Polycyclic aromatic dimeric compound

A compound and dimer technology, applied in the field of display devices and lighting devices, can solve the problems of insufficient life, unsuitable main material, insufficient redox stability of aromatic epoxies, etc.

Pending Publication Date: 2020-05-29
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 having the conventional aromatic ring as the host material is not sufficient.
On the other hand

Method used

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  • Polycyclic aromatic dimeric compound
  • Polycyclic aromatic dimeric compound
  • Polycyclic aromatic dimeric compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0664] Hereinafter, although an Example demonstrates this invention more concretely, this invention is not limited to these. First, a synthesis example of a polycyclic aromatic dimer compound will be described below.

Synthetic example (1

[0666] Compound (1-201): 1,3-bis(5,9-diphenyl-5,9-dihydro-5,9-diaza-13bborinaphtho[3,2,1-de] Synthesis of anthracene-7-yl)thio)benzene

[0667] [CH215]

[0668]

[0669] [paragraph 1]

[0670] Under nitrogen atmosphere, 1,3-diiodobenzene (4.48g, 14mmol), 3,5-dibromobenzenethiol (5.50g, 31mmol), potassium carbonate (4.27g, 31mmol) were dissolved in 150mL of N, In N-dimethylformamide (N,N-Dimethylformamide, DMF), copper iodide (0.286g, 1.5mmol) was added thereto, and after stirring at 100°C for 4 hours, the reaction solution was cooled, and The solvent was distilled off to obtain a crude product. The crude product obtained using silica gel was filtered (eluent: hexane), and the residue was washed with hexane using an ultrasonic pulverizer to obtain the target 1 as a white solid. 3-Bis((3,5-dichlorophenyl)thio)benzene (4.73 g, 81% yield).

[0671] [chem 216]

[0672]

[0673] The structures of the obtained compounds were confirmed by nuclear magnetic resonance (Nuclea...

Synthetic example (2

[0689] Compound (1-5400): 1,3-bis(5,9-diphenyl-5,9-dihydro-5,9-diaza-13bborinaphtho[3,2,1-de] Synthesis of anthracen-7-yl)oxy)benzene

[0690] [chem 219]

[0691]

[0692] [paragraph 1]

[0693] Under nitrogen atmosphere, dissolve resorcinol (11.6g, 105mmol), 1-bromo-3,5-dichlorobenzene (55.0g, 221mmol), potassium carbonate (4.27g, 31mmol) in 180mL of N-methyl Base-2-pyrrolidone (N-Methyl-2-Pyrrolidone, NMP), copper iodide (4.01g, 21.1mmol), tris (2,4-pentanedionyl) iron (III) (7.44g , 21.1mmol), triphenylphosphine (22.1g, 84.3mmol), and after stirring at 180° C. for 4 hours, the reaction solution was cooled and filtered with celite. The filtrate was washed 3 times with water, and dried with anhydrous sodium sulfate. The constituent organisms obtained by concentrating the obtained solution were purified by silica gel chromatography (toluene), and then concentrated to obtain 1,3-bis(3 , 5-dichlorophenoxy)benzene (15.5 g, 37% yield).

[0694] [Chemical 220]

[0695] ...

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Abstract

Provided is an excellent polycyclic aromatic dimeric compound which is composed of two partial structures represented by general formula (1) and a linking group L1 that binds the two partial structures to each other, and which is able to be used, for example, as a material for organic EL elements. In formula (1), each of ring A, ring B and ring C is an aryl ring, a heteroaryl ring or the like; Y1is B or the like; each of X1 and X2 is >O or the like; the linking group L1 is a single bond, an arylene group having 6-30 carbon atoms, a heteroarylene group having 2-30 carbon atoms, an alkylene group having 1-24 carbon atoms, an alkenylene group having 1-24 carbon atoms, an alkynylene group having 1-24 carbon atoms, -O-, -S-, >N-R or a combination of these groups; R in the >N-R moiety is an aryl group having 6-16 carbon atoms, a heteroarylene group having 2-20 carbon atoms, an alkyl group having 1-12 carbon atoms or a cycloalkyl group having 3-16 carbon atoms; at least one hydrogen atom inthe linking group L1 may be substituted by an aryl group having 6-16 carbon atoms, a heteroaryl group having 2-20 carbon atoms, an alkyl group having 1-12 carbon atoms or a cycloalkyl group having 3-16 carbon atoms; and at least one hydrogen atom in the dimeric compound may be substituted by a cyano group, a halogen atom or a deuterium atom.

Description

technical field [0001] The invention relates to a polycyclic aromatic dimer compound, an organic electroluminescent element using the same, an organic field effect transistor, an organic thin film solar cell, a display device and an illumination device. Background technique [0002] Conventionally, display devices using light-emitting elements that perform electroluminescence have been studied in various ways because they enable power saving and thinning. 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) Development, so far, regardless of ...

Claims

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Application Information

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IPC IPC(8): C07F5/02C09K11/06H01L51/05H01L51/46H01L51/50
CPCC07F5/02C09K11/06H10K10/00H10K50/00C09K2211/188H10K85/322
Inventor 畠山琢次田端敬太笹田康幸梁井元树生田利昭
Owner KWANSEI GAKUIN EDUCATIONAL FOUND
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