Photochromic thienochromene compounds

Patent metadata

Field	Value
Publication number	US-10501477-B2
Application number	US-201515556672-A
Country	US
Kind code	B2
Filing date	Mar 10, 2015
Priority date	Mar 10, 2015
Publication date	Dec 10, 2019
Grant date	Dec 10, 2019

Abstract

The present invention relates to photochromic compounds, such as thienochromene compounds represented by the following Formulas (1a) and/or (1b). The present invention also relates to photochromic compositions and articles containing one or more such photochromic thienochromene compounds.

First claim

What is claimed is:

1. A photochromic compound represented by at least one of the following Formulas (Ia) and (Ib),

wherein independently for each of Formulas (Ia) and (Ib),
R 3 , and R 4 are in each case independently selected from, hydrogen; hydrocarbyl;
substituted hydrocarbyl; interrupted hydrocarbyl; substituted interrupted hydrocarbyl, wherein each interrupted hydrocarbyl and each substituted interrupted hydrocarbyl, are in each case independently interrupted with at least one interrupting group selected from the group consisting of —O—, —S—, —C(O)—, —C(O)O—, —OC(O)O—, —B(R 11′ )—, —P(R 11′ )—, —P(O)(R 11′ )—, —S(O)—, —SO 2 —, —N═N—, —C(O)N(R 11′ )—, —OC(O)N(R 11′ )—, —N(R 11′ )C(O)N(R 11′ )—, —N(R 11′ )— where R 11 ′ in each case is independently selected from hydrogen, hydrocarbyl or substituted hydrocarbyl, —Si(OR 8 ′) w (R 8 ′) t —, where w and t are each independently selected from 0 to 2, provided that the sum of w and t is 2, and each R 8 ′ is independently selected from hydrogen, hydrocarbyl and substituted hydrocarbyl, and combinations of two or more interrupting groups thereof; halogen; cyano; and —N(R 11 ″)R 12 ′, wherein R 11 ″ and R 12 ′ are each independently selected from hydrogen, hydrocarbyl or substituted hydrocarbyl, or R 11 ″ and R 12 ′ together forma ring structure or a ring structure including at least one heteroatom; or
R 3 and R 4 together form a ring structure;
R 1 and R 2 together form a ring structure, and said ring structure is selected from the following Formulas (IIa), (IIb), (IIc), and (IId),

wherein each ring structure represented by Formulas (IIa), (IIb), (IIc), and (IId), is fused to said photochromic compound at carbons a and b,
n, independently for Formulas (IIa), (IIb), (IIc), and (IId), is 1 to 4,
p, independently for Formulas (IIb) and (IIc), is 1 or 2,
R 5 independently for each n, and independently for Formulas (IIa), (IIb), (IIc), and (IId), and
R 6 independently for each p, and independently for Formulas (IIb) and (IIc), are in each case independently selected from, hydrogen; hydrocarbyl; substituted hydrocarbyl; interrupted hydrocarbyl; substituted interrupted hydrocarbyl, wherein each interrupted hydrocarbyl and each substituted interrupted hydrocarbyl, are in each case independently interrupted with at least one interrupting group selected from the group consisting of —O—, —S—, —C(O)—, —C(O)O—, —OC(O)O—, —B(R 11′ )—, —P(R 11′ )—, —P(O)(R 11′ )—, —S(O)—, —SO 2 —, —N═N—, —C(O)N(R 11 ′)—, —OC(O)N(R 11 ′)—, —N(R 11 ′)C(O)N(R 11 ′)—, —N(R 11 ′)— where R 11 ′ in each case is independently selected from hydrogen, hydrocarbyl or substituted hydrocarbyl, —Si(OR 8 ′) w (R 8 ′) t —, where w and t are each independently selected from 0 to 2, provided that the sum of w and t is 2, and each R 8 ′ is independently selected from hydrogen, hydrocarbyl and substituted hydrocarbyl, and combinations of two or more interrupting groups thereof; halogen; cyano; and —N(R 11 ″)R 12 ′, wherein R 11 ″ and R 12 ′ are each independently selected from hydrogen, hydrocarbyl or substituted hydrocarbyl, or R 11 ″ and R 12 ′ together forma ring structure or a ring structure including at least one heteroatom; and
R 7 and R 8 independently for Formula (IId) are each independently selected from hydrogen; hydrocarbyl; substituted hydrocarbyl; interrupted hydrocarbyl; and substituted interrupted hydrocarbyl, wherein each interrupted hydrocarbyl and each substituted interrupted hydrocarbyl, are each independently interrupted with at least one interrupting group selected from the group consisting of —O—, —S—, —N(R 11 ′)—, where R 11 ′ is selected from hydrogen, hydrocarbyl or substituted hydrocarbyl, and combinations of two or more interrupting groups thereof; or R 7 and R 8 together forma ring structure; and
B and B′ are each independently selected from unsubstituted aryl, substituted aryl, unsubstituted heteroaryl, substituted heteroaryl, alkenyl, and alkynyl, or B and B′ taken together forma ring structure.

2. The photochromic compound of claim 1 , wherein
independently for Formulas (Ia) and (Ib), one of, R 3 is, R 4 is, R 5 is, R 6 is, B is substituted with, and B′ is substituted with,
in each case independently, a group L represented by the following Formula (III),
[S 1 ] c -[Q 1 -[S 2 ] d ] d′ -[Q 2 -[S 3 ] e ] e′ -[Q 3 -[S 4 ] f ] f′ —S 5 —P  Formula (III)

wherein:
(a) Q 1 , Q 2 , and Q 3 for each occurrence, are independently selected from a divalent group selected from unsubstituted aryl, substituted aryl, unsubstituted heteroaryl, substituted heteroaryl, unsubstituted cycloalkyl, substituted cycloalkyl, unsubstituted heterocycloalky, and substituted heterocycloalkyl;
wherein the aryl substituents, heteroaryl substituents, cycloalkyl substituents, and heterocycloalkyl substituents are each independently selected from P, liquid crystal mesogens, halogen, poly(C 1 -C 18 alkoxy), C 1 -C 18 alkoxycarbonyl, C 1 -C 18 alkylcarbonyl, C 1 -C 18 alkoxycarbonyloxy, aryloxycarbonyloxy, perfluoro(C 1 -C 18 )alkoxy, perfluoro(C 1 -C 18 )alkoxycarbonyl, perfluoro(C 1 -C 18 )alkylcarbonyl, perfluoro(C 1 -C 18 )alkylamino, di-(perfluoro(C 1 -C 18 )alkyl)amino, perfluoro(C 1 -C 18 )alkylthio, C 1 -C 18 alkylthio, C 1 -C 18 acetyl, C 3 -C 10 cycloalkyl, C 3 -C 10 cycloalkoxy, straight-chain C 1 -C 18 alkyl, and branched C 1 -C 18 alkyl;
wherein said straight-chain C 1 -C 18 alkyl and branched C 1 -C 18 alkyl are mono-substituted with a group selected from cyano, halogen, and C 1 -C 18 alkoxy; or
wherein said straight-chain C 1 -C 18 alkyl and branched C 1 -C 18 alkyl are poly-substituted with at least two groups independently selected from halogen, -M(T) (v-1) and -M(OT) (v-1) , wherein M is chosen from aluminum, antimony, tantalum, titanium, zirconium and silicon, T is chosen from organofunctional radicals, organofunctional hydrocarbon radicals, aliphatic hydrocarbon radicals and aromatic hydrocarbon radicals, and v is the valence of M;
(b) c, d, e, and f are each independently chosen from an integer of 1 to 20; and each S 1 , S 2 , S 3 , S 4 , and S 5 is independently chosen for each occurrence from a spacer unit selected from:
(i) alkylene, substituted alkylene, haloalkylene, substituted haloalkylene, —Si(CH 2 ) g —, and —(Si[(CH 3 ) 2 ]O) h —, wherein g for each occurrence is independently chosen from an integer from 1 to 20; h for each occurrence is independently chosen from an integer from 1 to 16; and said substitutes for the alkylene and haloalkylene are independently selected from C 1 -C 18 alkyl, C 3 -C 10 cycloalkyl and aryl;
(ii) —N(Z)—, —C(Z)═C(Z)—, —C(Z)═N—, —C(Z′) 2 —C(Z′) 2 —, and a single bond, wherein Z for each occurrence is independently selected from hydrogen, C 1 -C 18 alkyl, C 3 -C 10 cycloalkyl and aryl, and Z′ for each occurrence is independently selected from C 1 -C 18 alkyl, C 3 -C 10 cycloalkyl and aryl; and
(iii) —O—, —C(═O)—, —C≡C—, —N═N—, —S—, —S(═O)—, —(O═)S(═O)—, —(O═)S(═O)O—, —O(O═)S(═O)O— and straight-chain or branched C 1 -C 24 alkylene residue, said C 1 -C 24 alkylene residue being unsubstituted, mono-substituted by cyano or halogen, or poly-substituted by halogen,
provided that when two spacer units comprising heteroatoms are linked together the spacer units are linked so that heteroatoms are not directly linked to each other, and the bond between S 5 and P is free of two heteroatoms linked to each other;

(c) P for each occurrence is independently selected from hydroxy, amino, C 2 -C 18 alkenyl, C 2 -C 18 alkynyl, azido, silyl, siloxy, silylhydr

Assignees

• Transitions Optical Inc

Inventors

• Deng Jun
• Stepp Brian R
• Spitler Eric
• Xiao Wenjing
• Tomasulo Massimiliano
• Walters Robert W

Classifications

• C07D493/14

  Ortho-condensed systems · CPC title

• G02B5/23

  Photochromic filters · CPC title

• C07D495/14 Primary

  Ortho-condensed systems · CPC title

• C09K9/02

  Organic tenebrescent materials · CPC title

• G03C1/73

  containing organic compounds · CPC title