Fluorene oxime ester compound, photopolymerization initiator and photoresist composition containing the same

Patent metadata

Field	Value
Publication number	US-9316906-B2
Application number	US-201314398565-A
Country	US
Kind code	B2
Filing date	May 3, 2013
Priority date	May 3, 2012
Publication date	Apr 19, 2016
Grant date	Apr 19, 2016

Abstract

Provided are a novel fluorene oxime ester compound, and a photopolymerization initiator and a photoresist composition containing the same.

First claim

The invention claimed is:

1. A fluorene oxime ester compound represented by the following Chemical Formula 1:

where,
each R 1 is independently (C 1 -C 20 )alkyl;
R 2 is hydrogen, halogen, (C 1 -C 20 )alkyl, (C 6 -C 20 )aryl, (C 1 -C 20 )alkoxy, (C 6 -C 20 )aryl(C 1 -C 20 )alkyl, hydroxy(C 1 -C 20 )alkyl, hydroxy(C 1 -C 20 )alkoxy(C 1 -C 20 )alkyl, or (C 3 -C 20 )cycloalkyl;
R 3 is (C 1 -C 20 )alkyl, (C 6 -C 20 )aryl, (C 1 -C 20 )alkoxy, (C 6 -C 20 )aryl(C 1 -C 20 )alkyl, hydroxy(C 1 -C 20 )alkyl, hydroxy(C 1 -C 20 )alkoxy(C 1 -C 20 )alkyl, or (C 3 -C 20 )cycloalkyl; and
A is hydrogen, (C 1 -C 20 )alkyl, (C 6 -C 20 )aryl, (C 1 -C 20 )alkoxy, (C 6 -C 20 )aryl(C 1 -C 20 )alkyl, hydroxy(C 1 -C 20 )alkyl, hydroxy(C 1 -C 20 )alkoxy(C 1 -C 20 )alkyl, (C 3 -C 10 )cycloalkyl, amino, nitro, cyano, or hydroxyl.

2. The fluorene oxime ester compound of claim 1 , wherein each R 1 is independently methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, i-pentyl, n-hexyl, or i-hexyl;
R 2 is hydrogen, bromo, chloro, iodo, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, i-pentyl, n-hexyl, i-hexyl, phenyl, naphthyl, biphenyl, terphenyl, anthryl, indenyl, phenanthryl, methoxy, ethoxy, n-propyloxy, i-propyloxy, n-butoxy, i-butoxy, t-butoxy, hydroxymethy, hydroxyethyl, hydroxy-n-propyl, hydroxy-n-butyl, hydroxy-i-butyl, hydroxy-n-pentyl, hydroxy-i-pentyl, hydroxy-n-hexyl, hydroxy-i-hexyl, hydroxymethoxymethyl, hydroxymethoxyethyl, hydroxymethoxypropyl, hydroxymethoxybutyl, hydroxyethoxymethyl, hydroxyethoxyethyl, hydroxyethoxypropyl, hydroxyethoxybutyl, hydroxyethoxypentyl, or hydroxyethoxyhexyl;
R 3 is bromo, chloro, iodo, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, i-pentyl, n-hexyl, i-hexyl, phenyl, naphthyl, biphenyl, terphenyl, anthryl, indenyl, phenanthryl, methoxy, ethoxy, n-propyloxy, i-propyloxy, n-butoxy, i-butoxy, t-butoxy, hydroxymethy, hydroxyethyl, hydroxy-n-propyl, hydroxy-n-butyl, hydroxy-i-butyl, hydroxy-n-pentyl, hydroxy-i-pentyl, hydroxy-n-hexyl, hydroxy-i-hexyl, hydroxymethoxymethyl, hydroxymethoxyethyl, hydroxymethoxypropyl, hydroxymethoxybutyl, hydroxyethoxymethyl, hydroxyethoxyethyl, hydroxyethoxypropyl, hydroxyethoxybutyl, hydroxyethoxypentyl, or hydroxyethoxyhexyl; and
A is hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, phenyl, naphthyl, biphenyl, terphenyl, anthryl, indenyl, phenanthryl, methoxy, ethoxy, propyloxy, butoxy, hydroxymethyl, hydroxyethyl, hydroxypropyl, hydroxybutyl, hydroxymethoxymethyl, hydroxymethoxyethyl, hydroxymethoxypropyl, hydroxymethoxybutyl, hydroxyethoxymethyl, hydroxyethoxyethyl, hydroxyethoxypropyl, hydroxyethoxybutyl, amino, nitro, cyano, or hydroxy.

3. The fluorene oxime ester compound of claim 1 , wherein
each R 1 is independently hydrogen or n-butyl;
R 2 is methyl; and
R 3 is methyl, n-butyl, or phenyl.

4. A photopolymerization initiator comprising the fluorene oxime ester compound of claim 1 .

5. A photoresist composition comprising the fluorene oxime ester compound of claim 1 .

6. The photoresist composition of claim 5 , wherein the fluorene oxime ester compound of claim 1 is contained at a content of 0.01 to 10 weight % based on the photoresist composition.

7. A photoresist composition for a black matrix further comprising carbon black in addition to the photoresist composition of claim 5 .

8. A photoresist composition for a color matrix further comprising a color pigment dispersion solution in addition to the photoresist composition of claim 5 .

Assignees

• Korea Res Inst Chem Tech
• Samyang Corp

Inventors

• Shin Seung Rim
• Jun Kun
• Shin Jong Il
• Park Soo Youl
• An Kyoung Lyong
• Lee Sang Oh
• Moon Bong Seok
• Oh Chunrim
• Choi Anam
• So In-Young

Classifications

• C07C2103/18

  Chemistry & Metallurgy · mapped topic

• G03F7/0007

  Filters, e.g. additive colour filters; Components for display devices · CPC title

• G03F7/105

  having substances, e.g. indicators, for forming visible images · CPC title

• G03F7/031

  Organic compounds not covered by group G03F7/029 · CPC title

• C07C251/68

  with at least one of the esterifying carboxyl groups bound to a carbon atom of a six-membered aromatic ring · CPC title