H-annellated benzo[f]chromenes

A photochromic h-annellated benzo[f]chromene compound corresponding to formula (I):

• wherein
• n and m independently represent 0, 1 or 2,
• R1, R2, R3 and R4 each independently represent a substituent selected from:
• the group α consisting of a hydrogen atom, a (C1-C6) alkyl radical, a (C3-C7) cycloalkyl radical which may contain one or more heteroatoms, a (C1-C6) alkoxy radical, a hydroxy group, a trifluoromethyl group, bromine, chlorine and fluorine;
• the group β consisting of an unsubstituted, monosubstituted or disubstituted phenyl, phenoxy, benzyl, benzyloxy, naphthyl or naphthoxy radical, wherein any substituents are selected from the group □ and phenyl;
• the group χ wherein R1 and R2 or R3 and R4 form an —A—(CH2)k—B— group bound to the aromatic ring, wherein k =1 or 2, and A and B are independently selected from the group consisting of oxygen, sulfur, CH2, C(CH3)2 or C(C6H5)2, and wherein a benzo ring may in turn be annellated to the —A—(CH2)k—B— group;
• the group δ consisting of an unsubstituted, monosubstituted or disubstituted amino group, wherein any amine substituents are selected from a (C1-C6) alkyl radical, a (C3-C7) cycloalkyl radical, a phenyl or benzyl radical unsubstituted or substituted with one or more substituents from the group α, an N-morpholine group, an N-thiomorpholine group, an N-piperidine group, an N-azacycloheptane group, an N-piperazine group, an N-(N′-(C1-C6-alkyl)piperazine group, an N-pyrrolidine group, an N-imidazolidine group, an N-pyrazolidine group, an N-aziridine group, an N-azetidine group, an N-indoline group, an N-carbazole group, an N-phenothiazine group, an N-phenazine group, an N-phenoxazine group, an N-tetrahydroquinoline group, and an N-tetrahydroisoquinoline group;
• the group ε, wherein R1 and R2, or R3 and R4, respectively, together form a —D—(CH2)k—E— group bound to the benzo ring, wherein k=1 or 2;
• D is independently selected from the group consisting of N(CH3) and N(C6H5), and E is independently selected from the group consisting of oxygen, sulfur, CH2, C(CH3)2, C(C6H5)2, N(CH3) and N(C6H5), and wherein a benzo ring may in turn be annellated to the —D—(CH2)k—E-group;
• and
• the group φ wherein R1 and R2 or R3 and R4, respectively, together with the benzene ring to which they are bound, form a julolidinyl moiety;
• provided that at least one of R1, R2 R3 and R4 or R1/R2 and R3/R4 is selected from the groups δ, ε and φ;
• R5, R6, R7 and R8 are each independently selected from the group α and phenyl, or
• R5 and R6 together with R3 of a directly adjacent benzo ring form an unsubstituted, monosubstituted or disubstituted benzo or pyrido ring annellated thereto, wherein any substituents are selected from the group α and phenyl, or if m or n is 2, directly adjacent radicals R5 and R6 of two adjacent CR5R6 units or directly adjacent radicals R7 and R8 of two adjacent CR7R8 units together form an annellated, unsubstituted, monosubstituted or disubstituted benzo or pyrido ring wherein any substituents are selected from the group α and phenyl, or
• R5 and R6 and/or R7 and R8 together represent a (C3-C7) cycloalkyl radical, which may contain one or more heteroatoms, and wherein a benzo ring may be annellated to the cycloalkyl radical;
• X is selected from the group consisting of O, S, CR9R10 and NR11, wherein
• R11 is hydrogen, cyano, (C1-C6) alkyl, (C3-C7) cycloalkyl or phenyl, and
• R9 and R10 are independently selected from the group α and phenyl, or together represent a (C3-C7) cycloalkyl radical, which may contain one or more heteroatoms, or
• if X is CR9R10, R9 and R10 together with the radicals R5 and R6 or R7 and R8 of a directly adjacent CR5R6 or CR7R8 moiety may also represent an unsubstituted, monosubstituted or disubstituted benzo or pyrido ring annellated to the X—C(R5R6) or X—C(R7R8) bond, wherein any substituents are selected from the group α and phenyl;
• B and B′ are each independently selected from
• the group a) consisting of monosubstituted, disubstituted or trisubstituted aryl radicals selected from the group consisting of phenyl and naphthyl;
• the group b) consisting of unsubstituted, monosubstituted and disubstituted heteroaryl radicals selected from the group consisting of pyridyl, furanyl, benzofuran-2-yl, benzofuran-3-yl, thienyl, benzothieno-2-yl, benzothieno-3-yl, and julolidinyl;
• wherein any substituents on the aryl or the heteroaryl radicals in a) and b) are selected from the groups α, β or δ or two directly adjacent substituents together form a —D—(CH2)k—E— group bound to the benzo ring as defined above,
• the group c) consisting of structural units having either of the following formulas (V) or (W):
• wherein
• Y and Z are independently selected from the group consisting of O, S, CH, CH2 and NR11;
• R11 is as defined above;
• R12 and R13 independently represent hydrogen or a (C1-C5) alkyl radical,
• R14 is a substituent selected from the group α, and
• p is 1, 2, or 3;
• provided that, if Y in formula (V) is NR11, Z is carbon, and
• the group d) wherein B and B′ together form an unsubstituted, monosubstituted or disubstituted fluorene-9-ylidene radical or a saturated hydrocarbon radical, which is C3-C12 spiro-monocyclic, C7-C12 spiro-bicyclic or C7-C12 spiro-tricyclic, wherein any fluorene substituents are selected from the group α.