Cyclic olefins compounds, polymers comprising the same and liquid crystal alignment films including the polymers

The polymer comprising a repeating unit that is represented by the following Formula 11:

• wherein n is in the range of 50 to 5,000, p is an integer in the range of 0 to 4, and at least one of R1, R2, R3, and R4 is a radical that is represented by the following Formula 2:
• wherein m is an integer in the range of 1 to 5,
• A is any one selected from substituted or unsubstituted linear or branched alkylene having 1 to 20 carbon atoms;
• carbonyl;
• and substituted or unsubstituted arylene or haloarylene having 6 to 40 carbon atoms,
• B and B′ are the same as or different from each other, and oxygen or nitrogen,
• R9 is any one selected from a direct bond, linear or branched alkylene or haloalkylene having 1 to 20 carbon atoms;
• linear or branched alkenylene or haloalkenylene having 2 to 20 carbon atoms;
• substituted or unsubstituted cycloalkylene or halocycloalkylene having 5 to 12 carbon atoms;
• substituted or unsubstituted arylene or haloarylene having 6 to 40 carbon atoms;
• substituted or unsubstituted aralkylene or haloaralkylene having 7 to 15 carbon atoms;
• and alkynylene or haloalkynylene having 2 to 20 carbon atoms, and
• X is any one selected from functional groups that are represented by the following Formulae 3, 4 and 5,
• wherein * means a connection unit, and
• R10 is hydrogen;
• or an alkyl or cycloalkyl group having 1 to 4 carbon atoms,
• wherein * means a connection unit, and
• n is an integer in the range of 1 to 9,
• wherein n is an integer in the range of 0 to 9,
• among R1, R2, R3, and R4, the remainders other than the group that is represented by Formula 2 are each independently selected from hydrogen;
• halogen;
• linear or branched alkyl that has 1 to 20 carbon atoms and is substituted or unsubstituted with one or more substituent groups selected from the group consisting of halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, haloaryloxy, silyl, and siloxy;
• linear or branched alkenyl that has 2 to 20 carbon atoms and is substituted or unsubstituted with one or more substituent groups selected from the group consisting of halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, haloaryloxy, silyl, and siloxy;
• linear or branched alkynyl that has 2 to 20 carbon atoms and is substituted or unsubstituted with one or more substituent groups selected from the group consisting of halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, haloaryloxy, silyl, and siloxy;
• cycloalkyl that has 3 to 12 carbon atoms and is substituted or unsubstituted with one or more substituent groups selected from the group consisting of halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, haloaryloxy, silyl, and siloxy;
• aryl that has 6 to 40 carbon atoms and is substituted or unsubstituted with one or more substituent groups selected from the group consisting of halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, haloaryloxy, silyl, and siloxy;
• and a polar functional group that contains at least one of oxygen, nitrogen, phosphorus, sulfur, silicon, and boron,
• R1 and R2 or R3 and R4 may be bonded to each other to form an alkylidene group having 1 to 10 carbon atoms or R1 or R2 may be bonded to any one of R3 and R4 to form a saturated or unsaturated aliphatic ring having 4 to 12 carbon atoms or an aromatic ring having 6 to 24 carbon atoms,
• the polar functional group includes compounds represented by the following Formulae:
• —R5OR6, —OR6, —OC(O)OR6, —R5OC(O)OR6, —C(O)OR6, —R5C(O)OR6, —C(O)R6, —R5C(O)R6, —OC(O)R6, —R5OC(O)R6, —(R5O)p—OR6 (p is an integer in the range of 1 to 10), —(OR5)p—OR6 (p is an integer in the range of 1 to 10), —C(O)—O—C(O)R6, —R5C(O)—O—C(O)R6, —SR6, —R5SR6, —SSR6, —R5SSR6, —S(═O)R6, —R5S(═O)R6, —R5C(═S)R6—, —R5C(═S)SR6, —R5SO3R6, —SO3R6, —R5N═C═S, —N═C═S, —NCO, —R5—NCO, —CN, —R5CN, —NNC(═S)R6, —R5NNC(═S)R6, —NO2, —R5NO2,
• in the polar functional group, R5 is linear or branched alkylene that has 1 to 20 carbon atoms and is substituted or unsubstituted with one or more substituent groups selected from the group consisting of halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, haloaryloxy, silyl, and siloxy;
• linear or branched alkenylene that has 2 to 20 carbon atoms and is substituted or unsubstituted with one or more substituent groups selected from the group consisting of halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, haloaryloxy, silyl, and siloxy;
• linear or branched alkynylene that has 2 to 20 carbon atoms and is substituted or unsubstituted with one or more substituent groups selected from the group consisting of halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, haloaryloxy, silyl, and siloxy;
• cycloalkylene that has 3 to 12 carbon atoms and is substituted or unsubstituted with one or more substituent groups selected from the group consisting of halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, haloaryloxy, silyl, and siloxy;
• arylene that has 6 to 40 carbon atoms and is substituted or unsubstituted with one or more substituent groups selected from the group consisting of halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, haloaryloxy, silyl, and siloxy;
• or alkoxylene that has 1 to 20 carbon atoms and is substituted or unsubstituted with one or more substituent groups selected from the group consisting of halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, haloaryloxy, silyl, and siloxy;
• two or more R5s are the same as or different from each other when two or more R5s are present, and
• R6, R7, and R8 are the same as or different from each other, and hydrogen;
• halogen;
• linear or branched alkyl that has 1 to 20 carbon atoms and is substituted or unsubstituted with one or more substituent groups selected from the group consisting of halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, haloaryloxy, silyl, and siloxy;
• linear or branched alkenyl that has 2 to 20 carbon atoms and is substituted or unsubstituted with one or more substituent groups selected from the group consisting of halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, haloaryloxy, silyl, and siloxy;
• linear or branched alkynyl that has 2 to 20 carbon atoms and is substituted or unsubstituted with one or more substituent groups selected from the group consisting of halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, haloaryloxy, silyl, and siloxy;
• cycloalkyl that has 3 to 12 carbon atoms and is substituted or unsubstituted with one or more substituent groups selected from the group consisting of halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, haloaryloxy, silyl, and siloxy;
• aryl that has 6 to 40 carbon atoms and is substituted or unsubstituted with one or more substituent groups selected from the group consisting of halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, haloaryloxy, silyl, and siloxy;
• or alkoxy that has 1 to 20 carbon atoms and is substituted or unsubstituted with one or more substituent groups selected from the group consisting of halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, aralkyl, haloaralkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, haloaryloxy, silyl, and siloxy.