracted with toluene and water, the toluene phase evaporated to dryness, the solid was purified by column chromatography using toluene-petroleum ether, then concentrated in vacuo, and the concentrate was purified by recrystallization from toluene to give 9.4g of compound a1 in 70% yield. LCMS (ESI ion source) M/Z: 588.4. 1 H NMR(DMSO-d 6 ):δ,9.00(d,1H),8.58–8.49(m,1H),7.94–7.81(m,3H),7.79(d,1H),7.71–7.62(m,2H),7.62–7.34(m,15H),7.32(d,1H),2.78–2.64(m,4H),1.75(m,4H).
example 2
Synthesis of compound a 9:
synthesis of Compound A9-3:
a9-1(20g, 48.4mmol), A9-2(10g, 48.4mmol) were added to a three-necked flask,tris (dibenzylideneacetone) dipalladium (Pd) 2 (dba) 3 (0.4g, 0.96mmol), tri-tert-butylphosphine t-Bu 3 P (1.04g, 4.8mmol), sodium tert-butoxide NaOBu-t (13.9g, 145.2mmol) were stirred in toluene solvent (tolumen) under nitrogen atmosphere, and the reaction mixture was heated to 110 ℃ and stirred for reaction for 3 hours. Cooling the reaction liquid to room temperature, extracting with toluene and water, evaporating the toluene phase to dryness, separating and purifying the solid by column chromatography with toluene-petroleum ether, then concentrating in vacuum, and recrystallizing and purifying the concentrated solution with a toluene-ethanol mixed solvent to obtain 17.4g of the A9-3 compound with the yield of 67%. LCMS (ESI ion source) M/Z: 538.2.
synthesis of Compound A9-4:
a9-3(15g, 27.8mmol, K) was added sequentially to a three-necked flask 2 CO 3 (11.5g, 83.4mmol), Pd (OAc) palladium acetate 2 (0.06g, 0.27mmol), tricyclohexylphosphine tetrafluoroborate pcy3-HBF4(0.1g, 2.8mmol), and 300mL of N, N-Dimethylacetamide (DMA) were added to the reaction mixture, and the reaction mixture was stirred at 130 ℃ for 8 hours. After the reaction is finished, cooling, concentrating in vacuum, and performing column chromatography separation and purification on the residual solution by using toluene and petroleum ether as flushing liquid. The collected liquid was evaporated to dryness in vacuo and recrystallized from toluene to give a solid which was dried to obtain 10g of A9-4 intermediate compound in 74% yield. LCMS (ESI ion source) M/Z: 502.2.
synthesis of compound a 9:
a9-4(10g, 19.9mmol), A9-5(3.7g, 19.9mmol), tris (dibenzylideneacetone) dipalladium (Pd) were added to a three-necked flask 2 (dba) 3 (0.17g, 0.2mmol), tri-tert-butylphosphine t-Bu 3 P (0.43g, 2.0mmol), sodium tert-butoxide NaOBu-t, (5.7g, 59.7mmol) were stirred in toluene solvent (toluene) under nitrogen atmosphere, and the reaction mixture was heated to 110 ℃ and stirred for reaction for 3 hours. The reaction solution is cooled to room temperature, toluene and water are used for extraction, the toluene phase is evaporated to dryness, the solid is subjected to column chromatography separation and purification by using toluene-petroleum ether, then vacuum concentration is carried out, and the concentrated solution is subjected to recrystallization purification by using toluene to obtain 9.3g of A9 compound with the yield of 72%. LCMS (ESI ion source) M/Z: 654.8. 1 H NMR(DMSO-d 6 ):δ,8.98(s,1H),8.30–8.23(m,1H),8.07(m,1H),7.99–7.92(m,1H),7.85(d,1H),7.76–7.49(m,10H),7.49–7.27(m,12H),6.92(d,1H),5.93(s,2H)。
example 3
Synthesis of compound a 14:
synthesis of intermediate A14-3:
the synthesis method of A14-3 is the same as that of A1, except that raw material A14-1 is used instead of A1-1, and raw material A14-2 is used instead of A1-2. The yield thereof was found to be 48%. LCMS (ESI ion source) M/Z: 436.3.
synthesis of compound a 14:
the synthesis method of A14 was the same as that of A1, except that A1-3 was replaced with raw material A14-3 and A1-4 was replaced with raw material A14-4. The yield thereof was found to be 73%. LCMS (ESI ion source) M/Z: 602.4. 1 H NMR(DMSO-d 6 )δ，8.09–7.98(m,2H),7.82(d,1H),7.68(d,1H),7.63–7.56(m,3H),7.56–7.48(m,5H),7.48–7.37(m,7H),7.34–7.23(m,2H),7.13(d,1H),2.99–2.90(t,2H),2.76–2.67(t,2H),1.82–1.65(m,4H)。
the rest compounds can be obtained according to the same method of the three syntheses, and are replaced by corresponding raw materials. Compounds prepared by the same method as a1, the first step reaction intermediates of which are listed in table 1:
TABLE 1
The second reaction results of the compounds prepared in the same manner as in A1 are shown in Table 2:
TABLE 2
Compounds prepared by the same method as a9, the first step reaction intermediates of which are listed in table 3:
TABLE 3
Compounds of the same manufacturing process as a9, the second step reaction intermediates of which are listed in table 4:
TABLE 4
Compounds prepared by the same method as a9 and listed as reaction intermediates in the third step in table 5:
TABLE 5
The nuclear magnetic results of the tests are shown in table 6:
TABLE 6
The luminescent dopant that can be collocated can be selected from, but not limited to, the following compounds:
device embodiment:
the compounds of the invention used by the device are purified by sublimation, and the purity is more than 99.98%.
The following structures of the monochromatic device are employed, and the molecules of the present invention are used as host materials of the phosphorescent light-emitting layer or as emitter materials of the green light-emitting layer. Used as the host material of the light-emitting layer. The compound of the present invention can be used in a device of top emission, bottom emission, or two or more light emitting layers.
A top light emitting device as in fig. 1 and a bottom light emitting device as in fig. 2.
Device example 1: as the host material of the red light emitting layer, take the bottom light emitting fabrication method as an example
The preparation process comprises the following steps:
a transparent anode ITO film layer was formed on a glass substrate 101 to a film thickness of 150nm to obtain a first electrode 102 as an anode, and then PD1 was vapor-deposited thereon
And hole transportMaterial HT1
The hole injection layer 103 was formed of the mixed material (2) in a mixing ratio of 3:97 (mass ratio), and then the layer was deposited with HT1 in a thickness of 100nm by evaporation
The first hole transport layer 104 was obtained, and then the compound RP1 was evaporated to a thickness of 100nm
A second hole transport layer 105 was obtained, and then the compound A1 of the present invention was evaporated at an evaporation rate of 55:40:5
Electron transport type luminescent host material NH1
And a light emitting dopant D1
40nm, making red light-emitting unit 106, and vapor-depositing 10nm HB1
Hole blocking layer 107 is formed and then ET1 is evaporated
With Liq
An electron transport layer 108 having a thickness of 30nm was formed at a mixing ratio of 4:6 (mass ratio), and then magnesium silver having a thickness of 100nm (mass ratio of 1: 9) was formed as a second electrode 109.
The device test was performed using a combination test apparatus of keithley power supply, MS-75 spectroradiometer. The voltage is 10mA/cm 2 The voltage and efficiency are 10mA/cm 2 Current efficiency divided by the color coordinate CIEy numerical representation (in Cd/a)The service life is 10mA/cm 2 The time required for the brightness to decay to 95% of the initial brightness at current. The present invention is represented as a relative value with comparative example 1 as 100%.
Device examples 2 to 20 compound A1 in example 1 was replaced with a9, a14, a31, a38, a46, a57, a71, a81, a90, a98, a114, a125, a131, a135, a145, a150, a166, a180, a200 compounds, respectively. As in table 7.
TABLE 7
Comparative compound 1:
device example 21: as the host material of the red light emitting layer, take the top emission manufacturing method as an example
The preparation process comprises the following steps:
forming an Ag/ITO film layer with a thickness of 100nm/15nm on a glass substrate 101 to obtain a first electrode 102 as an anode, and evaporating PD1
With a hole-transporting material HT1
The hole injection layer 103 was formed of the mixed material (2) in a mixing ratio of 3:97 (mass ratio), and then the layer was deposited with HT1 in a thickness of 100nm by evaporation
The first hole transport layer 104 was obtained, and then the compound RP1 was evaporated to a thickness of 100nm
A second hole transport layer 105 was obtained, and then a compound B2 of the present invention was evaporated at an evaporation rate of 95:5
And a light emitting dopant D1
40nm, fabricating a red light emitting unit 106, and evaporating 10nm HB1
Hole blocking layer 107 is formed and then ET1 is evaporated
With Liq
An electron transport layer 108 having a thickness of 30nm was formed at a mixing ratio of 4:6 (mass ratio), a magnesium silver layer having a thickness of 15nm was formed as a second electrode 109 (mass ratio of 1: 9), and a light coupling layer CP1 having a thickness of 70nm was deposited by evaporation
.
The device test was performed using a combination test apparatus of keithley power supply, MS-75 spectroradiometer. The voltage is 10mA/cm 2 The voltage and efficiency are 10mA/cm 2 The current efficiency is divided by the color coordinate CIEy numerical value (unit is Cd/A), and the service life is 10mA/cm 2 The time required for the brightness to decay to 95% of the initial brightness at current. The present invention is represented as a relative value by taking comparative example 2 as 100%.
Device example 21 to device example 41 compound B2 in example 21 was replaced with B11, B18, B28, B39, B46, B58, B66, B81, B90, B99, B109, B115, B122, B133, B137, B152, B164, B170, B181, B189 compounds, respectively. As in table 8.
TABLE 8
Comparative compound 2:
some device configurations are different from the embodiments of the present invention, but still effective.
Thermal stability experiments:
in a chamber for simulating production evaporation, the chamber is provided with a vacuum system, a heating system and a speed detection system. The chamber is evacuated to 10-7torr
After heating for 200 hours, the chamber was opened and the material in the material container was removed and the purity of the remaining material was tested by HPLC. The high temperature resistance of the material was confirmed by comparing the initial material purity before heating and the material purity after heating for 200 hours. The test results are shown in table 8:
TABLE 8
From the results, it can be seen that the compound of the present invention has better heat-resistant stability.
The above description is only for the preferred embodiment of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art should be considered to be within the technical scope of the present invention, and the technical solutions and the inventive concepts thereof according to the present invention should be equivalent or changed within the scope of the present invention.
Claims (16)
1. An organic compound having the chemical structure of formula i:
at least two adjacent carbon atoms in formula I are joined to form a non-aromatic ring by additional carbon atoms and/or heteroatoms selected from O, S, or N;
x is selected from O, S, NR a Or CR a R b Wherein R is a 、R b Each independently selected from hydrogen, deuterium, substituted or unsubstituted straight or branched alkyl having C1-C10, substituted or unsubstituted cycloalkyl having C3-C20, substituted or unsubstituted heteroalkyl having C1-C10, substituted or unsubstituted aryl having C6-C60, substituted or unsubstituted heteroaryl having C5-C30, substituted or unsubstituted amine having C6-C30, or Ra and Rb are linked to form a substituted or unsubstituted ring;
y is selected from substituted or unsubstituted aryl of C6-C60, substituted or unsubstituted heteroaryl of C5-C60,
Wherein R is c To the nitrogen atom in formula I, R c Selected from the group consisting of substituted or unsubstituted C6-C60 arylene, substituted or unsubstituted C5-C30 heteroarylene; r is d 、R e And R f Each independently selected from the group consisting of hydrogen, deuterium, substituted or unsubstituted aryl groups of C6-C60, substituted or unsubstituted heteroaryl groups of C5-C30, substituted or unsubstituted amine groups of C6-C30, or R c 、R d 、R e And R f Any two of which are linked to form a substituted or unsubstituted ring; r 1 ～R 3 Each independently selected fromHydrogen, deuterium, fluorine, carbon trifluoride, cyano, nitro, substituted or unsubstituted C1-C10 linear or branched alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C10 heteroalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl, or wherein two or more adjacent groups are linked to each other to form a substituted or unsubstituted ring;
m is 0-6, n is 0-2, and q is 0-4.
2. The organic compound of claim 1, wherein the non-aromatic ring is selected from a substituted or unsubstituted cycloalkyl of C5-C12, or a substituted or unsubstituted heterocycloalkyl of C3-C10; preferably, the non-aromatic ring is selected from any one of the following groups:
any two adjacent carbon atom positions on the above groups coincide with any two adjacent carbon atom positions in formula i.
3. The organic compound of claim 1, wherein Y is selected from any one or a combination of any two or more of the following groups:
wherein the content of the first and second substances,
ar is selected from substituted or unsubstituted aryl of C6-C30, or substituted or unsubstituted heteroaryl of C5-C30;
A 1 and A 2 Each independently selected from the group consisting of hydrogen, deuterium, fluorine, and carbon trifluorideCyano, nitro, substituted or unsubstituted aryl of C6-C20, substituted or unsubstituted heteroaryl of C5-C20;
X 1 ～X 7 each independently selected from O, S or CR e R f Wherein R is e 、R f Each independently selected from hydrogen, deuterium, fluorine, carbon trifluoride, cyano, nitro, linear or branched C1-C10 alkyl, and substituted or unsubstituted C3-C20 cycloalkyl;
Z 1 ～Z 8 each independently selected from C, or N;
any position on the above groups can be used as a linking site to the nitrogen atom in formula I.
4. The organic compound of claim 1, wherein R is a Selected from any one or a combination of two or more of the following groups:
methyl, ethyl,
Any position on the group can be used as a connecting site of the adjacent group in the formula I;
and/or, said R b Selected from methyl, ethyl, or phenyl;
and/or, said R a Or R b Wherein the heteroatoms in the heteroalkyl or heteroaryl group are each independently selected from O, N, S, P, Si, Se, or B;
and/or, said R a Or R b Wherein the substituted or unsubstituted heteroaryl group of C5-C30 is selected from substituted or unsubstituted carbazolyl groups of C6-C30.
5. An organic compound of claim 1, wherein the CR is a R b In, R a 、R b Connection formation
6. The organic compound of claim 1, wherein R is 1 ～R 3 Each independently selected from hydrogen, deuterium, methyl, ethyl, isopropyl, tert-butyl, fluoro, carbon trifluoride, cyano, nitro, or phenyl.
7. The organic compound of claim 1, wherein R is c Wherein the hetero atom in the heteroarylene group is selected from O, N, S, P, Si, Se or B;
and/or, said R d 、R e And R f Wherein the heteroatoms in the heteroaryl group are each independently selected from O, N, S, P, Si, Se, or B; and/or, the substituted or unsubstituted C5-C30 heteroaryl is selected from substituted or unsubstituted C6-C30 carbazolyl.
8. The organic compound according to any one of claims 1 to 7, wherein the organic compound is selected from any one of the following chemical structures:
9. a composition comprising an organic compound according to any one of claims 1 to 8 and a second host compound selected from one or more of the following chemical structures:
10. a light-emitting host material comprising the organic compound according to any one of claims 1 to 8, and/or the composition according to claim 9.
11. An organic layer comprising the light-emitting host material of claim 10.
12. Use of an organic compound according to any one of claims 1 to 8, a composition according to claim 9, a light-emitting host material according to claim 10, and/or an organic layer according to claim 11 in an organic electroluminescent device.
13. An organic electroluminescent device comprising a first electrode, a second electrode and an organic layer, wherein the organic layer is at least one of a hole injection layer, a hole transport layer, a light emitting layer, an electron injection layer or an electron transport layer, and the organic layer comprises the organic compound according to any one of claims 1 to 8, the composition according to claim 9, and/or the light emitting host material according to claim 10.
14. The organic electroluminescent device according to claim 13, wherein the light-emitting layer comprises the organic compound according to any one of claims 1 to 8 and/or the composition according to claim 9.
15. The organic electroluminescent device according to claim 13 or 14, wherein the organic electroluminescent device comprises an organic photovoltaic device, an organic light-emitting device, an organic solar cell, electronic paper, an organic photoreceptor, or an organic thin film transistor.
16. A display or lighting device comprising the organic electroluminescent element as claimed in any one of claims 13 to 15.
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| KR102398180B1 (en) * | 2021-08-31 | 2022-05-17 | 덕산네오룩스 주식회사 | An organic electronic element comprising compound for organic electronic element and an electronic device thereof |
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