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Dibenzopyrromethene boron chelate compound, near-infrared light-absorbing material, thin-film, and organic electronic device

A compound and hydrogen atom technology, applied in the field of dibenzopyrromethine boron chelate compounds, can solve the problems of unmentioned photoelectric conversion characteristics, poor photoelectric conversion characteristics, etc.

Active Publication Date: 2019-12-31
NIPPON KAYAKU CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Moreover, its photoelectric conversion characteristics are also worse than those in the visible light domain
Furthermore, in Patent Document 5, there is no mention at all about the absorption wavelength or the photoelectric conversion characteristics in the near-infrared region.

Method used

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  • Dibenzopyrromethene boron chelate compound, near-infrared light-absorbing material, thin-film, and organic electronic device
  • Dibenzopyrromethene boron chelate compound, near-infrared light-absorbing material, thin-film, and organic electronic device
  • Dibenzopyrromethene boron chelate compound, near-infrared light-absorbing material, thin-film, and organic electronic device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0193] Embodiment 1 (synthesis of compound of the present invention)

[0194] The compound of the present invention represented by formula (1-22) is synthesized by the following scheme.

[0195]

[0196] (Step 1) In the described scheme, the synthesis of the intermediate compound represented by formula (2-2)

[0197] In a flask, (4-acetyl-3-biphenyl) (3-methoxy-2-thienyl) ketone (in the scheme, the compound represented by formula (2-1)) (68.3 mmol) Dissolve in ethanol (700mL) and acetic acid (150mL), add ammonium acetate (400mmol) and ammonium chloride (70mmol) after heating to 65°C, heat up to 90°C and stir for 3 hours. The reaction liquid was air-cooled, neutralized with a saturated hydrocarbon sodium aqueous solution, and the generated solid was collected by filtration to obtain an intermediate compound represented by formula (2-2) (31.4 mmol, yield 46% by mass).

[0198] The intermediate compound represented by formula (2-2) 1 The measurement results of H NMR are as ...

Embodiment 2

[0208] Embodiment 2 (synthesis of compound of the present invention)

[0209] (Step 4) Synthesis of the compound of the present invention represented by the formula (1-39) of the specific example

[0210] In addition to using (4-acetyl-3-biphenyl)(5-(2,1,3-benzothiadiazol-5-yl)-3-methoxy-2-thienyl)methanone substitution formula Except for the compound represented by (2-1), the compound of the present invention represented by formula (1-39) was obtained by following steps 1 to 3 of Example 1. (0.65mmol, yield 43% by mass)

[0211] The measurement results of the molecular weight of the compound represented by the formula (1-39) are as follows.

[0212] EI-MS (m / z): 868[M] +

Embodiment 3

[0213] Embodiment 3 (synthesis of compound of the present invention)

[0214] (Step 5) Synthesis of the compound of the present invention represented by the formula (1-48) of the specific example

[0215] In addition to using (3-acetyl-4-biphenyl)(5-(2,1,3-benzothiadiazol-5-yl)-3-methoxy-2-thienyl)methanone substitution formula Except for the compound represented by (2-1), the compound of the present invention represented by the formula (1-48) was obtained by following steps 1 to 3 of Example 1. (1.3 mmol, yield 84% by mass).

[0216] The measurement results of the molecular weight of the compound represented by the formula (1-48) are as follows.

[0217] EI-MS (m / z): 868[M] +

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Abstract

The present invention provides a compound represented by formula (1) (R1-R8 in formula (1) each represent a hydrogen atom, an alkyl group, an aromatic group, a heterocyclic group, a halogen atom, or the like. One of X1-X3 represents a sulfur atom, and the other two thereof represent a carbon atom having one R0. One of X4-X6 represents a sulfur atom, and the other two thereof represent a carbon atom having one R0. R0 represents a hydrogen atom, an alkyl group, an aromatic group, a heterocyclic group, a halogen atom, or the like.) is an organic compound which exhibits broad absorption across thenear-infrared region, and exhibits excellent photoelectric conversion efficiency in the near-infrared region. Provided are a near-infrared light-absorbing material which contains said compound, an organic thin-film which contains said near-infrared light-absorbing material, an organic electronic device which contains said organic thin-film, and an organic photoelectric conversion element which contains said organic thin-film.

Description

technical field [0001] The invention relates to a novel dibenzopyrromethine boron chelate compound with absorption band in the near-infrared light domain, as well as near-infrared light-absorbing materials, thin films and organic electronic devices containing the compound. Background technique [0002] A near-infrared light-absorbing material having an absorption band in a wavelength region of 700 to 2,500 nm has been studied for various industrial uses. Its concrete application can enumerate optical information recording media such as CD-R (compact disk-recordable); thermal CTP (computer to plate, computer to plate), flash toner fixing (flash toner fixing), Printing applications such as laser thermal recording; heat insulation film, etc. Furthermore, utilizing the characteristic of selectively absorbing a specific wavelength range, it can also be used in near-infrared light filters used in PDPs (plasma display panels), or films for plant growth adjustment. Furthermore, by...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02H01L51/42H01L51/50H10K99/00
CPCC07F5/022Y02E10/549H10K30/50H10K50/10C07F5/02H10K85/655H10K85/6572H10K30/00
Inventor 青竹达也品村祥司前田健太郎桥本雄太贞光雄一
Owner NIPPON KAYAKU CO LTD
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