JP-7856459-B2 - Compounds, hole transport materials, and photoelectric conversion elements using the same

Inventors

• 伊東 俊昭
• 高橋 秀聡
• 佐藤 洋

Assignees

• 保土谷化学工業株式会社

Dates

Publication Date

20260511

Application Date

20220325

Claims (3)

1. A compound represented by the following general formula (1). [In the formula, R1 , R2 , R4 , R5 , R6, R7 , R9 , R10 , R11 , R12 , R14 , R15 , R16 , R17 , R19 and R20 are hydrogen atoms, and R3 , R8 , R13 and R18 represent diphenylamino groups substituted with alkoxy groups having 1 to 18 carbon atoms . ] R5 and R6 , and R15 and R16 may be bonded to each other to form a ring. X1 and X2 are represented by the following general formula (2) . Y1 represents an oxygen atom. [In the formula, R23 to R28 are hydrogen atoms.] Z1 represents an oxygen atom, a sulfur atom, or a selenium atom, and m represents an integer of 1, and n represents an integer of 0 .
2. A hole transport material represented by the compound described in claim 1 .
3. A photoelectric conversion element using the hole transport material described in claim 2 .

Description

This invention relates to a compound, a hole transport material, and a photoelectric conversion element using the same. In recent years, solar power generation has attracted attention as a clean energy source, and the development of solar cells is thriving. Among these, the development of solar cells using perovskite materials in the photoelectric conversion layer (hereinafter referred to as perovskite solar cells) is attracting attention as a next-generation solar cell that is low-cost and can be manufactured using a solution process (for example, Patent Document 1, Non-Patent Documents 1-2). In perovskite solar cells, hole transport materials are often used within the device. The purposes of their use include (1) enhancing the selective hole transport function to improve photoelectric conversion efficiency, and (2) bonding with the perovskite photoelectric conversion layer to protect the perovskite material, which is susceptible to the effects of moisture and oxygen (see, for example, Non-Patent Document 3). Spiro-OMeTAD, a spirobifluorene-based organic compound, is often used as a standard hole transport material, but there are few reports of hole transport materials that contribute more significantly to photoelectric conversion characteristics than this material. International Publication No. 2017/104792 J. Am. Chem. Soc., 2009, Vol. 131, pp. 6050–6051Science, 2012, Vol. 388, pp. 643-647Chem. Sci. , 2019, 10, P. 6748-6769 This is a schematic cross-sectional view showing the configuration of the photoelectric conversion element in the embodiments and comparative examples of the present invention. The embodiments of the present invention will be described in detail below. The hole transport material of the present invention is used in photoelectric conversion elements and perovskite-type photoelectric conversion elements. The compounds represented by the general formula (1) of the present invention will be described in detail below, but the present invention is not limited to these. In general formula (1), R1 to R20 are each independent of each other. Hydrogen atom, halogen atom, carboxyl group, trimethylsilyl group, Linear or branched alkyl groups having 1 to 20 carbon atoms, which may have substituents. A linear or branched alkenyl group having 2 to 20 carbon atoms, which may have substituents. A cycloalkyl group having 3 to 12 carbon atoms, which may have substituents. A linear or branched alkoxy group having 1 to 20 carbon atoms, which may have substituents. A cycloalkoxy group having 3 to 10 carbon atoms, which may have substituents. A linear or branched acyl group having 1 to 20 carbon atoms, which may have substituents. A thio group having 1 to 18 carbon atoms, which may have substituents. An amino group having 1 to 20 carbon atoms, which may have substituents. This represents an aromatic hydrocarbon group having 6 to 36 carbon atoms and having substituents, or a heterocyclic group having 5 to 36 ring-forming atoms, which may have substituents. In general formula (1), examples of "halogen atoms" represented by R1 to R20 include fluorine, chlorine, bromine, and iodine. In general formula (1), the "linear or branched alkyl group having 1 to 20 carbon atoms, which may have substituents" represented by R1 to R20 , can specifically include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, n-pentyl group, isopentyl group, n-hexyl group, 2-ethylhexyl group, heptyl group, octyl group, isooctyl group, nonyl group, decyl group, and the like. In general formula (1), the "linear or branched alkenyl group having 2 to 20 carbon atoms, which may have substituents" represented by R 1 to R 20 , specifically include ethenyl group (vinyl group), 1-propenyl group, 2-propenyl group (allyl group), 1-methylethenyl group, 1-butenyl group, 2-butenyl group, 1-pentenyl group, 1-hexenyl group, 2-methyl-1-propenyl group, 2-methyl-2-propenyl group, 1-ethylethenyl group, or linear or branched alkenyl group having 2 to 20 carbon atoms formed by the bonding of multiple such alkenyl groups. In general formula (1), the "cycloalkyl group having 3 to 12 carbon atoms that may have substituents" represented by R1 to R20 can specifically include cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, cyclodecyl group, cyclododecyl group, 4-methylcyclohexyl group, 4-ethylcyclohexyl group, and the like. In general formula (1), the "linear or branched alkoxy groups having 1 to 20 carbon atoms, which may have substituents" represented by R1 to R20 , specifically include methoxy, ethoxy, propoxy, n-butoxy, n-pentyloxy, n-hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, isopropoxy, isobutoxy, s-butoxy, t-butoxy, isooctyloxy, t-octyloxy, phenoxy, tolyloxy, biphenylyloxy, terphenylyloxy, naphthyloxy, anthryloxy, phenanthryloxy, fluorenyloxy, and indenyloxy groups. In general formula (1), the "linear or branched cycloal