Positive-type photosensitive resin composition and display device

Abstract

The present invention relates to a positive-type photosensitive resin composition capable of implementing an organic film with improved chemical resistance and heat resistance, and a display device having an organic material including a cured product of the composition.

Description

Positive type photosensitive resin composition and display device

[0001] The present invention relates to a positive-type photosensitive resin composition and a display device.

[0002]

[0003] Recently, among display devices, OLEDs (Organic Light Emitting Diodes), particularly AMOLEDs (Active Matrix OLEDs), are gaining attention in the market for various reasons.

[0004] Typically, OLED devices include an organic insulating film, and a polyimide photosensitive resin composition is generally used to form the organic insulating film. In the past, components used in polyimide photosensitive resin compositions included perfluorinated compounds (PFAS), but recently, there has been a demand for polyimide photosensitive resin compositions that are free of perfluorinated compounds.

[0005] However, in the case of perfluorinated compound-free photosensitive resin compositions, the contact resistance between electrodes is improved due to increased developability compared to conventional PFAS photosensitive resin compositions, but there is a problem in that the chemical resistance to wet chemicals becomes weak.

[0006]

[0007] The present invention provides a display device equipped with an organic material comprising a positive-type photosensitive resin composition capable of realizing an organic film with improved chemical resistance and heat resistance, and a cured product thereof.

[0008] However, the problems that the present invention aims to solve are not limited to those mentioned above, and other unmentioned problems will be clearly understood by those skilled in the art from the description below.

[0009]

[0010] One embodiment of the present invention provides a positive-type photosensitive resin composition comprising: an alkali-soluble polymer resin; an esterified quinone-diazide compound; and a crosslinking agent containing a phenol group, wherein the positive-type photosensitive resin composition has a fluorine content of less than 250 ppm and, with respect to 100 parts by weight of the alkali-soluble polymer resin, the content of the crosslinking agent is 5 parts by weight or more and 50 parts by weight or less.

[0011] 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:

[0012] [Chemical Formula A]

[0013]

[0014] [Chemical Formula B]

[0015]

[0016] In the above chemical formulas A and B, the R a and R b Each is independently an organic group having 5 to 60 carbon atoms, a and b are independently integers from 0 to 4, and a+b is 1 or more.

[0017] According to one embodiment of the present invention, the alkali-soluble polymer resin may have at least 51 mol% of the repeating unit represented by Formula B based on a total of 100 mol% of the repeating unit represented by Formula A and the repeating unit represented by Formula B.

[0018] According to one embodiment of the present invention, the repeating unit represented by the formula A and the repeating unit represented by the formula B are R b It includes a structure derived from an amine-based compound containing, and the amine-based compound may include a diamine-based compound having at least one hydroxyl group attached.

[0019] According to one embodiment of the present invention, the repeating unit represented by the formula A and the repeating unit represented by the formula B are R a It includes a structure derived from an acid anhydride compound containing, and said acid anhydride compound may include a cyclic acid dianhydride compound.

[0020] According to one embodiment of the present invention, the esterified quinone-diazide compound may comprise a reaction product of a quinone-diazide compound and at least one of a phenolic compound represented by the following formulas 3-1 to 3-13:

[0021]

[0022]

[0023]

[0024] In the above chemical formulas, R 3-1 to R 3-84 Each is 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, or an alkyl group having 1 to 4 carbon atoms.

[0025] According to one embodiment of the present invention, the content of the esterified quinone-diazide 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.

[0026] According to one embodiment of the present invention, the crosslinking agent may include three or more phenol groups represented by the following chemical formula C:

[0027] [Chemical Formula C]

[0028]

[0029] In the above chemical formula, R c-1 and R c-2 Each independently comprises hydrogen, an organic group having 1 to 60 carbon atoms, or is, R c-1 and R c-2 At least one of them and R c-3 and R c-4 is each independently hydrogen, a hydroxyl group, or an organic group having 1 to 30 carbon atoms, m is an integer from 1 to 27, and R c-5 is an alkyl group having 1 to 3 carbon atoms.

[0030] According to one embodiment of the present invention, the crosslinking agent comprises at least one of a first crosslinking agent and a second crosslinking agent, wherein the first crosslinking agent comprises a compound represented by the following chemical formula 4, and the second crosslinking agent may comprise a compound represented by the following chemical formula 5:

[0031] [Chemical Formula 4]

[0032]

[0033] [Chemical Formula 5]

[0034]

[0035] In the above chemical formulas, R 4-1 and R 5-1 Each is independently an unsubstituted or substituted straight-chain or branched-chain alkylene having 1 to 20 carbon atoms; an unsubstituted or substituted straight-chain or branched-chain alkenylene having 2 to 20 carbon atoms; an unsubstituted or substituted straight-chain or branched-chain hydrocarbon linker having 6 to 12 carbon atoms comprising at least one unsubstituted or substituted aromatic group having 6 to 30 carbon atoms; or an unsubstituted or substituted straight-chain or branched-chain hydrocarbon linker having 4 to 16 carbon atoms comprising at least one unsubstituted or substituted cycloalkyl group having 5 to 10 carbon atoms; and R c-1 and R c-2 Each independently comprises hydrogen, an organic group having 1 to 60 carbon atoms, or is, R c-1 and R c-2 At least one of them and, m is an integer from 1 to 27, and Rc-5 is an alkyl group having 1 to 3 carbon atoms, and the substituents of the substituted alkylene, the substituted alkenylene, the substituted aromatic group, the substituted cycloalkyl group, and the substituted hydrocarbon are an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkynyl group having 2 to 5 carbon atoms.

[0036] According to one embodiment of the present invention, the first crosslinking agent may comprise at least one of the compounds represented by the following formulas 4-1 to 4-3:

[0037]

[0038]

[0039] In the above chemical formulas, R c-1 and R c-2 Each independently hydrogen, a carbon-1 to carbon-3 alkyl group, or is, R c-1 and R c-2 At least one of them and, m is an integer from 1 to 6, and R c-5 is an alkyl group having 1 to 3 carbon atoms.

[0040] According to one embodiment of the present invention, the crosslinking agent comprises a first crosslinking agent, and the content of the first crosslinking agent may be 16 parts by weight or more and 39 parts by weight or less with respect to 100 parts by weight of the alkali-soluble polymer resin.

[0041] According to one embodiment of the present invention, the second crosslinking agent may comprise at least one of the compounds represented by the following formulas 5-1 to 5-6:

[0042]

[0043]

[0044] In the above chemical formulas, R c-1 and R c-2 Each independently hydrogen, a carbon-1 to carbon-3 alkyl group, or is, R c-1 and R c-2 At least one of them and, m is an integer from 1 to 6, and R c-5 is an alkyl group having 1 to 3 carbon atoms.

[0045] According to one embodiment of the present invention, the crosslinking agent comprises a second crosslinking agent, and the content of the second crosslinking agent may be 10 parts by weight or more and 34 parts by weight or less with respect to 100 parts by weight of the alkali-soluble polymer resin.

[0046] According to one embodiment of the present invention, the positive type photosensitive resin composition may include at least one of an organic solvent, a surfactant, and an additive.

[0047] One embodiment of the present invention provides a display device comprising: a substrate; and an organic film disposed on the substrate; wherein the organic film comprises a cured product of the positive-type photosensitive resin composition.

[0048]

[0049] A positive-type photosensitive resin composition according to one embodiment of the present invention can effectively realize an organic film with improved chemical resistance and heat resistance.

[0050] In addition, a display device according to one embodiment of the present invention can effectively realize improved physical properties by using an organic film comprising a cured product of the positive-type photosensitive resin composition.

[0051] The effects of the present invention are not limited to those described above, and unmentioned effects will be clearly understood by those skilled in the art from the present specification and the accompanying drawings.

[0052]

[0053] Figure 1 is a diagram showing the formation of a patterned film on a patterned ITO substrate and the deposition of EL.

[0054]

[0055] Throughout this specification, when a part is described as "comprising" a certain component, this means that, unless specifically stated otherwise, it does not exclude other components but may include additional components.

[0056] Throughout this specification, when a component is described as being located "on" another component, this includes not only cases where a component is in contact with another component, but also cases where another component exists between the two components.

[0057] Throughout the entire specification, the unit "parts by weight" may refer to the ratio of weight between each component.

[0058] Throughout this specification, terms including ordinal numbers, such as “first” and “second,” are used for the purpose of distinguishing one component from another and are not limited by said ordinal numbers. For example, within the scope of the invention, the first component may also be named the second component, and similarly, the second component may be named the first component.

[0059] Throughout the entire specification, "at least one of a, b and c" may include a, b, or c alone, or two or more combinations selected from the group consisting of a, b, and c.

[0060] Throughout this specification, “*” in the chemical formula may indicate a bonding position.

[0061]

[0062] The present specification will be described in more detail below.

[0063] One embodiment of the present invention provides a positive-type photosensitive resin composition comprising: an alkali-soluble polymer resin; an esterified quinone-diazide compound; and a crosslinking agent containing a phenol group, wherein the positive-type photosensitive resin composition has a fluorine content of less than 250 ppm and, with respect to 100 parts by weight of the alkali-soluble polymer resin, the content of the crosslinking agent is 5 parts by weight or more and 50 parts by weight or less.

[0064] A positive-type photosensitive resin composition according to one embodiment of the present invention can effectively realize an organic film with improved chemical resistance and heat resistance. Specifically, the positive-type photosensitive resin composition can easily realize an organic film with excellent properties of sensitivity, residual film rate, adhesion, chemical resistance, heat resistance, solar resistance, driving reliability, bending characteristics, and contact resistance. More specifically, the positive-type photosensitive resin composition can effectively realize improved chemical resistance to wet chemicals and excellent heat resistance while improving contact resistance properties by not including fluorine components.

[0065] According to one embodiment of the present invention, the positive-type photosensitive resin composition may have a fluorine content of 0 ppm or more and less than 250 ppm. Specifically, the fluorine content of the positive-type photosensitive resin composition may be 0 ppm or more and 230 ppm or less, 0 ppm or more and 200 ppm or less, 0 ppm or more and 150 ppm or less, 0 ppm or more and 100 ppm or less, 0 ppm or more and 50 ppm or less, 0 ppm or more and 30 ppm or less, or 0 ppm or more and 10 ppm or less. The positive-type photosensitive resin composition satisfying the above-mentioned fluorine content can easily realize improved contact resistance properties.

[0066] 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 50 parts by weight or less, 10 parts by weight or more and 45 parts by weight or less, 15 parts by weight or more and 40 parts by weight or less, 20 parts by weight or more and 35 parts by weight or less, 25 parts by weight or more and 30 parts by weight or less, 5 parts by weight or more and 39 parts by weight or less, 5 parts by weight or more and 35 parts by weight or less, 5 parts by weight or more and 34 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, 16 parts by weight or more and 24 parts by weight or less, 21 parts by weight or more and 23 parts by weight or less, 30 parts by weight or more and 50 parts by weight or less, 32.5 parts by weight or more and 47.5 parts by weight or less, 36 parts by weight or more and 44 parts by weight or less, or 39 parts by weight or more and 41 parts by weight or less. When the content of the crosslinking agent is within the aforementioned range, the positive-type photosensitive resin composition can effectively realize an organic film with excellent mechanical properties such as adhesion and bending characteristics, while also improving driving reliability.

[0067] 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:

[0068] [Chemical Formula A]

[0069]

[0070] [Chemical Formula B]

[0071]

[0072] In the above chemical formulas A and B, the R a and R bEach is independently an organic group having 5 to 60 carbon atoms, a and b are independently integers from 0 to 4, and a+b is 1 or more. The repeating unit represented by the above chemical formula A includes an amic acid bond, and the repeating unit represented by the above chemical formula B may include an imide bond.

[0073] Specifically, the above R a may be an organic group comprising 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 having 5 to 10 carbon atoms. In addition, the above R b may be an organic group comprising at least one aromatic group having 6 to 30 carbon atoms. 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.

[0074] By using an alkali-soluble polymer resin comprising a repeating unit represented by the above chemical formula A and a repeating unit represented by the above chemical formula B, a positive-type photosensitive resin composition with improved chemical resistance and heat resistance can be provided.

[0075] According to one embodiment of the present invention, the alkali-soluble polymer resin may have at least 51 mol% of the repeating unit represented by Formula B based on a total of 100 mol% of the repeating unit represented by Formula A and the repeating unit represented by Formula B. That is, based on a total of 100 mol% of the repeating unit including an amic acid bond and the repeating unit including an imide bond, the content of the repeating unit including an imide bond may be at least 51 mol%.

[0076] Specifically, based on a total of 100 mol% of repeating units represented by the above chemical formula A and repeating units represented by the above chemical formula B, the content of the repeating unit represented by the above chemical formula B may be 51 mol% or more and 97 mol% or less, 60 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, or 90 mol% or more and 95 mol% or less. When the content of the repeating unit represented by the above chemical formula B satisfies the aforementioned range, a positive-type photosensitive resin composition capable of easily realizing the aforementioned effect can be provided.

[0077] According to one embodiment of the present invention, the repeating unit represented by the formula A and the repeating unit represented by the formula B are R b It may include a structure derived from an amine-based compound containing [the element]. Specifically, the amine-based compound may include a diamine-based compound. More specifically, the amine-based compound may include at least a first aromatic group having 6 to 30 carbon atoms to which one or more amine groups are attached, and a second aromatic group having 6 to 30 carbon atoms to which one or more amine groups are attached. In this case, the first aromatic group and the second aromatic group may not be directly bonded. When the first aromatic group and the second aromatic group are bonded in two or more ways, at least one bond may not be a direct bond. Specifically, the first aromatic group and the second aromatic group are bonded by a number of connecting atoms from one to twenty or fewer, and the connecting atoms may include at least one of carbon, oxygen, and sulfur. The number of connecting atoms may be 1 to 20, 2 to 18, 4 to 15, 6 to 10, 1 to 10, 1 to 8, or 10 to 20. As the first aromatic group and the second aromatic group are bonded by the aforementioned linking atom, the amine compound may have a bulky structure. The R bBy using an amine-based compound containing, a positive-type photosensitive resin composition that can easily realize the aforementioned effect can be provided.

[0078] According to one embodiment of the present invention, the repeating unit represented by the formula A and the repeating unit represented by the formula B are R b It includes a structure derived from an amine-based compound containing, and the amine-based compound may include a diamine-based compound having at least one hydroxyl group attached.

[0079] According to one embodiment of the present invention, the amine-based compound may include a compound represented by the following chemical formula 1:

[0080] [Chemical Formula 1]

[0081]

[0082] In the above chemical formula 1, R 1a is oxygen; unsubstituted or substituted alkylene having 1 to 5 carbon atoms; * -SO2- * ; or * -OR 1j -R 1k -R 1l -O- * ; and, R 1b and R 1c Each is independently hydrogen; or an alkyl group having 1 to 5 carbon atoms; or R 1b and R 1c are connected to each other to form a direct bond, and R 1d , R 1e , R 1f , R 1g , R 1h and R 1i At least two of them are amine groups, and the remainder are hydrogen, hydroxyl groups, or alkyl groups having 1 to 3 carbon atoms, and R 1j and R 1l is an unsubstituted or substituted aromatic group having 6 to 30 carbon atoms, and R 1kis an unsubstituted or substituted alkylene having 1 to 5 carbon atoms; or * -SO2- * ; and the substituent of the substituted alkylene is an aromatic group having 6 to 30 carbon atoms substituted with an unsubstituted or hydroxyl group; an aromatic group having 6 to 30 carbon atoms substituted with a phenoxy group; an aromatic group having 6 to 30 carbon atoms substituted with a phenoxy group to which a hydroxyl group is bonded; an alkenyl group having 2 to 4 carbon atoms bonded with an aromatic group having 6 to 30 carbon atoms substituted with an unsubstituted or hydroxyl group; an alkyl group having 1 to 10 carbon atoms; or a cycloalkyl group having 5 to 10 carbon atoms; and the substituent of the substituted aromatic group is an alkyl group having 1 to 5 carbon atoms.

[0083] Specifically, in Chemical Formula 1, R 1a may be an alkylene, and the number of carbon atoms of the alkylene may be 1 or more and 4 or less, 1 or more and 3 or less, or 1 or more and 2 or less. R 1b and R 1c Each may independently be an alkyl group, and the number of carbon atoms in the alkyl group may be 1 or more and 4 or less, 1 or more and 3 or less, or 1 or more and 2 or less. R 1d , R 1e and at least one of them is an amine group, and R 1g , R 1h and R 1i At least one of them may be an amine group. R 1j and R 1l The alkylene may be a benzene ring. The substituent of the substituted alkylene may be an unsubstituted or hydroxyl group substituted benzene ring; a phenoxy group substituted benzene ring to which a hydroxyl group is bonded; a carbon 2 to 4 alkenyl group to which an unsubstituted or hydroxyl group substituted benzene ring is bonded; a carbon 1 to 3 alkyl group; or a carbon 5 to 6 cycloalkyl group.

[0084] By using an amine-based compound represented by Chemical Formula 1 above, a positive-type photosensitive resin composition capable of easily realizing the aforementioned effects can be provided. In addition, since the amine-based compound represented by Chemical Formula 1 does not contain fluorine, the positive-type photosensitive resin composition comprising the alkali-soluble polymer resin can easily provide an organic film with significantly improved contact resistance properties.

[0085] According to one embodiment of the present invention, the amine-based compound may include at least one of the compounds represented by the following formulas 1-1 to 1-12:

[0086]

[0087]

[0088] In the above chemical formulas, at least two of a1, b1, c1, and d1 are amine groups and the remainder is hydrogen or a hydroxyl group, at least two of a2, b2, c2, and d2 are amine groups and the remainder is hydrogen or a hydroxyl group, and R 1-1 and R 1-2 Each is independently an alkyl group having 1 to 10 carbon atoms, at least two of a3, b3, c3, and d3 are amine groups, and the remainder are hydrogen or hydroxyl groups, and R 1-3 and R 1-4 Each is independently an alkyl group having 1 to 10 carbon atoms, and R 1-5 and R 1-6 Each is 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 remainder are hydrogen or hydroxyl groups, at least two of a5, b5, c5, and d5 are amine groups and the remainder are hydrogen or hydroxyl groups, and R 1-7 and R 1-8Each is independently an alkyl group having 1 to 10 carbon atoms, at least two of a6, b6, c6, and d6 are amine groups and the remainder is hydrogen or a hydroxyl group, at least two of a7, b7, c7, and d7 are amine groups and the remainder is hydrogen or a hydroxyl group, at least two of a8, b8, c8, and d8 are amine groups and the remainder is hydrogen or a hydroxyl group, and R 1-9 and R 1-10 Each is independently an alkyl group having 1 to 10 carbon atoms, at least two of a9, b9, c9, and d9 are amine groups, and the remainder are hydrogen or hydroxyl groups, and a 10 , b 10 , c 10 and d 10 At least two of them are amine groups, and the remainder are hydrogen or hydroxyl groups, and a 11 , b 11 , c 11 , d 11 , e 11 and f 11 At least two of them are amine groups, and the remainder are hydrogen or hydroxyl groups, and 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 or hydroxyl groups.

[0089] Specifically, in the above chemical formula 1-1, a1 and c1 are amine groups, and a first aromatic group and a second aromatic group may be bonded with one oxygen as a linking atom. In the above chemical formula 1-2, a2 ​​and c2 are amine groups, and a first aromatic group and a second aromatic group may be bonded with one carbon as a linking atom. In the above chemical formula 1-3, a3 and c3 are amine groups, and a first aromatic group and a second aromatic group may be bonded with one carbon as a linking atom. In the above chemical formula 1-4, a4 ​​and c4 are amine groups, and a first aromatic group and a second aromatic group may be bonded with one carbon as a linking atom. In the above chemical formula 1-5, b5 and d5 are amine groups, and a first aromatic group and a second aromatic group may be bonded with one carbon as a linking atom. In the above chemical formula 1-6, a6 and c6 are amine groups, and a first aromatic group and a second aromatic group may be bonded with one sulfur atom acting as a linking atom. In the above chemical formula 1-7, b7 and d7 are amine groups, and a first aromatic group and a second aromatic group may be bonded with one carbon atom acting as a linking atom. In the above chemical formula 1-8, a8 and d8 are amine groups, and a first aromatic group and a second aromatic group may be bonded with nine carbons and two oxygen atoms acting as linking atoms. In the above chemical formula 1-9, a9 and d9 are amine groups, and a first aromatic group and a second aromatic group may be bonded with eight carbons, two oxygen atoms, and one sulfur atom acting as linking atoms. In the above chemical formula 1-10, a 10 and c 10 is an amine group, and may be a first aromatic group and a second aromatic group bonded with one carbon as a linking atom. In the above chemical formula 1-11, b 11 and e 11 is an amine group, and may be a first aromatic group and a second aromatic group bonded with one carbon as a linking atom. In the above chemical formula 1-12, b 12 and e 12is an amine group, and may be a first aromatic group and a second aromatic group bonded with one carbon as a linking atom.

[0090] By using an amine-based compound comprising at least one of the compounds represented by Chemical Formulas 1-1 to 1-12, a positive-type photosensitive resin composition capable of easily realizing the aforementioned effects can be provided. In addition, since the amine-based compound does not contain fluorine, the positive-type photosensitive resin composition can easily provide an organic film with significantly improved contact resistance properties.

[0091] According to one embodiment of the present invention, the amine-based compound may include at least one of the following compounds 1-1 to 1-12.

[0092]

[0093]

[0094] By not containing fluorine, the amine-based compounds of the above compounds 1-1 to 1-12 can provide a positive-type photosensitive resin composition that can easily realize the aforementioned effects.

[0095] According to one embodiment of the present invention, the repeating unit represented by the formula A and the repeating unit represented by the formula B are R a It may include a structure derived from an acid anhydride compound containing [the component]. Specifically, the acid anhydride compound may include an acid dianhydride compound. More specifically, the acid anhydride compound may include a cyclic acid dianhydride compound.

[0096] According to one embodiment of the present invention, the acid anhydride compound may include a first cyclic acid anhydride group and a second cyclic acid anhydride group. In this case, the first cyclic acid anhydride group and the second cyclic acid anhydride group may not be directly bonded. Specifically, the first cyclic acid anhydride group and the second cyclic acid anhydride group are bonded by a number of linking atoms from 1 to 20, wherein the linking atoms may include at least one of carbon, oxygen, and sulfur. The number of linking atoms may be 1 to 20, 2 to 18, 4 to 15, 6 to 10, 1 to 10, 1 to 8, or 10 to 20. As the first cyclic acid anhydride group and the second cyclic acid anhydride group are bonded by the aforementioned linking atoms, the acid anhydride compound may have a bulky structure. R a By using an acid anhydride-based compound containing, a positive-type photosensitive resin composition that can easily realize the aforementioned effect can be provided.

[0097] According to one embodiment of the present invention, the acid anhydride compound may comprise 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. In this case, the third aromatic group and the fourth aromatic group may not be directly bonded. Specifically, the third aromatic group and the fourth aromatic group are bonded by a number of linking atoms from 1 to 20, wherein the linking atoms may comprise at least one of carbon, oxygen, and sulfur. The number of linking atoms may be 1 to 20, 2 to 18, 4 to 15, 6 to 10, 1 to 10, 1 to 8, or 10 to 20. As the third aromatic group and the fourth aromatic group are bonded by the aforementioned linking atoms, the acid anhydride compound may have a bulky structure. R aBy using an acid anhydride-based compound containing, a positive-type photosensitive resin composition that can easily realize the aforementioned effect can be provided.

[0098] According to one embodiment of the present invention, the repeating unit represented by the formula A and the repeating unit represented by the formula B are R a It comprises a structure derived from an acid anhydride compound containing, wherein the acid anhydride compound may include at least one of a compound represented by the following chemical formula 2A and a compound represented by chemical formula 2B:

[0099] [Chemical Formula 2A]

[0100]

[0101] [Chemical Formula 2B]

[0102]

[0103] In the above chemical formulas 2A and 2B, R 2a is an unsubstituted or substituted straight-chain or branched-chain alkylene having 1 to 20 carbon atoms; or * -SO2- * ; and, n1 is an integer of 0 or 1, and R 2b and R 2c are each independently an unsubstituted or substituted benzene ring; and n2 is an integer of 0 or 1, n3 is an integer of 0 or 1, and R 2d and R 2e Each independently, * -O- * ; or * -CO2- * ; and, n4 is an integer of 0 or 1, n5 is an integer of 0 or 1, and R 2f is a direct bond; or an unsubstituted or substituted alkylene having 1 to 5 carbon atoms; and R 2gis hydrogen; or an alkyl group having 1 to 5 carbon atoms, the dotted line is an optional double bond, and the substituent of the substituted alkylene or substituted benzene ring is an alkyl group having 1 to 10 carbon atoms; a cycloalkyl group having 5 to 10 carbon atoms; or a fluorene.

[0104] By using the alkali-soluble polymer resin comprising a structure derived from at least one of the acid anhydride compound represented by Chemical Formula 2A and the acid anhydride compound represented by Chemical Formula 2B, a positive-type photosensitive resin composition with improved chemical resistance and heat resistance can be effectively realized. In addition, since the acid anhydride compound does not contain fluorine, the positive-type photosensitive resin composition can easily provide an organic film with significantly improved contact resistance properties.

[0105] 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 2-8:

[0106]

[0107]

[0108] In the above chemical formulas, R 2-1 to R 2-7 Each is 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 to R 2-7Each of the alkyl groups may independently be an alkyl group, and the number of carbon atoms in the alkyl group may be 1 or more and 8 or less, 1 or more and 5 or less, 1 or more and 3 or less, or 1. In this case, the above chemical formula 2-1 may be a third aromatic group and a fourth aromatic group bonded with one carbon as a linking atom. The above chemical formula 2-2 may be a third aromatic group and a fourth aromatic group bonded with four carbons and two oxygens as linking atoms. The above chemical formula 2-3 may be a third aromatic group and a fourth aromatic group bonded with nine carbons and two oxygens as linking atoms. The above chemical formula 2-4 may be a third aromatic group and a fourth aromatic group bonded with one carbon as a linking atom. The above chemical formula 2-5 may be a third aromatic group and a fourth aromatic group bonded with one carbon and one oxygen as linking atoms. The above chemical formula 2-6 may be a third aromatic group and a fourth aromatic group bonded with one sulfur as a linking atom. The above chemical formula 2-7 may be formed by combining a third aromatic group and a fourth aromatic group with 11 carbons and 2 oxygens as connecting atoms. The above chemical formula 2-8 may be formed by combining a first cyclic acid anhydride group and a second cyclic acid anhydride group with 3 carbons as connecting atoms.

[0109] By using an acid anhydride compound comprising at least one of the compounds represented by Chemical Formulas 2-1 to 2-8, a positive-type photosensitive resin composition capable of easily realizing the aforementioned effects can be provided. Furthermore, since the acid anhydride compound does not contain fluorine, the positive-type photosensitive resin composition can easily provide an organic film with significantly improved contact resistance properties.

[0110] According to one embodiment of the present invention, the amine-based compound may include at least one of the following compounds 1-1 to 1-12.

[0111]

[0112]

[0113] The acid anhydride compounds of the above compounds 2-1 to 2-8 do not contain fluorine, thereby providing a positive-type photosensitive resin composition that can easily achieve the aforementioned effects.

[0114] According to one embodiment of the present invention, the alkali-soluble polymer resin may have the ends of the main chain end-capped with an end-capping compound comprising an acid anhydride compound. The end-capping compound may include a cyclic acid anhydride compound. The cyclic acid anhydride compound may include a benzene ring or a cyclohexene ring. For example, the end-capping compound may include at least one of the compounds represented by the following compounds E-1 to E-3.

[0115]

[0116]

[0117] According to one embodiment of the present invention, the esterified quinone-diazide compound may comprise a reaction product of a quinone-diazide compound and at least one of a phenolic compound represented by the following formulas 3-1 to 3-13:

[0118]

[0119]

[0120]

[0121]

[0122] In the above chemical formulas, R 3-1 to R 3-84 Each is 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, or an alkyl group having 1 to 4 carbon atoms.

[0123] Specifically, the quinone diazide compound may include a naphthoquinone diazide compound. That is, the esterified quinone diazide compound may include a reaction product of a naphthoquinone diazide compound and one of the phenol compounds represented by Chemical Formulas 3-1 to 3-13.

[0124] According to one embodiment of the present invention, the esterified quinone-diazide compound may include a compound represented by the following chemical formula 3-A.

[0125] [Chemical Formula 3-A]

[0126]

[0127] 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. By using the above esterified quinone-diazide compound, a positive-type photosensitive resin composition capable of easily realizing the aforementioned effect can be provided.

[0128] 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.

[0129]

[0130]

[0131] According to one embodiment of the present invention, the esterified quinone-diazide compound may have 2 mol or more of the quinone-diazide compound bonded to 1 mol of the phenol compound. Specifically, the content of the quinone-diazide compound bonded to the phenolic hydroxyl group of the phenol compound may be 2.0 mol or more and 3.5 mol or less, 2.0 mol or more and 3.0 mol or less, or 2.0 mol or more and 2.5 mol or less, based on 1 mol of the phenol compound. By using the esterified quinone-diazide compound bonded in the aforementioned content, the positive-type photosensitive resin composition can effectively produce an organic film with excellent chemical resistance and heat resistance.

[0132] The above quinone-diazide compound can react with the phenolic hydroxyl groups of the above phenolic compound. For example, the phenolic compound represented by Formula 3-7 contains four phenolic hydroxyl groups, so 1 mol of the phenolic compound contains 4 mol of reaction sites. When the above quinone-diazide compound reacts with the phenolic compound represented by Formula 3-7, the esterified quinone-diazide compound may include an unreacted phenolic compound containing four phenolic hydroxyl groups, a reaction product containing three phenolic hydroxyl groups and one quinone-diazide compound, a reaction product containing two phenolic hydroxyl groups and two quinone-diazide compounds, a reaction product containing one phenolic hydroxyl group and three quinone-diazide compounds, and a reaction product containing four quinone-diazide compounds. The content of the quinone-diazide compound bound to the aforementioned esterified quinone-diazide compound may be based on 1 mol of phenolic compound with respect to the entire reaction product. That is, the content of the quinone-diazide compound bound to the esterified quinone-diazide compound may correspond to the content of the quinone-diazide compound added to carry out the reaction with respect to 1 mol of phenolic compound.

[0133] According to one embodiment of the present invention, the content of the esterified quinone-diazide 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 quinone-diazide 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, 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 quinone-diazide compound is within the aforementioned range, the positive-type photosensitive resin composition can effectively realize an organic film with improved chemical resistance and heat resistance.

[0134] According to one embodiment of the present invention, the crosslinking agent may include three or more phenol groups represented by the following chemical formula C:

[0135] [Chemical Formula C]

[0136]

[0137] In the above chemical formula, R c-1 and R c-2 Each independently comprises hydrogen, an organic group having 1 to 60 carbon atoms, or is, R c-1 and R c-2 At least one of them and R c-3 and R c-4 is each independently hydrogen, a hydroxyl group, or an organic group having 1 to 30 carbon atoms, m is an integer from 1 to 27, and R c-5 is an alkyl group having 1 to 3 carbon atoms.

[0138] Specifically, R c-1 and R c-2 Each independently comprises hydrogen, an alkyl group having 1 to 10 carbon atoms, an alkene group having 2 to 10 carbon atoms, or It could be, R c-1 and R c-2At least one of them It could be. R c-3 and R c-4 Each can independently be hydrogen, a hydroxyl group, an alkyl group having 1 to 10 carbon atoms, or an alkene group having 2 to 10 carbon atoms.

[0139] By using a crosslinking agent containing three or more phenolic groups represented by the above chemical formula C, the positive-type photosensitive resin composition can effectively achieve improved chemical resistance to chemical solutions and excellent heat resistance while improving contact resistance properties by ensuring that no fluorine components are included.

[0140] According to one embodiment of the present invention, the crosslinking agent comprises at least one of a first crosslinking agent and a second crosslinking agent, wherein the first crosslinking agent comprises a compound represented by the following chemical formula 4, and the second crosslinking agent may comprise a compound represented by the following chemical formula 5:

[0141] [Chemical Formula 4]

[0142]

[0143] [Chemical Formula 5]

[0144]

[0145] In the above chemical formulas, R 4-1 and R 5-1 Each is independently an unsubstituted or substituted straight-chain or branched-chain alkylene having 1 to 20 carbon atoms; an unsubstituted or substituted straight-chain or branched-chain alkenylene having 2 to 20 carbon atoms; an unsubstituted or substituted straight-chain or branched-chain hydrocarbon linker having 6 to 12 carbon atoms comprising at least one unsubstituted or substituted aromatic group having 6 to 30 carbon atoms; or an unsubstituted or substituted straight-chain or branched-chain hydrocarbon linker having 4 to 16 carbon atoms comprising at least one unsubstituted or substituted cycloalkyl group having 5 to 10 carbon atoms; and R c-1 and R c-2Each independently comprises hydrogen, an organic group having 1 to 60 carbon atoms, or is, R c-1 and R c-2 At least one of them and, m is an integer from 1 to 27, and R c-5 is an alkyl group having 1 to 3 carbon atoms, and the substituents of the substituted alkylene, the substituted alkenylene, the substituted aromatic group, the substituted cycloalkyl group, and the substituted hydrocarbon are an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkynyl group having 2 to 5 carbon atoms.

[0146] Specifically, R 4-1 may be an unsubstituted or substituted alkylene with an alkyl group having 1 to 3 carbon atoms, and the number of carbon atoms contained in the alkylene may be 1 or more and 15 or less, 1 or more and 10 or less, 1 or more and 5 or less, or 1 or more and 3 or less. In addition, R 4-1 The hydrocarbon linker may be an unsubstituted or carbon-1 to carbon-3 alkyl group comprising at least one benzene ring within the main chain. That is, the benzene ring may be included within the main chain of the hydrocarbon linker. In this case, the hydrocarbon linker may be an alkylene having 1 to 5 carbon atoms in the main chain excluding the benzene ring, or 1 to 3 carbon atoms.

[0147] Also, R 5-1 may be unsubstituted alkenylene, and the number of carbon atoms contained in the alkenylene may be 2 or more and 10 or less, 2 or more and 5 or less, or 2 or more and 3 or less. In addition, R 5-1 ... may be a hydrocarbon linker substituted with an unsubstituted or C1 to C3 alkyl group containing at least one benzene ring within the main chain. That is, the benzene ring may be included within the main chain of the hydrocarbon linker. In this case, the hydrocarbon linker may be an alkylene having 1 to 5 carbon atoms in the main chain excluding the benzene ring, or 1 to 3 carbon atoms. Additionally, R 5-1The hydrocarbon linker may be an unsubstituted or carbon-1 to carbon-3 alkyl group comprising at least one cyclohexane ring within the main chain. That is, the cyclohexane ring may be included within the main chain of the hydrocarbon linker. In this case, the hydrocarbon linker may be an alkylene having 1 to 5 carbons, 1 to 3 carbons, or 1 to 2 carbons in the main chain excluding the cyclohexane ring.

[0148] The positive-type photosensitive resin composition comprising a crosslinking agent including at least one of a first crosslinking agent and a second crosslinking agent can effectively achieve improved chemical resistance to chemical solutions and excellent heat resistance while improving contact resistance properties by not including fluorine components.

[0149] According to one embodiment of the present invention, the first crosslinking agent may comprise at least one of the compounds represented by the following formulas 4-1 to 4-3:

[0150]

[0151]

[0152] In the above chemical formulas, R c-1 and R c-2 Each independently hydrogen, a carbon-1 to carbon-3 alkyl group, or is, R c-1 and R c-2 At least one of them and, m is an integer from 1 to 6, and R c-5 is an alkyl group having 1 to 3 carbon atoms.

[0153] The first crosslinking agent above has R at the ortho position based on the hydroxyl group of the phenol group. c-1 and R c-2 By having a structure in which two specific types of exposed substituents are combined, a positive type photosensitive resin composition having improved chemical resistance to chemical solutions and excellent heat resistance can be effectively provided.

[0154] According to one embodiment of the present invention, according to one embodiment of the present invention, the first crosslinking agent may comprise at least one of the following compounds 4-1 to 4-3:

[0155]

[0156] By using a crosslinking agent comprising at least one of the above compounds 4-1 to 4-3, the positive-type photosensitive resin composition can effectively achieve improved chemical resistance to chemical solutions and excellent heat resistance.

[0157] According to one embodiment of the present invention, the crosslinking agent comprises a first crosslinking agent, and with respect to 100 parts by weight of the alkali-soluble polymer resin, the content of the first crosslinking agent is 5 parts by weight or more and 50 parts by weight or less, 5 parts by weight or more and 39 parts by weight or less, 16 parts by weight or more and 39 parts by weight or less, 9 parts by weight or more and 38 parts by weight or less, 10 parts by weight or more and 37 parts by weight or less, 12 parts by weight or more and 35 parts by weight or less, 13 parts by weight or more and 33 parts by weight or less, 15 parts by weight or more and 30 parts by weight or less, 16 parts by weight or more and 28 parts by weight or less, 18 parts by weight or more and 25 parts by weight or less, 20 parts by weight or more and 22 parts by weight or less, 5 parts by weight or more and 30 parts by weight or less, 7 parts by weight or more and 27 parts by weight or less, 11 parts by weight or more and 24 parts by weight or less, 14 parts by weight or more and 21 parts by weight or less, 25 parts by weight or more and 39 parts by weight or less. It may be 27 parts by weight or more and 38 parts by weight or less, or 29 parts by weight or more and 36 parts by weight or less. When the content of the first crosslinking agent is within the aforementioned range, the positive-type photosensitive resin composition can effectively achieve improved chemical resistance to chemical solutions and excellent heat resistance.

[0158] According to one embodiment of the present invention, the second crosslinking agent may comprise at least one of the compounds represented by the following formulas 5-1 to 5-6:

[0159]

[0160]

[0161] In the above chemical formulas, R c-1 and R c-2 Each independently hydrogen, a carbon-1 to carbon-3 alkyl group, or is, R c-1 and R c-2 At least one of them and, m is an integer from 1 to 6, and R c-5 is an alkyl group having 1 to 3 carbon atoms.

[0162] The above second crosslinking agent has R at the ortho position based on the hydroxyl group of the phenol group. c-1 and R c-2 By having a structure in which two specific types of exposed substituents are combined, a positive type photosensitive resin composition having improved chemical resistance to chemical solutions and excellent heat resistance can be effectively provided.

[0163] According to one embodiment of the present invention, the second crosslinking agent may comprise at least one of the compounds represented by the following compounds 5-1 to 5-6:

[0164]

[0165]

[0166] By using a crosslinking agent comprising at least one of the above compounds 5-1 to 5-6, the positive-type photosensitive resin composition can effectively achieve improved chemical resistance to chemical solutions and excellent heat resistance.

[0167] According to one embodiment of the present invention, the crosslinking agent comprises a second crosslinking agent, and with respect to 100 parts by weight of the alkali-soluble polymer resin, the content of the second crosslinking agent is 5 parts by weight or more and 50 parts by weight or less, 5 parts by weight or more and 34 parts by weight or less, 10 parts by weight or more and 34 parts by weight or less, 9 parts by weight or more and 33 parts by weight or less, 10 parts by weight or more and 31 parts by weight or less, 12 parts by weight or more and 28 parts by weight or less, 13 parts by weight or more and 25 parts by weight or less, 15 parts by weight or more and 22 parts by weight or less, 16 parts by weight or more and 20 parts by weight or less, 5 parts by weight or more and 25 parts by weight or less, 7 parts by weight or more and 23 parts by weight or less, 11 parts by weight or more and 21 parts by weight or less, 14 parts by weight or more and 19 parts by weight or less, 20 parts by weight or more and 34 parts by weight or less, 21 parts by weight or more and 33 parts by weight or less, 23 parts by weight or more and 30 parts by weight or less, or The amount may be 24 parts by weight or more and 27 parts by weight or less. When the content of the second crosslinking agent is within the aforementioned range, the positive-type photosensitive resin composition can effectively achieve improved chemical resistance to chemical solutions and excellent heat resistance.

[0168] According to one embodiment of the present invention, the crosslinking agent may include the first crosslinking agent and the second crosslinking agent. In this case, the weight ratio of the first crosslinking agent to the second crosslinking agent may be 1:0.2 to 1:8, 1:0.3 to 1:7.5, 1:0.5 to 1:7, 1:0.6 to 1:6, 1:1 to 1:5, 1:2 to 1:4, or 1:5 to 1:8. When the weight ratio of the first crosslinking agent to the second crosslinking agent is within the aforementioned range, the positive-type photosensitive resin composition can effectively achieve improved chemical resistance to chemical solutions and excellent heat resistance.

[0169] According to one embodiment of the present invention, the crosslinking agent may include an additional crosslinking agent in addition to at least one of the first crosslinking agent and the second crosslinking agent. For example, the additional crosslinking agent may include a compound represented by the following chemical formula C-1.

[0170] [Chemical Formula C-1]

[0171]

[0172] In the above chemical formula C-1, R c-1 to R c-3 It is identical to that defined in the above chemical formula C.

[0173] According to one embodiment of the present invention, the crosslinking agent may include the first crosslinking agent and an additional crosslinking agent. In this case, the weight ratio of the additional crosslinking agent to the first crosslinking agent may be 1:1 to 1:8, 1:2 to 1:7, 1:3 to 1:6, 1:4 to 1:5, 1:1 to 1:5, or 1:4 to 1:8. When the weight ratio of the additional crosslinking agent to the first crosslinking agent is within the aforementioned range, the positive-type photosensitive resin composition can effectively achieve improved chemical resistance to chemical solutions and excellent heat resistance.

[0174] According to one embodiment of the present invention, the crosslinking agent may include the second crosslinking agent and an additional crosslinking agent. In this case, the weight ratio of the additional crosslinking agent to the second crosslinking agent may be 1:0.5 to 1:7, 1:1 to 1:6, 1:2 to 1:5, 1:3 to 1:4, 1:0.5 to 1:5, or 1:4 to 1:7. When the weight ratio of the additional crosslinking agent to the second crosslinking agent is within the aforementioned range, the positive-type photosensitive resin composition can effectively achieve improved chemical resistance to chemical solutions and excellent heat resistance.

[0175] According to one embodiment of the present invention, the positive-type photosensitive resin composition may include at least one of an organic solvent, a surfactant, and an additive. The organic solvent may be any used in the art without limitation. For example, 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), ethyl-3-ethoxypropionate (EEP), N,N-diethylformamide (DEF), propylene glycol monomethyl ether (PGME), diethyl glycol ethylmethyl ether (MEDG), diethyl glycol butyl methyl ether (MBDG), diethylene glycol dimethyl ester (DMDG), diethylene glycol diethyl ester (DEDG), and N,N-dimethylpropionamide (DMPA). In addition, the above additives may be used without limitation as those used in the industry. For example, the above additives may include thermal acid generators, UV absorbers, etc.

[0176]

[0177] One embodiment of the present invention provides a display device comprising: a substrate; and an organic film disposed on the substrate; wherein the organic film comprises a cured product of a positive-type photosensitive resin composition according to claim 1.

[0178] A display device according to one embodiment of the present invention can effectively realize improved physical properties by using an organic film comprising a cured product of the positive-type photosensitive resin composition.

[0179] According to one embodiment of the present invention, the organic film may be manufactured through a method of manufacturing an organic film from a positive-type photosensitive resin composition used in the art. For example, the organic film may be manufactured by the steps of: applying and drying a positive-type photosensitive resin composition according to the above embodiment on the substrate; exposing the dried layer to light; developing using an alkaline developer; and heating. At this time, the organic film may have a pattern, and the organic film may be used as a surface protective film or an interlayer insulating film.

[0180] According to one embodiment of the present invention, the display device may use any configuration used in the art for display devices without limitation, except that it includes 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.

[0181]

[0182] Hereinafter, the present invention will be described in detail with reference to examples to specifically explain the invention. However, the embodiments according to the present invention may be modified in various different forms, and the scope of the present invention is not to be interpreted as being limited to the embodiments described below. The embodiments of this specification are provided to more completely explain the present invention to those with average knowledge in the art.

[0183]

[0184] ingredient

[0185] amine compounds

[0186] The following compounds were prepared as amine-based compounds.

[0187]

[0188]

[0189]

[0190] acid anhydride compounds

[0191] The following compounds were prepared as acid anhydride compounds.

[0192]

[0193]

[0194]

[0195] End capping compound

[0196] The following compounds were prepared as end-capping compounds.

[0197]

[0198]

[0199] Esterified quinone diazide compounds

[0200] An esterified quinone diazide compound represented by the following chemical formula 3-A1 was prepared.

[0201] [Chemical Formula 3-A1]

[0202]

[0203] At this time, the above chemical formula 3-A1 corresponds to the reaction product of a naphthoquinone diazide compound and a phenolic compound disclosed in Table 4 below. In addition, “A” in the above chemical formula 3-A1 corresponds to the structure (moiety) of the phenolic compound listed in Table 4 below, and the oxygen of the “AO” bond corresponds to the oxygen of the phenolic hydroxyl group of the phenolic compound.

[0204]

[0205]

[0206]

[0207] In the case of the esterified quinone-diazide compound corresponding to the reaction product of the phenolic compound and the naphthoquinone-diazide compound in Code 3-1 of Table 4 above, 2 mol of the naphthoquinone-diazide compound were bonded based on 1 mol of the phenolic compound. In the case of the esterified quinone-diazide compound corresponding to the reaction product of the phenolic compound and the naphthoquinone-diazide compound in Code 3-2 of Table 4 above, 2 mol of the naphthoquinone-diazide compound were bonded based on 1 mol of the phenolic compound.

[0208]

[0209] crosslinking agent

[0210] The following compounds were prepared as crosslinking agents containing phenolic groups.

[0211]

[0212]

[0213]

[0214]

[0215] Preparation of alkali-soluble polymer resins

[0216] Example 1-1

[0217] The amine compounds of Code 1-1 and Code 1-2 of Table 1 were added to gamma-butyrolactone and dissolved at 90°C. Subsequently, the acid anhydride compounds of Code 2-2 and Code 2-8 of Table 2 were added and stirred at 105°C for 4 hours. Then, the end-capping compound of Code E-1 of Table 3 was added and reacted at 70°C for 2 hours, after which the temperature was raised to 150°C. Subsequently, the water produced by the reaction was removed using a Dean-Stark extractor, and the reaction was terminated after stirring at 180°C for 4 hours to synthesize an alkali-soluble polymer resin.

[0218] At this time, based on a total of 100 parts by weight of amine compounds, the content of the amine compound of Code 1-1 was 90 parts by weight, and the content of the amine compound of Code 1-2 was 10 parts by weight. Also, based on a total of 100 parts by weight of amine compounds, the content of the acid anhydride compound of Code 2-2 was 49.5 parts by weight, the content of the acid anhydride compound of Code 2-8 was 49.5 parts by weight, and the content of the end capping compound of Code E-1 was 2 parts by weight.

[0219] In addition, for the alkali-soluble polymer resin, the repeating unit represented by chemical formula B was 85 mol% based on a total of 100 mol% of repeating units represented by chemical formula A and repeating units represented by chemical formula B. At this time, the mol% of repeating units contained in the alkali-soluble polymer resin can be calculated by confirming the conversion rate through the comparison of the -CNC- peaks of the imide bonds 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 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 heated at a temperature of 350°C for 60 minutes to obtain sample (b).

[0220] FT-IR measurements are performed on the obtained samples (a) and (b). In this case, C = C(Aromatic, 1510 cm⁻¹). -1 ), CNC (1370 cm -1 ) was measured. Afterwards, the degree of imidization (CNC / C=C) was compared to calculate the mole% of the repeating unit represented by chemical formula B.

[0221]

[0222] Examples 1-2 to 1-25

[0223] Compared to Example 1-1 above, an alkali-soluble polymer resin was prepared in the same manner as Example 1-1, except that the type and content of the amine-based compound, the type and content of the acid anhydride-based compound, and the type and content of the end-capping compound were adjusted as shown in Table 6 below.

[0224] Amine-based compounds Acid anhydride-based compounds End capping compounds Chemical formula B Repeating unit Content (mol%) Code (parts by weight) Code (parts by weight) Code (parts by weight) Example 1-1 1-1(90) 1-2(10) 2-2(49.5) 2-8(49.5) E-1(2) 89 Example 1-2 1-1(80) 1-2(20) 2-2(49.5) 2-6(49.5) E-2(2) 90 Example 1-3 1-1(70) 1-2(30) 2-2(49.5) 2-5(49.5) E-3(2) 90 Example 1-4 1-2(100) 2-2(48) 2-4(48) E-1(8) 92 Example 1-5 1-2(90) 1-3(10) 2-1(48) 2-2(48) E-2(8) 91 Example 1-6 1-2(90) 1-4(10) 2-3(48) 2-8(48) E-3(8) 89 Example 1-7 1-2(90) 1-5(10) 2-3(46) 2-6(46) E-1(16) 95 Example 1-8 1-2(90) 1-6(10) 2-3(46) 2-5(46) E-2(16) 91 Example 1-9 1-2(90) 1-7(10) 2-3(46) 2-4(46) E-3(16) 85 Example 1-10 1-2(90)1-8(10)2-1(44)2-3(44)E-1(24)88 Example 1-11 1-2(90)1-9(10)2-7(44)2-8(44)E-2(24)90 Example 1-12 1-2(90)1-10(10)2-6(44)2-7(44)E-3(24)94 Example 1-13 1-2(90)1-11(10)2-4(42.5)2-7(42.5)E-1(30)93 Example 1-14 1-2(90)1-12(10)2-1(42.5)2-7(42.5)E-2(30)95 Example 1-15 1-1(50)1-2(50)2-2(42.5)2-8(42.5)E-3(30)91 Example 1-16 1-2(50)1-3(50)2-2(49.5)2-6(49.5)E-1(2)90 Example 1-17 1-2(50)1-4(50)2-2(49.5)2-5(49.5)E-2(2)90 Example 1-18 1-2(50)1-5(50)2-2(49.5)2-4(49.5) E-3(2)89 Example 1-19 1-2(50)1-6(50)2-1(48)2-2(48) E-1(8)92 Example 1-20 1-2(50)1-7(50)2-3(48)2-8(48) E-2(8)90 Example 1-21 1-2(50)1-8(50)2-3(48)2-6(48) E-3(8)89 Example 1-22 1-2(50)1-9(50)2-3(46)2-5(46) E-1(16)90 Example 1-23 1-2(50)1-10(50)2-3(46)2-4(46) E-2(16)90 Example 1-241-2(50)1-11(50)2-1(46)2-3(46)E-3(16)91 Example 1-251-2(50)1-12(50)2-7(44)2-8(44)E-1(24)89.

[0225]

[0226] In Table 6 above, the content (parts by weight) of the amine compounds is based on 100 parts by weight of the total amine compounds. Also, the content (parts by weight) of the acid anhydride compounds and the content (parts by weight) of the end capping compounds are based on 100 parts by weight of the total amine compounds.

[0227]

[0228] Comparative Examples 1-1 to 1-10

[0229] Compared to Example 1-1 above, an alkali-soluble polymer resin was prepared in the same manner as Example 1-1, except that the type and content of the amine-based compound, the type and content of the acid anhydride-based compound, and the type and content of the end-capping compound were adjusted as shown in Table 7 below.

[0230] Amine-based compounds Acid anhydride-based compounds End capping compounds Chemical formula B Repeating unit Content (mol%) Code (parts by weight) Code (parts by weight) Code (parts by weight) Comparative Example 1-11-2(90)1-A(10)2-2(44)2-8(44)E-2(24)90 Comparative Example 1-21-2(90)1-B(10)2-2(44)2-6(44)E-3(24)88 Comparative Example 1-31-2(90)1-C(10)2-2(42.5)2-5(42.5)E-1(30)92 Comparative Example 1-41-2(90)1-D(10)2-2(42.5)2-4(42.5)E-2(30)91 Comparative Example 1-5 1-2(10) 1-A(90) 2-1(42.5) 2-2(42.5) E-3(30) 93 Comparative Example 1-6 1-2(20) 1-A(80) 2-3(44) 2-8(48) E-1(24) 85 Comparative Example 1-7 1-2(30) 1-A(70) 2-3(44) 2-6(44) E-2(24) 88 Comparative Example 1-8 1-2(10) 1-B(90) 2-3(44) 2-5(44) E-3(24) 89 Comparative Example 1-9 1-2(20) 1-B(80) 2-3(42.5) 2-4(42.5) E-2(30) 90 Comparative Example 1-101-2(30)1-B(70)2-1(42.5)2-3(42.5)E-1(30)86

[0231]

[0232] In Table 7 above, the content (parts by weight) of the amine compounds is based on 100 parts by weight of the total amine compounds. Also, the content (parts by weight) of the acid anhydride compounds and the content (parts by weight) of the end capping compounds are based on 100 parts by weight of the total amine compounds.

[0233]

[0234] Preparation of a positive-type photosensitive resin composition

[0235] Example 2-1

[0236] A positive-type photosensitive resin composition was prepared by mixing the alkali-soluble polymer resin prepared in Example 1-1, an esterified quinone-diazide compound comprising the reaction product of a phenolic compound of Formula 3-1 (Code 3-1) and a naphthoquinone-diazide compound, and a crosslinking agent of Formula 4-1 (Code 4-1) with gamma-butyrolactone, an organic solvent.

[0237] At this time, for 100 parts by weight of alkali-soluble polymer resin, the content of the esterified quinone diazide compound was 25 parts by weight and the content of the crosslinking agent was 10 parts by weight.

[0238]

[0239] Examples 2-2 to 2-94

[0240] A positive-type photosensitive resin composition was prepared in the same manner as in Example 2-1, except that the type of alkali-soluble polymer resin, the type and content of the esterified quinone-diazide compound, and the type and content of the crosslinking agent were adjusted as shown in Table 8 below, in contrast to Example 2-1.

[0241] (1)(2)(3) Type (parts by weight) Phenolic compound Code (parts by weight) Code (parts by weight) Code (parts by weight) Example 2-1 Example 1-1 (100) 3-1 (25) 4-1 (5) - Example 2-2 Example 1-2 (100) 3-2 (25) 4-2 (9) - Example 2-3 Example 1-3 (100) 3-1 (25) 4-3 (10) - Example 2-4 Example 1-4 (100) 3-2 (25) 4-1 (12) - Example 2-5 Example 1-5 (100) 3-1 (25) 4-2 (13) - Example 2-6 Example 1-6 (100) 3-2 (25) 4-3 (15) - Example 2-7 Example 1-7(100)3-1(25)4-1(16)-Example 2-8 Example 1-8(100)3-2(25)4-2(18)-Example 2-9 Example 1-9(100)3-1(25)4-3(20)-Example 2-10 Example 1-10(100)3-2(25)4-1(22)-Example 2-11 Example 1-11(100)3-1(25)4-2(25)-Example 2-12 Example 1-12(100)3-2(25)4-3(28)-Example 2-13 Example 1-13(100)3-1(25)4-1(30)-Example 2-14 Example 1-14(100)3-2(25)4-2(33)-Example 2-15 Example 1-15(100)3-1(25)4-3(35)-Example 2-16 Example 1-16(100)3-2(25)4-1(37)-Example 2-17 Example 1-17(100)3-1(25)4-2(39)-Example 2-18 Example 1-18(100)3-2(25)4-2(10)5-3(5)Example 2-19 Example 1-19(100)3-1(25)C-1(5)4-3(15)Example 2-20 Example 1-20(100)3-2(25)4-2(15)5-1(10)Example 2-21Example 1-21(100)3-1(25)C-1(5)5-2(30)Example 2-22Example 1-22(100)3-2(25)4-2(15)5-3(5)Example 2-23Example 1-23(100)3-1(25)4-1(10)5-1(40)Example 2-24Example 1-24(100)3-2(25)4-2(20)5-1(10)Example 2-25Example 1-25(100)3-1(25)4-2(20)5-2(20)Example Example 2-261-1(100)3-1(25)5-1(5)-Example 2-27 Example 1-2(100)3-2(25)5-2(9)-Example 2-28 Example 1-3(100)3-1(25)5-3(10)-Example 2-29 Example 1-4(100)3-2(25)5-1(12)-Example 2-30 Example 1-5(100)3-1(25)5-2(13)-Example 2-31 Example 1-6(100)3-2(25)5-3(15)-Example 2-32 Example 1-7(100)3-1(25)5-1(16)-Example 2-33 Example 1-8(100)3-2(25)5-2(18)-Example 2-34 Example 1-9(100)3-1(25)5-3(20)-Example 2-35 Example 1-10(100)3-2(25)5-1(22)-Example 2-36 Example 1-11(100)3-1(25)5-2(25)-Example 2-37 Example 1-12(100)3-2(25)5-3(28)-Example 2-38 Example 1-13(100)3-1(25)5-1(31)-Example 2-39 Example 1-14(100)3-2(25)5-2(34)-Example 2-40 Example 1-1(100)3-1(25)C-1(5)4-1(13) Example 2-41 Example 1-2(100)3-2(25)C-1(5)4-2(14) Example 2-42 Example 1-3(100)3-1(25)C-1(5)4-3(17) Example 2-43 Example 1-4(100)3-2(25)C-1(5)4-1(20) Example 2-44 Example 1-5(100)3-1(25)C-1(5)4-2(25) Example 2-45 Example 1-6(100)3-2(25)C-1(5)4-3(30) Example 2-46 Example 1-7 (100) 3-1 (25) C-1 (5) 4-1 (38) Example 2-47 Example 1-11 (100) 3-1 (25) C-1 (5) 5-1 (9) Example 2-48 Example 1-12 (100) 3-2 (25) C-1 (5) 5-2 (10) Example 2-49 Example 1-13 (100) 3-1 (25) C-1 (5) 5-3 (15) Example 2-50 Example 1-14 (100) 3-2 (25) C-1 (5) 5-1 (20) Example 2-51 Example 1-15 (100) 3-1 (25) C-1 (5) 5-2 (25) Example 2-52 Example1-16(100)3-2(25)C-1(5)5-3(30)Example 2-53 Example 1-21(100)3-1(25)C-1(10)4-1(10)Example 2-54 Example 1-22(100)3-2(25)C-1(10)4-2(12)Example 2-55 Example 1-23(100)3-1(25)C-1(10)4-3(14)Example 2-56 Example 1-24(100)3-2(25)C-1(10)4-1(17)Example 2-57 Example 1-25(100)3-1(25)C-1(10)4-2(20)Example 2-58 Example 1-1(100)3-2(25)C-1(10)4-3(25) Example 2-59 Example 1-2(100)3-1(25)C-1(10)4-1(30) Example 2-60 Example 1-7(100)3-2(25)C-1(10)5-1(5) Example 2-61 Example 1-8(100)3-1(25)C-1(10)5-2(7) Example 2-62 Example 1-9(100)3-2(25)C-1(10)5-3(8) Example 2-63 Example 1-10(100)3-1(25)C-1(10)5-1(20) Example 2-64 Example 1-11 (100) 3-2 (25) C-1 (10) 5-2 (25) Example 2-65 Example 1-12 (100) 3-1 (25) C-1 (10) 5-3 (30) Example 2-66 Example 1-17 (100) 3-2 (25) 4-1 (5) 5-1 (5) Example 2-67 Example 1-18 (100) 3-1 (25) 4-2 (5) 5-2 (6) Example 2-68 Example 1-19 (100) 3-2 (25) 4-3 (5) 5-3 (8) Example 2-69 Example 1-20 (100) 3-1 (25) 4-1 (5) 5-1 (10) Example 2-70 Example 1-21 (100) 3-2 (25) 4-2 (5) 5-2 (20) Example 2-71 Example 1-22 (100) 3-1 (25) 4-3 (5) 5-3 (30) Example 2-72 Example 1-25 (100) 3-2 (25) 4-3 (10) 5-1 (2) Example 2-73 Example 1-1 (100) 3-1 (25) 4-1 (10) 5-2 (4) Example 2-74 Example 1-2 (100) 3-2 (25) 4-2 (10) 5-3 (8) Example 2-75 Example 1-3 (100) 3-1 (25) 4-3 (10) 5-1 (10) Example Example 2-761-4(100)3-2(25)4-1(10)5-2(20)Example 2-77 Example 1-18(100)3-2(25)4-3(40)-Example 2-78 Example 1-19(100)3-1(25)4-1(41)-Example 2-79 Example 1-20(100)3-2(25)4-2(45)-Example 2-80 Example 1-21(100)3-1(25)4-3(48)-Example 2-81 Example 1-22(100)3-2(25)4-1(50)-Example 2-82 Example 1-15(100)3-1(25)5-3(35)-Example 2-83 Example 1-16(100)3-2(25)5-1(37)-Example 2-84 Example 1-17(100)3-1(25)5-2(39)-Example 2-85 Example 1-18(100)3-2(25)5-3(40)-Example 2-86 Example 1-19(100)3-1(25)5-1(41)-Example 2-87 Example 1-20(100)3-2(25)5-2(45)-Example 2-88 Example 1-21(100)3-1(25)5-3(48)-Example 2-89 Example 1-22 (100) 3-2 (25) 5-1 (50) - Example 2-90 Example 1-17 (100) 3-1 (25) C-1 (5) 5-1 (38) Example 2-91 Example 1-3 (100) 3-2 (25) C-1 (5) 4-2 (38) Example 2-92 Example 1-13 (100) 3-2 (25) C-1 (10) 5-1 (38) Example 2-93 Example 1-23 (100) 3-2 (25) 4-1 (5) 5-1 (45) Example 2-94 Example 1-5 (100) 3-1 (25) 4-2 (10) 5-3 (30)

[0242]

[0243] In Table 8 above, (1) represents an alkali-soluble polymer resin, (2) represents an esterified quinone-diazide compound, and (3) represents a crosslinking agent. Also, in Table 8 above, the content (parts by weight) of the esterified quinone-diazide compound and the crosslinking agent is based on 100 parts by weight of the alkali-soluble polymer resin.

[0244]

[0245] Reference Examples 2-1 to 2-9, Comparative Examples 2-1 to 2-38

[0246] A positive-type photosensitive resin composition was prepared in the same manner as in Example 2-1, except that, in comparison to Example 2-1, the type of alkali-soluble polymer resin, the type and content of the esterified quinone-diazide compound, and the type and content of the crosslinking agent were adjusted as shown in Table 9 below.

[0247]

[0248] (1)(2)(3) Type (parts by weight) Phenolic compound Code (parts by weight) Code (parts by weight) Code (parts by weight) Reference Example 2-1 Example 1-1 (100) 3-1 (25) C-1 (5) - Reference Example 2-2 Example 1-2 (100) 3-2 (25) C-1 (10) - Reference Example 2-3 Example 1-3 (100) 3-1 (25) C-1 (20) - Reference Example 2-4 Example 1-4 (100) 3-2 (25) C-1 (50) - Reference Example 2-5 Example 1-5 (100) 3-1 (25) 4-1 (10) - Reference Example 2-6 Example 1-6 (100) 3-2 (25) 4-2 (50) - Reference Example 2-7 Example 1-7(100)3-1(25)4-3(50)-Reference Example 2-8 Example 1-8(100)3-2(25)5-1(5)-Reference Example 2-9 Example 1-9(100)3-1(25)5-2(50)-Comparative Example 2-1 Comparative Example 1-1(100)3-2(25)4-1(10)-Comparative Example 2-2 Comparative Example 1-2(100)3-1(25)4-2(20)-Comparative Example 2-3 Comparative Example 1-3(100)3-2(25)4-3(30)-Comparative Example 2-4 Comparative Example 1-4(100)3-1(25)5-1(13)-Comparative Example 2-5 Comparative Example 1-5(100)3-2(25)5-2(11)-Comparative Example 2-6 Comparative Example 1-6(100)3-1(25)5-3(15)-Comparative Example 2-7 Comparative Example 1-7(100)3-2(25)4-1(40)-Comparative Example 2-8 Comparative Example 1-8(100)3-1(25)4-2(50)-Comparative Example 2-9 Comparative Example 1-9(100)3-2(25)C-1(8)-Comparative Example 2-10 Comparative Example 1-10(100)3-1(25)C-1(10)-Comparative Example 2-11 Comparative Example 1-1(100)3-2(25)C-1(12)-Comparative Example 2-12 Comparative Example 1-2(100)3-1(25)C-1(14)-Comparative Example 2-13 Comparative Example 1-3(100)3-2(25)C-1(16)-Comparative Example 2-14 Comparative Example 1-4(100)3-1(25)C-1(18)-Comparative Example 2-15 Comparative Example 1-5(100)3-2(25)C-1(20)-Comparative Example 2-16 Comparative Example 1-6(100)3-1(25)C-1(22)-Comparative Example 2-17 Comparative Example 1-7(100)3-2(25)C-1(24)-Comparative Example 2-18 Example 1-23(100)3-1(25)4-2(51)-Comparative Example 2-19 Example1-24(100)3-2(25)4-3(53)-Comparative Example 2-20 Example 1-25(100)3-1(25)4-1(55)-Comparative Example 2-21 Example 1-23(100)3-1(25)5-2(51)-Comparative Example 2-22 Example 1-24(100)3-2(25)5-3(53)-Comparative Example 2-23 Example 1-25(100)3-1(25)5-1(55)-Comparative Example 2-24 Example 1-8(100)3-2(25)C-1(5)4-2(46)Comparative Example 2-25 Example 1-9(100)3-1(25)C-1(5)4-3(48)Comparative Example 2-26 Example 1-10(100)3-2(25)C-1(5)4-1(50)Comparative Example 2-27 Example 1-18(100)3-2(25)C-1(5)5-2(46)Comparative Example 2-28 Example 1-19(100)3-1(25)C-1(5)5-3(48)Comparative Example 2-29 Example 1-20(100)3-2(25)C-1(5)5-1(50)Comparative Example 2-30 Example 1-4(100)3-1(25)C-1(10)4-3(46)Comparative Example 2-31 Example 1-5(100)3-2(25)C-1(10)4-1(48)Comparative Example 2-32 Example 1-6(100)3-1(25)C-1(10)4-2(50)Comparative Example 2-33 Example 1-14(100)3-1(25)C-1(10)5-2(46)Comparative Example 2-34 Example 1-15(100)3-2(25)C-1(10)5-3(48)Comparative Example 2-35 Example 1-16(100)3-1(25)C-1(10)5-1(50)Comparative Example 2-36 Example 1-24(100)3-1(25)4-2(5)5-2(47)Comparative Example 2-37 Example 1-6 (100) 3-2 (25) 4-3 (10) 5-1 (45) Comparative Example 2-38 Example 1-7 (100) 3-1 (25) 4-1 (10) 5-2 (47)

[0249]

[0250] In Table 9 above, (1) represents an alkali-soluble polymer resin, (2) represents an esterified quinone-diazide compound, and (3) represents a crosslinking agent. Also, in Table 9 above, the content (parts by weight) of the esterified quinone-diazide compound and the crosslinking agent is based on 100 parts by weight of the alkali-soluble polymer resin.

[0251]

[0252] Experimental Example

[0253] For the positive-type photosensitive resin compositions prepared in the above examples, reference examples, and comparative examples, the fluorine content, sensitivity, residual film rate, adhesion, chemical resistance, heat resistance, solar resistance, driving reliability, bending characteristics, and contact resistance were measured by the following methods. The measured results are listed in Tables 10 to 13 below.

[0254]

[0255] Fluorine content measurement

[0256] The fluorine content in the photosensitive resin composition was measured using Combustion Ion Chromatography (CIC).

[0257]

[0258] Sensitivity measurement

[0259] A substrate coated with a photosensitive resin composition was irradiated with ultraviolet light having a broadband intensity of 20 mW / cm² using a predetermined pattern mask at a dose based on the formation of a 5 μm contact hole CD. Subsequently, the substrate was developed at 23°C for 1 minute using an aqueous solution of 2.38 parts by weight of tetramethylammonium hydroxide, followed by washing with ultrapure water for 1 minute. Afterward, the film was cured in an oven at 250°C for 60 minutes to obtain a patterned film with a contact hole CD of 7 μm. The sensitivity was 40 to 150 mJ / cm². 2 If this is satisfied with an appropriate result value, it is marked as O.

[0260]

[0261] Residual film rate measurement

[0262] The residual film rate of the above-mentioned manufactured substrate was measured by comparing the initial coating thickness and the final thickness after all processes. It was indicated as ◎ if the ratio of the final thickness to the initial thickness was 60% or more, and as ○ if it was less than 60%.

[0263]

[0264] Adhesion strength measurement

[0265] A pattern film was formed in the same manner as in the sensitivity measurement above, but the adhesion strength according to the bake temperature was compared based on the case where the line width and slit width were 1:1 of 10 μm. At this time, the case where adhesion strength was secured at a pre-bake of 90°C to 100°C was indicated as O, and the case where adhesion strength was secured or not secured at a pre-bake of 120°C or higher was indicated as X.

[0266]

[0267] Chemical resistance measurement

[0268] The above-mentioned substrate was immersed in an evaluation solvent (Stripper) at 25°C for 120 seconds, and the rate of change in cured film thickness before and after immersion was measured and indicated as ◎ for 0 Å or more and less than 150 Å, ○ for 150 Å or more and less than 300 Å, △ for 300 Å or more and less than 600 Å, and X for 600 Å or more (the evaluation solvent was propylene glycol methyl ether:propylene glycol methyl ether acetate = 7:3 molar ratio).

[0269]

[0270] Heat resistance measurement

[0271] For the above sensitivity evaluation, the organic film portion of the manufactured substrate (up to the completion of the curing process) was recovered and evaluated using a Thermogravimetric Analyzer (TGA) at 50 to 500°C and 10°C / min. Weight loss was indicated as ◎ when the temperature was 350°C or higher, ○ when it was 300°C or higher but less than 350°C, and △ when it was less than 300°C.

[0272]

[0273] Solar tolerance measurement

[0274] A pattern film is formed on a patterned ITO substrate in the same manner as the sensitivity measurement above, and EL is deposited. Al is deposited as a cathode electrode on top, and an encapsulation process is performed. After irradiating with an exposure amount of 2100 J 10 times using a Xenon Lamp Solar Simulator, the time (T97) for a 3% luminance drop in the On state was evaluated. ○ was indicated if 1000 hours or more were secured, and X was indicated if less than 1000 hours were secured.

[0275]

[0276] Driving reliability measurement

[0277] A pattern film can be formed in the same way as when measuring sensitivity above.

[0278] FIG. 1 is a diagram showing the formation of a pattern film on a patterned ITO substrate and the deposition of EL. Specifically, 10 in FIG. 1 is the source / drain (Ti / Al / Ti), 20 corresponds to the organic film, 30 is the anode (ITO / Ag / ITO), and 40 is the pixel define layer (PDL).

[0279] As shown in Fig. 1, Al is deposited as a cathode on the top, and an encapsulation process is performed. The time (T97) for a 3% brightness drop in the device On state was evaluated based on 85 ℃ and 85% RH. Cases where 1000 hours or more are secured are marked as ◎, cases where 950 hours or more but less than 1000 hours are marked as ○, and cases where 950 hours or less are less than 950 hours are marked as X.

[0280]

[0281] Bending characteristic measurement

[0282] A 100 μm thick polyimide (PI) film was coated with a material to a thickness of 3 μm and in-folded 200,000 times with a radius of curvature of 1R. If multiple cracks were observed in the folding part, it was marked X, and if no cracks were observed, it was marked O.

[0283]

[0284] Contact resistance measurement

[0285] A material is coated to a thickness of about 3 μm on a metal substrate identical to the electrode to create a hole pattern of 2.5 to 3.0 μm. Copper metal is deposited to a thickness of about 2,000 Å on the material to measure the resistance between the upper electrode and the lower electrode. A value less than 0.1 Ω is indicated as O, and a value greater than 0.1 Ω is indicated as X.

[0286]

[0287] Fluorine Content (ppm) Sensitivity Residual Film Rate Adhesion Chemical Resistance Example 2-10○◎○○ Example 2-20○◎○○ Example 2-30○◎○○ Example 2-40○◎○○ Example 2-50○◎○○ Example 2-60○◎○○ Example 2-70○◎○◎ Example 2-80○◎○◎ Example 2-90○◎○◎ Example 2-100○◎○◎ Example 2-110○◎○◎ Example 2-120○◎○◎ Example 2-130○◎○◎ Example 2-140○◎○◎ Example 2-150○◎○◎ Example 2-160○◎○◎ Example 2-170○◎○◎ Example 2-180○◎○◎ Example 2-190○◎○○ Example 2-200○◎○◎ Example 2-210○◎○○ Example 2-220○◎○◎ Example 2-230○◎○○ Example 2-240○◎○◎ Example 2-250○◎○◎ Example 2-260○◎○○ Example 2-270○◎○○ Example 2-280○◎○◎ Example 2-290○◎○◎ Example 2-300○◎○◎ Example 2-310○◎○◎ Example 2-320○◎○◎ Example 2-330○◎○◎ Example 2-340○◎○◎ Example 2-350○◎○◎ Example 2-360○◎○◎ Example 2-370○◎○◎Example 2-380○◎○◎Example 2-390○◎○◎Example 2-400○◎○○Example 2-410○◎○◎Example 2-420○◎○◎Example 2-430○◎○◎Example 2-440○◎○◎Example 2-450○◎○◎Example 2-460○◎○◎Example 2-470○◎○◎Example 2-480○◎○◎Example 2-490○◎○◎Example 2-500○◎○◎Example 2-510○◎○◎Example 2-520○◎○◎Example 2-530○◎○○Example 2-540○◎○◎Example 2-550○◎○◎Example 2-560○◎○◎Example 2-570○◎○◎Example 2-580○◎○◎Example 2-590○◎○◎Example 2-600○◎○○Example 2-610○◎○○Example 2-620○◎○◎Example 2-630○◎○◎Example 2-640○◎○◎Example 2-650○◎○◎Example 2-660○◎○○Example 2-670○◎○◎Example 2-680○◎○◎Example 2-690○◎○◎Example 2-700○◎○◎Example 2-710○◎○◎Example 2-720○◎○○Example 2-730○◎○◎Example 2-740○◎○◎Example 2-750○◎○◎Example2-760○◎○◎Example 2-770○○○◎Example 2-780○○○◎Example 2-790○○○◎Example 2-800○○○◎Example 2-810○○○◎Example 2-820○○○◎Example 2-830○○○◎Example 2-840○○○◎Example 2-850○○○◎Example 2-860○○○◎Example 2-870○○○◎Example 2-880○○○◎Example 2-890○○○◎Example 2-900○○○◎Example 2-910○◎○◎Example 2-920○○○◎Example 2-930○○○◎Example 2-940○○○◎

[0288]

[0289] Heat Resistance Solar Resistance Driving Reliability Bending Characteristics Contact Resistance Example 2-1 Example 2-2 Example 2-3 Example 2-4 Example 2-5 Example 2-6 Example 2-7 Example 2-8 Example 2-9 Example 2-10 Example 2-11 Example 2-12 Example 2-13 Example 2-14 Example 2-15 Example 2-16 Example 2-18 Example 2-17 Example 2-18 Example 2-19 Example 2-20 Example 2-21 Example 2-22 Example 2-23 Example 2-24 Example 2-25 Example 2-26 Example 2-27 Example 2-28 Example 2-29 Example 2-30 Example 2-31 Example 2-32 Example 2-33 Example 2-34 Example 2-35 Example 2-36 Example 2-3 2-37 ◎○◎○○ Example 2-38 ◎○◎○○ Example 2-39 ◎○◎○○ Example 2-40 ○○◎○○ Example 2-41 ◎○◎○○ Example 2-42 ◎○◎○○ Example 2-43 ◎○◎○○ Example 2-44 ◎○◎○○ Example 2-45 ◎○◎○○ Example 2-46 ◎○◎○○ Example 2-47 ◎○◎○○ Example 2-48 ◎○◎○○ Example 2-49 ◎○◎○○ Example 2-50 ◎○◎○○ Example 2-51 ◎○◎○○ Example 2-52 ◎○◎○○ Example 2-53 ○○◎○○ Example 2-54 ◎○◎○○ Example 2-55 ◎○◎○○ Example 2-56 ◎○◎○○ Example 2-57 ◎○◎○○ Example 2-58 ◎○◎○○ Example 2-59 ◎○◎○○ Example 2-60 ○○◎○○ Example 2-61 ○○◎○○ Example 2-62 ◎○◎○○ Example 2-63 ◎○◎○○ Example 2-64 ◎○◎○○ Example 2-65 ◎○◎○○ Example 2-66 ○○◎○○ Example 2-67 ◎○◎○○ Example 2-68 ◎○◎○○ Example 2-69 ◎○◎○○ Example 2-70 ◎○◎○○ Example 2-71 ◎○◎○○ Example 2-72 ○○◎○○ Example 2-73 ◎○◎○○ Example 2-74 ◎○◎○○ Example 2-75 ◎○◎○○ Example2-76 ◎○◎○○ Example 2-77 ◎○◎○○ Example 2-78 ◎○○○○ Example 2-79 ◎○○○○ Example 2-80 ◎○○○○ Example 2-81 ◎○○○○ Example 2-82 ◎○○○○ Example 2-83 ◎○○○○ Example 2-84 ◎○○○○ Example 2-85 ◎○○○○ Example 2-86 ◎○○○○ Example 2-87 ◎○○○○ Example 2-88 ◎○○○○ Example 2-89 ◎○○○○ Example 2-90 ◎○○○○ Example 2-91 ◎○◎○○ Example 2-92 ◎○○○○ Example 2-93 ◎○○○○ Example 2-94 ◎○◎○○

[0290]

[0291] Fluorine Content (ppm) Sensitivity Residual Film Rate Adhesion Chemical Resistance Reference Example 2-10○◎○△ Reference Example 2-20○◎○△ Reference Example 2-30○◎○△ Reference Example 2-40○◎○◎ Reference Example 2-50○◎○△ Reference Example 2-60○○○◎ Reference Example 2-70○○○◎ Reference Example 2-80○◎○△ Reference Example 2-90○○○◎ Comparative Example 2-12,042○◎○○ Comparative Example 2-22,010○◎○◎ Comparative Example 2-32,000○◎○◎ Comparative Example 2-42,038○◎○◎ Comparative Example 2-58,014○◎○◎ Comparative Example 2-67,333○◎○◎ Comparative Example 2-76,589○○○◎ Comparative Example 2-88,199○○○◎Comparative Example 2-97,514○◎○○Comparative Example 2-106,433○◎○○Comparative Example 2-112,042○◎○○Comparative Example 2-122,010○◎○○Comparative Example 2-132,000○◎○○Comparative Example 2-142,038○◎○○Comparative Example 2-158,014○◎○○Comparative Example 2-167,333○◎○○Comparative Example 2-176,589○◎○○Comparative Example 2-180○○○◎Comparative Example 2-190○○○◎Comparative Example 2-200○○○◎Comparative Example 2-210○○○◎Comparative Example 2-220○○○◎Comparative Example 2-230○○○◎Comparative Example 2-240○○○◎Comparative Example 2-250○○○◎Comparative Example 2-260○○○◎Comparative Example 2-270○○○◎Comparative Example 2-280○○○◎Comparative Example 2-290○○○◎Comparative Example 2-300○○○◎Comparative Example 2-310○○○◎Comparative Example 2-320○○○◎Comparative Example 2-330○○○◎Comparative Example 2-340○○○◎Comparative Example 2-350○○○◎Comparative Example 2-360○○○◎Comparative Example 2-370○○○◎Comparative Example 2-380○○○◎

[0292]

[0293] Heat Resistance Solar Resistance Driving Reliability Bending Characteristics Contact Resistance Reference Example 2-1 △○◎○○ Reference Example 2-2 △○◎○○ Reference Example 2-3 △○◎○○ Reference Example 2-4 ◎○X○○ Reference Example 2-5 △○◎○○ Reference Example 2-6 ◎○X○○ Reference Example 2-7 ◎○X○○ Reference Example 2-8 △○◎○○ Reference Example 2-9 ◎○X○○ Comparative Example 2-1 ○○◎○X Comparative Example 2-2 ◎○◎○X Comparative Example 2-3 ◎○◎○X Comparative Example 2-4 ◎○◎○X Comparative Example 2-5 ◎○◎○X Comparative Example 2-6 ◎○◎○X Comparative Example 2-7 ◎○◎○X Comparative Example 2-8 ◎○X○X Comparative Example 2-9 ○○◎○X Comparative Example 2-10○○◎○X Comparative Example 2-11○○◎○X Comparative Example 2-12○○◎○X Comparative Example 2-13○○◎○X Comparative Example 2-14○○◎○X Comparative Example 2-15○○◎○X Comparative Example 2-16○○◎○X Comparative Example 2-17○○◎○X Comparative Example 2-18◎○X○○ Comparative Example 2-19◎○X○○ Comparative Example 2-20◎○X○○ Comparative Example 2-21◎○X○○ Comparative Example 2-22◎○X○○ Comparative Example 2-23◎○X○○ Comparative Example 2-24◎○X○○ Comparative Example 2-25◎○X○○ Comparative Example 2-26◎○X○○ Comparative Example 2-27◎○X○○ Comparative Example 2-28 ◎○X○○ Comparative Example 2-29 ◎○X○○ Comparative Example 2-30 ◎○X○○ Comparative Example 2-31 ◎○X○○ Comparative Example 2-32 ◎○X○○ Comparative Example 2-33 ◎○X○○ Comparative Example 2-34 ◎○X○○ Comparative Example 2-35 ◎○X○○ Comparative Example 2-36 ◎○X○○ Comparative Example 2-37 ◎○X○○ Comparative Example 2-38 ◎○X○○

[0294]

[0295] Referring to Tables 10 to 13 above, it was confirmed that the positive-type photosensitive resin compositions prepared in Examples 2-1 to 2-94 exhibited excellent properties in terms of sensitivity, residual film rate, adhesion, chemical resistance, heat resistance, solar resistance, driving reliability, bending characteristics, and contact resistance. On the other hand, it was confirmed that the properties of Reference Examples 2-1 to 2-9 were somewhat inferior compared to Examples 2-1 to 2-94. Meanwhile, it was confirmed that the properties of Comparative Examples 2-1 to 2-38 were significantly inferior compared to Examples 2-1 to 2-94. Specifically, it was confirmed that in the case of the positive-type photosensitive resin compositions of Comparative Examples 2-1 to 2-38, none satisfied the requirements for excellent sensitivity, residual film rate, adhesion, chemical resistance, heat resistance, solar resistance, driving reliability, bending characteristics, and contact resistance properties.

[0296] Accordingly, it can be seen that the positive type photosensitive resin composition according to one embodiment of the present invention can easily realize an organic film with excellent properties such as sensitivity, residual film rate, adhesion, chemical resistance, heat resistance, solar resistance, driving reliability, bending characteristics, and contact resistance.

[0297] [Explanation of the symbol]

[0298] 10: Source Drain 20: Organic Film

[0299] 30: Anode 40: PDL

Claims

A positive type photosensitive resin composition, Alkali-soluble polymer resin; Esterified quinone-diazide compounds; and A crosslinking agent containing a phenol group: comprising, The above positive-type photosensitive resin composition has a fluorine content of less than 250 ppm, and A positive-type photosensitive resin composition having a content of 5 parts by weight or more and 50 parts by weight or less for every 100 parts by weight of the alkali-soluble polymer resin. In paragraph 1, A positive-type photosensitive resin composition wherein the above alkali-soluble polymer resin comprises a repeating unit represented by the following chemical formula A and a repeating unit represented by the following chemical formula B: [Chemical Formula A] [Chemical Formula B] In the above chemical formulas A and B, The above R a and R b Each is independently an organic group having 5 to 60 carbon atoms, and a and b are each independently integers from 0 to 4, and a+b is 1 or greater. In paragraph 2, The above alkali-soluble polymer resin is, A positive-type photosensitive resin composition having 51 mol% or more of the repeating unit represented by chemical formula B, based on a total of 100 mol% of the repeating unit represented by chemical formula A and the repeating unit represented by chemical formula B. In paragraph 2, The repeating unit represented by the above chemical formula A and the repeating unit represented by the above chemical formula B are R b It includes a structure derived from an amine-based compound containing, A positive-type photosensitive resin composition in which the above amine-based compound comprises a diamine-based compound having at least one hydroxyl group attached. In paragraph 2, The repeating unit represented by the above chemical formula A and the repeating unit represented by the above chemical formula B are R a It includes a structure derived from an acid anhydride compound containing, A positive-type photosensitive resin composition in which the above acid anhydride compound includes a cyclic acid dianhydride compound. In paragraph 1, A positive-type photosensitive resin composition wherein the esterified quinone-diazide compound comprises a reaction product of a quinone-diazide compound and at least one of a phenolic compound represented by the following chemical formulas 3-1 to 3-13: In the above chemical formulas, R 3-1 to R 3-84 Each is 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 and an alkyl group having 1 to 4 carbon atoms. In paragraph 1, A positive-type photosensitive resin composition having a content of 10 parts by weight or more and 40 parts by weight or less of the esterified quinone-diazide compound per 100 parts by weight of the alkali-soluble polymer resin. In paragraph 1, The above-mentioned crosslinking agent is, A positive-type photosensitive resin composition comprising three or more phenolic groups represented by the following chemical formula C: [Chemical Formula C] In the above chemical formula, R c-1 and R c-2 Each independently comprises hydrogen, an organic group having 1 to 60 carbon atoms, or is, R c-1 and R c-2 At least one of them And, R c-3 and R c-4 Each is independently hydrogen, a hydroxyl group, or an organic group having 1 to 30 carbon atoms, and m is an integer from 1 to 27, and R c-5 is an alkyl group having 1 to 3 carbon atoms. In paragraph 1, The above crosslinking agent comprises at least one of the first crosslinking agent and the second crosslinking agent, and A positive-type photosensitive resin composition wherein the first crosslinking agent comprises a compound represented by the following chemical formula 4, and the second crosslinking agent comprises a compound represented by the following chemical formula 5: [Chemical Formula 4] [Chemical Formula 5] In the above chemical formulas, R 4-1 and R 5-1 Each is independently an unsubstituted or substituted straight-chain or branched-chain alkylene having 1 to 20 carbon atoms; an unsubstituted or substituted straight-chain or branched-chain alkenylene having 2 to 20 carbon atoms; an unsubstituted or substituted straight-chain or branched-chain hydrocarbon linker having 6 to 12 carbon atoms comprising at least one unsubstituted or substituted aromatic group having 6 to 30 carbon atoms; or an unsubstituted or substituted straight-chain or branched-chain hydrocarbon linker having 4 to 16 carbon atoms comprising at least one unsubstituted or substituted cycloalkyl group having 5 to 10 carbon atoms; and R c-1 and R c-2 Each independently comprises hydrogen, an organic group having 1 to 60 carbon atoms, or is, R c-1 and R c-2 At least one of them And, m is an integer from 1 to 27, and R c-5 is an alkyl group having 1 to 3 carbon atoms, and The substituents of the substituted alkylene, the substituted alkenylene, the substituted aromatic group, the substituted cycloalkyl group, and the substituted hydrocarbon are alkyl groups having 1 to 5 carbon atoms, alkenyl groups having 2 to 5 carbon atoms, or alkynyl groups having 2 to 5 carbon atoms. In Paragraph 9, A positive-type photosensitive resin composition wherein the first crosslinking agent comprises at least one of the compounds represented by the following chemical formulas 4-1 to 4-3: In the above chemical formulas, R c-1 and R c-2 Each independently hydrogen, a carbon-1 to carbon-3 alkyl group, or is, R c-1 and R c-2 At least one of them And, m is an integer from 1 to 6, and R c-5 is an alkyl group having 1 to 3 carbon atoms. In Paragraph 9, The above crosslinking agent includes a first crosslinking agent, A positive-type photosensitive resin composition having a content of 16 parts by weight or more and 39 parts by weight or less of the first crosslinking agent per 100 parts by weight of the alkali-soluble polymer resin. In Paragraph 9, A positive-type photosensitive resin composition wherein the second crosslinking agent comprises at least one of the compounds represented by the following chemical formulas 5-1 to 5-6: In the above chemical formulas, R c-1 and R c-2 Each independently hydrogen, a carbon-1 to carbon-3 alkyl group, or is, R c-1 and R c-2 At least one of them And, m is an integer from 1 to 6, and R c-5 is an alkyl group having 1 to 3 carbon atoms. In Paragraph 9, The above crosslinking agent includes a second crosslinking agent, A positive-type photosensitive resin composition having a content of 10 parts by weight or more and 34 parts by weight or less of the second crosslinking agent per 100 parts by weight of the alkali-soluble polymer resin. In paragraph 1, A positive-type photosensitive resin composition comprising at least one of an organic solvent, a surfactant, and an additive. Substrate; and Includes an organic film disposed on the above substrate; The above organic film is a display device comprising a cured product of a positive-type photosensitive resin composition according to claim 1.

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