Compounds, coating compositions comprising the same, organic light emitting devices using the same, and methods of making the same

Abstract

The present specification relates to compounds of Chemical Formula 1, coating compositions comprising the compounds, organic light emitting devices using the coating compositions, and methods of manufacturing the same.

Description

Technical Field

[0001] This application claims priority and benefit to Korean Patent Application No. 10-2021-0121820, filed with the Korean Intellectual Property Office on September 13, 2021, the entire contents of which are incorporated herein by reference.

[0002] This specification relates to compounds, coating compositions comprising said compounds, organic light-emitting devices formed by using said coating compositions, and methods for manufacturing the same. Background Technology

[0003] Organic light emission (OLED) is one example of converting electric current into visible light through internal processes of specific organic molecules. The principle of OLED is as follows: When an organic material layer is placed between an anode and a cathode, and a current is applied between the two electrodes, electrons and holes are injected into the organic material layer from the cathode and anode, respectively. The injected electrons and holes recombine to form excitons, which then return to the ground state to emit light. OLED devices utilizing this principle typically consist of a cathode, an anode, and an organic material layer disposed therebetween (e.g., an organic material layer including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer).

[0004] Deposition methods are commonly used to manufacture organic light-emitting devices (OLEDs) in related fields. However, when manufacturing OLEDs by deposition, material loss is a frequent problem. Therefore, to address this issue, a solution-based method for manufacturing devices has been developed, which improves production efficiency due to lower material loss. Furthermore, it is necessary to develop materials that can be used during the solution-based method.

[0005] Materials used in organic light-emitting devices via solution processing need to have the properties described below.

[0006] First, the materials used in organic light-emitting devices need to be able to form a storable homogeneous solution. Because commercially available materials used in deposition methods have high crystallinity, they may not dissolve well in solution, or even if a solution is formed, crystals may easily form, potentially leading to changes in solution concentration gradients or the formation of defective devices depending on storage time.

[0007] Second, the materials used in the solution process need to be excellent in terms of coatability, so that a film with a uniform thickness can be formed during film formation without pores or agglomeration.

[0008] Third, in the manufacture of organic light-emitting devices, the solution-processed layers need to be resistant to the solvents and materials used in the formation of other layers, and need to have excellent current efficiency and excellent lifespan characteristics.

[0009] Therefore, there is a need in this field to develop new organic materials. Summary of the Invention

[0010] Technical issues

[0011] This specification provides compounds, coating compositions comprising the same, organic light-emitting devices using the same, and methods for manufacturing the same.

[0012] Technical solution

[0013] An exemplary embodiment of this specification provides a compound of the following chemical formula 1.

[0014] [Chemical Formula 1]

[0015]

[0016] In chemical formula 1,

[0017] L1 to L3 may be the same as or different from each other, and each is independently a direct bond; -O-; substituted or unsubstituted alkylene; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl.

[0018] L11 and L12 may be the same as or different from each other, and each may be independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0019] Ar1 to Ar4 may be identical or different from each other, and each is independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0020] X1 to X3 may be the same as or different from each other, and each is independently a photocurable group or a thermosetting group.

[0021] R1 to R3 and R11 to R16 may be the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0022] a1 to a3 are each integers from 1 to 3.

[0023] When a1 to a3 are each 2 or larger, the substituents in parentheses may be the same or different from each other.

[0024] n1 to n3 are each an integer from 1 to 5.

[0025] n11 and n16 are each integers from 1 to 4.

[0026] n12 to n15 are each an integer from 1 to 3, and

[0027] When n1 to n3 and n11 to n16 are each 2 or greater, the substituents in parentheses may be the same or different from each other.

[0028] Another exemplary embodiment of this specification provides a coating composition comprising the compound.

[0029] Another exemplary embodiment of this specification provides an organic light-emitting device comprising: a first electrode; a second electrode; and an organic material layer having one or more layers, including a light-emitting layer, disposed between the first electrode and the second electrode, wherein one or more layers of the organic material layer comprise the coating composition described above or a cured product thereof.

[0030] Another exemplary embodiment of this specification provides a method for manufacturing an organic light-emitting device, the method comprising: preparing a substrate; forming a first electrode on the substrate; forming an organic material layer having one or more layers on the first electrode; and forming a second electrode on the organic material layer, wherein forming the organic material layer comprises forming an organic material layer having one or more layers by using the coating composition.

[0031] Beneficial effects

[0032] Because the compound according to one exemplary embodiment of this specification has a suitable viscosity for the solvent, it is easy to perform inkjet printing.

[0033] Furthermore, since the compound according to one exemplary embodiment of this specification has excellent solubility, there is an advantage in being able to choose a variety of solvents when preparing the coating composition.

[0034] Furthermore, the compound according to an exemplary embodiment of this specification has the advantage of forming a stable film that is not damaged by subsequent solution methods by forming a fully cured film via heat treatment or light treatment.

[0035] Furthermore, since the compound according to one exemplary embodiment of this specification exhibits resistance to certain solvents after curing, a solution method can be used in the manufacture of the device, and thus the device can have a large area.

[0036] Furthermore, the compound according to an exemplary embodiment of this specification can be used as a material for an organic material layer in an organic light-emitting device, and can provide low driving voltage, high luminous efficiency, and / or long lifetime characteristics. In particular, the compound according to an exemplary embodiment of this specification has a long conjugation length, and therefore has the effect of reducing the driving voltage when applied to an organic light-emitting device. Attached Figure Description

[0037] Figure 1An example of an organic light-emitting device according to an exemplary embodiment of this specification is shown.

[0038] 101: Base

[0039] 201: Anode

[0040] 301: Hole Injection Layer

[0041] 401: Hole Transport Layer

[0042] 501: Emissive layer

[0043] 601: Layer that simultaneously transports and injects electrons

[0044] 701: Cathode Detailed Implementation

[0045] This instruction manual will be described in detail below.

[0046] An exemplary embodiment of this specification provides a compound of the following chemical formula 1.

[0047] [Chemical Formula 1]

[0048]

[0049] In chemical formula 1,

[0050] L1 to L3 may be the same as or different from each other, and each is independently a direct bond; -O-; substituted or unsubstituted alkylene; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl.

[0051] L11 and L12 may be the same as or different from each other, and each may be independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0052] Ar1 to Ar4 may be identical or different from each other, and each is independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0053] X1 to X3 may be the same as or different from each other, and each is independently a photocurable group or a thermosetting group.

[0054] R1 to R3 and R11 to R16 may be the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0055] a1 to a3 are each integers from 1 to 3.

[0056] When a1 to a3 are each 2 or larger, the substituents in parentheses may be the same or different from each other.

[0057] n1 to n3 are each an integer from 1 to 5.

[0058] n11 and n16 are each integers from 1 to 4.

[0059] n12 to n15 are each an integer from 1 to 3, and

[0060] When n1 to n3 and n11 to n16 are each 2 or greater, the substituents in parentheses may be the same or different from each other.

[0061] Typically, in the case of polymers, hole mobility is improved due to the long conjugation length, but there is a problem of difficulty in forming organic material layers by solution methods because polymers are not easily soluble in solvents. Conversely, in the case of monomolecular compounds, the compounds are easily soluble in solvents, thus favoring solution methods, but due to the short conjugation length, intramolecular hole migration is minimal, and intermolecular hole migration is the main factor, resulting in problems of increased driving voltage and reduced efficiency.

[0062] The compound according to an exemplary embodiment of this specification exhibits all the advantages of both polymers and monomolecules. Specifically, the compound is readily soluble in solvents and can therefore be used to form organic material layers via solution processing (or inkjet printing), and when applied to devices, it exhibits the effects of reduced drive voltage and increased efficiency due to the compound's excellent hole mobility.

[0063] Typically, when the relative number of nitrogen atoms in compounds with the same molecular weight increases, the HOMO energy level decreases (approaching the vacuum level), thus increasing the difference from the HOMO energy level of HTL, which leads to an increase in driving voltage. However, the compound of Formula 1 has a long conjugation length because the chains are linked by divalent fluorene groups and contain four nitrogen atoms simultaneously. Therefore, the compound of Formula 1 exhibits improved hole mobility and good ink properties due to its smaller molecular weight compared to polymers.

[0064] That is, when the compound of chemical formula 1 is applied to a device, it exhibits the effects of increasing conjugation length and improving hole mobility by containing -N-linker -N-divalent fluorene -N-linker -N-, and also exhibits the effects of reducing driving voltage and improving efficiency.

[0065] Furthermore, another layer can be formed by solution processing when another layer is stacked on the surface of an organic material layer formed using the compound. These effects are due to the structural characteristics of the compound of Formula 1. Specifically, the compound of Formula 1 has the advantages of higher solvent resistance by containing three or more curable groups, and the formation of a stable film that is not damaged by subsequent solution processing by forming a film that is fully cured by heat treatment or light treatment. Therefore, the compound of Formula 1 has the advantage of being applicable to solution processing because it helps to maintain the film after it is formed during device fabrication.

[0066] For example, in forming an organic material layer using the compound, cross-linking can be achieved through heat treatment or light treatment, enabling the provision of an organic material layer comprising a thin film structure. Furthermore, when another layer is stacked on the surface of the formed organic material layer, it is possible to prevent the organic material layer from dissolving, being morphologically affected, or decomposing due to solvents. Therefore, the range of solvents that can be used is broadened when forming another organic material layer on top of the organic material layer formed using the compound.

[0067] Furthermore, in the case of a compound according to an exemplary embodiment of this specification, an organic light-emitting device can be fabricated by solution application, thereby enabling the realization of a large-area device.

[0068] In this specification, "chain" means the -N-linking group -N- of Formula 1.

[0069] In this specification, the connection base refers to L11 and L12.

[0070] In one exemplary embodiment of this specification, N may be N contained in an amine group.

[0071] In one exemplary embodiment of this specification, the molecular weight of the compound of Formula 1 is from 1,000 g / mol to 5,000 g / mol. Therefore, the compound of Formula 1 exhibits the effect of having solvent resistance similar to that of a polymer, while its viscosity is similar to that of a monomer.

[0072] Therefore, compounds of Formula 1 do not have high viscosity for solvents, are easier to use in inkjet printing than polymers, and have the advantage of forming stable films that are not damaged by subsequent solution methods after curing.

[0073] In this specification, "monomer" means a material consisting of a structure without repeating units.

[0074] In one exemplary embodiment of this specification, the molecular weight of the monomolecule is less than 10,000 g / mol. Specifically, the molecular weight is from 100 g / mol to 5,000 g / mol.

[0075] In this specification, "polymer" means a polymer that repeats the same structure. That is, "polymer" means a polymer that contains repeating units.

[0076] In one exemplary embodiment of this specification, the polymer has a number-average molecular weight of 10,000 g / mol to 5,000,000 g / mol. Specifically, the number-average molecular weight is 10,000 g / mol to 1,000,000 g / mol.

[0077] In this specification, when a component is positioned "on" another component, this includes not only the case where one component is in contact with another component, but also the case where there is another component between the two components.

[0078] In this specification, when a component “includes” a constituent element, unless otherwise specifically described, this does not mean that other constituent elements are excluded, but rather that other constituent elements may be included.

[0079] In this specification, "photocurable group or thermosetting group" can mean a reactive substituent that crosslinks a compound by exposure to heat and / or light. Photocurable groups or thermosetting groups can be generated when free radicals generated by the decomposition of carbon-carbon multiple bonds or cyclic structures through light irradiation or heat treatment connect with each other.

[0080] In this specification, "curing group" means "photocurable group or thermosetting group".

[0081] The substituents in this specification will be described in detail below.

[0082] In this instruction manual, This refers to the portion that is bonded to another substituent or bonding portion.

[0083] In this specification, the term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is replaced by another substituent, and there is no restriction on the position to be substituted, as long as the position is where the hydrogen atom is substituted (i.e., the position where the substituent can be substituted), and when two or more substituents are substituted, the two or more substituents can be the same as or different from each other.

[0084] In this specification, the term "substituted or unsubstituted" means substituted with one or more substituents selected from: deuterium; halogen group; alkyl; cycloalkyl; alkoxy; aryloxy; amino; aryl; and heterocyclic group, substituted with two or more of the exemplified substituents linked together, or without substituents. For example, "substituents linked with two or more substituents" can be biphenyl. That is, biphenyl can also be aryl and can be interpreted as substituents linked with two phenyl groups.

[0085] Examples of substituents will be described below, but are not limited to.

[0086] Examples of halogen groups in this specification include fluorine (F), chlorine (Cl), bromine (Br), or iodine (I).

[0087] In this specification, alkyl groups can be straight-chain or branched, and their number of carbon atoms is not particularly limited, but is preferably from 1 to 60. According to one exemplary embodiment, the number of carbon atoms in the alkyl group is from 1 to 30. Specific examples of alkyl groups include, but are not limited to, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, etc.

[0088] In this specification, alkylene refers to a group having two bonding positions in an alkyl group, i.e., a divalent group. The above description of alkyl groups can be applied to alkylene groups, except that alkylene groups are divalent.

[0089] In this specification, the number of carbon atoms in the cycloalkyl group is not particularly limited, but is preferably from 3 to 60. According to one exemplary embodiment, the number of carbon atoms in the cycloalkyl group is from 3 to 30. Specific examples of cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, etc.

[0090] In this specification, alkoxy groups can be straight-chain, branched, or cyclic. The number of carbon atoms in an alkoxy group is not particularly limited, but is preferably 1 to 30. Specific examples of alkoxy groups include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, and n-decoxy.

[0091] In this specification, the amino group is composed of -NR 100 R 101 The group represented, and R 100 and R 101The amino groups may be the same as or different from each other, and each independently is hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl. Specifically, the amino group may be selected from -NH2; alkylamino; arylalkylamino; arylamino; arylheteroarylamino; alkylheteroarylamino; and heteroarylamino, and is not limited thereto. There is no particular limitation on the number of carbon atoms in the amino group, but it is preferably from 1 to 60.

[0092] In this specification, the aryl group is not particularly limited, but may have 6 to 60 carbon atoms, and may be monocyclic or polycyclic aryl. According to one exemplary embodiment, the aryl group has 6 to 30 carbon atoms. According to one exemplary embodiment, the aryl group has 6 to 20 carbon atoms. Examples of monocyclic aryl groups include, but are not limited to, phenyl, biphenyl, terphenyl, etc. Examples of polycyclic aryl groups include naphthyl, anthraceneyl, phenanthryl, pyrene, etc. Benzyl, triphenyl It includes, but is not limited to, methyl, fluorene, etc.

[0093] In this specification, the fluorene group may be substituted, and two substituents may bond together to form a spirocyclic structure.

[0094] When the fluorene group is substituted, the substituent can be... , , , And so on, and the illustrated structures can be substituted with other substituents. However, the structures are not limited to these.

[0095] In this specification, arylene refers to a group having two bonding positions within an aryl group, i.e., a divalent group. The above description of aryl groups can be applied to arylene groups, the difference being that arylene groups are divalent.

[0096] In this specification, a heterocyclic group is a heterocyclic group containing one or more of N, O, P, S, Si, and Se as heteroatoms, and its number of carbon atoms is not particularly limited, but can be from 2 to 60. According to one exemplary embodiment, the heterocyclic group has 2 to 30 carbon atoms. According to another exemplary embodiment, the heterocyclic group has 2 to 20 carbon atoms. Examples of heterocyclic groups include, but are not limited to, pyridinyl, pyrroloyl, pyrimidinyl, pyridazinyl, furanyl, thiopheneyl, benzothiopheneyl, benzofuranyl, dibenzothiopheneyl, dibenzofuranyl, etc.

[0097] In this specification, the above description of heterocyclic groups can be applied to heteroaryl groups, except that heteroaryl groups are aromatic.

[0098] In this specification, heteroaryl refers to a group having two bonding positions in a heteroaryl group, i.e., a divalent group. The above description of heteroaryl can be applied to heteroaryl, except that heteroaryl is divalent.

[0099] In one exemplary embodiment of this specification, L1 to L3 may be the same as or different from each other, and each is independently a direct bond; -O-; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0100] In one exemplary embodiment of this specification, L1 to L3 may be the same as or different from each other, and each is independently a direct bond; -O-; or a substituted or unsubstituted aryl group.

[0101] In one exemplary embodiment of this specification, L1 to L3 may be the same as or different from each other, and each is independently a direct bond; -O-; or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0102] In one exemplary embodiment of this specification, L1 to L3 may be the same as or different from each other, and each is independently a direct bond; -O-; substituted or unsubstituted phenylene; substituted or unsubstituted naphthylene; substituted or unsubstituted biphenylene; or substituted or unsubstituted terphenylene.

[0103] In one exemplary embodiment of this specification, L1 to L3 may be the same as or different from each other, and each is independently a direct bond; -O-; or a substituted or unsubstituted phenylene.

[0104] In one exemplary embodiment of this specification, chemical formula 1 is chemical formula 1-1 or 1-2.

[0105] [Chemical Formula 1-1]

[0106]

[0107] [Chemical Formula 1-2]

[0108]

[0109] In chemical formulas 1-1 and 1-2,

[0110] R1 to R3, R11 to R16, L11, L12, Ar1 to Ar4, n1 to n3 and n11 to n16 are the same as those defined in Formula 1.

[0111] L1' to L3' may be the same as or different from each other, and each is independently a direct bond or -O-; and

[0112] X1 to X3 may be the same as or different from each other, and each is independently a photocurable group or a thermosetting group.

[0113] In one exemplary embodiment of this specification, R11 to R16 are each hydrogen.

[0114] In one exemplary embodiment of this specification, R1 to R3 may be the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; or a substituted or unsubstituted alkyl group.

[0115] In one exemplary embodiment of this specification, R1 to R3 may be the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

[0116] In one exemplary embodiment of this specification, R1 to R3 may be the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; or an alkyl group.

[0117] In one exemplary embodiment of this specification, R1 to R3 may be the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; or a straight-chain or branched alkyl group.

[0118] In one exemplary embodiment of this specification, R1 to R3 may be the same as or different from each other, and each is independently hydrogen; F; methyl; or tert-butyl.

[0119] In another exemplary embodiment, Ar1 to Ar4 may be the same as or different from each other, and each is independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0120] In one exemplary embodiment of this specification, Ar1 to Ar4 may be the same as or different from each other, and each is independently any of the following structures. In this case, the following structures may be further substituted with additional substituents.

[0121]

[0122] In the structure,

[0123] W1 and W2 may be the same as or different from each other, and each is independently O, S, NRa, CRbRc or SiRdRe.

[0124] R101 to R111, Ra, Rb, Rc, Rd, and Re may be the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group.

[0125] p1 is an integer from 1 to 7.

[0126] p2, p4, and p5 are each integers from 1 to 4.

[0127] p3 and p6 are each integers from 1 to 5.

[0128] When p1 to p6 are each 2 or larger, the substituents in parentheses may be the same or different from each other, and

[0129] This refers to the portion that is bonded to chemical formula 1.

[0130] In one exemplary embodiment of this specification, R101 to R111 may be the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0131] In one exemplary embodiment of this specification, R101 to R111 may be the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0132] In another exemplary embodiment, R101 to R111 may be the same as or different from each other, and each is independently hydrogen; deuterium; or a halogen group.

[0133] In yet another exemplary embodiment, R101 to R111 may be the same as or different from each other, and each is independently hydrogen; deuterium; or F.

[0134] In one exemplary embodiment of this specification, W1 and W2 are each 0.

[0135] In one exemplary embodiment of this specification, W1 and W2 are each S.

[0136] In one exemplary embodiment of this specification, W1 and W2 are each CRbRc.

[0137] In one exemplary embodiment of this specification, Rb and Rc may be the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0138] In one exemplary embodiment of this specification, Rb and Rc may be the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0139] According to another exemplary embodiment, Rb and Rc may be the same as or different from each other, and each is independently hydrogen; deuterium; substituted or unsubstituted methyl; substituted or unsubstituted ethyl; or substituted or unsubstituted phenyl.

[0140] In one exemplary embodiment of this specification, Ar1 to Ar4 may be the same as or different from each other, and each is independently a substituted or unsubstituted phenyl; a substituted or unsubstituted biphenyl; a substituted or unsubstituted naphthyl; a substituted or unsubstituted fluorenyl; a substituted or unsubstituted dibenzofuranyl; or a substituted or unsubstituted dibenzothiopheneyl.

[0141] In one exemplary embodiment of this specification, Ar1 to Ar4 may be the same as or different from each other, and each is independently an unsubstituted or deuterated, halogenated or alkyl-substituted phenyl; an unsubstituted or deuterated, halogenated or alkyl-substituted biphenyl; an unsubstituted or deuterated, halogenated or alkyl-substituted naphthyl; an unsubstituted or deuterated, halogenated or alkyl-substituted fluorenyl; an unsubstituted or deuterated, halogenated or alkyl-substituted dibenzofuranyl; or an unsubstituted or deuterated, halogenated or alkyl-substituted dibenzothiophenyl.

[0142] In another exemplary embodiment, Ar1 to Ar4 may be the same as or different from each other, and each is independently an unsubstituted or halogenated phenyl; an unsubstituted or halogenated biphenyl; an unsubstituted or halogenated naphthyl; an unsubstituted or halogenated fluorenyl; an unsubstituted or halogenated dibenzofuranyl; or an unsubstituted or halogenated dibenzothiophenyl.

[0143] In yet another exemplary embodiment, Ar1 to Ar4 may be the same as or different from each other, and each is independently an unsubstituted or F-substituted phenyl; an unsubstituted or F-substituted biphenyl; an unsubstituted or F-substituted naphthyl; an unsubstituted or F-substituted fluorenyl; an unsubstituted or F-substituted dibenzofuranyl; or an unsubstituted or F-substituted dibenzothiophenyl.

[0144] In yet another exemplary embodiment, Ar1 to Ar4 may be the same as or different from each other, and each is independently an unsubstituted or F-substituted phenyl; or an unsubstituted or F-substituted dibenzofuranyl.

[0145] In one exemplary embodiment of this specification, L11 and L12 may be the same as or different from each other, and each is independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0146] In one exemplary embodiment of this specification, L11 and L12 may be the same as or different from each other, and each independently represents any of the following structures. In this case, the following structures may be further substituted with additional substituents.

[0147]

[0148] In the structure,

[0149] W11 to W22 may be the same as or different from each other, and each is independently O, S, CRuRv, SiRwRx or NRy.

[0150] R201 to R207, Ru, Rv, Rw, Rx, Ry, Rs, and Rt are identical or different from each other, and each is independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group.

[0151] q1 to q5 are each an integer from 1 to 4.

[0152] When q1 to q5 are each 2 or larger, the substituents in parentheses may be the same or different from each other, and

[0153] This refers to the portion that is bonded to chemical formula 1.

[0154] In one exemplary embodiment of this specification, R201 to R207, Ru, Rv, Rw, Rx, Ry, Rs and Rt are the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0155] In another exemplary embodiment, R201 to R207, Ru, Rv, Rw, Rx, Ry, Rs and Rt are the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0156] In one exemplary embodiment of this specification, L11 and L12 may be the same as or different from each other, and each independently represents any of the following structures. In this case, the following structures may be further substituted with a halogen group, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

[0157]

[0158] In the structure,

[0159] R201 to R205 may be the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group.

[0160] q1 to q5 are each an integer from 1 to 4.

[0161] When q1 to q5 are each 2 or larger, the substituents in parentheses may be the same or different from each other, and

[0162] This refers to the portion that is bonded to chemical formula 1.

[0163] According to yet another exemplary embodiment, L11 and L12 may be the same as or different from each other, and each is independently a substituted or unsubstituted phenylene; a substituted or unsubstituted biphenylene; a substituted or unsubstituted terphenylene; a substituted or unsubstituted fluorene; a substituted or unsubstituted phenanthroline; a substituted or unsubstituted naphthylene; or a substituted or unsubstituted naphthylene, or a group connected to two or more of the said substituents.

[0164] In one exemplary embodiment of this specification, L11 and L12 may be the same as or different from each other, and each is independently a substituted or unsubstituted phenylene; a substituted or unsubstituted biphenylene; or a substituted or unsubstituted terphenylene.

[0165] In one exemplary embodiment of this specification, L11 and L12 may be the same as or different from each other, and each is independently a substituted or unsubstituted biphenylene.

[0166] In one exemplary embodiment of this specification, the photocurable group or thermosetting group is any of the following structures.

[0167]

[0168] In the structure,

[0169] L50 to L55 may be the same as or different from each other, and each is independently a direct bond; -O-; or a substituted or unsubstituted alkylene group, and

[0170] This refers to the portion that is bonded to chemical formula 1.

[0171] In one exemplary embodiment of this specification, the photocurable group or thermosetting group is any of the following structures.

[0172]

[0173] In the structure,

[0174] L54 is a direct key or -O-, and

[0175] This refers to the portion that is bonded to chemical formula 1.

[0176] In one exemplary embodiment of this specification, the photocurable group or thermosetting group is , ,or And L54 is a direct key or -O-.

[0177] In one exemplary embodiment of this specification, the photocurable group or thermosetting group is any of the following structures.

[0178]

[0179] In one exemplary embodiment of this specification, the compound of Formula 1 is any of the following structures.

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207] In the structure described, hydrogen can be replaced by deuterium.

[0208] In one exemplary embodiment of this specification, the compound is deuterated by 10% or more.

[0209] In this specification, "deuteration" means that the available hydrogen atoms in the compound are replaced by deuterium.

[0210] In this specification, N% deuteration means N% of the hydrogens available in the corresponding structure are deuterated. For example, 50% deuteration of a phenyl means that three of the six hydrogens of the phenyl group are deuterated.

[0211] In this specification, the degree of deuteration can be determined by known methods such as nuclear magnetic resonance spectroscopy (NMR spectroscopy). 1 Determined by ¹H NMR or GC / MS.

[0212] In one exemplary embodiment of this specification, the compound is deuterated by 10% to 100%.

[0213] In one exemplary embodiment of this specification, the compound is deuterated by 10% to 90%.

[0214] In one exemplary embodiment of this specification, the compound is deuterated by 20% or more.

[0215] In one exemplary embodiment of this specification, the compound is deuterated by 20% to 100%.

[0216] In one exemplary embodiment of this specification, the compound is deuterated by 20% to 80%.

[0217] The compound according to an exemplary embodiment of this specification can be prepared by the preparation method described below.

[0218] For example, for a compound of formula 1, the core structure can be prepared by the following reaction scheme. Substituents can be bonded by methods known in the art, and the type and position of substituents or the number of substituents can be changed according to techniques known in the art.

[0219] <Reaction Protocol>

[0220]

[0221] In the reaction scheme, L1 to L3, L11, L12, Ar1 to Ar4, X1 to X3, R1 to R3, R11 to R16, a1 to a3, n1 to n3, and n11 to n16 are the same as those defined in Formula 1.

[0222] An exemplary embodiment of this specification provides a coating composition comprising a compound of chemical formula 1 described above.

[0223] In one exemplary embodiment of this specification, the coating composition further comprises a solvent. In one exemplary embodiment of this specification, the coating composition comprises a compound of Formula 1 and a solvent.

[0224] In one exemplary embodiment of this specification, the coating composition may be in a liquid phase. "Liquid phase" means that the composition is liquid at room temperature under atmospheric pressure.

[0225] In one exemplary embodiment of this specification, when the coating composition is applied to the organic material layer, a solvent that does not dissolve the material in the underlying layer is used. Therefore, there is an advantage that the organic material layer can be introduced via a solution method.

[0226] In one exemplary embodiment of this specification, solvent resistance is improved during heat treatment after coating because the compound contains photocurable or thermosetting groups. That is, the compound crosslinks after coating and is therefore insoluble in certain solvents.

[0227] For example, even if the coating composition is prepared by using a solvent to dissolve the compound and the layer is manufactured by a solution method, the layer can be resistant to the same solvent when cured by heat treatment.

[0228] Therefore, when an organic material layer is formed by using the compound and then subjecting it to a heat treatment process, a solution method can be used when applying another organic material layer.

[0229] For example, when the coating composition is applied to the hole injection layer, there is an advantage that the upper layer (hole transport layer, etc.) can be introduced by solution method using a specific solvent that exhibits resistance to the cured coating composition.

[0230] In one exemplary embodiment of this specification, the solvent included in the coating composition is a solvent that dissolves the compound. Examples of solvents include: chlorine-based solvents, such as chloroform, dichloromethane, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, and o-dichlorobenzene; ether-based solvents, such as tetrahydrofuran and dichlorobenzene. Alkanes; 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; polyols, such as ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxyethane, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerol, and 1,2-hexanediol and their derivatives; alcohol-based solvents, e.g. 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 solvents such as tetrahydronaphthalene, but may be used as long as the solvent can dissolve or disperse the compound according to one exemplary embodiment of this specification, and are not limited thereto.

[0231] In one exemplary embodiment of this specification, the solvent may be used alone or in a mixture of two or more solvents.

[0232] In one exemplary embodiment of this specification, the coating composition does not further contain p-doped material.

[0233] In one exemplary embodiment of this specification, the coating composition further comprises a p-doped material.

[0234] In this specification, p-doped material means a material that allows the host material to have p-semiconductor properties. p-semiconductor properties refer to the property of injecting or transporting holes at the highest occupied molecular orbital (HOMO) energy level, i.e., the property of a material with high hole conductivity.

[0235] In one exemplary embodiment of this specification, the p-doped material may be represented by any of the following chemical formulas A to H, but is not limited thereto.

[0236] [Chemical Formula A]

[0237]

[0238] [Chemical Formula B]

[0239]

[0240] [Chemical formula C]

[0241]

[0242] [Chemical formula D]

[0243]

[0244] [Chemical Formula E]

[0245]

[0246] [Chemical formula F]

[0247]

[0248] [Chemical formula G]

[0249]

[0250] [Chemical formula H]

[0251]

[0252] In this specification, any p-doped material that allows the host material to have p-semiconductor properties is sufficient; one or both or more of them may be used, and there is no limitation on their type.

[0253] In one exemplary embodiment of this specification, the p-doped material content is from 0 wt% to 500 wt% based on the compound of Formula 1. Specifically, the p-doped material content is from 100 wt% to 400 wt% based on the compound of Formula 1.

[0254] In one exemplary embodiment of this specification, the p-doped material is included in an amount from 0 wt% to 50 wt% based on the total solids content of the coating composition. In one exemplary embodiment of this specification, it is preferred that the p-doped material is included in an amount from 1 wt% to 50 wt% based on the total solids content of the coating composition, and more preferably, it is included in an amount from 10 wt% to 30 wt% based on the total solids content of the coating composition.

[0255] In another exemplary embodiment, the coating composition further comprises: a monomolecule containing functional groups that can be crosslinked by heat or light; or a monomolecule containing end groups that can form polymers by heat.

[0256] In one exemplary embodiment of this specification, a monomolecule containing functional groups that can be crosslinked by heat or light, or a monomolecule containing end groups that can form polymers by heat, may be a compound with a molecular weight of 3,000 g / mol or less.

[0257] In one exemplary embodiment of this specification, a monomolecule containing a functional group that can be crosslinked by heat or light, or a monomolecule containing an end group that can form a polymer by heat, may mean a monomolecule in which a functional group that can be crosslinked by heat or light or an end group that can form a polymer by heat is substituted in an aryl group (e.g., phenyl, biphenyl, fluorene, and naphthalene), an arylamine, or a fluorene.

[0258] In one exemplary embodiment of this specification, the viscosity of the coating composition at room temperature is 2 cP to 15 cP. Specifically, the viscosity of the coating composition is 2 cP to 10 cP. When the above viscosity is met, the device is easy to manufacture.

[0259] An exemplary embodiment of this specification provides an organic light-emitting device formed by using the coating composition.

[0260] An exemplary embodiment of this specification provides an organic light-emitting device comprising: a first electrode; a second electrode; and an organic material layer having one or more layers, including a light-emitting layer, disposed between the first electrode and the second electrode, wherein one or more layers of the organic material layer comprise a coating composition or a cured product thereof. In this case, the cured product of the coating composition is in a state in which the coating composition is cured by heat treatment or light treatment.

[0261] In one exemplary embodiment of this specification, the organic material layer comprising the coating composition or its cured product is a hole transport layer or a hole injection layer.

[0262] In one exemplary embodiment of this specification, the organic material layer comprising the coating composition or its cured product is an electron transport layer or an electron injection layer.

[0263] In one exemplary embodiment of this specification, the organic material layer comprising the coating composition or its cured product is a light-emitting layer.

[0264] In one exemplary embodiment of this specification, the organic material layer comprising the coating composition or its cured product is a light-emitting layer, and the light-emitting layer comprises a compound of Formula 1 as the body of the light-emitting layer.

[0265] In one exemplary embodiment of this specification, the organic material layer comprising the coating composition or its cured product is a light-emitting layer, and the light-emitting layer comprises a compound of Formula 1 as a dopant for the light-emitting layer.

[0266] In one exemplary embodiment of this specification, the organic light-emitting device includes one or more layers selected from hole injection layer, hole transport layer, electron transport layer, electron injection layer, electron blocking layer, hole blocking layer, layer that simultaneously transports and injects holes, and layer that simultaneously transports and injects electrons.

[0267] In one exemplary embodiment of this specification, the first electrode is an anode and the second electrode is a cathode.

[0268] According to another exemplary embodiment, the first electrode is a cathode, and the second electrode is an anode.

[0269] In another exemplary embodiment, the organic light-emitting device can be a conventional organic light-emitting device in which an anode, an organic material layer having one or more layers, and a cathode are sequentially stacked on a substrate.

[0270] In yet another exemplary embodiment, the organic light-emitting device may be an inverted organic light-emitting device in which a cathode, an organic material layer having one or more layers, and an anode are sequentially stacked on a substrate.

[0271] The organic material layer of the organic light-emitting device described in this specification can also have a single-layer structure, but it can have a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light-emitting device of the present invention can have a structure comprising a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, a layer that simultaneously transports and injects holes, and a layer that simultaneously transports and injects electrons as organic material layers. However, the structure of the organic light-emitting device is not limited to this, and it can include a smaller number of organic material layers.

[0272] For example, Figure 1 The structure of an organic light-emitting device according to an exemplary embodiment of this specification is illustrated below.

[0273] Figure 1 An example is shown of an organic light-emitting device in which an anode 201, a hole injection layer 301, a hole transport layer 401, a light-emitting layer 501, a layer 601 that simultaneously transports and injects electrons, and a cathode 701 are sequentially stacked on a substrate 101.

[0274] Figure 1 An organic light-emitting device is illustrated, but the structure of the organic light-emitting device of the present invention is not limited thereto.

[0275] When an organic light-emitting device comprises multiple layers of organic materials, the organic material layers can be formed from the same material or different materials.

[0276] The organic light-emitting devices of the present invention can be stacked as the structures shown in the following examples.

[0277] (1) Anode / hole transport layer / light-emitting layer / cathode

[0278] (2) Anode / hole injection layer / hole transport layer / light emission layer / cathode

[0279] (3) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / cathode

[0280] (4) Anode / hole transport layer / light-emitting layer / electron transport layer / cathode

[0281] (5) Anode / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0282] (6) Anode / hole injection layer / hole transport layer / light emission layer / electron transport layer / cathode

[0283] (7) Anode / hole injection layer / hole transport layer / light emission layer / electron transport layer / electron injection layer / cathode

[0284] (8) Anode / hole injection layer / hole buffer layer / hole transport layer / light emission layer / electron transport layer / cathode

[0285] (9) Anode / hole injection layer / hole buffer layer / hole transport layer / light emission layer / electron transport layer / electron injection layer / cathode

[0286] (10) Anode / Hole transport layer / Electron blocking layer / Light emitting layer / Electron transport layer / Cathode

[0287] (11) Anode / Hole transport layer / Electron blocking layer / Light emitting layer / Electron transport layer / Electron injection layer / Cathode

[0288] (12) Anode / hole injection layer / hole transport layer / electron blocking layer / light emission layer / electron transport layer / cathode

[0289] (13) Anode / Hole injection layer / Hole transport layer / Electron blocking layer / Light emission layer / Electron transport layer / Electron injection layer / Cathode

[0290] (14) Anode / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / cathode

[0291] (15) Anode / Hole transport layer / Light emission layer / Hole blocking layer / Electron transport layer / Electron injection layer / Cathode

[0292] (16) Anode / hole injection layer / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / cathode

[0293] (17) Anode / Hole injection layer / Hole transport layer / Light emission layer / Hole blocking layer / Electron transport layer / Electron injection layer / Cathode

[0294] (18) Anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / hole blocking layer / electron injection layer and transport layer / cathode

[0295] In the structure described, the “electron transport layer / electron injection layer” can be replaced by an “electron transport and injection layer” or a “layer that simultaneously transports and injects electrons”.

[0296] Furthermore, in the aforementioned structure, the “hole injection layer / hole transport layer” can be replaced by a “hole injection and transport layer” or a “layer that simultaneously injects and transports holes”.

[0297] The organic light-emitting devices described herein can be manufactured using materials and methods known in the art, except that one or more layers of organic material are formed by using a coating composition comprising a compound of formula 1.

[0298] For example, the organic light-emitting device of this specification can be manufactured by sequentially stacking an anode, an organic material layer, and a cathode on a substrate. In this case, the organic light-emitting device can be manufactured by depositing a metal or a conductive metal oxide or alloy thereof on the substrate using a physical vapor deposition (PVD) method such as sputtering or electron beam evaporation to form the anode; forming an organic material layer on the anode by a solution method, deposition method, etc., including a hole injection layer, a hole transport layer, a light-emitting layer, and a layer that simultaneously transports and injects electrons; and then depositing a material that can be used as a cathode on the organic material layer. In addition to the above method, the organic light-emitting device can also be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

[0299] This specification also provides a method for manufacturing organic light-emitting devices formed by using a coating composition.

[0300] Specifically, an exemplary embodiment of this specification includes: preparing a substrate; forming a first electrode on the substrate; forming an organic material layer having one or more layers on the first electrode; and forming a second electrode on the organic material layer, wherein forming the organic material layer includes forming an organic material layer having one or more layers by using a coating composition.

[0301] In one exemplary embodiment of this specification, spin coating is used to form an organic material layer having one or more layers by using a coating composition.

[0302] In another exemplary embodiment, a printing method is used to form an organic material layer having one or more layers by using a coating composition.

[0303] In one exemplary embodiment of this specification, examples of printing methods include, but are not limited to, inkjet printing, nozzle printing, offset printing, transfer printing, or screen printing.

[0304] Due to the structural characteristics of the coating composition according to an exemplary embodiment of this specification, the solution method is suitable for the coating composition, allowing the organic material layer to be formed by printing, and thus providing economic benefits in terms of time and cost when manufacturing devices.

[0305] In one exemplary embodiment of this specification, forming an organic material layer having one or more layers by using a coating composition includes: coating the coating composition onto a first electrode; and subjecting the coated composition to heat treatment or light treatment.

[0306] In one exemplary embodiment of this specification, heat treatment of the coated composition can be performed by heat treatment. The heat treatment temperature for heat treating the coated composition is from 85°C to 250°C. The heat treatment temperature can specifically be from 100°C to 250°C, and more specifically from 150°C to 250°C.

[0307] In one exemplary embodiment of this specification, the heat treatment time for heat-treating the coated composition can be from 1 minute to 2 hours, from 1 minute to 1 hour, and from 30 minutes to 1 hour, according to one exemplary embodiment.

[0308] In one exemplary embodiment of this specification, the coating composition can be light-treated by UV irradiation. The light-treatment of the coating composition can be performed for 30 minutes to 5 hours.

[0309] In one exemplary embodiment of this specification, coating a first electrode with a coating composition includes coating the first electrode with the coating composition and coating another organic material layer disposed on the first electrode with the coating composition.

[0310] In one exemplary embodiment of this specification, another organic material layer means an organic material layer formed of another material that does not contain the coating composition or its cured product.

[0311] In coating the first electrode with a coating composition, a solvent that does not dissolve the material in the underlying layer is used. For example, when the coating composition is applied to a hole transport layer, the coating composition contains a solvent that does not dissolve the material in the underlying layer (first electrode, hole injection layer, etc.). Therefore, there is an advantage that the hole transport layer can be introduced by a solution method.

[0312] By subjecting the coated composition to heat treatment or light treatment, the multiple compounds contained in the coated composition can form crosslinks, thereby providing an organic material layer comprising a thin film structure. In this case, when another layer is stacked on the surface of the organic material layer formed by using the coated composition, it is possible to prevent the organic material layer from dissolving, being morphologically affected, or decomposing due to solvents.

[0313] Therefore, when an organic material layer formed by using a coating composition is formed by a method including heat treatment or light treatment of the coated composition, solvent resistance is improved, allowing multiple layers to be formed by repeated solution deposition and crosslinking methods, and stability is improved, thereby improving the lifespan characteristics of the device.

[0314] In one exemplary embodiment of this specification, a material with a high work function is generally preferred as the anode material to facilitate hole injection into the organic material layer. Specific examples of anode materials include: metals, such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides, such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides, such as ZnO:Al or SnO2:Sb; conductive polymers, such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline; and so on, but are not limited thereto.

[0315] In one exemplary embodiment of this specification, a material with a low work function is generally preferred as the cathode material to facilitate electron injection into the organic material layer. Specific examples of cathode materials include: metals, such as barium, magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer materials, such as LiF / Al or LiO2 / Al; and so on, but are not limited thereto.

[0316] In one exemplary embodiment of this specification, the hole injection layer is a layer for injecting holes from the electrode, and the hole injection material is preferably a compound that has the ability to transport holes and thus has the effect of injecting holes at the anode and the excellent effect of injecting holes into the light-emitting layer or light-emitting material, preventing excitons generated by the light-emitting layer from moving to the electron injection layer or electron injection material, and also has excellent thin film formation ability. Furthermore, the highest occupied molecular orbital (HOMO) of the hole injection material is preferably a value between the work function of the anode material and the HOMO of the adjacent organic material layer. Specific examples of hole injection materials include compounds of the above-described chemical formula 1, metalloporphyrins, oligothiophenes, arylamine-based organic materials, hexanitrile hexaazabenzophenanthrene-based organic materials, quinacridone-based organic materials, and so on. Organic materials, anthraquinones, conductive polymers based on polyaniline and polythiophene, etc., but not limited to these.

[0317] In one exemplary embodiment of this specification, the hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer, and the hole transport material is suitably a material with high hole mobility that can receive holes from the anode or hole injection layer and transfer the holes to the light-emitting layer. Specific examples of hole transport materials include arylamine-based organic materials, conductive polymers, block copolymers having both conjugated and non-conjugated portions, etc., but the hole transport material is not limited to these. More specifically, compounds containing arylamine groups can be used in the hole transport layer.

[0318] In one exemplary embodiment of this specification, the hole transport layer comprises a compound with the following chemical formula HT-1.

[0319] [Chemical formula HT-1]

[0320]

[0321] In the chemical formula HT-1,

[0322] L201 is a substituted or unsubstituted aryl group, and

[0323] R201 to R204 may be the same as or different from each other, and each is independently hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heterocyclic.

[0324] In one exemplary embodiment of this specification, L201 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0325] In one exemplary embodiment of this specification, L201 is an aryl group.

[0326] In one exemplary embodiment of this specification, L201 is a substituted or unsubstituted phenylene; a substituted or unsubstituted biphenylene; or a substituted or unsubstituted naphthylene.

[0327] In one exemplary embodiment of this specification, L201 is phenylene; biphenylene; or naphthylene.

[0328] In one exemplary embodiment of this specification, L201 is a biphenylene oxide.

[0329] In one exemplary embodiment of this specification, R201 to R204 may be the same as or different from each other, and each is independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

[0330] In one exemplary embodiment of this specification, R201 to R204 may be the same as or different from each other, and each is independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0331] In one exemplary embodiment of this specification, R201 to R204 may be the same as or different from each other, and each is independently aryl.

[0332] In one exemplary embodiment of this specification, R201 to R204 may be the same as or different from each other, and each is independently a substituted or unsubstituted phenyl; a substituted or unsubstituted biphenyl; or a substituted or unsubstituted naphthyl.

[0333] In one exemplary embodiment of this specification, R201 to R204 may be the same as or different from each other, and each is independently phenyl; biphenyl; or naphthyl.

[0334] In one exemplary embodiment of this specification, the chemical formula HT-1 has the following structure.

[0335]

[0336] In one exemplary embodiment of this specification, the luminescent material contained in the luminescent layer is a material capable of receiving holes and electrons from the hole transport layer and the electron transport layer, respectively, and combining the holes and electrons to emit light in the visible light region, and preferably a material with good quantum efficiency for fluorescence or phosphorescence. Specific examples include: 8-hydroxyquinoline aluminum complexes (Alq3); carbazole-based compounds; dipolystyrene-based compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo[…]. Zyrazoles, benzothiazole-based and benzimidazole-based compounds; polymers based on poly(p-phenylenevinylene) (PPV); spirocyclic compounds; polyfluorene; red fluorene; etc., but not limited to these.

[0337] In one exemplary embodiment of this specification, the light-emitting layer may comprise a host material and a dopant material. Examples of host materials include fused aromatic ring derivatives, heterocyclic compounds, etc. Specifically, examples of fused aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentanebenzene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and examples of heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc., but are not limited to these examples. More specifically, anthracene derivatives may be used as the host.

[0338] In one exemplary embodiment of this specification, the body of the light-emitting layer comprises a compound with the following chemical formula EH-1.

[0339] [Chemical formula EH-1]

[0340]

[0341] In chemical formula EH-1,

[0342] L301 and L302 may be identical or different from each other, and each is independently a direct bond; a substituted or unsubstituted aryl group; or a substituted or unsubstituted divalent heterocyclic group.

[0343] Ar301 and Ar302 may be the same as or different from each other, and each is independently hydrogen; deuterium; substituted or unsubstituted aryl; or substituted or unsubstituted heterocyclic group.

[0344] R301 is hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, and

[0345] r301 is an integer from 1 to 7, and when r301 is 2 or greater, two or more R301s are the same or different from each other.

[0346] In one exemplary embodiment of this specification, L301 and L302 may be the same as or different from each other, and each is independently a direct bond; a substituted or unsubstituted monocyclic aryl group; or a substituted or unsubstituted polycyclic aryl group.

[0347] In one exemplary embodiment of this specification, L301 and L302 may be the same as or different from each other, and each is independently a direct bond; a substituted or unsubstituted phenylene; a substituted or unsubstituted biphenylene; or a substituted or unsubstituted naphthylene.

[0348] In one exemplary embodiment of this specification, L301 and L302 are each direct keys.

[0349] In one exemplary embodiment of this specification, Ar301 and Ar302 may be the same as or different from each other, and each is independently a substituted or unsubstituted aryl group.

[0350] In one exemplary embodiment of this specification, Ar301 and Ar302 may be the same as or different from each other, and each is independently a substituted or unsubstituted monocyclic aryl group; or a substituted or unsubstituted polycyclic aryl group.

[0351] In one exemplary embodiment of this specification, Ar301 and Ar302 may be the same as or different from each other, and each is independently a substituted or unsubstituted phenyl; a substituted or unsubstituted biphenyl; a substituted or unsubstituted terphenyl; a substituted or unsubstituted naphthyl; a substituted or unsubstituted anthraceneyl; a substituted or unsubstituted phenanthryl; a substituted or unsubstituted triphenylene; a substituted or unsubstituted pyrene; or a substituted or unsubstituted fluoreneyl.

[0352] In one exemplary embodiment of this specification, Ar301 and Ar302 may be the same as or different from each other, and each is independently a substituted or unsubstituted phenyl group; or a substituted or unsubstituted naphthyl group.

[0353] In one exemplary embodiment of this specification, Ar301 and Ar302 are each naphthyl.

[0354] In one exemplary embodiment of this specification, R301 is hydrogen.

[0355] In one exemplary embodiment of this specification, the chemical formula EH-1 is any of the following structures.

[0356]

[0357] In one exemplary embodiment of this specification, aromatic amine derivatives, styrene amine compounds, boron complexes, fluoranthene compounds, metal complexes, etc., can be used as dopant materials. Specifically, the aromatic amine derivative is a fused aromatic ring derivative having a substituted or unsubstituted aryl amino group, and examples include pyrene, anthracene, etc., having an aryl amino group. Examples of arylamines include benzo[a]pyrene, styrene amines, etc., and styrene amine compounds in which at least one aryl vinyl group is substituted with a substituted or unsubstituted aryl amine, and one or more substituents selected from aryl, silyl, alkyl, cycloalkyl, and arylamino groups are substituted or unsubstituted. Specific examples include, but are not limited to, styrene amines, styrene diamines, styrene triamines, styrene tetraamines, etc. Furthermore, examples of metal complexes include, but are not limited to, iridium complexes, platinum complexes, etc. More specifically, compounds containing aryl amine groups can be used as dopants.

[0358] In one exemplary embodiment of this specification, the dopant of the light-emitting layer comprises a compound with the following chemical formula ED-1.

[0359] [Chemical Formula ED-1]

[0360]

[0361] In chemical formula ED-1,

[0362] L401 is a substituted or unsubstituted arylene group; or a substituted or unsubstituted alkenyl group.

[0363] R401 to R404 may be the same as or different from each other, and each is independently hydrogen; deuterium; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heterocyclic.

[0364] r401 is an integer from 1 to 10, and

[0365] When r401 is 2 or greater, the structures within the parentheses may be the same or different from each other.

[0366] In one exemplary embodiment of this specification, L401 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms.

[0367] In one exemplary embodiment of this specification, L401 is arylene or alkenyl.

[0368] In one exemplary embodiment of this specification, L401 is a substituted or unsubstituted phenylene; a substituted or unsubstituted biphenylene; a substituted or unsubstituted naphthylene; or a substituted or unsubstituted vinylene.

[0369] In one exemplary embodiment of this specification, L401 is phenylene; biphenylene; naphthylene; or vinylene.

[0370] In one exemplary embodiment of this specification, R401 to R404 may be the same as or different from each other, and each is independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

[0371] In one exemplary embodiment of this specification, R401 to R404 may be the same as or different from each other, and each is independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0372] In one exemplary embodiment of this specification, R401 to R404 may be the same as or different from each other, and each is independently a substituted or unsubstituted phenyl; a substituted or unsubstituted biphenyl; or a substituted or unsubstituted naphthyl.

[0373] In one exemplary embodiment of this specification, R401 to R404 may be the same as or different from each other, and each is independently an unsubstituted or alkyl-substituted phenyl; an unsubstituted or alkyl-substituted biphenyl; or an unsubstituted or alkyl-substituted naphthyl.

[0374] In one exemplary embodiment of this specification, R401 to R404 may be the same as or different from each other, and each is independently an unsubstituted or alkyl-substituted phenyl.

[0375] In one exemplary embodiment of this specification, the chemical formula ED-1 has the following structure.

[0376]

[0377] In one exemplary embodiment of this specification, the electron transport layer is a layer that receives electrons from the electron injection layer and transports them to the light-emitting layer, and the electron transport material is suitably a material with high electron mobility that can readily receive electrons from the cathode and transfer them to the light-emitting layer. Specific examples include, but are not limited to, Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic radical compounds, hydroxyflavonoid-metal complexes, etc. The electron transport layer can be used with any desired cathode material according to the prior art. In particular, suitable examples of cathode materials are typical materials with low work functions followed by an aluminum or silver layer. Specific examples include cesium, barium, calcium, ytterbium, and samarium, each followed by an aluminum or silver layer.

[0378] In one exemplary embodiment of this specification, the electron injection layer is a layer that injects electrons from the electrode, and the electron injection material is preferably a compound that has the ability to transport electrons, the effect of injecting electrons from the cathode, and the excellent effect of injecting electrons into the light-emitting layer or light-emitting material, prevents excitons generated by the light-emitting layer from migrating to the hole injection layer, and also has excellent thin film formation ability. Specific examples include fluorenone, anthraquinone dimethyl ether, biphenylquinone, thiamethoxam dioxide, etc. azole, Diazole, triazole, imidazole, benzimidazole Tetracarboxylic acids, phenanthroline, fluorenemethane, anthrone and their derivatives, metal complexes, nitrogen-containing 5-membered ring derivatives, etc., but not limited to these.

[0379] In one exemplary embodiment of this specification, examples of metal complex compounds include, but are not limited to, lithium 8-hydroxyquinoline, bis(8-hydroxyquinoline)zinc, bis(8-hydroxyquinoline)copper, bis(8-hydroxyquinoline)manganese, tris(8-hydroxyquinoline)aluminum, tris(2-methyl-8-hydroxyquinoline)aluminum, tris(8-hydroxyquinoline)gallium, bis(10-hydroxybenzo[h]quinoline)beryllium, bis(10-hydroxybenzo[h]quinoline)zinc, bis(2-methyl-8-quinoline)chlorogallium, bis(2-methyl-8-quinoline)(o-cresol)gallium, bis(2-methyl-8-quinoline)(1-naphthol)aluminum, bis(2-methyl-8-quinoline)(2-naphthol)gallium, etc.

[0380] In one exemplary embodiment of this specification, the electron transport layer and the electron injection layer can be formed as layers that simultaneously transport and inject electrons. In this case, the material used in the layer that simultaneously transports and injects electrons can be either the electron transport material or the electron injection material described above. For example, phenanthroline-based compounds can be used in the layer that simultaneously transports and injects electrons.

[0381] In one exemplary embodiment of this specification, the layer that simultaneously transports and injects electrons comprises a compound with the chemical formula ET-1.

[0382] [Chemical formula ET-1]

[0383]

[0384] In the chemical formula ET-1,

[0385] R501 is hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group.

[0386] r501 is an integer from 1 to 8, and

[0387] When r501 is 2 or greater, the substituents in parentheses may be the same or different from each other.

[0388] In one exemplary embodiment of this specification, R501 is hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0389] In one exemplary embodiment of this specification, R501 is hydrogen; deuterium; alkyl; or aryl.

[0390] In one exemplary embodiment of this specification, R501 is hydrogen; deuterium; substituted or unsubstituted methyl; substituted or unsubstituted ethyl; substituted or unsubstituted propyl; substituted or unsubstituted butyl; substituted or unsubstituted phenyl; substituted or unsubstituted naphthyl; or substituted or unsubstituted biphenyl.

[0391] In one exemplary embodiment of this specification, R501 is hydrogen; deuterium; methyl; ethyl; propyl; butyl; phenyl; naphthyl; or biphenyl.

[0392] In one exemplary embodiment of this specification, R501 is hydrogen; methyl; or phenyl.

[0393] In one exemplary embodiment of this specification, the chemical formula ET-1 has the following structure.

[0394]

[0395] In one exemplary embodiment of this specification, the hole blocking layer is a layer that blocks holes from reaching the cathode, and can typically be formed under the same conditions as the hole injection layer. Specific examples of hole blocking materials include... Diazole or triazole derivatives, phenanthrene-rhein derivatives, BCP, aluminum complexes, etc., but not limited to these.

[0396] In one exemplary embodiment of this specification, the electron blocking layer is a layer that blocks electrons from reaching the anode, and materials known in the art can be used.

[0397] Depending on the material to be used, the organic light-emitting device according to this specification can be a top-emitting, bottom-emitting, or dual-emitting type.

[0398] Invention Embodiments

[0399] In the following description, this specification will be described in detail with reference to embodiments used to specifically describe this specification. However, various modifications may be made to the embodiments described herein, and they should not be construed as limiting the scope of this specification to the embodiments described below. The embodiments of this specification are provided to provide a more complete explanation of this specification to those skilled in the art.

[0400] <Synthesis example>

[0401] Synthesis example 1.

[0402]

[0403] Compound 1a (1.0 equivalent), compound 1b (2.2 equivalent), and sodium tert-butoxide (NaO) were used in the experiment. t Bu (3.0 equivalent) dissolved in toluene (relative to compound 1a, NaO) t The concentration of Bu was 0.2 M. The resulting solution was heated to 80°C, purged with nitrogen, and stirred for 30 minutes. Then, bis(tri-tert-butylphosphine)palladium(O) (Pd(P)) was added. t Bu3)2)(0.05 equivalent), and the resulting mixture was stirred for 3 hours. After evaporation of toluene, the crude product was obtained by extraction with CH2Cl2 / H2O, and purified by CH2Cl2 column chromatography to obtain compound 1. MS: [M+H] + =1783.3

[0404] Synthesis example 2.

[0405]

[0406] Compound 2 was prepared in the same manner as in Synthesis Example 1, except that compounds 1a and 1b in Synthesis Example 1 were prepared using compounds 2a and 2b, respectively. MS: [M+H + =1799.2

[0407] Synthesis example 3.

[0408]

[0409] Compound 3 was prepared in the same manner as in Synthesis Example 1, except that compounds 1a and 1b in Synthesis Example 1 were prepared using compounds 2a and 3b, respectively. MS: [M+H + =2095.6

[0410] Synthesis example 4.

[0411]

[0412] Compound 4 was prepared in the same manner as in Synthesis Example 1, except that compounds 1a and 1b in Synthesis Example 1 were prepared using compounds 2a and 4b, respectively. MS: [M+H + =2019.3

[0413] Synthesis example 5.

[0414]

[0415] Compound 5 was prepared in the same manner as in Synthesis Example 1, except that compounds 5a and 5b were used instead of compounds 1a and 1b in Synthesis Example 1, respectively. MS: [M+H + =2037.7

[0416] Synthesis example 6.

[0417]

[0418] Compound 6 was prepared in the same manner as in Synthesis Example 1, except that compounds 1a and 1b in Synthesis Example 1 were prepared using compounds 6a and 5b, respectively. MS: [M+H + =2389.7

[0419] Compare the synthesis example 1.

[0420]

[0421] Compound Z-1 was prepared in the same manner as in Synthesis Example 1, except that compound 7a was used instead of compound 1a in Synthesis Example 1. MS: [M+H + =1565.0

[0422] Compare with synthetic example 2.

[0423]

[0424] Compound Z-2 was prepared in the same manner as in Synthesis Example 1, except that compounds 1a and 1b in Synthesis Example 1 were prepared using compounds 8a and 5b, respectively. MS: [M+H + =2103.4

[0425] Compare the synthesis example 3.

[0426]

[0427] Compound Z-3 was prepared in the same manner as in Synthesis Example 1, except that compounds 1a and 1b in Synthesis Example 1 were prepared using compounds 9a and 9b, respectively. MS: [M+H + =2081.8

[0428] Compare the synthesis example 4.

[0429]

[0430] Compound Z-4 was prepared in the same manner as in Synthesis Example 1, except that compounds 1a and 1b in Synthesis Example 1 were replaced with compounds 10a and 9b, respectively. MS: [M+H] + =1600.3

[0431] <Experimental Example 1: Viscosity Measurement>

[0432] Experimental Example 1-1.

[0433] After dissolving 10 mg of compound 1 prepared in Synthesis Example 1 in 0.32 g of purified toluene to obtain a concentration of 3% by weight, the viscosity was measured using a viscometer, and the resulting solution exhibited a viscosity value of 4.8 cP.

[0434] Experimental Examples 1-2.

[0435] The viscosity of compound 2 was measured in the same manner as in Experimental Example 1-1, except that compound 2 was used instead of compound 1 in Experimental Example 1-1. The result was that compound 2 exhibited a viscosity value of 3.7 cP.

[0436] Experimental Examples 1-3

[0437] The viscosity of compound 3 was measured in the same manner as in Experimental Example 1-1, except that compound 3 was used instead of compound 1 in Experimental Example 1-1. The result was that compound 3 exhibited a viscosity value of 4.4 cP.

[0438] Experimental Examples 1-4.

[0439] The viscosity of compound 4 was measured in the same manner as in Experimental Example 1-1, except that compound 4 was used instead of compound 1 in Experimental Example 1-1. The result was that compound 4 exhibited a viscosity value of 6.2 cP.

[0440] Experimental Examples 1-5.

[0441] The viscosity of compound 5 was measured in the same manner as in Experimental Example 1-1, except that compound 5 was used instead of compound 1 in Experimental Example 1-1. The result was that compound 5 exhibited a viscosity value of 7.8 cP.

[0442] Experimental Examples 1-6.

[0443] The viscosity of compound 6 was measured in the same manner as in Experimental Example 1-1, except that compound 6 was used instead of compound 1 in Experimental Example 1-1. The result was that compound 6 exhibited a viscosity value of 5.1 cP.

[0444] Comparative Example 1-1.

[0445] The viscosity of compound A was measured in the same manner as in Experimental Example 1-1, except that the following compound A was used instead of compound 1 in Experimental Example 1-1. The result was that compound A exhibited a viscosity value of 3.4 cP.

[0446]

[0447] Comparative Examples 1-2.

[0448] The viscosity of compound B was measured in the same manner as in Experimental Example 1-1, except that the following compound B was used instead of compound 1 in Experimental Example 1-1. The result was that compound B exhibited a viscosity value of 14.2 cP.

[0449]

[0450] (n for compound B: an integer from 2 to 10,000)

[0451] (Mn of compound B: 23,600, Mw of compound B: 41,400)

[0452] As a result of comparing experimental examples 1-1 to 1-6 with comparative examples 1-1 and 1-2, it was determined that compounds 1 to 6 synthesized in the synthetic examples tend to have viscosities similar to those of the single molecular weight compounds in comparative example 1-1.

[0453] <Experimental Example 2. Fabrication of Organic Light-Emitting Devices>

[0454] Experimental Example 2-1.

[0455] A glass substrate thinly coated with 1,500 Å indium tin oxide (ITO) was immersed in distilled water containing a cleaning agent and ultrasonically washed. In this case, a product manufactured by Fischer Co. was used as the cleaning agent, and distilled water filtered twice using a filter manufactured by Millipore Co. was used as the distilled water. After washing the ITO for 30 minutes, ultrasonic washing was repeated twice for 10 minutes each time with distilled water. After washing with distilled water, the substrate was ultrasonically washed with isopropanol and acetone solvents, dried, then cleaned for 5 minutes, and transferred to a glove box.

[0456] On the ITO transparent electrode prepared above, 1.5 wt% cyclohexanone ink comprising Compound 1 prepared in Synthesis Example 1 and Compound P below, in a weight ratio of 8:2 (Compound 1:Compound P), was spin-coated onto the ITO surface and heat-treated (cured) at 230°C for 30 minutes to form a hole injection layer with a thickness of 30 nm. 2 wt% toluene ink of the following α-NPD compound was spin-coated onto the hole injection layer to form a hole transport layer with a thickness of 40 nm. Subsequently, the ITO transparent electrode was transferred to a vacuum depositor, and then the following ADN compound and the following DPAVBi compound were vacuum-deposited on the hole transport layer in a weight ratio of 20:1 (ADN:DPAVBi) to a thickness of 20 nm to form a light-emitting layer. The following BCP compound was vacuum-deposited on the light-emitting layer to a thickness of 35 nm to form a layer that simultaneously transports and injects electrons. LiF and aluminum were sequentially deposited on the layer that simultaneously transports and injects electrons to thicknesses of 1 nm and 100 nm, respectively, to form a cathode.

[0457]

[0458] In the above steps, the deposition rate of the organic material was maintained at 0.4 Å / s to 0.7 Å / s, the deposition rates of lithium fluoride and aluminum at the cathode were maintained at 0.3 Å / s and 2 Å / s, respectively, and the vacuum level during deposition was maintained at 2 × 10⁻⁶. -7 Up to 5×10 -6 Entrust.

[0459] Experimental Example 2-2.

[0460] Organic light-emitting devices were fabricated in the same manner as in Experimental Example 2-1, except that compound 2 was used instead of compound 1.

[0461] Experimental Example 2-3.

[0462] Organic light-emitting devices were fabricated in the same manner as in Experimental Example 2-1, except that compound 3 was used instead of compound 1.

[0463] Experimental Example 2-4.

[0464] Organic light-emitting devices were fabricated in the same manner as in Experimental Example 2-1, except that compound 4 was used instead of compound 1.

[0465] Experimental Example 2-5.

[0466] Organic light-emitting devices were fabricated in the same manner as in Experimental Example 2-1, except that compound 5 was used instead of compound 1.

[0467] Experimental Example 2-6.

[0468] Organic light-emitting devices were fabricated in the same manner as in Experimental Example 2-1, except that compound 6 was used instead of compound 1.

[0469] Comparative Example 2-1.

[0470] Organic light-emitting devices were fabricated in the same manner as in Experimental Example 2-1, except that compound Z-1 was used instead of compound 1.

[0471] Comparative Example 2-2.

[0472] Organic light-emitting devices were fabricated in the same manner as in Experimental Example 2-1, except that compound Z-2 was used instead of compound 1.

[0473] Comparative examples 2-3.

[0474] Organic light-emitting devices were fabricated in the same manner as in Experimental Example 2-1, except that compound Z-3 was used instead of compound 1.

[0475] Comparative Examples 2-4.

[0476] Organic light-emitting devices were fabricated in the same manner as in Experimental Example 2-1, except that compound Z-4 was used instead of compound 1.

[0477] For the organic light-emitting devices fabricated in Experimental Examples 2-1 to 2-6 and Comparative Examples 2-1 to 2-4, at 10 mA / cm 2 The driving voltage, current efficiency, power efficiency, and luminance value were measured at the measured current, as well as the time (T95) taken for the luminance to return to 95% of the initial luminance (1000 nits). The results are shown in Table 1 below.

[0478] [Table 1]

[0479]

[0480] As can be seen from Table 1, compared with organic light-emitting devices using other compounds (Comparative Examples 2-1 to 2-4), organic light-emitting devices using compounds according to the present invention (Experimental Examples 2-1 to 2-6) have low driving voltage, high power efficiency and excellent lifespan.

[0481] While preferred exemplary embodiments of the present invention (hole injection layer) have been described above, the present invention is not limited thereto, and various modifications can be made and implemented within the scope of the claims and detailed description of the present invention, and such modifications also fall within the scope of the present invention.

Claims

1. A compound with the following chemical formula 1-1 or 1-2: [Chemical Formula 1-1] [Chemical Formula 1-2] in, In chemical formulas 1-1 and 1-2, L1' to L3' may be the same as or different from each other, and each is independently a direct bond or -O-; and L11 and L12 may be the same as or different from each other, and each is independently a aryl group. Ar1 to Ar4 may be the same as or different from each other, and each is independently an aryl group substituted or unsubstituted with a halogen group; or a heteroaryl group substituted or unsubstituted with a halogen group. X1 to X3 may be the same as or different from each other, and each is independently a photocurable group or a thermosetting group. R1 to R3 and R11 to R16 may be the same as or different from each other, and each is independently hydrogen; deuterium; a halogen group; or an alkyl group. n1 to n3 are each an integer from 1 to 5. n11 and n16 are each integers from 1 to 4. n12 to n15 are each an integer from 1 to 3, and When n1 to n3 and n11 to n16 are each 2 or greater, the substituents in parentheses may be the same or different from each other, and The photocurable group or the thermosetting group is any one of the following structures: In the structure, L50 to L55 may be the same as or different from each other, and each is independently a direct bond; -O-; or alkylene; and The portion that is bonded to chemical formula 1-1 or 1-2.

2. The compound according to claim 1, wherein the compound has any of the following structures: 。 3. A coating composition comprising the compound according to any one of claims 1 and 2.

4. An organic light-emitting device, comprising: First electrode; Second electrode; as well as An organic material layer comprising one or more layers, including a light-emitting layer, disposed between the first electrode and the second electrode. One or more layers of the organic material layer comprise the coating composition or its cured product according to claim 3.

5. The organic light-emitting device according to claim 4, wherein the organic material layer comprising the coating composition or its cured product is a hole transport layer or a hole injection layer.

6. A method for manufacturing an organic light-emitting device, the method comprising: Prepare the base; A first electrode is formed on the substrate; An organic material layer having one or more layers is formed on the first electrode; as well as A second electrode is formed on the organic material layer. The formation of the organic material layer includes forming an organic material layer having one or more layers by using the coating composition according to claim 3.

7. The method of claim 6, wherein forming the organic material layer having one or more layers by using the coating composition comprises: The coating composition is coated onto the first electrode; as well as The coated composition is subjected to heat treatment or light treatment.

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