PUKYONG

LCD 컬러필터용 염료와 NIR 색소의 합성 및 특성 연구

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Alternative Title
Synthesis and characterization of Dye for LCD Color filter and NIR colorant
Abstract
The thesis entitled "Synthesis and characterization of dye for LCD color filter and NIR colorant" is divided into two parts. In the first part we focused our study on the development of coumarin dye for LCD color filter. The second part deals with development of pentarylene bisimide as an efficient NIR colorant.
For the synthesis of coumarin dye, we used the most accessable path which is originally presented by Sir William Perkin. It involves a Perkin reaction between salicylaldehyde and acetic anhydride. The formed coumarin further condensed with 2-amino phenol to get Coumarin-2-one benzoxazole type product. The cynation of Coumarin-2-one benzoxazole was performed to get a bathochromic product. The structure of coumarin dyes was characterized by using NMR, UV/visible spectroscopy and TGA.
In second part, we developed a novel NIR-absorbing pentarylene bisimide as a security colorant. We synthesized pentarylene bisimide in five step. In the first step, the dehydrative condensation of perylene-3,4,9,10-tetracarboxylicdianhydride with 2,6-diisopropylaniline in autoclave was proceeded to give perylene monoimide. After then, bromination of the formed perylene monoimide in second step and successive boronic esterification using Miyaura borylation reaction in third step were performed respectively. In forth step, Suzuki coupling of boronic ester derivative of perylene monoimide and dibromo naphthalene was performed to get coupled bisimide product. In final fifth step, we performed the cyclization of the previous coupled bisimide to get the target compound PBI (Pentarylene Bisimide). The synthesized pentarylene bisimide was characterised using UV/VIS/NIR spectrum, TGA and elemental analysis.
Author(s)
백관
Issued Date
2013
Awarded Date
2013. 2
Type
Dissertation
Publisher
부경대학교
URI
https://repository.pknu.ac.kr:8443/handle/2021.oak/24670
http://pknu.dcollection.net/jsp/common/DcLoOrgPer.jsp?sItemId=000001966048
Affiliation
부경대학교 대학원
Department
대학원 이미지시스템공학과
Advisor
정연태
Table Of Contents
목 차


List of Figures――――――――――――――――――――――iv
List of scheme――――――――――――――――――――――v
List of Table――――――――――――――――――――――v
Abstract――――――――――――――――――――――vi
PART1
Ⅰ. 서 론―――――――――――――――――――――――――1

Ⅱ. 이론적 배경――――――――――――――――――――――3
1. coumarin―――――――――――――――――3

Ⅲ. 실험 방법―――――――――――――――――――――――5
1. 시약 및 분석기기――――――――――――――――――――5
2. 컬러필터용 염료의 합성――――――――6
가.7-diethylamino-2-oxo-2H-1-benzopyran-3-carboxylic acid ethyl ester(1)의 합성.―――8
나.3-(benzo[d]oxazol-2-yl)-7-(diethylamino)-2H-chromen-2-one (2)의 합성. (co-Yellow-2)――――9
다.3-(benzo[d]oxazol-2-yl)-7-(diethylamino)-2-oxo-2H-chromene-4-carbonitrile(3)의 합성. (co-Yellow-6)――――10
라.3-(benzo[d]oxazol-2-yl)-7-(diethylamino)-2H-chromene-2-one(4) 의 합성.――――11
마.3-(1H-benzo[d]imidazol-2-yl)-7-(diethylamino)-2-oxo-2H-chromene-4-carbonitrile(5)의 합성. (co-Red-6)――――12
바.3-(6-chlorobenzo[d]oxazol-2-yl)-7-(diethylamino)-2-oxo-2H-chromene-4-carbonitrile(6)의 합성. (co-Red-3)
――――13
사. ethyl 3-oxo-3H-benzo[f]chromene-2-carboxylate(7)의 합성.――――14
아. 2-(benzo[d]oxazol-2-yl)-3H-benzo[f]chromen-3-one(8)의 합성.(co-Yellow-1)――――15

Ⅳ. 결과 및 고찰―――――――――――――――――――――16
1.Coumarin 유도체 구조와 치환기의 역할――――――――――――16
가. co-yellow-2의 흡광특성―――――――17
나. co-yellow-2의 열적 성질―――――――19
다. co-yellow-6의 흡광특성―――――――22
라. co-yellow-6의 열적 성질―――――――24
마. co-red-6의 흡광특성―――――――26
바. co-red-6의 열적 성질 ―――――――28
사. co-red-3의 흡광특성―――――――30
아. co-yellow-1의 흡광특성―――――――32

Ⅴ. 결 론―――――――――――――――――――――――――34

PART2
Ⅰ. 서 론―――――――――――――――――――――――――35

Ⅱ. 이론적 배경――――――――――――――――――――――37
1. Rylene 유도체의 특성―――――――――――――――――37

Ⅲ. 실험 방법―――――――――――――――――――――――39
1. 시약 및 분석기기――――――――――――――――――――39
2. NIR colornt의 합성――――――――40
가. N-(2,6-diisopropylphenyl)-perylene-3,4-dicarboximide (1)의 합성.――――――41
나. N-(2,6-diisopropylphenyl)-9-bromo-perylene-3,4-dicarboximide(2)의 합성.――――――42
다. N-(2,6-diisopropylphenyl)-9-boronic ester-3,4-dicarboximide(3), 1,4-diboronic ester naphthalene(4)의 합성.――――――43
라. Naphthalene-1,4-bis(N,N‘-2,6-diisopropylphenyl-perylene-3,4-dicarboximide)(6)의 합성.――――――45
마. N,N'-diisopropylphenyl-1,6,8,10,12,14,17,19,21,23-decachloropentarylene-3,4:15,16-tetra-carboxyl bisimide(7)의 합성.――――――46

Ⅳ. 결과 및 고찰―――――――――――――――――――――47
1. Imide 작용기의 역할―――――――――――――――――――47
가. pentarylene Bisimide의 흡광특성―――――48
나. pentarylene Bisimide의 열적 성질―――――――50
다. pentarylene Bisimide의 내용매성 및 내화학성――――――52

Ⅴ. 결 론―――――――――――――――――――――――――55

Ⅵ. 참고문헌―――――――――――――――――――――――56
Degree
Master
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