Electrochromic compounds, compositions, and devices containing the same

Abstract

This specification discloses a group of electrochromic compounds of formula (I) comprising a thiophene ring, a selenofene ring, or a furan ring, as well as electrochromic compositions and devices comprising at least one of the electrochromic compounds of formula (I).

Claims

1. Electrochromic compounds represented by formula (I): 【Chemistry 1】 (In the formula, (i) A １ and A ２ Both are H; n is 1, 2, or 3; M １ and M ２ These are H, 2,6-C, and C, respectively, independently. １～１２ Alkoxyphenyls, Ma, Mb, and Mc: 【Chemistry 2】 Selected from the group consisting of M １ and M ２ At least one of them is selected from the group consisting of Ma, Mb, and Mc, or (ii) n is 1; A ２ is H; A １ and M ２ together form a heterocyclic group fused to the central 5-member heterocyclic ring to which they are attached, and the formed heterocyclic group is Group Ia: 【Transformation 3】 It is the basis of; M １ H, 2,6-diC １～１２ Selected from the group consisting of alkoxyphenyls, Ma, Mb, and Mc; or (iii) n is 1; A １ H is M ２ H, 2,6-diC １～１２ Selected from the group consisting of alkoxyphenyls, Ma, Mb, and Mc; A ２ and M １ Together, they form a heterocyclic group fused to the central five-membered heteroaromatic ring to which they are bonded, and the heterocyclic group is Ib, Ic, and Id: 【Chemistry 4】 Selected from the group consisting of; A ３ H is M ３ H, 2,6-diC １～１２ Selected from the group consisting of alkoxyphenyls, Ma, Mb, and Mc, M ２ and M ３ At least one of these is selected from the group consisting of Ma, Mb, and Mc; During the ceremony, 【Transformation 5】 It is either a single bond or a double bond; Each X is an atom independently selected from the group consisting of S, Se, and O; Each Y is O, S, -NR ８ N-C(O)R ８ , and N-S(O) ２ R ８ Atom independently selected from the group consisting of; B may or may not exist, and if it exists, it may be CH or CH ２ And; D is CR １０ , CH, or (CH ２ ) ｍ And m is 1, 2, or 3; R １ R either exists or does not exist. １ If there exists, each R １ H and C are independent of each other. ３～１２ Cycloalkyl, linear C １～１２ Alkyl and branched C ３～１２ Selected from the group consisting of alkyl groups; each R ２ H and C are independent of each other. ３～１２ Cycloalkyl, linear C １～１２ Alkyl and branched C ３～１２ Selected from the group consisting of alkyl groups, or R １ and R ２ Together with the carbon atoms to which they are bonded, C ４～１２ It forms a spirocycloalkyl group; R １ If it does not exist, D is CR １０ And R ２ and R １０ Together with the carbon atoms to which they are bonded, R １０ and R ２ A C condensed in the ring to which it is bonded ６～１０ It forms an aryl group; Each R ３ Independently, linear C １～１２ Alkyl, branched C ３～１２ Alkyl, C １～１２ Haloalkyl, C ３～１２ Cycloalkyl, -C(O)NR ８ R ９ Selected from the group consisting of , and a six-membered heteroaromatic ring containing at least one oxygen atom; each R ４ H and C are independent of each other. １～１２ Alkoxy, C １～１２ Alkyl and -NR ８ R ９ Selected from the group consisting of R ４ and OR ３ However, if they are substituents on two adjacent carbon atoms of the benzene ring to which they are bonded, then R ４ and OR ３ Together with the carbon atoms to which they are bonded, R ４ and OR ３ It forms a 5-7 member oxygen-containing ring condensed to a benzene ring to which it is bonded; the 5-7 member oxygen-containing ring has one or more C １～６ It may be optionally substituted with an alkyl group; Each R ５ H, C １～１２ Alkoxy, C １～１２ Alkyl and -NR ８ R ９ Selected from the group consisting of; R ６ and R ７ These are H and linear C, respectively, independently. １～１２ Alkyl, branched C ３～１２ Alkyl, C ６～１０ Ariel, C １～１２ Selected from the group consisting of alkoxys; and R ８ and R ９ These are H and linear C, respectively, independently. １～１２ Alkyl, branched C ３～１２ Alkyl and C ６～１０ (Selected from a group consisting of aryls).

2. A １ and A ２ are both H; n is 1, 2, or 3; M １ and M ２ are each independently H, 2,6-diC １～１２ alkoxyphenyl, Ma, Mb, and Mc: 【Transformation 6】 Selected from the group consisting of M １ and M ２ At least one of them is selected from the group consisting of Ma, Mb, and Mc. R １ 、R ２ 、R ３ 、R ４ 、 【Transformation 7】 The electrochromic compound according to claim 1, wherein Y, B, and D are each independently as described in claim 1.

3. A １ and A ２ are both H, and n is 1, the electrochromic compound according to claim 2.

4. The electrochromic compound according to any one of claims 1 to 3, wherein the compound is represented by formula (II): 【Transformation 8】 (where R) １ R ２ R ３ R ４ , 【Chemistry 9】 (Y, B, and D are each independently as described in claim 1).

5. M １ or M ２ One of them is 2,6-diC １～１２ The electrochromic compound according to claim 1, wherein the group is an alkoxyphenyl group.

6. n is 1; A ２ H is; A １ and M ２ However, together they form a heterocyclic group fused to the central five-membered heterocyclic ring to which they are bonded, and the formed heterocyclic group is group Ia: 【Chemistry 10】 It is the basis of; M １ However, H, 2, 6-C １～１２ Selected from the group consisting of alkoxyphenyls, Ma, Mb, and Mc; R １ , R ２ , R ３ , R ４ The electrochromic compound according to claim 1, wherein Y, Ma, Mb, and Mc are each independently as described in claim 1.

7. n is 1; A １ H is M ２ However, H, 2, 6-C １～１２ Selected from the group consisting of alkoxyphenyls, Ma, Mb, and Mc; A ２ and M １ However, together they form a heterocyclic group fused to the central five-membered heteroaromatic ring to which they are bonded, and the heterocyclic group is Ib, Ic, and Id: 【Chemistry 11】 Selected from the group consisting of A ３ H is M ３ However, H, 2, 6-C １～１２ Selected from the group consisting of alkoxyphenyls, Ma, Mb, and Mc, M ２ and M ３ At least one of them is selected from the group consisting of Ma, Mb, and Mc; R ６ , R ７ The electrochromic compound according to claim 1, wherein X, Ma, Mb, and Mc are each independently as described in claim 1.

8. An electrochromic compound according to any one of claims 1 to 7, wherein one or more of X are S.

9. The electrochromic compound according to any one of claims 1 to 8, wherein one or more of the Ys are O. 【Request Item 10】 【Chemistry 12】 It is a single bond, and both B and D are CH ２ The electrochromic compound according to any one of claims 1 to 9.

11. R １ and R ２ However, each operates independently, linear C １～６ Alkyl alkyl group or branched C ３～６ It is an alkyl group; R ３ However, independently, linear C １～６ Alkyl alkyl group, branched C ３～６ Alkyl alkyl group, or C １～６ (Per)fluoroalkyl group; R ４ , R ５ , R ６ , and R ７ The electrochromic compound according to any one of claims 1 to 10, wherein all atoms are H.

12. The electrochromic compound according to claim 1, wherein the compound is selected from the group consisting of the following: Table 1 Table 2 Table 3 Table 4

13. An electrochromic composition comprising at least one electrochromic compound according to any one of claims 1 to 12 and a host medium.

14. An electrochromic device comprising at least one electrochromic compound according to any one of claims 1 to 12 or the electrochromic composition according to claim 13, the electrochromic device being selected from optical articles, windows, visors, mirrors, head-mounted devices, variable transmittance devices, and displays.

15. The electrochromic device according to claim 14, wherein the optical article is an optical lens, preferably an ophthalmic lens, or an optical filter.

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