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High performance electroluminescent organic material and application thereof in organic EL device

An electroluminescent material and high-performance technology, which is applied in the direction of luminescent materials, electric solid devices, electrical components, etc., can solve the problems of reducing fluorescence quenching efficiency, and achieve improved device stability, high efficiency, and high electroluminescent efficiency Effect

Inactive Publication Date: 2009-05-06
JILIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This three-dimensional structure can also prevent the aggregation of planar rigid aromatic molecules and reduce the fluorescence quenching efficiency.

Method used

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  • High performance electroluminescent organic material and application thereof in organic EL device
  • High performance electroluminescent organic material and application thereof in organic EL device
  • High performance electroluminescent organic material and application thereof in organic EL device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0072] Embodiment 1: TPA-(R 1 ) 3 Synthesis

[0073] Compound 1: Synthesis of 9-(4,4,5,5-tetramethyl-1,3,2-dioxaborinane)-naphthalene In 50 ml of refined tetrahydrofuran (THF), place it in a low-temperature reactor at -78°C, slowly inject 4.1 ml of n-BuLi (2.5 mol / L), and inject 5.0 ml of boroester one hour later, After half an hour, it was removed from room temperature and stirred for 2 days. A light earth red turbid liquid was obtained. Wash with water, then extract with ether for 3-4 times, combine the ether solutions, and dry over anhydrous magnesium sulfate overnight. The desiccant was filtered, the filtrate was spin-dried, and then the column was run with petroleum ether:dichloromethane (4:1) as the eluent to isolate the pure target product. Yield: 52%.

[0074] Compound 2: Synthesis of Tris(4-bromophenyl)amine

[0075] Weigh 8.0 grams of triphenylamine, add about 60 milliliters of chloroform to dissolve, and slowly add 5.2 milliliters of liquid bromine (Br 2 ) a...

Embodiment 2

[0079] Embodiment 2: TPA-(R 2 ) 3 Synthesis

[0080] Compound 3: Synthesis of 9-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)-anthracene

[0081] Weigh 2.57 grams of monobromoanthracene, dissolve it in about 120 milliliters of refined tetrahydrofuran (THF), place it in a low-temperature reactor to -78°C, and slowly inject 4.1 milliliters of n-butyllithium (n-BuLi) (2.5 mol / liter), inject 5.0 ml of boron ester one hour later, take it out after half an hour and stir at room temperature for 2 days. A dark orange-red cloudy solution was obtained. Wash with water, then extract with ether 3-4 times, combine the ether solution, anhydrous magnesium sulfate (MgSO 4 ) to dry overnight. The desiccant was filtered, the filtrate was spin-dried, and then the column was run with petroleum ether:dichloromethane (5:2) as the eluent to isolate the pure target product. Yield: 63%.

[0082] TPA-(R 2 ) 3 : Synthesis of Tris(4-(9-Anthracenyl)phenyl)amine

[0083] Weigh 216.9 mg of tris(4-bro...

Embodiment 3

[0085] Embodiment 3: TPA-(R 3 ) 3 Synthesis

[0086] Compound 4: Synthesis of 9-(4,4,5,5-tetramethyl-1,3,2-dioxaborinane)-phenanthrene

[0087] Weigh 2.0 g of monobromophenanthrene, dissolve it in about 100 ml of refined tetrahydrofuran (THF), place it in a low-temperature reactor to -78°C, and slowly inject 3.2 ml of n-butyllithium (2.5 mol / L) for one hour Then inject 5.0 ml of boron ester, take it out after half an hour and stir at room temperature for 2 days. A light green cloudy liquid was obtained. Wash with water, then extract with ether for 3-4 times, combine the ether solutions, and dry over anhydrous magnesium sulfate overnight. The desiccant was filtered, the filtrate was spin-dried, and then the column was run with petroleum ether:dichloromethane (5:2) as the eluent, and the pure target product was isolated. Yield: 26%.

[0088] TPA-(R 3 ) 3 : Synthesis of three (4-(9-phenanthrenyl) phenyl) amine

[0089] Weigh 216.9 mg of tris(4-bromophenyl)amine and 547.2...

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Abstract

The invention belongs to the technical field of organic electroluminescence, and in particular relates to a substituted organic electroluminescent material which takes triphenylamine as a core and takes a fused / heterocyclic ring aromatic group as periphery. The material is a single-arm ling-type, double-arm angle-type or three-arm star-type compound, the structural formula of which is shown on the right, wherein a peripheral group R is the substituted or unsubstituted fused or heterocyclic ring aromatic group, and the number of C atoms of the fused or heterocyclic ring aromatic group is between 6 and 50. The compound of the invention can be used as an electroluminescent material for preparing electroluminescent devices, and particularly can be used in active layers of the electroluminescent devices.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescence, and specifically relates to a class of organic electroluminescent materials with triphenylamine as the core and condensed / heterocyclic aromatic groups substituted on the periphery, and the preparation of such materials in high-efficiency and high-stability organic electroluminescent materials. Applications in organic electroluminescent devices. Background technique [0002] The discovery of the phenomenon of organic electroluminescence has a history of more than 40 years. In 1965, Gumee et al first published a patent on organic electroluminescent devices (U.S. Pat. No. 3,172,862, 3,173,050). In 1973 Dresner also published a patent for organic electroluminescent devices (U.S. Pat. No. 3,170,167). Polyaromatic ring organic compounds such as anthracene, tetracene, pentacene, etc. are used as organic electroluminescent materials in these inventions. The early device structure i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06H01L51/54H01L51/52
Inventor 马於光杨兵沈方中唐诗路萍许海顾成刘丹丹李维军
Owner JILIN UNIV
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