Cycloalkylnorbornene compounds with heterocyclic functionality for voc-free crosslinking and surface functionalization

A norbornene compound having formula (I), formula (II), formula (III), formula (IV), formula (V) or formula (VI):

• wherein p is 0, 1 or 2;
• Q1 and Q2 are independently O, S, N(R13), C═O, C(R14)(R15) or (R14)(R15)C—C—(R16)(R17);
• J1 and J2 are independently O, S, N(R18), C═O, or C(R19)(R20);
• J3 is N or C(R19);
• R11 is an (C5-C12)aliphatic group, (C5-C12)heterocyclic group, or (C6-C14)aromatic group bonded to both J1 and J2 or has formula [T]:
• wherein T1, T2, T3, and T4 are each independently selected from O, S, N(R21), C═O and C(R22)(R23), each of S1, S2, S3, and S4 is 0 or 1, provided that S1+S2+S3+S4>0;
• and wherein if S1+S2+S3+S4≥2, [T] is a bidentate ligand bonded to both J1 and J2;
• R12 a (C5-C12)aliphatic group or a (C5-C12)heterocyclic group bonded to both J3 and J2 or has formula [U]:
• wherein U1 is N or C(R22);
• U2, U3, and U4 are each independently selected from O, S, N(R21), C═O and C(R22)(R23) and each of S5, S6, and S7 is 0 or 1;
• wherein if S5+S6+S7≥1, [U] is a bidentate ligand bonded to both J1 and J3;
• R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R13, R14, R15, R16, R17, R18, R19, R20, R21, R22 and R23 are the same or different and are each independently selected from the group consisting of a single bond, hydrogen, halogen, hydroxy, methyl, ethyl, methoxy, ethoxy, linear or branched (C3-C18)alkyl, (C2-C18)alkenyl, (C3-C18)alkoxy, tri(C1-C6)alkylsilyl, tri(C1-C6)alkoxysilyl, di(C1-C6)alkylamino, di(C1-C6)alkyl(C1-C6)alkylamino, perfluoro(C1-C18)alkyl, (C3-C12)cycloalkyl, (C6-C12)bicyclo(C1-C6)alkyl, (C7-C14)tricyclo(C1-C6)alkyl, (C1-C18)thioalkyl, (C2-C6)acyl, (C2-C8)acyloxy, (C6-C14)aryl, (C6-C14)aryl(C1-C8)alkyl, perfluoro(C6-C14)aryl, perfluoro(C6-C14)aryl(C1-C3)alkyl, (C6-C14)aryloxy, (C6-C14)aryl(C1-C6)alkoxy, (C1-C12)alkyl(C1- C12)perfluoro, and at least one of R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R13, R14, R15, R16, R17, R18, R19, R20, R21, R22 and R23 comprises or is substituted with a heterocyclic group having formula (A), formula (B), formula (C), formula (D), formula (E), formula (F), formula (G), or formula (H):
• wherein Z is a Group 14 element other than carbon;
• X is a Group 15 element;
• Y is a Group 16 element;
• m and n are each independently an integer from 1 to 10;
• K1 and K2 are independently O, S, N(R34), or C(R35)(R36);
• R33 is an (C5-C12)aliphatic group, a (C5-C12)heterocyclic, a (C6-C14)aromatic group bonded to both J1 and J2, or has formula [W]:
• wherein W1, W2, W3, and W4 are each independently selected from O, S, N(R37), C═O and C(R39)(R39), each of S8, S9, S10, and S11 is 0 or 1, provided that S8+S9+S10+S11>0;
• wherein if S8+S9+S10+S11≥2, [W] is a bidentate ligand bonded to both K1 and K2;
• R24, R25, R26, R27, R28, R29, R30, R31, R32, R34, R35, R36, R37, R38, and R39 are the same or different and are each independently a single bond, hydrogen, halogen, hydroxy, methyl, ethyl, methoxy, ethoxy, linear or branched (C3-C18)alkyl, (C2-C18)alkenyl, (C3-C18)alkoxy, tri(C1-C6)alkylsilyl, tri(C1-C6)alkoxysilyl, di(C1-C6)alkylamino, di(C1-C6)alkyl(C1-C6)alkylamino, perfluoro(C1-C18)alkyl, (C3-C12)cycloalkyl, (C6-C12)bicyclo(C1-C6)alkyl, (C7-C14)tricyclo(C1-C6)alkyl, (C1-C18)thioalkyl, (C2-C6)acyl, (C2-C8)acyloxy, (C6-C14)aryl, (C6-C14)aryl(C1-C8)alkyl, perfluoro(C6-C14)aryl, perfluoro(C6-C14)aryl(C1-C3)alkyl, (C6-C14)aryloxy, (C6-C14)aryl(C1-C6)alkoxy, or (C1-C12)alkyl(C1-C12)perfluoro;
• where at least one of R24, R25, R26, R27, R28, R29, R30, R31, R32, R34, R35, R36, R37, R38, and R39 is a single bond connecting to a structure of formula (I), formula (II), formula (III), formula (IV), formula (V) or formula (VI).