Composition

Abstract

This invention relates to a composition comprising certain components; its use; the manufacture of layers; and the manufacture of electronic devices.

Description

Technical Field

[0001] This invention relates to a composition comprising (a) a monomer, (b) a metal catalyst, (c) a compound that releases brinsteinic acid, and (d) an absorbent; its use in manufacturing polycyclic olefin layers and in manufacturing electronic devices. Prior Technology

[0002] Electronic devices, and especially organic electronic devices, have become increasingly thinner in recent years, making them now rollable or bendable. This development has led to the development and recent market launch of smartphones, for example, featuring foldable displays based on organic light-emitting device technology.

[0003] However, this device is quite sensitive to environmental influences, especially oxygen and moisture. Without protection, its performance will deteriorate over time, and in some cases quite rapidly.

[0004] In addition, the mechanical stress induced by folding and bending can also cause breakage in any device layer, either directly or near the fold or bend.

[0005] Under these circumstances, many tests have now been completed, as shown in the following patent documents.

[0006] Patent document 1 studies the use of specific cyclic olefin monomers to manufacture layers and obtain improved optical properties.

[0007] Patent document 2 studies compositions with specific potential catalysts and compounds that can produce brucenic acid as ink compositions suitable for 3D objects.

[0008] Patent document 3 provides a single-component composition that can be bulk polymerized under OLED device manufacturing conditions. Furthermore, a composition having a specific cyclic olefin monomer, a catalyst, and a compound capable of releasing brinsteinic acid is also investigated.

[0009] Patent document 4 provides a stable single-component bulk polymerizable composition whose viscosity does not change under or below normal storage conditions, but is bulk polymerized only under the process conditions of the final manufacturing of the OLED device, such as, for example, using radiation and / or thermal processes.

[0010] Patent document 5 studies polycyclic olefin polymers for use in organic electronic devices, which can possess low dielectric properties. [Previous Technical Documents] [Patent Document 1] WO2020 / 002277A1 [Patent Document 2] US2020 / 002466A1 [Patent Document 3] US2019 / 0232267A1 [Patent Document 4] US2019 / 048130A1 [Patent Document 5] WO2015 / 135622A1 Summary of the Invention

[0011] [The technical means to be solved by this invention]

[0012] This invention addresses one or more technical problems that still require improvement.

[0013] Examples include: obtaining a polycyclic olefin layer that is transparent at visible light wavelengths; obtaining a polycyclic olefin layer that blocks non-visible light wavelengths; curing the layer using exposure at a shorter wavelength, although the absorber will absorb specific light; obtaining a polycyclic olefin layer that protects the underlying layer or substrate from damage; obtaining a polycyclic olefin layer with good capacitance or that can be used as a cover layer or insulating layer; obtaining a polycyclic olefin layer with good flexibility or that can be used in flexible display devices; obtaining a transparent composition with good solute solubility; obtaining a stable composition (e.g., that avoids turbidity); obtaining a composition with good printability or coating processability; obtaining a composition with good wetting properties, even on a wide substrate; and / or obtaining a smooth, uniform, closed, or pinhole-free polycyclic olefin layer. [Technical Methods for Problem Solving]

[0014] The present invention provides a composition comprising (a) one or more monomers of formula (I); (b) a potential organic-transition metal catalyst comprising a metal selected from the group consisting of ruthenium, osmium, or palladium; (c) a compound that releases brinsteinic acid when subjected to photodegradation conditions; and (d) an absorber compound with a maximum absorption wavelength between 280 and 410 nanometers. Equation (I) is represented by the following equation. Detailed descriptions of each element are provided below.

[0015] Furthermore, the present invention provides a method for manufacturing a polycyclic olefin layer, the steps of which include: (1) preparing a substrate component; (2) coating the composition of the present invention onto the substrate component; and (3) polymerizing the monomer (a) in the composition.

[0016] In another specific embodiment, the present invention provides a method for manufacturing an electronic device, which includes a method for manufacturing the polycyclic olefin layer of the present invention. In yet another aspect of the present invention, an electronic device manufactured by the method of the present invention is also provided. [Effects of this invention]

[0017] Using the components and / or methods of this invention, one or more of the following effects can be expected.

[0018] It can obtain polycyclic olefin layers that are transparent at visible light wavelengths. It can obtain polycyclic olefin layers that block non-visible light wavelengths (e.g., shorter wavelength regions, UV wavelengths). It can cure the layer using exposure to shorter wavelengths (e.g., UV), although the (d) absorber has absorption near this wavelength. It can obtain polycyclic olefin layers that protect the underlying layer or substrate from damage caused by exposure to shorter wavelengths (e.g., UV). It can obtain polycyclic olefin layers that protect the underlying layer or substrate from water, oxygen, or dust. It can obtain polycyclic olefin layers with good capacitance that can be used as overlays or insulating layers. It can obtain polycyclic olefin layers with good flexibility that can be used in flexible display devices. It can obtain transparent compositions in which the solute has good solubility. It can obtain stable compositions that avoid turbidity. It can obtain compositions with good printability or coating processability. It can obtain compositions with good wetting properties, even on wide substrates (e.g., in display devices). It can produce smooth, uniform, closed, or pinhole-free polycyclic olefin layers. Simple Explanation of the Diagram

[0019] none. Implementation

[0020] The following details specific embodiments of the present invention. [definition]

[0021] Unless otherwise indicated in this specification, the definitions and examples described in the following paragraphs shall apply.

[0022] The singular form includes the plural form, and "a" or "the" means "at least one". One element of a concept can be represented by a plural, and when describing a quantity (e.g., mass percentage or mole percentage), it represents the sum of the plural.

[0023] "And / or" includes all combinations of elements, as well as singular uses of elements.

[0024] When using "to" or "-" to indicate a numerical range, it includes both endpoints and shares the same units. For example, 5 to 25 moles percent means 5 moles or more and 25 moles or less.

[0025] The terms "C x -y", "C xC y", and "C x" indicate the number of carbons in a molecule or substituent. For example, C 1-6 alkyl indicates an alkane chain with one or more carbons and six or fewer carbons (methyl, ethyl, propyl, butyl, pentyl, hexyl, etc.).

[0026] When a polymer has a plurality of repeating units, these repeating units copolymerize. These copolymerizations can be any alternating copolymerization, random copolymerization, block copolymerization, graft copolymerization, or mixtures thereof. When a polymer or resin is represented by a structural formula, the n, m, etc., immediately following the formula indicate the number of repetitions.

[0027] Celsius is used as a unit of temperature. For example, 20 degrees means 20 degrees Celsius.

[0028] An additive refers to a compound that inherently possesses a function (e.g., in the case of a base-generating agent, the compound itself produces a base). It is also permissible for the compound to be dissolved or dispersed in a solvent and added to the composition. As a specific embodiment of the present invention, it is preferred that this solvent be included in the composition of the present invention as the solvent for the additive.

[0029] In summary, this case relates to a composition comprising (a) a monomer, (b) a metal catalyst, (c) a compound that releases brinsteinic acid, and (d) an absorbent. It should be noted that, for the purposes of this invention, the terms "cycloolefin" and "polycycloolefin" may preferably be referred to as "norcamphene" and "polynorcamphene," respectively. [Composition]

[0030] This invention provides a composition comprising (a) one or more monomers of formula (I); (b) a potential organic-transition metal catalyst comprising a metal selected from the group consisting of ruthenium, osmium, or palladium; (c) a compound that releases brinsteinic acid upon exposure to photodegradation conditions; and (d) an absorber compound with a maximum absorption wavelength between 280 and 410 nanometers. This composition is preferably a polycyclic olefin layer-forming composition (more preferably a visible-light-transparent polycyclic olefin layer-forming composition). Polycyclic olefin layer-forming compositions can be composed of the compositions of this invention. The components are described in detail below.

[0031] The viscosity of the composition of the present invention is preferably 5-20 mPass (more preferably 5-15 mPass; even more preferably 5-12 mPass). Viscosity can be measured by known methods. The temperature for measuring the viscosity of the composition of the present invention is preferably 20-40°C (more preferably 25-40°C; even more preferably 40°C).

[0032] The surface tension of the composition of this invention is preferably 10-50 mN / m (more preferably 20-40 mN / m; even more preferably 25-40 mN / m) at 25°C. Surface tension can be measured using known methods. Without wishing to be bound by theory, the composition of this invention exhibits good processability for printing and coating techniques, good wettability to a wide range of substrate materials, and / or, when coated onto a substrate component, produces a smooth, uniform, sealed, and / or pinhole-free film. [(a) Monomer]

[0033] The composition of the present invention comprises (a) one or more monomers of formula (I); wherein formula (I) is represented by the following formula.

[0034] m is an integer of 0, 1, or 2 (preferably 0 or 1). In one preferred embodiment of the present invention, m is 1. In another preferred embodiment of the present invention, m is 0.

[0035] R1, R2, R3, and R4 are each independently selected from the group consisting of hydrogen, halogen, methyl, ethyl, linear or branched C1-20 alkyl, perfluoroC1-12 alkyl, hydroxyC1-16 alkyl, C3-12 cycloalkyl, C6-12 bicycloalkyl, (CH2)aC6-12 bicycloalkenyl, C7-14 tricycloalkyl, substituted or unsubstituted C6-10 aryl, substituted or unsubstituted C6-10 arylC1-6 alkyl, perfluoroC6-10 aryl, perfluoroC6-10 arylC1-3 alkyl, and groups of formula (A). -Z-aryl(A).

[0036] R1, R2, R3, and R4 are preferably each independently selected from the group consisting of hydrogen, ethyl, linear or branched C3-8 alkyl, substituted or unsubstituted C6-10 aryl C1-6 alkyl, and alkyl of formula (A); more preferably selected from the group consisting of hydrogen, ethyl, linear or branched C3-8 alkyl, and unsubstituted C6-10 aryl C1-6 alkyl.

[0037] In one preferred embodiment of the present invention, R2, R3, and R4 are hydrogen. In another preferred embodiment of the present invention, R1 is not hydrogen.

[0038] Z is a single bond or a base selected from the group consisting of: (CR 5R 6)a, O(CR 5R 6)a, (CR 5R 6)aO, (CR 5R 6)aO-(CR 5R 6)b, (CR 5R 6)aO-(SiR 5R 6)b, (CR 5R 6)a-(CO)O-(CR 5R 6)b. Z is preferably (CR 5R 6)a.

[0039] a and b are each independent integers from 1 to 12 (preferably 1 to 3; more preferably 1 or 2; even more preferably 2).

[0040] R5 and R6 are each independently selected from the group consisting of hydrogen, methyl, ethyl, linear or branched C3-8 alkyl, hydroxyl, methoxy, ethoxy, linear or branched C3-6 alkoxy, acetoxy, C2-6 acetyl, hydroxymethyl, hydroxyethyl, linear or branched hydroxy C3-6 alkyl, substituted or unsubstituted phenyl, and substituted or unsubstituted phenoxy (preferably selected from the group consisting of hydrogen, methyl and tert-butyl; more preferably hydrogen).

[0041] The aryl group is phenyl, or is a phenyl group substituted with one or more alkyl groups selected from the group consisting of methyl, ethyl, linear or branched C3-6 alkyl, hydroxyl, methoxy, ethoxy, linear or branched C3-6 alkoxy, acetoxy, C2-6 acetyl, hydroxymethyl, hydroxyethyl, linear or branched C3-6 alkyl, phenyl, and phenoxy; preferably phenyl.

[0042] Depending on the circumstances, one of R1 or R2, together with one of R3 or R4 and the carbon atom to which they are attached, forms a C5-7 carbon ring, which may contain one or more double bonds. A preferred embodiment is one where neither R1 nor R2 forms a C5-7 carbon ring with either R3 or R4.

[0043] As one specific embodiment of the present invention, formula (I) can be formula (Ia).

[0044] a is either 0 or 1. In one specific embodiment, a is 0. In another specific embodiment, a is 1.

[0045] R1 is a linear or branched C1-20 alkyl, or an unsubstituted C6-10 aryl C1-6 alkyl (preferably methyl, ethyl, isopropyl, tributyl, n-butyl, n-hexyl, n-octyl, phenylmethyl, or phenethyl; more preferably n-butyl, n-hexyl, n-octyl, or phenethyl).

[0046] As a preferred embodiment, formula (I) may be selected from the group consisting of the following formulas (Ia-01) to (Ia-21):

[0047] As a preferred embodiment, formula (I) may be selected from the group consisting of formulas (Ia-04), (Ia-05), (Ia-07), (Ia-08), (Ia-19), (Ia-20), (Ia-21), and (Ia-22). As a further preferred embodiment, formula (I) may be selected from the group consisting of formulas (Ia-04), (Ia-07), (Ia-08), (Ia-20), and (Ia-21).

[0048] As a specific embodiment of one of the components of the present invention, (a) the content of the monomer is 80-99.99% by mass based on the composition (preferably 90-99.99% by mass; more preferably 90-99.95% by mass).

[0049] Regarding (a) monomers, the present invention can accept mixtures of isomers represented by formula (I). (b) Metal catalyst

[0050] The composition of this invention includes (b) a potential organic-transition metal catalyst comprising a metal selected from the group consisting of ruthenium, osmium, or palladium. The metal is preferably ruthenium or osmium (more preferably ruthenium).

[0051] The potential organo-transition metal catalyst may be an organorruthenium compound selected from the group consisting of compounds of formula (IIA), formula (IIB), formula (IIIA), formula (IIIB), formula (IIIC), and formula (IIID).

[0052] In a preferred embodiment of the present invention, the organoruthenium compound is selected from the group consisting of compounds of formula (IIB), formula (IIIA), formula (IIIB), and formula (IIID). In a more preferred embodiment of the present invention, the organoruthenium compound is a compound of formula (IIIA) or a compound of formula (IIID).

[0053] The ruthenium metal in formulas (IIA), (IIB), (IIIA), (IIIB), (IIIC), or (IIID) may be replaced by osmium or palladium, depending on the application. A further preferred embodiment of the invention is (b) where the metal catalyst is ruthenium.

[0054] X is independently selected from the group consisting of chlorine, bromine, iodine, -ORa, -O(CO)Ra, -S(Ra)2, -OSO2Ra, and -N(Ra)2. In a preferred embodiment, X is independently selected from the group consisting of chlorine, bromine, iodine, -S(Ra)2, -OSO2Ra, and -N(Ra)2. In a more preferred embodiment, X is independently selected from the group consisting of iodine, -S(Ra)2, and -N(Ra)2.

[0055] Ra is independently selected from the group consisting of single bonds, C1-12 alkyl groups, C3-12 cycloalkyl groups, C6-14 aryl groups, and =CH(Ra'). In a preferred embodiment, Ra is independently selected from the group consisting of single bonds, C1-4 alkyl groups, phenyl groups, and =CH(Ra'). In a more preferred embodiment, Ra is independently selected from the group consisting of single bonds, phenyl groups, and =CH(Ra').

[0056] Any combination of the two Ra can bond with each other.

[0057] Ra' is a single bond that bonds Ra or L (preferably L).

[0058] Y is selected from the group consisting of O, S and NCOCF 3 (preferably O and S; more preferably O).

[0059] Y' is selected from the group consisting of OR 9, SR 9, and -N=CHC(O)O (C 1-6 alkyl).

[0060] R 9 is selected from the group consisting of methyl, ethyl, linear or branched C1-6 alkyl, C6-10 aryl, methoxy, ethoxy, linear or branched C1-6 alkoxy, C6-10 aryl, and -OCH(CH 3)C(O)N(CH 3)(OCH 3). A preferred embodiment of R 9 is selected from the group consisting of methyl, ethyl, linear or branched C3-6 alkyl, C6-10 aryl, methoxy, ethoxy, linear or branched C3-6 alkoxy, C6-10 aryl, and -OCH(CH 3)C(O)N(CH 3)(OCH 3).

[0061] L is selected from the group consisting of pyridine, PR3, O=PR3, and -OR3 (preferably PR3 and -OR3).

[0062] R 3 is independently selected from the group consisting of isopropyl, secondary butyl, tertiary butyl, cyclohexyl, bicyclic C5-10 alkyl, phenyl, benzyl, isopropoxy, secondary butoxy, tertiary butoxy, cyclohexyloxy, phenoxy, and benzyloxy (preferably isopropyl, secondary butyl, tertiary butyl, cyclohexyl, bicyclic C5-10 alkyl, phenyl, benzyl, isopropoxy, secondary butoxy, tertiary butoxy, cyclohexyloxy, phenoxy, and benzyloxy; more preferably cyclohexyl and phenyl).

[0063] X and L can form an anionic ligand of the formula XL.

[0064] R 7 is selected from the group consisting of isopropyl, secondary butyl, tertiary butyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, and substituted or unsubstituted naphthyl (preferably isopropyl, secondary butyl, tertiary butyl, cyclohexyl, substituted phenyl, and substituted naphthyl; more preferably cyclohexyl, substituted phenyl, and substituted naphthyl).

[0065] R8 is selected from the group consisting of hydrogen, chlorine, methyl, ethyl, linear or branched C1-6 alkyl, C6-10 aryl, methoxy, ethoxy, linear or branched C1-6 alkoxy, C6-10 aryloxy, -NHCO(C1-6)alkyl, -NHCO-perfluoro(C1-6)alkyl, -SO2N((C1-6)alkyl)2, and -NO2. In one preferred embodiment of the invention, R8 is selected from the group consisting of hydrogen, chlorine, methyl, ethyl, phenyl, methoxy, ethoxy, and -NO2. More preferably, R8 is hydrogen.

[0066] Ar 1, Ar 2, Ar 3, and Ar 4 are each independently selected from the group consisting of substituted or unsubstituted phenyl groups, substituted or unsubstituted biphenyl groups, and substituted or unsubstituted naphthyl groups (preferably substituted or unsubstituted phenyl groups; more preferably substituted phenyl groups). As a specific embodiment of the invention, each Ar 1, Ar 2, Ar 3, and Ar 4 is preferably having 1 to 3 substituents on the selected group (more preferably 1 or 3 substituents; further preferably 3 substituents; or even more preferably 1 substituent).

[0067] When the above-mentioned group has substituents, each substituent is independently selected from the group consisting of methyl, ethyl, isopropyl, tert-butyl, phenyl, and OSi(SiMe 3) 3 (preferably methyl, ethyl, and isopropyl; more preferably methyl and isopropyl). Here, "Me" in "OSi(SiMe 3) 3" means methyl.

[0068] m is an integer of 1, 2, or 3 (preferably 1 or 2; more preferably 1). In another preferred embodiment of the invention, m is 2.

[0069] While not intended to limit the scope of the invention, (b) exemplary compounds of potential organic-transition metal catalysts can be described below.

[0070] (b) The content of the potential organic-transition metal catalyst is 0.0001-10% by mass based on the composition (preferably 0.001-0.5% by mass; more preferably 0.005-4% by mass; further preferably 0.010-0.10% by mass). [(c) Compounds that can release Brinzyl acid]

[0071] The composition of the present invention includes (c) a compound that releases brinster acid when subjected to photodecomposition conditions.

[0072] As one specific embodiment of the present invention, (c) the compound is represented by the following formula (V).

[0073] Y is a halogen (preferably chlorine, bromine, or iodine; more preferably chlorine).

[0074] R 30 and R 31 are each independently selected from the group consisting of hydrogen, methyl, ethyl, linear or branched C3-12 alkyl, C3-12 cycloalkyl, C6-12 bicycloalkyl, C7-14 tricycloalkyl, C6-10 aryl, C6-10 aryl-C1-3 alkyl, C1-12 alkoxy, C3-12 cycloalkoxy, C6-12 bicycloalkoxy, C7-14 tricycloalkoxy, C6-10 aryloxy-C1-3 alkyl, and C6-10 aryloxy.

[0075] R 30 is preferably selected from the group consisting of hydrogen, methyl, ethyl, isopropyl, n-propyl, phenyl, methoxy, ethoxy, isopropoxy, n-propoxy, and phenoxy (more preferably hydrogen, methyl, ethyl, and tert-butyl; further preferably hydrogen and tert-butyl; even more preferably hydrogen).

[0076] R 31 is preferably selected from the group consisting of methyl, ethyl, isopropyl, n-propyl, phenyl, methoxy, ethoxy, isopropoxy, n-propoxy, and phenoxy (more preferably methyl, ethyl, n-propyl, methoxy, ethoxy, n-propoxy, and phenoxy; further preferably ethoxy and n-propoxy; further preferably n-propoxy).

[0077] While not intended to limit the scope of the invention, (c) exemplary compounds that release brinsteric acid when subjected to photodecomposition conditions are described below.

[0078] (c) The content of the compound that releases Brønsted acid is 0.0001-1.0% by mass based on the composition (preferably 0.001-0.5% by mass; more preferably 0.01-0.40% by mass; further preferably 0.02-0.10% by mass). [(d) Absorbent compound]

[0079] The composition of this invention includes (d) an absorber compound with a maximum absorption wavelength between 280 and 410 nanometers. In one specific embodiment of this invention, the maximum absorption wavelength of (d) the absorber compound is preferably between 300 and 410 nanometers (more preferably 350 and 410 nanometers).

[0080] The light absorption characteristics can be measured using known methods. For example, the absorbent compound (d) is dissolved in a nonpolar organic solvent (e.g., 1-heptyl-2-norbornene), and the absorption spectra of the solution under various light sources (e.g., UV) are evaluated using known spectroscopic equipment.

[0081] (d) The absorbent compound is used to block UV by means of the "excited intramolecular proton transfer (ESIPT)" mechanism; and / or when it is formed (preferably by deposition) a layer, the (d) absorbent compound is excited by an electric field.

[0082] One preferred embodiment of the present invention is (d) an absorbent compound used to block UV via the ESIPT mechanism.

[0083] (d) The absorbent compound may have hydroxyl and / or methoxy groups (preferably hydroxyl or methoxy; more preferably hydroxyl).

[0084] As one specific embodiment of the present invention, (d) the absorbent compound is preferably represented by a formula selected from the group consisting of (d-1), (d-2), and (d-3) (more preferably (d-1) and (d-2); even more preferably (d-1)). This (d) absorbent compound preferably functions as an ESIPT mechanism in the layer formed by the composition of the present invention. The formulas are detailed below.

[0085] R21 and R22 are each independently hydrogen, linear or branched C1-5 alkyl or C6-10 aryl (preferably hydrogen or linear C1-5 alkyl).

[0086] Depending on the circumstances, the C1-5 alkyl groups of R21 and R22 may be bonded together to form a saturated or unsaturated ring. As one specific embodiment of the invention, the C1-5 alkyl groups of R21 and R22 are preferably bonded together to form a saturated ring (more preferably cyclopentane). Depending on the circumstances, one or more methylene groups of this saturated ring may be independently substituted with -(C=O)- or -NR 25-. As one specific embodiment of the invention, it is preferred that two or three methylene groups of this saturated ring are independently substituted with -(C=O)- or -NR 25-.

[0087] Formula (d-1) can be the formula (d-1-1) described below. When formula (d-1-1) is interpreted from formula (d-1), the C1-5 alkyl groups of R21 and R22 are bonded to each other to form a saturated ring (cyclopentane). Two methylene groups in this cyclopentane are replaced by -(C=O)-linking groups. One methylene group in this cyclopentane is replaced by -NR25-.

[0088] R 25 are each independently hydrogen, linear or branched C1-5 alkyl or C6-10 aryl (preferably hydrogen, methyl, ethyl, isopropyl, n-propyl, n-butyl, tributyl, or phenyl; more preferably hydrogen, methyl, n-propyl, n-butyl, or phenyl; even more preferably n-butyl).

[0089] m 21 is an integer from 1 to 3 (preferably 1 or 2; even more preferably 1).

[0090] R23 and R24 are each independently C1-10 alkyl, C6-18 aryl, C6-12 aryl-C1-5 alkyl, or C1-5 alkyl-C6-12 aryl (preferably C4-8 alkyl, phenyl and phenyl-C1-3 alkyl; more preferably C5-8 alkyl and phenyl-C1-3 alkyl).

[0091] The alkyl portions of R 23 and R 24 may each be linear or branched independently (preferably all or part of the alkyl portion is branched).

[0092] Depending on the circumstances, the methylene groups of the alkyl portions of R 23 and R 24 may be replaced by -CO-, -O-, or -COO- (preferably -COO-).

[0093] While not intended to limit the scope of the invention, the exemplary compounds of formula (d-1) are described below.

[0094] R32 and R33 are each independently a C1-21 hydrocarbon group (preferably linear or branched C1-21 alkyl; more preferably linear or branched C1-10 alkyl). The C1-20 hydrocarbon groups of R32 and R33 may, depending on the situation, form saturated or unsaturated rings (preferably benzene rings).

[0095] The compound represented by formula (d-2) may have one or more carbon-carbon single bonds replaced by carbon-carbon double bonds. Preferably, R32 and R33 may have one or more carbon-carbon single bonds replaced by carbon-carbon double bonds. The methylene moiety of R32 may be replaced by -O- or -CO-.

[0096] L 31 is a C1-12 hydrocarbon linker (preferably linear or branched C1-6 alkyl; more preferably linear or branched C1-4 alkyl; even more preferably methylene). L 31 may, depending on the case, form a saturated or unsaturated ring (preferably phenyl). The methylene moiety of L 31 may, depending on the case, be substituted with -O-.

[0097] L 32 is -CO-, -CH 2- or -CH(CH 3)- (preferably -CO- or -CH(CH 3)-; more preferably -CH(CH 3)-).

[0098] In the compound represented by formula (d-2), at least one methyl group is substituted with a hydroxyl or methoxy group.

[0099] While not intended to limit the scope of the invention, the exemplary compounds of formula (d-2) are described below.

[0100] R41, R42, and R43 are each independently a C1-20 hydrocarbon group. The C1-20 hydrocarbon group of R41, R42, or R43 may form a saturated or unsaturated ring (preferably a benzene ring). The methylene moiety of R41, R42, or R43 may be substituted with -O-.

[0101] In the compound represented by formula (d-3), at least one methyl group is substituted with a hydroxyl or methoxy group.

[0102] While not intended to limit the scope of the invention, the exemplary compounds of formula (d-3) are described below.

[0103] (d) The absorbent compounds are commercially available. Examples of commercially available (d) absorbents are selected from the group consisting of: Tinuvin 328, Tinuvin 477, Tinuvin 900, Tinuvin 928, Tinuvin 970, Tinuvin 384, Eusolex 9020, Oxynex ST, Eusolex S, BL1226, BL1337 (Jade New Material), FDB-009 (Yamada Chemical), LOTSORB B series (Jiangxi Lotchem), LA-F70 (Adeka Fine Chemicals), and any combination thereof.

[0104] As another preferred embodiment of the present invention, the (d) absorbent compound may have the characteristic of being excited by an electric field when it is formed into a layer. For example, chemical compounds used in OLEDs have this characteristic. A preferred embodiment of such a (d) absorbent compound is one that can be used in the emitter layer (EML, as a host or dopant), hole transport layer (HTL), hole injection layer (HIL), electron transport layer (ETL), or electron injection layer (EIL) of an OLED. Hereinafter, such a (d) absorbent compound that can exhibit properties for OLEDs is referred to as "(d) absorbent compound with OLED properties". A more preferred embodiment of such a (d) absorbent compound is one that can be used in the HTL or HIL of an OLED. A further preferred embodiment of such a (d) absorbent compound is one that can be used in the HTL of an OLED.

[0105] This layer can be formed by coating or deposition (preferably vacuum deposition).

[0106] (d) Preferred examples of absorber compounds with OLED properties are those that, when formed in a layer within an OLED, can exhibit hole injection and / or hole transport properties. These include, for example, triarylamines, benzidines, tetraaryl-p-phenylenediamines, triarylphosphines, and phenanthrene compounds. Class, coffee Class, dihydrophobic Class A, thiazolinones, dibenzo-p-dioxins, phenanthrene Thiarate derivatives (phenoxathiyne), carbazole derivatives, azulene derivatives, thiophene derivatives, pyrrole derivatives, furans, and their derivatives, as well as other heterocycles containing O, S, or N with high HOMO (HOMO = highest occupied molecular orbital).

[0107] Compounds exhibiting hole injection and / or hole transport properties may specifically be mentioned as follows: phenylenediamine derivatives (US 3615404), arylamine derivatives (US 3567450), amino-substituted chalcone derivatives (US 3526501), styrylanthracene derivatives (JP-A-56-46234), polycyclic aromatic compounds (EP 1009041), polyarylalkane derivatives (US 3615402), genistein derivatives (JP-A-54-110837), hydrazone derivatives (US 3717462), acetohydrazones, stilbene derivatives (JP-A-61-210363), silazane derivatives (US 4950950), polysilanes (JP-A-2-204996), aniline copolymers (JP-A-2-282263), and thiophene oligomers (JP Heisei 1). (1989) 211399), polythiophenes, poly(N-vinylcarbazole) (PVK), polypyrroles, polyanilines and other conductive macromolecules, porphyrin compounds (JP-A-63-2956965, US 4720432), aromatic dimethylene compounds; carbazole compounds, such as CDBP, CBP, mCP; aromatic tertiary amines and styrylamine compounds (US 4127412), such as benzidine-type triphenylamines, styrylamine-type triphenylamines, and diamine-type triphenylamines. Arylamine dendritic polymers (JP Heisei 8 (1996) 193191), monomeric triarylamines (US 3180730), triarylamines containing one or more vinyl groups and / or at least one active hydrogen functional group (US 3567450 and US 3658520), or tetraaryldiamines (two tertiary amine units linked by an aryl group) can also be used. The molecule may also contain more triarylamine groups. Phthalocyanine derivatives, naphthylphthalocyanine derivatives, butadiene derivatives, and quinoline derivatives, such as dipyridyl phthalocyanine, are also used. [2,3-f:2',3'-h]quinoline Linopyranitrile is also suitable.

[0108] Preferably, they are aromatic tertiary amines containing at least two tertiary amine units (US 2008 / 0102311 A1, US 4720432 and US 5061569), such as NPD (α-NPD=4,4'-di[N-(1-naphthyl)-N-phenylamino]biphenyl) (US 5061569), TPD 232 (=N,N'-di(N,N'-diphenyl-4-aminophenyl)-N,N-diphenyl-4,4'-diamino-1,1'-biphenyl) or MTDATA (MTDATA or m-MTDATA=4,4',4''-triphenylamine [(3-methylphenyl)phenylamino]) (JP-A-4-308688), TBDB (=N,N,N',N'-tetra(4-biphenyl)diaminobiphenylene), TAPC (=1,1-di(4-di-p-tolylaminophenyl)cyclohexane), TAPPP (=1,1-di(4-di-p-tolylaminophenyl)-3-phenylpropane), BD TAPVB (=1,4-di[2-[4-[N,N-di(p-tolyl)amino]phenyl]vinyl]benzene), TTB (=N,N,N',N'-tetra-p-tolyl-4,4'-diaminobiphenyl), TPD (=4,4'-di[N-3-methylphenyl]-N-phenylaminobiphenyl), N,N,N',N'-tetraphenyl-4,4'''-diamino-1,1',4',1'',4'',1'''-tetraphenyl, and tertiary amines containing carbazole units, such as TCTA (=4-(9H-carbazole-9-yl)-N,N-di[4-(9H-carbazole-9-yl)phenyl]aniline). Also preferred are hexaazine terphenyl compounds and phthalocyanine derivatives (e.g., H₂Pc, CuPc (=copper phthalocyanine), CoPc, NiPc, ZnPc, PdPc, FePc, MnPc, ClAlPc, ClGaPc, ClInPc, ClSnPc, Cl₂SiPc, (H₂O)AlPc, (H₂O)GaPc, VOPc, TiOPc, MoOPc, GaPc-O-GaPc) in accordance with US 2007 / 0092755A1.

[0109] (d) More preferred examples of absorber compounds with OLED properties are disclosed as follows (TA-1) to (TA-16), as disclosed in EP 1162193B1, EP 650955B1; Synth. Metals

[1997] , 91(1-3), 209;DE 19646119 A1, WO 2006 / 122630 A1, EP 1860097 A1, EP 1834945 A1, JP 08053397 A, US 6251531 B1, US 2005 / 0221124, JP 08292586 A、US 7399537 B2 [、]US 2006 / 0061265 A1, EP 1661888, and WO 2009 / 041635. Compounds of formulas (TA-1) to (TA-16) may also be substituted.

[0110] Other compounds that can be used as absorbent compounds with OLED properties (d) are disclosed in EP 0891121 A1, EP 1029909 A1 and US 2004 / 0174116 A1.

[0111] These arylamines and heterocycles, which are typically used as absorber compounds with OLED properties, preferably produce a HOMO greater than -5.8 eV (relative vacuum level) (more preferably greater than -5.5 eV) in the layers formed therefrom.

[0112] As a specific embodiment of one of the components of the present invention, the content of the (d) absorbent compound is 0.5-15% by mass (preferably 1-15% by mass; more preferably 2-10% by mass; further preferably 2-6% by mass) based on the composition. For clarity, when the composition contains a plurality of (d) absorbent compounds, the content is the sum of these (d) absorbent compounds. [additive]

[0113] The composition of this invention may further include additives. Here, additives are different from the components described above. Additives may be selected from the group consisting of antioxidants, synergists, viscosity modifiers, binders, solvents, other absorbents, and any combination thereof. Here, other absorbents refer to light-absorbing compounds that are different from any compound represented by formulas (d-1), (d-2), and (d-3), and different from any compound that can be excited by an electric field when formed into a laminate. As for the solvent, for example, an organic solvent may be used to dissolve specific compounds with low solubility. Specific embodiments described in US2020 / 002466A1 or WO2020 / 002277A1 can generally be used as this additive.

[0114] As one specific embodiment of the composition of the present invention, the content of this additive is 0-15% by mass based on the composition (preferably 0.01-10% by mass; more preferably 0.1-5% by mass; further preferably 0.1-1% by mass). Another preferred embodiment is that the composition of the present invention does not contain this additive (0.0% by mass based on the composition).

[0115] As a specific embodiment, the composition of the present invention may further include a solvent. The solvent is preferably an inorganic solvent or an organic solvent (more preferably an organic solvent). The content of this solvent, based on the composition, is preferably 0.0-1.0% by mass (more preferably 0.001-0.5% by mass; further preferably 0.001-0.1% by mass; even more preferably 0.001-0.01% by mass). Another preferred embodiment is that the composition of the present invention does not contain this solvent (0.000% by mass). [Layer formation]

[0116] This invention provides a method for manufacturing a polycyclic olefin layer, the steps of which include the following: (1) Preparation of the substrate component; (2) Applying the components of the present invention onto the substrate member; and (3) Polymerize (a) monomer in the composition.

[0117] The numbers in parentheses indicate the order of the steps. For example, when steps (1), (2), and (3) are described, the order of the steps is as stated above. The same applies below, unless otherwise stated.

[0118] Here, in this invention, "above" includes cases in which a polycyclic olefin layer is formed on a substrate member (in direct contact) and cases in which a polycyclic olefin layer is formed on a substrate member via another layer. For example, a planarization film may be formed on a substrate member, and the composition of this invention may be coated on the planarization film.

[0119] In summary, the present invention also relates to an electronic device, preferably an organic electronic device, comprising a substrate component and a polycyclic olefin layer that can be manufactured according to the method of the present invention described herein.

[0120] The substrate component is not particularly limited and can, in principle, be any component on which a polycyclic olefin layer can be deposited (e.g., a substrate, device, or device assembly, all described below). It is not intended to be theoretically constrained, but it is believed that this polycyclic olefin layer helps protect the underlying substrate component from water, oxygen, dust, or any other materials harmful to the underlying substrate component.

[0121] The substrate component is preferably an electronic device or a component of an electronic device, and more preferably an organic electronic device or a component of an organic electronic device.

[0122] Examples of this substrate component can be selected from the group consisting of electronic devices such as light-emitting diodes, photovoltaic cells, photodetector cells, semiconductor devices, and thin-film transistors, which can be organic, inorganic, or hybrid.

[0123] This electronic device typically includes (preferably in sequence) a first electrode, a functional layer, and a second electrode. The functional layer may be selected, for example, from the group consisting of a light-emitting layer, a semiconductor layer, and a photoactive layer.

[0124] Depending on the architecture of the resulting electronic device, the polycyclic olefin layer may be attached to either the first or second electrode side (but not necessarily directly).

[0125] The substrate is not particularly limited, whether it is part of or constitutes part of the substrate structure. A suitable substrate is preferably inert under operating conditions. This substrate may, for example, be flexible. Preferred examples of suitable substrate materials include polymers, glasses, metals, and any blends thereof, including, for example, blends of more than one polymer or metal. Preferred polymeric materials include, but are not limited to, alkyd resins, allyl esters, benzocyclobutenes, butadiene-styrene, cellulose, cellulose acetate, epoxides, epoxy polymers, ethylene-chlorotrifluoroethylene copolymers, ethylene-tetrafluoroethylene copolymers, glass fiber reinforced polymers, fluorocarbon polymers, hexafluoropropylene-vinylidene fluoride copolymers, high-density polyethylene, parylene, polyamides, polyimides, polyarylamides, polysiloxanes (e.g., polydimethylsiloxane), polyether ethers, polyethylene, polyethylene naphthalate, polyethylene terephthalate, polyketones, polymethyl methacrylate, polypropylene, polystyrene, polyurethane, polytetrafluoroethylene, polyurethane, polyvinyl chloride, polycyclic olefins, polysiloxane rubbers, polysiloxanes, and cis-butadiene-imide type resins. Preferably, the substrate is made of polyethylene terephthalate, polyimide, polycyclic olefin, or polyethylene naphthalate. In some specific embodiments of the invention, the substrate can be any suitable material, such as a polymeric material coated with one or more of the above-mentioned materials or coated with one or more metals (e.g., titanium), a metal, or a glass material. It should be understood that methods such as extrusion, stretching, friction, or photochemical techniques can be used in forming this substrate to provide a uniform surface for device manufacturing. Alternatively, the substrate can be a polymeric material coated with one or more of the above-mentioned polymeric materials, a metal, or a glass.

[0126] In step (2) of the present invention, the means of "coating" the composition is preferably selected from the group consisting of deposition, dip coating, spin coating, inkjet printing, nozzle printing, letterpress printing, screen printing, gravure printing, doctor blade coating, roller printing, reverse roller printing, lithography, dry lithography, flexographic printing, roll-to-roll printing, spraying, curtain coating, brush coating, slot dye coating, and pad printing (more preferably deposition, spin coating, inkjet printing, or nozzle printing; further preferably spin coating and inkjet printing; even more preferably inkjet printing).

[0127] In step (3) of the present invention, monomer (a) is polymerized into a polycyclic olefin layer. The "polymerization" in step (3) is carried out by irradiation and / or heat (preferably irradiation).

[0128] The irradiation described above is preferably performed using a wavelength with a peak value of 260-430 nm (more preferably 350-410 nm; even more preferably 380-400 nm). UV irradiation is a preferred embodiment of this irradiation. The gaseous environment for this irradiation can be selected from known conditions, such as air, nitrogen, and mixtures thereof. The temperature can be controlled according to known conditions, such as 20-27°C (preferably 25-27°C).

[0129] As described above, applying a heat treatment at increased temperature to the components on the substrate is one specific embodiment of the present invention. 50-150°C (preferably 70-120°C) is one specific embodiment of this condition. 10-180 minutes (preferably 10-60 minutes) is another specific embodiment of this condition. The gaseous environment for this heat treatment can be selected from known conditions, such as air, nitrogen, and mixtures thereof. The temperature can be controlled according to known conditions, such as 20-27°C (preferably 25-27°C).

[0130] Using the compositions of this invention, a substantially transparent layer can be formed when exposed to suitable radiation. Polycyclic olefin polymers manufactured by the methods described herein can form substantially transparent layers. Suitable radiation sources can be natural light or artificial light (e.g., LED light).

[0131] The transparent layer is preferably 80-99.9% (more preferably 90-99.9%; further preferably 95-99.9%; further preferably 97-99.9%) for light with wavelengths in the range of 450-800 nanometers.

[0132] In a preferred embodiment of the present invention, most visible light passes through the layer. Therefore, in one specific embodiment of the present invention, the visible light transmittance of this layer is preferably 90-100% (more preferably 90-99.9%; further preferably 95-99.9%). This visible light is preferably 360-830 nanometers (more preferably 400-830 nanometers; further preferably 400-760 nanometers).

[0133] The substantially transparent layer may have an average transmittance of 5-60% for light in the wavelength range of 250-450 nanometers. Without being bound by theory, the composition of this invention includes (d) an absorbent compound, which avoids chemical process barriers (e.g., turbidity, insoluble residues), and / or the substantially transparent layer transmits most visible light while reducing light in a specific range. Without being bound by theory, the substantially transparent layer may be incorporated into a light-emitting device that provides good visibility.

[0134] A preferred embodiment of the present invention is that the substantially transparent layer has an average transmittance of 5-25% for light with wavelengths in the range of 310-360 nanometers. A preferred embodiment of the present invention is that the substantially transparent layer has an average transmittance of 1-20% for light with wavelengths in the range of 370-410 nanometers.

[0135] The amount of penetration can be measured and evaluated using known methods.

[0136] In one specific embodiment of the present invention, the capacitance of the manufactured polycyclic olefin layer is preferably 3 or less (more preferably 2.6 or less; even more preferably 2.5 or less). The capacitance of the polycyclic olefin layer can be evaluated by known methods. Without being bound by theory, the polycyclic olefin layer having the above capacitance can exhibit the characteristics of a coating layer or an insulating layer.

[0137] One specific embodiment of the present invention is that the polymer system of the polycyclic olefin of the present invention is formed with a weight average molecular weight (Mw) of 5,000 to 500,000 (more preferably 10,000 to 400,000; even more preferably 20,000 to 250,000). In the present invention, Mw and Mn can be measured by gel permeation chromatography (GPC). A preferred example of this measurement is using a GPC column at 40°C, a dissolving agent of tetrahydrofuran at 0.6 mL / min, and monodisperse polystyrene as a standard.

[0138] The present invention manufactures a polycyclic olefin layer, comprising the steps (1), (2), (3), and above. (4) Apply one or more additional layers to the polycyclic olefin layer.

[0139] In one specific embodiment of the present invention, the additional layer is preferably selected from the group consisting of organic layers, inorganic layers, and hybrid layers; more preferably selected from the group consisting of inorganic layers, comprising materials selected from the group consisting of silicon oxide, silicon nitride, silicon oxynitride, aluminum oxynitride, magnesium oxide, aluminum oxide, aluminum nitride, titanium oxide, titanium nitride, tantalum oxide, tantalum nitride, hafnium oxide, hafnium nitride, zirconium oxide, zirconium nitride, cerium oxide, cerium nitride, indium oxide, tin oxide, tin nitride, and any dopant thereof. Further preferably, this additional layer forms a touch panel. [Equipment Manufacturing]

[0140] Without being bound by theory, the polycyclic olefin layer manufactured by the present invention can have good transparency or flexibility. Including this polycyclic olefin layer in electronic devices is advantageous. It is also advantageous to place this polycyclic olefin layer on a substrate component of the present invention (preferably an electronic device).

[0141] The present invention provides a method for manufacturing an electronic device, which includes a method for manufacturing the above-mentioned polycyclic olefin layer.

[0142] In one specific embodiment of the present invention, the electronic device is preferably a light-emitting device (more preferably an organic light-emitting device).

[0143] Preferably, the light-emitting device sequentially comprises a first electrode (more preferably an anode), a light-emitting layer, and a second electrode (more preferably a cathode). Preferably, the organic light-emitting device sequentially comprises a first electrode (more preferably an anode), a hole transport layer, a light-emitting layer, an electron transport layer, and a second electrode (more preferably a cathode).

[0144] Known methods may be applied for further processing purposes. For example, after forming the substrate component of the present invention, the substrate component may be diced into wafers if necessary, connected to a lead frame, and encapsulated in resin. As another specific embodiment, the polycyclic olefin layer of the present invention may form a manufacturing layer in a device (e.g., a light-emitting device).

[0145] The present invention also provides an electronic device manufactured by the above method.

[0146] The present invention will now be described in more detail with reference to the following embodiments, which are merely illustrative and not intended to limit the scope of the invention. [Comparative Example] [1-3]

[0147] Comparative compositions without (d) absorbent were prepared as follows.

[0148] In a glass bottle, Ru-I (0.0046 g) and CPTX (0.0030 g) were dissolved in PENB (10 g) without solvent to form a transparent composition.

[0149] The components were spin-coated onto a pre-cleaned quartz substrate under nitrogen atmosphere to form a wet film. The wet film was then cured by irradiation with 395 nm UV light under nitrogen atmosphere, with the applied dose typically between 0.5 and 5 joules per square centimeter. The doses used for comparative examples are shown in Table 1. The spin-coating parameters were optimized to obtain a film thickness of 8 micrometers. This film thickness was measured by profilometry after the photopolymerization was completed and the film was scribed onto the substrate surface.

[0150] After sample preparation, the transmission spectrum in the wavelength range of 250-800 nanometers was recorded. [Homework Example] [1-17]

[0151] The composition of the working example was prepared as follows. Except for the addition of absorbent (d), the composition of the working example was prepared in the same manner as that of composition 1 of comparative example. The amount of absorbent (d) relative to the total composition is shown in Table 1.

[0152] The confirmed case composition showed good transmittance in the visible light range (450-800 nm) and reduced UV light transmittance (250-450 nm). Table 1: Curing UV dose and transmittance data for films prepared with and without added UV blocking agents. [Weight Percentage] (d) Absorbent At a dose of 395 nanometers [J / cm²] Penetration rate Minimum transmittance @ wavelength [%T @nano] In the 250-450 nanometer range Average penetration rate [%T] In 450-800 nanometers Average penetration rate [%T] Com Ex.1 - 1 81.2 @ 256 94 98.8 Com Ex2 - 1.5 81.7 @ 256 94.2 98.9 Com Ex.3 - 2 82.2 @ 256 94.3 98.9 Ex.1 4% LA-F70 2 38.1 @ 334 58.8 99.7 Ex.2 8% BL1337 1 42.4 @ 367 75.8 98.6 Ex.3 8% BL1337 1.5 42.5 @ 367 75.9 [[ID=�2]] 98.8 Ex.4 4% FDB-009 1 2.0 @ 393 48.1 [[ID=⵶4]] 99.3 Ex.5 4% FDB-009 1.5 1.4 @ 393 43.9 99.1 Ex.6 2% LA-F70 and 2% Tinuvin970 1 6.0 @338 28.3 99 Ex.7 2% LA-F70 and 2% Tinuvin970 It should be noted that there may be some errors in the original text, such as "⵶4" and "⵵2" which seem to be incorrect characters. I have translated based on the best understanding of the text. 2 9.5 @338 32.5 98.4 Ex8 1% LA-F70 and 1% Tinuvin970 1 26.9 @ 338 51.3 99 Ex9 1% LA-F70 and 1% Tinuvin970 2 27.5 @ 338 51.8 99 Ex.10 4% Tinuvin970 and 2% Tinuvin928 2 3.3 @ 280 twenty two 99 Ex.11 1.5% Tinuvin970 1.5% Tinuvin477 and 1.5% Tinuvin928 2 1.8 @ 340 28.2 99.3 Ex.12 1% Tinuvin970 1% Tinuvin477 and 1% Tinuvin928 2 7.2 @ 356 38.4 99.3 Ex.13 8% BL1226 1 42.5 @ 367 75.8 98.6 Ex.14 3% absorbent 01 1 10.4 @347 40.2 98.6 Ex.15 4% absorbent 02 1 6.5 @ 346 32.7 98.3 Ex.16 4% absorbent 03 1 9.1 @ 347 35.9 98.5 Ex.17 3% absorbent 04 1 81.2 @255 91.8 98.7

[0153] In Table 1 above, “Com Ex.” indicates “Comparative Example”. In Table 1 above, the simple “Ex.” indicates “Operational Example” and applies to the following table. Table 2: Structure of Absorbent 01-04 Absorbent 01 Absorbent 02 Absorbent 03 Absorbent 04 [Homework Example] [18-36]

[0154] The solubility of each (d) absorbent was tested by dissolving it in Comparative Example Composition 1 at room temperature. This test was conducted for a maximum of 4 weeks. Table 3 lists the compositions and their solution stability as determined by visual inspection. Table 3: Stability of formulations at room temperature (d) Absorbent Solution stability Ex.18 2% Tinuvin970 2% Tinuvin477 and 2% Tinuvin928 Unstable, becoming cloudy after 3 days Ex.19 2% Tinuvin477 Unstable, becoming cloudy after 3 days Ex.20 15% Tinuvin928 Incompletely dissolved Ex.21 8% BL1337 Incompletely dissolved Ex.22 4% LA-F70 Unstable, becoming cloudy after 3 days Ex.23 4% FDB-009 Unstable, becoming cloudy after 7 days Ex.24 1% LA-F70 and 1% Tinuvin970 stable Ex.25 2% LA-F70 and 2% Tinuvin970 stable Ex.26 4% Tinuvin970 and 2% Tinuvin928 Unstable, becoming cloudy after 7 days Ex.27 1% Tinuvin970 1% Tinuvin477 and 1% Tinuvin928 stable Ex.28 1.5% Tinuvin970 1.5% Tinuvin477 and 1.5% Tinuvin928 stable Ex.29 8% BL1226 stable Ex.30 3% absorbent 01 stable Ex.31 4% absorbent 02 stable Ex.32 4% absorbent 03 stable Ex.33 3% absorbent 04 stable Ex.34 4% Eusolex 9020 Undissolved Ex.35 4% Oxynex ST Unstable, cloudy after 2 hours Ex.36 4% Eusolex S stable

[0155] none

Claims

1. A composition comprising (a) one or more monomers of formula (I); (b) a potential organic-transition metal catalyst comprising a metal selected from the group consisting of ruthenium, osmium, or palladium; (c) a compound that releases brinsteinic acid when subjected to photodegradation conditions; and (d) an absorber compound with a maximum absorption wavelength in the range of 280-410 nanometers; wherein formula (I) is represented by the following formula: m is an integer of 0, 1, or 2; R1, R2, R3, and R4 are each independently selected from the group consisting of hydrogen, halogen, methyl, ethyl, linear or branched C1-20 alkyl, perfluoroC1-12 alkyl, hydroxyC1-16 alkyl, C3-12 cycloalkyl, C6-12 bicycloalkyl, (CH2)a-C6-12 bicycloalkenyl, C7-14 tricycloalkyl, substituted or unsubstituted C6-10 aryl, substituted or unsubstituted C6-10 arylC1-6 alkyl, perfluoroC6-10 aryl, perfluoroC6-10 arylC1-3 alkyl, and an alkyl group of formula (A): -Z-aryl(A), wherein: Z is a single bond or a group selected from the group consisting of: (CR5R6)a, O(CR5R6)a, (CR5R6)aO, (CR5R6)aO-(CR5R6)b, (CR5R6)aO-(SiR5R6)b, (CR5R6)a-(CO)O-(CR5R6)b, where a and b are each an integer from 1 to 12; R5 and R6 are each independently selected from the group consisting of hydrogen, methyl, ethyl, linear or branched C3-6 alkyl, hydroxyl, methoxy, ethoxy, linear or branched C3-6 alkoxy, acetoxy, C2-6 acetyl, hydroxymethyl, hydroxyethyl, linear or branched hydroxy C3-6 alkyl, substituted or unsubstituted phenyl, and substituted or unsubstituted phenoxy. The aryl group is phenyl, or a phenyl group substituted with one or more alkyl groups selected from the group consisting of methyl, ethyl, linear or branched C3-6 alkyl, hydroxy, methoxy, ethoxy, linear or branched C3-6 alkoxy, acetoxy, C2-6 acetyl, hydroxymethyl, hydroxyethyl, linear or branched hydroxy C3-6 alkyl, phenyl, and phenoxy; and, where appropriate, one of R1 or R2 and one of R3 or R4 together with the carbon atoms to which they are attached form a C5-7 carbon ring, wherein the C5-7 carbon ring contains one or more double bonds; wherein (c) a compound that can produce Brønsted acid when subjected to photodegradation conditions has the formula (V): Wherein Y is a halogen; and R30 and R31 are each independently selected from the group consisting of hydrogen, methyl, ethyl, linear or branched C3-12 alkyl, C3-12 cycloalkyl, C6-12 bicycloalkyl, C7-14 tricycloalkyl, C6-10 aryl, C6-10 arylC1-3 alkyl, C1-12 alkoxy, C3-12 cycloalkoxy, C6-12 bicycloalkoxy, C7-14 tricycloalkoxy, C6-10 aryloxyC1-3 alkyl, and C6-10 aryloxy; wherein (d) the absorbent compound is represented by a formula selected from the group consisting of (d-1), (d-2), and (d-3), or (d) the absorbent compound is a compound selected from the group consisting of aromatic tertiary amines containing at least two tertiary amine units, tertiary amines containing carbazole units, hexaazine terphenyl compounds, and phthalocyanine derivatives. R21 and R22 are each independently hydrogen, linear or branched C1-5 alkyl, or C6-10 aryl; where appropriate, the C1-5 alkyl groups of R21 and R22 may be bonded to each other to form a saturated or unsaturated ring; where appropriate, one or more methylene groups of this saturated ring may be independently substituted by -(C=O)- or -NR25-; where R25 are each independently hydrogen, linear or branched C1-5 alkyl, or C6-10 aryl; m21 is an integer from 1 to 3; and R23 and R24 are each independently C1-10 alkyl, C6-18 aryl, C6-12 aryl C1-5 alkyl, or C1-5 alkyl C6-12 aryl; where the alkyl portions of R23 and R24 may each be independently linear or branched;And, as appropriate, the methylene groups of the alkyl moieties of R23 and R24 may be substituted with -CO-, -O-, or -COO-; R32 and R33 are each independently C1-21 hydrocarbon groups, which may form saturated or unsaturated rings as appropriate, wherein, as appropriate, the carbon-carbon single bonds of one or more moieties of the compound represented by formula (d-2) may be substituted with carbon-carbon double bonds; and, as appropriate, the methylene moieties of R32 may be substituted with -O- or -C(=O)-; L31 is a C1-12 hydrocarbon linker group, which may form saturated or unsaturated rings as appropriate, wherein the methylene moieties of L31 may be substituted with -O- as appropriate; L32 is -CO-, -CH2-, or -CH(CH3)-; and at least one methyl group in the compound represented by formula (d-2) is substituted with a hydroxyl or methoxy group; R41, R42, and R43 are each independently a C1-20 hydrocarbon group, which may form saturated or unsaturated rings as desired. The methylene portion of R41, R42, or R43 may be substituted with -O- as desired; and at least one methyl group in the compound represented by formula (d-3) is substituted with a hydroxyl or methoxy group.

2. A composition as claimed in claim 1, wherein the composition forms a substantially transparent layer when exposed to suitable radiation.

3. The composition of claim 1, wherein the substantially transparent layer has an average transmittance of 90-100% for visible light.

4. The composition of any one of claims 1 to 3, wherein (d) the absorbent compound is a compound selected from the group consisting of aromatic tertiary amines containing at least two tertiary amine units, tertiary amines containing carbazole units, hexaazine terphenyl compounds, and phthalocyanine derivatives, and is excited by an electric field when formed into a layer.

5. The composition of any one of claims 1 to 3, wherein (d) the absorber compound is represented by a formula selected from the group consisting of formulas (d-1), (d-2) and (d-3), and (d) the absorber compound is used to block UV by means of an excited-state intramolecular proton transfer (ESIPT) mechanism.

6. A composition of any one of claims 1 to 3, wherein the monomer (a) of formula (I) is of formula (Ia), wherein a is 0 or 1, and R1 is a linear or branched C1-20 alkyl, or an unsubstituted C6-10 aryl C1-6 alkyl.

7. As in any of claims 1 to 3, wherein the monomer (a) of formula (I) is selected from the group consisting of the following formulas (Ia-01) to (Ia-21):

8. A composition of any one of claims 1 to 3, wherein the potential catalyst is an organorruthenium compound selected from the group consisting of compounds of formula (IIA), formula (IIB), formula (IIIA), formula (IIIB), formula (IIIC), and formula (IIID): wherein: X is independently selected from the group consisting of chlorine, bromine, iodine, -ORa, -O(CO)Ra, -S(Ra)2, -OSO2Ra, and -N(Ra)2, wherein Ra is independently selected from the group consisting of single bond, C1-12 alkyl, C3-12 cycloalkyl, C6-14 aryl, and =CH(Ra'); wherein any combination of two Ra can be bonded to each other; and Ra' is a single bond bonded to Ra or L; Y is selected from the group consisting of O, S, and NCOCF3; Y' is selected from the group consisting of OR9, SR9, and -N=CHC(O)O(C1-6 alkyl); wherein R9 is selected from the group consisting of methyl, ethyl, linear or branched C1-6 alkyl, C6-10 aryl, methoxy, ethoxy, linear or branched C1-6 alkoxy, C6-10 aryloxy, and -OCH(CH3)C(O)N(CH3)(OCH3); L is selected from the group consisting of pyridine, PR3, O=PR3, and -O-R3, wherein each R3 is independently selected from the group consisting of isopropyl, secondary butyl, tertiary butyl, cyclohexyl, bicyclic C5-10 alkyl, phenyl, benzyl, isopropoxy, secondary butoxy, tertiary butoxy, cyclohexyloxy, phenoxy, and benzyloxy; wherein one of X and L can form an anionic ligand of formula XL; R7 is selected from the group consisting of isopropyl, secondary butyl, tertiary butyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, and substituted or unsubstituted naphthyl. R8 is selected from the group consisting of hydrogen, chlorine, methyl, ethyl, linear or branched C1-6 alkyl, C6-10 aryl, methoxy, ethoxy, linear or branched C1-6 alkoxy, C6-10 aryloxy, -NHCO(C1-6)alkyl, -NHCO-perfluoro(C1-6)alkyl, -SO2N((C1-6)alkyl)2, and -NO2; Ar1, Ar2, Ar3, and Ar4 are each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, and substituted or unsubstituted naphthyl; wherein each substituent is independently selected from the group consisting of methyl, ethyl, isopropyl, tributyl, phenyl, and OSi(SiMe3)3; m is an integer of 1, 2, or 3.

9. The composition of any one of claims 1 to 3, wherein (a) the content of monomers is 80-99.99% by mass based on the composition; (b) the content of potential organo-transition metal catalysts is 0.0001-1.0% by mass based on the composition; (c) the content of compounds that release Brinzyl acid is 0.0001-1.0% by mass based on the composition; and (d) the content of absorbent compounds is 0.5-15% by mass based on the composition.

10. A composition of any one of claims 1 to 3, wherein the viscosity of the composition is 5-20 mPass at 40°C; and the surface tension of the composition is 10-50 millinewtons / meter at 25°C.

11. A method for manufacturing a polycyclic olefin layer, the steps of which include: (1) preparing a substrate component; (2) coating the substrate component with a composition of any one of claims 1 to 10; and (3) polymerizing the monomer (a) in the composition.

12. The method of manufacturing a polycyclic olefin layer as claimed in claim 11, wherein the capacitance of the polycyclic olefin layer is 3 or less.

13. The method of manufacturing a polycyclic olefin layer as claimed in claim 11 or 12, wherein the means of coating the composition in step (2) is selected from the group consisting of deposition, dip coating, spin coating, inkjet printing, nozzle printing, letterpress printing, screen printing, gravure printing, doctor blade coating, roller printing, reverse roller printing, lithography, dry lithography, flexographic printing, roll-to-roll printing, spraying, curtain coating, brush coating, slot dye coating, and pad printing.

14. A method for manufacturing a polycyclic olefin layer as claimed in any of claims 11 to 12, wherein step (3) is performed by irradiation and / or heat.

15. The method of manufacturing a polycyclic olefin layer as claimed in any of claims 11 to 12, further comprising the steps of: (4) applying one or more additional layers over the polycyclic olefin layer; the additional layers being selected from the group consisting of organic layers, inorganic layers and hybrid layers; and the additional layers forming a touch panel.

16. A method of manufacturing an electronic device, comprising: a method of manufacturing a polycyclic olefin layer as described in any one of claims 11 to 15.

17. The method of manufacturing an electronic device as claimed in claim 16, wherein the substrate component of the method of manufacturing the polycyclic olefin is an electronic device; the electronic device is a light-emitting device; the light-emitting device sequentially comprises a first electrode, a light-emitting layer, and a second electrode.

18. An electronic device manufactured by the method of claim 16 or 17.