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Tertiary-alkyl-substituted polycyclic aromatic compounds

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

Pending Publication Date: 2020-11-13
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 aromatic ring with a small conjugated system is not sufficient, and the life of the device using the molecule linked to 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 the triplet excitation energy (E T ) is low and therefore considered unsuitable for host materials

Method used

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Examples

Experimental program
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Embodiment

[1045] 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

[1046] Synthesis Example (1): Synthesis of Compound (1-151)

[1047] [chem 200]

[1048]

[1049]Under a nitrogen atmosphere, 4-(tert-amyl)aniline (15.0 g) was dissolved in acetonitrile (150 ml), bromine (22.5 g) was added dropwise thereto under ice-cooling, and the mixture was stirred for 0.5 hours. After the reaction, water and ethyl acetate were added to the reaction liquid and stirred, and the organic layer was separated and washed with water. Thereafter, the organic layer was concentrated to obtain a crude product. The crude product was purified with a silica gel short column (eluent: toluene), thereby obtaining an intermediate (I-A) (20.0 g).

[1050] [CH201]

[1051]

[1052] Under a nitrogen atmosphere, copper chloride (10.1 g), intermediate (I-A) (20.0 g) were dissolved in acetonitrile (100 ml), and nitrous acid dissolved in acetonitrile (50 ml) was added dropwise thereto at 60° C. Tert-butyl ester (9.6 g), stirred at 60°C for 0.5 hour. After the reaction, ...

Synthetic example (2

[1063] Synthesis Example (2): Synthesis of Compound (1-147)

[1064] [CH205]

[1065]

[1066] Under a nitrogen atmosphere, 2,3-dichloroaniline (15.0 g), 1-bromo-4-tert-amylbenzene (52.6 g), Pd-132 (1.32 g) as a palladium catalyst, NaOtBu (22.0 g) and xylene (150 ml) were put into a flask, and heated at 130° C. for 4 hours. After the reaction, water and ethyl acetate were added to the reaction liquid and stirred, and the organic layer was separated and washed with water. Thereafter, the organic layer was concentrated to obtain a crude product. The crude product was purified with a silica gel short column (eluent: toluene / heptane=1 / 1 (volume ratio)), thereby obtaining an intermediate (I-D) (38.0 g).

[1067] [chem 206]

[1068]

[1069] Under a nitrogen atmosphere, the intermediate (I-D) (15.0g), bis(4-tert-butylphenyl)amine (8.4g), Pd-132 (0.21g) as a palladium catalyst, NaOtBu (4.3g) and Xylene (60 ml) was put into the flask, and heated at 120° C. for 1 hour. Afte...

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Abstract

The present invention increases the options for organic device materials such as organic EL element materials by introducing a specific tertiary alkyl group into novel polycyclic aromatic compounds inwhich a plurality of aromatic rings are linked by boron atoms and oxygen atoms or the like. The present invention also provides an organic EL element that has, for example, excellent luminous efficiency by using a novel cycloalkyl-substituted polycyclic aromatic compound as an organic EL element material.

Description

technical field [0001] The invention relates to a tertiary alkyl-substituted polycyclic aromatic compound, an organic electroluminescence element, an organic field-effect transistor, an organic thin-film solar cell, a display device and an illumination device using the same. In addition, in this specification, an "organic electroluminescence element" may be expressed as an "organic EL (electroluminescence) element" or simply as a "device". Background technique [0002] In the past, display devices using light-emitting elements that perform electroluminescence have been researched in various ways because they can be made smaller or thinner. 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, regarding the development of organic materials having luminescent properties such as blue, which is one of the three primary colors of light, and the deve...

Claims

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Application Information

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IPC IPC(8): C07F5/02C09K11/06H01L27/32H01L51/50
CPCC07F5/02C09K11/06H10K85/658H10K50/12C07F5/027C09D11/03C09K2211/188
Inventor 畠山琢次枝连一志小林孝弘笹田康幸
Owner KWANSEI GAKUIN EDUCATIONAL FOUND
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