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Nitrogen-containing condensed heterocyclic compounds for oleds

A technology of compounds and heteroaromatic rings, applied in the field of materials in organic electroluminescent devices, can solve the problems of no disclosure and the like

Inactive Publication Date: 2012-07-25
MERCK PATENT GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, compounds in which one or more carbon atoms of the undisclosed skeleton are replaced by nitrogen

Method used

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  • Nitrogen-containing condensed heterocyclic compounds for oleds
  • Nitrogen-containing condensed heterocyclic compounds for oleds
  • Nitrogen-containing condensed heterocyclic compounds for oleds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0212] Example 1: 6-bromo-8,8-dimethyl-8H-3,12b-diazabenzo[a]acethracene

[0213]

[0214] 1a) Methyl 2-pyrido[4,3-b]indol-5-ylbenzoate

[0215]

[0216] 16.8g (100mmol) of 5H-pyrido[4,3-b]indole[244-69-9], 28.8g(110mmol) of methyl 2-iodobenzoate[610-97 -9], 34.6g (250mmol) of potassium carbonate, 6.4g (100mmol) of copper powder and 100g of glass beads (3mm in diameter) in 300ml of DMF were stirred at 130°C for 24h. After cooling, the mixture was filtered through a short bed of celite, the bed was rinsed with DMF, and the DMF was removed in vacuo. The residue was dissolved in 500 ml of dichloromethane, and the solution was washed three times with 200 ml each of 0.5N sodium hydroxide solution and dried over magnesium sulfate. After removal of the dichloromethane under vacuum, the residue was recrystallized once from ethyl acetate and dried under vacuum (p=0.1 mbar, T=60°C). Yield: 19.3 g (64 mmol), 64%; Purity: 97% ( 1 H-NMR).

[0217] The following compounds are sim...

Embodiment 2

[0232] Example 2: 8,8-dimethyl-6,10-bis[1,1′; 3′,1″]terphenyl-5′-yl-8H-3,12b-diazabenzo[a ]acethracene

[0233] 2a) 6,10-Dibromo-8,8-dimethyl-H-3,12b-diazabenzo[a]acethracene

[0234]

[0235] 28.4g (100mmol) of 8,8-dimethyl-H-3,12b-diazabenzo[a]acethracene and 36.5g (205mmol) of N-bromosuccinimide in The mixture in 200ml DMF was stirred at 80°C for 16h. After cooling, 100 ml of ethanol were added, the precipitated solid was filtered off with suction, washed three times with 50 ml of ethanol and dried under vacuum (p=0.1 mbar, T=60° C.). Yield: 16.3 g (77 mmol), 77%; Purity: 98% ( 1 H-NMR).

[0236] 2b) 8,8-Dimethyl-6,10-bis[1,1′;3′,1″]terphenyl-5′-yl-8H-3,12b-diazabenzo[a]ester Anthracene

[0237]

[0238] 13.3g (30mmol) of 6,10-dibromo-8,8-dimethyl-H-3,12b-diazabenzo[a]acethracene, 24.7g (90mmol) of [1 , 1′: 3′, 1″-terphenyl]-5′-ylboronic acid [128388-54-5], 34.8g (180mmol) tripotassium phosphate, 67mg (0.3mmol) palladium(II), 548mg (1.8mmol) tri-o-tolylphosphi...

Embodiment 3

[0239] Example 3: Spiro[fluorenyl-9,8'-H-3,12b-diazabenzo[a]acethracene]

[0240] 3a) 3,12b-diazabenzo[a]acethren-8-one

[0241]

[0242]15.1 g (50 mmol) of methyl 2-pyrido[4,3-b]indol-5-ylbenzoate were suspended in a mixture of 200 ml of glacial acetic acid and 5 ml of concentrated sulfuric acid. The suspension was heated to reflux for 5 h, then the acetic acid was removed in vacuo, the residue was dissolved in 500 ml of dichloromethane and neutralized with 1N sodium hydroxide solution. The organic phase was separated off, dried over magnesium sulfate and evaporated under vacuum. The residue was dissolved in 30ml of ethyl acetate, and 100ml of ethanol was slowly added at high temperature. After cooling, the precipitated solid was filtered off with suction, washed three times with 50 ml of ethanol and dried under vacuum (p=0.1 mbar, T=60° C.). Yield: 10.5 g (39 mmol), 78%; Purity: 97% ( 1 H-NMR).

[0243] 3b) spiro[fluorenyl-9,8'-H-3,12b-diazabenzo[a]acethracene]

[0...

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Abstract

The invention relates to compounds according to formula (1), formula (2), formula (3) and formula (4), which are suitable for being used in electronic devices, in particular organic electroluminescent devices.

Description

technical field [0001] The present invention relates to materials for use in electronic devices, especially in organic electroluminescent devices. Background technique [0002] Structures of organic electroluminescent devices (OLEDs) in which organic semiconductors are used as functional materials are described, for example, in US 4539507, US 5151629, EP 0676461 and WO 98 / 27136. The luminescent materials used here are increasingly organometallic complexes which exhibit phosphorescence rather than fluorescence (M.A. Baldo et al., Appl. Phys. Lett. 1999, 75, 4-6). For quantum mechanical reasons, up to a four-fold increase in energy and power efficiency can be achieved using organometallic compounds as phosphorescent emitters. In general, however, improvements are still required in OLEDs, in particular also in OLEDs showing triplet emission (phosphorescence), for example in terms of efficiency, operating voltage and lifetime. This applies in particular to OLEDs that emit, for...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04C07D471/22C07D455/03C07D471/14C07D498/14C07D519/00C07D498/22C07D513/14C07D513/22C07F7/08C07F9/6568C07F15/00C07D513/04C09K11/06H05B33/14
CPCC09K2211/1011C07F7/0816C07D498/14C09K2211/1048C09K2211/1033C07D519/00C09B57/00C09K11/06C07F9/65685C07D498/22C07D471/04C09K2211/1044C07D471/22C09K2211/1092C09K2211/1029C09K2211/104C07D513/04C07D513/22C09K2211/1037C07F15/0086C07D513/14C09K2211/1096C07D455/03C07F15/0033H05B33/14C07F9/65683C07D471/14C09K2211/1059C09K2211/1088C07F15/0026
Inventor 菲利普·施特塞尔埃斯特·布罗伊宁多米尼克·约斯滕克里斯托夫·普夫卢姆埃米尔·侯赛因·帕勒姆
Owner MERCK PATENT GMBH
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