Positive photosensitive resin composition, electronic component, and display device
The positive photosensitive resin composition addresses solubility and sensitivity issues in OLED devices by incorporating an alkali-soluble polymer resin, esterified quinonediazide, and crosslinking agent, enhancing performance in sensitivity, film retention, and resistance properties.
Patent Information
- Application Number
- PCT/KR2025/099151
- Authority / Receiving Office
- WO · WO
- Patent Type
- Applications
- Current Assignee / Owner
- Priority Date
- 2025-01-24
- Filing Date
- 2025-01-31
- Publication Date
- 2025-08-07
AI Technical Summary
Conventional polyimide photosensitive resin compositions used in OLED devices face challenges with solubility control and low sensitivity, necessitating improved solutions for better sensitivity, film retention, adhesive strength, chemical resistance, and heat resistance.
A positive photosensitive resin composition comprising an alkali-soluble polymer resin, an esterified quinonediazide-based compound, and a crosslinking agent with specific CTC value conditions, along with a controlled fluorine content, to enhance sensitivity, film retention, adhesive strength, chemical resistance, and heat resistance.
The composition achieves improved sensitivity, film retention, adhesive strength, chemical resistance, heat resistance, solar resistance, hygroscopicity, and operating reliability, with specific CTC value and fluorine content optimizations.
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Figure KR2025099151_07082025_PF_FP_ABST
Abstract
Description
Positive photosensitive resin composition, electronic component and display device
[0001] The present invention relates to a positive photosensitive resin composition, an electronic component, and a display device.
[0002]
[0003] Recently, among display devices, OLED (Organic Light Emitting Diodes), especially AMOLED (Active matrix OLED), is attracting attention for various reasons.
[0004] Typically, OLED devices include an organic insulating film, and a polyimide photosensitive resin composition is typically used to form the organic insulating film. Among the polyimide precursors used in conventional polyimide photosensitive resin compositions, a technology for substituting polyamic esters with alkyl groups has been applied. However, alkyl-substituted polyamic esters have difficulty controlling solubility and low sensitivity, and thus, there is an urgent need for improved solutions.
[0005]
[0006] The present invention provides a positive photosensitive resin composition having excellent sensitivity, film retention, adhesive strength, chemical resistance, hygroscopicity and heat resistance, and an electronic component and a display device including a cured product thereof.
[0007] However, the problems to be solved by the present invention are not limited to the problems mentioned above, and other problems not mentioned will be clearly understood by those skilled in the art from the description below.
[0008]
[0009] One embodiment of the present invention provides a positive photosensitive resin composition comprising: an alkali-soluble polymer resin; an esterified quinonediazide-based compound; and a crosslinking agent including a phenol group; wherein the alkali-soluble polymer resin comprises a reaction product of a mixture including an amine-based compound, an acid anhydride-based compound, and a capping compound, and satisfies the following formula 1:
[0010] [Formula 1]
[0011] (A+B) / 2 < 6.0 eV
[0012] In the above formula 1, A is the CTC value (eV) of the amine compound, B is the sum of the CTC value (eV) of the acid anhydride compound and the CTC value (eV) of the capping compound in a mixture of the acid anhydride compound and the capping compound, and the CTC value means a quantum calculation simulation value for the energy level difference between the electron donor and electron acceptor of the compound, assuming that the compound forms a charge transfer complex.
[0013] According to one embodiment of the present invention, the fluorine content of the positive photosensitive composition may be 10,000 ppm or less.
[0014] According to one embodiment of the present invention, the alkali-soluble polymer resin includes a repeating unit represented by the following chemical formula A and a repeating unit represented by the following chemical formula B, and the repeating unit represented by the above chemical formula A and the repeating unit represented by the above chemical formula B are R b Structure derived from an amine compound containing and R a It may include a structure derived from an acid anhydride compound containing:
[0015] [Chemical Formula A]
[0016]
[0017] [Chemical Formula B]
[0018]
[0019] In the above chemical formula A and chemical formula B, the R a and R b are each independently an organic group having 5 to 60 carbon atoms, X1 and X2 are each independently hydrogen or an alkyl group having 1 to 10 carbon atoms, a and b are each independently an integer from 0 to 4, c and d are each independently an integer from 0 to 2, and a+b is 1 or more.
[0020] According to one embodiment of the present invention, the alkali-soluble polymer resin may have a repeating unit represented by the chemical formula B in an amount of 51 mol% or more, based on a total of 100 mol% of the repeating unit represented by the chemical formula A and the repeating unit represented by the chemical formula B.
[0021] According to one embodiment of the present invention, the amine compound may include at least one of the compounds represented by the following chemical formulas 1-1 to 1-19.
[0022] [Chemical Formula 1-1] [Chemical Formula 1-2]
[0023]
[0024] [Chemical Formula 1-3] [Chemical Formula 1-4]
[0025]
[0026] [Chemical Formula 1-5] [Chemical Formula 1-6]
[0027]
[0028] [Chemical Formula 1-7]
[0029]
[0030] [Chemical Formula 1-8]
[0031]
[0032] [Chemical Formula 1-9]
[0033]
[0034] [Chemical Formula 1-10]
[0035]
[0036] [Chemical Formula 1-11] [Chemical Formula 1-12]
[0037]
[0038] [Chemical Formula 1-13] [Chemical Formula 1-14]
[0039]
[0040] [Chemical Formula 1-15]
[0041]
[0042] [Chemical Formula 1-16]
[0043]
[0044] [Chemical Formula 1-17]
[0045]
[0046] [Chemical Formula 1-18]
[0047]
[0048] [Chemical Formula 1-19]
[0049]
[0050] At least two of a1, b1, c1, d1, e1 and f1 are amine groups, and the rest are hydrogen, a hydroxyl group, an alkyl group having 1 to 3 carbon atoms substituted with a halogen element or -COOX2, and at least two of a2, b2, c2 and d2 are amine groups, and the rest are hydrogen, a hydroxyl group or -COOX2, and R 1-1 and R 1-2are each independently hydrogen, an alkyl group having 1 to 10 carbon atoms, an alkyl group having 1 to 3 carbon atoms substituted with a halogen element, or a cycloalkyl group having 5 to 10 carbon atoms, and at least two of a3, b3, c3, and d3 are amine groups, and the rest are hydrogen, a hydroxy group, or -COOX2, and R 1-3 and R 1-4 are each independently an alkyl group having 1 to 10 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms, and R 1-5 and R 1-6 are each independently hydrogen or an alkyl group having 1 to 10 carbon atoms, at least two of a4, b4, c4 and d4 are amine groups, and the rest are hydrogen, a hydroxy group or -COOX2, at least two of a5, b5, c5 and d5 are amine groups, and the rest are hydrogen, a hydroxy group or -COOX2, and R 1-7 and R 1-8 are each independently an alkyl group having 1 to 10 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms, at least two of a6, b6, c6 and d6 are amine groups, and the rest are hydrogen, a hydroxyl group or -COOX2, at least two of a7, b7, c7 and d7 are amine groups, and the rest are hydrogen, a hydroxyl group or -COOX2, at least two of a8, b8, c8 and d8 are amine groups, and the rest are hydrogen, a hydroxyl group or -COOX2, and R 1-9 and R 1-10 are each independently an alkyl group having 1 to 10 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms, at least two of a9, b9, c9 and d9 are amine groups, and the rest are hydrogen, hydroxyl groups or -COOX2, and a 10 , b 10 , c 10 and d 10 At least two of them are amine groups, the rest are hydrogen, hydroxyl groups or -COOX2, and a 11 , b 11 , c 11 , d 11 , e11 and f 11 At least two of them are amine groups, the rest are hydrogen, hydroxyl groups or -COOX2, and a 12 , b 12 , c 12 , d 12 , e 12, f 12 and g 12 At least two of them are amine groups, the rest are hydrogen, hydroxyl groups or -COOX2, and a 13 , b 13 , c 13 , d 13 , e 13 and f 13 At least two of which are amine groups, and the rest are hydrogen, hydroxyl groups, alkyl groups having 1 to 3 carbon atoms unsubstituted or substituted with halogen elements, or -COOX2, and a 14 is a thiol group, an amine group or a hydroxy group, and X2 is hydrogen or an alkyl group having 1 to 10 carbon atoms.
[0051] According to one embodiment of the present invention, the acid anhydride compound may include at least one of the compounds represented by the following chemical formulas 2-1 to 2-16:
[0052] [Chemical Formula 2-1]
[0053]
[0054] [Chemical Formula 2-2]
[0055]
[0056] [Chemical Formula 2-3]
[0057]
[0058] [Chemical Formula 2-4] [Chemical Formula 2-5]
[0059]
[0060] [Chemical Formula 2-6]
[0061]
[0062] [Chemical Formula 2-7]
[0063]
[0064] [Chemical Formula 2-8]
[0065]
[0066] [Chemical Formula 2-9] [Chemical Formula 2-10]
[0067]
[0068] [Chemical Formula 2-11] [Chemical Formula 2-12]
[0069]
[0070] [Chemical Formula 2-13] [Chemical Formula 2-14]
[0071]
[0072] [Chemical Formula 2-15]
[0073]
[0074] [Chemical Formula 2-16]
[0075]
[0076] In the above chemical formulas, R 2-1 Inland R 2-6 are each independently an alkyl group having 1 to 10 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms, and n is an integer from 2 to 20.
[0077] In the above chemical formulas, R 2-1 Inland R 2-6 are each independently an alkyl group having 1 to 10 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms, and n is an integer from 2 to 20.
[0078] According to one embodiment of the present invention, the capping compound may include at least one of the following compounds C-1 to C-5:
[0079] [Compound C-1] [Compound C-2]
[0080]
[0081] [Compound C-3] [Compound C-4]
[0082]
[0083] [Compound C-5]
[0084] .
[0085] According to one embodiment of the present invention, the esterified quinonediazide compound may include a reaction product of at least one of the phenol compounds represented by the following chemical formulas 3-1 to 3-13 and a quinonediazide compound:
[0086] [Chemical Formula 3-1] [Chemical Formula 3-2]
[0087]
[0088] [Chemical Formula 3-3]
[0089]
[0090] [Chemical Formula 3-4] [Chemical Formula 3-5]
[0091]
[0092] [Chemical Formula 3-6]
[0093]
[0094] [Chemical Formula 3-7] [Chemical Formula 3-8]
[0095]
[0096] [Chemical Formula 3-9] [Chemical Formula 3-10]
[0097]
[0098] [Chemical Formula 3-11] [Chemical Formula 3-12]
[0099]
[0100] [Chemical Formula 3-13]
[0101]
[0102] In the above chemical formulas, R 3-1 Inland R 3-84 are each independently hydrogen, an alkyl group having 1 to 4 carbon atoms, or an alkenyl group having 2 to 4 carbon atoms, and Z1 to Z4 are each independently hydrogen, an alkyl group having 1 to 4 carbon atoms.
[0103] According to one embodiment of the present invention, the content of the esterified quinonediazide compound may be 10 parts by weight or more and 40 parts by weight or less with respect to 100 parts by weight of the alkali-soluble polymer resin.
[0104] According to one embodiment of the present invention, the crosslinking agent may include at least one of the compounds represented by the following chemical formulas 4-1 to 4-21:
[0105] [Chemical Formula 4-1] [Chemical Formula 4-2]
[0106]
[0107] [Chemical Formula 4-3] [Chemical Formula 4-4]
[0108]
[0109] [Chemical Formula 4-5] [Chemical Formula 4-6]
[0110]
[0111] [Chemical Formula 4-7] [Chemical Formula 4-8]
[0112]
[0113] [Chemical Formula 4-9] [Chemical Formula 4-10]
[0114]
[0115] [Chemical Formula 4-11] [Chemical Formula 4-12]
[0116]
[0117] [Chemical Formula 4-13] [Chemical Formula 4-14]
[0118]
[0119] [Chemical Formula 4-15] [Chemical Formula 4-16]
[0120]
[0121] [Chemical Formula 4-17]
[0122]
[0123] [Chemical Formula 4-18]
[0124]
[0125] [Chemical Formula 4-19]
[0126]
[0127] [Chemical Formula 4-20]
[0128]
[0129] [Chemical Formula 4-21]
[0130]
[0131] In the above chemical formulas, R 4a Inland R 4h are each independently hydrogen, an alkyl group having 1 to 3 carbon atoms, or , and in the chemical formulas 4-1 to 4-8, R 4a and R 4b At least one of them And, in the above chemical formula 4-9, R 4a Inland R 4c At least one of them And, in the chemical formulas 4-10 to 4-15, R4a Inland R 4d At least one of them And, in the chemical formulas 4-16 to 4-18, R 4a Inland R 4f At least one of them And, in the chemical formulas 4-19 to 4-21, R 4a Inland R 4h At least one of them , m is an integer from 1 to 6, and R 4-1 is an alkyl group having 1 to 3 carbon atoms.
[0132] According to one embodiment of the present invention, the content of the crosslinking agent may be 5 parts by weight or more and 30 parts by weight or less for 100 parts by weight of the alkali-soluble polymer resin.
[0133] According to one embodiment of the present invention, the positive photosensitive resin composition may further include at least one of an organic solvent, a surfactant, and an additive.
[0134] One embodiment of the present invention provides an electronic component including an insulating film including a cured product of the positive photosensitive resin composition.
[0135] One embodiment of the present invention provides a display device including an insulating film including a cured product of the positive photosensitive resin composition.
[0136]
[0137] A positive photosensitive resin composition according to one embodiment of the present invention may have excellent sensitivity, film retention, adhesive strength, chemical resistance, heat resistance, solar resistance, hygroscopicity, operating reliability, and bending characteristics.
[0138] In addition, an electronic component according to one embodiment of the present invention may have excellent sensitivity, film retention, adhesive strength, chemical resistance, heat resistance, solar resistance, moisture absorption, operating reliability, and bending characteristics.
[0139] In addition, a display device according to one embodiment of the present invention may have excellent sensitivity, film retention rate, adhesive strength, chemical resistance, heat resistance, solar resistance, hygroscopicity, operating reliability, and bending characteristics.
[0140] The effects of the present invention are not limited to the effects described above, and effects not mentioned will be clearly understood by those skilled in the art from the present specification and the attached drawings.
[0141]
[0142] Figure 1 is a drawing showing forming a pattern film on an ITO substrate on which a pattern has been formed and depositing EL.
[0143]
[0144] Throughout this specification, whenever a part is said to "include" a component, this does not mean that it excludes other components, but rather that it may include other components, unless otherwise specifically stated.
[0145] Throughout this specification, when it is said that an element is "on" another element, this includes not only cases where the element is in contact with the other element, but also cases where another element exists between the two elements.
[0146] Throughout this specification, the unit “parts by weight” may mean the weight ratio between each component.
[0147] Throughout this specification, terms containing ordinal numbers, such as "first" and "second," are used to distinguish one component from another and are not limited by the ordinal numbers. For example, within the scope of the invention, the first component may also be referred to as the second component, and similarly, the second component may be referred to as the first component.
[0148] Throughout the present specification, the "weight average molecular weight", "molecular weight", etc. of a compound can be calculated using the molecular weight and molecular weight distribution of the compound. Specifically, a sample having a concentration of 1 wt% of the compound is prepared by adding tetrahydrofuran (THF) and the compound to a 1 ml glass bottle, and a standard sample (polystyrene) and the sample sample are filtered through a filter (pore size: 0.45 μm), and then injected into a GPC injector. The elution time of the sample sample is compared with the calibration curve of the standard sample, thereby obtaining the molecular weight and molecular weight distribution of the compound. At this time, Infinity II 1260 (Agilient) can be used as the measuring device, and the flow rate can be set to 1.00 mL / min and the column temperature to 40.0 °C.
[0149] Throughout this specification, “*” indicates a bond position.
[0150]
[0151] Hereinafter, the present specification will be described in more detail.
[0152] One embodiment of the present invention provides a positive photosensitive resin composition comprising: an alkali-soluble polymer resin; an esterified quinonediazide-based compound; and a crosslinking agent including a phenol group; wherein the alkali-soluble polymer resin comprises a reaction product of a mixture including an amine-based compound, an acid anhydride-based compound, and a capping compound, and satisfies the following formula 1:
[0153] [Formula 1]
[0154] (A+B) / 2 < 6.0 eV
[0155] In the above formula 1, A is the CTC value (eV) of the amine compound, B is the sum of the CTC value (eV) of the acid anhydride compound and the CTC value (eV) of the capping compound in a mixture of the acid anhydride compound and the capping compound, and the CTC value means a quantum calculation simulation value for the energy level difference between the electron donor and electron acceptor of the compound, assuming that the compound forms a charge transfer complex.
[0156] A positive photosensitive resin composition according to one embodiment of the present invention may have excellent sensitivity, film retention, adhesive strength, chemical resistance, heat resistance, solar resistance, hygroscopicity, operating reliability, and bending characteristics.
[0157] According to one embodiment of the present invention, the alkali-soluble polymer resin satisfies the above formula 1. Specifically, the CTC value of the alkali-soluble polymer resin calculated by the following formula 1-1 may be 3.5 eV or more and less than 6.0 ev.
[0158] [Formula 1-1]
[0159] CTC(ev) of alkali-soluble polymer resin = (A+B) / 2
[0160] In the above equation 1-1, A and B are the same as defined in the above equation 1. At this time, the CTC value means a quantum calculation simulation value for the energy level difference between the electron donor (HOMO) and electron acceptor (LUMO) of each of the amine compound, acid anhydride compound, or capping compound, assuming that each of the amine compound, acid anhydride compound, or capping compound forms a charge transfer complex. At this time, the quantum calculation simulation value can be calculated through M06-2X / 6-311G by applying Gaussian 16, Density Functional Theory.
[0161] According to one embodiment of the present invention, the CTC value of the amine compound may be a CTC value based on 100 parts by weight of the amine compound. For example, based on 100 parts by weight of the amine compound represented by Compound 1-2 described below, the CTC value of Compound 1-2 may be 4.56 ev. In addition, based on 100 parts by weight of the amine compound represented by Compound 1-15 described below, the CTC value of Compound 1-15 may be 5.49 ev. Meanwhile, the amine compound may include one or more amine compounds. At this time, the CTC value of the amine compound may be calculated through the CTC value of each of the amine compounds included in the amine compound and the weight ratio (mixing ratio) of the amine compounds. For example, based on 100 parts by weight of the amine compound, the content of Compound 1-2 may be 30 parts by weight and the content of Compound 1-15 may be 70 parts by weight. At this time, the CTC value (A) of the amine compound in the above formula 1 and formula 1-1 may be the sum of the CTC value of compound 1-2 (4.56 ev X (30 / 100)) and the CTC value of compound 1-15 (5.49 ev X (70 / 100)) in the amine compound.
[0162] According to one embodiment of the present invention, the CTC value of the acid anhydride compound may be a CTC value based on 100 parts by weight of the acid anhydride compound. In this case, 100 parts by weight of the acid anhydride compound may be a content based on 100 parts by weight of the amine compound. For example, based on 100 parts by weight of the acid anhydride compound represented by Compound 2-4 described below, the CTC value of Compound 2-4 may be 5.92 ev. In addition, the CTC value of the capping compound may be a CTC value based on 100 parts by weight of the capping compound. In this case, 100 parts by weight of the capping compound may be a content based on 100 parts by weight of the amine compound. For example, based on 100 parts by weight of the capping compound represented by Compound C-4 described below, the CTC value of Compound C-4 may be 4.60 ev.
[0163] In the above formula 1 and formula 1-1, the sum (B) of the CTC value (eV) of the acid anhydride compound and the CTC value (eV) of the capping compound can be calculated as follows. For example, based on 100 parts by weight of the amine compound, the content of compound 2-4 can be 80 parts by weight and the content of compound C-4 can be 40 parts by weight. In the above formula 1 and formula 1-1, B can be the sum of the CTC value of compound 2-4 (5.92 ev X (80 / 120)) and the CTC value of compound C-4 (4.60 ev X (40 / 120)) in the mixture of the acid anhydride compound and the capping compound.
[0164] According to one embodiment of the present invention, the CTC value of the alkali-soluble polymer resin calculated by the above formula 1-1 is 3.5 eV or more and less than 6.0 ev, 3.7 eV or more and 5.99 ev or less, 3.9 eV or more and 5.95 ev or less, 4.0 eV or more and 5.9 ev or less, 4.2 eV or more and 5.8 ev or less, 4.4 eV or more and 5.7 ev or less, 4.6 eV or more and 5.6 ev or less, 4.8 eV or more and 5.5 ev or less, 5.0 eV or more and 5.4 ev or less, 4.0 eV or more and 5.5 ev or less, 4.3 eV or more and 5.2 ev or less, 4.6 eV or more and 5.1 ev or less, 4.7 eV or more and 5.0 ev or less, 5.0 eV or more and 5.99 ev or less, 5.2 It can be 5.95 eV or more and 5.4 eV or more and 5.9 eV or less, or 5.6 eV or more and 5.8 eV or less. It is possible to effectively provide a cured product having excellent sensitivity, film retention rate, adhesion, chemical resistance, heat resistance, solar resistance, hygroscopicity, operating reliability, and bending characteristics, including the alkali-soluble polymer resin satisfying the range of the above-mentioned CTC values.
[0165] According to one embodiment of the present invention, the fluorine content of the positive photosensitive composition may be 10,000 ppm or less. Specifically, the positive photosensitive composition has a fluorine content of 0 ppm or more and 10,000 ppm or less, 500 ppm or more and 9,500 ppm or less, 1,000 ppm or more and 9,000 ppm or less, 2,000 ppm or more and 8,000 ppm or less, 3,000 ppm or more and 7,000 ppm or less, 4,000 ppm or more and 6,000 ppm or less, 0 ppm or more and 6,000 ppm or less, 100 ppm or more and 5,500 ppm or less, 300 ppm or more and 5,000 ppm or less, 700 ppm or more and 4,500 ppm or less, 900 ppm or more and 4,000 ppm or less, 1,100 ppm or more and 3,500 ppm or less, 1,500 ppm or more and 3,300 The fluorine content may be 1,700 ppm or less, 1,700 ppm or more and 2,900 ppm or less, 5,000 ppm or more and 10,000 ppm or less, 5,500 ppm or more and 9,000 ppm or less, 6,000 ppm or more and 8,500 ppm or less, or 6,500 ppm or more and 8,000 ppm or less. The positive photosensitive resin composition having a fluorine content satisfying the above-mentioned range may have excellent physical properties such as heat resistance, solar resistance, hygroscopicity, and operating reliability.
[0166] According to one embodiment of the present invention, the alkali-soluble polymer resin may include a repeating unit represented by the following chemical formula A and a repeating unit represented by the following chemical formula B:
[0167] [Chemical Formula A]
[0168]
[0169] [Chemical Formula B]
[0170]
[0171] In the above chemical formula A and chemical formula B, the R a and R bare each independently an organic group having 5 to 60 carbon atoms, X1 and X2 are each independently hydrogen or an alkyl group having 1 to 10 carbon atoms, a and b are each independently an integer from 0 to 4, c and d are each independently an integer from 0 to 2, and a+b is 1 or more.
[0172] Specifically, the above R a may include at least one of an aromatic group having 6 to 30 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, and a cycloalkene group having 5 to 10 carbon atoms. In addition, the R b may contain at least one aromatic group having 6 to 30 carbon atoms. X1 and X2 may be hydrogen. a may be 0 to 3, 0 to 2, 0 to 1, or 0. b may be 1 to 3, 2 to 3, or 2. c may be 1 to 2, or 2. d may be 0 to 1, or 0.
[0173] By using an alkali-soluble polymer resin including a repeating unit represented by the above chemical formula A and a repeating unit represented by the above chemical formula B, a positive photosensitive resin composition with improved sensitivity, film retention rate, adhesive strength, chemical resistance, heat resistance, solar resistance, hygroscopicity, operating reliability, and bending characteristics can be provided.
[0174] According to one embodiment of the present invention, the repeating unit represented by the chemical formula A may be a repeating unit represented by the following chemical formula A-1, and the repeating unit represented by the chemical formula B may be a repeating unit represented by the following chemical formula B-1.
[0175] [Chemical Formula A-1]
[0176]
[0177] [Chemical Formula B-1]
[0178]
[0179] R in the above chemical formula A-1 and chemical formula B-1a , R b , X1, X2, a to d are the same as defined in the above-described chemical formulas A and B. That is, the repeating unit represented by the chemical formula A-1 may include an amic acid bond, and the repeating unit represented by the chemical formula B-1 may include an imide bond.
[0180] According to one embodiment of the present invention, the alkali-soluble polymer resin may have a repeating unit represented by the chemical formula B in an amount of 51 mol% or more, based on 100 mol% of the total of the repeating unit represented by the chemical formula A and the repeating unit represented by the chemical formula B. That is, the content of the repeating unit including the imide bond may be 51 mol% or more, based on 100 mol% of the total of the repeating unit including the amic acid bond and the repeating unit including the imide bond.
[0181] Specifically, based on a total of 100 mol% of the repeating unit represented by the chemical formula A and the repeating unit represented by the chemical formula B, the content of the repeating unit represented by the chemical formula B may be 51 mol% or more and 97 mol% or less, 55 mol% or more and 97 mol% or less, 60 mol% or more and 97 mol% or less, 65 mol% or more and 97 mol% or less, 70 mol% or more and 97 mol% or less, 75 mol% or more and 97 mol% or less, 80 mol% or more and 97 mol% or less, 85 mol% or more and 95 mol% or less, 88 mol% or more and 95 mol% or less, 89 mol% or more and 95 mol% or less, 90 mol% or more and 95 mol% or less, 91 mol% or more and 95 mol% or less, or 93 mol% or more and 95 mol% or less. By using the alkali-soluble polymer resin having a content of a repeating unit represented by chemical formula B that satisfies the above-mentioned range, a positive-type photosensitive resin composition with improved chemical resistance and heat resistance can be provided.
[0182] According to one embodiment of the present invention, the repeating unit represented by the chemical formula A and the repeating unit represented by the chemical formula B are Rb It may include a structure derived from an amine compound containing. Specifically, the amine compound may contain one or more amine groups in the structure. The amine compound may include a diamine compound. More specifically, the amine compound may include at least a first aromatic group having 6 to 30 carbon atoms to which one or more amine groups are bonded and a second aromatic group having 6 to 30 carbon atoms to which one or more amine groups are bonded. The R b By using the alkali-soluble polymer resin having a structure derived from an amine compound containing , a positive photosensitive resin composition having improved sensitivity, film retention rate, adhesive strength, chemical resistance, heat resistance, solar resistance, hygroscopicity, operating reliability, and bending characteristics can be provided.
[0183] According to one embodiment of the present invention, the amine compound may include at least one of the compounds represented by the following chemical formulas 1-1 to 1-19.
[0184] [Chemical Formula 1-1] [Chemical Formula 1-2]
[0185]
[0186] [Chemical Formula 1-3] [Chemical Formula 1-4]
[0187]
[0188] [Chemical Formula 1-5] [Chemical Formula 1-6]
[0189]
[0190] [Chemical Formula 1-7]
[0191]
[0192] [Chemical Formula 1-8]
[0193]
[0194] [Chemical Formula 1-9]
[0195]
[0196] [Chemical Formula 1-10]
[0197]
[0198] [Chemical Formula 1-11] [Chemical Formula 1-12]
[0199]
[0200] [Chemical Formula 1-13] [Chemical Formula 1-14]
[0201]
[0202] [Chemical Formula 1-15]
[0203]
[0204] [Chemical Formula 1-16]
[0205]
[0206] [Chemical Formula 1-17]
[0207]
[0208] [Chemical Formula 1-18]
[0209]
[0210] [Chemical Formula 1-19]
[0211]
[0212] At least two of a1, b1, c1, d1, e1 and f1 are amine groups, and the rest are hydrogen, a hydroxyl group, an alkyl group having 1 to 3 carbon atoms substituted with a halogen element or -COOX2, and at least two of a2, b2, c2 and d2 are amine groups, and the rest are hydrogen, a hydroxyl group or -COOX2, and R 1-1 and R 1-2are each independently hydrogen, an alkyl group having 1 to 10 carbon atoms, an alkyl group having 1 to 3 carbon atoms substituted with a halogen element, or a cycloalkyl group having 5 to 10 carbon atoms, and at least two of a3, b3, c3, and d3 are amine groups, and the rest are hydrogen, a hydroxy group, or -COOX2, and R 1-3 and R 1-4 are each independently an alkyl group having 1 to 10 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms, and R 1-5 and R 1-6 are each independently hydrogen or an alkyl group having 1 to 10 carbon atoms, at least two of a4, b4, c4 and d4 are amine groups, and the rest are hydrogen, a hydroxy group or -COOX2, at least two of a5, b5, c5 and d5 are amine groups, and the rest are hydrogen, a hydroxy group or -COOX2, and R 1-7 and R 1-8 are each independently an alkyl group having 1 to 10 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms, at least two of a6, b6, c6 and d6 are amine groups, and the rest are hydrogen, a hydroxyl group or -COOX2, at least two of a7, b7, c7 and d7 are amine groups, and the rest are hydrogen, a hydroxyl group or -COOX2, at least two of a8, b8, c8 and d8 are amine groups, and the rest are hydrogen, a hydroxyl group or -COOX2, and R 1-9 and R 1-10 are each independently an alkyl group having 1 to 10 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms, at least two of a9, b9, c9 and d9 are amine groups, and the rest are hydrogen, hydroxyl groups or -COOX2, and a 10 , b 10 , c 10 and d 10 At least two of them are amine groups, the rest are hydrogen, hydroxyl groups or -COOX2, and a 11 , b 11 , c 11 , d 11 , e11 and f 11 At least two of them are amine groups, the rest are hydrogen, hydroxyl groups or -COOX2, and a 12 , b 12 , c 12 , d 12 , e 12, f 12 and g 12 At least two of them are amine groups, the rest are hydrogen, hydroxyl groups or -COOX2, and a 13 , b 13 , c 13 , d 13 , e 13 and f 13 At least two of which are amine groups, and the rest are hydrogen, hydroxyl groups, alkyl groups having 1 to 3 carbon atoms unsubstituted or substituted with halogen elements, or -COOX2, and a 14 is a thiol group, an amine group or a hydroxy group, and X2 is hydrogen or an alkyl group having 1 to 10 carbon atoms. In this case, the halogen element may be fluorine (F).
[0213] Specifically, in Chemical Formula 1-1, b1 and e1 may be amine groups. In addition, in Chemical Formula 1-1, c1 and d1 may be amine groups. In Chemical Formula 1-2, a2 and c2 may be amine groups. In addition, in Chemical Formula 1-2, b2 and d2 may be amine groups. In Chemical Formula 1-3, a3 and c3 may be amine groups. In Chemical Formula 1-4, a4 and c4 may be amine groups. In Chemical Formula 1-5, b5 and d5 may be amine groups. In Chemical Formula 1-6, a6 and c6 may be amine groups. In addition, in Chemical Formula 1-6, b6 and d6 may be amine groups. In Chemical Formula 1-7, b7 and d7 may be amine groups. In the above chemical formula 1-8, a8 and d8 may be amine groups. In the above chemical formula 1-9, a9 and d9 may be amine groups. In the above chemical formula 1-10, a 10 and c 10may be an amine group. In the above chemical formula 1-11, b 11 and e 11 may be an amine group. In the above chemical formula 1-12, b 12 and e 12 may be an amine group. In the above chemical formula 1-13, c 13 and d 13 may be an amine group.
[0214] By using the alkali-soluble polymer resin having a structure derived from an amine compound including at least one of the compounds represented by the above chemical formulae 1-1 to 1-19, a positive-type photosensitive resin composition having improved sensitivity, film retention rate, adhesive strength, chemical resistance, heat resistance, solar resistance, hygroscopicity, operating reliability, and bending characteristics can be effectively implemented.
[0215] According to one embodiment of the present invention, the CTC value of the amine compound may be 4.0 eV or more and 8.0 eV or less. That is, the CTC value of each of the compounds represented by Chemical Formulas 1-1 to 1-19 may be 4.0 eV or more and 8.0 eV or less. In this case, the CTC value of the amine compound may be based on 100 parts by weight of the amine compound. Specifically, the CTC value of the amine compound may be 4.2 eV or more and 7.5 eV or less, 4.4 eV or more and 7.0 eV or less, 4.6 eV or more and 7.0 eV or less, 4.8 eV or more and 7.0 eV or less, 5.0 eV or more and 7.0 eV or less, 5.2 eV or more and 7.0 eV or less, 5.4 eV or more and 7.0 eV or less, 5.6 eV or more and 7.0 eV or less, 5.8 eV or more and 7.0 eV or less, 6.0 eV or more and 7.0 eV or less, 6.2 eV or more and 7.0 eV or less, or 6.5 eV or more and 7.0 eV or less. When the CTC value of the above amine compound is within the above-mentioned range, a positive photosensitive resin composition with improved sensitivity, film retention rate, adhesion, chemical resistance, heat resistance, solar resistance, hygroscopicity, operating reliability, and bending characteristics can be effectively implemented.
[0216] According to one embodiment of the present invention, the amine compound may include at least one of the following compounds 1-1 to 1-32.
[0217] [Compound 1-1] [Compound 1-2]
[0218]
[0219] [Compound 1-3] [Compound 1-4]
[0220]
[0221] [Compound 1-5] [Compound 1-6]
[0222]
[0223] [Compound 1-7]
[0224]
[0225] [Compound 1-8]
[0226]
[0227] [Compound 1-9]
[0228]
[0229] [Compounds 1-10]
[0230]
[0231] [Compound 1-11] [Compound 1-12]
[0232]
[0233] [Compound 1-13]
[0234]
[0235] [Compound 1-14]
[0236]
[0237] [Compound 1-15] [Compound 1-16]
[0238]
[0239] [Compound 1-17]
[0240]
[0241] [Compound 1-18]
[0242]
[0243] [Compound 1-19] [Compound 1-20]
[0244]
[0245] [Compound 1-21] [Compound 1-22]
[0246]
[0247] [Compound 1-23] [Compound 1-24]
[0248]
[0249] [Compound 1-25]
[0250]
[0251] [Compound 1-26] [Compound 1-27]
[0252]
[0253] [Compound 1-28]
[0254]
[0255] [Compound 1-29] [Compound 1-30]
[0256]
[0257] [Compound 1-31]
[0258]
[0259] [Compound 1-32]
[0260]
[0261] When an amine compound including at least one of the compounds 1-1 to 1-32 is used, the positive photosensitive resin composition can have excellent sensitivity, film retention rate, adhesive strength, chemical resistance, heat resistance, solar resistance, hygroscopicity, operating reliability, and bending characteristics.
[0262] According to one embodiment of the present invention, the repeating unit represented by the chemical formula A and the repeating unit represented by the chemical formula B are R aIt may include a structure derived from an acid anhydride compound containing. Specifically, the acid anhydride compound may include an acid dianhydride compound. More specifically, the acid anhydride compound may include a cyclic acid dianhydride compound. More specifically, the acid anhydride compound may include at least a third aromatic group having 6 to 30 carbon atoms to which an acid anhydride group is bonded and a fourth aromatic group having 6 to 30 carbon atoms to which an acid anhydride group is bonded. The R a By using the alkali-soluble polymer resin having a structure derived from an acid anhydride compound containing , a positive photosensitive resin composition having improved sensitivity, film retention rate, adhesive strength, chemical resistance, heat resistance, solar resistance, hygroscopicity, operating reliability, and bending characteristics can be provided.
[0263] According to one embodiment of the present invention, the acid anhydride compound may include at least one of the compounds represented by the following chemical formulas 2-1 to 2-16:
[0264] [Chemical Formula 2-1]
[0265]
[0266] [Chemical Formula 2-2]
[0267]
[0268] [Chemical Formula 2-3]
[0269]
[0270] [Chemical Formula 2-4] [Chemical Formula 2-5]
[0271]
[0272] [Chemical Formula 2-6]
[0273]
[0274] [Chemical Formula 2-7]
[0275]
[0276] [Chemical Formula 2-8]
[0277]
[0278] [Chemical Formula 2-9] [Chemical Formula 2-10]
[0279]
[0280] [Chemical Formula 2-11] [Chemical Formula 2-12]
[0281]
[0282] [Chemical Formula 2-13] [Chemical Formula 2-14]
[0283]
[0284] [Chemical Formula 2-15]
[0285]
[0286] [Chemical Formula 2-16]
[0287]
[0288] In the above chemical formulas, R 2-1 Inland R 2-6 are each independently an alkyl group having 1 to 10 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms, and n is an integer from 2 to 20. Specifically, R 2-1 Inland R 2-6 may each independently be an alkyl group, and the number of carbon atoms in the alkyl group may be 1 to 8, 1 to 5, 1 to 3, or 1. n may be an integer of 2 to 18, 2 to 16, 2 to 14, 2 to 12, 2 to 10, 2 to 8, 2 to 6, or 2 to 4.
[0289] By using the alkali-soluble polymer resin having a structure derived from an acid anhydride compound including at least one of the compounds represented by the above chemical formulas 2-1 to 2-17, a positive photosensitive resin composition having improved sensitivity, film retention rate, adhesive strength, chemical resistance, heat resistance, solar resistance, hygroscopicity, operating reliability, and bending characteristics can be effectively realized.
[0290] According to one embodiment of the present invention, the CTC value of the acid anhydride compound may be 4.0 eV or more and 7.0 eV or less. That is, the CTC value of each of the compounds represented by Chemical Formulas 2-1 to 2-16 may be 4.0 eV or more and 7.0 eV or less. In this case, the CTC value of the acid anhydride compound may be based on 100 parts by weight of the acid anhydride compound per 100 parts by weight of the amine compound. Specifically, the CTC value of the acid anhydride compound may be 4.2 eV or more and 6.5 eV or less, 4.4 eV or more and 6.0 eV or less, 4.6 eV or more and 6.0 eV or less, 4.8 eV or more and 6.0 eV or less, 5.0 eV or more and 6.0 eV or less, 5.2 eV or more and 6.0 eV or less, 5.4 eV or more and 6.0 eV or less, 5.6 eV or more and 6.0 eV or less, or 5.8 eV or more and 6.0 eV or less. When the CTC value of the acid anhydride compound is within the above-mentioned range, a positive photosensitive resin composition with improved sensitivity, film residue rate, adhesion, chemical resistance, heat resistance, solar resistance, hygroscopicity, operating reliability, and bending characteristics can be effectively implemented.
[0291] According to one embodiment of the present invention, the acid anhydride compound may include at least one of the following compounds 2-1 to 2-17.
[0292] [Compound 2-1]
[0293]
[0294] [Compound 2-2]
[0295]
[0296] (n is an integer of 2)
[0297] [Compound 2-3]
[0298]
[0299] (n is an integer of 4)
[0300] [Compound 2-4]
[0301]
[0302] [Compound 2-5] [Compound 2-6]
[0303]
[0304] [Compound 2-7]
[0305]
[0306] [Compound 2-8]
[0307]
[0308] [Compound 2-9]
[0309]
[0310] [Compound 2-10] [Compound 2-11]
[0311]
[0312] [Compound 2-12] [Compound 2-13]
[0313]
[0314] [Compound 2-14] [Compound 2-15]
[0315]
[0316] [Compound 2-16]
[0317]
[0318] [Compound 2-17]
[0319]
[0320] When an acid anhydride compound including at least one of the compounds 2-1 to 2-17 is used, the positive photosensitive resin composition can have excellent sensitivity, film retention rate, adhesive strength, chemical resistance, heat resistance, solar resistance, hygroscopicity, operating reliability, and bending characteristics.
[0321] According to one embodiment of the present invention, the alkali-soluble polymer resin may have a main chain end-capped with a capping compound comprising an acid anhydride compound. The capping compound may comprise a cyclic acid anhydride compound. The cyclic acid anhydride compound may comprise a benzene ring or a cyclohexene ring.
[0322] According to one embodiment of the present invention, the capping compound may include at least one of the following compounds C-1 to C-5:
[0323] [Compound C-1] [Compound C-2]
[0324]
[0325] [Compound C-3] [Compound C-4]
[0326]
[0327] [Compound C-5]
[0328] .
[0329] When the alkali-soluble polymer resin includes a terminal group derived from the capping compound, the positive photosensitive resin composition can have excellent sensitivity, film retention rate, adhesion, chemical resistance, heat resistance, solar resistance, hygroscopicity, operating reliability, and bending characteristics.
[0330] According to one embodiment of the present invention, the CTC value of the capping compound may be 4.0 eV or more and 6.0 eV or less. That is, the CTC value of each of the compounds represented by Compound C-1 to Compound C-5 may be 4.0 eV or more and 6.0 eV or less. At this time, the CTC value of the capping compound may be based on 100 parts by weight of the capping compound per 100 parts by weight of the amine compound. Specifically, the CTC value of the capping compound may be 4.2 eV or more and 5.5 eV or less, 4.4 eV or more and 5.0 eV or less, 4.6 eV or more and 5.0 eV or less, or 4.8 eV or more and 5.0 eV or less. When the CTC value of the capping compound is within the above-mentioned range, a positive photosensitive resin composition with improved sensitivity, film retention rate, adhesion, chemical resistance, heat resistance, solar resistance, hygroscopicity, operating reliability, and bending characteristics can be effectively implemented.
[0331] According to one embodiment of the present invention, the esterified quinonediazide compound may include a reaction product of at least one of the phenol compounds represented by the following chemical formulas 3-1 to 3-13 and a quinonediazide compound:
[0332] [Chemical Formula 3-1] [Chemical Formula 3-2]
[0333]
[0334] [Chemical Formula 3-3]
[0335]
[0336] [Chemical Formula 3-4] [Chemical Formula 3-5]
[0337]
[0338] [Chemical Formula 3-6]
[0339]
[0340] [Chemical Formula 3-7] [Chemical Formula 3-8]
[0341]
[0342] [Chemical Formula 3-9] [Chemical Formula 3-10]
[0343]
[0344] [Chemical Formula 3-11] [Chemical Formula 3-12]
[0345]
[0346] [Chemical Formula 3-13]
[0347]
[0348] In the above chemical formulas, R 3-1 Inland R 3-84 are each independently hydrogen, an alkyl group having 1 to 4 carbon atoms, or an alkenyl group having 2 to 4 carbon atoms, and Z1 to Z4 are each independently hydrogen, an alkyl group having 1 to 4 carbon atoms.
[0349] Specifically, the quinonediazide compound may include a naphthoquinonediazide compound. That is, the esterified quinonediazide compound may include a reaction product of a naphthoquinonediazide compound and one of the phenol compounds represented by the following chemical formulas 3-1 to 3-13:
[0350] According to one embodiment of the present invention, the esterified quinonediazide compound may include a compound represented by the following chemical formula 3-A.
[0351] [Chemical Formula 3-A]
[0352]
[0353] In the above chemical formula 3-A, “A” corresponds to the structure (moiety) of the phenolic compound, and the oxygen of the “AO” bond corresponds to the oxygen of the phenolic hydroxyl group of the phenolic compound. The positive photosensitive resin composition including the esterified quinonediazide compound can easily realize an organic film having excellent sensitivity, film retention rate, adhesive strength, chemical resistance, heat resistance, solar resistance, hygroscopicity, operating reliability, and bending characteristics.
[0354] According to one embodiment of the present invention, the phenolic compound may include at least one of the following compounds 3-1 to 3-13.
[0355] [Compound 3-1] [Compound 3-2]
[0356]
[0357] [Compound 3-3]
[0358]
[0359] [Compound 3-4] [Compound 3-5]
[0360]
[0361] [Compound 3-6]
[0362]
[0363] [Compound 3-7] [Compound 3-8]
[0364]
[0365] [Compound 3-9] [Compound 3-10]
[0366]
[0367] [Compound 3-11] [Compound 3-12]
[0368]
[0369] [Compound 3-13]
[0370]
[0371] According to one embodiment of the present invention, the esterified quinonediazide compound may be bound to 2 mol or more of the quinonediazide compound based on 1 mol of the phenolic compound. Specifically, based on 1 mol of the phenolic compound, the content of the quinonediazide compound bound to the phenolic hydroxy group of the phenolic compound may be 2.0 mol or more and 3.5 mol or less, 2.5 mol or more and 3.5 mol or less, 3.2 mol or more and 3.5 mol or less, 2.0 mol or more and 3.0 mol or less, 2.2 mol or more and 2.8 mol or less, 2.4 mol or more and 2.6 mol or less, 2.5 mol or more and 3.5 mol or less, 2.8 mol or more and 3.3 mol or less, or 3.0 mol or more and 3.2 mol or less. By using the esterified quinonediazide compound in which the quinonediazide compound is combined in the above-mentioned amount, the positive photosensitive resin composition can effectively produce an organic film having excellent chemical resistance and heat resistance.
[0372] The quinonediazide compound can react with the phenolic hydroxy group of the phenolic compound. For example, the phenolic compound represented by Chemical Formula 3-7 contains four phenolic hydroxy groups, and 1 mol of the phenolic compound contains 4 mol of reaction sites. When the quinonediazide compound reacts with the phenolic compound represented by Chemical Formula 3-7, the esterified quinonediazide compound may include an unreacted phenolic compound containing four phenolic hydroxy groups, a reaction product containing three phenolic hydroxy groups and bonded to one quinonediazide compound, a reaction product containing two phenolic hydroxy groups and bonded to two quinonediazide compounds, a reaction product containing one phenolic hydroxy group and bonded to three quinonediazide compounds, and a reaction product containing four quinonediazide compounds. The content of the quinonediazide compound bound to the above-mentioned esterified quinonediazide compound may be based on 1 mol of the phenol compound for the entire reaction product. That is, the content of the quinonediazide compound bound to the esterified quinonediazide compound may correspond to the content of the quinonediazide compound added to perform the reaction for 1 mol of the phenol compound.
[0373] According to one embodiment of the present invention, the content of the esterified quinonediazide-based compound may be 10 parts by weight or more and 40 parts by weight or less with respect to 100 parts by weight of the alkali-soluble polymer resin. Specifically, the content of the esterified quinonediazide-based compound may be 15 parts by weight or more and 35 parts by weight or less, 20 parts by weight or more and 30 parts by weight or less, 10 parts by weight or more and 30 parts by weight or less, 12.5 parts by weight or more and 27.5 parts by weight or less, 17.5 parts by weight or more and 27.5 parts by weight or less, 22.5 parts by weight or more and 25 parts by weight or less, 20 parts by weight or more and 40 parts by weight or less, 20 parts by weight or more and 37.5 parts by weight or less, 20 parts by weight or more and 32.5 parts by weight or less, 20 parts by weight or more and 27.5 parts by weight or less, or 20 parts by weight or more and 25 parts by weight or less with respect to 100 parts by weight of the alkali-soluble polymer resin. When the content of the esterified quinonediazide compound is within the above-mentioned range, the positive photosensitive resin composition can effectively implement an organic film with improved chemical resistance and heat resistance.
[0374] According to one embodiment of the present invention, the crosslinking agent may include at least one of the compounds represented by the following chemical formulas 4-1 to 4-21:
[0375] [Chemical Formula 4-1] [Chemical Formula 4-2]
[0376]
[0377] [Chemical Formula 4-3] [Chemical Formula 4-4]
[0378]
[0379] [Chemical Formula 4-5] [Chemical Formula 4-6]
[0380]
[0381] [Chemical Formula 4-7] [Chemical Formula 4-8]
[0382]
[0383] [Chemical Formula 4-9] [Chemical Formula 4-10]
[0384]
[0385] [Chemical Formula 4-11] [Chemical Formula 4-12]
[0386]
[0387] [Chemical Formula 4-13] [Chemical Formula 4-14]
[0388]
[0389] [Chemical Formula 4-15] [Chemical Formula 4-16]
[0390]
[0391] [Chemical Formula 4-17]
[0392]
[0393] [Chemical Formula 4-18]
[0394]
[0395] [Chemical Formula 4-19]
[0396]
[0397] [Chemical Formula 4-20]
[0398]
[0399] [Chemical Formula 4-21]
[0400]
[0401] In the above chemical formulas, R 4a Inland R 4h are each independently hydrogen, an alkyl group having 1 to 3 carbon atoms, or , and in the chemical formulas 4-1 to 4-8, R 4a and R 4b At least one of them And, in the above chemical formula 4-9, R 4a Inland R 4c At least one of them And, in the chemical formulas 4-10 to 4-15, R 4a Inland R 4d At least one of them And, in the chemical formulas 4-16 to 4-18, R 4a Inland R 4f At least one of them And, in the chemical formulas 4-19 to 4-21, R 4a Inland R 4h At least one of them , m is an integer from 1 to 6, and R 4-1 is an alkyl group having 1 to 3 carbon atoms.
[0402] Specifically, in the above chemical formulas, R 4a Inland R 4h Is may be. m may be 1 to 4, 1 to 2, or 1. R 4-1 can be a methyl group. More specifically, R 4a Inland R 4h may be -CH2-O-CH3. By using the above-described type of crosslinking agent, the positive photosensitive resin composition can stably form an organic film.
[0403] According to one embodiment of the present invention, with respect to 100 parts by weight of the alkali-soluble polymer resin, the content of the crosslinking agent may be 5 parts by weight or more and 30 parts by weight or less. 8 parts by weight or more and 28 parts by weight or less, 8 parts by weight or more and 25 parts by weight or less, 8 parts by weight or more and 20 parts by weight or less, 10 parts by weight or more and 25 parts by weight or less, 15 parts by weight or more and 20 parts by weight or less, 5 parts by weight or more and 20 parts by weight or less, 8 parts by weight or more and 17 parts by weight or less, 12 parts by weight or more and 14 parts by weight or less, 10 parts by weight or more and 30 parts by weight or less, 12 parts by weight or more and 25 parts by weight or less, 14 parts by weight or more and 23 parts by weight or less, or 15 parts by weight or more and 20 parts by weight or less. When the content of the crosslinking agent is within the above-mentioned range, the positive photosensitive resin composition can effectively implement an organic film having excellent chemical resistance, heat resistance, solar resistance, hygroscopicity, operating reliability, and bending characteristics.
[0404] According to one embodiment of the present invention, the positive photosensitive resin composition may further include at least one of an organic solvent, a surfactant, and an additive. The organic solvent may include at least one 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), diethyl glycol ethyl methyl ether (MEDG), diethyl glycol butyl methyl ether (MBDG), diethylene glycol dimethyl ester (DMDG), and diethylene glycol diethyl ester (DEDG). The surfactant and additive may be used without limitation as those used in the art. For example, the additive may include a thermal acid generator, a UV absorber, and the like.
[0405]
[0406] One embodiment of the present invention provides a method for manufacturing an insulating film, including the steps of applying a positive photosensitive resin precursor composition onto a substrate and drying it, exposing it, developing it using an alkaline developer, and heating it.
[0407] A manufacturing method according to one embodiment of the present invention can easily manufacture an insulating film having excellent sensitivity, film retention rate, adhesive strength, chemical resistance, heat resistance, solar resistance, hygroscopicity, operating reliability, and bending characteristics using the positive photosensitive resin composition.
[0408]
[0409] One embodiment of the present invention provides an electronic component including an insulating film including a cured product of the positive photosensitive resin composition.
[0410] An electronic component according to one embodiment of the present invention may have excellent sensitivity, film retention, adhesive strength, chemical resistance, heat resistance, solar resistance, moisture absorption, operating reliability, and bending characteristics.
[0411] According to one embodiment of the present invention, the insulating film can be used as an insulating film such as an interlayer insulating film, a protective insulating film, a gate insulating film, and a planarizing film. In addition, an electronic component including the insulating film can be an electronic component for OLED, an electronic component for semiconductors, an electronic component for displays, etc.
[0412]
[0413] One embodiment of the present invention provides a display device including an insulating film including a cured product of the positive photosensitive resin composition.
[0414] A display device for an organic light emitting element according to one embodiment of the present invention may have excellent sensitivity, film retention rate, adhesive strength, chemical resistance, heat resistance, solar resistance, hygroscopicity, operating reliability, and bending characteristics.
[0415] According to one embodiment of the present invention, the display device may include a first electrode provided on a substrate; an insulating film provided on the first electrode so as to partially expose the first electrode; and a second electrode provided opposite the first electrode. At this time, the insulating film may be provided so as to cover an edge portion of the first electrode.
[0416] According to one embodiment of the present invention, the cross-section of the insulating film at the boundary portion where the insulating film exposes the first electrode may have a purely tapered shape.
[0417] According to one embodiment of the present invention, the display device may include a display device comprising an organic electroluminescent element including a first electrode formed on a substrate, a thin film layer including a light-emitting layer formed on the first electrode and composed of at least an organic compound, and a second electrode formed on the thin film layer.
[0418] According to one embodiment of the present invention, the display device can utilize without limitation any components used in display devices in the art, except for including the organic film. The display device may be a liquid crystal display (LCD), an organic light emitting display (OLED), a plasma display panel (PDP), or an electrophoretic display.
[0419]
[0420] Hereinafter, the present invention will be described in detail using examples. However, the examples according to the present invention may be modified in various ways, and the scope of the present invention is not limited to the examples described below. The examples in this specification are provided to more fully explain the present invention to those of ordinary skill in the art.
[0421]
[0422] ingredient
[0423] Amine compounds for manufacturing alkali-soluble polymer resins
[0424] The values of amine compounds (diamine compounds) and charge transfer complexes (CTC) for manufacturing alkali-soluble polymer resins are shown in Table 1 below.
[0425] The CTC values of amine compounds can be calculated through quantum computation (Gaussian 16, Density Functional Theory_M06-2X / 6-311G) simulations.
[0426]
[0427] Code Structure CTC Standard (Parts by Weight) CTC Value (ev) A-1 (Compound 1-2) 1004.56A-2 (Compound 1-3) 1005.50A-3 (Compound 1-4) 1006.50A-4 (Compounds 1-5) 1006.00A-5 (Compound 1-6) 1004.80A-6 (Compound 1-7) 1006.70A-7 (Compound 1-8) 1004.93A-8 (Compound 1-32) 1005.29A-9 (Compound 1-13) 1004.55A-10 (Compound 1-14) 1004.60A-11 (Compound 1-15) 1005.49A-12 (Compound 1-28) 1006.85A-13 (Compound 1-30) 1007.00A-14 (Compound 1-31) 1006.80
[0428]
[0429] Acid anhydride compounds for manufacturing alkali-soluble polymer resins
[0430] The values of acid anhydride compounds and charge transfer complex (CTC) for manufacturing alkali-soluble polymer resins are shown in Table 2 below.
[0431] The CTC value of an acid anhydride compound can be calculated through quantum calculation (Gaussian 16, Density Functional Theory_M06-2X / 6-311G) simulation. At this time, the CTC value of the acid anhydride compound in Table 2 below is calculated for 100 parts by weight of the acid anhydride compound per 100 parts by weight of the amine compound.
[0432]
[0433] Code Structure CTC Standard (Parts by Weight) CTC Value (ev) B-1 (Compound 2-1) 1004.57B-2 (Compound 2-2) (n is an integer of 2)1005.95B-3 (compound 2-3) (n is an integer of 4)1006.00B-4 (compound 2-4) 1005.92B-5 (Compound 2-5) 1006.71B-6 (Compound 2-6) 1004.57B-7 (Compound 2-7) 1004.80B-8 (Compound 2-8) 1005.93B-9 (Compound 2-15) 1004.56B-10 (Compound 2-16) 1005.50
[0434]
[0435] Capping compounds for the manufacture of alkali-soluble polymer resins
[0436] The capping compound and charge transfer complex (CTC) values for manufacturing alkali-soluble polymer resin are shown in Table 3 below.
[0437] The CTC value of the capping compound can be calculated through quantum calculation (Gaussian 16, Density Functional Theory_M06-2X / 6-311G) simulation. At this time, the CTC value of the capping compound in Table 3 below is calculated for 100 parts by weight of the capping compound per 100 parts by weight of the amine compound.
[0438]
[0439] Code Structure CTC Standard (Parts by Weight) CTC Value (ev) C-1 (Compound C-1) 1004.56C-2 (Compound C-2) 1004.65C-3 (Compound C-3) 1004.60C-4 (compound C-4) 1004.60C-5 (Compound C-5) 1004.56
[0440]
[0441] Preparation of alkali-soluble polymer resins
[0442] Combination of amine compounds (diamine compounds)
[0443] A combination of diamine compounds was prepared as follows.
[0444]
[0445] 1st diamine 2nd diamine Diamine Total synthesis example code content (parts by weight) / CTC (ev) code content (parts by weight) / CTC (ev) content (parts by weight) / CTC (ev) 1A-1 content 30A-11 content 70 content 100.00 CTC 1.368 CTC 3.84 CTC 5.21 2A-2 content 30A-12 content 70 content 100.00 CTC 1.65 CTC 4.80 CTC 6.45 3A-4 content 30A-12 content 70 content 100.00 CTC 1.8 CTC 4.80 CTC 6.60 4A-5 content 30A-11 content 70 content 100.00 CTC 1.44 CTC 3.84 CTC 5.28 5A-6 content 30A-12 Content 70 Content 100.00 CTC 2.01 CTC 4.80 CTC 6.8 16A-7 Content 30A-11 Content 70.00 Content 100.00 CTC 1.479 CTC 3.84 CTC 5.327A-9 Content 30.00 A-11 Content 70.00 Content 100.00 CTC 1.37 CTC 3.84 CTC 5.218A-1 Content 40A-11 Content 60.00 Content 100.00 CTC 1.824 CTC 3.29 CTC 5.129A-3 Content 40A-11 Content 60.00 Content 100.00 CTC 2.6 CTC 3.29 CTC 5.89 10A-4 Content 40A-12 Content 6 0.00 Content 100.00 CTC2.4 CTC4.11 CTC6.5 111A-5 Content 40A-11 Content 60.00 Content 100.00 CTC1.92 CTC3.29 CTC5.2 12A-6 Content 40A-12 Content 60.00 Content 100.00 CTC2.68 CTC4.11 CTC6.79 13A-7 Content 40A-11 Content 60.00 Content 100.00 CTC1.97 2 CTC3.29 CTC5.27 14A-9 Content 40.00 A-11 Content 60.00 Content 100.00 CTC1.82 CTC3.29 CTC5.11 15A-1 Content 50A-11 Content 50.00 Content 100.00 CTC 2.28 CTC 2.75 CTC 5.03 16A-3 Content 50A-11 Content 50.00 Content 100.00 CTC 3.25 CTC 2.75 CTC 6.00 17A-4 Content 50A-12 Content 50.00 Content 100.00 CTC 3 CTC 3.43 CTC 6.43 18A-5 Content 50A-11 Content 50.00 Content 100.00 CTC 2.4 CTC 2.75 CTC 5.15 19A-6 Content 50A-12 Content 50.00 Content 100.00 CTC 3.35 CTC 3.43 CTC 6.78 20A-7 Content 50A-11 Content 50.00Content 100.00CTC2.465CTC2.75CTC5.2121A-8Content 50A-12Content 50.00Content 100.00CTC2.645CTC3.43CTC6.0722A-9Content 50.00A-11Content 50.00Content 100.00CTC2.28CTC2.75CTC5.02.
[0446]
[0447] 1st diamine 2nd diamine 3rd diamine diamine Total synthesis example code content / CTC code content / CTC code content / CTC content / CTC 2 3A-1 content 50 A-9 content 10A-11 content 40 content 100 CTC 2.28 CTC 0.46 CTC 2.20 CTC 4.9 3 24A-2 content 50 A-9 content 10A-12 content 40 content 100 CTC 2.75 CTC 0.46 CTC 2.74 CTC 5.9 5 25A-3 content 50 A-9 content 10A-11 content 40 content 100 CTC 3.25 CTC 0.46 CTC 2.20 CTC 5.9 0 26A-4 content 50 A-9 content 10A-12 content 40 content 100 CTC3CTC0.46CTC2.74CTC6.2027A-5Content 40A-9Content 20A-11Content 40Content 100CTC1.92CTC0.91CTC2.20CTC5.0328A-6Content 40A-9Content 20A-12Content 40Content 100CTC2.68CTC0.91CTC2.74CTC6.3329A-7Content 40A-9Content 20A-11Content 40Content 100CTC1.972CTC0.91CTC2.20CTC5.0831A-2Content 35A-9Content 30A-12Content 35Content 100CTC1.925 CTC1.37CTC2.40CTC5.6932A-3Content 45A-9Content 30A-11Content 25Content 100CTC2.925CTC1.37CTC1.37CTC5.6633A-4Content 45A-9Content 30A-12Content 25Content 100CTC2.7CTC1.37CTC1.71CTC5.7834A-5Content 55A-9Content 30A-11Content 15Content 100CTC2.64CTC1.37CTC0.82CTC4.8335A-7Content 55A-9Content 30A-11Content 15Content 100CTC2.71CTC1.3 7CTC0.82CTC4.936A-8Content55A-9Content30A-12Content15Content100CTC2.90CTC1.37CTC1.03CTC5.337A-1Content30A-2Content60A-9Content10Content100CTC1.36CTC3.3CTC0.46CTC5.1238A-3Content40A-4Content40A-9Content20Content100CTC2.6CTC2.4CTC0.91CTC5.9139A-5Content30A-6Content40A-9Content30Content100CTC1.44CTC2.68CTC1.37CTC5.49
[0448]
[0449] 1st diamine 2nd diamine Diamine Total synthesis example code content (weight parts) / CTC (ev) code content (weight parts) / CTC (ev) content (weight parts) / CTC (ev) 40A-1 content 50A-3 content 50 content 100.00 CTC 2.28 CTC 3.25 CTC 5.5 3 41A-2 content 50A-4 content 50 content 100.00 CTC 2.75 CTC 3 CTC 5 .7542A-3Content 50A-5Content 50Content 100.00CTC3.25CTC2.4CTC5.6543A-5Content 50A-7Content 50Content 100.00CTC2.4CTC2.465CTC4.8744A-6Content 50A-8Content 50Content 100.00CTC3.35CTC2.65CTC6.00
[0450]
[0451] 1st diamine 2nd diamine 3rd diamine diamine Total synthesis example code content / CTC code content / CTC code content / CTC content / CTC 4 5A-1 content 80A-9 content 10A-11 content 10 content 100 CTC 3.6 48 CTC 0.46 CTC 0.55 CTC 4.65 46A-2 content 80A-9 content 10A-12 content 10 content 100 CTC 4.4 CTC 0.46 CTC 0.69 CTC 5.54 47A-3 content 80A-9 content 10A-11 content 10 content 100 CTC 5.2 CTC 0.46 CTC 0.55 CTC 6.20 48A-4 content 80A- 9 Content 10A-12 Content 10 Content 100 CTC 4.8 CTC 0.46 CTC 0.69 CTC 5.94 49A-5 Content 80A-9 Content 10A-11 Content 10 Content 100 CTC 3.84 CTC 0.46 CTC 0.55 CTC 4.84 50A-8 Content 80A-9 Content 10A-12 Content 10 Content 100 CTC 4.23 2 CTC 0.46 CTC 0.69 CTC 5.37 51A-1 Content 40A-2 Content 40A-9 Content 20 Content 100 CTC 1.82 4 CTC 2.2 CTC 0.91 CTC 4.93
[0452]
[0453] 1st diamine 2nd diamine Diamine Total synthesis example code content (weight parts) / CTC (ev) code content (weight parts) / CTC (ev) content (weight parts) / CTC (ev) 52A-2 content 80A-9 content 20.00 content 100.00 CTC4.4 CTC0.91 CTC5.3 153A-3 content 80A-9 content 20.00 content 100.00 CTC5.2 CTC0.91 CTC6.1 154A-4 content 80A-9 content 20.00 content 100.00 CTC4.8 CTC0.91 CTC5.7 155A-5 content 80A-9 content 20.00 content 100.00 CTC3.84CTC0.91CTC4.7556A-6Content 80A-9Content 20.00Content 100.00CTC5.36CTC0.91CTC6.2757A-7Content 80A-9Content 20.00Content 100.00CTC3.944CTC0.91CTC4.8558A-1Content 30A-11Content 70.00Content 100.00CTC1.368CTC3.84CTC5.2159A-3Content 30A-11Content 70.00Content 100.00CTC1.95CTC3.84CTC5.7960A- 6 Content 30A-12 Content 70.00 Content 100.00 CTC 2.01 CTC 4.80 CTC 6.81 61A-7 Content 30A-11 Content 70.00 Content 100.00 CTC 1.479 CTC 3.84 CTC 5.32 62A-1 Content 40A-11 Content 60.00 Content 100.00 CTC 1.824 CTC 3.29 CTC 5.12 63A-3 Content 40A-11 Content 60.00 Content 100.00 CTC 2.6 CTC 3.29 CTC 5.89 64A-5 Content 40A-11 Content 60.00 Content 100.00 CTC1.92CTC3.29CTC5.2165A-6Content 40A-12Content 60.00Content 100.00CTC2.68CTC4.11CTC6.7966A-7Content 40A-11Content 60.00Content 100.00CTC1.972CTC3.29CTC5.2767A-9Content 40.00A-11Content 60.00Content 100.00CTC1.82CTC3.29CTC5.1168A-1Content 50A-11Content 50.00Content 100.00CTC2.28CTC2.75CTC5.03
[0454]
[0455] 1st diamine 2nd diamine 3rd diamine diamine Total synthesis example code content / CTC code content / CTC code content / CTC content / CTC 69 A-8 content 80 A-10 content 10 A-12 content 10 content 100 CTC 4.2 3 2 CTC 0.46 CTC 0.69 CTC 5.3 8 70 A-1 content 40 A-2 content 40 A-10 content 20 content 100 CTC 1.8 2 4 CTC 2.2 CTC 0.92 CTC 4.9 4 71 A-2 content 80 A-10 content 20- content 100 CTC 4.4 CTC 0.92 CTC 5.3 2 72 A-3 content 80 A-10 content 20- content 100 CTC 5.2 CTC 0.9 2CTC6.1273A-4Content 80A-10Content 20-Content 100CTC4.8CTC0.92CTC5.7274A-5Content 80A-10Content 20-Content 100CTC3.84CTC0.92CTC4.7675A-7Content 80A-10Content 20-Content 100CTC3.944CTC0.92CTC4.8676A-7Content 40A-11Content 60-Content 100CTC1.972CTC3.29CTC5.2777A-11Content 70A-13Content 30Content 100CTC3.84CTC2.10CTC5.94
[0456]
[0457] Synthesis examples 78 to 80
[0458] Synthesis Example 78: Combination of a first diamine (code: A-1; content: 30 parts by weight; CTC: 1.368 ev), a second diamine (code: A-9; content: 10 parts by weight; CTC: 0.46 ev), a third diamine (code: A-11; content: 30 parts by weight; CTC: 1.65 ev), and a fourth diamine (code: A-13; content: 30 parts by weight; CTC: 2.1 ev)
[0459] Diamine total (content: 100 parts by weight; CTC: 5.57ev)
[0460]
[0461] Synthesis Example 79: Combination of a first diamine (code: A-3; content: 10 parts by weight; CTC: 0.65 ev), a second diamine (code: A-9; content: 30 parts by weight; CTC: 1.37 ev), a third diamine (code: A-11; content: 30 parts by weight; CTC: 1.65 ev), and a fourth diamine (code: A-14; content: 30 parts by weight; CTC: 2.04 ev)
[0462] Diamine total (content: 100 parts by weight; CTC: 5.7ev)
[0463]
[0464] Synthesis Example 80: Combination of a first diamine (code: A-5; content: 10 parts by weight; CTC: 0.48 ev), a second diamine (code: A-9; content: 20 parts by weight; CTC: 0.91 ev), a third diamine (code: A-11; content: 35 parts by weight; CTC: 1.92 ev), and a fourth diamine (code: A-13; content: 35 parts by weight; CTC: 2.45 ev)
[0465] Diamine total (content: 100 parts by weight; CTC: 5.76ev)
[0466]
[0467] 1st diamine 2nd diamine 3rd diamine diamine Total synthesis example code content / CTC code content / CTC code content / CTC content / CTC 8 1A-3 content 20 A-11 content 40 A-13 content 40 content 100 CTC 1.3 CTC 2.20 CTC 2.80 CTC 6.30 8 2A-9 content 40.00 A-11 content 60.00 content 100 CTC 1.82 CTC 3.29 CTC 5.11 8 3A-1 content 50 A-11 content 50.00 content 100 CTC 2.28 CTC 2.75 CTC 5.0 3 8 4A-3 content 40 A-11 content 60.00 content 100 CTC 2.6 CTC 3.29 CTC 5.89 8 5A- 4 Content 40A-12 Content 60.00 Content 100 CTC 2.4 CTC 4.11 CTC 6.5 18 6A-5 Content 40A-11 Content 60.00 Content 100 CTC 1.92 CTC 3.29 CTC 5.2 18 7A-6 Content 40A-12 Content 60.00 Content 100 CTC 2.68 CTC 4.11 CTC 6.79 88A-5 Content 20A-11 Content 40.00 A-14 Content 40 Content 100 CTC 0.96 CTC 2.20 CTC 2.72 CTC 5.8 8 9A-8 Content 40A-9 Content 20.00 A-12 Content 40 Content 100 CTC 2.1 16CT C0.91CTC2.74CTC5.7790A-7Content80A-9Content10.00A-11Content10Content100CTC3.944CTC0.46CTC0.55CTC4.9591A-4Content30A-12Content70.00Content100CTC1.8CTC4.80CTC6.6092A-5Content30A-11Content70.00Content100CTC1.44CTC3.84CTC5.2893A-9Content30.00A-11Content70.00Content100CTC1.37CTC3.84CTC5.2194A-4Content40A-12Content 60.00 Content 100 CTC 2.4 CTC 4.11 CTC 6.5 195A-8 Content 40 A-12 Content 60.00 Content 100 CTC 2.11 6 CTC 4.11 CTC 6.23 96A-7 Content 80 A-10 Content 10.00 A-11 Content 10. Content 100 CTC 3.9 4 CTC 0.46 CTC 0.55 CTC 4.95 97A-6 Content 80 A-10 Content 20.00 Content 100 CTC 5.36 CTC 0.92 CTC 6.28 98A-11 Content 70.00 A-14 Content 30.00 Content 100 CTC 3.84 CTC 2.04 CTC 5.88
[0468]
[0469] Synthesis examples 99 to 100
[0470] Synthesis Example 99: Combination of a first diamine (code: A-2; content: 20 parts by weight; CTC: 1.1 ev), a second diamine (code: A-9; content: 20 parts by weight; CTC: 0.91 ev), a third diamine (code: A-12; content: 30 parts by weight; CTC: 2.06 ev), and a fourth diamine (code: A-13; content: 30 parts by weight; CTC: 2.10 ev)
[0471] Diamine total (content: 100 parts by weight; CTC: 6.17ev)
[0472]
[0473] Synthesis Example 100: Combination of a first diamine (code: A-4; content: 30 parts by weight; CTC: 1.8 ev), a second diamine (code: A-9; content: 10 parts by weight; CTC: 0.46 ev), a third diamine (code: A-12; content: 30 parts by weight; CTC: 2.06 ev), and a fourth diamine (code: A-14; content: 30 parts by weight; CTC: 2.04 ev).
[0474] Diamine total (content: 100 parts by weight; CTC: 6.35 ev)
[0475]
[0476] 1st diamine 2nd diamine 3rd diamine diamine Total synthesis example code content / CTC code content / CTC code content / CTC content / CTC 101A-9 content 30.00A-12 content 35.00A-13 content 35 content 100CTC 1.37CTC 2.40CTC 2.45CTC 6.21102A-1 content 30A-11 content 35.00A-14 content 35 content 100CTC 1.368CTC 1.92CTC 2.38CTC 5.67103A-6 content 20A-1 2 Content 40.00A-14 Content 40 Content 100 CTC 1.34 CTC 2.74 CTC 2.72 CTC 6.80 104A-7 Content 10A-11 Content 45.00A-13 Content 45 Content 100 CTC 0.49 3 CTC 2.47 CTC 3.15 CTC 6.11 105A-8 Content 10A-12 Content 45.00A-13 Content 45 Content 100 CTC 0.52 9 CTC 3.08 CTC 3.15 CTC 6.76
[0477]
[0478] Synthesis Examples 106 and 107
[0479] Synthesis Example 106: Combination of a first diamine (code: A-5; content: 10 parts by weight; CTC: 0.48 ev), a second diamine (code: A-9; content: 10 parts by weight; CTC: 0.46 ev), a third diamine (code: A-11; content: 40 parts by weight; CTC: 2.20 ev), and a fourth diamine (code: A-14; content: 40 parts by weight; CTC: 2.72 ev)
[0480] Diamine total (content: 100 parts by weight; CTC: 5.85 ev)
[0481]
[0482] Synthesis Example 107: Combination of a first diamine (code: A-6; content: 10 parts by weight; CTC: 0.67 ev), a second diamine (code: A-9; content: 10 parts by weight; CTC: 0.46 ev), a third diamine (code: A-12; content: 40 parts by weight; CTC: 2.74 ev), and a fourth diamine (code: A-14; content: 40 parts by weight; CTC: 2.72 ev)
[0483] Diamine total (content: 100 parts by weight; CTC: 6.59 ev)
[0484]
[0485] 1st diamine 2nd diamine 3rd diamine Diamine Total synthesis example code content / CTC code content / CTC code content / CTC content / CTC 108 A-7 content 10A-9 content 10.00 A-13 content 80 content 100 CTC 0.49 3 CTC 0.46 CTC 5.60 CTC 6.55 109 A-8 content 40 A-12 content 60.00 content 100 CTC 2.11 6 CTC 4.11 CTC 6. 23110A-2 Content 40A-12 Content 60.00 Content 100 CTC 2.2 CTC 4.11 CTC 6.3 1111A-8 Content 30A-12 Content 70.00 Content 100 CTC 1.587 CTC 4.80 CTC 6.38 112A-3 Content 30A-11 Content 70.00 Content 100 CTC 1.95 CTC 3.84 CTC 5.79
[0486]
[0487] Synthesis Examples 113 and 114
[0488] Synthesis Example 113: Combination of a first diamine (code: A-3; content: 10 parts by weight; CTC: 0.65 ev), a second diamine (code: A-9; content: 10 parts by weight; CTC: 0.46 ev), a third diamine (code: A-11; content: 40 parts by weight; CTC: 2.20 ev), and a fourth diamine (code: A-13; content: 40 parts by weight; CTC: 2.80 ev)
[0489] Diamine total (content: 100 parts by weight; CTC: 6.10ev)
[0490]
[0491] Synthesis Example 114: Combination of a first diamine (code: A-4; content: 10 parts by weight; CTC: 0.6 ev), a second diamine (code: A-9; content: 10 parts by weight; CTC: 0.46 ev), a third diamine (code: A-12; content: 40 parts by weight; CTC: 2.74 ev), and a fourth diamine (code: A-13; content: 40 parts by weight; CTC: 2.80 ev)
[0492] Diamine total (content: 100 parts by weight; CTC: 6.60 ev)
[0493]
[0494] 1st diamine 2nd diamine 3rd diamine diamine Total synthesis example code content / CTC code content / CTC code content / CTC content / CTC 1 15A-8 content 10A-9 content 10.00 A-14 content 80 content 100 CTC 0.529 CTC 0.46 CTC 5.44 CTC 6.42 116A-9 content 20.00 A-13 content 80.00 content 100 CTC 0.91 CTC 5.60 CTC 6.5 1 17A-6 content 50 A-8 content 50 content 100 CTC 3.35 CTC 2.64 5 CTC 6.00 118A-1 content 80 A-9 content 10.00 A-11 content 10 content 100 CTC 3.64 8 CTC 0.46 CTC 0.55 CT C4.65 119A-8 Content 80A-9 Content 10.00 A-12 Content 10 Content 100 CTC 4.232 CTC 0.46 CTC 0.69 CTC 5.37 120A-1 Content 40A-2 Content 40A-9 Content 20 Content 100 CTC 1.824 CTC 1.84 CTC 0.91 CTC 4.57 121A-8 Content 80A-10 Content 10.00 A-12 Content 10 Content 100 CTC 4.232 CTC 0.46 CTC 0.69 CTC 5.38 122A-1 Content 40A-2 Content 40A-10 Content 20 Content 100 CTC 1.824 CTC 1.84 CTC 0.92 CTC 4.58
[0495]
[0496] 1st diamine 2nd diamine 3rd diamine Diamine Total synthesis example code content / CTC code content / CTC code content / CTC content / CTC 123 A-9 content 14.00 A-11 content 86.00 content 100 CTC 0.64 CTC 4.72 CTC 5.36 124 A-1 content 40 A-9 content 20.00 A-11 content 40 content 100 CTC 1.82 4 CTC 0.91 CTC 2.20 CTC 4.93
[0497]
[0498] 1st diamine 2nd diamine 3rd diamine diamine Total comparative synthesis example code content / CTC code content / CTC code content / CTC content / CTC 1A-6 content 30A-14 content 70.00 content 100CTC 2.01CTC 4.76CTC 6.77 2A-12 content 50.00A-14 content 50.00 content 100CTC 3.43CTC 3.40CTC 6.83 3A-2 content 10A-12 content 70.00A-13 content 20 content 100CTC 0.55CTC 4.80CTC 1.40CTC 6.75 4A-12 content 30.00A-13 content 70.00 content 100CTC 2.06CTC 4.90CTC 6.96 5A-2 Content 20A-12 Content 60.00A-14 Content 20 Content 100 CTC 1.1 CTC 4.11 CTC 1.36 CTC 6.5 76A-2 Content 25A-12 Content 50.00A-13 Content 25 Content 100 CTC 1.37 5 CTC 3.43 CTC 1.75 CTC 6.5 5 7A-2 Content 40A-12 Content 20.00A-13 Content 40 Content 100 CTC 2.2 CTC 1.37 CTC 2.80 CTC 6.37 8A-2 Content 30A-12 Content 35.00A-14 Content 35 Content 100 CTC 1.65 CTC 2.40 CTC 2.38 CTC 6.4 39A-2 Content 10A -12 content 45.00A-14 content 45 content 100 CTC 0.55 CTC 3.08 CTC 3.06 CTC 6.69 10A-8 content 30A-12 content 30.00A-14 content 40 content 100 CTC 1.58 7 CTC 2.06 CTC 2.80 CTC 6.44 11A-2 content 20A-12 content 80 content 100 CTC 1.1 CTC 5.48 CTC 6.58 12A-2 content 70.00A-12 content 30.00 content 100 CTC 4.80 CTC 2.10 CTC 6.90 13A-12 content 40.00A-13 content 40.00A-14 content 20 content 100 CT C2.74CTC2.80CTC1.36CTC6.9014A-9Content 30.00A-14Content 70.00Content 100CTC1.37CTC4.76CTC6.1315A-6Content 40A-12Content 60.00Content 100CTC2.68CTC4.11CTC6.7916A-1Content 10A-11Content 45.00A-13Content 45Content 100CTC0.456CTC2.47CTC3.15CTC6.0817A-13Content 90.00A-14Content 10.00Content 100CTC6.30CTC0.68CTC6.9818A-12Content 10.00A-14 Content 90.00 Content 100 CTC 0.69 CTC 6.12 CTC 6.8 119A-12 Content 40.00 A-13 Content 60.00 Content 100 CTC 2.74 CTC 4.20 CTC 6.9 420A-6 Content 20A-13 Content 60.00 A-14 Content 20 Content 100 CTC 1.34 CTC 4.20 CTC 1.36 CTC 6.9 0 21A-6 Content 20A-12 Content 40 .00A-14Content 40Content 100CTC1.34CTC2.74CTC2.72CTC6.8022A-7Content 10A-13Content 80.00A-14Content 10Content 100CTC0.493CTC5.60CTC0.68CTC6.7723A-3Content 50A-12Content 25.00A-13Content 25Content 100CTC3.25CTC1.71CTC1.75CTC6.71.
[0499]
[0500] Comparative Synthesis Examples 24 to 26
[0501] Comparative Synthesis Example 24: Combination of a first diamine (type: A-6; content: 20 parts by weight; CTC: 1.34 ev), a second diamine (type: A-9; content: 10 parts by weight; CTC: 0.46 ev), a third diamine (type: A-12; content: 10 parts by weight; CTC: 0.69 ev), and a fourth diamine (type: A-13; content: 60 parts by weight; CTC: 4.20 ev).
[0502] Diamine total (content: 100 parts by weight; CTC: 6.68ev)
[0503]
[0504] Comparative Synthesis Example 25: Combination of a first diamine (type: A-6; content: 20 parts by weight; CTC: 1.34 ev), a second diamine (type: A-10; content: 10 parts by weight; CTC: 0.46 ev), a third diamine (type: A-12; content: 10 parts by weight; CTC: 0.69 ev), and a fourth diamine (type: A-13; content: 60 parts by weight; CTC: 4.20 ev).
[0505] Diamine total (content: 100 parts by weight; CTC: 6.69 ev)
[0506]
[0507] Comparative Synthesis Example 26: Combination of a first diamine (type: A-6; content: 25 parts by weight; CTC: 1.675 ev), a second diamine (type: A-12; content: 15 parts by weight; CTC: 1.03 ev), a third diamine (type: A-13; content: 30 parts by weight; CTC: 2.10 ev), and a fourth diamine (type: A-14; content: 30 parts by weight; CTC: 2.04 ev).
[0508] Diamine total (content: 100 parts by weight; CTC: 6.84ev)
[0509]
[0510] Synthesis of alkali-soluble polymer resins
[0511] For the above combination of diamine compounds (total diamine compounds), an acid anhydride compound and a capping compound were reacted as follows to produce an alkali-soluble polymer resin. In the tables below, the content of the acid anhydride compound and the content of the capping compound (parts by weight) are based on 100 parts by weight of the combination of diamine compounds (total diamine compounds).
[0512] Specifically, the above-described amine compound (a combination of diamine compounds) was added to gamma-butyrolactone and dissolved at 90°C. Thereafter, an acid anhydride compound was added according to the following recipe and stirred at 105°C for 4 hours. Thereafter, a capping compound was added according to the following recipe and reacted at 70°C for 2 hours, and then the temperature was raised to 150°C. Thereafter, water generated by the reaction was removed using a Dean-Stark extractor, and the reaction was terminated after stirring at 180°C for 4 hours, thereby synthesizing an alkali-soluble polymer resin.
[0513]
[0514] Acid anhydride compound (B) Capping compound (C) (B) + (C) Synthesis example Code content (parts by weight) / CTC (ev) Code content (parts by weight) / CTC (ev) Content (parts by weight) / CTC (ev) 1 B-4 content 80.00 C-4 content 40.00 content 120.00 CTC 3.95 CTC 1.53 CTC 5.48 2 B-5 content 50.00 C-1 content 100.00 content 150.00 CTC 2.24 CTC 3.04 CTC 5.28 3 B-7 content 70.00 C-3 content 60.00 content 130.00 CTC 0.05 CTC 2.12 CTC 2.18 4 B-8 content 80.00 C-4 content 40.00 content 120.0 0CTC3.95CTC1.53CTC5.495B-9Content 50.00C-1Content 100.00Content 150.00CTC1.52CTC3.04CTC4.566B-1Content 60.00C-2Content 80.00Content 140.00CTC1.96CTC2.66CTC4.627B-3Content 80.00C-4Content 40.00Content 120.00CTC4.00CTC1.53CTC5.538B-4Content 50.00C-1Content 100.00Content 150.00CTC1.97CTC3.04CTC5.019B-6Content 70.00C-3Content 60.00 Content 130.00CTC2.46CTC2.12CTC4.5810B-7Content 80.00C-4Content 40.00Content 120.00CTC3.20CTC1.53CTC4.7311B-8Content 50.00C-1Content 100.00Content 150.00CTC1.98CTC3.04CTC5.0212B-9Content 60.00C-2Content 80.00Content 140.00CTC1.95CTC2.66CTC4.6113B-1Content 70.00C-3Content 60.00Content 130.00CTC2.46CTC2.12CTC4.5814B-3Content 50. 00C-1 Content 100.00 Content 150.00 CTC 2.00 CTC 3.04 CTC 5.04 15B-4 Content 60.00 C-2 Content 80.00 Content 140.00 CTC 2.54 CTC 2.66 CTC 5.19 16B-6 Content 80.00 C-4 Content 40.00 Content 120.00 CTC 3.05 CTC 1.53 CTC 4.58 17B-7 Content 50.00 C-1 Content 100.00 Content 150.00 CTC 1.60 CTC 3.04 CTC 4.64 18B-8 Content 60.00 C-2 Content 80.00 Content 140.00 CTC 2.54 CTC 2.66 CTC 5.2019B-9 Content 70.00C-3 Content 60.00Content 130.00CTC2.46CTC2.12CTC4.5820B-1 Content 80.00C-4 Content 40.00Content 120.00CTC3.05CTC1.53CTC4.5821B-2 Content 50.00C-1 Content 100.00Content 150.00CTC1.98CTC3.04CTC5.0222B-3 Content 60C-2 Content 80Content 140CTC2.57CTC2.66CTC5.2323B-1 Content 50C-1 Content 100Content 150CTC1.52CTC3.04CTC4.5624B-2 Content 60 C-2 content 80 content 140 CTC 2.55 CTC 2.66 CTC 5.2 125 B-3 content 70 C-3 content 60 content 130 CTC 3.23 CTC 2.12 CTC 5.35 26 B-4 content 80 C-4 content 40 content 120 CTC 3.95 CTC 1.53 CTC 5.48 27 B-5 content 50 C-1 content 50 content 100 CTC 3.36 CTC 2.28 CTC 5.64 28 B-6 content 60 C-2 content 40 content 100 CTC 2.74 CTC 1.86 CTC 4.60 29 B-7 content 70 C-3 content 30 content 100 CTC 3.36 CTC 1.38 CTC 4.74 30 B-9 content 50C-1 Content 100 Content 150CTC 1.52CTC 3.04CTC 4.56 31B-1 Content 60C-2 Content 80 Content 140CTC 1.96CTC 2.66CTC 4.62 32B-2 Content 70C-3 Content 60 Content 130CTC 3.20CTC 2.12CTC 5.33 33B-3 Content 80C-4 Content 40 Content 120CTC 4.00CTC 1.53CTC 5.53 34B-4 Content 50C-1 Content 50 Content 100CTC 2.96CTC 2.28CTC 5.24 35B-6 Content 70C-3 Content 30 Content 100CTC 3.20CTC 1.38CTC 4.58 36B- 7 Content 80C-4 Content 20 Content 100CTC3.84CTC0.92CTC4.7637B-8 Content 50C-1 Content 100 Content 150CTC1.98CTC3.04CTC5.0238B-9 Content 60C-2 Content 80 Content 140CTC1.95CTC2.66CTC4.6139B-1 Content 50C-3 Content 60 Content 110CTC2.08CTC2.51CTC4.5940B-2 Content 60.00C-4 Content 40.00Content 100.00CTC3.57CTC1.84CTC5.4141B-3 Content 70.00C-1 Content 50.00Content 120.00CTC3.50CTC1.90CTC5.4042B-4Content 80.00C-2Content 40.00Content 120.00CTC3.95CTC1.55CTC5.5043B-6Content 60.00C-4Content 20.00Content 80.00CTC3.43CTC1.15CTC4.5844B-7Content 70.00C-1Content 100.00Content 170.00CTC1.98CTC2.68CTC4.6645B-8Content 80C-2Content 80Content 160CTC2.97CTC2.33CTC5.29 46B-9 Content 50C-3 Content 60 Content 110CTC 2.07CTC 2.51CTC 4.58 47B-1 Content 60C-4 Content 40 Content 100CTC 2.74CTC 1.84CTC 4.58 48B-2 Content 70C-1 Content 50 Content 120CTC 3.47CTC 1.90CTC 5.37 49B-3 Content 80C-2 Content 40 Content 120CTC 4.00CTC 1.55CTC 5.55 50B-6 Content 70C-1 Content 100 Content 170CTC 1.88CTC 2.68CTC 4.56.
[0515]
[0516] Acid anhydride compound (B) Capping compound (C) (B) + (C) Synthesis example Code content (parts by weight) / CTC (ev) Code content (parts by weight) / CTC (ev) Content (parts by weight) / CTC (ev) 51 B-7 content 80 C-2 content 80 content 160 CTC 2.40 CTC 2.33 CTC 4.73 52 B-8 content 50.00 C-3 content 60.00 content 110.00 CTC 2.70 CTC 2.5 1 CTC 5.20 53 B-9 content 60.00 C-4 content 40.00 content 100.00 CTC 2.74 CTC 1.84 CTC 4.58 54 B-1 content 50.00 C-1 content 50.00 content 100.00 CTC 2.29 CTC2.28CTC4.5755B-2Content 60.00C-2Content 40.00Content 100.00CTC3.57CTC1.86CTC5.4356B-3Content 70.00C-3Content 30.00Content 100.00CTC4.20CTC1.38CTC5.5857B-4Content 80.00C-4Content 20.00Content 100.00CTC4.74CTC0.92CTC5.6658B-4Content 80.00C-4Content 20.00Content 100.00CTC4.74CTC0.92CTC5.6659B-6Content 60.00C-2Content 40.00Content 100. 00CTC2.74CTC1.86CTC4.6060B-9Content 50.00C-1Content 50.00Content 100.00CTC2.28CTC2.28CTC4.5661B-1Content 60.00C-2Content 40.00Content 100.00CTC2.74CTC1.86CTC4.6062B-4Content 50.00C-1Content 50.00Content 100.00CTC2.96CTC2.28CTC5.2463B-6Content 70.00C-3Content 45.00Content 115.00CTC2.78CTC1.80CTC4.5864B-8Content 50.00C-1Content 75 .00Content 125.00CTC2.37CTC2.74CTC5.1165B-9Content 60.00C-2Content 60.00Content 120.00CTC2.28CTC2.33CTC4.6166B-1Content 70.00C-3Content 45.00Content 115.00CTC2.78CTC1.80CTC4.5867B-3Content 50.00C-1Content 75.00Content 125.00CTC2.40CTC2.74CTC5.1468B-4Content 60.00C-2Content 60.00Content 120.00CTC2.96CTC2.33CTC5.2969B-6Content 70.00C-1 Content 100.00 Content 170.00 CTC 1.88 CTC 2.68 CTC 4.5 6 70B-7 Content 80.00 C-2 Content 80.00 Content 160.00 CTC 2.40 CTC 2.33 CTC 4.7 3 71B-8 Content 50.00 C-3 Content 60.00 Content 110.00 CTC 2.70 CTC 2.5 1 CTC 5.2 0 72B-9 Content 60.00 C-4 Content 40.00 Content 100.00 CTC 2.74 CTC 1.84 CTC 4.5 8 73B-1 Content 50.00 C-1 Content 50.00 Content 100.00 CTC 2.29 CTC 2.28 CTC 4.5 7 4B- 2 Content 60.00 C-2 Content 40.00 Content 100.00 CTC 3.57 CTC 1.86 CTC 5.43 75 B-4 Content 80.00 C-4 Content 20.00 Content 100.00 CTC 4.74 CTC 0.92 CTC 5.66 76 B-1 Content 100.00 Content 100.00 CTC 4.57 CTC 4.57 77 B-9 Content 60.00 C-1 Content 80.00 Content 140.00 CTC 1.95 CTC 2.61 CTC 4.56 78 B-5 Content 50.00 C-1 Content 100.00 Content 150.00 CTC 2.24 CTC 3.04 CTC 5.28 79 B-7 Content 70.00 C- 3 Content 60.00 Content 130.00 CTC 2.58 CTC 2.12 CTC 4.7 180 B-9 Content 50.00 C-1 Content 50.00 Content 100.00 CTC 2.28 CTC 2.28 CTC 4.5 681 B-4 Content 50.00 C-1 Content 100.00 Content 150.00 CTC 1.97 CTC 3.04 CTC 5.0 182 B-3 Content 120.00 C-5 Content 40.00 Content 160.00 CTC 4.50 CTC 1.14 CTC 5.6 483 B-4 Content 130.00 C-5 Content 60.00 Content 190.00 CTC 4.05 CTC 1.44 CTC 5.4 984 B-6 Amount 110.00C-5Content 20.00Content 130.00CTC3.87CTC0.70CTC4.5785B-7Content 120.00C-5Content 40.00Content 160.00CTC3.60CTC1.14CTC4.7486B-8Content 130.00C-5Content 60.00Content 190.00CTC4.06CTC1.44CTC5.5087B-9Content 140.00C-5Content 80.00Content 220.00CTC2.90CTC1.66CTC4.5688B-6Content 70.00C-3Content 60.00Content 130.00CTC2.46CTC2.12CTC4.5889B-8 Content 80.00C-4 Content 20.00Content 100.00CTC4.74CTC0.92CTC5.6690B-5 Content 60.00C-4 Content 20.00Content 80.00CTC5.03CTC1.15CTC6.1891B-7 Content 70.00C-3 Content 30.00Content 100.00CTC3.36CTC1.38CTC4.7 492B-8 Content 80.00C-4 Content 20.00Content 100.00CTC4.74CTC0.92CTC5.6693B-3 Content 80.00C-4 Content 20.00Content 100.00CTC4.80CTC0.92CTC5.7294B-7 Content 80.00C-4 Content 30.00Content 110.00CTC3.49CTC1.25CTC4.75 95B-2 Content 80.00C-4 Content 30.00Content 110.00CTC4.33CTC1.25CTC5.5896B-5 Content 60.00C-4 Content 20.00Content 80.00CTC5.03CTC1.15CTC6.1897B-3 Content 70.00C-3 Content 30.00Content 100.00CTC4.20CTC1.38CTC5.589 8B-3 Content 70.00C-3 Content 60.00Content 130.00CTC3.23CTC2.12CTC5.3599B-6 Content 60.00C-2 Content 80.00Content 140.00CTC1.96CTC2.66CTC4.62100B-8 Content 80.00C-4 Content 40.00Content 120.00CTC3.95CTC1.53CTC5.49.
[0517]
[0518] Acid anhydride compound (B) Capping compound (C) (B) + (C) Synthesis example Code content (parts by weight) / CTC (ev) Code content (parts by weight) / CTC (ev) Content (parts by weight) / CTC (ev) 101 B-1 content 60.00 C-2 content 40.00 content 100.00 CTC 2.74 CTC 1.86 CTC 4.60 102 B-2 content 70.00 C-3 content 30.00 content 100.00 CTC 4.17 CTC 1.38 CTC 5.55 103 B-7 content 80.00 C-4 content 40.00 content 120.00 CTC 3.20 CTC 1.53 CTC 4.73 104 B-8 content 50.00 C-1 content 50.00 Amount 100.00 CTC2.97 CTC2.28 CTC5.25 105B-9 Content 60.00 C-2 Content 40.00 Content 100.00 CTC2.74 CTC1.86 CTC4.60 106B-5 Content 50.00 C-3 Content 60.00 Content 110.00 CTC3.05 CTC2.51 CTC5.56 107B-6 Content 60.00 C-4 Content 40.00 Content 100.00 CTC2.74 CTC1.84 CTC4.58 108B-7 Content 70.00 C-1 Content 50.00 Content 120.00 CTC2.80 CTC1.90 CTC4.70 109B-2 Content 80 .00C-4 content 40.00 content 120.00CTC 3.97CTC 1.53CTC 5.50110B-5 content 60.00C-2 content 80.00 content 140.00CTC 2.88CTC 2.66CTC 5.53111B-2 content 70.00C-3 content 60.00 content 130.00CTC 3.20CTC 2.12CTC 5.33112B-6 content 60.00C-2 content 80.00 content 140.00CTC 2.51CTC 2.66CTC 5.17113B-3 content 70.00C-1 content 100.00 content 170.00CTC 2.47CTC 2.68CT C5.15114B-4Content 80.00C-2Content 80.00Content 160.00CTC2.96CTC2.33CTC5.29115B-8Content 80.00C-2Content 40.00Content 120.00CTC3.95CTC1.55CTC5.50116B-2Content 70.00C-1Content 100.00Content 170.00CTC2.45CTC2.68CTC5.13117B-10Content 70.00C-1Content 100.00Content 170.00CTC2.26CTC2.68CTC4.95118B-10Content 80.00C-2Content 80.00Content 160.00CTC2.75CTC2.33CTC5.08119B-10Content 70.00C-1Content 100.00Content 170.00CTC2.26CTC2.68CTC4.95120B-10Content 80.00C-2Content 80.00Content 160.00CTC2.75CTC2.33CTC5.08121B-10Content 70.00C-1Content 100.00Content 170.00CTC2.26CTC2.68CTC4.95122B-10Content 80.00C-2Content 80.00Content 160.00CTC2.75CTC2.33CTC5.08.
[0519]
[0520] Acid anhydride compound (B) Capping compound (C) (B) + (C) 1st 2nd diamine Total composition code content / CTC code content / CTC code content / CTC content / CTC 123 B-2 content 42 B-9 content 42.00 C-3 content 32 content 116 CTC 2.15 CTC 1.65 CTC 1.27 CTC 5.07 124 B-2 content 32 B-9 content 32.00 C-3 content 36 content 100 CTC 1.90 CTC 1.46 CTC 1.66 CTC 5.02
[0521]
[0522] Acid anhydride compound (B) capping compound (C) (B) + (C) primary secondary diamine Total Comparative Synthesis Example Code Content / CTC Code Content / CTC Code Content / CTC Content / CTC1B-3 Content 10B-10 Content 40.00C-2 Content 30 Content 80CTC0.75CTC2.75CTC1.74CTC5.242B-4 Content 25B-10 Content 25.00C-2 Content 30 Content 80CTC1.85CTC1.72CTC1.74CTC5.313B-5 Content 70C-2 Content 60 Content 130CTC3.61CTC2.15CTC5.764B-5 Content 30B-10 Content 30.00C-2 Content 40 Content 100CTC2.01CTC1.65CT C1.86CTC5.525B-5content35B-10content15.00C-4content50content100CTC2.35CTC0.83CTC2.30CTC5.476B-2content40B-10content30.00C-3content30content100CTC2.38CTC1.65CTC1.38CTC5.417B-5content35B-10content25.00C-2content60content120CTC1.96CTC1.15CTC2.33CTC5.438B-5content30B-10content40.00C-2content45content115CTC1.75CTC1.91CTC1.82 CTC5.489B-5Content50B-10Content50Content100CTC3.36CTC2.75CTC6.1110B-3Content80C-4Content20Content100CTC4.80CTC0.92CTC5.7211B-2Content60C-4Content20Content80CTC4.46CTC1.15CTC5.6112B-2Content70B-10Content40.00C-5Content20Content130CTC3.20CTC1.69CTC0.70CTC5.6013B-5Content50B-10Content90C-5Content80Content220CTC1.53CTC2.25CTC1. 66CTC5.4314B-2Content 30B-10Content 30C-2Content 80Content 140CTC1.28CTC1.18CTC2.66CTC5.1115B-5Content 30B-10Content 30C-2Content 80Content 140CTC1.44CTC1.18CTC2.66CTC5.2716B-10Content 80C-2Content 80Content 80CTC2.75CTC3.72CTC3.7217B-10Content 140C-5Content 60Content 200CTC3.85CTC1.37CTC5.2218B-5Content 50C-2Content 30Content 80CTC4.19CTC1.74CTC5.9419B-10Content 70C-3Content 30Content 100CTC3.85CTC1.38CTC5.2320B-10Content 60C-2Content 20Content 80CTC4.13CTC1.16CTC5.2921B-5Content 50B-10Content 50Content 100CTC3.36CTC2.75CTC6.1122B-10Content 100Content 100CTC5.50CTC5 .5023B-10Content 80C-2Content 40Content 120CTC3.67CTC1.55CTC5.2224B-5Content 30B-10Content 40.00C-1Content 50Content 120CTC1.68CTC1.83CTC1.90CTC5.4125B-2Content 40B-10Content 100C-5Content 50Content 190CTC1.25CTC2.89CTC1.20CTC5.35.
[0523]
[0524] Comparative Synthesis Example 26: Combination of a first acid anhydride compound (type: B-5; content: 20 parts by weight; CTC: 1.68 ev), a second acid anhydride compound (type: B-10; content: 30 parts by weight; CTC: 2.06 ev), a first capping compound (type: C-2; content: 20 parts by weight; CTC: 1.16 ev), and a second capping compound (type: C-3; content: 10 parts by weight; CTC: 0.58 ev)
[0525] Total amount of acid anhydride compound and capping compound (content: 80 parts by weight; CTC: 5.48 ev)
[0526]
[0527] Physical property analysis of alkali-soluble polymer resins
[0528] The CTC value (ev) and imidization degree of the alkali-soluble polymer resins manufactured in the above synthetic examples and comparative synthetic examples were calculated and shown in the tables below.
[0529] In Tables 21 to 24 below, the CTC calculation values are derived using the above formula 1-1.
[0530] [Formula 1-1]
[0531] CTC(ev) of alkali-soluble polymer resin = (A+B) / 2
[0532] In addition, in Tables 21 to 24 below, the degree of imidization means the content of the repeating unit represented by the chemical formula B based on 100 mol% of the total of the repeating unit represented by the chemical formula A and the repeating unit represented by the chemical formula B in the alkali-soluble polymer resin.
[0533] At this time, the mol% of the repeating unit contained in the alkali-soluble polymer resin can be calculated by confirming the conversion rate through comparison of the -CNC- peak of the imide bond in the FT-IR measurement results. Specifically, the alkali-soluble polymer resin was coated on a glass surface, and heated at a temperature of 120 °C for 120 seconds to obtain a sample (a). In addition, the alkali-soluble polymer resin was coated on a glass surface, and heated at a temperature of 120 °C for 120 seconds, and then heated at a temperature of 350 °C for 60 minutes to obtain a sample (b).
[0534] FT-IR measurements are performed on the obtained samples (a) and (b). At this time, C=C (Aromatic, 1510 cm -1 ), CNC(1370 cm -1 ) was measured. Afterwards, the degree of imidization (CNC / C=C) was compared to calculate the molar % (degree of imidization) of the repeating unit represented by chemical formula B.
[0535]
[0536] Synthesis Example CTC Calculation (eV) Degree of imidization (mol%) 15.3590 25.8680 34.3985 45.3870 55.6885 64.9795 75.3760 85.0755 95.245 1105.6270 115.1275 125.7065 134.925 2145.0880 155.1190 165.2995 175.5385 185.1780 195.6885 204.9070 215.5580 225.1275 234.7565 245.5860 255. 6370265.8475275.3355285.4795294.9190304.7251315.1590325.4980335.6675345.0375354.7465365.0370375.0760385.2651395.0465405.4770415.5880425.5790434.7295445.3390454.9780465.0685475.3975485.6660495.2055504.9775
[0537]
[0538] Synthesis Example CTC Calculation (eV) Degree of imidization (mol%) 514.8370525.2685535.3485545.1490555.0990565.9355575.2660585.4365595.2080605.6880614.9685625.1890635.2480645.1680655.7075664.9295675.1380685.1685694.9785704.8380715.2680725.3580735.1495745.1080 755.2680764.9275775.2580785.4285795.2090805.1695815.6580825.3885835.2655845.2365855.6370865.3660875.6880885.2355895.7265905.5785915.6780925.4790935.4695945.6380955.9085965.5775975.9370985.6265995.39601005.9255
[0539]
[0540] Synthesis Example CTC Calculation (eV) Degree of imidization (mol%) 1015.4 180 1025.6 185 1035.7790 1045.6895 1055.6880 1065.7180 1075.5885 1085.6280 1095.8675 1105.9275 1115.8580 1125.4870 1135.6365 1145.9460 1155.9680 1165.8255 1175.4755 1184.8680 1195.1685 1204.8275 1215.1670 1224.8365 1235.2280 1244.9780
[0541]
[0542] Comparative Synthesis Example CTC Calculation (eV) Degree of Imidation (mol%) 16.0 150 26.08 40 36.00 45 46.29 40 56.18 30 66.11 50 76.18 45 86.00 45 96.02 40 106.24 30 116.07 45 126.15 45 136.02 50 146.01 50 156.00 30 166.09 40 176.30 35 186.00 40 196.01 50 206.11 45 216.05 50 226.5 245 236.20 50 246.01 40 256.09 30 266.03 35
[0543]
[0544] Example (Preparation of positive photosensitive resin composition)
[0545] Esterified quinonediazide compounds
[0546] An esterified quinonediazide compound represented by the following chemical formula 3-A1 was prepared.
[0547] [Chemical Formula 3-A1]
[0548]
[0549] At this time, the chemical formula 3-A1 includes a reaction product of a naphthoquinonediazide compound and a phenolic compound disclosed in Table 25 below. In addition, “A” of the chemical formula 3-A1 corresponds to the structure (moiety) of the phenolic compound described in Table 25 below, and the oxygen of the “AO” bond corresponds to the oxygen of the phenolic hydroxy group of the phenolic compound.
[0550]
[0551] Code (code) Phenolic compound structure (3-1) <Compound 3-1> (3-2)<Compound 3-2>
[0552] In the case of the esterified quinonediazide compound corresponding to the reaction product of the phenol compound of Code 3-1 of Table 25 and the naphthoquinonediazide compound, 2 mol of the naphthoquinonediazide compound was combined based on 1 mol of the phenol compound. In the case of the esterified quinonediazide compound corresponding to the reaction product of the phenol compound of Code 3-2 of Table 25 and the naphthoquinonediazide compound, 2 mol of the naphthoquinonediazide compound was combined based on 1 mol of the phenol compound.
[0553]
[0554] crosslinking agent
[0555] The following compounds were prepared as crosslinking agents containing a phenol group.
[0556]
[0557] Code structure (4-1) <Chemical formula 4-9> R 4a , R 4b : -CH2OCH3(4-2)<Chemical Formula 4-1> R 4a , R 4b : -CH2OCH3(4-3)<Chemical formula 4-2> R 4a , R 4b : -CH2OCH3(4-4)<Chemical formula 4-3> R 4a , R 4b : -CH2OCH3(4-5)<Chemical Formula 4-10> R 4a , R 4b , R 4c , R 4d : -CH2OCH3(4-6)<Chemical Formula 4-11> R 4a , R 4b , R4c , R 4d : -CH2OCH3(4-7)<Chemical Formula 4-16> R 4a , R 4b , R 4c , R 4d , R 4e , R 4f : -CH2OCH3(4-8)<Chemical Formula 4-17> R 4a , R 4b , R 4c , R 4d , R 4e , R 4f : -CH2OCH3
[0558]
[0559] For the alkali-soluble polymer resin (polyimide polymer) manufactured in the above synthesis example, a quinonediazide compound and a cross-linking agent were mixed as follows to manufacture a positive photosensitive resin composition. The content (parts by weight) of the quinonediazide compound and the cross-linking agent is based on 100 parts by weight of the alkali-soluble polymer resin (polyimide polymer).
[0560]
[0561]
[0562]
[0563]
[0564]
[0565] Comparative example (manufacture of positive photosensitive resin composition)
[0566] For the alkali-soluble polymer resin (polyimide polymer) manufactured in the above synthesis example, a quinonediazide compound and a cross-linking agent were mixed as follows to manufacture a positive photosensitive resin composition. The content (parts by weight) of the quinonediazide compound and the cross-linking agent is based on 100 parts by weight of the alkali-soluble polymer resin (polyimide polymer).
[0567]
[0568] Polyimide polymer quinone diazide compound crosslinker Comparative example Type Content code Content code Content structure Content Total content 1 Comparative synthesis example 1 1003-1254-31--12 Comparative synthesis example 2 1003-2254-43--33 Comparative synthesis example 3 1003-1254-55--54 Comparative synthesis example 4 1003-2254-67--75 Comparative synthesis example 5 1003-1254-724-1246 Comparative synthesis example 6 1003-2254-834-2367 Comparative synthesis example 71 003-1254-1154-310258Comparative Synthesis Example 81003-2254-2154-415309Comparative Synthesis Example 91003-1254-3104-5152510Comparative Synthesis Example 101003-2254-425--2511Comparative Synthesis Example 111003-1254-530--3012Comparative Synthesis Example 121003-2254-61--113Comparative Synthesis Example 131003-1254-73-- 314Comparative Synthesis Example 141003-2254-85--515Comparative Synthesis Example 151003-1254-17--716Comparative Synthesis Example 161003-2254-224-82417Comparative Synthesis Example 171003-1254-334-73618Comparative Synthesis Example 181003-2254-4154-6102519Comparative Synthesis Example 191003-1254-5154-5153020Comparative Synthesis Example 201003 -2254-6104-4152521Comparative synthesis example 211003-1254-725--2522Comparative synthesis example 221003-2254-825--2523Comparative synthesis example 231003-1254-125--2524Comparative synthesis example 241003-2254-230--3025Comparative synthesis example 251003-1254-330--3026Comparative synthesis example 261003-2254-430--30
[0569]
[0570] Experimental example
[0571] For the positive photosensitive resin compositions manufactured in the above examples and comparative examples, the fluorine content, sensitivity, film retention rate, adhesive strength, chemical resistance, heat resistance, solar resistance, hygroscopicity, operating reliability, and bending characteristics were measured by the following methods. The measured results are shown in Tables 30 to 33 below.
[0572]
[0573] Fluorine content measurement
[0574] The content of fluorine contained in the photosensitive resin composition was measured using combustion ion chromatography (CIC).
[0575]
[0576] Sensitivity measurement
[0577] A substrate coated with a photosensitive resin composition was irradiated with ultraviolet rays having an intensity of 20 mW / cm2 in a broadband using a predetermined pattern mask at a standard dose for forming a 5 μm contact hole CD, and then developed with an aqueous solution of 2.38 parts by weight of tetramethylammonium hydroxide at 23°C for 1 minute and washed with ultrapure water for 1 minute. Thereafter, the film was cured in an oven at 250°C for 60 minutes to obtain a pattern film having a contact hole CD of 7 μm. The sensitivity was 40 to 150 mJ / cm. 2 If this is satisfied with the appropriate result value, it is marked as O.
[0578]
[0579] Measurement of residual film ratio
[0580] The residual film ratio of the above-mentioned manufactured substrate was measured by comparing the initial coating thickness and the final thickness after all processes were performed. If the ratio of the final thickness to the initial thickness was 60% or more, it was marked as O, and if it was less than 60%, it was marked as X.
[0581]
[0582] Adhesion measurement
[0583] A pattern film was formed in the same manner as in the sensitivity measurement above, but the adhesive strength according to the baking temperature was compared based on a case where the line width and slit width were 10 ㎛ and 1:1. At this time, a case where the adhesive strength was secured at a prebake of 90 ℃ to 100 ℃ was marked as O, and a case where the adhesive strength was secured at a prebake of 120 ℃ or higher or not was marked as X.
[0584]
[0585] Chemical resistance measurement
[0586] The above-mentioned manufactured substrate was immersed in an evaluation solvent (Stripper) at 25°C for 120 seconds, and the change rate of the cured film thickness before and after immersion was measured. 0 Å or more and less than 150 Å was marked as ◎, 150 Å or more and less than 300 Å was marked as ○, 300 Å or more and less than 600 Å was marked as △, and 600 Å or more was marked as X (evaluation solvent was propylene glycol methyl ether: propylene glycol methyl ether acetate = 7:3 molar ratio).
[0587]
[0588] Heat resistance measurement
[0589] For the above sensitivity evaluation, the organic film portion of the manufactured substrate (up to the curing process completion) was recovered and evaluated using a TGA (Thermogravimetric Analyzer) at 50 to 500°C, 10°C / min. If the standard temperature for weight loss (5% of weight loss) was 350°C or higher, it was marked as ◎, if it was 300°C or higher but less than 350°C, it was marked as ○, and if it was less than 300°C, it was marked as X.
[0590]
[0591] Solar resistance measurement
[0592] In the same way as the sensitivity measurement above, a pattern film is formed on a patterned ITO substrate, and EL is deposited. Al is deposited on top as a cathode electrode, and an encapsulation process is performed. After irradiating 2100 J of exposure dose 10 times using a xenon lamp solar simulator, the time (T97) for a 3% luminance drop in the on state is evaluated. If it is secured for 1000 hours or more, it is marked with ○, and if it is secured for less than 1000 hours, it is marked with X.
[0593]
[0594] Hygroscopicity measurement
[0595] For the above sensitivity evaluation, the manufactured substrate was purified in a constant temperature and humidity oven at 85°C and 85% RH for 240 hours, and then the hygroscopicity was evaluated based on the change in film thickness before and after being placed in the oven. If the thickness change rate was less than 300 Å, it was marked as ◎, if it was 300 Å or more but less than 600 Å, it was marked as ○, and if it was 600 Å or more, it was marked as X.
[0596]
[0597] Drive reliability measurement
[0598] A pattern film can be formed using the same method as in the above sensitivity measurement.
[0599] Fig. 1 is a drawing showing forming a pattern film on an ITO substrate on which a pattern has been formed and depositing EL. Specifically, 10 in Fig. 1 represents a source / drain (Ti / Al / Ti), 20 represents an organic film, 30 represents an anode (ITO / Ag / ITO), and 40 represents a pixel define layer (PDL).
[0600] As shown in Fig. 1, Al is deposited as a cathode on the upper side, and an encapsulation process is performed. The time (T97) for a 3% luminance drop in the device ON state at 85 ℃ and 85% RH was evaluated. If it is secured for 1000 hours or more, it is marked with ◎, if it is less than 1000 hours but more than 950 hours, it is marked with ○, and if it is less than 950 hours, it is marked with X.
[0601]
[0602] Measurement of bending characteristics
[0603] A 100 ㎛ thick polyimide (PI) film was coated with a material in a thickness of 3 ㎛ and folded 200,000 times with a radius of curvature of 1R. If numerous cracks were observed in the folding portion, it was marked as X, and if no cracks were observed, it was marked as O.
[0604]
[0605] Fluorine Content (ppm) Sensitivity Residual film rate Adhesion Chemical resistance Example 16, 569○○○○ Example 25, 781○○○○ Example 36, 283○○○○ Example 46, 569○○○○ Example 55, 781○○○○ Example 66, 021○○○○ Example 76, 569○○○○ Example 84, 955○○○○ Example 95, 386○○○○ Example 105, 630○○○○ Example 114, 955○○○○ Example 125, 161○○○○ Example 135, 386○○○○ Example 144, 955○○○○ Example 154, 301○○○○ Example 164, 692○○○○ Example 174, 129○○ ○○Example 184,301○○○○Example 194,488○○○○Example 204,692○○○○Example 214,129○○○○Example 224,301○○○○Example 233,303○○○○Example 243,441○○○○Example 253,590○○○○Example 263,75 4○○○○Example 274,129○○○○Example 284,129○○○○Example 294,129○○○○Example 302,890○○○○Example 313,011○○○○Example 322,244○○○○Example 332,346○○○○Example 341,548○○○○Example 351 ,548○○○○Embodiment 361,548○○○○Embodiment 370○○○○Embodiment 380○○○○Embodiment 390○○○○Embodiment 400○○○○Embodiment 410○○○○Embodiment 420○○○○Embodiment 430○○○○Embodiment 440○○○○Embodiment 45794○○○○Embodiment 46983○ ○○○Example 471,032○○○○Example 48938○○○○Example 49938○○○○Example 50765○○○○Example 510○○○○Example 520○○○○Example 530○○○○Example 540○○○○Example 550○○○○Example 560○○○○Example 570○○○○Example 587,226○○○○Example 597,226○○○○Example 607,226○○○○Example 617,226○○○○Example 626,194○○○○Example 635,761○○○○Example 645,505○○○○Example 655,630○○○○Example 665,761○ ○○○Example 675,505○○○○Example 684,692○○○○Example 69765○○○○Example 700○○○○Example 710○○○○Example 720○○○○Example 730○○○○Example 740○○○○Example 750○○○○Example 766,194○○○○Example 778,602○○○○Embodiment 784,955○○○○Embodiment 795,386○○○○Embodiment 807,226○○○○Embodiment 816,606○○○○Embodiment 824,764○○○○Embodiment 833,559○○○○Embodiment 845,386○○○○Embodiment 854,764○○○○Embodiment 864,271○○○○Embodiment 873,871○○○○Embodiment 887,181○○○○Embodiment 894,129 ○○○○Example 901,147○○○○Example 917,226○○○○Example 927,226○○○○Example 937,226○○○○Example 945,899○○○○Example 955,899○○○○Example 961,147○○○○Example 970○○○○Example 988,976○○○○Example 995,161○○○○Example 1005,630○○○○Example 1017,226○○○○Example Example 1027, 226○○○○Embodiment 1037, 507○○○○Embodiment 1049, 290○○○○Embodiment 1059, 290○○○○Embodiment 1067, 865○○○○Embodiment 1078, 258○○○○Embodiment 1087, 507○○○○Embodiment 1095, 630○○○○Embodiment 1105, 161○○○○Embodiment 1116, 283○○○○Embodiment 1126, 021○○○○Embodiment 1136, 1 17○○○○Embodiment 1146, 352○○○○Embodiment 1157, 507○○○○Embodiment 1166, 117○○○○Embodiment 1175, 352○○○○Embodiment 1187, 146○○○○Embodiment 1196, 117○○○○Embodiment 1206, 352○○○○Embodiment 1216, 117○○○○Embodiment 1226, 352○○○○Embodiment 1238, 220○○○○Embodiment 1243, 380○○○○,
[0606]
[0607]
[0608]
[0609] Classification Fluorine content (ppm) Sensitivity Residual film rate Adhesion Chemical resistance Comparative example 112,616○○○X Comparative example 211,469○○○X Comparative example 310,896○○○X Comparative example 48,976○○○X Comparative example 510,839○○○X Comparative example 610,839○○○X Comparative example 713,419○○○X Comparative example 89,853○○○X Comparative example 911,043○○○X Comparative example 1011,355○○○X Comparative example 117,226○○○X Comparative example 1210,323○○○X Comparative example 139,874○ ○○X Comparative Example 1410,968○○○X Comparative Example 1511,183○○○X Comparative Example 1611,183○○○X Comparative Example 1711,911○○○X Comparative Example 1813,763○○○X Comparative Example 1910,323○○○X Comparative Example 2017,548○○○X Comparative Example 2118,351○○○X Comparative Example 2215,484○○○X Comparative Example 2318,581○○○X Comparative Example 2415,015○○○X Comparative Example 2512,199○○○X Comparative Example 2610,678○○○X
[0610]
[0611] ClassificationHeat resistanceSolar resistanceHygroscopicityOperation reliabilityBending characteristicsComparison example 1XXXX○Comparison example 2XXXX○Comparison example 3XXXX○Comparison example 4XXXX○Comparison example 5XXXX○Comparison example 6XXXX○Comparison example 7XXXX○Comparison example 8XXXX○Comparison example 9XXXX○Comparison example 10XXXX○Comparison example 11XXXX○Comparison example 12XXXX○Comparison example 13XXXX○Comparison example 14XXXX○Comparison example 15XXXX○Comparison example 16XXXX○Comparison example 17XXXX○Comparison example 18XXXX○Comparison example 19XXXX○Comparison example 20XXXX○Comparison example 21XXXX○Comparison example 22XXXX○Comparison example 23XXXX○Comparison example 24XXXX○Comparison example 25XXXX○Comparison example 26XXXX○
[0612]
[0613] Referring to Tables 30 to 33 above, it was confirmed that the positive photosensitive resin compositions manufactured in Examples 1 to 124 had excellent sensitivity, film retention rate, adhesive strength, chemical resistance, heat resistance, solar resistance, hygroscopicity, operating reliability, and bending characteristics.
[0614] On the other hand, in the case of Comparative Examples 1 to 26, it was confirmed that the physical properties were inferior to those of Examples 1 to 124. Specifically, in the case of the positive photosensitive resin compositions of Comparative Examples 1 to 26, it was confirmed that the chemical resistance, heat resistance, solar resistance, hygroscopicity, operating reliability, and bending characteristics were very inferior.
[0615] Therefore, it can be seen that the positive photosensitive resin composition according to one embodiment of the present invention can easily implement an organic film having excellent sensitivity, film retention rate, adhesive strength, chemical resistance, heat resistance, solar resistance, hygroscopicity, operating reliability, and bending characteristics.
[0616]
[0617] [Explanation of symbols]
[0618] 10: Source drain 20: Organic film
[0619] 30: Positive 40: PDL
Claims
1. Alkali-soluble polymer resin; Esterified quinonediazide compounds; and A crosslinking agent containing a phenol group; Includes, The above alkali-soluble polymer resin is, A reaction product of a mixture comprising an amine compound, an acid anhydride compound, and a capping compound, A positive photosensitive resin composition satisfying the following formula 1: [Formula 1] (A+B) / 2 < 6.0 eV In the above equation 1, A is the CTC value (eV) of the above amine compound, B is the sum of the CTC value (eV) of the acid anhydride compound and the CTC value (eV) of the capping compound in the mixture of the acid anhydride compound and the capping compound, The CTC value represents a quantum computational simulation value of the energy level difference between the electron donor and electron acceptor of a compound, assuming that the compound forms a charge transfer complex.
2. In paragraph 1, A positive photosensitive resin composition, wherein the fluorine content of the positive photosensitive composition is 10,000 ppm or less.
3. In paragraph 1, The above alkali-soluble polymer resin includes a repeating unit represented by the following chemical formula A and a repeating unit represented by the following chemical formula B, The repeating unit represented by the above chemical formula A and the repeating unit represented by the above chemical formula B are R b Structure derived from an amine compound containing and R a A positive photosensitive resin composition comprising a structure derived from an acid anhydride compound containing: [Chemical Formula A] [Chemical Formula B] In the above chemical formulas A and B, The above R a and R b are each independently an organic group having 5 to 60 carbon atoms, The above X1 and X2 are each independently hydrogen or an alkyl group having 1 to 10 carbon atoms, a and b are each independently integers from 0 to 4, c and d are each independently integers from 0 to 2, and a+b is 1 or greater.
4. In paragraph 3, The above alkali-soluble polymer resin is, A positive photosensitive resin composition having a repeating unit represented by chemical formula B in an amount of 51 mol% or more, based on a total of 100 mol% of repeating units represented by chemical formula A and repeating units represented by chemical formula B.
5. In paragraph 3, A positive photosensitive resin composition wherein the amine compound comprises at least one of the compounds represented by the following chemical formulas 1-1 to 1-19: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] [Chemical Formula 1-4] [Chemical Formula 1-5] [Chemical Formula 1-6] [Chemical Formula 1-7] [Chemical Formula 1-8] [Chemical Formula 1-9] [Chemical Formula 1-10] [Chemical Formula 1-11] [Chemical Formula 1-12] [Chemical Formula 1-13] [Chemical Formula 1-14] [Chemical Formula 1-15] [Chemical Formula 1-16] [Chemical Formula 1-17] [Chemical Formula 1-18] [Chemical Formula 1-19] At least two of a1, b1, c1, d1, e1 and f1 are amine groups, and the rest are hydrogen, hydroxyl, halogen element substituted alkyl groups having 1 to 3 carbon atoms or -COOX2, At least two of a2, b2, c2 and d2 are amine groups, the rest are hydrogen, hydroxyl groups or -COOX2, and R 1-1 and R 1-2 are each independently hydrogen, an alkyl group having 1 to 10 carbon atoms, an alkyl group having 1 to 3 carbon atoms substituted with a halogen element, or a cycloalkyl group having 5 to 10 carbon atoms, At least two of a3, b3, c3 and d3 are amine groups, the rest are hydrogen, hydroxyl groups or -COOX2, and R 1-3 and R 1-4 are each independently an alkyl group having 1 to 10 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms, and R 1-5 and R 1-6 are each independently hydrogen or an alkyl group having 1 to 10 carbon atoms, At least two of a4, b4, c4 and d4 are amine groups, and the rest are hydrogen, hydroxyl or -COOX2, At least two of a5, b5, c5 and d5 are amine groups, the rest are hydrogen, hydroxyl groups or -COOX2, and R 1-7 and R 1-8 are each independently an alkyl group having 1 to 10 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms, At least two of a6, b6, c6 and d6 are amine groups, and the rest are hydrogen, hydroxyl or -COOX2, At least two of a7, b7, c7 and d7 are amine groups, and the rest are hydrogen, hydroxyl or -COOX2, At least two of a8, b8, c8 and d8 are amine groups, the rest are hydrogen, hydroxyl groups or -COOX2, and R 1-9 and R 1-10 are each independently an alkyl group having 1 to 10 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms, At least two of a9, b9, c9 and d9 are amine groups, and the rest are hydrogen, hydroxyl groups or -COOX2, a 10 , b 10 , c 10 and d 10 At least two of them are amine groups, and the rest are hydrogen, hydroxyl groups or -COOX2, a 11 , b 11 , c 11 , d 11 , e 11 and f 11 At least two of them are amine groups, and the rest are hydrogen, hydroxyl groups or -COOX2, a 12 , b 12 , c 12 , d 12 , e 12, f 12 and g 12 At least two of them are amine groups, and the rest are hydrogen, hydroxyl groups or -COOX2, a 13 , b 13 , c 13 , d 13 , e 13 and f 13 At least two of which are amine groups, and the remainder are hydrogen, a hydroxyl group, an alkyl group having 1 to 3 carbon atoms unsubstituted or substituted with a halogen element, or -COOX2, a 14 is a thiol group, an amine group or a hydroxy group, X2 is hydrogen or an alkyl group having 1 to 10 carbon atoms.
6. In paragraph 3, A positive photosensitive resin composition wherein the acid anhydride compound comprises at least one of the compounds represented by the following chemical formulas 2-1 to 2-16: [Chemical Formula 2-1] [Chemical Formula 2-2] [Chemical Formula 2-3] [Chemical Formula 2-4] [Chemical Formula 2-5] [Chemical Formula 2-6] [Chemical Formula 2-7] [Chemical Formula 2-8] [Chemical Formula 2-9] [Chemical Formula 2-10] [Chemical Formula 2-11] [Chemical Formula 2-12] [Chemical Formula 2-13] [Chemical Formula 2-14] [Chemical Formula 2-15] [Chemical Formula 2-16] In the above chemical formulas, R 2-1 Inland R 2-6 are each independently an alkyl group having 1 to 10 carbon atoms or a cycloalkyl group having 5 to 10 carbon atoms, n is an integer between 2 and 20.
7. In paragraph 1, A positive photosensitive resin composition wherein the capping compound comprises at least one of the following compounds C-1 to C-5: [Compound C-1] [Compound C-2] [Compound C-3] [Compound C-4] [Compound C-5] .
8. In paragraph 1, A positive photosensitive resin composition wherein the esterified quinonediazide compound comprises a reaction product of at least one of the phenol compounds represented by the following chemical formulae 3-1 to 3-13 and a quinonediazide compound: [Chemical Formula 3-1] [Chemical Formula 3-2] [Chemical Formula 3-3] [Chemical Formula 3-4] [Chemical Formula 3-5] [Chemical Formula 3-6] [Chemical Formula 3-7] [Chemical Formula 3-8] [Chemical Formula 3-9] [Chemical Formula 3-10] [Chemical Formula 3-11] [Chemical Formula 3-12] [Chemical Formula 3-13] In the above chemical formulas, R 3-1 Inland R 3-84 are each independently hydrogen, an alkyl group having 1 to 4 carbon atoms, or an alkenyl group having 2 to 4 carbon atoms, Z1 to Z4 are each independently hydrogen and an alkyl group having 1 to 4 carbon atoms.
9. In paragraph 1, A positive photosensitive resin composition, wherein the content of the esterified quinonediazide compound is 10 parts by weight or more and 40 parts by weight or less, based on 100 parts by weight of the alkali-soluble polymer resin.
10. In paragraph 1, A positive photosensitive resin composition wherein the crosslinking agent comprises at least one of the compounds represented by the following chemical formulae 4-1 to 4-21: [Chemical Formula 4-1] [Chemical Formula 4-2] [Chemical Formula 4-3] [Chemical Formula 4-4] [Chemical Formula 4-5] [Chemical Formula 4-6] [Chemical Formula 4-7] [Chemical Formula 4-8] [Chemical Formula 4-9] [Chemical Formula 4-10] [Chemical Formula 4-11] [Chemical Formula 4-12] [Chemical Formula 4-13] [Chemical Formula 4-14] [Chemical Formula 4-15] [Chemical Formula 4-16] [Chemical Formula 4-17] [Chemical Formula 4-18] [Chemical Formula 4-19] [Chemical Formula 4-20] [Chemical Formula 4-21] In the above chemical formulas, R 4a Inland R 4h are each independently hydrogen, an alkyl group having 1 to 3 carbon atoms, or and, In the above chemical formulas 4-1 to 4-8, R 4a and R 4b At least one of them And, In the above chemical formula 4-9, R 4a Inland R 4c At least one of them And, In the above chemical formulas 4-10 to 4-15, R 4a Inland R 4d At least one of them And, In the above chemical formulas 4-16 to 4-18, R 4a Inland R 4f At least one of them And, In the above chemical formulas 4-19 to 4-21, R 4a Inland R 4h At least one of them And, m is an integer from 1 to 6, and R 4-1 is an alkyl group having 1 to 3 carbon atoms.
11. In paragraph 1, A positive photosensitive resin composition, wherein the content of the crosslinking agent is 5 parts by weight or more and 30 parts by weight or less, based on 100 parts by weight of the alkali-soluble polymer resin.
12. In paragraph 1, A positive photosensitive resin composition further comprising at least one of an organic solvent, a surfactant, and an additive.
13. An electronic component including an insulating film containing a cured product of a positive photosensitive resin composition according to Article 1.
14. A display device including an insulating film containing a cured product of a positive photosensitive resin composition according to Article 1.
Citation Information
Patent Citations
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