JP-2026075584-A - Photosensitive compositions, films, optical filters, solid-state image sensors, image display devices, and infrared sensors

Abstract

[Problem] To provide a photosensitive composition that exhibits excellent storage stability, development resistance, and pattern formation after standing. [Solution] A photosensitive composition comprising a resin (A), a polymerizable compound (B), and at least one polymerization initiator (C) selected from the group consisting of an oxime ester initiator of the following formula (1) having a specific structure and a bisoxime ester initiator having a specific structure. [Selection Diagram] Figure 1

Inventors

• 近藤 慶一
• 吉田 寛之

Assignees

• ａｒｔｉｅｎｃｅ株式会社

Dates

Publication Date

20260508

Application Date

20250523

Claims (14)

1. A photosensitive composition comprising a resin (A), a polymerizable compound (B), and a polymerization initiator (C), A photosensitive composition wherein the polymerization initiator (C) comprises at least one selected from the group consisting of a compound represented by the following formula (1) (C1) and a compound represented by the following formula (2) (C2). (In formula (1), R1 represents a monovalent substituent.) R2 represents R21 or OR21 , where R21 represents an alkyl group having 1 to 20 carbon atoms, or a heterocyclic group having 2 to 20 carbon atoms, and the methylene group of the alkylene portion within the alkyl group having 1 to 20 carbon atoms may be interrupted by an ether bond. R3 represents an alkyl group having 1 to 20 carbon atoms, a heterocyclic group having 2 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, or an aralkyl group having 7 to 30 carbon atoms. m represents an integer between 0 and 4. n represents an integer between 0 and 5. (In formula (2), R5 and R6 each independently represent an alkyl group having 1 to 20 carbon atoms, a heterocyclic group having 2 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, or an aralkyl group having 7 to 30 carbon atoms.) a and b each independently represent the integers 1 or 2. x represents an integer between 3 and 8. y and z each represent an integer of either 0 or 1 independently.
2. The photosensitive composition according to claim 1, wherein the resin (A) comprises at least one selected from the group consisting of a resin having a graft structure (A1) and a resin having a block structure (A2).
3. The photosensitive composition according to claim 2, wherein the resin (A1) having the graft structure has an acidic group.
4. The photosensitive composition according to claim 2, wherein the resin (A2) having the block structure has a basic group.
5. The photosensitive composition according to claim 1, wherein the resin (A) comprises a resin (A3) having a random structure.
6. The photosensitive composition according to claim 5, wherein the resin (A3) having the random structure comprises at least one selected from the group consisting of a thermally crosslinkable group and a polymerizable unsaturated group.
7. The photosensitive composition according to claim 1, wherein the polymerizable compound (B) comprises a polymerizable compound (B1) having at least one selected from the group consisting of a hydroxyl group, an acidic group, and an alkylene oxide group.
8. The photosensitive composition according to claim 1, wherein the polymerization initiator (C) comprises a compound (C3) other than the compound (C1) represented by formula (1) and the compound (C2) represented by formula (2).
9. Furthermore, the photosensitive composition according to claim 1, comprising a coloring agent (D).
10. A film formed from the photosensitive composition described in any one of claims 1 to 9.
11. An optical filter having the film described in claim 10.
12. A solid-state image sensor having the optical filter described in claim 11.
13. An image display device having the optical filter described in claim 11.
14. An infrared sensor having the optical filter described in claim 11.

Description

This invention relates to a photosensitive composition used for forming optical filters used in solid-state image sensors, image display devices, and infrared sensors, etc. Color filters, a type of optical filter used in image display devices and solid-state image sensors, are generally manufactured by forming patterns using photolithography. Photolithography involves several steps: applying a photosensitive composition to a glass or film substrate and removing the solvent from the coating by drying (hereinafter referred to as coating); irradiating and curing the coating with radiation through a photomask having the desired pattern shape (hereinafter referred to as exposure); then cleaning and removing the unexposed areas of the coating (hereinafter referred to as development); and finally, heat treatment to sufficiently harden the cured film (hereinafter referred to as post-bake) to create the pattern. The color filter is completed by repeating these steps multiple times. In recent years, image display devices and solid-state image sensors equipped with optical filters such as color filters have been achieving higher resolution. Therefore, miniaturization of the pixel size of optical filters such as color filters is being considered. However, when forming pixels by creating patterns using photolithography, as the pixel size becomes smaller, adhesion tends to become insufficient, and pixel defects and peeling tend to occur during the development process. Furthermore, miniaturization and thinning of image display devices and solid-state image sensors are progressing. For this reason, thinning of optical filters such as color filters is being considered. Thinning requires increasing the concentration of colorants in the solid components of the photosensitive composition. However, increasing the concentration of colorants in the solid components tended to worsen the storage stability of the photosensitive composition. Furthermore, when the time between coating the photosensitive composition and the exposure process was extended (long standing time), defects tended to occur and pattern formation deteriorated. Patent Document 1 discloses a photosensitive resin composition that allows for the formation of small line widths and small apertures without defects such as peeling, comprising a photopolymerizable compound, a photopolymerization initiator having a specific structure, an alkali-soluble resin, and a compound having a crosslinking group and a fluorine atom and/or a siloxane chain. Patent Document 2 discloses a photosensitive colored resin composition that has excellent curability, a high residual film rate, and can form a colored layer that is less prone to foreign matter precipitation, comprising a colorant, an alkali-soluble resin, a photopolymerizable compound, a specific oxime ester compound, and a solvent. Patent Document 3 discloses a bisoxime ester-based photopolymerization initiator having a specific structure, which is highly sensitive to light at wavelengths such as 365 nm and highly soluble. International Publication No. 2024/143067Japanese Patent Publication No. 2018-173461Japanese Patent Publication No. 2021-155642 Figure 1 shows a schematic cross-sectional view of an infrared sensor having the optical filter of the present invention. The following describes in detail embodiments of 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 this specification, 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. In this specification, "C.I." means Color Index (C.I.; published by The Society of Dyers and Colourists). In this specification, a polymerizable unsaturated group is an ethylenically unsaturated double bond or a carbon-carbon triple bond group. Regarding the molecular weight of the compounds in this invention, for low molecular weight compounds whose molecular weight can be specified, the molecular weight is calculated by formula weight or measured by ESI-MS (electrospray ionization mass spectrometry), and 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. In this specification, a numerical range represented by "~" means a range that includes the numbers written before and after "~" as the lower and upper limits, respectively. <Photosensitive composition> A photosensitive composition according to one embodiment of the present invention is a photosensitive composition comprising a resin (A), a polymerizable compound (B), and a polymerization init