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Hole-transporting type blue luminescent material as well as preparation and uses thereof

A technology of hole transport and blue light, applied in the direction of organic chemistry, etc., can solve the problems of complicated device preparation, poor carrier injection and transport, etc., and achieve the effect of good application prospects

Inactive Publication Date: 2012-05-30
INST OF CHEM CHINESE ACAD OF SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The blue light material has a large energy gap width. Usually, when preparing blue light-emitting devices, blue light materials need to be doped into some host materials to improve the shortcomings of poor carrier injection and transport, but this will complicate the preparation of the device.

Method used

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  • Hole-transporting type blue luminescent material as well as preparation and uses thereof
  • Hole-transporting type blue luminescent material as well as preparation and uses thereof
  • Hole-transporting type blue luminescent material as well as preparation and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0064] Synthesis of the precursor 9,9-bis[4-(N,N-dimethylanilino)phenyl]-2-bromofluorene (compound 3).

[0065] 2-Bromofluorenone (4g, 15.4mmol) was mixed with 4,4'-dimethyltriphenylamine (15g, 55mmol), and heated to 120°C under nitrogen atmosphere. After the mixture was completely melted, the catalyst trifluoromethyl Sulfonic acid 1mL, keep heating overnight. After the reaction, dichloromethane was added to dissolve all unreacted raw materials and other impurities, and the white solid obtained by filtration was 9,9-bis[4-(N,N-di-p-toluidyl)phenyl]-2-bromofluorene (Formula 3) 11.0 g, yield 90%. Mass spectrum: m / z 786.7 (M + +1); elemental analysis (%) C 53 h 43 BrN 2 : theoretical value C 80.80, H 5.50, N 3.56; found value C 80.05, H 5.64, N 3.57.

Embodiment 2

[0067] Synthesis of the precursor 9,9-bis[4-(N,N-di-p-toluidyl)phenyl]fluorene-2,7-diboronic acid pinacate (compound 2).

[0068] 2,7-dibromofluorenone (4g, 12mmol) was mixed with 4,4'-dimethyltriphenylamine (15g, 55mmol), and heated to 120°C under nitrogen atmosphere. After the mixture was completely melted, the catalyst trifluoro Methanesulfonic acid 0.75mL, kept heating overnight. After the reaction, the crude product was dissolved in dichloromethane, and part of the solvent was removed under reduced pressure, then poured into a large amount of acetone for precipitation, and the white solid obtained after filtration was 9,9-bis[4-(N,N-di-p-methyl Anilino)phenyl]-2,7-dibromofluorene (compound 1) 8.7g, yield 83%.

[0069] Mass spectrum: m / z 864.9 (M + +1); NMR[ 1 H NMR (CDCl 3 , 300MHz)]: δ=7.57(d, 2H), 7.49(s, 2H), 7.47(d, 2H), 7.06-6.92(m, 20H), 6.86(d, 2H), 2.29(s, 12H) ;Elemental analysis (%) C 53 h 42 Br 2 N 2 : theoretical value C 73.45, H 4.88, N 3.23; found v...

Embodiment 3

[0073] Combination bromides of conjugated groups: Synthesis of 4-(10-bromoanthracen-9-yl)-N,N-diphenylaniline (Compound 8).

[0074] 4-Bromotriphenylamine (3.24g, 10mmol) was dissolved in tetrahydrofuran (30mL), cooled to -78°C under a nitrogen atmosphere, added n-butyllithium (4.8mL, 12mmol), kept at low temperature for about 1 hour, and added isopropoxy boronic acid pinacidate (2.45mL, 12mmol), warmed up to room temperature and stirred overnight. After the reaction, the solvent was removed by rotary evaporation, and petroleum ether was used as the eluent. Silica gel column chromatography gave 2.2 g of the white solid product 4-dianilinophenylboronic acid pinacid (compound 7), with a yield of 59%. Mass spectrum: m / z371 (M + +1); elemental analysis (%) C 24 h 26 BNO 2 : Theoretical value C 77.64, H 7.06, N 3.77; found value C 77.42, H 7.18, N 3.75.

[0075] Compound 7 (1.86g, 5mmol), 9,10-dibromoanthracene (5.04g, 15mmol), tetrahydrofuran (100mL), potassium carbonate aque...

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Abstract

The invention relates to a hole-transporting blue color compound, which is a fluorine derivative based on 9, 9-bi-(4-(bi-p-methypheny) aminophenyl). The preparation method is to first mix 9, 9-bi-[4-(N, N-bi-p-toluidine) phenyl]-2-dibromofluorine and boric acid pinacol ester of conjugate radicle, or to mix 9, 9-bi-[4-(N, N-bi-p-tolyl-amino) phenyl] fluorine -2, 7-bi-boric acid pinacol ester and bromide of conjugate radicle; and then add in toluene, potash solution, aliquat336 and catalyst tetrakis (triphenylphosphine) palladium, and heat and reflow for 10 to 30 hours in nitrogen environment; when the reaction is done, decompress, remove the solution and get the target product, the derivative based on 9, 9-bi-(4-(bi-p-methypheny) aminophenyl) fluorine substituted by unilateral conjugate radical. The compound can be used as the hole-transporting layer and the luminescent layer as well in electroluminescent devices.

Description

technical field [0001] The invention relates to a hole-transporting blue light-emitting material. [0002] The present invention also relates to a preparation method of the above-mentioned luminescent material. [0003] The present invention also relates to the application of the above-mentioned luminescent material in the field of electroluminescence. Background technique [0004] Organic light-emitting diodes (OLEDs) have achieved rapid development since they were reported in 1987 (C.W.Tang, S.A. VanSlyke, Appl. Phys. Lett. 1987, 51, 913). Red, green and blue three-color luminescent materials are required for display and lighting, among which blue light materials are particularly important, because light of other colors can be obtained by down-conversion of blue light. Green and red light-emitting materials with excellent performance have been widely reported, but blue-light materials with excellent performance still need to be developed. The blue light material has a l...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C13/547
Inventor 于贵矫士博徐新军王丽萍狄重安刘云圻朱道本
Owner INST OF CHEM CHINESE ACAD OF SCI
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