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US 9,982,071 B2Granted
Cyclic olefin compound having photoreactive group and photoreactive polymer
AssigneeLG Chem, Ltd.
InventorsEun Seok Park, Sung-Ho Chun, Dai Seung Choi
Life of this patent
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Abstract
There are provided a novel cyclic olefin compound having a photoreactive group and a photoreactive polymer. The cyclic olefin compound is applicable to various photoreactions, such as of liquid crystal alignment layers and can be preferably used as a precursor of various organic compounds or polymers.
Claims12
A cyclic olefin compound having a photoreactive group represented by the following Chemical Formula 1:
- in Chemical Formula 1,
- q is an integer from 0 to 4;
- at least one of R1, R2, R3, and R4 is a radical represented by the following Chemical Formula 1a,
- among R1 to R4, the remainders other than the radical of Chemical Formula 1a are the same as or different from one another and each independently selected from the group consisting of hydrogen;
- halogen;
- substituted or unsubstituted linear or branched alkyl having 1 to 20 carbon atoms;
- substituted or unsubstituted linear or branched alkenyl having 2 to 20 carbon atoms;
- substituted or unsubstituted linear or branched alkynyl having 2 to 20 carbon atoms;
- substituted or unsubstituted cycloalkyl having 3 to 12 carbon atoms;
- substituted or unsubstituted aryl having 6 to 40 carbon atoms;
- substituted or unsubstituted arylalkyl having 5 to 12 carbon atoms;
- and a polar functional group including at least one selected from oxygen, nitrogen, phosphorus, sulfur, silicon, and boron,
- when R1 to R4 are not hydrogen, halogen, or a polar functional group, at least one combination of R1 and R2 or R3 and R4 is bonded to each other to form an alkylidene group having 1 to 10 carbon atoms, or R1 or R2 is bonded to either R3 or 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,
- in Chemical Formula 1a,
- A is selected from the group consisting of a single bond, substituted or unsubstituted alkylene having 1 to 20 carbon atoms, substituted or unsubstituted alkenylene having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkylene having 3 to 12 carbon atoms, substituted or unsubstituted arylene having 6 to 40 carbon atoms, substituted or unsubstituted arylalkylene having 7 to 15 carbon atoms, and substituted or unsubstituted alkynylene having 2 to 20 carbon atoms,
- B is a single bond, oxygen, sulfur, —NH—, or 1,4-phenylene,
- R9 is selected from the group consisting of a single bond, substituted or unsubstituted alkylene having 1 to 20 carbon atoms, substituted or unsubstituted alkenylene having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkylene having 3 to 12 carbon atoms, substituted or unsubstituted arylene having 6 to 40 carbon atoms, substituted or unsubstituted arylalkylene having 7 to 15 carbon atoms, and substituted or unsubstituted alkynylene having 2 to 20 carbon atoms,
- C1 is C6-C40 arylene unsubstituted or substituted with at least one functional group selected from the group consisting of halogen, cyano, and nitro;
- C7-C15 arylalkylene unsubstituted or substituted with at least one functional group selected from halogen, cyano, and nitro;
- or C4-C40 heteroarylene including a hetero element in Group 14, 15 or 16,
- C2 is C6-C40 arylene unsubstituted or substituted with at least one functional group selected from the group consisting of halogen, cyano, and nitro;
- C4-C40 heteroarylene including a hetero element in Group 14, 15 or 16;
- C5-C10 cycloalkylene;
- or C4-C40 heterocycloalkylene including a hetero element in Group 14, 15, or 16,
- C3 is C5-C10 cycloalkylene unsubstituted or substituted with at least one functional group selected from the group consisting of halogen, cyano, and nitro, or C4-C40 heterocycloalkylene including a hetero element in Group 14, 15, or 16,
- D is selected from the group consisting of a single bond, substituted or unsubstituted alkylene having 1 to 20 carbon atoms, substituted or unsubstituted alkenylene having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkylene having 3 to 12 carbon atoms, substituted or unsubstituted arylene having 6 to 40 carbon atoms, substituted or unsubstituted arylalkylene having 7 to 15 carbon atoms, and substituted or unsubstituted alkynylene having 2 to 20 carbon atoms, and
- R10 is selected from the group consisting of hydrogen;
- halogen;
- cyano;
- nitro;
- —NCS;
- substituted or unsubstituted linear or branched alkyl having 1 to 20 carbon atoms;
- substituted or unsubstituted alkoxy having 1 to 20 carbon atoms;
- and substituted or unsubstituted aryloxy having 6 to 30 carbon atoms.
31 more elements
A photoreactive polymer comprising a repeating unit represented by the following Chemical Formula 2a or 2b:
- in Chemical Formulas 2a and 2b, each independently,
- m is 50 to 5000,
- q is an integer from 0 to 4;
- at least one of R1, R2, R3, and R4 is a radical represented by the following Chemical Formula 1a,
- among R1 to R4, the remainders other than the radical of Chemical Formula 1a are the same as or different from one another and each independently selected from the group consisting of hydrogen;
- halogen;
- substituted or unsubstituted linear or branched alkyl having 1 to 20 carbon atoms;
- substituted or unsubstituted linear or branched alkenyl having 2 to 20 carbon atoms;
- substituted or unsubstituted linear or branched alkynyl having 2 to 20 carbon atoms;
- substituted or unsubstituted cycloalkyl having 3 to 12 carbon atoms;
- substituted or unsubstituted aryl having 6 to 40 carbon atoms;
- substituted or unsubstituted arylalkyl having 5 to 12 carbon atoms;
- and a polar functional group including at least one selected from oxygen, nitrogen, phosphorus, sulfur, silicon, and boron,
- when R1 to R4 are not hydrogen, halogen, or a polar functional group, at least one combination of R1 and R2 or R3 and R4 is bonded to each other to form an alkylidene group having 1 to 10 carbon atoms, or R1 or R2 is bonded to either R3 or 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,
- in Chemical Formula 1a,
- A is selected from the group consisting of a single bond, substituted or unsubstituted alkylene having 1 to 20 carbon atoms, substituted or unsubstituted alkenylene having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkylene having 3 to 12 carbon atoms, substituted or unsubstituted arylene having 6 to 40 carbon atoms, substituted or unsubstituted arylalkylene having 7 to 15 carbon atoms, and substituted or unsubstituted alkynylene having 2 to 20 carbon atoms,
- B is a single bond, oxygen, sulfur, —NH—, or 1,4-phenylene,
- R9 is selected from the group consisting of a single bond, substituted or unsubstituted alkylene having 1 to 20 carbon atoms, substituted or unsubstituted alkenylene having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkylene having 3 to 12 carbon atoms, substituted or unsubstituted arylene having 6 to 40 carbon atoms, substituted or unsubstituted arylalkylene having 7 to 15 carbon atoms, and substituted or unsubstituted alkynylene having 2 to 20 carbon atoms,
- C1 is C6-C40 arylene unsubstituted or substituted with at least one functional group selected from the group consisting of halogen, cyano, and nitro;
- C7-C15 arylalkylene unsubstituted or substituted with at least one functional group selected from halogen, cyano, and nitro;
- or C4-C40 heteroarylene including a hetero element in Group 14, 15 or 16,
- C2 is C6-C40 arylene unsubstituted or substituted with at least one functional group selected from the group consisting of halogen, cyano, and nitro;
- C4-C40 heteroarylene including a hetero element in Group 14, 15 or 16;
- C5-C10 cycloalkylene;
- or C4-C40 heterocycloalkylene including a hetero element in Group 14, 15, or 16,
- C3 is C5-C10 cycloalkylene unsubstituted or substituted with at least one functional group selected from the group consisting of halogen, cyano, and nitro, or C4-C40 heterocycloalkylene including a hetero element in Group 14, 15, or 16,
- D is selected from the group consisting of a single bond, substituted or unsubstituted alkylene having 1 to 20 carbon atoms, substituted or unsubstituted alkenylene having 2 to 20 carbon atoms, substituted or unsubstituted cycloalkylene having 3 to 12 carbon atoms, substituted or unsubstituted arylene having 6 to 40 carbon atoms, substituted or unsubstituted arylalkylene having 7 to 15 carbon atoms, and substituted or unsubstituted alkynylene having 2 to 20 carbon atoms, and
- R10 is selected from the group consisting of hydrogen;
- halogen;
- cyano;
- nitro;
- —NCS;
- substituted or unsubstituted linear or branched alkyl having 1 to 20 carbon atoms;
- substituted or unsubstituted alkoxy having 1 to 20 carbon atoms;
- and substituted or unsubstituted aryloxy having 6 to 30 carbon atoms.
32 more elements
Dependencies are inferred from the claim text.