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Charge-transporting varnish

A technology of charge transport and varnish, applied in the direction of circuits, electric light sources, electrical components, etc.

Active Publication Date: 2016-11-16
NISSAN CHEM IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, on the other hand, this method also has the disadvantage that in the manufacturing process of the organic EL element, a separate process is generally required for forming these layers

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0253] Hereinafter, the present invention will be described more specifically with reference to synthesis examples, examples, and comparative examples, but the present invention is not limited to the following examples. In addition, the apparatuses used are as follows.

[0254] (1) NMR: ECX-300 manufactured by JEOL Ltd.

[0255] (2) LC / MS: ZQ2000 manufactured by Waters Co., Ltd.

[0256] (3) Substrate cleaning: Substrate cleaning device manufactured by Choshu Sangyo Co., Ltd. (decompression plasma method)

[0257] (4) Coating of varnish: spin coater MS-A100 manufactured by Mikasa Co., Ltd.

[0258] (5) Film thickness measurement: Micro shape measuring machine Surfcorder ET-4000 manufactured by Kosaka Laboratory

[0259] (6) Determination of polymer molecular weight: manufactured by Shimadzu Corporation (column: SHODEX GPC KF-803L+GPC KF-804L, column temperature: 40°C, detector: UV detector (254nm) and RI detector, Eluent: THF, column flow rate: 1.0ml / min.)

[0260] (7) Ma...

Synthetic example 1

[0263] [Synthesis Example 1] Synthesis of Compound 1

[0264] [chem 29]

[0265]

[0266] Add potassium carbonate (7.60g, 55mmol) and diethylene glycol 2-bromoethyl methyl ether (9535μL, 55mmol) to 3-bromophenol (8.65g, 50mmol) in acetonitrile solution (170mL), stir at room temperature for 18 After 1 hour, heat to reflux for 7 hours. Potassium carbonate (1.50 g, 10 mmol) and diethylene glycol 2-bromoethyl methyl ether (1900 μL, 10 mmol) were added to the suspension, followed by heating under reflux for 4 hours. After the reaction, the insoluble matter was removed by filtration, the filtrate was concentrated, and the obtained crude product was purified by silica gel column chromatography (eluent: hexane / ethyl acetate) to obtain compound 1 (16.13 g, 100% yield) as a colorless liquid. Rate).

[0267] 1 H-NMR (300MHz, CDCl 3 ): δ3.38(s, 3H), 3.53-3.58(m, 2H), 3.64-3.75(m, 6H), 3.84(app t, J=4.8Hz, 2H), 4.11(app t, J=4.8 Hz, 2H), 6.83-6.87(m, 1H), 7.05-7.16(m, 3H).

[026...

Synthetic example 2

[0269] [Synthesis Example 2] Synthesis of Compound 2

[0270] [chem 30]

[0271]

[0272] To N,N'-diphenylbenzidine (4.88g, 14.5mmol), compound 1 (11.15g, 35mmol) prepared in Synthesis Example 1 in toluene suspension (70mL), add Pd(dba) 2 (834mg, 1.5mmol), t-BuONa (4.18g, 43.5mmol), [(t-Bu) 3 PH]BF 4 (841mg, 2.9mmol), toluene (30mL), after nitrogen replacement, heated to reflux for 3 hours. After the reaction was completed, it was filtered with celite, the filtrate was concentrated, and the obtained crude product was purified by silica gel column chromatography (eluate: hexane / ethyl acetate) to obtain Compound 2 (12.06 g, 100% yield) as a brown liquid. Rate).

[0273] 1 H-NMR (300MHz, CDCl 3 ): δ3.36(s, 6H), 3.52-3.55(m, 4H), 3.62-3.73(m, 12H), 3.80(app t, J=4.8Hz, 4H), 4.04(app t, J=4.8 Hz, 4H), 6.57-6.59(m, 2H), 6.68-6.71(m, 4H), 7.02(app t, J=7.2Hz, 2H), 7.11-7.17(m, 10H), 7.23-7.28(m , 4H), 7.44 (d, J=8.7Hz, 4H).

[0274] LC / MS (ESI + )m / z; 813[M+1] +

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Abstract

This charge-transporting varnish includes: a fluorine-containing charge-transporting substance; a non-fluorine-containing charge-transporting substance; a dopant substance comprising a heteropoly acid; and an organic solvent. The fluorine-containing charge-transporting substance is a polymer which has a weight average molecular weight of 500-200,000, and which is obtained by condensing: at least one compound selected from triarylamine compounds and tetraarylbenzidine compounds; a tetraarylbenzidine compound having at least one aryl group substituted with an alkoxy group which may include ether bonds; a fluorine-containing aryl aldehyde compound; and a fluorene derivative having a carbonyl group. The non-fluorine-containing charge-transporting substance is an oligoaniline compound. The charge-transporting varnish provides a thin film with which an organic electroluminescent element exhibiting excellent luminance characteristics can be achieved, even in cases when employed as a single layer in a state of being provided between and in contact with a positive electrode and a light-emission layer.

Description

technical field [0001] The present invention relates to charge-transporting varnishes. Background technique [0002] A charge-transporting thin film is used in an organic electroluminescence (hereinafter referred to as organic EL) element. [0003] The method of forming the charge transport thin film is roughly divided into a dry method represented by a vapor deposition method and a wet method represented by a spin coating method. These methods can be appropriately used separately depending on the area of ​​the thin film to be formed and the solubility of the substance to be thinned in an organic solvent. [0004] In general, two layers of a layer called a hole injection layer and a layer called a hole transport layer are arranged in order from the anode side between the anode and the light emitting layer of the organic EL element. By providing such two layers, an organic EL element capable of efficiently performing charge transport and having high luminance characteristic...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09D161/00C08K3/24C08L61/20C08L79/00C09D5/22C09D7/12C09K11/06H01B1/06H01L51/50H05B33/10H10K99/00
CPCC09D161/00C08G16/0231C08G16/06C09D179/02C08G73/026C09D7/40H10K85/111H10K50/15C08K3/24C09D5/24
Inventor 大谷直树太田博史
Owner NISSAN CHEM IND LTD
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