Cyclic olefin compound having photoreactive group and photoreactive polymer

Patent metadata

Field	Value
Publication number	US-9982071-B2
Application number	US-201414911462-A
Country	US
Kind code	B2
Filing date	Sep 26, 2014
Priority date	Sep 30, 2013
Publication date	May 29, 2018
Grant date	May 29, 2018

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.

First claim

The invention claimed is:

1. 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.

2. The cyclic olefin compound of claim 1 , wherein the polar functional group including at least one selected from oxygen, nitrogen, phosphorus, sulfur, silicon, and boron is selected from the group consisting of the following functional groups:
—OR 6 , —OC(O)OR 6 , —R 5 OC(O)OR 6 , —C(O)OR 6 , —R 5 C(O)OR 6 , —C(O)R 6 , —R 5 C(O)R 6 , —OC(O)R 6 , —R 5 OC(O)R 6 , —(R 5 O) p —OR 6 , —(OR 5 ) p —OR 6 , —C(O)—O—C(O)R 6 , —R 5 C(O)—O—C(O)R 6 , —SR 6 , —R 5 SR 6 , —SSR 6 , —R 5 SSR 6 , —S(═O)R 6 , —R 5 S(═O)R 6 , —R 5 C(═S)R 6 —, —R 5 C(═S)SR 6 , —R 5 SO 3 R 6 , —SO 3 R 6 , —R 5 N═C═S, —N═C═S, —NCO, —R 5 —NCO, —CN, —R 5 CN, —NNC(═S)R 6 , —R 5 NNC(═S)R 6 , —NO 2 , —R 5 NO 2 ,

in the polar functional groups, each p is independently an integer from 1 to 10,
R 5 is substituted or unsubstituted linear or branched alkylene having 1 to 20 carbon atoms; substituted or unsubstituted linear or branched alkenylene having 2 to 20 carbon atoms; substituted or unsubstituted linear or branched alkynylene 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 carbonyloxylene having 1 to 20 carbon atoms; or substituted or unsubstituted alkoxylene having 1 to 20 carbon atoms; and
R 6 , R 7 , and R 8 are 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 alkoxy having 1 to 20 carbon atoms; and substituted or unsubstituted carbonyloxy having 1 to 20 carbon atoms.

3. The cyclic olefin compound of claim 2 , wherein each functional group of R5 to R8 is unsubstituted or substituted with a functional group selected from the group consisting of halogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, aryl, haloaryl, arylalkyl, haloarylalkyl, alkoxy, haloalkoxy, carbonyloxy, halocarbonyloxy, aryloxy, haloaryloxy, silyl, and siloxy.

4. 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 o

Assignees

• Lg Chemical Ltd

Inventors

• Park Eun Seok
• Chun Sung-Ho
• Choi Dai Seung

Classifications

• C07C2603/91

  Polycyclopentadienes; Hydrogenated polycyclopentadienes · CPC title

• C08G2261/76

  crosslinking · CPC title

• C07C69/618

  having unsaturation outside the six-membered aromatic ring · CPC title

• C07C2601/14

  The ring being saturated · CPC title

• G02F1/13363

  Birefringent elements, e.g. for optical compensation · CPC title