CN111423428A - Organic compound, preparation method thereof and organic light-emitting diode - Google Patents
Organic compound, preparation method thereof and organic light-emitting diode Download PDFInfo
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- CN111423428A CN111423428A CN202010379715.8A CN202010379715A CN111423428A CN 111423428 A CN111423428 A CN 111423428A CN 202010379715 A CN202010379715 A CN 202010379715A CN 111423428 A CN111423428 A CN 111423428A
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- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 65
- 238000002360 preparation method Methods 0.000 title claims abstract description 36
- 125000005843 halogen group Chemical group 0.000 claims abstract description 29
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 24
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 14
- 239000002994 raw material Substances 0.000 claims description 61
- 229910052736 halogen Inorganic materials 0.000 claims description 50
- 150000002367 halogens Chemical class 0.000 claims description 50
- 239000000463 material Substances 0.000 claims description 39
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 claims description 28
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 26
- 229910052757 nitrogen Inorganic materials 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 22
- 239000007795 chemical reaction product Substances 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 238000002156 mixing Methods 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 230000035484 reaction time Effects 0.000 claims description 7
- MEMRDSMVFLMGRE-UHFFFAOYSA-N 3-chloronaphthalene-1,2-dione Chemical compound C1=CC=C2C(=O)C(=O)C(Cl)=CC2=C1 MEMRDSMVFLMGRE-UHFFFAOYSA-N 0.000 claims description 6
- 150000001335 aliphatic alkanes Chemical group 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 239000012535 impurity Substances 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- SVPKNMBRVBMTLB-UHFFFAOYSA-N 2,3-dichloronaphthalene-1,4-dione Chemical compound C1=CC=C2C(=O)C(Cl)=C(Cl)C(=O)C2=C1 SVPKNMBRVBMTLB-UHFFFAOYSA-N 0.000 claims description 5
- CCTJHVLTAJTPBV-UHFFFAOYSA-N 2-chloro-1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C(Cl)=CC(=O)C2=C1 CCTJHVLTAJTPBV-UHFFFAOYSA-N 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- 239000007810 chemical reaction solvent Substances 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- JHRIPENGTGSNPJ-UHFFFAOYSA-N 2-amino-4-bromophenol Chemical compound NC1=CC(Br)=CC=C1O JHRIPENGTGSNPJ-UHFFFAOYSA-N 0.000 claims description 4
- DRQWUAAWZFIVTF-UHFFFAOYSA-N 2-amino-5-bromophenol Chemical compound NC1=CC=C(Br)C=C1O DRQWUAAWZFIVTF-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 238000006467 substitution reaction Methods 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 abstract description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 57
- 239000010410 layer Substances 0.000 description 55
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 47
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 238000002347 injection Methods 0.000 description 19
- 239000007924 injection Substances 0.000 description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- 239000007788 liquid Substances 0.000 description 14
- 238000001914 filtration Methods 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical group [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 238000010586 diagram Methods 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000003208 petroleum Substances 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 8
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical group [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 239000012153 distilled water Substances 0.000 description 8
- 230000005525 hole transport Effects 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- CINYXYWQPZSTOT-UHFFFAOYSA-N 3-[3-[3,5-bis(3-pyridin-3-ylphenyl)phenyl]phenyl]pyridine Chemical compound C1=CN=CC(C=2C=C(C=CC=2)C=2C=C(C=C(C=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)=C1 CINYXYWQPZSTOT-UHFFFAOYSA-N 0.000 description 7
- 239000012530 fluid Substances 0.000 description 7
- -1 tri-tert-butylphosphine tetrafluoroborate Chemical compound 0.000 description 7
- 238000001514 detection method Methods 0.000 description 6
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical group [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 6
- 229940125904 compound 1 Drugs 0.000 description 5
- 229940125782 compound 2 Drugs 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- JSEQNGYLWKBMJI-UHFFFAOYSA-N 9,9-dimethyl-10h-acridine Chemical compound C1=CC=C2C(C)(C)C3=CC=CC=C3NC2=C1 JSEQNGYLWKBMJI-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 229940126214 compound 3 Drugs 0.000 description 4
- 229940125898 compound 5 Drugs 0.000 description 4
- 230000003111 delayed effect Effects 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 125000006575 electron-withdrawing group Chemical group 0.000 description 4
- VOFUROIFQGPCGE-UHFFFAOYSA-N nile red Chemical group C1=CC=C2C3=NC4=CC=C(N(CC)CC)C=C4OC3=CC(=O)C2=C1 VOFUROIFQGPCGE-UHFFFAOYSA-N 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000009987 spinning Methods 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 238000007738 vacuum evaporation Methods 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 229920000144 PEDOT:PSS Polymers 0.000 description 2
- 238000001994 activation Methods 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 238000000137 annealing Methods 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000002346 layers by function Substances 0.000 description 2
- 239000012263 liquid product Substances 0.000 description 2
- 229910000510 noble metal Inorganic materials 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- JGAVTCVHDMOQTJ-UHFFFAOYSA-N (4-carbazol-9-ylphenyl)boronic acid Chemical compound C1=CC(B(O)O)=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 JGAVTCVHDMOQTJ-UHFFFAOYSA-N 0.000 description 1
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 1
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- GWXZLFGQCADAEX-UHFFFAOYSA-N CC1(C2=CC=CC=C2N(C=2C=CC=CC12)C1=CC=C(C=C1)OB(O)O)C Chemical compound CC1(C2=CC=CC=C2N(C=2C=CC=CC12)C1=CC=C(C=C1)OB(O)O)C GWXZLFGQCADAEX-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- MBTJJIPZMXCOMB-UHFFFAOYSA-N [4-(9,9-dimethylacridin-10-yl)phenyl]boronic acid Chemical compound C12=CC=CC=C2C(C)(C)C2=CC=CC=C2N1C1=CC=C(B(O)O)C=C1 MBTJJIPZMXCOMB-UHFFFAOYSA-N 0.000 description 1
- TWWQCBRELPOMER-UHFFFAOYSA-N [4-(n-phenylanilino)phenyl]boronic acid Chemical compound C1=CC(B(O)O)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 TWWQCBRELPOMER-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- CELAVSIYCCQNGG-UHFFFAOYSA-N n-(4-cyclohexylphenyl)-4-methyl-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1CCCCC1)C1=CC=C(C)C=C1 CELAVSIYCCQNGG-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007725 thermal activation Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
Abstract
The invention discloses an organic compound, a preparation method thereof and an organic light-emitting diode, wherein the molecular structure of the organic compound is
In the molecular structure, X is selected from carbon atoms or nitrogen atoms, Y is selected from hydrogen atoms, halogen atoms or R, Z is selected from hydrogen atoms, halogen atoms or R, M is selected from hydrogen atoms, halogen atoms or R, and at least one of Y, Z and M is selected from R, and R is an electron-donating group. It can be understood that the technical scheme of the invention provides the organic matterThe compound has high luminous efficiency.
Description
Technical Field
The invention relates to the technical field of organic light emitting, in particular to an organic compound, a preparation method thereof and an organic light emitting diode.
Background
Organic electroluminescent devices (Organic L light-Emitting Diode, O L ED) are receiving attention because of their high efficiency, wide color gamut, low energy consumption, crimpability, and the like, especially in the field of display and lighting, at present, guest materials used in the light-Emitting layer of O L ED are mainly fluorescent materials and phosphorescent materials, fluorescent materials can only utilize singlet excitons, the theoretical maximum internal quantum efficiency can only reach 25%, and the application of fluorescent electroluminescent devices is greatly limited, while phosphorescent materials can utilize singlet excitons and triplet excitons, the theoretical maximum internal quantum efficiency can reach 100%, but phosphorescent materials usually contain rare noble heavy metals, and thus, the development of a substitute material with high light-Emitting efficiency is of great significance.
Disclosure of Invention
The invention mainly aims to provide an organic compound and aims to provide an organic luminescent material with high luminescent efficiency.
In order to achieve the above object, the present invention provides an organic compound having a molecular structure of:
in the molecular structure, X is selected from carbon atoms or nitrogen atoms, Y is selected from hydrogen atoms, halogen atoms or R, Z is selected from hydrogen atoms, halogen atoms or R, M is selected from hydrogen atoms, halogen atoms or R, and at least one of Y, Z and M is selected from R, and R is an electron donating group.
Optionally, in the molecular structure, R is an electron donating group comprising a nitrogen atom and a cyclic structure.
Optionally, R in the molecular structure of the organic compound is selected from any one of the following groups:
R1selected from oxygen atom, sulfur atom, methylene group,
R2Selected from carbon atoms or silicon atoms, R3And R4Each independently selected from a hydrogen atom or an alkane group.
Optionally, the molecular structure of the organic compound is selected from any one of:
the invention also provides a preparation method of the organic compound, and the organic compound has a structural general formula shown in the formula (I):
the preparation method of the organic compound comprises the following steps:
providing a halogen raw material and an electron donor, wherein the halogen raw material has a general structural formula shown in a formula (II):
in the formula (II), X is selected from carbon atom or nitrogen atom, A1、A2And A3Are respectively selected from halogen atoms or hydrogen atoms, and at least one is selected from halogen atoms; the electron donor has the formula R-H, R is an electron donating group;
mixing the halogen raw material and the electron donor to form a mixture, controlling reaction conditions, and enabling the halogen raw material and the electron donor to perform substitution reaction to obtain the organic compound, wherein the reaction process is as follows:
wherein Y is A3Or R, Z are A1Or R, M are A2Or R, and at least one of Y, Z, M is R.
Alternatively, the step of "controlling the reaction conditions" comprises:
adding a catalyst, an alkaline substance and a reaction solvent into the mixture, adjusting the reaction temperature to be 90-120 ℃, and controlling the reaction time to be 24-36 hours under the protection of nitrogen.
Optionally, the preparation method of the halogen raw material comprises the steps of:
providing an aminophenol raw material and chloronaphthalene diketone, wherein the aminophenol raw material has a general structural formula shown in a formula (III):
the chloronaphthalene diketone has a general structural formula shown in a formula (IV):
mixing the aminophenol raw material, the chloronaphthalene diketone and a solvent; under the alkaline condition, the aminophenol raw material and the chloronaphthalene diketone react to obtain a reaction product, and the reaction product is subjected to impurity removal treatment to obtain a halogen raw material, wherein the reaction process comprises the following steps:
optionally, the aminophenol type starting material is selected from 2-aminophenol, 2-amino-4-bromophenol, or 2-amino-5-bromophenol, and the chloronaphthalene dione is selected from 2, 3-dichloronaphthalene-1, 4-dione or 2-chloronaphthalene-1, 4-dione.
The invention also provides an organic light-emitting diode which comprises an anode, a light-emitting layer and a cathode which are arranged in a laminated manner, wherein the light-emitting layer comprises a guest material and a host material, and the guest material contains the organic compound;
and/or the guest material comprises an organic compound prepared by the preparation method of the organic compound described in any one of the above.
Optionally, the weight ratio of the host material to the guest material is (60-99): 1-40.
According to the technical scheme, the electron-donating group is introduced to form a D-A type molecular structure, D is the electron-donating group, A is the electron-withdrawing group, and the compound with the D-A type molecular structure has very small energy level difference between a triplet state and a singlet state, so that the probability of converting triplet state excitons into singlet state excitons through back gap transition is greatly increased, the energy of the triplet state excitons is fully utilized, and light emission is realized. At this time, since triplet excitons and singlet excitons are simultaneously utilized, the organic compound prepared has high luminous efficiency without containing a noble metal. It can be understood that the technical scheme of the invention provides an organic compound with high luminous efficiency.
Drawings
Fig. 1 is a schematic structural diagram of an organic light emitting diode according to an embodiment of the invention;
FIG. 2 is a schematic structural diagram of an OLED according to another embodiment of the present invention;
FIG. 3 is a schematic diagram showing the preparation of Compound 1 in example 1 of the present invention;
FIG. 4 is a schematic diagram showing the preparation of halogen starting material E in example 1 of the present invention;
FIG. 5 is a schematic diagram showing the preparation of Compound 2 in example 2 of the present invention;
FIG. 6 is a schematic diagram showing the preparation of halogen raw material B in example 2 of the present invention;
FIG. 7 is a schematic diagram showing the preparation of Compound 3 in example 3 of the present invention;
FIG. 8 is a schematic diagram showing the preparation of a halogen raw material C in example 3 of the present invention;
FIG. 9 is a schematic diagram showing the preparation of Compound 4 in example 4 of the present invention;
FIG. 10 is a schematic diagram showing the preparation of Compound 5 in example 5 of the present invention;
FIG. 11 is a schematic diagram showing the preparation of Compound 6 in example 6 of the present invention.
The reference numbers illustrate:
| reference numerals | Name (R) | Reference numerals | Name (R) |
| 10 | Organic |
500 | |
| 100 | |
600 | |
| 200 | |
700 | |
| 300 | |
800 | |
| 400 | Hole transport layer |
Detailed Description
In order to make the objects, technical solutions and advantages of the embodiments of the present invention clearer, the technical solutions in the embodiments of the present invention will be clearly and completely described below. The examples, in which specific conditions are not specified, were conducted under conventional conditions or conditions recommended by the manufacturer. The reagents or instruments used are not indicated by the manufacturer, and are all conventional products available commercially.
In one embodiment of the present invention, the organic compound has a formula:
in the molecular structure, X is selected from carbon atoms or nitrogen atoms, Y is selected from hydrogen atoms, halogen atoms or R, Z is selected from hydrogen atoms, halogen atoms or R, M is selected from hydrogen atoms, halogen atoms or R, and at least one of Y, Z and M is selected from R, and R is an electron-donating group. The halogen atom includes a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
According to the technical scheme, the electron-donating group is introduced to form a D-A type molecular structure, D is the electron-donating group, A is the electron-withdrawing group, and the compound with the D-A type molecular structure has very small energy level difference between a triplet state and a singlet state, so that the probability of converting triplet state excitons into singlet state excitons through back gap transition is greatly increased, the energy of the triplet state excitons is fully utilized, and light emission is realized. At this time, since triplet excitons and singlet excitons are simultaneously utilized, the organic compound prepared has high luminous efficiency without containing a noble metal. It can be understood that the technical scheme of the invention provides an organic compound with high luminous efficiency. Specifically, the electron-donating group is R, and the structural formula of the electron-withdrawing group comprises
Wherein X is selected from carbon atoms or nitrogen atoms, at least 1 site of 3 connecting sites is connected with halogen atoms, the electron-withdrawing group belongs to a Nile red derivative group, the Nile red derivative group has the characteristics of strong electricity-withdrawing capability, large conjugate surface and wide electron delocalization and is combined with an electron-donating group R,organic compounds having bipolar red light and deep red light with high luminous efficiency can be designed.
In one embodiment of the present invention, in the molecular structure, R is an electron-donating group including a nitrogen atom and a cyclic structure. In the embodiment, the ring structure can be a five-membered ring or a benzene ring, and the invention improves the glass transition stable temperature of the prepared organic compound while forming a D-A type molecular structure by introducing a nitrogen atom and a ring structure with a conjugation effect.
In one embodiment of the present invention, the organic compound has a formula wherein R is selected from any one of the following groups:
R1selected from oxygen atom, sulfur atom, methylene group,
R2Selected from carbon atoms or silicon atoms, R3And R4Each independently selected from a hydrogen atom or an alkane group. The alkane group includes a linear alkane group and a branched alkane group, and even a methyl group, and the embodiments of the present invention are not limited thereto, and the above organic compounds containing different electron donating groups are within the scope of the present invention. This example introduces different electron donating groups, whereby the glass transition stability temperature of the produced organic compound is increased by the introduced electron donating groups.
In one embodiment of the present invention, the molecular structure of the organic compound is selected from any one of the following:
the organic compound provided by the embodiment of the invention has high luminous efficiency, high glass transition temperature and good chemical stability, and when the organic compound is applied to preparation of a luminous layer, the technical scheme provided by the invention can obtain high-performance thermally activated delayed fluorescence.
The invention provides a preparation method of an organic compound, which comprises the following steps: providing a halogen raw material and an electron donor, wherein the halogen raw material has a structural general formula shown in a formula (II):
in the formula (II), X is selected from carbon atom or nitrogen atom, A1、A2And A3Are respectively selected from halogen atoms or hydrogen atoms, and at least one is selected from halogen atoms; the electron donor has the formula R-H, R is an electron donating group; mixing a halogen raw material and an electron donor to form a mixture, controlling reaction conditions to enable the halogen raw material and the electron donor to perform substitution reaction to obtain an organic compound, wherein the reaction process is as follows:
wherein Y is A3Or R, Z are A1Or R, M are A2Or R, and at least one of Y, Z, M is R. In order to ensure sufficient reaction of the halogen raw material and the electron donor, the molar ratio of the halogen raw material to the electron donor is preferably 1 (1.05-2). In addition, in order to obtain a high-purity organic compound, in the embodiment of the present invention, dichloromethane may be added to a reaction product of an electron donor and a halogen raw material, so that the impurity is dissolved in dichloromethane, and thus, after filtering, a part of the impurity can be effectively removed by rotary distillation, and certainly, in order to further remove the remaining impurity and ensure the light emitting efficiency of the organic compound, the reaction product after rotary distillation may be separated by column chromatography, and petroleum ether and dichloromethane in a volume ratio of 1:1 are selected as a mobile phase for the column chromatography separation, so as to obtain a red liquid product. Alternatively, the red liquid product may be subjected to a further rotary distillation to obtain a solid organic compound, the organic compoundThe yield reaches 65 percent.
In one embodiment of the present invention, the step of "controlling the reaction conditions" comprises: adding a catalyst, an alkaline substance and a reaction solvent into the mixture, adjusting the reaction temperature to be 90-120 ℃, and controlling the reaction time to be 24-36 hours under the protection of nitrogen. Of course, the embodiments of the present invention can adjust the reaction temperature and the reaction time according to the differences of the halogen raw material and the electron donor, and the adjustment of the reaction temperature and the reaction time is within the protection scope of the embodiments of the present invention.
In one embodiment of the present invention, when the electron donor has the formula
In the process, the catalyst is tetratriphenylphosphine palladium, the alkaline substance is sodium carbonate, and the reaction solvent is toluene and water. In this example, tetrakistriphenylphosphine palladium, sodium carbonate, toluene, and water were added to a mixture of a halogen raw material and an electron donor, a reaction temperature was adjusted to 90 ℃ to 120 ℃, and a reaction time was controlled to 24 hours to 36 hours under nitrogen protection, thereby realizing the preparation of an organic compound.
Specifically, in one embodiment of the present invention, the preparation method of the organic compound comprises the steps of adding 1.0g of the halogen raw material, 0.71g of (4- (9, 9-dimethylacridin-10 (9H) -yl) phenyl) boric acid, 0.08g of tetrakistriphenylphosphine palladium, 0.7g of anhydrous sodium carbonate and 20m L of anhydrous toluene into a two-neck flask, adding 2ml of distilled water under the protection of nitrogen, refluxing at 110 ℃ for 48H, cooling to room temperature, adding dichloromethane, filtering, performing rotary distillation until no liquid fluid exists, passing through a column with a volume ratio of petroleum ether to dichloromethane of 1:1, and distilling to obtain a red product, namely the organic compound.
In one embodiment of the present invention, when the electron donor has the formula
When the catalyst is palladium acetate and tri-tert-butylphosphine tetrafluoroborate, the alkaline substance is sodium tert-butoxide, and the reaction solvent is anhydrous toluene. In this example, the halogen starting material and the electron donor were added to a mixtureAdding palladium acetate, tri-tert-butylphosphine tetrafluoroborate, sodium tert-butoxide and anhydrous toluene, adjusting the reaction temperature to 90-120 ℃, and controlling the reaction time to 24-36 hours under the protection of nitrogen, thereby realizing the preparation of the organic compound.
Specifically, in one embodiment of the present invention, the method for producing an organic compound comprises the steps of adding 1.0g of a halogen raw material, 0.71g of 9, 9-dimethyl-9, 10-dihydroacridine, 0.08g of palladium acetate, 0.3g of tri-tert-butylphosphine tetrafluoroborate, 0.7g of sodium tert-butoxide, and 30m of L anhydrous toluene into a two-neck flask, refluxing for 2 days under nitrogen protection, cooling to room temperature, adding dichloromethane for filtration, performing rotary distillation until no liquid flows out, and then passing through a column with a volume ratio of petroleum ether to dichloromethane of 1:1, and distilling to obtain a red product, i.e., an organic compound.
In one embodiment of the present invention, the preparation method of the halogen raw material comprises the steps of: providing an aminophenol raw material and chloronaphthalene diketone, wherein the aminophenol raw material has a general structural formula shown in a formula (III):
preferably, the solvent is methanol, and the embodiment of the present invention may be adjusted to alkaline conditions by adding sodium hydroxide or potassium hydroxide, so that the aminophenol raw material and the chloronaphthalene dione are reacted under alkaline conditions to thereby achieve the preparation of the halogen raw material.
In one embodiment of the present invention, in the step of "mixing an aminophenol raw material, a chloronaphthalene dione and a solvent", the aminophenol raw material is selected from 2-aminophenol, 2-amino-4-bromophenol or 2-amino-5-bromophenol, and the chloronaphthalene dione is selected from 2, 3-dichloronaphthalene-1, 4-dione or 2-chloronaphthalene-1, 4-dione. The invention realizes the preparation of different halogen raw materials by adopting different aminophenol raw materials and different chloronaphthalene diones to react.
Specifically, in one embodiment of the present invention, the preparation of the halogen raw material comprises dissolving 20mmol of 2-aminophenol and 20mmol of 2, 3-dichloronaphthalene-1, 4-dione in 100m L methanol, stirring thoroughly, adding 20mmol of KOH, stirring at room temperature for 10 hours, removing methanol to obtain a yellowish brown solid, adding the prepared yellowish brown solid into 50ml of distilled water, stirring and filtering, washing with 25ml of 5% hydrochloric acid, drying, and recrystallizing with benzene and toluene to obtain 4.2g of the halogen raw material E, which is calculated to show a yield of 71%.
Referring to fig. 1, the present invention further provides an organic light emitting diode 10, which includes an anode 200, a light emitting layer 500, and a cathode 800, which are stacked, wherein the light emitting layer 500 includes a guest material and a host material, and the guest material includes the organic compound or includes the organic compound prepared by the above method. Since the guest material of the light emitting layer 500 has high light emitting efficiency, when the organic compound is applied to the light emitting layer 500 of the organic light emitting diode 10 as a substitute material, it can be understood that the present invention improves the light emitting efficiency of the organic light emitting diode 10.
In an embodiment of the invention, the light emitting layer is composed of a host material and a guest material, and the amount of the organic compound can be adjusted according to the host material, so that the light emitting layer prepared has stable light emitting performance. In one embodiment, the weight ratio of the host material to the guest material is (60-99): 1-40, and the guest material is the organic compound.
In one embodiment of the invention, the host material is selected from one or more of CBP and TPBI. The main material and the organic compound are mixed to form the light-emitting layer, the organic compound has a Nile red derivative group, and the Nile red derivative group has the characteristics of strong absorption point capacity, large conjugate surface and wide electron delocalization. The organic compound synthesized by the invention has the characteristics of heat activation delayed fluorescence, large molecular weight, high temperature resistance and luminous intensity, and can be used as a heat activation delayed fluorescence material. The luminescent layer prepared by taking the organic compound as the thermal activation delayed fluorescence material has the characteristics of red light emitting and high luminescent efficiency. In the present invention, the light emitting layer may be formed between the anode and the cathode by a vacuum evaporation method, but is not limited thereto.
Referring to fig. 2, in an embodiment of the invention, the organic light emitting diode 10 further includes a hole injection layer 300, a hole transport layer 400, an electron transport layer 600, and an electron injection layer 700, wherein the hole transport layer 400 is disposed between the anode 200 and the light emitting layer 500, the hole injection layer 300 is disposed between the hole transport layer 400 and the anode 200, the electron transport layer 600 is disposed between the light emitting layer 500 and the cathode 800, and the electron injection layer 700 is disposed between the electron transport layer 600 and the cathode 800.
In the case of producing an organic light-emitting device, the surface of the anode 200 facing away from the functional layer (the hole injection layer 300, the hole transport layer 400, the electron transport layer 600, the electron injection layer 700, and the like) may be provided on the substrate 100, or the surface of the cathode 800 facing away from the functional layer may be provided on the substrate 100. Of course, the base 100 may be a glass substrate.
In one embodiment of the present invention, PSS is PEDOT, the thickness of the hole injection layer is 50nm, and the preparation process of the hole injection layer comprises: PSS is coated on the surface of the anode in a spinning mode, the rotating speed of the anode in the spinning mode is adjusted to be 2000 rpm, the anode is coated for 60s in the spinning mode, and then annealing treatment is carried out for 20min at the temperature of 150 ℃ to obtain a hole injection layer. After the hole injection layer is prepared, a high vacuum (10)-7Torr) Vacuum evaporation is sequentially carried out on the surface of the hole injection layer under the condition, so that a hole transport layer with the thickness of 30nm, a light emitting layer with the thickness of 30nm, an electron transport layer with the thickness of 50nm, an electron injection layer with the thickness of 1nm and a cathode with the thickness of 100nm are formed.
The technical solution of the present invention is further described below with reference to specific examples. It should be understood that the specific embodiments described herein are merely illustrative of the invention and do not limit the scope of the invention.
Example 1
As shown in FIG. 3, the process for the preparation of Compound 1, which is the reaction scheme, comprises charging 1.0g (3.5mmol) of halogen raw material E, 0.85g (4.0mmol) of 9, 9-dimethyl-9, 10-dihydroacridine, 0.08g of palladium acetate, 0.3g of tri-tert-butylphosphine tetrafluoroborate, 0.7g of sodium tert-butoxide and 30M L of anhydrous toluene into a two-necked flask, refluxing at 110 ℃ under nitrogen for 48 hours, cooling to room temperature, adding dichloromethane for filtration, rotary distilling until there is no liquid fluid, passing the collected red liquid through a column at a volume ratio of petroleum ether to dichloromethane of 1:1, distilling to give 1.05g of Compound 1, and calculating the yield to 65%. the results of nuclear magnetic resonance detection of Compound 1 are as follows: 8.05-8.02(t,2H),7.80(t,1H),7.71(t,1H),7.28(t,1H), 7.16(d,1H), 7.01.01 (t,1H), 7.5H (M,5H), and M, M.
As shown in FIG. 4, the halogen source material E was prepared by dissolving 20mmol of 2-aminophenol and 20mmol of 2, 3-dichloronaphthalene-1, 4-dione in 100m L methanol, stirring well, adding 20mmol of KOH, stirring at room temperature for 10 hours, removing methanol to obtain a yellowish brown solid, adding the prepared yellowish brown solid to 50ml of distilled water, stirring and filtering, washing with 25ml of 5% hydrochloric acid, drying, and recrystallizing with benzene and toluene to obtain 4.2g of the halogen source material E, which was calculated to give 71% yield of the halogen source material E whose molecular structure was determined by nuclear magnetic resonance 1H MR 8.05-8.02(t,2H),7.80(t,1H),7.71(t,1H),7.28(t,1H)7.16(d,1H),7.01-6.95(m,2H), and thus the structural formula was determined.
Example 2
As shown in FIG. 5, the process for the preparation of Compound 2, which is the reaction scheme, includes charging 1.0g (3.1mmol) of halogen raw material B, 0.71g (3.4mmol) of 9, 9-dimethyl-9, 10-dihydroacridine, 0.08g of palladium acetate, 0.3g of tri-tert-butylphosphine tetrafluoroborate, 0.7g of sodium tert-butoxide and 30M L of anhydrous toluene into a two-necked flask, refluxing at 110 ℃ under nitrogen for 48 hours, cooling to room temperature, adding dichloromethane for filtration, rotary distilling until there is no liquid fluid, passing the collected red liquid through a column at a volume ratio of petroleum ether to dichloromethane of 1:1, distilling to obtain 0.91g of Compound 2, and calculating the yield to 65%. the results of NMR detection of Compound 2 are as follows: 1H MR 8.05-8.02(t,2H),7.80(t,1H),7.71(t,1H),7.05-7.02(M,4H), 6.70 (M-3H), 3H (M, 6H), 5H (M,5H) and M.
As shown in FIG. 6, the preparation of halogen raw material B comprises dissolving 20mmol of 2-chloronaphthalene-1, 4-dione and 20mmol of 2-amino-4-bromophenol in 100m L of methanol, stirring thoroughly, adding KOH 20mmol, stirring at room temperature for 10H, removing methanol to obtain a yellowish brown solid, adding the prepared yellowish brown solid into 50ml of distilled water, stirring, filtering, washing with 25ml of 5% hydrochloric acid, drying, and recrystallizing with benzene and toluene to obtain halogen raw material B, wherein the mass of the prepared halogen raw material B is 4.2g, and the yield of halogen raw material E is 64%.
Example 3
As shown in FIG. 7, the preparation of Compound 3 comprises charging 1.0g (3.1mmol) of halogen raw material C, 0.71g (3.4mmol) of 9, 9-dimethyl-9, 10-dihydroacridine, 0.08g of palladium acetate, 0.3g of tri-tert-butylphosphine tetrafluoroborate, 0.7g of sodium tert-butoxide and 30M L of anhydrous toluene into a two-necked flask, refluxing at 110 ℃ for 48 hours under nitrogen protection, cooling to room temperature, adding dichloromethane for filtration, rotary distilling until there is no liquid fluid, passing through a column with a volume ratio of petroleum ether to dichloromethane of 1:1, distilling the collected red liquid to obtain 0.91g of Compound, and calculating the yield to 65%. the results of NMR detection of Compound 3 are as follows: 1 MR 8.05-8.02(t,2H),7.80(t,1H),7.71(t,1H),7.05 (M,4H),6.91(d, 6H), 356H (t,2H), mass spectra (t,1H, 5.5H, 5H, M.
As shown in FIG. 8, the preparation of halogen raw material C comprises dissolving 20mmol of 2-chloronaphthalene-1, 4-dione and 20mmol of 2-amino-5-bromophenol in 100m L methanol, stirring thoroughly, adding KOH 20mmol, stirring at room temperature for 10H, removing methanol to obtain a yellowish brown solid, adding the prepared yellowish brown solid into 50ml of distilled water, stirring and filtering, washing with 25ml of 5% hydrochloric acid, drying, and recrystallizing with benzene and toluene to obtain halogen raw material 3. the mass of the prepared halogen raw material 3 is 4.2g, from which the yield of halogen raw material E is 64%.
Example 4
As shown in FIG. 9, the preparation of Compound 4 comprises charging 1.0g (3.1mmol) of halogen raw material C, 0.71g (3.4mmol) of (4- (9, 9-dimethylacridin-10 (9H) -yl) phenyl) boronic acid, 0.08g of tetrakistriphenylphosphine palladium, 0.7g of anhydrous sodium carbonate and 20M L of anhydrous toluene into a two-necked flask, adding 2ml of distilled water under nitrogen protection, refluxing at 110 ℃ for 48 hours, cooling to room temperature, adding dichloromethane, filtering, rotary distilling until there is no liquid fluid, passing through a column with a volume ratio of petroleum ether to dichloromethane of 1:1, distilling the collected red liquid to obtain 0.91g of Compound 4, and calculating the yield to 65%. the results of NMR detection of Compound 4 are as follows: 8.05-8.02(t,2H),7.80(t,1H),7.71(t,1H), 7.54(d,2H),7.32(s,1H), 7.05(d,1H), 7.02 (d, 5H), 5.5H (M, 6H), 5M, 5H (M,5H), and M,5H, 5M, 5H, 6H, 5H, 6.
Example 5
As shown in FIG. 10, the preparation of compound 5 includes charging 1.0g (3.1mmol) of halogen raw material C, 0.71g (3.4mmol) of (4- (9H-carbazol-9-yl) phenyl) boronic acid, 0.08g of tetratriphenylphosphonium palladium, 0.7g of anhydrous sodium carbonate and 20M L anhydrous toluene into a two-neck flask, adding 2ml of distilled water under nitrogen protection, refluxing at 110 ℃ for 48H, cooling to room temperature, adding dichloromethane for filtration, rotary distilling until there is no liquid fluid, passing through a column with a volume ratio of petroleum ether to dichloromethane of 1:1, distilling the collected red liquid to obtain 0.91g of compound, and calculating the yield to 65%, and the NMR detection results of compound 5 are as follows, 8.55(d,1H),8.12(d,1H),8.05 to 8.02(t,2H 733), 7.94(d,1H),7.80 to 7.79(M,3H), 7.68 (d, 7.7.5H), 7.5 (M,3H), 7.1H, 3H, 5(M, 5, M.
Example 6
As shown in FIG. 11, the preparation of Compound 6 comprises charging 1.0g (3.1mmol) of halogen raw material C, 0.71g (3.4mmol) of (4- (diphenylamino) phenyl) boronic acid, 0.08g of tetrakistriphenylphosphine palladium, 0.7g of anhydrous sodium carbonate and 20M L of anhydrous toluene into a two-necked flask, adding 2ml of distilled water under nitrogen protection, refluxing at 110 ℃ for 48 hours, cooling to room temperature, adding dichloromethane, filtering, rotary distilling until there is no liquid fluid, passing through a column with a volume ratio of petroleum ether to dichloromethane of 1:1, distilling the collected red liquid to obtain 0.91g of Compound 6, and calculating the yield to 65%, the NMR detection results of Compound 6 are as follows, 8.05 to 8.02(t,2H),7.80(t,1H),7.71(t,1H),7.54(d,2H),7.32(s,1H), 7.22.20 (M), 7.5 (t,1H), 7.81 (d, 6H), 1H (M,5H), the charge ratio of Compound 6 is determined by NMR, 1.1.1H, 5M, and the charge ratio of the following (M, M + 6, M.
Example 7
The host material of CBP was doped with 10% of the compounds 1 to 7 prepared according to the present invention to prepare a light-emitting layer, wherein the compound 7 was HAP-3TPA (4,4',4 ″ - (1,3,3a1,4,6,7, 9-heptaaza-styrene-2, 5, 8-triyl) -tris (N, bis- (tert-butyl) phenyl) aniline), and the structure of the device included the sequential stacking of an anode 200, a hole injection layer 300(PEDOT: PSS), a hole transport layer 400 (1-bis [4- [ N, N-bis (4-tolyl) amino ] phenyl ] -cyclohexane (TAPC), a light-emitting layer 500, an electron transport layer 600 (pypb), an electron injection layer 700 (L iF), and a cathode (aluminum) and specifically, the method for preparing the device includes the steps of spin-coating the surface of the anode 200 with PEDOT: PSS, adjusting the number of spin-coating, after 60s, annealing at 150 ℃ for 20min to obtain an injection layer 300, preparing a hole injection layer 300, and then performing vacuum evaporation of the obtained hole injection layer 300 nm, forming a light-emitting layer, a hole transport layer, a cathode, and a light-emitting layer formed by vacuum evaporation of 30nm, 400 nm, and 800 nm:
the device 1 comprises ITO/PEDOT, PSS/TAPC/CBP, compound 1/TmPyPB/L iF/Al;
the device 2 comprises ITO/PEDOT, PSS/TAPC/CBP, compound 2/TmPyPB/L iF/Al;
the device 3 comprises ITO/PEDOT, PSS/TAPC/CBP, a compound 3/TmPyPB/L iF/Al;
the device 4 comprises ITO/PEDOT, PSS/TAPC/CBP, compound 4/TmPyPB/L iF/Al;
the device 5 comprises ITO/PEDOT, PSS/TAPC/CBP, and a compound 5/TmPyPB/L iF/Al;
the device 6 comprises ITO/PEDOT, PSS/TAPC/CBP, compound 6/TmPyPB/L iF/Al;
the device 7 comprises ITO/PEDOT, PSS/TAPC/CBP, a compound 7/TmPyPB/L iF/Al;
the performance data of devices 1-7 are shown in the following table:
remarking: the rate of change of current efficiency at an efficiency roll-off of 1000 nit.
As can be seen from the above table, compared with the device 7 prepared from the existing compound 7, the devices prepared from the compounds 1 to 6 of the embodiment of the present invention have high brightness, high external quantum efficiency, and low efficiency roll off, and can be applied to the fields of display and illumination.
The above description is only a preferred embodiment of the present invention, and is not intended to limit the scope of the present invention, and all modifications and equivalents of the present invention, which are made by the contents of the present specification and the accompanying drawings, or directly/indirectly applied to other related technical fields, are included in the scope of the present invention.
Claims (10)
1. An organic compound having a molecular structure of:
in the molecular structure, X is selected from carbon atoms or nitrogen atoms, Y is selected from hydrogen atoms, halogen atoms or R, Z is selected from hydrogen atoms, halogen atoms or R, M is selected from hydrogen atoms, halogen atoms or R, and at least one of Y, Z and M is selected from R, and R is an electron donating group.
2. The organic compound according to claim 1, wherein in the molecular structure, R is an electron donating group comprising a nitrogen atom and a cyclic structure.
3. The organic compound according to claim 2, wherein R in the molecular structure of the organic compound is selected from any one of the following groups:
R1selected from oxygen atom, sulfur atom, methylene group,
R2Selected from carbon atoms or silicon atoms, R3And R4Each independently selected from a hydrogen atom or an alkane group.
4. The organic compound according to any one of claims 1 to 3, wherein the molecular structure of the organic compound is selected from any one of:
5. a method for preparing an organic compound, wherein the organic compound has a general structural formula shown in formula (I):
the preparation method of the organic compound comprises the following steps:
providing a halogen raw material and an electron donor, wherein the halogen raw material has a structural general formula shown in a formula (II):
in the formula (II), X is selected from carbon atom or nitrogen atom, A1、A2And A3Are respectively selected from halogen atoms or hydrogen atoms, and at least one is selected from halogen atoms; what is needed isThe electron donor has a formula R-H, R is an electron donating group;
mixing the halogen raw material and the electron donor to form a mixture, controlling reaction conditions, and enabling the halogen raw material and the electron donor to perform substitution reaction to obtain the organic compound, wherein the reaction process is as follows:
wherein Y is A3Or R, Z are A1Or R, M are A2Or R, and at least one of Y, Z, M is R.
6. The method for producing an organic compound according to claim 5, wherein the step of "controlling the reaction conditions" comprises:
adding a catalyst, an alkaline substance and a reaction solvent into the mixture, adjusting the reaction temperature to be 90-120 ℃, and controlling the reaction time to be 24-36 hours under the protection of nitrogen.
7. The method of producing an organic compound according to claim 5, wherein the method of producing the halogen raw material comprises the steps of:
providing an aminophenol raw material and chloronaphthalene diketone, wherein the aminophenol raw material has a general structural formula shown in a formula (III):
the chloronaphthalene diketone has a general structural formula shown in a formula (IV):
mixing the aminophenol raw material, the chloronaphthalene diketone and a solvent; under the alkaline condition, the aminophenol raw material and the chloronaphthalene diketone react to obtain a reaction product, and the reaction product is subjected to impurity removal treatment to obtain a halogen raw material, wherein the reaction process comprises the following steps:
8. the method for producing an organic compound according to claim 7, wherein the aminophenol-based starting material is selected from the group consisting of 2-aminophenol, 2-amino-4-bromophenol and 2-amino-5-bromophenol, and the chloronaphthalene dione is selected from the group consisting of 2, 3-dichloronaphthalene-1, 4-dione and 2-chloronaphthalene-1, 4-dione.
9. An organic light-emitting diode comprising an anode, a light-emitting layer, and a cathode, which are stacked, wherein the light-emitting layer comprises a guest material and a host material, and the guest material contains the organic compound according to any one of claims 1 to 4;
and/or the guest material comprises an organic compound produced by the method for producing an organic compound according to any one of claims 5 to 8.
10. The organic light emitting diode of claim 9, wherein the weight ratio of the host material to the guest material is (60-99): 1-40.
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2020
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