Composition, film, lens, solid state imaging element, and compounds

Abstract

An object of the present invention is to provide a composition capable of forming a film having a high refractive index and excellent exterior characteristics. Another object of the present invention is to provide a film, a lens, and a solid-state imaging element in which the composition is used. Still another object of the present invention is to provide novel compounds. The composition according to an embodiment of the present invention contains a compound represented by General Formula (I), a solvent, and a resin, in which a solubility of the compound represented by General Formula (I) in the solvent is less than 0.5% by mass at 25° C., and a maximum absorption wavelength of the compound represented by General Formula (I) at a wavelength range of 300 to 800 nm is equal to or shorter than 450 nm.
AB-C).sub.n  (I)

Claims

1. A composition comprising: a compound represented by General Formula (I); a solvent; and a resin wherein a solubility of the compound represented by General Formula (I) in the solvent is less than 0.5% by mass at 25° C., a maximum absorption wavelength of the compound represented by General Formula (I) at a wavelength range of 300 to 800 nm is equal to or shorter than 450 nm, and the resin is selected from the group consisting of a graft copolymer containing a repeating unit represented by any of General Formula (11) to General Formula (14), and a resin having phosphorus atom-containing group,
AB-C).sub.n  (I) in General Formula (I), n represents 2 or 3, A represents a triazine ring group, B represents a single bond, —O—, —NR.sup.a—, or —S—, R.sup.a represents a hydrogen atom, an alkyl group, or an aryl group, C represents an alkyl group, an aryl group, or a heterocyclic group, a plurality of B's may be the same as or different from each other, and a plurality of C's may be the same as or different from each other, ##STR00046## in General Formula (11) to General Formula (14), W.sup.1, W.sup.2, W.sup.3, and W.sup.4 each independently represent an oxygen atom or NH, X.sup.1, X.sup.2, X.sup.3, X.sup.4, and X.sup.5 each independently represent a hydrogen atom or a monovalent group, Y.sup.1, Y.sup.2, Y.sup.3, and Y.sup.4 each independently represent a divalent linking group, Z.sup.1, Z.sup.2, Z.sup.3, and Z.sup.4 each independently represent a monovalent group, R.sup.3 represents an alkylene group, R.sup.4 represents a hydrogen atom or a monovalent group, n, m, p, and q each independently represent an integer of 1 to 500, and j and k each independently represent an integer of 2 to 8; in General Formula (13), in a case where p is 2 to 500, a plurality of R3'S may be the same as or different from each other; in General Formula (14), in a case where q is 2 to 500, a plurality of X.sup.5's and R.sup.4'S may be the same as or different from each other respectively.

2. The composition according to claim 1, wherein B is —NR.sup.a.

3. The composition according to claim 2, wherein B is —NH—.

4. The composition according to claim 1, wherein C is an aryl group or a heterocyclic group.

5. The composition according to claim 1, wherein the solvent is one or more kinds of solvents selected from the group consisting of esters, alcohols, aromatic hydrocarbons, aliphatic hydrocarbons, nitriles, ketones, and halogen compounds.

6. The composition according to claim 1, further comprising: a polymerizable compound.

7. The composition according to claim 1, further comprising: a photopolymerization initiator.

8. The composition according to claim 7, wherein the photopolymerization initiator is an oxime compound.

9. The composition according to claim 1, wherein the graft copolymer further contains a carbon-carbon double bond group in a molecule, and the resin having phosphorus atom-containing group further contains a carbon-carbon double bond group in a molecule.

10. A film formed of the composition according to claim 1.

11. A lens formed of the film according to claim 10.

12. A solid-state imaging element comprising: the lens according to claim 11.

13. A compound represented by General Formula (V), ##STR00047## in General Formula (V), R.sup.f represents a hydrogen atom or an alkyl group, Ar.sup.1 to Ar.sup.3 each independently represent an aryl group or a heterocyclic group, and at least one of Ar.sup.1, Ar.sup.2, or Ar.sup.3 represents a group represented by General Formula (VI), ##STR00048## in General Formula (VI), R.sup.g represents a phenyl group, a biphenyl group, or a cyano group, R.sup.h represents a substituent, p represents an integer of 1 to 5, q represents an integer of 0 to 4, * represents a binding position, and in a case where there is a plurality of R.sup.g's and a plurality of R.sup.h's, the plurality of R.sup.g's may be the same as or different from each other, and the plurality of R.sup.h's may be the same as or different from each other.

14. A composition comprising: a compound represented by General Formula (I); a solvent; and a resin wherein a solubility of the compound represented by General Formula (I) in the solvent is less than 0.5% by mass at 25° C., a maximum absorption wavelength of the compound represented by General Formula (I) at a wavelength range of 300 to 800 nm is equal to or shorter than 450 nm, and the resin is selected from the group consisting of a graft copolymer containing a repeating unit represented by any of General Formula (11) to General Formula (14), and a resin having phosphorus atom-containing group,
AB-C).sub.n  (I) in General Formula (I), n represents 3, A represents a triazine ring group, B represents a single bond, —O—, —NR.sup.a—, or —S—, R.sup.a represents a hydrogen atom, an alkyl group, or an aryl group, C represents an aryl group, a plurality of B's may be the same as or different from each other, and a plurality of C's may be the same as or different from each other, ##STR00049## in General Formula (11) to General Formula (14), W.sup.1, W.sup.2, W.sup.3, and W.sup.4 each independently represent an oxygen atom or NH, X.sup.1, X.sup.2, X.sup.3, X.sup.4, and X.sup.5 each independently represent a hydrogen atom or a monovalent group, Y.sup.1, Y.sup.2, Y.sup.3, and Y.sup.4 each independently represent a divalent linking group, Z.sup.1, Z.sup.2, Z.sup.3, and Z.sup.4 each independently represent a monovalent group, R.sup.3 represents an alkylene group, R.sup.4 represents a hydrogen atom or a monovalent group, n, m, p, and q each independently represent an integer of 1 to 500, and j and k each independently represent an integer of 2 to 8; in General Formula (13), in a case where p is 2 to 500, a plurality of R.sup.3's may be the same as or different from each other; in General Formula (14), in a case where q is 2 to 500, a plurality of X.sup.5's and R.sup.4's may be the same as or different from each other respectively.

Description

EXAMPLES

(1) Hereinafter, the present invention will be more specifically described based on examples. The materials, the amounts of the materials used, the proportion of the materials, the contents of treatments, the procedure of treatments, and the like shown in the following examples can be appropriately changed as long as the gist of the present invention is maintained. Accordingly, the scope of the present invention is not limited to the following examples.

(2) [1] Synthesis of Compound Represented by General Formula (I)

(Synthesis Example 1) Synthesis of Compound (A-1)

(3) ##STR00029##

(4) Cyanuric acid chloride (10.0 g) and 192 g of acetic acid were put into a three-neck flask and stirred under a nitrogen stream. Aniline (16.7 g) was added dropwise to the solution, and the solution was stirred for 2 hours while being heated at an external temperature of 110° C. Then, the obtained solution was cooled to 50° C., and 192 g of water was added thereto. The obtained solution was ice-cooled and stirred for 1 hour at an internal temperature of 0° C. to 5° C., and then the precipitated solids were collected by filtration, and the materials obtained by filtration were rinsed with 100 g of water. By using a vacuum dryer, the materials obtained by filtration were dried for 24 hours at 60° C., thereby obtaining 17.1 g of a compound (A-1).

(Synthesis Examples 2 to 8) Synthesis of Compounds (A-2) to (A-9)

(5) Compounds (A-2) to (A-9) were synthesized by performing the same operation as in Synthesis Example 1, except that aniline (an amino compound) as a raw material was changed to amino compounds corresponding to the compounds (A-2) to (A-9).

(6) The compound (A-1) and compounds (A-2) to (A-9) will be shown below. “Ac” represents an acetyl group, and “Me” represents a methyl group.

(7) ##STR00030## ##STR00031## ##STR00032##

(Synthesis Example 10) Synthesis of Compound (A-10)

(8) ##STR00033##

(9) Cyanuric acid chloride (5.0 g) and 50 g of tetrahydrofuran were put into a three-neck flask. Then, the three-neck flask was cooled in an ice bath obtained by adding ice to methanol, and in this state, the solution in the three-neck flask was stirred under a nitrogen stream. A solution, which was prepared by dissolving 3.2 g of N-methylaniline in 32.3 g of tetrahydrofuran, was added dropwise to the aforementioned solution for 1.5 hours, and the obtained solution was further stirred for 2 hours. Water (100 g) was put into the three-neck flask, the solution in the flask was stirred for 1 hour at an internal temperature of 0° C. to 5° C., then the precipitated solids were collected by filtration, and the materials obtained by filtration were rinsed with 100 g of water. By using a vacuum dryer, the materials obtained by filtration were dried for 24 hours at 60° C., thereby obtaining 12.1 g of an intermediate (a-10).

(10) The intermediate (a-10) (11.0 g), 10.5 g of aniline, 5.0 g of potassium carbonate, and 100 mL of N,N-dimethylacetamide were put into a three-neck flask and stirred for 2 hours while being heated at an external temperature of 110° C. under a nitrogen stream. Thereafter, the obtained solution was cooled to an internal temperature of 5° C., and 250 g of 1N hydrochloric acid was added dropwise to the three-neck flask. The three-neck flask was ice-cooled, the solution in the flask was stirred for 1 hour at an internal temperature of 0° C. to 5° C., the precipitated solids were collected by filtration, and the materials obtained by filtration were rinsed with 100 g of water. The materials obtained by filtration were dried for 24 hours at 60° C. by using a vacuum dryer, thereby obtaining 10.0 g of a compound (A-10).

(Synthesis Examples 11 to 13) Synthesis of Compounds (A-11) to (A-13)

(11) Compounds (A-11) to (A-13) were obtained by performing the same operation as in Synthesis Example 10, except that N-methylaniline in Synthesis Example 10 was changed to phenol, thiophenol, or 2-aminobenzimidazole.

(12) The compound (A-10) and compounds (A-11) to (A-13) will be shown below.

(13) ##STR00034##

(Synthesis Example 14) Synthesis of Compound (A-14)

(14) ##STR00035##

(15) Trimellitic acid chloride (10.0 g) and 100 mL of N,N-dimethylacetamide were put into a three-neck flask, and the flask was ice-cooled under a nitrogen stream. Then, 21.0 g of aniline was slowly added dropwise to the three-neck flask, and the flask was kept at an internal temperature equal to or lower than 10° C. After aniline was completely added dropwise to the flask, the internal temperature of the flask was increased to 25° C., and the solution in the flask was stirred for 2 hours. Thereafter, 250 g of 1N hydrochloric acid was added dropwise to the three-neck flask. The flask was ice-cooled, the solution in the flask was stirred for 1 hour at an internal temperature of 0° C. to 5° C., the precipitated solids were collected by filtration, and the materials obtained by filtration were rinsed with 100 g of water. The materials obtained by filtration were dried for 24 hours at 60° C. by using a vacuum dryer, thereby obtaining 12.3 g of a compound (A-14).

(Synthesis Examples 15 to 17) Synthesis of Compounds (A-15) to (A-17)

(16) Compounds (A-15) to (A-17) were obtained by performing the same operation as Synthesis Example 14, except that either or both of the acid chloride and aniline (an amino compound) in Synthesis Example 14 were changed to either or both of the acid chloride and amino compound corresponding to the compounds (A-15) to (A-17).

(17) The compound (A-14) and the compounds (A-15) to (A-17) will be shown below.

(18) ##STR00036## ##STR00037##

(Synthesis Example 18) Synthesis of Compound (A-18)

(19) ##STR00038##

(20) 2-Amino-6-methyl benzothiazole (33 g), 0.5 g of 4-dimethylaminopyridine, and 177 g of N,N-dimethylformamide were put into a three-neck flask. Then, 17 g of 1,4-phenylenediisothiocyanate was put into the three-neck flask, and the solution in the flask was stirred for 1 hour and then heated for 2 hours at an external temperature of 105° C. Thereafter, the solution was cooled to 50° C., and 100 mL of 1N hydrochloric acid was put into the three-neck flask. The flask was ice-cooled, the solution in the flask was stirred for 1 hour at an internal temperature of 0° C. to 5° C., the precipitated solids were then collected by filtration, and the materials obtained by filtration were rinsed with 500 g of water. By using a vacuum dryer, the materials obtained by filtration were dried for 24 hours at 60° C., thereby obtaining 10.7 g of an intermediate (a-18).

(21) The intermediate (a-18) (10 g) and 80 g of N-methylpyrrolidone were put into a three-neck flask and stirred. Tetrabutylammonium bromide (20 g) was slowly added thereto in divided portions. The precipitated solids were filtered and washed with 100 mL of acetone, 100 mL of 5% by mass aqueous sodium bicarbonate, and 100 mL of water in this order. By using a vacuum dryer, the materials obtained by filtration were dried for 24 hours at 60° C., thereby obtaining 8.7 g of a compound (A-18).

(Synthesis Examples 19 and 20) Synthesis of Compounds (A-19) and (A-20)

(22) Based on the synthesis method for the compound (A-10), compounds (A-19) and (A-20) were synthesized.

(23) The compounds (A-19) and (A-20) will be shown below.

(24) ##STR00039##

(Synthesis Examples 21 and 22) Synthesis of Compounds (A-21) and (A-22)

(25) Based on the synthesis method for the compound (A-1), compounds (A-21) and (A-22) were synthesized.

(26) The compounds (A-21) and (A-22) will be shown below.

(27) ##STR00040##

(Synthesis Examples 23 and 24) Synthesis of Compounds (A-23) and (A-24)

(28) Based on the synthesis method for the compound (A-10), compounds (A-23) and (A-24) were synthesized.

(29) The compounds (A-23) and (A-24) will be shown below.

(30) ##STR00041##

(31) Each of the compound (A-7), the compound (A-8), and the compounds (A-19) to (A-24) was identified by measuring a Mass Spectrum (MS).

(32) Specifically, a sample was dissolved (suspended) in dimethyl sulfoxide and mixed with a dimethyl sulfoxide solution containing α-cyano-4-hydroxycinnamic acid (CHCA) matrix, a Matrix Assisted Laser Desorption/Ionization (MALDI) plate was coated with the obtained mixture, and a mass spectrum was measured. The mass spectrum was measured using autoflex manufactured by Bruker in a positive mode. The results will be shown below.

(33) Compound (A-7) detected M.sup.++1 (posi): 811

(34) Compound (A-8) detected M.sup.++1 (posi): 658

(35) Compound (A-19) detected M.sup.++1 (posi): 504

(36) Compound (A-20) detected M.sup.++1 (posi): 713

(37) Compound (A-21) detected M.sup.++1 (posi): 1036

(38) Compound (A-22) detected M.sup.++1 (posi): 682

(39) Compound (A-23) detected M.sup.++1 (posi): 670

(40) Compound (A-24) detected M.sup.++1 (posi): 555

(41) Furthermore, the obtained compound (A-18) was also identified by MS measurement.

(42) Specifically, a sample was dissolved (suspended) in acetone and mixed with a CHCA matrix solution (acetone), and a MALDI plate was coated with the obtained mixture. MS was measured using autoflex from Bruker in a positive mode.

(43) Compound (A-18) detected M.sup.++1 (posi): 571.10

(44) [2] Dissolution Test

(45) (Dissolution Test 1)

(46) By the following method, the solubility of the compound represented by General Formula (I) in a solvent was investigated.

(47) The compound represented by General Formula (I) (compound (A-1), 1 g) was added to 50 g of a solvent (PGMEA) shown in Table 1, and the obtained solution was stirred for 1 hour at 25° C. Then, solids were removed using a 0.5 μm TEFLON (registered trademark) filter. Thereafter, the obtained filtrate was caused to volatilize for 3 hours at 150° C. in a vacuum, and the content of residues was measured, thereby quantifying the content of solids dissolved in the solvent.

(48) As a result, the solubility of the compound (A-1) in the solvent PGMEA was found to be less than 0.5% by mass.

(49) (Dissolution Tests 2 to 54)

(50) Dissolution tests 2 to 54 were carried out by performing the same operation as in the dissolution test 1, except that the compound represented by General Formula (I) and the solvent were changed to those described in Table 1.

(51) As a result, the solubility of the compounds (A-1) to (A-24) in the solvents shown in Table 1 was found to be less than 0.5% by mass.

(52) Table 1 shows the results of the dissolution tests 1 to 54.

(53) In Table 1, “PGMEA” means propylene glycol monomethyl ether acetate, and “PGME” means propylene glycol monomethyl ether.

(54) TABLE-US-00001 TABLE 1 Compound represented by General Formula (I) Solvent Solubility Dissolution test 1 A-1 PGMEA Less than 0.5% by mass Dissolution test 2 A-2 PGMEA Less than 0.5% by mass Dissolution test 3 A-3 PGMEA Less than 0.5% by mass Dissolution test 4 A-4 PGMEA Less than 0.5% by mass Dissolution test 5 A-5 PGMEA Less than 0.5% by mass Dissolution test 6 A-6 PGMEA Less than 0.5% by mass Dissolution test 7 A-7 PGMEA Less than 0.5% by mass Dissolution test 8 A-8 PGMEA Less than 0.5% by mass Dissolution test 9 A-9 PGMEA Less than 0.5% by mass Dissolution test A-10 PGMEA Less than 0.5% by 10 mass Dissolution test A-11 PGMEA Less than 0.5% by 11 mass Dissolution test A-12 PGMEA Less than 0.5% by 12 mass Dissolution test A-13 PGMEA Less than 0.5% by 13 mass Dissolution test A-14 PGMEA Less than 0.5% by 14 mass Dissolution test A-15 PGMEA Less than 0.5% by 15 mass Dissolution test A-16 PGMEA Less than 0.5% by 16 mass Dissolution test A-17 PGMEA Less than 0.5% by 17 mass Dissolution test A-18 PGMEA Less than 0.5% by 18 mass

(55) TABLE-US-00002 TABLE 2 Continued from Table 1 Compound represented by General Formula (I) Solvent Solubility Dissolution test 19 A-1 Toluene Less than 0.5% by mass Dissolution test 20 A-2 Cyclohexyl methyl ether Less than 0.5% by mass Dissolution test 21 A-3 PGME Less than 0.5% by mass Dissolution test 22 A-4 Butyl acetate Less than 0.5% by mass Dissolution test 23 A-5 3-methoxybutyl acetate Less than 0.5% by mass Dissolution test 24 A-6 Cyclohexyl acetate Less than 0.5% by mass Dissolution test 25 A-7 PGMEA/PGME (90% by Less than mass/10% by mass) 0.5% by mass Dissolution test 26 A-8 Cyclopentanone Less than 0.5% by mass Dissolution test 27 A-9 Cyclobutyl ether Less than 0.5% by mass Dissolution test 28 A-10 Propylene glycol diacetate Less than 0.5% by mass Dissolution test 29 A-11 Dipropylene glycol Less than dimethyl ether 0.5% by mass Dissolution test 30 A-12 Diethylene glycol Less than monobutyl ether acetate 0.5% by mass Dissolution test 31 A-13 Xylene Less than 0.5% by mass Dissolution test 32 A-14 Ethyl lactate Less than 0.5% by mass Dissolution test 33 A-15 PGMEA/PGME (90% Less than by mass/10% by mass) 0.5% by mass Dissolution test 34 A-16 PGMEA/PGME (80% Less than by mass/20% by mass) 0.5% by mass Dissolution test 35 A-17 Cyclopentanone/PGME Less than (90% by mass/10% by mass) 0.5% by mass Dissolution test 36 A-18 PGMEA/butyl acetate Less than (70% by mass/30% by mass) 0.5% by mass Dissolution test 37 A-3 Cyclohexanone Less than 0.5% by mass Dissolution test 38 A-4 PGME Less than 0.5% by mass Dissolution test 39 A-7 PGMEA/PGME (70% by Less than mass/30% by mass) 0.5% by mass Dissolution test 40 A-9 Diethylene glycol Less than monobutyl ether acetate 0.5% by mass Dissolution test 41 A-10 Anisole Less than 0.5% by mass Dissolution test 42 A-12 3-Methoxybutyl acetate Less than 0.5% by mass Dissolution test 43 A-13 Propylene glycol diacetate Less than 0.5% by mass Dissolution test 44 A-15 Cyclohexyl acetate Less than 0.5% by mass Dissolution test 45 A-16 3-Methoxybutyl acetate Less than 0.5% by mass Dissolution test 46 A-18 Dipropylene glycol Less than dimethyl ether 0.5% by mass Dissolution test 47 A-7 PGMEA/PGME (70% Less than by mass/30% by mass) 0.5% by mass Dissolution test 48 A-10 Anisole Less than 0.5% by mass

(56) TABLE-US-00003 TABLE 3 Continued from Table 1 Compound represented by General Formula (I) Solvent Solubility Dissolution test 49 A-19 PGMEA Less than 0.5% by mass Dissolution test 50 A-20 PGMEA Less than 0.5% by mass Dissolution test 51 A-21 PGMEA Less than 0.5% by mass Dissolution test 52 A-22 PGMEA Less than 0.5% by mass Dissolution test 53 A-23 PGMEA Less than 0.5% by mass Dissolution test 54 A-24 PGMEA Less than 0.5% by mass

(57) [3] Preparation of Dispersion Liquid (Dispersion Composition)

(58) A solution obtained by mixing together the following components was mixed and dispersed for 3 hours by using a beads mill (zirconia beads having a diameter of 0.3 mm), thereby preparing a dispersion liquid (dispersion composition). Table 4 shows the maximum absorption wavelength of the compound represented by General Formula (I) in a wavelength range of 300 to 800 nm. The method for measuring the maximum absorption wavelength will be described later as “spectral characteristics”.

(59) Components

(60) TABLE-US-00004 Compound represented by General Formula (I) shown 20 parts by mass in Table 2 (any of compounds (A-1) to (A-24)) Dispersant shown in Table 2 (any of resins 1 to 3)  5 parts by mass Solvent shown in Table 2 80 parts by mass

(61) The structures of the dispersants (resins 1 to 3) will be shown below.

(62) ##STR00042##

(63) TABLE-US-00005 TABLE 4 Table 2 Makeup of dispersion liquid Compound represented by General Formula (I) Solvent Dispersed resin Dispersion A-1 Toluene Resin 1 liquid 1 Dispersion A-2 PGMEA Resin 1 liquid 2 Dispersion A-3 Cyclohexanone Resin 1 liquid 3 Dispersion A-4 PGME Resin 1 liquid 4 Dispersion A-5 3-Methoxybutyl acetate Resin 1 liquid 5 Dispersion A-6 Cyclohexyl acetate Resin 1 liquid 6 Dispersion A-7 PGMEA/PGME (70/30: Resin 1 liquid 7 mass ratio) Dispersion A-8 Cyclopentanone Resin 1/Resin 3 liquid 8 (80/20: mass ratio) Dispersion A-9 Diethylene glycol Resin 1 liquid 9 monobutyl ether acetate Dispersion A-10 Anisole Resin 1 liquid 10 Dispersion A-11 PGMEA Resin 1 liquid 11 Dispersion A-12 3-Methoxybutyl acetate Resin 1 liquid 12 Dispersion A-13 Propylene glycol Resin 1 liquid 13 diacetate Dispersion A-14 PGMEA Resin 1 liquid 14 Dispersion A-15 Cyclohexyl acetate Resin 1 liquid 15 Dispersion A-16 3-Methoxybutyl acetate Resin 1 liquid 16 Dispersion A-17 PGMEA Resin 1 liquid 17 Dispersion A-18 Dipropylene glycol Resin 1 liquid 18 dimethyl ether Dispersion A-2/A-8 = 50/50 PGMEA Resin 1 liquid 19 (mass ratio) Dispersion A-2 PGMEA Resin 2 liquid 20 Dispersion A-7 PGMEA/PGME Resin 2 liquid 21 (70/30: mass ratio) Dispersion A-10 Anisole Resin 2 liquid 22 Dispersion A-19 PGMEA Resin 1 liquid 23 Dispersion A-20 PGMEA Resin 1 liquid 24 Dispersion A-21 PGMEA Resin 1 liquid 25 Dispersion A-22 PGMEA Resin 1 liquid 26 Dispersion A-23 PGMEA Resin 1 liquid 27 Dispersion A-24 PGMEA Resin 1 liquid 28

(64) [4] Preparation of Composition (Curable Composition) (Examples 1 to 31)

(65) Compositions (curable compositions) were prepared by mixing together the following components. The prepared compositions 1 to 31 were named Examples 1 to 31 respectively and evaluated as will be described later.

(66) Components Dispersion liquid shown in Table 3 (any of dispersion liquids 1 to 28) 100 parts by mass Polymerizable compound shown in Table 3 mixing amount shown in Table 3 (part by mass) Binder shown in Table 3 mixing amount shown in Table 3 (part by mass) Photopolymerization initiator shown in Table 3 mixing amount shown in Table 3 (part by mass) Surfactant MEGAFACE R-40 (DIC Corporation) shown in Table 3 0.1 parts by mass

(67) The structure of each of the polymerizable compounds (M-1 to M-6), the binders (J-1 to J-3), and the photopolymerization initiators (I-1 to I-10) will be shown below. x, y, z, and w shown in the binder J-2 mean mass ratio.

(68) ##STR00043## ##STR00044## ##STR00045##

(69) TABLE-US-00006 TABLE 5 Makeup of composition (curable composition) Polymerizable compound Binder Photopolymerization initiator Dispersion Added Added Added Table 3 liquid Type amount Type amount Type amount Composition 1 Dispersion M-1 2 J-1 1 I-1 1 liquid 1 Composition 2 Dispersion M-1 2 J-1 1 I-2 1 liquid 2 Composition 3 Dispersion M-3 1 J-2 2 I-3 1 liquid 3 Composition 4 Dispersion M-4 2 J-2 1 I-1/I-4 0.5/0.5 liquid 4 Composition 5 Dispersion M-5 2 J-2 1 I-1 1 liquid 5 Composition 6 Dispersion M-1 2 J-1 1 I-2 1 liquid 6 Composition 7 Dispersion M-1/M-3 1/1 J-2 1 I-3 1 liquid 7 Composition 8 Dispersion M-2 2 J-2 1 I-4 I liquid 8 Composition 9 Dispersion M-4 1 J-1/J-2 1/1 I-2 1 liquid 9 Composition 10 Dispersion M-5 2 J-1 1 I-7 1 liquid 10 Composition 11 Dispersion M-1 2 J-2 1 I-8 1 liquid 11 Composition 12 Dispersion M-2 2 J-1 1 I-9 1 liquid 12 Composition 13 Dispersion M-1 2 J-1 1 I-1 1 liquid 13 Composition 14 Dispersion M-2 2 J-1 1 I-9 1 liquid 14 Composition 15 Dispersion M-5 1 J-2 2 I-8 1 liquid 15 Composition 16 Dispersion M-6 2 J-2 1 I-10 1 liquid 16 Composition 17 Dispersion M-3 2 J-1 1 I-10 1 liquid 17 Composition 18 Dispersion M-2 2 J-2 1 I-2 1 liquid 18 Composition 19 Dispersion M-6 1 J-1 2 I-5 1 liquid 19 Composition 20 Dispersion M-1 1 J-2 2 I-7 1 liquid 20 Composition 21 Dispersion M-2 2 J-1 1 I-9 1 liquid 21 Composition 22 Dispersion M-4 2 J-2 1 I-8 1 liquid 22 Composition 23 Dispersion M-1 1 J-2 1 I-7 1 liquid 1 Composition 24 Dispersion M-2 1 J-3 1 I-6 1 liquid 1 Composition 25 Dispersion M-4 1 J-3 1 I-8 1 liquid 1 Composition 26 Dispersion M-1 2 J-1 1 I-1 1 liquid 23 Composition 27 Dispersion M-1 2 J-1 1 I-1 1 liquid 24 Composition 28 Dispersion M-1 2 J-1 I I-1 1 liquid 25 Composition 29 Dispersion M-I 2 J-1 1 I-1 1 liquid 26 Composition 30 Dispersion M-1 2 J-1 1 I-1 1 liquid 27 Composition 31 Dispersion M-1 2 J-1 1 I-1 1 liquid 28

(70) [5] Evaluation of Composition

(71) Each of the obtained compositions 1 to 31 was evaluated in terms of spectral characteristics, refractive index, exterior characteristics (dispersibility), moisture resistance, light fastness, developability, and pattern shape.

(72) <Evaluation of Spectral Characteristics>

(73) Each of the dispersion liquids 1 to 28 was diluted 1,000× with the solvent used for dispersion. By using Carry 5000 (manufactured by Agilent Technologies, Inc.), spectrometry was performed on the obtained solution at 300 to 800 nm. As references, samples containing the resin and the solvent used in the dispersion liquids 1 to 28 (samples that did not contain the compound represented by General Formula (I)) were used. The maximum absorption wavelength in the obtained optical spectrum was measured. The results are shown in Table 4. The evaluation result from the dispersion liquid 1 corresponds to Examples 1 and 23 to 25, the evaluation results from the dispersion liquids 2 to 22 correspond to Examples 2 to 22, and the evaluation results from the dispersion liquids 23 to 28 correspond to Examples 26 to 31.

(74) (Evaluation Standards)

(75) “A”: The maximum absorption wavelength of the material of high refractive index is less than 450 nm.

(76) “B”: The maximum absorption wavelength of the material of high refractive index is equal to or longer than 450 nm.

(77) The material of high refractive index means the compound represented by General Formula (I).

(78) <Measurement of Refractive Index>

(79) A 5 cm×5 cm glass substrate, on which an epoxy resin layer was formed using an epoxy resin (JER-827, manufactured by Japan Epoxy Resins Co., Ltd.), was spin-coated with each of the compositions 1 to 31, and then the obtained coating film was baked for 3 minutes at 100° C. Then, by using a high-pressure mercury lamp, the coating film was exposed such that the cumulative exposure amount became 200 mJ/cm.sup.2.

(80) By using VASE manufactured by J. A. Woollam, the refractive index of the obtained cured film at a wavelength of 300 to 1,500 nm was measured, and a refractive index n.sub.589 nm at a wavelength 589 nm was measured. Based on the measured refractive index (n.sub.589 nm), the compositions were evaluated according to the following evaluation standards. The results are shown in Table 4.

(81) (Evaluation Standards)

(82) “A”: The refractive index (n.sub.589 nm) is equal to or higher than 1.70.

(83) “B”: The refractive index (n.sub.589 nm) is equal to or higher than 1.65 and less than 1.70.

(84) “C”: The refractive index (n.sub.589 nm) is equal to or higher than 1.60 and less than 1.65.

(85) “D”: The refractive index (n.sub.589 nm) is less than 1.60.

(86) <Evaluation of Exterior Characteristics (Dispersibility)>

(87) The surface of the glass substrate with a cured film obtained in the process of evaluating refractive index characteristics described above was observed with an optical microscope, and the exterior characteristics thereof were evaluated based on the following evaluation standards. The results are shown in Table 4.

(88) (Evaluation Standards)

(89) “A”: The surface is smooth and has no problem such as a crack.

(90) “B”: Asperities are observed in a portion of the surface but are on a level that is unproblematic for practical use.

(91) “C”: Asperities and cracks are observed in a portion of the surface but are on a level that is unproblematic for practical use.

(92) “D”: Asperities or cracks are observed in a portion of the surface and are on a level that is problematic for practical use.

(93) <Evaluation of Moisture Resistance>

(94) The glass substrate with a cured film obtained in the process of evaluating refractive index characteristics described above was stored for 720 hours in an atmosphere with a temperature of 85° C. and a relative humidity of 85%. After the storage, the surface condition of the cured film was observed using a Scanning Electron Microscope (SEM) and evaluated based on the following evaluation standards. The results are shown in Table 4.

(95) (Evaluation Standards)

(96) “A”: The surface condition does not change before and after the moisture resistance test.

(97) “B”: One to five abnormalities (cracking, swelling, and the like) are observed within the surface after the moisture resistance test but are on a level that is unproblematic for practical use.

(98) “C”: Six to ten abnormalities (cracking, swelling, and the like) are observed within the surface after the moisture resistance test but are on a level that is unproblematic for practical use.

(99) “D”: More than ten abnormalities (cracking, swelling, and the like) are observed within the surface after the moisture resistance test.

(100) <Evaluation of Light Fastness>

(101) By using a xenon lamp, the glass substrate with a cured film obtained in the process of evaluating the refractive index characteristics described above was irradiated with light for 20 hours at 100,000 lux (equivalent to 2,000,000 lux.Math.h), and then the film thickness of the cured film was measured. The smaller the rate of change in film thickness, the better the performance.

(102) The rate of change in film thickness was determined by the following equation based on the film thickness before the light fastness test. Furthermore, based on the rate of change in film thickness, light fastness was evaluated according to the following evaluation standards. The results are shown in Table 4.
(Rate of change in film thickness)={(film thickness before light fastness test)−(film thickness after light fastness test)/(film thickness before light fastness test)}×100

(103) (Evaluation Standards)

(104) “A”: The rate of change in film thickness is less than 5%.

(105) “B”: The rate of change in film thickness is equal to or higher than 5% and less than 10%.

(106) “C”: The rate of change in film thickness is equal to or higher than 10%.

(107) <Developability-Pattern Shape>

(108) A 5 cm×5 cm glass substrate, on which an epoxy resin layer was formed using an epoxy resin (JER-827, manufactured by Japan Epoxy Resins Co., Ltd.), was spin-coated with each of the compositions 1 to 31, and the obtained coating film was baked for 3 minutes at 100° C. Then, by using an i-line stepper exposure machine FPA-3000i5+ (manufactured by Canon Inc.), the coating film was exposed at a wavelength of 365 nm through a mask having a 1 μM island pattern in various exposure amounts within a range of 50 to 1,200 mJ/cm.sup.2. Thereafter, the glass substrate having the exposed coating film was placed on a horizontal rotating table of a spin-shower developing machine (DW-30 model, manufactured by Chemitronics Co., Ltd.,) and subjected to puddle exposure for 60 seconds at 23° C. by using a developer CD-2000 (manufactured by FUJIFILM Electronic Materials Co., Ltd.), thereby forming a pattern on the glass substrate.

(109) The glass substrate with a pattern formed thereon was fixed on the aforementioned horizontal rotating table by a vacuum chucking method, and the table was caused to rotate at a rotation speed of 50 r.p.m. In this state, a rinsing treatment was performed by supplying pure water thereon in the form of shower from a spray nozzle from above the center of rotation, and then the substrate was spray-dried.

(110) Subsequently, by using a critical dimension SEM “S-9260A” (manufactured by Hitachi High-Technologies Corporation), 100 patterns and 100 developed portions were observed, and the pattern shape and the developability were evaluated based on the following evaluation standards. The results are shown in Table 4.

(111) (Evaluation Standards for Developability)

(112) “A”: No residue is checked in developed portions.

(113) “B”: Although residues are checked in 1 to 10 developed portions, the developability is unproblematic for practical use.

(114) “C”: Residues are checked in 11 or more developed portions.

(115) (Pattern Shape)

(116) “A”: A rectangular pattern is formed.

(117) “B”: Although 1 to 10 defectively developed portions (non-rectangular portions) are checked at the edge of the pattern, the pattern shape is unproblematic for practical use.

(118) “C”: Eleven or more defectively developed portions (non-rectangular portions) are checked at the edge of the pattern.

(119) TABLE-US-00007 TABLE 6 Exterior Spectral refractive characteristics Moisture Light Develop- Pattern Table 4 Composition characteristics index (Dispersibility) resistance fastness ability shape Example 1 Composition A A A A A B A 1 Example 2 Composition A A A A A A A 2 Example 3 Composition A A A A A A A 3 Example 4 Composition A A A A A A A 4 Example 5 Composition A A A A A A A 5 Example 6 Composition A A A A A A A 6 Example 7 Composition A A A A A A A 7 Example 8 Composition A A A A A A A 8 Example 9 Composition A A A A A A A 9 Example 10 Composition A B B B B B A 10 Example 11 Composition A B C B B A A 11 Example 12 Composition A B C B B A A 12 Example 13 Composition A A A A A A A 13 Example 14 Composition A C B C B A A 14 Example 15 Composition A C B C B A A 15 Example 16 Composition A C B C B A A 16 Example 17 Composition A C B C B A A 17 Example 18 Composition A B B B A A A 18 Example 19 Composition A A A A A A A 19 Example 20 Composition A A A A B A B 20 Example 21 Composition A A A A B A B 21 Example 22 Composition A B B B B B B 22 Example 23 Composition A A A A B B A 23 Example 24 Composition A A A A B B A 24 Example 25 Composition A A A A B B A 25 Example 26 Composition A A A A A A A 26 Example 27 Composition A A A A A A A 27 Example 28 Composition A A A A A A A 28 Example 29 Composition A A A A A A A 29 Example 30 Composition A A B B A A A 30 Example 31 Composition A A B B A A A 31

(120) As is evident from the results in Table 4, according to the composition of the according to the embodiment of the present invention, it is possible to form a film which has a high refractive index and excellent external exterior characteristics.

(121) Furthermore, by comparing Examples 2 to 9, Example 13, Example 19, and Examples 26 to 29 (corresponding to examples graded A in terms of all the evaluation items) with Examples 10 to 12, Examples 14 to 18, Example 22, Example 30, and Example 31, it was confirmed that in a case where A in the compound represented General Formula (I) is a heterocyclic group or in a case where B in the compound represented by General Formula (I) is —NR.sup.a—, —CONR.sup.b—, or —SO.sub.2NR.sup.c—, at least one of refractive index, exterior characteristics, or moisture resistance is further improved. It was confirmed that especially in a case where A in the compound represented by General Formula (I) is a triazine ring group and B in the compound represented by General Formula (I) is —NH—, refractive index, exterior characteristics, and moisture resistance are particularly excellent.

(122) By comparing Examples 2 to 9, Example 13, Example 19, and Examples 26 to 29 (corresponding to examples graded A in terms of all the evaluation items) with Example 1, Example 10, and Examples 22 to 25, it was confirmed that in a case where esters, ketones, or alcohols are used as a solvent, developability is further improved.

(123) By comparing Examples 2 to 9, Example 13, Example 19, and Examples 26 to 29 (corresponding to examples graded A in terms of all the evaluation items) with Examples 20 to 22, it was confirmed that in a case where the dispersant contains a carbon-carbon double bond group, the pattern shape is further improved.

(124) By comparing Examples 2 to 9, Example 13, Example 19, and Examples 26 to 29 (corresponding to examples graded A in terms of all the evaluation items) with Examples 10 to 12, Examples 14 to 17, and Examples 20 to 25, it was confirmed that in a case where an oxime-based initiator is contained as the photopolymerization initiator and/or in a case where a carbon-carbon double bond group is contained in the binder, light fastness is further improved.