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Polycyclic aromatic compound and multimer of same

A polycyclic aromatic compound technology, which is applied in the field of display devices and lighting devices, can solve the problems of insufficient aromatic epoxidation-reduction stability, insufficient life, and unsuitable host materials.

Pending Publication Date: 2021-01-15
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 lifetime of the device using the molecule connecting 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 of the film) or triplet excitation energy (E T ) is low and therefore considered unsuitable for host materials

Method used

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  • Polycyclic aromatic compound and multimer of same
  • Polycyclic aromatic compound and multimer of same
  • Polycyclic aromatic compound and multimer of same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[1208] Hereinafter, although an Example demonstrates this invention concretely, this invention is not limited by these Examples at all. The following are compounds synthesized by Examples.

Synthetic example (1

[1210] Compound (BOCz-0001): Synthesis of 5-oxa-8b-aza-15b-borabenzo[a]naphtho[1,2,3-hi]aceanthrylene

[1211] [chem 354]

[1212]

[1213] Under nitrogen atmosphere, put 1,6-difluoro-2-bromobenzene (1.68ml, 15mmol), carbazole (1.62g, 10mmol), tert-BuOK (1.68g, 15mmol) and 1,3- A flask of dimethyl-2-imidazolidinone (DMI, 30ml) was heated to 120°C and stirred for 20 hours. The reaction solution was cooled to room temperature, and the DMI was distilled off under reduced pressure, filtered using a silica gel short-path column (eluent: hexane), and the solvent was distilled off under reduced pressure to obtain 9-(2-bromo-3- Fluorophenyl)-9H-carbazole (1.56 g, 56% yield).

[1214] [chem 355]

[1215]

[1216] The structure of the obtained compound was confirmed by nuclear magnetic resonance (nuclear magnetic resonance, NMR) measurement.

[1217] 1 H-NMR (400MHz, CDCl 3 ): δ=7.07(d,2H),7.30-7.36(m,4H),7.41(t,2H),7.51(d,1H),8.15(d,2H).

[1218] Under nitrogen atmosphere,...

Synthetic example (2

[1231] Compound (BNpCz-12mS-0230-1): N,N,5-tris(3,5-dimethylphenyl)-1,3-dimethyl-5H-5,8b-diaza-15b, Synthesis of Borabenzo[a]naphtho[1,2,3-hi]acethracen-7-amine

[1232] [chem 358]

[1233]

[1234] Under nitrogen atmosphere, put 1-fluoro-3,5-dibromobenzene (3.77g, 15mmol), carbazole (17.4g, 18mmol), cesium carbonate (9.77g, 30mmol) and N-methylpyrrolidone (NMP, 50ml) flask was heated to 120°C and stirred for 20 hours. The reaction solution was cooled to room temperature, and NMP was distilled off under reduced pressure, then filtered using a silica gel short path column (eluent: hexane), and the solvent was distilled off under reduced pressure to obtain 9-(3,5-di Bromophenyl)-9H-carbazole (2.69 g, 47% yield).

[1235] [chem 359]

[1236]

[1237] The structure of the obtained compound was confirmed by NMR measurement.

[1238] 1 H-NMR (400MHz, CDCl 3 ): δ=7.29(s,2H),7.40-7.46(m,4H),7.70(s,2H),7.76(s,1H),8.12(d,2H).

[1239] Under a nitrogen atmosphere, bis(3,5-d...

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Abstract

The present invention increases options for materials for organic EL elements by providing a novel polycyclic aromatic compound wherein a plurality of aromatic rings are linked by means of boron atomsand nitrogen atoms, or the like. In addition, the present invention provides an excellent organic EL element by using this novel polycyclic aromatic compound as a material for an organic electroluminescent element.

Description

technical field [0001] The present invention relates to a polycyclic aromatic compound and its multimer (hereinafter, these are also collectively referred to as "polycyclic aromatic compound"), an organic electroluminescent device using the same, an organic field effect transistor and Organic devices such as organic thin film solar cells, display devices and lighting devices. Background technique [0002] Previously, display devices using light-emitting elements that perform electroluminescence have been researched in various ways because they can achieve power saving or thinning, and organic electroluminescent elements made of organic materials have been actively researched because they can be easily reduced in weight or increased in size. . In particular, regarding the development of organic materials having luminescent properties such as blue, which is one of the three primary colors of light, and the development of organic materials having charge transport capabilities ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06G02F1/13357G02F1/1368H01L27/32H01L51/50H10K99/00
CPCC07F5/02C09K11/06G02F1/1368H10K85/658H10K50/12H10K50/85Y02E10/549C07F5/027C09K2211/188
Inventor 畠山琢次近藤靖宏笹田康幸小林孝弘王国防梁井元树
Owner KWANSEI GAKUIN EDUCTIONAL FOUND