# US 8,147,725 B2 · Photochromic materials having extended pi-conjugated systems and compositions and articles including the same

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- Number: US 8,147,725 B2
- Document ID: US8147725B2
- Status: Granted
- Kind: B2
- Application number: 12/873,735
- Filed: 2010-09-01
- Published: 2011-02-24
- Granted: 2012-04-03
- Earliest claimed: 2005-04-08
- Assignees: Transitions Optical, Inc.
- Inventors: Anu Chopra; Jun Deng; Beon-Kyu Kim; David B. Knowles; Frank Molock; Victor A. Montes; Stephen D. Straight; Wenjing Xiao; Huayun Yu
- Web page: https://patentgrep.com/patent/US8147725B2

## CPC

- C07D 311/78: Ring systems having three or more relevant rings
- C07D 405/04: directly linked by a ring-member-to-ring-member bond
- C07D 407/12: linked by a chain containing hetero atoms as chain links
- C07D 409/04: directly linked by a ring-member-to-ring-member bond
- C07D 493/04: Ortho-condensed systems
- C07D 495/04: Ortho-condensed systems
- C09K 9/02: Organic tenebrescent materials
- G03C 1/73: containing organic compounds
- C09K 2211/1007: Non-condensed systems
- C09K 2211/1011: Condensed systems
- C09K 2211/1022: bridged by heteroatoms, e.g. N, P, Si or B
- C09K 2211/1059: containing three nitrogen atoms as heteroatoms
- C09K 2211/1088: containing oxygen as the only heteroatom
- C09K 2211/1096: containing other heteroatoms
- G03C 1/685: Compositions containing spiro-condensed pyran compounds or derivatives thereof, as photosensitive substances
- Y10T 428/31504: Composite [nonstructural laminate]
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- G03C: PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES (for photomechanical purposes G03F); PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY (photographic processes characterised by the use or manipulation of apparatus classifiable per se in subclass G03B, see G03B; photomechanical production of textured or patterned surfaces G03F; electrophotography, magnetography G03G)
- Y10T: TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION

## Abstract

The present invention provides a photochromic material which is an indeno-fused naphthopyran having a pi-conjugation extending group bonded to the 11-position of the indeno-fused naphthopyran, the pi-conjugation extending group having at least one pendent halo-substituted group bonded thereto. The pi-conjugation extending group extends the pi-conjugation system of said indeno-fused naphthopyran. The 13-position of the indeno-fused naphthopyran is substantially free of spiro-substituents. The invention further provides photochromic materials of specified structure, photochromic compositions, photochromic articles and optical elements that include the photochromic material.

## Claims

### Claim 1

A photochromic material comprising an indeno-fused naphthopyran having the following general structural formula (I) or (II):
the photochromic material having a pi-conjugation extending group bonded to the 11-position of said indeno-fused naphthopyran, said pi-conjugation extending group having at least one pendent halo-substituted group bonded thereto, said pi-conjugation extending group extending the pi-conjugation system of said indeno-fused naphthopyran, wherein the 13-position of said indeno-fused naphthopyran is substantially free of spiro-substituents.

### Claim 2 (depends on 1)

The photochromic material of claim 1 wherein said pi-conjugation extending group is a group represented by —C(R30)═C(R31)(R32) or —C≡C—R33, wherein R30, R31 and R32 are each independently, amino, dialkyl amino, diaryl amino, acyloxy, acylamino, a substituted or unsubstituted C1-C20 alkyl, a substituted or unsubstituted C2-C20 alkenyl, a substituted or unsubstituted C2-C20 alkynyl, halogen, hydrogen, hydroxy, oxygen, a polyol residue, a substituted or unsubstituted phenoxy, a substituted or unsubstituted benzyloxy, a substituted or unsubstituted alkoxy, a substituted or unsubstituted oxyalkoxy, alkylamino, mercapto, alkylthio, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted heterocyclic group, provided that at least one of R30, R31 and R32 is said pendent halo-substituted group, and R33 is said pendent halo-substituted group.

### Claim 3 (depends on 1)

The photochromic material of claim 1 wherein said pi-conjugation extending group is selected from:
a substituted or unsubstituted aryl; and
a substituted or unsubstituted heteroaryl.

### Claim 4 (depends on 3)

The photochromic material of claim 3 wherein said pi-conjugation extending group bonded to the 11-position of said indeno-fused naphthopyran is selected from substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl,
wherein said substituted aryl and said substituted heteroaryl are in each case independently substituted with at least one member selected from substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted oxyalkoxy, amide, substituted or unsubstituted amino, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, azide, carbonyl, carboxy, ester, ether, halogen, hydroxy, polyol residue, substituted or unsubstituted phenoxy, substituted or unsubstituted benzyloxy, cyano, nitro, sulfonyl, thiol, and substituted or unsubstituted heterocyclic group, provided that if the aryl group or the heteroaryl group comprises more than one substituent, each substituent may be independently chosen.

### Claim 5 (depends on 1)

The photochromic material of claim 1 wherein said pendent halo-substituted group of said pi-conjugation extending group is selected from halo-substituted(C1-C10)alkyl, halo-substituted(C2-C10)alkenyl, halo-substituted(C2-C10)alkynyl, halo-substituted(C1-C10)alkoxy and halo-substituted(C3-C10)cycloalkyl, and wherein each halo group of each pendent halo-substituted group being independently selected from fluorine, chlorine, bromine and iodine.

### Claim 6 (depends on 1)

The photochromic material of claim 1 wherein said photochromic material displays hyperchromic absorption of electromagnetic radiation having a wavelength from 320 nm to 420 nm as compared to a comparative photochromic material comprising a comparable indeno-fused naphthopyran that is substantially free of said pi-conjugation extending group bonded to the 11-position of said comparable indeno-fused naphthopyran.

### Claim 7 (depends on 1)

A photochromic article comprising a substrate and a photochromic material according to claim 1 connected to at least a portion of the substrate.

### Claim 8 (depends on 7)

The photochromic article of claim 7 wherein the photochromic article is an optical element, said optical element being at least one of an ophthalmic element, a display element, a window, a mirror and a liquid crystal cell element.

### Claim 9 (depends on 8)

The photochromic article of claim 8 wherein the optical element is an ophthalmic element, said ophthalmic element being at least one of a corrective lens, a non-corrective lens, a magnifying lens, a protective lens, a visor, goggles and a lens for an optical instrument.

### Claim 10 (depends on 7)

The photochromic article of claim 7 wherein the substrate comprises a polymeric material and the photochromic material is incorporated into at least a portion of the polymeric material.

### Claim 11 (depends on 10)

The photochromic article of claim 10 wherein the photochromic material is at least one of blended with at least a portion of the polymeric material, bonded to at least a portion of the polymeric material, and imbibed into at least a portion of the polymeric material.