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CN-122003642-A - Curable composition, method for producing pixel, film, solid-state imaging element, image display device, and photopolymerization initiator

CN122003642ACN 122003642 ACN122003642 ACN 122003642ACN-122003642-A

Abstract

The present invention provides a curable composition containing a photopolymerization initiator and a polymerizable compound, wherein the photopolymerization initiator contains a compound represented by formula (1). The invention also provides a method for manufacturing a pixel using the curable composition, a film, a solid-state imaging element, and an image display device.

Inventors

  • MAKINO MASAOMI

Assignees

  • 富士胶片株式会社

Dates

Publication Date
20260508
Application Date
20241021
Priority Date
20231102

Claims (14)

  1. 1. A curable composition comprising a photopolymerization initiator and a polymerizable compound, The photopolymerization initiator comprises a compound represented by the formula (1), [ Chemical formula 1] In the formula (1), R 11 represents a hydrogen atom or a 1-valent organic group; X 11 represents-OR X11 OR-NR X12 R X13 , R X11 represents a hydrogen atom, an alkyl group, an alkoxy group, an aryl group, an aryloxy group, a heteroaryl group or a heteroaryloxy group, R X12 and R X13 each independently represent a hydrogen atom, an alkyl group or an aryl group, and R X12 and R X13 may be bonded via a single bond or a linking group to form a ring; r 12 and R 13 each independently represent an alkyl group, an alkoxy group, an aryl group, an aryloxy group, a heteroaryl group or a heteroaryloxy group, R 12 and R 13 may be bonded via a single bond or a linking group to form a ring, and R 12 or R 13 and R 14 may be bonded via a single bond or a linking group to form a ring; R 14 represents a substituent, and when n is 2 or more, R 14 in which a plurality of R 14 are present may be the same or different, and 2 of R 14 in which a plurality of R 14 are present may be bonded via a single bond or a linking group to form a ring; n represents an integer of 0 to 3.
  2. 2. The curable composition according to claim 1, wherein, X 11 in the formula (1) is a group represented by the formula (X-1), [ Chemical formula 2] In formula (X-1), represents a bond, R 101 ～R 104 each independently represents a hydrogen atom or an alkyl group, Y 101 represents O, S, NR Y1 or CR Y2 R Y3 ,R Y1 ～R Y3 each independently represents a hydrogen atom, an alkyl group or an aryl group, L 101 and L 102 each independently represent a single bond or an alkylene group.
  3. 3. The curable composition according to claim 1 or 2, wherein, The compound represented by the formula (1) is a compound represented by the formula (2), [ Chemical formula 3] In the formula (2), R 21 represents a hydrogen atom or a 1-valent organic group; X 21 represents-OR X21 OR-NR X22 R X23 , R X21 represents a hydrogen atom, an alkyl group, an alkoxy group, an aryl group, an aryloxy group, a heteroaryl group or a heteroaryloxy group, R X22 and R X23 each independently represent a hydrogen atom, an alkyl group or an aryl group, and R X22 and R X23 may be bonded via a single bond or a linking group to form a ring; R 22 and R 23 each independently represent an alkyl group, an alkoxy group, an aryl group, an aryloxy group, a heteroaryl group or a heteroaryloxy group, and R 22 and R 23 may be bonded via a single bond or a linking group to form a ring; r 24 represents a hydrogen atom or an alkyl group; R 25 ～R 28 each independently represents a hydrogen atom or a substituent, and adjacent 2 of R 25 ～R 28 may be bonded via a single bond or a linking group to form a ring; R 24 and R 22 or R 23 may be bonded via a single bond or a linking group to form a ring, R 28 and R 22 or R 23 may be bonded via a single bond or a linking group to form a ring.
  4. 4. The curable composition according to claim 1 or 2, wherein, The compound represented by the formula (1) is a compound represented by the formula (3), [ Chemical formula 4] In the formula (3), ar 31 represents an aryl group which may have a substituent or a heteroaryl group which may have a substituent; X 31 represents-OR X31 OR-NR X32 R X33 , R X31 represents a hydrogen atom, an alkyl group, an alkoxy group, an aryl group, an aryloxy group, a heteroaryl group or a heteroaryloxy group, R X32 and R X33 each independently represent a hydrogen atom, an alkyl group or an aryl group, and R X32 and R X33 may be bonded via a single bond or a linking group to form a ring; R 32 and R 33 each independently represent an alkyl group, an alkoxy group, an aryl group, an aryloxy group, a heteroaryl group or a heteroaryloxy group, and R 32 and R 33 may be bonded via a single bond or a linking group to form a ring; r 34 represents a hydrogen atom or an alkyl group; R 35 ～R 38 each independently represents a hydrogen atom or a substituent, and adjacent 2 of R 35 ～R 38 may be bonded via a single bond or a linking group to form a ring; R 34 and R 32 or R 33 may be bonded via a single bond or a linking group to form a ring, R 38 and R 32 or R 33 may be bonded via a single bond or a linking group to form a ring.
  5. 5. The curable composition according to claim 4, wherein, Ar 31 in the formula (3) is a group represented by the formula (Az-1), [ Chemical formula 5] In formula (Az-1), represents a bond, Z 41 represents a hydrogen atom, an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an alkylthio group, an aryloxy group, an arylthio group, a heteroaryloxy group, a heteroarylthio group, an amino group, a cyano group, a nitro group, a hydroxyl group, a thiol group, a carboxyl group, a halogen atom or an acyl group, R 49 represents an alkyl group, an aryl group or a halogen atom, P represents an integer of 0 to 4, When p is 2 or more, a plurality of R 49 may be the same or different, and 2 of R 49 may be bonded to form a ring via a single bond or a linking group.
  6. 6. The curable composition according to claim 5, wherein, In the formula (Az-1), Z 41 is a group represented by the formula (Z-1), [ Chemical formula 6] In the formula (Z-1), ar Z1 represents an aromatic ring group or a heterocyclic group, The aromatic ring group or heterocyclic group represented by Ar Z1 may have at least 1 selected from the group consisting of an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an alkylthio group, an aryloxy group, an arylthio group, a heteroaryloxy group, a heteroarylthio group, an amino group, a cyano group, a nitro group, a hydroxyl group, a thiol group, a carboxyl group, a halogen atom, and an acyl group as a substituent.
  7. 7. The curable composition according to claim 1 or 2, wherein, The photopolymerization initiator further comprises an oxime compound.
  8. 8. The curable composition according to claim 1 or 2, further comprising a coloring material.
  9. 9. The curable composition according to claim 1 or 2, further comprising a chain transfer agent.
  10. 10. A method of manufacturing a pixel, comprising: A step of forming a curable composition layer on a support using the curable composition according to claim 1 or 2; A step of exposing the curable composition layer to light having a wavelength of 150 to 300nm to form a pattern, and And developing and removing the unexposed portion of the curable composition layer.
  11. 11. A film obtained by curing the curable composition according to claim 1 or 2.
  12. 12. A solid-state imaging element comprising the film according to claim 11.
  13. 13. An image display device comprising the film of claim 11.
  14. 14. A photopolymerization initiator comprising a compound represented by the formula (1 a) or (3 a), [ Chemical formula 7] In the formula (1 a), ar 11a represents an aryl group which may have a substituent or a heteroaryl group which may have a substituent, the substituent being an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an alkylthio group, an aryloxy group, an arylthio group, a heteroaryloxy group, a heteroarylthio group, an amino group, a cyano group, a nitro group, a hydroxyl group, a thiol group, a carboxyl group, a halogen atom or an acyl group; X 11a represents-OR X11 OR-NR X12 R X13 , R X11 represents a hydrogen atom, an alkyl group, an alkoxy group, an aryl group, an aryloxy group, a heteroaryl group or a heteroaryloxy group, R X12 and R X13 each independently represent a hydrogen atom, an alkyl group or an aryl group, and R X12 and R X13 may be bonded via a single bond or a linking group to form a ring; R 12a and R 13a each independently represent an alkyl group, an alkoxy group, an aryl group, an aryloxy group, a heteroaryl group or a heteroaryloxy group, R 12a and R 13a may be bonded via a single bond or a linking group to form a ring, and R 12a or R 13a and R 14a may be bonded via a single bond or a linking group to form a ring; R 14a represents an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkylthio group, an arylthio group, a heteroarylthio group, an amino group, a nitro group, a cyano group, or a halogen atom, and when n is 2 or more, R 14a may be the same or different in plural, and 2 of R 14a may be bonded to each other via a single bond or a linking group to form a non-aromatic ring; n represents an integer of 0 to 3, [ Chemical formula 8] In the formula (3 a), ar 31a represents an aryl group which may have a substituent or a heteroaryl group which may have a substituent, the substituent being an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an alkylthio group, an aryloxy group, an arylthio group, a heteroaryloxy group, a heteroarylthio group, an amino group, a cyano group, a nitro group, a hydroxyl group, a thiol group, a carboxyl group, a halogen atom or an acyl group; X 31a represents-OR X31 OR-NR X32 R X33 , R X31 represents a hydrogen atom, an alkyl group, an alkoxy group, an aryl group, an aryloxy group, a heteroaryl group or a heteroaryloxy group, R X32 and R X33 each independently represent a hydrogen atom, an alkyl group or an aryl group, and R X32 and R X33 may be bonded via a single bond or a linking group to form a ring; r 32a and R 33a each independently represent an alkyl group, an alkoxy group, an aryl group, an aryloxy group, a heteroaryl group or a heteroaryloxy group, and R 32a and R 33a may be bonded via a single bond or a linking group to form a ring; R 34a represents a hydrogen atom or an alkyl group; R 35a ～R 38a independently represents a hydrogen atom, an alkyl group, an aryl group, a heteroaryl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkylthio group, an arylthio group, a heteroarylthio group, an amino group, a nitro group, a cyano group or a halogen atom, and adjacent 2 of R 35a ～R 38a may be bonded via a single bond or a linking group to form a ring; R 34a and R 32a or R 33a may be bonded via a single bond or a linking group to form a ring, R 38a and R 32a or R 33a may be bonded via a single bond or a linking group to form a ring.

Description

Curable composition, method for producing pixel, film, solid-state imaging element, image display device, and photopolymerization initiator Technical Field The present invention relates to a curable composition containing a photopolymerization initiator and a polymerizable compound. The present invention also relates to a method for manufacturing a pixel using the curable composition, a film, a solid-state imaging element, and an image display device. The present invention also relates to a photopolymerization initiator. Background The curable composition containing a photopolymerization initiator and a polymerizable compound is capable of being polymerized and cured by irradiation of light, and is therefore used for optical filters, photocurable inks, photosensitive printing plates, various photoresists, and the like. Patent document 1 discloses that pixels are formed by patterning by photolithography using a curable composition containing a photopolymerization initiator containing an aminoketone compound having a specific structure, a polymerizable compound, and an alkali-soluble resin. Technical literature of the prior art Patent literature Patent document 1 Japanese patent laid-open No. 2007-163542 Disclosure of Invention Technical problem to be solved by the invention In recent years, high resolution has been developed for solid-state imaging devices including filters such as color filters. Accordingly, with respect to filters such as color filters, further miniaturization of the size of pixels is being studied. When pixels are formed by patterning using a curable composition by a method such as photolithography, voids may be generated in the pixels. As the size of the pixel is miniaturized, the influence of voids on performance is large and product defects are likely to be caused. Accordingly, an object of the present invention is to provide a curable composition capable of forming a film that suppresses the occurrence of voids. Further, an object of the present invention is to provide a method for manufacturing a pixel, a film, a solid-state imaging element, an image display device, and a photopolymerization initiator. Means for solving the technical problems According to the studies of the present inventors, it has been found that the above object can be achieved by a curable composition described later, and the present invention has been completed. Accordingly, the present invention provides the following. <1> A curable composition comprising a photopolymerization initiator and a polymerizable compound, The photopolymerization initiator includes a compound represented by the formula (1); [ chemical formula 1] In the formula (1), R 11 represents a hydrogen atom or a 1-valent organic group; X 11 represents-OR X11 OR-NR X12RX13, R X11 represents a hydrogen atom, an alkyl group, an alkoxy group, an aryl group, an aryloxy group, a heteroaryl group or a heteroaryloxy group, R X12 and R X13 each independently represent a hydrogen atom, an alkyl group or an aryl group, and R X12 and R X13 may be bonded via a single bond or a linking group to form a ring; r 12 and R 13 each independently represent an alkyl group, an alkoxy group, an aryl group, an aryloxy group, a heteroaryl group or a heteroaryloxy group, R 12 and R 13 may be bonded via a single bond or a linking group to form a ring, and R 12 or R 13 and R 14 may be bonded via a single bond or a linking group to form a ring; R 14 represents a substituent, and when n is 2 or more, R 14 in which a plurality of R 14 are present may be the same or different, and 2 of R 14 in which a plurality of R 14 are present may be bonded via a single bond or a linking group to form a ring; n represents an integer of 0 to 3. <2> The curable composition according to <1>, wherein, X 11 in the above formula (1) is a group represented by the formula (X-1); [ chemical formula 2] In formula (X-1), represents a bond, R 101～R104 each independently represents a hydrogen atom or an alkyl group, Y 101 represents O, S, NR Y1 or CR Y2RY3,RY1～RY3 each independently represents a hydrogen atom, an alkyl group or an aryl group, L 101 and L 102 each independently represent a single bond or an alkylene group. <3> The curable composition according to <1> or <2>, wherein, The compound represented by the formula (1) is a compound represented by the formula (2); [ chemical formula 3] In the formula (2), R 21 represents a hydrogen atom or a 1-valent organic group; X 21 represents-OR X21 OR-NR X22RX23, R X21 represents a hydrogen atom, an alkyl group, an alkoxy group, an aryl group, an aryloxy group, a heteroaryl group or a heteroaryloxy group, R X22 and R X23 each independently represent a hydrogen atom, an alkyl group or an aryl group, and R X22 and R X23 may be bonded via a single bond or a linking group to form a ring; R 22 and R 23 each independently represent an alkyl group, an alkoxy group, an aryl group, an aryloxy group, a heteroaryl group or a heteroaryloxy group, and R 22 and R 23 may