Photochromic Indeno-Fused Naphthopyran Compounds, Compositions, and Articles Containing Same

Patent metadata

Field	Value
Publication number	US-2026070881-A1
Application number	US-202219106256-A
Country	US
Kind code	A1
Filing date	Aug 30, 2022
Priority date	Aug 30, 2022
Publication date	Mar 12, 2026
Grant date	—

Abstract

An indeno-fused naphthopyran having the core skeletal structure (I): (I) wherein R 1 is a substituted or unsubstituted alkyl group; R 2 is substituted or unsubstituted amino; substituted or unsubstituted alkyl; substituted or unsubstituted alkenyl; substituted or unsubstituted alkynyl; substituted or unsubstituted aryl; substituted or unsubstituted heteroaryl; substituted or unsubstituted alkoxy; substituted or unsubstituted aryloxy; substituted or unsubstituted alkylthio; substituted or unsubstituted aryl thio; or substituted or unsubstituted amide, urea, and carbamate; and at least one of R 3 and R 4 is an electron donating group, wherein the sum of the Hammett σ p values for R 3 and R 4 is less than −0.40, wherein when R 1 is a substituted alkyl group, a carbon atom of the alkyl group is directly bonded to the 7-position carbon atom, and the carbon atom of the alkyl group that is directly bonded to the 7-position carbon atom is unsubstituted.

First claim

1 . An indeno-fused naphthopyran having the following core skeletal structure (I):

wherein:
R 1 is a substituted or unsubstituted alkyl group;
R 2 is substituted or unsubstituted amino;
substituted or unsubstituted alkyl;
substituted or unsubstituted alkenyl;
substituted or unsubstituted alkynyl;
substituted or unsubstituted aryl;
substituted or unsubstituted heteroaryl;
substituted or unsubstituted alkoxy;
substituted or unsubstituted aryloxy;
substituted or unsubstituted alkylthio;
substituted or unsubstituted arylthio;
substituted or unsubstituted amide;
substituted or unsubstituted urea; or
substituted or unsubstituted carbamate; and
at least one of R 3 and R 4 is an electron donating group, wherein the sum of the Hammett σ p values for R 3 and R 4 is less than −0.40,
wherein when R 1 is a substituted alkyl group, a carbon atom of the alkyl group is directly bonded to the 7-position carbon atom, and the carbon atom of the alkyl group that is directly bonded to the 7-position carbon atom is unsubstituted.

2 . The indeno-fused naphthopyran of claim 1 , wherein R 1 is a C 1 to C 20 substituted or unsubstituted alkyl group.

3 . The indeno-fused naphthopyran of claim 1 , wherein R 1 is an unsubstituted C 1 to C 6 alkyl group.

4 . The indeno-fused naphthopyran of claim 1 , wherein R 2 is selected from the group consisting of substituted or unsubstituted aryl, substituted or unsubstituted amino, substituted or unsubstituted alkyoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted alkylthio, and substituted or unsubstituted arylthiol.

5 . The indeno-fused naphthopyran of claim 1 , wherein R 2 is substituted or unsubstituted aryl.

6 . The indeno-fused naphthopyran of claim 1 , wherein at least one of R 3 and R 4 is a substituted or unsubstituted amino group.

7 . The indeno-fused naphthopyran of claim 1 , wherein at least one of R 3 and R 4 is a substituted or unsubstituted cyclic amino group.

8 . The indeno-fused naphthopyran of claim 7 , wherein at least one of R3 and R4 is a cyclic amino group which is a nitrogen-containing heterocycle selected from the group consisting of morpholino, piperidino, substituted piperazino, and pyrrolidino.

9 . The indeno-fused naphthopyran of claim 1 , wherein R 3 and R 4 are the same or different, and each is independently substituted or unsubstituted alkoxy or substituted or unsubstituted amino.

10 . The indeno-fused naphthopyran of claim 1 , wherein at least one of R 3 and R 4 is selected from the group consisting of methoxy, morpholino, piperazino, substituted piperazino, and dialkyl (C 1 to C 6 ) amino.

11 . The indeno-naphthopyran of claim 1 , having the following core skeletal structure (Ia);

wherein:
R 1 , R 2 , R 3 , and R 4 are each as described above with respect to core skeletal structure (I); and
R 5 and R 6 are each independently:
(i) hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted heterocycloalkyl, allyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl;
(ii) alkoxy, hydroxyl, alkylthio, ketone, aldehyde, ester, carboxylic acid, carboxylate, siloxane, alkoxysilane, or polysiloxane;
(iii) a group comprising polyester, polyether, polycarbonate, polyurethane or combinations thereof; or
(iv) R 5 and R 6 together form an aliphatic ring having 3 to 20 ring member carbon atoms, a condensed polycyclic ring having an aromatic ring or aromatic hetero ring condensed to the above aliphatic ring, a hetero ring having 3 to 20 ring member atoms, or a condensed polycyclic ring having an aromatic ring or aromatic hetero ring condensed to the above hetero ring, together with the 13-position carbon atom bonded thereto.

12 . The indeno-fused naphthopyran of claim 11 , wherein R 5 and R 6 are each independently substituted or unsubstituted alkyl.

13 . The indeno-fused naphthopyran of claim 11 , wherein
R 1 is unsubstituted C 1 to C 6 alkyl; R 2 is substituted or unsubstituted phenyl; R 3 and R 4 are each independently C 1 to C 4 alkoxy or a nitrogen-containing heterocycle; and R 5 and R 6 are each independently C 1 to C 4 alkyl.

14 . A photochromic composition comprising the indeno-fused naphthopyran of claim 1 .

15 . A photochromic article comprising the indeno-fused naphthopyran of claim 1 ,
wherein the photochromic article is selected from ophthalmic articles, display articles, windows, mirrors, active liquid crystal cell articles, or passive liquid crystal cell articles; or wherein the photochromic article is selected from ophthalmic articles, and the ophthalmic articles are selected from corrective lenses, non-corrective lenses, contact lenses, intra-ocular lenses, magnifying lenses, protective lenses, or visors; or wherein the photochromic article is selected from display articles, and the display articles are selected from screens, monitors, or security elements.

Assignees

• Transitions Optical Ltd

Inventors

• Xiao Wenjing
• Brown Patrick M
• Chiu Chien-Yang
• Walters Robert W

Classifications

• G02C7/102

  Photochromic filters · CPC title

• G02B5/23

  Photochromic filters · CPC title

• C09K2211/1018

  Heterocyclic compounds · CPC title

• C09K2211/1011

  Condensed systems · CPC title

• C09K2211/1007

  Non-condensed systems · CPC title