Polymer, coating composition containing the same, and organic light-emitting element using the same

Abstract

The present specification relates to a polymer including a unit represented by Chemical Formula 1, a coating composition including the same, and an organic light-emitting device formed using the same.

Description

Technical Field

[0001] This application claims priority to and the benefit of Korean Patent Application No. 10-2020-0111664, filed on September 2, 2020, in the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference.

[0002] The present disclosure relates to polymers, coating compositions containing the same, and organic light-emitting devices formed using the same. Background Art

[0003] Organic light emitting phenomenon is one of the examples of converting electric current into visible light through the internal process of specific organic molecules. The principle of organic light emitting phenomenon is as follows. When the organic material layer is placed between the anode and the cathode and a current is applied between the two electrodes, electrons and holes are injected into the organic material layer from the cathode and the anode, respectively. The holes and electrons injected into the organic material layer recombine to form excitons, which emit light when these excitons fall back to the ground state. An organic electroluminescent device utilizing such a principle can generally be formed by a cathode, an anode and an organic material layer placed therebetween (for example, an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, etc.).

[0004] The materials used in organic light-emitting devices are mainly pure organic materials or complex compounds in which organic materials and metals form complexes, and can be divided into hole injection materials, hole transport materials, luminescent materials, electron transport materials, electron injection materials, etc. according to the application. In this article, as hole injection materials or hole transport materials, organic materials with p-type characteristics are generally used, that is, organic materials that are easily oxidized and have an electrochemically stable state when oxidized. At the same time, as electron injection materials or electron transport materials, organic materials with n-type characteristics are generally used, that is, organic materials that are easily reduced and have an electrochemically stable state when reduced. As light-emitting materials, materials with both p-type characteristics and n-type characteristics, that is, materials with stable forms in both oxidized and reduced states are preferred, and materials with high luminous efficiency of converting excitons into light when excitons are formed are preferred.

[0005] Deposition methods are commonly used in the art to manufacture organic light-emitting devices. However, deposition methods have the problem of causing significant material loss and difficulty in manufacturing large-area devices. Devices using solution methods have been developed to address these issues.

[0006] Therefore, materials for a solution method are being developed, and there is a need to develop a material that has excellent solubility in an organic solvent and, while having an appropriate viscosity when dissolved in the solvent.

[0007] [Prior art literature]

[0008] (Patent Document 1) Korean Patent Application Publication No. 10-2008-012337 Summary of the Invention

[0009] Technical issues

[0010] The present disclosure provides polymers, coating compositions containing the same, and organic light-emitting devices formed using the same.

[0011] Technical Solution

[0012] One embodiment of the present specification provides a polymer including a unit represented by the following Chemical Formula 1.

[0013] [Chemical Formula 1]

[0014]

[0015] In Chemical Formula 1,

[0016] R1 and R2 are the same as or different from each other and are each independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,

[0017] L is unsubstituted or selected from hydrogen, deuterium and C1-C 30 alkyl substituted with one or more substituents; or unsubstituted or substituted with one or more substituents selected from hydrogen, deuterium and C1-C 30 a heteroarylene group substituted with one or more substituents of an alkyl group,

[0018] L1 to L4 are the same as or different from each other and are each independently a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group,

[0019] a and b are each 1 or 2, and when a and b are 2, the substituents in the two brackets are the same as or different from each other,

[0020] n1 and n2 are each an integer from 0 to 4, and when n1 and n2 are 2 or greater, two or more substituents in the brackets are the same as or different from each other, and

[0021] m1, which is the number of repetitions of the unit, is an integer from 1 to 10,000.

[0022] Another embodiment of the present specification provides a coating composition including the above-mentioned polymer including the unit represented by Chemical Formula 1.

[0023] One embodiment of the present specification provides an organic light-emitting device including: a first electrode; a second electrode; and an organic material layer disposed between the first electrode and the second electrode, wherein the organic material layer includes the polymer including the unit represented by Chemical Formula 1 described above.

[0024] In addition, one embodiment of the present specification provides a method for manufacturing an organic light-emitting device, the method comprising: preparing a first electrode; forming one or more organic material layers on the first electrode; and forming a second electrode on the one or more organic material layers, wherein forming the one or more organic material layers comprises forming the organic material layers using the above-mentioned coating composition.

[0025] Beneficial effects

[0026] Compared to a linear polymer formed using a unit having two bonding points, the unit represented by Chemical Formula 1 according to one embodiment of the present specification has four bonding points, thereby being able to induce a branched polymer form and having solubility and viscosity for an organic solvent suitable for a solution process.

[0027] An organic material layer including the polymer according to one embodiment of the present specification has excellent hole transport characteristics, and an organic light-emitting device including the polymer has greatly improved efficiency and lifespan characteristics. BRIEF DESCRIPTION OF THE DRAWINGS

[0028] Figure 1 An example of an organic light-emitting device according to one embodiment of the present specification is shown.

[0029] [reference numerals]

[0030] 101: Base

[0031] 201: First electrode

[0032] 301: Hole injection layer

[0033] 401: Hole transport layer

[0034] 501: Luminous layer

[0035] 601: Electron injection and transport layer

[0036] 701: Second electrode DETAILED DESCRIPTION

[0037] Hereinafter, this specification will be described in more detail.

[0038] One embodiment of the present specification provides a polymer including a unit represented by Chemical Formula 1.

[0039] According to one embodiment of the present specification, the polymer including the unit represented by Chemical Formula 1 may include one or more types of the unit represented by Chemical Formula 1.

[0040] In one embodiment of the present specification, the polymer including the unit represented by Chemical Formula 1 may include two or more types of units represented by Chemical Formula 1. In this case, the polymer including the unit represented by Chemical Formula 1 may be a random copolymer or a block copolymer.

[0041] In one embodiment of the present specification, the polymer including the unit represented by Chemical Formula 1 may be a homopolymer. Herein, the homopolymer means a polymer formed of only one type of monomer.

[0042] According to one embodiment of the present specification, the polymer including the unit represented by Chemical Formula 1 may include additional units in addition to the unit represented by Chemical Formula 1.

[0043] In this specification, a "unit" is a structure in which a monomer is contained in a polymer and repeated, and means a structure in which a monomer is bonded in a polymer by polymerization.

[0044] In the present specification, the meaning of "comprising a unit" means that the corresponding unit is included in the main chain in the polymer.

[0045] In one embodiment of the present specification, the unit represented by Chemical Formula 1 has a structure in which two amines are connected by three or more linking groups and has a repeating structure at 4 bonding points, and therefore, the polymer including the unit represented by Chemical Formula 1 has excellent solubility in organic solvents and has appropriate viscosity for a solution method.

[0046] Therefore, when a polymer containing the unit represented by Chemical Formula 1 is used in a hole transport layer, a hole injection layer, or a hole injection and transport layer of an organic light-emitting device, the prepared hole transport layer, the hole injection layer, or the hole injection and transport layer has excellent uniformity and surface characteristics, etc., which can improve device performance and life characteristics.

[0047] According to one embodiment of the present specification, the repetition number (m1) of the unit represented by Chemical Formula 1 may be 1 to 400, however, the repetition number is not limited thereto.

[0048] In one embodiment of the present specification, a material forming a specific organic material layer of an organic light-emitting device may be analyzed through MS and NMR analysis after obtaining the corresponding organic material layer from the organic light-emitting device.

[0049] In this specification, description that a certain member is placed “on” another member includes not only a case where one member is in contact with another member but also a case where another member exists between the two members.

[0050] In the present specification, unless otherwise specified, description that a part “includes” a certain constituent element means that other constituent elements can also be included, and does not exclude other constituent elements.

[0051] Examples of the substituent in the present specification are described below, however, the substituent is not limited thereto.

[0052] The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is changed to another substituent. The position of the substitution is not limited as long as it is a position where the hydrogen atom is substituted (i.e., a position where a substituent can replace it), and when two or more substituents are substituted, the two or more substituents may be the same or different from each other.

[0053] In this specification, the term "substituted or unsubstituted" means substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a hydroxyl group, a cyano group, a silyl group, an alkyl group, a cycloalkyl group, an alkenyl group, an alkoxy group, an aryloxy group, -N(Rm)(Rn), an aryl group, and a heteroaryl group, or substituted with two or more of the substituents listed above linked together, or having no substituents, Rm and Rn being the same or different and each independently hydrogen, an alkyl group, an aryl group, or a heteroaryl group. For example, "a substituent in which two or more substituents are linked together" may include a biphenyl group. In other words, the biphenyl group may be an aryl group, or may be interpreted as a substituent in which two phenyl groups are linked together.

[0054] In the present specification, examples of the halogen group may include fluorine, chlorine, bromine or iodine.

[0055] In this specification, the silyl group may be an alkylsilyl group or an arylsilyl group, and may be a trialkylsilyl group or a triarylsilyl group. The number of carbon atoms in the silyl group is not particularly limited, but is preferably 1 to 30. The alkylsilyl group may have 1 to 30 carbon atoms, and the arylsilyl group may have 6 to 30 carbon atoms. Specific examples thereof may include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, etc., but are not limited thereto.

[0056] In the present specification, the alkyl group may be linear or branched, and although not particularly limited thereto, the number of carbon atoms is preferably 1 to 30. Specific examples thereof may include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1-dimethylpropyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like, but are not limited thereto.

[0057] In the present specification, the cycloalkyl group is not particularly limited but preferably has 3 to 30 carbon atoms, and specific examples thereof may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl and the like, but are not limited thereto.

[0058] In the present specification, the alkenyl group may be linear or branched, and although not particularly limited thereto, the number of carbon atoms is preferably 2 to 30. Specific examples thereof may include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbene, styryl, and the like, but are not limited thereto.

[0059] In this specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms in the alkoxy group is not particularly limited, but is preferably 1 to 30. Specific examples thereof may include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc., but are not limited thereto.

[0060] In the present specification, the aryl group is not particularly limited, but may have 6 to 60 carbon atoms, and may have 6 to 30 carbon atoms.

[0061] In this specification, the aryl group may include a structure in which two or more aryl groups are connected. For example, the aryl group may include a biphenyl group in which two phenyl groups are connected, may include a terphenyl group in which three phenyl groups are connected, and may include a binaphthyl group in which two naphthyl groups are connected.

[0062] The aryl group may be monocyclic or polycyclic. When the aryl group is a monocyclic aryl group, examples thereof may include, but are not limited to, phenyl, biphenyl, terphenyl, etc. When the aryl group is a polycyclic aryl group, examples thereof may include, but are not limited to, naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, phenanthrenyl, perylene, fluorenyl, etc., but not limited thereto.

[0063] In the present specification, the fluorenyl group may be substituted, and adjacent groups may be bonded to each other to form a ring.

[0064] When the fluorenyl group is substituted, the substituted fluorenyl group may be, for example, any one selected from the following compounds, but is not limited thereto.

[0065]

[0066] In this specification, an "adjacent" group may refer to a substituent that replaces an atom directly connected to the atom replaced by the corresponding substituent, a substituent that is spatially located closest to the corresponding substituent, or another substituent that replaces the atom replaced by the corresponding substituent. For example, two substituents substituted at ortho positions in a benzene ring and two substituents replacing the same carbon in an aliphatic ring can be interpreted as groups "adjacent" to each other.

[0067] In the present specification, the heteroaryl group contains one or more heteroatoms as non-carbon atoms, specifically, the heteroatoms may include one or more atoms selected from O, N, Se and S. The number of carbon atoms is not particularly limited, but is preferably 2 to 30, and the heteroaryl group may be monocyclic or polycyclic. Examples of the heteroaryl group may include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, Azolyl, oxadiazole, pyridyl, bipyridyl, pyrimidinyl, triazinyl, triazolyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzo[omicron] oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothiophenyl, dibenzothiophenyl, benzofuranyl, phenanthridinyl, phenanthroline, isophthalic acid oxazolyl, thiadiazolyl, phenothiazinyl, dibenzofuranyl, etc., but are not limited thereto.

[0068] In this specification, the aryl group in the aryloxy group is the same as the example of the aryl group described above. Specific examples of the aryloxy group may include phenoxy, p-tolyloxy, m-tolyloxy, 3,5-dimethyl-phenoxy, 2,4,6-trimethylphenoxy, p-tert-butylphenoxy, 3-biphenyloxy, 4-biphenyloxy, 1-naphthyloxy, 2-naphthyloxy, 4-methyl-1-naphthyloxy, 5-methyl-2-naphthyloxy, 1-anthryloxy, 2-anthryloxy, 9-anthryloxy, 1-phenanthrenoxy, 3-phenanthrenoxy, 9-phenanthrenoxy, etc., but are not limited thereto.

[0069] In the present specification, specific examples of -N(Rm)(Rn) may include methylamino, dimethylamino, ethylamino, diethylamino, phenylamino, naphthylamino, biphenylamino, anthrylamino, 9-methyl-anthrylamino, diphenylamino, dimethylphenylamino, N-phenyltolylamino, triphenylamino, N-phenylbiphenylamino, N-phenylnaphthylamino, N-biphenylnaphthylamino, N-naphthylfluorenylamino, N-phenylphenanthrenylamino, N-biphenylphenanthrenylamino, N-phenylfluorenylamino, N-phenylterphenylamino, N-phenanthrenylfluorenylamino, N-biphenylfluorenylamino, etc., but are not limited thereto.

[0070] In the present specification, an arylene group means an aryl group having two bonding sites, that is, a divalent group. The description provided above regarding the aryl group can be applied to the arylene group, except that the arylene group is a divalent group.

[0071] In the present specification, a heteroarylene group means a heteroaryl group having two bonding sites, that is, a divalent group. The description provided above regarding the heteroaryl group can be applied to the heteroarylene group, except that the heteroarylene group is a divalent group.

[0072] Hereinafter, the substituents of Chemical Formula 1 will be described.

[0073] According to one embodiment of the present specification, R1 and R2 are the same as or different from each other and are each independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted silyl group; a substituted or unsubstituted C1-C 30 Alkyl; substituted or unsubstituted C1-C 30 Alkoxy; substituted or unsubstituted C6-C 60 Aryl; or substituted or unsubstituted C2-C 60 Heteroaryl.

[0074] According to one embodiment of the present specification, R1 and R2 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted C1-C 30 Alkylsilyl; substituted or unsubstituted C1-C 30 Alkyl; substituted or unsubstituted C1-C30 Alkoxy; substituted or unsubstituted C6-C 60 Aryl; or substituted or unsubstituted C2-C 60 Heteroaryl.

[0075] According to one embodiment of the present specification, R1 and R2 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a C1-C 20 Alkylsilyl; C1-C 20 Alkyl; substituted or unsubstituted C1-C 20 Alkoxy; substituted or unsubstituted C6-C 30 Aryl; or substituted or unsubstituted C2-C 30 Heteroaryl.

[0076] In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and are each independently hydrogen or C1-C 20 alkyl.

[0077] According to another embodiment, R1 and R2 are identical to or different from each other and are each independently hydrogen or methyl.

[0078] According to one embodiment of the present specification, L is unsubstituted or selected from hydrogen, deuterium and C1-C 30 alkyl substituted with one or more substituents; or unsubstituted or substituted with one or more substituents selected from hydrogen, deuterium and C1-C 30 A heteroarylene group substituted with one or more substituents of the alkyl group. Due to L in Chemical Formula 1 having the above range, when the polymer including the unit represented by Chemical Formula 1 is used in an organic light-emitting device, the device efficiency and lifespan are improved.

[0079] According to one embodiment of the present specification, L is unsubstituted or selected from hydrogen, deuterium and C1-C 30 One or more substituents of the alkyl group substituted with C6-C 60 Arylene; or unsubstituted or selected from hydrogen, deuterium and C1-C 30 One or more substituents of the alkyl group substituted with C2-C 60 Heteroarylene.

[0080] According to one embodiment of the present specification, L is unsubstituted or selected from hydrogen, deuterium and C1-C 20 One or more substituents of the alkyl group substituted with C6-C 30 Arylene; or unsubstituted or selected from hydrogen, deuterium and C1-C 20 One or more substituents of the alkyl group substituted with C2-C 30 Heteroarylene containing O, S or N.

[0081] In one embodiment of the present specification, L is unsubstituted or selected from hydrogen, deuterium and C1-C 30 Phenylene substituted with one or more substituents of alkyl; unsubstituted or substituted with one or more substituents selected from hydrogen, deuterium and C1-C 30 Benzofluorenyl substituted with one or more substituents of alkyl; unsubstituted or substituted with one or more substituents selected from hydrogen, deuterium and C1-C 30 Binaphthyl substituted with one or more substituents of alkyl; unsubstituted or substituted with one or more substituents selected from hydrogen, deuterium and C1-C 30 A divalent dibenzofuranyl group substituted with one or more substituents of an alkyl group; unsubstituted or substituted with one or more substituents selected from hydrogen, deuterium and C1-C 30 A divalent dibenzothienyl group substituted with one or more substituents of an alkyl group; or unsubstituted or substituted with one or more substituents selected from hydrogen, deuterium and C1-C 30 A divalent carbazolyl group substituted with one or more substituents of an alkyl group.

[0082] In one embodiment of the present specification, L is an unsubstituted or hexyl-substituted phenylene group; an unsubstituted or hexyl-substituted benzofluorenylene group; an unsubstituted or octyl-substituted binaphthylene group; or an unsubstituted or tridecyl (-C 13 H 27 ) substituted divalent carbazolyl group.

[0083] In one embodiment of the present specification, L is any one selected from the following structural formulae.

[0084]

[0085] In the structural formula, Means the connection location,

[0086] G1 to G6 are the same as or different from each other and are each independently hydrogen; deuterium; or C1-C 30 alkyl,

[0087] g1 is an integer from 0 to 4, and when g1 is 2 or greater, two or more G1s are the same as or different from each other, and

[0088] g5 and g6 are each an integer from 0 to 2, and when g5 and g6 are each 2, both G5 and G6 are the same as or different from each other.

[0089] In one embodiment of the present specification, G1 to G6 are the same as or different from each other, and are each independently hydrogen; deuterium; or C1-C 20 alkyl.

[0090] In one embodiment of the present specification, G1 to G6 are the same as or different from each other, and are each independently hydrogen; or C1-C 20 alkyl.

[0091] In one embodiment of the present specification, G1 to G6 are the same as or different from each other, and are each independently hydrogen; hexyl; octyl; or tridecyl.

[0092] In one embodiment of the present specification, G1 is hydrogen; or a hexyl group.

[0093] In one embodiment of the present specification, G2 and G3 are hexyl groups.

[0094] In one embodiment of the present specification, G4 is a tridecyl group.

[0095] In one embodiment of the present specification, G5 is octyl.

[0096] In one embodiment of the present specification, the tridecyl group may be branched, and may specifically have -C(C6H 13 )2 structure.

[0097] In one embodiment of the present specification, g1 is 0 to 2.

[0098] In one embodiment of the present specification, g1 is 2.

[0099] In one embodiment of the present specification, g5 and g6 are 1.

[0100] In one embodiment of the present specification, L is any one selected from the following structural formulae.

[0101]

[0102] In the structural formula, Indicates the connection location.

[0103] In one embodiment of the present specification, Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-4.

[0104] [Chemical Formula 1-1]

[0105]

[0106] [Chemical formula 1-2]

[0107]

[0108] [Chemical formula 1-3]

[0109]

[0110] [Chemical formula 1-4]

[0111]

[0112] In Chemical Formulas 1-1 to 1-4,

[0113] R1, R2, L1 to L4, a, b, n1, n2 and m1 have the same definitions as in Chemical Formula 1,

[0114] X is O, S or NR,

[0115] R, R3 to R8, Ar1 and Ar2 are the same as or different from each other and are each independently hydrogen, deuterium or C1-C 30 alkyl,

[0116] c is 1 or 2, and when c is 2, the substituents in the two brackets are the same as or different from each other,

[0117] n3 is an integer from 0 to 4,

[0118] n4, n6 and n7 are each an integer from 0 to 3,

[0119] n5 is an integer from 0 to 5,

[0120] n8 is an integer from 0 to 6, and

[0121] When n3 to n8 are each 2 or greater, two or more substituents in the brackets are the same as or different from each other.

[0122] In one embodiment of the present specification, X is O, S or NR.

[0123] In one embodiment of the present specification, X is NR.

[0124] According to one embodiment of the present specification, R, R3 to R8, Ar1 and Ar2 are the same as or different from each other, and are each independently hydrogen, deuterium or C1-C 30 alkyl.

[0125] According to one embodiment of the present specification, R, R3 to R8, Ar1 and Ar2 are the same as or different from each other, and are each independently hydrogen, deuterium, or a linear or branched C1-C 30 alkyl.

[0126] According to one embodiment of the present specification, R is a linear or branched C1-C 30 alkyl.

[0127] According to one embodiment of the present specification, R is a tridecyl group.

[0128] According to one embodiment of the present specification, R is a branched tridecyl group.

[0129] In one embodiment of the present specification, R3 to R7, Ar1 and Ar2 are the same as or different from each other, and are each independently hydrogen, deuterium or hexyl.

[0130] In one embodiment of the present specification, R8 is octyl.

[0131] According to one embodiment of the present specification, L1 to L4 are the same as or different from each other, and are each independently a substituted or unsubstituted C6-C 60 Arylene; or substituted or unsubstituted C2-C 60 Heteroarylene.

[0132] According to another embodiment, L1 to L4 are the same as or different from each other, and are each independently a substituted or unsubstituted biphenylene; or a substituted or unsubstituted terphenylene.

[0133] In another embodiment, L1 to L4 are the same or different from each other and are each independently unsubstituted or substituted with C1-C 30 Alkyl-substituted biphenylene; or unsubstituted or C1-C 30 Alkyl-substituted terphenylene.

[0134] In another embodiment, L1 to L4 are the same as or different from each other, and are each independently unsubstituted or propyl-substituted terphenylene; or biphenylene.

[0135] In another embodiment, L1 to L4 are the same as or different from each other, and are each independently unsubstituted or propyl-substituted terphenylene; or biphenylene.

[0136] In another embodiment, L1 to L4 are the same as or different from each other, and are each independently represented by any one of the following structural formulae.

[0137]

[0138] In the structural formula, Means the connection location,

[0139] G 11 to G 13 are the same as or different from each other and are each independently hydrogen, deuterium or C1-C 30 Alkyl, and

[0140] g11 to g13 are each an integer of 0 to 4, and when g11 to g13 are 2 or greater, the structures in parentheses are each the same as or different from each other.

[0141] In one embodiment of the present specification, G 11 to G 13are the same as or different from each other and are each independently hydrogen or propyl.

[0142] In one embodiment of the present specification, G 11 and G 12 For hydrogen.

[0143] In one embodiment of the present specification, G 13 is hydrogen or propyl.

[0144] In one embodiment of the present specification, G 13 It is propyl.

[0145] In one embodiment of the present specification, g11 and g12 are each an integer of 1 to 4.

[0146] In one embodiment of the present specification, g13 is 2.

[0147] In one embodiment of the present specification, a and b are 1.

[0148] In one embodiment of the present specification, n1 and n2 are each 0 or 1.

[0149] In another embodiment, L1 to L4 are the same as or different from each other, and are each independently represented by any one of the following structural formulae.

[0150]

[0151] In the structural formula, Indicates the connection location.

[0152] In one embodiment of the present specification, m1 which is the repetition number of the unit is an integer from 1 to 10,000.

[0153] In another embodiment, m1 as the number of repetitions of the unit is an integer from 5 to 5,000.

[0154] In another embodiment, m1 as the repetition number of the unit is an integer from 5 to 1,000.

[0155] In another embodiment, m1 as the number of repetitions of the unit is an integer from 10 to 300.

[0156] According to one embodiment of the present specification, the unit represented by Chemical Formula 1 is any one selected from the following structures.

[0157]

[0158]

[0159] In the structure described,

[0160] m1, which is the number of repetitions of the unit, is an integer from 1 to 10,000.

[0161] In this specification, the terminal group of the polymer may be hydrogen or an aromatic group.

[0162] In one embodiment of the present specification, the polymer comprising the unit represented by Chemical Formula 1 has a number average molecular weight of 500 g / mol to 1,000,000 g / mol, more preferably 10,000 g / mol to 300,000 g / mol. In another embodiment, the number average molecular weight is 10,000 g / mol to 100,000 g / mol. When the number average molecular weight of the polymer comprising the unit represented by Chemical Formula 1 is less than the above range, it is difficult to obtain the performance of the device targeted in the present disclosure, and a number average molecular weight greater than the above range has the problem of reducing the solubility of the polymer in the solvent, and therefore, it is preferably a molecular weight within the above range.

[0163] In one embodiment of the present specification, the polymer including the unit represented by Chemical Formula 1 has a weight average molecular weight of 10,000 g / mol to 1,000,000 g / mol, more preferably 10,000 g / mol to 300,000 g / mol. In another embodiment, the weight average molecular weight is 20,000 g / mol to 200,000 g / mol.

[0164] In one embodiment of the present specification, the molecular weight distribution of the polymer may be 1 to 10. Preferably, the molecular weight distribution of the polymer is 1 to 4.

[0165] In this specification, the terms number average molecular weight (Mn) and weight average molecular weight (Mw) mean converted molecular weights with respect to standard polystyrene measured using GPC (gel permeation chromatography). In this specification, molecular weight distribution means the value obtained by dividing the weight average molecular weight (Mw) by the number average molecular weight (Mn), that is, weight average molecular weight (Mw) / number average molecular weight (Mn).

[0166] Number average molecular weight (Mn) and molecular weight distribution (PDI) can be measured using GPC (gel permeation chromatography). The target object to be analyzed is placed in a 5 mL vial and diluted in tetrahydrofuran (THF) to have a concentration of about 1 mg / mL. Thereafter, the standard sample for calibration and the sample to be analyzed are filtered through a syringe filter (pore size = 0.45 μm) and measured. As an analytical procedure, using Agilent Technologies' ChemStation, after obtaining each of the weight average molecular weight (Mw) and number average molecular weight (Mn) by comparing the elution time of the sample with a calibration curve, the molecular weight distribution (PDI) can be calculated by ratio (Mw / Mn). The measurement conditions of GPC can be as follows.

[0167] Instrument: Agilent Technologies 1200 Series

[0168] Column: Two PL gel mixed B from Polymer Laboratories

[0169] Solvent: THF

[0170] Column temperature: 40°C

[0171] Sample concentration: 1 mg / mL, inject 10 μL

[0172] Standard sample: polystyrene (Mp: 3900000, 723000, 316500, 52200, 31400, 7200, 3940, 485)

[0173] In one embodiment of the present specification, the polymer including the unit represented by Chemical Formula 1 may have a viscosity of 1 cP to 60 cP at room temperature. In another embodiment, the viscosity may be 1 cP to 40 cP, 2 cP to 20 cP, 2 cP to 12 cP, or 3 cP to 8 cP. In another embodiment, the viscosity of the polymer may be 4 cP to 6.5 cP at room temperature.

[0174] The viscosity can be measured using a Brookfield viscometer CV Nest Cone & Plate rheometer while maintaining 25° C. Herein, 1 mL of a sample (solvent: toluene) containing 2 wt % of a specimen can be used.

[0175] When the polymer viscosity satisfies the above range, a viscosity suitable for solution processes is achieved, and devices can be easily manufactured. On the other hand, a polymer viscosity less than the above range may cause fluidity problems, making it difficult to use the polymer in the process, and a viscosity greater than the above range may cause problems such as high viscosity that may make the polymer unusable for high-resolution panel manufacturing.

[0176] One embodiment of the present specification provides a coating composition including a polymer including a unit represented by Chemical Formula 1.

[0177] According to one embodiment of the present specification, the coating composition may further include a solvent.

[0178] In one embodiment of the present specification, the coating composition may be in a liquid phase. “Liquid phase” means being in a liquid state at room temperature and atmospheric pressure.

[0179] In one embodiment of the present specification, examples of the solvent may include: chlorine-based solvents such as chloroform, dichloromethane, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, or o-dichlorobenzene; ether-based solvents such as tetrahydrofuran or dichloromethane; solvents based on aromatic hydrocarbons, such as toluene, xylene, trimethylbenzene or mesitylene; solvents based on aliphatic hydrocarbons, such as cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane or n-decane; solvents based on ketones, such as acetone, methyl ethyl ketone or cyclohexanone; solvents based on esters, such as ethyl acetate, butyl acetate or ethyl cellosolve acetate; polyols, such as ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxyethane, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, Ether, glycerol or 1,2-hexanediol, and derivatives thereof; alcohol-based solvents such as methanol, ethanol, propanol, isopropanol or cyclohexanol; sulfoxide-based solvents such as dimethyl sulfoxide; amide-based solvents such as N-methyl-2-pyrrolidone or N,N-dimethylformamide; benzoate-based solvents such as methyl benzoate, butyl benzoate or 3-phenoxybenzoate; tetralin; and the like, however, the solvent is not limited thereto as long as it is a solvent capable of dissolving or dispersing the compound according to one embodiment of the present specification.

[0180] In another embodiment, the solvent may be used as one type alone, or as a mixture of two or more solvent types.

[0181] In another embodiment, the viscosity of the single solvent or the mixed solvent at room temperature is preferably 1 cP to 10 cP, more preferably 3 cP to 8 cP, but is not limited thereto.

[0182] In another embodiment, the coating composition has a concentration of preferably 0.1 to 20 weight / volume %, more preferably 0.5 to 5 weight / volume %, however, the concentration is not limited thereto.

[0183] Furthermore, one embodiment of the present specification provides an organic light-emitting device formed using the coating composition.

[0184] One embodiment of the present specification provides an organic light-emitting device including: a first electrode; a second electrode; and an organic material layer disposed between the first electrode and the second electrode, wherein the organic material layer includes the polymer including the unit represented by Chemical Formula 1 described above.

[0185] In one embodiment of the present specification, the first electrode is a cathode, and the second electrode is an anode.

[0186] In another embodiment, the first electrode is an anode and the second electrode is a cathode.

[0187] In one embodiment of the present specification, the organic material layer including the polymer including the unit represented by Chemical Formula 1 is an electron blocking layer; a hole transport layer; a hole injection layer; or a hole injection and transport layer.

[0188] According to one embodiment of the present specification, the organic material layer including the polymer including the unit represented by Chemical Formula 1 is a hole transport layer.

[0189] In another embodiment of the present specification, the organic material layer including the polymer including the unit represented by Chemical Formula 1 is a hole blocking layer; an electron transport layer; an electron injection layer; or an electron injection and transport layer.

[0190] In one embodiment of the present specification, the organic light-emitting device may further include one, two or more layers selected from the following: a hole injection layer; a hole transport layer; a light-emitting layer; an electron transport layer; an electron injection layer; an electron blocking layer; a hole blocking layer; a hole injection and transport layer; and an electron injection and transport layer.

[0191] In another embodiment, the organic light emitting device may be an organic light emitting device (normal type) having a forward structure in which an anode, one or more organic material layers, and a cathode are sequentially laminated on a substrate.

[0192] In another embodiment, the organic light emitting device may be an organic light emitting device having an inverted structure (inverted type) in which a cathode, one or more organic material layers, and an anode are sequentially laminated on a substrate.

[0193] The organic material layer of the organic light-emitting device of the present specification may be formed into a single-layer structure, but may also be formed into a multilayer structure in which two or more organic material layers are laminated. For example, the organic light-emitting device of the present specification may have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, a hole injection and transport layer, and an electron injection and transport layer as organic material layers. However, the structure of the organic light-emitting device is not limited thereto and may include a smaller number of organic layers.

[0194] For example, Figure 1 The structure of an organic light-emitting device according to one embodiment of the present specification is shown.

[0195] Figure 1 The structure of an organic light-emitting device is shown in which a first electrode 201, a hole injection layer 301, a hole transport layer 401, a light-emitting layer 501, an electron injection and transport layer 601, and a second electrode 701 are sequentially stacked on a substrate 101. Herein, the electron injection and transport layer means a layer that simultaneously performs electron injection and electron transport.

[0196] In one embodiment of the present specification, Figure 1 The hole injection layer 301 or the hole transport layer 401 may be formed using a coating composition including a polymer including a unit represented by Chemical Formula 1.

[0197] Figure 1 An organic light emitting device is shown, however, the organic light emitting device is not limited thereto.

[0198] When the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material as or different materials from each other.

[0199] The organic light-emitting device of the present specification can be manufactured using materials and methods known in the art, except that one or more layers of the organic material layer are formed using the above-mentioned coating composition.

[0200] For example, the organic light-emitting device of the present specification can be manufactured by sequentially laminating an anode, an organic material layer, and a cathode on a substrate. In this article, the organic light-emitting device can be manufactured by forming an anode on a substrate by depositing a metal, a conductive metal oxide, or an alloy thereof using a physical vapor deposition (PVD) method such as sputtering or electron beam evaporation, forming an organic material layer including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, etc. on the anode, and then depositing a material that can be used as a cathode on the organic material layer. In addition to such a method, an organic light-emitting device can also be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

[0201] The present invention provides a method for manufacturing an organic light-emitting device formed using a coating composition. Herein, the coating composition refers to a coating composition including a polymer containing a unit represented by Chemical Formula 1.

[0202] One embodiment of the present specification provides a method for manufacturing an organic light-emitting device, the method comprising: preparing a first electrode; forming one or more organic material layers on the first electrode; and forming a second electrode on the one or more organic material layers, wherein forming the one or more organic material layers comprises forming the organic material layers using a coating composition comprising the above-mentioned polymer containing the unit represented by Chemical Formula 1.

[0203] In the method for manufacturing an organic light-emitting device, forming an organic material layer using the coating composition includes coating the coating composition; and performing a heat treatment or a light treatment on the coated coating composition.

[0204] In the method for manufacturing an organic light-emitting device, forming an organic material layer using a coating composition includes coating the coating composition on a first electrode or one or more organic material layers; and performing heat treatment or light treatment on the coated coating composition.

[0205] In one embodiment of the present specification, the organic material layer formed using the coating composition is formed using spin coating or inkjet.

[0206] In another embodiment, the organic material layer formed using the coating composition is formed using a printing method.

[0207] In one embodiment of the present specification, examples of the printing method include inkjet printing, nozzle printing, offset printing, transfer printing, screen printing, and the like, but are not limited thereto.

[0208] The coating composition according to one embodiment of the present specification is suitable for a solution method due to its structural characteristics and can be formed using a printing method, and thus is economical in terms of time and cost when manufacturing a device.

[0209] In one embodiment of the present specification, in the case of heat treatment or light treatment, the heat treatment time is preferably within 1 hour, more preferably within 30 minutes.

[0210] In one embodiment of the present specification, in the case of heat treatment or light treatment, the atmosphere of the heat treatment is preferably an inert gas such as argon or nitrogen.

[0211] In one embodiment, when a coating composition including a polymer including a unit represented by Chemical Formula 1 is used as the coating composition, heat-treating or light-treating the coated coating composition may remove the solvent from the coated coating composition.

[0212] When using coating composition to form organic material layer comprises heat treatment or light treatment, can provide the organic material layer comprising wherein coating composition by thin film structure.In this case, can prevent the organic material layer formed using coating composition from dissolving, being affected in form, or decomposing because of the solvent on the surface of organic material layer.

[0213] In addition, the organic material layer according to one embodiment of the present specification may solely include a polymer including the unit represented by Chemical Formula 1, but may also additionally include other monomers or other polymers.

[0214] As the anode material, a material having a large work function is generally preferred so that hole injection into the organic material layer is smooth. Specific examples of anode materials that can be used in this specification include: metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline; etc., but are not limited thereto.

[0215] The cathode material is preferably a material with a small work function that facilitates electron injection into the organic material layer. Specific examples of cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; and multilayer structure materials such as LiF / Al or LiO2 / Al.

[0216] The hole injection layer is a layer that injects holes from the electrode, and the hole injection material is preferably a compound that has the ability to transport holes, and therefore has the effect of injecting holes in the anode and an excellent hole injection effect on the light-emitting layer or the light-emitting material, preventing the excitons generated in the light-emitting layer from moving to the electron injection layer or the electron injection material. In addition, it has excellent thin film forming ability. The highest occupied molecular orbital (HOMO) of the hole injection material is preferably between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of hole injection materials include metalloporphyrins, oligothiophenes, organic materials based on arylamines, organic materials based on hexanitrile hexaazatriphenylene, organic materials based on quinacridone, organic materials based on perylene, anthraquinone, conductive polymers based on polyaniline and polythiophene, but are not limited thereto.

[0217] The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer. When the organic light-emitting device includes an additional hole transport layer in addition to the hole transport layer comprising a polymer containing the unit represented by Chemical Formula 1, a material that can receive holes from the anode or hole injection layer, move the holes to the light-emitting layer, and has high hole mobility is suitable for use as the hole transport material. Specific examples include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers having both conjugated and non-conjugated portions.

[0218] The electron blocking layer is a layer that can improve the device life and efficiency by preventing electrons injected from the electron injection layer from entering the hole injection layer after passing through the light-emitting layer, and can be formed in an appropriate portion between the light-emitting layer and the hole injection layer using known materials as needed.

[0219] The light-emitting material is a material that can emit light in the visible region by receiving holes and electrons from the hole transport layer and the electron transport layer, respectively, and combining the holes and electrons, and is preferably a material having a favorable quantum efficiency for fluorescence or phosphorescence. Specific examples thereof include 8-hydroxy-quinoline aluminum complex (Alq3); carbazole-based compounds; diphenylvinyl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo-based azole-, benzothiazole-, and benzimidazole-based compounds; poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; polyfluorenes; rubrene; and the like, but are not limited thereto.

[0220] The light-emitting layer may include a host material and a dopant material. The host material includes fused aromatic ring derivatives, heterocyclic compounds, and the like. Specifically, fused aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds. Heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, and pyrimidine derivatives. However, the materials are not limited thereto.

[0221] Dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, aromatic amine derivatives are fused aromatic ring derivatives having substituted or unsubstituted arylamine groups, and include pyrene, anthracene, , diindenopyrene, etc. Styrylamine compounds are compounds in which a substituted or unsubstituted arylamine is substituted with at least one arylvinyl group. Compounds that are unsubstituted or substituted with one, two, or more substituents selected from aryl, silyl, alkyl, cycloalkyl, and arylamine groups can be used. Specifically, examples include styrylamine, styryldiamine, styryltriamine, and styryltetramine, but are not limited thereto. Furthermore, metal complexes include, but are not limited to, iridium complexes and platinum complexes.

[0222] The electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light-emitting layer. As the electron transport material, a material that can advantageously receive electrons from the cathode, move the electrons to the light-emitting layer, and has high electron mobility is suitable. Specific examples thereof include Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic free radical compounds; hydroxyflavone-metal complexes, etc., but are not limited thereto. The electron transport layer can be used with any desired cathode material as used in the art. In particular, examples of suitable cathode materials include common materials having a small work function and followed by an aluminum layer or a silver layer. Specifically, cathode materials include cesium, barium, calcium, ytterbium, and samarium, in each case followed by an aluminum layer or a silver layer.

[0223] The electron injection layer is a layer that injects electrons from the electrode, and the electron injection material is preferably a compound that has the ability to transport electrons, has an effect of injecting electrons from the cathode, has an excellent electron injection effect on the light-emitting layer or the light-emitting material, prevents the excitons generated in the light-emitting layer from moving to the hole injection layer, and has excellent thin film forming ability. Specific examples thereof include fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, Azoles, The examples include, but are not limited to, diazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylmethane, anthrone, and derivatives thereof, metal complex compounds, nitrogen-containing 5-membered ring derivatives, and the like.

[0224] Metal complex compounds include 8-hydroxyquinolinate lithium, bis(8-hydroxyquinolinate) zinc, bis(8-hydroxyquinolinate) copper, bis(8-hydroxyquinolinate) manganese, tris(8-hydroxyquinolinate) aluminum, tris(2-methyl-8-hydroxyquinolinate) aluminum, tris(8-hydroxyquinolinate) gallium, bis(10-hydroxybenzo[h]quinolinate) beryllium, bis(10-hydroxybenzo[h]quinolinate) zinc, bis(2-methyl-8-quinolinate) chlorogallium, bis(2-methyl-8-quinolinate)(o-cresol) gallium, bis(2-methyl-8-quinolinate)(1-naphthol) aluminum, bis(2-methyl-8-quinolinate)(2-naphthol) gallium, and the like, but are not limited thereto.

[0225] The hole blocking layer is a layer that blocks holes from reaching the cathode and can generally be formed under the same conditions as the hole injection layer. Specific examples thereof may include Oxadiazole derivatives or triazole derivatives, phenanthroline derivatives, aluminum complexes, etc., but not limited thereto.

[0226] The organic light emitting device according to the present specification may be a top emission type, a bottom emission type, or a dual emission type according to the materials used.

[0227] The organic light-emitting device according to the present invention can be included in and used in various electronic devices. For example, the electronic device can be a display panel, a touch panel, a solar module, a lighting system, etc., but is not limited thereto.

[0228] Embodiments of the invention

[0229] Hereinafter, this specification will be described in detail with reference to the embodiments to specifically describe this specification. However, the embodiments according to this specification can be modified into various different forms, and the scope of this specification should not be interpreted as being limited to the embodiments described below. The embodiments of this specification are provided to more fully describe this specification to those of ordinary skill in the art.

[0230] [Preparation of polymer]

[0231] Preparation Example 1.

[0232]

[0233] Compound M1 (1 mmol) was added to a scintillation vial and dissolved in toluene (11 mL) to prepare a first solution.

[0234] A 50 mL Schlenk tube was filled with bis(1,5-cyclooctadiene)nickel(0) (1.01 mmol), 2,2′-bipyridyl (1.01 mmol) and 1,5-cyclooctadiene (1.01 mmol) were weighed and introduced into a scintillation vial, and dissolved in N,N-dimethylformamide (5.5 mL) and toluene (11 mL) to prepare a second solution.

[0235] The second solution is introduced in the Schlenk tube, stirred at 50 ℃ for 30 minutes. The first solution is further added in the Schlenk tube, and the gained is stirred at 50 ℃ for 180 minutes. Then, the Schlenk tube is cooled to room temperature, then poured in HCl / methanol (5% volume / volume, concentrated HCl). After stirring for 45 minutes, collect polymer by vacuum filtration, and dry under high vacuum. Polymer is dissolved in toluene (1% weight / volume), and by the post of the basic aluminum oxide (6g) that is layered on silica gel (6g). Polymer / toluene filtrate is concentrated (5% weight / volume toluene), grind with acetone. Obtain polymer 1 with 60% productive rate.

[0236] Preparation Example 2.

[0237]

[0238] Polymer 2 was prepared in the same manner as in the method for preparing Polymer 1, except that Compounds M2 and M3 were used instead of Compound M1.

[0239] Preparation Example 3.

[0240]

[0241] Polymer 3 was prepared in the same manner as in the method for preparing Polymer 1, except that Compound M4 was used instead of Compound M1.

[0242] Preparation Example 4.

[0243]

[0244] Polymer 4 was prepared in the same manner as in the method for preparing Polymer 1, except that Compound M5 was used instead of Compound M1.

[0245] Preparation Example 5.

[0246]

[0247] Polymer 5 was prepared in the same manner as in the method for preparing Polymer 1, except that Compound M6 was used instead of Compound M1.

[0248] The number average molecular weight (Mn), weight average molecular weight (Mw), molecular weight distribution (PDI) value, and viscosity value of each of Polymers 1 to 5 prepared in Preparation Examples 1 to 5 are described in Table 1 below.

[0249] Specifically, the number average molecular weight (Mn), the weight average molecular weight (Mw), and the molecular weight distribution (PDI) are measured using GPC (gel permeation chromatography).

[0250] The viscosity was measured using a Brookfield Viscometer CV Nest Cone & Plate Rheometer using a sample (1 mL) containing 2 wt% of the polymer (solvent: toluene) while maintaining 25°C.

[0251] [Table 1]

[0252]

[0253] [Experimental example]

[0254] Example 1.

[0255] Acetone solvent was used to deposit a layer with a thickness of A glass substrate with an ITO film was ultrasonically cleaned for 10 minutes. The substrate was then placed in distilled water containing a detergent and ultrasonically cleaned for 10 minutes. The ultrasonic cleaning was then repeated twice with distilled water for 10 minutes. Following the distilled water cleaning, the substrate was ultrasonically cleaned for 10 minutes with isopropyl alcohol and then dried. The substrate was then transferred to a glove box.

[0256] On the transparent ITO electrode prepared as above, 2 wt% cyclohexanone ink of compound A: chemical formula B (weight ratio of 8:2) was spin-coated (4000 rpm) on the ITO surface and heat-treated at 230°C for 30 minutes to form a hole injection layer with a thickness of 40 nm.

[0257] A toluene solution containing polymer 1 at 0.8 wt % was prepared and then spin-coated on the hole injection layer to form a hole transport layer having a thickness of 100 nm.

[0258] Subsequently, a light-emitting layer was formed on the hole transport layer using a solution process using the following compound C and compound D at a weight ratio of 9:1. Compound E was vacuum-deposited on the light-emitting layer to form a 40 nm thick electron injection and transport layer. On the electron injection and transport layer, LiF was sequentially deposited to a thickness of 0.5 nm and aluminum to a thickness of 100 nm to form a cathode.

[0259] During the above process, the deposition rate of the organic material is kept at / second to / sec, and the deposition rates of LiF and aluminum were kept at / second and / sec, and the vacuum degree during deposition was maintained at 2 × 10 -8 Up to 5×10 -6 Entrust.

[0260] [Compound A]

[0261]

[0262] [Compound B]

[0263]

[0264] [Compounds C, D, E]

[0265]

[0266] Examples 2 to 5 and Comparative Examples 1 and 2

[0267] Organic light-emitting devices were manufactured in the same manner as in Example 1, except that the polymers described in the following Table 3 were each used instead of Polymer 1 as a hole transport layer material in Example 1.

[0268] [Comparative polymer 1]

[0269]

[0270] [Comparative polymer 2]

[0271]

[0272] [Table 2]

[0273] polymer Mn (g / mol) Mw(g / mol) PDI Comparative polymer 1 23600 84900 3.6 Comparative polymer 2 4890 16100 3.29

[0274] For the organic light emitting devices manufactured in Examples 1 to 5 and Comparative Examples 1 and 2, the 2 The driving voltage and external quantum efficiency were measured at a current density of , and the time (lifetime) taken for the luminance to become 95% relative to the initial luminance (1000 nits) at the current density was measured. The results are shown in Table 3 below.

[0275] [Table 3]

[0276] Experimental example polymer Voltage (V) <![CDATA[J(mA / cm 2 )]]> EQE (%) T95 (hours) Example 1 1 4.31 10 5.67 167 Example 2 2 4.42 10 5.99 173 Example 3 3 4.30 10 5.63 171 Example 4 4 4.40 10 5.96 151 Example 5 5 4.29 10 5.58 125 Comparative Example 1 Comparative polymer 1 5.31 10 3.96 10 Comparative Example 2 Comparative polymer 2 4.75 10 0.66 8

[0277] According to Table 3, it is determined that Examples 1 to 5 of the present application have lower device driving voltage and excellent efficiency and lifespan compared with Comparative Examples 1 and 2 using Comparative Polymer 1 or Comparative Polymer 2 having a structure different from that of the polymer of the present application as the hole transport layer material.

[0278] Specifically, in Comparative Polymer 1, the fluorenyl substituent includes O. This imparts hydrophilic properties to the polymer, but requires primarily polar solvents to be selected as solvents for solution processes, which limits the types of solvents that can be used compared to the polymers of the present disclosure. Furthermore, during the process, the O in the substituent of Comparative Polymer 1 readily binds to moisture, reducing process efficiency. Consequently, devices using Comparative Polymer 1 exhibit significantly degraded voltage, efficiency, and lifetime characteristics.

[0279] Comparative Polymer 2 has a structure in which the L position of Chemical Formula 1 of the present disclosure is a direct bond, and a device using Comparative Polymer 2 has significantly deteriorated voltage, efficiency, and lifespan characteristics.

Claims

1. A polymer comprising a unit represented by the following Chemical Formula 1: [Chemical Formula 1] in, In Chemical Formula 1, R1 and R2 are the same as or different from each other and are each independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group; L is an arylene group substituted with one or more substituents selected from hexyl, octyl and tridecyl; or a heteroarylene group substituted with one or more substituents selected from hexyl, octyl and tridecyl; L1 to L4 are the same as or different from each other and are each independently a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group; a and b are each 1 or 2, and when a and b are 2, the substituents in the two brackets are the same as or different from each other; n1 and n2 are each an integer from 0 to 4, and when n1 and n2 are 2 or greater, two or more substituents in the brackets are the same as or different from each other; and m1, which is the repetition number of the unit, is an integer from 5 to 5,000.

2. The polymer according to claim 1, wherein Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-4: [Chemical Formula 1-1] [Chemical formula 1-2] [Chemical formula 1-3] [Chemical formula 1-4] In Chemical Formulas 1-1 to 1-4, R1, R2, L1 to L4, a, b, n1, n2 and m1 have the same definitions as in Chemical Formula 1; X is O, S or NR; R, R3 to R8, Ar1 and Ar2 are the same as or different from each other and are each independently hexyl, octyl or tridecyl; c is 1 or 2, and when c is 2, the substituents in the two brackets are the same as or different from each other; n3 is an integer from 1 to 4; n4, n6 and n7 are each an integer from 0 to 3; If X is O or S, then n6+n7 is 1 or more, n5 is an integer from 0 to 5; n8 is an integer from 1 to 6; and When n3 to n8 are each 2 or greater, two or more substituents in the brackets are the same as or different from each other. 3 . The polymer according to claim 1 , wherein L 1 to L 4 are the same as or different from each other and are each independently a substituted or unsubstituted biphenylene group; or a substituted or unsubstituted terphenylene group.

4. The polymer according to claim 1, wherein the unit represented by Chemical Formula 1 is any one selected from the following structures: In the structure described, m1, which is the repetition number of the unit, is an integer from 5 to 5,000.

5. A coating composition comprising the polymer according to any one of claims 1 to 4.

6. An organic light-emitting device comprising: a first electrode; a second electrode; as well as an organic material layer disposed between the first electrode and the second electrode, The organic material layer comprises the polymer according to any one of claims 1 to 4. 7 . The organic light-emitting device according to claim 6 , wherein the organic material layer comprising the polymer is an electron blocking layer; a hole transport layer; a hole injection layer; or a hole injection and transport layer. 8 . The organic light-emitting device according to claim 6 , wherein the organic material layer comprising the polymer is a hole blocking layer; an electron transport layer; an electron injection layer; or an electron injection and transport layer.

9. A method for manufacturing an organic light-emitting device, the method comprising: preparing a first electrode; forming one or more organic material layers on the first electrode; as well as forming a second electrode on the one or more organic material layers, Wherein forming one or more organic material layers comprises forming the organic material layers using the coating composition according to claim 5 . 10 . The method for manufacturing an organic light-emitting device according to claim 9 , wherein forming the organic material layer using the coating composition comprises applying the coating composition; and performing a heat treatment or a light treatment on the applied coating composition.

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