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

An electroluminescence element and an electroluminescence technology, which are applied in the field of materials for organic electroluminescence elements and organic electroluminescence elements, and can solve the problems of small molecular weight, insufficient heat resistance stability, and shortened life span.

Inactive Publication Date: 2009-04-15
IDEMITSU KOSAN CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the electron-accepting compounds used in these have problems in that they are unstable in operation in the production process of organic EL elements, or have insufficient stability such as heat resistance when driving organic EL elements, and have problems such as reduced lifespan.
[0009] In addition, tetrafluorodicyanobenzoquinodimethane, which is an electron-accepting compound exemplified in Patent Documents 5, 7, 8, etc., has a small molecular weight or is substituted with fluorine and has high sublimation properties. When manufacturing organic EL elements, it may diffuse in the device and contaminate the device or element. In addition, there are problems such as current leakage due to crystallization when manufacturing an element

Method used

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0287] Synthesis of (A-19)

[0288] 4.5 g of potassium tert-butoxide and 10 mL of DMSO were mixed at room temperature under a nitrogen atmosphere, and 5.2 g of 3-trifluoromethylphenol was added thereto. A solution of 4.3 g of 2,5-dibromobenzoquinone and 15 mL of DMSO was added dropwise to the mixed liquid, followed by stirring at room temperature for 8 hours. Thereafter, ethyl acetate and water were added for layering operation, anhydrous sodium sulfate was added to filter the organic layer, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 3.0 g of compound (A-19).

[0289] Measure the IR of the compound, at 1665cm -1 The absorption of the carbonyl group was confirmed. M / Z = 428 was confirmed by mass spectrometry.

[0290] The resulting compound was dissolved in acetonitrile at a concentration of 0.01 mol / L, using tetrabutylammonium perchlorate (TBAP) as the supporting electrolyte, and a satura...

Embodiment 2

[0292] Synthesis of (A-1)

[0293] First, a solution obtained by mixing 1.7 g of (A-19), 0.54 g of malononitrile, and dichloromethane was stirred while cooling with ice under a nitrogen atmosphere, and 2.4 mL of titanium tetrachloride was added dropwise, and then Add 3.6 mL of pyridine dropwise. Then, after stirring for 5 hours, dichloromethane was distilled off under reduced pressure, and 5 mL of 1N hydrochloric acid was added thereto. The precipitate was recrystallized from acetonitrile, followed by sublimation purification to obtain 0.8 g.

[0294] Measure the IR of the compound, at 2222cm -1 Confirm the absorption of cyano group. M / Z = 524 was confirmed by mass spectrometry.

[0295] The resulting compound was dissolved in acetonitrile at a concentration of 0.01 mol / L, using tetrabutylammonium perchlorate (TBAP) as the supporting electrolyte, and a saturated calomel (SCE) electrode as the reference electrode, by cyclic voltaic The reduction potential was determined by...

Embodiment 3

[0297] Synthesis of (B-7)

[0298] In Example 1, 5.0 g of 1,5-dibromo-2,6-naphthoquinone was used instead of 2,5-dibromobenzoquinone, and 5.2 g of 4-trifluoromethylphenol was used instead of 3-trifluoromethyl Phenol was synthesized in the same manner as in Example 1 except that, to obtain 2.7 g of (B-7).

[0299] Measure the IR of the compound, at 1658cm -1 The absorption of the carbonyl group was confirmed. M / Z = 478 was confirmed by mass spectrometry.

[0300]In addition, the reduction potential measured by cyclic voltammetry was 0.01V.

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Abstract

A material for an organic electroluminescent device including a quinone derivative represented by the following formula (1), (2) or (3): wherein R<1 >to R<16 >are each a hydrogen atom, a halogen atom, a cyano group, an alkoxy group, a substituted or unsubstituted aryloxy group, an alkyl group, a fluoroalkyl group, an aryl group or a heterocyclic group; provided that at least one of R<1 >to R<4>, at least one of R<5 >to R<10 >or at least one of R<11 >to R<16 >is an aryloxy group; and X is a substituent represented by any one of the following formulas (a) to (f): wherein R<17 >to R<19 >are a hydrogen atom, an alkyl group, or aryl group; and R<18 >and R<19 >may be bonded together to form a ring.

Description

technical field [0001] The present invention relates to a material for organic electroluminescent elements and an organic electroluminescent element using the same. Background technique [0002] An organic electroluminescent element (hereafter, "electroluminescence" is abbreviated as "EL") is a self-luminous element utilizing the principle that, by applying an electric field, the The recombination energy of the fluorescent substance emits light. [0003] Since the report (Non-Patent Document 1, etc.) of low-voltage driving organic EL elements based on multilayer elements researched by C.W.Tang of Iselman Kudak (Istman Kodatsuku) Co., Ltd. Research on materials for organic EL elements has been actively carried out. [0004] The organic EL device reported by Tang et al. has a laminated structure in which tris(8-quinoline aluminum) is used as a light-emitting layer and a triphenyldiamine derivative is used as a hole transport layer. As the advantages of the laminated structu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C50/28C07C50/32C07C255/37C07C261/04C09K11/06H01L51/50
CPCC09K2211/1011C07C261/04H01L51/0059H01L51/0051C07C211/54H01L51/5048H01L51/0052H01L51/5092C07C50/32C09K2211/1007H05B33/14C09K11/06C07C255/37C07C49/755C07C50/28C07C46/00C09K2211/1014H01L51/0081H10K85/611H10K85/615H10K85/631H10K85/324H10K50/14H10K50/171
Inventor 森下浩延川村久幸细川地潮
Owner IDEMITSU KOSAN CO LTD
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