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charge transport varnish

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

Active Publication Date: 2019-06-11
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

The present invention provides a charge-transporting varnish comprising a charge-transporting substance containing a fluorine atom, a charge-transporting substance not containing a fluorine atom, a dopant substance containing a heteropolyacid, and an organic solvent; wherein the charge-transporting substance containing a fluorine atom is The transporting substance is a tetraarylbenzidine compound selected from at least one of triarylamine compounds and tetraarylbenzidine compounds, at least one aryl group of which is substituted by an alkoxy group that may contain an ether bond, containing The polymer obtained by condensing an aryl aldehyde compound having a fluorine atom and a fluorene derivative having a carbonyl group has a weight average molecular weight of 500 to 200,000, and the charge-transporting substance not containing a fluorine atom is an oligoaniline compound. The charge-transporting varnish can form a thin film capable of realizing an organic EL element having excellent luminance characteristics even when it is used as a single layer in a state of being in contact with the anode and the light-emitting 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 Patents(China)
IPC IPC(8): C09D161/00C08K3/24C08L61/20C08L79/00C09D5/22C09D7/63C09D7/65C09K11/06H01B1/06H01L51/50H05B33/10
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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