Dihydroquinoline photochromic compounds
The present invention relates to a photochromic compound having a core fused ring structure represented by at least one of the following Formula (Ia) or Formula (IIa), (Ia) (IIa) Independently for each of Formula (Ia) and Formula (IIa): R 1 is in each case independently selected from substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, —SO 2 R 5 , or —C(O)—XR 5 , where, X is selected from a single bond, —N(R 5 )—, or —O—, and R 5 in each case is independently selected from hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl; and B and B′ are each independently selected from substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl. The present invention also relates to photochromic compositions and articles including such photochromic compounds.
1. A photochromic compound having a core fused ring structure represented by at least one of the following Formula (Ia) or Formula (IIa),
wherein independently for Formula (Ia) and Formula (IIa),
R 1 is in each case independently selected from substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, —SO 2 R 5 , or —C(O)—XR 5 , wherein,
X is selected from a single bond, —N(R 5 )—, or —O—, and
R 5 in each case is independently selected from hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, and
B and B′ are each independently selected from substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.
2. The photochromic compound of claim 1 , wherein the photochromic compound is represented by at least one of the following Formula (Ib) or Formula (IIb),
wherein independently for Formula (Ib) and Formula (IIb),
m in each case is independently 0 to 2,
n in each case is independently 0 to 4,
R 2 independently for each m, and R 3 independently for each n, are each independently selected from the group consisting of:
hydroxyl;
cyano;
(meth)acrylate;
amino or nitrogen-containing heterocycle;
a halo group;
a perhalogenated group;
substituted or unsubstituted alkyl;
substituted or unsubstituted alkenyl;
substituted or unsubstituted alkynyl;
substituted or unsubstituted heterocycloalkyl;
substituted or unsubstituted aryl;
substituted or unsubstituted heteroaryl;
boronic acid or boronic acid ester;
substituted or unsubstituted alkoxy or substituted or unsubstituted aryloxy;
substituted or unsubstituted alkylthio or substituted or unsubstituted arylthio;
ketone, aldehyde, carboxylic acid ester, carboxylic acid, carboxylate, or amide;
carbonate, carbamate, or urea;
polyether, polyester, polycarbonate, or polyurethane; and
siloxy, alkoxysilane, or polysiloxane; or
two adjacent R 2 groups at position-5 and position-6 together form a substituted or unsubstituted fused benzene ring, or a substituted or unsubstituted fused indeno ring.
3. The photochromic compound of claim 1 , wherein
independently for R 1 , each aryl substituent, and each heteroaryl substituent,
independently for R 5 , each alkyl substituent, each aryl substituent, and each heteroaryl substituent, and
independently for R 2 and R 3 , each alkyl substituent, each alkenyl substituent, each alkynyl substituent, each aryl substituent, each heterocycloalkyl substituent, each heteroaryl substituent, each alkoxy substituent, each aryloxy substituent, each alkylthio substituent, each arylthio substituent, each fused benzene ring substituent, and each fused indeno ring substituent,
is in each case independently selected from halo, cyano, nitro, alkyl, alkenyl, alkynyl, haloalkyl, perhaloalkyl, heterocycloalkyl, aryl, heteroaryl, hydroxyl, thiol, alkyl ether, alkyl thioether, aryl ether, aryl thioether, ketone, aldehyde, carboxylic acid ester, carboxylic acid, carboxylate, siloxy, alkoxysilane, polysiloxane, amide, amino, nitrogen-containing heterocycle, carbamate, carbonate, urea, polyester group, polyether group, polycarbonate group, polyurethane group, an acrylate group, a methacrylate group, combinations thereof, or two or more thereof.
4. The photochromic compound of claim 2 , wherein B and B′ are each independently selected from substituted or unsubstituted phenyl.
5. The photochromic compound of claim 4 , wherein independently for B and B′, each phenyl substituent is independently selected from alkyl, halo, perhaloalkyl, hydroxyl, thiol, alkyl ether, phenyl ether, alkyl thioether, phenyl thioether, morpholino, thiomorpholino, piperidino, piperazino, N-alkylpiperazino, or N-phenylpiperizino.
6. The photochromic compound of claim 3 , wherein
R 1 is in each case independently selected from substituted or unsubstituted phenyl, and —C(O)—XR 5 , wherein
X is selected from a single bond, —N(R 5 )—, or —O—, and
R 5 in each case is independently selected from hydrogen or substituted or unsubstituted phenyl,
wherein each phenyl substituent of R 1 and R 5 is in each case independently selected from the group consisting of halo, cyano, nitro, alkyl, alkenyl, alkynyl, haloalkyl, perhaloalkyl, heterocycloalkyl, aryl, heteroaryl, hydroxyl, thiol, alkyl ether, alkyl thioether, aryl thioether, ketone, aldehyde, carboxylic acid ester, carboxylic acid, carboxylate, siloxy, alkoxysilane, polysiloxane, amide, amino, nitrogen-containing heterocycle, carbamate, carbonate, urea, polyester group, polyether group, polycarbonate group, polyurethane group, an acrylate group, a methacrylate group, combinations thereof, and two or more thereof.
7. The photochromic compound of claim 6 , wherein
each phenyl substituent of R 1 and R 5 is in each case independently selected from the group consisting of halo, alkyl, perhaloalkyl, and alkyl ether,
R 2 independently for each m, and R 3 independently for each n, are each independently selected from alkyl, perhaloalkyl, alkyl ether, unsubstituted phenyl, and phenyl substituted with at least one substituent selected from alkyl, perhaloalkyl, or alkyl ether, or
two adjacent R 2 groups at position-5 and position-6 together form a substituted or unsubstituted fused benzene ring, wherein each fused benzene ring substituent is independently selected from halo, alkyl, perhaloalkyl, or alkyl ether, and
B and B′ are each independently selected from substituted or unsubstituted phenyl, wherein each phenyl substituent of B and B′ is independently selected from halo, alkyl, perhaloalkyl, hydroxyl, alkyl ether, phenyl ether, morpholino, piperidino, piperazino, N-alkylpiperazino, or N-phenylpiperizino.
8. A photochromic composition comprising the photochromic compound of claim 1 .
9. A photochromic article comprising the photochromic compound of claim 1 , wherein the photochromic article is selected from the group consisting of ophthalmic articles, display articles, windows, mirrors, active liquid crystal cell articles, and passive liquid crystal cell articles.
10. The photochromic article of claim 9 , wherein the photochromic article is selected from ophthalmic articles, and the ophthalmic articles are selected from the group consisting of corrective lenses, non-corrective lenses, contact lenses, intra-ocular lenses, magnifying lenses, protective lenses, or visors.
11. The photochromic article of claim 9 , wherein the photochromic article is selected from display articles, and the display articles are selected from the group consisting of screens, monitors, or security elements.
12. The photochromic compound of claim 2 , wherein
independently for R 1 , each aryl substituent, and each heteroaryl substituent,
independently for R 5 , each alkyl substituent, each aryl substituent, and each heteroaryl substituent, and
independently for R 2 and R 3 , each alkyl substituent, each alkenyl substituent, each alkynyl substituent, each aryl substituent, each heterocycloalkyl substituent, each heteroaryl substituent, each alkoxy substituent, each aryloxy substituent, each alkylthio substituent, each arylthio substituent, each fused benzene ring substituent, and each fused indeno ring substituent,
is in each case independently selected from halo, cyano, nitro, alkyl, alkenyl, alkynyl, haloalkyl, perhaloalkyl, heterocycloalkyl, aryl, heteroaryl, hydroxyl, thiol, alkyl ether, alkyl thioether, aryl ether, aryl thioether, ketone, aldehyde, carboxylic acid ester, carboxylic acid, carboxylate, siloxy, alkoxysilane, polysiloxane, amide, amino, nitrogen-containing heterocycle, carbamate, carbonate, urea, polyester group, polyether group, polycarbonate group, polyurethane group, an acrylate group, a methacrylate group, combinations thereof, or two or more thereof.
13. The photochromic compound of claim 12 , wherein
R 1 is in each case independently selected from substituted or unsubstituted phenyl, and —C(O)—XR 5 , wherein
X is selected from a single bond, —N(R 5 )—, or —O—, and
R 5 in each case is independently selected from hydrogen or substituted or unsubstituted phenyl,
wherein each phenyl substituent of R 1 and R 5 is in each case independently selected from the group consisting of halo, cyano, nitro, alkyl, alkenyl, alkynyl, haloalkyl, perhaloalkyl, heterocycloalkyl, aryl, heteroaryl, hydroxyl, thiol, alkyl ether, alkyl thioether, aryl thioether, ketone, aldehyde, carboxylic acid ester, carboxylic acid, carboxylate, siloxy, alkoxysilane, polysiloxane, amide, amino, nitrogen-containing heterocycle, carbamate, carbonate, urea, polyester group, polyether group, polycarbonate group, polyurethane group, an acrylate group, a methacrylate group, combinations thereof, and two or more thereof.
14. The photochromic compound of claim 13 , wherein
each phenyl substituent of R 1 and R 5 is in each case independently selected from the group consisting of halo, alkyl, perhaloalkyl, and alkyl ether,
R 2 independently for each m, and R 3 independently for each n, are each independently selected from alkyl, perhaloalkyl, alkyl ether, unsubstituted phenyl, and phenyl substituted with at least one substituent selected from alkyl, perhaloalkyl, or alkyl ether, or
two adjacent R 2 groups at position-5 and position-6 together form a substituted or unsubstituted fused benzene ring, wherein each fused benzene ring substituent is independently selected from halo, alkyl, perhaloalkyl, or alkyl ether, and
B and B′ are each independently selected from substituted or unsubstituted phenyl, wherein each phenyl substituent of B and B′ is independently selected from halo, alkyl, perhaloalkyl, hydroxyl, alkyl ether, phenyl ether, morpholino, piperidino, piperazino, N-alkylpiperazino, or N-phenylpiperizino.