Polycyclic aromatic compound

A polycyclic aromatic compound technology, applied in the field of display devices and lighting devices, can solve the problems of unsuitable main materials, insufficient life, and insufficient stability of aromatic epoxy redox

Active Publication Date: 2016-03-23
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
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Embodiment

[0766] 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 compound will be described below.

Synthetic example (1

[0768] Synthesis of 5,9-dioxa-13b-boranaphtho[3,2,1-de]anthracene

[0769] [chem 252]

[0770]

[0771] First, add 1.6M n-butyllithium hexane solution (0.75ml) to a flask containing diphenoxybenzene (0.26g) and o-xylene (3.0ml) at 0°C under a nitrogen atmosphere . After stirring for 30 minutes, the temperature was raised to 70° C., and stirring was continued for 4 hours. After heating and stirring at 100° C. under a nitrogen stream to distill off hexane, the mixture was cooled to -20° C., boron tribromide (0.114 ml) was added, and stirred for 1 hour. After heating up to room temperature and stirring for 1 hour, N,N- diisopropylethylamine (0.342 ml) was added, and it heated and stirred at 120 degreeC for 5 hours. Then, N,N-diisopropylethylamine (0.171 ml) was added, it filtered using the magnesium silicate short path column (Florisil short path column), and the solvent was distilled off under reduced pressure to obtain a crude product. The crude organism was washed with ...

Synthetic example (2

[0777] Synthesis of 15b-bora-5,9-dioxaphenanthro[1,2,3-ij]tetraphene

[0778] [chem 254]

[0779]

[0780] First, copper (I) iodide (19.7 mg), α-picolinic acid (26.2 mg), potassium phosphate (0.429 g), resorcinol (57.5 mg) and 1-bromonaphthalene (0.154 ml) was added to a flask containing dimethyl sulfoxide (2.0 ml). After heating and stirring at 90° C. for 33.5 hours, 1N aqueous ammonia (3.0 ml) was added at room temperature, and the aqueous layer was extracted three times with toluene, and the solvent was distilled off under reduced pressure. The obtained solid was purified by silica gel column chromatography (developing liquid: toluene) to obtain 1,3-bis(1-naphthyloxy)benzene (0.155 g) as a white solid.

[0781] [chem 255]

[0782]

[0783] Under nitrogen atmosphere, 1.6M n-butyllithium hexyl Alkanes solution (9.0ml). After heating up to 70°C and stirring for 4 hours, the temperature was further raised to 100°C, and hexane was distilled off. After cooling to 0° C...

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Abstract

The present invention addresses the problem of providing a novel polycyclic aromatic compound and an organic electroluminescent element using the same. The above problem is solved by providing a novel polycyclic aromatic compound in which a plurality of aromatic rings are connected by boron atoms, oxygen atoms, or the like, thereby increasing the number of options for organic EL element materials, and also solved by providing a superior organic EL element using said novel polycyclic aromatic compound as an organic EL element material.

Description

technical field [0001] The invention relates to a polycyclic aromatic compound and an organic electroluminescent element using it, an organic field effect transistor, an organic thin film solar cell, a display device and a lighting device. Background technique [0002] Conventionally, display devices using light-emitting elements that perform electroluminescence have been researched in various ways because they can be reduced in power or thinned. 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 compounds and lo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C07F9/6571C07F9/6578C09K11/06H01L29/786H01L51/05H01L51/30H01L51/46H01L51/50
CPCC07F9/657163C09K11/06C09K2211/1011C09K2211/1029C09K2211/1007C09K2211/1096H10K85/653H10K85/657H10K85/6572H10K2102/00C07F9/65685Y02E10/549C09B57/00H10K85/322C07F5/027H01L29/786C07F9/65683
Inventor 畠山琢次中塚宗一郎中嶋贵一平井大贵小野洋平枝连一志倪静萍松下武司生田利昭
Owner KWANSEI GAKUIN EDUCTIONAL FOUND
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