Electrochromic material and a method for producing the same
An electrochromic material containing a π-electron based conjugated polymer that changes from a desired color developed state to a decolored state, and a method for producing the electrochromic material, are provided. The electrochromic material contains aπ-electron based conjugated polymer as shown in chemical formula (1). In formula (1), each X is any one selected from —S—, —O—, —Se— and —Te—; each Y is any one selected from a hydrogen atom and an organic group having 1 to 20 carbon atoms; W is an arylene group or divalent heteroaromatic ring group; and n is a number of 2 to 1,000. Repetition of this structure forms a structure of random copolymers, graft copolymers, block copolymers and/or dendrimers.
1. An electrochromic material comprising aπ-electron based conjugated polymer represented by formula (1) shown below:
where in the formula (1):
each X is respectively any one selected from —S—, —O—, —Se— and —Te—;
each Y is respectively any one selected from a hydrogen atom and an organic group having 1 to 20 carbon atoms;
W is an arylene group or divalent heteroaromatic ring group; n is a number of 2 to 1,000; and
repetition of this structure forms a structure of a random copolymer, a graft copolymer, a block copolymer and/or a dendrimer.
2. A method for producing the electrochromic material according to claim 1 , comprising:
halogenating a compound represented by formula (2) shown below to obtain a compound represented by formula (3) shown below, and cross-coupling the compound represented by the formula (3) with a compound represented by formula (4) shown below to prepare a monomer ingredient represented by formula (7) shown below; or
reacting the compound represented by the formula (2), in the presence of a base, with one kind selected from MgCl 2 , MgBr 2 , MgI 2 , ZnCl 2 , ZnBr 2 , ZnI 2 , Sn(R 2 ) 3 Cl, Sn(R 2 ) 3 Br, Sn(R 2 ) 3 I (each R 2 is independently an alkyl group or alkoxy group having 1 to 20 carbon atoms), a boron acid, and a boronate ester to obtain a compound represented by formula (5) shown below, and cross-coupling the compound represented by the formula (5) with a compound represented by formula (6) shown below to prepare the monomer ingredient represented by the formula (7); and
carrying out a polymerization of the monomer ingredient to produce a π-electron based conjugated polymer and then to produce an electrochromic material containing the polymer according to claim 1 ,
where in the formula (2),
X is any one selected from —S—, —O—, —Se— and —Te—, and
Y is any one selected from a hydrogen atom and an organic group having 1 to 20 carbon atoms,
where in the formula (3),
X and Y are the same as described above, and
Q 1 is a halogen atom,
Q 2 -W-Q 2 (4)
where in the formula (4),
W is an arylene group or a divalent heteroaromatic ring group, and
Q 2 is one kind selected from a boron acid group, a boronate ester group, —MgCl, —MgBr, —MgI, —ZnCl, —ZnBr, —ZnI, and —Sn(R 1 ) 3 , where each R 1 is independently a alkyl group or alkoxy group having 1 to 20 carbon atoms,
where in the formula (5),
X and Y are the same as described above, and
Q 3 is one kind selected from a boron acid group, a boronate ester group, —MgCl, —MgBr, —MgI, ZnCl, ZnBr, ZnI, Sn(R 1 ) 3 , where each R 1 is independently an alkyl group and alkoxy group having 1 to 20 carbon atoms,
Q 4 -W-Q 4 (6)
where in the formula (6),
W is the same as described before, and
each Q 4 is independently a halogen atom,
where in the formula (7),
each X is respectively any one selected from —S—, —O—, —Se— and —Te—,
each Y is respectively any one selected from a hydrogen atom and an organic group having 1 to 20 carbon atoms, and
W is an arylene group or a divalent hetero aromatic ring group.
3. The method for producing the electrochromic material according to claim 2 , wherein:
the polymerization is carried out using a chemical polymerization of the monomer ingredient in the presence of or under a contact with a polyanion and an oxidant to produce the π-electron based conjugated polymer; or
the polymerization is carried out using an electrolytic polymerization by supplying an electric current to a mixture containing the monomer ingredient and an electrolyte to produce the electron based conjugated polymer.