IP Library › Granted Patent US 9,312,491
Granted Patent B2
US 9,312,491 · App. 14/016,749 · Granted Apr 12, 2016

Polymer and photoelectric conversion element

Inventors: Seunghun Eu (Chiyoda-ku, JP); Tsuyoshi Asano (Chiyoda-ku, JP); Itaru Osaka (Higashi-Hiroshima, JP); Kazuo Takimiya (Higashi-Hiroshima, JP)
Assignees: JX NIPPON OIL & ENERGY CORPORATION; NATIONAL UNIVERSITY CORPORATION OF HIROSHIMA UNIVERSITY
H01L51/0036C08G61/123C08G61/126H01L31/0256C08G2261/124C08G2261/1412C08G2261/3223C08G2261/3246C08G2261/414C08G2261/91H01L51/0043H01L51/4253
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Quick Facts
Patent No.
US 9,312,491
App. No.
14/016,749
Granted
Apr 12, 2016
Kind
B2
Abstract

A photoelectric conversion element has a structure where a hole transport layer, a photoelectric conversion layer, and an electron transport layer are held between a first electrode and a second electrode. The photoelectric conversion layer is a bulk heterojunction layer, and fullerene or a fullerene derivative is used as an n-type organic semiconductor. As a p-type organic semiconductor, a polymer represented by the following Expression is used. In the Expression, R 1 , R 2 , R 3 , and R 4 each independently represent any one of a branched alkyl group, a linear alkyl group, an alkyl ester group, a carboxy alkyl group, and an alkoxy group. Independently, X is any one of S, O, and N.

Claims (17)

1. A polymer comprising a repeating unit that includes a five-membered ring including a thiazolothiazole framework and a heteroatom, which is expressed by the following Expression (1),

wherein a number average molecular weight is not less than 15,000 and not more than 48,000 in terms of polystyrene,

wherein hole mobility measured by a SCLC method is 7.5*10 −5 cm 2 /Vs or more,

wherein solubility with respect to 1 mL of chlorobenzene is 10 mg or more,

wherein R 1 , R 2 , R 3 , and R 4 each independently represent any one of a branched alkyl group, a linear alkyl group, an alkyl ester group, a carboxy alkyl group, and an alkoxy group,

wherein a percentage of linear alkyl groups in R 1 , R 2 , R 3 , and R 4 does not exceed 50 percent,

wherein X is independently any one of S, O, and N, and

wherein n is an integer of 1 or more.

2. The polymer according to claim 1 , wherein, in Expression (1), R 1 and R 2 are branched alkyl groups, and R 3 and R 4 are linear alkyl groups.

3. The polymer according to claim 1 , wherein a wavelength of a light absorption terminal of the polymer is 650 nm or more.

4. The polymer according to claim 1 , wherein a highest occupied molecular orbital (HOMO) of the polymer is deeper than 5.1 eV.

5. A photoelectric conversion element comprising: a p-type organic semiconductor; a photoelectric conversion layer having the p-type organic semiconductor and an n-type organic semiconductor that forms bulk heterojunction; a first electrode electrically connected to the photoelectric conversion layer on a side of a light-receiving surface of the photoelectric conversion layer; and a second electrode electrically connected to the photoelectric conversion layer on a side of the photoelectric conversion layer opposite to the light-receiving side thereof,

wherein the p-type organic semiconductor is a polymer comprising a repeating unit that includes a five-membered ring including a thiazolothiazole framework and a heteroatom, which is expressed by the following Expression (1), a number average molecular weight of the polymer being not less than 15,000 and not more than 48,000 in terms of polystyrene, hole mobility of the polymer measured by a SCLC method being 7.5*10 −5 cm 2 /Vs or more, solubility of the polymer with respect to 1 mL of chlorobenzene being 10 mg or more,

wherein R 1 , R 2 , R 3 , and R 4 each independently represent any one of a branched alkyl group, a linear alkyl group, an alkyl ester group, a carboxy alkyl group, and an alkoxy group,

wherein a percentage of linear alkyl groups in R 1 , R 2 , R 3 , and R 4 does not exceed 50 percent,

wherein X is independently any one of S, O, and N, and

wherein n is an integer of 1 or more.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 3, 2013
From: EU, SEUNGHUN; ASANO, TSUYOSHI; OSAKA, ITARU; TAKIMIYA, KAZUO
To: JX NIPPON OIL & ENERGY CORPORATION; NATIONAL UNIVERSITY CORPORATION OF HISOSHIMA UNIVERSITY
Reel/Frame 031128/0188 →
Priority Claims (1)
JP 2011-047014 · Mar 3, 2011 · national
Continuity (2)
Continuation PCTJP2012001391 · Feb 29, 2012
Related Publication 20140000716A1 · Jan 2, 2014