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A polycyclic aromatic compound and a polymer thereof, a material for an organic element, an organic electroluminescent element, a display device, or a lighting device.

A polycyclic aromatic compound technology, applied in the field of polycyclic aromatic compounds and their polymers, can solve the problems of insufficient aromatic epoxidation-reduction stability, insufficient life, and unsuitable main materials

Pending Publication Date: 2019-07-19
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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  • A polycyclic aromatic compound and a polymer thereof, a material for an organic element, an organic electroluminescent element, a display device, or a lighting device.
  • A polycyclic aromatic compound and a polymer thereof, a material for an organic element, an organic electroluminescent element, a display device, or a lighting device.
  • A polycyclic aromatic compound and a polymer thereof, a material for an organic element, an organic electroluminescent element, a display device, or a lighting device.

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0675] Hereinafter, although an Example demonstrates this invention more concretely, this invention is not limited to these. First, a synthesis example of a polycyclic aromatic compound will be described below.

Synthetic example (1

[0676] Synthesis Example (1): Synthesis of Compound (1-22)

[0677] [Chemical 122]

[0678]

[0679] Under nitrogen atmosphere, 3,4,5-trichloroaniline (12.0 g), d 5 -Bromobenzene (30.0 g), dichlorobis[(di-tert-butyl(4-dimethylaminophenyl)phosphino)]palladium (Pd-132, 0.43 g) as a palladium catalyst, tert-butanol Sodium (NaOtBu, 14.7 g) and xylene (200 ml) were put into the flask and heated at 120° C. for 3 hours. After the reaction, water and ethyl acetate were added to the reaction liquid and stirred, and then the organic layer was separated and washed with water. Then, the organic layer was concentrated to obtain a crude product. The crude product was purified with a silica gel short-path column (eluent: toluene / heptane=1 / 1 (volume ratio)) to obtain Intermediate (I-A) (15.0 g).

[0680] [Chemical 123]

[0681]

[0682]Under nitrogen atmosphere, intermediate (I-A) (15.0 g), bis(4-tert-butylphenyl)amine (25.9 g), bis(dibenzylideneacetone)palladium (0.48 g), 2-diphen...

Synthetic example (2

[0690] Synthesis Example (2): Synthesis of Compound (1-102)

[0691] [Chemical 126]

[0692]

[0693] Under nitrogen atmosphere, the d 5 - Aniline (5.0g), d 5 -Bromobenzene (8.25 g), Pd-132 (0.36 g) as a palladium catalyst, NaOtBu (7.1 g) and xylene (100 ml) were put into a flask, and heated at 120° C. for 1.5 hours. After the reaction, water and ethyl acetate were added to the reaction liquid and stirred, and then the organic layer was separated and washed with water. Then, the organic layer was concentrated to obtain a crude product. The crude product was purified with a silica gel short-path column (eluent: toluene / heptane=1 / 1 (volume ratio)) to obtain Intermediate (I-C) (8.1 g).

[0694] [Chemical 127]

[0695]

[0696] Under nitrogen atmosphere, intermediate (I-C) (8.0 g), intermediate (I-D) (20.6 g), Pd-132 (0.31 g) as a palladium catalyst, NaOtBu (6.4 g) and xylene (100 ml) were put together into a flask and heated at 120°C for 1 hour. After the reaction, w...

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Abstract

Provided are a novel polycyclic aromatic compound and a polymer thereof, a material for an organic element, an organic electroluminescent element, a display device, or a lighting device. By introducing deuterium at a natural abundance ratio or higher into a novel polycyclic aromatic compound in which a plurality of aromatic rings is linked via a boron atom, an oxygen atom, or the like, options ofa material for an organic device such as a material for an organic EL element are increased. Furthermore, by using a novel deuterium-substituted polycyclic aromatic compound as a material for an organic EL element, for example, an organic EL element having excellent luminous efficiency and element lifetime is provided.

Description

technical field [0001] The present invention relates to a polycyclic aromatic compound and a multimer thereof, a material for an organic element, an organic electroluminescence element, a display device or a lighting device. In addition, in this specification, an "organic electroluminescence element" may be expressed as an "organic EL (Electroluminescence) element" or simply as an "element". Background technique [0002] Conventionally, various studies have been conducted on display devices using light-emitting elements that perform electroluminescence to achieve low power consumption and thinning. Further, organic electroluminescence elements including organic materials have been actively studied because they are easy to reduce in weight or increase in size. In particular, development of organic materials having light-emitting properties such as blue, which is one of the three primary colors of light, and 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): C07F5/02C09K11/06H01L51/54
CPCC07F5/02C09K11/06C09K2211/104H10K85/657Y02E10/549H10K85/636H10K85/615H10K85/322H10K85/6574H10K85/6572H10K50/11H10K2101/10C07F5/027C07B2200/05H10K50/12H10K50/16H10K50/171H10K85/631H10K85/654
Inventor 畠山琢次广田敬幸枝连一志笹田康幸
Owner KWANSEI GAKUIN EDUCTIONAL FOUND
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