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Material for organic electroluminescent device and organic electroluminescent device using same

一种电致发光元件、致发光的技术，应用在有机电致发光元件用材料,有机电致发光元件用材料及使用此材料的有机电致发光元件领域，能够解决3重态激发态能量降低、3重态激发态能量变小、发光效率降低等问题

Inactive Publication Date: 2007-01-10
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, although the heat resistance is improved, most of the phenylene structures constituting the compound are bonded in the para position, and the bond in the meta position is only the central benzene ring, so the symmetry is still good , the problem of crystallization cannot be avoided
In Patent Document 7 and Patent Document 8, it is disclosed that a host material of a heterocyclic skeleton such as a triazine skeleton is further introduced on the basis of a carbazole skeleton. Combination, so the linearity of the compound is high, the energy of the triplet excited state of the host compound becomes smaller, it is difficult to transfer energy from the host to the phosphorescent dopant, especially in the blue phosphorescent element, which causes a decrease in luminous efficiency The problem
Patent Document 9 discloses a compound in which five or more groups having benzene rings are bonded to a carbazole skeleton. However, since the compound skeleton has high symmetry and is easy to crystallize, straight lines having five or more groups having benzene rings The property is high, so there is a problem that the energy of the triplet excited state decreases

Method used

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  • Material for organic electroluminescent device and organic electroluminescent device using same
  • Material for organic electroluminescent device and organic electroluminescent device using same
  • Material for organic electroluminescent device and organic electroluminescent device using same

Examples

Experimental program
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Effect test

Embodiment

[0182] Next, the present invention will be described in further detail using examples.

Synthetic example 1

[0183] Synthesis Example 1 (Synthesis of Compound (C5))

[0184] The synthetic route of compound (C5) is shown below.

[0185]

[0186] (1) Synthesis of intermediate (IM1)

[0187] In a 1-liter three-necked flask, add 50g (160mmol) 3,3'-dibromobiphenyl, 18.4g (110mmol) carbazole, 3.0g (16mmol) copper iodide, 46.6g (220mmol) potassium phosphate, 18.2g ( 160 mmol) of trans-1,2-cyclohexanediamine, 500 ml of 1,4-dioxane, and stirred under an argon atmosphere at 150° C. for 12 hours. Thereafter, the reaction solution was cooled to room temperature, 160 ml of water was added, and extracted three times with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure.

[0188] The residue is applied to a silica gel column, and the dicarbazole-based substances and unreacted substances are removed and purified. 11.2 g of intermediate (IM1) (28 mmol, yield 25%) were obtained. The obtained compound was measured by FD-MS (f...

Synthetic example 2

[0196] Synthesis Example 2 (Synthesis of Compound (C8))

[0197] The synthetic route of compound (C8) is shown below.

[0198]

[0199]

[0200] (1) Synthesis of intermediate (IM3)

[0201] Under an argon atmosphere, 6.2g (20mmol) of 3,5-dibromobiphenyl, 5.8g (20mmol) of p-(carbazol-9-yl)phenylboronic acid, 460mg (0.4mmol) of four Triphenylphosphine palladium 0 valent (Pd(PPh 3 ) 4 ), 100 milliliters of dimethoxyethane, 64 g (60 mmol) of a 10% by weight aqueous solution of sodium carbonate, and stirred at 78° C. for 10 hours.

[0202] After the reaction is terminated, cool to room temperature, filter the precipitated crystals, add 100 ml of toluene to the filtrate, use a separatory funnel to wash the organic layer with water and saturated saline in sequence, dry it with anhydrous magnesium sulfate, and depressurize the organic layer after filtration Concentration afforded a brown sticky solid. This was purified using a silica gel column to obtain 5.2 g of an interme...

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Abstract

Provided is a material for organic electroluminescent devices which is composed of a compound having a specific structure which is low in symmetry. An organic electroluminescent device comprising an organic thin film layer which is composed of one or more layers including at least a light-emitting layer and sandwiched between an anode and a cathode is also disclosed wherein at least one layer of the organic thin film layer contains the above-described material for organic electroluminescent devices. The material for organic electroluminescent devices or an organic electroluminescent device that has high irradiance efficiency wihout pixel defects and has a high luminous efficiency, excellent heat resistance and long life.

Description

technical field [0001] The present invention relates to a material for an organic electroluminescent element and an organic electroluminescent element using the material, and in particular to a material for an organic electroluminescent element and an organic electroluminescent element having high luminous efficiency, no pixel defect, excellent heat resistance, and a long service life. Luminescent elements. Background technique [0002] Organic electroluminescent elements (hereinafter referred to as EL sometimes referred to as electroluminescence) are self-luminous elements that utilize the following principle, that is, utilizing the recombination energy of holes injected from the anode and electrons injected from the cathode through an external electric field, fluorescent The principle of matter luminescence. Since C.W.Tang et al. of イストマン・コダツク company reported low-voltage driving organic EL elements of laminated elements (C.W.Tang, S.A.Vanslyke, (Applied Physics Letters),...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): H05B33/14H05B33/22C09K11/06H01L51/00H01L51/50
CPCH01L51/0072H01L51/0059C09K2211/1029C09K2211/104C09K2211/1037H01L51/5092C09K11/06C09K2211/185C09K2211/1033C09K2211/1007H05B33/14C09K2211/186C09K2211/1059C09K2211/1044H01L51/0081H01L51/5016Y10S428/917H10K85/631H10K85/6572H10K85/324H10K50/171H10K50/11H10K2101/10
Inventor 岩隈俊裕富田诚司伊藤光则
Owner IDEMITSU KOSAN CO LTD
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