Colored photo sensitive resin composition, blue bank, organic light emitting diode by using the same and image display device

Abstract

The colored photosensitive resin composition according to the embodiments of the present invention comprises an alkali-soluble resin, a photopolymerizable compound, a colorant, a photopolymerization initiator, and a solvent. The alkali-soluble resin comprises a copolymer represented by Formula 1 and a cardo-based resin.

Description

Technology Field

[0001] The present disclosure provides a colored photosensitive resin composition, a blue bank, an organic light-emitting element, and an image display device. Background Technology

[0003] Organic light-emitting diodes are self-emissive, so they offer superior viewing angles and contrast compared to liquid crystal display devices. Since they do not require a backlight, they can be lightweight and thin, and they are also advantageous in terms of power consumption.

[0004] It is desirable for the above organic light-emitting diode to have high contrast, and the contrast decreases when the external light is bright. In particular, in the case of a back-emitting type organic light-emitting diode, since the device includes a cathode made of a metal material with high reflectivity, light incident from the outside into the device is reflected on the cathode surface and mixes with the light emitted from the light-emitting layer. To solve this problem, a bank can be formed that absorbs external incident light to improve contrast.

[0005] The bank may be a black bank, a transparent bank, etc., and may be formed from a photosensitive resin composition. For example, after forming the photosensitive resin composition on a substrate, the bank may be formed through exposure and development processes. However, residue and / or scum may increase during development processes such as puddle development. Therefore, it is necessary to develop a material for the bank to reduce the residue / scum. The problem to be solved

[0007] One objective of the present disclosure is to provide a colored photosensitive resin composition having improved optical properties.

[0008] One objective of the present disclosure is to provide a blue bank having improved optical properties.

[0009] One objective of the present disclosure is to provide an organic light-emitting device having improved optical properties.

[0010] One objective of the present disclosure is to provide an image display device having improved optical properties. means of solving the problem

[0012] 1. An alkali-soluble resin comprising a copolymer represented by the following chemical formula 1 and a cardo-based resin;

[0013] Photopolymerizable compound;

[0014] coloring agent;

[0015] Photopolymerization initiator; and

[0016] Colored photosensitive resin composition containing a solvent:

[0017] [Chemical Formula 1]

[0018]

[0019] (In Chemical Formula 1, A is or Displayed as,

[0020] B is Displayed as,

[0021] X is oxygen (O) or nitrogen (N), and

[0022] R1 to R4 are each independently hydrogen, a halogen, a hydroxyl group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted hydroxyalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted hydroxyalkoxyalkyl group having 2 to 40 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms.

[0023] a to c are each independently integers from 1 to 20, and

[0024] d is an integer from 0 to 10).

[0025] 2. A colored photosensitive resin composition according to 1, wherein in the above chemical formula 1, a to c are each independently integers from 1 to 10, and the ratio of b to a is from 0.1 to 8.

[0026] 3. In the above 1, among the above chemical formula 1, B is or Displayed as,

[0027] R5 is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms or a substituted or unsubstituted hydroxyalkyl group having 1 to 30 carbon atoms, and

[0028] R6 is a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms, and

[0029] d is an integer from 1 to 10, and

[0030] A colored photosensitive resin composition in which e is an integer from 1 to 3.

[0031] 4. In the above 3, among the above chemical formula 1, B is Displayed as,

[0032] X is oxygen, and d is an integer from 1 to 5, and

[0033] A colored photosensitive resin composition in which R5 is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms or a substituted or unsubstituted hydroxyalkyl group having 1 to 10 carbon atoms.

[0034] 5. In the above 3, among the above chemical formula 1, B is A colored photosensitive resin composition represented by, wherein R6 comprises a substituted or unsubstituted tertiary alkylene group having 1 to 30 carbon atoms.

[0035] 6. A colored photosensitive resin composition according to 1, wherein the cardo-based resin comprises a unit derived from the following chemical formula 2:

[0036] [Chemical Formula 2]

[0037]

[0038] (In Chemical Formula 2, R6 and R7 are each independently hydrogen or a methyl group, and

[0039] L1 to L4 are each independently an alkylene group having 1 to 10 carbon atoms).

[0040] 7. A colored photosensitive resin composition according to 1, wherein the weight average molecular weight of the cardo-based resin is 1,000 g / mol to 30,000 g / mol.

[0041] 8. A colored photosensitive resin composition, wherein the weight ratio of the cardo-based resin to the copolymer represented by Chemical Formula 1 is 1 to 8.

[0042] 9. A colored photosensitive resin composition according to 1, wherein the content of the alkali-soluble resin in the total weight of the composition is 1% to 50% by weight.

[0043] 10. The colored photosensitive resin composition of 1 above, wherein the coloring agent comprises CI pigment blue 15:6 and pigment violet 29.

[0044] 11. A colored photosensitive resin composition according to 1, wherein the content of the coloring agent in the total weight of the composition is 10% to 40% by weight.

[0045] 12. Blue bank formed from the colored photosensitive resin composition according to 1 above.

[0046] 13. An organic light-emitting device comprising a blue bank according to 12 above.

[0047] 14. An image display device comprising an organic light-emitting element according to 13 above. Effects of the invention

[0049] The colored photosensitive resin composition according to exemplary embodiments of the present invention may have a low particle size change rate during the development process. Accordingly, it may have improved reworkability.

[0050] A blue bank comprising a photocurable pattern formed from a colored photosensitive resin composition according to exemplary embodiments of the present invention may be formed. The photocurable pattern may have enhanced chemical resistance / rework solution solubility, and the occurrence of residue of the pattern may be suppressed.

[0051] Blue banks according to exemplary embodiments of the present invention can provide improved optical density by having low light transmittance and high light absorption. Accordingly, high-quality organic light-emitting devices can be provided. Specific details for implementing the invention

[0053] The colored photosensitive resin composition of the present invention comprises an alkali-soluble resin, a photopolymerizable compound, a colorant, a photopolymerization initiator, and a solvent. Additionally, the blue bank of the present invention is formed from the colored photosensitive resin composition, and the organic light-emitting device of the present invention comprises the blue bank.

[0054] The present invention will be described in detail below. However, this is merely illustrative and the present invention is not limited to the specific embodiments described illustratively.

[0055] A colored photosensitive resin composition according to exemplary embodiments (hereinafter abbreviated as composition) comprises an alkali-soluble resin.

[0056] The above alkali-soluble resin includes a copolymer represented by Chemical Formula 1.

[0057] [Chemical Formula 1]

[0058]

[0059] In the above chemical formula 1, A is or It can be displayed as.

[0060] B is It can be displayed as.

[0061] X can be oxygen (O) or nitrogen (N).

[0062] R1 to R4 may each independently be hydrogen, a halogen, a hydroxyl group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted hydroxyalkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted hydroxyalkoxyalkyl group having 2 to 40 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms. In one embodiment, R1 to R4 may each independently be hydrogen, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted hydroxyalkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted hydroxyalkoxyalkyl group having 2 to 30 carbon atoms.

[0063] In some embodiments, B of Formula 1 is or It may be represented as. In one embodiment, R5 may be a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms or a substituted or unsubstituted hydroxyalkyl group having 1 to 30 carbon atoms. For example, R5 may be a hydroxyalkyl group having 1 to 30 carbon atoms. For example, R6 may be a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms. Accordingly, the dispersibility of the alkali-soluble resin may be further improved. For example, B may include a hydroxy acrylate derivative. Accordingly, the formation of a fine pattern can be sufficiently realized.

[0064] In some embodiments, a to c may each be an integer from 1 to 20 independently. In one embodiment, a to c may each be an integer from 1 to 10 independently, and the ratio of b to a may be from 0.1 to 8, from 1 to 5, or from 1.2 to 4. Within the above ranges, the heat resistance and chemical resistance of the composition may be further improved.

[0065] In some embodiments, d may be an integer from 0 to 10. In one embodiment, d may be an integer from 1 to 10 or an integer from 1 to 5.

[0066] In one embodiment, B is It is represented as such, where X is oxygen, and R5 may be a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms or a substituted or unsubstituted hydroxyalkyl group having 1 to 10 carbon atoms.

[0067] In one embodiment, B is It is represented as such, where R6 comprises a substituted or unsubstituted tertiary alkylene group having 1 to 30 carbon atoms, and e may be an integer from 1 to 3.

[0068] In some embodiments, B is N-methyl(meth)acrylamide, N,N-dimethyl(meth)acrylamide, N,N-diethyl(meth)acrylamide, N-isopropylacrylamide, N-butyl(meth)acrylamide, N-hexyl(meth)acrylamide, N-methylol(meth)acrylamide, N-hydroxyethyl(meth)acrylamide, N-hydroxypropyl(meth)acrylamide, N-hydroxybutyl(meth)acrylamide, N-methylol-N-propane(meth)acrylamide, aminomethyl(meth)acrylamide, aminoethyl(meth)acrylamide, mercaptomethyl(meth)acrylamide, N-acryloylmorpholine, 2-hydroxy-3-phenoxypropyl(meth)acrylate, It may be a unit derived from 2-hydroxy-3-t-butylphenoxypropyl(meth)acrylate, methyl(meth)acrylate, ethyl(meth)acrylate, n-butyl(meth)acrylate, 2-ethylhexyl(meth)acrylate, isooctyl(meth)acrylate, isononyl(meth)acrylate, lauryl(meth)acrylate, methoxyethyl(meth)acrylate, ethoxyethyl(meth)acrylate, 2-hydroxyethyl(meth)acrylate, 2-hydroxypropyl(meth)acrylate, 4-hydroxybutyl(meth)acrylate, 6-hydroxyhexyl(meth)acrylate, 8-hydroxyoctyl(meth)acrylate, etc. These can be used individually or in combination of two or more.

[0069] In one embodiment, B is 2-hydroxyethyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, 6-hydroxyhexyl (meth)acrylate, ω-hydroxydecyl (meth)acrylate, 2-(2-methoxyethoxy)-ethyl ester acrylic acid, tetraoxatridecane-13-yl (meth)acrylate, 2-(2-{2-[2-(2-methoxyethoxy)ethoxy]ethoxy}ethoxy)ethyl (meth)acrylate, diethylene glycol mono(meth)acrylate, tetraethylene glycol mono(meth)acrylate, methoxypolyethylene glycol mono(meth)acrylate, 2,3-dihydroxypropyl (meth)acrylate, The unit may be derived from pentaerythritol mono(meth)acrylate, trimethylolpropane mono(meth)acrylate, 2-glycol mono(meth)acrylate, 5,6-hydroxyhexyl(meth)acrylate, N-(tris(hydroxymethyl)methyl)acrylimide, N,N-bis(2-hydroxyethyl)aminomethyl-acrylamide, etc. Accordingly, the degree of curing of the photocurable pattern prepared from the above composition may be further increased and pattern residue may be further suppressed. In addition, changes in the particle size of the waste developer may be further suppressed.

[0070] For example, the colored photosensitive resin composition may include a copolymer represented by Chemical Formula 1 to have improved dispersibility while having a low rate of change in particle size of the waste developer during the development process. Accordingly, the blue bank produced from the colored photosensitive resin composition may have improved chemical resistance / heat resistance.

[0071] The above alkali-soluble resin includes a cardo-based resin. Accordingly, residue of the photocured pattern can be suppressed during the photocured pattern formation and development processes.

[0072] For example, the above cardo-based resin is bis(4-hydroxyphenyl)sulfone, bis(4-hydroxy-3,5-dimethylphenyl)sulfone and bis(4-hydroxy-3,5-dichlorophenyl)sulfone; bis(4-hydroxyphenyl)hexafluoropropane, bis(4-hydroxy-3,5-dimethylphenyl)hexafluoropropane and bis(4-hydroxy-3,5-dichlorophenyl)hexafluoropropane; bis(4-hydroxyphenyl)dimethylsilane, bis(4-hydroxy-3,5-dimethylphenyl)dimethylsilane and bis(4-hydroxy-3,5-dichlorophenyl)dimethylsilane; Bis(4-hydroxyphenyl)methane, bis(4-hydroxy-3,5-dichlorophenyl)methane and bis(4-hydroxy-3,5-dibromophenyl)methane; 2,2-bis(4-hydroxyphenyl)propane, 2,2-bis(4-hydroxy-3,5-dimethylphenyl)propane, 2,2-bis(4-hydroxy-3,5-dichlorophenyl)propane, 2,2-bis(4-hydroxy-3-methylphenyl)propane and 2,2-bis(4-hydroxy-3-chlorophenyl)propane; bis(4-hydroxyphenyl)ether, bis(4-hydroxy-3,5-dimethylphenyl)ether and bis(4-hydroxy-3,5-dichlorophenyl)ether; It may include copolymers of monomer mixtures such as 9,9-bis(4-hydroxyphenyl)fluorene, 9,9-bis(4-hydroxy-3-methylphenyl)fluorene, 9,9-bis(4-hydroxy-3-chlorophenyl)fluorene, 9,9-bis(4-hydroxy-3-bromophenyl)fluorene, 9,9-bis(4-hydroxy-3-fluorophenyl)fluorene, 9,9-bis(4-hydroxy-3-methoxyphenyl)fluorene, 9,9-bis(4-hydroxy-3,5-dimethylphenyl)fluorene, 9,9-bis(4-hydroxy-3,5-dichlorophenyl)fluorene, and 9,9-bis(4-hydroxy-3,5-dibromophenyl)fluorene. These may be used alone or in combination of two or more.

[0073] In some embodiments, the cardo resin may comprise a copolymer of a fluorene compound and an acid anhydride compound.

[0074] For example, the above fluorene-based compounds may be 9,9-bis(3-cinnamic diester)fluorene, 9,9-bis(3-cinnamoyl, 4-hydroxyphenyl)fluorene, 9,9-bis(glycidyl methacrylate ether)fluorene, 9,9-bis(3,4-dihydroxyphenyl)fluorene dicinamic ester, 3,6-diglycidyl methacrylate ether spiro(fluorene-9,9-xanthen), 9,9-bis(3-allyl, 4-hydroxyphenylfluorene), 9,9-bis(4-allyloxyphenyl)fluorene, 9,9-bis(3,4-methacrylic diester)fluorene, etc. These may be used alone or in combination of two or more.

[0075] For example, the acid anhydride compound may include an acid anhydride or an acid dihydride. The acid anhydride may include maleic anhydride, succinic anhydride, itaconic anhydride, phthalic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, methylenedo-methylenetetrahydrophthalic anhydride, chlorenedic anhydride, methyltetrahydrophthalic anhydride, etc. The acid dihydride may include pyrromellitic anhydride, benzophenone tetracarboxylic acid dihydride, biphenyltetracarboxylic acid dihydride, bitenyl ether tetracarboxylic acid dihydride, etc. These may be used alone or in combination of two or more.

[0076] In some embodiments, the alkali-soluble resin may include a unit derived from a compound represented by the following chemical formula 2.

[0077] [Chemical Formula 2]

[0078]

[0079] In the above chemical formula 2, R6 and R7 may each independently be hydrogen or a methyl group.

[0080] In the above Chemical Formula 2, L1 to L4 may each independently be an alkylene group having 1 to 10 carbon atoms. For example, L1 to L4 may each independently have 1 to 8 carbon atoms. , 1 to 5 carbon atoms, or It may be an alkylene group having 1 to 3 carbon atoms. For example, L1 to L4 may be a methylene group.

[0081] The above alkali-soluble resin may further include repeating units derived from carboxyl group-containing monomers.

[0082] The above carboxyl group-containing monomer may include an unsaturated monocarboxylic acid or an unsaturated dicarboxylic acid. For example, the above carboxyl group-containing monomer may include acrylic acid, methacrylic acid, crotonic acid, itaconic acid, maleic acid, fumaric acid, etc. These may be used alone or in combination of two or more.

[0083] The alkali-soluble resin may further include repeating units derived from a reactive monomer copolymerizable with the carboxyl group-containing monomer.

[0084] As a non-limiting example, the reactive monomer is an aromatic vinyl compound such as styrene, α-methylstyrene, o-vinyltoluene, m-vinyltoluene, p-vinyltoluene, p-chlorostyrene, o-methoxystyrene, m-methoxystyrene, p-methoxystyrene, o-vinylbenzylmethyl ether, m-vinylbenzylmethyl ether, p-vinylbenzylmethyl ether, o-vinylbenzylglycidyl ether, m-vinylbenzylglycidyl ether, p-vinylbenzylglycidyl ether, indene, etc. Methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, butyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, 3-hydroxybutyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, allyl (meth)acrylate, benzyl (meth)acrylate, cyclohexyl (meth)acrylate, phenyl (meth)acrylate, 2-methoxyethyl (meth)acrylate, 2-phenoxyethyl (meth)acrylate, methoxydiethylene glycol (meth)acrylate, Unsaturated carboxylic acid ester compounds such as methoxytriethylene glycol (meth)acrylate, methoxypropylene glycol (meth)acrylate, methoxydipropylene glycol (meth)acrylate, isobornyl (meth)acrylate, dicyclopentadienyl (meth)acrylate, 2-hydroxy-3-phenoxypropyl (meth)acrylate, glycerol mono(meth)acrylate, and 3-(acryloyloxy)-2-hydroxypropyl methacrylate; Unsaturated aminoalkyl ester compounds such as 2-aminoethyl (meth)acrylate, 2-dimethylaminoethyl (meth)acrylate, 2-aminopropyl (meth)acrylate, 2-dimethylaminopropyl (meth)acrylate, 3-aminopropyl (meth)acrylate, and 3-dimethylaminopropyl (meth)acrylate; unsaturated carboxylic acid glycidyl ester compounds such as glycidyl (meth)acrylate and glycidyl methacrylate; vinyl ester compounds such as vinyl acetate, vinyl propionate, vinyl butyrate, and vinyl benzoate;It may include unsaturated ether compounds such as vinylmethyl ether, vinylethyl ether, and allylglycidyl ether; vinyl cyanide compounds such as acrylonitrile, methacrylonitrile, α-chloroacrylonitrile, and vinylidene cyanide; unsaturated amide compounds such as acrylamide, methacrylamide, α-chloroacrylamide, N-2-hydroxyethylacrylamide, and N-2-hydroxyethylmethacrylamide; aliphatic conjugated dienes such as 1,3-butadiene, isoprene, and chloroprene; and maleimide compounds such as N-benzylmaleimide, N-phenylmaleimide, and N-cyclohexylmaleimide.

[0085] These can be used individually or in combination of two or more.

[0086] The weight average molecular weight of the above cardo-based resin may be 1,000 g / mol to 30,000 g / mol. Within this range, the hardness of the photocured pattern formed from the composition is improved, and the residual film rate is increased, thereby improving durability.

[0087] The acid value of the above cardo-based resin may be 50 to 130 mgKOH / g. Accordingly, the solubility of the photocuring film formed from the above composition in the developer is sufficiently high so that residue generation is suppressed and a fine photocuring pattern can be formed.

[0088] In some embodiments, the weight ratio of the cardo-based resin to the copolymer represented by Formula 1 may be 1 to 8, 1.2 to 6, 1.5 to 5, or 2 to 4. Within these ranges, compounds such as photopolymerizable compounds and photopolymerization initiators can be sufficiently dispersed while providing improved adhesion and durability / chemical resistance.

[0089] The content of the alkali-soluble resin may be 1% to 50% by weight. In some embodiments, the content of the alkali-soluble resin may be 5% to 30% by weight or 10% to 20% by weight. Within the above range, the alkali-soluble resin can be sufficiently dissolved in the developer, thereby improving the pattern formation quality and speed.

[0090] In the case of a colored photosensitive resin composition according to the embodiments of the present invention, solubility in the rework solution is further improved and particle size change during the development process is further suppressed, thereby further improving the reworkability of the composition.

[0091] The above composition may include a photopolymerizable compound to further improve the curability of the coloring pattern. For example, the photopolymerizable compound may be cross-linked by a photopolymerization initiator described later to form a cured network.

[0092] The photopolymerizable compound may include a monofunctional or polyfunctional (two or more functional) compound containing ethylenically unsaturated bonds (e.g., (meth)acrylate-based compounds). In exemplary embodiments, the photopolymerizable compound may include a (meth)acrylate-based compound having two or more functionalities. In some embodiments, considering the stability of the fine coloring pattern, the photopolymerizable compound may include a (meth)acrylate-based compound having two to six functionalities.

[0093] Examples of the above monofunctional ethylenically unsaturated bond-containing compounds may include nonylphenylcarbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexylcarbitol acrylate, 2-hydroxyethyl acrylate, N-vinylpyrrolidone, etc.

[0094] Examples of the above-mentioned difunctional ethylenically unsaturated bond-containing compounds include 1,6-hexanediol di(meth)acrylate, ethylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, bis(acryloyloxyethyl) ether of bisphenol A, 3-methylpentanediol di(meth)acrylate, etc.

[0095] Examples of the above compounds containing three or more ethylene unsaturated bonds include trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, etc.

[0096] These can be used individually or in combination of two or more.

[0097] The content of the photopolymerizable compound may be about 1% to 15% by weight of the total weight of the colored photosensitive resin composition. According to some embodiments, the content of the photopolymerizable compound may be about 0.5% to 10% by weight or 1% to 5% by weight of the total weight of the colored photosensitive resin composition. Within the above range, the intensity and smoothness of the coloring pattern can be enhanced while suppressing the occurrence of reverse taper and residue.

[0098] A colored photosensitive resin composition according to exemplary embodiments comprises a coloring agent. The coloring agent may include a blue pigment and / or a violet pigment. For example, the coloring agent may include Pigment Blue 15:6, Pigment Blue 16, Pigment Blue 60, etc. as a blue pigment. These may be used alone or in combination of two or more. The coloring agent may include Pigment Violet 23, Pigment Violet 29, etc. as a violet pigment. These may be used alone or in combination of two or more.

[0099] In one embodiment, the coloring agent may include pigment blue 15:6 and pigment violet 23. Accordingly, the optical density of the photocured pattern produced from the composition may be further improved.

[0100] The content of pigment blue 15:6 in the total weight of the above coloring agent may be 60% to 70% by weight, and the content of pigment violet 29 may be 30% to 40% by weight. Within the above range, the dispersibility of the coloring agent may be improved.

[0101] The content of the coloring agent may be 10% to 40% by weight of the total weight of the composition. According to some embodiments, the content of the coloring agent may be 15% to 30% by weight of the total weight of the composition.

[0102] In some embodiments, the pigment may be used together with a pigment dispersant. The pigment dispersant may be added together with the pigment to suppress the aggregation of the pigment and enhance dispersion properties.

[0103] Examples of the above pigment dispersants include cationic, anionic, nonionic, amphoteric, polyester, and polyamine surfactants.

[0104] For example, the content of the pigment dispersant may be included in an amount of 5% to 50% by weight relative to the total weight of the solid content of the pigment. Within this range, excessive viscosity increase can be suppressed, and the aggregation of the pigment and gelation of the composition can be prevented.

[0105] The above photopolymerization initiator can, for example, induce a cross-linking reaction of the above-described photopolymerizable compound to provide curing pattern characteristics. The photopolymerization initiator may include compounds widely used in the field that can induce a cross-linking reaction of the above-described ethylenically unsaturated bond-containing compound.

[0106] In some embodiments, the photopolymerization initiator may comprise a compound comprising a carbazole unit or a fluorene unit. For example, the photopolymerization initiator may be an oxime ester-based initiator comprising a carbazole unit or a fluorene unit. In this case, deep curing of the coloring pattern can be promoted more effectively even in a low-temperature process.

[0107] By using the aforementioned photopolymerization initiator, degradation of exposure / development characteristics and resolution for fine pattern formation caused by the use of the alkali-soluble resin can be suppressed, and the reliability of the colored pattern can be improved.

[0108] The above photopolymerization initiator may further include additional initiators widely used in the field that can induce a cross-linking reaction of the aforementioned ethylenically unsaturated bond-containing compound.

[0109] The above additional photopolymerization initiator may include acetophenone-based initiators, benzophenone-based initiators, benzoin-based initiators, thioxantone-based initiators, triazine-based initiators, oxime-based initiators, etc.

[0110] Examples of the above-mentioned acetophenone-based initiators include diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, benzyldimethylketal, 2-hydroxy-1-[4-(2-hydroxyethoxy)phenyl]-2-methylpropan-1-one, 1-hydroxycyclohexylphenylketone, 2-methyl-1-(4-methylthiophenyl)-2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)butan-1-one, 2-hydroxy-2-methyl-1-[4-(1-methylvinyl)phenyl]propan-1-one, 2-(4-methylbenzyl)-2-(dimethylamino)-1-(4-morpholinophenyl)butan-1-one, etc.

[0111] Examples of the above-mentioned benzoin-based initiators include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, etc.

[0112] Examples of the above-mentioned benzophenone-based initiators include benzophenone, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenylsulfide, 3,3',4,4'-tetra(tert-butylperoxycarbonyl)benzophenone, 2,4,6-trimethylbenzophenone, etc.

[0113] Examples of the above-mentioned thioxantone-based initiators include 2-isopropylthioxantone, 2,4-diethylthioxantone, 2,4-dichlorothioxantone, and 1-chloro-4-propoxythioxantone.

[0114] Examples of the above triazine-based initiators include 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxynaphthyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxystyryl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(5-methylfuran-2-yl)ethenyl]-1,3,5-triazine, and 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)ethenyl]-1,3,5-triazine. Examples include 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)ethenyl]-1,3,5-triazine.

[0115] Examples of the above-mentioned oxime-based initiators include o-ethoxycarbonyl-α-oxyimino-1-phenylpropan-1-one, and commercially available products include BASF's OXE-01 and OXE-02.

[0116] In one embodiment, the colored photosensitive resin composition may further include a photopolymerization initiation aid. The photopolymerization initiation aid promotes the polymerization of a photopolymerizable compound and can be used together with a photopolymerization initiator.

[0117] For example, the above photopolymerization initiation aid may include amine-based initiation aids, alkoxyanthracene-based photopolymerization initiation aids, etc.

[0118] The content of the photopolymerization initiator may be 0.01% to 3% by weight of the total weight of the composition. According to some embodiments, the content of the photopolymerization initiator may be 0.1% to 2% by weight or 0.3% to 1% by weight of the total weight of the composition. Within this range, the curability of the coloring pattern is improved, while preventing the pattern from falling off during the development process and preventing the occurrence of wrinkles caused by excessive cross-linking reactions.

[0119] The above solvent may include an organic solvent that has solubility for the alkali-soluble resin described above and can provide coating properties for the colored photosensitive resin composition.

[0120] For example, ether-based solvents, acetate-based solvents, aromatic hydrocarbon-based solvents, ketone-based solvents, alcohol-based solvents and / or ester-based solvents may be used.

[0121] Examples of the above ether-based solvents include ethylene glycol monoalkyl ether compounds, diethylene glycol dialkyl ether compounds, propylene glycol monomethyl ether, etc.

[0122] Examples of the above acetate-based solvents include methyl cellosolve acetate, ethyl cellosolve acetate, alkyl acetate, alkoxyalkyl acetate, ethylene glycol monoacetate, ethylene glycol diacetate, propylene glycol methyl ether acetate, ethylene glycol monoalkyl ether acetate, diethylene glycol monoalkyl ether acetate, dipropylene glycol methyl ether acetate, diethylene glycol monoacetate, diethylene glycol diacetate, diethylene glycol monoalkyl ether acetate, propylene glycol monoacetate, propylene glycol diacetate, propylene glycol monoalkyl ether acetate, etc.

[0123] Examples of the above aromatic hydrocarbon solvents include benzene, toluene, xylene, mesitylene, etc.

[0124] Examples of the above-mentioned ketone-based solvents include methyl ethyl ketone, acetone, methyl amyl ketone, methyl isobutyl ketone, cyclohexanone, etc.

[0125] Examples of the above alcohol-based solvents include ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, glycerin, 4-hydroxy-4-methyl-2-pentanone, etc.

[0126] The amount of the above solvent can be appropriately adjusted considering the sufficient solubility of components such as the above alkali-soluble resin and the coating properties of the composition, and may be included as the remainder of the above colored photosensitive resin composition.

[0127] The term "residual amount" as used in this application is used in an open sense, adjusted according to components or additives added in variable amounts.

[0128] In exemplary embodiments, the content of the solvent may be 50% to 95% by weight of the total weight of the colored photosensitive resin composition. In some embodiments, the content of the solvent may be 60% to 90% by weight, or 70% to 90% by weight, of the total weight of the colored photosensitive resin composition. Within these ranges, the applicability may be improved when applied using an application device such as a roll coater, spin coater, slit-and-spin coater, slit coater, inkjet, etc.

[0129] According to exemplary embodiments, a colored photosensitive resin composition can be prepared as follows.

[0130] In some embodiments, the coloring agent may be dissolved in the solvent to prepare a coloring solution. The alkali-soluble resin, the photopolymerizable compound, and the photopolymerization initiator may be added to the coloring solution to prepare a photosensitive resin composition according to the embodiments of the present invention.

[0131] The above coloring agent may be dissolved or dispersed in the solvent. In one embodiment, the coloring solution can be prepared more easily by adding the pigment dispersant described above.

[0132] In some embodiments, a first solution in which the coloring agent is dissolved in the solvent, and a second solution in which the alkali-soluble resin, the photopolymerizable compound, and the photopolymerization initiator are mixed in the solvent can each be prepared. The colored photosensitive resin composition can be prepared by mixing the first solution and the second solution together.

[0133] In some embodiments, the colored photosensitive resin composition may further include additives within a range that does not impair the low-temperature curing characteristics of the alkali-soluble resin described above and the pattern stability / high-resolution characteristics of the colored photosensitive resin composition.

[0134] For example, the above additive may include an antioxidant or a UV absorber, a surfactant, an adhesion promoter, a UV absorber, etc.

[0135] Examples of the above antioxidants or ultraviolet absorbers include benzotriazole compounds, alkyl phenol compounds, alkoxybenzophenone compounds, phenolic antioxidants, phosphorus-based antioxidants, etc.

[0136] An example of the above-mentioned leveling agent is SH-8400 of Dow Chemical Inc.

[0137] The above surfactant can be used to further improve the film-forming ability of the photosensitive resin composition, and silicone-based surfactants or fluorine-based surfactants, etc., may be preferably used.

[0138] Examples of the above silicone-based surfactants include commercially available products such as DC3PA, DC7PA, SH11PA, SH21PA, and SH-8400 from Dow Corning Toray Silicon, and TSF-4440, TSF-4300, TSF-4445, TSF-4446, TSF-4460, and TSF-4452 from GE Toshiba Silicon. Examples of the above fluorine-based surfactants include commercially available products such as Megapiece F-470, F-471, F-475, F-482, F-489, and F-554 (Dai Nippon Ink Kagaku Kogyo), BM-1000, BM-1100 (BM Chemie), and Proride FC-135 / FC-170C / FC-430 (Sumitomo 3M). The surfactants exemplified above can each be used individually or in combination of two or more types.

[0139] Examples of the above surfactants include silicone-based surfactants or fluorine-based surfactants.

[0140] Examples of the above-mentioned adhesion promoters include linear silane coupling agents such as single silane compounds or alkoxysilane series compounds. For example, the above adhesion promoter may include vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris(2-methoxyethoxy)silane, N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane, N-(2-aminoethyl)-3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-isocyanatepropyltrimethoxysilane, 3-isocyanatepropyltriethoxysilane, etc. These can be used individually or in combination of two or more.

[0141] For example, the content of the additive may be 0.001% to 10% by weight or 0.01% to 5% by weight of the total weight of the colored photosensitive resin composition.

[0142] In some embodiments, the particle size change rate defined by Formula 1 below may be 10% or less, 8% or less, or 5% or less.

[0143] [Equation 1]

[0144] Particle size change rate = A / B

[0145] In the above Equation 1, A is the average particle size (D50) of the composition contained in the remaining developer after the colored coating layer formed from the composition is immersed in the developer for 2 minutes, and B is the average particle size (D50) of the composition before the formation of the colored coating layer.

[0146] For example, the term average particle size (D50) as used in this specification may represent the particle size at 50% of the cumulative count when accumulating from the smallest particles. The particle size can be measured using a particle size analyzer (ELSZ-2000).

[0147] For example, the above composition can be spin-coated onto a 5cm × 5cm ITO substrate and dried at 80°C to 120°C for 50 to 100 seconds to form a colored coating layer. The substrate with the colored coating layer formed thereon can be puddle developed by immersing it in 20g of a 0.04% KOH developer for 2 minutes. After removing the substrate, the remaining developer is recovered, and the average particle size of the above composition contained in the remaining developer can be measured by the particle size analyzer.

[0148] Within the above range, the change in particle size of the composition during development may be reduced, thereby improving reworkability. For example, as the rate of change in particle size increases, the change in particle size of the composition before and after development increases, which may deteriorate reworkability.

[0149] In one embodiment, the particle size change rate of the composition may be 0.0001% to 10%, 0.001% to 8%, or 0.01% to 5%. Within the above range, the reworkability of the composition may be further improved.

[0150] A blue bank according to exemplary embodiments may be formed from the composition. For example, the blue bank may include a photocurable pattern formed from the composition on a substrate. The blue bank can prevent light scattering of the organic light-emitting diode by absorbing light incident from the outside without reflecting it, and visual information can be conveyed to the user accurately and clearly.

[0151] According to exemplary embodiments, the blue bank can be manufactured as follows.

[0152] In some embodiments, the colored photosensitive resin composition may be applied onto a substrate. The application may be performed by a wet coating method using an application device such as a roll coater, spin coater, slit-and-spin coater, slit coater (die coater), or inkjet.

[0153] Next, pre-baking can be performed to dry the solvent from the applied composition.

[0154] Pre-baking is performed by heating the composition applied on the substrate using an oven, a hot plate, etc. The heating temperature and heating time of the pre-baking can be adjusted according to the solvent used, and for example, the pre-baking can be performed at a temperature of 80 to 150°C for 1 to 5 minutes.

[0155] After pre-baking, a coating film may be formed on the substrate. A photomask may be superimposed on the coating film, and an active light may be irradiated to cure the exposed portion. The exposure may be performed using an exposure machine including a light source, and the coating film in the portion (exposed portion) corresponding to the opening of the photomask may be photocured. The light source may include, for example, visible light, ultraviolet light, X-rays, and electron beams.

[0156] The thickness of the coating film may be, for example, 0.5 μm to 3.0 μm, and this can be adjusted considering the scale and purpose of use of the organic light-emitting device to be applied.

[0157] After the above exposure, the unexposed portion can be removed using an alkaline aqueous solution. Accordingly, the unexposed portion is developed and the exposed portion remains to form a preliminary photocuring pattern. The alkaline aqueous solution is an aqueous solution of KOH (potassium hydroxide) or TMAH (tetramethylammonium hydroxide).

[0158] For example, the above developing process can be performed using an alkaline aqueous solution containing about 0.02% to 3% by weight of KOH (potassium hydroxide) or TMAH (tetramethylammonium hydroxide) at a temperature of about 20°C to 30°C using a developing machine or an ultrasonic cleaner, etc.

[0159] For example, the above development process can be performed using a puddle phenomenon. Accordingly, damage to fine patterns is reduced, and high-resolution patterns can be realized.

[0160] The above preliminary photocuring pattern can be re-dried. After the development process, a cleaning process may be performed one or more times to remove the alkaline aqueous solution remaining on the substrate, and the substrate may be dried again to remove the solvent contained in the cleaning solution and / or the alkaline aqueous solution.

[0161] Subsequently, the above-mentioned preliminary photocuring pattern can be post-baked. The post-baking can be performed to increase the adhesion between the patterned coating film and the substrate, and, for example, can be performed at a temperature of 80°C to 240°C for about 60 to 120 minutes. The post-baking can be performed using an oven, a hot plate, etc.

[0162] The organic light-emitting element according to exemplary embodiments may have improved reliability by including the blue bank having improved optical properties and durability, and the quality of the image display device including the organic light-emitting element may also be improved.

[0164] In the following, embodiments of the present invention are further described with reference to specific experimental examples. The embodiments and comparative examples included in the experimental examples are merely illustrative of the present invention and are not intended to limit the appended claims. It is obvious to those skilled in the art that various changes and modifications to the embodiments are possible within the scope and spirit of the present invention, and that such variations and modifications fall within the scope of the appended claims.

[0165] 제조예

[0166] (A) Colorant dispersion

[0167] For every 100 parts by weight of the total colorant dispersion, 16 parts by weight of colorant pigment, 0.5 parts by weight of Solsperse 5000 (manufactured by Lubrisol) and 3.5 parts by weight of DiperBYK-163 (manufactured by BYK) as pigment dispersants, and 3 parts by weight of n-butanol and 17 parts by weight of propylene glycol monomethyl ether acetate (PGMEA) as solvents were placed in a container and stirred for 2 hours using a high-speed stirrer. Subsequently, 40 parts by weight of PGMEA were additionally mixed and dispersed for 3 hours. Afterward, the remaining 20 parts by weight of PGMEA were further mixed to prepare colorant dispersions (A-1 to A-5). The type and content of the colorant pigment were adjusted as shown in Table 1.

[0168] 구분 착색 안료 청색 안료 바이올렛색 안료 종류 함량 종류 함량 A-1 Blue 15:6 10.5 Violet 23 5.5 A-2 Blue 15:6 10.5 Violet 29 5.5 A-3 Blue 16 10.5 Violet 23 5.5 A-4 Blue 60 10.5 Violet 23 5.5 A-5 Blue 15:6 16 - -

[0169] Blue 15:6: Pigment Blue 15:6 (Fastogen Blue EP-101, manufactured by BASF)

[0170] Blue 16: Pigment Blue 16 (Manufactured by CPMA)

[0171] Blue 60: Pigment Blue 60 (Manufactured by CPMA)

[0172] Violet 23: Pigment Violet 23 (Fastogen Super Violet 140VS, manufactured by DIC)

[0173] Violet 29: Pigment Violet 29 (Palamid Violet 50-1105, manufactured by BASF)

[0175] (B) Alkali-soluble resin

[0176] (B-1) Synthesis of a copolymer represented by Chemical Formula 1

[0177] Nitrogen was flowed at a rate of 0.02 L / min into a 1 L flask equipped with a reflux condenser, a dropping funnel, and a stirrer, 150 g of diethylene glycol methyl ethyl ether was added, and the mixture was heated to 70 °C while stirring. Subsequently, 3,4-epoxycyclohexylmethyl(meth)acrylate (EDCPA), compound M, and acrylic acid were dissolved in 150 g of diethyl glycol methyl ethyl ether to prepare a mixed solution. The type of compound M and the content (mol) of each compound were controlled as shown in Table 2 below.

[0178] The above mixed solution was added dropwise into a flask using a dropping funnel. Subsequently, 27.9 g (0.11 mol) of the polymerization initiator 2,2'-azobis(2,4-dimethylvaleronitrile) was dissolved in 200 g of diethylene glycol methyl ethyl ether to prepare a polymerization initiator solution, which was then added dropwise into the flask over a period of 4 hours using a separate dropping funnel. Afterward, the binder resins (BP-1 to BP-24) were prepared by maintaining the temperature at 70°C for 4 hours and cooling to room temperature.

[0179] 구분 EDCPA 아크릴산 화합물 M 함량 함량 함량 종류 BP-1 0.1 0.2 0.7 2-Hydroxyethyl methacrylate BP-2 0.1 0.2 0.7 4-hydroxybutyl acrylate BP-3 0.1 0.2 0.7 6-hydroxyhexyl acrylate BP-4 0.1 0.2 0.7 8-acryloyloxy-1-octanol BP-5 0.1 0.2 0.7 ω-Hydroxydecylacrylate BP-6 0.1 0.2 0.7 acrylic acid 2-(2-methoxy-ethoxy)-ethyl ester BP-7 0.1 0.2 0.7 2,5,8,11-tetraoxatridecan-13-yl acrylate BP-8 0.1 0.2 0.7 2-(2-{2-[2-(2-methoxyethoxy)ethoxy]ethoxy}ethoxy)ethyl acrylate BP-9 0.1 0.2 0.7 diethylene glycol monoacrylate BP-10 0.1 0.2 0.7 tetraethylene glycol monoacrylate BP-11 0.1 0.2 0.7 methoxy PEG(350) monoacrylate BP-12 0.1 0.2 0.7 2,3-dihydroxypropyl acrylate BP-13 0.1 0.2 0.7 pentaerythritol monoacrylate BP-14 0.1 0.2 0.7 2-glycerol monoacrylate BP-15 0.1 0.2 0.7 5,6-dihydroxyhexyl acrylate BP-16 0.1 0.2 0.7 N-(tris(hydroxymethyl)methyl)acrylamide BP-17 0.1 0.2 0.7 N,N-bis(2-hydroxyethyl)aminomethyl-acrylamide BP-18 0.3 0.2 0.5 2-Hydroxyethyl methacrylate BP-19 0.5 0.2 0.3 2-Hydroxyethyl methacrylate BP-20 0.7 0.2 0.1 2-Hydroxyethyl methacrylate BP-21 0.75 0.2 0.05 2-Hydroxyethyl methacrylate BP-22 0.05 0.2 0.75 2-Hydroxyethyl methacrylate BP-23 × 0.2 0.8 2-Hydroxyethyl methacrylate BP-24 0.8 0.2 × 2-Hydroxyethyl methacrylate

[0180] (B-2) Cardo-based resin

[0181] 42.5 g of 9,9-Bisphenolfluorene was placed in a 3-Neck flask, and 220 mL of 2-(chloromethyl)oxirane was added. After adding 100 mg of tetrabutylammonium bromide, stirring was started while raising the temperature to 90 o The temperature was raised to C. After confirming that the unreacted material content was less than 0.3%, vacuum distillation was performed. The temperature was raised to 30 oAfter lowering the temperature to C, dichloromethane was injected, and NaOH was slowly added. After confirming that the product yield was 96% or higher using high-performance liquid chromatography (HPLC), the reaction was terminated by adding 5% HCl dropwise.

[0182] After extracting the product and separating the layers, the organic layer was washed with water and neutralized. The organic layer was dried with MgSO4 and concentrated by vacuum distillation using a rotary evaporator. Dichloromethane was added to the concentrated product and 40 o Methanol was added while raising the temperature to C. The solution temperature was lowered and the resulting solid was filtered while stirring, and then vacuum dried at room temperature to obtain 52.7 g of white solid powder.

[0183] The above solid powder was placed in a 3-neck flask, 27 g of thiophenol and 32 g of ethanol were added, and the mixture was stirred. 16.3 g of triethylamine was slowly added dropwise to the reaction solution. Subsequently, the ethanol was removed by vacuum distillation, the organic matter was dissolved in dichloromethane and washed with water, and the dichloromethane was removed by vacuum distillation. Propylene glycol monomethyl ether acetate (PGMEA) was added to the 3-neck flask to prepare a solution with a solid content of 50 wt%, and then 115 o Raised the temperature to C. 115 o After adding 31.1 g of 3,3',4,4'-Biphenyltetracarboxylic dianhydride dropwise at C, 115 for 6 hours o Stirring was performed while maintaining C. 7.35 g of phthalic anhydride was added to this, and stirring was continued for 2 hours to obtain a cardo-based alkali-soluble resin with a weight-average molecular weight of 3,500 g / mol.

[0185] 실시예들 및 비교예들

[0186] Colored photosensitive resin compositions were prepared by changing the types and contents of the components as shown in Table 3 below. The contents were expressed as weight% of the total weight of the composition.

[0187] 구분 (A) (B-1) (B-2) (C) (D) (E) (F) (중량%) 종류 Content type Content Content Content Content Content Content Example 1 A-1 18 BP1 2 7 5 0.3 0.01 67.69 Example 2 A-2 18 BP1 2 7 5 0.3 0.01 67.69 Example 3 A-3 18 BP1 2 7 5 0.3 0.01 67.69 Example 4 A-4 18 BP1 2 7 5 0.3 0.01 67.69 Example 5 A-5 18 BP1 2 7 5 0.3 0.01 67.69 Example 6 A-1 18 BP2 2 7 5 0.3 0.01 67.69 Example 7 A-1 18 BP3 2 7 5 0.3 0.01 67.69 Example 8 A-1 18 BP4 2 7 5 0.3 0.01 67.69 Example 9 A-1 18 BP5 2 7 5 0.3 0.01 67.69 Example 10 A-1 18 BP6 2 7 5 0.3 0.01 67.69 Example 11 A-1 18 BP7 2 7 5 0.3 0.01 67.69 Example 12 A-1 18 BP8 2 7 5 0.3 0.01 67.69 Example 13 A-1 18 BP9 2 7 5 0.3 0.01 67.69 Example 14 A-1 18 BP10 2 7 5 0.3 0.01 67.69 Example 15 A-1 18 BP11 2 7 5 0.3 0.01 67.69 Example 16 A-1 18 BP12 2 7 5 0.3 0.01 67.69 Example 17 A-1 18 BP13 2 7 5 0.3 0.01 67.69 Example 18 A-1 18 BP14 2 7 5 0.3 0.01 67.69 Example 19 A-1 18 BP15 2 7 5 0.3 0.01 67.69 Example 20 A-1 18 BP16 2 7 5 0.3 0.01 67.69 Example 21 A-1 18 BP17 2 7 5 0.3 0.01 67.69 Example 22 A-1 18 BP18 2 7 5 0.3 0.01 67.69 Example 23 A-1 18 BP19 2 7 5 0.3 0.01 67.69 Example 24 A-1 18 BP20 2 7 5 0.3 0.01 67.69 Example 25 A-1 18 BP21 2 7 5 0.3 0.01 67.69 Example 26 A-1 18 BP22 2 7 5 0.3 0.01 67.69 Example 27 A-1 18 BP1 4.5 4.5 5 0.3 0.01 67.69 Example 28 A-1 18 BP1 7 2 5 0.3 0.01 67.69 Comparative Example 1 A-1 18 BP1 9 - 5 0.3 0.01 67.69 Comparative Example 2 A-1 18 - - 7 5 0.3 0.01 67.69 Comparative Example 3 A-1 18 BP-23 2 7 5 0.3 0.01 67.69 Comparative Example 4 A-1 18 BP-24 2 7 5 0.3 0.01 67.69

[0189] (A) Colorant dispersion: Colorant dispersions A-1 to A-5 prepared in the preparation example

[0190] (B) Alkali-soluble resin

[0191] (B-1) Binder resins BP-1 to BP-24 prepared in the preparation example

[0192] (B-2) Cardo-based resin prepared in the preparation example

[0193] (C) Photopolymerizable compound: A9550NS (Dipentaerythritol polyacrylate, manufactured by Cinnakamura)

[0194] (D) Photopolymerization initiator: TR-PBG-345 (Tronley)

[0195] (E) Additive: F-554 (DIC)

[0196] (F) Solvent: Propylene glycol monomethyl ether acetate (PGMEA)

[0198] Experimental Example 1: Evaluation of Optical Density, Chemical Resistance, and Residue

[0199] The colored photosensitive compositions of the examples and comparative examples were spin-coated onto a 5cm × 5cm ITO substrate, and then dried at 100°C for 90 seconds to form a colored coating layer. Subsequently, an exposure dose of 80 mJ / cm² 2 A pattern was formed by exposure to light, and the unexposed area was puddle-developed by immersing it in 20g of a 0.04% KOH developer for 2 minutes. Subsequently, a blue bank having a photocured pattern formed on a substrate was prepared by post-baking at 230°C for 20 minutes. The physical properties of the blue bank were evaluated as follows.

[0201] (1) Optical density evaluation

[0202] The optical density (OD) of the above photocuring pattern was measured using an optical density meter (manufactured by X-Rite).

[0203] Rate of change in optical density (%) = {(Optical density after immersion) - (Optical density before immersion)} / Optical density before immersion × 100

[0205] (2) Chemical resistance evaluation

[0206] Chemical resistance was evaluated by immersing the substrate with the above photocured pattern in an NMP (N-methyl-2-pyrrolidone) solution and measuring the rate of change in optical density.

[0207] Chemical Resistance Evaluation Criteria

[0208] ○: Optical density change rate -10% or less

[0209] △: Rate of change in optical density -50% or more and less than -10%

[0210] ×: Rate of change in optical density less than -50%

[0212] (3) Residue evaluation

[0213] InO of the substrate on which the above photocuring pattern is formed using a secondary ion mass spectrometer - The residue was evaluated by measuring the concentration of the components. Specifically, the InO in the non-exposed area - Concentration of the component and InO of the ITO substrate before the formation of the colored coating layer - The residue was evaluated by measuring the concentration of the component and determining the residue ratio (%) as follows.

[0214] Residue ratio (%) = (InO in unexposed area - Concentration) / (InO of ITO) - Concentration) × 100

[0215] <Residue Evaluation Criteria>

[0216] ○: Maintain 80% or higher

[0217] △: Maintain 50% or more and less than 80%

[0218] ×: Maintain less than 50%

[0220] Experimental Example 2: Evaluation of Particle Size Change

[0221] The colored photosensitive compositions of the examples and comparative examples were spin-coated onto a 5cm × 5cm ITO substrate, and then dried at 100°C for 90 seconds to form a colored coating layer. Subsequently, the substrate with the colored coating layer formed thereon was immersed in 20g of a 0.04% KOH developer for 2 minutes, after which the substrate was removed and the remaining developer was recovered. The average particle size (D50) at 50% of the cumulative count was measured for the composition contained in the recovered remaining developer using a particle size analyzer (ELSZ-2000).

[0222] The change rate (%) of the residual developer particle size defined by Equation 1 was calculated and evaluated as follows.

[0223] <Criteria for Evaluating Changes in Particle Size>

[0224] ○: Particle size change rate less than 10%

[0225] △: Particle size change rate exceeding 10% and less than 50%

[0226] ×: Particle size change rate of 50% or more

[0228] Experimental Example 3: Evaluation of Rework Solution Solubility

[0229] The colored photosensitive compositions of the examples and comparative examples were spin-coated onto a 5cm × 5cm ITO substrate, and then dried at 100°C for 90 seconds to form a colored coating layer. Subsequently, an exposure dose of 80 mJ / cm² 2 The solubility in the rework solution was evaluated as follows by exposing to light and immersing in the rework solution at 50°C for 1 minute.

[0230] <Solubility Evaluation Criteria>

[0231] ○: Full melting

[0232] △: Film peeling off or small amount dissolving

[0233] ×: Cannot be dissolved

[0234] The results are shown in Table 4 below.

[0235] division Optical density ( / ㎛) Chemical resistance Residue Change in particle size Solubility Example 1 0.65 ○ ○ ○ ○ Example 2 0.71 ○ ○ ○ ○ Example 3 0.66 ○ ○ ○ ○ Example 4 0.65 ○ ○ ○ ○ Example 5 0.52 △ △ △ △ Example 6 0.72 ○ ○ ○ ○ Example 7 0.72 ○ ○ ○ ○ Example 8 0.71 ○ ○ ○ ○ Example 9 0.72 ○ ○ ○ ○ Example 10 0.72 ○ ○ ○ ○ Example 11 0.71 ○ ○ ○ ○ Example 12 0.72 ○ ○ ○ ○ Example 13 0.72 ○ ○ ○ ○ Example 14 0.71 ○ ○ ○ ○ Example 15 0.72 ○ ○ ○ ○ Example 16 0.72 ○ ○ ○ ○ Example 17 0.72 ○ ○ ○ ○ Example 18 0.72 ○ ○ ○ ○ Example 19 0.71 ○ ○ ○ ○ Example 20 0.72 ○ ○ ○ ○ Example 21 0.72 ○ ○ ○ ○ Example 22 0.72 ○ ○ ○ ○ Example 23 0.71 ○ ○ ○ ○ Example 24 0.71 ○ ○ ○ ○ Example 25 0.71 △ ○ △ △ Example 26 0.53 ○ △ ○ △ Example 27 0.71 ○ ○ ○ ○ Example 28 0.52 △ △ △ △ Comparative Example 1 0.72 △ × △ △ Comparative Example 2 0.71 × ○ × ○ Comparative Example 3 0.71 ○ × ○ △ Comparative Example 4 0.52 × ○ ○ △

[0237] Referring to Table 4 above, the photocurable patterns prepared from the colored photosensitive resin compositions of the examples exhibited improved optical density and chemical resistance / solubility, and the degree of curing was improved, resulting in reduced pattern residue. In addition, the compositions of the examples showed low change in waste developer particle size, thereby exhibiting improved reworkability.

[0238] In the case of photocurable patterns prepared from colored photosensitive resin compositions of comparative examples, optical density was reduced and chemical resistance / solubility deteriorated.

[0239] In the case of a photocured pattern prepared from the composition of Comparative Example 1 that does not contain a cardo-based resin, curing was not performed sufficiently, resulting in an excessive increase in pattern residue.

[0240] In the case of photocuring patterns prepared from the compositions of Comparative Examples 2 to 4 that do not contain the binder resin represented by Chemical Formula 1, the change in particle size with respect to the waste developer increased excessively, resulting in reduced reworkability.

[0242] The description above is merely an example of applying the principles of the present invention, and other configurations may be included without departing from the scope of the present invention.

Claims

Claim 1 A colored photosensitive resin composition comprising: an alkali-soluble resin comprising a copolymer represented by the following chemical formula 1 and a cardo-based resin; a photopolymerizable compound; a colorant; a photopolymerization initiator; and a solvent: [Chemical Formula 1] (In Chemical Formula 1, A is or It is indicated as, and B is Represented by, where X is oxygen (O) or nitrogen (N), and R1 to R4 are each independently hydrogen, halogen, hydroxyl group, substituted or unsubstituted C1 to 30 alkyl group, substituted or unsubstituted C1 to 30 alkenyl group, substituted or unsubstituted C1 to 30 alkynyl group, substituted or unsubstituted C1 to 30 aryl group, substituted or unsubstituted C1 to 30 alkoxy group, substituted or unsubstituted C1 to 30 hydroxyalkyl group, substituted or unsubstituted C2 to 40 hydroxyalkoxyalkyl group, or substituted or unsubstituted C3 to 30 cycloalkyl group, a to c are each independently integers from 1 to 20, and d is an integer from 0 to 10). Claim 2 A colored photosensitive resin composition according to claim 1, wherein in the formula 1, a to c are each independently integers from 1 to 10, and the ratio of b to a is from 0.1 to 8. Claim 3 In claim 1, in the above formula 1, B is or A colored photosensitive resin composition represented by, wherein R5 is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms or a substituted or unsubstituted hydroxyalkyl group having 1 to 30 carbon atoms, R6 is a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms, d is an integer from 1 to 10, and e is an integer from 1 to 3. Claim 4 In claim 3, in the above formula 1, B is A colored photosensitive resin composition represented by, where X is oxygen, d is an integer from 1 to 5, and R5 is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms or a substituted or unsubstituted hydroxyalkyl group having 1 to 10 carbon atoms. Claim 5 In claim 3, in the above formula 1, B is A colored photosensitive resin composition represented by, wherein R6 comprises a substituted or unsubstituted tertiary alkylene group having 1 to 30 carbon atoms. Claim 6 A colored photosensitive resin composition according to claim 1, wherein the cardo-based resin comprises a unit derived from the following chemical formula 2: [Chemical Formula 2] (In Chemical Formula 2, R6 and R7 are each independently hydrogen or a methyl group, and L1 to L4 are each independently an alkylene group having 1 to 10 carbon atoms). Claim 7 A colored photosensitive resin composition according to claim 1, wherein the weight average molecular weight of the cardo-based resin is 1,000 g / mol to 30,000 g / mol. Claim 8 A colored photosensitive resin composition according to claim 1, wherein the weight ratio of the cardo-based resin to the copolymer represented by the chemical formula 1 is 1 to 8. Claim 9 A colored photosensitive resin composition according to claim 1, wherein the content of the alkali-soluble resin in the total weight of the composition is 1% to 50% by weight. Claim 10 A colored photosensitive resin composition according to claim 1, wherein the coloring agent comprises CI pigment blue 15:6 and pigment violet 29. Claim 11 A colored photosensitive resin composition according to claim 1, wherein the content of the coloring agent in the total weight of the composition is 10% to 40% by weight. Claim 12 Blue bank formed from a colored photosensitive resin composition according to claim 1. Claim 13 An organic light-emitting device comprising a blue bank according to claim 12. Claim 14 An image display device comprising an organic light-emitting element according to claim 13.

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