Photochromic Double-Fused Naphthopyrans

Photochromic naphthopyrans having the general formula (I) or (II):

• where the residues R1, R2, R3, R4 and R5 are each independently a substituent selected from the group α, consisting of a hydrogen atom, a (C1-C6)-alkyl residue, a (C1-C6)-thioalkyl residue, a (C3-C7)-cycloalkyl residue, which may have one or more heteroatoms selected from O or S, a (C1-C6)-alkoxy residue, a hydroxyl group, a trifluoromethyl group, bromine, chlorine, fluorine, an unsubstituted, monosubstituted or disubstituted phenyl, phenoxy, benzyl, benzyloxy, naphthyl or naphthoxy residue, in which the substituents may in turn be selected from the group α;
• or
• two residues R3 (if in a position ortho to one another) are an unsubstituted, monosubstituted or disubstituted fused benzo, pyrido, naphtho, benzofuro or benzothieno ring, of which the substituents may be selected from the group α;
• n is an integer from 1 to 4,
• X and Y are each independently selected from the group consisting of —O—, —S—, —N(C1-C6)alkyl, —NC6H5, —CH2, —C(CH3)2— and —C(C6H5)2—,
• the residues R6 and R7 in the —CR6R7 moiety are each independently a substituent selected from the group α, m is an integer from 1 to 4,
• or two or more adjacent —CR6R7 moieties are part of a fused benzene ring, which may be unsubstituted, monosubstituted or disubstituted, of which the substituents may be selected from the group α, or
• X and/or Y together with the respective adjacent —CR6R7 moiety are a fused benzene ring, which may be unsubstituted, monosubstituted or disubstituted, of which the substituents may be selected from the group α,
• and B and B′ are each independently selected from one of the following groups a) or b), where
• a) are mono-, di- and trisubstituted aryl residues, where the aryl residue is phenyl, naphthyl or phenanthryl;
• b) are unsubstituted, mono- and disubstituted heteroaryl residues, where the heteroaryl residue is pyridyl, furanyl, benzofuranyl, thienyl, benzothienyl, 1,2,3,4-tetrahydrocarbazolyl or julolidinyl,
• where the substituents of the aryl or heteroaryl residues in a) and b) are those selected from the previously defined group α or the group χ, consisting of amino, mono-(C1-C6)-alkylamino, di-(C1-C6)-alkylamino, mono- and diphenylamino unsubstituted, mono- or disubstituted on the phenyl ring, piperidinyl, N-substituted piperazinyl, pyrrolidinyl, imidazolidinyl, pyrazolidinyl, indolinyl, morpholinyl, 2,6-dimethylmorpholinyl, thiomorpholinyl, azacycloheptyl, azacyclooctyl, unsubstituted, mono- or disubstituted phenothiazinyl, unsubstituted, mono- or disubstituted phenoxazinyl, unsubstituted, mono- or disubstituted 1,2,3,4-tetrahydroquinolinyl, unsubstituted, mono- or disubstituted 2,3-dihydro-1,4-benzoxazinyl, unsubstituted, mono- or disubstituted 1,2,3,4-tetrahydroisoquinolinyl, unsubstituted, mono- or disubstituted phenazinyl, unsubstituted, mono- or disubstituted carbazolyl, unsubstituted, mono- or disubstituted 1,2,3,4-tetrahydrocarbazolyl and unsubstituted, mono- or disubstituted 10,11-dihydrodibenz[b,f]azepinyl, where the substituents in turn may each independently be selected from (C1-C6)-alkyl, (C1-C6)-alkoxy, bromine, chlorine or fluorine;
• or where two directly adjacent substituents of the aryl or heteroaryl residues in a) and b) are a V—(CR8R9)p—W moiety, where p=1, 2 or 3, the residues R8 and R9 are each independently a substituent selected from the group α, and where V and W may each independently be —O—, —S—, —N(C1-C6)alkyl, —NC6H5, —CH2—, —C(CH3)2— or —C(C6H5)2—, where two or more adjacent CR8R9 units of this V—(CR8R9)p—W moiety may be part of a benzene ring fused thereto, which in turn may each have one or more substituents selected from the group α, or V and/or W together with the respective adjacent CR8R9 unit is a fused benzene ring, which may be unsubstituted, mono- or disubstituted, of which the substituents may be selected from the group α.