CN115141189A - Organic electroluminescent compound and application thereof - Google Patents
Organic electroluminescent compound and application thereof Download PDFInfo
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- CN115141189A CN115141189A CN202110347971.3A CN202110347971A CN115141189A CN 115141189 A CN115141189 A CN 115141189A CN 202110347971 A CN202110347971 A CN 202110347971A CN 115141189 A CN115141189 A CN 115141189A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 55
- 239000000463 material Substances 0.000 claims abstract description 51
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 11
- 239000010410 layer Substances 0.000 claims description 78
- 238000002347 injection Methods 0.000 claims description 13
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- 239000000758 substrate Substances 0.000 claims description 8
- 239000002346 layers by function Substances 0.000 claims description 6
- 239000002019 doping agent Substances 0.000 claims description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 abstract description 9
- 230000009477 glass transition Effects 0.000 abstract description 5
- 230000005540 biological transmission Effects 0.000 abstract description 4
- 238000002425 crystallisation Methods 0.000 abstract description 2
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- 230000002950 deficient Effects 0.000 abstract description 2
- 230000000694 effects Effects 0.000 abstract description 2
- 230000002349 favourable effect Effects 0.000 abstract description 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 28
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 25
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
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- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 8
- 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 8
- 239000012141 concentrate Substances 0.000 description 7
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- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 4
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
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- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 3
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- UNXISIRQWPTTSN-UHFFFAOYSA-N boron;2,3-dimethylbutane-2,3-diol Chemical compound [B].[B].CC(C)(O)C(C)(C)O UNXISIRQWPTTSN-UHFFFAOYSA-N 0.000 description 3
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- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
- 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 1
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 1
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
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- 238000001514 detection method Methods 0.000 description 1
- 238000011982 device technology Methods 0.000 description 1
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- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical compound C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 1
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- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
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- 239000011368 organic material Substances 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 230000008569 process Effects 0.000 description 1
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- 238000005215 recombination Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000006617 triphenylamine group Chemical group 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000003313 weakening effect Effects 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D411/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms
- C07D411/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D411/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/14—Ortho-condensed systems
- C07D491/153—Ortho-condensed systems the condensed system containing two rings with oxygen as ring hetero atom and one ring with nitrogen as ring hetero atom
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- 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
- 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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- 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
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- 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
- 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
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- 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
- 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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- 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
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention provides an organic electroluminescent compound and application thereof, wherein the organic electroluminescent compound has a structure shown in a formula I, and a carbazole derivative group in the organic electroluminescent compound can increase the molecular weight of the compound, so that the obtained material has high glass transition temperature and can prevent crystallization, and the compound has certain distortion on a spatial three-dimensional structure and the film-forming property of the compound is improved; and an electron-deficient dibenzo-thiooxy six-membered heterocyclic ring structure is introduced into the other side of the benzene ring, so that the benzene ring is more favorable for receiving electrons and has good transmission performance. The invention also provides an organic electroluminescent device, and compared with the existing organic electroluminescent device, the organic electroluminescent device has better luminous performance and longer service life. The compound has good application effect in OLED devices and good industrialization prospect.
Description
Technical Field
The invention belongs to the technical field of semiconductors, and relates to an organic electroluminescent compound and application thereof.
Background
The Organic Light Emission Diodes (OLED) device technology has the unique advantages of self-luminescence, wide viewing angle, low energy consumption, high efficiency, thinness, rich colors, high response speed, wide applicable temperature range, low driving voltage, capability of manufacturing flexible, bendable and transparent display panels, environmental friendliness and the like, and has a very wide application prospect. Generally consisting of two opposing electrodes and at least one layer of an organic light-emissive compound interposed between the two electrodes. Electric charges are injected into an organic layer formed between an anode and a cathode to form electron and hole pairs, causing an organic compound having fluorescent or phosphorescent characteristics to produce light emission.
The light emitting material is classified into a fluorescent material and a phosphorescent material, and the formation method of the light emitting layer is a method of doping a phosphorescent material (organic metal) in a fluorescent host material and a method of doping a fluorescent host material with a fluorescent (organic matter containing nitrogen) dopant. In order to achieve efficient energy transfer, it is generally required that the host material has an energy gap larger than that of the dye and a triplet energy level higher than that of the dye molecule. Therefore, the T1 state energy can be smoothly transferred from the host material to the phosphorescent dye or the triplet excitons are limited in the dye molecules, so that the high-efficiency phosphorescent emission is realized.
At present, in organic light emitting devices prepared by using phosphorescent materials, materials containing triphenylamine groups such as CBP are mostly used as host light emitting materials of a light emitting layer, however, the glass transition temperature Tg of the materials is generally low and the thermal stability is poor, so that the service life of the organic light emitting device using the phosphorescent materials is short, and the use degree of the materials is reduced. How to design new materials with better performance for adjustment is always a problem to be solved by those skilled in the art.
Disclosure of Invention
In view of the defects of the prior art, the invention aims to provide an organic electroluminescent compound and application thereof. The organic electroluminescent compound can improve the luminous performance of an organic electroluminescent device, so that the organic electroluminescent device has low driving voltage and long service life.
In order to achieve the purpose, the invention adopts the following technical scheme:
in one aspect, the present invention provides an organic electroluminescent compound having a structure represented by formula I below:
wherein R is 1 、R 2 Independently selected from one of the structures shown below:
wherein the bond at the asterisk is R 1 Or R 2 The position where the benzene ring forms a common bond; L1-L4 represent the position of C-C bond on benzene ring, and R is 1 Or R 2 Through C L1 -C L2 Bond, C L2 -C L3 Bond or C L3 -C L4 The bond is to the benzene ring in the structure described by formula I.
The carbazole derivative group in the invention can increase the molecular weight of the compound, so that the obtained material has high glass transition temperature and can prevent crystallization, and the carbazole derivative group can ensure that the compound has certain distortion on a spatial three-dimensional structure and improve the film-forming property of the compound; and an electron-deficient dibenzo-thiooxy six-membered heterocyclic ring structure is introduced into the other side of the benzene ring, so that the benzene ring is more favorable for receiving electrons and has good transmission performance.
In the present invention, the
The group is any one of the following groups:
preferably, the organic electroluminescent compound is selected from any one of the following compounds:
in the present invention, the organic electroluminescent compounds can be synthesized by the following synthetic route: step (1)
Adding the raw material (l 0 mmol) into a 100mL two-mouth bottle, adding 30mL acetic acid, adding 6 times of hydrogen peroxide, and heating to reflux reaction for 2 hours; cooling to room temperature after reaction, separating out solid, washing with ethanol and water, and passing through MgSO 4 Dried, filtered, concentrated and purified by column chromatography (silica gel, from 50 2 Cl 2 To 3 2 Cl 2 ) Intermediate a (82% yield) was obtained as a white solid.
Step (2)
To a reaction flask, intermediate A (10 mmol), carbazole derivative (20 mmol), pd 2 (dba) 3 (0.2 mmol), tri-tert-butylphosphine (0.2 mmol), sodium tert-butoxide (22 mmol) and toluene (100 ml), nitrogen is pumped out for three times, heating is started until the temperature of the reaction solution reaches 95-105 ℃, the temperature is kept for reaction for 16-24h, and TLC and HPLC are sampled, and the raw materials are completely reacted. Heating was stopped, the temperature was reduced to room temperature, filtration was carried out, the organic layer was separated from the filtrate, the aqueous layer was extracted with ethyl acetate again, the organic layers were combined, dried over anhydrous magnesium sulfate, filtration was carried out, the filtrate was concentrated and purified by column chromatography (silica gel, purified from 30 2 Cl 2 To 5, 1PE/CH 2 Cl 2 Gradient elution) to obtain the target product.
Step (3)
Adding the intermediate B (20 mmol), pinacol diboron (25 mmol), potassium acetate (40 mmol) and Pd (dppf) Cl into a 250ml three-necked flask in sequence under the protection of nitrogen 2 (2 mmol) and 100ml 1, 4-dioxane, stirring and mixing, heating to 80 ℃, reacting for 24 hours, sampling a sample point plate, showing that no intermediate B remains and the reaction is complete; naturally cooling to room temperature, and concentrating the filtrateAnd purified by column chromatography (silica gel, purified 20 2 Cl 2 To 5 2 Cl 2 Gradient elution of) to obtain the target product.
Step (4)
In a 250mL three-necked flask, under the protection of nitrogen, the raw material A (10 mmol), the intermediate C (12 mmol) and 150mL of toluene/50 mL of ethanol were added, stirred and mixed, and then 20mL of aqueous potassium carbonate (2M) and 0.4mmol of Pd (PPh) were added 3 ) 4 Heating to 105 ℃, carrying out reflux reaction for 24 hours, sampling a point plate, and displaying that no raw material remains and the reaction is complete; naturally cool to room temperature, concentrate the filtrate and chromatographe on a column (silica gel, purified 20 2 Cl 2 To 2 2 Cl 2 Gradient elution) to obtain the target product.
In another aspect, the present invention provides an organic light emitting material comprising the organic electroluminescent compound as described above.
In another aspect, the present invention provides a light emitting layer comprising the organic electroluminescent compound as described above.
In another aspect, the present invention provides an organic electroluminescent device comprising a substrate, an anode layer, a cathode layer, and organic functional layers interposed between the anode layer and the cathode layer, at least one of the organic functional layers comprising an organic electroluminescent compound as described above.
Compared with the existing organic electroluminescent device, the organic electroluminescent device has better luminous performance and longer service life.
Preferably, the organic functional layer comprises a hole injection layer, a hole transport layer, an organic light emitting layer and an electron transport layer, the organic light emitting layer comprises a host material and a doping dye, and the host material contains the organic electroluminescent compound.
The hole transport region of the organic electroluminescent device of the invention requires materials with good hole transport performance, and can effectively transport holes from the anode to the luminescent layer. The hole transport region may be a single-layer structure formed of a single material, a single-layer structure formed of a plurality of different materials, or a multi-layer structure formed of a plurality of different materials. The hole transport region may have a structure of a hole transport layer/a hole injection layer, a structure of an electron blocking layer/a hole transport layer/a hole injection layer, but is not limited thereto; among them, NPB is a commonly used hole transport material.
The light-emitting layer of the organic electroluminescent device has good light-emitting characteristics, and the range of visible light can be adjusted according to requirements. The organic electroluminescent device structure may be a single light emitting layer or a multiple light emitting layer structure.
The organic electron transport material of the organic electroluminescent device of the invention is required to have good electron transport performance, can effectively transport electrons from the cathode to the luminescent layer, and has high electron mobility. The electron transport region includes one or more of a hole blocking layer and an electron transport layer, for example: the electron transport region may have a structure of an electron transport layer, a structure of a hole blocking layer/electron transport layer, but is not limited thereto.
The electron injection layer of the organic electroluminescent device can effectively inject electrons from the cathode into the organic layer, and is mainly selected from alkali metals or compounds of alkali metals, or compounds of alkaline earth metals or complexes of alkali metals.
Preferably, the doped dye is a red phosphorescent material.
Preferably, the mass doping concentration of the doping material is 3% -30%; among them, the mass doping concentration of the doping material in the light-emitting layer is preferably 5% to 15%.
Compared with the prior art, the invention has the following beneficial effects:
the organic electroluminescent compound is beneficial to receiving electrons and has good transmission performance on one hand by connecting the electron donor and the electron acceptor on two sides of the benzene ring. The sulfuryl can form a hydrogen bond with nearby hydrogen atoms, so that bond energy weakening caused by excessive distortion of a compound bond angle is avoided, and better chemical stability can be maintained. The other side is connected with a series of groups of carbazole derivatives, the triplet state energy level of the molecule is improved, and the exciton composite region can be effectively widened, so that excitons are uniformly distributed, the recombination of current carriers at an interface is avoided, and the triplet state-triplet state quenching of the excitons at high concentration is reduced, thereby obtaining the excellent phosphorescent main body material with higher triplet state and wider energy gap.
The carbazole derivative group with a larger conjugated structure of the organic electroluminescent compound is beneficial to the solid-state accumulation among molecules in the evaporation film-forming process of material molecules, effectively improves the transfer and transfer capacity of charges among molecules, has very high carrier mobility, and simultaneously has a larger space structure so as to greatly improve the glass transition temperature Tg of the compound, so that the organic electroluminescent material has higher thermal and chemical stability.
The organic electroluminescent compound of the invention has simple synthesis and is beneficial to the industrial application of materials. The organic electroluminescent device is applied to the organic electroluminescent device, so that the device has better luminous performance and longer service life compared with the existing organic electroluminescent device. The compound has good application effect in OLED devices and good industrialization prospect.
Detailed Description
The technical solution of the present invention is further explained by the following embodiments. It should be understood by those skilled in the art that the examples are only for the understanding of the present invention and should not be construed as the specific limitation of the present invention.
Preparation of example 1
The preparation method comprises the following specific steps:
to a reaction flask were added 10mmol of p-dibromobenzene, 20mmol of carbazole derivative, and Pd 2 (dba) 3 (0.2 mmol), tri-tert-butylphosphine (0.2 mmol), sodium tert-butoxide (22 mmol), toluene (100 mL), nitrogen was purged three times and heating was started,keeping the temperature of the reaction solution at 95-105 ℃, reacting for 16-24h, sampling TLC and HPLC, and completely reacting the raw materials. Heating was stopped, the temperature was reduced to room temperature, filtration was carried out, the organic layer was separated from the filtrate, the aqueous layer was extracted with ethyl acetate again, the organic layers were combined, dried over anhydrous magnesium sulfate, filtration was carried out, the filtrate was concentrated and purified by column chromatography (silica gel, purified from 30 2 Cl 2 To 5, 1PE/CH 2 Cl 2 Gradient elution of) to yield intermediate B1.
Adding the intermediate B (20 mmol), pinacol diborate (25 mmol), potassium acetate (40 mmol) and Pd (dppf) Cl into a 250mL three-neck flask in sequence under the protection of nitrogen 2 (2 mmol) and 100mL of 1, 4-dioxane, stirring and mixing, heating to 80 ℃, reacting for 24 hours, sampling a sample point plate, and showing that no intermediate B remains and the reaction is complete; naturally cool to room temperature, concentrate the filtrate and chromatographe on a column (silica gel, purified 20 2 Cl 2 To 5 2 Cl 2 Gradient elution of) to yield intermediate C1.
In a 250mL three-necked flask, under the protection of nitrogen, the raw material A (10 mmol), the intermediate C1 (12 mmol) and 150mL of toluene/50 mL of ethanol were added, stirred and mixed, and then 20mL of aqueous potassium carbonate (2M) and 0.4mmol of Pd (PPh) were added 3 ) 4 Heating to 105 ℃, carrying out reflux reaction for 24 hours, sampling a sample, and indicating that no raw material remains and the reaction is complete; naturally cool to room temperature, concentrate the filtrate and chromatographe on a column (silica gel, purified 20 2 Cl 2 To 2 2 Cl 2 Gradient elution of) to give compound 1.
Further purification of compound 1 using reverse phase column chromatography with acetonitrile as eluent gave a white solid and its structure was confirmed by mass spectrometry, HRMS Calcd for C 38 H 23 NSO 3 ：573.14，Found：573.13。C 38 H 23 NSO 3 Theoretical value of elemental analysis: c,79.56; h,4.04; n,2.44. Elemental analysis found: c,79.56; h,4.06; and N,2.4.
Preparation of example 2
The preparation method comprises the following specific steps:
to a reaction flask were added 10mmol of p-dibromobenzene, 20mmol of carbazole derivative, and Pd 2 (dba) 3 (0.2 mmol), tri-tert-butylphosphine (0.2 mmol), sodium tert-butoxide (22 mmol) and toluene (100 mL), nitrogen is pumped out for three times, heating is started, the temperature of the reaction solution reaches 95-105 ℃, the reaction is kept at the temperature for 16-24h, and TLC and HPLC are sampled, so that the raw materials are completely reacted. Heating was stopped, the temperature was reduced to room temperature, filtration was carried out, the organic layer was separated from the filtrate, the aqueous layer was extracted with ethyl acetate again, the organic layers were combined, dried over anhydrous magnesium sulfate, filtration was carried out, the filtrate was concentrated and purified by column chromatography (silica gel, purified from 30 2 Cl 2 To 5, 1PE/CH 2 Cl 2 Gradient elution of) to yield intermediate B2.
Adding the intermediate B (20 mmol), pinacol diboron (25 mmol), potassium acetate (40 mmol) and Pd (dppf) Cl into a 250mL three-necked flask in sequence under the protection of nitrogen 2 (2 mmol) and 100mL of 1, 4-dioxane, stirring and mixing, heating to 80 ℃, reacting for 24 hours, sampling a sample point plate, and showing that no intermediate B remains and the reaction is complete; cool to room temperature naturally, concentrate the filtrate and perform column chromatography (silica gel, from pure 20 2 Cl 2 To 5, 1PE/CH 2 Cl 2 Gradient elution of) to yield intermediate C2.
In a 250mL three-necked flask, under the protection of nitrogen, the raw material A (10 mmol), the intermediate C1 (12 mmol) and 150mL of toluene/50 mL of ethanol were added, stirred and mixed, and then 20mL of aqueous potassium carbonate (2M) and 0.4mmol of Pd (PPh) were added 3 ) 4 Heating to 105 ℃, carrying out reflux reaction for 24 hours, sampling a point plate, and displaying that no raw material remains and the reaction is complete; naturally cool to room temperature, concentrate the filtrate and chromatographe on a column (silica gel, purified 20 2 Cl 2 To 2 2 Cl 2 Gradient elution of (d) to give compound 5 was further purified using reverse phase column chromatography with acetonitrile as eluent to give a white solid and its structure determined by mass spectrometry, HRMS Calcd for C 42 H 23 NSO 5 ：653.13，Found：653.15。C 42 H 23 NSO 5 Theoretical value of elemental analysis: c,77.17; h,3.55; and N,2.14. Elemental analysis found: c,77.17; h,3.55; n,2.14.
Preparation of example 3
The preparation method comprises the following specific steps:
to a reaction flask were added 10mmol of p-dibromobenzene, 20mmol of carbazole derivative, and Pd 2 (dba) 3 (0.2 mmol), tri-tert-butylphosphine (0.2 mmol), sodium tert-butoxide (22 mmol) and toluene (100 mL), nitrogen is pumped out for three times, heating is started, the temperature of the reaction solution reaches 95-105 ℃, the reaction is kept at the temperature for 16-24h, and TLC and HPLC are sampled, so that the raw materials are completely reacted. Heating was stopped, the temperature was reduced to room temperature, filtration was carried out, the organic layer was separated from the filtrate, the aqueous layer was extracted with ethyl acetate again, the organic layers were combined, dried over anhydrous magnesium sulfate, filtration was carried out, the filtrate was concentrated and purified by column chromatography (silica gel, purified from 30 2 Cl 2 To 5, 1PE/CH 2 Cl 2 Gradient elution of) to yield intermediate B3.
Adding the intermediate B (20 mmol), pinacol diboron (25 mmol), potassium acetate (40 mmol) and Pd (dppf) Cl into a 250mL three-necked flask in sequence under the protection of nitrogen 2 (2 mmol) and 100mL of 1, 4-dioxane, stirring and mixing, heating to 80 ℃, reacting for 24 hours, sampling a sample point plate, and showing that no intermediate B remains and the reaction is complete; naturally cool to room temperature, concentrate the filtrate and chromatographe on a column (silica gel, purified 20 2 Cl 2 To 5 2 Cl 2 Gradient elution of (iv) to yield intermediate C3.
In a 250mL three-necked flask, under the protection of nitrogen, the raw material A (10 mmol), the intermediate C1 (12 mmol) and 150mL of toluene/50 mL of ethanol were added, stirred and mixed, and then 20mL of aqueous potassium carbonate (2M) and 0.4mmol of Pd (PPh) were added 3 ) 4 Heating to 105 ℃, carrying out reflux reaction for 24 hours, sampling a point plate, and displaying that no raw material remains and the reaction is complete; cool to room temperature naturally, concentrate the filtrate and perform column chromatography (silica gel, from pure 20 2 Cl 2 To 2 2 Cl 2 Gradient elution of) to give compound 14
Compound 14 was further purified using reverse phase column chromatography with acetonitrile as eluent to give a white solid and its structure determined by mass spectrometry, HRMS Calcd for C 48 H 35 NSO 3 ：705.23，Found：705.23。C 48 H 35 NSO 3 Theoretical value of elemental analysis: c,81.68; h,5.00; n,1.98. Elemental analysis found: c,81.69; h,5.02; and N,1.99.
The remaining compounds were synthesized according to the method of the present invention as described above, and the mass spectrum and elemental analysis data of all the synthesized compounds are shown in the following table 1:
TABLE 1
Detection example 1
This test example T was conducted on production example 1, production example 2 and production example 3, and other obtained products, respectively 1 And measuring the energy level, the thermal property and the HOMO energy level, and detecting the results as shown in the following table 2:
TABLE 2
| Compound (I) | T 1 (eV) | Tg(℃) | Td(℃) | HOMO energy level (eV) |
| Compound 1 | 2.57 | 133 | 399 | -5.64 |
| Compound 2 | 2.64 | 139 | 410 | -5.56 |
| Compound 3 | 2.62 | 140 | 406 | -5.62 |
| Compound 4 | 2.57 | 136 | 384 | -5.49 |
| Compound 5 | 2.65 | 133 | 392 | -5.58 |
| Compound 6 | 2.6 | 135 | 389 | -5.39 |
| Compound 7 | 2.67 | 138 | 385 | -5.45 |
| Compound 8 | 2.52 | 133 | 394 | -5.57 |
| Compound 9 | 2.58 | 138 | 392 | -5.56 |
| Compound 10 | 2.54 | 139 | 387 | -5.48 |
| Compound 11 | 2.59 | 134 | 393 | -5.58 |
| Compound 12 | 2.6 | 135 | 394 | -5.53 |
| Compound 13 | 2.62 | 137 | 390 | -5.59 |
| Compound 14 | 2.61 | 136 | 388 | -5.56 |
| Compound 15 | 2.62 | 135 | 395 | -5.58 |
| CBP | 2.52 | 62 | 370 | -5.80 |
Wherein the triplet energy level T 1 Is tested by an F4600 fluorescence spectrometer of Hitachi, and the test condition of the material is 2 multiplied by 10 - 5 A toluene solution of mol/L; the glass transition temperature Tg is measured by differential scanning calorimetry (DSC, DSC204F1 differential scanning calorimeter of Germany Tissian corporation), and the heating rate is 10 ℃/min; the thermogravimetric loss temperature Td is a temperature at which 1% of the weight is lost in a nitrogen atmosphere, and is measured on a TGA-50H thermogravimetric analyzer of Shimadzu corporation, japan, and the nitrogen flow rate is 20mL/min; the highest occupied molecular orbital HOMO energy level was tested by the ionization energy test system (IPS 3) in an atmospheric environment.
As can be seen from table 1, the compound of the present invention has a high triplet level, a high thermal stability, and a suitable HOMO level, and is suitable for use as a light emitting layer material.
Application examples
This application embodiment provides an OLED device, and its structure includes in proper order: transparent substrate layer, anode layer, hole injection layer, hole transport layer, light emitting layer, electron transport layer/hole blocking layer, electron injection layer, cathode electrode layer.
The substrate may be a substrate used in a conventional organic light emitting organic electroluminescent device, for example: glass or plastic. The anode material may be a transparent high conductive material, such as Indium Tin Oxide (ITO), indium Zinc Oxide (IZO), tin dioxide (SnO) 2 ) Zinc oxide (ZnO), and the like. In the fabrication of the organic electroluminescent device according to the embodiment, a glass substrate and ITO are used as an anode material.
In the fabrication of the organic electroluminescent device according to the application embodiment, NPB is selected as a hole transport material.
In the present embodiment, a single light emitting layer structure is adopted. In this application embodiment, the light-emitting layer of the organic electroluminescent device includes a host material and a dopant material. The host material is composed of the compound of the invention; the doping material is Ir (pq) 2acac.
The specific structural formula of the material is as follows:
preparation of organic electroluminescent device:
comparative example 1
Firstly, cleaning an ITO anode layer on a transparent glass substrate layer, respectively ultrasonically cleaning the ITO anode layer for 15 minutes by using deionized water, acetone and ethanol, and then treating the ITO anode layer for 2 minutes in a plasma cleaner;
then HAT-CN is evaporated on the substrate, the film thickness is 10nm, and the layer is a hole injection layer;
then, TAPC with a film thickness of 50nm is evaporated to form a hole transport layer; TCTA was evaporated to a thickness of 5nm as an electron blocking layer.
Then, a 40nm light emitting layer was evaporated: wherein CBP is the main material, ir (pq) 2 acac is used as a phosphorescent doped object, and the doping mass concentration is 6%;
evaporating BmYPB on the light-emitting layer in a vacuum evaporation mode, wherein the thickness of the BmYPB is 35nm, and the organic material layer serves as an electron transmission layer;
vacuum evaporating an electron injection layer LiF on the hole blocking/electron transport layer, wherein the thickness of the electron injection layer LiF is 1nm, and the electron injection layer is the electron injection layer; on top of the electron injection layer, cathode Al (80 nm) was vacuum evaporated, which layer was a cathode electrode layer.
Examples 1 to 15
The method of fabricating the device of the example was the same as that of the comparative example except that the compound of the present invention was used as a host material instead of CBP. The device performance was tested and the results are shown in table 3.
TABLE 3
Wherein, the device test performance is compared with that of comparative example CBP, and the current efficiency is 10mA/cm 2 Measured under the condition; the life test system is an OLED device life tester of MODEL MODEL 58131 of Chroma, and LT95 life attenuation is carried out under the test of 5000nit brightness.
As can be seen from Table 3, the novel organic electroluminescent material of the present invention, when used in an organic electroluminescent device, has a greatly improved efficiency and lifetime compared to the known OLED materials, and particularly, the driving lifetime of the device is greatly improved, and the novel organic electroluminescent material is a phosphorescent host material with excellent performance. As described above, the compound of the present invention has high thermal stability, and the organic electroluminescent device produced has a high device lifetime.
The applicant states that the present invention is illustrated by the above examples of the organic electroluminescent compounds and their applications, but the present invention is not limited to the above examples, i.e. it is not meant that the present invention must be implemented by means of the above examples. It should be understood by those skilled in the art that any modifications of the present invention, equivalent substitutions of the raw materials of the product of the present invention, and the addition of auxiliary components, selection of specific modes, etc., are within the scope and disclosure of the present invention.
Claims (8)
1. An organic electroluminescent compound, wherein the organic electroluminescent compound has a structure represented by formula I:
wherein R is 1 、R 2 Independently selected from one of the structures shown below:
wherein the bond at the asterisk is R 1 Or R 2 The positions of the benzene rings where the bond is shared; L1-L4 represent the position of C-C bond on benzene ring, and R 1 Or R 2 Is connected to the benzene ring in the structure shown in the formula I through a CL1-CL2 bond, a CL2-CL3 bond or a CL3-CL4 bond.
2. The organic electroluminescent compound according to claim 1, wherein the organic electroluminescent compound is represented by
The group is any one of the following groups:
3. the organic electroluminescent compound according to claim 1 or 2, wherein the organic electroluminescent compound is selected from any one of the following compounds:
4. an organic light-emitting material comprising the organic electroluminescent compound according to any one of claims 1 to 3.
5. A light-emitting layer characterized in that the light-emitting layer comprises the organic electroluminescent compound according to any one of claims 1 to 3.
6. An organic electroluminescent device comprising a substrate, an anode layer, a cathode layer, and organic functional layers interposed between the anode layer and the cathode layer, at least one of the organic functional layers comprising the organic electroluminescent compound according to any one of claims 1 to 3.
7. The organic electroluminescent device according to claim 6, wherein the organic functional layer comprises a hole injection layer, a hole transport layer, an organic light emitting layer, an electron transport layer, the organic light emitting layer comprises a host material and a dopant dye, and the host material comprises the organic electroluminescent compound according to any one of claims 1 to 3.
8. The organic electroluminescent device according to claim 6 or 7, wherein the doped dye is a red phosphorescent material.
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