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Arylsulfonic acid compound and use thereof as electron-acceptor material

An aryl sulfonic acid and compound technology, applied in the field of aryl sulfonic acid compounds, can solve the problems of reduced characteristics, limited selection range, uneven surface unevenness, and achieves the effects of reducing driving voltage, improving current efficiency, and uniform light-emitting surface

Active Publication Date: 2007-09-19
NISSAN CHEM CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] However, CuPC, which is a common hole-injecting material in OLED devices, has uneven surfaces, and when a small amount of it is mixed into other organic layers, its characteristics will be greatly reduced.
[0009] In addition, the polyaniline-based materials and polythiophene-based materials currently used in PLED elements still have some problems, such as containing water as a solvent that may promote the deterioration of the element, the selection of solvents is limited, and due to the aggregation or low solubility of the material. Coating methods that can form a uniform film are limited, etc.
[0010] Furthermore, even when an organic solvent-based charge-transporting varnish containing a highly soluble low-molecular-weight oligoaniline material is used, the types of electron-accepting dopants that can be used are limited, and problems with the electron-accepting dopant may occur. Problems such as heat resistance and low amorphousness

Method used

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  • Arylsulfonic acid compound and use thereof as electron-acceptor material
  • Arylsulfonic acid compound and use thereof as electron-acceptor material
  • Arylsulfonic acid compound and use thereof as electron-acceptor material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0149] Naphthalene disulfonic acid compound oligomer 1 (hereinafter abbreviated as NSO-1) was synthesized according to the following reaction formula (14).

[0150]

[0151] That is, in a nitrogen atmosphere, 449 mg of perfluorobiphenyl, 60% hydrogenated 161 mg of sodium and 50 ml of anhydrous N,N-dimethylimidazolidinone were replaced with nitrogen in the reaction system, and stirred at 80° C. for 43 hours.

[0152] After cooling to room temperature, add water to stop the reaction, reduce pressure, concentrate and evaporate to dryness. 5 ml of methanol was added to the residue, and the resulting suspension was added to 100 ml of diethyl ether while stirring. After stirring at room temperature for 1 hour, the precipitated solid was collected by filtration, 50 ml of methanol was added to the filtrate, and the mixture was suspended by ultrasonication. The insoluble solid was removed by filtration, and the filtrate was concentrated under reduced pressure and evaporated to dry...

Embodiment 2

[0157] Naphthalene disulfonic acid compound oligomer 2 (hereinafter abbreviated as NSO-2) was synthesized according to the following reaction formula (15).

[0158]

[0159] That is, in a nitrogen atmosphere, 450 mg of perfluorobiphenyl and 166 mg of 60% sodium hydride were sequentially added to 934 mg of fully dried sodium 1-naphthol-3,6-disulfonate (manufactured by Tokyo Chemical Industry Co., Ltd.) and 50 ml of anhydrous N,N-dimethylimidazolidinone, the inside of the reaction system was replaced with nitrogen, and stirred at 80°C for 43 hours.

[0160]After cooling to room temperature, water was added to stop the reaction, and concentrated under reduced pressure and evaporated to dryness. 5 ml of methanol was added to the residue, and the resulting suspension was added to 100 ml of diethyl ether while stirring. After stirring at room temperature for 1 hour, the precipitated solid was collected by filtration, and 25 ml of methanol was added to the filtrate, followed by u...

Synthetic example 1

[0164] [Synthesis Example 1] Synthesis of Phenyltetraphenylamine

[0165]

[0166] Based on the method described in Bulletin of Chemical Society of Japan, 1994, Vol. 67, p. 1749-1752, phenyltetraphenylamine (PTA) was produced in the following manner.

[0167] That is, 12.977 g of p-phenylenediamine was dissolved in 2 L of toluene, 245.05 g of tetra-n-butoxytitanium as a dehydration condensation agent was added thereto, and dissolved at 70° C. for 30 minutes. Thereafter, 53.346 g of p-hydroxydiphenylamine was added, and reacted at a reaction temperature of 100° C. for 24 hours under a nitrogen atmosphere. After the reaction, the reaction liquid was filtered, and the filtrate was washed with toluene and diethyl ether in sequence, and dried to obtain silver crystals. 25 parts by mass of dioxane and 0.2 equivalent of hydrazine monohydrate were added to the obtained crystals, and the inside of the reaction system was replaced with nitrogen, followed by heating to reflux to diss...

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Abstract

An excellent EL device having low driving voltage, high luminous efficiency and long life can be obtained by using a charge-transporting thin film composed of a charge-transporting varnish which contains an arylsulfonic acid compound represented by the formula (1) or (2) below as an electron-acceptor material especially in an OLED device or a PLED device. [In the formulae, X represents O, S or NH; A represents a naphthalene ring or anthracene ring having a substituent other than X and n SO 3 H groups; B represents a substituted or unsubstituted hydrocarbon group, 1,3,5-triazine group or a substituted of unsubstituted group represented by the following formula (3) or (4): (wherein W 1 and W 2 each independently represents O, S, an S(O) group, an S(O 2 ) group, or a substituted or unsubstituted N, Si, P or P(O) group); n indicates the number of sulfonic acid groups bonded to A which is an integer satisfying 1<=n<=4; q indicates the number of B-X bonds which is an integer satisfying 1= C07C 309 / 43 H01L 51 / 50 0 23 2 2005 / 8 / 30 101039899 2007 / 9 / 19 000000000 Nissan Chemical Ind Ltd. Japan Yoshimoto Takuji Ono Go chencuan 11038 The Patent Agency of the Chinese Council for the Promotion of International Trade (CCPIT) No.1 Waidajie, Fuxingmen, Beijing 100086 Japan 2004 / 8 / 31 251774 / 2004 2007 / 4 / 11 PCT / JP2005 / 015689 2005 / 8 / 30 WO2006 / 025342 2006 / 3 / 9 Japanese

Description

technical field [0001] The present invention relates to arylsulfonic acid compounds and the use of such compounds as electron-accepting substances. Such utilization includes a varnish having an electron-accepting substance containing an arylsulfonic acid compound, a charge-transporting film made using the varnish, or organic electroluminescence (hereinafter simply referred to as organic EL) using the charge-transporting film. ) components, etc. Background technique [0002] Eastman Kodak Company has greatly improved its characteristics (non- Patent Document 1: Applied Physics Letters, United States, 1987, Vol. 51, p.913-915). [0003] In addition, the University of Cambridge proposed an organic EL (hereinafter referred to as PLED) element using a polymer light-emitting material (Non-Patent Document 2: Nature, UK, 1990, Vol. 347, p.539-541). The characteristics of EL elements have been continuously improved, and have reached a level comparable to that of previous OLEDs. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C309/43H01L51/50
CPCC07C309/43H01L51/0058H01L51/5052H10K85/626H10K50/155H10K85/615
Inventor 吉本卓司小野豪
Owner NISSAN CHEM CORP
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