Polymers and organic light-emitting devices using the same

Abstract

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

Description

Technical Field

[0001] This application claims the benefit of the filing date of Korean Patent Application No. 10-2022-0070659, filed with the Korean Intellectual Property Office on June 10, 2022, and all of its contents are incorporated herein by reference.

[0002] The present invention relates to a polymer and an organic light-emitting device formed using the same.

Background Art

[0003] The organic light-emitting phenomenon is one example in which current is converted into visible light by an internal process of specific organic molecules. The principle of the organic light-emitting phenomenon 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 an exciton, and the exciton falls back to the ground state again, emitting light. An organic electroluminescent device using such a principle can generally be composed of an organic layer including a cathode, an anode, and an organic layer positioned therebetween, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer.

[0004] The majority of materials used in organic light-emitting devices are pure organic substances or complex compounds formed by the combination of organic substances and metals. These can be classified into hole injection materials, hole transport materials, light-emitting materials, electron transport materials, and electron injection materials depending on their application. Here, hole injection materials and hole transport materials mainly consist of organic substances with p-type properties, that is, organic substances that are easily oxidized and have an electrochemically stable state when oxidized. On the other hand, electron injection materials and electron transport materials mainly consist of organic substances with n-type properties, that is, organic substances that are easily reduced and have an electrochemically stable state when reduced. As light-emitting materials, substances that simultaneously possess both p-type and n-type properties, that is, substances that have stable forms in both oxidized and reduced states, are preferred, and substances with high luminescence efficiency that convert excitons into light when they are formed are preferred.

[0005] In addition to the above, it is preferable that the material used in the organic light-emitting element has the following further properties.

[0006] Firstly, it is preferable that the material used in organic light-emitting devices has excellent thermal stability. This is because Joule heating occurs within organic light-emitting devices due to the transfer of electric charge. Currently, NPB (N,N'-di(1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine), which is mainly used as a hole transport material, has a glass transition temperature of 100°C or less, which presents a problem in that it is difficult to use in organic light-emitting devices that require high currents.

[0007] Secondly, in order to obtain a highly efficient organic light-emitting element that can be driven at low voltage, holes or electrons injected into the organic light-emitting element must be smoothly transferred to the light-emitting layer, and the injected holes and electrons must not escape to the outside of the light-emitting layer. For this reason, the material used in the organic light-emitting element must have a suitable band gap and HOMO (Highest Occupied Molecular Orbital) or LUMO (Lowest Unoccupied Molecular Orbital) energy level. Currently, in organic light-emitting elements manufactured by the solution coating method, if PEDOT:PSS (Poly(3,4-ethylenedioxythiophene) doped:poly(styrenesulfonic acid)) is used as a hole transport material, its LUMO energy level is lower than that of the organic material used as the light-emitting layer material, making it difficult to manufacture highly efficient, long-life organic light-emitting elements.

[0008] In addition, the materials used in organic light-emitting devices must have excellent chemical stability, charge mobility, and interface properties with electrodes and adjacent layers. Specifically, the materials used in organic light-emitting devices should exhibit minimal deformation due to moisture and oxygen. Furthermore, by possessing suitable hole or electron mobility, the density of holes and electrons in the light-emitting layer of the organic light-emitting device must be balanced to maximize exciton formation. Finally, for device stability, the interface with electrodes containing metal or metal oxides should be optimized.

[0009] In addition to the above, the material used in the organic light-emitting element for solution processes must also possess the following properties.

[0010] Firstly, a storable, homogeneous solution must be formed. In the case of commercially available materials for vapor deposition processes, they are highly crystalline and do not dissolve well in solution, or even if a solution is formed, crystals tend to form easily. Therefore, there is a high possibility that the concentration gradient of the solution will differ depending on the storage period, or that defective elements will be formed.

[0011] Secondly, the layer in which the solution process is performed must have resistance to solvents and substances relative to other layers. For this reason, it is preferable to use a substance that can introduce a curing group, such as VNPB (N4,N4'-di(naphthalene-1-yl)-N4,N4'-bis(4-vinylphenyl)biphenyl-4,4'-diamine), and after solution coating, form a self-crosslinked polymer on the substrate by heat treatment or UV (ultraviolet) irradiation, or a polymer that can form with sufficient resistance to the next process. Substances that can acquire self-resistance to solvents, such as HATCN (Hexaazatriphenylenehexacarbonitrile), are also preferred.

[0012] Therefore, in this technical field, there is a need for the development of organic materials that meet the aforementioned requirements. [Overview of the Initiative] [Problems that the invention aims to solve]

[0013] The present invention aims to provide a polymer and an organic light-emitting element formed using the same. [Means for solving the problem]

[0014] One embodiment of the present invention provides a polymer comprising a first unit represented by the following chemical formula 1; a second unit represented by the following chemical formula 2; a third unit represented by the following chemical formula 4, which differs from the first unit; and a terminal group represented by the following chemical formula 3.

[0015] [ka] [ka]

[0016] In the above chemical formulas 1 to 4, Ar1 to Ar4 are either identical or different from each other, and each is independently a substituted or unsubstituted arylene group. L1-L4 are identical or different from each other, and each is independently directly bonded; or substituted or unsubstituted arylene groups. R1 to R6 are either identical or different from each other, and each is independently a hydrogen; deuterium; halogen group; substituted or unsubstituted alkyl group; substituted or unsubstituted silyl group; substituted or unsubstituted aryl group; substituted or unsubstituted heterocyclic group; substituted or unsubstituted arylamine group; or substituted or unsubstituted siloxane group. R11 to R16 are either identical or different from each other, and each is independently an alkyl group having 1 to 3 carbon atoms. R21 and R22 are either identical or different from each other, and independently of each other, are hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group. r1 to r6 are integers from 1 to 4, and if r1 to r6 are each 2 or greater, then the substituents in each parenthese are either identical or different from each other. l1 to l4 are integers from 1 to 5, and if l1 to l4 are all 2 or greater, the structures within each set of parentheses are either identical or different from one another. 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. If Y is directly bonded; or a substituted or unsubstituted alkylene group, then 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 crosslinkable group; or a combination thereof, * is a bonding point in the polymer.

[0017] Another embodiment of the present invention provides an organic light-emitting device including a first electrode; a second electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers contain the polymer.

Advantages of the Invention

[0018] The polymer according to one embodiment of the present invention contains a unit of Chemical Formula 1 substituted with three alkyl groups having 1 to 3 carbon atoms. This shows the effect of improving the solubility of the produced polymer. Also, the polymer according to one embodiment of the present invention can be applied to an organic light-emitting device to improve the performance and / or stability of the device.

Brief Description of the Drawings

[0019] [Figure 1] It is an exemplary diagram of the structure of an organic light-emitting device according to an embodiment of the present invention. [Figure 2] It is an exemplary diagram of the structure of an organic light-emitting device according to an embodiment of the present invention. [Figure 3] It is a diagram showing the experimental results of the film retention rate of the thin film formed from the coating composition 1 produced in Example 2-1. [Figure 4] It is a diagram showing the experimental results of the film retention rate of the thin film formed from the coating composition 2 produced in Comparative Example 2-1. [Figure 5] It is a diagram showing the experimental results of the film retention rate of the thin film formed from the coating composition 3 produced in Comparative Example 2-2.

Modes for Carrying Out the Invention

[0020] The present invention will be described in more detail below. The present invention provides a polymer comprising a first unit represented by the following chemical formula 1; a second unit represented by the following chemical formula 2; a third unit represented by the following chemical formula 4, which differs from the first unit; and a terminal group represented by the following chemical formula 3.

[0021] [ka] [ka]

[0022] In the above chemical formulas 1 to 4, Ar1 to Ar4 are either identical or different from each other, and each is independently a substituted or unsubstituted arylene group. L1-L4 are identical or different from each other, and each is independently directly bonded; or substituted or unsubstituted arylene groups. R1 to R6 are either identical or different from each other, and each is independently a hydrogen; deuterium; halogen group; substituted or unsubstituted alkyl group; substituted or unsubstituted silyl group; substituted or unsubstituted aryl group; substituted or unsubstituted heterocyclic group; substituted or unsubstituted arylamine group; or substituted or unsubstituted siloxane group. R11 to R16 are either identical or different from each other, and each is independently an alkyl group having 1 to 3 carbon atoms. R21 and R22 are either identical or different from each other, and independently of each other, are hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group. r1 to r6 are integers from 1 to 4, and if r1 to r6 are each 2 or greater, then the substituents in each parenthese are either identical or different from each other. l1 to l4 are integers from 1 to 5, and if l1 to l4 are all 2 or greater, the structures within each set of parentheses are either identical or different from one another. 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. If Y is directly bonded; or a substituted or unsubstituted alkylene group, then Z is a trivalent or tetravalent substituted or unsubstituted aryl group. E is hydrogen; deuterium; substituted or unsubstituted alkyl group; substituted or unsubstituted silyl group; substituted or unsubstituted aryl group; substituted or unsubstituted arylamine group; substituted or unsubstituted siloxane group; crosslinking group; or a combination thereof. * indicates a bond point within the polymer.

[0023] In one embodiment of the present invention, the first unit contained in the polymer contains three substituted or unsubstituted phenylene groups as a core, and a conjugation is formed with a -(L-phenyl group) substituted with an amine group. In this case, the substitution of three alkyl groups at specific positions on the phenyl group in the -(L-phenyl group) breaks the conjugation, resulting in an effect of improving charge mobility. Therefore, by containing a phenyl group substituted with three alkyl groups, the polymer can exhibit a low drive voltage, improved efficiency, and / or long life characteristics when applied to a device.

[0024] In this specification, when a member (layer) is said to be located "on top of" another member (layer), this includes not only cases where the member (layer) is in contact with the other member, but also cases where another member (layer) exists between the two members (layers).

[0025] In this specification, when a part is described as "including" a component, unless otherwise stated, this does not mean that it excludes other components, but rather that it may include other components.

[0026] In this specification, the term "layer" is interchangeable with "film" or "membrane" as commonly used in the art, and refers to a coating that covers a target area. The size of the "layer" is not limited, and each "layer" may be the same size or different in size. In one embodiment, the size of the "layer" may be the same as the entire element, may correspond to the size of a specific functional area, or may be smaller by only a single sub-pixel.

[0027] In this specification, "or" means an inclusive "or" and not an exclusive "or". For example, condition A or B means that one of the following is satisfied: A is true (or exists) and B is false (or does not exist); A is false (or does not exist) and B is true (or exists); and both A and B are true (or exist).

[0028] In this specification, the inclusion of a specific substance A in a layer B includes both i) the inclusion of one or more substances A in a single layer B, and ii) the inclusion of one or more layers B, with substance A being present in one or more of the multilayered layers B.

[0029] In this specification, if a particular substance A is said to be contained in a C layer or a D layer, it means that substance A is i) contained in one or more C layers, ii) contained in one or more D layers, or iii) contained in one or more C layers and one or more D layers, respectively.

[0030] In this specification, "mole fraction" means the ratio of the number of moles of a given component to the total number of moles of all components.

[0031] In this specification, “adjacent” groups may mean a substituent substituted on an atom directly connected to the atom on which the substituent is substituted, a substituent that is stereostructically closest to the substituent, or another substituent substituted on the atom on which the substituent is substituted. 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, can be interpreted as “adjacent” groups.

[0032] In this specification, in a ring formed by the bonding of adjacent groups to each other, “ring” means a substituted or unsubstituted hydrocarbon ring; or a substituted or unsubstituted heteroring.

[0033] In this specification, unless otherwise defined, all technical and scientific terms used herein have the same meaning as those commonly understood by those skilled in the art to which the present invention pertains. Similar or equivalent methods and materials to those described herein may be used in carrying out or testing embodiments of the present invention, but suitable methods and materials will be described later. All publications, patents, and other references referenced herein are incorporated herein by reference in whole, and in the event of any conflict, unless a specific passage is mentioned, this specification shall prevail, including definitions. The materials, methods, and examples are illustrative and not intended to be limiting.

[0034] In this specification, [ka] This refers to a site that is connected to another substituent or bond.

[0035] In this specification, "*" represents a bond point within the polymer.

[0036] The term "substitution" above means that a hydrogen atom bonded to a carbon atom of a compound is replaced by another substituent. The position of substitution is not limited to any position where a hydrogen atom can be substituted, i.e., any position where a substituent can be substituted. If two or more substituents are substituted, the two or more substituents may be the same or different from each other.

[0037] In this specification, the term “substituted or unsubstituted” means that a molecule is substituted with one or more substituents selected from the group consisting of deuterium; halogen groups; alkyl groups; cycloalkyl groups; alkoxy groups; aryloxy groups; amine groups; aryl groups; heterocyclic groups; and crosslinkable groups, or is substituted with substituents in which two or more substituents from the exemplified substituents are linked together, or has no substituents at all. For example, “substituents in which two or more substituents are linked together” may be biphenyl groups. That is, a biphenyl group may be an aryl group, and can also be interpreted as a substituent in which two phenyl groups are linked together.

[0038] Examples of the substituents are described below, but are not limited to these.

[0039] Examples of halogen groups used herein include fluorine (F), chlorine (Cl), bromine (Br), or iodine (I).

[0040] In this 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. In 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, and an octyl group.

[0041] In this specification, an alkylene group means a group that has two bonding positions on an alkyl group, i.e., a divalent group. The above-mentioned description of alkyl groups may apply, except that each of these is a divalent group.

[0042] In this specification, the number of carbon atoms in the cycloalkyl group is not particularly limited, but is preferably 3 to 60. In one embodiment, the number of carbon atoms in 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, and a cyclooctyl group.

[0043] In this specification, the alkoxy group may be linear, branched, or cyclic. The number of carbon atoms in the alkoxy group is not particularly limited, but it is preferably 1 to 30. 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, and an n-decyloxy group.

[0044] In this specification, the amine group may be selected from, but is not limited to, the group consisting of -NH2; alkylamine group; arylalkylamine group; arylamine group; arylheteroarylamine group; alkylheteroarylamine group; and heteroarylamine group. The number of carbon atoms in the amine group is not particularly limited, but is preferably 1 to 60.

[0045] In this specification, the number of carbon atoms in the aryl group is not particularly limited, but is preferably 6 to 60. In one embodiment, the number of carbon atoms in the aryl group is 6 to 30. In one embodiment of the present invention, the aryl group may be a monocyclic aryl group or a polycyclic aryl group. Examples of the monocyclic aryl group include, but are not limited to, a phenyl group, a biphenyl group, a terphenyl group, etc. Examples of the polycyclic aryl group include, but are not limited to, a naphthyl group, anthracenyl group, phenantrenyl group, pyrenyl group, perilenyl group, triphenylenyl group, chrysenyl group, fluorenyl group, etc.

[0046] In this specification, an arylene group refers to a group in which an aryl group has two bonding positions, i.e., a divalent group. The description of the aryl group described above may apply, except that these are each divalent groups.

[0047] In this specification, examples of arylamine groups include substituted or unsubstituted monoarylamine groups, substituted or unsubstituted diarylamine groups, or substituted or unsubstituted triarylamine groups. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group containing two or more aryl groups may contain a monocyclic aryl group, a polycyclic aryl group, or both a monocyclic and a polycyclic aryl group. For example, the aryl group in the arylamine group may be selected from the examples of aryl groups described above. The number of carbon atoms in the arylamine group is not particularly limited, but is preferably 6 to 60.

[0048] In this specification, a heterocyclic group is an aromatic, aliphatic, or aromatic-aliphatic fused ring group containing one or more non-carbon atoms or heteroatoms. Specifically, the heteroatoms 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 between 2 and 60. Examples of the aforementioned heterocyclic groups include, but are not limited to, thiophene groups, furan groups, pyrrole groups, imidazole groups, thiazole groups, oxazole groups, oxadiazole groups, pyridine groups, bipyridine groups, pyrimidine groups, triazine groups, triazole groups, acridine groups, pyridazine groups, pyrazine groups, quinoline groups, quinazoline groups, quinoxaline groups, phthalazine groups, pyridopyrimidine groups, pyridopyrazine groups, pyrazinopyrazine groups, isoquinoline groups, indole groups, carbazole groups, benzoxazole groups, benzimidazole groups, benzothiazole groups, benzocarbazole groups, benzothiophene groups, dibenzothiophene groups, benzofuran groups, phenanthridine groups, phenanthroline groups, isoxazole groups, thiadiazole groups, phenothiazine groups, and dibenzofuran groups.

[0049] In this 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, a carbazole group, and the like.

[0050] In this specification, an aryloxy group is a group represented by -OR200, where R200 is an aryl group. The aryl group in an aryloxy group is the same as the examples of aryl groups described above. Specifically, examples of aryloxy groups include, but are not limited to, phenoxy, benzyloxy, p-methylbenzyloxy, p-tolyloxy, m-tolyloxy, 3,5-dimethylphenoxy, 2,4,6-trimethylphenoxy, p-tert-butylphenoxy, 3-biphenyloxy, 4-biphenyloxy, 1-naphthyloxy, 2-naphthyloxy, 4-methyl-1-naphthyloxy, 5-methyl-2-naphthyloxy, 1-anthryloxy, 2-anthryloxy, 9-anthryloxy, 1-phenanthryloxy, 3-phenanthryloxy, and 9-phenanthryloxy.

[0051] In this specification, a silyl group is a group represented as -SiR201R202R203, where R201, R202, and R203 are identical or different from each other and are independently 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, trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, and phenylsilyl groups.

[0052] In this specification, a siloxane group is a group represented by -Si(R204)2OSi(R205)3, where R204 and R205 are identical or different from each other and are independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group.

[0053] In this specification, the hydrocarbon ring group may be an aromatic ring, an aliphatic ring, or a ring formed by the fusion of an aromatic ring and an aliphatic ring.

[0054] In this specification, the aromatic ring may be defined as such by the description of the aryl group described above.

[0055] In this specification, the aliphatic ring may be defined as such in accordance with the description of cycloalkyl groups described above.

[0056] In this specification, a combination of substituents means a substituent in which two or more substituents from the exemplified substituents are linked together. For example, in hydrogen; deuterium; substituted or unsubstituted alkyl groups; substituted or unsubstituted aryl groups; crosslinkable groups; or combinations thereof, "combination" means a substituent in which two or more substituents from the exemplified substituents are linked together. Examples include, but are not limited to, a structure in which an alkyl group and a crosslinkable group are linked together, or a structure in which an alkyl group and an aryl group are linked together.

[0057] In this specification, a crosslinkable group may mean a reactive substituent that crosslinks compounds when exposed to heat, light, and / or radiation. Crosslinking can be generated by the linking of radicals produced when carbon-carbon multiple bonds or cyclic structures are broken down by heat treatment, light irradiation, and / or radiation irradiation.

[0058] In this specification, a crosslinkable group is one of the following structures.

[0059] [ka]

[0060] In the above structure, L30~L36 are either identical or different from each other, and each is independently directly bonded; -O-; -COO-; substituted or unsubstituted alkylene groups; substituted or unsubstituted arylene groups; or a combination thereof. [ka] This is a site that binds to other substituents or bonding sites.

[0061] One embodiment of the present invention, the above [ka] This is chemical formula 3 of [ka] This corresponds to the part represented by [the symbol].

[0062] The following explains the first unit.

[0063] In one embodiment of the present invention, the first unit is a unit having two connection points.

[0064] In one embodiment of the present invention, the chemical formula 1 is the following chemical formula 1-1. [ka]

[0065] In the above chemical formula 1-1, Ar1, Ar2, L1, L2, R11~R16, l1, and l2 are defined as in the above chemical formula 1, R1, R2, R2', and R3 are either identical or different from each other and are 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.

[0066] In one embodiment of the present invention, L1 and L2 are identical or different from each other, and are independently substituted or unsubstituted arylene groups having 6 to 30 carbon atoms.

[0067] In one embodiment of the present invention, L1 and L2 are the same or different from each other and are independently a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted terphenylene group; or a substituted or unsubstituted naphthylene group.

[0068] In one embodiment of the present invention, L1 and L2 are the same or different from each other and are independently a phenylene group; a biphenylene group; a terphenylene group; or a naphthylene group.

[0069] In one embodiment of the present invention, the chemical formula 1 is the following chemical formula 1-2. [ka]

[0070] In the above chemical formula 1-2, Ar1, Ar2, R1-R3, R11-R16, and r1-r3 are defined as in the above chemical formula 1, R17 and R18 are either identical or different to each other and are independently hydrogen; deuterium; halogen group; substituted or unsubstituted alkyl group; substituted or unsubstituted silyl group; substituted or unsubstituted aryl group; substituted or unsubstituted heterocyclic group; substituted or unsubstituted arylamine group; or substituted or unsubstituted siloxane group. r17 and r18 are integers from 1 to 4, and if r17 and r18 are each 2 or greater, the substituents in their respective parentheses are either identical or different from each other. p1 and p2 are integers from 1 to 3, and if p1 and p2 are both 2 or greater, the structures within each set of parentheses are either identical or different. * indicates a bond point within the polymer.

[0071] In one embodiment of the present invention, Ar1 and Ar2 are identical or different, substituted or unsubstituted arylene groups having 6 to 30 carbon atoms.

[0072] In one embodiment of the present invention, Ar1 and Ar2 are identical or different from each other and are independently a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted terphenylene group; or a substituted or unsubstituted naphthylene group.

[0073] In one embodiment of the present invention, the chemical formula 1 is the following chemical formulas 1-3. [ka]

[0074] In the above chemical formulas 1 and 3, R1-R3, R11-R16, and r1-r3 are defined as in the same way as in Chemical Formula 1 above. R17, R18, R20, and R21 are identical or different from each other and are independently hydrogen; deuterium; halogen group; substituted or unsubstituted alkyl group; substituted or unsubstituted silyl group; substituted or unsubstituted aryl group; substituted or unsubstituted heterocyclic group; substituted or unsubstituted arylamine group; or substituted or unsubstituted siloxane group. r17, r18, r20, and r21 are each integers from 1 to 4, and if r17, r18, r20, and r21 are each 2 or greater, then the substituents in each parenthese are either identical or different from each other. p1 to p4 are integers from 1 to 3, and if p1 to p4 are each 2 or greater, the structures within each set of parentheses are either identical or different from one another. * indicates a bond point within the polymer.

[0075] In one embodiment of the present invention, the chemical formula 1 is the following chemical formulas 1-4. [ka]

[0076] In the above chemical formulas 1 and 4, R11 to R16 are defined in the same way as in Chemical Formula 1 above. R1, R2, R2', R3, R17, R18, R20, and R21 are either identical or different from each other, and each is independently a hydrogen; deuterium; halogen group; substituted or unsubstituted alkyl group; substituted or unsubstituted silyl group; substituted or unsubstituted aryl group; substituted or unsubstituted heterocyclic group; substituted or unsubstituted arylamine group; or substituted or unsubstituted siloxane group. r17, r18, r20, and r21 are each integers from 1 to 4, and if r17, r18, r20, and r21 are each 2 or greater, then the substituents in each parenthese are either identical or different from each other. p1 to p4 are integers from 1 to 3, and if p1 to p4 are each 2 or greater, the structures within each set of parentheses are either identical or different from one another. * indicates a bond point within the polymer.

[0077] In one embodiment of the present invention, R1 to R3 are identical or different from each other, and each is independently hydrogen; or a substituted or unsubstituted alkyl group.

[0078] In one embodiment of the present invention, R1 to R3 are identical or different from each other, and each is independently hydrogen; or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

[0079] In one embodiment of the present invention, R1 to R3 are identical or different from each other, and each is independently hydrogen; or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

[0080] In one embodiment of the present invention, R1 to R3 are identical or different from each other, and each is independently hydrogen; or an alkyl group.

[0081] In one embodiment of the present invention, at least one of R1 to R3 is a substituted or unsubstituted alkyl group.

[0082] In one embodiment of the present invention, R1 to R3 are identical or different from each other, and each is independently hydrogen; or a substituted or unsubstituted alkyl group, and at least one of R1 to R3 is a substituted or unsubstituted alkyl group.

[0083] In one embodiment of the present invention, R1 to R3 are identical or different from each other, and each is independently hydrogen; or a substituted or unsubstituted C1 to C10 alkyl group, and at least one of R1 to R3 is a substituted or unsubstituted C1 to C10 alkyl group.

[0084] In one embodiment of the present invention, R1, R2, R2', and R3 are identical or different from each other and are independently hydrogen; or a substituted or unsubstituted alkyl group.

[0085] In one embodiment of the present invention, R1, R2, R2', and R3 are identical or different from each other, and each is independently hydrogen; or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

[0086] In one embodiment of the present invention, R1, R2, R2', and R3 are identical or different from each other, and each is independently hydrogen; or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

[0087] In one embodiment of the present invention, R1, R2, R2', and R3 are identical or different from each other and are independently hydrogen; or alkyl groups.

[0088] In one embodiment of the present invention, at least one of R1, R2, R2', and R3 is a substituted or unsubstituted alkyl group.

[0089] In one embodiment of the present invention, R1, R2, R2', and R3 are identical or different from each other, and each is independently hydrogen; or a substituted or unsubstituted alkyl group, wherein at least one of R1, R2, R2', and R3 is a substituted or unsubstituted alkyl group.

[0090] In one embodiment of the present invention, R1, R2, R2', and R3 are identical or different from each other, and each is independently hydrogen; or a substituted or unsubstituted C1-C10 alkyl group, and at least one of R1, R2, R2', and R3 is a substituted or unsubstituted C1-C10 alkyl group.

[0091] In one embodiment of the present invention, R1 and R3 are hydrogen; or substituted or unsubstituted alkyl groups.

[0092] In one embodiment of the present invention, R1 and R3 are hydrogen; or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

[0093] In one embodiment of the present invention, R1 and R3 are hydrogen; or alkyl groups.

[0094] In one embodiment of the present invention, R1 and R3 are hydrogen; or a methyl group.

[0095] In one embodiment of the present invention, R2 is a substituted or unsubstituted alkyl group.

[0096] In one embodiment of the present invention, R2 is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

[0097] In one embodiment of the present invention, R2 is an alkyl group having 1 to 10 carbon atoms.

[0098] In one embodiment of the present invention, R2 is a hexyl group.

[0099] In one embodiment of the present invention, R2 and R2' are either the same as or different from each other, and are independently substituted or unsubstituted alkyl groups.

[0100] In one embodiment of the present invention, R2 and R2' are identical or different from each other, and each is independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

[0101] In one embodiment of the present invention, R2 and R2' are either the same as or different from each other, and are each independently an alkyl group having 1 to 10 carbon atoms.

[0102] In one embodiment of the present invention, R2 and R2' are each hexyl groups.

[0103] In one embodiment of the present invention, R11 to R16 are either the same as or different from each other, and each is independently a methyl group; an ethyl group; or a propyl group.

[0104] In one embodiment of the present invention, R11 to R16 are each methyl groups.

[0105] In one embodiment of the present invention, R17, R18, R20, and R21 are identical or different from each other and are independently hydrogen; deuterium; or a substituted or unsubstituted alkyl group.

[0106] In one embodiment of the present invention, R17, R18, R20, and R21 are identical or different from each other and are independently hydrogen; deuterium; or alkyl group.

[0107] In one embodiment of the present invention, R17, R18, R20, and R21 are each hydrogen.

[0108] In one embodiment of the present invention, p1 to p4 are each 1 or 2.

[0109] In one embodiment of the present invention, p1 and p2 are each 1.

[0110] In one embodiment of the present invention, p3 and p4 are each 2.

[0111] In one embodiment of the present invention, the chemical formula 1 is one of the following structures. [ka]

[0112] In the above structure, * represents a bonding point within the polymer.

[0113] In one embodiment of the present invention, hydrogen can be substituted with deuterium. For example, the hydrogen contained in the structure can be substituted with deuterium.

[0114] The third unit will be explained below.

[0115] In one embodiment of the present invention, the third unit is a unit having two connection points.

[0116] In one embodiment of the present invention, the chemical formula 4 is the following chemical formula 4-1. [ka]

[0117] In the aforementioned chemical formula 4-1, R4~R6, Ar3, Ar4, L3, L4, r4~r6, l3, and l4 are defined as in the same way as in Chemical Formula 4 above. R23 and R24 are either identical or different to each other and are independently hydrogen; deuterium; halogen group; substituted or unsubstituted alkyl group; substituted or unsubstituted silyl group; substituted or unsubstituted aryl group; substituted or unsubstituted heterocyclic group; substituted or unsubstituted arylamine group; or substituted or unsubstituted siloxane group. r23 and r24 are integers from 1 to 5, and if r23 and r24 are 2 or greater, the substituents in their respective parentheses are either identical or different. * indicates a bond point within the polymer.

[0118] In one embodiment of the present invention, the chemical formula 4 is the following chemical formula 4-2. [ka]

[0119] In the aforementioned chemical formula 4-2, R4~R6, Ar3, Ar4, L3, L4, r4~r6, l3, and l4 are defined as in the same way as in Chemical Formula 4 above. R23 and R24 are either identical or different to each other and are independently of each other: deuterium; halogen group; substituted or unsubstituted alkyl group; substituted or unsubstituted silyl group; substituted or unsubstituted aryl group; substituted or unsubstituted heterocyclic group; substituted or unsubstituted arylamine group; or substituted or unsubstituted siloxane group. R25 and R26 are either identical or different to each other and are independently hydrogen; deuterium; halogen group; substituted or unsubstituted alkyl group; substituted or unsubstituted silyl group; substituted or unsubstituted aryl group; substituted or unsubstituted heterocyclic group; substituted or unsubstituted arylamine group; or substituted or unsubstituted siloxane group. r25 and r26 are integers from 1 to 4, and if r25 and r26 are each 2 or greater, the substituents in their respective parentheses are either identical or different. * indicates a bond point within the polymer.

[0120] In one embodiment of the present invention, the chemical formula 4 is the following chemical formula 4-3. [ka]

[0121] In the aforementioned chemical formula 4-3, R4~R6, Ar3, Ar4, and r4~r6 are defined as in the same way as in Chemical Formula 4 above. R23 and R24 are either identical or different to each other and are independently of each other: deuterium; halogen group; substituted or unsubstituted alkyl group; substituted or unsubstituted silyl group; substituted or unsubstituted aryl group; substituted or unsubstituted heterocyclic group; substituted or unsubstituted arylamine group; or substituted or unsubstituted siloxane group. R25~R28 are either identical or different from each other, and each is independently a hydrogen; deuterium; halogen group; substituted or unsubstituted alkyl group; substituted or unsubstituted silyl group; substituted or unsubstituted aryl group; substituted or unsubstituted heterocyclic group; substituted or unsubstituted arylamine group; or substituted or unsubstituted siloxane group. r25~r28 are integers from 1 to 4, and if r25~r28 are each 2 or greater, then the substituents in each parentheses are either identical or different from each other. p5 and p6 are integers from 1 to 3, and if p5 and p6 are both 2 or greater, the structures within each set of parentheses are either identical or different. * indicates a bond point within the polymer.

[0122] In one embodiment of the present invention, the chemical formula 4 is the following chemical formula 4-4. [ka]

[0123] In the aforementioned chemical formula 4-4, R4~R6 and r4~r6 are defined in the same way as in the above chemical formula 4. R23 and R24 are either identical or different to each other and are independently of each other: deuterium; halogen group; substituted or unsubstituted alkyl group; substituted or unsubstituted silyl group; substituted or unsubstituted aryl group; substituted or unsubstituted heterocyclic group; substituted or unsubstituted arylamine group; or substituted or unsubstituted siloxane group. R25~R30 are either identical or different from each other, and each is independently hydrogen; deuterium; halogen group; substituted or unsubstituted alkyl group; substituted or unsubstituted silyl group; substituted or unsubstituted aryl group; substituted or unsubstituted heterocyclic group; substituted or unsubstituted arylamine group; or substituted or unsubstituted siloxane group. r25~r30 are integers from 1 to 4, and if r25~r30 are each 2 or greater, then the substituents in each parentheses are either identical or different from each other. p5 to p8 are integers from 1 to 3, and if p5 to p8 are each 2 or greater, the structures within each set of parentheses are either identical or different from one another. * indicates a bond point within the polymer.

[0124] In one embodiment of the present invention, the chemical formula 4 is the following chemical formula 4-5. [ka]

[0125] In the aforementioned chemical formula 4-5, Ar3, Ar4, L3, L4, l3, and l4 are defined as in the same way as in the above chemical formula 4. R4, R5, R5', R6, R23, and R24 are identical or different from each other and are independently hydrogen; deuterium; halogen group; substituted or unsubstituted alkyl group; substituted or unsubstituted silyl group; substituted or unsubstituted aryl group; substituted or unsubstituted heterocyclic group; substituted or unsubstituted arylamine group; or substituted or unsubstituted siloxane group. r23 and r24 are integers from 1 to 5, and if r23 and r24 are 2 or greater, the substituents in their respective parentheses are either identical or different. * indicates a bond point within the polymer.

[0126] In one embodiment of the present invention, the chemical formula 4 is the following chemical formula 4-6. [ka]

[0127] In the aforementioned chemical formula 4-6, Ar3, Ar4, L3, L4, l3, and l4 are defined as in the same way as in the above chemical formula 4. R4, R5, R5', R6, R25, and R26 are identical or different from each other and are independently hydrogen; deuterium; halogen group; substituted or unsubstituted alkyl group; substituted or unsubstituted silyl group; substituted or unsubstituted aryl group; substituted or unsubstituted heterocyclic group; substituted or unsubstituted arylamine group; or substituted or unsubstituted siloxane group. R23 and R24 are either identical or different to each other and are independently of each other: deuterium; halogen group; substituted or unsubstituted alkyl group; substituted or unsubstituted silyl group; substituted or unsubstituted aryl group; substituted or unsubstituted heterocyclic group; substituted or unsubstituted arylamine group; or substituted or unsubstituted siloxane group. r25 and r26 are integers from 1 to 4, and if r25 and r26 are each 2 or greater, the substituents in their respective parentheses are either identical or different. * indicates a bond point within the polymer.

[0128] In one embodiment of the present invention, the chemical formula 4 is the following chemical formula 4-7. [ka]

[0129] In the aforementioned chemical formula 4-7, R4, R5, R5', R6, and R25~R30 are either identical or different from each other, and each is independently a hydrogen; deuterium; halogen group; substituted or unsubstituted alkyl group; substituted or unsubstituted silyl group; substituted or unsubstituted aryl group; substituted or unsubstituted heterocyclic group; substituted or unsubstituted arylamine group; or substituted or unsubstituted siloxane group. R23 and R24 are either identical or different to each other and are independently of each other: deuterium; halogen group; substituted or unsubstituted alkyl group; substituted or unsubstituted silyl group; substituted or unsubstituted aryl group; substituted or unsubstituted heterocyclic group; substituted or unsubstituted arylamine group; or substituted or unsubstituted siloxane group. r25~r30 are integers from 1 to 4, and if r25~r30 are each 2 or greater, then the substituents in each parentheses are either identical or different from each other. p5 to p8 are integers from 1 to 3, and if p5 to p8 are each 2 or greater, the structures within each set of parentheses are either identical or different from one another. * indicates a bond point within the polymer.

[0130] In one embodiment of the present invention, R4 to R6 are identical or different from each other, and each is independently hydrogen; or a substituted or unsubstituted alkyl group.

[0131] In one embodiment of the present invention, R4 to R6 are identical or different from each other, and each is independently hydrogen; or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

[0132] In one embodiment of the present invention, R4 to R6 are identical or different from each other, and each is independently hydrogen; or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

[0133] In one embodiment of the present invention, R4 to R6 are either the same as or different from each other, and each is independently hydrogen; or an alkyl group.

[0134] In one embodiment of the present invention, at least one of R4 to R6 is a substituted or unsubstituted alkyl group.

[0135] In one embodiment of the present invention, R4 to R6 are either the same as or different from each other, and each is independently hydrogen; or a substituted or unsubstituted alkyl group, and at least one of R4 to R6 is a substituted or unsubstituted alkyl group.

[0136] In one embodiment of the present invention, R4 to R6 are identical or different from each other, and each is independently hydrogen; or a substituted or unsubstituted C1 to C10 alkyl group, and at least one of R4 to R6 is a substituted or unsubstituted C1 to C10 alkyl group.

[0137] In one embodiment of the present invention, R4, R5, R5', and R6 are identical or different from each other and are independently hydrogen; or a substituted or unsubstituted alkyl group.

[0138] In one embodiment of the present invention, R4, R5, R5', and R6 are identical or different from each other and are independently hydrogen; or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

[0139] In one embodiment of the present invention, R4, R5, R5', and R6 are identical or different from each other and are independently hydrogen; or a substituted or unsubstituted C1-C10 alkyl group.

[0140] In one embodiment of the present invention, R4, R5, R5', and R6 are identical or different from each other and are independently hydrogen; or alkyl groups.

[0141] In one embodiment of the present invention, at least one of R4, R5, R5', and R6 is a substituted or unsubstituted alkyl group.

[0142] In one embodiment of the present invention, R4, R5, R5', and R6 are identical or different from each other, and each is independently hydrogen; or a substituted or unsubstituted alkyl group, and at least one of R4, R5, R5', and R6 is a substituted or unsubstituted alkyl group.

[0143] In one embodiment of the present invention, R4, R5, R5', and R6 are identical or different from each other, and each is independently hydrogen; or a substituted or unsubstituted C1-C10 alkyl group, and at least one of R4, R5, R5', and R6 is a substituted or unsubstituted C1-C10 alkyl group.

[0144] In one embodiment of the present invention, R4 and R6 are hydrogen; or substituted or unsubstituted alkyl groups.

[0145] In one embodiment of the present invention, R4 and R6 are hydrogen; or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

[0146] In one embodiment of the present invention, R4 and R6 are hydrogen; or alkyl groups.

[0147] In one embodiment of the present invention, R4 and R6 are hydrogen; or a methyl group.

[0148] In one embodiment of the present invention, R5 is a substituted or unsubstituted alkyl group.

[0149] In one embodiment of the present invention, R5 is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

[0150] In one embodiment of the present invention, R5 is an alkyl group having 1 to 10 carbon atoms.

[0151] In one embodiment of the present invention, R5 is a hexyl group.

[0152] In one embodiment of the present invention, R5 and R5' are either the same as or different from each other, and are independently substituted or unsubstituted alkyl groups.

[0153] In one embodiment of the present invention, R5 and R5' are identical or different from each other, and each is independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

[0154] In one embodiment of the present invention, R5 and R5' are either the same as or different from each other, and are each independently an alkyl group having 1 to 10 carbon atoms.

[0155] In one embodiment of the present invention, R5 and R5' are each hexyl groups.

[0156] In one embodiment of the present invention, R23 and R24 are identical or different from each other, and are independently substituted or unsubstituted alkyl groups.

[0157] In one embodiment of the present invention, R23 and R24 are identical or different from each other, and are independently substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms.

[0158] In one embodiment of the present invention, R23 and R24 are identical or different from each other and are independently a linear alkyl group having 1 to 30 carbon atoms; or a branched alkyl group having 4 to 30 carbon atoms.

[0159] In one embodiment of the present invention, R23 and R24 are identical or different from each other and are independently a linear alkyl group having 1 to 15 carbon atoms; or a branched alkyl group having 4 to 15 carbon atoms.

[0160] In one embodiment of the present invention, R25 to R30 are identical or different from each other and are independently hydrogen; deuterium; or a substituted or unsubstituted alkyl group.

[0161] In one embodiment of the present invention, R25 to R30 are either the same as or different from each other, and each is independently hydrogen; deuterium; or an alkyl group.

[0162] In one embodiment of the present invention, R25 to R30 are each hydrogen.

[0163] In one embodiment of the present invention, p5 to p8 are each 1 or 2.

[0164] In one embodiment of the present invention, p5 and p6 are each 1.

[0165] In one embodiment of the present invention, p7 and p8 are each 2.

[0166] In one embodiment of the present invention, the chemical formula 4 is one of the following structures. [ka]

[0167] The following explains the second unit.

[0168] In one embodiment of the present invention, the second unit is a unit having three or four connection points.

[0169] In one embodiment of the present invention, Y is a directly bonded, or substituted or unsubstituted arylene group.

[0170] In one embodiment of the present invention, Y is a directly bonded, substituted, or unsubstituted phenylene group.

[0171] In one embodiment of the present invention, the chemical formula 2 is one of the following chemical formulas 2-1 to 2-4. [ka] [ka]

[0172] In the aforementioned chemical formulas 2-1 to 2-4, Z1 is CRa;SiRa;N; or a trivalent substituted or unsubstituted aryl group. Z2 and Z3 are either identical or different from each other, and each is independently a C;Si; or a tetravalent substituted or unsubstituted aryl group. L10 is a directly bonded; 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 either identical or different from each other, and each is independently a hydrogen; deuterium; halogen group; cyano group; alkoxy group; aryloxy group; siloxane group; substituted or unsubstituted amine group; substituted or unsubstituted alkyl group; substituted or unsubstituted aryl group; substituted or unsubstituted heterocyclic group; or crosslinkable group, and adjacent groups may bond to each other to form a ring. If r50 to r59 are integers from 1 to 4, and r60 is an integer from 1 to 5, and if r50 to r60 are each 2 or greater, then the substituents in each set of parentheses are either identical or different from each other. * indicates a bond point within the polymer.

[0173] In one embodiment of the present invention, the chemical formula 2 is the chemical formula 2-1.

[0174] In one embodiment of the present invention, if Z1 is CRa or SiRa and Ra is a substituted or unsubstituted aryl group, then L10 is a substituted or unsubstituted arylene group.

[0175] In one embodiment of the present invention, Z1 is CH;SiH;N; or a substituted or unsubstituted trivalent aryl group.

[0176] In one embodiment of the present invention, Z1 is CH;SiH;N; or a substituted or unsubstituted trivalent phenyl group.

[0177] In one embodiment of the present invention, Z1 is N or a trivalent phenyl group.

[0178] In one embodiment of the present invention, L10 is a directly bonded, substituted, or unsubstituted arylene group having 6 to 30 carbon atoms.

[0179] In one embodiment of the present invention, L10 is directly bonded; or an arylene group having 6 to 30 carbon atoms.

[0180] In one embodiment of the present invention, L10 is a direct bond; or a phenylene group.

[0181] In one embodiment of the present invention, L10 is a direct bond.

[0182] In one embodiment of the present invention, the chemical formula 2 is the chemical formula 2-2.

[0183] In one embodiment of the present invention, Z2 is C; or Si.

[0184] In one embodiment of the present invention, the chemical formula 2 is the chemical formula 2-3.

[0185] In one embodiment of the present invention, Z3 is C or Si.

[0186] In one embodiment of the present invention, the chemical formula 2 is the chemical formula 2-4.

[0187] In one embodiment of the present invention, the chemical formula 2 is one of the following structures. [ka]

[0188] In the above structure, R50~R61 and R52' are either identical or different from each other, and each is independently a hydrogen; deuterium; halogen group; cyano group; alkoxy group; aryloxy group; siloxane group; substituted or unsubstituted amine group; substituted or unsubstituted alkyl group; substituted or unsubstituted aryl group; substituted or unsubstituted heterocyclic group; or crosslinkable group, and adjacent groups may bond to each other to form a ring. If r50~r59 and r52' are integers from 1 to 4, r60 is an integer from 1 to 5, r61 is an integer from 1 to 3, and r50~r61 and r52' are each 2 or greater, then the substituents in each parentheses are either identical or different from each other. * indicates a bond point within the polymer.

[0189] In one embodiment of the present invention, R50 to R61 and R52' are each hydrogen.

[0190] Specifically, the chemical formula 2 is one of the following structures. [ka]

[0191] In the above structure, * represents a bonding point within the polymer.

[0192] More specifically, the above chemical formula 2 is one of the following structures. [ka] In the above structure, * represents a bonding point within the polymer.

[0193] More specifically, the above chemical formula 2 is one of the following structures. [ka] In the above structure, * represents a bonding point within the polymer.

[0194] The terminal groups will be explained below.

[0195] In one embodiment of the present invention, E is an end-capping unit of the polymer.

[0196] In one embodiment of the present invention, E is a unit having only one connection point.

[0197] In one embodiment of the present invention, E is a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a crosslinkable group; or a combination thereof.

[0198] In one embodiment of the present invention, E is a substituted or unsubstituted C1-C30 alkyl group; a substituted or unsubstituted C6-C30 aryl group; a crosslinkable group; or a combination thereof.

[0199] In one embodiment of the present invention, E is a substituted or unsubstituted C1-C10 alkyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a crosslinkable group; or a combination thereof.

[0200] In one embodiment of the present invention, E is a crosslinkable group; or one of the following structures. [ka]

[0201] In the above structure, R70~R72 are either identical or different from each other, and each is independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; or a crosslinking group. L70 is a direct bond; a substituted or unsubstituted alkylene group; or a substituted or unsubstituted arylene group. i1 is an integer between 1 and 10, and if i1 is 2 or greater, then L70 values ​​greater than or equal to 2 are either identical 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 more, the substituents in each parentheses are the same as or different from each other. * is a crosslinking point in the polymer.

[0202] In one embodiment of the present invention, the E is any one of the following structures. [Chemical formula]

[0203] In the above structure, R70 to R72, L70, i1, n70 to n72, and * are as described above.

[0204] In one embodiment of the present invention, R70 to R72 are the same as or different from each other, and each is independently hydrogen; deuterium; an alkyl group having 1 to 10 carbon atoms; or a crosslinkable group.

[0205] In one embodiment of the present invention, L70 is a direct bond; an alkylene group having 1 to 10 carbon atoms; or an arylene group having 6 to 30 carbon atoms.

[0206] In one embodiment of the present invention, the E is any one of the following structures. [Chemical formula] In the above structure, * is a crosslinking point in the polymer.

[0207] More specifically, the E is any one of the following structures. [Chemical formula] In the above structure, * is a crosslinking point in the polymer.

[0208] Hereinafter, the polymer will be described.

[0209] In one embodiment of the present invention, the polymer is represented by the following Chemical Formula 5. [Chemical Formula]

[0210] In Chemical Formula 5, A1 is the first unit represented by Chemical Formula 1, B1 is the second unit represented by Chemical Formula 2, C1 is different from the first unit and is the third unit represented by Chemical Formula 4, E1 and E2 are the same as or different from each other and are each end groups represented by Chemical Formula 3, a, b, and c are molar fractions, respectively. a is a real number where 0 < a < 1, b is a real number where 0 < b < 1, c is a real number where 0 < c < 1, and a + b + c = 1.

[0211] In one embodiment of the present invention, a, b, and c are determined according to the equivalent ratio of the monomers used in the production of the polymer.

[0212] In one embodiment of the present invention, a is a real number of 0.05 or more and less than 1. In one embodiment of the present invention, a is a real number of 0.1 or more and less than 1. In one embodiment of the present invention, a is a real number of 0.05 to 0.9. In one embodiment of the present invention, a is a real number of 0.1 to 0.9. In one embodiment of the present invention, a is a real number of 0.2 to 0.9.

[0213] In one embodiment of the present invention, b is a real number greater than 0 and less than 1. In one embodiment of the present invention, b is a real number greater than 0 and less than or equal to 0.9. In one embodiment of the present invention, b is a real number of 0.05 to 0.9. In one embodiment of the present invention, b is a real number of 0.05 to 0.8. In one embodiment of the present invention, b is a real number of 0.1 to 0.8.

[0214] In one embodiment of the present invention, c is a real number greater than 0 and less than 1. In one embodiment of the present invention, c is a real number greater than 0 and less than or equal to 0.9. In one embodiment of the present invention, c is a real number greater than 0 and less than or equal to 0.8.

[0215] In one embodiment of the present invention, a is a real number between 0.05 and less than 1, b is a real number greater than 0 and less than 1, and c is a real number greater than 0 and less than 1.

[0216] In one embodiment of the present invention, a is a real number between 0.05 and 0.9, b is a real number between 0.05 and 0.8, and c is a real number greater than 0 and less than or equal to 0.9.

[0217] In this specification, a, b, and c are mole fractions based on the sum of A1, B1, and C1, not on the mole fraction of the entire polymer represented by chemical formula 5 including E1 and E2.

[0218] In one embodiment of the present invention, the molar ratio of (A1+B1+C1):(E1+E2) is 40:60 to 98:2.

[0219] In one embodiment of the present invention, the polymer is an alternating polymer, a block polymer, or a random polymer.

[0220] In one embodiment of the present invention, the chemical formula 5 does not mean only that A1, B1, and C1 are arranged in a specific order in the polymer. Specifically, A1, B1, and C1 may be arranged in various orders in the polymer. For example, the polymer may be in the order 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.

[0221] Also, in the polymer, the chemical formula 5 does not have a structure in which only one of A1, B1, and C1 is linked. For example, the polymer may be linked in various content ranges in the polymer, such as E1-A1-B1-A1-C1-E2, E1-A1-C1-B1-C1-E2, E1-A1-B1-C1-A1-E2, etc. At this time, the content ranges of A1, B1, and C1 are determined according to the equivalent ratio of the monomers used in the production of the polymer.

[0222] In one embodiment of the present invention, 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.

[0223] In one embodiment of the present invention, the number average molecular weight (Mn) of the polymer is 5,000 g / mol to 3,000,000 g / mol. Specifically, the number average molecular weight (Mn) of the polymer is 5,000 g / mol to 1,000,000 g / mol. More specifically, the number average molecular weight (Mn) of the polymer is 10,000 g / mol to 300,000 g / mol.

[0224] In one embodiment of the present invention, the molecular weight of the polymer is measured by a Gel Permeation Chromatography (GPC) method.

[0225] Specifically, the molecular weight can be measured as a relative value to a standard polystyrene (PS) sample by GPC (Gel Permeation Chromatography, waters breeze) using THF (tetrahydrofuran) as the eluate. More precisely, it is a value obtained by applying the weight-average molecular weight (Mw) and number-average molecular weight (Mn) on a polystyrene basis, which were determined by gel permeation chromatography (GPC: PLgel HFIPGEL, Agilent Technologies).

[0226] More specifically, the polymer to be measured is dissolved in tetrahydrofuran to a concentration of 1%, and 10 μl is injected into the GPC at a flow rate of 0.3 mL / min. Analysis can be performed at 30°C for a sample concentration of 2.0 mg / mL (100 μl injection). The column may consist of two Waters PLgel HFIPGEL columns connected in series, and the detector may be an RI detector (Agilent Waters, 2414) measured at 40°C, followed by data processing using ChemStation.

[0227] When the weight-average molecular weight of the polymer satisfies the aforementioned range, the viscosity is suitable, and it exhibits the effect of facilitating the fabrication of inkjet elements and organic light-emitting elements using fine pixels.

[0228] In one embodiment of the present invention, the polymer has a molecular weight distribution (PDI) of 1 to 10. Preferably, the polymer has a molecular weight distribution of 1 to 5. More preferably, the polymer has a molecular weight distribution of 1 to 4.

[0229] In this specification, the molecular weight distribution (PDI) is calculated by the following formula (1). Formula (1): PDI=weight average molecular weight (Mw) / number average molecular weight (Mn)

[0230] A large molecular weight distribution in a polymer means that molecules of various molecular weights are distributed, which makes it difficult to synthesize the polymer reproducibly. Therefore, the larger the molecular weight distribution, the lower the uniformity of the polymer. In other words, the closer the molecular weight distribution is to 1, the more homogeneous the polymer produced.

[0231] In one embodiment of the present invention, in the polymer, the first unit represented by chemical formula 1; the second unit represented by chemical formula 2; the third unit represented by chemical formula 4, which is different from the first unit; and the terminal group represented by chemical formula 3 can be distributed in such a way that the properties of the polymer are optimized.

[0232] In one embodiment of the present invention, when a1 is the mole fraction of the first unit represented by chemical formula 1 in the polymer, b1 is the mole fraction of the second unit represented by chemical formula 2, c1 is the mole fraction of the third unit represented by chemical formula 4 (which is different from the first unit), and e1 is the mole fraction of the terminal group represented by chemical formula 3, then a1, b1, c1, and e1 are each real numbers, and 0 <a1<1、0<b1<1、0<c1<1、0<e1<1であり、a1+b1+c1+e1=1である。

[0233] In one embodiment of the present invention, a1 is a real number between 0.05 and less than 1. In one embodiment of the present invention, a1 is a real number between 0.05 and 0.95. In one embodiment of the present invention, a1 is a real number between 0.1 and 0.9. In one embodiment of the present invention, a1 is a real number between 0.05 and 0.8.

[0234] In one embodiment of the present invention, b1 is a real number between 0.05 and less than 1. In one embodiment of the present invention, b1 is a real number between 0.05 and 0.95. In one embodiment of the present invention, b1 is a real number between 0.05 and 0.8. In one embodiment of the present invention, b1 is a real number between 0.1 and 0.8.

[0235] In one embodiment of the present invention, c1 is a real number greater than 0 and less than 1. In one embodiment of the present invention, c1 is a real number greater than 0 and less than or equal to 0.95. In one embodiment of the present invention, c1 is a real number greater than 0 and less than or equal to 0.9. In one embodiment of the present invention, c1 is a real number greater than 0 and less than or equal to 0.8. In one embodiment of the present invention, c1 is a real number between 0.05 and less than 1. In one embodiment of the present invention, c1 is a real number between 0.05 and 0.95. In one embodiment of the present invention, c1 is a real number between 0.1 and 0.9. In one embodiment of the present invention, c1 is a real number between 0.05 and 0.8.

[0236] In one embodiment of the present invention, e1 is a real number between 0.05 and less than 1. In one embodiment of the present invention, e1 is a real number between 0.05 and 0.95. In one embodiment of the present invention, e1 is a real number between 0.1 and 0.9. In one embodiment of the present invention, e1 is a real number between 0.05 and 0.8. In one embodiment of the present invention, e1 is a real number between 0.1 and 0.8.

[0237] In one embodiment of the present invention, a1 is a real number between 0.05 and less than 1, b1 is a real number between 0.05 and less than 1, c1 is a real number greater than 0 and less than 1, e1 is a real number between 0.05 and less than 1, and a1 + b1 + c1 + e1 = 1.

[0238] In one embodiment of the present invention, a1 is a real number between 0.05 and 0.8, b1 is a real number between 0.05 and 0.8, c1 is a real number greater than 0 and less than or equal to 0.8, and e1 is a real number between 0.05 and 0.8, and a1 + b1 + c1 + e1 = 1.

[0239] In one embodiment of the present invention, 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 0.05 to 0.8, e1 is a real number from 0.05 to 0.8, and a1 + b1 + c1 + e1 = 1.

[0240] In one embodiment of the present invention, the polymer is any one of the following structures.

[0241]

Chemical formula

[0242]

Chemical formula

[0243]

Chemical formula

[0244] [[ID=三十三]]

Chemical formula

[0245]

Chemical formula

[0246]

Chemical formula

[0247] In the above structure, a1 is a real number where 0 < a1 < 1, b1 is a real number where 0 < b1 < 1, c1 is a real number where 0 < c1 < 1, e1 is a real number where 0 < e1 < 1, and a1 + b1 + c1 + e1 = 1.

[0248] In one embodiment of the present invention, a1 is a real number between 0.05 and 0.8, b1 is a real number between 0.05 and 0.8, c1 is a real number greater than 0 and less than or equal to 0.8, and e1 is a real number between 0.05 and 0.8, and a1 + b1 + c1 + e1 = 1.

[0249] In one embodiment of the present invention, a1 is a real number between 0.05 and 0.8, b1 is a real number between 0.05 and 0.8, c1 is a real number between 0.05 and 0.8, and e1 is a real number between 0.05 and 0.8, and a1 + b1 + c1 + e1 = 1.

[0250] In the above structure, a1, b1, c1, and e1 are determined according to the equivalent amounts of monomers added during the production of the polymer.

[0251] In one embodiment of the present invention, the polymer may be produced using known polymerization techniques. For example, production methods such as the Suzuki, Yamamoto, Still, metal-catalyzed CN coupling reaction, and metal-catalyzed arylation reaction may be applied.

[0252] In one embodiment of the present invention, the polymer may be substituted with deuterium. In this case, the deuterium may be substituted by applying a method using a precursor material. For example, deuterium can be substituted by treating the undeuterated monomer and / or polymer with a deuterating solvent in the presence of a Lewis acid H / D exchange catalyst.

[0253] In one embodiment of the present invention, the molecular weight of the polymer may be controlled by adjusting the ratio of the monomers used. In some embodiments, the molecular weight of the polymer may also be controlled using a quenching reaction.

[0254] In one embodiment of the present invention, the polymer may be used as a hole transport material. For example, the polymer may be a "hole transport polymer".

[0255] In one embodiment of the present invention, the "layers," "films," and "layers" may be formed by any conventional coating technique, 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.

[0256] In one embodiment of the present invention, the polymer has an intrinsic viscosity of less than 20 cP. This is particularly useful for inkjet printing applications, as the lower viscosity allows for the ejection of a more concentrated solution. Specifically, the polymer has an intrinsic viscosity of less than 15 cP, more specifically less than 10 cP, and even more specifically less than 8 cP.

[0257] In one embodiment of the present invention, the intrinsic viscosity of the polymer is 1 cP or more and less than 20 cP, specifically 1 cP to 10 cP, and more specifically 1 cP to 8 cP.

[0258] The aforementioned intrinsic viscosity was obtained by dissolving the polymer to be measured in chloroform solvent at a concentration of 0.5 g / dl, and then measuring it at 25°C using an Ubbelohde viscometer.

[0259] The following describes the coating composition containing the polymer.

[0260] One embodiment of the present invention provides a coating composition comprising the polymer described above.

[0261] In one embodiment of the present invention, the coating composition further comprises a solvent. In one embodiment of this specification, the coating composition comprises the polymer and a solvent.

[0262] In one embodiment of the present invention, the coating composition may be in liquid form. The term "liquid form" means being in a liquid state at room temperature and atmospheric pressure.

[0263] In one embodiment of the present invention, it is preferable that the solvent does not dissolve the substance applied to the lower layer.

[0264] In one embodiment of the present invention, when the coating composition is applied to the organic layer of an organic light-emitting element, a solvent that does not dissolve the material of the lower layer is used. For example, when the coating composition is applied to the hole transport layer, a solvent that does not dissolve the material of the lower layer (first electrode, hole injection layer, etc.) is used. This has the advantage that the hole transport layer can be introduced by a solution process.

[0265] In one embodiment of the present invention, the coating composition exhibits improved resistance to solvents during heat treatment after coating.

[0266] For example, even if a coating composition is manufactured using a solvent that dissolves the polymer, and a layer is produced by a solution process, the coating can still be resistant to the same solvent after heat treatment.

[0267] Therefore, if an organic layer is formed using the polymer and then subjected to a heat treatment process, a solution process becomes possible when applying other organic layers.

[0268] In one embodiment of the present invention, the solvent contained in the coating composition is, for example, a chlorine-based solvent such as chloroform, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, o-dichlorobenzene; an ether-based solvent such as tetrahydrofuran, dioxane; an aromatic hydrocarbon-based solvent such as toluene, xylene, trimethylbenzene, mesitylene; a ketone-based solvent such as acetone, methyl ethyl ketone, cyclohexanone; an ester-based solvent such as ethyl acetate, butyl acetate, ethyl cellosolve acetate; ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, Examples of suitable solvents include polyhydric alcohols and their derivatives such as dimethoxyethane, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerin, and 1,2-hexanediol; alcoholic 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-phenoxybenzoate; and tetralin. However, any solvent capable of dissolving or dispersing the polymer according to one embodiment of the present invention is acceptable and not limited to these.

[0269] In one embodiment of the present invention, the solvent may be used alone or as a mixture of two or more solvents.

[0270] In one embodiment of the present invention, the boiling point of the solvent is preferably 40°C to 350°C, more preferably 80°C to 330°C, but is not limited to these values.

[0271] In one embodiment of the present invention, 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 to these values.

[0272] In one embodiment of the present invention, the remaining components in the coating composition, excluding the polymer, are solvents.

[0273] The following describes an organic light-emitting device containing the aforementioned polymer.

[0274] One embodiment of the present invention provides an organic light-emitting element comprising a first electrode; a second electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers contain the polymer.

[0275] The organic layer of the organic light-emitting element of the present invention may have a single-layer structure, or it may have a multilayer structure in which two or more organic layers are stacked. For example, the organic light-emitting element of the present invention may have a structure in which the organic layer includes a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, a layer that performs hole injection and hole transport simultaneously, and a layer that performs electron injection and electron transport simultaneously. However, the structure of the organic light-emitting element is not limited thereto and may include even fewer organic layers.

[0276] If the organic light-emitting element includes multiple organic layers, the organic layers may be formed from the same substance or different substances.

[0277] In one embodiment of the present invention, the organic light-emitting element includes a first electrode; a second electrode; and a light-emitting layer provided between the first electrode and the second electrode, further comprising a single layer of organic material between the light-emitting layer and the first electrode, wherein the organic material layer comprises the polymer.

[0278] In one embodiment of the present invention, the organic light-emitting element includes a first electrode; a second electrode; and a light-emitting layer provided between the first electrode and the second electrode, further comprising a multilayer organic material layer between the light-emitting layer and the first electrode, wherein one or more of the organic material layers contain the polymer.

[0279] In one embodiment of the present invention, the organic layer containing the polymer is a hole injection layer, a hole transport layer, or a layer that performs both hole injection and hole transport simultaneously.

[0280] In one embodiment of the present invention, the organic light-emitting element includes a first electrode; a second electrode; and a light-emitting layer provided between the first electrode and the second electrode, further comprising one or more layers selected from a hole injection layer, a hole transport layer, and an electron barrier layer between the light-emitting layer and the first electrode, wherein one or more of the hole injection layer, hole transport layer, and electron barrier layer comprises the polymer.

[0281] In one embodiment of the present invention, the organic light-emitting element 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, wherein one or more of the hole injection layer and the hole transport layer contain the polymer.

[0282] In one embodiment of the present invention, the organic light-emitting element 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 stacked, and one or more of the hole injection layer and hole transport layer contain the polymer.

[0283] In one embodiment of the present invention, the organic light-emitting element 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 stacked, and the hole injection layer or the hole transport layer contains the polymer.

[0284] In one embodiment of the present invention, the organic light-emitting element 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 stacked, and the hole transport layer contains the polymer.

[0285] In one embodiment of the present invention, an additional organic layer may be further included between the light-emitting layer and the second electrode.

[0286] In one embodiment of the present invention, a single layer of organic material may be further included between the light-emitting layer and the second electrode.

[0287] In one embodiment of the present invention, a multilayer organic material layer may be further included between the light-emitting layer and the second electrode. For example, one or more layers selected from a hole-blocking layer, an electron-injection layer, an electron-transport layer, and a layer that performs both electron injection and electron transport may be further included between the light-emitting layer and the second electrode.

[0288] In one embodiment of the present invention, the organic light-emitting element 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 stacked, and one or more of the hole injection layer and hole transport layer contain the polymer.

[0289] In one embodiment of the present invention, the organic light-emitting element 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 stacked, and the hole injection layer or the hole transport layer contains the polymer.

[0290] In one embodiment of the present invention, the organic light-emitting element 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 stacked, and the hole transport layer contains the polymer.

[0291] An example of an organic light-emitting element according to one embodiment of the present invention is shown in Figures 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 stacked. Figure 2 illustrates the structure of an organic light-emitting element in which a substrate 1, anode 2, hole injection layer 5, hole transport layer 6, light-emitting layer 3, electron injection and transport layer 7, and cathode 4 are sequentially stacked. Figures 1 and 2 illustrate organic light-emitting devices, but the structure of the organic light-emitting device of the present invention is not limited to these.

[0292] In one embodiment of the present invention, 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.

[0293] In one embodiment, the organic light-emitting element may be an organic light-emitting element with a structure (normal type) in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate.

[0294] In one embodiment, the organic light-emitting element may be an inverted type organic light-emitting element in which a cathode, one or more organic layers, and an anode are sequentially stacked on a substrate.

[0295] The organic light-emitting element of the present invention may be stacked in a structure as illustrated below. (1) Anode / Hole transport layer / Emitting layer / Cathode (2) Anode / Hole injection layer / Hole transport layer / Emitting layer / Cathode (3) Anode / Hole injection layer / Hole buffer layer / Hole transport layer / Emission layer / Cathode (4) Anode / Hole transport layer / Emitting layer / Electron transport layer / Cathode (5) Anode / Hole transport layer / Emitting layer / Electron transport layer / Electron injection layer / Cathode (6) Anode / Hole injection layer / Hole transport layer / Emitting layer / Electron transport layer / Cathode (7) Anode / Hole injection layer / Hole transport layer / Emitting layer / Electron transport layer / Electron injection layer / Cathode (8) Anode / Hole injection layer / Hole buffer layer / Hole transport layer / Emitting layer / Electron transport layer / Cathode (9) Anode / Hole injection layer / Hole buffer layer / Hole transport layer / Emitting layer / Electron transport layer / Electron injection layer / Cathode (10) Anode / Hole transport layer / Electron suppression layer / Emitting layer / Electron transport layer / Cathode (11) Anode / Hole transport layer / Electron suppression layer / Emitting layer / Electron transport layer / Electron injection layer / Cathode (12) Anode / Hole injection layer / Hole transport layer / Electron suppression layer / Emitting layer / Electron transport layer / Cathode (13) Anode / Hole injection layer / Hole transport layer / Electron suppression layer / Emitting layer / Electron transport layer / Electron injection layer / Cathode (14) Anode / Hole transport layer / Emitting layer / Hole suppression layer / Electron transport layer / Cathode (15) Anode / Hole transport layer / Emitting layer / Hole suppression layer / Electron transport layer / Electron injection layer / Cathode (16) Anode / Hole injection layer / Hole transport layer / Emitting layer / Hole suppression layer / Electron transport layer / Cathode (17) Anode / Hole injection layer / Hole transport layer / Emitting layer / Hole suppression layer / Electron transport layer / Electron injection layer / Cathode (18) Anode / Hole injection layer / Hole transport layer / Electron suppression layer / Emitting layer / Hole blocking layer / Electron injection layer and transport layer / Cathode

[0296] In the above structure, the "electron transport layer / electron injection layer" may be replaced with an "electron injection and transport layer" or a "layer that performs electron injection and electron transport simultaneously."

[0297] For example, the organic light-emitting element of the present invention may be stacked 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.

[0298] In the above structure, the "hole injection layer / hole transport layer" may be replaced with a "hole injection and transport layer" or a "layer that performs hole injection and hole transport simultaneously."

[0299] The organic light-emitting element of the present invention may be manufactured by materials and methods well known in the art, except that one or more layers of the organic material are made to contain the polymer. Specifically, the organic light-emitting element may be formed using a coating composition in which one or more layers of the organic material are made to contain the polymer.

[0300] For example, the organic light-emitting device of the present invention can be manufactured by sequentially stacking an anode, an organic layer, and a cathode on a substrate. In this case, a metal or a conductive metal oxide or an alloy thereof can be deposited on the substrate using a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation to form the anode, and then an organic layer including a hole injection layer, a hole transport layer, an emissive layer, and an electron injection and transport layer can be formed on top of that, and finally a material that can be used as a cathode can be deposited on top of that. In addition to this method, an organic light-emitting device can also be manufactured by sequentially depositing the cathode material, organic layer, and anode material on a substrate.

[0301] Furthermore, the present invention provides a method for manufacturing an organic light-emitting element formed using the coating composition described above.

[0302] Specifically, in one embodiment of the present invention, the steps include: 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.

[0303] In one embodiment of the present invention, the organic layer formed using the coating composition is formed using spin coating.

[0304] In another embodiment, the organic layer formed using the coating composition is formed by a printing method.

[0305] In one embodiment of the present invention, the printing method may include, but is not limited to, inkjet printing, nozzle printing, offset printing, transfer printing, or screen printing.

[0306] A coating composition according to one embodiment of the present invention is suitable for solution processing due to its structural properties and can be formed by a printing method, thus having the effect of being economical in terms of time and cost during the manufacturing of the device.

[0307] In one embodiment of the present invention, the step of forming an organic layer using the coating composition includes the step of coating the first electrode with the coating composition; and the step of heat-treating or photo-treating the coated coating composition.

[0308] In one embodiment, the heat treatment time in the heat treatment step may be within 1 hour. Specifically, it may be within 30 minutes.

[0309] In one embodiment of the present invention, the atmosphere used to heat-treat the organic layer formed using the coating composition is preferably an inert gas atmosphere such as argon or nitrogen.

[0310] If the organic layer formed using the coating composition includes a heat treatment or phototreatment step, the resistance to the solvent increases, the solution deposition and crosslinking method can be repeated to form a multilayer, the stability increases, and the lifespan characteristics of the device can be improved.

[0311] In one embodiment of the present invention, layers other than the organic layer formed using the coating composition are formed by spin coating, printing, or vapor deposition. For example, when the coating composition is applied to a hole injection layer or a hole transport layer, the hole injection layer or hole transport layer is formed by spin coating, and the other organic layers may be formed by spin coating, printing, or vapor deposition. Furthermore, an upper layer provided in contact with the organic layer formed using the coating composition may be formed by spin coating. As an example, when the coating composition is applied to a hole transport layer, the hole transport layer is formed by spin coating, an emissive layer formed on the hole transport layer in contact with the hole transport layer is formed by spin coating, and an electron injection and transport layer formed on the emissive layer may be formed by vapor deposition.

[0312] In one embodiment of the present invention, the anode material is usually preferably a material with a large work function to facilitate hole injection into the organic layer. Specific examples of anode materials usable in the present invention include, but are not limited to, metals or alloys thereof such as vanadium, chromium, copper, zinc, and gold; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline.

[0313] In one embodiment of the present invention, the cathode material is usually preferably a material with 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 or alloys thereof such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead; and multilayer materials such as LiF / Al or LiO2 / Al.

[0314] In one embodiment of the present invention, the hole injection layer is a layer into which holes are injected from the electrode. The hole injection material is preferably a compound that has the ability to transport holes, has an excellent hole injection effect on the light-emitting layer or light-emitting material, prevents the movement of excitons generated from the light-emitting layer to the electron injection layer or electron injection material, and has excellent thin-film formation ability. Furthermore, the HOMO (highest occupied molecular orbital) of the hole injection material is preferably between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of hole injection materials include, but are not limited to, metal porphyrins, oligothiophenes, arylamine-based organic compounds, hexanitrile-hexazatriphenylene-based organic compounds, quinacridone-based organic compounds, perylene-based organic compounds, carbazole-based organic compounds, anthraquinones, and conductive polymers of polyaniline and polythiophene. Specifically, the hole-injection layer may be, but is not limited to, a carbazole compound, an arylamine compound, or a compound in which a substituted or unsubstituted carbazole is linked to an arylamine group.

[0315] In one embodiment of the present invention, 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 the hole transport material is a material that can receive holes from the anode or hole injection layer and transfer them to the light-emitting layer, and a material with high mobility for holes is preferred. In one embodiment of the present invention, the hole transport layer includes the polymer.

[0316] In one embodiment of the present invention, the light-emitting layer includes an organic compound. The organic compound is a substance that can emit light in the visible light region by receiving and bonding holes and electrons from a hole transport layer and an electron transport layer, respectively, and is preferably a substance with good quantum efficiency for fluorescence and phosphorescence. Specific examples include, but are not limited to, 8-hydroxyquinoline aluminum complex (Alq3); carbazole compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzoxazole, benzothiazole, and benzimidazole compounds; poly(p-phenylenevinylene) (PPV) polymers; spiro compounds; polyfluorene; rubrene; and others.

[0317] In one embodiment of the present invention, the light-emitting layer may include a host material and a dopant material. Examples of the host material include condensed aromatic ring derivatives or heterocycle-containing compounds. Specifically, examples of condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluorantene compounds, while examples of heterocycle-containing compounds include, but are not limited to, carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, and pyrimidine derivatives. Examples of the dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, boron-containing compounds, fluorantene compounds, and metal complexes. For example, aromatic amine derivatives are condensed aromatic ring derivatives substituted with substituted or unsubstituted arylamino groups, such as fluorene, benzofluorene, pyrene, anthracene, chrysene, and perifurantene substituted with arylamino groups. Styrylamine compounds are compounds in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, and one or more substituents selected from the group consisting of aryl groups, silyl groups, alkyl groups, cycloalkyl groups, and arylamino groups are substituted or unsubstituted. Specifically, examples of styrylamine compounds include, but are not limited to, styrylamine, styryldiamine, styryltriamine, and styryltetraamine. Examples of metal complexes include, but are not limited to, iridium complexes and platinum complexes.

[0318] In one embodiment of the present invention, the host material is an anthracene derivative, and the dopant material is a benzofluorene compound substituted with an arylamine group or a compound containing boron. Specifically, the host material may be a deuterium-substituted or unsubstituted anthracene derivative, and the dopant material may be a bis(diarylamino)benzofluorene compound or a compound containing boron, but is not limited to these.

[0319] In one embodiment of the present invention, 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 quantum dots may be those well known in the art.

[0320] When the light-emitting layer contains quantum dots, it exhibits a lower HOMO energy level than when the light-emitting layer contains an organic compound; therefore, the common layer must also exhibit a lower HOMO energy level. The compound according to one embodiment of the present invention exhibits a low HOMO energy level by containing a halogen group, thus enabling the introduction of quantum dots into the light-emitting layer.

[0321] In one embodiment of the present invention, the common layer is a hole injection layer, a hole transport layer, a layer that performs hole injection and hole transport simultaneously, an electron injection layer, an electron transport layer, or a layer that performs electron injection and electron transport simultaneously.

[0322] In one embodiment of the present invention, the electron transport layer is a layer that receives electrons and transports them to the light-emitting layer, and the electron transport material is a material that can smoothly receive electron injection from the cathode and transfer them to the light-emitting layer, and a material with high electron mobility is preferred. Specific examples include, but are not limited to, Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic radical compounds; and hydroxyflavone-metal complexes. The electron transport layer may be used with any desired cathode material, as used in the prior art. In particular, examples of preferred cathode materials are ordinary materials having a low work function followed by an aluminum layer or a silver layer. Specifically, these include cesium, barium, calcium, ytterbium, and samarium, each of which is followed by an aluminum layer or a silver layer.

[0323] In one embodiment of the present invention, 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 on the light-emitting layer or light-emitting material, prevents the movement of excitons generated from the light-emitting layer to the hole injection layer, and is preferably a compound with excellent thin-film formation ability. Specifically, examples include, but are not limited to, fluorenone, anthraquinodimethane, diphenoquinone, thiopyrandioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidenemethane, anthrone, bathocuproine (BCP) and its derivatives, metal complex compounds, and nitrogen-containing five-membered ring derivatives.

[0324] In one embodiment of the present invention, the metal complex compound includes, but is not limited to, lithium 8-hydroxyquinolinate, bis(8-hydroxyquinolinate)zinc, bis(8-hydroxyquinolinate)copper, bis(8-hydroxyquinolinate)manganese, tris(8-hydroxyquinolinate)aluminum, tris(2-methyl-8-hydroxyquinolinate)aluminum, tris(8-hydroxyquinolinate)gallium, bis(10-hydroxybenzo[h]quinolinate)beryllium, bis(10-hydroxybenzo[h]quinolinate)zinc, bis(2-methyl-8-quinolinate)chlorogallium, bis(2-methyl-8-quinolinate)(o-crezolate)gallium, bis(2-methyl-8-quinolinate)(1-naphtholate)aluminum, and bis(2-methyl-8-quinolinate)(2-naphtholate)gallium.

[0325] In one embodiment of the present invention, the hole blocking layer is a layer that prevents holes from reaching the cathode, and may be formed under conditions generally similar to those of the hole injection layer. Specifically, examples include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, and aluminum complexes.

[0326] In one embodiment of the present invention, a layer adjacent to the organic layer containing the polymer represented by chemical formula 5, for example, a bank layer, contains a compound having fluorine as a substituent.

[0327] For example, if the polymer represented by chemical formula 5 is included in the hole transport layer, then one or more of the bank layer, hole injection layer, and light-emitting layer adjacent to the hole transport layer contain fluorine.

[0328] As described above, when an organic layer containing the polymer including the first unit, second unit, third unit, and terminal group is adjacent to a layer containing fluorine, the dipole moment changes due to the fluorine, resulting in the effect of forming a uniform layer.

[0329] The organic light-emitting element according to the present invention may be a top-emission type, a bottom-emission type, or a double-sided light-emitting type, depending on the material used. [Examples]

[0330] The present invention will be described in detail below with reference to examples. However, the examples of the present invention may be modified into various different forms, and the scope of this application should not be construed as being limited to the examples described below. The examples of this application are provided to give a more complete explanation of this specification to a person of average skill in the industry.

[0331] <Example of synthesis> <Synthesis Example 1: Production of Polymer 1> [ka]

[0332] (1-1) Preparation of compound Q-1 Compound w-1 (50.0 g, 1.00 eq), compound w-2 (65.2 g, 1.35 eq), potassium carbonate (K2CO3) (78.7 g, 2.5 eq), and bis(tri-tert-butylphosphine)palladium (0) (1.74 g, 0.015 eq) were placed in a round-bottom flask equipped with a condenser. Then, THF (500 mL) and distilled water (300 mL) were added, and the mixture was heated to 60°C and stirred for 6 hours. After adding distilled water to terminate the reaction, the organic solvent was extracted, and the mixture was concentrated under reduced pressure to obtain compound Q-1 (50.1 g) in liquid form.

[0333] (1-2) Preparation of compound P-1 Compound Q-2 (41.0 g, 1.00 eq) and the previously prepared compound Q-1 (50.0 g, 3.0 eq) were dissolved in xylene (200 mL) in a round-bottom flask with a condenser. Once completely dissolved, sodium tert-butoxide (40.0 g, 5.00 eq) and bis(tri-tert-butylphosphine)palladium (0) (2.1 g, 0.05 eq) were added, and the mixture was refluxed at 120°C for 3 hours. After terminating the reaction by injecting distilled water, the organic solvent was extracted with ethyl acetate and distilled water, and the mixture was precipitated with toluene and hexane to obtain compound P-1 as a white solid.

[0334] (1-3) Preparation of compound P-2 In a round-bottom flask with a condenser, compound P-1 (15.1 g, 1.00 eq), 4-bromo-4'-iodo-1,1'-biphenyl (13.16 g, 2.50 eq), and sodium tert-butoxide (7.0 g, 5.00 eq) were dissolved in toluene (200 mL). After complete dissolution, tris(dibenzylideneacetone)dipalladium(0) (0.67 g, 0.05 eq) and 1,1'-bis(diphenylphosphino)ferrocene (0.81 g, 0.10 eq) were added, and the mixture was refluxed at 90°C for 8 hours. After terminating the reaction by injecting distilled water, the organic solvent was extracted with ethyl acetate and distilled water, and compound P-2 with a purity of 99.7% was obtained by column chromatography.

[0335] (1-4) Preparation of Compound A-1 In a round-bottom flask equipped with a condenser, the previously prepared compound P-2 (10.00 g, 1.00 eq), 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. Once completely dissolved, 0.20 g (0.04 eq) of [1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (Pd(dppf)) was added, and the mixture was refluxed at 90°C for 8 hours. After terminating the reaction with deionized water (DI water), the organic solvent was extracted with ethyl acetate and distilled water, and compound A-1 with a purity of 99.3% was obtained by column chromatography.

[0336] (2) Production of compound B-2 [ka]

[0337] Compound B-1 (10.00 g, 1.00 eq), bis(pinacolato)diboron (14 g, 2.00 eq), and potassium tert-butoxide (1.60 g, 3.00 eq) were dissolved in 200 mL of toluene in a round-bottom flask with a condenser. Once completely dissolved, 0.20 g (0.04 eq) of [1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (Pd(dppf)) was added, and the mixture was refluxed at 90°C for 8 hours. After terminating the reaction with deionized water (DI water), the organic solvent was extracted with ethyl acetate and distilled water, and compound B-2 with a purity of 99.4% was obtained by column chromatography.

[0338] (3) Production of polymer 1 [ka]

[0339] Compound B-2 (0.382 mmol), Compound A-1 (0.382 mmol), 4,4''-dibromo-5'-(4-bromophenyl)-1,1':3',1''-terphenyl (0.158 mmol), and 4-bromo-4'-propyl-1,1'-biphenyl (0.369 mmol) were placed in a round-bottom flask and dissolved in toluene (11 mL). Then, tetrakis(triphenylphosphine)palladium(0)(Pd(PPh3)4) (0.05 mmol), 5 mL of 2 M potassium carbonate (K2CO3) solution, and Aliquat as a phase transfer catalyst were added. After injecting 0.1 mL of 336, the mixture was refluxed at 100°C for 12 hours. The reaction was terminated by gradually adding the reaction products dropwise to methanol, then the mixture was stirred for 45 minutes, and the resulting solid was filtered. The dried solid was dissolved in toluene (1% wt / v) and purified by passing it through a column containing silica gel and basic aluminum oxide (6 g each). The resulting toluene solution was triturated with acetone to produce polymer 1 (5.2 g).

[0340] <Synthesis Example 2: Preparation of Polymer 2> (1) Production of compound C-2 [ka]

[0341] Compound C-2 was prepared in the same manner as in Synthesis Example 1(2), except that compound C-1 was used instead of compound B-1.

[0342] (2) Production of polymer 2 [ka]

[0343] Polymer 2 was produced in the same manner as in Synthesis Example 1 (3), except that compound C-2 was used instead of compound B-2.

[0344] <Synthesis Example 3: Production of Polymer 3> (1) Preparation of compound D-2 [ka]

[0345] Compound D-2 was prepared in the same manner as in Synthesis Example 1(2), except that compound D-1 was used instead of compound B-1.

[0346] (2) Production of polymer 3 [ka]

[0347] Polymer 3 was produced in the same manner as in Synthesis Example 1 (3), except that compound D-2 was used instead of compound B-2.

[0348] <Synthesis Example 4: Production of Polymer 4> (1) Production of compound A-2 [ka]

[0349] Compound A-2 was prepared in the same manner as in Synthesis Example 1 (1-1) to (1-4), except that compound Q-3 was used instead of compound Q-2 in Synthesis Example 1 (1-2).

[0350] (2) Production of polymer 4 [ka]

[0351] Polymer 4 was produced in the same manner as in Synthesis Example 1, except that compound A-2 was used instead of compound A-1 in Synthesis Example 1 (3).

[0352] <Synthesis Example 5: Production of Polymer 5> [ka]

[0353] Polymer 5 was produced in the same manner as in Synthesis Example 2 (2), except that compound A-2 was used instead of compound A-1.

[0354] <Synthesis Example 6: Manufacturing of Modification 6> [ka]

[0355] Polymer 6 was produced in the same manner as in Synthesis Example 3 (2), except that compound A-2 was used instead of compound A-1.

[0356] <Synthesis Example 7: Production of Polymer X-1> [ka]

[0357] Compound A-1 (0.765 mmol), 4,4''-dibromo-5'-(4-bromophenyl)-1,1':3',1''-terphenyl (0.158 mmol), and 4-bromo-4'-propyl-1,1'-biphenyl (0.369 mmol) were placed in a round-bottom flask and dissolved in toluene (11 mL) to prepare the first solution.

[0358] Bis(1,5-cyclooctadiene)nickel(0)(2.42 mmol) was placed in a 50 mL Schlenk tube. 2,2'-dipyridyl(2.42 mmol) and 1,5-cyclooctadiene(2.42 mmol) were placed in a scintillation vial, and then dissolved in N,N'-dimethylformamide(5.5 mL) and toluene(11 mL) to prepare the second solution.

[0359] The second solution was placed in a Schlenk tube and stirred at 50°C for 30 minutes. The first solution was then placed in a Schlenk tube and stirred at 50°C for 3 hours. HCl and methanol (methanol:HCl = 95:5 (v:v)) were gradually added dropwise to terminate the reaction, after which the mixture was stirred for 45 minutes and the resulting solid was filtered. The dried solid was dissolved in toluene (1% wt / v) and purified by passing it through a column containing silica gel and basic aluminum oxide (6 g each). The resulting toluene solution was triturated with acetone to produce polymer X-1.

[0360] <Synthesis Example 8: Production of Polymer X-2> [ka]

[0361] Polymer X-2 was produced in the same manner as in Synthesis Example 7, except that 3,3''-dibromo-5'-(3-bromophenyl)-1,1':3',1''-terphenyl was used instead of 4,4''-dibromo-5'-(4-bromophenyl)-1,1':3',1''-terphenyl.

[0362] <Synthesis Example 9: Production of Polymer X-3> [ka]

[0363] Polymer X-3 was produced in the same manner as in the production method of Synthesis Example 7, except that 1,3,5-tribromobenzene was used instead of 4,4''-dibromo-5'-(4-bromophenyl)-1,1':3',1''-terphenyl.

[0364] Example 1: Measurement of Molecular Weight Molecular weight measurements confirmed the synthesis of polymers 1-6 and X-1-X-3.

[0365] <Example 1-1> The number-average molecular weight (Mn), weight-average molecular weight (Mw), and molecular weight distribution (PDI) of polymer 1 produced in Synthesis Example 1 were measured using GPC (Agilent, PLgel HFIPGEL column). The molecular weight distribution was calculated using the following formula (1). Formula (1): PDI=weight average molecular weight (Mw) / number average molecular weight (Mn)

[0366] <Examples 1-2 to 1-6> Except for using the polymers listed in Table 1 below instead of polymer 1 in Example 1-1, the number-average molecular weight (Mn), weight-average molecular weight (Mw), and molecular weight distribution (PDI) were measured in the same manner as in Example 1-1.

[0367] <Comparative Example 1-1> The number-average molecular weight (Mn), weight-average molecular weight (Mw), and molecular weight distribution (PDI) were measured in the same manner as in Example 1-1, except that polymer Q was used instead of polymer 1. [ka]

[0368] <Comparative Examples 1-2 to 1-4> Except for using the polymers listed in Table 2 below instead of polymer 1 in Example 1-1, the number-average molecular weight (Mn), weight-average molecular weight (Mw), and molecular weight distribution (PDI) were measured in the same manner as in Example 1-1.

[0369] The GPC results measured in Examples 1-1 to 1-6 and Comparative Examples 1-1 to 1-4 are shown in Tables 1 and 2 below.

[0370] [Table 1]

[0371] [Table 2]

[0372] Example 2: Measurement of thin film retention rate <Example 2-1> The polymer 1 produced in the above synthesis example 1 was dissolved in toluene at a concentration of 2 wt% to produce coating composition 1.

[0373] <Comparative Example 2-1> The following compound P-2, produced in (1-3) of Synthesis Example 1, was dissolved in toluene at a concentration of 2 wt% to produce coating composition 2.

[0374] <Comparative Example 2-2> The following compound P-4, produced in the above synthesis example 4, was dissolved in toluene at a concentration of 2 wt% to produce coating composition 3.

[0375] [ka]

[0376] Each of the coating compositions 1 to 3 was spin-coated onto glass to form a thin film, and the UV-vis absorption was measured. This thin film was then immersed again in cyclohexanone for 3 minutes, dried, and the UV-vis absorption was measured again. The retention rate of the thin film was confirmed by comparing the magnitude of the maximum peak of UV absorption before and after immersion.

[0377] Figure 3 shows the experimental results of the film retention rate of the thin film formed from coating composition 1. Figure 4 shows the experimental results of the film retention rate of the thin film formed from coating composition 2. Figure 5 shows the experimental results of the film retention rate of the thin film formed from coating composition 3. In Figures 3 to 5, (a) shows the UV measurement results immediately after the thin film was formed (before immersion in cyclohexanone for 3 minutes), and (b) shows the UV measurement results after immersion of the thin film in cyclohexanone for 3 minutes.

[0378] Figure 3 shows that in the case of a thin film formed from coating composition 1, the thin film retention rate is 100%. In other words, it can be confirmed that the polymer according to one embodiment of the present invention has excellent resistance to solvents. In contrast, Figures 4 and 5 show that the thin films formed from coating compositions 2 and 3 have a high thin film loss rate. In other words, it can be confirmed that the compounds used in the comparative example lack resistance to solvents.

[0379] Example 3: Manufacturing of an organic light-emitting element <Example 3-1> A glass substrate coated with a thin film of ITO (indium tin oxide) to a thickness of 1,500 Å was placed in distilled water with a detergent solution and cleaned ultrasonically. The detergent used was from Fischer Co., and the distilled water was distilled water that had been secondarily filtered using a Millipore Co. filter. After washing the ITO for 30 minutes, ultrasonic cleaning was repeated twice with distilled water for 10 minutes each time. After the distilled water cleaning, ultrasonic cleaning was performed with isopropyl alcohol and acetone solvents, followed by drying. The substrate was then washed for 5 minutes and dried again.

[0380] Immediately before fabricating the device, the cleaned and patterned ITO was treated with UV ozone for 10 minutes. After ozone treatment, a 2 wt% cyclohexanone solution containing compound A and compound B in an 8:2 weight ratio was spin-coated onto the ITO surface, and the solvent was removed by heat treatment to form a hole injection layer approximately 40 nm thick. On the hole injection layer formed above, a toluene (toluene) solution containing 1.5 wt% of polymer 1 produced in synthesis example 1 was spin-coated, and the solvent was removed by heat treatment to form a hole transport layer approximately 100 nm thick. On the hole transport layer, a methyl benzoate solution containing compound C and compound D (compound C:compound D = 93:7 (wt%)) at a concentration of 2.0 wt% was spin-coated to form an emissive layer approximately 100 nm thick. After being transferred to a vacuum deposition machine, BCP was vacuum-deposited onto the emissive layer to a thickness of 35 nm to form electron injection and transport layers. A cathode was formed on the electron injection and transport layer by sequentially depositing LiF to a thickness of 1 nm and aluminum to a thickness of 100 nm.

[0381] [ka]

[0382] In the process described above, the deposition rate of organic matter was maintained at 0.4 Å / sec to 1.0 Å / sec, the deposition rate of cathode LiF was maintained at 0.3 Å / sec, and the deposition rate of aluminum was maintained at 2 Å / sec. The vacuum level during deposition was 2 × 10⁻¹⁰ -8 torr~5×10 -6 Torr was maintained.

[0383] <Examples 3-2 to 3-6> Examples 3-2 to 3-6 were manufactured in the same manner as in Example 3-1, except that the polymers listed in Table 3 below were used instead of polymer 1.

[0384] <Comparative Examples 3-1 to 3-4> Comparative Examples 3-1 to 3-4 were manufactured in the same manner as in Example 3-1, except that polymer Q and polymers X-1 to X-3 were used instead of polymer 1.

[0385] [Table 3]

[0386] Unless otherwise specified in Table 3, the measurements are taken at 1000 nits, and V is 10 mA / cm². 2 The driving voltage (in volts) is given by the external quantum efficiency (QE), calculated as (number of emitted photons) / (number of injected charge carriers), the color coordinates (x) and (y) are the x and y coordinates according to the CIE chromaticity diagram (Commission Internationale de L'Eclairage, 1931), and CE / CIEy is the value obtained by dividing the luminous efficiency (cd / A) by the color coordinate (y) value.

[0387] As shown in Table 3, it was confirmed that the organic light-emitting devices (Examples 3-1 to 3-6) using the polymer according to the present invention had a lower or similar driving voltage and improved efficiency (luminous efficiency, power efficiency, and external quantum efficiency) compared to organic light-emitting devices (Comparative Examples 3-1 to 3-4) using polymers that did not contain the third unit.

[0388] Although preferred embodiments of the present invention (hole transport layer) have been described above, the present invention is not limited thereto and can be implemented in various ways within the scope of the claims and the detailed description of the invention, and this also falls within the scope of the invention. [Explanation of Symbols]

[0389] 1 ··· Circuit board 2 ···Anode 3 ···Emitting layer 4 ···Cathode 5 ···Hole injection layer 6 ···Hole transport layer 7 ···Electron injection and transport layer

Claims

1. The first unit represented by the following chemical formula 1; The second unit, represented by the following chemical formula 2; Unlike the first unit, the third unit is represented by the following chemical formula 4; and Polymers containing terminal groups represented by the following chemical formula 3: 【Chemistry 1】 【Chemistry 2】 In the aforementioned chemical formulas 1 to 4, Ar1 to Ar4 are either identical or different from each other, and each is independently a substituted or unsubstituted arylene group. L1 to L4 are identical or different from each other, and each is independently directly bonded; or substituted or unsubstituted arylene groups. R1 to R6 are either identical or different from each other, and each is independently hydrogen; deuterium; halogen group; substituted or unsubstituted alkyl group; substituted or unsubstituted silyl group; substituted or unsubstituted aryl group; substituted or unsubstituted heterocyclic group; substituted or unsubstituted arylamine group; or substituted or unsubstituted siloxane group. R11 to R16 are either identical or different from each other, and each is independently an alkyl group having 1 to 3 carbon atoms. R21 and R22 are either identical or different from each other, and independently of each other, are hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group. r1 to r6 are integers from 1 to 4, and if r1 to r6 are each 2 or greater, the substituents in each parentheses are either identical or different from each other. l1 to l4 are integers from 1 to 5, and if l1 to l4 are each 2 or greater, the structures within each set of parentheses are either identical or different from one another. 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. If Y is directly bonded; or a substituted or unsubstituted alkylene group, then Z is a trivalent or tetravalent substituted or unsubstituted aryl group. E is hydrogen; deuterium; substituted or unsubstituted alkyl group; substituted or unsubstituted silyl group; substituted or unsubstituted aryl group; substituted or unsubstituted arylamine group; substituted or unsubstituted siloxane group; crosslinking group; or a combination thereof. * indicates a bond point within the polymer.

2. The polymer is the polymer according to claim 1, represented by the following chemical formula 5: 【Transformation 3】 In the aforementioned chemical formula 5, A1 is the first unit represented by the chemical formula 1, B1 is the second unit represented by the chemical formula 2, Unlike the first unit, C1 is a third unit represented by the chemical formula 4. E1 and E2 are terminal groups that are identical or different from each other and are represented by the chemical formula 3. a, b, and c are mole fractions, where a is a real number such that 0 < a < 1, b is a real number such that 0 < b < 1, and c is a real number such that 0 < c < 1, and a + b + c = 1.

3. The polymer according to claim 1, wherein the chemical formula 4 is the following chemical formula 4-1: 【Chemistry 4】 In the aforementioned chemical formula 4-1, R4-R6, Ar3, Ar4, L3, L4, r4-r6, l3, and l4 are defined as in the same way as in the chemical formula 4 above. R23 and R24 are either identical or different to each other and are independently hydrogen; deuterium; halogen group; substituted or unsubstituted alkyl group; substituted or unsubstituted silyl group; substituted or unsubstituted aryl group; substituted or unsubstituted heterocyclic group; substituted or unsubstituted arylamine group; or substituted or unsubstituted siloxane group. r23 and r24 are integers from 1 to 5, and if r23 and r24 are each 2 or greater, the substituents in their respective parentheses are either identical or different.

4. The polymer according to claim 1, wherein the chemical formula 1 is the following chemical formula 1-1: 【Transformation 5】 In the above chemical formula 1-1, Ar1, Ar2, L1, L2, R11-R16, l1, and l2 are defined as in the same way as in Chemical Formula 1 above. R1, R2, R2', and R3 are identical or different from each other and are independently hydrogen; deuterium; halogen group; substituted or unsubstituted alkyl group; substituted or unsubstituted silyl group; substituted or unsubstituted aryl group; substituted or unsubstituted heterocyclic group; substituted or unsubstituted arylamine group; or substituted or unsubstituted siloxane group.

5. The polymer according to claim 1, wherein L1 and L2 are the same or different from each other, and each is independently a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

6. The polymer according to claim 1, wherein the chemical formula 2 is one of the following chemical formulas 2-1 to 2-4: 【Transformation 6】 【Transformation 7】 In the aforementioned chemical formulas 2-1 to 2-4, Z1 is CRa; SiRa; N; or a trivalent substituted or unsubstituted aryl group. Z2 and Z3 are either identical or different from each other, and each is independently a C; Si; or a tetravalent substituted or unsubstituted aryl group. L10 is a directly bonded; 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 may be the same or different from each other, and each may independently be hydrogen; deuterium; halogen group; cyano group; alkoxy group; aryloxy group; siloxane group; substituted or unsubstituted amine group; substituted or unsubstituted alkyl group; substituted or unsubstituted aryl group; substituted or unsubstituted heterocyclic group; or a crosslinking group, and adjacent groups may bond to each other to form a ring. If r50 to r59 are integers from 1 to 4, and r60 is an integer from 1 to 5, and if r50 to r60 are each 2 or greater, then the substituents in each parentheses are either identical or different from each other. * indicates a bond point within the polymer.

7. The polymer according to claim 1, wherein E is a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a crosslinkable group; or a combination thereof.

8. The polymer according to claim 1, wherein E is a crosslinkable group; or one of the following structures: 【Transformation 8】 In the above structure, R70 to R72 are either identical or different from each other, and each is independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; or a crosslinkable 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, then L70 values ​​of 2 or greater are either identical or different from each other. If n70 and n72 are integers from 1 to 5, n71 is an integer from 1 to 4, and n70 to n72 are each 2 or greater, then the substituents in each parentheses are either identical or different from each other. * indicates a bond point within the polymer.

9. The polymer according to claim 1, wherein the crosslinkable group represented by the chemical formula 3 is one of the following structures: 【Chemistry 9】 In the above structure, L30 to L36 are identical or different from each other, and independently consist of: directly bonded; -O-; -COO-; substituted or unsubstituted alkylene group; substituted or unsubstituted arylene group; or a combination thereof. 【Chemistry 10A】 The part represented by the chemical formula 3 is 【Chemistry 10B】 This corresponds to the part represented by [the symbol].

10. The polymer according to claim 1, wherein the polymer has one of the following structures: 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】 【Chemistry 16】 In the above structure, a1 is a real number such that 0 < a1 < 1, b1 is a real number such that 0 < b1 < 1, c1 is a real number such that 0 < c1 < 1, e1 is a real number such that 0 < e1 < 1, and a1 + b1 + c1 + e1 = 1.

11. first electrode; Second electrode; and The first electrode and the second electrode include one or more organic layers, An organic light-emitting element, wherein one or more of the organic layers contain the polymer described in any one of claims 1 to 10.

12. The organic light-emitting element according to claim 11, wherein the organic layer containing the polymer is a hole injection layer, a hole transport layer, or a layer that performs both hole injection and hole transport simultaneously.

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