Photosensitive resin composition with low reflectance and light shielding layer using the same

Abstract

According to an embodiment of the present application, there is provided a display device including: a photosensitive resin composition including: a resin including a repeating unit represented by Chemical Formula (1), a dye represented by Chemical Formula (2), a reactive unsaturated compound, a pigment, an initiator, and a solvent; and a pattern layer including: a polymerization product of the photosensitive resin composition.

Description

Technical Field

[0001] The present invention relates to a photosensitive resin composition that includes dyes in addition to conventionally used black and black combination pigments, thereby effectively reducing reflectivity, and a coloring and light-blocking layer utilizing the same. Background Technology

[0002] Flat panel displays widely utilize liquid crystal displays (LCDs) and organic light-emitting displays (OLEDs). In particular, OLEDs offer advantages such as low power consumption, fast response time, high color reproduction rate, high brightness, and wide viewing angle.

[0003] The purpose of using a polarizing film in the organic light-emitting display device is to block the light reflected from the panel after incident external light. Its drawback is that, due to its lack of bending characteristics, it is not suitable for use in flexible devices.

[0004] To address the aforementioned issues, previous suggestions have included using color filters, a black matrix, and forming a light-shielding inorganic film on the upper substrate. However, these methods have limitations in achieving the desired level of anti-reflection effect and do not specifically provide a method to replace the polarizing film.

[0005] In addition, colored light-shielding layers, particularly black light-shielding layers, are used in liquid crystal display devices to prevent color interference between red, green, and blue color filters, thereby improving image quality. Recently, organic light-emitting displays have also been researching the use of such colored light-shielding layers to achieve the same purpose and improve image visibility through low reflectivity.

[0006] When manufacturing the light-shielding layer, carbon black and organic pigments are used as black colorants. Due to their isodispersed application, the pigment dispersion is mixed with other compositions to form a pattern.

[0007] At this point, multiple black or black-displaying combination pigments are used. To achieve this goal, it is necessary to study how to effectively reduce the reflectivity around 550nm, as the area around 550nm has the greatest impact on visibility.

[0008] [Preliminary Technology Documents]

[0009] [Patent Documents]

[0010] (Patent Document 1) Korean Patent No. 10-1141566 Summary of the Invention

[0011] The problem to be solved

[0012] The purpose of this invention is to provide a photosensitive resin composition that can reduce the reflectivity at a wavelength of 550 nm to improve visibility.

[0013] Furthermore, the object of the present invention is to provide a light-shielding layer manufactured using the photosensitive resin composition and a display device including the light-shielding layer.

[0014] Problem Solution

[0015] An embodiment of the photosensitive resin composition of the present invention comprises:

[0016] Adhesive resin, comprising repeating units represented by the following chemical formula (1);

[0017] The dye represented by the following chemical formula (2);

[0018] pigment;

[0019] Reactive unsaturated compounds;

[0020] Photoinitiators; and

[0021] Solvent,

[0022] Chemical formula (1):

[0023]

[0024] In the chemical formula (1),

[0025] 1) * indicates the part where the key is connected by repeating units.

[0026] 2)R 1 and R 2 Independently defined: hydrogen; deuterium; halogen; C6–C 30 aryl group; C2-C containing at least one heteroatom from O, N, S, Si, and P. 30 Heterocyclyl group; C6~C 30 Cyclo group of aliphatic and aromatic rings; C1~C 20 Alkyl group; C2-C 20 alkenyl group; C2~C 20 alkinyl group; C1-C 20 alkoxy group; C6~C 30The aryloxy group; fluorenyl group; carbonyl group; ether group; or C1-C2. 20 The alkoxy carbonyl group,

[0027] 3)R 1 and R 2 They can form rings with adjacent groups,

[0028] 4) a and b are independent integers from 0 to 4.

[0029] 5)X 1 It is a single bond, O, CO, SO2, CR'R", SiR'R", chemical formula (A) or chemical formula (B).

[0030] 6)X 2 It is C6~C 30 aryl group; C2-C containing at least one heteroatom from O, N, S, Si, and P. 30 heterocyclyl group; C6~C 30 Cyclo group of aliphatic and aromatic rings; C1~C 20 Alkyl group; C2~C 20 alkenyl group; C2~C 20 alkinyl group; C1-C 20 alkoxy group; C6~C 30 aryloxy groups; or combinations thereof,

[0031] 7) R' and R" are independently: hydrogen; deuterium; halogen; C6~C 30 aryl group; C2-C containing at least one heteroatom from O, N, S, Si, and P. 30 Heterocyclyl group; C6~C 30 Cyclo group of aliphatic and aromatic rings; C1~C 20 Alkyl group; C2-C 20 alkenyl group; C2~C 20alkinyl group; C1-C 20 alkoxy group; C6~C 30 The aryloxy group; fluorenyl group; carbonyl group; ether group; or C1-C2. 20 The alkoxy carbonyl group,

[0032] 8) R' and R" can form rings with adjacent groups, respectively.

[0033] 9)A 1 and A 2 They are independently represented by the chemical formula (C) or the chemical formula (D).

[0034] 10) The resin comprises repeating units represented by chemical formula (1), wherein within the polymer chain, the ratio of chemical formula (C) to chemical formula (D) satisfies 1:9 to 9:1.

[0035] Chemical formula (A):

[0036]

[0037] Chemical formula (B):

[0038]

[0039] In the chemical formulas (A) and (B),

[0040] 11-1)* indicates the bonding position.

[0041] 11-2)X3 is O, S, SO2 or NR',

[0042] 11-3) R' is hydrogen; deuterium; halogen; C6~C 30 aryl group; C2-C containing at least one heteroatom from O, N, S, Si, and P. 30 heterocyclyl group; C6~C 30 Cyclo group of aliphatic and aromatic rings; C1~C 20 Alkyl group; C2~C 20 alkenyl group; C2~C 20 alkinyl group; C1-C 20alkoxy group; C6~C 30 The aryloxy group; fluorenyl group; carbonyl group; ether group; or C1-C2. 20 The alkoxy carbonyl group,

[0043] 11-4)R 3 ~R 6 Independently defined: hydrogen; deuterium; halogen; C6–C 30 aryl group; C2-C containing at least one heteroatom from O, N, S, Si, and P. 30 heterocyclyl group; C6~C 30 Cyclo group of aliphatic and aromatic rings; C1~C 20 Alkyl group; C2~C 20 alkenyl group; C2~C 20 alkinyl group; C1-C 20 alkoxy group; C6~C 30 The aryloxy group; fluorenyl group; carbonyl group; ether group; or C1-C2. 20 The alkoxycarbonyl group,

[0044] 11-5)R 3 ~R 6 They can form rings with adjacent groups,

[0045] 11-6) c to f are independent integers from 0 to 4.

[0046] Chemical formula (C):

[0047]

[0048] Chemical formula (D):

[0049]

[0050] In the chemical formulas (C) and (D),

[0051] 12-1)* indicates the bonding position.

[0052] 12-2)R 7 ~R 10 Independently defined: hydrogen; deuterium; halogen; C6–C 30 aryl group; C2-C containing at least one heteroatom from O, N, S, Si, and P. 30 heterocyclyl group; C6~C 30 Cyclo group of aliphatic and aromatic rings; C1~C 20 Alkyl group; C2~C 20 alkenyl group; C2~C 20 alkinyl group; C1-C 20 alkoxy group; C6~C 30 The aryloxy group; fluorenyl group; carbonyl group; ether group; or C1-C2. 20 The alkoxycarbonyl group,

[0053] 12-3)Y 1 and Y 2 It is the chemical formula (E).

[0054] Chemical formula (E):

[0055]

[0056] In the chemical formula (E),

[0057] 13-1)* indicates the bonding position.

[0058] 13-2)R 11 It is hydrogen; deuterium; halogen; C6-C 30 aryl group; C2-C containing at least one heteroatom from O, N, S, Si, and P. 30 heterocyclyl group; C6~C 30 Cyclo group of aliphatic and aromatic rings; C1~C 20Alkyl group; C2~C 20 alkenyl group; C2~C 20 alkinyl group; C1-C 20 alkoxy group; C6~C 30 The aryloxy group; fluorenyl group; carbonyl group; ether group; or C1-C2. 20 The alkoxy carbonyl group,

[0059] 13-3)L 1 It is a single bond, C1~C 30 Alkylene, C6-C 30 arylene or C2-C 30 heterocyclic rings

[0060] 14) The R 1 ~R 11 、R'、R"、X 1 ~X 2 L 1 The rings formed by the bonding between adjacent groups can be further substituted by one or more substituents selected from the group consisting of: deuterium; halogen; C1-C2 substituents. 30 Alkyl group or C6-C 30 Aryl (aryl group) substituted or unsubstituted silane (silane group); siloxane (siloxane group); boron group; germanium group; cyano group; amino group; nitro group; C1-C 30 alkylthio group; C1~C 30 alkoxy group; C6~C 30 aryl alkoxy group; C1~C 30 Alkyl group; C2-C 30 alkenyl group; C2~C 30 alkinyl group; C6~C 30aryl group; C6-C substituted with deuterium 30 Aryl group; fluorenyl group; C2~C 30 The heterocyclyl group contains at least one heteroatom selected from the group consisting of O, N, S, Si, and P; C3~C 30 Aliphatic cyclic groups; C7~C 30 aryl alkyl group; C8~C 30 aryl alkenyl group; and combinations thereof,

[0061] Furthermore, rings can be formed between adjacent substituents.

[0062] Chemical formula (2):

[0063]

[0064] In the chemical formula (2),

[0065] 15-1) M is Zn, Cu, Ti, Fe, V=O (vanadium oxide), Ni, Mn, or Co.

[0066] 15-2)R 20 ~R 27 Independently defined: hydrogen; deuterium; halogen; C6–C 30 aryl group; C2-C containing at least one heteroatom from O, N, S, Si, and P. 30 heterocyclyl group; C6~C 30 Cyclo group of aliphatic and aromatic rings; C1~C 20 Alkyl group; C2~C 20 alkenyl group; C2~C 20 alkinyl group; C1-C 20 alkoxy group; C6~C 30 The aryloxy group; fluorenyl group; carbonyl group; ether group; or C1-C2. 20The alkoxycarbonyl group,

[0067] 15-3)R 20 ~R 27 They can form rings with adjacent groups,

[0068] 16) The R 20 ~R 27 The rings formed by the bonding between adjacent groups can be further substituted by one or more substituents selected from the group consisting of: deuterium; halogen; C1-C2 substituents. 30 Alkyl group or C6-C 30 Aryl (aryl group) substituted or unsubstituted silane (silane group); siloxane (siloxane group); boron group; germanium group; cyano group; amino group; nitro group; C1-C 30 alkylthio group; C1~C 30 alkoxy group; C6~C 30 aryl alkoxy group; C1~C 30 Alkyl group; C2~C 30 alkenyl group; C2~C 30 alkinyl group; C6~C 30 aryl group; C6-C substituted with deuterium 30 Aryl group; fluorenyl group; C2~C 30 The heterocyclyl group contains at least one heteroatom selected from the group consisting of O, N, S, Si, and P; C3~C 30 Aliphatic cyclic groups; C7~C 30 aryl alkyl group; C8~C 30 aryl alkenyl group; and combinations thereof,

[0069] Furthermore, rings can be formed between adjacent substituents.

[0070] Preferably, in the photosensitive resin composition, X represented by chemical formula 1 1 It is chemical formula (A) or chemical formula (B), or, more preferably, chemical formula (A).

[0071] Furthermore, preferably, the maximum absorption wavelength of the dye represented by the chemical formula (2) is in the region of 500 nm to 620 nm.

[0072] Furthermore, preferably, the hardened film formed using the photosensitive resin composition has an optical density of 1 or more per 1 μm film thickness at a wavelength of 550 nm, and a reflectance of 9% or less per 1 μm film thickness at a wavelength of 550 nm.

[0073] Furthermore, preferably, the adhesive resin comprises repeating units represented by the chemical formula (1) having a weight average molecular weight of 1,000 to 50,000 g / mol.

[0074] Furthermore, preferably, the photosensitive resin composition comprises: 1 to 30% by weight of a resin comprising repeating units as shown in the chemical formula (1); 0.1 to 10% by weight of a dye as shown in the chemical formula (2); 1 to 30% by weight of the pigment; 1 to 40% by weight of the reactive unsaturated compound; 0.01 to 10% by weight of the photoinitiator; and the balance of the solvent.

[0075] Furthermore, preferably, the patterned layer of the present invention comprises a polymer of the photosensitive resin composition.

[0076] Furthermore, preferably, the patterned layer is a light-shielding layer.

[0077] Furthermore, preferably, the pattern layer is a pixel definition layer that divides into multiple sub-pixels.

[0078] Furthermore, preferably, the sub-pixel includes a light-emitting element, and more preferably, it includes an organic light-emitting element.

[0079] Furthermore, preferably, the display device of the present invention includes the pattern layer.

[0080] Furthermore, preferably, the electronic device of the present invention includes the display device and a control unit for driving the display device.

[0081] Invention Effects

[0082] In one embodiment of the photosensitive resin composition of the present invention, a polymer comprising repeating units as shown in chemical formula (1) contains chemical formula (C) and chemical formula (D) in a ratio of 1:9 to 9:1, and has a relatively nonlinear structure compared to a polymer containing only one of the structures of chemical formula (C) or chemical formula (D). Therefore, the polymer comprising repeating units as shown in chemical formula (1) exhibits better dye adsorption after exposure and development steps compared to a polymer containing only one of the structures of chemical formula (C) or chemical formula (D), thereby achieving high optical density and low reflectivity.

[0083] Furthermore, the photosensitive resin composition of the present invention, in addition to the black pigment, also contains the dye represented by the chemical formula (2). The dye represented by the chemical formula (2) has a maximum absorption wavelength in the range of 500 nm to 620 nm, thereby effectively reducing the reflectivity near 550 nm, which has the greatest impact on visibility.

[0084] Thus, according to the present invention, the visibility of the display device utilizing the photosensitive resin composition is improved. Detailed Implementation

[0085] An embodiment of the photosensitive resin composition of the present invention comprises: a binder resin including repeating units represented by the following chemical formula (1); a dye represented by the following chemical formula (2); a pigment; a reactive unsaturated compound; a photoinitiator; and a solvent.

[0086] Chemical formula (1):

[0087]

[0088] Chemical formula (2):

[0089]

[0090] In describing this invention, detailed descriptions of related well-known structures or functions may be omitted if they are considered to obscure the essence of the invention. When the invention uses terms such as "comprising," "having," or "forming," other parts may be added unless "only" is used. When a constituent element is expressed in the singular, it includes cases expressed in the plural unless specifically stated otherwise.

[0091] Furthermore, in describing the constituent elements of the present invention, terms such as first, second, A, B, (a), and (b) may be used. These terms are only used to distinguish its constituent elements from other constituent elements, and the nature, order, sequence, or number of the constituent elements are not limited by the terms.

[0092] When describing the positional relationship of constituent elements, and mentioning that two or more constituent elements achieve "connection," "combination," or "access," it should be understood that two or more constituent elements can be directly "connected," "combined," or "accessed," but they can also be further "included" by two or more constituent elements and other constituent elements to achieve "connection," "combination," or "access." Among these, other constituent elements can include one or more of the two or more constituent elements that are mutually "connected," "combined," or "accessed."

[0093] Furthermore, when a component such as a layer, membrane, region, or plate is located "on" or "above" another component, it should be understood that this includes not only being located "directly above" another component, but also having another component in between. Conversely, when a component is located "directly above" another part, it should be understood that there is no other part in between.

[0094] When describing time-flow relationships related to constituent elements, work methods, or manufacturing methods, such as describing time sequence relationships or process sequence relationships like "after," "next," "then," or "before," since "immediately" or "directly" is not used, discontinuous situations can be further included.

[0095] In addition, when referring to the numerical values ​​of constituent elements or their corresponding information, even if not explicitly stated separately, it should be interpreted that the numerical values ​​or their corresponding information include the range of errors caused by various factors (e.g., engineering factors, internal or external impacts, noise).

[0096] Unless otherwise described, the terminology used in this specification and the appended claims is as follows without departing from the spirit of the invention.

[0097] Unless otherwise stated, the terms “halo” or “halogen” as used in this application include fluorine (F), fluorine (Cl), bromine (Br) and iodine (I).

[0098] Unless otherwise stated, the term "alkyl" or "alkyl group" as used herein refers to a radical containing 1 to 60 carbons linked by a single bond, representing a free radical of a saturated aliphatic functional group, such as a straight-chain alkyl group, a branched alkyl group, a cycloalkyl (alicyclic) group, an alkyl-substituted cycloalkyl group, or a cycloalkyl-substituted alkyl group.

[0099] Unless otherwise stated, the terms “haloalkyl group” or “halogenalkyl group” as used in this application refer to halogen-substituted alkyl groups.

[0100] Unless otherwise stated, the terms “alkenyl” or “alkynyl” as used herein have double or triple bonds, contain straight or side-chain groups, and have 2 to 60 carbons, but are not limited thereto.

[0101] Unless otherwise stated, the term "cycloalkyl" as used in this application refers to a cyclic alkane having 3 to 60 carbons, but is not limited thereto.

[0102] As used in this application, the term "alkoxy group" or "alkyloxy group" refers to an alkyl group that bonds to an oxygen radical and has 1 to 60 carbons unless otherwise described, but is not limited thereto.

[0103] As used in this application, the terms "alkenoxyl group", "alkenoxyl group", "alkenyloxyl group" or "alkenyloxyl group" refer to an alkenyl group that binds oxygen free radicals and, unless otherwise described, has 2 to 60 carbons, but are not limited thereto.

[0104] Unless otherwise stated, the terms "aryl group" and "arylenel group" as used in this application each have 6 to 60 carbons, but are not limited thereto. In this application, aryl group or arylenel group includes monocyclic, cyclic polymeric, and fused polycyclic compounds. For example, the aryl group may include phenyl group, monovalent functional groups of biphenyl, monovalent functional groups of naphthalene, fluorenyl group, and substituted fluorenyl group. The arylenel group may include fluorenylene group and substituted fluorenylene group.

[0105] As used in this application, the term "ring assemblies" refers to two or more ring systems (monocyclic or fused ring systems) directly linked by single or double bonds, indicating that the number of directly linked rings is less than the total number of ring systems contained in the compound. Ring assemblies can be composed of the same or different ring systems directly linked by single or double bonds.

[0106] In this application, the aryl group includes cyclic polymers; therefore, the aryl group includes biphenyl and terphenyl compounds, which are monocyclic aromatic compounds with benzene rings linked by single bonds. Furthermore, the aryl group also includes compounds with aromatic ring systems fused to aromatic monocyclic rings and linked by single bonds; therefore, for example, it also includes compounds with aromatic ring systems fused to benzene rings, i.e., fluorene, linked by single bonds.

[0107] As used in this application, the term "fused polycyclic system" refers to a ring structure that shares at least two atoms and is fused together, including: a morphology of fused two or more hydrocarbon ring systems and a morphology of fused at least one heterocyclic system containing at least one heteroatom. The fused polycyclic system can be an aromatic ring, an aromatic heterocycle, an aliphatic ring, or a combination thereof. For example, the aryl group can be a naphthalenyl group, a phenanthrenyl group, a fluorenyl group, etc., but is not limited thereto.

[0108] The term "spiro compound" as used in this application has the connotation of "spiro union," which refers to a connection formed by two rings sharing only one atom. In this case, the atom shared by the two rings is called the "spiro union atom," and according to the number of spiro atoms contained in a compound, it is referred to as a "monospiro-", "dispiro-", or "trispiro-" compound.

[0109] Unless otherwise stated, the terms "fluorenyl group," "fluorenylene group," and "fluorene-triyl group" used in this application respectively indicate that R, R', R" and R'" are all monovalent, divalent, or trivalent functional groups of hydrogen. "Substituted fluorenyl group," "substituted fluorenylene group," or "substituted fluorene-triyl group" indicates that at least one of the substituents R, R', R" and R'" is a substituent other than hydrogen, including cases where R and R' are bonded to each other and together with the carbon atoms bonded thereto, form a spiro compound. In this specification, the terms fluorenyl group, fluorenylene group, and fluorene-triyl group are all referred to as fluorenyl group, regardless of monovalent, divalent, or trivalent valence.

[0110]

[0111] Furthermore, R, R', R" and R'" can independently represent an alkyl group having 1 to 20 carbons, an olefinic group having 1 to 20 carbons, an aryl group having 6 to 30 carbons, or a heterocyclyl group having 2 to 30 carbons. For example, the aryl group can be phenyl, biphenyl, naphthalene, anthracene, or phenanthrene. The group can be pyrrole, furan, thiophene, pyrazole, imidazole, triazole, pyridine, pyrimidone, pyridazine, pyrazine, triazine, indole, benzofuran, quinazoline, or quinoxaline. For example, the substituted fluorenyl group and fluorenylene group can be monovalent or divalent functional groups of 9,9-dimethylfluorene, 9,9-diphenylfluorene, and 9,9'-spirobi[9H-fluorene], respectively.

[0112] The term "heterocyclyl group" as used in this application includes not only aromatic rings such as "heteroaryl group" or "heteroarylenel group," but also non-aromatic rings, which, unless otherwise described, refer to rings containing one or more heteroatoms and having 2 to 60 carbon atoms, but are not limited thereto. Unless otherwise described, the term "heteroatom" as used in this application means N, O, S, P, or Si, and "heterocyclyl group" refers to monocyclic, cyclic polymer, fused polycyclic, or spiro compounds containing heteroatoms.

[0113] For example, "heterocyclyl group" can also replace cyclic carbon, including compounds containing heteroatom end groups such as SO2 and P=O.

[0114]

[0115] The term "ring" as used in this application includes monocyclic and polycyclic rings. Of course, hydrocarbon rings include heterocyclic rings containing at least one hetero atom and containing aromatic and non-aromatic rings.

[0116] As used in this application, the term "polycyclic" includes ring assemblies such as biphenyl and terphenyl, as well as fused polycyclic systems and spiro compounds, including not only aromatic but also non-aromatic compounds. Of course, hydrocarbon rings include heterocycles containing at least one hetero atom.

[0117] As used in this application, the term "cyclo group" refers to cyclic hydrocarbons other than aromatic hydrocarbons, including monocyclic, cyclic polymers, fused polycyclic systems, spiro compounds, etc., and unless otherwise described, it refers to a ring with 3 to 60 carbon atoms, but is not limited thereto. For example, the fused aromatic cyclobenzene and non-aromatic cyclohexane are also equivalent to an aliphatic ring.

[0118] Furthermore, when prefixes are used consecutively in naming, it indicates that the substituents are arranged in the order they are recorded. For example, aryl alkoxy group indicates an alkoxy group substituted with an aryl group, alkoxy carbonyl group indicates a carbonyl group substituted with an alkoxy group, and aryl carbonyl alkenyl group indicates an alkenyl group substituted with an aryl carbonyl group, where aryl carbonyl group is a carbonyl group substituted with an aryl group.

[0119] Furthermore, unless explicitly stated otherwise, in the terms “substituted” or “unsubstituted” used in this application, “substituted” means substituted by one or more substituents selected from C2-C3. 20 The group consisting of heterocyclyl groups, which is composed of C2-C 20 The group consisting of heterocyclyl groups contains at least one hetero atom selected from the group consisting of the following components: deuterium, halogen, amino group, nitrile group, nitro group, C1-C 20 Alkyl group, C1-C 20 alkoxy group, C1-C 20 alkylamine group, C1-C 20 alkylthiophene group, C6-C 20 aryl thiophene group, C2-C 20 alkenyl group, C2-C 20 alkinyl group, C3-C 20 cycloalkyl group, C6-C 20 aryl group, C6-C substituted with deuterium 20 Aryl group, C8-C 20 Aryl alkenyl group, silane group, boron group, germanium group, and O, N, S, Si, and P.

[0120] In this application, the 'functional group name' corresponding to the aryl group, arylenel group, heterocyclyl group, etc., as described in the examples of each label and its substituents can be recorded as 'functional group name reflecting valence' or as 'name of parent compound'. For example, 'phenanthrene' is an aryl group, and the name of the 'group' can be recorded according to valence, such as recording a monovalent 'group' as 'phenanthryl (group)' and a divalent 'group' as 'phenanthrylene (group)', etc. However, it is also possible to disregard valence and record it as the name of the parent compound 'phenanthrene'.

[0121] Similarly, pyrimidone can be written as 'pyrimidone' regardless of its valence, or, if monovalent, as pyrimidinyl (group), and if divalent, as the name of the group with the corresponding valence, such as pyrimidinylene (group). Therefore, in this application, when the type of substituent is written as the name of the parent compound, it can represent an n-valent 'group' formed by the desorption of hydrogen atoms bonded to carbon atoms and / or heteroatoms of the parent compound.

[0122] Furthermore, in this specification, when listing compound names or substituent names, numbers or letters indicating positions may be omitted. For example, pyrido[4,3-d]pyrimidone may be listed as pyrido pyrimidone, benzo furan[2,3-d]pyrimidone as benzo furan pyrimidone, and 9,9-dimethyl-9H-fluorene as dimethylfluorene, etc. Therefore, benzo[g]quinoxaline or benzo[f]quinoxaline may both be listed as benzo quinoxaline.

[0123] Furthermore, unless otherwise stated, the chemical formulas used in this application are also subject to the definitions of substituents based on the following definitions of chemical formulas.

[0124]

[0125] When a is an integer of 0, it represents the substituent R. 1 This does not exist; that is, when a is 0, all carbons forming the benzene ring are bonded to hydrogen. In this case, the labeling of the hydrogens bonded to the carbons can be omitted, and the chemical formula or compound can be written. Furthermore, when a is an integer of 1, one substituent R... 1 It bonds to any carbon atom in the benzene ring. When a is an integer of 2 or 3, the bonding can be as follows. When a is an integer from 4 to 6, it can be bonded to the carbon atom in the benzene ring using a similar method. When a is an integer greater than 2, R... 1 They can be the same or different.

[0126]

[0127] Unless otherwise stated, ring formation means that adjacent groups bond together to form a monocyclic or fused polycyclic ring. Monocyclic rings and fused polycyclic rings include not only hydrocarbon rings but also heterocycles containing at least one heteroatom and may include aromatic and non-aromatic rings.

[0128] Furthermore, in this specification, unless otherwise stated, when referring to condensed rings, the number in 'number-condensed ring' indicates the number of condensed rings. For example, the morphology of three rings condensed together can be represented as a 3-condensed ring, such as anthracene, phenanthrene, benzoquinoxaline, etc.

[0129] Furthermore, unless otherwise stated, the term "bridged bicyclic compound" as used in this application refers to a compound in which two rings share three or more atoms to form a ring. In this case, the shared atoms may include carbon or heteroatoms.

[0130] In this application, organic electronic components refer to (a number of) components between an anode and a cathode, or organic light-emitting diodes (OLEDs) including (a number of) components located between an anode and a cathode and therebetween.

[0131] Furthermore, depending on the context, the display device in this application refers to organic electronic components, organic light-emitting diodes (OLEDs), and panels including them, or electronic devices including panels and circuitry. For example, electronic devices include all lighting devices, solar cells, portable or mobile terminals (e.g., smartphones, tablets, PDAs, electronic dictionaries, PMPs, etc.), navigation terminals, game consoles, various TVs, various computer monitors, etc., but are not limited thereto; any device of any form can be used as long as it includes the aforementioned components(s).

[0132] An embodiment of the photosensitive resin composition of the present invention comprises: an adhesive resin including repeating units of the following chemical formula (1), a dye represented by the following chemical formula (2), a reactive unsaturated compound, a pigment, an initiator, and a solvent.

[0133] The resin comprises repeating units of the structure shown in the chemical formula (1), which in the polymer chain contain structures represented by the following chemical formulas (C) and (D). Specifically, the polymer comprises repeating units represented by the chemical formula (1), which contain chemical formulas (C) and (D) in a ratio of 1:9 to 9:1, and has a relatively nonlinear structure compared to polymers that contain only one of the structures of chemical formula (C) or chemical formula (D).

[0134] Therefore, the polymer includes repeating units represented by chemical formula (1), which, compared to polymers containing only one of chemical formula (C) or chemical formula (D), has good dye adsorption after exposure and development steps, thereby achieving high optical density and low reflectivity.

[0135] Furthermore, the photosensitive resin composition of the present invention, in addition to the black pigment, also contains the dye represented by the chemical formula (2). The dye represented by the chemical formula (2) has a maximum absorption wavelength in the range of 500 nm to 620 nm, thereby effectively reducing the reflectivity near 550 nm, which has the greatest impact on visibility.

[0136] This improves the visibility of the display device utilizing the photosensitive resin composition according to the present invention.

[0137] Hereinafter, implementation examples of the present invention will be described in detail. However, this description is merely illustrative and the present invention is not limited thereto; it is defined only by the scope of the appended claims. The individual components will be described in detail below.

[0138] (A) Adhesive resin

[0139] An adhesive resin according to an embodiment of the present invention comprises repeating units of the following chemical formula (1).

[0140] Chemical formula (1):

[0141]

[0142] In the chemical formula (1),

[0143] 1) * indicates the part where the key is connected by repeating units.

[0144] 2)R 1 and R 2Independently defined: hydrogen; deuterium; halogen; C6–C 30 aryl group; C2-C containing at least one heteroatom from O, N, S, Si, and P. 30 Heterocyclyl group; C6~C 30 Cyclo group of aliphatic and aromatic rings; C1~C 20 Alkyl group; C2-C 20 alkenyl group; C2~C 20 alkinyl group; C1-C 20 alkoxy group; C6~C 30 The aryloxy group; fluorenyl group; carbonyl group; ether group; or C1-C2. 20 The alkoxy carbonyl group,

[0145] 3)R 1 and R 2 They can form rings with adjacent groups,

[0146] 4) a and b are independent integers from 0 to 4.

[0147] 5)X 1 It is a single bond, O, CO, SO2, CR'R", SiR'R", chemical formula (A) or chemical formula (B).

[0148] 6)X 2 It is C6~C 30 aryl group; C2-C containing at least one heteroatom from O, N, S, Si, and P. 30 heterocyclyl group; C6~C 30 Cyclo group of aliphatic and aromatic rings; C1~C 20 Alkyl group; C2~C 20 alkenyl group; C2~C 20 alkinyl group; C1-C 20 alkoxy group; C6~C30 aryloxy groups; or combinations thereof,

[0149] 7) R' and R" are independently: hydrogen; deuterium; halogen; C6-C 30 aryl group; C2-C containing at least one heteroatom from O, N, S, Si, and P. 30 Heterocyclyl group; C6~C 30 Cyclo group of aliphatic and aromatic rings; C1~C 20 Alkyl group; C2-C 20 alkenyl group; C2~C 20 alkinyl group; C1-C 20 alkoxy group; C6~C 30 The aryloxy group; fluorenyl group; carbonyl group; ether group; or C1-C2. 20 The alkoxy carbonyl group,

[0150] 8) R' and R" can form rings with adjacent groups, respectively.

[0151] 9)A 1 and A 2 They are independently represented by the chemical formula (C) or the chemical formula (D).

[0152] 10) The resin comprises repeating units represented by chemical formula (1), wherein within the polymer chain, the ratio of chemical formula (C) to chemical formula (D) satisfies 1:9 to 9:1.

[0153] When R' and R" are bonded together to form a ring, the following is an example.

[0154]

[0155] Specific examples of the chemical formulas (A) and (B) are as follows.

[0156] Chemical formula (A):

[0157]

[0158] Chemical formula (B):

[0159]

[0160] In the chemical formulas (A) and (B),

[0161] 11-1)* indicates the bonding position.

[0162] 11-2)X3 is O, S, SO2 or NR',

[0163] 11-3) R' is hydrogen; deuterium; halogen; C6~C 30 aryl group; C2-C containing at least one heteroatom from O, N, S, Si, and P. 30 heterocyclyl group; C6~C 30 Cyclo group of aliphatic and aromatic rings; C1~C 20 Alkyl group; C2~C 20 alkenyl group; C2~C 20 alkinyl group; C1-C 20 alkoxy group; C6~C 30 The aryloxy group; fluorenyl group; carbonyl group; ether group; or C1-C2. 20 The alkoxy carbonyl group,

[0164] 11-4)R 3 ~R 6 Independently defined: hydrogen; deuterium; halogen; C6–C 30 aryl group; C2-C containing at least one heteroatom from O, N, S, Si, and P. 30 heterocyclyl group; C6~C 30 Cyclo group of aliphatic and aromatic rings; C1~C 20 Alkyl group; C2~C 20 alkenyl group; C2~C 20 alkinyl group; C1-C 20alkoxy group; C6~C 30 The aryloxy group; fluorenyl group; carbonyl group; ether group; or C1-C2. 20 The alkoxycarbonyl group,

[0165] 11-5)R 3 ~R 6 They can form rings with adjacent groups,

[0166] 11-6) c~f are independent integers from 0 to 4.

[0167] Specific examples of the chemical formulas (C) and (D) are as follows.

[0168] Chemical formula (C):

[0169]

[0170] Chemical formula (D):

[0171]

[0172] In the chemical formulas (C) and (D),

[0173] 12-1)* indicates the bonding position.

[0174] 12-2)R 7 ~R 10 Independently defined: hydrogen; deuterium; halogen; C6–C 30 aryl group; C2-C containing at least one heteroatom from O, N, S, Si, and P. 30 heterocyclyl group; C6~C 30 Cyclo group of aliphatic and aromatic rings; C1~C 20 Alkyl group; C2~C 20 alkenyl group; C2~C 20 alkinyl group; C1-C 20 alkoxy group; C6~C 30The aryloxy group; fluorenyl group; carbonyl group; ether group; or C1-C2. 20 The alkoxycarbonyl group,

[0175] 12-3)Y 1 and Y 2 It has the chemical formula (E).

[0176] A specific example of the chemical formula (E) is as follows.

[0177] Chemical formula (E):

[0178]

[0179] In the chemical formula (E),

[0180] 13-1)* indicates the bonding position.

[0181] 13-2)R 11 It is hydrogen; deuterium; halogen; C6-C 30 aryl group; C2-C containing at least one heteroatom from O, N, S, Si, and P. 30 heterocyclyl group; C6~C 30 Cyclo group of aliphatic and aromatic rings; C1~C 20 Alkyl group; C2~C 20 alkenyl group; C2~C 20 alkinyl group; C1-C 20 alkoxy group; C6~C 30 The aryloxy group; fluorenyl group; carbonyl group; ether group; or C1-C2. 20 The alkoxy carbonyl group,

[0182] 13-3)L 1 It is a single bond, C1~C 30 Alkylene, C6-C 30 arylene or C2-C30 heterocyclic rings

[0183] 14) The R 1 ~R 11 、R'、R"、X 1 ~X 2 L 1 The rings formed by the bonding between adjacent groups can be further substituted by one or more substituents selected from the group consisting of: deuterium; halogen; C1-C2 substituents. 30 Alkyl group or C6-C 30 Substituted or unsubstituted aryl groups; silane groups; siloxane groups; boron groups; germanium groups; cyano groups; amino groups; nitro groups; C1–C2 30 alkylthio group; C1~C 30 alkoxy group; C6~C 30 aryl alkoxy group; C1~C 30 Alkyl group; C2-C 30 alkenyl group; C2~C 30 alkinyl group; C6~C 30 aryl group; C6-C substituted with deuterium 30 Aryl group; fluorenyl group; C2~C 30 The heterocyclyl group contains at least one heteroatom selected from the group consisting of O, N, S, Si, and P; C3~C 30 Aliphatic cyclic groups; C7~C 30 aryl alkyl group; C8~C 30 aryl alkenyl group; and combinations thereof,

[0184] Furthermore, rings can be formed between adjacent substituents.

[0185] The R 1 ~R 11 、R'、R" and X 1 ~X2 When it is an aryl group, it is preferably C6 to C6. 30 The aryl group, more preferably, can be C6-C6. 18 The aryl group can be, for example, phenyl, biphenyl, naphthyl, terphenyl, etc.

[0186] The R 1 ~R 11 、R'、R"、X 1 ~X 2 and L 1 When the group is a heterocyclyl group, it is preferably C2 to C3. 30 The heterocyclyl group, more preferably, can be C2 to C3. 18 The heterocyclyl group can be, for example, dibenzo furan, dibenzothiophen, naphtho benzo thiophen, naphtho benzofuran, etc.

[0187] The R 1 ~R 11 、R'、R" and X 1 ~X 2 When the fluorenyl group is used, it is preferably 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorenyl, 9,9'-spirobi-fluorene, etc.

[0188] The L 1 When the methyl group is arylene, it is preferably C6 to C6. 30 The arylene, more preferably, can be C6-C6. 18 The arylene group can be, for example, phenyl, biphenyl, naphthyl, terphenyl, etc.

[0189] The R 1 ~R 11When R' and R" are alkyl groups, they are preferably C1 to C2 groups. 10 Alkyl group, for example, can be methyl, t-butyl, etc.

[0190] The R 1 ~R 11 When R' and R" are alkoxy groups, they are preferably C1 to C2 groups. 20 The alkoxy group, more preferably, can be C1 to C2. 10 The alkoxy group can be, for example, methoxy, butoxy, etc.

[0191] The R 1 ~R 11 、R'、R"、X 1 ~X 2 And in L 1 The ring formed by bonding adjacent groups can be C6 to C6. 60 Aromatic cyclic groups; fluorenyl group; C2-C2 groups containing at least one heteroatom from O, N, S, Si, and P. 60 heterocyclyl group; or C3~C 60 When an aliphatic cyclic group, for example, forms an aromatic ring by bonding adjacent groups together, preferably, a C6-C6 ring can be formed. 20 The aromatic ring, more preferably, can form C6-C6 rings. 14 Aromatic rings, for example, can form benzene, naphthalene, phenanthrene, etc.

[0192] According to the present invention, the weight average molecular weight of the resin is 1,000 to 100,000 g / mol, preferably 1,000 to 50,000 g / mol, and more preferably 1,000 to 30,000 g / mol. If the weight average molecular weight of the resin falls within the range described above, no residue is generated during the fabrication of the patterned layer, the pattern formation effect is excellent, and there is no loss of film thickness during development, resulting in a good pattern.

[0193] In the total amount of the photosensitive resin composition, the resin content can be from 1 to 30% by weight, more preferably from 3 to 20% by weight. When the resin content is within the range described above, excellent sensitivity, developability, and adhesion (bearing capacity) can be obtained.

[0194] In addition to the aforementioned resin, the photosensitive resin composition may further comprise an acrylic resin. The acrylic resin is a copolymer of a first vinyl unsaturated monomer and a second vinyl unsaturated monomer thereto, and may be a resin comprising one or more repeating acrylic units.

[0195] (B) Dyes

[0196] The dye of one embodiment of the present invention comprises the structure represented by the following chemical formula (2).

[0197] Chemical formula (2):

[0198]

[0199] In the chemical formula (2),

[0200] 15-1) M is Zn, Cu, Ti, Fe, V=O, Ni, Mn, or Co.

[0201] 15-2)R 20 ~R 27 Independently defined: hydrogen; deuterium; halogen; C6–C 30 aryl group; C2-C containing at least one heteroatom from O, N, S, Si, and P. 30 heterocyclyl group; C6~C 30 Cyclo group of aliphatic and aromatic rings; C1~C 20 Alkyl group; C3~C 20 alkenyl group; C2~C 20 alkinyl group; C1-C 20 alkoxy group; C6~C 30 The aryloxy group; fluorenyl group; carbonyl group; ether group; or C1-C2. 20 The alkoxycarbonyl group,

[0202] 15-3)R 20 ~R 27 They can form rings with adjacent groups,

[0203] 16) The R 20 ~R 27 The rings formed by the bonding between adjacent groups can be further substituted by one or more substituents selected from the group consisting of: deuterium; halogen; C1-C2 substituents. 30 Alkyl group or C6-C 30 Aryl (aryl group) substituted or unsubstituted silane (silane group); siloxane (siloxane group); boron group; germanium group; cyano group; amino group; nitro group; C1-C 30 alkylthio group; C1~C 30 alkoxy group; C6~C 30 aryl alkoxy group; C1~C 30 Alkyl group; C2~C 30 alkenyl group; C2~C 30 alkinyl group; C6~C 30 aryl group; C6-C substituted with deuterium 30 Aryl group; fluorenyl group; C2~C 30 The heterocyclyl group contains at least one heteroatom selected from the group consisting of O, N, S, Si, and P; C3~C 30 Aliphatic cyclic groups; C7~C 30 aryl alkyl group; C8~C 30 aryl alkenyl group; and combinations thereof,

[0204] Furthermore, rings can be formed between adjacent substituents.

[0205] The R 20 ~R 27 When it is an aryl group, it is preferably C6 to C6. 30 The aryl group, more preferably, can be C6-C6. 18The aryl group can be, for example, phenyl, biphenyl, naphthyl, terphenyl, etc.

[0206] The R 20 ~R 27 When the group is a heterocyclyl group, it is preferably C2 to C3. 30 The heterocyclyl group, more preferably, can be C2 to C3. 18 The heterocyclyl group can be, for example, dibenzo furan, dibenzo thiophen, naphtho benzo thiophen, naphtho benzo furan, etc.

[0207] The R 20 ~R 27 When the fluorenyl group is used, it is preferably 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorenyl, 9,9'-spirobi-fluorene, etc.

[0208] The R 20 ~R 27 When the alkyl group is used, it is preferably C1 to C2. 10 Alkyl groups, for example, can be methyl, t-butyl, etc.

[0209] The R 20 ~R 27 When the group is alkoxy group, it is preferably C1 to C2. 20 The alkoxy group, more preferably, can be C1 to C2. 10 The alkoxy group can be, for example, methoxy, butoxy, etc.

[0210] The R 20 ~R 27 The ring formed by bonding adjacent groups can be C6 to C6. 60Aromatic cyclic group; fluorenyl group; C2~C 60 The heterocyclyl group contains at least one heteroatom selected from O, N, S, Si, and P; or C3~C 60 When an aliphatic cyclic group, for example, forms an aromatic ring by bonding adjacent groups together, preferably, a C6-C6 ring can be formed. 20 The aromatic ring, more preferably, can form C6-C6 rings. 14 Aromatic rings, for example, can form benzene, naphthalene, phenanthrene, etc.

[0211] The dye with the polypyrazine structure shown in chemical formula (2) has high absorbance, thus achieving high optical density even in small amounts, and maximizing absorbance at a narrow, specific wavelength. In particular, it has the advantage of allowing for wavelength tuning through the modification of substituents and the central metal.

[0212] The dye can be mixed with one or more different colorants. The mixing ratio with different colorants can be 1:99 to 99:1, preferably 3:97 to 97:3, and more preferably 10:90 to 90:10. When used within the range described, the desired optical density can be obtained, which is beneficial for pattern formation.

[0213] In specific examples of the dyes mentioned, CI solvent dyes include: CI solvent yellow 4, 14, 15, 16, 21, 23, 24, 38, 56, 62, 63, 68, 79, 82, 93, 94, 98, 99, 151, 162, 163, etc.; CI solvent red 8, 45, 49, 89, 111, 122, 125, 130, 132, 146, 179, etc. Materials; CI solvent orange 2, 7, 11, 15, 26, 41, 45, 56, 62 and other orange dyes; CI solvent blue 5, 35, 36, 37, 44, 59, 67, 70 and other blue dyes; CI solvent violet 8, 9, 13, 14, 36, 37, 47, 49 and other purple dyes; CI solvent green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35 and other green dyes, etc.

[0214] Among the CI solvent dyes, preferably, CI Solvent Yellow 14, 16, 21, 56, 151, 79, 93; CI Solvent Red 8, 49, 89, 111, 122, 132, 146, 179; CI Solvent Orange 41, 45, 62; CI Solvent Blue 35, 36, 44, 45, 70; and CI Solvent Violet 13 are used. More preferably, CI Solvent Yellow 21, 79; CI Solvent Red 8, 122, 132; and CI Solvent Orange 45, 62 are used.

[0215] Furthermore, the CI acid dyes include: CI Acid Yellow 1, 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112, 113, 114, 116, 119, 123, 128, 134, 135, 138, 139, 140, 144, 150, 155, 157, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214. Yellow dyes including 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, and 251; Acid Red CI 1, 4, 8, 14, 17, 18, 26, 27, 29, 31, 34, 35, 37, 42, 44, 50, 51, 52, 57, 66, 73, 80, 87, 88, 91, 92, 94, 97, 103, 111, 114, 129, 133, 134, 138, 143, 145, 150, 151, 158, 176, 182, 183, 198, 206, 211, 215, 216, 217, 227, 228, 249, and 252. Red dyes including 257, 258, 260, 261, 266, 268, 270, 274, 277, 280, 281, 195, 308, 312, 315, 316, 339, 341, 345, 346, 349, 382, ​​383, 394, 401, 412, 417, 418, 422, 426, etc.; Acid Orange (CI) dyes including 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 169, 173, etc.; Acid Blue (CI) dyes including 1, 7, 9, 15, 18, 23, 25, 27, 29, 40, 42, 4, etc. Blue dyes including 5, 51, 62, 70, 74, 80, 83, 86, 87, 90, 92, 96, 103, 112, 113, 120, 129, 138, 147, 150, 158, 171, 182, 192, 210, 242, 243, 256, 259, 267, 278, 280, 285, 290, 296, 315, 324:1, 335, 340; purple dyes including CI Acid Violet 6B, 7, 9, 17, 19, 66; and green dyes including CI Acid Green 1, 3, 5, 9, 16, 25, 27, 50, 58, 63, 65, 80, 104, 105, 106, 109.

[0216] Preferably, the acid dyes used are CI Acid Yellow 42, CI Acid Red 92, CI Acid Blue 80 and 90, CI Acid Violet 66, and CI Acid Green 27, which have excellent solubility in organic solvents.

[0217] Furthermore, CI direct dyes include: CI Direct Yellow 2, 33, 34, 35, 38, 39, 43, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129, 136, 138, 141, etc.; CI Direct Red 79, 82, 83, 84, 91, 92, 96, 97, 98, 99, 105, 106, 107, 172, 173, 176, 177, 179, 181, 182, 184, 204, 207. Red dyes including 211, 213, 218, 220, 221, 222, 232, 233, 234, 241, 243, 246, 250; Direct Orange (CI) dyes including 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107; Direct Blue (CI) dyes including 38, 44, 57, 70, 77, 80, 81, 84, 85, 86, 90, 93, 94, 95, 97, 98, 99, 100, 101, 106, 107, 1 08, 109, 113, 114, 115, 117, 119, 137, 149, 150, 153, 155, 156, 158, 159, 160, 161, 162, 163, 164, 166, 167, 170, 171, 172, 173, 188, 189, 190, 192, 193, 194, 196, 198, 199, 200, 207, 209, 210, 212, 213, 214, 222, 228, 229, 237, 238, 242, 243 Blue dyes such as 244, 245, 247, 248, 250, 251, 252, 256, 257, 259, 260, 268, 274, 275, 293; purple dyes such as CI direct violet 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104; and green dyes such as CI direct green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 77, 79, 82.

[0218] Furthermore, CI mordant dyes include: CI mordant yellow dyes 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65, etc.; CI mordant red dyes 1, 2, 3, 4, 9, 11, 12, 14, 17, 18, 19, 22, 23, 24, 25, 26, 30, 32, 33, 36, 37, 38, 39, 41, 43, 45, 46, 48, 53, 56, 63, 71, 74, 85, 86, 88, 90, 94, 95, etc.; and CI mordant orange dyes 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, etc. Orange dyes such as 37, 42, 43, 47, 48, etc.; CI meddle blue dyes such as 1, 2, 3, 7, 8, 9, 12, 13, 15, 16, 19, 20, 21, 22, 23, 24, 26, 30, 31, 32, 39, 40, 41, 43, 44, 48, 49, 53, 61, 74, 77, 83, 84, etc.; CI meddle violet dyes such as 1, 2, 4, 5, 7, 14, 22, 24, 30, 31, 32, 37, 40, 41, 44, 45, 47, 48, 53, 58, etc.; CI meddle green dyes such as 1, 3, 4, 5, 10, 15, 19, 26, 29, 33, 34, 35, 41, 43, 53, etc.

[0219] In this invention, the dyes can be used individually or in combination of two or more.

[0220] The maximum absorption wavelength of the dye is in the range of 500 nm to 620 nm, more preferably in the wavelength range of 520 nm to 580 nm. When the maximum absorption wavelength of the dye is within the range described above, the display device using the photosensitive resin composition of the present invention will reduce the reflectivity due to external visible light, thereby improving visibility.

[0221] The dye content in the total amount of the photosensitive resin composition may be from 0.1% to 10% by weight, more preferably from 0.3% to 8% by weight. When the dye content is within the range described above, the curability and adhesion of the pattern are excellent, and the reflectivity at 550 nm wavelength can be reduced to improve the visibility of the display device.

[0222] (C) Pigment

[0223] The pigment can be one or more of organic and inorganic pigments. The pigment can be red, green, blue, yellow, black, etc.

[0224] For example, the red pigments mentioned include: CI red pigment 254, CI red pigment 255, CI red pigment 264, CI red pigment 270, CI red pigment 272, CI red pigment 177, CI red pigment 89, etc.

[0225] For example, the green pigments mentioned include copper phthalocyanine pigments that replace halogens, such as CI green pigment 36 and CI green pigment 7.

[0226] For example, the blue pigments include: CI blue pigment 15:6, CI blue pigment 15, CI blue pigment 15:1, CI blue pigment 15:2, CI blue pigment 15:3, CI blue pigment 15:4, CI blue pigment 15:5, CI blue pigment 16, etc., copper phthalocyanine pigments.

[0227] For example, the yellow pigments include: isoindoline pigments such as CI yellow pigment 139, quinophthalone pigments such as CI yellow pigment 138, nickel composite pigments such as CI yellow pigment 150, etc.

[0228] For example, the black pigments mentioned include: lactam black, aniline black, perylene black, titanium black, carbon black, etc.

[0229] The pigments may be used alone or in combination of two or more, without being limited to any of them.

[0230] When a pattern layer formed using a photosensitive resin composition requires high light-blocking properties, the aforementioned black pigment can be used for effective light blocking. When using the aforementioned black pigment, it can also be used in conjunction with color correctors such as anthraquinone-based pigments, perylene-based pigments, phthalocyanine-based pigments, and azo-based pigments.

[0231] To disperse the pigment on the photosensitive resin composition, a dispersant may be used together. The pigment may be used after surface pretreatment with the dispersant, or it may be used after the dispersant is added together with the pigment during the preparation of the photosensitive resin composition.

[0232] The dispersant can be a nonionic dispersant, anionic dispersant, or a cationic dispersant. Specific examples of the dispersant include: polyalkylene glycol and its esters, polyoxyalkylene, alkylene oxide polyol ester additives, alcohol alkylene oxide additives, sulfonates, sulfonates, carboxylic acid esters, carboxylates, alkylene oxide alkylamide additives, alkylamines, etc., which can be used alone or in combination of two or more.

[0233] Commercially available products of the dispersant include, for example, BYK's DISPERBYK-101, DISPERBYK-130, DISPERBYK-140, DISPERBYK-160, DISPERBYK-161, DISPERBYK-162, DISPERBYK-163, DISPERBYK-164, DISPERBYK-165, DISPERBYK-166, and DISPERBYK. -170, DISPERBYK-171, DISPERBYK-182, DISPERBYK-2000, DISPERBYK-2001, etc.; or BASF's EFKA-47, EFKA-47EA, EFKA-48, EFKA-49, EFKA-100, EFKA-400, EFKA-450, etc.; or Zeneka's Solsperse5000, Solsperse 12000, Solsperse 13240, Solsperse 13940, Solsperse 17000, Solsperse 20000, Solsperse 24000GR, Solsperse 27000, Solsperse 28000, etc.; or Ajinomoto's PB711, PB821, etc.

[0234] The dispersant content in the total amount of the photosensitive resin composition can be from 0.1% to 15% by weight. When the content of the dispersant is within the range described above, the photosensitive resin composition exhibits excellent dispersibility, and consequently, excellent stability, developability, and patterning properties when preparing a light-shielding layer.

[0235] The pigment can also be used after pretreatment with water-soluble inorganic salts and wetting agents. As described above, when the pigment is used after pretreatment, the primary particle size of the pigment can be refined. The pretreatment is carried out through the following steps: kneading the pigment together with water-soluble inorganic salts and wetting agents; then, filtering and rinsing the pigment obtained in the kneading step. The kneading can be carried out at a temperature of 40°C to 100°C, and the filtering and rinsing can be done by rinsing the inorganic salts with water and filtering. For example, the water-soluble inorganic salts include sodium chloride, potassium chloride, etc., but are not limited thereto.

[0236] The wetting agent is uniformly mixed with the pigment and the water-soluble inorganic salt, thereby acting as a medium that makes the pigment easier to pulverize. For example, it includes alkylene glycol monoalkyl ether, propylene glycol monomethyl ether, diethylene glycol monomethyl ether, and other alkylene glycol monoalkyl ethers; ethanol, isopropanol, butanol, hexanol, cyclohexanol, ethylene glycol, diethylene glycol, polyethylene glycol, polyethylene glycol glycerin, and other alcohols, which can be used alone or in combination of two or more.

[0237] The pigments produced by the kneading step can have an average particle size of 20 nm to 110 nm. When the average particle size of the pigment falls within this range, it exhibits excellent heat resistance and lightfastness, and can effectively form fine patterns.

[0238] The pigment content in the total amount of the photosensitive resin composition can be from 1% to 40% by weight, 1% to 30% by weight, or 2% to 30% by weight. When the pigment content is within the range described above, the photosensitive resin composition exhibits excellent color reproduction and can form a patterned layer with excellent curability and adhesion.

[0239] The pigment and dye content in the total amount of the photosensitive resin composition may be 5 to 40% by weight, more specifically, 8 to 30% by weight. When the pigment and dye are included within the range described above, the clarity, curability, and adhesion of the pattern are excellent.

[0240] (D) Reactive unsaturated compounds

[0241] The reactive unsaturated compound may be one or more esters, which are (meth)acrylic acids having at least one ethylene-unsaturated double bond and being monofunctional or polyfunctional. The reactive unsaturated compound may be a monomer or an oligomer.

[0242] In this specification, "(meth)acrylic acid" can be methacrylic acid, acrylic acid, or a mixture of methacrylic acid and acrylic acid.

[0243] The reactive unsaturated compound can be a photopolymerizable compound. Since the reactive unsaturated compound is a photopolymerizable compound, sufficient polymerization is initiated when the photosensitive resin composition is exposed during the patterning process, resulting in a pattern with excellent heat resistance, light resistance, and chemical resistance.

[0244] For example, the reactive unsaturated compound may be selected from one or more of the following: ethylene glycol diacrylate, ethylene glycol dimethacrylate, diethylene glycol diacrylate, triethylene glycol diacrylate, triethylene glycol dimethacrylate, 1,6-hexanediol diacrylate, 1,6-hexanediol dimethacrylate, pentaerythritol triacrylate, pentaerythritol tetraacrylate, dipentaerythritol pentaacrylate, dipentaerythritol hexaacrylate, bisphenol A epoxy acrylate, ethylene glycol monomethyl ether acrylate, trimethylolpropane triacrylate, and trisacryloyl oxyethyl phosphate, but is not limited thereto.

[0245] Commercially available products of the aforementioned reactive unsaturated compounds include, for example, the following.

[0246] For example, the difunctional esters of (meth)acrylic acid include: aronyx M-210, M-240, M-6200, etc. from Toa Synthetic Chemical Industries, Ltd.; KAYARAD HDDA, HX-220, R-604, etc. from Nippon Chemical Industries, Ltd.; and V-260, V-312, V-335 HP, etc. from Osaka Organic Chemical Industries, Ltd.

[0247] For example, the trifunctional esters of (meth)acrylic acid include: aronyx M-309, M-400, M-405, M-450, M-7100, M-8030, and M-8060 from Toa Synthetic Chemical Industries, Ltd.; KAYARAD TMPTA, DPCA-20, DPCA-60, and DPCA-120 from Nippon Chemical Industries, Ltd.; and V-295, V-300, and V-360 from Osaka Organic Chemical Industries, Ltd.

[0248] The above products can be used alone or in combination of two or more.

[0249] To achieve superior developability, the reactive unsaturated compound can be used after treatment with acid anhydride. The content of the reactive unsaturated compound in the total amount of the photosensitive resin composition can be from 1 to 40% by weight, for example, from 1 to 20% by weight. When the content of the reactive unsaturated compound is within this range, sufficient curing is initiated during exposure in the patterning process, resulting in excellent reliability, excellent heat resistance, light resistance, and chemical resistance of the pattern, as well as excellent clarity and adhesion.

[0250] (E) Photoinitiator

[0251] *241 The initiator may be a combination of a photopolymerization initiator, a free radical polymerization initiator, or the like.

[0252] For example, the photopolymerization initiator may be one or more of acetophenone compounds, benzophenone compounds, thioxanone compounds, benzoethanol ketone compounds, oxime compounds, and triazine compounds.

[0253] For example, the acetophenone compounds include: 2,2'-diethoxyacetophenone, 2,2'-dibutoxyacetophenone, 2-hydroxy-2-methylacetophenone, pt-butyltrichloroacetophenone, pt-butyldichloroacetophenone, 4-chloroacetophenone, 2,2'-dichloro-4-phenoxyacetophenone, 2-methyl-1-(4-(methylthio)phenyl)-2-morpholinylprop-1-one, 2-benzyl-2-dimethylamino-1-(4-l-morpholinylphenyl)-butane-1-one, etc.

[0254] For example, the benzophenone compounds include: benzophenone, benzoylbenzoic acid, methyl benzoylbenzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone, 4,4'-bis(dimethylamino)benzophenone, 4,4'-bis(diethylamino)benzophenone, 4,4'-dimethylaminobenzophenone, 4,4'-dichlorobenzophenone, 3,3'-dimethyl-2-methoxybenzophenone, etc.

[0255] For example, thioxanthone compounds include: thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-diisopropylthioxanthone, 2-chlorothioxanthone, etc.

[0256] For example, the diphenylethanol ketone compounds include: diphenylethanol ketone, diphenylethanol ketone methyl ether, diphenylethanol ketone ethyl ether, diphenylethanol ketone isopropyl ether, diphenylethanol ketone isobutyl ether, benzyl dimethyl ketone acetal, etc.

[0257] For example, the oxime compounds include: 2-(o-benzoyloxime)-1-[4-(phenylthio)phenyl]-1,2-octanedione, 1-(o-acetyloxime)-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-ol]ethanol, O-ethoxycarbonyl-α-oxyamino-1-phenylpropane-1-one, 2-dimethylamino-2-(4-methylbenzyl)-1-(4-morpholin-4-ol-phenyl)-butane-1-one, 1-(4-benzenesulfonylbenzene)-butane-1,2-dione. 2-oxime-O-benzoic acid, 1-(4-benzenesulfonylbenzene)-octane-1,2-dione-oxime-O-benzoic acid, 1-(4-benzenesulfonylbenzene)-octane-1-one oxime-O-acetate, 1-(4-benzenesulfonylbenzene)-butane-1-one oxime-O-acetate, 1-(4-methylsulfonyl-phenyl)-butane-1-one oxime-O-acetate, hydroxyimino-(4-methylsulfonyl-phenyl)-ethyl acetate-O-acetate, hydroxyimino-(4-methylsulfonyl-phenyl)-ethyl acetate-O-benzoic acid, etc.

[0258] For example, the triazine compounds include: 2,4,6-trichloro-s-triazine, 2-phenyl-4,6-bis(trichloromethyl)-s-triazine, 2-(3',4'-dimethoxystyryl)-4,6-bis(trichloromethyl)-s-triazine, 2-(4'-methoxynaphthyl)-4,6-bis(trichloromethyl)-s-triazine, 2-(p-methoxyphenyl)-4,6-bis(trichloromethyl)-s-triazine, and 2-(p-tolyl)-4,6-bis(trichloromethyl)-s-triazine. (trichloromethyl)-s-triazine, 2-biphenyl-4,6-bis(trichloromethyl)-s-triazine, bis(trichloromethyl)-6-styryl-s-triazine, 2-(naphtho-1-ol)-4,6-bis(trichloromethyl)-s-triazine, 2-(4-methoxynaphtho-1-ol)-4,6-bis(trichloromethyl)-s-triazine, 2-4-trichloromethyl(piperyl)-6-triazine, 2-4-trichloromethyl(4'-methoxystyryl)-6-triazine, etc.

[0259] In addition to compounds, the photopolymerization initiator can also be carbazole compounds, diketone compounds, sulfonium borate compounds, diazo compounds, imidazole compounds, non-imidazole compounds, etc.

[0260] The free radical polymerization initiator can be a peroxide-based compound, an azo-based compound, etc.

[0261] For example, the peroxide compounds include: ketone peroxides such as methyl ethyl ketone peroxide, methyl isobutyl ketone peroxide, cyclohexanone peroxide, methyl cyclohexanone peroxide, and acetylacetone peroxide; diacyl peroxides such as isobutyryl peroxide, 2,4-dichlorobenzoyl peroxide, o-methylbenzoyl peroxide, and bis-3,5,5-trimethylhexanoyl peroxide; hydrogen peroxides such as 2,4,4-trimethylpentyl-2-hydrogen peroxide, dicumyl hydroperoxide, isocumyl hydroperoxide, and t-butyl hydroperoxide; and dicumyl peroxide, 2,5-dimethyl-2,5-di(t-butylperoxide) Dialkyl peroxides, such as 1,3-bis(t-butoxyisopropyl)benzene and t-butyl peroxypentanoate; alkyl succinates, such as 2,4,4-trimethylpentyl peroxyphenoxyacetic acid, α-peroxynedecanoate, t-butyl peroxybenzoic acid, and di-t-butyl peroxytrimethyl adipic acid; percarbonates, such as di-3-methoxydicarbonate, di-2-ethylhexyl peroxydicarbonate, bis-4-t-cyclohexyl peroxydicarbonate, diisopropyl peroxydicarbonate, acetyl peroxycyclohexylsulfonyl, and t-peroxyaryl carbonate.

[0262] For example, the azobis compounds include: 1,1'-azobiscyclohexane-1-carboxylonitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), 2,2'-azobis(methyl isobutyrate), 2,2'-azobis(4-methoxy-2,4-dimethylvaleronitrile), α,α'-azobis(isobutyrate), and 4,4'-azobis(4-cyanopentanoic acid), etc.

[0263] After the initiator absorbs light and transitions to an excited state, it transfers its energy, thus enabling its use in conjunction with a photosensitizer that produces a chemical reaction. Examples of photosensitizers include: triethylene glycol bis-3-mercaptopropionate, pentaerythritol tetra-3-mercaptopropionate, and dipentaerythritol tetra-3-mercaptopropionate.

[0264] The initiator content in the total amount of the photosensitive resin composition can be from 0.01 to 10% by weight or from 0.1 to 5% by weight. When the initiator content is within the range described above, sufficient curing is initiated during exposure in a patterning process using the photosensitive resin composition. Therefore, excellent reliability, excellent heat resistance, light resistance, and chemical resistance of the pattern, as well as excellent clarity and adhesion are achieved. Furthermore, it prevents a decrease in transmittance caused by unreacted initiator.

[0265] (F) Solvent

[0266] The solvent is compatible with the binder resin, the reactive unsaturated compound, the pigment, and the initiator, and non-reactive substances can be used.

[0267] For example, the solvents include: alcohols such as methanol and ethanol; ethers such as dichloroethyl ether, n-butyl ether, diisopentyl ether, anisole, and tetrahydrofuran; ethylene glycol ethers such as ethylene glycol monomethyl ether and ethylene glycol monoethyl ether; ethylene glycol ethyl acetate such as methoxyethyl acetate, ethoxyethyl acetate, and ethyl acetate; carbitols such as methyl ethyl carbitol, diethyl carbitol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, and diethylene glycol diethyl ether; and propylene glycol. Propylene glycol alkyl ether acetates such as methyl ether acetate and propylene glycol propyl ether acetate; aromatic hydrocarbons such as toluene and xylene; ketones such as methyl ethyl ketone, cyclohexanone, 4-hydroxy-4-methyl-2-pentanone, methyl-n-propyl ketone, methyl-n-butyl ketone, methyl-n-di-n-pentanone, and 2-heptanone; saturated aliphatic monocarboxylic acid alkyl esters such as ethyl acetate, n-butyl acetate, and isobutyl acetate; lactate esters such as methyl lactate and ethyl lactate; oxyacetic acid alkyl esters such as methyl oxyacetate, ethyl oxyacetate, methyl oxyacetate, and butyl oxyacetate; methoxy Alkoxyalkyl acetate esters such as methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, and ethyl ethoxyacetate; alkyl 3-oxopropionic acid esters such as methyl 3-oxopropionic acid and ethyl 3-oxopropionic acid; alkyl 3-alkoxypropionic acid esters such as methyl 3-methoxypropionic acid, ethyl 3-methoxypropionic acid, ethyl 3-ethoxypropionic acid, and methyl 3-ethoxypropionic acid; alkyl 2-oxopropionic acid esters such as methyl 2-oxopropionic acid, ethyl 2-oxopropionic acid, and propyl 2-oxopropionic acid; methyl 2-methoxypropionic acid, ethyl 2-methoxypropionic acid, and propyl 2-ethoxypropionic acid. Alkyl alkoxypropionic acid esters such as ethyl 2-ethoxypropionate and methyl 2-ethoxypropionate; alkyl 2-oxy-2-methylpropionates such as methyl 2-oxy-2-methylpropionate and ethyl 2-oxy-2-methylpropionate; alkyl monooxycarboxylic acid esters such as methyl 2-methoxy-2-methylpropionate and ethyl 2-ethoxy-2-methylpropionate; esters such as ethyl 2-hydroxypropionate, ethyl 2-hydroxy-2-methylpropionate, ethyl hydroxyacetate, and methyl 2-hydroxy-3-methylbutanoate; and ketoesters such as ethyl pyruvate.

[0268] Furthermore, high-boiling-point solvents such as N-methylformamide, N,N-dimethylformamide, N-methylformaniline, N-methylacetamide, N-dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide, benzyl ethyl ether, dihexyl ether, acetylacetone, isophorone, hexanoic acid, octanoic acid, 1-octanol, 1-nonanol, benzyl alcohol, benzyl acetate, ethyl benzoate, diethyl oxalate, diethyl maleate, γ-butyrolactone, ethylene carbonate, propylene carbonate, and ethylene glycol phenyl ether acetate can be used.

[0269] Considering the compatibility and reactivity of the solvents, ethylene glycol ethers such as ethylene glycol monoethyl ether; ethylene glycol alkoxy ethers such as ethoxyethyl acetate; ethers such as ethyl 2-hydroxypropionate; carbitols such as diethylene glycol monomethyl ether; and propylene glycol alkyl ether acetates such as propylene glycol methyl ether acetate and propylene glycol propyl ether acetate.

[0270] The solvent may be included in the balance of the total amount of the photosensitive resin composition, specifically, the content may be 50 to 90% by weight. When the solvent content is within the range described above, the photosensitive resin composition can have an appropriate viscosity, thereby achieving excellent processability when preparing patterned layers.

[0271] Furthermore, additional embodiments of the present invention may provide a display device.

[0272] The display device of the present invention includes a pattern layer comprising a polymer of a photosensitive resin composition.

[0273] In the display device of the present invention, the relevant content of the photosensitive resin composition is the same as that of the photosensitive resin composition of the present invention described above, and its description is omitted here.

[0274] For example, the polymer of the photosensitive resin composition can be formed by coating the photosensitive resin composition onto a TFT substrate and curing the coated photosensitive resin composition.

[0275] The patterned layer contains polymers of the photosensitive resin composition, resulting in excellent clarity and a large cone angle.

[0276] The display device includes multiple sub-pixels, and the pattern layer may be a pixel definition layer that divides the multiple sub-pixels.

[0277] For example, the sub-pixels of the display device include light-emitting elements, which may be organic light-emitting elements (OLEDs). For instance, the OLED may be formed by sequentially stacking a first electrode, an organic layer, and a second electrode. In this example, the pattern layer is located on the first electrode, and the pattern layer has an opening on the first electrode. The organic layer is disposed within the opening and on the first electrode, and the second electrode is disposed on the organic layer. The light-emitting area of ​​the sub-pixel is defined by the opening area of ​​the pattern layer; therefore, the pattern layer may be a pixel definition layer.

[0278] Furthermore, preferably, the patterned layer is a light-blocking layer that blocks light.

[0279] In one embodiment of the present invention, the pattern layer may have a large cone angle. For example, in one embodiment of the present invention, the tilt angle of the pattern layer may be 20° to 40°. The tilt angle may be the tilt angle relative to the direction parallel to the marking surface at the beginning of the tilt.

[0280] The pattern layer, which serves as the pixel definition layer, has an opening, and the inclined portion connecting the opening and the non-opening portion has an inclined angle.

[0281] In one embodiment of the present invention, the patterned layer comprises a polymer of the photosensitive resin composition, which can form the patterned layer without residue and can achieve a large tilt angle because melt flow is suppressed during the patterning process.

[0282] Consequently, the pattern layer has a large tilt angle, which shortens the length of the tilted portion. Therefore, the distance between the openings can be reduced, and sub-pixels can be densely arranged, giving the display device high definition.

[0283] Hereinafter, specific examples of synthesis and embodiments of the present invention will be described, but the present invention is not limited to the examples of synthesis and embodiments.

[0284] (Synthesis example 1)

[0285] (Preparation of compound 1-1)

[0286] 20 g of 9,9'-bisphenol fluorene (Sigma-Aldrich), 8.67 g of glycidyl chloride (Sigma-Aldrich), 30 g of anhydrous potassium carbonate, and 100 ml of dimethylformamide were poured into a 300 ml three-necked round-bottom flask equipped with a distillation tube. The mixture was heated to 80 °C and reacted for 4 hours. Then, the temperature was lowered to 25 °C, and the reaction solution was filtered. The filtrate was then stirred and added dropwise to 1000 ml of water. The precipitated powder was filtered out, washed with water, and dried under reduced pressure at 40 °C to obtain compound 1-1 (25 g). The purity of the powder was determined by HPLC, and the result showed a purity of 98%.

[0287] <Compound 1-1>

[0288]

[0289] (Synthesis example 2)

[0290] (Preparation of compounds 2-1 to 2-3)

[0291] 25 g (54 mmol) of compound 1-1 obtained in Synthetic Example 1, 8 g of acrylic acid (Ōi Kakin), 0.2 g of benzyl triethylammonium chloride (Ōi Kakin), 0.2 g of hydroquinone (Ōi Kakin), and 52 g of toluene (Sigma Aldrich) were poured into a 300 mL three-necked round-bottom flask equipped with a distillation tube and stirred at 110 °C for 6 hours. After the reaction was completed, the toluene was removed by vacuum distillation to obtain the product. 500 g of silica gel 60 (230–400 mesh, Merck) was packed into a 220 mm diameter glass column, followed by 20 g of the product. 10 L of solvent was prepared by mixing hexane and ethyl acetate in a 4:1 volume ratio. Then, 10 L of this solvent was used for separation to isolate compounds 2-1 to 2-3.

[0292] <Compound 2-1>

[0293]

[0294] <Compound 2-2>

[0295]

[0296] <Compounds 2-3>

[0297]

[0298] (Synthetic Examples 3 to 9)

[0299] (Preparation of polymers 1 to 7)

[0300] As shown in Table 1, compounds 2-1, 2-2, and 2-3 obtained from Synthesis Example 2 were poured into 50 ml three-necked round-bottom flasks equipped with distillation tubes. 0.1 g of tetraethylammonium bromide (Ōi Kakin), 0.03 g of hydroquinone (Ōi Kakin), and 8.05 g of propylene glycol methyl ether acetate (Sigma-Aldrich) were then added to the flasks. Further, 1.22 g of biphenyltetracarboxylic acid dianhydride (Mitsubishi Gas) and 0.38 g of tetrahydrophthalic acid (Sigma-Aldrich) were added. The mixture was then stirred at 110 °C for 6 hours. After the reaction was complete, the reaction solution was recovered to obtain polymers 1 to 7, which consisted of repeating units identical to those in compounds 2-1, 2-2, and 2-3, and were in solution form containing 45% solid powder. The weight-average molecular weight (Mw) of the synthesized polymer was analyzed using gel permeation chromatography (GPC) (Agilent Technologies).

[0301] Table 1

[0302]

[0303] (Synthesis Example 10)

[0304] (Preparation of compound 3-1)

[0305] In a 250 ml three-necked round-bottom flask equipped with a distillation tube, 17 g of (Z)3,4-Dicyano-3-hexene (Hongkong Chemhere), 10 g of 1,8-Diazabicyclo[5,4,0]-7-undecene (Aldrich), 5 g of Vanadium trichloride (Aldrich), and 100 ml of n-Pentanol (Aldrich) were added. The mixture was heated to 120 °C and stirred for 18 hours. All N-Pentanol was removed by vacuum distillation. 100 ml of methanol (Aldrich) was added, and the mixture was stirred for 30 minutes. The mixture was then filtered under reduced pressure to obtain a blue solid. Compound 3-1 was purified by silica gel column chromatography to obtain 11 g of compound 3-1.

[0306] <Compound 3-1>

[0307]

[0308] (Synthesis Example 11)

[0309] (Preparation of compound 3-2)

[0310] The same method as in Synthesis Example 10 was used to synthesize compound 3-2 13.4 g, except that in Synthesis Example 10, 24.4 g of (Z)2-(3-Ethoxypropyl)-3-ethyl-2-butenedinitrile (Shanghai Chemical Products List Co., Ltd.) was used to replace 17 g of (Z)3,4-Dicyano-3-hexene (Hong Kong Chemhere Co., Ltd.).

[0311] <Compound 3-2>

[0312]

[0313] (Synthesis Example 12)

[0314] (Preparation of compound 3-3)

[0315] The same method as in Synthesis Example 10 was used to synthesize compound 3-3 13.4 g, except that in Synthesis Example 10 above, 4.1 g of Nickel dichloride (Aldirich) was used instead of 5 g of Vanadium trichloride (Aldirich).

[0316] <Compound 3-3>

[0317]

[0318] The maximum absorption wavelengths of compounds 3-1 to 3-3 synthesized in Synthetic Examples 10 to 12 are shown in Table 2 below.

[0319] Table 2

[0320] Compound 3-1 Compound 3-2 Compound 3-3 <![CDATA[Absorption λ max (nm)]]> 590 594 585

[0321] (Synthesis Example 13)

[0322] (Preparation of acrylic adhesive)

[0323] 34.2 g of styrene (Aldrich), 10.8 g of methacrylic acid (Aldrich), 9 g of phenylmaleimide (TCI), 6 g of methyl methacrylate (Aldrich), and 6 g of 2,2'-azobis(2,4-dimethylpentanonitrile) (initiator) were poured together with propylene glycol monomethyl ether acetate into a 300 mL flask equipped with a cooling tube and a stirrer. The mixture was then heated to 80 °C and stirred for 4 hours to obtain compound 4-1, which has a weight average molecular weight of 11,000, exists as a solution, and contains 30% solid powder.

[0324] (Preparation Example 1)

[0325] (Preparation of a black pigment dispersion)

[0326] 15g of Irgaphor Black S 100CF (black pigment / BASF), 8.5g of Disperbyk 163 (BYK), and 6.5g of SR-3613 (SMS) were dispersed together with 70g of propylene glycol methyl ether acetate and 100g of zirconia beads with a diameter of 0.5mm (Toray) using a paint shaker (Asada) for 10 hours to obtain a dispersion.

[0327] (Examples 1 to 7)

[0328] The photosensitive combination solution was prepared using the components listed in Table 3 below.

[0329] Table 3

[0330]

[0331]

[0332] (Comparative Examples 1 to 4)

[0333] The photosensitive combination solution was prepared using the components listed in Table 4 below.

[0334] Table 4

[0335]

[0336]

[0337] The method for preparing the light-shielding layer using the combined solutions in Tables 3 and 4 above is as follows:

[0338] (1) Coating and film formation steps

[0339] The black photosensitive resin composition was applied to a cleaned 10cm*10cm glass substrate using a spin coater to a thickness of 1.5μm. Then, the substrate was heated at 100°C for 1 minute to remove the solvent and form a coating film.

[0340] (2) Exposure steps

[0341] A mask of a given morphology is intercalated onto the obtained coating to facilitate the formation of the desired pattern. Then, the coating is irradiated with photochemical rays ranging from 190 nm to 500 nm. An MA-6 exposure unit is used, with an exposure dose of 100 mJ / cm². 2 Standard irradiation.

[0342] (3) Development step

[0343] After performing the exposure step, the image is then developed at 25°C for 1 minute using AZEM's AX 300MIF developer via dipping. The unexposed areas are then rinsed with water to dissolve and remove them, leaving only the exposed areas to form the image pattern.

[0344] (4) Post-processing steps

[0345] In order to obtain a pattern with excellent heat resistance, light resistance, adhesion, crack resistance, chemical resistance, high strength and storage safety, the image pattern obtained by development is post-baked in an oven at 230°C for 30 minutes.

[0346] The reflectivity of the pattern and the highest resolution of the pattern formed on the substrate (the smallest size pattern on the substrate) are recorded in Tables 5 and 6.

[0347] Table 5

[0348]

[0349]

[0350] Table 6

[0351]

[0352] As shown in Tables 5 and 6 above, comparing Examples 1 to 7 using synthetic dyes 10 to 12 with Comparative Examples 2 and 3, it can be seen that the reflectance at a wavelength of 550 nm is lower than that of Comparative Examples 1 and 4 using dyes. Therefore, it can be concluded that the pattern formed by the photosensitive resin composition with added dye has a lower reflectance than the pattern formed by the photosensitive resin composition without added dye, and its application in a display can improve visibility.

[0353] Furthermore, in the 365nm region, Examples 1 to 7 using the dye described in this invention have minimal impact on the reduction of transmittance. It has been verified that, compared with Comparative Example 1 using the same weight % black pigment dispersion, it can improve optical density and reduce reflectance while maintaining similar levels of transmittance and clarity.

[0354] Conversely, Comparative Example 4 did not use the dye described in this invention, but increased the ratio of black pigment dispersion. Compared to Comparative Example 1, its reflectivity decreased, but its transmittance in the 365nm region decreased significantly. This caused the photoinitiator to not receive enough energy from the light source, resulting in a decrease in polymerization degree, a larger minimum size pattern, and a decrease in clarity.

[0355] Comparative Examples 2 or 3 used polymer 6 or polymer 7, which is formed by polymerizing a single monomer. Compared to polymers 1 to 5, polymers 6 and 7 have a relatively linear morphology due to the structure of the monomer. Conversely, Examples 1 to 7 used polymers 1 to 5, which are polymerized into three monomers with different structures. Compared to polymers 6 and 7, polymers 6 and 7 have a relatively network structure. Subsequently, after exposure and development steps, Examples 1 to 7, which used polymers 1 to 5 to form patterns, still exhibited good dye adsorption. It was verified that compared to Comparative Examples 2 and 3, which used linear polymers 6 and 7, they had higher optical density and lower reflectivity.

[0356] Furthermore, comparing the minimum size patterns of Examples 1 to 7 using polymers 1 to 5 with those of Comparative Examples 2 and 3 using polymers 6 and 7, it is evident that Examples 1 to 7 formed patterns of 5.7 to 6.2 μm. Therefore, it is believed that polymers 1 to 5 used in Examples 1 to 7, based on their structural characteristics, effectively achieve intermolecular bonding with the surrounding compounds. Consequently, this structure is more suitable for photolithography processes, resulting in higher resolution during the development process.

[0357] Conversely, the polymers 6 and 7 used in Comparative Examples 2 and 3 have a relatively linear structure compared to polymers 1 to 5. When achieving the smallest pattern size, they start at 9.7 to 9.8 μm, and their clarity has been verified to be relatively low.

[0358] As can be seen from Table 6 above, when the acrylic binder is used together with the dye of the present invention, as in Comparative Example 5, instead of the alkaline soluble resin of the present invention, the clarity is the lowest compared to the alkaline soluble resin of the present invention due to the differences in the structure and characteristics of the polymer chain and branches.

[0359] The above description is merely an example to illustrate the present invention. Anyone skilled in the art can make various modifications without departing from the essential characteristics of the present invention.

[0360] Therefore, the embodiments disclosed in this specification are used to describe the invention and not to limit it. The spirit and scope of the invention are not limited by such embodiments. The scope of the claims of this invention should be interpreted in accordance with the appended claims, and should be interpreted as including all technologies within the same scope as those claims.

[0361] [Potential for Industrial Applications]

[0362] This invention provides a display device comprising:

[0363] A photosensitive resin composition comprising: a resin comprising a repeating unit represented by chemical formula (1), a dye represented by chemical formula (2), a reactive unsaturated compound, a pigment, an initiator, and a solvent; and

[0364] A patterned layer comprising: a polymer of the photosensitive resin composition.

Claims

1. A photosensitive resin composition, characterized in that: The photosensitive resin composition comprises: Adhesive resin, comprising repeating units represented by the following chemical formula (1); The dye is represented by the following chemical formula (2); pigment; Reactive unsaturated compounds; Photoinitiators; and solvent, Chemical formula (1): In the chemical formula (1), 1) This indicates the part where the key is connected by repeating units. 2) R 1 and R 2 Independently defined as: hydrogen; deuterium; or C1 to C2. 20 alkyl groups, 3) a and b are 4 independently. 4) X 1 It is the chemical formula (A). 5) X 2 It is C6~C 30 Aryl, 6) A 1 and A 2 A and B are chemical formulas (C) or (D) that are independent of each other. 1 and A 2 They are different. 7) The adhesive resin comprises repeating units represented by chemical formula (1), wherein the ratio of chemical formula (C) to chemical formula (D) within the polymer chain satisfies 1:9 to 9:

1. Chemical formula (A): In the chemical formula (A), 11-1) Indicates the bonding location, 11-2) R 3 ~R 4 Independently defined as: hydrogen; deuterium; or C1 to C2. 20 alkyl groups, 11-3) c to d are 4 independently of each other. Chemical formula (C): Chemical formula (D): In the chemical formulas (C) and (D), 12-1) Indicates the bonding location, 12-2) R 7 ~R 10 Independently defined as: hydrogen; deuterium; or C1 to C2. 20 alkyl groups, 12-3) Y 1 and Y 2 It is the chemical formula (E). Chemical formula (E): In the chemical formula (E), 13-1) Indicates the bonding location, 13-2) R 11 It is hydrogen; deuterium; or C1 to C2. 20 alkyl groups, 13-3)L 1 It's a single key. Chemical formula (2): In the chemical formula (2), 15-1) M is V=O or Ni, 15-2) R 20 ~R 27 Independently defined as: hydrogen; deuterium; C1 to C2 20 Alkyl groups; or C1-C1 alkyl groups. 20 hydrocarbon oxygen, 16) The R 20 ~R 27 Each may be further substituted by one or more substituents selected from the group consisting of: C1 to C2. 30 Hydroxyl groups; C1~C 30 Alkyl groups; C2-C 30 alkenyl groups; or C2~C 30 The acetylin group.

2. The photosensitive resin composition according to claim 1, characterized in that: The dye represented by the chemical formula (2) has a maximum absorption wavelength of 500 nm to 620 nm.

3. The photosensitive resin composition according to claim 1, characterized in that: The hardened film formed by the photosensitive resin composition has an optical density of more than 1 per 1 μm of film thickness at a wavelength of 550 nm, and a reflectance of less than 9% per 1 μm of film thickness at a wavelength of 550 nm.

4. The photosensitive resin composition according to claim 1, characterized in that: The adhesive resin comprises repeating units represented by the chemical formula (1) and has a weight average molecular weight of 1,000 to 50,000 g / mol.

5. The photosensitive resin composition according to claim 1, characterized in that: The photosensitive resin composition comprises: The adhesive resin comprising 1 to 30% by weight of the repeating units shown in the chemical formula (1) Containing 0.1 to 10% by weight of the dye represented by the chemical formula (2). The pigment is 1 to 30% by weight. The reactive unsaturated compound is 1 to 40% by weight. The photoinitiator is 0.01 to 10% by weight; and The remaining amount of solvent.

6. A patterned layer, characterized in that: Polymerization reactants comprising the photosensitive resin composition of claim 1.

7. The patterned layer according to claim 6, characterized in that: The pattern layer is a light-shielding layer.

8. The patterned layer according to claim 6, characterized in that: The pattern layer is a pixel definition layer that divides into multiple sub-pixels.

9. The patterned layer according to claim 8, characterized in that: The sub-pixel includes a light-emitting component.

10. The patterned layer according to claim 8, characterized in that: The sub-pixel includes an organic light-emitting device.

11. A display device, characterized in that: Includes the patterned layer as described in any one of claims 6 to 10.

12. An electronic device, characterized in that: It includes the display device as described in claim 11 and the control unit that drives the display device.

Images