Photochromic indeno fused phenanthrenopyran compounds

A photochromic compound represented by the following Formula (I),

• wherein n is 1 to 3, and m is 1 to 4,
• R2 is selected from the group consisting of, hydrogen;
• halogen;
• linear or branched C1-C20 alkyl;
• linear or branched C1-C20 perhaloalkyl;
• —ORa;
• —SRa, where each Ra is independently selected from the group consisting of hydrogen, linear or branched C1-C20 alkyl, and linear or branched C1-C20 perhaloalkyl;
• —C(O)ORb, where Rb is hydrogen or linear or branched C1-C10 alkyl;
• substituted or unsubstituted aryl, each aryl substituent being independently selected from the group consisting of hydroxyl, halogen, carbonyl, linear or branched C1-C20 alkoxycarbonyl, cyano, linear or branched C1-C20 haloalkyl, linear or branched C1-C20 alkyl, linear or branched C1-C20 alkoxy, and linear or branched C1-C20 perhaloalkyl;
• and a group Y1;
• R6 and R7 are each independently selected from the group consisting of, hydrogen;
• halogen;
• a lengthening group L1;
• —ORc, and —SRc, where each Rc is independently selected from the group consisting of hydrogen, a lengthening group L2, linear or branched C1-C20 alkyl, —C(O)—Rd, and —S(O)(O)—Re, where Rd and Re are each independently selected from the group consisting of linear or branched C1-C10 alkyl, linear or branched C1-C10 perhaloalkyl, phenyl, linear or branched C1-C10 alkyl substituted phenyl, and linear or branched C1-C10 perhaloalkyl substituted phenyl,
• provided that at least one of R6 and R7 is other than hydrogen;
• R1 independently for each n, and R3 independently for each m are each independently selected from the group consisting of,
• hydrogen;
• cyano;
• a reactive substituent;
• a lengthening group L3;
• halogen selected from the group consisting of fluoro, chloro, and bromo;
• linear or branched C1-C20 alkyl;
• linear or branched C1-C20 perhaloalkyl;
• C3-C10 cycloalkyl;
• a group Y2;
• substituted or unsubstituted phenyl, the phenyl substituents being selected from the group consisting of at least one of hydroxyl, halogen, carbonyl, linear or branched C1-C20 alkoxycarbonyl, cyano, linear or branched C1-C20 haloalkyl, linear or branched C1-C20 alkyl, linear or branched C1-C20 alkoxy, linear or branched C1-C20 perhaloalkyl, and combinations thereof;
• —O—R10′, —S—R10′, —C(O)—R10′, —C(O)—OR10′, —OC(O)—R10′, —OC(O)O—R10′, —C(O)N(R10′)R10′, —N(R10′)C(O)N(R10′)(R10′), or —Si(OR10′)w(R10′)t, wherein each R10′ independently is hydrogen, linear or branched C1-C20 alkyl, phenyl(C1-C20)alkyl, mono(C1-C20)alkyl substituted phenyl(C1-C20)alkyl, mono(C1-C20)alkoxy substituted phenyl(C1-C20)alkyl, (C1-C20)alkoxy(C2-C20)alkyl, C3-C10 cycloalkyl, or mono(C1-C20)alkyl substituted C3-C10 cycloalkyl, and w and t are each independently 0 to 3, provided that w+t is 3;
• and
• —N(R11′)R12′, wherein R11′ and R12′ are each independently hydrogen, linear or branched C1-C20 alkyl, phenyl, naphthyl, furanyl, benzofuran-2-yl, benzofuran-3-yl, thienyl, benzothien-2-yl, benzothien-3-yl, dibenzofuranyl, dibenzothienyl, benzopyridyl, fluorenyl, linear or branched C1-C20 alkylaryl, C3-C10 cycloalkyl, C4-C20 bicycloalkyl, C5-C20 tricycloalkyl or linear or branched C1-C20 alkoxyalkyl, wherein the aryl group is phenyl or naphthyl, or R11′ and R12′ come together with the nitrogen atom to form a ring;
• R4 and R5 are each independently selected from the group consisting of,
• (i) hydrogen, hydroxyl, linear or branched C1-C20 alkyl, linear or branched C1-C20 haloalkyl, C3-C10 cycloalkyl, allyl, benzyl, or substituted benzyl, the benzyl substituents being selected from the group consisting of halogen, linear or branched C1-C20 alkyl or linear or branched C1-C20 alkoxy;
• (ii) an unsubstituted, mono- di- or tri-substituted group selected from the group consisting of phenyl, naphthyl, phenanthryl, pyrenyl, quinolyl, isoquinolyl, benzofuranyl, thienyl, benzothienyl, dibenzofuranyl, dibenzothienyl, carbazolyl, or indolyl, the group substituents in each case being independently selected from the group consisting of halogen, linear or branched C1-C20 alkyl or linear or branched C1-C20 alkoxy;
• and
• (iii) a group Y3;
• or
• (iv) R4 and R5 together form a spiro substituent selected from the group consisting of a substituted or unsubstituted spiro-carbocyclic ring containing 3 to 10 carbon atoms, a substituted or unsubstituted spiro-heterocyclic ring containing 1 or 2 oxygen atoms and 3 to 10 carbon atoms including the spirocarbon atom, the spiro-carbocyclic ring and spiro-heterocyclic ring being annellated with 0, 1 or 2 benzene rings, the substituents being hydrogen or linear or branched C1-C20 alkyl;
• and
• B and B′ are each independently selected from the group consisting of unsubstituted aryl, substituted aryl, unsubstituted heteroaryl, substituted heteroaryl, alkenyl, and alkynyl, or B and B′ taken together form a ring structure,
• wherein each group Y1, Y2, and Y3 independently comprises at least one residue of a ring-opened cyclic monomer, wherein each ring-opened cyclic monomer is independently selected from the group consisting of a ring-opened cyclic ester monomer and a ring-opened cyclic carbonate monomer, and
• wherein each the lengthening group L1, L2, and L3 is independently selected from the group consisting of,
• L(5) 4-(4-pentyl-phenylazo)-phenylcarbamoyl
• L(7) {4-[5-(4-propyl-benzoyloxy)-pyrimidin-2-yl]-phenyl} ester
• L(8) {4-[2-(4′-methyl-biphenyl-4-carbonyloxy)-1,2-diphenyl-ethoxycarbonyl]-phenyl} ester
• L(10) 4-[4-(4-{4-[3-(6-{4-[4-(4-nonyl-benzoyloxy)-phenoxycarbonyl]-phenoxy}-hexyloxycarbonyl)-propionyloxy]-benzoyloxy}-benzoyloxy)-phenyl]-piperazin-1-yl
• L(11) {4-[4-(4-{4-[4-(4-nonyl-benzoyloxy)-benzoyloxy]-benzoyloxy}-benzoyloxy)-phenyl]-piperazin-1-yl}
• L(12) 4-(4′-propyl-biphenyl-4-ylethynyl)-phenyl
• L(16) 4-(biphenyl-4-carbonyloxy)-piperidin-1-yl
• L(18) 4-(4-phenylcarbamoyl-phenylcarbamoyl)-piperidin-1-yl
• L(19) 4-(4-(4-phenylpiperidin-1-yl)-benzoyloxy)-piperidin-1-yl
• L(20) 4-butyl-[1,1′;4′,1″]terphenyl-4-yl
• L(21) 4-(4-pentadecafluoroheptyloxy-phenylcarbamoyl)-benzyloxy
• L(24) 4-[4-(4-cyclohexyl-phenylcarbamoyl)-benzoyloxy]-piperidin-1-yl
• L(25) N-{4-[(4-pentyl-benzylidene)-amino]-phenyl}-acetamidyl
• L(28) 4-(4′-hexyloxy-biphenyl-4-carbonyloxy)-piperidin-1-yl
• L(30a) 1-methyl-4-((4′-(((1-methylpiperidin-4-yl)oxy)carbonyl)-[1,1′-biphenyl]-4-carbonyl)oxy)piperidin-1-yl
• L(30b) bis(1-yl-piperidin-4-yl) [1,1′-biphenyl]-4,4′-dicarboxylate
• L(31)-(4-(9-(4-butylphenyl)-2,4,8,10-tetraoxaspiro[5.5]undec-3-yl)phenyl)piperazin-1-yl
• L(32) 4-(6-(4-butylphenyl)carbonyloxy-(4,8-dioxabicyclo[3.3.0]oct-2-yl))oxycarbonyl)phenyl
• L(33) 1-{4-[5-(4-butyl-phenyl)-[1,3]dioxan-2-yl]-phenyl}-4-methyl-piperazin-1-yl
• L(34) 4-(7-(4-propylphenylcarbonyloxy)bicyclo[3.3.0]oct-2-yl)oxycarbonyl)phenyl
• L(35) 4-[17-(1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxycarbonyloxy
• L(a)
• L(c)
• L(g)
• L(h)
• L(i)
• L(j)
• L(k)
• L(l)
• L(m)
• L(r)
• L(t)
• L(v)
• L(z)
• L(ac)
• L(ad)
• L-DC-(a) (4-trans-(4-pentylcyclohexyl)benzamido)phenyl,
• L-DC-(d) 4-((trans-(4′-pentyl-[1,1′-bi(cyclohexan)]-4-yl)oxy)carbonyl)phenyl,
• L-DC-(g) 4-(4′-(4-pentylcyclohexyl)-[1,1′-biphenyl]-4-carbonyl)piperazin-1-yl,
• L-DC-(h) 4-(4-(4-trans-(4-pentylcyclohexyl) phenyl)benzamido)-2-(trifluoromethyl)phenyl,
• L-DC-(i) 2-methyl-4-trans-(4-((4′-trans-(4-pentylcyclohexyl)biphenyl-4-yloxy)carbonyl)cyclohexanecarboxamido)phenyl,
• L-DC-(j) 4′-(4′-pentylbi(cyclohexane-4-)carbonyloxy)biphenylcarbonyloxy,
• L-DC-(k) 4-(((3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yloxy)carbonyl)piperazin-1-yl, and
• L-DC-(l) 4-((S)-2-methylbutoxy)phenyl)-10-(4-(((3R,3aS,6S,6aS)-6-(4′-trans-(4-pentylcyclohexyl)biphenylcarbonyloxy)hexahydrofuro[3,2-b]furan-3-yloxy)carbonyl)phenyl,
• provided that for —ORc where Rc is the lengthening group L2, the bond between —O and the lengthening group L2 is free of two heteroatoms linked to each other.