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charge transport varnish

A charge-transporting, varnish-based technology applied in the field of organic EL to improve light extraction efficiency, lower drive voltage, and ensure color reproducibility

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

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Problems solved by technology

[0004] In view of this, the present inventors have found that by using an oligoaniline compound partially cutting off a conjugated system in a molecule, an oligoaniline compound partially containing a conjugated system composed of a repeating unit structure different from aniline units , so that the coloring in the visible region is suppressed, and a charge-transporting film with excellent transparency is obtained (refer to Patent Document 2). The thin-film organic EL device described in 2 has room for improvement in terms of device characteristics, life performance, etc.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0152] The following examples and comparative examples are given 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.

[0153] (1) 1 H-NMR measurement: High-resolution nuclear magnetic resonance equipment manufactured by Barian

[0154] (2) Substrate cleaning: Substrate cleaning equipment manufactured by Changzhou Sangyo Co., Ltd. (decompression plasma method)

[0155] (3) Coating of varnish: spin coater MS-A100 manufactured by Mikasa Co., Ltd.

[0156] (4) Film thickness measurement: Micro shape measuring machine Surfcorder ET-4000 manufactured by Kosaka Laboratories Co., Ltd.

[0157] (5) Transmittance measurement: Visible ultraviolet absorption spectrometer UV-3100PC manufactured by Shimadzu Corporation

[0158] (6) Manufacture of EL elements: Multifunctional vapor deposition system C-E2L1G1-N manufactured by Changzhou Sangyo Co., Ltd.

[0159] (7) Meas...

Synthetic example 1

[0161] [Synthesis Example 1] Synthesis of Aniline Derivative A (Formula (f))

[0162] [chemical 12]

[0163]

[0164] Add tetrakis(triphenyl 0.5799 g (0.5018 mmol) of phosphine) palladium and 10.13 g (105.40 mmol) of sodium tert-butoxide were stirred at 130° C. for 14 hours under nitrogen.

[0165] Then, the reaction mixture was filtered, saturated brine was added to the filtrate, and after liquid separation treatment, the solvent was distilled off from the organic layer, and the obtained solid was recrystallized using 1,4-dioxane to obtain aniline Derivative A (yield: 22.37 g, yield: 65%).

Synthetic example 2

[0166] [Synthesis Example 2] Synthesis of Aryl Sulfonic Acid C (Formula (8))

[0167] [chemical 13]

[0168]

[0169] In 11.0 g (31.59 mmoles) of fully dried 1-naphthol-3,6-sodium disulfonate, 4.797 g (14.36 moles) of perfluorobiphenyl and 4.167 g (30.15 moles) of potassium carbonate were added successively under a nitrogen atmosphere. ) and 100 mL of N,N-dimethylformamide, and the reaction system was replaced with nitrogen, and stirred at an internal temperature of 100° C. for 6 hours.

[0170] After naturally cooling to room temperature, 500 mL of N,N-dimethylformamide was further added in order to redissolve the arylsulfonic acid C precipitated after the reaction, and the mixture was stirred at room temperature for 90 minutes. After stirring, the solution was filtered to remove potassium carbonate residue and concentrated under reduced pressure. Furthermore, in order to remove remaining impurities, 100 mL of methanol was added to the residue, and the mixture was stirre...

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Abstract

A charge-transporting varnish comprising: a charge-transporting substance containing an oligoaniline derivative represented by formula (1), a charge-transporting substance containing an N,N'-diarylbenzidine derivative represented by formula (2) Sexual substances, dopants and organic solvents. (In formula (1), R1 represents hydrogen, alkyl, alkenyl, alkynyl, aryl or heteroaryl, R2~R7 represents hydrogen, halogen, nitro, cyano, amino, aldehyde, hydroxyl, thiol group, sulfonic acid group, carboxylic acid group, alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, ‑NHY1, ‑NY2Y3, ‑C(O)Y4, ‑OY5, ‑SY6, ‑SO3Y7, ‑C (O)OY8, -OC(O)Y9, -C(O)NHY10 or -C(O)NY11Y12 base.) (In formula (2), R8~R15 represent hydrogen, alkyl, alkenyl or alkynyl, Ar1 and Ar2 represent groups represented by formula (3) or (4).)

Description

technical field [0001] The present invention relates to a charge-transporting varnish. Specifically, it relates to a charge-transporting film capable of imparting excellent transparency and charge-transporting properties and realizing high brightness when applied to organic electroluminescent (hereinafter referred to as organic EL) devices. Sexual varnish. Background technique [0002] The present inventors have reported that a charge-transporting film obtained from an organic solvent-based charge-transporting varnish using a charge-transporting substance containing a low-molecular-weight oligoaniline compound exhibits excellent electroluminescence device characteristics (refer to Patent Document 1) . In the charge-transporting varnish described in Patent Document 1, the low-molecular-weight oligoaniline compound constituting the charge-transporting material has the same repeating unit structure in the molecule, and the more elongated the conjugated system is, the easier it...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): H01L51/50C07C211/54C08G73/00C09D5/24C09D179/00H01B1/12H01B1/20H01B5/14H05B33/10
CPCC07C211/54C09D5/24H01B1/128C07C211/55C09D179/06C08G73/026H10K85/615H10K85/631H10K50/17
Inventor 中家直树森山彰治
Owner NISSAN CHEM CORP
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