Composition for producing alkali-soluble resin, alkali-soluble resin produced from the composition, and photosensitive resin composition containing the same

Abstract

The present invention relates to a composition for producing an alkali-soluble resin, which is a compound for producing an alkali-soluble resin, comprising a dicarboxylic acid anhydride, a tetracarboxylic acid dianhydride, and a diamine, wherein the alkali-soluble resin contains a structural unit derived from the dicarboxylic acid anhydride at at least one of both ends, and the dicarboxylic acid anhydride accounts for 5 to 40 mol % of the dicarboxylic acid anhydride, based on 100 mol % in total of the diamine, the tetracarboxylic acid dianhydride, and the dicarboxylic acid anhydride; an alkali-soluble resin produced from the composition; a photosensitive resin composition containing the alkali-soluble resin; an insulating film formed from the photosensitive resin composition; and a display device including the insulating film.

Description

[Technical Field]

[0001] The present invention relates to a composition for producing an alkali-soluble resin, an alkali-soluble resin produced from the composition, a photosensitive resin composition containing the alkali-soluble resin, an insulating film formed from the photosensitive resin composition, and a display device including the insulating film. [Background technology]

[0002] Photosensitive resin compositions are representative functional polymer materials that have been put to practical use in the production of various precision electronics products, and are currently used in the high-tech industry, particularly in the production of semiconductors and displays. Generally, a photosensitive resin composition refers to a composition that undergoes a chemical change in molecular structure within a short period of time upon irradiation with light, resulting in changes in physical properties such as solubility in a specific solvent, coloration, and curing.

[0003] Photosensitive resin compositions enable micro-precision processing, significantly reduce energy and raw material consumption compared to thermal reaction processes, and can be used quickly and accurately in a small installation space. These compositions are widely used in various precision electronics industries, including advanced printing, semiconductor production, display production, and photocurable surface coating materials. Photosensitive resin compositions can be broadly classified into negative-type and positive-type photosensitive resin compositions, with negative-type photosensitive resin compositions being insoluble in a developer when irradiated with light, and positive-type photosensitive resin compositions being soluble in a developer when irradiated with light. In recent years, as electronic devices have become highly integrated and finer-patterned, positive-type photosensitive resin compositions have become increasingly popular because they can minimize defect rates and improve processing efficiency and resolution.

[0004] Meanwhile, organic light-emitting displays (OLEDs) have attracted attention in the display industry due to their high resolution and the self-luminance of red, green, and blue pixels. OLED devices typically include an organic insulating film, which is typically formed using a polyimide photosensitive resin composition. However, polyimide photosensitive resin compositions generally lack sensitivity compared to photosensitive resin compositions containing siloxane resins, and suffer from a high rate of change in film thickness during processing, resulting in reduced productivity. Furthermore, the insolubility of polyimide resins can lead to development residues during development. Summary of the Invention [Problem to be solved by the invention]

[0005] An object of the present invention is to provide a composition for producing an alkali-soluble resin.

[0006] Another object of the present invention is to provide an alkali-soluble resin produced from the composition for producing an alkali-soluble resin.

[0007] Another object of the present invention is to provide a photosensitive resin composition containing the alkali-soluble resin.

[0008] Another object of the present invention is to provide an insulating film formed from the photosensitive resin composition, and a display device including the insulating film. [Means for solving the problem]

[0009] In order to achieve the above object, the present invention provides a composition for producing an alkali-soluble resin, which is a compound for producing an alkali-soluble resin, comprising a dicarboxylic acid anhydride, a tetracarboxylic acid dianhydride, and a diamine, wherein the alkali-soluble resin contains a structural unit derived from the dicarboxylic acid anhydride at at least one of both ends, and the composition contains 5 to 40 mol % of the dicarboxylic acid anhydride, based on 100 mol % in total of the diamine, the tetracarboxylic acid dianhydride, and the dicarboxylic acid anhydride.

[0010] The dicarboxylic acid anhydride may include at least one of a compound represented by the following Chemical Formula 1 and a compound represented by the following Chemical Formula 2:

[0011] [C1]

[0012] JPEG2026507813000002.jpg28170

[0013] [Case 2]

[0014] JPEG2026507813000003.jpg27170

[0015] In the above Chemical Formula 1 and Chemical Formula 2,

[0016] R1, R2, R3, and R4 each independently represent hydrogen, halogen, a substituted or unsubstituted alkyl having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl having 2 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 30 carbon atoms, a substituted or unsubstituted aryl having 3 to 30 carbon atoms, or a substituted or unsubstituted 3 to 30-membered heteroaryl, or are bonded to adjacent groups to form a ring;

[0017] R5 and R6 each independently represent hydrogen, halogen, a substituted or unsubstituted alkyl having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 30 carbon atoms, a substituted or unsubstituted aryl having 3 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl having 3 to 30 members, or they are bonded to each other with adjacent groups to form a ring.

[0018] The compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 can be represented by any one of Chemical Formulas A-1 to A-14 below.

[0019] JPEG2026507813000004.jpg160170

[0020] The tetracarboxylic dianhydride may include at least one of a compound represented by the following Chemical Formula 3 and a compound represented by the following Chemical Formula 4:

[0021] [C3]

[0022] JPEG2026507813000005.jpg32170

[0023] [C4]

[0024] JPEG2026507813000006.jpg31170

[0025] In the above Chemical Formula 3 and Chemical Formula 4,

[0026] L1 is a single bond, a substituted or unsubstituted alkylene having 1 to 10 carbon atoms, an ether bond (-O-), -R a -OR b - or -(C=O)-OR c -O-(C=O)-,

[0027] R7 and R8 are each independently hydrogen, halogen, substituted or unsubstituted alkyl having 1 to 10 carbon atoms, or haloalkyl having 1 to 10 carbon atoms;

[0028] R a , R b , and R c are each independently substituted or unsubstituted alkylene having 1 to 10 carbon atoms or haloalkyl having 1 to 10 carbon atoms.

[0029] The compound represented by Chemical Formula 3 and the compound represented by Chemical Formula 4 can be represented by any one of the following Chemical Formulas B-1 to B-6.

[0030] JPEG2026507813000007.jpg135170

[0031] The diamine may include a compound represented by the following Chemical Formula 5:

[0032] [5]

[0033] JPEG2026507813000008.jpg22170

[0034] In the above Chemical Formula 5,

[0035] R 10 and R 11 each independently represents hydrogen, hydroxy, halogen, haloalkyl having 1 to 10 carbon atoms, or substituted or unsubstituted alkyl having 1 to 10 carbon atoms;

[0036] L2 and L3 each independently represent a single bond, an ether bond (-O-), -(C=O)-O-, -(C=O)-NH-, -OR d -, -(C=O)-OR e -, -(C=O)-NH-R f -, haloalkylene having 1 to 10 carbon atoms, or substituted or unsubstituted alkylene having 1 to 10 carbon atoms;

[0037] R d , R e , and R f are each independently a substituted or unsubstituted arylene having 3 to 30 carbon atoms,

[0038] R9 is a single bond, an ether bond (-O-), haloalkylene having 1 to 10 carbon atoms, substituted or unsubstituted alkylene having 1 to 10 carbon atoms, or substituted or unsubstituted arylene having 3 to 30 carbon atoms.

[0039] The compound represented by Chemical Formula 5 can be represented by any one of the following Chemical Formulae C-1 to C-8.

[0040] JPEG2026507813000009.jpg128170

[0041] JPEG2026507813000010.jpg75170

[0042] The present invention also provides an alkali-soluble resin produced using the composition for producing an alkali-soluble resin, the alkali-soluble resin comprising a dicarboxylic acid anhydride-derived structural unit, a tetracarboxylic acid dianhydride-derived structural unit, and a diamine-derived structural unit, wherein the alkali-soluble resin contains the dicarboxylic acid anhydride-derived structural unit at at least one of both ends, and the dicarboxylic acid anhydride-derived structural unit accounts for 5 to 40 mol % of the dicarboxylic acid anhydride-derived structural unit, based on 100 mol % in total of the diamine-derived structural unit, the tetracarboxylic acid dianhydride-derived structural unit, and the dicarboxylic acid anhydride-derived structural unit.

[0043] The alkali-soluble resin may have a weight average molecular weight Mw of 1,000 to 50,000.

[0044] The present invention also provides a photosensitive resin composition comprising the alkali-soluble resin; a photosensitizer; and a solvent.

[0045] The alkali-soluble resin can be contained in an amount of 3 to 50% by weight based on 100% by weight of the total photosensitive resin composition.

[0046] The present invention also provides an insulating film comprising a cured product obtained by curing the photosensitive resin composition.

[0047] The present invention also provides a display device including the insulating film. [Effects of the Invention]

[0048] By using the alkali-soluble resin according to the present invention, it is possible to provide a photosensitive resin composition that is excellent in chemical resistance, sensitivity, heat resistance, device performance, bending characteristics, and the like.

[0049] The effects of the present invention are not limited to the effects described above, but must be understood to include all effects that can be inferred from the detailed description of the present invention or the structure of the claims. [Brief explanation of the drawings]

[0050] [Figure 1] 1 is a vertical cross-sectional view of a display device according to an embodiment of the present invention. DETAILED DESCRIPTION OF THE INVENTION

[0051] Hereinafter, each component of the present invention will be described in more detail so that a person having ordinary skill in the art to which the present invention pertains can easily implement the present invention. However, this is merely an example, and the scope of the present invention is not limited to the following content.

[0052] As used herein, "substituted or unsubstituted" may mean substituted or unsubstituted with one or more substituents selected from the group consisting of a deuterium atom, a halogen atom, a hydroxy group, a cyano group, a nitro group, an amino group, a silyl group, an oxy group, a thio group, a sulfinyl group, a sulfonyl group, a carbonyl group, a boron group, a phosphine oxide group, a phosphine sulfide group, an alkyl group, an alkenyl group, an alkynyl group, a haloalkyl group, a hydrocarbon ring group, an aryl group, and a heterocyclic group. Each of the exemplified substituents may be substituted or unsubstituted. For example, a biphenyl group may be interpreted as an aryl group, or as a phenyl group substituted with a phenyl group.

[0053] As used herein, "adjacent groups bond to each other to form a ring" may mean that adjacent groups bond to each other to form a substituted or unsubstituted hydrocarbon ring, or a substituted or unsubstituted hetero ring. The hydrocarbon ring includes an aliphatic hydrocarbon ring, but does not include an aromatic hydrocarbon ring. The hetero ring includes an aliphatic hetero ring and an aromatic hetero ring. The hydrocarbon ring and the hetero ring may be monocyclic or polycyclic. Furthermore, the ring formed by bonding to each other may be linked to another ring to form a spiro structure.

[0054] As used herein, the term "adjacent group" refers to a substituent substituted on an atom directly connected to the atom on which the substituent is substituted, another substituent substituted on the atom on which the substituent is substituted, or the substituent sterically closest to the substituent. For example, two methyl groups in 1,2-dimethylbenzene can be interpreted as "adjacent groups" to each other, and two ethyl groups in 1,1-diethylcyclopentane can be interpreted as "adjacent groups" to each other. Also, two methyl groups in 4,5-dimethylphenanthrene can be interpreted as "adjacent groups" to each other.

[0055] In this specification, "C1 to C10 alkyl (alkylene)" means a straight-chain or branched-chain alkyl having 1 to 10 carbon atoms, and the number of carbon atoms may be 1 to 6 or 1 to 5. Specific examples of the alkyl include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, and tert-butyl.

[0056] As used herein, "alkenyl having 2 to 10 carbon atoms" refers to straight-chain or branched-chain alkenyl having 2 to 10 carbon atoms, and the number of carbon atoms may be 2 to 6 or 2 to 5. Specific examples of the alkenyl include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, and 2-methylbutyl-2-enyl.

[0057] As used herein, "cycloalkyl (or cycloalkane) having 3 to 30 carbon atoms" refers to a monocyclic or polycyclic hydrocarbon having 3 to 30 carbon atoms, and the number of carbon atoms may be 3 to 20 or 3 to 7. Examples of the cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.

[0058] As used herein, "cycloalkenyl (or cycloalkene) having 3 to 30 carbon atoms" refers to a monocyclic or polycyclic unsaturated hydrocarbon having 3 to 30 carbon atoms, and the number of carbon atoms may be 3 to 20 or 3 to 7. Examples of the cycloalkenyl include cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, 1,3-cyclohexadienyl, 1,4-cyclohexadienyl, and norbornenyl.

[0059] As used herein, "aryl (arylene) having 3 to 30 carbon atoms" refers to a monocyclic or polycyclic (fused ring) radical derived from an aromatic hydrocarbon having 3 to 30 carbon atoms, and the number of carbon atoms in the ring skeleton may be 3 to 20. Examples of the aryl include phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, and fluoranthenyl.

[0060] As used herein, "3- to 30-membered heteroaryl (arylene)" refers to an aryl group having 3 to 30 ring skeletal atoms and containing one or more heteroatoms selected from the group consisting of B, N, O, S, Si, and P. The number of heteroatoms is 1 to 4, or 1 or 2, and the group may be a monocyclic ring or a polycyclic (fused ring) ring condensed with one or more benzene rings, and may be partially saturated. Furthermore, as used herein, the heteroaryl also includes a form in which one or more heteroaryl or aryl groups are linked to a heteroaryl by a single bond. Examples of the heteroaryl include monocyclic heteroaryls such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, and pyridazinyl, and polycyclic heteroaryls such as benzofuranyl, benzothiopenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiopenyl, benzonaphthothiopenyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, cabazolyl, penoxazinyl, penanthridinyl, and benzodioxolyl.

[0061] As used herein, "halogen" includes F, Cl, Br, and I atoms.

[0062]

[0063] The configuration of the present invention will be described in more detail below.

[0064] In one embodiment of the present invention, there is provided a composition for producing an alkali-soluble resin, the composition comprising a dicarboxylic acid anhydride, a tetracarboxylic acid dianhydride, and a diamine, the alkali-soluble resin containing a structural unit derived from the dicarboxylic acid anhydride at at least one of both ends, and the composition containing 5 to 40 mol % of the dicarboxylic acid anhydride based on 100 mol % in total of the diamine, the tetracarboxylic acid dianhydride, and the dicarboxylic acid anhydride.

[0065] In one embodiment, the dicarboxylic acid anhydride may include at least one of a compound represented by the following Chemical Formula 1 and a compound represented by the following Chemical Formula 2:

[0066] [C1]

[0067] JPEG2026507813000011.jpg28170

[0068] [Case 2]

[0069] JPEG2026507813000012.jpg27170

[0070] In the above Chemical Formula 1 and Chemical Formula 2,

[0071] R1, R2, R3, and R4 each independently represent hydrogen, halogen, a substituted or unsubstituted alkyl having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl having 2 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 30 carbon atoms, a substituted or unsubstituted aryl having 3 to 30 carbon atoms, or a substituted or unsubstituted 3 to 30-membered heteroaryl, or are bonded to adjacent groups to form a ring;

[0072] R5 and R6 each independently represent hydrogen, halogen, a substituted or unsubstituted alkyl having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 30 carbon atoms, a substituted or unsubstituted aryl having 3 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl having 3 to 30 members, or they are bonded to each other with adjacent groups to form a ring.

[0073] In one embodiment, the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 may be represented by any one of Chemical Formulas A-1 to A-14 below.

[0074] JPEG2026507813000013.jpg160170

[0075] In one embodiment, the alkali-soluble resin may contain 5 to 40 mol%, 10 to 35 mol%, 15 to 35 mol%, or 20 to 25 mol% of dicarboxylic acid anhydride, based on 100 mol% of the total of the diamine, tetracarboxylic acid dianhydride, and dicarboxylic acid anhydride. Specifically, the alkali-soluble resin may contain a structural unit derived from the diamine, a structural unit derived from the tetracarboxylic acid dianhydride, and a structural unit derived from the dicarboxylic acid anhydride.

[0076] That is, the alkali-soluble resin may contain 5 to 40 mol%, 10 to 35 mol%, 15 to 35 mol%, or 20 to 25 mol% of dicarboxylic acid anhydride-derived structural units, based on 100 mol% of the total of the tetracarboxylic acid dianhydride-derived structural units and the dicarboxylic acid anhydride-derived structural units. When the dicarboxylic acid anhydride content falls within the above range, the resin may exhibit advantageous chemical resistance and heat resistance while satisfying bending properties.

[0077] In one embodiment, the tetracarboxylic dianhydride may be contained in an amount of 5 mol% to 60 mol%, 10 mol% to 50 mol%, or 15 mol% to 45 mol%, based on 100 mol% of the total of the diamine, tetracarboxylic dianhydride, and dicarboxylic anhydride. When the tetracarboxylic dianhydride is contained in the above range, excellent heat resistance can be achieved.

[0078] In one embodiment, the diamine may be included in an amount of 10 mol% to 70 mol%, 15 mol% to 60 mol%, or 20 mol% to 50 mol% based on 100 mol% of the total of the diamine, tetracarboxylic dianhydride, and dicarboxylic anhydride. When the diamine is included in the above numerical range, it may be advantageous for sensitivity.

[0079] In one embodiment, the tetracarboxylic dianhydride may include at least one of a compound represented by the following Chemical Formula 3 and a compound represented by the following Chemical Formula 4:

[0080] [C3]

[0081] JPEG2026507813000014.jpg32170

[0082] [C4]

[0083] JPEG2026507813000015.jpg31170

[0084] In the above Chemical Formula 3 and Chemical Formula 4,

[0085] L1 is a single bond, a substituted or unsubstituted alkylene having 1 to 10 carbon atoms, an ether bond (-O-), -R a -OR b - or -(C=O)-OR c -O-(C=O)-,

[0086] R7 and R8 are each independently hydrogen, halogen, substituted or unsubstituted alkyl having 1 to 10 carbon atoms, or haloalkyl having 1 to 10 carbon atoms;

[0087] R a , R b , and R c are each independently substituted or unsubstituted alkylene having 1 to 10 carbon atoms or haloalkyl having 1 to 10 carbon atoms.

[0088] In one embodiment, the compound represented by Chemical Formula 3 and the compound represented by Chemical Formula 4 may be represented by any one of the following Chemical Formulas B-1 to B-6.

[0089] JPEG2026507813000016.jpg135170

[0090] In one embodiment, the diamine may include a compound represented by the following formula 5:

[0091] [5]

[0092] JPEG2026507813000017.jpg22170

[0093] In the above Chemical Formula 5,

[0094] R 10 and R 11 each independently represents hydrogen, hydroxy, halogen, haloalkyl having 1 to 10 carbon atoms, or substituted or unsubstituted alkyl having 1 to 10 carbon atoms;

[0095] L2 and L3 each independently represent a single bond, an ether bond (-O-), -(C=O)-O-, -(C=O)-NH-, -OR d -, -(C=O)-OR e -, -(C=O)-NH-R f-, haloalkylene having 1 to 10 carbon atoms, or substituted or unsubstituted alkylene having 1 to 10 carbon atoms;

[0096] R d , R e , and R f are each independently a substituted or unsubstituted arylene having 3 to 30 carbon atoms,

[0097] R9 is a single bond, an ether bond (-O-), haloalkylene having 1 to 10 carbon atoms, substituted or unsubstituted alkylene having 1 to 10 carbon atoms, or substituted or unsubstituted arylene having 3 to 30 carbon atoms.

[0098] In one embodiment, the compound represented by Chemical Formula 5 may be represented by any one of Chemical Formulas C-1 to C-8 below.

[0099] JPEG2026507813000018.jpg128170

[0100] JPEG2026507813000019.jpg75170

[0101] In one embodiment, the composition for producing an alkali-soluble resin contains the above-mentioned diamine, tetracarboxylic dianhydride, and dicarboxylic anhydride, thereby achieving excellent sensitivity, heat resistance, and chemical resistance, and also satisfying bending properties.

[0102]

[0103] In one embodiment of the present invention, there is provided an alkali-soluble resin produced from the above-described composition for producing an alkali-soluble resin.

[0104] Details that overlap with those explained in the composition for producing an alkali-soluble resin will not be explained further.

[0105] In one embodiment, the alkali-soluble resin comprises a dicarboxylic acid anhydride-derived structural unit; a tetracarboxylic acid dianhydride-derived structural unit; and a diamine-derived structural unit. The alkali-soluble resin contains the dicarboxylic acid anhydride-derived structural unit at at least one of both ends, and may contain 5 to 40 mol % of the dicarboxylic acid anhydride-derived structural unit, based on a total of 100 mol % of the diamine-derived structural unit, the tetracarboxylic acid dianhydride-derived structural unit, and the dicarboxylic acid anhydride-derived structural unit.

[0106] In one embodiment, the alkali-soluble resin may include any one selected from the group consisting of polyamic acid, polyamic ester, and polyimide, and specifically may include polyimide. When the alkali-soluble resin is polyimide, it may have better heat resistance and chemical reaction resistance than other resins.

[0107] In one embodiment, the alkali-soluble resin may include a dicarboxylic acid anhydride-derived structural unit at at least one of both ends. When the alkali-soluble resin includes a dicarboxylic acid anhydride-derived structural unit at at least one of both ends, the required level of sensitivity can be ensured while satisfying bending characteristics.

[0108] In one embodiment, when the alkali-soluble resin contains dicarboxylic acid anhydride-derived structural units at both ends, it can be represented by the following Formula 6-1 or 6-2.

[0109] [C6-1]

[0110] JPEG2026507813000020.jpg19170

[0111] [C6-2]

[0112] JPEG2026507813000021.jpg14170

[0113] In Chemical Formula 6-1 or Chemical Formula 6-2, A1 is a compound derived from a dicarboxylic acid anhydride, B1 is a compound derived from a tetracarboxylic acid dianhydride, C1 is a compound derived from a diamine, X3 or X4 are each independently H, n1 or n2 are each independently an integer of 1 to 50, a, b, c, and d are each independently an integer of 0 to 4, the sum of a, b, c, and d in Chemical Formula 6-1 is 1 or more, and the sum of a, b, and c in Chemical Formula 6-2 is 1 or more.

[0114]

[0115] In one embodiment, the weight average molecular weight Mw of the alkali-soluble resin may be 1,000 to 50,000 g / mol, and within this range, chemical resistance, sensitivity performance, heat resistance, device performance, and bending characteristics may be satisfied.

[0116] In one embodiment of the present invention, there is provided a photosensitive resin composition comprising the above-described alkali-soluble resin; a photosensitizer; and a solvent.

[0117] The details overlapping with those explained in the composition for producing an alkali-soluble resin and the alkali-soluble resin will not be further explained.

[0118] In one embodiment, the alkali-soluble resin may be contained in an amount of 3 to 50 wt % based on the total weight of the photosensitive resin composition. When the alkali-soluble resin is contained in the photosensitive resin composition in this range, the sensitivity, heat resistance, and bending properties may be advantageous.

[0119] In one embodiment, the photosensitive resin composition includes a photosensitizer that imparts alkaline developability to the exposed area after exposure. Specifically, the photosensitizer may be an esterified quinone diazide compound.

[0120] In one embodiment, the esterified quinone diazide compound may include a phenolic compound as a ballast.

[0121] In one embodiment, the esterified quinone diazide compound may include at least one of compounds represented by the following formulas D-1 to D-10.

[0122] JPEG2026507813000022.jpg169170

[0123] JPEG2026507813000023.jpg179170

[0124] In the chemical formulas D-1 to D-10,

[0125] R 12 ~R 15 and R 18 ~R 74 are each independently a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an alkenyl group having 2 to 4 carbon atoms, and 12 ~R 15 and R 18 ~R 74 must essentially contain at least one alkyl group having 1 to 4 carbon atoms or an alkenyl group having 2 to 4 carbon atoms,

[0126] X1, X2, R 16 , and R 17 are each independently hydrogen or an alkyl group having 1 to 4 carbon atoms.

[0127] In one embodiment, the photosensitizer may be present in an amount of 5 to 40 parts by weight, 10 to 35 parts by weight, 15 to 30 parts by weight, or 20 to 28 parts by weight relative to 100 parts by weight of the alkali-soluble resin. When the content of the photosensitizer is within this range, the pattern shape can be properly maintained, and proper photosensitivity and heat resistance can be ensured.

[0128] In one embodiment, the photosensitive resin composition may contain a solvent to disperse or dissolve each component contained in the composition.

[0129] In one embodiment, the solvent may be any one selected from the group consisting of gamma butyrolactone (GBL), N-methylpyrrolidone (NMP), propylene glycol methyl ether acetate (PGMEA), ethyl lactate (EL), methyl-3-methoxypropionate (MMP), propylene glycol monomethyl ether (PGME), diethylene glycol ethyl methyl ether (MEDG), diethyl glycol butyl methyl ether (MBDG), diethyl glycol dimethyl ester (DMDG), diethylene glycol diethyl ester (DEDG), and mixtures thereof.

[0130] In one embodiment, the photosensitive resin composition may further include at least one of a crosslinking agent, a heat dissipation agent, and a UV absorber. The crosslinking agent may undergo a crosslinking reaction with the alkali-soluble resin by light or heat, thereby effectively controlling the pattern shape. For example, the crosslinking agent may include at least one of compounds represented by the following formulas E-1 to E-18:

[0131] JPEG2026507813000024.jpg176170

[0132] JPEG2026507813000025.jpg92170

[0133] In the group represented by the above chemical formulas, R' are each independently one of a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, or a substituent of the following chemical formula F, and at least one of R' is a substituent of the following chemical formula F, in which n is an integer of 1 to 6, and R a is an alkyl group having 1 to 3 carbon atoms.

[0134] [F]

[0135] JPEG2026507813000026.jpg18170

[0136] In one embodiment, when the photosensitive resin composition further contains a heat dissipation agent or a UV absorber, the heat resistance, moisture absorption, etc. of the resin composition are improved, which can result in better panel reliability.

[0137] In one embodiment, the photosensitive resin composition can be a positive photosensitive resin composition.

[0138]

[0139] In one embodiment of the present invention, there is provided an insulating film including a cured product obtained by curing the above-described photosensitive resin composition.

[0140] In one embodiment of the present invention, a display device including the insulating film is provided.

[0141] FIG. 1 is a vertical cross-sectional view of a display device according to one embodiment of the present invention.

[0142] In one embodiment, the display device may be a display device for an organic electroluminescent device.

[0143] The display device for an organic electroluminescent device may include a first electrode formed on a substrate, an insulating layer formed on the first electrode, and a second electrode formed on the insulating layer, and the insulating layer may be formed by curing the positive-type photosensitive resin composition according to one embodiment of the present invention.

[0144] The insulating layer may be patterned to partially expose an upper surface of the first electrode, and may be formed to cover an edge portion of the first electrode.

[0145] The insulating layer may be patterned to partially expose an upper surface of the first electrode, and may be formed to cover an edge portion of the first electrode.

[0146]

[0147] The above description has been given by way of an example of the technical concept of the present invention, and various modifications and variations may be made by a person skilled in the art without departing from the essential characteristics of the present invention. Therefore, the embodiments described in the present invention are for illustrative purposes only, and are not intended to limit the technical concept of the present invention. The scope of the technical concept of the present invention should be interpreted by the scope of the claims, and all technical concepts within the scope equivalent thereto should be interpreted as being included in the scope of the present invention.

[0148] <Preparation example>

[0149] In order to synthesize the alkali-soluble resin, the dicarboxylic acid anhydride compounds shown in Table 1 below, the tetracarboxylic acid dianhydride compounds shown in Table 2 below, and the diamine compounds shown in Table 3 below were prepared.

[0150] [Table 1]

[0151] [Table 2]

[0152] [Table 3]

[0153] <Example>

[0154] A diamine having the composition and content shown in Table 4 below was dissolved in gamma-butyrolactone under a dry nitrogen stream, and then a tetracarboxylic dianhydride having the composition and content shown in Table 4 below was added and dissolved with stirring, followed by stirring at 70°C for 4 hours. A dicarboxylic anhydride having the composition and content shown in Table 4 below was then added and stirred at 70°C for 2 hours. After further stirring at 180°C for 4 hours, the reaction was terminated to finally synthesize a polyimide polymer (the units of each composition in Table 4 below are in moles).

[0155] [Table 4] JPEG2026507813000031.jpg235167JPEG2026507813000032.jpg234168JPEG2026507813000033.jpg234167JPEG20265078130 00034.jpg234167JPEG2026507813000035.jpg234167JPEG2026507813000036.jpg233167JPEG2026507813000037.jpg125170

[0156] <Comparative Example>

[0157] Polyimide was synthesized in the same manner as in Example 1, except that diamine, tetracarboxylic dianhydride, and dicarboxylic anhydride having the compositions and contents shown in Table 5 below were used.

[0158] [Table 5] JPEG2026507813000039.jpg230170JPEG2026507813000040.jpg230170JPEG2026507813000041.jpg227170

[0159] <Production example>

[0160] An alkali-soluble resin (polyimide polymer), a photosensitizer (quinone diazide compound), and a crosslinker (crosslinkable compound) having the composition and content shown in Table 6 below were mixed, and then a solvent was added to prepare a photosensitive resin composition having a total solid content of 10 wt%.

[0161] [Table 6] JPEG2026507813000043.jpg253168JPEG2026507813000044.jpg254168JPEG2026507813000045.jpg85170

[0162] In Table 6, the chemical formula D-1 is JPEG2026507813000046.jpg60170, and the chemical formula D-2 is JPEG2026507813000047.jpg38170, and in chemical formulas E-4, E-5, E-7, E-13, and E-14, R' is JPEG2026507813000048.jpg19170, where n is 1 and R a is CH3.

[0163] <Experimental Example: Photosensitive Resin Composition and Insulating Film Evaluation>

[0164] For the prepared Examples 1 to 92 and Comparative Examples 1 to 31, physical properties such as sensitivity, residual film rate, adhesive strength, chemical resistance, heat resistance, solar reliability, moisture absorption, driving reliability, and bending characteristics were measured according to the following criteria, and the results are shown in Table 7.

[0165] The photosensitive resin compositions of Examples 1 to 92 and Comparative Examples 1 to 31 were coated onto a glass substrate using a slit coater, and then subjected to a VCD (vacuum drying) process up to a pressure of 40 Pa. The coating was then pre-baked on a hot plate at 120°C for 2 minutes to form a film having a thickness of 3.0 μm.

[0166] a) Sensitivity

[0167] The film formed as above was exposed to a broadband intensity of 20 mW / cm using a pattern mask. 2 The sample was irradiated with UV light at a dose based on a 2.5μm contact hole CD, developed in a 2.38 wt% tetramethylammonium hydroxide aqueous solution at 23°C for 1 minute, and then washed in ultrapure water for 1 minute. The sample was then cured in an oven at 250°C for 60 minutes to obtain a patterned film with a thickness of 2.0μm. Sensitivity of 100mJ or less was marked with a circle, and sensitivity of over 120mJ was marked with an X. The results are shown in Table 7 below.

[0168]

[0169] b) Remaining film rate

[0170] The change in film thickness formed during the sensitivity measurement of the above item (a) was measured.

[0171] The remaining film ratio was expressed as (thickness after curing / thickness after pre-baking), and a remaining film ratio of 60% or more was marked with ○, and a remaining film ratio of less than 50% was marked with ×. The results are shown in Table 7 below.

[0172]

[0173] c) Adhesion strength

[0174] A pattern film was formed in the same manner as in the sensitivity measurement in (a) above, but the adhesive strength was evaluated based on the minimum CD of the dot pattern. A circle was marked if adhesive strength was ensured when the minimum CD of the dot pattern was 5 μm or more, and an X was marked if adhesive strength was not ensured when the minimum CD of the dot pattern was 15 μm or more. The results are shown in Table 7 below.

[0175]

[0176] D) Chemical resistance

[0177] The substrate was immersed in methylpyrrolidone (NMP) at 60°C for 120 seconds, and the change in cured film thickness before and after immersion was measured. A change in cured film thickness of less than 300 Å was marked with ○, and a change in cured film thickness of 600 Å or more was marked with X. The results are shown in Table 7 below.

[0178]

[0179] E) Heat resistance

[0180] Heat resistance was measured using TGA. The pattern film formed during the sensitivity measurement in (a) above was sampled and then heated from room temperature to 900°C at a rate of 10°C per minute using TGA. A 5 wt% loss temperature exceeding 300°C was marked with an O, and a 5 wt% loss temperature below 280°C was marked with an X. The results are shown in Table 7 below.

[0181]

[0182] F) Solar reliability

[0183] FIG. 1 shows a simplified diagram of a display device (device) in which a pattern film is formed on an ITO (Indium Tin Oxide) substrate on which a pattern is formed, and EL (Electroluminescent Lighting) and Al are deposited. The device was measured at 85°C and 420 nm wavelength with an output of 1.42 W / m 2 After 120 hours of solar processing at 1000 Hz, the time (T97) until a 3% brightness drop occurred with the device on was evaluated. A value of 1000 hours or more but less than 1100 hours was marked O, a value of 900-1000 hours was marked △, and a value of less than 900 hours was marked X. The results are shown in Table 7 below.

[0184]

[0185] g) Hygroscopicity

[0186] The pattern film formed during the sensitivity measurement in (a) above was purified in a constant temperature and humidity oven at 85°C and 85% RH for 240 hours, and the moisture absorption was evaluated based on the change in film thickness before and after placing it in the oven. A thickness change rate of less than 600 Å was marked with ○, and a change of 600 Å or more was marked with X. The results are shown in Table 7 below.

[0187]

[0188] H) OLED driving reliability

[0189] Using the same method as in the sensitivity measurement method (a) above, a pattern film was formed on the patterned ITO substrate shown in Figure 1, and an EL layer was deposited on it. Al was deposited on top as a cathode electrode, and the encapsulation process was carried out. The time until a 3% luminance drop (T97) occurred with the device on was evaluated at 85°C and 85% RH. A 3% drop in luminance was measured for 1000 hours or more but less than 1100 hours, a △ for 900 to 1000 hours, and an X for less than 900 hours. The results are shown in Table 7 below.

[0190]

[0191] Flexibility (folding & cracking)

[0192] A 100 μm polyimide film was coated with the photosensitive resin composition of the above Preparation Example to a thickness of 3 μm, and then infolded 200,000 times with a curvature radius of 1R. If cracks of 3 mm or more were observed within 100,000 repetitions, they were marked with an X, and if no cracks were observed within 200,000 repetitions, they were marked with an O. To check, the film was visually inspected and observed under a microscope at 100x magnification. The results are shown in Table 7 below.

[0193] [Table 7] JPEG2026507813000050.jpg232170JPEG2026507813000051.jpg231170JPEG2026507813000052.jpg231170JPEG202 6507813000053.jpg232170JPEG2026507813000054.jpg232170JPEG2026507813000055.jpg231170JPEG20265078130 00056.jpg231170JPEG2026507813000057.jpg231170JPEG2026507813000058.jpg231170JPEG2026507813000059.j pg232170JPEG2026507813000060.jpg232170JPEG2026507813000061.jpg232170JPEG2026507813000062.jpg175170

[0194]

[0195] While the present invention has been described above with reference to preferred embodiments, those skilled in the art will appreciate that various modifications and variations can be made to the present invention without departing from the spirit and scope of the invention as set forth in the following claims.

Claims

1. A compound for producing an alkali-soluble resin, the compound comprising a dicarboxylic acid anhydride, a tetracarboxylic acid dianhydride, and a diamine, the alkali-soluble resin contains the dicarboxylic acid anhydride-derived structural unit at at least one of both ends, The composition for producing an alkali-soluble resin contains 5 to 40 mol % of a dicarboxylic acid anhydride, based on 100 mol % in total of the diamine, the tetracarboxylic acid dianhydride, and the dicarboxylic acid anhydride.

2. The composition for producing an alkali-soluble resin according to claim 1, wherein the dicarboxylic acid anhydride comprises at least one of a compound represented by the following Chemical Formula 1 and a compound represented by the following Chemical Formula 2: [Chemical formula 1] [Chemical 2] In the above Chemical Formula 1 and Chemical Formula 2, R １ , R ２ , R ３ , and R ４ are each independently hydrogen, halogen, a substituted or unsubstituted alkyl having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl having 2 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 30 carbon atoms, a substituted or unsubstituted aryl having 3 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl having 3 to 30 members, or are bonded to adjacent groups to form a ring; R ５ and R ６ are each independently hydrogen, halogen, a substituted or unsubstituted alkyl having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl having 3 to 30 carbon atoms, a substituted or unsubstituted aryl having 3 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl having 3 to 30 members, or are bonded to adjacent groups to form a ring.

3. The composition for producing an alkali-soluble resin according to claim 2, wherein the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 are represented by any one of the following Chemical Formulas A-1 to A-14.

4. 2. The composition for producing an alkali-soluble resin according to claim 1, wherein the tetracarboxylic dianhydride comprises at least one of a compound represented by the following Chemical Formula 3 and a compound represented by the following Chemical Formula 4: [Chemical 3] [C4] In the above Chemical Formula 3 and Chemical Formula 4, L １ represents a single bond, a substituted or unsubstituted alkylene having 1 to 10 carbon atoms, an ether bond (—O—), —R ａ -O-R ｂ - or -(C=O)-O-R ｃ —O—(C═O)—, R ７ and R ８ are each independently hydrogen, halogen, substituted or unsubstituted alkyl having 1 to 10 carbon atoms, or haloalkyl having 1 to 10 carbon atoms; R ａ , R ｂ , and R ｃ are each independently substituted or unsubstituted alkylene having 1 to 10 carbon atoms or haloalkyl having 1 to 10 carbon atoms.

5. The compound represented by Chemical Formula 3 and the compound represented by Chemical Formula 4 are represented by any one of the following Chemical Formulas B-1 to B-6.

6. The composition for preparing an alkali-soluble resin according to claim 1 , wherein the diamine comprises a compound represented by the following Chemical Formula 5: [C5] In the above Chemical Formula 5, R １０ and R １１ are each independently hydrogen, hydroxy, halogen, haloalkyl having 1 to 10 carbon atoms, or substituted or unsubstituted alkyl having 1 to 10 carbon atoms; L ２ and L ３ each independently represents a single bond, an ether bond (—O—), —(C═O)—O—, —(C═O)—NH—, or —O—R ｄ -, -(C=O)-OR ｅ -, -(C=O)-NH-R ｆ -, haloalkylene having 1 to 10 carbon atoms, or substituted or unsubstituted alkylene having 1 to 10 carbon atoms; R ｄ , R ｅ , and R ｆ each independently represents a substituted or unsubstituted arylene having 3 to 30 carbon atoms; R ９ is a single bond, an ether bond (—O—), a haloalkylene having 1 to 10 carbon atoms, a substituted or unsubstituted alkylene having 1 to 10 carbon atoms, or a substituted or unsubstituted arylene having 3 to 30 carbon atoms.

7. The compound represented by Chemical Formula 5 is represented by any one of the following Chemical Formulas C-1 to C-8.

8. An alkali-soluble resin produced using the composition for producing an alkali-soluble resin according to any one of claims 1 to 7, comprising: a dicarboxylic acid anhydride-derived structural unit; a tetracarboxylic acid dianhydride-derived structural unit; and a diamine-derived structural unit; the alkali-soluble resin contains the dicarboxylic acid anhydride-derived structural unit at at least one of both ends, an alkali-soluble resin containing 5 to 40 mol % of dicarboxylic acid anhydride-derived structural units, based on a total of 100 mol % of the diamine-derived structural units, the tetracarboxylic acid dianhydride-derived structural units, and the dicarboxylic acid anhydride-derived structural units.

9. 9. The alkali-soluble resin according to claim 8, wherein the weight average molecular weight Mw of the alkali-soluble resin is 1,000 to 50,000 g / mol.

10. The alkali-soluble resin according to claim 8; A photosensitizer and a solvent; A photosensitive resin composition comprising:

11. The photosensitive resin composition according to claim 10, wherein the alkali-soluble resin is contained in an amount of 3 to 50% by weight based on 100% by weight of the total photosensitive resin composition.

12. An insulating film comprising a cured product obtained by curing the photosensitive resin composition according to claim 10.

13. A display device comprising the insulating film according to claim 12.

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