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Photoactive compound and photosensitive resin composition comprising the same

一种光活性化合物、感光性树脂的技术，应用在感光性树脂组合物领域，能够解决困难、不能有效地吸收UV光源、启动剂保存稳定性差等问题

Active Publication Date: 2010-12-15
LG CHEM LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] As photoinitiators with oxime ester structure, α-oxooxime derivatives, substances used together with thioxanthone and oxime ester compounds, p-dialkylaminobenzene (p-dialkylaminobenzene) have been developed. Oxime esters used as synergists, photoinitiators using β-amino oximes, and oxime ester photoinitiators containing ethylenically unsaturated groups in the molecular structure, but the oxime derivative compounds developed initially, There are the following problems: the light starting efficiency is low, and the UV light source cannot be effectively absorbed in the case of good color characteristics
[0010] Therefore, although some development work has been carried out to improve the efficiency of light activation, the development has also not sufficiently satisfied the shortening of the processing time.
Especially in the formation of fine patterns, there are still difficulties due to the increase of the pigment concentration or the inability to fully meet the hardness of the thick film with a coating film thickness of 2.5 μm or more, and the formed pattern cannot meet the critical dimension (CD) required by the product. and mechanical strength
[0011] In recent years, the sensitivity of the commonly used oxime ester photopolymerization initiator Irgacure OXE 01 or Irgacure OXE 02 of Ciba specialty chemical company has been greatly improved, but there are the following disadvantages: because the price is very expensive, it cannot be used economically To achieve sufficient sensitivity to use, and the storage stability of the starter itself is poor

Method used

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  • Photoactive compound and photosensitive resin composition comprising the same
  • Photoactive compound and photosensitive resin composition comprising the same
  • Photoactive compound and photosensitive resin composition comprising the same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0101] Embodiment 1: Preparation of photoactive compound 1

[0102] (1) Preparation of 4-fluorobenzoyl chloride (1b)

[0103]

[0104] Thionyl chloride ( Thionyl chloride) (3.8g, 32.1mmol). The mixture was stirred at 60°C for 2 hours. The solvent was removed under reduced pressure to afford 4-fluorobenzoyl chloride (1b). Yield: 3.0 g (88%).

[0105] 1H NMR (500MHz, CDCl 3 , ppm) 8.16-8.13 (2H, m, ArH), 7.20-7.16 (2H, m, ArH).

[0106] (2) Preparation of 1d

[0107]

[0108] After mixing N-ethylcarbazole (2.7g, 13.8mmol), zinc chloride (0.17g, 1.2mmol) and chlorobenzene (10mL), the temperature was raised to 80°C, and slowly added dropwise to the (1) Compound 1b obtained in (2.0 g, 12.6 mol). After stirring at 80° C. for 1 hour, it was cooled to room temperature. N-hexane (20 g) and water (30 g) were added, and the organic layer was separated, then the water was removed with anhydrous sodium sulfate, and the solvent was removed under vacuum, followed by column ch...

experiment example 1

[0145] Experimental Example 1: Solubility Determination

[0146] In order to compare the solubility of the compound containing oxime ester, measure the Irgacure OXE-02 (comparative example 1) of Ciba SpecialtyChemical, the compound of comparative example 2 and comparative example 3 and embodiment in solvent propylene glycol methyl ether acetate (Propylene glycol methylether acetate, (PGMEA)), dipropylene glycol methyl ether (Dipropylene glycol methylether, (DPM)), 3-methoxybutyl acetate (3-methoxybutyl acetate, (MBA)), 3-ethoxy ethyl propionate ((Ethyl Solubility in -3-ethoxy propionate (EEP)), cyclohexanone (cyclohexanone (CH)). How many grams (g) photoinitiator is completely dissolved in 100g solvent as benchmark measurement solubility. Measurement result is shown in table 1 below Show.

[0147] 【Table 1】

[0148]

[0149]

experiment example 2

[0150] Experimental Example 2: Sensitivity Measurement

[0151] 12 g of alkali-soluble resin binder benzyl methacrylate / methacrylic acid (BzMA / MAA) (molar ratio: 70 / 30, Mw: 20,000), 12 g of polymerizable compound dipentaerythritol hexaacrylate, and 1 g each The compounds of starting agent Example 1, Comparative Example 1, Comparative Example 2, and Comparative Example 3 were mixed with 75 g of organic solvent PGMEA with a shaker for 3 hours. After that, the solution was filtered with a filter of 5 micrometers, and the obtained solution of the photosensitive composition was spin-coated on glass to form a film with a thickness of 2.5 micrometers, and heated at 100° C. for 2 minutes using a hot plate , to remove the solvent. Measure the FT-IR of the film, and simultaneously use a high-pressure mercury lamp at 20mW / cm 2 The irradiation dose was exposed for 5 seconds, and then the conversion rate of acrylate (acrylate) was compared. The experimental results are shown in Table ...

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Abstract

The present invention relates to a photoactive compound having a novel structure expressed in Chemical Formula 1 and to a photosensitive resin composition comprising the same. The photoactive compound of the present invention exhibits high efficiency in absorbing ultraviolet rays and generating radicals, and in photopolymerization with an unsaturated group. The photosensitive resin composition comprising the photoactive compound of the invention exhibits improved sensitivity through efficient absorption of ultraviolet rays, and improved residual film thickness, mechanical strength, heat resistance, chemical resistance and development resistance. Therefore, the photosensitive resin composition of the present invention is advantageous in hardening a column spacer, overcoat, and passivation material of a liquid crystal display, and also in a high temperature process.

Description

technical field [0001] This application claims priority from Korean Patent Application No. 10-2008-0033089 filed with the Korean Patent Office on April 10, 2008, and Korean Patent Application No. 10-2008-0033097 filed with the Korean Patent Office on the same date, both The entire content of the Korean patent application is incorporated in this specification. [0002] The present invention relates to a photoactive compound having a new structure and a photosensitive resin composition containing the photoactive compound, and relates to a photosensitive resin composition having high absorption rate to UV light source, excellent sensitivity and high-temperature processing properties, and excellent general-purpose use in photosensitive resin compositions A photoactive compound, and a photosensitive resin composition containing the photoactive compound. Background technique [0003] A photoactive compound is a substance that absorbs light and is decomposed to generate chemically...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/12G03F7/027
CPCC07D405/12G03F7/031
Inventor 赵昌镐金星炫R·卡巴施李健雨郭尚圭吴东宫李昌淳闵庚勋
Owner LG CHEM LTD
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