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Positive photoresist composition, coating film thereof, and novolac phenol resin

A photoresist, novolak-type technology that can be applied to coatings, optics, and optomechanical devices, and can solve problems such as the inability to adequately respond to the level of demand for high heat resistance

Active Publication Date: 2013-11-06
DIC CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, even the positive-type photoresist compositions described in Patent Documents 2 and 3 cannot sufficiently meet the level of demand for high heat resistance in recent years.

Method used

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  • Positive photoresist composition, coating film thereof, and novolac phenol resin
  • Positive photoresist composition, coating film thereof, and novolac phenol resin
  • Positive photoresist composition, coating film thereof, and novolac phenol resin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0181] Specific examples can be listed below to further illustrate the present invention in detail. The measurement conditions of GPC are as follows.

[0182] [GPC measurement conditions]

[0183] Measuring device: "HLC-8220GPC" manufactured by Tosoh Corporation

[0184] Column: "Shodex KF802" (8.0mmФ×300mm) manufactured by Showa Denko Corporation

[0185] + "Shodex KF802" made by Showa Denko Corporation (8.0mmФ×300mm)

[0186] + "Shodex KF803" made by Showa Denko Corporation (8.0mmФ×300mm)

[0187] + "Shodex KF804" (8.0mmФ×300mm) manufactured by Showa Denko Corporation

[0188] Column temperature: 40℃

[0189] Detector: RI (differential refractometer)

[0190] Data processing: "GPC-8020 Model II Version 4.30" manufactured by Tosoh Corporation

[0191] Developing solvent: tetrahydrofuran

[0192] Flow rate: 1.0ml / min

[0193] Sample: A tetrahydrofuran solution of 0.5% by mass in terms of resin solid content is filtered with a microfilter

[0194] Injection volume: 0.1ml

[0195] Standard sample...

Synthetic example 1

[0211] [Synthesis example 1] Synthesis of cresol novolac resin (A)

[0212] In a 2-liter four-necked flask equipped with a stirrer and a thermometer, 648 g of m-cresol, 432 g of p-cresol, 2.5 g of oxalic acid, and 534 g of a 42% by mass formaldehyde aqueous solution were added, and the mixture was heated to 100° C. and reacted for 3 hours. Next, the temperature was raised to 210°C, dehydrated under reduced pressure, and distilled to obtain 948 g of cresol novolac resin (A1). As a result of GPC measurement of this cresol novolak resin (A1), the number average molecular weight (Mn) was 2715, the weight average molecular weight (Mw) was 19738, and the polydispersity (Mw / Mn)=7.270.

Synthetic example 2

[0213] [Synthesis example 2] Synthesis of polycondensate (C)

[0214] In a 100-ml two-necked flask equipped with a condenser and a thermometer, 3.66 g of 2,5-xylenol and 1.22 g of 4-hydroxybenzaldehyde were added and dissolved in 10 ml of 2-ethoxyethanol. After adding 1 ml of sulfuric acid while cooling in an ice bath, it was heated at 100°C for 2 hours, and stirred and reacted. After the reaction, the obtained solution was subjected to a reprecipitation operation with water to obtain a recovered product [crude product of polycondensate (C)]. The crude product of the polycondensate (C) was re-dissolved in acetone, and then subjected to reprecipitation with water, and then the obtained product was filtered and dried under vacuum to obtain the polycondensation of light brown crystals represented by the following formula (2-1) 物(C1) 2.82g. Here, the purity of the polycondensate (C) in the crude product was 87% by mass in terms of the area ratio of GPC, and the purity of the polycon...

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Abstract

An object of the present invention is to provide a positive photoresist composition having excellent developing properties and heat resistance and a coating film made from the composition. A positive photoresist composition includes 3 to 80 parts by mass of a novolac phenol resin (B) relative to 100 parts by mass of a cresol novolac resin (A). The novolac phenol resin (B) has a repeating structural unit represented by formula (1) [In the formula, R represents a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms and X represents a structure (x1) represented by formula (2) (In the formula, R 1 , R 2 , and R 3 each independently represent a hydrogen atom or an alkyl group having 1 to 8 carbon atoms; m and n each independently represent an integer of 1 to 4; p represents an integer of 0 to 4; and t represents 1 or 2) or an aromatic hydrocarbon group (x2) other than the structure (x1)]. The content of the structure (x1) relative to the total number of the structure (x1) and the structure (x2) is 85% or more.

Description

Technical field [0001] The present invention relates to a positive photoresist composition excellent in developability and heat resistance, and a coating film using the same. Background technique [0002] As a resist used in the manufacture of semiconductors such as ICs and LSIs, the manufacture of display devices such as LCDs, and the manufacture of printing original plates, a positive type using alkali-soluble resins and photosensitizers such as 1,2-naphthoquinonediazide compounds is known. Photoresist. Regarding the aforementioned alkali-soluble resin, a positive photoresist composition using a mixture of m-cresol novolak resin and p-cresol novolak resin as alkali-soluble resin has been proposed (for example, refer to Patent Document 1). [0003] The positive photoresist composition described in Patent Document 1 was developed to improve the developability such as sensitivity. In recent years, the high integration of semiconductors has increased, and the pattern tends to be thi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): G03F7/023C08G8/20H01L21/027
CPCC08G8/12C08L61/06C08G8/08G03F7/039C08L2205/02C08G8/20C09D161/06G03F7/0236G03F7/11C08L71/10G03F7/0233
Inventor 今田知之鹿毛孝和今泉规史
Owner DIC CORP
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