Polycyclic aromatic compound

A polycyclic aromatic compound technology, applied in the field of display devices and lighting devices, can solve the problems of insufficient redox stability, insufficient lifetime, and low triplet excitation energy of small aromatic rings

Pending Publication Date: 2021-08-06
KWANSEI GAKUIN EDUCATIONAL 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 small aromatic ring of the conjugated system is insufficient, and the lifetime of the device using a molecule obtained by linking conventional aromatic rings as a host material is insufficient.
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), triplet excitation energy (ET ) is low, therefore, it can be considered unsuitable for the host material

Method used

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  • Polycyclic aromatic compound
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Examples

Experimental program
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Effect test

Embodiment

[0787] Hereinafter, although an Example demonstrates this invention more concretely, this invention is not limited to them. First, a synthesis example of a polycyclic aromatic compound will be described below.

Synthetic example (1

[0789] Compound (1-230): 7,10-bis(trimethylphenyl)-2,15,18-trimethyl-5,12-dioxa-8b-aza-16b,19b-diboronanthracene[ Synthesis of 1,9-ab]benzo[j]perylene

[0790]

[0791] Under a nitrogen atmosphere, a mixture of 1-bromo-3-chloro-5-fluorobenzene (compound I-A, 14.7g, 70mmol), p-cresol (compound I-B, 7.95g, 74mmol), potassium carbonate (14.5g, 105mmol) ) and N-methylpyrrolidone (NMP) 500ml flask was heated to 150°C and stirred for 15 hours. The reaction solution was cooled to room temperature, filtered through a short column (eluent: toluene) using Florisil, and extracted with hydrochloric acid and toluene to obtain 1-bromo-3-chloro-5-(p-tolyloxy ) Benzene (Compound I-C) (18.4 g, 88% yield).

[0792]

[0793] The structure of the obtained compound was confirmed by NMR measurement.

[0794] 1 H-NMR (400MHz, CDCl 3 ): δ=2.35(s,3H), 6.86-6.98(m,4H), 7.13-7.18(m,3H).

[0795] Under nitrogen atmosphere, the compound I-C (13.1g, 44mmol), p-toluidine (compound I-D, 2.15g, 20...

Synthetic example (2

[0809] Compound (1-28): 7,10-di(trimethylphenyl)-2,15,18-trimethyl-5,12-di-p-tolyl-5,12H-dihydro-5,8b,12- Synthesis of triaza-16b,19b-diboronanthracene[1,9-ab]benzo[j]perylene

[0810]

[0811] Under a nitrogen atmosphere, 1,3-dibromo-5-chlorobenzene (compound I-H, 5.41g, 20mmol), di-p-toluidine (compound I-I, 3.95g, 20mmol), Pd 2 (dba) 3 (0.183mg, 0.2mmol), BINAP (0.249mg, 0.4mmol), tBuONa (2.12g, 22mmol) and toluene (100ml) were heated to 80°C and stirred for 40 hours. The reaction solution was cooled to room temperature, filtered using a short column filled with Florisil (eluent: toluene), and then filtered using a short column filled with silica gel (eluent: hexane), thereby obtaining 3-bromo -5-Chloro-N,N-di(p-tolyl)amine (compound I-J) (7.29 g, yield 50%).

[0812]

[0813] The structure of the obtained compound was confirmed by NMR measurement.

[0814] 1 H-NMR (400MHz, CDCl 3): δ=2.33(s,6H), 6.82(s,1H), 6.94-7.00(m,5H), 7.10-7.12(s,4H).

[0815] Under nitr...

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Abstract

[Problem] To provide: a polycyclic aromatic compound which has a novel structure; and an organic EL element which uses this polycyclic aromatic compound. [Solution] The present invention increases the number of options for materials for organic devices such as materials for organic EL elements by providing a polycyclic aromatic compound which has a novel structure wherein a plurality of aromatic rings are connected to each other by boron atoms, nitrogen atoms, oxygen atoms and the like. In addition, the present invention provides an organic EL element which is excellent in terms of, for example, luminous efficiency and element service life by using this polycyclic aromatic compound having a novel structure as a material for the organic EL element.

Description

technical field [0001] The present invention relates to a polycyclic aromatic compound, an organic electroluminescence element using the same, an organic field effect transistor and an organic thin film solar cell, as well as a display device and a lighting device. In addition, in this specification, "organic electroluminescent element" may be expressed as "organic EL element" or abbreviated as "element". Background technique [0002] Conventionally, display devices obtained by using light-emitting elements that perform electroluminescence have received various researches because they can realize power saving and thinning. Furthermore, organic electroluminescent elements formed of organic materials have received positive attention because they are easy to reduce in weight and increase in size. Research. In particular, for 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...

Claims

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Application Information

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IPC IPC(8): C07F5/02C09K11/06H01L51/50
CPCC07F5/02C09K11/06H10K50/00Y02E10/549C07F5/027C09K2211/188H10K85/322H10K50/11H10K71/00
Inventor 畠山琢次吉浦一基笹田康幸近藤靖宏
Owner KWANSEI GAKUIN EDUCATIONAL FOUND
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