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Kafe 바로가기국가/구분 | United States(US) Patent 등록 |
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국제특허분류(IPC7판) |
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출원번호 | US-0222457 (2011-08-31) |
등록번호 | US-8698117 (2014-04-15) |
발명자 / 주소 |
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출원인 / 주소 |
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대리인 / 주소 |
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인용정보 | 피인용 횟수 : 4 인용 특허 : 171 |
The present invention relates to compounds represented by the following Formulas (I) and (II), Ring-A of Formulas I and II can be, for example, an aryl group, and Q′ and Q′″ can each be independently selected from groups, such as, halogen, —OH, —CN, amine groups, amide groups, carboxylic acid ester
The present invention relates to compounds represented by the following Formulas (I) and (II), Ring-A of Formulas I and II can be, for example, an aryl group, and Q′ and Q′″ can each be independently selected from groups, such as, halogen, —OH, —CN, amine groups, amide groups, carboxylic acid ester groups, carboxylic acid groups, alkenyl groups, alkynyl groups, carbonate groups, sulfide groups, and sulfonic acid ester groups. The present invention also relates to photochromic compositions and photochromic articles that include one or more photochromic compounds, such as represented by Formula II.
1. An indeno-fused ring compound represented by the following Formula I, wherein,(A) Ring-A is selected from unsubstituted aryl, substituted aryl, unsubstituted fused ring aryl, or substituted fused ring aryl,(B) Q′ is selected from halogen, —OH, —N3, —NRaRa, —N(Ra)C(O)Q″, —CN, —C(O)ORa, —C(O)Ra, —C
1. An indeno-fused ring compound represented by the following Formula I, wherein,(A) Ring-A is selected from unsubstituted aryl, substituted aryl, unsubstituted fused ring aryl, or substituted fused ring aryl,(B) Q′ is selected from halogen, —OH, —N3, —NRaRa, —N(Ra)C(O)Q″, —CN, —C(O)ORa, —C(O)Ra, —C≡C—Ra, —C(Ra)═C(Ra)(Ra), —OC(O)Ra, —OC(O)ORa, —SRa, —OS(O2)Rb, —C(O)NRaRa and a lengthening agent L, wherein each Ra is independently selected from hydrogen, hydrocarbyl and substituted hydrocarbyl each optionally and independently interrupted with at least one of —O—, —S—, —C(O)—, —C(O)O—, —S(O)—, —S(O2)—, —N═N—, —N(R11′)— where R11′ is selected from hydrogen, hydrocarbyl or substituted hydrocarbyl, —Si(OR14)u(R14)v—, where u and v are each independently selected from 0 to 2, provided that the sum of u and v is 2, and each R14 is independently selected from hydrogen, hydrocarbyl and substituted hydrocarbyl, and combinations of two or more thereof, or two Ra groups come together with —N and optionally an additional hetero atom selected from N and O to form a heterocycloalkyl, and Rb is selected from perhalohydrocarbyl, and Q″ is selected from halo, —ORa, —NRaRa, —C(O)ORa, —SRa, and hydrocarbyl or substituted hydrocarbyl, wherein said substituents are selected from —OH, —NRaRa, —C(O)ORa, —SRa, wherein said lengthening agent L is represented by the following formula, —(S1)c-(Q1-(S2)d)d′-(Q2-(S3)e)e′-(Q3-(S4)f)f′-S5-Pwherein, (i) each Q1, Q2, and Q3 is independently chosen for each occurrence from, a divalent group chosen from, an unsubstituted or a substituted aromatic group, an unsubstituted or a substituted alicyclic group, an unsubstituted or a substituted heterocyclic group, and mixtures thereof, wherein substituents are chosen from, a group represented by P, liquid crystal mesogens, halogen, poly(C1-C18 alkoxy), C1-C18 alkoxycarbonyl, C1-C18 alkylcarbonyl, C1-C18 alkoxycarbonyloxy, aryloxycarbonyloxy, perfluoro(C1-C18)alkoxy, perfluoro(C1-C18)alkoxycarbonyl, perfluoro(C1-C18)alkylcarbonyl, perfluoro(C1-C18)alkylamino, di-(perfluoro(C1-C18)alkyl)amino, perfluoro(C1-C18)alkylthio, C1-C18 alkylthio, C1-C18 acetyl, C3-C10 cycloalkyl, C3-C10 cycloalkoxy, a straight-chain or branched C1-C18 alkyl group that is mono-substituted with cyano, halo, or C1-C18 alkoxy, or poly-substituted with halo, and a group comprising one of the following formulae: -M(T)(t-1) and -M(OT)(t-1), wherein M is chosen from aluminum, antimony, tantalum, titanium, zirconium and silicon, T is chosen from organofunctional radicals, organofunctional hydrocarbon radicals, aliphatic hydrocarbon radicals and aromatic hydrocarbon radicals, and t is the valence of M,(ii) c, d, e, and f are each independently chosen from an integer ranging from 0 to 20, inclusive; and each S1, S2, S3, S4, and S5 is independently chosen for each occurrence from a spacer unit chosen from:(1) optionally substituted alkylene, optionally substituted haloalkylene, —Si(Z′)2(CH2)g—, and wherein each Z′ is independently selected from hydrogen, C1-C18 alkyl, C3-C10 cycloalkyl, and aryl; g for each occurrence is independently chosen from an integer from 1 to 20; h for each occurrence is independently chosen from an integer from 1 to 16; and said substituents for the alkylene and haloalkylene are independently selected from C1-C18 alkyl, C3-C10 cycloalkyl and aryl;(2) —N(Z)—, —C(Z)═C(Z)—, —C(Z)═N—, —C(Z′)2—C(Z′)2—, or a single bond, wherein Z is independently chosen for each occurrence from hydrogen, C1-C8 alkyl, C3-C10 cycloalkyl and aryl, and Z′ is independently chosen for each occurrence from C1-C18 alkyl, C3-C10 cycloalkyl and aryl; and(3) —O—, —C(O)—, —C≡C—, —N═N—, —S—, —S(O)—, —S(O)(O)—, —(O)S(O)—, —(O)S(O)O—, —O(O)S(O)O—, or straight-chain or branched C1-C24 alkylene residue, said C1-C24 alkylene residue being unsubstituted, mono-substituted by cyano or halo, or poly-substituted by halo,provided that when two spacer units comprising heteroatoms are linked together the spacer units are linked so that heteroatoms are not directly linked to each other, andprovided that when S1 and S5 are linked to Formula I and P, respectively, they are linked so that two heteroatoms are not directly linked to each other, (iii) P is chosen from: hydroxy, amino, C2-C18 alkenyl, C2-C18 alkynyl, azido, silyl, siloxy, silylhydride, (tetrahydro-2H-pyran-2-yl)oxy, thio, isocyanato, thioisocyanato, acryloyloxy, methacryloyloxy, 2-(acryloyloxy)ethylcarbamyl, 2-(methacryloyloxy)ethylcarbamyl, aziridinyl, allyloxycarbonyloxy, epoxy, carboxylic acid, carboxylic ester, acryloylamino, methacryloylamino, aminocarbonyl, C1-C18 alkyl aminocarbonyl, aminocarbonyl(C1-C18)alkyl, C1-C18 alkyloxycarbonyloxy, halocarbonyl, hydrogen, aryl, hydroxy(C1-C18)alkyl, C1-C18 alkyl, C1-C18 alkoxy, amino(C1-C18)alkyl, C1-C18 alkylamino, di-(C1-C18)alkylamino, C1-C18 alkyl(C1-C18)alkoxy, C1-C18 alkoxy(C1-C18)alkoxy, nitro, poly(C1-C18)alkyl ether, (C1-C18)alkyl(C1-C18)alkoxy(C1-C18)alkyl, polyethyleneoxy, polypropyleneoxy, ethylenyl, acryloyl, acryloyloxy(C1-C18)alkyl, methacryloyl, methacryloyloxy(C1-C18)alkyl, 2-chloroacryloyl, 2-phenylacryloyl, acryloyloxyphenyl, 2-chloroacryloylamino, 2-phenylacryloylaminocarbonyl, oxetanyl, glycidyl, cyano, isocyanato(C1-C18)alkyl, itaconic acid ester, vinyl ether, vinyl ester, a styrene derivative, main-chain and side-chain liquid crystal polymers, siloxane derivatives, ethyleneimine derivatives, maleic acid derivatives, fumaric acid derivatives, unsubstituted cinnamic acid derivatives, cinnamic acid derivatives that are substituted with at least one of methyl, methoxy, cyano and halogen, or substituted or unsubstituted chiral or non-chiral monovalent or divalent groups chosen from steroid radicals, terpenoid radicals, alkaloid radicals and mixtures thereof, wherein the substituents are independently chosen from C1-C18 alkyl, C1-C18 alkoxy, amino, C3-C10 cycloalkyl, C1-C18 alkyl(C1-C18)alkoxy, fluoro(C1-C18)alkyl, cyano, cyano(C1-C18)alkyl, cyano(C1-C18)alkoxy or mixtures thereof, or P is a structure having from 2 to 4 reactive groups or P is an unsubstituted or substituted ring opening metathesis polymerization precursor; and(iv) d′, e′ and f′ are each independently chosen from 0, 1, 2, 3, and 4, provided that a sum of d′+e′+f′ is at least 1;(C) i is selected from 0 to 3, t is selected from 0 to a total number of positions to which R2 can be bonded, and R1 for each i, and R2 for each t, are each independently selected from, hydrocarbyl and substituted hydrocarbyl each optionally and independently interrupted with at least one of —O—, —S—, —C(O)—, —C(O)O—, —S(O)—, —S(O2)—, —N═N—, —N(R11′)— where R11′ is selected from hydrogen, hydrocarbyl or substituted hydrocarbyl, —Si(OR14)u(R14)v—, where u and v are each independently selected from 0 to 2, provided that the sum of u and v is 2, and each R14 is independently selected from hydrogen, hydrocarbyl and substituted hydrocarbyl, and combinations of two or more thereof; halogen; cyano; and —N(R11′)R12′, wherein R11′ and R12′ are each independently selected from hydrogen, hydrocarbyl or substituted hydrocarbyl, or R11′ and R12′ together form a ring structure optionally including at least one heteroatom,(D) R3 and R4 are each independently selected from, hydrogen; hydrocarbyl and substituted hydrocarbyl each optionally and independently interrupted with at least one of —O—, —S—, —C(O)—, —C(O)O—, —S(O)—, —S(O2)—, —N═N—, —N(R11′)— where R11′ is selected from hydrogen, hydrocarbyl or substituted hydrocarbyl, —Si(OR4)u(R14)v—, where u and v are each independently selected from 0 to 2, provided that the sum of u and v is 2, and each R14 is independently selected from hydrogen, hydrocarbyl and substituted hydrocarbyl, and combinations of two or more thereof; or R3 and R4 together form a ring structure optionally including at least one heteroatom, and(E) R5 is selected from hydrogen, —C(O)—R13 or —S(O2)R13 wherein R13 is hydrocarbyl, or halohydrocarbyl. 2. The indeno-fused ring compound of claim 1, wherein, (A) Ring-A is unsubstituted aryl or substituted aryl;(B) Q′ is selected from bromo, fluoro, chloro, —N3, —NRaRa, —N(Ra)C(O)Q″, —C(O)ORa, —C(O)Ra, —C≡C—Ra, —C(Ra)═C(Ra)(Ra), —OC(O)Ra, —OC(O)ORa, —SRa, —OS(O2)Rb, —C(O)NRaRa, and said lengthening agent L, wherein each R′ is independently selected from hydrogen, an unsubstituted or substituted alkyl group having from 1 to 18 carbon atoms, an unsubstituted or substituted aryl group, an unsubstituted or substituted alkene or alkyne group having from 2 to 18 carbon atoms, wherein said substituents are chosen from halo and hydroxyl, or two Ra groups come together with —N and an additional hetero atom selected from N and O to form a heterocycloalkyl and Rb is selected from a perfluorinated alkyl group having from 1 to 18 carbon atoms, and Q″ is selected from —ORa, —NRaRa, —C(O)ORa, —SRa, and hydrocarbyl or substituted hydrocarbyl, wherein said substituents are selected from —OH, —NRaRa, —C(O)ORa, —SRa, and for lengthening agent L, d′, e′ and f′ are each independently chosen from 0, 1, 2, 3, and 4, provided that a sum of d′+e′+f′ is at least 2;(C) R1 for each i, and R2 for each t, are each independently selected from, (a) —C(O)X24, wherein X24 is chosen from said lengthening agent L, hydroxy, C1-C18 alkyl, C1-C18 alkoxy, phenyl that is unsubstituted or mono-substituted with C1-C18 alkyl or C1-C18 alkoxy, amino that is unsubstituted, mono- or di-substituted with at least one of C1-C18 alkyl, phenyl, benzyl, and naphthyl,(b) —OX7 and —N(X7)2; wherein X7 is chosen from: (i) hydrogen, a lengthening agent L, C1-C18 alkyl, C1-C18 acyl, phenyl(C1-C18)alkyl, mono(C1-C18)alkyl substituted phenyl(C1-C18)alkyl, mono(C1-C18)alkoxy substituted phenyl(C1-C18)alkyl; C1-C18 alkoxy(C1-C18)alkyl; C3-C10 cycloalkyl; mono(C1-C18)alkyl substituted C3-C10 cycloalkyl, C1-C18 haloalkyl, allyl, benzoyl, mono-substituted benzoyl, naphthoyl or mono-substituted naphthoyl, wherein each of said benzoyl and naphthoyl substituents are independently chosen from C1-C18 alkyl, and C1-C18 alkoxy,(ii) —CH(X8)X9, wherein X8 is chosen from hydrogen, a lengthening agent L, or C1-C18 alkyl, and X9 is chosen from a lengthening agent L, —CN, —CF3, or —COOX10, wherein X10 is chosen from hydrogen, a lengthening agent L, or C1-C18 alkyl,(iii) —C(O)X6, wherein X6 is chosen from at least one of, hydrogen, a lengthening agent L, C1-C18 alkoxy, phenoxy that is unsubstituted, mono- or di-substituted with C1-C18 alkyl or C1-C18 alkoxy, an aryl group that is unsubstituted, mono- or di-substituted with C1-C18 alkyl or C1-C18 alkoxy, an amino group that is unsubstituted, mono- or di-substituted with C1-C18 alkyl, and a phenylamino group that is unsubstituted, mono- or di-substituted with C1-C18 alkyl or C1-C18 alkoxy, or(iv) tri(C1-C18)alkylsilyl, tri(C1-C18)alkylsilyloxy, tri(C1-C18)alkoxysilyl, tri(C1-C18)alkoxysilyloxy, di(C1-C18)alkyl(C1-C18 alkoxy)silyl, di(C1-C18)alkyl(C1-C18 alkoxy)silyloxy, di(C1-C18)alkoxy(C1-C18 alkyl)silyl or di(C1-C18)alkoxy(C1-C18 alkyl)silyloxy;(c) —SX11, wherein X11 is chosen from hydrogen, a lengthening agent L, C1-C18 alkyl, C1-C18 haloalkyl, an aryl group that is unsubstituted, or mono- or di-substituted with C1-C18 alkyl, C1-C18 alkoxy, or halogen;(d) a nitrogen containing ring represented by Formula i: wherein, each —Y— is independently chosen for each occurrence from —CH2—, —CH(R13′)—, —C(R13′)2—, —CH(aryl)-, —C(aryl)2-, and —C(R13′)(aryl)-, and Z is —Y—, —O—, —S—, —S(O)—, —SO2—, —NH—, —N(R13′)—, or —N(aryl)-, wherein each R13′ is independently a lengthening group L, or C1-C20 alkyl, each aryl is independently phenyl or naphthyl, m is an integer 1, 2 or 3, and p is an integer 0, 1, 2, or 3, provided that when p is 0, Z is —Y—;(e) a group represented by Formula ii or iii, wherein X14, X15, and X16 are independently chosen for each occurrence from hydrogen, a lengthening agent L, C1-C18 alkyl, phenyl or naphthyl, or X14 and X15 together form a ring of 5 to 8 carbon atoms, p is an integer chosen from 0, 1, or 2, and X17 is independently chosen for each occurrence from a lengthening agent L, C1-C18 alkyl, C1-C18 alkoxy, or halogen;(f) immediately adjacent R1 groups, and immediately adjacent R2 groups, in each case independently together form a group represented by Formula vii, viii, or ix, wherein, (i) W and W′ are independently chosen for each occurrence from —O—, —N(X7)—, —C(X14)—, and —C(Xr17)—,(ii) wherein X14 and X15 are independently chosen for each occurrence from hydrogen, a lengthening agent L, C1-C18 alkyl, phenyl or naphthyl, or X14 and X15 together form a ring of 5 to 8 carbon atoms; and X17 is independently chosen for each occurrence from a lengthening agent L, C1-C18 alkyl, C1-C18 alkoxy, or halogen, and(iii) q is an integer chosen from 0, 1, 2, 3, and 4;(g) lengthening agent L;(h) a group B selected from, (i) hydrogen, C1-C18 alkyl, C2-C18 alkylidene, C2-C18 alkylidyne, vinyl, C3-C10 cycloalkyl, C1-C18 haloalkyl, allyl, halogen, and benzyl that is unsubstituted or mono-substituted with at least one of C1-C18 alkyl and C1-C18 alkoxy;(ii) phenyl that is mono-substituted at the para position with at least one substituent chosen from: C1-C18 alkoxy, linear or branched chain C1-C20 alkylene, linear or branched chain C1-C4 polyoxyalkylene, cyclic C3-C20 alkylene, phenylene, naphthylene, C1-C18 alkyl substituted phenylene, mono- or poly-urethane(C1-C20)alkylene, mono- or poly-ester(C1-C20)alkylene, mono- or poly-carbonate(C1-C20)alkylene, polysilanylene, polysiloxanylene and mixtures thereof, wherein the at least one substituent is connected to an aryl group of a photochromic material,(iii) —CH(CN)2 and —CH(COOX1)2, wherein X1 is chosen from at least one of hydrogen, a lengthening agent L, C1-C18 alkyl that is unsubstituted or mono-substituted with phenyl, phenyl(C1-C18)alkyl that is mono-substituted with C1-C18 alkyl, C1-C18 haloalkyl or C1-C18 alkoxy, and an aryl group that is unsubstituted, mono- or di-substituted, wherein each aryl substituent is independently chosen from C1-C18 alkyl and C1-C18 alkoxy, and lengthening agent L,(iv) —CH(X2)(X3), wherein,(1) X2 is chosen from at least one of hydrogen, a lengthening agent L, C1-C18 alkyl, and an aryl group that is unsubstituted, mono- or di-substituted, wherein each aryl substituent is independently chosen from C1-C18 alkyl and C1-C18 alkoxy; and(2) X3 is chosen from at least one of —COOX1, —COX1, —COX4, and —CH2OX5, wherein, X4 is chosen from at least one of morpholino, piperidino, amino that is unsubstituted, mono- or di-substituted with C1-C18 alkyl, and an unsubstituted, mono- or di-substituted group chosen from phenylamino and diphenylamino, wherein each substituent is independently chosen from C1-C18 alkyl or C1-C18 alkoxy; and X5 is chosen from hydrogen, a lengthening agent L, —C(O)X2, C1-C18 alkyl that is unsubstituted or mono-substituted with (C1-C18)alkoxy or phenyl, phenyl(C1-C18)alkyl that is mono-substituted with (C1-C18)alkoxy, and an aryl group that is unsubstituted, mono- or di-substituted, wherein each aryl substituent is independently chosen from C1-C18 alkyl and C1-C18 alkoxy;(v) an unsubstituted, mono-, di-, or tri-substituted aryl group; 9-julolidinyl; or an unsubstituted, mono- or di-substituted heteroaromatic group chosen from pyridyl, furanyl, benzofuran-2-yl, benzofuran-3-yl, thienyl, benzothien-2-yl, benzothien-3-yl, dibenzofuranyl, dibenzothienyl, carbazoyl, benzopyridyl, indolinyl, or fluorenyl; wherein each aryl and heteroaromatic group substituent is independently chosen for each occurrence from:(1) lengthening agent L,(2) —COOX1 or —C(O)X6;(3) aryl, halogen, haloaryl, C3-C10 cycloalkylaryl, and an aryl group that is mono- or di-substituted with C1-C18 alkyl or C1-C18 alkoxy;(4) C1-C18 alkyl, C3-C10 cycloalkyl, C3-C10 cycloalkyloxy(C1-C18)alkyl, aryl(C1-C18)alkyl, aryloxy(C1-C18)alkyl, mono- or di-(C1-C18)alkylaryl(C1-C18)alkyl, mono- or di-(C1-C18)alkoxyaryl(C1-C18)alkyl, C1-C18 haloalkyl, and mono(C1-C18)alkoxy(C1-C18)alkyl;(5) C1-C18 alkoxy, C3-C10 cycloalkoxy, cycloalkyloxy(C1-C18)alkoxy, aryl(C1-C18)alkoxy, aryloxy(C1-C18)alkoxy, mono- or di-(C1-C18)alkylaryl(C1-C18)alkoxy, and mono- or di-(C1-C18)alkoxyaryl(C1-C18)alkoxy;(6) aminocarbonyl, aminocarbonyl(C1-C18)alkylene, amino, mono- or di-alkylamino, diarylamino, piperazino, N—(C1-C18)alkylpiperazino, N-arylpiperazino, aziridino, indolino, piperidino, morpholino, thiomorpholino, tetrahydroquinolino, tetrahydroisoquinolino, pyrrolidyl, hydroxy, acryloxy, methacryloxy, and halogen;(7) —OX7 or —N(X7)2;(8) —SX11;(9) a nitrogen containing ring represented by Formula i;(10) a group represented by Formula ii or iii;(11) an unsubstituted or mono-substituted group chosen from pyrazolyl, imidazolyl, pyrazolinyl, imidazolinyl, pyrrolidinyl, phenothiazinyl, phenoxazinyl, phenazinyl, or acridinyl, wherein each substituent is independently chosen from a lengthening agent L, C1-C18 alkyl, C1-C18 alkoxy, phenyl, hydroxy, amino or halogen;(12) a group represented by Formula iv or v: wherein, (I) V′ is independently chosen in each formula from —O—, —CH—, C1-C6 alkylene, and C3-C10 cycloalkylene,(II) V is independently chosen in each formula from —O— or —N(X21)—, wherein X21 is hydrogen, a lengthening agent L, C1-C18 alkyl, and C2-C18 acyl, provided that if V is —N(X21)—, V′ is —CH2—,(III) X18 and X19 are each independently chosen from hydrogen, a lengthening agent L, and C1-C18 alkyl, and(IV) k is chosen from 0, 1, and 2, and each X20 is independently chosen for each occurrence from a lengthening agent L, C1-C18 alkyl, C1-C18 alkoxy, hydroxy and halogen, and(13) a group represented by Formula vi: wherein (I) X22 is chosen from hydrogen, a lengthening agent L, and C1-C18 alkyl, and(II) X23 is chosen from a lengthening agent L and an unsubstituted, mono-, or di-substituted group chosen from naphthyl, phenyl, furanyl and thienyl, wherein each substituent is independently chosen for each occurrence from C1-C18 alkyl, C1-C18 alkoxy, and halogen;(D) R3 and R4 are each independently selected from, (i) hydrogen, C1-C20 alkyl, C1-C20 haloalkyl, C3-C10 cycloalkyl, allyl, benzyl, or mono-substituted benzyl, said benzyl substituents being chosen from halogen, C1-C20 alkyl or C1-C20 alkoxy;(ii) an unsubstituted, mono- di- or tri-substituted group chosen from phenyl, naphthyl, phenanthryl, pyrenyl, quinolyl, isoquinolyl, benzofuranyl, thienyl, benzothienyl, dibenzofuranyl, dibenzothienyl, carbazolyl, or indolyl, said group substituents in each case being independently chosen from halogen, C1-C20 alkyl or C1-C20 alkoxy;(iii) mono-substituted phenyl, said substituent located at the para position being —(CH2)t— or —O—(CH2)t—, wherein t is the integer 1, 2, 3, 4, 5 or 6, said substituent being connected to an aryl group which is a member of a photochromic material;(iv) the group —CH(R10)G, wherein R10 is hydrogen, C1-C20 alkyl or the unsubstituted, mono- or di-substituted aryl groups phenyl or naphthyl, and G is —CH2OR11, wherein R11 is hydrogen, —C(O)R10, C1-C20 alkyl, C1-C20 alkoxy(C1-C20)alkyl, phenyl(C1-C20)alkyl, mono(C1-C20)alkoxy substituted phenyl(C1-C20)alkyl, or the unsubstituted, mono- or di-substituted aryl groups phenyl or naphthyl, each of said phenyl and naphthyl group substituents being C1-C20 alkyl or C1-C20 alkoxy; or(v) R3 and R4 together form a spiro substituent selected from a substituted or unsubstituted spiro-carbocyclic ring containing 3 to 6 carbon atoms, a substituted or unsubstituted spiro-heterocyclic ring containing 1 or 2 oxygen atoms and 3 to 6 carbon atoms including the spirocarbon atom, said spiro-carbocyclic ring and spiro-heterocyclic ring being annellated with 0, 1 or 2 benzene rings, said substituents being hydrogen or C1-C20 alkyl; and(E) R5 is selected from hydrogen and —C(O)—R13. 3. The indeno-fused ring compound of claim 1, wherein, (A) Ring-A is unsubstituted aryl or substituted aryl;(B) Q′ is selected from bromo, chloro, —NRaRa, —C(O)Ra, —C(O)ORa, and lengthening agent L, wherein each Ra is independently selected from hydrogen and an alkyl group having from 1 to 6 carbon atoms, or two Ra groups come together with —N and an additional N atom to form a heterocycloalkyl and Rb is selected from a perfluorinated alkyl group having from 1 to 6 carbon atoms, and for lengthening agent L, d′, e′ and f′ are each independently chosen from 0, 1, 2, 3, and 4, provided that a sum of d′+e′+f′ is at least 3;(C) R1 for each i, and R2 for each t, are each independently selected from, (a) —C(O)X24, wherein X24 is chosen from lengthening agent L, hydroxy, C1-C12 alkyl, C1-C12 alkoxy, phenyl that is unsubstituted or mono-substituted with C1-C6 alkyl or C1-C6 alkoxy, amino that is unsubstituted, mono- or di-substituted with at least one of C1-C6 alkyl, phenyl, benzyl, and naphthyl;(b) —OX7 and —N(X7)2; wherein X7 is chosen from, (i) hydrogen, a lengthening agent L, C1-C12 alkyl, C1-C12 acyl, phenyl(C1-C12)alkyl, mono(C1-C12)alkyl substituted phenyl(C1-C12)alkyl, mono(C1-C12)alkoxy substituted phenyl(C1-C12)alkyl; C1-C12 alkoxy(C1-C12)alkyl; C3-C7 cycloalkyl; mono(C1-C12)alkyl substituted C3-C7 cycloalkyl, C1-C12 haloalkyl, allyl, benzoyl, mono-substituted benzoyl, naphthoyl or mono-substituted naphthoyl, wherein each of said benzoyl and naphthoyl substituents are independently chosen from C1-C6 alkyl, and C1-C6 alkoxy;(ii) —CH(X8)X9, wherein X8 is chosen from hydrogen, a lengthening agent L, or C1-C12 alkyl; and X9 is chosen from a lengthening agent L, —CN, —CF3, or —COOX10, wherein X10 is chosen from hydrogen, a lengthening agent L, or C1-C12 alkyl;(iii) —C(O)X6, wherein X6 is chosen from at least one of, hydrogen, a lengthening agent L, C1-C12 alkoxy, phenoxy that is unsubstituted, mono- or di-substituted with C1-C12 alkyl or C1-C12 alkoxy, an aryl group that is unsubstituted, mono- or di-substituted with C1-C6 alkyl or C1-C6 alkoxy, an amino group that is unsubstituted, mono- or di-substituted with C1-C6 alkyl, and a phenylamino group that is unsubstituted, mono- or di-substituted with C1-C6 alkyl or C1-C6 alkoxy;(c) a nitrogen containing ring represented by Formula i; wherein, each —Y— is independently chosen for each occurrence from —CH2—, —CH(R13′)—, —C(R13′)r, —CH(aryl)-, —C(aryl)2-, and —C(R13′)(aryl)-, and Z is —Y—, —O—, —S—, —S(O)—, —SO2≦, —NH—, —N(R13′)—, or —N(aryl)-, wherein each R13′ is independently a lengthening group L, or C1-C20 alkyl, each aryl is independently phenyl or naphthyl, m is an integer 1, 2 or 3, and p is an integer 0, 1, 2, or 3, provided that when p is 0, Z is —Y—;(d) the group represented by Formula II or iii; wherein X14, X15, and X16 are independently chosen for each occurrence from hydrogen, a lengthening agent L, C1-C12 alkyl, phenyl or naphthyl, or X14 and X15 together form a ring of 5 to 7 carbon atoms; p is an integer chosen from 0, 1, or 2, and X17 is independently chosen for each occurrence from a lengthening agent L, C1-C12 alkyl, C1-C12 alkoxy, or halogen;(e) immediately adjacent R1 groups, and immediately adjacent R2 groups, in each case independently together form a group represented by Formula vii, viii, or ix, wherein, (i) W and W′ are independently chosen for each occurrence from —O—, —N(X7)—, —C(X14)—, and —C(X17)—,(ii) wherein X14 and X15 are independently chosen for each occurrence from hydrogen, a lengthening agent L, C1-C12 alkyl, phenyl or naphthyl, or X14 and X15 together form a ring of 5 to 7 carbon atoms; and X17 is independently chosen for each occurrence from a lengthening agent L, C1-C12 alkyl, C1-C12 alkoxy, or halogen, and(iii) q is an integer chosen from 0 to 3;(f) lengthening agent L,(g) a group B selected from, (i) C1-C12 alkyl, C3-C7 cycloalkyl, C1-C12 haloalkyl and benzyl that is unsubstituted or mono-substituted with at least one of C1-C8 alkyl and C1-C6 alkoxy;(ii) —CH(CN)2 and —CH(COOX1)2, wherein X1 is chosen from at least one of hydrogen, lengthening agent L, C1-C12 alkyl that is unsubstituted or mono-substituted with phenyl, phenyl(C1-C6)alkyl that is mono-substituted with C1-C6 alkyl or C1-C6 alkoxy, and an aryl group that is unsubstituted, mono- or di-substituted, wherein each aryl substituent is independently chosen from C1-C6 alkyl and C1-C6 alkoxy; and lengthening agent L;(iii) —CH(X2)(X3), wherein,(1) X2 is chosen from at least one of lengthening agent L, C1-C12 alkyl, and an aryl group that is unsubstituted, mono- or di-substituted, wherein each aryl substituent is independently chosen from C1-C6 alkyl and C1-C6 alkoxy; and(2) X3 is chosen from at least one of —COOX1, —COX1, —COX4, and —CH2OX5, wherein: X4 is chosen from at least one of morpholino, piperidino, amino that is unsubstituted, mono- or di-substituted with C1-C6 alkyl, and an unsubstituted, mono or di-substituted group chosen from phenylamino and diphenylamino, wherein each substituent is independently chosen from C1-C6 alkyl or C1-C6 alkoxy; and X5 is chosen from hydrogen, lengthening agent L, —C(O)X2, C1-C12 alkyl that is unsubstituted or mono-substituted with (C1-C12)alkoxy or phenyl, phenyl(C1-C12)alkyl that is mono-substituted with (C1-C12)alkoxy, and an aryl group that is unsubstituted, mono- or di-substituted, wherein each aryl substituent is independently chosen from C1-C6 alkyl and C1-C6 alkoxy;(iv) an unsubstituted, mono-, di-, or tri-substituted aryl group; 9-julolidinyl; or an unsubstituted, mono- or di-substituted heteroaromatic group chosen from pyridyl, furanyl, benzofuran-2-yl, benzofuran-3-yl, thienyl, benzothien-2-yl, benzothien-3-yl, dibenzofuranyl, dibenzothienyl, carbazoyl, benzopyridyl, indolinyl, or fluorenyl; wherein each aryl and heteroaromatic group substituent is independently chosen for each occurrence from:(1) lengthening agent L;(2) —COOX1 or —C(O)X6;(3) aryl, haloaryl, C3-C7 cycloalkylaryl, and an aryl group that is mono- or di-substituted with C1-C12 alkyl or C1-C12 alkoxy;(4) C1-C12 alkyl, C3-C7 cycloalkyl, C3-C7 cycloalkyloxy(C1-C12)alkyl, aryl(C1-C12)alkyl, aryloxy(C1-C12)alkyl, mono- or di-(C1-C12)alkylaryl(C1-C12)alkyl, mono- or di-(C1-C12)alkoxyaryl(C1-C12)alkyl, haloalkyl, and mono(C1-C12)alkoxy(C1-C12)alkyl;(5) C1-C12 alkoxy, C3-C7 cycloalkoxy, cycloalkyloxy(C1-C12)alkoxy, aryl(C1-C12)alkoxy, aryloxy(C1-C12)alkoxy, mono- or di-(C1-C12)alkylaryl(C1-C12)alkoxy, and mono- or di-(C1-C12)alkoxyaryl(C1-C12)alkoxy;(6) amido, amino, mono- or di-alkylamino, diarylamino, piperazino, N—(C1-C18)alkylpiperazino, N-arylpiperazino, aziridino, indolino, piperidino, morpholino, thiomorpholino, tetrahydroquinolino, tetrahydroisoquinolino, pyrrolidyl, hydroxy, acryloxy, methacryloxy, and halogen;(7) —OX7 or —N(X7)2;(8) an unsubstituted or mono-substituted group chosen from pyrazolyl, imidazolyl, pyrazolinyl, imidazolinyl, pyrrolidinyl, phenothiazinyl, phenoxazinyl, phenazinyl, or acridinyl, wherein each substituent is independently chosen from lengthening agent L, C1-C8 alkyl, C1-C8 alkoxy, phenyl, hydroxy, amino or halogen;(D) R3 and R4 are each independently selected from hydrogen, C1-C8 alkyl, C1-C8 haloalkyl, and C3-C7 cycloalkyl, or R3 and R4 together form a spiro substituent selected from a substituted or unsubstituted spiro-carbocyclic ring containing 3 to 6 carbon atoms; and(E) R5 is selected from hydrogen and —C(O)—R13. 4. The indeno-fused ring compound of claim 1, wherein, (A) Ring-A is unsubstituted aryl or substituted aryl;(B) for Q′, each Ra is independently selected from hydrogen and an alkyl group having from 1 to 6 carbon atoms, and Rb is selected from a perfluorinated alkyl group having from 1 to 6 carbon atoms;(C) R1 for each i, and R2 for each t, are each independently selected from, (a) —C(O)X24, wherein X24 is chosen from hydroxy, C1-C6 alkyl, C1-C6 alkoxy, phenyl that is unsubstituted or mono-substituted with C1-C6 alkyl or C1-C6 alkoxy, amino that is unsubstituted, mono- or di-substituted with at least one of C1-C6 alkyl, phenyl, benzyl, and naphthyl;(b) —OX7 and —N(X7)2; wherein X7 is chosen from, (i) hydrogen, C1-C6 alkyl, C1-C6 acyl, phenyl(C1-C6)alkyl, mono(C1-C6)alkyl substituted phenyl(C1-C6)alkyl, mono(C1-C6)alkoxy substituted phenyl(C1-C6)alkyl; C1-C6 alkoxy(C1-C6)alkyl; C3-C5 cycloalkyl; mono(C1-C6)alkyl substituted C3-C5 cycloalkyl, C1-C6 haloalkyl, allyl, benzoyl, mono-substituted benzoyl, naphthoyl or mono-substituted naphthoyl, wherein each of said benzoyl and naphthoyl substituents are independently chosen from C1-C3 alkyl, and C1-C3 alkoxy,(ii) —CH(X8)X9, wherein X8 is chosen from hydrogen or C1-C6 alkyl; and X9 is chosen from —CN, —CF3, or —COOX10, wherein X10 is chosen from hydrogen or C1-C6 alkyl, and(iii) —C(O)X6, wherein X6 is chosen from hydrogen, C1-C12 alkoxy, phenoxy that is unsubstituted, mono- or di-substituted with C1-C6 alkyl or C1-C6 alkoxy, an aryl group that is unsubstituted, mono- or di-substituted with C1-C3 alkyl or C1-C3 alkoxy, an amino group that is unsubstituted, mono- or di-substituted with C1-C3 alkyl, and a phenylamino group that is unsubstituted, mono- or di-substituted with C1-C3 alkyl or C1-C3 alkoxy;(c) nitrogen containing ring represented by Formula i, wherein, each —Y— is independently chosen for each occurrence from —CH2—, —CH(R13′)—, —C(R13′)2—, —CH(aryl)-, —C(aryl)2-, and —C(R13′)(aryl)-, and Z is —Y—, —O—, —S—, —S(O)—, —SO2—, —NH—, —N(R13′)—, or —N(aryl)-, wherein each R13′ is independently lengthening group L, or C1-C20 alkyl, each aryl is independently phenyl or naphthyl, m is an integer 1, 2 or 3, and p is an integer 0, 1, 2, or 3, provided that when p is 0, Z is —Y—;(d) a group represented by Formula ii or iii, wherein X14, X15, and X16 are independently chosen for each occurrence from hydrogen, C1-C6 alkyl, or phenyl or X14 and X15 together form a ring of 5 to 7 carbon atoms; p is an integer chosen from 0, 1, or 2, and X17 is independently chosen for each occurrence from C1-C6 alkyl, C1-C6 alkoxy, or halogen;(e) immediately adjacent R1 groups, and immediately adjacent R2 groups, in each case independently together form a group represented by Formula vii, viii, or ix, wherein, (i) W and W′ are independently chosen for each occurrence from —O—, —N(X7)—, —C(X14)—, and —C(X17)—,(ii) wherein X14 and X15 are independently chosen for each occurrence from hydrogen, C1-C6 alkyl, phenyl or naphthyl, or X14 and X15 together form a ring of 5 to 7 carbon atoms; and X17 is independently chosen for each occurrence from C1-C6 alkyl, C1-C6 alkoxy, or halogen, and(iii) q is an integer chosen from 0 to 3;(f) lengthening agent L,(g) a group B selected from, (i) C1-C6 alkyl, C3-C5 cycloalkyl, C1-C6 haloalkyl and benzyl that is unsubstituted or mono-substituted with at least one of C1-C3 alkyl and C1-C3 alkoxy;(ii) —CH(CN)2 and —CH(COOX1)2, wherein X1 is chosen from hydrogen, C1-C6 alkyl that is unsubstituted or mono-substituted with phenyl, phenyl(C1-C3)alkyl that is mono-substituted with C1-C3 alkyl or C1-C3 alkoxy, and an aryl group that is unsubstituted, mono- or di-substituted, wherein each aryl substituent is independently chosen from C1-C3 alkyl and C1-C3 alkoxy; and lengthening agent L;(iv) —CH(X2)(X3), wherein,(1) X2 is chosen from at least one of lengthening agent L, C1-C6 alkyl, and an aryl group that is unsubstituted, mono- or di-substituted, wherein each aryl substituent is independently chosen from C1-C3 alkyl and C1-C3 alkoxy; and(2) X3 is chosen from at least one of —COOX1, —COX1, —COX4, and —CH2OX5, wherein: X4 is chosen from at least one of morpholino, piperidino, amino that is unsubstituted, mono- or di-substituted with C1-C3 alkyl, and an unsubstituted, mono or di-substituted group chosen from phenylamino and diphenylamino, wherein each substituent is independently chosen from C1-C3 alkyl or C1-C3 alkoxy; and X5 is chosen from hydrogen, lengthening agent L, —C(O)X2, C1-C6 alkyl that is unsubstituted or mono-substituted with (C1-C6)alkoxy or phenyl, phenyl(C1-C12)alkyl that is mono-substituted with (C1-C6)alkoxy, and an aryl group that is unsubstituted, mono- or di-substituted, wherein each aryl substituent is independently chosen from C1-C3 alkyl and C1-C3 alkoxy;(v) an unsubstituted, mono-, di-, or tri-substituted aryl group; 9-julolidinyl; or an unsubstituted, mono- or di-substituted heteroaromatic group chosen from pyridyl, furanyl, benzofuran-2-yl, benzofuran-3-yl, thienyl, benzothien-2-yl, benzothien-3-yl, dibenzofuranyl, dibenzothienyl, carbazoyl, benzopyridyl, indolinyl, or fluorenyl; wherein each substituent is independently chosen for each occurrence from,(1) lengthening agent L;(2) —C(O)X6;(3) aryl, haloaryl, C3-C7 cycloalkylaryl, and an aryl group that is mono- or di-substituted with C1-C12 alkyl or C1-C12 alkoxy;(4) C1-C6 alkyl, C3-C6 cycloalkyl, C3-C5 cycloalkyloxy(C1-C6)alkyl, aryl(C1-C6)alkyl, aryloxy(C1-C6)alkyl, mono- or di-(C1-C6)alkylaryl(C1-C6)alkyl, mono- or di-(C1-C6)alkoxyaryl(C1-C6)alkyl, haloalkyl, and mono(C1-C6)alkoxy(C1-C6)alkyl;(5) C1-C6 alkoxy, C3-C5 cycloalkoxy, cycloalkyloxy(C1-C6)alkoxy, aryl(C1-C6)alkoxy, aryloxy(C1-C6)alkoxy, mono- or di-(C1-C6)alkylaryl(C1-C6)alkoxy, and mono- or di-(C1-C6)alkoxyaryl(C1-C6)alkoxy;(6) aminocarbonyl, aminocarbonyl(C1-C18)alkylene, amino, mono- or di-alkylamino, diarylamino, piperazino, N—(C1-C18)alkylpiperazino, N-arylpiperazino, aziridino, indolino, piperidino, morpholino, thiomorpholino, tetrahydroquinolino, tetrahydroisoquinolino, pyrrolidyl, hydroxy, acryloxy, methacryloxy, and halogen;(7) —OX7 or —N(X7)2, and(8) an unsubstituted or mono-substituted group chosen from pyrazolyl, imidazolyl, pyrazolinyl, imidazolinyl, pyrrolidinyl, phenothiazinyl, phenoxazinyl, phenazinyl, or acridinyl, wherein each substituent is independently chosen from lengthening agent L, C1-C3 alkyl, C1-C3 alkoxy, phenyl, hydroxy, amino or halogen;(D) R3 and R4 are each independently selected from hydrogen, C1-C8 alkyl, C1-C8 haloalkyl, and C3-C7 cycloalkyl, or R3 and R4 together form a spiro substituent selected from a substituted or unsubstituted spiro-carbocyclic ring containing 3 to 6 carbon atoms; and(E) R5 is selected from hydrogen and —C(O)—R13. 5. The indeno-fused ring compound of claim 4, wherein said indeno-fused ring compound is represented by the following Formula Ia, wherein t is selected from 0 to 4. 6. The indeno-fused ring compound of claim 5, wherein Q′ is selected from —CN, —C(O)ORa, —C(O)Ra, —C≡C—Ra, —C(Ra)═C(Ra)(Ra), —OC(O)Ra, —OC(O)ORa, —SRa, —OS(O2)Rb and —C(O)NRaRa.
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