Hindered amine stabilized UV active organopalladium catalyzed polycycloolefin compositions as optical materials

A kit for forming a substantially transparent film comprising:

• a) one or more olefinic monomers of the formula (V):
• wherein:
• m is an integer 0, 1 or 2;
• is a single bond or a double bond;
• R13, R14, R15 and R16 are the same or different and each independently selected from the group consisting of hydrogen, halogen, a hydrocarbyl or halohydrocarbyl group selected from methyl, ethyl, linear or branched (C3-C16)alkyl, perfluoro(C1-C12)alkyl, (C3-C12)cycloalkyl, (C6-C12)bicycloalkyl, (C7-C14)tricycloalkyl, (C6-C10)aryl, (C6-C10)aryl(C1-C6)alkyl, perfluoro(C6-C10)aryl, perfluoro(C6-C10)aryl(C1-C6)alkyl, methoxy, ethoxy, linear or branched (C3-C16)alkoxy, epoxy(C1-C10)alkyl, epoxy(C1-C10)alkyloxy(C1-C10)alkyl, epoxy(C3-C10)cycloalkyl, perfluoro(C1-C12)alkoxy, (C3-C12)cycloalkoxy, (C6-C12)bicycloalkoxy, (C7-C14)tricycloalkoxy, (C6-C10)aryloxy, (C6-C10)aryl(C1-C6)alkoxy, perfluoro(C6-C10)aryloxy, perfluoro(C6-C10)aryl(C1-C3)alkoxy,
• a group of formula (A):
• —Z-Aryl (A);
• a group of formula (A1):
• a group of formula (A2):
• a group of formula (A3):
• and
• a group of formula (A4):
• wherein:
• Z is selected from the group consisting of:
• O, CO, C(O)O, OC(O), OC(O)O, S, (CR17R18)b, O(CR17R18)b, (CR17R18)bO, C(O)(CR17R18)b, (CR17R18)bC(O), C(O)O(CR17R18)b, (CR17R18)bC(O)O, OC(O)(CR17R18)b, (CR17R18)bOC(O), (CR17R18)bOC(O)O, (CR17R18)bOC(O)O(CR17R18)b, OC(O)O(CR17R18)b, S(CR17R18)b, (CR17R18)bS, (SiR17R18)b, O(SiR17R18)b, and (SiR17R18)bO, where
• R17 and R18 are the same or different and each independently selected from hydrogen, methyl, ethyl, linear or branched (C3-C12)alkyl, substituted or unsubstituted (C6-C14)aryl, methoxy, ethoxy, linear or branched (C3-C6)alkyloxy, (C2-C6)acyl, (C2-C6)acyloxy, and substituted or unsubstituted (C6-C14)aryloxy;
• and
• b is an integer from 0 to 12, inclusive;
• Aryl is selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl and substituted or unsubstituted naphthyl, substituted or unsubstituted terphenyl, substituted or unsubstituted anthracenyl substituted or unsubstituted fluorenyl, wherein substituents are selected from the group consisting of halogen, methyl, ethyl, linear or branched (C3-C6)alkyl, perfluoro(C1-C12)alkyl, (C3-C12)cycloalkyl, (C6-C10)aryl, (C6-C10)aryl(C1-C6)alkyl, perfluoro(C6-C10)aryl, perfluoro(C6-C10)aryl(C1-C6)alkyl, methoxy, ethoxy, linear or branched (C3-C16)alkoxy, perfluoro(C1-C12)alkoxy, (C3-C12)cycloalkoxy, (C6-C10)aryloxy, (C6-C10)aryl(C1-C6)alkoxy, perfluoro(C6-C10)aryloxy and perfluoro(C6-C10)aryl(C1-C3)alkoxy;
• k is an integer from 1 to 12;
• R23, R24 and R25 are the same or different and each independently selected from the group consisting of hydrogen, methyl, ethyl, linear or branched (C3-C12)alkyl, perfluoro(C1-C12)alkyl, methoxy, ethoxy, linear or branched (C3-C12)alkoxy, (C3-C12)cycloalkyl, (C6-C12)bicycloalkyl, (C7-C14)tricycloalkyl, (C6-C10)aryl, (C6-C10)aryl(C1-C6)alkyl, perfluoro(C6-C10)aryl and perfluoro(C6-C10)aryl(C1-C6)alkyl;
• or
• R23 and R24 taken together with the intervening carbon atoms to which they are attached to form a substituted or unsubstituted (C5-C14)cyclic, (C5-C14)bicyclic or (C5-C14)tricyclic ring;
• and Arylene is substituted or unsubstituted bivalent (C6-C14)arylene;
• or
• one of R1 and R2 taken together with one of R3 and R4 and the carbon atoms to which they are attached to form a substituted or unsubstituted (C5-C14)cyclic, (C5-C14)bicyclic or (C5-C14)tricyclic ring;
• b) an organopalladium compound selected from the group consisting of a compound of formula (I), a compound of formula (IA) and a compound of formula (IB):
• wherein:
• L is a ligand selected from the group consisting of P(R)3, P(OR)3, O═P(R)3, RCN and substituted or unsubstituted pyridines, where R is selected from the group consisting of methyl, ethyl, linear or branched (C3-C16)alkyl, (C1-C16)perfluoroalkyl, (C3-C10)cycloalkyl, (C6-C10)aryl(C1-C16)alkyl and substituted or unsubstituted (C6-C10)aryl;
• each A independently is a bidentate monoanionic ligand of formula (II):
• wherein:
• n is an integer 0, 1 or 2;
• X and Y are independently of each other selected from O, N and S;
• R1, R2, R3, R4, R5, R6 and R7 are the same or different and each independently selected from the group consisting of hydrogen, methyl, ethyl, linear or branched (C3-C16)alkyl, (C3-C10)cycloalkyl, (C6-C10)aryl(C1-C16)alkyl and substituted or unsubstituted (C6-C10)aryl;
• provided when either X or Y is O or S, R1 and R5, respectively, do not exist;
• c) a photoacid generator selected from the group consisting of:
• a compound of formula (III):
• and
• a compound of formula (IV):
• wherein:
• a is an integer from 0 to 5;
• An⊖ is selected from the group consisting of Cl⊖, Br⊖, I⊖, BF4⊖, tetrakis(pentafluorophenyl)borate, tetrakis(3,5-bis(trifluoromethyl)phenyl)borate, tetrakis(2-fluorophenyl)borate, tetrakis(3-fluorophenyl)borate, tetrakis(4-fluorophenyl)borate, tetrakis(3,5-difluorophenyl)borate, tetrakis(2,3,4,5-tetrafluorophenyl)borate, tetrakis(3,4,5,6-tetrafluorophenyl)borate, tetrakis(3,4,5-trifluorophenyl)borate, methyltris(perfluorophenyl)borate, ethyltris(perfluorophenyl)borate, phenyltris(perfluorophenyl)borate, tetrakis(1,2,2-trifluoroethylenyl)borate, tetrakis(4-tri-1-propylsilyltetrafluorophenyl)borate, tetrakis(4-dimethyl-tert-butylsilyltetrafluorophenyl)borate, (triphenylsiloxy)tris(pentafluorophenyl)borate, (octyloxy)tris(pentafluorophenyl)borate, tetrakis[3,5-bis[1-methoxy-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]pheny-l]borate, tetrakis[3-[1-methoxy-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]-5-(trifluoromethyl)phenyl]borate, and tetrakis[3-[2,2,2-trifluoro-1-(2,2,2-trifluoroethoxy)-1-(trifluoromethyl)-ethyl]-5-(trifluoromethyl)phenyl]borate,
• PF6⊖, SbF6⊖, n-C4F9SO3⊖, CF3SO3⊖ and p-CH3(C6H4)—SO3⊖;
• R8, R9, R10, R11 and R12 are the same or different and each independently selected from the group consisting of halogen, methyl, ethyl, linear or branched (C3-C20)alkyl, (C3-C12)cycloalkyl, (C6-C12)bicycloalkyl, (C7-C14)tricycloalkyl, (C6-C10)aryl, (C6-C10)aryl(C1-C3)alkyl, (C1-C12)alkoxy, (C3-C12)cycloalkoxy, (C6-C12)bicycloalkoxy, (C7-C14)tricycloalkoxy, (C6-C10)aryloxy(C1-C3)alkyl, (C6-C10)-aryloxy, (C6-C10)-thioaryl, (C1-C6)alkanoyl(C6-C10)thioaryl, (C1-C6)alkoxy(C6-C10)aroyl(C1-C6)alkyl and (C6-C10)-thioaryl-(C6-C10)diarylsulfonium salt;
• d) a compound selected from the group consisting of:
• a compound of formula (X):
• where Z1, Z2 and Z3 are the same or different and each independently is ((CH2)gO)h(CH2)g) where g and h are integers from 2 to 4;
• a compound of formula (XI):
• where R49, R50, R51 and R52 are the same or different and each independently selected from the group consisting of hydrogen, methyl, ethyl and linear or branched (C3-C20)alkyl;
• and
• a compound of formula (XII):
• a compound of formula (XIII):
• where j is an integer from 6 to 16;
• R53, R54, R56, R57 and R58 are the same or different and each independently selected from the group consisting of hydrogen, methyl, ethyl and linear or branched (C3-C20)alkyl;
• R55 is selected from the group consisting of methyl, ethyl, linear or branched (C3-C20)alkyl, methoxy, ethoxy and linear or branched (C3-C20)alkoxy;
• and
• a compound of formula (XIV):
• where each m maybe same or different and is an integer from 2 to 6;
• R59 is a group of formula:
• R60, R61, R62, R63, R64 and R65 are the same or different and each independently selected from the group consisting of hydrogen, methyl, ethyl and linear or branched (C3-C20)alkyl;
• and
• a compound of formula (XV):
• where p is an integer from 1 to 5;
• each R66 maybe the same or different and each independently selected from the group consisting of halogen, methyl, ethyl and linear or branched (C3-C20)alkyl and NR67R68, where each R67 and R67 are the same or different and each independently selected from the group consisting of methyl, ethyl and linear or branched (C3-C20)alkyl;
• and
• e) a photosensitizer.