CN113248520A - Organic compound and organic light-emitting device using same - Google Patents
Organic compound and organic light-emitting device using same Download PDFInfo
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- CN113248520A CN113248520A CN202110372983.1A CN202110372983A CN113248520A CN 113248520 A CN113248520 A CN 113248520A CN 202110372983 A CN202110372983 A CN 202110372983A CN 113248520 A CN113248520 A CN 113248520A
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- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 26
- 125000003118 aryl group Chemical group 0.000 claims abstract description 14
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 14
- 150000001412 amines Chemical class 0.000 claims abstract description 7
- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims abstract description 7
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 27
- 239000000463 material Substances 0.000 claims description 26
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
- 238000002347 injection Methods 0.000 claims description 13
- 239000007924 injection Substances 0.000 claims description 13
- 230000005525 hole transport Effects 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000006732 (C1-C15) alkyl group Chemical group 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 239000010410 layer Substances 0.000 description 43
- 238000006243 chemical reaction Methods 0.000 description 23
- 239000000543 intermediate Substances 0.000 description 19
- 230000000052 comparative effect Effects 0.000 description 17
- 230000015572 biosynthetic process Effects 0.000 description 16
- 238000003786 synthesis reaction Methods 0.000 description 16
- 239000012044 organic layer Substances 0.000 description 13
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 12
- 229940125904 compound 1 Drugs 0.000 description 12
- 238000000034 method Methods 0.000 description 11
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 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 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 6
- 239000002346 layers by function Substances 0.000 description 5
- HUWSZNZAROKDRZ-RRLWZMAJSA-N (3r,4r)-3-azaniumyl-5-[[(2s,3r)-1-[(2s)-2,3-dicarboxypyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]amino]-5-oxo-4-sulfanylpentane-1-sulfonate Chemical compound OS(=O)(=O)CC[C@@H](N)[C@@H](S)C(=O)N[C@@H]([C@H](C)CC)C(=O)N1CCC(C(O)=O)[C@H]1C(O)=O HUWSZNZAROKDRZ-RRLWZMAJSA-N 0.000 description 4
- YQOLEILXOBUDMU-KRWDZBQOSA-N (4R)-5-[(6-bromo-3-methyl-2-pyrrolidin-1-ylquinoline-4-carbonyl)amino]-4-(2-chlorophenyl)pentanoic acid Chemical compound CC1=C(C2=C(C=CC(=C2)Br)N=C1N3CCCC3)C(=O)NC[C@H](CCC(=O)O)C4=CC=CC=C4Cl YQOLEILXOBUDMU-KRWDZBQOSA-N 0.000 description 4
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 4
- QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 230000000903 blocking effect Effects 0.000 description 4
- 150000001716 carbazoles Chemical class 0.000 description 4
- 229940125846 compound 25 Drugs 0.000 description 4
- 229940125844 compound 46 Drugs 0.000 description 4
- 239000002019 doping agent Substances 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 230000002194 synthesizing effect Effects 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 238000013461 design Methods 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 229940078552 o-xylene Drugs 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
- 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 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- -1 carbazole series compound Chemical class 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000005283 ground state Effects 0.000 description 2
- 238000004770 highest occupied molecular orbital Methods 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 235000015320 potassium carbonate Nutrition 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- JWJQEUDGBZMPAX-UHFFFAOYSA-N (9-phenylcarbazol-3-yl)boronic acid Chemical compound C12=CC=CC=C2C2=CC(B(O)O)=CC=C2N1C1=CC=CC=C1 JWJQEUDGBZMPAX-UHFFFAOYSA-N 0.000 description 1
- IBXMKLPFLZYRQZ-UHFFFAOYSA-N 1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1C=CC(=O)C=CC1=CC=CC=C1 IBXMKLPFLZYRQZ-UHFFFAOYSA-N 0.000 description 1
- RINOYHWVBUKAQE-UHFFFAOYSA-N 1-iodo-2-methylbenzene Chemical compound CC1=CC=CC=C1I RINOYHWVBUKAQE-UHFFFAOYSA-N 0.000 description 1
- VWDMDPDGACOPSR-UHFFFAOYSA-N 4-bromo-2-iodo-1-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Br)C=C1I VWDMDPDGACOPSR-UHFFFAOYSA-N 0.000 description 1
- WGUUKVJNVYAFFI-UHFFFAOYSA-N 9h-carbazol-3-ylboronic acid Chemical compound C1=CC=C2C3=CC(B(O)O)=CC=C3NC2=C1 WGUUKVJNVYAFFI-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- 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
-
- 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
-
- 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]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
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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]
- H10K50/18—Carrier blocking layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- 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
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- 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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- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- 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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- 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
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- 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
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
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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
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
- C09K2211/1048—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with oxygen
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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
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
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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
- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
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- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Organic Chemistry (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The present invention provides an organic compound and an organic light emitting device using the same, and more particularly, to a soluble organic compound having excellent color purity and high brightness and light emitting efficiency and an OLED device using the same. The structure of the organic compound provided by the invention is shown as formula 1:
in the above structural formula, Ar1、Ar2And Ar3Each independently selected from substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C10-C30 condensed ring group, substituted or unsubstituted C4-A C30 heteroaryl, a substituted or unsubstituted C13-C30 amine derivative, or a fluorene derivative.
Description
Technical Field
The present invention relates to an organic compound and an organic light emitting device using the same, and more particularly, to a soluble organic compound having excellent color purity and high brightness and high luminous efficiency and an OLED device using the same.
Background
With the development of multimedia technology and the increase of information-oriented requirements, the requirements for the performance of panel displays are increasing. The OLED has a series of advantages of autonomous light emission, low-voltage direct current driving, full curing, wide viewing angle, rich colors and the like, is widely noticed due to potential application in new-generation displays and lighting technologies, and has a very wide application prospect. The organic electroluminescent device is a spontaneous light emitting device, and the OLED light emitting mechanism is that under the action of an external electric field, electrons and holes are respectively injected from positive and negative electrodes and then migrate, recombine and attenuate in an organic material to generate light emission. A typical structure of an OLED comprises one or more functional layers of a cathode layer, an anode layer, an electron injection layer, an electron transport layer, a hole blocking layer, a hole transport layer, a hole injection layer and an organic light emitting layer.
Although the research on organic electroluminescence is rapidly progressing, there are still many problems to be solved, such as the improvement of External Quantum Efficiency (EQE), the design and synthesis of new materials with higher color purity, the efficient electron transport, the design and synthesis of new hole blocking materials, and the like. For the organic electroluminescent device, the luminous quantum efficiency of the device is the comprehensive reflection of various factors and is an important index for measuring the quality of the device.
Luminescence can be divided into fluorescence and phosphorescence. In fluorescence emission, an organic molecule in a singlet excited state transits to a ground state, thereby emitting light. On the other hand, in phosphorescence, organic molecules in a triplet excited state transition to a ground state, thereby emitting light.
At present, some organic electroluminescent materials have been commercially used due to their excellent properties, but as host materials in organic electroluminescent devices, it is more important to have good hole transport properties in addition to the triplet energy level higher than that of the guest materials, which prevents the energy reverse transfer of exciton transition release. Currently, materials having both high triplet energy levels and good hole mobility in the host material are still lacking. Therefore, how to design a new main material with better performance is a problem to be solved urgently by those skilled in the art.
Disclosure of Invention
An object of the present invention is to provide an organic compound having excellent pure chromaticity, high luminance and excellent luminous efficiency, and an organic light emitting device using the same.
The invention provides an organic compound, the structural formula of which is shown as 1:
in the structural formula, Ar1, Ar2 and Ar3 are respectively and independently selected from substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C10-C30 condensed ring group, substituted or unsubstituted C4-C30 heteroaryl, substituted or unsubstituted C13-C30 amine derivative or fluorene derivative.
Preferably, an organic compound characterized by: the structural formula is shown as I-1-I-4:
wherein Ar1, Ar2 and Ar3 are each independently selected from substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C10-C30 fused ring group, substituted or unsubstituted C4-C30 heteroaryl, substituted or unsubstituted C13-C30 amine derivative or fluorene derivative.
Further preferred is a structure wherein R1 and R2 are independently selected from the following structures:
wherein R1 and R2 are independently selected from one of hydrogen, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C4-C30 heteroaryl, or a combination thereof;
X1、X2、X3independently selected from nitrogen (N) or carbon (C);
l1 is a single bond or is selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C10-C30 fused ring group, substituted or unsubstituted C4-C30 heteroaryl, substituted or unsubstituted C13-C30 amine derivative or fluorene derivative.
Further preferred is a structure wherein R1 and R2 are independently selected from the following structures:
wherein R8, R9 and R10 are independently selected from one of substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C4-C30 heteroaryl or the combination of the alkyl, the aryl and the heteroaryl;
l2 is a single bond or is selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C10-C30 fused ring, substituted or unsubstituted C4-C30 heteroaryl.
In a further preferred manner, the organic compounds are independently selected from the following compounds:
the invention also provides application of the carbazole series-containing compound in an organic light-emitting device.
Preferably, the organic light emitting device comprises an anode, a cathode and a plurality of organic functional layers positioned between the anode and the cathode, wherein the organic functional layers contain the compound containing the carbazole series.
The invention has the beneficial effects that:
the invention provides a carbazole series-containing compound, which has a structure shown in a formula 1, wherein an electron-rich structure in the carbazole series compound has great influence on the photoelectric property of the whole compound molecule, so that unnecessary vibration energy loss is reduced, and high-efficiency luminous performance is realized. By adjusting substituent groups, the compound has better thermal stability and chemical properties. The compound containing carbazole series has the advantages of simple preparation method and easily obtained raw materials, and can meet the industrial requirements.
The carbazole series compounds are prepared into devices, particularly used as main materials, the devices have the advantages of low driving voltage and high luminous efficiency, and are superior to the conventional common OLED devices.
In the present invention, the organic electroluminescent device preferably includes an anode, a cathode, and several organic layers located between the anode and the cathode, and the "organic layer" refers to a term of all layers disposed between the anode and the cathode in the organic electroluminescent device. The organic layer may be a layer having a hole characteristic and a layer having an electron characteristic. For example, the organic layer includes one or more of a hole injection layer, a hole transport layer, a functional layer having both hole injection and hole transport, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a functional layer having both electron transport and electron injection.
In the present invention, the hole injection layer, the hole transport layer, and the hole transport layer may be formed of a conventional hole injection material, a hole transport material, or a material having both hole injection and hole transport functions, in addition to the electron-generating material.
For example, the organic layer includes a light emitting layer, and the light emitting layer includes one or more of a phosphorescent host, a fluorescent host, a phosphorescent dopant, and a fluorescent dopant. In the present invention, the compound for an organic electroluminescent device can be used as a fluorescent host, as a fluorescent dopant, and as both a fluorescent host and a fluorescent dopant.
In the present invention, the light emitting layer may be a red, yellow or blue light emitting layer. In the present invention, when the light-emitting layer is a light-emitting layer, an organic electroluminescent device having high efficiency, high resolution, high luminance and long life can be obtained by using the above-mentioned compound for an organic electroluminescent device as a host.
In the present invention, the organic electroluminescent diode device of the organic compound is characterized in that the organic electroluminescent diode device comprises an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer and a cathode, which are sequentially deposited, and the organic compound is used as a host material of the light emitting layer.
The present invention is not particularly limited in the method for preparing the organic electroluminescent device, and may be prepared by using a method and materials for preparing a light emitting device, which are well known to those skilled in the art, in addition to the organic compound of formula 1.
Detailed Description
In order to make the technical means, the creation features, the achievement purposes and the effects of the invention easy to understand, the invention is further described with reference to specific embodiments.
1. Synthesis of intermediate 2-1-1
To a 500 ml reaction flask were added intermediate 2-1(22.79 g, 61.4 mmol), 4-bromo-2-iodo-1-nitrobenzene (20.13 g, 61.4 mmol), tetrakis (triphenylphosphine) palladium (5 mol%), potassium carbonate (17.0 g, 122.8 mmol), 1, 4-dioxane (200 ml) and water (50 ml). The reaction system is heated to 80 ℃ and reacts for 12 hours under the protection of nitrogen. After completion of the reaction, the reaction solution was cooled to room temperature and extracted with o-dichlorobenzene and water. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and recrystallized to give a crude product, which was then subjected to silica gel column chromatography to give intermediate 2-1-1(20.38 g, yield 80%). LC-MS: M/Z444.01(M + H)+。
2. Synthesis of intermediates 2-2-1-8-4-1
The method for synthesizing the intermediate 2-1-1 is used for synthesizing the compound intermediate 2-2-1-8-4-1.
3. Synthesis of intermediate 2-1-2
A250 ml reaction flask was charged with 2-1-1(1.82 g, 4.0 mmol), triethyl phosphite (1.02 g, 6.0 mmol), and reacted overnight at 145 deg.C under nitrogen. The reaction was stopped, 2M hydrochloric acid was added after cooling, stirred to full white, and extracted with a small amount of dichloromethane. The organic layer was separated and collected to obtain 2-1-2(1.26 g, yield 79%). LC-MS: M/Z399.01(M + H)+。
4. Synthesis of intermediate 2-2-2-8-4-2
The method for synthesizing the intermediate 2-1-1 is used for synthesizing the compound intermediate 2-2-1-8-4-1.
Example 1: synthesis of Compound 1
1. Synthesis of intermediate 1-1
To a 500 ml reaction flask were added intermediate 2-1-2(25.37 g, 61.4 mmol), 9-phenyl-9H-carbazol-3-ylboronic acid (17.63 g, 61.4 mmol), tetrakis (triphenylphosphine) palladium (5 mol%), K2CO3(17.0 g, 122.8 mmol), 1, 4-dioxane (200 ml) and water (50 ml). The reaction system is heated to 80 ℃ and reacts for 12 hours under the protection of nitrogen. After completion of the reaction, the reaction solution was cooled to room temperature and extracted with o-dichlorobenzene and water. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and recrystallized to give crude product, which was then passed through silica gel column to obtain intermediate 1-1(24.74 g, yield 70%). LC-MS: M/Z575.20(M + H)+。
2. Synthesis of Compound 1
A250 mL three-necked flask was charged with intermediate 1-1(11.51 g, 20 mmol), A (5.05 g, 21.0 mmol), tris (dibenzylideneacetone) dipalladium (4 mol%), tri-tert-butylphosphine (8 mol%), potassium tert-butoxide (3.8)G, 33.6 mmol) and o-xylene (80 ml). The reaction system is heated to 120 ℃ and reacts for 12 hours under the protection of nitrogen. After completion of the reaction, the reaction solution was cooled to room temperature and extracted with o-dichlorobenzene and water. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and recrystallized to obtain a crude product, which was then subjected to silica gel column to obtain Compound 1(9.36 g, yield 60%). LC-MS: M/Z779.27(M + H)+。
Example 2: synthesis of Compound 13
1. Synthesis of intermediate 13-1
In a 250 ml three-necked flask were added intermediate 2-1-2(8.27 g, 20 mmol), iodotoluene (4.28 g, 21.0 mmol), tris (dibenzylideneacetone) dipalladium (4 mol%), tri-tert-butylphosphine (8 mol%), potassium tert-butoxide (3.8 g, 33.6 mmol) and o-xylene (80 ml). The reaction system is heated to 120 ℃ and reacts for 12 hours under the protection of nitrogen. After the reaction was completed, the reaction solution was cooled to room temperature, and extracted with o-dichlorobenzene and water. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and recrystallized to give a crude product, which was then subjected to silica gel column chromatography to give compound 13-1(8.12 g, yield 83%). LC-MS: M/Z488.05(M + H)+。
2. Synthesis of intermediate 13-2
To a 500 ml reaction flask were added intermediate 13-1(30.05 g, 61.4 mmol), carbazol-3-ylboronic acid (12.96 g, 61.4 mmol), tetrakis (triphenylphosphine) palladium (5 mol%), K2CO3(17.0 g, 122.8 mmol), 1, 4-dioxane (200 ml) and water (50 ml). The reaction system is heated to 80 ℃ and reacts for 12 hours under the protection of nitrogen. After completion of the reaction, the reaction solution was cooled to room temperature and extracted with o-dichlorobenzene and water. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and recrystallized to give a crude product, which was then passed through a silica gel column to obtain intermediate 1-1(24.03 g, yield 68%). LC-MS: M/Z575.20(M + H)+。
3. Synthesis of Compound 13
Example 3: synthesis of Compound 25
Compound 25 was synthesized by the method of reference example 1 to give compound 25(10.36 g, yield 70%). LC-MS: M/Z779.25(M + H)+。
Example 4: synthesis of Compound 40
Compound 40 was synthesized by the method of reference example 2 to give compound 40(11.65 g, yield 82%). LC-MS: M/Z779.26(M + H)+。
Example 5: synthesis of Compound 46
Compound 46 was synthesized by the method of reference example 1 to give compound 46(10.46 g, yield 78%). LC-MS: M/Z806.28(M + H)+。
Evaluation example 1: HOMO, LUMO, triplet energy level, and S1-T1 energy level evaluation of the compounds:
the above data show that the HOMO value of the substance decreases after the amine-series compound is introduced into the compound, that the Eg (eV) value conforms to the RH (phosphorescent red host) condition, and that the delayed fluorescence property (S1-T1) is enhanced after the amine-series compound is introduced into the compound.
Device embodiments
(I) Evaluation of luminescent Material devices
The compounds of the respective organic layers used in the device examples are as follows:
1. first embodiment
The ITO glass substrate was patterned to have a light emitting area of 3 mm × 3 mm. The patterned ITO glass substrate was then washed.
The substrate is then placed in a vacuum chamber. The standard pressure was set to 1X 10-6And (4) supporting. Thereafter on an ITO substrate
Compound (I)
And
the sequence of (a) and (b) forming layers of organic material.
2. Second embodiment
An organic light-emitting device of the second embodiment was fabricated by the same method as that of the first embodiment described above, except that the host material layer of the organic light-emitting device was replaced with compound 13 from compound 1 of the first embodiment.
3. Third embodiment
An organic light-emitting device of the third embodiment was fabricated by the same method as that of the first embodiment described above, except that the host material layer of the organic light-emitting device was replaced with compound 25 from compound 1 of the first embodiment.
4. Fourth embodiment
An organic light-emitting device of the fourth embodiment was fabricated by the same method as that of the first embodiment described above, except that the host material layer of the organic light-emitting device was replaced with compound 40 from compound 1 of the first embodiment.
5. Fifth embodiment
An organic light-emitting device of the fifth embodiment was fabricated by the same method as that of the first embodiment described above, except that the host material layer of the organic light-emitting device was replaced with compound 46 from compound 1 of the first embodiment.
6. Comparative example 1
An organic light-emitting device of comparative example was prepared in the same manner as in the first embodiment described above, except that the host material layer of the organic light-emitting device was replaced with compound RH1 from compound 1 of the first embodiment.
7. Comparative example 2
An organic light-emitting device of comparative example was prepared in the same manner as in the first embodiment described above, except that the host material layer of the organic light-emitting device was replaced with compound RH2 from compound 1 of the first embodiment.
8. Comparative example 3
An organic light-emitting device of comparative example was prepared in the same manner as in the first embodiment described above, except that the host material layer of the organic light-emitting device was replaced with compound RH3 from compound 1 of the first embodiment.
9. Comparative example 4
An organic light-emitting device of comparative example was prepared in the same manner as in the first embodiment described above, except that the host material layer of the organic light-emitting device was replaced with compound RH4 from compound 1 of the first embodiment.
10. Comparative example 5
An organic light-emitting device of comparative example was prepared in the same manner as in the first embodiment described above, except that the host material layer of the organic light-emitting device was replaced with compound RH5 from compound 1 of the first embodiment.
The prepared organic light-emitting device is at 10mA/cm2Voltage, efficiency and life were tested under current conditions.
Table 1 shows the performance test results of the organic light emitting devices prepared in the examples of the present invention and the comparative examples.
TABLE 1
As shown in table 1, the device also operated efficiently at the same voltage. And the current efficiency and the lifetime of the embodiment are significantly increased compared to the comparative example, for example, the device performance is significantly improved when comparing example 1 and comparative example 1, example 2 and comparative example 2, example 3 and comparative example 3, example 4 and comparative example 4, example 5 and comparative example 5.
The foregoing has described the general principles, principal features, and advantages of the invention. It will be understood by those skilled in the art that the present invention is not limited to the embodiments described above, which are given by way of illustration of the principles of the present invention, and that various changes and modifications may be made without departing from the spirit and scope of the invention as defined by the appended claims.
Claims (10)
1. An organic compound characterized by: the structural formula is shown as 1:
in the above structural formula, Ar1、Ar2And Ar3Each independently selected from substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C10-C30 condensed ring group,Substituted or unsubstituted C4-C30 heteroaryl, substituted or unsubstituted C13-C30 amine derivatives, or fluorene derivatives.
2. An organic compound characterized by: the structural formula is shown as 1-4:
wherein Ar is1、Ar2And Ar3Each independently selected from substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C10-C30 condensed ring group, substituted or unsubstituted C4-C30 heteroaryl, substituted or unsubstituted C13-C30 amine derivative or fluorene derivative.
3. An organic compound according to claim 1, wherein: ar is1And Ar2Independently selected from the following:
wherein R is1And R2Independently selected from hydrogen, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C4-C30 heteroaryl, or a combination thereof;
X1、X2、X3independently selected from nitrogen (N) or carbon (C);
L1is a single bond or is selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C10-C30 condensed ring group, substituted or unsubstituted C4-C30 heteroaryl, substituted or unsubstituted C13-C30 amine derivative or fluorene derivative.
4. The organic compound of claim 3, wherein R is1、R2Independently selected from one of the following compounds:
wherein R is8、R9、R10Independently selected from substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C4-C30 heteroaryl, or the combination thereof;
L2is a single bond or is selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C10-C30 condensed ring group, and substituted or unsubstituted C4-C30 heteroaryl.
5. The organic compound according to any one of claims 1 to 4, wherein: the organic compound is independently selected from one of the following compounds:
6. an organic light-emitting device using the organic compound according to any one of claims 1 to 5, characterized in that: the organic light-emitting device sequentially comprises a deposited anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer and a cathode, wherein the organic compound is used as a main body material of the light-emitting layer.
7. The organic light-emitting device according to claim 6, wherein the organic compound according to any one of claims 1 to 5 is used alone or in combination with other compounds.
8. The organic light-emitting device according to claim 6, wherein the organic compound according to any one of claims 1 to 5 is used as a light-emitting layer or an active layer.
9. An organic light-emitting device according to claim 6, wherein the organic compound according to any one of claims 1 to 5 is used as a hole-blocking layer.
10. An organic light-emitting device according to claim 6, wherein the organic compound according to any one of claims 1 to 5 is used as an electron-transporting layer.
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