Polycyclic aromatic amino compound

An amino compound and polycyclic aromatic technology, applied in the field of polycyclic aromatic amino compounds, can solve the problems of unsuitable main material, insufficient life, insufficient redox stability of aromatic epoxies, etc.

Active Publication Date: 2019-07-23
KWANSEI GAKUIN EDUCTIONAL FOUND +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the oxidation-reduction stability of the aromatic ring with a small conjugated system is not sufficient, and the life of the device using the molecule having the conventional aromatic ring as the host material is not sufficient.
On the other hand, polycyclic aromatic compounds with extended π-conjugated systems usually have excellent redox stability, but the HOMO-LUMO gap (band gap Eg in thin films) or triplet excitation energy (E T ) are low and are therefore considered unsuitable for host materials

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0419] Hereinafter, although an Example demonstrates this invention more concretely, this invention is not limited to these Examples. First, a synthesis example of a polycyclic aromatic amino compound will be described below.

Synthetic example (1

[0421] Compound of formula (1A-1): N 5 ,N 5 ,N 13 ,N 13 -Synthesis of tetraphenyl-7,11-dioxa-17c-boraphenanthrene[2,3,4-no]tetraphenol-5,13-diamine

[0422] [chem 94]

[0423]

[0424]

[0425] Under nitrogen atmosphere, put diphenylamine (22.3g), 4-bromonaphthalene-2-ol (28.0g), Pd-132 (Johnson Matthey) (0.9g), NaOtBu (30.0g) and toluene (252ml) were heated and refluxed for 4 hours. After cooling the reaction liquid to room temperature, water and ethyl acetate were added and liquid-separated. Further, purification was carried out with a silica gel column (eluent: toluene) to obtain 35 g of 4-(diphenylamino)naphth-2-ol as an intermediate compound (yield: 89.5%).

[0426] [chem 95]

[0427]

[0428]

[0429] Under a nitrogen atmosphere, put 4-(diphenylamino)naphthalene-2-ol (16.0g), 2-bromo-1,3-difluorobenzene (5.0g), potassium carbonate (17.8g) and A flask containing 1-methyl-2-pyrrolidone (30 ml) was heated and stirred at reflux temperature for 8 hours. Aft...

Synthetic example (2

[0443] Compounds of formula (1A-173): N 5 ,N 5 ,N 13 ,N 13 ,Synthesis of 8,10-hexaphenyl-7,11-dioxa-17c-boraphenanthrene[2,3,4-no]tetraphenol-5,13-diamine

[0444] [chem 99]

[0445]

[0446]

[0447] Under nitrogen atmosphere, add 4-(diphenylamino)naphthalene-2-ol (16.1g), 5'-bromo-4',6'-difluoro-1,1':3',1 A flask of "-terphenyl (8.5g), potassium carbonate (13.6g) and 1-methyl-2-pyrrolidone (43ml) was heated and stirred at reflux temperature for 3 hours. After the reaction was stopped, the reaction solution was cooled to At room temperature, the precipitate precipitated after adding water was extracted by suction filtration. After the obtained precipitate was washed with water and methanol in sequence, it was washed with a silica gel short path column (eluent: toluene) ) for purification. Next, reprecipitate with ethyl acetate to obtain 3,3'-((5'-bromo-[1,1':3',1"-terphenyl]- 4',6'-diyl)bis(oxy))bis(N,N-diphenylnaphthalen-1-amine) 22.6 g (yield: 98.9%).

[0448] [...

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Abstract

The invention provides novel polycyclic aromatic amino compounds of the general formula, for example, the compounds having an amino substituent and having a plurality of aromatic rings linked by boronatoms, oxygen atoms, etc, whereby the options for materials for organic EL elements are increased. Also, novel polycyclic aromatic amino compounds are used as materials for organic electroluminescentelements, whereby exceptional organic EL elements are provided.

Description

technical field [0001] The invention relates to a polycyclic aromatic amino compound, an organic electroluminescent element using the same, an organic field effect transistor, an organic thin film solar cell, a display device and an illumination device. Background technique [0002] Conventionally, display devices using light-emitting elements that perform electroluminescence have been studied in various ways because they enable power saving and thinning. Furthermore, organic electroluminescent elements made of organic materials have been actively studied because they can be easily reduced in weight or increased in size. In particular, 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 having charge transport capabilities such as holes and electrons (with the possibility of becoming semiconductors or superconductors) So far, both high molecular compoun...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06H01L51/05H01L51/30H01L51/46H01L51/50
CPCC09K11/06C07F5/027Y02E10/549H10K85/322H10K50/11C09K2211/188C09K2211/1018H10K50/15H10K50/16H10K50/17H10K50/165H10K50/171
Inventor 畠山琢次王国防笹田康幸
Owner KWANSEI GAKUIN EDUCTIONAL FOUND
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