Additives for dye-sensitized solar cells

Patent metadata

Field	Value
Publication number	US-9287052-B2
Application number	US-201313901821-A
Country	US
Kind code	B2
Filing date	May 24, 2013
Priority date	Dec 8, 2010
Publication date	Mar 15, 2016
Grant date	Mar 15, 2016

Abstract

The present invention relates to the use of at least one tertiary amine-N-oxide of formula I as additive in dye-sensitized solar cells and to special electrolyte formulations and a dye-sensitized solar cell comprising at least one compound of formula I.

First claim

The invention claimed is:

1. A dye-sensitized solar cell comprising at least one compound of formula I

wherein
R 1 , R 2 , R 3 are independently selected at each occurrence from:
straight-chain or branched alkyl with 1 to 20 C atoms, which can be substituted by at least one R; or
aryl with 6 to 10 C atoms, which can be substituted by at least one R,
or
R 1 , R 2 and R 3 are fused to form a heteroaromatic ring structure in which 1, 2 or 3 N atoms or 1N atom and 1 S or 1 O atom are present which ring can be substituted by at least one R,
or
R 1 and R 2 are fused to form a heteroaliphatic ring structure in which 1, 2 or 3 N atoms or 1N atom and 1 S or 1 O atom are present which ring can be substituted by at least one R and R 3 is straight-chain or branched alkyl with 1 to 20 C atoms or fused to form a tricyclic structure containing at least 1 N atom and in which a second or third N atom of the heteroaliphatic ring structure or tricyclic ring structure may be substituted by —O − and a straight-chain or branched alkyl with 1 to 20 C-atoms;
wherein a straight-chain or branched alkyl group having 1 to 20 C atoms is upon each occurrence independently selected from the group consisting of methyl, ethyl, propyl, isopropyl, n-butyl, sec.-butyl, tert.-butyl, 1-(2,2-dimethyl)-propyl, pentyl, hexyl, heptyl, octyl, x-methylbutyl with x being 1; 2 or 3 x-methylpentyl with x being 1; 2; 3 or 4 x-methylhexyl with x being 1; 2; 3; 4 or 5, x-ethylpentyl with x being 1, 2 or 3 x-ethylhexyl with x being 1; 2; 3 or 4 n-nonyl, n-decyl, n-undecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl and n-eicosyl, which can be substituted by at least one R; and
R is independently: Hal; CN; C(O)H; straight-chain or branched alkyl with 1 to 20 C atoms, which alkyl can be substituted by cycloalkyl having 5 to 6 C atoms or aryl having 6 to 10 C atoms in which the aryl group may be substituted by straight-chain or branched alkyl groups or alkoxy groups with 1 to 4 C atoms or by heteroaryl having 5 or 6 C atoms; straight-chain or branched alkenyl with 2 to 20 C atoms, which alkenyl can be substituted by aryl having 6 to 10 C atoms in which the aryl group may be substituted by straight-chain or branched alkyl groups with 1 to 4 C atoms; cycloalkyl having 5 or 6 C atoms; straight-chain or branched hydroxyalkyl with 1 to 20 C atoms; straight-chain or branched alkoxy with 1 to 20 C atoms, which alkoxy can be substituted by aryl having 6 to 10 C atoms; straight-chain or branched alkylthio with 1 to 20 C atoms; aryl with 6 to 10 C atoms in which the aryl group may be substituted by straight-chain or branched alkyl groups or alkoxy groups with 1 to 4 C atoms or by heteroaryl having 5 or 6 C atoms; heteroaryl with 5 to 10 C atoms in which a N atom of the heteroaryl group may be substituted by —O − ; aryloxy with 6 to 10 C atoms; arylthio with 6 to 10 C atoms; straight-chain or branched alkylamino; or dialkylamino with 1 to 20 C atoms; and
Hal is F, Cl, Br or I;
including all tautomeric or stereoisomeric forms thereof.

2. The dye-sensitized solar cell of claim 1 , wherein: R 1 , R 2 and R 3 are fused to form a heteroaromatic ring structure in which 1, 2 or 3 N atoms, or 1N and 1 S or 1 O atom are present, which heteroaromatic ring can be substituted by at least one R; or wherein R 1 and R 2 are fused to form a heteroaliphatic ring structure in which 1, 2 or 3 N atoms, or 1N atom and 1 S or 1 O atom are present, which heteroaliphatic ring can be substituted by at least one R; and R 3 is straight-chain or branched alkyl with 1 to 20 C atoms.

3. The dye-sensitized solar cell of claim 1 , wherein:
a) the at least one compound of formula I is further defined as any compound of formula IIa to IIg

wherein
R′ is independently at each occurrence H or R;
R′″ is independently selected at each occurrence from H, straight-chain or branched alkyl or alkoxy with 1 to 4 C atoms, or heteroaryl having 5 or 6 C atoms;
R* is independently selected at each occurrence from H, straight-chain or branched alkyl having 1 to 4 C atoms; and
R x is independently selected at each occurrence from H, straight-chain or branched alkyl with 1 to 20 C atoms, which can be substituted by cycloalkyl having 5 to 6 C atoms or aryl having 6 to 10 C atoms in which the aryl group may be substituted by straight-chain or branched alkyl groups or alkoxy groups with 1 to 4 C atoms or by heteroaryl having 5 or 6 C atoms; or

b) the at least one compound of formula I is further defined as any compound of formula IIa to IId

wherein
X is CH 2 , O or NR;
Y is CH, N, N + R, or N + —O − ;
R″ is straight-chain or branched alkyl with 1 to 20 C atoms; and
R′ is H or R.

4. The dye-sensitized solar cell of claim 3 , wherein for the compound of Formula Ha R′ is located in position-4 of the pyridine ring and is H or R, wherein R is selected from the group consisting of: C(O)H; straight-chain or branched alkyl with 1 to 20 C atoms, which can be substituted by aryl having 6 to 10 C atoms in which the aryl group may be substituted by straight-chain or branched alkyl groups or alkoxy groups with 1 to 4 C atoms; straight-chain or branched hydroxyalkyl with 1 to 20 C atoms; straight-chain or branched alkoxy with 1 to 20 C atoms, which can be substituted by aryl having 6 to 10 C atoms; aryl with 6 to 10 C atoms; or straight-chain or branched alkylamino or dialkylamino with 1 to 20 C atoms. R within formula IIa is preferably: straight-chain or branched alkyl with 1 to 9 C atoms, which can be substituted by phenyl; straight-chain or branched hydroxyalkyl with 1 to 4 C atoms; straight-chain or branched alkoxy with 1 to 4 C atoms, which can be substituted by phenyl; phenyl; and straight-chain or branched dialkylamino with 1 to 4 C atoms.

5. The dye-sensitized solar cell of claim 3 , wherein for the compound of Formula IIb R′ can be located in the 4, 5, 6 or 7 position of the quinoline ring and R′ is H or R, wherein R is selected from the group consisting of: straight-chain or branched alkyl with 1 to 20 C atoms, which can be substituted by aryl having 6 to 10 C atoms in which the aryl group may be substituted by straight-chain or branched alkyl groups or alkoxy groups with 1 to 4 C atoms; straight-chain or branched hydroxyalkyl with 1 to 20 C atoms; straight-chain or branched alkoxy with 1 to 20 C atoms, which can be substituted by aryl having 6 to 10 C atoms; aryl with 6 to 10 C atoms; and straight-chain or branched alkylamino or dialkylamino with 1 to 20 C atoms.

6. The dye-sensitized solar cell of claim 3 , wherein for the compound of Formula IIc R′ is H, and R x is independently selected at each occurrence from H, straight-chain or branched alkyl with 1 to 20 C atoms, which can be substituted by cycloalkyl having 5 to 6 C atoms or aryl having 6 to 10 C atoms in which the aryl group may be substituted by straight-chain or branched alkyl groups or alkoxy groups with 1 to 4 C atoms or by heteroaryl having 5 or 6 C atoms.

7. The dye-sensitized solar cell of claim 3 , wherein for the compound of Formula IId R′ is H or R, wherein R is selected from the group consisting of: straight-chain or branched alkyl with 1 to 20 C atoms, which can be substituted by aryl having 6 to 10 C at

Assignees

• Merck Patent Gmbh

Inventors

• Yoshizaki Hiroki
• Kawata Kentaro
• Goto Tomohisa
• Shinohara Hiromi
• Kirsch Peter

Classifications

• H01G9/2031 Primary

  comprising titanium oxide, e.g. TiO2 (H01G9/2036 takes precedence) · CPC title

• Y02E10/542

  Dye sensitized solar cells · CPC title

• H01G9/2013

  the electrolyte comprising ionic liquids, e.g. alkyl imidazolium iodide · CPC title

• H01G9/038 Primary

  Electricity · mapped topic

• H01G9/2059

  comprising an organic dye as the active light absorbing material, e.g. adsorbed on an electrode or dissolved in solution · CPC title