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Compounds for electronic devices

A technology of compounds and atoms, applied in the field of electronic devices containing these compounds, can solve problems such as reducing the life of electronic devices and low electronic stability

Active Publication Date: 2012-11-14
MERCK PATENT GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, hole transport materials known in the prior art generally have low electron stability, which reduces the lifetime of electronic devices comprising these compounds

Method used

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  • Compounds for electronic devices
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  • Compounds for electronic devices

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0215] Example 1: 10-biphenyl-4-yl-9,9-dimethyl-2-(9-phenyl-9H-carbazol-3-yl)-9,10-dihydroacridine (HTM2) Synthesis

[0216]

[0217] a) Methyl 2-[4-(9-phenyl-9H-carbazol-3-yl)phenylamino]benzoate

[0218] Cesium carbonate (25.4 g, 78 mmol), palladium acetate (0.9 g, 4 mmol) and Xantphos (1.5 g, 8 mmol) were added to 3-(4-bromo-phenyl)-9-phenyl-9H-carbazole (CAS 1028647-93-9, 31.0 g, 78 mmol) and methyl anthranilate (10.1 ml, 78 mmol) in degassed toluene (300 ml), and the mixture was heated at reflux for 8 hours. The precipitated salts were filtered off and the mother liquor was evaporated under vacuum. The residue was extracted with chloroform in a Soxhlet extractor and subsequently recrystallized from toluene.

[0219] Yield: 26.0 g (55 mmol), 71% of theory, colorless solid.

[0220] b) 9,9-Dimethyl-2-(9-phenyl-9H-carbazol-3-yl)-9,10-dihydroacridine

[0221] Methyl 2-[4-(9-phenyl-9H-carbazol-3-yl)phenylamino]benzoate (26.0 g, 55 mmol) was added in portions to anhydro...

Embodiment 2

[0227] Example 2: Synthesis of 10-biphenyl-4-yl-2-(4-carbazol-9-ylphenyl)-9,9-dimethyl-9,10-dihydroacridine (HTM3)

[0228]

[0229] Similar to example 1, starting from 9-(4′-bromo-[1,1′-biphenyl]-4-yl)-9H-carbazole (CAS 212385-73-4) and methyl anthranilate , 10-biphenyl-4-yl-2-(4-carbazol-9-ylphenyl)-9,9-dimethyl-9,10-dihydroacridine was prepared in three steps.

[0230] Yield after sublimation: 7.2 g (12 mmol), 37% of theory, purity >99.9% by HPLC, colorless solid.

Embodiment 3

[0231] Example 3: Synthesis of 9,9-diphenyl-10-(9-phenyl-9H-carbazol-3-yl)-9,10-dihydroacridine (H3)

[0232]

[0233] Cesium carbonate (30.6 g, 94 mmol), palladium acetate (0.5 g, 2 mmol) and Xantphos (0.9 g, 5 mmol) were added to 9,10-dihydro-9,9-diphenylacridine (CAS 20474-15- 1, 15.7g, 47mmol) and 3-bromo-9-phenyl-9H-carbazole (CAS 1153-85-1, 15.1g, 47mmol) in a solution of degassed toluene (300ml), and the mixture Heated at reflux for 8 hours. The precipitated salts were filtered off and the mother liquor was evaporated under vacuum. The residue was extracted with toluene in a Soxhlet extractor. The crude product was subsequently recrystallized three times from toluene and sublimed twice in vacuum (p = 5 × 10 -5 mbar, T=280°C) for purification.

[0234] Yield: 10.5 g (18 mmol), 38% of theory, purity >99.9% by HPLC, colorless solid.

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Abstract

The present invention relates to compounds of formula (1) or (2) and the use thereof in electronic devices and to electronic devices containing said compounds. The invention further relates to the production of the compounds of formula (1) or (2) and to formulations containing one or more compounds according to formula (1) or (2).

Description

technical field [0001] The present invention relates to compounds of formula (1) or (2), to their use in electronic devices, and to electronic devices comprising these compounds. The invention also relates to the preparation of compounds of formula (1) or (2) and to formulations comprising one or more compounds of formula (1) or (2). Background technique [0002] The compounds of the formula (1) or (2) are used according to the invention in electronic devices, preferably in organic electroluminescent devices (OLEDs). The general structure of these devices is described, for example, in US 4539507, US 5151629, EP 0676461 and WO 98 / 27136. [0003] Hole-transport and injection materials for organic electroluminescent devices are known in the prior art, especially arylamine compounds. Materials of this type based on an indenofluorene framework are disclosed, for example, in WO 2006 / 100896 and WO 2006 / 122630. [0004] However, hole transport materials known in the prior art gen...

Claims

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Application Information

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IPC IPC(8): H01L51/00
CPCC07D519/00C09B57/00H01L51/0072H01L2251/5384H01L51/0061H01L51/5048C07D471/06C07D401/10C07D471/16C07D401/04Y02E10/549C09B19/00C07D498/06C07D513/06C09K11/025H10K85/636H10K85/6572H10K50/14H10K2101/90H05B33/20H10K85/657H10K50/11H10K50/15H10K50/17H10K2101/10
Inventor 康斯坦策·布罗克克里斯托夫·普夫卢姆侯赛因·埃米尔·帕勒姆罗科·福特
Owner MERCK PATENT GMBH
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