CN114890985A - Preparation method of electron donating group substituted thiafluorene derivative - Google Patents
Preparation method of electron donating group substituted thiafluorene derivative Download PDFInfo
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- CN114890985A CN114890985A CN202210526531.9A CN202210526531A CN114890985A CN 114890985 A CN114890985 A CN 114890985A CN 202210526531 A CN202210526531 A CN 202210526531A CN 114890985 A CN114890985 A CN 114890985A
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- 238000002360 preparation method Methods 0.000 title claims abstract description 28
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 229910000160 potassium phosphate Inorganic materials 0.000 claims description 9
- 235000011009 potassium phosphates Nutrition 0.000 claims description 9
- 229940125782 compound 2 Drugs 0.000 claims description 6
- 229940126214 compound 3 Drugs 0.000 claims description 6
- 229940125904 compound 1 Drugs 0.000 claims description 5
- LBQQNHMLQQLHPI-UHFFFAOYSA-N CC1(C)OB(C(C=C2)=CC=C2N(C(C=C2)=CC=C2N(C)C)C(C=C2)=CC=C2N(C)C)OC1(C)C Chemical compound CC1(C)OB(C(C=C2)=CC=C2N(C(C=C2)=CC=C2N(C)C)C(C=C2)=CC=C2N(C)C)OC1(C)C LBQQNHMLQQLHPI-UHFFFAOYSA-N 0.000 claims description 3
- BTJQFRZWDBZGJA-UHFFFAOYSA-N CCN(CC)C(C=C1)=CC=C1N(C1=CC=C(B2OC(C)(C)C(C)(C)O2)C=C1)C(C=C1)=CC=C1N(CC)CC Chemical compound CCN(CC)C(C=C1)=CC=C1N(C1=CC=C(B2OC(C)(C)C(C)(C)O2)C=C1)C(C=C1)=CC=C1N(CC)CC BTJQFRZWDBZGJA-UHFFFAOYSA-N 0.000 claims description 3
- YTMVIIRAWJJGCT-UHFFFAOYSA-N 1-n,1-n-diphenyl-4-n-[4-(n-phenylanilino)phenyl]-4-n-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]benzene-1,4-diamine Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=C(N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC=CC=2)C=C1 YTMVIIRAWJJGCT-UHFFFAOYSA-N 0.000 claims description 2
- SNRCKKQHDUIRIY-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloromethane;dichloropalladium;iron(2+) Chemical compound [Fe+2].ClCCl.Cl[Pd]Cl.C1=C[CH-]C(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.C1=C[CH-]C(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 SNRCKKQHDUIRIY-UHFFFAOYSA-L 0.000 claims 3
- 239000000376 reactant Substances 0.000 claims 3
- 230000035484 reaction time Effects 0.000 claims 3
- 150000001875 compounds Chemical class 0.000 abstract description 8
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical class C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 abstract description 8
- 238000000926 separation method Methods 0.000 abstract description 8
- 238000000034 method Methods 0.000 abstract description 7
- 238000003786 synthesis reaction Methods 0.000 abstract description 5
- 238000001308 synthesis method Methods 0.000 abstract description 3
- 238000011403 purification operation Methods 0.000 abstract description 2
- 239000008204 material by function Substances 0.000 abstract 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical class C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- 239000002904 solvent Substances 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Natural products ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000012074 organic phase Substances 0.000 description 12
- 239000012043 crude product Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 239000012295 chemical reaction liquid Substances 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- 238000007865 diluting Methods 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- WNEXSUAHKVAPFK-UHFFFAOYSA-N 2,8-dibromodibenzothiophene Chemical compound C1=C(Br)C=C2C3=CC(Br)=CC=C3SC2=C1 WNEXSUAHKVAPFK-UHFFFAOYSA-N 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- KKLCYBZPQDOFQK-UHFFFAOYSA-N 4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolane Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=CC=C1 KKLCYBZPQDOFQK-UHFFFAOYSA-N 0.000 description 1
- 238000006069 Suzuki reaction reaction Methods 0.000 description 1
- 238000012984 biological imaging Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 239000012216 imaging agent Substances 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 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
- 230000035515 penetration Effects 0.000 description 1
- 230000005622 photoelectricity Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 150000001651 triphenylamine derivatives Chemical class 0.000 description 1
- 125000006617 triphenylamine group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides a preparation method of electron donating group substituted thiafluorene derivatives, and relates to the field of organic synthesis. The electron-donating group-substituted dibenzothiophene derivative has a structure shown in formula 1-3, the synthesis method of the compound is simple, and the separation and purification operation process of the product is simple and convenient. By introducing different substituted triphenylamine structural units as electron donating groups, the thiafluorene derivative with a donor-acceptor-donor structure is synthesized, the variety of the thiafluorene derivative is enriched, and the compound has wide application prospect in the field of organic functional materials.
Description
Technical Field
The invention relates to the technical field of organic synthesis, in particular to a preparation method of electron-donating group-substituted dibenzothiophene derivatives.
Background
The dibenzothiophene has good plane conjugation and abundant electronic properties, and the characteristic of easy modification of the dibenzothiophene makes many dibenzothiophene derivatives have wide application in the fields of biomedicine, organic photoelectricity, intelligent materials and the like, and become an important organic compound.
Among the numerous kinds of dibenzothiophene derivatives, dibenzothiophene derivatives having a donor-acceptor-donor structure have been the focus of research. On the one hand, the donor-acceptor-donor structure can effectively separate electron cloud distribution between the highest occupied orbital (HOMO) and the lowest unoccupied orbital (LUMO), thereby forming an effective intramolecular charge transfer effect, reducing the molecular band gap, finally realizing emission with longer wavelength, and contributing to the development of a biological imaging agent with deeper tissue penetration depth. On the other hand, heteroatom substitution can effectively increase the transition mode of n → pi, can enhance intersystem crossing, and is helpful for developing a photodynamic agent with good performance. Therefore, the design and synthesis of the dibenzothiophene derivative with a donor-acceptor-donor structure are of great significance.
Disclosure of Invention
The present invention aims to provide a process for the preparation of electron group substituted dibenzothiophene derivatives. The compound provided by the invention has simple synthesis method and simple and convenient separation and purification operation process.
The invention provides a preparation method of electron donating group substituted thiafluorene derivatives, which is characterized in that a target product has the following structure:
the invention provides a preparation method of the compound, which comprises the following synthesis steps:
a method for preparing compound 1:
mixing a certain amount of 2, 8-dibromo-sulfur-heterofluorene, 4- [ N, N-di (4-dimethylaminophenyl) amino ] phenylboronic acid pinacol ester, [1,1' -bis (diphenylphosphino) ferrocene ] palladium dichloride dichloromethane complex, potassium phosphate and a certain amount of tetrahydrofuran in a reaction bottle, heating to a certain temperature, stirring and reacting at the temperature for a certain time, obtaining a crude product by the steps of diluting the reaction mixture with a solvent, extracting, separating, drying, recovering the solvent and the like, obtaining a solution of a target product by utilizing column chromatography separation, and recovering the solvent to obtain a compound 1.
The preparation method of the compound 2 comprises the following steps:
mixing a certain amount of 2, 8-dibromo-sulfur-heterofluorene, 4- [ N, N-di (4-diethylaminophenyl) amino ] phenylboronic acid pinacol ester, [1,1' -bis (diphenylphosphino) ferrocene ] palladium dichloride dichloromethane complex, potassium phosphate and a certain amount of tetrahydrofuran in a reaction bottle, heating to a certain temperature, stirring and reacting at the temperature for a certain time, obtaining a crude product by the steps of diluting the reaction mixture with a solvent, extracting, separating, drying, recovering the solvent and the like, obtaining a solution of a target product by utilizing column chromatography separation, and recovering the solvent to obtain a compound 2.
A method for preparing compound 3:
mixing a certain amount of 2, 8-dibromo-sulfur-heterofluorene, 4- [ N, N-di (4-diphenylamine-phenyl) amino ] phenylboronic acid pinacol ester, [1,1' -bis (diphenylphosphino) ferrocene ] palladium dichloride dichloromethane complex, potassium phosphate and a certain amount of tetrahydrofuran in a reaction bottle, heating to a certain temperature, stirring and reacting at the temperature for a certain time, obtaining a crude product by the steps of diluting the reaction mixture with a solvent, extracting, separating, drying, recovering the solvent and the like, obtaining a solution of a target product by utilizing column chromatography separation, and recovering the solvent to obtain a compound 3.
The electron-donating group-substituted dibenzothiophene derivative provided by the invention has a donor-acceptor-donor structure and can be synthesized through one-step Suzuki coupling reaction. The thiafluorene group in the structure of the compound is used as an acceptor, two sides of the thiafluorene group are respectively connected with triphenylamine derivatives with strong electron donating property, and different electron donating groups modified on the triphenylamine group further enhance the intramolecular charge transfer property of the compound, are favorable for realizing the emission of the compound with longer wavelength, and enrich the variety of the thiafluorene derivatives.
The invention provides a preparation method of the compound, and the synthesis method provided by the invention is simple, the operation process of separation and purification is simple and convenient, the raw materials are easy to obtain, the yield is higher, and the method is suitable for large-scale synthesis and future large-scale production.
Detailed Description
Example 1
171 mg of 2, 8-dibromodibenzothiophene, 457 mg of 4- [ N, N-bis (4-dimethylaminophenyl) amino ] phenylboronic acid pinacol ester, 29 mg of [1,1' -bis (diphenylphosphino) ferrocene ] palladium dichloride dichloromethane complex, 212 mg of potassium phosphate and 8 mL of tetrahydrofuran are mixed in a reaction bottle, stirred for 5 min to fully dissolve the raw materials, and stirred and reacted for 16 h at 60 ℃ under the protection of nitrogen. After the reaction is finished, cooling to room temperature, diluting the reaction liquid with 30 mL of ethyl acetate, transferring the reaction liquid into a separating funnel, washing an organic phase twice with 35 mL of saturated ammonium chloride aqueous solution each time, separating out the organic phase, combining the aqueous phases, extracting twice with 20 mL of ethyl acetate each time, drying the combined organic phase for 20 min with 3 g of anhydrous sodium sulfate, recovering the solvent from the dried organic phase through reduced pressure distillation to obtain a crude product, performing column chromatography separation with 200-mesh and 300-mesh silica gel, wherein the used eluent is petroleum ether and ethyl acetate with the ratio of 5:1, collecting the fourth zone as a target product solution, and recovering the solvent through reduced pressure distillation to obtain 308 mg of yellow solid, namely the compound 1, and the yield is 73%.
Example 2
171 mg of 2, 8-dibromodibenzothiophene, 514 mg of 4- [ N, N-bis (4-diethylaminophenyl) amino ] phenylboronic acid pinacol ester, 29 mg of [1,1' -bis (diphenylphosphino) ferrocene ] palladium dichloride dichloromethane complex, 212 mg of potassium phosphate and 8 mL of tetrahydrofuran are mixed in a reaction bottle, stirred for 5 min to fully dissolve the raw materials, and stirred and reacted for 16 h at 60 ℃ under the protection of nitrogen. After the reaction is finished, the temperature is reduced to room temperature, the reaction liquid is diluted by 30 mL of ethyl acetate and transferred to a separating funnel, an organic phase is washed twice with 35 mL of saturated ammonium chloride aqueous solution each time, after an organic phase is separated, an aqueous phase is combined and extracted twice with 20 mL of ethyl acetate each time, the combined organic phase is dried for 20 min by 3 g of anhydrous sodium sulfate, the dried organic phase is subjected to reduced pressure distillation to recover a solvent to obtain a crude product, the crude product is separated by 200-mesh 300-mesh silica gel column chromatography, the used eluent is petroleum ether and ethyl acetate with the ratio of 5:1, the fourth zone is collected as a target product solution, the solvent is recovered by reduced pressure distillation to obtain 393 mg of yellow solid, namely a compound 2, and the yield is 76%.
Example 3
171 mg of 2, 8-dibromodibenzothiophene, 706 mg of 4- [ N, N-bis (4-diphenylaminophenyl) amino ] phenylboronic acid pinacol ester, 29 mg of [1,1' -bis (diphenylphosphino) ferrocene ] palladium dichloride dichloromethane complex, 212 mg of potassium phosphate and 8 mL of tetrahydrofuran are mixed in a reaction bottle, stirred for 5 min to fully dissolve the raw materials, and stirred and reacted for 16 h at 60 ℃ under the protection of nitrogen. After the reaction is finished, cooling to room temperature, diluting the reaction liquid with 30 mL of ethyl acetate, transferring the reaction liquid into a separating funnel, washing an organic phase twice with 35 mL of saturated ammonium chloride aqueous solution each time, separating out the organic phase, combining the aqueous phases, extracting twice with 20 mL of ethyl acetate each time, drying the combined organic phase for 20 min with 3 g of anhydrous sodium sulfate, recovering the solvent from the dried organic phase through reduced pressure distillation to obtain a crude product, performing column chromatography separation with 200-mesh and 300-mesh silica gel, wherein the used eluent is 3:1 petroleum ether and ethyl acetate, collecting the fourth zone as a target product solution, and recovering the solvent through reduced pressure distillation to obtain 469 mg of yellow solid, namely the compound 3, and the yield is 70%.
Claims (10)
1. The preparation method of electron donating group substituted thiafluorene derivative is characterized by comprising the following steps: the electron-donating group-substituted thiafluorene derivative has the following structure:
2. the preparation method of electron donating group substituted thiafluorene derivative is characterized by comprising the following steps: in the preparation method of the compound 1, the mass ratio of reactants is 2, 8-dibromo-sulfur-heterofluorene: 4- [ N, N-bis (4-dimethylaminophenyl) amino ] phenylboronic acid pinacol ester: [1,1' -bis (diphenylphosphino) ferrocene ] dichloropalladium dichloromethane complex: potassium phosphate = 1: 2.673: 0.170: 1.240.
3. the preparation method of electron donating group substituted thiafluorene derivative is characterized by comprising the following steps: the reaction temperature in the preparation method of the compound 1 is 60 ℃.
4. The preparation method of electron donating group substituted thiafluorene derivative is characterized by comprising the following steps: the reaction time in the preparation method of the compound 1 is 16 h.
5. The preparation method of electron donating group substituted thiafluorene derivative is characterized by comprising the following steps: in the preparation method of the compound 2, the mass ratio of reactants is 2, 8-dibromo-sulfur-heterofluorene: 4- [ N, N-bis (4-diethylaminophenyl) amino ] phenylboronic acid pinacol ester: [1,1' -bis (diphenylphosphino) ferrocene ] dichloropalladium dichloromethane complex: potassium phosphate = 1: 3.006: 0.170: 1.240.
6. the preparation method of electron donating group substituted thiafluorene derivative is characterized by comprising the following steps: the reaction temperature in the preparation method of the compound 2 is 60 ℃.
7. The preparation method of electron donating group substituted thiafluorene derivative is characterized by comprising the following steps: the reaction time in the preparation method of the compound 2 is 16 h.
8. The preparation method of electron donating group substituted thiafluorene derivative is characterized by comprising the following steps: in the preparation method of the compound 3, the mass ratio of reactants is 2, 8-dibromo-sulfur-heterofluorene: 4- [ N, N-bis (4-diphenylaminophenyl) amino ] phenylboronic acid pinacol ester: [1,1' -bis (diphenylphosphino) ferrocene ] dichloropalladium dichloromethane complex: potassium phosphate = 1: 4.129: 0.170: 1.240.
9. the preparation method of electron donating group substituted thiafluorene derivative is characterized by comprising the following steps: the reaction temperature in the preparation method of the compound 3 is 60 ℃.
10. The preparation method of electron donating group substituted thiafluorene derivative is characterized by comprising the following steps: the reaction time in the preparation method of the compound 3 is 16 h.
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005112765A (en) * | 2003-10-07 | 2005-04-28 | Mitsui Chemicals Inc | Heterocyclic compound and organic electroluminescent device containing the compound |
| CN109564972A (en) * | 2017-03-09 | 2019-04-02 | 株式会社Lg化学 | Organic illuminating element |
| CN114163338A (en) * | 2020-09-11 | 2022-03-11 | 东进世美肯株式会社 | Compound for reflective electrode protection layer and back light-emitting element comprising same |
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2022
- 2022-05-16 CN CN202210526531.9A patent/CN114890985A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005112765A (en) * | 2003-10-07 | 2005-04-28 | Mitsui Chemicals Inc | Heterocyclic compound and organic electroluminescent device containing the compound |
| CN109564972A (en) * | 2017-03-09 | 2019-04-02 | 株式会社Lg化学 | Organic illuminating element |
| CN114163338A (en) * | 2020-09-11 | 2022-03-11 | 东进世美肯株式会社 | Compound for reflective electrode protection layer and back light-emitting element comprising same |
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