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End-blocked triarylamine and carbazoles material, handling method and uses

A kind of technology of triarylamine and carbazole, applied in the field of optoelectronic materials

Inactive Publication Date: 2006-05-10
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is still no report on the patent of using this type of structure and its derivative structure as a unit with a high glass transition temperature to end-cap the material to improve the thermal stability of the organic optoelectronic material

Method used

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  • End-blocked triarylamine and carbazoles material, handling method and uses
  • End-blocked triarylamine and carbazoles material, handling method and uses
  • End-blocked triarylamine and carbazoles material, handling method and uses

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0097] Example 1, 9-phenyl-fluoren-9-ol as a capping agent for the preparation of capping materials for triphenylamine:

[0098] 9-Phenyl-fluoren-9-ol

[0099] 9-phenyl-9H-fluoren-9-ol

[0100] Take bromo-benzene (2.1mmol) and magnesium Mg (0.502g, 2.1mmol) to react to generate Grignard reagent, and react with fluorenone (2.1mmol) dissolved in 16mL tetrahydrofuran at 60°C for 24 hours to form a large amount of white precipitate, and finally add Saturated color NHCl 4 Convert Grignard salts to alcohols. After the reaction was completed, ether was extracted, dried and rotary evaporated, and purified on a silica gel column with a mixed solvent of petroleum ether:dichloromethane (3:2) to obtain a slightly pale yellow solid tertiary alcohol (yield 90%).

[0101] GC-MS (EI-m / z): 258.1 (M + ).

[0102] 1 H NMR (400MHz, CDCl 3 , ppm): δ7.691-7.672 (d, J=7.6Hz, 2H), 7.406-7.325 (m, 6H), 7.292-7.236 (m, 5H), 2.508 (s, 1H).

[0103] 13 C NMR (CDCl 3 , ppm): δ150.658, 143.391, 139...

Embodiment 2

[0109] Example 2, 9-phenyl-fluorene-9-ol is used as a capping agent to treat the capping material preparation of triphenylamine:

[0110] N,N-bis(-4-(9-phenyl-fluoren-9-yl)phenyl)aniline

[0111] N,N-bis(4-(9-phenyl-fluoren-9-yl)phenyl)phenylamine

[0112]

[0113] Dissolve 9-phenyl-fluorene-9-alcohol and triphenylamine in dichloromethane at 2:1 equivalent, and add a few drops of boron trifluoride. Ether complex to react for 30 minutes at room temperature, add ethanol and Quench the reaction with water, extract with dichloromethane, dry and rotary evaporate, petroleum ether: the mixed solvent of dichloromethane is used as the silica gel column purification of the eluent, recrystallize with tetrahydrofuran and petroleum ether to obtain light yellow powder solid N, N-bis( 4-(9-Phenyl-fluoren-9-yl)phenyl)aniline (91% yield).

[0114] MALDI-TOF-MS (m / z): 725.4 (M + ).

Embodiment 3

[0115] Example 3, 9-phenyl-fluoren-9-ol is used as a capping agent to treat the capping material preparation of triphenylamine:

[0116] Tris(4-(9-phenyl-fluoren-9-yl)phenyl)amine

[0117] tris(4-(9-phenyl-fluoren-9-yl)phenyl)amine

[0118]

[0119] Dissolve 9-phenyl-fluorene-9-alcohol and triphenylamine in dichloromethane at a ratio of 3:1, add a few drops of boron trifluoride-ether complex dropwise at room temperature for 30 minutes, add ethanol and Quenching the reaction with water, extracting with dichloromethane, drying and rotary evaporating, petroleum ether: dichloromethane mixed solvent as the silica gel column purification of the eluent, recrystallization with tetrahydrofuran and petroleum ether to obtain light yellow powder solid three (tetra(9- Phenyl-fluoren-9-yl)phenyl)amine (90% yield).

[0120] MALDI-TOF-MS (m / z): 965.3 (M + ).

[0121] 1 H NMR (400MHz, CDCl 3 , ppm): δ7.74-7.721 (d, J=7.6Hz, 6H), 7.38-7.361 (d, J=7.6Hz, 6H), 7.346-7.308 (t, J=7.6Hz, 6H...

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Abstract

The invention, belonging to photoelectric material scientific and technical sphere, relates the new handling method of diarylamine and carbazoles materials and the application as the hole transmission material. Compared with the untreated material, the dead-end diarylamine and carbazoles poessess the high heat stability and glass transition temperature. Comprared with the other methods of preparing the material, the handling method has the following advantages: 1. convenient handling method, simple technology; 2. mild reaction condition, not needing transient metal accelerant; 3. high productivity, direct processing polymeric material; 4. mass production. The said hole transmission material will become the photoelectric material of low cost and commercialization potentiality.

Description

technical field [0001] The invention belongs to the technical field of photoelectric materials. It specifically relates to capped triarylamine and carbazole materials and their simple capping treatment methods, and relates to the application of such materials in organic electroluminescence, organic field effect tubes, organic solar cells, nonlinear optics, biosensing and lasers, etc. field applications. technical background [0002] Since 1987, the Tang Research Group of Kodak Company in the United States [Tang, C.W.; Van Slyke, S.A.Appl. Phys. Lett. Marks, R.N.; Mackay, K.; Friend, R.H.; Bum, P.L.; Holmes, A.B.Nature 1990, 347, 539.] published thin-film organic electroluminescent devices (Organic Light -emitting Diodes) and polymer light-emitting diodes (Polymeric Light-emitting Diodes), organic flat panel display has become another generation of market-oriented display products after liquid crystal display. At the same time, other organic electronics and optoelectronic ...

Claims

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Application Information

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IPC IPC(8): C07D209/82C07B43/00C09K11/06H01L51/30
Inventor 黄维解令海侯晓雅范曲立华育然
Owner FUDAN UNIV
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