Charge-transporting varnish

A technology of charge transport and varnish, which is applied in circuits, electric light sources, photovoltaic power generation, etc., can solve unconfirmed problems and achieve high charge transport effects

Active Publication Date: 2017-05-10
NISSAN CHEM IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] However, an example of a charge-transporting material formed using a cross-linked product of an arylbenzidine derivative in which both of the two nitrogen atoms are bonded to a hydrogen atom has not yet been confirmed.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0186] Synthesis examples and examples are given below to describe the present invention more specifically, but the present invention is not limited to the following examples. In addition, the apparatuses used are as follows.

[0187] (1) 1 H-NMR: ECX-300 manufactured by JEOL Ltd.

[0188] (2) LC / MS: Waters (Waters) Co., Ltd., ZQ2000

[0189] (3) Substrate cleaning: Substrate cleaning device manufactured by Choshu Sangyo Co., Ltd. (decompression plasma method)

[0190] (4) Coating of varnish: Mikasa (ミカサ) Co., Ltd. spin coater MS-A100

[0191] (5) Film thickness measurement: Micro shape measuring machine Suifcorder (Surfcorder) ET-4000 manufactured by Kosaka Laboratory

[0192] (6) Production of EL elements: Multi-functional vapor deposition system C-E2L1G1-N manufactured by Choshu Sangyo Co., Ltd.

[0193] (7) Measurement of luminance, etc. of EL elements: (Yes) I-V-L measurement system manufactured by Tech World Inc. (Tech World Inc.)

[0194] [1] Synthesis of Arylamin...

Synthetic example 1

[0195] [Synthesis Example 1] Synthesis of Compound 1

[0196] [chemical 18]

[0197]

[0198] To a toluene suspension (90 mL) of 4-bromo-4′-iodobiphenyl (8.98 g, 25 mmol, manufactured by Tokyo Chemical Industry Co., Ltd.), aniline (2.56 g, 27.5 mmol), was added Pd(PPh 3 ) 4(1.44g, 1.25mmol) and t-BuONa (2.88g, 30mmol) were replaced with nitrogen, and heated to reflux for 10 hours. After the reaction, let cool to room temperature, and filtered with celite. The filtrate was concentrated, the obtained crude product was purified by silica gel column chromatography (eluent: toluene), and the fraction containing Compound 1 was concentrated. A mixed solvent of ethanol / toluene (3:1 (w / w)) was added to the obtained crude product, and it was dissolved under heating and reflux. After cooling to room temperature, the precipitated solid was filtered to obtain Compound 1 (6.96 g, yield 86%) as a light brown solid. 1 The measurement results of H-NMR and LC / MS are shown below.

[019...

Synthetic example 2

[0201] [Synthesis Example 2] Synthesis of Arylamine Derivative H1

[0202] [chemical 19]

[0203]

[0204] Xylene suspension of compound 1 (1.95 g, 6.0 mmol) prepared in Synthesis Example 1 to 9,9-bis(4-aminophenyl)fluorene (1 g, 2.87 mmol, manufactured by Tokyo Chemical Industry Co., Ltd.) (10mL), add Pd(PPh 3 ) 4 (166mg, 0.14mmol), t-BuONa (0.66g, 6.89mmol), after being replaced with nitrogen, heated to reflux for 4 hours. Then, Compound 1 (0.37 g, 1.1 mmol) and t-BuONa (0.11 g, 1.21 mmol) obtained in Synthesis Example 1 were added, followed by heating under reflux for 6 hours. After completion of the reaction, let cool to room temperature, add chloroform (40 mL) and water (40 mL), and stir at room temperature for 30 minutes. The insoluble solid was collected by filtration, dissolved in THF, and filtered through celite. The filtrate was concentrated, and the obtained crude product was purified by silica gel column chromatography (eluent: hexane / ethyl acetate (1 / 1 (v / ...

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Abstract

A charge-transporting substance which comprises an arylamine derivative represented by formula (1), the charge-transporting substance showing satisfactory solubility in organic solvents. When a thin film produced from a charge-transporting varnish which contains the charge-transporting substance is applied as a hole injection layer, then an organic EL element having excellent luminance characteristics is rendered possible. [In formula (1), R1 to R8 each independently represent a hydrogen atom, etc.; Ar1 represents a phenyl group, etc.; n is an integer of 1 to 3; and X represents a divalent organic group represented by formula (2a) or (2b). (In formulae (2a) and (2b), R9 and R10 each independently represent a C1-20 alkyl group, etc.; R11 and R12 each independently represent a hydrogen atom or a fluorine atom; R13 to R20 each independently represent a hydrogen atom, etc.; and m is an integer of 1 to 4.)]

Description

technical field [0001] The present invention relates to charge-transporting varnishes. Background technique [0002] In an organic electroluminescent (hereinafter referred to as organic EL) device, a charge-transporting thin film containing an organic compound can be used as a light-emitting layer or a charge injection layer. In particular, the hole-injection layer is responsible for the exchange of charge between the anode and the hole-transport layer or the light-emitting layer, and plays an important function for realizing low-voltage drive and high-luminance of the organic EL element. [0003] The methods for forming charge transport thin films are roughly divided into dry methods represented by vapor deposition and wet methods represented by spin coating methods. Comparing these methods, the wet method can efficiently produce large-area and excellent flatness. film. Therefore, a hole injection layer that can be formed by a wet method is desired at the present time whe...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/55H01L51/50H05B33/10
CPCC07C211/55H05B33/10H10K50/00H10K71/12H10K85/631H10K50/16H10K50/15
Inventor 森山彰治太田博史
Owner NISSAN CHEM IND LTD
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