KR102817427B1 - Polymer and organic light emitting device using the same - Google Patents

Abstract

The present specification relates to a polymer comprising a first unit represented by chemical formula 1; a second unit represented by chemical formula 1 and different from the first unit; a third unit represented by chemical formula 2; and a terminal group represented by chemical formula 3, and an organic light-emitting device using the same.

Description

Polymer and organic light emitting device using the same {POLYMER AND ORGANIC LIGHT EMITTING DEVICE USING THE SAME}

This application claims the benefit of Korean Patent Application No. 10-2021-0095599 filed with the Korean Intellectual Property Office on July 21, 2021, the entire contents of which are incorporated herein by reference.

The present specification relates to a polymer and an organic light-emitting device formed using the same.

Organic luminescence is an example of an electric current being converted into visible light by an internal process of a specific organic molecule. The principle of the organic luminescence is as follows. When an organic layer is positioned between an anode and a cathode and a current is applied between the two electrodes, electrons and holes are injected into the organic layer from the cathode and the anode, respectively. The electrons and holes injected into the organic layer recombine to form excitons, and when these excitons fall back to the ground state, light is emitted. An organic electroluminescent device utilizing this principle can generally be composed of an organic layer including a cathode and an anode and an organic layer positioned therebetween, such as a hole injection layer, a hole transport layer, an emission layer, an electron transport layer, and an electron injection layer.

Most of the materials used in organic light-emitting devices are pure organic substances or complex compounds formed by complexing organic substances with metals, and can be classified into hole injection materials, hole transport materials, luminescent materials, electron transport materials, and electron injecting materials depending on the purpose. Here, organic substances with p-type properties, that is, organic substances that are easily oxidized and electrochemically stable when oxidized, are mainly used as hole injection materials or hole transport materials. On the other hand, organic substances with n-type properties, that is, organic substances that are easily reduced and electrochemically stable when reduced, are mainly used as electron injection materials or electron transport materials. As luminescent materials, a material that has both p-type and n-type properties, that is, a material that is stable in both oxidized and reduced states, and a material with high luminescent efficiency that converts excitons into light when formed is preferable.

In addition to those mentioned above, it is desirable for materials used in organic light-emitting devices to have the following additional properties.

First, it is desirable that the material used in the organic light-emitting device have excellent thermal stability. This is because Joule heating occurs due to the movement of charges within the organic light-emitting device. NPB (N,N'-Di(1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine), which is currently mainly used as a hole transport layer material, has a glass transition temperature of less than 100℃, and therefore has a problem in that it is difficult to use in organic light-emitting devices that require high current.

Second, in order to obtain a high-efficiency organic light-emitting device that can be driven at low voltage, the holes or electrons injected into the organic light-emitting device must be smoothly transferred to the light-emitting layer, while the injected holes and electrons must be prevented from escaping out of the light-emitting layer. To this end, the material used in the organic light-emitting device must have an appropriate band gap and HOMO (Highest Occupied Molecular Orbital) or LUMO (Lowest Unoccupied Molecular Orbital) energy level. In the case of PEDOT:PSS (Poly(3,4-ethylenedioxythiophene) doped:poly(styrenesulfonic acid)), which is currently used as a hole transport material in organic light-emitting devices manufactured by the solution coating method, the LUMO energy level is lower than that of the organic material used as the light-emitting layer material, making it difficult to manufacture high-efficiency, long-life organic light-emitting devices.

In addition, the material used in the organic light-emitting device must have excellent chemical stability, charge mobility, and interface characteristics with the electrode or adjacent layer. In other words, the material used in the organic light-emitting device must be less deformed by moisture or oxygen. In addition, it must have appropriate hole or electron mobility so that the density of holes and electrons in the light-emitting layer of the organic light-emitting device is balanced to maximize exciton formation. In addition, it must be able to improve the interface with the electrode including a metal or metal oxide for the stability of the device.

In addition to those mentioned above, materials used in organic light-emitting devices for solution processes must additionally have the following properties.

First, a storable, homogeneous solution must be formed. In the case of commercialized deposition process materials, they have good crystallinity and do not dissolve well in the solution, or even if a solution is formed, crystals are easily formed, so the concentration gradient of the solution changes depending on the storage period, or there is a high possibility of forming a defective element.

Second, the layers in which the solution process is performed must have solvent and material resistance with respect to other layers. To this end, a material that can form a self-cross-linked polymer on the substrate through heat treatment or UV (ultraviolet) irradiation after solution application by introducing a curing agent, such as VNPB (N4,N4'-di(naphthalen-1-yl)-N4,N4'-bis(4-vinylphenyl)biphenyl-4,4'-diamine), or a polymer that has sufficient resistance to the next process is preferable. A material that can have solvent resistance on its own, such as HATCN (Hexaazatriphenylenehexacarbonitrile), is also preferable.

Therefore, in the field of party technology, there is a demand for the development of organic materials having the above requirements.

Korean Patent Publication No. 10-2004-0028954

The present specification provides a polymer and an organic light-emitting device formed using the same.

One embodiment of the present specification provides a polymer comprising a first unit represented by the following chemical formula 1; a second unit represented by the following chemical formula 1 and different from the first unit; a third unit represented by the following chemical formula 2; and a terminal group represented by the following chemical formula 3.

[Chemical Formula 1]

[Chemical formula 2]

[Chemical Formula 3]

In the above chemical formulas 1 to 3,

L1, L3 and L4 are the same or different from each other, and each independently represents a direct bond; or a substituted or unsubstituted arylene group,

Ar1, Ar2 and L2 are the same or different from each other and are each independently a substituted or unsubstituted arylene group,

R1 and R2 are the same as or different from each other, and each independently represents hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted arylamine group; or a substituted or unsubstituted siloxane group,

R10 and R11 are the same as or different from each other, and each independently represents a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; or a substituted or unsubstituted arylamine group,

n1 and n2 are each an integer from 1 to 4, and when n1 and n2 are each 2 or greater, the substituents in each parenthesis are the same or different,

m is an integer of 3 or 4,

When m is 3, Z is CRa; SiRa; N; or a trivalent substituted or unsubstituted aryl group,

When m is 4, Z is C; Si; or a tetravalent substituted or unsubstituted aryl group,

Ra is hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group,

Y is a direct bond; a substituted or unsubstituted alkylene group; or a substituted or unsubstituted arylene group,

When Y is a direct bond; or a substituted or unsubstituted alkylene group, Z is a trivalent or tetravalent substituted or unsubstituted aryl group,

E is hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted arylamine group; a substituted or unsubstituted siloxane group; a substituted or unsubstituted heterocyclic group; a crosslinking group; or a combination thereof,

* is an attachment point within the polymer.

Another embodiment of the present specification provides an organic light-emitting device comprising: a first electrode; a second electrode; and at least one organic layer provided between the first electrode and the second electrode, wherein at least one of the organic layers comprises the polymer.

The polymer according to one embodiment of the present specification can easily control electrical properties by simultaneously including different first and second units. Accordingly, it exhibits the effect of improving hole mobility.

In addition, the polymer according to one embodiment of the present specification can be applied to an organic layer of an organic light-emitting device to improve the performance and/or lifespan characteristics of the device. Specifically, it can be applied to a hole transport layer of an organic light-emitting device to improve the efficiency and/or lifespan of the device.

FIGS. 1 and 2 are diagrams illustrating the structure of an organic light-emitting device according to some embodiments of the present specification.

Hereinafter, the specification is described in detail.

The present specification provides a polymer comprising a first unit represented by the following chemical formula 1; a second unit represented by the following chemical formula 1 and different from the first unit; a third unit represented by the following chemical formula 2; and a terminal group represented by the following chemical formula 3.

[Chemical Formula 1]

[Chemical formula 2]

[Chemical Formula 3]

In the above chemical formulas 1 to 3,

L1, L3 and L4 are the same or different from each other, and each independently represents a direct bond; or a substituted or unsubstituted arylene group,

Ar1, Ar2 and L2 are the same or different from each other and are each independently a substituted or unsubstituted arylene group,

R1 and R2 are the same as or different from each other, and each independently represents hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted arylamine group; or a substituted or unsubstituted siloxane group,

R10 and R11 are the same as or different from each other, and each independently represents a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; or a substituted or unsubstituted arylamine group,

n1 and n2 are each an integer from 1 to 4, and when n1 and n2 are each 2 or greater, the substituents in each parenthesis are the same or different,

m is an integer of 3 or 4,

When m is 3, Z is CRa; SiRa; N; or a trivalent substituted or unsubstituted aryl group,

When m is 4, Z is C; Si; or a tetravalent substituted or unsubstituted aryl group,

Ra is hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group,

Y is a direct bond; a substituted or unsubstituted alkylene group; or a substituted or unsubstituted arylene group,

When Y is a direct bond; or a substituted or unsubstituted alkylene group, Z is a trivalent or tetravalent substituted or unsubstituted aryl group,

E is hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted arylamine group; a substituted or unsubstituted siloxane group; a substituted or unsubstituted heterocyclic group; a crosslinking group; or a combination thereof,

* is an attachment point within the polymer.

In one embodiment of the present specification, the polymer includes first and second units that are different from each other. When the first unit is included alone or the second unit is included alone, there is a problem that it is difficult to finely control the electrical characteristics because the electrical characteristics are determined only by the first unit or the second unit. On the other hand, the polymer of the present specification includes both the first unit and the second unit having different electrical characteristics, so it has an advantage that the electrical characteristics can be finely controlled by controlling the two units. Therefore, the polymer according to one embodiment of the present specification includes both the first unit and the second unit that are different from each other, thereby showing an effect of improving hole mobility compared to the case where the first unit or the second unit is included alone, and thus the effect of improving the efficiency and lifespan of the organic light-emitting device to which the polymer is applied can be obtained.

In this specification, when it is said that a certain member (layer) is located “on” another member (layer), this includes not only cases where a certain member (layer) is in contact with another member, but also cases where another member (layer) exists between the two members (layers).

In this specification, when a part is said to "include" a certain component, this does not mean that other components are excluded, but rather that other components may be included, unless otherwise specifically stated.

As used herein, “mole fraction” means the ratio of the number of moles of a given component to the total number of moles of all components.

In this specification, the term "adjacent" may refer to a substituent substituted on an atom directly connected to the atom substituted by the substituent, a substituent stereostructurally closest to the substituent, or another substituent substituted on the atom substituted by the substituent. For example, two substituents substituted at the ortho position in a benzene ring and two substituents substituted on the same carbon in an aliphatic ring may be interpreted as "adjacent" groups to each other.

In the present specification, in a ring formed by bonding adjacent groups to each other, “ring” means a substituted or unsubstituted hydrocarbon ring; or a substituted or unsubstituted heterocycle.

Unless otherwise defined herein, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. Although methods and materials similar or equivalent to those described herein can be used in the practice or testing of embodiments of the present invention, suitable methods and materials are described below. All publications, patents, and other references mentioned in this invention are incorporated herein by reference in their entirety, and in case of conflict, the present invention, including definitions, will control unless a specific passage is cited. In addition, the materials, methods, and examples are illustrative only and not intended to be limiting.

Examples of substituents in this specification are described below, but are not limited thereto.

"는 다른 치환기 또는 결합부에 연결되는 부위를 의미한다.In this specification, "

" means a moiety that is connected to another substituent or bonding moiety.

In this specification, “*” represents an attachment point within the polymer.

The term "substitution" above means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position of the substitution is not limited to the position at which the hydrogen atom is replaced, i.e., a position at which the substituent can be replaced, and when two or more are substituted, the two or more substituents may be the same or different from each other.

The term "substituted or unsubstituted" as used herein means substituted with one or more substituents selected from the group consisting of deuterium; a halogen group; an alkyl group; a cycloalkyl group; an alkoxy group; an aryloxy group; an amine group; an aryl group; a heterocyclic group; and a cross-linking group, or substituted with a substituent in which two or more substituents are linked among the above-mentioned substituents, or has no substituents. For example, "a substituent linked with two or more substituents" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may also be interpreted as a substituent in which two phenyl groups are linked.

Examples of the above substituents are described below, but are not limited thereto.

In this specification, examples of halogen groups include fluorine (F), chlorine (Cl), bromine (Br), or iodine (I).

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to one embodiment, the number of carbon atoms of the alkyl group is 1 to 30. Specific examples of the alkyl group include, but are not limited to, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, and the like.

In this specification, an alkylene group means a group having two bonding positions to an aryl group, i.e., a divalent group. The description of the alkyl group described above can be applied to each of these groups, except that they are each divalent.

In the present specification, the carbon number of the cycloalkyl group is not particularly limited, but is preferably 3 to 60. According to one embodiment, the carbon number of the cycloalkyl group is 3 to 30. Specific examples of the cycloalkyl group include, but are not limited to, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and the like.

In the present specification, the alkoxy group may be linear, branched or cyclic. The carbon number of the alkoxy group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specific examples of the alkoxy group include, but are not limited to, a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, an isobutoxy group, a tert-butoxy group, a sec-butoxy group, an n-pentyloxy group, a neopentyloxy group, an isopentyloxy group, an n-hexyloxy group, a 3,3-dimethylbutyloxy group, a 2-ethylbutyloxy group, an n-octyloxy group, an n-nonyloxy group, an n-decyloxy group, and the like.

In the present specification, the amine group may be selected from the group consisting of -NH ₂ ; an alkylamine group; an arylalkylamine group; an arylamine group; an arylheteroarylamine group; an alkylheteroarylamine group, and a heteroarylamine group, but is not limited thereto. The number of carbon atoms in the amine group is not particularly limited, but is preferably 1 to 60.

In the present specification, the carbon number of the aryl group is not particularly limited, but is preferably 6 to 60. According to one embodiment, the carbon number of the aryl group is 6 to 30. In one embodiment of the present specification, the aryl group may be a monocyclic aryl group or a polycyclic aryl group. The monocyclic aryl group may be, but is not limited to, a phenyl group, a biphenyl group, a terphenyl group, or the like. The polycyclic aryl group may be, but is not limited to, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a triphenylenyl group, a chrysenyl group, a fluorenyl group, or the like.

In this specification, an arylene group means a group having two bonding positions to an aryl group, i.e., a divalent group. The description of the aryl group described above can be applied to each of these groups, except that they are each divalent.

In the present specification, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group including two or more aryl groups may include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time. For example, the aryl group in the arylamine group may be selected from the examples of the above-mentioned aryl groups. The carbon number of the arylamine group is not particularly limited, but is preferably 6 to 60.

In the present specification, a heterocyclic group is an aromatic, aliphatic, or aromatic-aliphatic condensed ring group containing one or more non-carbon atoms or heteroatoms. Specifically, the heteroatom may contain one or more atoms selected from the group consisting of O, N, Se, and S. The number of carbon atoms in the heterocyclic group is not particularly limited, but may be 2 to 60. Examples of the above heterocyclic group include a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a pyridine group, a bipyridine group, a pyrimidine group, a triazine group, a triazole group, an acridine group, a pyridazine group, a pyrazine group, a quinoline group, a quinazoline group, a quinoxaline group, a phthalazine group, a pyrido pyrimidine group, a pyrido pyrazine group, a pyrazino pyrazine group, an isoquinoline group, an indole group, a carbazole group, a benzoxazole group, a benzimidazole group, a benzothiazole group, a benzocarbazole group, a benzothiophene group, a dibenzothiophene group, a benzofuran group, a phenanthridine group, a phenanthroline group, an isoxazole group, a thiadiazole group, Examples include, but are not limited to, phenothiazine groups and dibenzofuran groups.

In the present specification, a heteroaryl group is an aromatic ring group containing one or more heteroatoms. The number of carbon atoms in the heteroaryl group is not particularly limited, but may be 2 to 60. Examples of the heteroaryl group include, but are not limited to, a pyridine group, a pyrrole group, a pyrimidine group, a pyridazine group, a furan group, a thiophene group, a benzothiophene group, a benzofuran group, a dibenzothiophene group, a dibenzofuran group, and a carbazole group.

In this specification, an aryloxy group is a group represented by -OR ₂₀₀ , where R ₂₀₀ is an aryl group. The aryl group in the aryloxy group is the same as the examples of the aryl group described above. Specifically, examples of the aryloxy group include, but are not limited to, a phenoxy group, a benzyloxy group, a p-methylbenzyloxy group, a p-tolyloxy group, a m-tolyloxy group, a 3,5-dimethyl-phenoxy group, a 2,4,6-trimethylphenoxy group, a p-tert-butylphenoxy group, a 3-biphenyloxy group, a 4-biphenyloxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, a 4-methyl-1-naphthyloxy group, a 5-methyl-2-naphthyloxy group, a 1-anthryloxy group, a 2-anthryloxy group, a 9-anthryloxy group, a 1-phenanthryloxy group, a 3-phenanthryloxy group, and a 9-phenanthryloxy group.

In the present specification, a silyl group is a group represented by -SiR ₂₀₁ R ₂₀₂ R ₂₀₃ , wherein R ₂₀₁ , R ₂₀₂ and R ₂₀₃ are the same or different, and each independently represent hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group. Examples of the silyl group include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, and a phenylsilyl group.

In the present specification, the siloxane group is a group represented by -Si(R ₂₀₄ ) ₂ OSi(R ₂₀₅ ) ₃ , wherein R ₂₀₄ and R ₂₀₅ are the same as or different from each other, and each independently represent hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group.

In the present specification, the hydrocarbon ring group may be an aromatic ring, an aliphatic ring, or a ring in which an aromatic ring and an aliphatic ring are fused.

In this specification, the description of the above-mentioned aryl group can be applied to the aromatic ring.

In this specification, the aliphatic ring may be applied with the description of the cycloalkyl group described above.

In the present specification, a combination of substituents means a substituent in which two or more of the exemplified substituents are connected. For example, hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a cross-linking group; or a combination thereof, in which the term 'combination' means a substituent in which two or more of the exemplified substituents are connected. For example, it may be a structure in which an alkyl group and a cross-linking group are connected, or a structure in which an alkyl group and an aryl group are connected, but is not limited thereto.

In the present specification, a cross-linking group may mean a reactive substituent that forms a cross-link between compounds by exposure to heat, light, and/or radiation. The cross-linking may be formed by the connection of radicals generated by the decomposition of carbon-carbon multiple bonds and cyclic structures by heat treatment, light irradiation, and/or radiation irradiation.

In this specification, the cross-linking group has any of the following structures.

In the above structure,

L30 to L36 are the same or different from each other, and each independently represents a direct bond; -O-; -COO-; a substituted or unsubstituted alkylene group; a substituted or unsubstituted arylene group; or a combination thereof,

은 상기 화학식 3에 결합되는 부위이다.

is a portion that is bonded to the above chemical formula 3.

Below, the first and second units are described.

In one embodiment of the present specification, the first unit and the second unit are units having two attachment points.

In one embodiment of the present specification, the first unit and the second unit are both represented by chemical formula 1, but are different from each other.

In one embodiment of the present specification, L1 is a direct bond; or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

In one embodiment of the present specification, L1 is a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted naphthylene group.

In one embodiment of the present specification, L2 is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

In one embodiment of the present specification, L2 is a substituted or unsubstituted phenylene group; or a substituted or unsubstituted naphthylene group.

In one embodiment of the present specification, the 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 the above chemical formulas 1-1 to 1-4,

R1, R2, R10, R11, Ar1, Ar2, L3, L4, n1 and n2 are the same as defined in the chemical formula 1 above,

R3 to R9 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted arylamine group; or a substituted or unsubstituted siloxane group,

n3 to n6 are each an integer from 1 to 4, and when n3 to n6 are each 2 or greater, the substituents in each parenthesis are the same or different,

n7 to n9 are each an integer from 1 to 6, and when n7 to n9 are each 2 or greater, the substituents in each parenthesis are the same or different,

* is an attachment point within the polymer.

In one embodiment of the present specification, the chemical formula 1 is represented by any one of the following chemical formulas 1-11 to 1-18.

[Chemical Formula 1-11]

[Chemical Formula 1-12]

[Chemical Formula 1-13]

[Chemical Formula 1-14]

[Chemical Formula 1-15]

[Chemical Formula 1-16]

[Chemical Formula 1-17]

[Chemical Formula 1-18]

In the above chemical formulas 1-11 to 1-18,

R1, R2, R10, R11, Ar1, Ar2, L3, L4, n1 and n2 are the same as defined in the chemical formula 1 above,

R3 to R9 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted arylamine group; or a substituted or unsubstituted siloxane group,

n3 to n6 are each an integer from 1 to 4, and when n3 to n6 are each 2 or greater, the substituents in each parenthesis are the same or different,

n7 to n9 are each an integer from 1 to 6, and when n7 to n9 are each 2 or greater, the substituents in each parenthesis are the same or different,

* is an attachment point within the polymer.

In one embodiment of the present specification, L3 and L4 are the same as or different from each other, and each independently represents a substituted or unsubstituted arylene group.

In one embodiment of the present specification, L3 and L4 are the same as or different from each other, and each independently represents a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

In one embodiment of the present specification, L3 and L4 are the same as or different from each other, and each independently represents a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; or a substituted or unsubstituted naphthylene group.

In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other and are substituted or unsubstituted arylene groups having 6 to 30 carbon atoms.

In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; or a substituted or unsubstituted naphthylene group.

In one embodiment of the present specification, the chemical formula 1 is represented by any one of the following chemical formulas 1-5 to 1-8.

[Chemical Formula 1-5]

[Chemical Formula 1-6]

[Chemical Formula 1-7]

[Chemical Formula 1-8]

In the above chemical formulas 1-5 to 1-8,

R1, R2, R10, R11, n1 and n2 are the same as defined in the chemical formula 1 above,

R3 to R9, R20 to R27 and R30 to R37 are the same as or different from each other and are each independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted arylamine group; or a substituted or unsubstituted siloxane group,

n3 to n6, n20 to n27 and n30 to n37 are each an integer of 1 to 4, n7 to n9 are each an integer of 1 to 6, and when n3 to n9, n20 to n27 and n30 to n37 are each 2 or more, the substituents in each parenthesis are the same or different,

p1 to p4 are each an integer from 1 to 3, and when p1 to p4 are each 2 or greater, the structures in each parenthesis are the same or different from each other.

* is an attachment point within the polymer.

In one embodiment of the present specification, the chemical formula 1 is represented by any one of the following chemical formulas 1-21 to 1-28.

[Chemical Formula 1-21]

[Chemical Formula 1-22]

[Chemical Formula 1-23]

[Chemical Formula 1-24]

[Chemical Formula 1-25]

[Chemical Formula 1-26]

[Chemical Formula 1-27]

[Chemical Formula 1-28]

In the above chemical formulas 1-21 to 1-28,

R1, R2, R10, R11, n1 and n2 are the same as defined in the chemical formula 1 above,

R3 to R9, R20 to R27 and R30 to R37 are the same as or different from each other and are each independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted arylamine group; or a substituted or unsubstituted siloxane group,

n3 to n6, n20 to n27 and n30 to n37 are each an integer of 1 to 4, n7 to n9 are each an integer of 1 to 6, and when n3 to n9, n20 to n27 and n30 to n37 are each 2 or more, the substituents in each parenthesis are the same or different,

p1 to p4 are each an integer from 1 to 3, and when p1 to p4 are each 2 or greater, the structures in each parenthesis are the same or different from each other.

* is an attachment point within the polymer.

In one embodiment of the present specification, each of p1 to p4 is 1 or 2.

In one embodiment of the present specification, p1 and p2 are 2.

In one embodiment of the present specification, p3 and p4 are 1 or 2.

In one embodiment of the present specification, R10 and R11 are the same as or different from each other, and each independently represent a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted arylamine group having 6 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

In one embodiment of the present specification, R10 and R11 are the same as or different from each other, and each independently represents a substituted or unsubstituted arylamine group; or a substituted or unsubstituted aryl group.

In one embodiment of the present specification, R10 and R11 are the same as or different from each other, and each independently represent an arylamine group; or an aryl group unsubstituted or substituted with an alkyl group.

In one embodiment of the present specification, R10 and R11 are the same as or different from each other, and each independently represent an arylamine group; a phenyl group unsubstituted or substituted with an alkyl group; a biphenyl group unsubstituted or substituted with an alkyl group; or a naphthyl group unsubstituted or substituted with an alkyl group.

In one embodiment of the present specification, R10 and R11 are the same as or different from each other, and each independently represent an arylamine group; or a phenyl group substituted or unsubstituted with an alkyl group.

In one embodiment of the present specification, the chemical formula 1 is the following chemical formula 1-A or 1-B.

[Chemical Formula 1-A]

[Chemical Formula 1-B]

In the above chemical formulas 1-A and 1-B,

L1 to L4, Ar1, Ar2, R1, R2, n1 and n2 are the same as defined in chemical formula 1,

Rz1 and Rz2 are the same or different from each other, and each independently represents hydrogen; deuterium; or a substituted or unsubstituted alkyl group,

Rz3 to Rz6 are the same or different from each other, and each independently represents hydrogen; deuterium; or a substituted or unsubstituted aryl group,

rz1 and rz2 are integers from 1 to 5, and when rz1 and rz2 are each 2 or greater, the substituents in each parenthesis are the same or different,

* is an attachment point within the polymer.

In one embodiment of the present specification, at least one of Rz3 and Rz4 and at least one of Rz5 and Rz6 is a substituted or unsubstituted aryl group.

In one embodiment of the present specification, Rz3 to Rz6 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group.

In one embodiment of the present specification, the chemical formula 1 is the following chemical formula 1-A-1 or 1-B-1.

[Chemical Formula 1-A-1]

[Chemical Formula 1-B-1]

In the above chemical formulas 1-A-1 and 1-B-1,

L1 to L4, R1, R2, Ar1, Ar2, n1 and n2 are the same as defined in chemical formula 1,

Rp1 and Rq1 are the same or different and each independently represents a substituted or unsubstituted alkyl group,

Rp2 to Rp4 and Rq2 to Rq4 are the same or different from each other, and each independently represents hydrogen; deuterium; or a substituted or unsubstituted alkyl group,

rp2 and rq2 are each an integer from 1 to 4, rp3, rp4, rq3 and rq4 are each an integer from 1 to 5, and when rp2, rp3, rp4, rq2, rq3 and rq4 are each 2 or greater, the substituents in each parenthesis are the same or different,

* is an attachment point within the polymer.

In one embodiment of the present specification, at least one of the first unit and the second unit is the chemical formula 1-A-1.

In one embodiment of the present specification, the chemical formula 1 is the following chemical formula 1-A1.

[Chemical Formula 1-A1]

In the above chemical formula 1-A1,

L1 to L4, R1, R2, Ar1, Ar2, n1 and n2 are the same as defined in chemical formula 1,

Rx1 to Rx3 and Ry1 to Ry3 are the same or different from each other, and each independently represents hydrogen; deuterium; or a substituted or unsubstituted alkyl group,

At least one of Rx1 to Rx3 and at least one of Ry1 to Ry3 is a substituted or unsubstituted alkyl group,

* is an attachment point within the polymer.

In one embodiment of the present specification, at least one of the first unit and the second unit is the chemical formula 1-A1.

In one embodiment of the present specification, Rx1 to Rx3 and Ry1 to Ry3 are the same as or different from each other, and each independently represent hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, and at least one of Rx1 to Rx3 and at least one of Ry1 to Ry3 is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

In one embodiment of the present specification, Rx1 to Rx3 and Ry1 to Ry3 are the same as or different from each other, and each independently represent hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and at least one of Rx1 to Rx3 and at least one of Ry1 to Ry3 is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

In one embodiment of the present specification, Rx1 to Rx3 and Ry1 to Ry3 are the same as or different from each other, and are each independently hydrogen; deuterium; a straight-chain alkyl group having 1 to 10 carbon atoms; or a branched-chain alkyl group having 4 to 10 carbon atoms. At least one of Rx1 to Rx3 and at least one of Ry1 to Ry3 is a straight-chain alkyl group having 1 to 10 carbon atoms; or a branched-chain alkyl group having 4 to 10 carbon atoms.

In one embodiment of the present specification, Rx1 to Rx3 and Ry1 to Ry3 are the same as or different from each other, and are each independently hydrogen; deuterium; a methyl group; an ethyl group; a propyl group; an n-butyl group; a sec-butyl group; an isobutyl group; or a tert-butyl group, and at least one of Rx1 to Rx3 and at least one of Ry1 to Ry3 is a methyl group; an ethyl group; a propyl group; an n-butyl group; a sec-butyl group; an isobutyl group; or a tert-butyl group.

In one embodiment of the present specification, at least one of Rx1 to Rx3 and at least one of Ry1 to Ry3 is a methyl group; a sec-butyl group; an isobutyl group; or a tert-butyl group.

In one embodiment of the present specification, at least one of Rx1 to Rx3 and at least one of Ry1 to Ry3 is a sec-butyl group; an isobutyl group; or a tert-butyl group.

In one embodiment of the present specification, Rx2 and Ry2 are the same as or different from each other, and each independently represent a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

In one embodiment of the present specification, Rx2 and Ry2 are the same as or different from each other, and each independently represent a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

In one embodiment of the present specification, Rx2 and Ry2 are the same as or different from each other, and each independently represents a substituted or unsubstituted straight-chain alkyl group having 1 to 30 carbon atoms or a substituted or unsubstituted branched-chain alkyl group having 4 to 30 carbon atoms.

In one embodiment of the present specification, Rx2 and Ry2 are the same as or different from each other, and each independently represents a substituted or unsubstituted straight-chain alkyl group having 1 to 10 carbon atoms or a substituted or unsubstituted branched-chain alkyl group having 4 to 10 carbon atoms.

In one embodiment of the present specification, Rx2 and Ry2 are the same as or different from each other, and each independently represents a straight-chain alkyl group having 1 to 10 carbon atoms or a branched-chain alkyl group having 4 to 10 carbon atoms.

In one embodiment of the present specification, Rx2 and Ry2 are the same as or different from each other, and each independently represent a substituted or unsubstituted branched-chain alkyl group having 4 to 30 carbon atoms.

In one embodiment of the present specification, Rx2 and Ry2 are the same as or different from each other, and each independently represent hydrogen; deuterium; a methyl group; an ethyl group; a propyl group; an n-butyl group; a sec-butyl group; an isobutyl group; or a tert-butyl group.

In one embodiment of the present specification, Rx2 and Ry2 are the same as or different from each other, and each independently represents a methyl group; an ethyl group; a propyl group; an n-butyl group; a sec-butyl group; an isobutyl group; or a tert-butyl group.

In one embodiment of the present specification, Rx2 and Ry2 are the same as or different from each other, and each independently represents a methyl group; a sec-butyl group; an isobutyl group; or a tert-butyl group.

In one embodiment of the present specification, Rx2 and Ry2 are the same as or different from each other, and each independently represents a sec-butyl group; an isobutyl group; or a tert-butyl group.

In one embodiment of the present specification, L1 of the chemical formula 1-A1 is a direct bond, and L2 is a substituted or unsubstituted phenylene group.

In one embodiment of the present specification, the chemical formula 1-A is any one of the following chemical formulas 1-A2 to 1-A4.

[Chemical Formula 1-A2]

[Chemical Formula 1-A3]

[Chemical Formula 1-A4]

In the above chemical formulas 1-A2 to 1-A4,

L3, L4, Ar1 and Ar2 are the same as defined in chemical formula 1,

R1 to R3, Rx1, Rx3, Ry1 and Ry3 are the same or different from each other, and each independently represents hydrogen; deuterium; or a substituted or unsubstituted alkyl group,

n1 to n3 are each an integer from 1 to 4, and when n1 to n3 are each 2 or greater, the substituents in each parenthesis are the same or different,

* is an attachment point within the polymer.

In one embodiment of the present specification, at least one of the first unit and the second unit is chemical formula 1-A2, 1-A3 or 1-A4.

In one embodiment of the present specification, the chemical formula 1 is any one of the following chemical formulas 1-A-11 to 1-A-14 and 1-B-11 to 1-B-14.

[Chemical Formula 1-A-11]

[Chemical Formula 1-A-12]

[Chemical Formula 1-A-13]

[Chemical Formula 1-A-14]

[Chemical Formula 1-B-11]

[Chemical Formula 1-B-12]

[Chemical Formula 1-B-13]

[Chemical Formula 1-B-14]

In the above chemical formulas 1-A-11 to 1-A-14 and 1-B-11 to 1-B-14,

R1, R2, n1 and n2 are the same as defined in the chemical formula 1 above,

R3 to R9, R20 to R27 and R30 to R37 are the same as or different from each other and are each independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted arylamine group; or a substituted or unsubstituted siloxane group,

Rx4 to Rx6, Ry4 to Ry6, Rp3, Rp4, Rq3 and Rq4 are the same or different from each other, and each independently represents hydrogen; deuterium; or a substituted or unsubstituted alkyl group,

n3 to n6, n20 to n27 and n30 to n37 are each an integer of 1 to 4, n7 to n9 are each an integer of 1 to 6, and when n3 to n9, n20 to n27 and n30 to n37 are each 2 or more, the substituents in each parenthesis are the same or different,

p1 to p4 are each an integer from 1 to 3, and when p1 to p4 are each 2 or greater, the structures in each parenthesis are the same or different from each other.

rp3, rp4, rq3 and rq4 are each an integer from 1 to 5, and when rp3, rp4, rq3 and rq4 are each 2 or greater, the substituents in each parenthesis are the same or different,

* is an attachment point within the polymer.

In one embodiment of the present specification, the first unit and the second unit are different from each other and are each one of the chemical formulas 1-A-11 to 1-A-14 and 1-B-11 to 1-B-14.

In one embodiment of the present specification, at least one of the first unit and the second unit is the chemical formula 1-A-11.

In one embodiment of the present specification, R20 to R27 are the same as or different from each other, and each independently represent hydrogen; deuterium; a halogen group; or a substituted or unsubstituted alkyl group.

In one embodiment of the present specification, R20 to R27 are the same as or different from each other, and each independently represent hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

In one embodiment of the present specification, R20 to R27 are the same as or different from each other, and are each independently hydrogen or deuterium.

In one embodiment of the present specification, R30 to R37 are the same as or different from each other, and each independently represents hydrogen; deuterium; a halogen group; or a substituted or unsubstituted alkyl group.

In one embodiment of the present specification, R30 to R37 are the same as or different from each other, and each independently represent hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

In one embodiment of the present specification, R30 to R37 are the same as or different from each other, and are each independently hydrogen or deuterium.

In one embodiment of the present specification, Rx4 to Rx6 and Ry4 to Ry6 are the same as or different from each other, and each independently represent hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

In one embodiment of the present specification, Rx4 to Rx6 and Ry4 to Ry6 are the same as or different from each other, and each independently represents hydrogen; deuterium; a substituted or unsubstituted straight-chain alkyl group having 1 to 30 carbon atoms; or a substituted or unsubstituted branched-chain alkyl group having 4 to 30 carbon atoms.

In one embodiment of the present specification, at least one of Rx4 to Rx6 and at least one of Ry4 to Ry6 is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

In one embodiment of the present specification, Rx4 to Rx6 and Ry4 to Ry6 are the same as or different from each other, and are each independently hydrogen; deuterium; a straight-chain alkyl group having 1 to 30 carbon atoms; or a branched-chain alkyl group having 4 to 30 carbon atoms.

In one embodiment of the present specification, Rx4 to Rx6 and Ry4 to Ry6 are the same as or different from each other, and are each independently hydrogen; deuterium; a straight-chain alkyl group having 1 to 10 carbon atoms; or a branched-chain alkyl group having 4 to 10 carbon atoms.

In one embodiment of the present specification, at least one of Rx4 to Rx6 and at least one of Ry4 to Ry6 is a straight-chain alkyl group having 1 to 10 carbon atoms; or a branched-chain alkyl group having 4 to 10 carbon atoms.

In one embodiment of the present specification, at least one of Rx4 to Rx6 and at least one of Ry4 to Ry6 is a branched-chain alkyl group having 4 to 10 carbon atoms.

In one embodiment of the present specification, any one of Rx4 to Rx6 and any one of Ry4 to Ry6 is a straight-chain alkyl group having 1 to 30 carbon atoms; or a branched-chain alkyl group having 4 to 30 carbon atoms.

In one embodiment of the present specification, any one of Rx4 to Rx6 and any one of Ry4 to Ry6 is a branched-chain alkyl group having 4 to 30 carbon atoms.

In one embodiment of the present specification, Rx4 to Rx6 and Ry4 to Ry6 are the same as or different from each other, and are each independently hydrogen; deuterium; a methyl group; an ethyl group; a propyl group; an n-butyl group; a sec-butyl group; an isobutyl group; or a tert-butyl group.

In one embodiment of the present specification, at least one of Rx4 to Rx6 and at least one of Ry4 to Ry6 is a methyl group; a sec-butyl group; an isobutyl group; or a tert-butyl group.

In one embodiment of the present specification, at least one of Rx4 to Rx6 and at least one of Ry4 to Ry6 is a sec-butyl group; an isobutyl group; or a tert-butyl group.

In one embodiment of the present specification, Rx5 and Ry5 are the same as or different from each other, and each independently is an alkyl group having 1 to 30 carbon atoms.

In one embodiment of the present specification, Rx5 and Ry5 are the same as or different from each other, and each independently is a branched-chain alkyl group having 4 to 30 carbon atoms.

In one embodiment of the present specification, Rx5 and Ry5 are the same as or different from each other, and each independently represents a methyl group; a sec-butyl group; an isobutyl group; or a tert-butyl group.

In one embodiment of the present specification, Rx5 and Ry5 are the same as or different from each other, and each independently represents a sec-butyl group; an isobutyl group; or a tert-butyl group.

In one embodiment of the present specification, Rp3, Rp4, Rq3 and Rq4 are the same as or different from each other, and each independently represents hydrogen; deuterium; a halogen group; or a substituted or unsubstituted alkyl group.

In one embodiment of the present specification, Rp3, Rp4, Rq3 and Rq4 are the same as or different from each other, and are each independently hydrogen or deuterium.

In one embodiment of the present specification, at least one of R1 to R3 is a substituted or unsubstituted alkyl group.

In one embodiment of the present specification, one of R1 to R3 is a substituted or unsubstituted alkyl group.

In one embodiment of the present specification, two of R1 to R3 are substituted or unsubstituted alkyl groups.

In one embodiment of the present specification, all of R1 to R3 are substituted or unsubstituted alkyl groups.

In one embodiment of the present specification, at least one of R1, R2, R4 and R5 is a substituted or unsubstituted alkyl group.

In one embodiment of the present specification, one of R1, R2, R4 and R5 is a substituted or unsubstituted alkyl group.

In one embodiment of the present specification, two of R1, R2, R4 and R5 are substituted or unsubstituted alkyl groups.

In one embodiment of the present specification, R1, R2, R4 and R5 are all substituted or unsubstituted alkyl groups.

In one embodiment of the present specification, at least one of R1, R2, R6 and R7 is a substituted or unsubstituted alkyl group.

In one embodiment of the present specification, one of R1, R2, R6 and R7 is a substituted or unsubstituted alkyl group.

In one embodiment of the present specification, two of R1, R2, R6 and R7 are substituted or unsubstituted alkyl groups.

In one embodiment of the present specification, R1, R2, R6 and R7 are all substituted or unsubstituted alkyl groups.

In one embodiment of the present specification, at least one of R1, R2, R8 and R9 is a substituted or unsubstituted alkyl group.

In one embodiment of the present specification, one of R1, R2, R8 and R9 is a substituted or unsubstituted alkyl group.

In one embodiment of the present specification, two of R1, R2, R8 and R9 are substituted or unsubstituted alkyl groups.

In one embodiment of the present specification, R1, R2, R8 and R9 are all substituted or unsubstituted alkyl groups.

In one embodiment of the present specification, R1 to R9 are the same as or different from each other, and each independently represent hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

In one embodiment of the present specification, at least one of R1, R2, R8 and R9 is an alkyl group.

In one embodiment of the present specification, at least one of R1, R2, R8 and R9 is an alkyl group having 1 to 10 carbon atoms.

In one embodiment of the present specification, R1 to R9 are the same as or different from each other, and each independently represent hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and at least one of R1 to R9 is an alkyl group having 1 to 10 carbon atoms.

In one embodiment of the present specification, the chemical formula 1 is the following chemical formula 1-31 or the following chemical formula 1-32.

[Chemical Formula 1-31]

[Chemical Formula 1-32]

In the above chemical formulas 1-31 and 1-32,

R1, R2, R10, R11, Ar1, Ar2, L3, L4, n1 and n2 are the same as defined in the chemical formula 1 above,

R3, R3', R8 and R9 are the same as or different from each other, and each independently represents hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted arylamine group; or a substituted or unsubstituted siloxane group,

* is an attachment point within the polymer.

In one embodiment of the present specification, the chemical formula 1 is the chemical formula 1-31 or the following chemical formula 1-33.

[Chemical Formula 1-33]

In the above chemical formula 1-33,

R10, R11, Ar1, Ar2, L3 and L4 are the same as defined in the above chemical formula 1,

R8 and R9 are the same as or different from each other, and each independently represents hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted arylamine group; or a substituted or unsubstituted siloxane group,

* is an attachment point within the polymer.

In one embodiment of the present specification, the chemical formula 1 is the following chemical formula 1-34 or the following chemical formula 1-35.

[Chemical Formula 1-34]

[Chemical Formula 1-35]

In the above chemical formulas 1-34 and 1-35,

R1, R2, R10, R11, n1 and n2 are the same as defined in the chemical formula 1 above,

R3, R3', R8, R9, R20, R21, R26, R27, R30, R31, R36 and R37 are the same as or different from each other, and each independently represents hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted arylamine group; or a substituted or unsubstituted siloxane group,

n20, n21, n26, n27, n30, n31, n36 and n37 are each an integer from 1 to 4, and when n20, n21, n26, n27, n30, n31, n36 and n37 are each 2 or greater, the substituents in each parenthesis are the same or different,

p1 to p4 are each an integer from 1 to 3, and when p1 to p4 are each 2 or greater, the structures in each parenthesis are the same or different from each other.

* is an attachment point within the polymer.

In one embodiment of the present specification, the chemical formula 1 is the chemical formula 1-34 or the following chemical formula 1-36.

[Chemical Formula 1-36]

In the above chemical formula 1-36,

R10 and R11 are the same as defined in the above chemical formula 1,

R8, R9, R26, R27, R36 and R37 are the same as or different from each other and are each independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted arylamine group; or a substituted or unsubstituted siloxane group,

n26, n27, n36 and n37 are each an integer from 1 to 4, and when n26, n27, n36 and n37 are each 2 or greater, the substituents in each parenthesis are the same or different,

p1 to p4 are each an integer from 1 to 3, and when p1 to p4 are each 2 or greater, the structures in each parenthesis are the same or different from each other.

* is an attachment point within the polymer.

In one embodiment of the present specification, R1, R2, R3, R3', R8 and R9 are the same as or different from each other, and each independently represents a substituted or unsubstituted alkyl group.

In one embodiment of the present specification, R1, R2, R3, R3', R8 and R9 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

In one embodiment of the present specification, R1, R2, R3, R3', R8 and R9 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

In one embodiment of the present specification, R1, R2, R3, R3', R8 and R9 are the same as or different from each other, and each independently is a straight-chain alkyl group having 1 to 30 carbon atoms.

In one embodiment of the present specification, R1, R2, R3, R3', R8 and R9 are the same as or different from each other, and each independently represents a substituted or unsubstituted straight-chain alkyl group having 1 to 10 carbon atoms.

In one embodiment of the present specification, R1, R2, R3, R3', R8 and R9 are the same as or different from each other, and each independently represents a methyl group; a hexyl group; or an octyl group.

In one embodiment of the present specification, R1 and R2 are each a methyl group.

In one embodiment of the present specification, R3 and R3' are each a hexyl group or an octyl group.

In one embodiment of the present specification, R8 and R9 are each a hexyl group or an octyl group.

In one embodiment of the present specification, the first unit and the second unit are different from each other and each has one of the following structures.

In the above structure, * represents an attachment point within the polymer.

In one embodiment of the present specification, hydrogen can be replaced with deuterium. For example, hydrogen included in the structure can be replaced with deuterium.

Below, the third unit is described.

In one embodiment of the present specification, the third unit is a unit having three or four attachment points.

In one embodiment of the present specification, Y is a direct bond; or a substituted or unsubstituted arylene group.

In one embodiment of the present specification, Y is a direct bond; or a substituted or unsubstituted phenylene group.

In one embodiment of the present specification, the chemical formula 2 is any one of the following chemical formulas 2-1 to 2-4.

[Chemical Formula 2-1]

[Chemical Formula 2-2]

[Chemical Formula 2-3]

[Chemical Formula 2-4]

In the above chemical formulas 2-1 to 2-4,

Z1 is CRa; SiRa; N; or a trivalent substituted or unsubstituted aryl group,

Z2 and Z3 are the same or different, and each independently represents C; Si; or a tetravalent substituted or unsubstituted aryl group,

L10 is a direct bond; or a substituted or unsubstituted arylene group,

Ra is hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group,

R50 to R60 are the same as or different from each other, and each independently represents hydrogen; deuterium; a halogen group; a cyano group; an alkoxy group; an aryloxy group; a siloxane group; a substituted or unsubstituted amine group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; or a crosslinking group, and adjacent groups may be bonded to each other to form a ring,

r50 to r59 are each an integer from 1 to 4, r60 is an integer from 1 to 5, and when r50 to r60 are each 2 or greater, the substituents in each parenthesis are the same or different,

* is an attachment point within the polymer.

In one embodiment of the present specification, the chemical formula 2 is the chemical formula 2-1.

In one embodiment of the present specification, when Z1 is CRa or SiRa and Ra is a substituted or unsubstituted aryl group, L10 is a substituted or unsubstituted arylene group.

In one embodiment of the present specification, Z1 is CH; SiH; N; or a substituted or unsubstituted trivalent aryl group.

In one embodiment of the present specification, Z1 is CH; SiH; N; or a substituted or unsubstituted trivalent phenyl group.

In one embodiment of the present specification, Z1 is N; or a trivalent phenyl group.

In one embodiment of the present specification, L10 is a direct bond; or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

In one embodiment of the present specification, L10 is a direct bond; or an arylene group having 6 to 30 carbon atoms.

In one embodiment of the present specification, L10 is a direct bond; or a phenylene group.

In one embodiment of the present specification, L10 is a direct bond.

In one embodiment of the present specification, the chemical formula 2 is the chemical formula 2-2.

In one embodiment of the present specification, Z2 is C; or Si.

In one embodiment of the present specification, the chemical formula 2 is the chemical formula 2-3.

In one embodiment of the present specification, Z3 is C; or Si.

In one embodiment of the present specification, the chemical formula 2 is the chemical formula 2-4.

In one embodiment of the present specification, the chemical formula 2 is one of the following structures.

In the above structure,

R50 to R60, R52' and R61 are the same as or different from each other, and each independently represents hydrogen; deuterium; a halogen group; a cyano group; an alkoxy group; an aryloxy group; a fluoroalkoxy group; a siloxane group; a substituted or unsubstituted amine group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; or a crosslinkable group, and adjacent groups may be bonded to each other to form a ring,

r50 to r59 and r52' are each an integer from 1 to 4, r60 is an integer from 1 to 5, r6 is an integer from 1 to 3, and when r50 to r61 and r52' are each 2 or more, the substituents in each parenthesis are the same or different,

* is an attachment point within the polymer.

In one embodiment of the present specification, R50 to R61 and R52' are each hydrogen; or deuterium.

Specifically, the chemical formula 2 is one of the following structures.

In the above structure, * represents an attachment point within the polymer.

More specifically, the chemical formula 2 is one of the following structures.

In the above structure, * represents an attachment point within the polymer.

More specifically, the chemical formula 2 is one of the following structures.

In the above structure, * represents an attachment point within the polymer.

Below, the terminal section is described.

In one embodiment of the present specification, E is an end-capping unit of a polymer.

In one embodiment of the present specification, E is a unit having only one attachment point.

In one embodiment of the present specification, E is a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a cross-linking group; or a combination thereof.

In one embodiment of the present specification, E is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; a cross-linking group; or a combination thereof.

In one embodiment of the present specification, E is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a cross-linking group; or a combination thereof.

In one embodiment of the present specification, E is a cross-linking group; or one of the following structures.

In the above structure,

R70 to R72 are the same as or different from each other, and each independently represents hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; or a cross-linking group,

L70 is a direct bond; a substituted or unsubstituted alkylene group; or a substituted or unsubstituted arylene group,

i1 is an integer from 1 to 10, and if i1 is 2 or greater, L70 of 2 or greater are equal to or different from each other,

n70 and n72 are each an integer from 1 to 5, n71 is an integer from 1 to 4, and when n70 to n72 are each 2 or greater, the substituents in each parenthesis are the same or different,

* is an attachment point within the polymer.

In one embodiment of the present specification, E is any one of the following structures.

In the above structure,

R70 to R72, L70, i1, n70 to n72 and * are as described above.

In one embodiment of the present specification, R70 to R72 are the same as or different from each other, and each independently represent hydrogen; deuterium; an alkyl group having 1 to 10 carbon atoms; or a cross-linking group.

In one embodiment of the present specification, L70 is a direct bond; an alkylene group having 1 to 10 carbon atoms; or an arylene group having 6 to 30 carbon atoms.

In one embodiment of the present specification, E is any one of the following structures.

In the above structure, * represents an attachment point within the polymer.

More specifically, the E is one of the following structures.

In the above structure, * represents an attachment point within the polymer.

Below, the polymer is described.

In one embodiment of the present specification, the polymer is represented by the following chemical formula 4.

[Chemical Formula 4]

In the above chemical formula 4,

A1 is the first unit represented by the chemical formula 1 above,

B1 is represented by the chemical formula 1 above and is a second unit different from the first unit,

C1 is the third unit represented by the chemical formula 2 above,

E1 and E2 are the same or different from each other, and each independently represents a terminal group represented by the chemical formula 3,

a, b, and c are mole fractions, respectively, where a is a real number 0<a<1, b is a real number 0<b<1, c is a real number 0<c<1, and a+b+c is 1.

In one embodiment of the present specification, a, b and c are determined according to the equivalent ratio of monomers used in the production of the polymer.

In one embodiment of the present specification, a is a real number greater than or equal to 0.05 and less than 1.

In one embodiment of the present specification, a is a real number greater than or equal to 0.1 and less than 1.

In one embodiment of the present specification, a is a real number from 0.1 to 0.9.

In one embodiment of the present specification, a is a real number from 0.1 to 0.8.

In one embodiment of the present specification, a is a real number from 0.2 to 0.9.

In one embodiment of the present specification, a is a real number from 0.2 to 0.8.

In one embodiment of the present specification, b is a real number greater than or equal to 0.05 and less than 1.

In one embodiment of the present specification, b is a real number greater than or equal to 0.1 and less than 1.

In one embodiment of the present specification, b is a real number from 0.1 to 0.9.

In one embodiment of the present specification, b is a real number from 0.1 to 0.8.

In one embodiment of the present specification, b is a real number from 0.2 to 0.9.

In one embodiment of the present specification, b is a real number from 0.2 to 0.8.

In one embodiment of the present specification, c is a real number greater than 0 and less than 1.

In one embodiment of the present specification, c is a real number greater than 0 and less than or equal to 0.9.

In one embodiment of the present specification, c is a real number from 0.1 to 0.8.

In one embodiment of the present specification, a is a real number greater than or equal to 0.05 and less than 1, b is a real number greater than or equal to 0.05 and less than 1, and c is a real number greater than 0 and less than or equal to 0.9.

In one embodiment of the present specification, a is a real number from 0.1 to 0.8, b is a real number from 0.1 to 0.8, and c is a real number from 0.1 to 0.8.

In this specification, the above a, b, and c are mole fractions based on the sum of A1, B1, and C1, not the mole fraction of the entire polymer represented by chemical formula 1 including E1 and E2.

In one embodiment of the present specification, the molar ratio of (A1+B1+C1):(E1+E2) is 40:60 to 98:2.

In one embodiment of the present specification, the polymer is an alternating polymer, a block polymer or a random polymer.

In one embodiment of the present specification, the chemical formula 4 does not only mean that A1, B1, and C1 are in that order within the polymer. Specifically, A1, B1, and C1 may be in various orders within the polymer. For example, the polymer may be in the order of E1-A1-B1-C1-E2, E1-A1-C1-B1-E2, E1-B1-A1-C1-E2, E1-B1-C1-A1-E2, E1-C1-A1-B1-E2, or E1-C1-B1-A1-E2.

In addition, the chemical formula 4 is not a structure in which only one of A1, B1, and C1 is connected within the polymer. For example, the polymer may be connected in various content ranges within the polymer, such as E1-A1-B1-A1-C1-E2, E1-A1-C1-B1-C1-E2, E1-A1-B1-C1-A1-E2, etc. In this case, the content range of A1, B1, and C1 is determined according to the equivalent ratio of the monomers used in the production of the polymer.

In one embodiment of the present specification, the weight average molecular weight (Mw) of the polymer is 10,000 g/mol to 3,000,000 g/mol. Specifically, the weight average molecular weight (Mw) of the polymer is 10,000 g/mol to 1,000,000 g/mol. More specifically, the weight average molecular weight (Mw) of the polymer is 10,000 g/mol to 300,000 g/mol.

In one embodiment of the present specification, the number average molecular weight (Mw) of the polymer is 5,000 g/mol to 3,000,000 g/mol. Specifically, the weight average molecular weight (Mw) of the polymer is 5,000 g/mol to 1,000,000 g/mol. More specifically, the weight average molecular weight (Mw) of the polymer is 10,000 g/mol to 300,000 g/mol.

The above molecular weight can be measured as a relative value to a standard PS (standard polystyrene) sample through GPC (Gel Permeation Chromatography, waters breeze) using THF (tetrahydrofuran) as an eluent, and specifically, it is a value obtained by applying the polystyrene-converted weight-average molecular weight (Mw) and number-average molecular weight (Mw) obtained by gel permeation chromatography (GPC: gel permeation chromatography, PLgel HFIPGEL, Agilent Technologies).

Specifically, the polymer to be measured is dissolved in tetrahydrofuran at a concentration of 1%, 10 ㎕ is injected into the GPC at a flow rate of 0.3 mL/min, and analysis can be performed at 30°C for a sample concentration of 2.0 mg/mL (100 ㎕ injection). Here, two PLgel HFIPGEL columns from Waters are connected in series, and an RI detector (Agilent Waters product, 2414) is used as the detector, and measurement is performed at 40°C, and then the data can be processed using ChemStation.

When the weight average molecular weight of the polymer satisfies the above range, the viscosity is appropriate, which facilitates the production of inkjet devices and organic light-emitting devices using fine pixels.

In one embodiment of the present specification, the molecular weight distribution (PDI) of the polymer is 1 to 10. Specifically, the molecular weight of the polymer is 1 to 8.

In one embodiment of the present specification, in a polymer, a first unit represented by the chemical formula 1; a second unit represented by the chemical formula 1 and different from the first unit; a third unit represented by the chemical formula 2; and a terminal group represented by the chemical formula 3 can be distributed so as to optimize the properties of the polymer.

In one embodiment of the present specification, when the mole fraction of the first unit represented by chemical formula 1 in the polymer is a1, the mole fraction of the second unit represented by chemical formula 1 and different from the first unit is b1, the mole fraction of the third unit represented by chemical formula 2 is c1, and the mole fraction of the terminal group represented by chemical formula 3 is e1, a1, b1, c1, and e1 are each real numbers, and 0<a1<1, 0<b1<1, 0<c1<1, 0<e1<1, and a1+b1+c1+e1=1.

In one embodiment of the present specification, a1, b1, c1 and e1 are each real numbers, 0<a1<1, 0<b1<1, 0<c1<1, 0<e1<1, and a1+b1+c1+e1=1.

In one embodiment of the present specification, a1 is a real number greater than or equal to 0.05 and less than 1.

In one embodiment of the present specification, a1 is a real number from 0.05 to 0.95.

In one embodiment of the present specification, a1 is a real number from 0.1 to 0.9.

In one embodiment of the present specification, a1 is a real number from 0.05 to 0.8.

In one embodiment of the present specification, a1 is a real number from 0.1 to 0.8.

In one embodiment of the present specification, b1 is a real number greater than or equal to 0.05 and less than 1.

In one embodiment of the present specification, b1 is a real number between 0.05 and 0.95.

In one embodiment of the present specification, b1 is a real number from 0.1 to 0.9.

In one embodiment of the present specification, b1 is a real number between 0.05 and 0.8.

In one embodiment of the present specification, b1 is a real number from 0.1 to 0.8.

In one embodiment of the present specification, c1 is a real number greater than or equal to 0 and less than 1.

In one embodiment of the present specification, c1 is a real number greater than or equal to 0.05 and less than 1.

In one embodiment of the present specification, c1 is a real number from 0.1 to 0.9.

In one embodiment of the present specification, c1 is a real number from 0.1 to 0.8.

In one embodiment of the present specification, e1 is a real number greater than or equal to 0.05 and less than 1.

In one embodiment of the present specification, e1 is a real number from 0.05 to 0.95.

In one embodiment of the present specification, e1 is a real number from 0.1 to 0.9.

In one embodiment of the present specification, e1 is a real number between 0.05 and 0.8.

In one embodiment of the present specification, e1 is a real number from 0.1 to 0.8.

In one embodiment of the present specification, a1 is a real number greater than or equal to 0.05 and less than 1, b1 is a real number greater than or equal to 0.05 and less than 1, c1 is a real number from 0.05 to 0.9, e1 is a real number from 0.05 to 0.95, and a1+b1+c1+e1=1.

In one embodiment of the present specification, a1 is a real number from 0.05 to 0.8, b1 is a real number from 0.05 to 0.8, c1 is a real number from 0.1 to 0.8, e1 is a real number from 0.05 to 0.8, and a1+b1+c1+e1=1.

In one embodiment of the present specification, the polymer has one of the following structures.

In the above structure, a1 is a real number 0<a1<1, b1 is a real number 0<b1<1, c1 is a real number 0<c1<1, e1 is a real number 0<e1<1, and a1+b1+c1+e1 is 1.

Specifically, a1 is a real number greater than or equal to 0.05 and less than 1, b1 is a real number greater than or equal to 0.05 and less than 1, c1 is a real number between 0.05 and 0.9, e1 is a real number between 0.05 and 0.9, and a1+b1+c1+e1=1.

In one embodiment of the present specification, a1 is a real number from 0.05 to 0.8, b1 is a real number from 0.05 to 0.8, c1 is a real number from 0.1 to 0.8, e1 is a real number from 0.05 to 0.8, and a1+b1+c1+e1=1.

In the above structure, a1, b1, c1 and e1 are determined according to the equivalent weight of the monomers introduced during the production of the polymer.

In one embodiment of the present disclosure, the polymer can be produced using a known polymerization technique. For example, production methods such as Suzuki, Yamamoto, Stille, metal-catalyzed C-N coupling reaction and metal-catalyzed arylation reaction can be applied.

In one embodiment of the present disclosure, the polymer can be substituted with deuterium. At this time, the deuterium can be substituted by applying a method using a precursor material. For example, the deuterium can be substituted by treating a non-deuterated monomer and/or polymer with a deuterated solvent in the presence of a Lewis acid H/D exchange catalyst.

In one embodiment of the present specification, the molecular weight of the polymer can be controlled by adjusting the ratio of the monomers used. Additionally, in some embodiments, the molecular weight of the polymer can be controlled using a quenching reaction.

In one embodiment of the present specification, the polymer can be used as a hole transport material. For example, the polymer can be a 'hole transport polymer.'

In one embodiment of the present disclosure, the polymer can be formed into a layer through a solution process. The term 'layer' is used interchangeably with the term 'membrane' or 'film' and refers to a coating covering a desired area. The term is not limited by size. The area can be as large as the entire device, as small as a specific functional area such as an actual visual display, or as small as a single sub-pixel.

In one embodiment of the present disclosure, the layers, membranes and films can be formed by any conventional deposition techniques including vapor deposition, liquid deposition (continuous and discontinuous techniques) and thermal transfer. Continuous deposition techniques include, but are not limited to, spin coating, gravure coating, curtain coating, dip coating, slot-die coating, spray coating, and continuous nozzle coating. Discontinuous deposition techniques include, but are not limited to, inkjet printing, gravure printing and screen printing.

In one embodiment of the present disclosure, the polymer has an intrinsic viscosity of less than 20 cP. This is particularly useful for inkjet printing applications, where the lower viscosity allows for thicker solutions to be jetted. Specifically, the polymer has an intrinsic viscosity of less than 15 cP, more specifically less than 10 cP, and more specifically less than 8 cP.

In one embodiment of the present specification, the intrinsic viscosity of the polymer is 1 cP or more and less than 20 cP, specifically 1 cP to 10 cP, more specifically 1 cP to 8 cP.

The above intrinsic viscosity is a value measured at 25°C using an Ubbelohde viscometer after dissolving the polymer to be measured in a chloroform solvent at a concentration of 0.5 g/dl.

Below, a coating composition containing the above polymer is described.

One embodiment of the present disclosure provides a coating composition comprising the polymer described above.

In one embodiment of the present specification, the coating composition further comprises a solvent. In one embodiment of the present specification, the coating composition comprises the polymer and a solvent.

In one embodiment of the present specification, the coating composition may be in a liquid state. The term "liquid" means in a liquid state at room temperature and pressure.

In one embodiment of the present specification, it is preferable that the solvent does not dissolve the material applied to the lower layer.

In one embodiment of the present specification, when the coating composition is applied to an organic layer of an organic light-emitting device, a solvent that does not dissolve a material of a lower layer is used. For example, when the coating composition is applied to a hole transport layer, a solvent that does not dissolve a material of a lower layer (first electrode, hole injection layer, etc.) is used. Accordingly, there is an advantage in that the hole transport layer can be introduced through a solution process.

In one embodiment of the present specification, the solvent resistance of the coating composition is improved when heat-treated after coating.

For example, even if a coating composition is prepared using a solvent that dissolves the polymer and a layer is prepared by a solution process, it can have resistance to the same solvent after heat treatment.

Therefore, after forming an organic layer using the above polymer and then performing a heat treatment process, a solution process is possible when applying another organic layer.

In one embodiment of the present specification, the solvent included in the coating composition is, for example, a chlorine solvent such as chloroform, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, o-dichlorobenzene; an ether solvent such as tetrahydrofuran, dioxane; an aromatic hydrocarbon solvent such as toluene, xylene, trimethylbenzene, mesitylene; a ketone solvent such as acetone, methyl ethyl ketone, cyclohexanone; an ester solvent such as ethyl acetate, butyl acetate, ethyl cellosolve acetate; a polyhydric alcohol and derivatives thereof such as ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxyethane, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerin, 1,2-hexanediol; Examples of the solvent include alcohol solvents such as methanol, ethanol, propanol, isopropanol, and cyclohexanol; sulfoxide solvents such as dimethyl sulfoxide; amide solvents such as N-methyl-2-pyrrolidone and N,N-dimethylformamide; benzoate solvents such as methyl benzoate, butyl benzoate, and 3-phenoxy benzoate; and tetralin. However, any solvent capable of dissolving or dispersing a polymer according to one embodiment of the present specification is possible, and is not limited thereto.

In one embodiment of the present specification, the solvent may be used alone or as a mixture of two or more solvents.

In one embodiment of the present specification, the boiling point of the solvent is preferably 40°C to 350°C, more preferably 80°C to 330°C, but is not limited thereto.

In one embodiment of the present specification, the concentration of the polymer in the coating composition is preferably 0.1 wt/v% to 20 wt/v%, more preferably 0.5 wt/v% to 10 wt/v%, but is not limited thereto.

In one embodiment of the present specification, the remaining components in the coating composition other than the polymer are solvents.

Below, an organic light-emitting device including the above polymer is described.

One embodiment of the present specification provides an organic light-emitting device including a first electrode; a second electrode; and at least one organic layer provided between the first electrode and the second electrode, wherein at least one of the organic layers includes the polymer.

The organic layer of the organic light-emitting device of the present specification may be formed as a single-layer structure, but may be formed as a multilayer structure in which two or more organic layers are laminated. For example, the organic light-emitting device of the present invention may have a structure including, as organic layers, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, a layer that simultaneously injects holes and transports holes, a layer that simultaneously injects electrons and transports electrons, etc. However, the structure of the organic light-emitting device is not limited thereto, and may include a smaller number of organic layers.

When the organic light-emitting device includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.

In one embodiment of the present specification, the organic light-emitting device includes a first electrode; a second electrode; and a light-emitting layer provided between the first electrode and the second electrode, and further includes a single-layer organic layer between the light-emitting layer and the first electrode, wherein the organic layer includes the polymer.

In one embodiment of the present specification, the organic light-emitting device includes a first electrode; a second electrode; and a light-emitting layer provided between the first electrode and the second electrode, and further includes multiple organic layers between the light-emitting layer and the first electrode, wherein at least one of the organic layers includes the polymer.

In one embodiment of the present specification, the organic layer including the polymer is a hole injection layer, a hole transport layer, or a layer that simultaneously injects holes and transports holes.

In one embodiment of the present specification, the organic light-emitting device includes a first electrode; a second electrode; and a light-emitting layer provided between the first electrode and the second electrode, and further includes at least one layer of a hole injection layer, a hole transport layer, and an electron blocking layer between the light-emitting layer and the first electrode, and at least one layer of the hole injection layer, the hole transport layer, and the electron blocking layer includes the polymer.

In one embodiment of the present specification, the organic light-emitting device includes a first electrode; a second electrode; and a light-emitting layer provided between the first electrode and the second electrode, and includes a hole injection layer and a hole transport layer between the first electrode and the light-emitting layer, and at least one layer of the hole injection layer and the hole transport layer includes the polymer.

In one embodiment of the present specification, the organic light-emitting device has a structure in which a first electrode; a hole injection layer; a hole transport layer; a light-emitting layer; and a second electrode are sequentially provided, and at least one layer of the hole injection layer and the hole transport layer includes the polymer.

In one embodiment of the present specification, the organic light-emitting device has a structure in which a first electrode; a hole injection layer; a hole transport layer; a light-emitting layer; and a second electrode are sequentially laminated, and the hole injection layer or the hole transport layer includes the polymer.

In one embodiment of the present specification, the organic light-emitting device has a structure in which a first electrode; a hole injection layer; a hole transport layer; a light-emitting layer; and a second electrode are sequentially laminated, and the hole transport layer includes the polymer.

In one embodiment of the present specification, an additional organic layer may be further included between the light-emitting layer and the second electrode.

In one embodiment of the present specification, a single-layer organic layer may further be included between the light-emitting layer and the second electrode.

In one embodiment of the present specification, multiple organic layers may be further included between the light-emitting layer and the second electrode. For example, at least one layer of a hole-blocking layer, an electron injection layer, an electron transport layer, and a layer that simultaneously injects and transports electrons may be further included between the light-emitting layer and the second electrode.

In one embodiment of the present specification, the organic light-emitting device has a structure in which a first electrode; a hole injection layer; a hole transport layer; a light-emitting layer; an electron injection and transport layer; and a second electrode are sequentially laminated, and at least one layer of the hole injection layer and the hole transport layer includes the polymer.

In one embodiment of the present specification, the organic light-emitting device has a structure in which a first electrode; a hole injection layer; a hole transport layer; a light-emitting layer; an electron injection and transport layer; and a second electrode are sequentially laminated, and the hole injection layer or the hole transport layer includes the polymer.

In one embodiment of the present specification, the organic light-emitting device has a structure in which a first electrode; a hole injection layer; a hole transport layer; a light-emitting layer; an electron injection and transport layer; and a second electrode are sequentially laminated, and the hole transport layer includes the polymer.

The structure of an organic light-emitting device according to one embodiment of the present specification is illustrated in FIGS. 1 and 2.

Figure 1 illustrates the structure of an organic light-emitting device in which a substrate (1), an anode (2), a light-emitting layer (3), and a cathode (4) are sequentially laminated.

FIG. 2 illustrates the structure of an organic light-emitting device in which a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), a light-emitting layer (3), an electron injection and transport layer (7), and a cathode (4) are sequentially laminated.

The above drawings 1 and 2 are examples of organic light-emitting devices, and the structure of the organic light-emitting device of the present invention is not limited thereto.

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

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

In another embodiment, the organic light-emitting device may be an inverted type organic light-emitting device in which a cathode, one or more organic material layers, and an anode are sequentially laminated on a substrate.

The organic light-emitting device of the present invention can be laminated in a structure as shown in the following example.

(1) Anode/hole transport layer/light emitting layer/cathode

(2) Anode/hole injection layer/hole transport layer/light emitting layer/cathode

(3) Anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/cathode

(4) Anode/hole transport layer/light emitting layer/electron transport layer/cathode

(5) Anode/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode

(6) Anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/cathode

(7) Anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode

(8) Anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/electron transport layer/cathode

(9) Anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode

(10) Anode/hole transport layer/electron suppression layer/light emitting layer/electron transport layer/cathode

(11) Anode/hole transport layer/electron suppression layer/light emitting layer/electron transport layer/electron injection layer/cathode

(12) Anode/hole injection layer/hole transport layer/electron suppression layer/light emitting layer/electron transport layer/cathode

(13) Anode/hole injection layer/hole transport layer/electron suppression layer/light emitting layer/electron transport layer/electron injection layer/cathode

(14) Anode/hole transport layer/light emitting layer/hole suppression layer/electron transport layer/cathode

(15) Anode/hole transport layer/light emitting layer/hole suppression layer/electron transport layer/electron injection layer/cathode

(16) Anode/hole injection layer/hole transport layer/light emitting layer/hole suppression layer/electron transport layer/cathode

(17) Anode/hole injection layer/hole transport layer/light emitting layer/hole suppression layer/electron transport layer/electron injection layer/cathode

(18) Anode/hole injection layer/hole transport layer/electron suppression layer/light emitting layer/hole blocking layer/electron injection layer and transport layer/cathode

In the above structure, “electron transport layer/electron injection layer” can be replaced with “electron injection and transport layer” or “layer that simultaneously performs electron injection and electron transport.”

For example, the organic light-emitting device of the present invention can be laminated in a structure such as 'anode/hole injection layer/hole transport layer/light-emitting layer/electron injection and transport layer/cathode', in which the electron transport layer/electron injection layer of (7) above is replaced with an electron injection and transport layer.

In the above structure, “hole injection layer/hole transport layer” can be replaced with “hole injection and transport layer” or “layer that simultaneously injects holes and transports holes.”

The organic light-emitting device of the present specification can be manufactured using materials and methods known in the art, except that at least one of the organic layers is manufactured to include the polymer. Specifically, the organic light-emitting device can be formed using a coating composition in which at least one of the organic layers includes the polymer.

For example, the organic light-emitting device of the present specification can be manufactured by sequentially stacking an anode, an organic layer, and a cathode on a substrate. At this time, a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation is used to deposit a metal or a conductive metal oxide or an alloy thereof on the substrate to form an anode, and then an organic layer including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron injection and transport layer is formed thereon, and then a material that can be used as a cathode is deposited thereon. In addition to this method, the organic light-emitting device can be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.

The present specification also provides a method for manufacturing an organic light-emitting device formed using the coating composition.

Specifically, in one embodiment of the present specification, the method comprises the steps of: preparing a substrate; forming a first electrode on the substrate; forming one or more organic layers on the first electrode; and forming a second electrode on the organic layers, wherein one or more of the organic layers are formed using the coating composition.

In one embodiment of the present specification, the organic layer formed using the coating composition is formed using spin coating.

In another embodiment, the organic layer formed using the coating composition is formed by a printing method.

In the context of the present specification, the printing method includes, but is not limited to, inkjet printing, nozzle printing, offset printing, transfer printing or screen printing.

A coating composition according to one embodiment of the present specification is suitable for a solution process due to its structural characteristics and can be formed by a printing method, so it has an economical effect in terms of time and cost when manufacturing a device.

In one embodiment of the present specification, the step of forming an organic layer using the coating composition includes the step of coating the coating composition on the first electrode; and the step of heat-treating or light-treating the coated coating composition.

In another embodiment, the heat treatment time in the heat treatment step may be within 1 hour. Specifically, it may be within 30 minutes.

In one embodiment of the present specification, it is preferable that the atmosphere for heat-treating the organic layer formed using the coating composition is an inert gas atmosphere such as argon or nitrogen.

When the organic layer formed using the above coating composition is formed by including a heat treatment or light treatment step, the resistance to solvent increases, so that multiple layers can be formed by repeatedly performing solution deposition and cross-linking methods, and the stability increases, so that the life characteristics of the device can be increased.

In one embodiment of the present specification, other layers than the organic layer formed using the coating composition are formed through spin coating, printing, or a deposition process. For example, when the coating composition is applied to a hole injection layer or a hole transport layer, the hole injection layer or the hole transport layer may be formed by spin coating, and other organic layers may be formed by spin coating, printing, or a deposition process. In addition, an upper layer provided in contact with the organic layer formed using the coating composition may be formed through spin coating. For example, when the coating composition is applied to a hole transport layer, the hole transport layer is formed by spin coating, an emitting layer formed on the hole transport layer so as to be in contact with the hole transport layer is formed by spin coating, and an electron injection and transport layer formed on the emitting layer may be formed by a deposition process.

In one embodiment of the present specification, the anode material is preferably a material having a high work function so that holes can be smoothly injected into the organic layer. Specific examples of the anode material that can be used in the present invention include, but are not limited to, 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 SnO ₂ :Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline.

In one embodiment of the present specification, it is preferable that the cathode material be a material having a small work function so as to facilitate electron injection into the organic layer. Specific examples of the cathode material 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; multilayered materials such as LiF/Al or LiO ₂ /Al.

In one embodiment of the present specification, the hole injection layer is a layer that injects holes from an electrode, and the hole injection material is preferably a compound that has the ability to transport holes, has an excellent hole injection effect for the light-emitting layer or the light-emitting material, prevents movement of excitons generated in the light-emitting layer to the electron injection layer or the electron injection material, and has excellent thin film forming ability. In addition, it is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include, but are not limited to, metal porphyrin, oligothiophene, arylamine-based organic compounds, hexanitrilehexaazatriphenylene-based organic compounds, quinacridone-based organic compounds, perylene-based organic compounds, carbazole-based organic compounds, anthraquinone, and conductive polymers of polyaniline and polythiophene-based compounds. Specifically, the hole injection layer may be, but is not limited to, a carbazole-based compound, an arylamine-based compound, or a compound in which a substituted or unsubstituted carbazole and an arylamine group are linked.

In one embodiment of the present specification, the hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer, and as the hole transport material, a material having high mobility for holes is suitable, which can transport holes from the anode or the hole injection layer and transfer them to the light-emitting layer. In one embodiment of the present specification, the hole transport layer includes the polymer.

In one embodiment of the present specification, the light-emitting layer includes an organic compound. The organic compound is a material that can emit light in the visible light range by transporting holes and electrons from the hole transport layer and the electron transport layer respectively and combining them, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include, but are not limited to, 8-hydroxy-quinoline aluminum complex (Alq ₃ ); carbazole series compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compounds; benzoxazole, benzthiazole, and benzimidazole series compounds; poly(p-phenylenevinylene) (PPV) series polymers; spiro compounds; polyfluorene; rubrene, etc.

In one embodiment of the present specification, the light-emitting layer may include a host material and a dopant material. The host material may include a condensed aromatic ring derivative or a heterocycle-containing compound. For example, the condensed aromatic ring derivative may include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and the heterocycle-containing compounds may include, but are not limited to, carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc. The dopant material may include, but is not limited to, an aromatic amine derivative, a strylamin compound, a boron complex, a compound containing boron, a fluoranthene compound, a metal complex, etc. For example, as an aromatic amine derivative, there are fused aromatic ring derivatives substituted with a substituted or unsubstituted arylamino group, such as fluorene, benzofluorene, pyrene, anthracene, chrysene, periflanthene, etc. substituted with an arylamino group, and as a styrylamine compound, there is a compound in which at least one arylvinyl group is substituted in a substituted or unsubstituted arylamine, and one or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamino group are substituted or unsubstituted. Specifically, the styrylamine compound includes, but is not limited to, styrylamine, styryldiamine, styryltriamine, styryltetraamine, etc. In addition, the metal complex includes, but is not limited to, an iridium complex, a platinum complex, etc.

In one embodiment of the present specification, the host material is an anthracene derivative, and the dopant material is a benzofluorene-based compound substituted with an arylamine group or a compound containing boron. Specifically, the host material is an anthracene derivative unsubstituted or substituted with deuterium, and the dopant material may be a bis(diarylamino)benzofluorene-based compound or a compound containing boron, but is not limited thereto.

In one embodiment of the present specification, the light-emitting layer includes quantum dots. For example, the light-emitting layer may include a matrix resin and quantum dots, and the type and content of the quantum dots may be those known in the art.

When a quantum dot is included in the light-emitting layer, it exhibits a lower HOMO energy level than when an organic compound is included in the light-emitting layer, and therefore the common layer must also exhibit a low HOMO energy level. Since the compound according to one embodiment of the present specification exhibits a low HOMO energy level by including a halogen group, introduction of a quantum dot into the light-emitting layer is possible.

In one embodiment of the present specification, the common layer is a hole injection layer, a hole transport layer, a layer performing hole injection and hole transport simultaneously, an electron injection layer, an electron transport layer, or a layer performing electron injection and electron transport simultaneously.

In one embodiment of the present specification, the electron transport layer is a layer that receives electrons and transports them to the light-emitting layer, and as the electron transport material, a material that can well receive electrons from the cathode and transfer them to the light-emitting layer, and a material with high electron mobility is suitable. Specific examples include, but are not limited to, Al complexes of 8-hydroxyquinoline; complexes containing Alq ₃ ; organic radical compounds; hydroxyflavone-metal complexes. The electron transport layer can be used with any desired cathode material as used according to the prior art. In particular, examples of suitable cathode materials are conventional materials having a low work function and followed by an aluminum layer or a silver layer. Specifically, cesium, barium, calcium, ytterbium, and samarium, in each case followed by an aluminum layer or a silver layer.

In one embodiment of the present specification, the electron injection layer is a layer that injects electrons from an electrode, has the ability to transport electrons, has an excellent electron injection effect for the light-emitting layer or the light-emitting material, prevents movement of excitons generated in the light-emitting layer to the hole injection layer, and is preferably a compound having excellent thin-film forming ability. Specific examples thereof include, but are not limited to, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidene methane, anthrone, bathocuproine (BCP), and the like, derivatives thereof, metal complex compounds, and nitrogen-containing 5-membered ring derivatives.

In one embodiment of the present specification, the metal complex compound is selected from the group consisting of 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h]quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)(o-cresolato)gallium, These include, but are not limited to, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, etc.

In one embodiment of the present specification, 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. Specifically, it includes, but is not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, etc.

In one embodiment of the present specification, a layer adjacent to an organic layer including a polymer represented by the chemical formula 1; or a polymer including a unit represented by the chemical formula 2 and a terminal group represented by the chemical formula 5, for example, a bank layer, includes a compound having fluorine as a substituent.

For example, when the polymer represented by the chemical formula 1 is included in the hole transport layer, at least one of the bank layer, hole injection layer, and light-emitting layer adjacent to the hole transport layer contains fluorine.

When a layer adjacent to an organic layer including a polymer including the first unit, the second unit, the third unit, and a terminal group as described above contains fluorine, the dipole moment changes due to fluorine, so there is an effect of forming a uniform layer.

The organic light-emitting device according to the present specification may be a front-emitting, back-emitting or double-sided emitting type depending on the material used.

Hereinafter, in order to specifically explain this specification, examples will be given and described in detail. However, the examples according to this specification may be modified in various different forms, and the scope of this application is not construed as being limited to the examples described below. The examples of this application are provided to more completely explain this specification to a person having average knowledge in the art.

Synthetic example 1. Preparation of monomer

(1) Preparation of monomer A-2

In a round bottom flask equipped with a condenser, 10.00 g (1.00 eq) of monomer A-1, 14 g (2.00 eq) of bis(pinacolato)diboron, and 1.60 g (3.00 eq) of potassium tert-butoxide were dissolved in 200 mL of toluene. When completely dissolved, 0.20 g (0.04 eq) of [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (Pd(dppf))) was added, and then refluxed at 90°C for 8 hours. After the reaction was terminated with DI water, the organic solvent was extracted with ethyl acetate and distilled water, and monomer A-2 with 99.4% purity was obtained through column chromatography.

(2) Preparation of monomer B-2

Monomer B-2 was prepared in the same manner as (1) of Synthetic Example 1, except that monomer B-1 was used instead of monomer A-1 in (1) of Synthetic Example 1.

(3) Preparation of monomer C-2

Monomer C-2 was prepared in the same manner as (1) of Synthetic Example 1, except that monomer C-1 was used instead of monomer A-1 in (1) of Synthetic Example 1.

(4) Preparation of monomer D-2

Monomer D-2 was prepared in the same manner as (1) of Synthetic Example 1, except that monomer D-1 was used instead of monomer A-1 in (1) of Synthetic Example 1.

Synthetic example 2. Preparation of polymer 1

Monomer A-2 (0.382 mmol), monomer B-2 (0.382 mmol), monomer X-1 (0.158 mmol), and monomer Y-1 (0.369 mmol) were placed in a round bottom flask and dissolved in toluene (11 mL), then tetrakis(triphenylphosphine)palladium(0) (Pd(PPh ₃ ) ₄ ) (0.05 mmol) and 5 mL of a 2M solution of potassium carbonate (K ₂ CO ₃ ) and 0.1 mL of a phase transfer catalyst, Aliquat 336, were injected, and the mixture was refluxed at 100°C for 12 hours. The reactants were slowly added dropwise to methanol to terminate the reaction, stirred for 45 minutes, and the resulting solid was filtered. The dried solid was dissolved in toluene (1% wt/v), and silica gel and a basic The toluene solution was purified by passing it through a column containing aluminum oxide (6 g each). The obtained toluene solution was triturated with acetone to prepare polymer 1 (5.2 g).

Synthetic example 3. Preparation of polymer 2

Polymer 2 was prepared in the same manner as in Synthesis Example 2, except that monomer C-2 was used instead of monomer A-2 in Synthesis Example 2.

Synthetic example 4. Preparation of polymer 3

Polymer 3 was prepared in the same manner as in Synthesis Example 2, except that monomer D-2 was used instead of monomer B-2 in Synthesis Example 2.

Synthetic example 5. Preparation of polymer 4

Polymer 4 was prepared in the same manner as in Synthesis Example 2, except that monomer C-2 was used instead of monomer A-2 and monomer D-2 was used instead of monomer B-2.

Synthetic example 6. Preparation of polymer 5

Polymer 5 was prepared in the same manner as in Synthesis Example 2, except that monomer D-2 was used instead of monomer A-2 in Synthesis Example 2.

Synthetic example 7. Preparation of polymer 6

Under inert gas conditions, monomer A-1 (0.26 mmol), monomer C-1 (0.20 mmol), monomer X-2 (0.24 mmol), Aliquat 336 (0.041 mmol), 1.24 mL of aqueous potassium carbonate solution (0.5 M), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (0.013 mmol) and toluene (6.0 mL) were added to a scintillation vial equipped with a magnetic stir bar. The vial was sealed with a screw cap with a septum, inserted into an aluminum block, heated to an external temperature of 105 °C over a period of 30 min and stirred under reflux at that temperature for 5 h. Monomer Y-2 (0.3 mmol) and toluene (1 mL) were then added. The reaction was heated for an additional 1.5 hours and cooled to room temperature. The aqueous layer was removed and the organic layer was washed twice with 20 mL of deionized water each. The toluene layer was dried by passing it through 10 g of silica gel and the silica was rinsed with toluene. The solvent was removed to obtain 250 mg of the crude product. The toluene solution was passed through alumina, silica gel and Florisil® to further purify the crude product. After concentration, the solvent-soaked product was diluted with toluene to about 14 mL and then added to ethyl acetate (150 mL) to obtain the copolymer. The product toluene solution was reprecipitated in 3-pentanone to prepare polymer 6. (Yield: 70%)

Synthetic example 8. Preparation of polymer 7

Monomer C-1 (0.3 mmol), monomer B-1 (0.2 mmol), monomer X-3 (0.2 mmol), and monomer Y-3 (0.3 mmol) were added to a scintillation vial and dissolved in toluene (10 mL) to prepare a first solution.

A 50 mL Schlenk tube was charged with bis(1,5-cyclooctadiene)nickel(0) (2.1 mmol). 2,2'-Dipyridyl (2.1 mmol) and 1,5-cyclooctadiene (2.1 mmol) were weighed into a scintillation vial and dissolved in N,N'-dimethylformamide (5.5 mL) and toluene (11 mL) to prepare a second solution.

The second solution was poured into the Schlenk tube and stirred at 50°C for 30 minutes. The first solution was further added to the Schlenk tube and stirred at 50°C for 180 minutes. The Schlenk tube was then cooled to room temperature and poured into HCl/methanol (5 % v/v, conc. HCl). After stirring for 45 minutes, the polymer was collected by vacuum filtration and dried under high vacuum. The polymer was dissolved in toluene (1% wt/v) and passed through a column containing basic aluminum oxide (6 g) layered on silica gel (6 g). The polymer/toluene filtrate was concentrated (2.5% wt/v toluene) and triturated with 3-pentanone. The toluene/3-pentanone solution was decanted from the semisolid polymer, dissolved in toluene (15 mL), and then poured into stirred methanol to prepare polymer 7. (Yield: 60%)

Synthetic example 9. Preparation of polymer 8

Polymer 8 was prepared in the same manner as in Synthesis Example 7, except that monomer E-1 was used instead of monomer A-1, monomer A-2 was used instead of monomer C-1, monomer X-4 was used instead of monomer X-2, and monomer Y-1 was used instead of monomer Y-2. (Yield: 55%)

Synthetic example 10. Preparation of polymer 9

Polymer 9 was prepared in the same manner as in Synthesis Example 7, except that monomer F-1 was used instead of monomer A-1, monomer B-1 was used instead of monomer C-1, and monomer Y-4 was used instead of monomer Y-2. (Yield: 60%)

Synthetic example 11. Preparation of polymer 10

Polymer 10 was prepared in the same manner as in Synthesis Example 7, except that monomer B-2 was used instead of monomer A-1, monomer G-2 was used instead of monomer C-1, monomer X-5 was used instead of monomer X-2, and monomer Y-5 was used instead of monomer Y-2. (Yield: 60%)

Synthetic example 12. Preparation of polymer 11

Polymer 11 was prepared in the same manner as in Synthesis Example 8, except that monomer B-3 was used instead of monomer C-1, monomer F-1 was used instead of monomer B-1, monomer X-1 was used instead of monomer X-3, and monomer Y-2 was used instead of monomer Y-3. (Yield: 60%)

Synthetic example 13. Preparation of polymer 12

Polymer 12 was prepared in the same manner as in Synthesis Example 7, except that monomer A-3 was used instead of monomer C-1 and monomer Y-1 was used instead of monomer Y-2. (Yield: 50%)

Synthetic example 14. Preparation of polymer 13

Polymer 13 was prepared in the same manner as in Synthesis Example 8, except that monomer A-4 was used instead of monomer C-1, monomer X-1 was used instead of monomer X-3, and monomer Y-6 was used instead of monomer Y-3. (Yield: 60%)

Synthetic example 15. Preparation of polymer 14

Polymer 14 was prepared in the same manner as in Synthesis Example 8, except that monomer A-1 was used instead of monomer C-1, monomer C-1 was used instead of monomer B-1, monomer X-1 was used instead of monomer X-3, and monomer Y-1 was used instead of monomer Y-3. (Yield: 70%)

comparison Synthetic example 1. Preparation of comparative polymer Q1

Polymer Q1 was prepared in the same manner as in Synthesis Example 2, except that the monomer B-2 was not used in Synthesis Example 2.

comparison Synthetic example 2. Preparation of comparative polymer Q2

Polymer Q2 was prepared in the same manner as in Synthesis Example 2, except that the monomer A-2 was not used in Synthesis Example 2.

comparison Synthetic example 3. Preparation of comparative polymer Q3

Polymer Q3 was prepared in the same manner as in Comparative Synthesis Example 1, except that monomer Y-4 was used instead of monomer Y-1 in Comparative Synthesis Example 1.

comparison Synthetic example 4. Preparation of comparative polymer Q4

Polymer Q4 was prepared in the same manner as in Synthesis Example 8, except that monomer C-1 was not used, monomer F-1 was used instead of monomer B-1, monomer X-4 was used instead of monomer X-3, and monomer Y-2 was used instead of monomer Y-3.

< Example 1> Molecular weight measurement

It was confirmed through molecular weight measurements that polymers 1 to 14 and comparative polymers Q1 to Q4 were synthesized.

Example 1-1.

The number average molecular weight (Mn), weight average molecular weight (Mw), and molecular weight distribution (PDI) of polymer 1 prepared in Synthesis Example 2 were measured using GPC (Agilent, PLgel HFIPGEL column) with THF (tetrahydrofuran).

The molecular weight distribution was calculated using the following equation (1).

Equation (1): PDI = weight average molecular weight (Mw) / number average molecular weight (Mn)

Example 1-2 to 1-14.

Examples 1-2 to 1-4 measured the number average molecular weight (Mn), weight average molecular weight (Mw), and molecular weight distribution (PDI) in the same manner as Example 1-1, except that the polymer of Table 1 below was used instead of polymer 1 in Example 1-1.

Comparative example 1-1 and 1-2

Comparative Examples 1-1 and 1-2 measured the number average molecular weight (Mn), weight average molecular weight (Mw), and molecular weight distribution (PDI) in the same manner as Example 1-1, except that the polymer of Table 2 below was used instead of polymer 1 in Example 1-1.

polymer a1:b1:c1:e1
(Molbi) Mn Mw PDI Example 1-1 1 0.27:0.27:0.18:0.28 32,000 86,000 2.69 Example 1-2 2 0.27:0.27:0.18:0.28 35,000 91,000 2.60 Example 1-3 3 0.29:0.29:0.18:0.24 39,000 126,000 3.23 Example 1-4 4 0.29:0.29:0.19:0.23 38,000 122,000 3.21 Example 1-5 5 0.28:0.28:0.18:0.26 39,000 129,000 3.31 Example 1-6 6 0.26:0.20:0.24:0.30 31,988 150,860 4.72 Example 1-7 7 0.30:0.20:0.20:0.30 29,075 92,422 3.18 Example 1-8 8 0.25:0.25:0.30:0.20 31,151 159,230 5.11 Example 1-9 9 0.25:0.25:0.40:0.10 32,366 157,961 4.88 Example 1-10 10 0.30:0.30:0.30:0.10 28,658 137,076 4.78 Example 1-11 11 0.05:0.75:0.10:0.10 29,991 140,238 4.68 Example 1-12 12 0.30:0.20:0.20:0.30 25,077 87,709 3.50 Example 1-13 13 0.05:0.45:0.30:0.20 29,242 76,642 2.62 Example 1-14 14 0.50:0.15:0.15:0.20 46,978 156,933 3.34

polymer a1:c1:e1
(Molbi) Mn Mw PDI Comparative Example 1-1 Q1 0.56:0.18:0.26 39,000 129,000 3.31 Comparative Example 1-2 Q2 0.54:0.18:0.28 30,000 100,000 3.33 Comparative Example 1-3 Q3 0.60:0.10:0.30 36,213 186,079 5.14 Comparative Example 1-4 Q4 0.50:0.25:0.25 42,667 236,535 5.54

< Example 2> Manufacturing of organic light-emitting devices

Example 2-1.

A glass substrate coated with a 1,500Å thick ITO (indium tin oxide) film was placed in distilled water containing a detergent and ultrasonically cleaned. The detergent used was a Fischer Co. product, and the distilled water used was distilled water that had been filtered twice through a Millipore Co. filter. After washing the ITO for 30 minutes, ultrasonic cleaning was performed twice with distilled water for 10 minutes. After the distilled water washing was complete, ultrasonic cleaning was performed with a solvent of isopropyl alcohol and acetone, and after drying, the substrate was washed for 5 minutes and then dried.

Immediately before the fabrication of the device, the cleaned and patterned ITO was treated with UV ozone for 10 minutes. After the ozone treatment, a 2 wt% cyclohexanone solution containing compound A and the following compound B in a weight ratio of 8:2 was spin-coated on the ITO surface, and the solvent was removed through heat treatment to form a hole injection layer with a thickness of about 40 nm. A toluene solution containing 1.5 wt% of the polymer 1 prepared in Synthesis Example 2 was spin-coated on the hole injection layer formed above, and the solvent was removed through heat treatment to form a hole transport layer with a thickness of about 100 nm. A methyl benzoate solution containing the following compounds C and D (Compound C:Compound D = 93:7 (wt%)) dissolved at a concentration of 2.0 wt% was spin-coated on the hole transport layer to form a light-emitting layer with a thickness of about 100 nm. Thereafter, after transferring to a vacuum deposition machine, BCP was vacuum-deposited on the light-emitting layer to a thickness of 35 nm to form an electron injection and transport layer. LiF was sequentially deposited to a thickness of 1 nm and aluminum to a thickness of 100 nm on the electron injection and transport layer to form a cathode.

In the above process, the deposition rate of lithium fluoride on the cathode was maintained at 0.3 Å/sec, and that of aluminum was maintained at 2 Å/sec, and the vacuum during deposition was maintained at 2 x 10 ^-7 torr to 5 x 10 ^-6 torr.

Example 2-2 to 2-5.

Examples 2-2 to 2-5 produced organic light-emitting devices in the same manner as Example 2-1, except that the polymer in Table 3 below was used instead of polymer 1 in Example 2-1.

Comparative example 2-1 and 2-2.

Comparative Examples 2-1 and 2-2 produced organic light-emitting devices in the same manner as in Example 2-1, except that the polymer in Table 3 below was used instead of polymer 1 in Example 2-1.

The results of performance measurements of the organic light-emitting devices manufactured in Examples 2-1 to 2-5 and Comparative Examples 2-1 and 2-2 at a current density of 10 mA/cm ² are shown in Table 3 below.

hole transport layer V J
(mA/cm ² ) cd/A lm/W QE(%) Cd/m ² CIEx CIEy CE
/CIEy Comparative example
2-1 Polymer Q1 7.81 10.0 1.21 0.49 1.41 121.05 0.150 0.107 11.3 Comparative example
2-2 Polymer Q2 5.45 10.00 5.72 3.30 5.56 572.33 0.106 0.175 32.69 Example
2-1 Polymer 1 5.04 10.00 5.90 3.68 9.90 590.40 0.126 0.076 77.36 Example
2-2 Polymer 2 4.96 10.00 5.66 3.59 10.87 566.40 0.132 0.062 92.10 Example
2-3 Polymer 3 5.16 10.00 5.95 3.62 10.37 595.20 0.128 0.072 83.00 Example
2-4 Polymer 4 5.15 10.00 6.08 3.71 11.08 608.30 0.130 0.067 91.08 Example
2-5 Polymer 5 5.29 10.00 5.48 3.26 11.48 547.90 0.135 0.054 102.50

Unless otherwise specified in the above Table 3, the measurements are at 1000 nit, V is the driving voltage (in volts) at 10 mA/cm ² , the external quantum efficiency (QE) is calculated as (number of emitted photons)/(number of injected charge carriers), cd/A (CE) is the current efficiency, lm/W is the source efficiency, CIEx and CIEy are the x and y coordinates according to the CIE chromaticity diagram (Commission Internationale de L'Eclairage, 1931), and CE/CIEy is the luminous efficacy (cd/A) divided by the chromaticity (y) value.

Through the above Table 3, it can be confirmed that the organic light-emitting devices (Examples 2-1 to 2-5) applying the polymer according to the present invention exhibit higher efficiency than the organic light-emitting devices (Comparative Examples 2-1 and 2-2) applying other polymers. This is because the polymer of the present invention includes first and second units having different charge mobilities, thereby controlling the movement balance of charge/hole.

Example 2-6.

A glass substrate on which ITO was deposited as a thin film with a thickness of 1500Å was ultrasonically cleaned for 10 minutes using acetone solvent. Then, it was placed in distilled water containing detergent and ultrasonically washed for 10 minutes. Then, it was ultrasonically washed twice with distilled water for 10 minutes. After the distilled water washing was finished, it was ultrasonically washed for 10 minutes using isopropyl alcohol solvent and then dried. Then, the substrate was transported to a glove box.

As described above, a 2 wt% cyclohexanone solution containing Compound A and Compound B in a weight ratio of 8:2 was spin-coated onto the prepared ITO transparent electrode, and heat-treated at 230°C for 30 minutes to form a hole injection layer having a thickness of 600 Å. A 0.8 wt% toluene solution containing Polymer 6 in Synthesis Example 7 was spin-coated onto the hole injection layer to form a hole transport layer having a thickness of 1000 Å. On the hole transport layer, Compound C and Compound D in toluene were dissolved in a weight ratio of 9:1, and an emitting layer having a thickness of 550 Å was formed through a solution process. On the emitting layer, Compound E was vacuum-deposited to form an electron injection and transport layer having a thickness of 400 Å. LiF having a thickness of 5 Å and aluminum having a thickness of 1000 Å were sequentially deposited on the electron injection and transport layer to form a cathode.

In the above process, the deposition rate of the organic material was maintained at 0.4Å/sec to 1.0Å/sec, the LiF of the cathode was maintained at 0.3Å/sec, and the aluminum was maintained at 2Å/sec, and the vacuum during deposition was maintained at 2×10 ^-8 torr to 5×10 ^-6 torr.

Example 2-7 to 2-14.

Examples 2-7 to 2-14 produced organic light-emitting devices in the same manner as Example 2-6, except that the polymer in Table 4 below was used instead of polymer 6 in Example 2-6.

Comparative example 2-3 to 2-5.

Comparative Examples 2-3 to 2-5 produced organic light-emitting devices in the same manner as in Example 2-6, except that compound Q5, polymer Q3, and polymer Q4 were used instead of polymer 6 in Example 2-6.

hole transport layer Volt
(V) J
(mA/cm ² ) EQE
(%) T95
(h) Example 2-6 Polymer 6 4.50 10 6.08 201 Example 2-7 Polymer 7 4.47 10 5.86 173 Example 2-8 Polymer 8 4.24 10 5.46 188 Example 2-9 Polymer 9 4.42 10 5.99 184 Example 2-10 Polymer 10 4.51 10 6.25 199 Example 2-11 Polymer 11 4.24 10 5.41 146 Example 2-12 Polymer 12 4.67 10 6.72 110 Example 2-13 Polymer 13 4.34 10 6.66 225 Example 2-14 Polymer 14 4.32 10 6.63 217 Comparative Example 2-3 Compound Q5 3.89 10 3.24 19 Comparative Example 2-4 Polymer Q3 4.46 10 5.16 53 Comparative Example 2-5 Polymer Q4 4.00 10 3.7 32

Through the above Table 4, it can be confirmed that the organic light-emitting device (Examples 2-6 to 2-14) applying the polymer according to the present invention exhibits higher efficiency than the organic light-emitting device (Comparative Examples 2-3 to 2-5) applying other polymers or compound Q5. This is because the polymer of the present invention includes first and second units having different charge mobilities, thereby controlling the movement balance of charge/hole.

In summary, through the above Tables 3 and 4, it can be confirmed that the polymer including the first unit and the second unit has superior performance compared to the polymer including only one of the two units.

Although the preferred embodiment (hole transport layer) of the present invention has been described above, the present invention is not limited thereto, and various modifications may be made and implemented within the scope of the claims and the detailed description of the invention, which also fall within the scope of the invention.

1: Substrate
2: Anode
3: Emissive layer
4: Cathode
5: Hole injection layer
6: Hole transport layer
7: Electron injection and transport layer

Claims (14)

A first unit represented by the following chemical formula 1;
A second unit represented by the following chemical formula 1 and different from the first unit;
A third unit represented by the following chemical formula 2; and
A polymer comprising a terminal group represented by the following chemical formula 3:
[Chemical Formula 1]

[Chemical formula 2]

[Chemical Formula 3]

In the above chemical formulas 1 to 3,
L1 is a direct bond,
L3 and L4 are the same or different from each other, and each independently represents a direct bond; or a substituted or unsubstituted arylene group,
L2 is a substituted or unsubstituted phenylene group,
Ar1 and Ar2 are the same or different and each independently represents a substituted or unsubstituted arylene group,
R1 and R2 are the same as or different from each other, and each independently represents hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted arylamine group; or a substituted or unsubstituted siloxane group,
R10 and R11 are the same as or different from each other, and each independently represents a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; or a substituted or unsubstituted arylamine group,
n1 and n2 are each an integer from 1 to 4, and when n1 and n2 are each 2 or greater, the substituents in each parenthesis are the same or different,
m is an integer of 3 or 4,
When m is 3, Z is CRa; SiRa; N; or a trivalent substituted or unsubstituted aryl group,
When m is 4, Z is C; Si; or a tetravalent substituted or unsubstituted aryl group,
Ra is hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group,
Y is a direct bond; a substituted or unsubstituted alkylene group; or a substituted or unsubstituted arylene group,
When Y is a direct bond; or a substituted or unsubstituted alkylene group, Z is a trivalent or tetravalent substituted or unsubstituted aryl group,
E is hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted arylamine group; a substituted or unsubstituted siloxane group; a substituted or unsubstituted heterocyclic group; a crosslinking group; or a combination thereof,
* is an attachment point within the polymer. In claim 1,
The above polymer is a polymer represented by the following chemical formula 4:
[Chemical Formula 4]

In the above chemical formula 4,
A1 is the first unit represented by the chemical formula 1 above,
B1 is represented by the chemical formula 1 above and is a second unit different from the first unit,
C1 is the third unit represented by the chemical formula 2 above,
E1 and E2 are the same or different from each other, and are each independently a terminal group represented by the chemical formula 3,
a, b, and c are mole fractions, respectively, where a is a real number 0<a<1, b is a real number 0<b<1, c is a real number 0<c<1, and a+b+c is 1. In claim 1,
The above chemical formula 1 is a polymer represented by the following chemical formula 1-1:
[Chemical Formula 1-1]

In the above chemical formula 1-1,
R1, R2, R10, R11, Ar1, Ar2, L3, L4, n1 and n2 are the same as defined in the chemical formula 1 above,
R3 is hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted arylamine group; or a substituted or unsubstituted siloxane group,
n3 is an integer from 1 to 4, and when n3 is 2 or greater, the substituents in the parentheses are the same or different.
* is an attachment point within the polymer. In claim 1,
A polymer wherein at least one of the first unit and the second unit has the following chemical formula 1-A1:
[Chemical Formula 1-A1]

In the above chemical formula 1-A1,
L1 to L4, R1, R2, Ar1, Ar2, n1 and n2 are the same as defined in chemical formula 1,
Rx1 to Rx3 and Ry1 to Ry3 are the same or different from each other, and each independently represents hydrogen; or a substituted or unsubstituted alkyl group,
At least one of Rx1 to Rx3 and at least one of Ry1 to Ry3 is a substituted or unsubstituted alkyl group,
* is an attachment point within the polymer. In claim 4,
A polymer wherein the above Rx2 and Ry2 are the same or different and each independently a branched-chain alkyl group having 4 to 30 carbon atoms. delete In claim 1,
The above chemical formula 2 is a polymer having any one of the following chemical formulas 2-1 to 2-4:
[Chemical Formula 2-1]

[Chemical Formula 2-2]

[Chemical Formula 2-3]

[Chemical Formula 2-4]

In the above chemical formulas 2-1 to 2-4,
Z1 is CRa; SiRa; N; or a trivalent substituted or unsubstituted aryl group,
Z2 and Z3 are the same or different, and each independently represents C; Si; or a tetravalent substituted or unsubstituted aryl group,
L10 is a direct bond; or a substituted or unsubstituted arylene group,
Ra is hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group,
R50 to R60 are the same as or different from each other, and each independently represents hydrogen; deuterium; a halogen group; a cyano group; an alkoxy group; an aryloxy group; a siloxane group; a substituted or unsubstituted amine group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; or a crosslinking group, and adjacent groups may be bonded to each other to form a ring,
r50 to r59 are each an integer from 1 to 4, r60 is an integer from 1 to 5, and when r50 to r60 are each 2 or greater, the substituents in each parenthesis are the same or different,
* is an attachment point within the polymer. In claim 1,
A polymer wherein E is a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a cross-linking group; or a combination thereof. In claim 1,
wherein E is a cross-linking group; or a polymer having one of the following structures:

In the above structure,
R70 to R72 are the same as or different from each other, and each independently represents hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; or a cross-linking group,
L70 is a direct bond; a substituted or unsubstituted alkylene group; or a substituted or unsubstituted arylene group,
i1 is an integer from 1 to 10, and if i1 is 2 or greater, L70 of 2 or greater are equal to or different from each other,
n70 and n72 are each an integer from 1 to 5, n71 is an integer from 1 to 4, and when n70 to n72 are each 2 or greater, the substituents in each parenthesis are the same or different,
* is an attachment point within the polymer. In claim 1,
A polymer wherein the cross-linking group has one of the following structures:

In the above structure,
L30 to L36 are the same or different from each other, and each independently represents a direct bond; -O-; -COO-; a substituted or unsubstituted alkylene group; a substituted or unsubstituted arylene group; or a combination thereof,

is a portion that is bonded to the above chemical formula 3. In claim 1,
The first unit and the second unit are different from each other and each have one of the following structures:
. In claim 1,
The above polymer is a polymer having any one of the following structures:

In the above structure, a1 is a real number 0<a1<1, b1 is a real number 0<b1<1, c1 is a real number 0<c1<1, e1 is a real number 0<e1<1, and a1+b1+c1+e1 is 1. First electrode;
a second electrode; and
Comprising at least one organic layer provided between the first electrode and the second electrode,
An organic light-emitting device, wherein at least one of the organic layers comprises a polymer according to any one of claims 1 to 5 and 7 to 12. In claim 13,
An organic light-emitting device wherein the organic layer including the polymer is a hole injection layer, a hole transport layer, or a layer that simultaneously injects holes and transports holes.