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Benzofluorene compound, material for light-emitting layer using same, organic electroluminescent element, display device, and lighting device

An organic electric field and compound technology, which is applied in the field of benzofluorene compounds, can solve problems such as unreported properties, and achieve the effect of improving properties

Active Publication Date: 2016-11-30
爱思开新材料捷恩智株式会社
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, only its structural formula is disclosed in said document, and its specific characteristics are not reported.

Method used

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  • Benzofluorene compound, material for light-emitting layer using same, organic electroluminescent element, display device, and lighting device
  • Benzofluorene compound, material for light-emitting layer using same, organic electroluminescent element, display device, and lighting device
  • Benzofluorene compound, material for light-emitting layer using same, organic electroluminescent element, display device, and lighting device

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Experimental program
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Effect test

Embodiment

[0272]

[0273] Hereinafter, the formula (1-1-11), formula (1-2-11), formula (1-1-1), formula (1-2-1) and formula (1-1-46) represent The synthesis example of the compound will be described.

Synthetic example 1

[0274] [Synthesis Example 1] Synthesis of Compound (1-1-11)

[0275] [chem 45]

[0276]

[0277]

[0278] Under nitrogen atmosphere, 1-naphthylboronic acid (38.0g), 2-bromo-5-chlorobenzoic acid methyl ester (50.0g), Pd(PPh 3 ) 4 (2.3g), potassium phosphate (85.0g), toluene (500ml), 2-propanol (150ml) and water (50ml) were stirred at reflux temperature for 2 hours. After cooling the reaction liquid to room temperature, water was added and liquid-separated, and the solvent was distilled off under reduced pressure. The obtained oily substance was purified by silica gel column chromatography (developing solution: toluene / heptane mixed solvent). At this time, referring to the method described in "Introduction to Organic Chemistry Experiments (1) - Substance Treatment and Separation and Purification -" published by Chemical Doujin Co., Ltd., page 94, slowly increase the ratio of toluene in the developing solution to make The target substance is dissolved. The eluate was di...

Synthetic example 2

[0291] [Synthesis Example 2] Synthesis of Compound (1-2-11)

[0292] [chem 46]

[0293]

[0294]

[0295] Under nitrogen atmosphere, N-phenylnaphthalene-1-amine (1.1g), 9-chloro-5-iodo-7,7-dimethyl-7H-benzo[c]fluorene (2.0g) were added A flask of dichlorobis(tri-o-tolylphosphine)palladium(II) (0.2g), sodium tert-butoxide (0.7g) and 1,2,4-trimethylbenzene (20ml) was stirred at 140°C 12 hours. After cooling the reaction liquid to room temperature, water and ethyl acetate were added and liquid-separated. After the solvent was distilled off under reduced pressure, it was purified by silica gel chromatography (developing solution: toluene / heptane / ethyl acetate=9 / 90 / 1 (volume ratio)). After distilling off the solvent under reduced pressure, the obtained solid was washed with heptane to obtain 9-chloro-7,7-dimethyl-N-(naphthalene-1-yl)-N-phenyl-7H- Benzo[c]fluoren-5-amine (1.0 g).

[0296]

[0297] Under nitrogen atmosphere, N-phenyl-4-(trimethylsilyl)aniline (0.53g), 9-c...

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Abstract

The present invention provides a benzofluorene compound, a material for a light-emitting layer using the compound, an organic electroluminescent device, a display device, and a lighting device. The benzofluorene compound is used, for example, in an organic electroluminescent device to exhibit excellent performance. A benzofluorene compound represented by the following general formula (1) in which the benzofluorene ring is substituted by N,N-diphenylamino and N-naphthyl-N-phenylamino is used, for example, as a light-emitting layer of an organic electroluminescence element materials used, thereby forming components with excellent lifetime characteristics, [Chemical 521 In the above general formula, R is an alkyl group having 1 to 6 carbon atoms, etc., any one of A and B is a group represented by the above general formula (2), and the other is a group represented by the above general formula (3). group, R 1 It is a hydrogen atom or a silyl group substituted with an alkyl group having 1 to 4 carbon atoms, and n is an integer of 0 to 5.

Description

technical field [0001] The present invention relates to a benzofluorene compound, a material for a light-emitting layer using the compound, and an organic electroluminescent device. Background technique [0002] The organic electroluminescence element is a self-luminous light-emitting element, and is expected as a light-emitting element for display or illumination. Currently, various researches have been conducted on display devices using light-emitting elements that perform electroluminescence because they enable power saving and thinning. Furthermore, organic electroluminescence elements made of organic materials are actively studied because they are easy to reduce in weight or increase in size. In particular, with regard to the development of organic materials having light-emitting properties such as blue, which is one of the three primary colors of light, and the development of organic materials capable of transporting charges such as holes and electrons (possibly becomi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C211/61C07F7/10C09K11/06H01L51/50
Inventor 小野洋平枝连一志影山明子
Owner 爱思开新材料捷恩智株式会社