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Hole transporting varnish for metal positive electrodes and composite metal positive electrode

A hole-transporting, metal anode technology, applied in electrical components, circuits, organic chemistry, etc., can solve problems such as no specific reports, and achieve the effect of good reproducibility and excellent hole accepting ability

Inactive Publication Date: 2015-12-02
NISSAN CHEM IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] For the element of the top emission structure, the hole injection layer is formed directly on the metal, and a thin film showing excellent hole injection performance can be formed when the layer is directly laminated on the metal, and regarding the varnish that can adopt the wet method, So far there are no specific reports

Method used

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  • Hole transporting varnish for metal positive electrodes and composite metal positive electrode
  • Hole transporting varnish for metal positive electrodes and composite metal positive electrode
  • Hole transporting varnish for metal positive electrodes and composite metal positive electrode

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0188] Hereinafter, although synthesis examples, examples, and comparative examples are given, and the present invention is more specifically described, the present invention is not limited to the following examples. In addition, the apparatuses used are as follows.

[0189] (1) 1 H-NMR measurement: Varian high-resolution nuclear magnetic resonance device

[0190] (2) Anode cleaning: Substrate cleaning device manufactured by Choshu Sangyo Co., Ltd. (decompression plasma method)

[0191] (3) Coating of varnish: Spin coater MS-A100 manufactured by MiKasa Co., Ltd.

[0192] (4) Film thickness measurement: Micro shape measuring machine SurfcodaET-4000 manufactured by Kosaka Laboratory

[0193] (5) Manufacture of components: Multifunctional vapor deposition system C-E2L1G1-N manufactured by Choshu Sangyo Co., Ltd.

[0194] (6) Measurement of current density, etc. of components: (Yes) I-V-L measurement system manufactured by TechWorld

[0195][1] Synthesis of charge-transportin...

Synthetic example 1

[0196] [Synthesis Example 1] Synthesis of Aniline Derivative A

[0197] The aniline derivative A used in the examples was synthesized according to the following reaction formula.

[0198] [chemical 10]

[0199]

[0200] To the mixed suspension of 4,4'-diaminodiphenylamine (10.00g, 50.19mmol) and 4-bromotriphenylamine (34.17g, 105.40mmol) in xylene (100g), add as metal complex catalyst Pd(PPh 3 ) 4 (0.5799g, 0.5018mmol) and t-BuONa (10.13g, 105.40mmol) as a base were stirred at 130° C. for 14 hours in nitrogen to react.

[0201] The cooled reaction mixture was filtered, and saturated brine was added to the filtrate for liquid separation and extraction. Then, the solvent was distilled off under reduced pressure, followed by 1,4-bis The target product was recrystallized from alkanes to obtain aniline derivative A (yield 65%).

[0202] 1 H-NMR (CDCl 3 ): δ7.83(S, 2H), 7.68(S, 1H), 7.26-7.20(m, 8H), 7.01-6.89(m, 28H).

Synthetic example 2

[0203] [Synthesis Example 2] Synthesis of Aniline Derivative B

[0204] The aniline derivative B used in the examples was synthesized according to the following reaction formula.

[0205] [chemical 11]

[0206]

[0207] To N,N'-bis(4-aminophenyl)-p-phenylenediamine (5.00g, 17.22mmol) and 4-bromotriphenylamine (9.30g, 28.70mmol) in xylene (140g) In the suspension, Pd(PPh 3 ) 4 (0.33g, 0.29mmol) and t-BuONa (2.76g, 28.70mmol) as a base were stirred at 135° C. for 8 hours in nitrogen to react.

[0208] The cooled reaction mixture was filtered, and the solvent was distilled off under reduced pressure. Next, use 1,4-2 The target product was recrystallized from alkanes to obtain aniline derivative B (yield 53%).

[0209] 1 H-NMR (DMSO-d 6 ): δ7.81(S, 2H), 7.61(S, 2H), 7.27-7.18(m, 8H), 7.05-6.65(m, 32H).

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Abstract

This hole transporting varnish for metal positive electrodes, which contains, for example, a charge transporting material that is composed of an aniline derivative represented by formula (1), a dopant material that is composed of a heteropolyacid, and an organic solvent, provides a thin film that has excellent ability of accepting holes from a metal positive electrode and is suitable for use as a hole injection layer which is formed on the metal positive electrode. (In the formula, X1 represents -NY1-, -O-, -S-, -(CR7R8)l- or a single bond; each Y1 independently represents a hydrogen atom or the like; each of R1-R8 independently represents a hydrogen atom, a halogen atom or the like; and each of m and n independently represents an integer of 0 or more, while satisfying 1 ≤ m + n ≤ 20, provided that in cases where m or n is 0, X1 represents -NY1-.)

Description

technical field [0001] The present invention relates to a hole-transporting varnish for a metal anode and a composite metal anode. More specifically, it relates to the hole-transporting property of a thin film formed on a metal anode and exhibiting a high ability to accept holes from the metal anode A varnish and a composite metal anode comprising such a thin film and metal laminate. Background technique [0002] In an organic electroluminescent (hereinafter, referred to as organic EL) device, a charge-transporting thin film containing an organic compound is used as a light-emitting layer and a charge injection layer. In particular, the hole injection layer is responsible for the exchange of charges between the anode and the hole transport layer or the light emitting layer, and plays an important function for realizing low-voltage driving and high luminance. [0003] The method of forming the hole injection layer is roughly divided into a dry method represented by the evapo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): H01L51/50C07C211/54C07C211/55C07D333/18H05B33/10H05B33/26H10K99/00
CPCC07C211/55C07D333/18C07D519/00H01L51/0059H01L51/0068H01L51/5088H10K85/655H10K85/631H10K50/17
Inventor 古贺春香中家直树
Owner NISSAN CHEM IND LTD
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