JP-7855914-B2 - Photosensitive composition, cured film using the same, optical filter, image display device, solid-state image sensor, and infrared sensor

Inventors

• 吉田 寛之

Assignees

• ａｒｔｉｅｎｃｅ株式会社
• 東洋ビジュアルソリューションズ株式会社

Dates

Publication Date

20260511

Application Date

20220510

Priority Date

20210531

Claims (7)

1. A photosensitive composition comprising a near-infrared absorbing dye (A), a polymerizable compound (B), a photopolymerization initiator (C) , a sensitizer (D) , and a binder resin (E) , The near-infrared absorbing dye (A) comprises at least one selected from the group consisting of naphthalocyanine compounds, pyrrolopyrrole compounds, squarylium compounds, and indigo compounds. The polymerizable compound (B) contains 55% by mass or more of polymerizable compound (B1) represented by the following general formula (1) in 100% by mass, The photopolymerization initiator (C) comprises at least one selected from the group consisting of alkylphenone compounds, acylphosphine oxide compounds, and biimidazole compounds. The sensitizer (D) comprises a benzophenone compound (D1), The benzophenone compound (D1) includes 4,4'-bis(diethylamino)benzophenone, The photopolymerization initiator (C) is a photosensitive composition that is substantially free of oxime compounds. General formula (1) (In general formula (1), R1 independently represents either a hydrogen atom or a methyl group, and X is either a hydrogen atom or a group represented by general formula (2) below.) General formula (2) (In general formula (2), L represents a divalent linking group, and * represents a bond that connects to the oxygen atom in general formula (1).)
2. The photosensitive composition according to claim 1 , wherein the content of the sensitizer (D) is 150 to 400 parts by mass per 100 parts by mass of the photopolymerization initiator (C).
3. A cured film obtained by curing the photosensitive composition according to claim 1 or 2 .
4. An optical filter having the cured film described in claim 3 .
5. An image display device having the cured film according to claim 3 .
6. A solid-state image sensor having the cured film described in claim 3 .
7. An infrared sensor having a cured film as described in claim 3 .

Description

This invention relates to a photosensitive composition, a cured film using the same, an optical filter, an image display device, a solid-state image sensor, and an infrared sensor. Video cameras, digital cameras, and portable devices with camera functions utilize CCDs (charge-coupled devices) and CMOS (complementary metal-oxide-semiconductor) solid-state image sensors for color images. Because these solid-state image sensors use silicon photodiodes, which are sensitive to infrared light, it is necessary to perform luminous sensitivity correction, and infrared cut filters are placed accordingly. Infrared cut filters are manufactured, for example, using compositions containing near-infrared absorbing dyes. Traditionally, infrared cut filters were used as flat films, but in recent years, there has been research into forming patterns in infrared cut filters using photolithography. When forming patterns using photolithography, oxime compounds have been widely used as photopolymerization initiators due to their high sensitivity. However, compositions containing near-infrared absorbing dyes readily transmit active energy rays (such as i-rays). Therefore, when exposed via a photomask, the unexposed areas around the mask are easily exposed by reflected and scattered light from the substrate. Using highly sensitive oxime compounds can lead to accelerated reactions in the masked areas. This results in reduced solubility in the developer, thicker line widths in the resulting patterns, poor pattern shape, and the generation of development residue. Furthermore, when the near-infrared absorbing dye is a pigment, dispersion is difficult, and using highly sensitive oxime compounds can lead to poor storage stability and the formation of aggregates of the near-infrared absorbing dye. Various approaches have been taken to address the above problems. For example, Patent Document 1 discloses a photosensitive composition comprising a phthalocyanine compound having an absorption maximum wavelength in the near-infrared region, a binder resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent. Patent Document 2 discloses a pattern-forming composition comprising an infrared-absorbing dye and a resin with a glass transition temperature of 150-300°C, which exhibits excellent suppression of development residue and superior shape and heat resistance of the resulting pattern. Japanese Patent Publication No. 2010-160380International Publication No. 2019/058882 Figure 1 shows a schematic cross-sectional view of an infrared sensor equipped with the cured film of the present invention. The following describes in detail embodiments for carrying out the photosensitive composition of the present invention. However, the present invention is not limited to the following embodiments and can be modified and implemented within the scope of solving the problem. In the present invention, unless otherwise specified, "(meth)acryloyl,""(meth)acrylic,""(meth)acrylicacid,""(meth)acrylate," or "(meth)acrylamide" means "acryloyl and/or methacryloyl,""acrylic and/or methacrylic,""acrylic acid and/or methacrylic acid,""acrylate and/or methacrylate," or "acrylamide and/or methacrylamide," respectively. Also, "C.I." means Color Index (C.I.; issued by The Society of Dyers and Colourists). A polymerizable unsaturated group is an ethylenically unsaturated double bond. Regarding the molecular weight of the compounds in this invention, for low molecular weight compounds whose molecular weight can be determined, the value is calculated or measured by ESI-MS (electrospray ionization mass spectrometry). For compounds with a molecular weight distribution, the weight-average molecular weight in polystyrene terms is measured by gel permeation chromatography using tetrahydrofuran as the solvent. A monomer is a compound that forms a resin through polymerization. A monomer is in an unreacted state, while a monomer unit is the state in which the monomer has polymerized and formed a resin. <Photosensitive composition> One embodiment of the present invention relates to a photosensitive composition. The photosensitive composition of the present invention is a photosensitive composition comprising a near-infrared absorbing dye (A), a polymerizable compound (B), a photopolymerization initiator (C), and a sensitizer (D), The polymerizable compound (B) contains 55% by mass or more of polymerizable compound (B1) represented by the following general formula (1) in 100% by mass, The photopolymerization initiator (C) is characterized by being substantially free of oxime compounds. General formula (1) In general formula (1), R1 independently represents either a hydrogen atom or a methyl group, and X is either a hydrogen atom or a group represented by the following general formula (2). General formula (2) In general formula (2), L represents a divalent linking group, and * represents a bond that connects to the oxygen atom in general formula (1). The mechanism by