Polymer and organic light-emitting device using 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, the entire contents of which are incorporated herein by reference.

[0002] The present invention relates to a polymer and an organic light-emitting device formed therewith. [Background technology]

[0003] The organic light-emitting phenomenon is an example of a phenomenon in which electric current is converted into visible light by an internal process of a specific organic molecule. The principle of the organic light-emitting phenomenon is as follows. When an organic layer is placed between an anode and a cathode, and an electric current is applied between the two electrodes, electrons and holes are injected into the organic layer from the cathode and anode, respectively. The electrons and holes injected into the organic layer recombine to form excitons, which then fall back to the ground state to emit light. An organic electroluminescent device using this principle may generally be composed of a cathode, an anode, and organic layers positioned therebetween, such as a hole injection layer, a hole transport layer, an emission layer, an electron transport layer, and an electron injection layer.

[0004] The majority of materials used in organic light-emitting devices are pure organic materials or complex compounds in which an organic material and a metal form a complex. They can be classified into hole injection materials, hole transport materials, light-emitting materials, electron transport materials, electron injection materials, etc. according to their applications. Here, organic materials having p-type properties, i.e., organic materials that are easily oxidized and have an electrochemically stable state when oxidized, are mainly used as hole injection materials and hole transport materials. On the other hand, organic materials having n-type properties, i.e., organic materials that are easily reduced and have an electrochemically stable state when reduced, are mainly used as electron injection materials and electron transport materials. As light-emitting materials, materials having both p-type properties and n-type properties at the same time, i.e., materials that are stable in both oxidized and reduced states, and materials with high luminous 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 device further has the following properties.

[0006] First, it is preferable that the material used in the organic light emitting device has excellent thermal stability. This is because Joule heating occurs due to the movement of charges in the organic light emitting device. 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 makes it difficult to use it in organic light emitting devices that require high current.

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

[0008] In addition, materials used in organic light emitting devices should have excellent chemical stability, charge mobility, and interface properties with electrodes and adjacent layers. That is, materials used in organic light emitting devices should be less susceptible to deformation due to moisture or oxygen. In addition, materials should have suitable hole or electron mobility to balance the density of holes and electrons in the light emitting layer of the organic light emitting device and maximize the formation of excitons. In addition, materials should have good interface properties with electrodes containing metals or metal oxides for device stability.

[0009] In addition to the above, materials used in the solution processable organic light emitting device should further have the following properties.

[0010] First, a homogeneous solution that can be stored must be formed. Commercially available materials for deposition processes have good crystallinity and do not dissolve well in solution, or even if a solution is formed, crystals tend to form, so there is a high possibility that the concentration gradient of the solution will change or defective devices will be formed depending on the storage period.

[0011] Secondly, the layer undergoing the solution process must be resistant to solvents and materials compared to other layers. For this purpose, materials that can form a polymer that is crosslinked by itself on the substrate by heat treatment or UV (ultraviolet) irradiation after introducing a curing group such as VNPB (N4,N4'-di(naphthalene-1-yl)-N4,N4'-bis(4-vinylphenyl)biphenyl-4,4'-diamine) or that can form a polymer that is sufficiently resistant to the next process after solution coating are preferred, and materials that can be resistant to solvents by themselves such as HATCN (hexaazatriphenylenehexacarbonitrile) are also preferred.

[0012] Therefore, there is a need in this technical field to develop an organic material that satisfies the above requirements. Summary of the Invention [Problem to be solved by the invention]

[0013] An object of the present invention is to provide a polymer and an organic light-emitting device formed using the polymer. [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 different from the first unit and represented by the following chemical formula 4: and an end group represented by the following chemical formula 3:

[0015] [ka] [ka]

[0016] In the above Chemical Formulas 1 to 4, Ar1 to Ar4 are the same or different and each independently represents a substituted or unsubstituted arylene group; L1 to L4 are the same or different and each independently represents a direct bond; or a substituted or unsubstituted arylene group; R1 to R6 are the same or different and each independently represents hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted arylamine group; or a substituted or unsubstituted siloxane group; R11 to R16 are the same or different and each independently represents an alkyl group having 1 to 3 carbon atoms; R21 and R22 are the same or different and each independently represents hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group; Each of r1 to r6 is an integer of 1 to 4, and when each of r1 to r6 is 2 or more, the substituents in each parentheses are the same or different. l1 to l4 are each an integer of 1 to 5, and when l1 to l4 are each 2 or more, the structures in the respective brackets are the same or different from each other, m is an integer of 3 or 4, When m is 3, Z is CRa; SiRa; N; or a trivalent substituted or unsubstituted aryl group; When m is 4, Z is C; Si; or a tetravalent substituted or unsubstituted aryl group; Ra is hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group; Y is a direct bond; a substituted or unsubstituted alkylene group; or a substituted or unsubstituted arylene group; When Y is a direct bond; or a substituted or unsubstituted alkylene group, Z is a trivalent or tetravalent substituted or unsubstituted aryl group; E is hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted arylamine group; a substituted or unsubstituted siloxane group; a crosslinkable group; or a combination thereof; * indicates a point of attachment within the polymer.

[0017] Another embodiment of the present invention provides an organic light-emitting device comprising: a first electrode; a second electrode; and one or more organic layers disposed between the first electrode and the second electrode, wherein one or more of the organic layers contains the polymer. Effect of the Invention

[0018] The polymer according to one embodiment of the present invention includes a unit of Chemical Formula 1 substituted with three alkyl groups having 1 to 3 carbon atoms, thereby exhibiting an effect of improving the solubility of the produced polymer. Furthermore, the polymer according to an embodiment of the present invention may 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] 1 is a diagram illustrating a structure of an organic light emitting device according to an embodiment of the present invention; [Diagram 2] 1 is a diagram illustrating a structure of an organic light emitting device according to an embodiment of the present invention; [Diagram 3] FIG. 2 is a diagram showing the experimental results of the film retention rate of a thin film formed from the coating composition 1 prepared in Example 2-1. [Figure 4] FIG. 2 is a diagram showing the experimental results of the film retention rate of a thin film formed from the coating composition 2 prepared in Comparative Example 2-1. [Diagram 5] FIG. 2 is a diagram showing the experimental results of the film retention rate of the thin film formed from the coating composition 3 prepared in Comparative Example 2-2. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0020] The present invention will now be described in more detail. 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 different from the first unit and represented by the following chemical formula 4: 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 the same or different and each independently represents a substituted or unsubstituted arylene group; L1 to L4 are the same or different and each independently represents a direct bond; or a substituted or unsubstituted arylene group; R1 to R6 are the same or different and each independently represents hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted arylamine group; or a substituted or unsubstituted siloxane group; R11 to R16 are the same or different and each independently represents an alkyl group having 1 to 3 carbon atoms; R21 and R22 are the same or different and each independently represents hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group; Each of r1 to r6 is an integer of 1 to 4, and when each of r1 to r6 is 2 or more, the substituents in each parentheses are the same or different. l1 to l4 are each an integer of 1 to 5, and when l1 to l4 are each 2 or more, the structures in the respective brackets are the same or different from each other, m is an integer of 3 or 4, When m is 3, Z is CRa; SiRa; N; or a trivalent substituted or unsubstituted aryl group; When m is 4, Z is C; Si; or a tetravalent substituted or unsubstituted aryl group; Ra is hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group; Y is a direct bond; a substituted or unsubstituted alkylene group; or a substituted or unsubstituted arylene group; When Y is a direct bond; or a substituted or unsubstituted alkylene group, Z is a trivalent or tetravalent substituted or unsubstituted aryl group; E is hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted arylamine group; a substituted or unsubstituted siloxane group; a crosslinkable group; or a combination thereof; * indicates a point of attachment 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 in the core, and is conjugated with -(L-phenyl group) substituted with an amine group. In this case, three alkyl groups are substituted at specific positions on the phenyl group in the -(L-phenyl group), thereby breaking the conjugation and improving charge mobility. Therefore, the polymer contains a phenyl group substituted with three alkyl groups, and thus can exhibit low driving 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" another member (layer), this includes not only the case where a member (layer) is in contact with the other member, but also the case where another member (layer) exists between two members (layers).

[0025] In this specification, when a part "comprises" a certain component, this does not mean excluding other components, but means that the part may further include other components, unless otherwise specified to the contrary.

[0026] In this specification, the term "layer" is interchangeable with the term "membrane" or "film" used primarily in this technical field, and refers to a coating that covers a desired area. The size of the "layer" is not limited, and each "layer" may be the same 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 a single sub-pixel.

[0027] As used herein, "or" refers to an inclusive "or" and not an exclusive "or." For example, a condition A or B means that the condition is satisfied by any one of the following: 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 layer B includes both i) one or more types of substance A being contained in one layer B, and ii) layer B being composed of one or more layers and substance A being contained in one or more of the multiple layer Bs.

[0029] In this specification, when a specific substance A is contained in layer C or layer D, it means that substance A is i) contained in one or more of one or more C layers, ii) contained in one or more of one or more D layers, or iii) contained in one or more C layers and one or more D layers.

[0030] As used herein, "mole fraction" means the ratio of moles of a given component to the total number of moles of all components.

[0031] In this specification, the term "adjacent" groups may refer to a substituent substituted on an atom directly connected to the atom on which the substituent is substituted, a substituent sterically 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 positions on a benzene ring and two substituents substituted on the same carbon atom on an aliphatic ring can be interpreted as "adjacent" groups to each other.

[0032] As used herein, in a ring formed by bonding adjacent groups to each other, the term "ring" refers to a substituted or unsubstituted hydrocarbon ring; or a substituted or unsubstituted heterocycle.

[0033] In this specification, unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by those skilled in the art to which the present invention belongs. Methods and materials similar or equivalent to those described in this specification may be used in the practice or testing of embodiments of the present invention, and suitable methods and materials are described below. All publications, patents, and other references mentioned in this specification are incorporated by reference in their entirety, and in the event of a conflict, the present specification, including definitions, will take precedence unless a specific passage is mentioned. It should be noted that the materials, methods, and examples are merely illustrative and are not intended to be limiting.

[0034] In this specification, [ka] denotes a moiety that is connected to another substituent or bond.

[0035] In this specification, "*" denotes a point of attachment within the polymer.

[0036] The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position of the substitution is not limited as long as it is a position at which a hydrogen atom is substituted, i.e., a position at which a substituent can be substituted, and when two or more substituents are substituted, the two or more substituents may be the same or different.

[0037] In this specification, the term "substituted or unsubstituted" means that it is substituted with one or more substituents selected from the group consisting of deuterium, halogen group, alkyl group, cycloalkyl group, alkoxy group, aryloxy group, amine group, aryl group, heterocyclic group, and crosslinkable group, or that it is substituted with a substituent in which two or more of the above-listed substituents are linked, or that it does not have any substituent. For example, the "substituent in which two or more substituents are linked" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may also be interpreted as a substituent in which two phenyl groups are linked.

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

[0039] As used herein, examples of halogen groups 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. According to one embodiment, the number of carbon atoms of the alkyl group is 1 to 30. Specific examples of the alkyl group include, but are not limited to, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, and an octyl group.

[0041] In this specification, the alkylene group refers to an alkyl group having two bonding positions, i.e., a divalent group. The above description of the alkyl group may be applied, 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. According to 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 of the alkoxy group is not particularly limited, but it is preferable that the number of carbon atoms is 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] As used herein, an amine group is defined as -NH 2 The amine group may be selected from the group consisting of, but is not limited to, an alkylamine group, an arylalkylamine group, an arylamine group, an arylheteroarylamine group, an alkylheteroarylamine group, and a heteroarylamine group. The number of carbon atoms in the amine group is not particularly limited, but is preferably 1 to 60.

[0045] In the present specification, the number of carbon atoms of the aryl group is not particularly limited, but is preferably 6 to 60. According to one embodiment, the number of carbon atoms of 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, and a terphenyl group. Examples of the polycyclic aryl group include, but are not limited to, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a triphenylenyl group, a chrysenyl group, and a fluorenyl group.

[0046] In the present specification, an arylene group refers to an aryl group having two bonding positions, i.e., a divalent group. The above description of the aryl group may be applied, except that each of these is a divalent group.

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

[0048] In the present specification, the heterocyclic group is an aromatic, aliphatic, or aromatic-aliphatic fused ring group containing one or more non-carbon atoms or heteroatoms. Specifically, the heteroatom may contain one or more atoms selected from the group consisting of O, N, Se, and S. The number of carbon atoms in the heterocyclic group is not particularly limited, but may be 2 to 60. Examples of the heterocyclic group include, but are not limited to, a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a pyridine group, a bipyridine group, a pyrimidine group, a triazine group, a triazole group, an acridine group, a pyridazine group, a pyrazine group, a quinoline group, a quinazoline group, a quinoxaline group, a phthalazine group, a pyridopyrimidine group, a pyridopyrazine group, a pyrazinopyrazine group, an isoquinoline group, an indole group, a carbazole group, a benzoxazole group, a benzimidazole group, a benzothiazole group, a benzocarbazole group, a benzothiophene group, a dibenzothiophene group, a benzofuran group, a phenanthridine group, a phenanthroline group, an isoxazole group, a thiadiazole group, a phenothiazine group, and a dibenzofuran group.

[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, and a carbazole group.

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

[0051] In this specification, the silyl group is a group represented by -SiR201R202R203, where R201, R202, and R203 are the same or different, and each is 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, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, and a phenylsilyl group.

[0052] As used herein, a siloxane group is -Si(R204) 2 OSi(R205) 3 wherein R204 and R205 are the same or different and each independently represents a hydrogen atom; a deuterium atom; 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 in which an aromatic ring and an aliphatic ring are condensed.

[0054] In this specification, the aromatic ring may be the same as the above description of the aryl group.

[0055] In this specification, the above description of the cycloalkyl group may be applied to the aliphatic ring.

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

[0057] In the present specification, a crosslinkable group may refer to a reactive substituent that crosslinks compounds when exposed to heat, light, and / or radiation. Crosslinks can be generated by linking radicals generated by decomposing carbon-carbon multiple bonds and cyclic structures by heat treatment, light irradiation, and / or radiation.

[0058] In this specification, the crosslinkable group has one of the following structures:

[0059] [ka]

[0060] In the above structure, L30 to L36 are the same or different and each independently represent a direct bond; -O-; -COO-; a substituted or unsubstituted alkylene group; a substituted or unsubstituted arylene group; or a combination thereof; [ka] is the site of attachment to another substituent or bond.

[0061] In one embodiment of the present invention, [ka] is the site of attachment to Chemical Formula 3.

[0062] The first unit will be explained below.

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

[0064] In one embodiment of the present invention, the above-mentioned Chemical Formula 1 is the following Chemical Formula 1-1. [ka]

[0065] In the above Chemical Formula 1-1, Ar1, Ar2, L1, L2, R11 to R16, l1, and l2 are the same as defined in Chemical Formula 1. R1, R2, R2', and R3 are the same or different and each independently represents hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted arylamine group; or a substituted or unsubstituted siloxane group.

[0066] In one embodiment of the present invention, L1 and L2 are the same or different and each independently represents a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

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

[0069] In one embodiment of the present invention, the above-mentioned Chemical Formula 1 is the following Chemical Formula 1-2. [ka]

[0070] In the above Chemical Formula 1-2, Ar1, Ar2, R1 to R3, R11 to R16, and r1 to r3 are the same as defined in Chemical Formula 1. R17 and R18 are the same or different, and each independently represents hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted arylamine group; or a substituted or unsubstituted siloxane group; r17 and r18 each represent an integer of 1 to 4, and when r17 and r18 each represent an integer of 2 or more, the substituents in each bracket are the same or different from each other. p1 and p2 are each an integer of 1 to 3, and when p1 and p2 are each an integer of 2 or more, the structures in the respective brackets are the same or different from each other, * indicates a point of attachment within the polymer.

[0071] In one embodiment of the present invention, Ar1 and Ar2 are the same or different and each is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

[0072] In one embodiment of the present invention, Ar1 and Ar2 are the same or different and each independently represent 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 above-mentioned formula 1 is the following formula 1-3. [ka]

[0074] In the above Chemical Formula 1-3, R1 to R3, R11 to R16, and r1 to r3 are the same as defined in Chemical Formula 1. R17, R18, R20, and R21 are the same or different, and each independently represents hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted arylamine group; or a substituted or unsubstituted siloxane group; r17, r18, r20, and r21 each represent an integer of 1 to 4, and when r17, r18, r20, and r21 each represent an integer of 2 or more, the substituents in each bracket are the same or different from each other, p1 to p4 each represent an integer of 1 to 3, and when p1 to p4 each represent an integer of 2 or more, the structures in the respective brackets are the same or different from each other, * indicates a point of attachment within the polymer.

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

[0076] In the above Chemical Formula 1-4, R11 to R16 are the same as defined in Chemical Formula 1. R1, R2, R2', R3, R17, R18, R20, and R21 are the same or different, and each independently represents hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted arylamine group; or a substituted or unsubstituted siloxane group; r17, r18, r20, and r21 each represent an integer of 1 to 4, and when r17, r18, r20, and r21 each represent an integer of 2 or more, the substituents in each bracket are the same or different from each other, p1 to p4 each represent an integer of 1 to 3, and when p1 to p4 each represent an integer of 2 or more, the structures in the respective brackets are the same or different from each other, * indicates a point of attachment within the polymer.

[0077] In one embodiment of the present invention, R1 to R3 are the same or different and each independently represents hydrogen or a substituted or unsubstituted alkyl group.

[0078] In one embodiment of the present invention, R1 to R3 are the same or different and each independently represents 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 the same or different and each independently represents 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 the same or different and each independently represents a hydrogen atom 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 the same or different and each independently represent a hydrogen atom 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 the same or different and each independently represent a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and at least one of R1 to R3 is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

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

[0085] In one embodiment of the present invention, R1, R2, R2', and R3 are the same or different and each independently represents 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 the same or different and each independently represents 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 the same or different and each independently represent a hydrogen atom or an alkyl group.

[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 the same or different from each other and each independently represent hydrogen or a substituted or unsubstituted alkyl group, and 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 the same or different and each independently represent hydrogen or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and at least one of R1, R2, R2', and R3 is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

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

[0092] In one embodiment of the present invention, R1 and R3 each represent a hydrogen atom 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 an alkyl group.

[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 the same or different and each independently represents a substituted or unsubstituted alkyl group.

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

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

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

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

[0104] In one embodiment of the present invention, R11 to R16 each represent a methyl group.

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

[0106] In one embodiment of the present invention, R17, R18, R20, and R21 are the same or different and each independently represent hydrogen; deuterium; or an 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 formula 1 has any one of the following structures: [ka]

[0112] In the above structure, * is the point of attachment within the polymer.

[0113] In one embodiment of the invention, hydrogen can be replaced by deuterium, e.g., hydrogen in the above structure can be replaced by deuterium.

[0114] The third unit will be explained below.

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

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

[0117] In the above Chemical Formula 4-1, R4 to R6, Ar3, Ar4, L3, L4, r4 to r6, l3, and l4 are the same as defined in Chemical Formula 4; R23 and R24 are the same or different and each independently represents hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted arylamine group; or a substituted or unsubstituted siloxane group; r23 and r24 each represent an integer of 1 to 5, and when r23 and r24 each represent an integer of 2 or more, the substituents in each bracket are the same or different from each other. * indicates a point of attachment within the polymer.

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

[0119] In the above Chemical Formula 4-2, R4 to R6, Ar3, Ar4, L3, L4, r4 to r6, l3, and l4 are the same as defined in Chemical Formula 4; R23 and R24 are the same or different and each independently represents 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; R25 and R26 are the same or different, and each independently represents hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted arylamine group; or a substituted or unsubstituted siloxane group; r25 and r26 each represent an integer of 1 to 4, and when r25 and r26 each represent an integer of 2 or more, the substituents in each bracket are the same or different from each other, * indicates a point of attachment within the polymer.

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

[0121] In the above Chemical Formula 4-3, R4 to R6, Ar3, Ar4, and r4 to r6 are the same as defined in Chemical Formula 4, R23 and R24 are the same or different and each independently represents 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; R25 to R28 are the same or different and each independently represents hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted arylamine group; or a substituted or unsubstituted siloxane group; Each of r25 to r28 is an integer of 1 to 4, and when each of r25 to r28 is 2 or more, the substituents in each bracket are the same or different. p5 and p6 are each an integer of 1 to 3, and when p5 and p6 are each an integer of 2 or more, the structures in the respective brackets are the same or different from each other, * indicates a point of attachment within the polymer.

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

[0123] In the above Chemical Formula 4-4, R4 to R6 and r4 to r6 are the same as defined in Chemical Formula 4. R23 and R24 are the same or different and each independently represents 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; R25 to R30 are the same or different and each independently represents hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted arylamine group; or a substituted or unsubstituted siloxane group; Each of r25 to r30 is an integer of 1 to 4, and when each of r25 to r30 is 2 or more, the substituents in each bracket are the same or different. p5 to p8 each represent an integer of 1 to 3, and when p5 to p8 each represent an integer of 2 or more, the structures in the respective brackets are the same or different from each other, * indicates a point of attachment within the polymer.

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

[0125] In the above Chemical Formula 4-5, Ar3, Ar4, L3, L4, l3, and l4 are defined as in Chemical Formula 4. R4, R5, R5', R6, R23, and R24 are the same or different and each independently represents hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted arylamine group; or a substituted or unsubstituted siloxane group; r23 and r24 each represent an integer of 1 to 5, and when r23 and r24 each represent an integer of 2 or more, the substituents in each bracket are the same or different from each other. * indicates a point of attachment within the polymer.

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

[0127] In the above Chemical Formula 4-6, Ar3, Ar4, L3, L4, l3, and l4 are defined as in Chemical Formula 4. R4, R5, R5', R6, R25, and R26 are the same or different and each independently represents hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted arylamine group; or a substituted or unsubstituted siloxane group; R23 and R24 are the same or different and each independently represents 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; r25 and r26 each represent an integer of 1 to 4, and when r25 and r26 each represent an integer of 2 or more, the substituents in each bracket are the same or different from each other, * indicates a point of attachment within the polymer.

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

[0129] In the above Chemical Formula 4-7, R4, R5, R5', R6, and R25 to R30 are the same or different and each independently represents hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted arylamine group; or a substituted or unsubstituted siloxane group; R23 and R24 are the same or different and each independently represents 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; Each of r25 to r30 is an integer of 1 to 4, and when each of r25 to r30 is 2 or more, the substituents in each bracket are the same or different. p5 to p8 each represent an integer of 1 to 3, and when p5 to p8 each represent an integer of 2 or more, the structures in the respective brackets are the same or different from each other, * indicates a point of attachment within the polymer.

[0130] In one embodiment of the present invention, R4 to R6 are the same or different and each independently represents hydrogen or a substituted or unsubstituted alkyl group.

[0131] In one embodiment of the present invention, R4 to R6 are the same or different and each independently represent a hydrogen atom 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 the same or different and each independently represent a hydrogen atom 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 the same or different and each independently represents a hydrogen atom 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 the same or different and each independently represent a hydrogen atom 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 the same or different and each independently represent a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and at least one of R4 to R6 is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

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

[0138] In one embodiment of the present invention, R4, R5, R5', and R6 are the same or different and each independently represent a hydrogen atom 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 the same or different and each independently represent a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

[0140] In one embodiment of the present invention, R4, R5, R5', and R6 are the same or different and each independently represent a hydrogen atom or an alkyl group.

[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 the same or different from each other and each independently represent 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 the same or different and each independently represent hydrogen or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and at least one of R4, R5, R5', and R6 is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

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

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

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

[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 the same or different and each independently represents a substituted or unsubstituted alkyl group.

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

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

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

[0156] In one embodiment of the present invention, R23 and R24 are the same or different and each independently a substituted or unsubstituted alkyl group.

[0157] In one embodiment of the present invention, R23 and R24 are the same or different and each independently represent a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

[0158] In one embodiment of the present invention, R23 and R24 are the same or different and each independently represent 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 the same or different and each independently represent 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 the same or different and each independently represent hydrogen; deuterium; or a substituted or unsubstituted alkyl group.

[0161] In one embodiment of the present invention, R25 to R30 are the same or different and each independently represents 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 1 or 2, respectively.

[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 formula 4 has any one of the following structures: [ka]

[0167] The second unit will be explained below.

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

[0169] In one embodiment of the invention, Y is a direct bond; or a substituted or unsubstituted arylene group.

[0170] In one embodiment of the invention, Y is a direct bond; or a substituted or unsubstituted phenylene group.

[0171] In one embodiment of the present invention, the above-mentioned Chemical Formula 2 is any one of the following Chemical Formulas 2-1 to 2-4. [ka] [ka]

[0172] In the above Chemical Formulas 2-1 to 2-4, Z1 is CRa; SiRa; N; or a trivalent substituted or unsubstituted aryl group; Z2 and Z3 are the same or different and each independently represents C; Si; or a tetravalent substituted or unsubstituted aryl group; L10 is a direct bond; or a substituted or unsubstituted arylene group; Ra is hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group; R50 to R60 are the same or different and each independently represents hydrogen; deuterium; a halogen group; a cyano group; an alkoxy group; an aryloxy group; a siloxane group; a substituted or unsubstituted amine group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; or a crosslinkable group, and adjacent groups may be bonded to each other to form a ring; Each of r50 to r59 is an integer of 1 to 4, and r60 is an integer of 1 to 5. When each of r50 to r60 is 2 or more, the substituents in each parentheses are the same or different. * indicates a point of attachment within the polymer.

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

[0174] In one embodiment of the present invention, when Z1 is CRa or SiRa, and Ra is a substituted or unsubstituted aryl group, 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 direct bond; or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

[0179] In one embodiment of the present invention, L10 is a direct bond; 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 formula 2 is the 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 formula 2 is the 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 formula 2 is the formula 2-4.

[0187] In one embodiment of the present invention, the formula 2 has any one of the following structures: [ka]

[0188] In the above structure, R50 to R61 and R52' are the same or different and each independently represents hydrogen; deuterium; a halogen group; a cyano group; an alkoxy group; an aryloxy group; a siloxane group; a substituted or unsubstituted amine group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; or a crosslinkable group, and adjacent groups may be bonded to each other to form a ring; each of r50 to r59 and r52' is an integer of 1 to 4, r60 is an integer of 1 to 5, and r61 is an integer of 1 to 3; when each of r50 to r61 and r52' is 2 or more, the substituents in each bracket are the same or different from each other; * indicates a point of attachment within the polymer.

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

[0190] Specifically, the formula 2 is any one of the following structures: [ka]

[0191] In the above structure, * is the point of attachment within the polymer.

[0192] More specifically, the formula 2 is any one of the following structures: [ka] In the above structure, * is the point of attachment within the polymer.

[0193] More specifically, the formula 2 is any one of the following structures: [ka] In the above structure, * is the point of attachment within the polymer.

[0194] The terminal groups will now be described.

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

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

[0197] In one embodiment of the 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 alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; a crosslinkable group; or a combination thereof.

[0199] In one embodiment of the present invention, E is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a 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 to R72 are the same or different and each independently represents hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; or a 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 when i1 is 2 or more, two or more L70 are the same or different; n70 and n72 each represents an integer of 1 to 5, n71 represents an integer of 1 to 4, and when n70 to n72 each represents 2 or more, the substituents in each bracket are the same or different from each other, * indicates a point of attachment within the polymer.

[0202] In one embodiment of the present invention, E is any one of the following structures: [ka]

[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 or different and each independently represents 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, E is any one of the following structures: [ka] In the above structure, * is the point of attachment within the polymer.

[0207] More specifically, E is any one of the following structures: [ka] In the above structure, * is the point of attachment within the polymer.

[0208] The polymer will be described below.

[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 a terminal group 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 greater than 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 of 0.05 to 0.9, b is a real number of 0.05 to 0.8, and c is a real number exceeding 0 and not exceeding 0.9.

[0217] In this specification, the a, b, and c are not based on the molar fraction of the entire polymer represented by Chemical Formula 5 including E1 and E2, but are based on the molar fraction of the sum of A1, B1, and C1.

[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 invention, the polymer is an alternating, block, or random polymer.

[0220] In one embodiment of the present invention, the formula 5 does not mean that A1, B1, and C1 are arranged in the same order in the polymer. Specifically, the A1, B1, and C1 may be arranged in various orders in the polymer. For example, the polymer may be arranged in the order of E1-A1-B1-C1-E2, E1-A1-C1-B1-E2, E1-B1-A1-C1-E2, E1-B1-C1-A1-E2, E1-C1-A1-B1-E2, or E1-C1-B1-A1-E2.

[0221] In addition, the formula 5 does not mean that A1, B1, and C1 are linked to each other only once in the polymer. For example, the polymer may be linked to each other in various ranges of content, such as E1-A1-B1-A1-C1-E2, E1-A1-C1-B1-C1-E2, E1-A1-B1-C1-A1-E2, etc. In this case, the ranges of content of A1, B1, and C1 are determined according to the equivalent ratio of monomers used in the preparation 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 gel permeation chromatography (GPC, waters breeze) using THF (tetrahydrofuran) as an eluent. More specifically, the molecular weight is a value obtained by applying the weight average molecular weight (Mw) and number average molecular weight (Mn) calculated in terms of polystyrene 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 which time the flow rate is 0.3 mL / min, and the analysis can be performed at 30° C. for a sample concentration of 2.0 mg / mL (100 μl injection). Here, the column is two Waters PLgel HFIPGEL columns connected in series, and the detector is an RI detector (Agilent Waters, 2414), which is used for measurement at 40° C., and the data may be processed using ChemStation.

[0227] When the weight-average molecular weight of the polymer falls within the above range, the viscosity is suitable, and the effect of facilitating the production of an ink-jet device and an organic light-emitting device using fine pixels is exhibited.

[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 of a polymer means that molecules of various molecular weights are distributed, which means that it is difficult to synthesize a polymer with good reproducibility. 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 is produced.

[0231] In one embodiment of the present invention, in the polymer, the first unit represented by the chemical formula 1; the second unit represented by the chemical formula 2; the third unit represented by the chemical formula 4 and different from the first unit; and the end group represented by the chemical formula 3 can be distributed so as to optimize the properties of the polymer.

[0232] In one embodiment of the present invention, a1 is a molar fraction of a first unit represented by chemical formula 1 in a polymer, b1 is a molar fraction of a second unit represented by chemical formula 2, c1 is a molar fraction of a third unit different from the first unit and represented by chemical formula 4, and e1 is a molar fraction of a terminal group represented by chemical formula 3. Each of a1, b1, c1, and e1 is a real number and is equal to or smaller than 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 equal to or greater than 0.05 and less than 1. In one embodiment of the present invention, a1 is a real number of 0.05 to 0.95. In one embodiment of the present invention, a1 is a real number of 0.1 to 0.9. In one embodiment of the present invention, a1 is a real number of 0.05 to 0.8.

[0234] In one embodiment of the present invention, b1 is a real number greater than or equal to 0.05 and less than 1. In one embodiment of the present invention, b1 is a real number of 0.05 to 0.95. In one embodiment of the present invention, b1 is a real number of 0.05 to 0.8. In one embodiment of the present invention, b1 is a real number of 0.1 to 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 greater than or equal to 0.05 and less than 1. In one embodiment of the present invention, c1 is a real number from 0.05 to 0.95. In one embodiment of the present invention, c1 is a real number from 0.1 to 0.9. In one embodiment of the present invention, c1 is a real number from 0.05 to 0.8.

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

[0237] In one embodiment of the present invention, a1 is a real number that is equal to or greater than 0.05 and less than 1, b1 is a real number that is equal to or greater than 0.05 and less than 1, c1 is a real number that is greater than 0 and less than 1, e1 is a real number that is equal to or greater than 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 of 0.05 to 0.8, b1 is a real number of 0.05 to 0.8, c1 is a real number exceeding 0 and not exceeding 0.8, e1 is a real number of 0.05 to 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]

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 of 0.05 to 0.8, b1 is a real number of 0.05 to 0.8, c1 is a real number exceeding 0 and not exceeding 0.8, e1 is a real number of 0.05 to 0.8, and a1+b1+c1+e1=1.

[0249] 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.

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

[0251] In one embodiment of the present invention, the polymer may be prepared using known polymerization techniques, such as Suzuki, Yamamoto, Stille, metal-catalyzed C-N coupling reactions, and metal-catalyzed arylation reactions.

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

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

[0254] In one embodiment of the 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 invention, the "layers", "membranes" and "films" 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 invention, the polymer has an intrinsic viscosity of less than 20 cP. This is particularly useful for inkjet printing applications, where the lower viscosity allows a thicker solution to be jetted. 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, more specifically 1 cP to 8 cP.

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

[0259] The coating composition containing the polymer will now be described.

[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 the present invention, the coating composition comprises the polymer and a solvent.

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

[0263] In one embodiment of the invention, the solvent preferably does not dissolve the material applied to the underlayer.

[0264] In one embodiment of the present invention, when the coating composition is applied to an organic layer of an organic light-emitting device, a solvent that does not dissolve the material of the lower layer is used. For example, when the coating composition is applied to a 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 solution processing.

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

[0266] For example, if a coating composition is prepared using a solvent that dissolves the polymer and the layer is prepared by solution processing, it will be resistant to the same solvent after heat treatment.

[0267] Therefore, when an organic layer is formed using the polymer and then heat-treated, solution processing is possible when applying another organic layer.

[0268] In one embodiment of the present invention, examples of the solvent contained in the coating composition include chlorine-based solvents such as chloroform, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, and o-dichlorobenzene; ether-based solvents such as tetrahydrofuran and dioxane; aromatic hydrocarbon-based solvents such as toluene, xylene, trimethylbenzene, and mesitylene; ketone-based solvents such as acetone, methyl ethyl ketone, and cyclohexanone; ester-based solvents such as ethyl acetate, butyl acetate, and ethyl cellosolve acetate; ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, and ethylene glycol monomethyl ether. Examples of solvents include polyhydric alcohols and derivatives thereof, such as dimethoxyethane, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerin, and 1,2-hexanediol; alcohol-based solvents, such as methanol, ethanol, propanol, isopropanol, and cyclohexanol; sulfoxide-based solvents, such as dimethyl sulfoxide; amide-based solvents, such as N-methyl-2-pyrrolidone and N,N-dimethylformamide; benzoate-based solvents, such as methyl benzoate, butyl benzoate, and 3-phenoxybenzoate; and tetralin. However, the solvent is not limited to these, as long as it is capable of dissolving or dispersing the polymer according to one embodiment of the present invention.

[0269] In one embodiment of the present invention, the solvent may be used alone or in combination of two or more kinds.

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

[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 thereto.

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

[0273] The organic light-emitting device containing the polymer will now be described.

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

[0275] The organic layer of the organic light-emitting device of the present invention may have a single-layer structure, or may have a multi-layer structure in which two or more organic layers are laminated. For example, the organic light-emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, a layer that simultaneously injects holes and transports holes, a layer that simultaneously injects electrons and transports electrons, etc., as the organic layer. However, the structure of the organic light-emitting device is not limited thereto, and may include a smaller number of organic layers.

[0276] When the organic light emitting device includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.

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

[0278] In one embodiment of the present invention, the organic light-emitting element includes a first electrode; a second electrode; and an emitting layer provided between the first electrode and the second electrode, and further includes multiple organic layers between the emitting layer and the first electrode, at least one of the organic layers including the polymer.

[0279] In one embodiment of the present invention, the organic layer containing a polymer is a hole injection layer, a hole transport layer, or a layer which simultaneously injects and transports holes.

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

[0281] In one embodiment of the present invention, the organic light-emitting element comprises a first electrode; a second electrode; and an emitting layer provided between the first electrode and the second electrode, and comprises a hole injection layer and a hole transport layer between the first electrode and the emitting layer, and at least one of the hole injection layer and the hole transport layer comprises 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, an emission layer, and a second electrode are sequentially stacked, and at least one of the hole injection layer and the hole transport layer contains 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, an emission layer, and a second electrode are sequentially laminated, 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 device has a structure in which a first electrode, a hole injection layer, a hole transport layer, a light-emitting layer, and a second electrode are laminated in this order, and the hole transport layer contains the polymer.

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

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

[0287] In one embodiment of the present invention, multiple organic layers may be further included between the light-emitting layer and the second electrode, for example, one or more of a hole-blocking layer, an electron-injecting layer, an electron-transporting layer, and a layer that simultaneously injects and transports electrons 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 device has a structure in which a first electrode; a hole injection layer; a hole transport layer; an emission layer; an electron injection and transport layer; and a second electrode are sequentially laminated, and at least one of the hole injection layer and the hole transport layer contains 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; an emission layer; an electron injection and transport layer; and a second electrode are sequentially laminated, 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; an emission layer; an electron injection and transport layer; and a second electrode are sequentially laminated, and the hole transport layer contains the polymer.

[0291] The structure of an organic light-emitting device according to one embodiment of the present invention is illustrated in FIGS. FIG. 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 laminated in this order. FIG. 2 illustrates the structure of an organic light-emitting device in which a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 3, an electron injection and transport layer 7, and a cathode 4 are laminated in this order. 1 and 2 are merely examples of the organic light-emitting device, but the structure of the organic light-emitting device of the present invention is not limited to these.

[0292] In one embodiment of the invention, the first electrode is an anode and the second electrode is a cathode, and in another embodiment, the first electrode is a cathode and the second electrode is an anode.

[0293] In one embodiment, the organic light-emitting device may be a normal type organic light-emitting device having a structure in which an anode, one or more organic layers, and a cathode are laminated in this order on a substrate.

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

[0295] The organic light-emitting device of the present invention may be laminated in a structure such as the following examples. (1) Anode / hole transport layer / light emitting layer / cathode (2) Anode / hole injection layer / hole transport layer / light emitting layer / cathode (3) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / cathode (4) Anode / hole transport layer / light emitting layer / electron transport layer / cathode (5) Anode / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode (6) Anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / cathode (7) Anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode (8) Anode / hole injection layer / hole buffer layer / hole transport layer / light emitting layer / electron transport layer / cathode (9) Anode / hole injection layer / hole buffer layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode (10) Anode / hole transport layer / electron inhibiting layer / light emitting layer / electron transport layer / cathode (11) Anode / hole transport layer / electron inhibiting layer / light emitting layer / electron transport layer / electron injection layer / cathode (12) Anode / hole injection layer / hole transport layer / electron inhibiting layer / light emitting layer / electron transport layer / cathode (13) Anode / hole injection layer / hole transport layer / electron inhibition layer / light emitting layer / electron transport layer / electron injection layer / cathode (14) Anode / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / cathode (15) Anode / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode (16) Anode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / cathode (17) Anode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode (18) Anode / hole injection layer / hole transport layer / electron inhibition layer / light 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 simultaneously injects and transports electrons".

[0297] For example, the organic light-emitting device of the present invention may be laminated in a structure such as "anode / hole injection layer / hole transport layer / light-emitting layer / electron injection and transport layer / cathode" in which the electron transport layer / electron injection layer of (7) above is replaced with an electron injection and transport layer.

[0298] In the above structure, the "hole injection layer / hole transport layer" may be replaced by a "hole injection and transport layer" or a "simultaneous hole injection and transport layer".

[0299] The organic light emitting device of the present invention may be manufactured by materials and methods well known in the art, except that at least one of the organic layers is manufactured to include the polymer. Specifically, the organic light emitting device may be formed by using a coating composition in which at least one of the organic layers includes the polymer.

[0300] For example, the organic light emitting device of the present invention can be fabricated 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 is deposited on a substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation to form an anode, and an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron injection and transport layer is formed thereon, and then a material usable as a cathode is deposited thereon. In addition to this method, an organic light emitting device can be fabricated by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.

[0301] The present invention also provides a method for manufacturing an organic light emitting device formed using the coating composition.

[0302] Specifically, in one embodiment of the present invention, the method includes the steps of: preparing a substrate; forming a first electrode on the substrate; forming one or more organic layers on the first electrode; and forming a second electrode on the organic layers, wherein one or more of the organic layers are formed using the coating composition.

[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 includes, but is not limited to, inkjet printing, nozzle printing, offset printing, transfer printing, screen printing, and the like.

[0306] The coating composition according to one embodiment of the present invention has structural properties that make it suitable for solution processing and can be formed by a printing method, which has the effect of being time- and cost-effective in the manufacture of devices.

[0307] In one embodiment of the present invention, the step of forming an organic layer using the coating composition includes the steps of coating the coating composition on the first electrode; and subjecting the coated coating composition to a heat treatment or a light treatment.

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

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

[0310] When the organic layer formed using the coating composition includes a heat treatment or light treatment step, the resistance to a solvent is increased, and multiple layers can be formed by repeatedly performing solution deposition and crosslinking methods, thereby increasing stability and improving the life characteristics of the device.

[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 deposition. For example, when the coating composition is applied to a hole injection layer or a hole transport layer, the hole injection layer or the hole transport layer may be formed by spin coating, and other organic layers may be formed by spin coating, printing, or deposition. In addition, 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 may be formed by spin coating, an emitting layer formed on the hole transport layer so as to be in contact with the hole transport layer may be formed by spin coating, and an electron injection and transport layer formed on the emitting layer may be formed by deposition.

[0312] In one embodiment of the present invention, the anode material is preferably a material having a large work function so that holes can be easily injected into the organic layer. Specific examples of anode materials that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO:Al, or SnO 2 These include, but are not limited to: a combination of a metal and an oxide, such as 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 preferably a material having a small work function so as to facilitate electron injection into the organic layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; LiF / Al or LiO 2Examples of the material include, but are not limited to, multi-layered materials such as / Al.

[0314] In one embodiment of the present invention, the hole injection layer is a layer that injects holes from the electrode, and the hole injection material is preferably a compound that has the ability to transport holes, 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 forming ability. In addition, 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 the hole injection material include, but are not limited to, metal porphyrin, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, perylene-based organic materials, carbazole-based organic materials, anthraquinone, and polyaniline and polythiophene-based conductive polymers. Specifically, the hole injection layer may be, but is not limited to, a carbazole-based compound, an arylamine-based compound, or a compound in which a substituted or unsubstituted carbazole and an arylamine group are linked together.

[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 the hole injection layer and move them to the light emitting layer, and is preferably a material that has high mobility for holes.

[0316] In one embodiment of the present invention, the light-emitting layer contains an organic compound. The organic compound is a substance that can emit light in the visible light range by receiving and combining holes and electrons transported from the hole transport layer and electron transport layer, respectively, and is preferably a substance with good quantum efficiency for fluorescence or phosphorescence. A specific example is 8-hydroxy-quinoline aluminum complex (Alq 3); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzoxazole, benzothiazole, and benzimidazole-based compounds; poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; polyfluorene; rubrene, and the like, but are not limited to these.

[0317] In one embodiment of the present invention, the light-emitting layer may include a host material and a dopant material. The host material may include a fused aromatic ring derivative or a heterocyclic ring-containing compound. Specifically, the fused aromatic ring derivative may include an anthracene derivative, a pyrene derivative, a naphthalene derivative, a pentacene derivative, a phenanthrene compound, a fluoranthene compound, and the like, and the heterocyclic ring-containing compound may include, but is not limited to, a carbazole derivative, a dibenzofuran derivative, a ladder-type furan compound, a pyrimidine derivative, and the like. The dopant material may include an aromatic amine derivative, a styrylamine compound, a boron complex, a compound containing boron, a fluoranthene compound, a metal complex, and the like. For example, the aromatic amine derivative is a condensed aromatic ring derivative substituted with a substituted or unsubstituted arylamino group, and includes fluorene, benzofluorene, pyrene, anthracene, chrysene, periflanthene, etc., which are substituted with an arylamino group, and the styrylamine compound is a compound in which at least one arylvinyl group is substituted with a substituted or unsubstituted arylamine, and one or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamino group are substituted or unsubstituted.Specifically, the styrylamine compound includes, but is not limited to, styrylamine, styryldiamine, styryltriamine, styryltetraamine, etc. In addition, the metal complex includes, but is not limited to, an iridium complex, a platinum complex, etc.

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

[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 the quantum dots may be those known in the art.

[0320] When the light-emitting layer contains quantum dots, the HOMO energy level is lower than when the light-emitting layer contains an organic compound, so the common layer must also have a low HOMO energy level. The compound according to one embodiment of the present invention contains a halogen group and therefore has a low HOMO energy level, making it possible to introduce 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 which simultaneously injects holes and transports holes, an electron injection layer, an electron transport layer, or a layer which simultaneously injects electrons and transports electrons.

[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 electrons injected from the cathode and transfer them to the light-emitting layer, and is preferably a material that has high mobility for electrons. Specific examples include Al complex of 8-hydroxyquinoline; Alq 3The electron transport layer may be used with any desired cathode material, as used by the prior art. In particular, examples of suitable cathode materials are conventional materials with low work functions, followed by an aluminum or silver layer. Specifically, cesium, barium, calcium, ytterbium, and samarium, each followed by an aluminum or silver layer.

[0323] In one embodiment of the present invention, the electron injection layer is a layer that injects electrons from an electrode, and is preferably a compound that 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 has excellent thin-film forming ability.Specific examples of the compound include, but are not limited to, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidenemethane, anthrone, bathocuproine (BCP), and derivatives thereof, metal complex compounds, and nitrogen-containing five-membered ring derivatives.

[0324] In one embodiment of the present invention, the metal complex compound may be, but is not limited to, 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato) zinc, bis(8-hydroxyquinolinato) copper, bis(8-hydroxyquinolinato) manganese, tris(8-hydroxyquinolinato) aluminum, tris(2-methyl-8-hydroxyquinolinato) aluminum, tris(8-hydroxyquinolinato) gallium, bis(10-hydroxybenzo[h]quinolinato) beryllium, bis(10-hydroxybenzo[h]quinolinato) zinc, bis(2-methyl-8-quinolinato) chlorogallium, bis(2-methyl-8-quinolinato) (o-cresolate) gallium, bis(2-methyl-8-quinolinato) (1-naphtholato) aluminum, bis(2-methyl-8-quinolinato) (2-naphtholato) gallium, etc.

[0325] In one embodiment of the present invention, the hole blocking layer is a layer that blocks holes from reaching the cathode, and may be generally formed under the same conditions as the hole injection layer.Specific examples of the hole blocking layer 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, when the polymer represented by Formula 5 is contained in a hole transport layer, at least one of the bank layer adjacent to the hole transport layer, the hole injection layer, and the light emitting layer contains fluorine.

[0328] When a layer adjacent to the organic layer including the polymer including the first unit, the second unit, the third unit, and the end group contains fluorine, a dipole moment is changed by the fluorine, so that a uniform layer can be formed.

[0329] The organic light emitting device according to the present invention may be top-emitting, bottom-emitting or double-sided emitting, depending on the materials used. EXAMPLES

[0330] Hereinafter, the present invention will be described in detail with reference to examples in order to specifically explain the present invention. However, the examples according to the present invention may be modified in various different forms, and the scope of the present application is not to be construed as being limited to the examples described below. The examples of the present application are provided to more completely explain the present specification to those having average knowledge in the art.

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

[0332] (1-1) Preparation of Compound Q-1 In a round-bottom flask equipped with a condenser, compound w-1 (50.0 g, 1.00 eq), compound w-2 (65.2 g, 1.35 eq), and potassium carbonate (K 2 CO 3 ) (78.7 g, 2.5 eq) and bis(tri-tert-butylphosphine)palladium(0) (1.74 g, 0.015 eq) were added, followed by the addition of THF (500 mL) and distilled water (300 mL), which was then heated to 60°C and stirred for 6 hours. Distilled water was added to terminate the reaction, and the organic solvent was extracted and concentrated under reduced pressure to obtain compound Q-1 (50.1 g) in a liquid state.

[0333] (1-2) Preparation of Compound P-1 Compound Q-2 (41.0 g, 1.00 eq) and compound Q-1 (50.0 g, 3.0 eq) prepared above were dissolved in xylene (200 mL) in a round-bottom flask equipped 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 refluxed at 120°C for 3 hours. After the reaction was terminated by injecting distilled water, the organic solvent was extracted with ethyl acetate and distilled water, and the compound P-1 was obtained as a white solid by precipitation with toluene and hexane.

[0334] (1-3) Preparation of Compound P-2 In a round-bottom flask equipped with a condenser, the previously prepared 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). When completely dissolved, 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 refluxed at 90 °C for 8 hours. After the reaction was terminated 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 refluxed at 90 °C for 8 hours. After the reaction was terminated 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) Preparation of Compound B-2 [ka]

[0337] In a round-bottom flask equipped with a condenser, 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 toluene (200 mL). After complete dissolution, [1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (Pd(dppf)) (0.20 g, 0.04 eq) was added and the mixture was refluxed at 90°C for 8 hours. After the reaction was terminated 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) Preparation 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), followed by addition of tetrakis(triphenylphosphine)palladium(0) (Pd(PPh 3 ) 4 ) (0.05 mmol), potassium carbonate (K 2 CO 3After injecting 5 mL of 2M solution of 1,2-dichlorophenyl ether and 0.1 mL of Aliquat 336 as a phase transfer catalyst, the mixture was refluxed at 100°C for 12 hours. The reaction was terminated by gradually dropping the reactant into methanol, and 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 through a column containing silica gel and basic aluminum oxide (6 g each). The obtained toluene solution was triturated with acetone to produce polymer 1 (5.2 g).

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

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

[0342] (2) Preparation of Polymer 2 [ka]

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

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

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

[0346] (2) Preparation of Polymer 3 [ka]

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

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

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

[0350] (2) Preparation of Polymer 4 [ka]

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

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

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

[0354] <Synthesis Example 6: Production of Polymer 6> [ka]

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

[0356] <Synthesis Example 7: Preparation 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 a first solution.

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

[0359] The second solution was added to a Schlenk tube and stirred at 50°C for 30 minutes. The first solution was further added to a Schlenk tube and stirred at 50°C for 3 hours. HCl and methanol (methanol:HCl = 95:5 (v:v)) were slowly added dropwise to terminate the reaction, and 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 through a column containing silica gel and basic aluminum oxide (6 g each). The obtained toluene solution was triturated with acetone to produce polymer X-1.

[0360] <Synthesis Example 8: Preparation 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 in Synthesis Example 7.

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

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

[0364] Example 1: Molecular weight measurement By measuring the molecular weight, it was confirmed that polymers 1 to 6 and X-1 to X-3 were synthesized.

[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 according to the following formula (1). Formula (1): PDI=weight average molecular weight (Mw) / number average molecular weight (Mn)

[0366] <Examples 1-2 to 1-6> 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 the polymer in Table 1 below was used instead of Polymer 1 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 the following polymer Q was used instead of polymer 1 in Example 1-1. [ka]

[0368] <Comparative Examples 1-2 to 1-4> 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 the polymer in Table 2 below was used instead of Polymer 1 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: Thin film retention measurement <Example 2-1> The polymer 1 prepared in Synthesis Example 1 was dissolved in toluene at a concentration of 2 wt % to prepare a coating composition 1.

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

[0374] <Comparative Example 2-2> The following compound P-4 prepared in Synthesis Example 4 was dissolved in toluene at a concentration of 2 wt % to prepare coating composition 3.

[0375] [ka]

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

[0377] FIG. 3 is a graph showing the experimental results of the film retention rate of the thin film formed from Coating Composition 1. FIG. 4 shows the experimental results of the film retention rate of the thin film formed from Coating Composition 2. FIG. 5 shows the experimental results of the film retention rate of the thin film formed from Coating Composition 3. 3 to 5, (a) shows the UV measurement result immediately after the thin film was formed (before it was immersed in cyclohexanone for 3 minutes), and (b) shows the UV measurement result after the thin film was immersed in cyclohexanone for 3 minutes.

[0378] 3, it can be seen that the thin film retention rate is 100% in the case of the thin film formed from Coating Composition 1. In other words, it can be seen that the polymer according to one embodiment of the present invention has excellent resistance to solvents. In contrast, it can be seen from Figures 4 and 5 that the thin films formed from Coating Compositions 2 and 3 have a large thin film loss rate. In other words, it can be seen that the compounds used in the Comparative Examples have no resistance to solvents.

[0379] Example 3: Fabrication of organic light-emitting device <Example 3-1> A glass substrate coated with a 1,500 Å-thick thin film of ITO (indium tin oxide) was placed in distilled water with detergent dissolved therein and ultrasonically cleaned. The detergent used was from Fischer Co., and the distilled water used was distilled water that had been filtered a second time with a Millipore Co. filter. The ITO was washed for 30 minutes, and then ultrasonically cleaned twice with distilled water for 10 minutes. After the distilled water cleaning was completed, the substrate was ultrasonically cleaned with a solvent of isopropyl alcohol and acetone, dried, and then washed for 5 minutes and dried.

[0380] Immediately before the fabrication of the device, the washed and patterned ITO was treated with UV ozone for 10 minutes. After the ozone treatment, a 2 wt% cyclohexanone solution containing the following compound A and the following compound B in a weight ratio of 8:2 was spin-coated on the ITO surface, and the solvent was removed by heat treatment to form a hole injection layer with a thickness of about 40 nm. On the hole injection layer formed above, a toluene solution in which 1.5 wt% of the polymer 1 produced in Synthesis Example 1 was dissolved was spin-coated, and the solvent was removed by heat treatment to form a hole transport layer with a thickness of about 100 nm. On the hole transport layer, a methyl benzoate solution in which the following compound C and the following compound D (compound C:compound D=93:7 (wt%)) were dissolved at a concentration of 2.0 wt% was spin-coated to form a light-emitting layer with a thickness of about 100 nm. After that, it was transferred to a vacuum deposition machine, and BCP was vacuum-deposited to a thickness of 35 nm on the light-emitting layer to form an electron injection and transport layer. A cathode was formed on the electron injecting and transporting layer by sequentially depositing LiF to a thickness of 1 nm and aluminum to a thickness of 100 nm.

[0381] [ka]

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

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

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

[0385] [Table 3]

[0386] Unless otherwise noted in Table 3, measurements are at 1000 nits and V is 10 mA / cm 2 where CE is the driving voltage (in volts) at 1000 Hz, external quantum efficiency (QE) is the number of photons emitted divided by the number of charge carriers injected, and color coordinate (x) and color coordinate (y) are the x and y coordinates on the CIE chromaticity diagram (Commission Internationale de L'Eclairage, 1931), and CE / CIEy is the luminous efficacy (cd / A) divided by the color coordinate (y) value.

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

[0388] Although a preferred embodiment (hole transport layer) of the present invention has been described above, the present invention is not limited thereto, and various modifications can be made within the scope of the claims and the detailed description of the invention, which also belong to 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. A first unit represented by the following chemical formula 1: A second unit represented by the following chemical formula 2: A third unit different from the first unit and represented by the following formula 4: A polymer having an end group represented by the following formula 3: 【Chemistry 1】 【Chemistry 2】 In the above Chemical Formulas 1 to 4, Ar1 to Ar4 are the same or different and each independently represents a substituted or unsubstituted arylene group; L1 to L4 are the same or different and each independently represents a direct bond; or a substituted or unsubstituted arylene group; R1 to R6 are the same or different and each independently represents hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted arylamine group; or a substituted or unsubstituted siloxane group; R11 to R16 are the same or different and each independently represents an alkyl group having 1 to 3 carbon atoms; R21 and R22 are the same or different and each independently represents hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group; Each of r1 to r6 is an integer of 1 to 4, and when each of r1 to r6 is 2 or more, the substituents in each bracket are the same or different. l1 to l4 each represents an integer of 1 to 5, and when l1 to l4 each represents 2 or more, the structures in the respective brackets are the same or different from each other, m is an integer of 3 or 4; When m is 3, Z is CRa; SiRa; N; or a trivalent substituted or unsubstituted aryl group; When m is 4, Z is C; Si; or a tetravalent substituted or unsubstituted aryl group; Ra is hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group; Y is a direct bond; a substituted or unsubstituted alkylene group; or a substituted or unsubstituted arylene group; When Y is a direct bond; or a substituted or unsubstituted alkylene group, Z is a trivalent or tetravalent substituted or unsubstituted aryl group; E is hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted arylamine group; a substituted or unsubstituted siloxane group; a crosslinkable group; or a combination thereof; * denotes attachment points within the polymer.

2. The polymer according to claim 1 , which is represented by the following chemical formula 5: 【Chemistry 3】 In the above Chemical Formula 5, A1 is a first unit represented by Chemical Formula 1; B1 is a second unit represented by Chemical Formula 2, C1 is a third unit different from the first unit and represented by Chemical Formula 4; E1 and E2 are the same or different and each is an end group represented by the above formula 3, a, b, and c are each a mole fraction, a is a real number in the range of 0<a<1, b is a real number in the range of 0<b<1, c is a real number in the range of 0<c<1, and a+b+c is 1.

3. The polymer according to claim 1, wherein the chemical formula 4 is the following chemical formula 4-1: 【Chemistry 4】 In the above Chemical Formula 4-1, R4 to R6, Ar3, Ar4, L3, L4, r4 to r6, l3, and l4 are the same as defined in Chemical Formula 4; R23 and R24 are the same or different, and each independently represents hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; a substituted or unsubstituted arylamine group; or a substituted or unsubstituted siloxane group; Each of r23 and r24 is an integer of 1 to 5, and when each of r23 and r24 is 2 or more, the substituents in each parentheses are the same or different.

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

5. 2. The polymer according to claim 1, wherein L1 and L2 are the same or different and each independently represents 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 any one of the following chemical formulas 2-1 to 2-4: 【Chemistry 6】 【Chemistry 7】 In the above Chemical Formulas 2-1 to 2-4, Z1 is CRa; SiRa; N; or a trivalent substituted or unsubstituted aryl group; Z2 and Z3 are the same or different and each independently represents C; Si; or a tetravalent substituted or unsubstituted aryl group; L10 is a direct bond; or a substituted or unsubstituted arylene group; Ra is hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group; R50 to R60 are the same or different and each independently represents hydrogen; deuterium; a halogen group; a cyano group; an alkoxy group; an aryloxy group; a siloxane group; a substituted or unsubstituted amine group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; or a crosslinkable group, and adjacent groups may be bonded to each other to form a ring; Each of r50 to r59 is an integer of 1 to 4, and r60 is an integer of 1 to 5. When each of r50 to r60 is 2 or more, the substituents in each bracket are the same or different. * denotes attachment points within the polymer.

7. 2. The polymer of 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. 2. The polymer of claim 1, wherein E is a crosslinkable group; or one of the following structures: 【Chemistry 8】 In the above structure, R70 to R72 are the same or different and each independently represents hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heterocyclic group; or a 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 when i1 is 2 or more, two or more L70 are the same or different from each other, n70 and n72 each represent an integer of 1 to 5, n71 represents an integer of 1 to 4, and when n70 to n72 each represent 2 or more, the substituents in each parentheses are the same or different from each other, * denotes attachment points within the polymer.

9. The polymer of claim 1 , wherein the crosslinkable group has one of the following structures: 【Chemistry 9】 In the above structure, L30 to L36 are the same or different and each independently represent a direct bond; -O-; -COO-; a substituted or unsubstituted alkylene group; a substituted or unsubstituted arylene group; or a combination thereof; 【Chemistry 10】 is a binding site to Chemical Formula 3.

10. The polymer of claim 1 having 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 in the range of 0<a1<1, b1 is a real number in the range of 0<b1<1, c1 is a real number in the range of 0<c1<1, e1 is a real number in the range of 0<e1<1, and a1+b1+c1+e1 is 1.

11. first electrode; A second electrode; and one or more organic layers provided between the first electrode and the second electrode; An organic light-emitting device, wherein at least one of the organic layers comprises the polymer according to any one of claims 1 to 10.

12. The organic light-emitting device according to claim 11, wherein the polymer-containing organic layer is a hole injection layer, a hole transport layer, or a layer that simultaneously injects and transports holes.

Images