Patent ID: 6660727
Filing Date: 2003-12-09
Classification: C07D,C08K,C09K,G02B

Abstract:
A photochromic indenochromene compound corresponding to formula (I): whereinR1 and R2 represent radicals independently selected from the group A, consisting of hydrogen, fluorine, chlorine, bromine, hydroxy, (C1-C6)-alkyl, (C1-C6)-alkoxy, (C3-C7)-cycloalkyl which may include one or more heteroatoms, (C1-C6)-acyl, unsubstituted or monosubstituted phenyl, and unsubstituted or monosubstituted benzyl, wherein the phenyl or benzyl substituents are selected from the group consisting of (C1-C6)-alkyl and (C1-C6)-alkoxy; or R1 and R2 together represent an annellated, unsubstituted, monosubstituted or disubstituted benzo or pyrido ring wherein the ring substituents are selected from group A; R3 represents a substituent selected from the group consisting of hydrogen, (C1-C6)-alkyl, and â€”OM, wherein M is a substituent selected from group A; R4 is a substituent selected from the group consisting of hydrogen, hydroxy, (C1-C6)-alkyl, (C1-C6)-alkoxy, (C3-C7)-cycloalkyl, (C1-C6)-acyl; unsubstituted, monosubstituted, disubstituted or trisubstituted phenyl, benzyl, naphthyl, phenanthryl, pyrenyl, quinolyl, isoquinolyl, benzofuranyl, thienyl, benzothienyl, dibenzofuranyl, dibenzothienyl, carbazolyl and indolyl, wherein the substituents are selected from group A; (C1-C6)-4-phenylalkyl and (C1-C6)-4-phenoxyalkyl, wherein the phenyl ring in 4-position in turn may be part of an additional photochromic pyran system; or R3 and R4 together with the spiro carbon atom represent a saturated and/or unsaturated ring with 5 to 8 carbon atoms, of which at most one may be substituted by a heteroatom selected from the group consisting of O, S and NR5, wherein R5 is selected from group A, and wherein at least one aromatic or heteroaromatic ring system selected from group E consisting of benzene, naphthalene, phenanthrene, pyridine, quinoline, furan, thiophene, pyrrole, benzofuran, benzothiophene, indole and carbazole, is annellated to the ring, wherein said ring system may have one or more substituents selected from group A; the annellated ring (Het) represents a 5 or 6-member heteroaromatic ring corresponding to one of the following formulas: â€ƒwherein Y is selected from the group consisting of oxygen, sulfur and NR5, and Z, U, V and W are each independently selected from the group consisting of nitrogen and CR6, wherein R6 and R7 represent substituents independently selected from group A, or R6 and R7 if they are ortho to one another together represent an unsubstituted or monosubstituted benzene ring wherein the ring substituents are independently selected from group A; and B and Bâ€² are each independently selected from the following groups a), b), c) or d); wherein group a) consists of monosubstituted, disubstituted and trisubstituted aryl selected from the group consisting of phenyl and naphthyl; group b) consists of unsubstituted, monosubstituted and disubstituted heteroaryl selected from the group consisting of pyridyl, furanyl, benzofuran-2-yl, benzofuran-3-yl, thien-2-yl, thien-3-yl, benzothien-2-yl, benzothien-3-yl, phenazinyl, phenoxazinyl, phenothiazinyl and julolidinyl; wherein the substituents of the aryl or heteroaryl in groups a) and b) are selected from the group consisting of the above-defined group A, amino, mono-(C1-C6)-alkylamino, di-(C1-C6)-alkylamino, monophenylamino and diphenylamino unsubstituted, monosubstituted or disubstituted on the phenyl rings, wherein the phenyl ring substituents in turn are selected from group A, pyrrolidinyl, piperidinyl, morpholinyl, thiomorpholinyl, phenazinyl, phenoxazinyl, phenothiazinyl, carbazolyl, unsubstituted, monosubstituted and disubstituted pyrryl, wherein the pyrryl substituents are selected from group A, group c) consists of structural units with the following structural formulas (B) and (C): â€ƒwherein D and E are independently selected from the group consisting of oxygen, sulfur, carbon or NR8; R8, R9, R10 and R11 are each independently selected from the group A; and n is 1, 2, or 3; provided that if D represents NR8 in formula (B), E represents carbon, or d) B and Bâ€² together form an unsubstituted, monosubstituted or disubstituted fluorene-9-ylidene group or a saturated hydrocarbon group, which is C3-C12 spiro monocyclic, C7-C12 spiro bicyclic or C7-C12 spiro tricyclic, wherein the fluorene substituents are selected from group A.