Purification method of photoreactive compound and photoreactive compound

Patent metadata

Field	Value
Publication number	US-9963418-B2
Application number	US-201414909426-A
Country	US
Kind code	B2
Filing date	Aug 1, 2014
Priority date	Aug 2, 2013
Publication date	May 8, 2018
Grant date	May 8, 2018

Abstract

Provided is a purification method of a photoreactive compound, and a photoreactive compound. According to the purification method of the present invention, a light and heat-sensitive photoreactive compound may be purified in high purity, thereby polymerizing a photoreactive polymer having improved physical properties.

First claim

What is claimed is:

1. A method of purifying a photoreactive compound, the method comprising the steps of:
preparing a crude product including the photoreactive compound of the following Chemical Formula 1;
performing molecular distillation of the crude product including the photoreactive compound at a temperature of 90 to 240° C. and a pressure of 0.001 to 0.8 mbar; and
recovering the photoreactive compound:

wherein p is an integer of 0 to 4,
at least one of R 1 , R 2 , R 3 , and R 4 is a radical selected from the group consisting of Chemical Formulae 2, 3 and 4,
the others are each independently hydrogen, halogen, substituted or unsubstituted C 1 -C 20 alkyl, substituted or unsubstituted C 2 -C 20 alkenyl, substituted or unsubstituted C 3 -C 12 cycloalkyl, substituted or unsubstituted C 6 -C 40 aryl, substituted or unsubstituted C 7 -C 15 aralkyl; substituted or unsubstituted C 2 -C 20 alkynyl, or a polar functional group including a non-hydrocarbonaceous polar group containing at least one element selected from the group consisting of oxygen, nitrogen, phosphorus, sulfur, silicon, and boron, and
if R 1 , R 2 , R 3 , and R 4 are not hydrogen, halogen, or a polar functional group, R 1 and R 2 , or R 3 and R 4 are connected to each other to form a C 1 -C 10 alkylidene group, or R 1 or R 2 is connected to any one of R 3 and R 4 to form a C 4 -C 12 saturated or unsaturated cyclic group or a C 6 -C 24 aromatic ring compound;

wherein A is selected from a single bond, substituted or unsubstituted C 1 -C 20 alkylene, carbonyl, carboxyl, substituted or unsubstituted C 6 -C 40 arylene, and substituted or unsubstituted C 6 -C 40 heteroarylene;
B is a single bond, oxygen, sulfur, or —NH—;
X is oxygen or sulfur;
R 9 is selected from a single bond, substituted or unsubstituted C 1 -C 20 alkylene, substituted or unsubstituted C 2 -C 20 alkenylene, substituted or unsubstituted C 3 -C 12 cycloalkylene, substituted or unsubstituted C 6 -C 40 arylene, substituted or unsubstituted C 7 -C 15 aralkylene, and substituted or unsubstituted C 2 -C 20 alkynylene; and
R 10 , R 11 , R 12 , R 13 , and R 14 are the same as or different from each other, and each independently selected from the group consisting of hydrogen, a hydroxy group, a halogen group, substituted or unsubstituted C 7 -C 15 aralkyl, substituted or unsubstituted C 2 -C 20 alkynyl, substituted or unsubstituted C 1 -C 20 alkyl, substituted or unsubstituted C 1 -C 20 alkoxy, substituted or unsubstituted C 6 -C 30 aryloxy, substituted or unsubstituted C 6 -C 40 aryl, C 6 -C 40 heteroaryl including a heteroatom of Group 14, Group 15, or Group 16, and substituted or unsubstituted C 6 -C 40 alkoxyaryl.

2. The method of claim 1 , wherein R 1 of Chemical Formula 1 is a compound of Chemical Formula 2, and at least one of R 2 , R 3 , and R 4 is selected from the group consisting of Chemical Formulae 2, 3 and 4.

3. The method of claim 1 , wherein the non-hydrocarbonaceous polar group includes the following compounds:
one or more selected from the group consisting of —OR 6 , —R 5 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 (p is an integer of 1 to 10), —(OR 5 ) p —OR 6 (p is an integer of 1 to 10), —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 functional groups, each R 5 is selected from substituted or unsubstituted C 1 -C 20 alkylene, substituted or unsubstituted C 2 -C 20 alkenylene, substituted or unsubstituted C 3 -C 12 cycloalkylene, substituted or unsubstituted C 6 -C 40 arylene, substituted or unsubstituted C 7 -C 15 aralkylene, and substituted or unsubstituted C 2 -C 20 alkynylene, and
R 6 , R 7 , and R 8 are each independently selected from hydrogen, halogen, substituted or unsubstituted C 1 -C 20 alkyl, substituted or unsubstituted C 2 -C 20 alkenyl, substituted or unsubstituted C 3 -C 12 cycloalkyl, substituted or unsubstituted C 6 -C 40 aryl, substituted or unsubstituted C 7 -C 15 aralkyl, and substituted or unsubstituted C 2 -C 20 alkynyl.

4. The method of claim 1 , wherein C 6 -C 40 aryl and C 6 -C 40 heteroaryl containing a heteroatom of Group 14, 15, or 16 in the substituents includes the following Chemical Formulae:

wherein at least one of R′ 10 to R′ 18 should be substituted or unsubstituted C 1 -C 20 alkoxy, or substituted or unsubstituted C 6 -C 30 aryloxy, and
the others are each independently selected from the group consisting of substituted or unsubstituted C 1 -C 20 alkyl, substituted or unsubstituted C 1 -C 20 alkoxy, substituted or unsubstituted C 6 -C 30 aryloxy, and substituted or unsubstituted C 6 -C 40 aryl.

5. The method of claim 1 , wherein the photoreactive compound has a boiling point of 180° C. or higher.

6. The method of claim 1 , further comprising a step of performing preliminary distillation at a temperature of 20 to 200° C. and a pressure of 0.01 to 100 mbar, prior to the step of performing molecular distillation of the crude product.

7. The method of claim 1 , wherein the photoreactive compound recovered after molecular distillation has purity of 90% or higher.

8. The method of claim 1 , wherein the photoreactive compound recovered after molecular distillation has an APHA value of less than 50.

Assignees

• Lg Chemical Ltd

Inventors

• Choi Dai Seung
• Chun Sung-Ho

Classifications

• C07C2602/42

  the bicyclo ring system containing seven carbon atoms · CPC title

• C07C67/54 Primary

  by distillation · CPC title

• C07C69/65

  of unsaturated acids · CPC title

• C07C69/734

  Ethers · CPC title