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Material for organic electroluminescent element and organic electroluminescent element employing the same

An electroluminescent element and electroluminescent technology, applied in electroluminescent light sources, luminescent materials, electrical components, etc., can solve the problems of increased linearity, decreased luminous efficiency, and difficult to avoid crystallization, and achieve excellent heat resistance, The effect of long life and high luminous efficiency

Inactive Publication Date: 2007-03-21
IDEMITSU KOSAN CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In Patent Document 6, the heat resistance is improved, but most of the phenylene structures constituting the compound are in the form of para-position bonding, and the meta-position bonding is only the central benzene ring, so its symmetry remains. Good, but it is difficult to avoid the problem of crystallization
In addition, Patent Document 7 and Patent Document 8 disclose host materials in which a heterocyclic skeleton such as a triazine skeleton is introduced in addition to the carbazole skeleton, but the triazine is bound in the para position via the phenylene skeleton from the carbazole skeleton. Ring, so the linearity of the compound increases, the energy of the triplet excited state of the host decreases, and it is difficult to transfer energy from the host to the phosphorescent dopant, especially in blue phosphorescent elements, causing a decrease in luminous efficiency.
Furthermore, in Patent Document 9 and Patent Document 10, in the phenylene structure constituting the compound, a structure in which a diarylaminophenyl group and an aryl group are bonded at the meta position on the benzene ring can improve life and heat resistance. , but not enough for practical application

Method used

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  • Material for organic electroluminescent element and organic electroluminescent element employing the same
  • Material for organic electroluminescent element and organic electroluminescent element employing the same
  • Material for organic electroluminescent element and organic electroluminescent element employing the same

Examples

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Effect test

Embodiment

[0104] Next, the present invention will be described in further detail using examples, but the present invention is not limited to these examples.

[0105] Intermediate Synthesis Example 1 (4-(carbazol-9-yl)phenylboronic acid: (Intermediate A))

[0106] 254 g of 4-bromoiodobenzene (manufactured by Tokyo Kasei Co., Ltd.), 100 g of carbazole (manufactured by Tokyo Kasei Co., Ltd.), 1 g of copper iodide (manufactured by Wako Pure Chemical Industries, Ltd.), and 267 g of potassium phosphate (manufactured by Wako Pure Chemical Industries, Ltd.) were suspended in 1. To 500 ml of 4-dioxane (manufactured by Wako Pure Chemical Industries, Ltd.), 7 ml of trans-1,2-cyclohexanediamine was added, and the mixture was heated to reflux for 14 hours under an argon atmosphere.

[0107] The reaction solution was cooled to room temperature, dichloromethane and water were added to separate the two layers, and then the organic layer was washed with 5% hydrochloric acid and water, and dried with anhydro...

Synthetic example 3

[0116] Intermediate Synthesis Example 3 (Synthesis of 3,5-diphenylphenylboronic acid (Intermediate C))

[0117] To 150 g of 2,4,6-tribromoaniline (manufactured by Aldrich Corporation), 2.2 liters of water and 2.2 liters of concentrated hydrochloric acid were added, and the mixture was stirred at room temperature for 30 minutes. It was then cooled to 0°C, and a 120 ml solution of 60 g of sodium nitrite (manufactured by Wako Pure Chemical Industries, Ltd.) in water was added dropwise below 5°C. After the dripping, it was stirred at 5°C or lower for 1 hour, and a 150 ml water solution of potassium iodide 150 g (manufactured by Wako Pure Chemical Industries, Ltd.) was dropped at 5°C or lower. After stirring for 1 hour at 5°C or less, the precipitated crystals were filtered, washed with water, dried, and purified by silica gel column chromatography to obtain 165 g of 2,4,6-tribromoiodobenzene.

[0118] 160 g of this was dissolved in 1.6 liters of dehydrated THF (tetrahydrofuran) (manuf...

Synthetic example 1

[0120] Synthesis Example 1 (Compound (A-1)) Synthesis

[0121] Add 1.0 g of Intermediate B, 0.2 g of phenylboronic acid (manufactured by Tokyo Chemical Industry Co., Ltd.), and 0.1 g of tetrakis(triphenylphosphine)palladium (O) (manufactured by Tokyo Chemical Industry Co., Ltd.), and add 4 ml of 2M sodium carbonate aqueous solution and 7 ml of DME The mixed solution (manufactured by Kanto Chemical Co., Ltd.) was heated to reflux at 90°C for 10 hours.

[0122] After the completion of the reaction, it was placed at room temperature, filtered, and the crystals were washed with DME, water, and methanol successively and dried. It was further purified by column chromatography to obtain 0.72 g of white powder. Measure its FD-MS (field desorption mass spectrometry), the result is relative to C 48 H 32 N 2 =636, a peak of m / z=636 was obtained, so it was identified as the compound (A-1) (yield 73%).

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Abstract

A material for organic electroluminescent elements which comprises a compound having a specific structure showing enhanced steric hindrance; and an organic electroluminescent element which comprises a cathode and an anode and, sandwiched therebetween, an organic thin film layer consisting of one or more layers comprising at least a luminescent layer, wherein at least one layer of the organic thin film layer comprises the material for organic electroluminescent elements. The organic electroluminescent element has a high luminescent efficiency, excellent heat resistance, and a long life.

Description

Technical field [0001] The present invention relates to a material for an organic electroluminescence element and an organic electroluminescence element using the material, in particular to a material for an organic electroluminescence element and an organic electroluminescence element with high luminous efficiency, excellent heat resistance, and long life element. Background technique [0002] Organic electroluminescence element (hereinafter sometimes abbreviated as EL) is a self-luminescence based on the principle of light emission by applying an electric field and using a fluorescent substance to emit light with the combined energy of holes injected from the anode and electrons injected from the cathode. element. Since CWTang of Iistman Co., Ltd. and others reported low-voltage drive organic EL elements based on laminated elements (CWTang, SAVanslyke, Applied Physics Letters, Vol. 51, Page 913, 1987, etc.) Research on organic materials as constituent materials of organic EL el...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): H05B33/14C09K11/06H10K99/00
CPCC09K2211/1011H01L51/5012H01L51/0078C07D209/86C09K2211/1029C09K2211/1092H01L51/006H01L51/0085C09K2211/185C09K2211/1007H05B33/14H01L51/0067C09K11/06H01L51/0071C09K2211/188C09K2211/186C09K2211/1014H01L51/0081H10K85/633H10K85/654H10K85/657H10K85/311H10K85/324H10K85/342H10K50/11
Inventor 荒金崇士岩隈俊裕池田秀嗣中村浩昭渡边隆佐池田洁
Owner IDEMITSU KOSAN CO LTD
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