Composition for organic material layer of organic light-emitting device, organic light-emitting device including composition, and method for manufacturing organic light-emitting device

Abstract

The present specification relates to a composition for an organic material layer of an organic light-emitting device, an organic light-emitting device including the composition, and a method for manufacturing the organic light-emitting device.

Description

TECHNICAL FIELD

[0001] The present specification relates to a composition for an organic material layer of an organic light emitting device, an organic light emitting device including the composition, and a method for manufacturing an organic light emitting device.

[0002] This application claims the benefit of the filing date of Korean Patent Application No. 10-2023-0109910 filed on August 22, 2023, in the Korean Intellectual Property Office, the disclosure of which is hereby incorporated by reference in its entirety. BACKGROUND

[0003] An electroluminescent device is a self-emissive display device, and has advantages in that it has a wide viewing angle, excellent contrast, and a fast response speed.

[0004] An organic light emitting device has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to an organic light emitting device having such a structure, electrons and holes injected from the two electrodes form pairs by recombining in the organic thin film, and then emit light while being annihilated. The organic thin film can be configured as a single layer or multiple layers as needed.

[0005] The material of the organic thin film can have a light emitting function as needed. For example, as an organic thin film material, a compound that can itself constitute an emission layer alone can be used, or a compound that can serve as a host or a dopant of a host-dopant type emission layer can be used. In addition, as a material of the organic thin film, a compound capable of performing at least one function selected from hole injection, hole transport, electron blocking, hole blocking, electron transport, and electron injection can be used.

[0006] There is a continuing need to develop materials for organic thin films in order to improve the performance, lifespan, or efficiency of an organic light emitting device.

[0007] [Related Art Documents]

[0008] (Patent Document 1) U.S. Patent No. 4,356,429 SUMMARY [Technical Objectives] The present specification aims to provide a composition for an organic material layer of an organic light emitting device, an organic light emitting device including the composition, and a method for manufacturing an organic light emitting device.

[0009] [Technical Solution] One embodiment of the present specification provides a composition for an organic material layer of an organic light emitting device, the composition including: a compound of the following Chemical Formula 1; a compound of the following Chemical Formula 2; and a compound of the following Chemical Formula 3.

[0010] [Chemical Formula 1]

[0011] wherein, in Chemical Formula 1, X is O or S, R1and R2, R2and R3, or R3and R4are bonded to each other to form a substituted or unsubstituted benzene ring, when R3and R4are bonded to each other to form a substituted or unsubstituted benzene ring, R1is hydrogen or deuterium, any one of the remaining groups among R1to R4and R5to R8is -(L1)l1-N(Ar1)(Ar2), and the other is -(L2)l2-Ar3, the remaining groups among R1to R8are each independently selected from the group consisting of hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; and a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, L1and L2are each independently selected from the group consisting of a direct bond; and a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, l1and l2are each an integer of 1 to 3, and when l1and l2are each 2 or more, the substituents in each set of parentheses can be the same as or different from each other, Ar1and Ar2are each independently selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; and a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, Ar3is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, [Chemical Formula 2]

[0012] wherein, in Chemical Formula 2, L11is a direct bond; a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms, and l11is an integer of 1 to 3, and when l11is 2 or more, the corresponding L11may be the same as or different from each other, R11is: a halogen group; a cyano group; a substituted or unsubstituted alkyl group having from 1 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having from 3 to 60 carbon atoms; a substituted or unsubstituted heterocycloalkyl group having from 2 to 60 carbon atoms; a substituted or unsubstituted aryl group having from 6 to 60 carbon atoms; a substituted or unsubstituted heteroaryl group having from 2 to 60 carbon atoms; or a substituted or unsubstituted silyl group, and Any one of R12to R19is a substituted or unsubstituted carbazolyl group, or two adjacent ones among R12to R19are bonded to each other to form a substituted or unsubstituted heterocyclic ring having from 2 to 30 carbon atoms, and The remaining ones among R12to R19are each independently: hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having from 1 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having from 3 to 60 carbon atoms; a substituted or unsubstituted heterocycloalkyl group having from 2 to 60 carbon atoms; a substituted or unsubstituted aryl group having from 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having from 2 to 60 carbon atoms, [Chemical Formula 3]

[0013] wherein, in Chemical Formula 3, Y is O or S, Any one of R21to R28is -(L21)l21-(N-Het), L21is: a direct bond; or a substituted or unsubstituted arylene group having from 6 to 60 carbon atoms, l21is an integer of from 1 to 3, and when l21is 2 or more, L21are the same or different, N-Het is a substituted or unsubstituted heteroaryl group including a C=N bond, The remaining ones among R21to R28are each independently selected from the group consisting of: hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted alkyl group having from 1 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having from 3 to 60 carbon atoms; a substituted or unsubstituted heterocycloalkyl group having from 2 to 60 carbon atoms; a substituted or unsubstituted aryl group having from 6 to 60 carbon atoms; a substituted or unsubstituted heteroaryl group having from 2 to 60 carbon atoms; a substituted or unsubstituted silyl group; and a substituted or unsubstituted phosphine oxide group.

[0014] Another embodiment of the present specification provides an organic light emitting device including: a first electrode; a second electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein at least one layer among the organic material layers includes a composition for an organic material layer of the organic light emitting device.

[0015] Another 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 one or more organic material layers on the first electrode; and forming a second electrode on the organic material layers, wherein the step of forming the organic material layers comprises forming one or more organic material layers by using a composition for organic material layers of an organic light-emitting device as described above.

[0016] [Beneficial Effects] The compositions for organic material layers in organic light-emitting devices described in this specification include all three compounds represented by chemical formulas 1 to 3, and therefore, when used as materials for organic light-emitting devices, they can improve the luminous efficiency and lifetime characteristics of the devices.

[0017] Specifically, the compound of Formula 1 is characterized by a relatively long lifetime, the compound of Formula 2 provides high efficiency, and the compound of Formula 3 is a unipolar N-host with high electron mobility. When these three compounds are mixed in appropriate proportions and used as materials for the device, improvements in the device's efficiency and lifetime can be confirmed. Attached Figure Description

[0018] Figures 1 to 3 These are views illustrating, respectively, the stacked structures of organic light-emitting devices according to embodiments of this specification.

[0019] [Figure Labels] 100: Base 200: Anode 300: Organic material layer 301: Hole Injection Layer 302: Hole transport layer 303: Launch Layer 304: Cavity Blocking Layer 305: Electron Transport Layer 306: Electron Injection Layer 400: Cathode Best Mode This disclosure will be described in more detail below.

[0020] In this specification, when a part is referred to as "comprising" a component, it means that, unless expressly stated to the contrary, the presence of one or more other components is not excluded, but rather other components may be included.

[0021] In this specification, “N to N’” means N or more and N’ or less.

[0022] In this specification, in the chemical formula, Indicates the location where the bond occurred.

[0023] The term “substitution” means that a hydrogen atom bonded to a carbon or nitrogen atom in a compound is replaced by another substituent, and the position to be substituted is not restricted, as long as the position is where the hydrogen atom can be substituted (i.e., the substituent is the position where it can be substituted), and when two or more substitutions occur, the two or more substituents can be the same or different from each other.

[0024] In this specification, the term "substituted or unsubstituted" means substituted by at least one substituent selected from the group consisting of: deuterium; halogen group; cyano; alkyl having 1 to 60 carbon atoms; alkenyl having 2 to 60 carbon atoms; alkynyl having 2 to 60 carbon atoms; haloalkyl having 1 to 60 carbon atoms; alkoxy having 1 to 60 carbon atoms; aryloxy having 6 to 60 carbon atoms; alkylthio having 1 to 60 carbon atoms; alkylthio having 6 ... arylthio group having 60 carbon atoms; alkylsulfonyl group having 1 to 60 carbon atoms; arylsulfonyl group having 6 to 60 carbon atoms; cycloalkyl group having 3 to 60 carbon atoms; heterocycloalkyl group having 2 to 60 carbon atoms; aryl group having 6 to 60 carbon atoms; heteroaryl group having 2 to 60 carbon atoms; silyl group; phosphine oxide group; and amino group, or meaning substituted by a substituent connected to two or more substituents selected from the above substituents, or meaning unsubstituted.

[0025] In this specification, the statement "when no substituent is indicated in the chemical formula or compound structure" means that the hydrogen atom is bonded to the carbon atom. However, due to deuterium ( 2 H (deuterium) is an isotope of hydrogen, therefore some hydrogen atoms can be deuterium.

[0026] In one embodiment of this application, the statement "when no substituent is indicated in the chemical formula or compound structure" can mean that all positions where a substituent can be present are hydrogen or deuterium. That is, in the case of deuterium as an isotope of hydrogen, some of the hydrogen atoms can be deuterium as an isotope, and in this case, the deuterium content can be from 0% to 100%, and the deuterium content can also be expressed as the deuterium substitution rate.

[0027] In one embodiment of this application, when stating "when no substituent is indicated in the chemical formula or compound structure", hydrogen and deuterium can be used in a mixed state in the compound without explicitly excluding deuterium (such as "deuterium content is 0%, hydrogen content is 100%" or "all substituents are hydrogen").

[0028] In one embodiment of this application, deuterium is an isotope of hydrogen and is an element having a deuterium nucleus consisting of one proton and one neutron as its atomic nucleus, and can be represented as hydrogen-2, and its element symbol can also be written as D or 2 H.

[0029] In one embodiment of this application, an isotope refers to an atom having the same atomic number (Z) but different mass numbers (A), and can also be interpreted as an element having the same number of protons but different numbers of neutrons.

[0030] In one embodiment of this application, the substitution rate T% of a specific substituent can be defined as such that when the total number of substituents that the basic compound can have is defined as T1 and the number of specific substituents among them is defined as T2, T% can be defined as T2 / T1×100.

[0031] In other words, in one example, "by" The statement "20% deuterium substitution rate in phenyl" means that the total number of substituted positions that a phenyl group can have is 5 (T1 in the formula), and when the number of deuterium atoms among them is 1 (T2 in the formula), it can be expressed as 20%. That is, 20% deuterium substitution rate in phenyl can be represented by the following structural formula.

[0032]

[0033] Furthermore, in one embodiment of this application, in the case of "phenyl with 0% deuterium substitution rate", this may mean a phenyl that does not contain deuterium atoms as substituents, that is, a phenyl with five hydrogen atoms.

[0034] In this specification, halogen can be fluorine, chlorine, bromine or iodine.

[0035] In this specification, alkyl groups comprise straight or branched chains having 1 to 60 carbon atoms and may be further substituted by another substituent. The number of carbon atoms in an alkyl group may be 1 to 60, specifically 1 to 40, and more specifically 1 to 20. Specific examples include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1-dimethylpropyl, isohexyl, 2-methylpentyl, 4-methylhexyl, and 5-methylhexyl.

[0036] In this specification, alkenyl groups comprise straight or branched chains having 2 to 60 carbon atoms and may be further substituted by another substituent. The number of carbon atoms in an alkenyl group can be 2 to 60, specifically 2 to 40, and more specifically 2 to 20. Specific examples include, but are not limited to, vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(1-naphthyl)vinyl-1-yl, 2,2-bis(1-diphenyl)vinyl-1-yl, bis(1-diphenyl)vinyl-1-yl, styreneyl, and styreneyl.

[0037] In this specification, the alkynyl group comprises a straight or branched chain having 2 to 60 carbon atoms and may be further substituted by another substituent. The number of carbon atoms in the alkynyl group can be 2 to 60, specifically 2 to 40, and more specifically 2 to 20.

[0038] In this specification, alkyl halogroup means an alkyl group substituted with a halogen group, and specific examples of alkyl halogroups include, but are not limited to, -CF3 and -CF2CF3.

[0039] In this specification, alkoxy groups are represented by -O (R101), and examples of alkyl groups as described above can be applied to R101.

[0040] In this specification, aryl groups are represented by -O (R102), and the examples of aryl groups described above can be applied to R102.

[0041] In this specification, alkyl thio groups are represented by -S(R103), and examples of alkyl groups as described above can be applied to R103.

[0042] In this specification, aryl thio groups are represented by -S(R104), and the examples of aryl groups described above can be applied to R104.

[0043] In this specification, alkyl sulfonyl groups are represented by -S(=O)2(R105), and examples of alkyl groups as described above can be applied to R105.

[0044] In this specification, arylsulfonyl group is represented by -S(=O)2(R106), and the examples of aryl groups described above can be applied to R106.

[0045] In this specification, cycloalkyl groups comprise monocyclic or polycyclic groups having 3 to 60 carbon atoms and may be further substituted by another substituent. Here, the term "polycyclic" means a group in which the cycloalkyl group is directly bonded to or fused with another cyclic group. Here, the "other cyclic group" can be a cycloalkyl group, but can also be a different type of cyclic group, such as heterocycloalkyl, aryl, and heteroaryl groups. The number of carbon atoms in a cycloalkyl group can be 3 to 60, specifically 3 to 40, and more specifically 5 to 20. Specific examples include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, and cyclooctyl.

[0046] In this specification, heterocyclic alkyl groups include O, S, Se, N, or Si as heteroatoms and comprise monocyclic or polycyclic groups having 2 to 60 carbon atoms, and may be further substituted by another substituent. Here, the term "polycyclic" means a group in which the heterocyclic alkyl group is directly bonded to or fused with another cyclic group. Here, "another cyclic group" can be a heterocyclic alkyl group, but can also be a different type of cyclic group, such as cycloalkyl, aryl, and heteroaryl groups. The number of carbon atoms in a heterocyclic alkyl group can be 2 to 60, specifically 2 to 40, and more specifically 3 to 20.

[0047] In this specification, aryl groups comprise monocyclic or polycyclic groups having 6 to 60 carbon atoms and may be further substituted by another substituent. Here, the term "polycyclic" means a group in which the aryl group is directly bonded to or fused with another cyclic group. Here, the "other cyclic group" can be an aryl group, but can also be a different type of cyclic group, such as cycloalkyl, heterocycloalkyl, and heteroaryl groups. Aryl groups include spirocyclic groups. The number of carbon atoms in an aryl group can be 6 to 60, specifically 6 to 40, and more specifically 6 to 25. Specific examples of aryl groups include, but are not limited to, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, perylene, fluoranthracene, benzo[phenanthrene], phenatenyl, pyrene, tetraphenyl, pentaphenyl, fluorenyl, indene, acenaphthene, benzo[fluorenyl], spirobisfluorenyl, 2,3-dihydro-1H-indene, and their fused-ring groups.

[0048] In this specification, terphenyl may be selected from the following structures.

[0049]

[0050] In this specification, the fluorene group may be substituted, and adjacent substituents may bond to each other to form a ring.

[0051] When the fluorene group is substituted, it can have the following structures, but is not limited to these.

[0052]

[0053] In this specification, heteroaryl groups include S, O, Se, N, or Si as heteroatoms, and include monocyclic or polycyclic groups having 2 to 60 carbon atoms, and may be further substituted by other substituents. Here, the term "polycyclic" means a group in which the heteroaryl group is directly bonded to or fused with another cyclic group. Here, the "other cyclic group" can be a heteroaryl group, but it can also be another type of cyclic group, such as cycloalkyl, heterocycloalkyl, and aryl groups. The number of carbon atoms in a heteroaryl group can be 2 to 60, specifically 2 to 40, and more specifically 3 to 25. Specific examples of heteroaryl groups include, but are not limited to, pyridyl, pyrroloyl, pyrimidinyl, pyridazinyl, furanyl, thiopheneyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, furazanyl, oxadiazolyl, thiazolyl, dithiazolyl, tetrazolyl, pyranyl, thiaranyl, diazinyl, oxazinyl, thiazolyl, dioxinyl, triazinyl, tetraazinyl, quinolinyl, isoquinolinyl, etc. Quinazolinyl, isoquinazolinyl, quinoxalinyl, naphridinyl, acridineyl, phenanthridineyl, imidazopyridyl, diazanaphthyl, triazaindenyl, indoleyl, indazinyl, benzothiazolyl, benzoxazolyl, benzoimidazolyl, benzothiopheneyl, benzofuranyl, dibenzothiopheneyl, dibenzofuranyl, carbazoleyl, benzocarbazoleyl, dibenzocarbazoleyl, phenazinyl, dibenzothiopheneyl, spirobis(dibenzothiazolyl) (P- ... [5] Thiadiazolyl, 2,3-dihydrobenzo[b]thiophenyl, 2,3-dihydrobenzofuranyl, 5,10-dihydrodibenzo[b,e][1,4]azasilyl, pyrazolo[1,5-c]quinazolinyl, pyrido[1,2-b]inzolyl, pyrido[1,2-a]imidazo[1,2-e]indololinyl and 5,11-dihydroindozo[1,2-b]carbazoyl.

[0054] In this specification, when the substituent is carbazolyl, benzocarbazolyl, or dibenzocarbazolyl, it means that the substituent is bonded to the nitrogen or carbon of the carbazolyl, benzocarbazolyl, or dibenzocarbazolyl group.

[0055] In this specification, when carbazolyl, benzocarbazolyl, or dibenzocarbazolyl is substituted, additional substituents may be substituted on the nitrogen or carbon of carbazolyl, benzocarbazolyl, or dibenzocarbazolyl.

[0056] In this specification, silyl is a substituent comprising Si and wherein the Si atom is directly attached as a free radical, represented by -Si(R107)(R108)(R109), and R107 to R109 may be the same as or different from each other, and may each independently be a substituent selected from the group consisting of: hydrogen; deuterium; halogen group; alkyl; alkenyl; alkoxy; cycloalkyl; heterocycloalkyl; aryl; and heteroaryl.

[0057] In this specification, the phosphine oxide group is represented by -P(=O)(R110)(R111), and R110 and R111 may be the same as or different from each other, and may each independently be a substituent selected from the group consisting of: hydrogen; deuterium; halogen group; alkyl; alkenyl; alkoxy; cycloalkyl; heterocycloalkyl; aryl; and heteroaryl. Specifically, the phosphine oxide group may be substituted with alkyl or aryl groups, and the above examples for alkyl and aryl groups may be applied. For example, the phosphine oxide group may be dimethylphosphine oxide, diphenylphosphine oxide, or dinaphthylphosphine oxide, but is not limited thereto.

[0058] In this specification, amino groups are represented by -N(R112)(R113), and R112 and R113 may be the same as or different from each other, and may each be a substituent selected from the group consisting of: hydrogen; deuterium; halogen group; alkyl; alkenyl; alkoxy; cycloalkyl; heterocycloalkyl; aryl; and heteroaryl. The amino group may be selected from the group consisting of -NH2, monoalkylamino, monoarylamino, monoheteroarylamino, dialkylamino, diarylamino, diheteroarylamino, alkylarylamino, alkylheteroarylamino, and arylheteroarylamino, and the number of carbon atoms is not particularly limited, but is preferably from 1 to 30. Specific examples of amino groups include, but are not limited to, methylamino, dimethylamino, ethylamino, diethylamino, phenylamino, naphthylamino, biphenylamino, diphenylamino, anthraceneamino, 9-methyl-anthraylamino, diphenylamino, phenylnaphthylamino, xylylamino, phenyltolylamino, triphenylamino, biphenylnaphthylamino, phenylbiphenylamino, biphenylfluorenylamino, phenylbenzophenanthreneamino, and biphenylbenzophenanthreneamino.

[0059] In this specification, the description of aryl as described above can be applied to arylene, except that arylene is divalent.

[0060] In this specification, the description of heteroaryl as described above can be applied to heteroaryl, except that the heteroaryl is divalent.

[0061] One embodiment of this specification provides a composition for an organic material layer in an organic light-emitting device, the composition comprising: a compound of formula 1; a compound of formula 2; and a compound of formula 3.

[0062] In one embodiment of this specification, X in chemical formula 1 is O or S.

[0063] In one embodiment of this specification, X can be 0.

[0064] In one embodiment of this specification, chemical formula 1 may be represented by the following chemical formula 1-A.

[0065] [Chemical Formula 1-A]

[0066] In chemical formula 1-A, The definitions of the corresponding substituents are the same as those defined in Formula 1.

[0067] In one embodiment of this specification, R1 and R2, R2 and R3, or R3 and R4 of Formula 1 are bonded to each other to form a substituted or unsubstituted benzene ring, and when R3 and R4 are bonded to each other to form a substituted or unsubstituted benzene ring, R1 is hydrogen or deuterium.

[0068] In other words, Formula 1 includes a 4-membered heterocycle containing O or S. Or, Formula 1 includes a naphthobenzofuran ring or a naphthobenzothiophene ring.

[0069] Furthermore, when R3 and R4 of Formula 1 are bonded to each other, there are no substituents other than hydrogen or deuterium at the 6-carbon position of naphthobenzofuran or naphthobenzothiophene.

[0070] In one embodiment of this specification, R1 and R2 may be bonded to each other to form substituted or unsubstituted benzene rings.

[0071] In one embodiment of this specification, R2 and R3 may be bonded to each other to form substituted or unsubstituted benzene rings.

[0072] In one embodiment of this specification, R3 and R4 may be bonded to each other to form a substituted or unsubstituted benzene ring, and R1 may be hydrogen or deuterium.

[0073] In one embodiment of this specification, the benzene ring may be substituted with deuterium or may not be substituted.

[0074] In one embodiment of this specification, one of the remaining groups among R1 to R4 and any one of R5 to R8 is -(L1)l1-N(Ar1)(Ar2), and the other is -(L2)l2-Ar3.

[0075] The term "the remaining groups among R1 to R4" refers to the substituents among R1 to R4 that do not form a benzene ring.

[0076] When R3 and R4 are bonded to each other, the remaining groups among R1 to R4 can be R2.

[0077] That is, chemical formula 1 includes a naphthobenzofuran ring or a naphthobenzothiophene ring, and the naphthobenzofuran ring or naphthobenzothiophene ring includes -(L1)l1-N(Ar1)(Ar2) and -(L2)l2-Ar3 as substituents.

[0078] In one embodiment of this specification, the remaining groups among R1 to R8 are each independently selected from the group consisting of: hydrogen; deuterium; halogen group; cyano; substituted or unsubstituted alkyl having 1 to 60 carbon atoms; substituted or unsubstituted cycloalkyl having 3 to 60 carbon atoms; substituted or unsubstituted heterocycloalkyl having 2 to 60 carbon atoms; substituted or unsubstituted aryl having 6 to 60 carbon atoms; and substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms.

[0079] The term “the remaining groups among R1 to R8” refers to substituents among R1 to R8 other than the following groups: i) two substituents that form the benzene ring (both of R1 to R4); ii) -(L1)l1-N(Ar1)(Ar2); and iii) -(L2)l2-Ar3.

[0080] When R3 and R4 are bonded to each other, R1 can be further excluded.

[0081] In one embodiment of this specification, the remaining groups among R1 to R8 are each independently selected from the group consisting of: hydrogen; deuterium; substituted or unsubstituted alkyl groups having 1 to 60 carbon atoms; substituted or unsubstituted cycloalkyl groups having 3 to 60 carbon atoms; and substituted or unsubstituted heterocycloalkyl groups having 2 to 60 carbon atoms.

[0082] In one embodiment of this specification, the remaining groups among R1 to R8 are each independently selected from the group consisting of: hydrogen; deuterium; substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms; substituted or unsubstituted cycloalkyl groups having 3 to 30 carbon atoms; and substituted or unsubstituted heterocycloalkyl groups having 2 to 30 carbon atoms.

[0083] In one embodiment of this specification, the remaining groups among R1 to R8 are each independently selected from the group consisting of hydrogen and deuterium.

[0084] In one embodiment of this specification, chemical formula 1 may be represented by any of the following chemical formulas 1-1 to 1-3.

[0085] [Chemical Formula 1-1]

[0086] [Chemical Formula 1-2]

[0087] [Chemical Formulas 1-3]

[0088] Among them, in chemical formulas 1-1 to 1-3, Either S1 or S2 is -(L1)l1-N(Ar1)(Ar2), and the other is -(L2)l2-Ar3. H1 to H3 are each independently hydrogen or deuterium.

[0089] m is an integer from 1 to 3, n is an integer from 1 to 5, o is 1 or 2, p is an integer from 1 to 4, and q is an integer from 1 to 6. The substituents in each set of parentheses are the same or different when o is 2, or when each of m, n, p, and q is 2 or greater. The definitions of X, L1, L2, l1, l2 and Ar1 to Ar3 are the same as those defined in the above chemical formula 1.

[0090] In one embodiment of this specification, L1 and L2 of Formula 1 are each independently: a direct bond; or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

[0091] In one embodiment of this specification, L1 and L2 may each be independently: a direct bond; or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0092] In one embodiment of this specification, L1 and L2 may each be independently: a direct bond; or a substituted or unsubstituted aryl group having 6 to 15 carbon atoms.

[0093] In one embodiment of this specification, L1 and L2 may each be independently: a direct bond; a substituted or unsubstituted phenylene; a substituted or unsubstituted biphenylene; or a substituted or unsubstituted naphthylene.

[0094] In one embodiment of this specification, L1 and L2 may each be independently: a direct bond; or a deuterated or unsubstituted aryl group having 6 to 60 carbon atoms.

[0095] In one embodiment of this specification, L1 and L2 may each be independently: a direct bond; or a deuterated or unsubstituted aryl group having 6 to 30 carbon atoms.

[0096] In one embodiment of this specification, L1 and L2 may each be independently: a direct bond; or a deuterated or unsubstituted aryl group having 6 to 15 carbon atoms.

[0097] In one embodiment of this specification, L1 and L2 may each be independently: a direct bond; a deuterated or unsubstituted phenylene; a deuterated or unsubstituted biphenylene; or a deuterated or unsubstituted naphthylene.

[0098] In one embodiment of this specification, when l1 is 2, it can be represented as -L1-L1'-, and the definition of L1' is the same as the definition of L1.

[0099] In one embodiment of this specification, when l2 is 2, it can be represented as -L2-L2'-, and the definition of L2' is the same as the definition of L2.

[0100] In one embodiment of this specification, Ar1 and Ar2 of Formula 1 are each independently: a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0101] In one embodiment of this specification, Ar1 and Ar2 may each be independently: a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms and including O or S.

[0102] In one embodiment of this specification, Ar1 and Ar2 may each be 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 and including O or S.

[0103] In one embodiment of this specification, Ar1 and Ar2 may each be independently: substituted or unsubstituted phenyl; substituted or unsubstituted biphenyl; substituted or unsubstituted terphenyl; substituted or unsubstituted naphthyl; substituted or unsubstituted phenanthyl; substituted or unsubstituted fluorenyl; substituted or unsubstituted dibenzofuranyl; or substituted or unsubstituted dibenzothiopheneyl.

[0104] In one embodiment of this specification, Ar1 and Ar2 may each be independently: a substituted or unsubstituted aryl group having 6 to 60 carbon atoms (the aryl group being substituted by at least one substituent selected from the group consisting of: deuterium; alkyl; and deuterated or unsubstituted aryl); spirobisfluorene; or a deuterated or unsubstituted heteroaryl group having 2 to 60 carbon atoms and including O or S.

[0105] In one embodiment of this specification, Ar1 and Ar2 may each be independently: a substituted or unsubstituted aryl group having 6 to 30 carbon atoms (the aryl group being substituted by at least one substituent selected from the group consisting of: deuterium; alkyl; and deuterated or unsubstituted aryl); spirobisfluorene; or a deuterated or unsubstituted heteroaryl group having 2 to 30 carbon atoms and including O or S.

[0106] In one embodiment of this specification, Ar3 of Formula 1 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

[0107] In one embodiment of this specification, Ar3 may be a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0108] In one embodiment of this specification, Ar3 may be: a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; or a substituted or unsubstituted phenanthryl group.

[0109] In one embodiment of this specification, Ar3 may be a deuterated or unsubstituted aryl group having 6 to 60 carbon atoms.

[0110] In one embodiment of this specification, Ar3 may be a deuterated or unsubstituted aryl group having 6 to 30 carbon atoms.

[0111] In one embodiment of this specification, Ar3 may be a deuterated or unsubstituted aryl group having 6 to 20 carbon atoms.

[0112] In one embodiment of this specification, chemical formula 1 may be represented by any of the following compounds.

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120] In one embodiment of this specification, L11 of Formula 2 is: a direct bond; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0121] In one embodiment of this specification, L11 can be: a direct bond; 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.

[0122] In one embodiment of this specification, L11 can be: a direct bond; a substituted or unsubstituted aryl group having 6 to 15 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 15 carbon atoms.

[0123] In one embodiment of this specification, L11 can be: a direct bond; a substituted or unsubstituted phenylene; a substituted or unsubstituted biphenylene; or a substituted or unsubstituted divalent dibenzofuranyl.

[0124] In one embodiment of this specification, L11 can be: a direct bond; a deuterated or unsubstituted aryl group having 6 to 30 carbon atoms; or a deuterated or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0125] In one embodiment of this specification, L11 can be: a direct bond; a deuterated or unsubstituted aryl group having 6 to 15 carbon atoms; or a deuterated or unsubstituted heteroaryl group having 2 to 15 carbon atoms.

[0126] In one embodiment of this specification, L11 can be: a direct bond; a deuterated or unsubstituted aryl group having 6 to 15 carbon atoms; or a deuterated or unsubstituted heteroaryl group having 2 to 15 carbon atoms and including O.

[0127] In one embodiment of this specification, L11 can be: a direct bond; or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

[0128] In one embodiment of this specification, L11 can be: a direct bond; or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0129] In one embodiment of this specification, L11 can be: a direct bond; or a substituted or unsubstituted aryl group having 6 to 15 carbon atoms.

[0130] In one embodiment of this specification, L11 can be: a direct bond; a substituted or unsubstituted phenylene; or a substituted or unsubstituted biphenylene.

[0131] In one embodiment of this specification, L11 can be: a direct bond; or a deuterated or unsubstituted aryl group having 6 to 15 carbon atoms.

[0132] In one embodiment of this specification, L11 can be: a direct bond; a deuterated or unsubstituted phenylene; or a deuterated or unsubstituted biphenylene.

[0133] In one embodiment of this specification, when l11 is 2, it can be represented as -L11-L11'-, and the definition of L11' is the same as the definition of L11.

[0134] In one embodiment of this specification, R11 of Formula 2 is: a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; or a substituted or unsubstituted silyl group.

[0135] In one embodiment of this specification, R11 may be: cyano; substituted or unsubstituted aryl having 6 to 60 carbon atoms; substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms; or substituted or unsubstituted silyl.

[0136] In one embodiment of this specification, R11 may be: cyano; substituted or unsubstituted aryl having 6 to 30 carbon atoms; substituted or unsubstituted heteroaryl having 2 to 30 carbon atoms; or substituted or unsubstituted silyl.

[0137] In one embodiment of this specification, R11 may be: cyano; substituted or unsubstituted phenyl; substituted or unsubstituted biphenyl; substituted or unsubstituted terphenyl; substituted or unsubstituted naphthyl; substituted or unsubstituted fluorenyl; substituted or unsubstituted benzophenanthryl; substituted or unsubstituted dibenzofuranyl; or aryl-substituted or unsubstituted silyl.

[0138] In one embodiment of this specification, R11 may be: a cyano group; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted with at least one substituent selected from deuterium, alkyl, and aryl; a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, substituted with at least one substituent selected from deuterium and aryl groups substituted with or unsubstituted with deuterium; or a silyl group substituted with an aryl group.

[0139] In one embodiment of this specification, any one of R12 to R19 of Formula 2 is a substituted or unsubstituted carbazole group, or two adjacent groups of R12 to R19 are bonded to each other to form a substituted or unsubstituted heterocycle having 2 to 30 carbon atoms.

[0140] In one embodiment of this specification, any of R12 to R19 may be a substituted or unsubstituted carbazole group.

[0141] In one embodiment of this specification, any one of R12 to R19 may be a carbazolyl group substituted with or unsubstituted with at least one substituent selected from deuterium and deuterated or unsubstituted aryl groups.

[0142] In one embodiment of this specification, two adjacent groups among R12 to R19 may be bonded to each other to form a substituted or unsubstituted heterocycle having 2 to 30 carbon atoms.

[0143] In one embodiment of this specification, two adjacent groups among R12 to R19 may be bonded to each other to form a substituted or unsubstituted N-containing heterocycle having 2 to 30 carbon atoms.

[0144] In one embodiment of this specification, two adjacent groups among R12 to R19 may be bonded to each other to form a substituted or unsubstituted indole ring.

[0145] In one embodiment of this specification, the remaining groups of Formula 2, R12 to R19, are each independently selected from the group consisting of: hydrogen; deuterium; halogen group; cyano; substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; substituted or unsubstituted aryl group having 6 to 60 carbon atoms; and substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0146] The term "the remaining groups among R12 to R19" refers to substituents among R12 to R19 that are not substituted or unsubstituted carbazole groups, or that are not substituents that bond with each other to form substituted or unsubstituted heterocycles having 2 to 30 carbon atoms.

[0147] In one embodiment of this specification, the remaining groups among R12 to R19 may each be independently selected from the group consisting of: hydrogen; deuterium; substituted or unsubstituted alkyl groups having 1 to 60 carbon atoms; substituted or unsubstituted cycloalkyl groups having 3 to 60 carbon atoms; and substituted or unsubstituted heterocycloalkyl groups having 2 to 60 carbon atoms.

[0148] In one embodiment of this specification, the remaining groups among R12 to R19 may each be independently selected from the group consisting of: hydrogen; deuterium; substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms; substituted or unsubstituted cycloalkyl groups having 3 to 30 carbon atoms; and substituted or unsubstituted heterocycloalkyl groups having 2 to 30 carbon atoms.

[0149] In one embodiment of this specification, the remaining groups among R12 to R19 may each be independently selected from the group consisting of hydrogen and deuterium.

[0150] In one embodiment of this specification, chemical formula 2 may be represented by chemical formula 2-1 or chemical formula 2-2.

[0151] [Chemical Formula 2-1]

[0152] [Chemical Formula 2-2]

[0153] Among them, in chemical formula 2-1 and chemical formula 2-2, The definitions of L11, l11, and R11 are the same as those in chemical formula 2, and Q1 and Q2 are each 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, and H11 and H12 are respectively: hydrogen; or deuterium, and e and f are each integers from 1 to 7, g is an integer from 1 to 6, and h is an integer from 1 to 4. When e, f, g, and h are each 2 or greater, the substituents in each set of parentheses may be the same or different.

[0154] In one embodiment of this specification, Q1 and Q2 may each be independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0155] In one embodiment of this specification, Q1 and Q2 may each be independently: a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; or a substituted or unsubstituted naphthyl group.

[0156] In one embodiment of this specification, Q1 and Q2 may each be independently a deuterium-substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0157] In one embodiment of this specification, Q1 and Q2 may each be independently: a deuterated or unsubstituted phenyl group; a deuterated or unsubstituted biphenyl group; a deuterated or unsubstituted terphenyl group; or a deuterated or unsubstituted naphthyl group.

[0158] In one embodiment of this specification, chemical formula 2 may be represented by any of the following compounds.

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165] In one embodiment of this specification, Y in chemical formula 3 is O or S.

[0166] In one embodiment of this specification, Y can be O.

[0167] In one embodiment of this specification, any one of R21 to R28 of Formula 3 is -(L21)l21-(N-Het), wherein L21 is a direct bond or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, l21 is an integer from 1 to 3, and when l21 is 2 or more, L21 is the same or different, and N-Het is a substituted or unsubstituted heteroaryl group including a C=N bond.

[0168] In one embodiment of this specification, the remaining groups among R21 to R28 are each independently: hydrogen; deuterium; halogen group; cyano; substituted or unsubstituted alkyl having 1 to 60 carbon atoms; substituted or unsubstituted cycloalkyl having 3 to 60 carbon atoms; substituted or unsubstituted heterocycloalkyl having 2 to 60 carbon atoms; substituted or unsubstituted aryl having 6 to 60 carbon atoms; substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms; substituted or unsubstituted silyl; or substituted or unsubstituted phosphine oxide.

[0169] In one embodiment of this specification, any of the remaining groups among R21 to R28 is -(L22)l22-Ar11, wherein L22 is a direct bond or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, l22 is an integer from 1 to 3, and when l22 is 2 or greater, L22 is the same or different, and Ar11 can be: cyano; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; a substituted or unsubstituted silyl group; or a substituted or unsubstituted phosphine oxide group.

[0170] In one embodiment of this specification, the remaining groups among R21 to R28, excluding -(L21)l21-(N-Het) and -(L22)l22-Ar11, may be: hydrogen; deuterium; substituted or unsubstituted alkyl groups having 1 to 60 carbon atoms; substituted or unsubstituted cycloalkyl groups having 3 to 60 carbon atoms; or substituted or unsubstituted heterocycloalkyl groups having 2 to 60 carbon atoms.

[0171] In one embodiment of this specification, the remaining groups among R21 to R28, except for -(L21)l21-(N-Het) and -(L22)l22-Ar11, may be hydrogen or deuterium.

[0172] In one embodiment of this specification, chemical formula 3 may be represented by the following chemical formula 3-1.

[0173] [Chemical Formula 3-1]

[0174] In chemical formula 3-1, L21 and L22 are each independently: a direct bond; or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, and l21 and l22 are each integers from 1 to 3, and when l21 and l22 are 2 or more, the substituents in each pair of parentheses can be the same or different from each other. N-Het is a substituted or unsubstituted heteroaryl group including a C=N bond, and Ar11 is: cyano; substituted or unsubstituted aryl group having 6 to 60 carbon atoms; substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; substituted or unsubstituted silyl group; or substituted or unsubstituted phosphine oxide group, and H13 and H14 are each independently: hydrogen; or deuterium, and i and j are each integers from 1 to 4, the sum of i and j is an integer from 2 to 6, and when i and j are each 2 or greater, the substituents in each set of parentheses are the same or different.

[0175] In one embodiment of this specification, L21 may be: a direct bond; or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0176] In one embodiment of this specification, L21 may be: a direct bond; or a substituted or unsubstituted aryl group having 6 to 15 carbon atoms.

[0177] In one embodiment of this specification, L21 can be: a direct bond; a substituted or unsubstituted phenylene; a substituted or unsubstituted biphenylene; or a substituted or unsubstituted naphthylene.

[0178] In one embodiment of this specification, L21 can be: a direct bond; or a deuterated or unsubstituted aryl group having 6 to 30 carbon atoms.

[0179] In one embodiment of this specification, L21 can be: a direct bond; or a deuterated or unsubstituted aryl group having 6 to 15 carbon atoms.

[0180] In one embodiment of this specification, N-Het can be: a substituted or unsubstituted pyridinyl group; a substituted or unsubstituted pyrimidinyl group; or a substituted or unsubstituted triazine group.

[0181] In one embodiment of this specification, N-Het may be a substituted or unsubstituted triazine group.

[0182] In one embodiment of this specification, N-Het may be a triazine group substituted with at least one substituent selected from the following groups: an aryl group substituted with or unsubstituted with at least one substituent selected from deuterium, halogen groups, cyano and alkyl; and a heteroaryl group substituted with or unsubstituted with deuterium; or it may be a triazine group substituted with two or more linking groups.

[0183] In one embodiment of this specification, N-Het may be a triazine group substituted with at least one substituent selected from the following groups: a phenyl group substituted with or unsubstituted with deuterium, a halogen group or a cyano group; a biphenyl group substituted with or unsubstituted with deuterium; a terphenyl group substituted with or unsubstituted with deuterium; a naphthyl group substituted with or unsubstituted with deuterium; a phenanthryl group substituted with or unsubstituted with deuterium; a fluorenyl group substituted with or unsubstituted with deuterium; a carbazolyl group substituted with or unsubstituted with deuterium; a dibenzofuranyl group substituted with or unsubstituted with deuterium; and a dibenzothiophenyl group substituted with or unsubstituted with deuterium, or may be a triazine group substituted with two or more linking groups.

[0184] In one embodiment of this specification, L22 may be: a direct bond; or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0185] In one embodiment of this specification, L22 may be: a direct bond; or a substituted or unsubstituted aryl group having 6 to 15 carbon atoms.

[0186] In one embodiment of this specification, L22 can be: a direct bond; a substituted or unsubstituted phenylene; a substituted or unsubstituted biphenylene; or a substituted or unsubstituted naphthylene.

[0187] In one embodiment of this specification, L22 may be: a direct bond; or a deuterated or unsubstituted aryl group having 6 to 30 carbon atoms.

[0188] In one embodiment of this specification, L22 can be: a direct bond; or a deuterated or unsubstituted aryl group having 6 to 15 carbon atoms.

[0189] In one embodiment of this specification, Ar11 may be: cyano; substituted or unsubstituted aryl having 6 to 30 carbon atoms; substituted or unsubstituted heteroaryl having 2 to 30 carbon atoms; substituted or unsubstituted silyl; or substituted or unsubstituted phosphine oxide.

[0190] In one embodiment of this specification, Ar11 may be: cyano; substituted or unsubstituted aryl having 6 to 30 carbon atoms; substituted or unsubstituted heteroaryl having 2 to 30 carbon atoms and including O or S; substituted or unsubstituted carbazolyl; substituted or unsubstituted silyl; or substituted or unsubstituted phosphine oxide.

[0191] In one embodiment of this specification, Ar11 may be: cyano; substituted or unsubstituted aryl having 6 to 30 carbon atoms; substituted or unsubstituted heteroaryl having 2 to 30 carbon atoms; silyl substituted with alkyl or aryl; or phosphine oxide substituted with aryl.

[0192] In one embodiment of this specification, Ar11 can be: cyano; substituted or unsubstituted phenyl; substituted or unsubstituted biphenyl; substituted or unsubstituted terphenyl; substituted or unsubstituted naphthyl; substituted or unsubstituted phenanthryl; substituted or unsubstituted benzophenanthryl; substituted or unsubstituted carbazole; substituted or unsubstituted dibenzofuranyl; substituted or unsubstituted dibenzothiopheneyl; alkyl- or aryl-substituted silyl; or aryl-substituted phosphine oxide.

[0193] In one embodiment of this specification, chemical formula 3 may be represented by any of the following compounds.

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202] In one embodiment of this specification, the weight ratio of the compound of formula 1 to the compound of formula 3 and the weight ratio of the compound of formula 2 to the compound of formula 3 may each be from 1:1 to 1:10.

[0203] In other words, the content of compounds of Formula 1 and Formula 2 shall not exceed that of compounds of Formula 3. When compounds of Formula 1 or Formula 2 are included in higher amounts than compounds of Formula 3, due to charge imbalance, maximum efficiency cannot be achieved when used as materials for organic light-emitting devices, and problems such as reduced device stability and shortened lifespan occur.

[0204] In one embodiment of this specification, the weight ratio of the compound of formula 1 to the compound of formula 3 and the weight ratio of the compound of formula 2 to the compound of formula 3 may each be from 1:1 to 1:5.

[0205] In one embodiment of this specification, the weight ratio of the compound of formula 1 to the compound of formula 3 and the weight ratio of the compound of formula 2 to the compound of formula 3 may each be from 1:1 to 1:3.

[0206] In one embodiment of this specification, the deuterium substitution rate of Formula 1 can be from 0% to 100%.

[0207] In one embodiment of this specification, the deuterium substitution rate of Formula 1 may be 0%.

[0208] In one embodiment of this specification, the deuterium substitution rate of Formula 1 can be from 10% to 100%.

[0209] In one embodiment of this specification, the deuterium substitution rate of chemical formula 2 can be from 0% to 100%.

[0210] In one embodiment of this specification, the deuterium substitution rate of chemical formula 2 may be 0%.

[0211] In one embodiment of this specification, the deuterium substitution rate of chemical formula 2 can be from 10% to 100%.

[0212] In one embodiment of this specification, the deuterium substitution rate of chemical formula 3 can be from 0% to 100%.

[0213] In one embodiment of this specification, the deuterium substitution rate of chemical formula 3 may be 0%.

[0214] In one embodiment of this specification, the deuterium substitution rate of chemical formula 3 may be greater than 0% and less than or equal to 100%.

[0215] In one embodiment of this specification, the deuterium substitution rate of chemical formula 3 can be from 3% to 100%.

[0216] In one embodiment of this specification, the deuterium substitution rate of each of the compounds of formulas 1 to 3 is 0%, or greater than 0% and less than or equal to 100%.

[0217] In this specification, the deuterium substitution rate of Formulas 1 to 3 refers to the substitution rate of deuterium relative to the total number of hydrogen and deuterium atoms included in each of Formulas 1 to 3. For example, when Formula 1 includes 20 hydrogen atoms and 20 deuterium atoms, the deuterium substitution rate of Formula 1 is 50%, which is the substitution rate of 20 deuterium atoms relative to a total of 40 hydrogen and deuterium atoms.

[0218] In one embodiment of this specification, when the deuterium substitution rate of compounds of formulas 1 to 3 is greater than 0%, the photochemical properties of deuterium-free and deuterium-containing compounds are almost similar; however, when deposited as thin films, deuterium-containing materials tend to be packed with narrower intermolecular distances.

[0219] Therefore, when manufacturing EOD (electronic devices only) and HOD (hole devices only) and examining the current density according to the applied voltage, it can be confirmed that, among the compounds of the present invention, the deuterium-containing compounds exhibit much more balanced charge transport characteristics than the deuterium-free compounds.

[0220] Furthermore, observation of the film surface using atomic force microscopy (AFM) confirmed that the film made from the deuterium-containing compound was deposited on a more uniform surface without any aggregated areas.

[0221] Furthermore, since the single bond dissociation energy of carbon and deuterium is higher than that of carbon and hydrogen, in the case of compounds of chemical formulas 1 to 3 of the present invention in which the deuterium substitution rate is greater than 0%, the stability of the entire molecule is increased, thereby providing the effect of improving device lifespan.

[0222] Furthermore, by introducing various substituents into structures of Chemical Formulas 1 to 3, compounds possessing the inherent properties of the introduced substituents can be synthesized. For example, materials satisfying the requirements of each organic material layer can be synthesized by introducing substituents primarily used in the manufacture of hole injection layer materials, hole transport layer materials, emission layer materials, electron transport layer materials, and charge generation layer materials into the core structure.

[0223] Furthermore, by introducing various substituents into the structures of chemical formulas 1 to 3, it becomes possible to finely tune the band gap, and on the other hand, it becomes possible to improve the interfacial properties between organic materials and to diversify the applications of the materials.

[0224] In another embodiment of this specification, an organic light-emitting device is provided, the organic light-emitting device comprising: a first electrode; a second electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises the composition of organic material layers for an organic light-emitting device as described above.

[0225] In one embodiment of this specification, the organic material layer includes an emitting layer, and the emitting layer may include a composition of organic material layers for an organic light-emitting device.

[0226] In one embodiment of this specification, the organic material layer includes an emitting layer, the emitting layer includes a body, and the body may include a composition of the organic material layer for an organic light-emitting device.

[0227] In one embodiment of this specification, the compound of Formula 1 may be a P-body.

[0228] In one embodiment of this specification, the compound of formula 2 may be a P-body.

[0229] In one embodiment of this specification, the compound of formula 3 may be an N-body.

[0230] In one embodiment of this specification, the organic material layer may include an emitting layer, the emitting layer may include a body, the body may include a green body, and the green body may include a composition of the organic material layer for an organic light-emitting device.

[0231] In one embodiment of this specification, the organic material layer may include an emitting layer, the emitting layer may include a body, the body may include a red body, and the red body may include a composition of organic material layers for an organic light-emitting device.

[0232] In one embodiment of this specification, the organic material layer may include an emitting layer, the emitting layer may include a body, the body may include a blue body, and the blue body may include a composition of organic material layers for an organic light-emitting device.

[0233] The organic material layer of the organic light-emitting device of the present invention can be formed as a single-layer structure, but it can also be formed as a multilayer 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 in which at least one of a hole injection layer, a hole transport layer, an emission layer, an electron transport layer, and an electron injection layer is included as an organic material layer. 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.

[0234] In one embodiment of this specification, the first electrode may be an anode, and the second electrode may be a cathode.

[0235] In another embodiment of this specification, the first electrode may be a cathode, and the second electrode may be an anode.

[0236] In one embodiment of this specification, the organic light-emitting device according to the embodiments of this specification can be manufactured by conventional manufacturing methods and materials for organic light-emitting devices, except that at least one organic material layer is formed by using a composition for the organic material layer of the above-described organic light-emitting device.

[0237] In the manufacture of organic light-emitting devices, compounds of chemical formulas 1 to 3 can be formed into organic material layers not only by vacuum deposition but also by solution application methods. Here, the term "solution application method" refers to, for example, spin coating, dip coating, inkjet printing, screen printing, spray coating, and roll coating, but is not limited to these.

[0238] In one embodiment of this specification, the organic light-emitting device may be a blue organic light-emitting device, and the composition of the organic material layer for the organic light-emitting device may be used as the material for the blue organic light-emitting device. For example, the composition of the organic material layer for the organic light-emitting device may be included in the emitting layer of the blue organic light-emitting device.

[0239] In another embodiment of this specification, the organic light-emitting device may be a green organic light-emitting device, and the composition of the organic material layer for the organic light-emitting device may be used as the material for the green organic light-emitting device. For example, the composition of the organic material layer for the organic light-emitting device may be included in the emitting layer of the green organic light-emitting device.

[0240] In another embodiment of this specification, the organic light-emitting device may be a red organic light-emitting device, and the composition of the organic material layer for the organic light-emitting device may be used as the material for the red organic light-emitting device. For example, the composition of the organic material layer for the organic light-emitting device may be included in the emitting layer of the red organic light-emitting device.

[0241] The organic light-emitting device of the present invention may further include at least one layer selected from the group consisting of an emission layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer.

[0242] exist Figures 1 to 3 The figures illustrate the stacking order of electrodes and organic material layers in an organic light-emitting device according to one embodiment of this specification. However, these figures are not intended to limit the scope of this application, and structures of organic light-emitting devices known in the art can also be applied to this application.

[0243] according to Figure 1 This illustrates an organic light-emitting device in which an anode 200, an organic material layer 300, and a cathode 400 are sequentially stacked on a substrate 100. However, the invention is not limited to this structure, and as shown... Figure 2 As shown, an organic light-emitting device in which the cathode, organic material layer and anode are sequentially stacked on a substrate can also be realized.

[0244] Figure 3 This illustrates a case where the organic material layers are multiple. According to... Figure 3 The organic light-emitting device includes: a hole injection layer 301; a hole transport layer 302; an emission layer 303; a hole blocking layer 304; an electron transport layer 305; and an electron injection layer 306. However, the scope of this application is not limited to this stacked structure, and if necessary, the remaining layers except the emission layer can be omitted, and other functional layers can be added as needed.

[0245] If necessary, the organic material layer of the composition comprising the organic material layer for an organic light-emitting device of the present invention may also include other materials.

[0246] In an organic light-emitting device according to one embodiment described in this specification, materials other than compounds of chemical formulas 1 to 3 are illustrated below; however, these are merely for illustrative purposes and are not intended to limit the scope of this application, and they may be replaced with materials known in the art.

[0247] As anode materials, materials with relatively large work functions can be used, and transparent conductive oxides, metals, or conductive polymers can be employed. Specific examples of anode materials include, but are not limited to: metals such as vanadium, chromium, copper, zinc, and gold or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline.

[0248] As cathode materials, materials with relatively low work functions can be used, and can be metals, metal oxides, or conductive polymers, etc. Specific examples of cathode materials include, but are not limited to: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; and multilayer structure materials such as LiF / Al or LiO2 / Al.

[0249] Known hole-injection materials can also be used as hole-injection materials. For example, phthalocyanine compounds, such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429, can be used; starburst-type amine derivatives described in [Advanced Material, 6, p. 677 (1994)], such as tris(4-carbazolyl-9-ylphenyl)amine (TCTA), 4,4',4"-tris[phenyl(m-tolyl)amino]triphenylamine (m-MTDATA), and 1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene (m-MTDAPB); soluble conductive polymers, such as polyaniline / dodecylbenzenesulfonic acid or poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate); and polyaniline / camphorsulfonic acid or polyaniline / poly(4-styrenesulfonate).

[0250] As hole transport materials, pyrazoline derivatives, arylamine derivatives, succinyl styrene derivatives, and triphenyl diamine derivatives can be used, and low molecular weight materials or polymer materials can also be used.

[0251] As electron transport materials, the following can be used: oxadiazole derivatives; anthraquinone dimethyl ether and its derivatives; benzoquinone and its derivatives; naphthoquinone and its derivatives; anthraquinone and its derivatives; tetracyanoanthraquinone dimethyl ether and its derivatives; fluorenone derivatives; diphenyl dicyanoethylene and its derivatives; biphenylquinone derivatives; and metal complexes of 8-hydroxyquinoline and its derivatives, and not only low molecular weight substances but also polymeric substances can be used.

[0252] As an electron injection material, LiF is commonly used in the art, for example; however, this application is not limited thereto.

[0253] Red, green, or blue luminescent materials can be used, and two or more luminescent materials can be mixed if necessary. In this case, the two or more luminescent materials can be deposited from separate sources, or they can be premixed and deposited from a single source. Furthermore, fluorescent or phosphorescent materials can be used as luminescent materials. Materials that induce light emission by recombination of holes and electrons injected from the anode and cathode, respectively, can be used, or materials in which both the host material and the dopant material participate in light emission can be used.

[0254] When the luminescent materials are used in combination, they can be from the same series or different series. For example, as the luminescent layer material, any two or more materials selected from N-type or P-type luminescent materials can be used.

[0255] Depending on the materials used, an organic light-emitting device according to one embodiment of this specification may be a top-emitting, bottom-emitting, or dual-emitting type.

[0256] The composition of the organic material layer for an organic light-emitting device according to one embodiment of this specification can also be operated in organic electronic devices such as organic solar cells, organic photoconductors, and organic transistors based on principles similar to those applied to organic light-emitting devices.

[0257] Furthermore, by introducing various substituents into the structures of chemical formulas 1 to 3, it becomes possible to finely tune the band gap, and on the other hand, it becomes possible to improve the interfacial properties between organic materials and to diversify the applications of the materials.

[0258] Another 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 at least one organic material layer on the first electrode; and forming a second electrode on the organic material layer, wherein the step of forming the organic material layer comprises forming at least one organic material layer using a composition for an organic material layer of an organic light-emitting device.

[0259] In one embodiment of this specification, the step of forming an organic material layer may include pre-mixing a composition for an organic light-emitting device and depositing the pre-mixed composition from a single source. Specific Embodiment The present disclosure will be described in detail below with reference to the following examples. However, the following examples are for illustrative purposes only, and the scope of the disclosure is not limited thereto.

[0261] [Preparation Example 1] Preparation of compound A26 and compounds in Table 1

[0262] 1) Preparation of intermediate A26-1 30.0 g (90.5 mmol) of 5-bromo-9-chloronaphtho[1,2-b]benzofuran (A), 12.1 g (99.6 mmol) of phenylboronic acid (B), 5.2 g (4.5 mmol) of Pd(PPh3)4 (tetra(triphenylphosphine)palladium(0)) and 25.0 g (181.0 mmol) of K2CO3 were dissolved in 1,4-dioxane / H2O (300 ml / 60 ml) and then refluxed for 1 h. The reaction mixture was purified by recrystallization from methanol to obtain intermediate A26-1 (24.8 g, 83.3% yield).

[0263] 2) Preparation of compound A26 10.0 g (30.4 mmol) of intermediate A26-1 dissolved in toluene (150 ml), 11.3 g (30.4 mmol) of di([1,1'-biphenyl]-4-yl)amine (C), 1.4 g (1.5 mmol) of Pd2(dba)3 (tris(dibenzylacetone)dipalladium(0)), 1.4 g (3.0 mmol) of Xphos (2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl), and 5.8 g (60.8 mmol) of NaOtBu (sodium tert-butoxide) were added to a 500 ml double-necked flask, followed by reflux for 1 h. The reaction mixture was purified by recrystallization from methanol to obtain the target compound A26 (17.6 g, 87.2% yield).

[0264] The following compounds were synthesized in the same manner as in the preparation of compound A26, except that (A), (B) and (C) of Table 1 below were used instead of (A), (B) and (C) in preparation example 1.

[0265] [Table 1]

[0266]

[0267] [Preparation Example 2] Preparation of compound A20 and compounds in Table 2

[0268] 1) Preparation of intermediate A20-1 In a 1 L double-necked flask, 30.0 g (90.5 mmol) of 5-bromo-7-chloronaphtho[1,2-b]benzofuran (A), 12.1 g (99.6 mmol) of phenylboronic acid (B), 5.2 g (4.5 mmol) of Pd(PPh3)4 and 25.0 g (181.0 mmol) of K2CO3 were dissolved in 1,4-dioxane / H2O (300 mL / 60 mL), followed by reflux for 1 hour. The reaction mixture was purified by recrystallization from methanol to obtain intermediate A20-1 (24.8 g, 83.3% yield).

[0269] 2) Preparation of compound A20 In a 250 mL double-necked flask, 10.0 g (30.4 mmol) of intermediate A20-1, 11.1 g (30.4 mmol) of (4-([1,1'-biphenyl]-4-yl(phenyl)amino)phenyl)boronic acid (C), 1.4 g (1.5 mmol) of Pd2dba3, 1.4 g (3.0 mmol) of XPhos, and 8.4 g (60.8 mmol) of K2CO3 were dissolved in 1,4-dioxane / H2O (100 mL / 20 mL), followed by reflux for 1 hour. The reaction mixture was purified by recrystallization from methanol to obtain the target compound A20 (15.1 g, 80.9% yield).

[0270] The following compounds were synthesized in the same manner as those for the preparation of compound A20, except that (A), (B) and (C) in preparation example 2 were replaced with (A), (B) and (C) in Table 2 below.

[0271] [Table 2]

[0272]

[0273] [Preparation Example 3] Preparation of compound A88 and compounds in Table 3

[0274] 1) Preparation of intermediate A88-1 10.0 g (30.31 mmol) of 5-bromo-9-chloronaphtho[2,1-b]benzofuran (A), 11.3 g (30.31 mmol) of N-(4-(naphthyl-2-yl)phenyl)-[1,1'-biphenyl]-4-amine (B), 0.34 g (1.5 mmol) of Pd2dba3, 1.4 g (60.62 mmol) of Xphos, and 5.8 g (60.62 mmol) of NaOtBu were placed in a 500 mL double-necked flask, dissolved in 150 mL of toluene, and refluxed for 1 hour. The reaction mixture was purified by recrystallization from methanol to obtain 16.57 g of intermediate A88-1 (yield: 88%).

[0275] 2) Preparation of compound A88 16.57 g (26.67 mmol) of A88-1, 4.88 g (40.01 mmol) of phenylboronic acid (C), 1.54 g (1.33 mmol) of Pd(PPh3)4, and 11.06 g (80.02 mmol) of K2CO3 were placed in a 1 L double-necked flask, then dissolved in 1,4-dioxane / H2O (300 mL / 60 mL) and refluxed for 1 hour. The reaction mixture was purified by recrystallization from methanol to obtain 15.22 g of the target compound A88 (yield: 86%).

[0276] The following compounds were synthesized in the same manner as in the preparation of compound A88, except that (A), (B) and (C) in preparation example 3 were replaced with (A), (B) and (C) in Table 3 below.

[0277] [Table 3]

[0278] The compounds were prepared in the same manner as in the preparation examples above, and the confirmation results of their synthesis are shown in Tables 4 and 5 below. Table 4 shows... 1 The measurements were obtained by H NMR (CDCl3, 400 MHz), and Table 5 shows the measurements obtained by FD mass spectrometry (FD-MS: field desorption mass spectrometry).

[0279] [Table 4]

[0280] [Table 5]

[0281] <Preparation Example 4> Preparation of Compound B1 and Compounds in Table 6

[0282] 1) Preparation of intermediate B1-1 10 g (49.59 mmol) of 3-bromo-9H-carbazole, 24.2 g (148.77 mmol) of 2-bromobenzene-1-onium(a), 2.27 g (2.48 mmol) of Pd2(dba)3, 2.42 mL (9.92 mmol) of P(t-Bu)3 (tri-tert-butylphosphine), and 9.53 g (99.18 mmol) of NaOtBu were added to a reaction flask, followed by the addition of 100 mL of toluene. The mixture was then heated at 135 °C for 15 hours. After the reaction was complete, the mixture was extracted with dichloromethane (MC) and water, and then purified by column chromatography to obtain 14 g of intermediate B1-1 (yield: 98%).

[0283] 2) Preparation of compound B1 14 g (43.4 mmol) of intermediate B1-1, 14.9 g (52 mmol) of (9-phenyl-9H-carbazol-3-yl)boronic acid (b), 2.5 g (2.17 mmol) of Pd(PPh3)4, and 17.9 g (130 mmol) of K2CO3 were added to a reaction flask, followed by 140 mL of 1,4-dioxane and 35 mL of distilled water. The mixture was stirred at 120 °C for 4 hours. The temperature was then lowered to room temperature, and the resulting solid was washed with distilled water and methanol to obtain 17 g of the target compound B1 (yield: 80%).

[0284] The following compounds were synthesized in the same manner as in the preparation of compound B1, except that (a) and (b) of Table 6 below were used instead of (a) and (b) in preparation example 4.

[0285] [Table 6]

[0286]

[0287]

[0288]

[0289]

[0290]

[0291]

[0292]

[0293] <Preparation Example 5> Preparation of Compound B41 and the compounds in Table 7

[0294] 1) Preparation of intermediate B41-1 10 g (39.0 mmol) of 5,8-dihydroindolo[2,3-c]carbazole (a), 6.12 g (39.0 mmol) of 1-bromobenzene (b), 1.79 g (1.95 mmol) of Pd2(dba)3, 0.92 mL (3.9 mmol) of P(t-Bu)3, and 7.50 g (78.0 mmol) of NaOtBu were placed in a reaction flask, followed by the addition of 100 mL of toluene, and the mixture was heated at 135 °C for 15 hours. After the reaction was complete, the mixture was extracted with MC and water, and then purified by column chromatography to obtain 7.3 g of intermediate B41-1 (yield: 56%).

[0295] 2) Preparation of compound B41 7.3 g (22.0 mmol) of intermediate B41-1, 3.8 g (24.2 mmol) of 1-bromobenzene(c), 1.01 g (1.1 mmol) of Pd2(dba)3, 0.52 mL (3.9 mmol) of P(t-Bu)3, and 4.23 g (44.0 mmol) of NaOtBu were placed in a reaction vessel, followed by the addition of 70 mL of toluene, and the mixture was heated at 135 °C for 15 hours. After the reaction was complete, the mixture was extracted with MC and water, and then purified by column chromatography to obtain 8.3 g of compound B41 (yield: 93%).

[0296] The following compounds were synthesized in the same manner as in the preparation of compound B41, except that (a), (b), and (c) of Table 7 below were used instead of (a), (b), and (c) in preparation example 5.

[0297] [Table 7]

[0298]

[0299] The compounds were prepared in the same manner as in the preparation examples above, and the confirmation results of their synthesis are shown in Tables 8 and 9 below. Table 8 shows... 1 The measurements were obtained by H NMR (CDCl3, 400 MHz), and Table 9 shows the measurements obtained by FD mass spectrometry (FD-MS: field desorption mass spectrometry).

[0300] [Table 8]

[0301] [Table 9]

[0302] [Preparation Example 6] Preparation of compound C24 and compounds in Table 10

[0303] 1) Preparation of intermediate C24-1 2-(7-chlorodibenzo[b,d]furan-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxacycloborane (A) (8 g, 24.35 mmol), 2-chloro-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine (B) (8.62 g, 23.86 mmol), Pd(PPh3)4 (1.41 g, 1.22 mmol), and K2CO3 (7.74 g, 73.04 mmol) were added to 1,4-dioxane / H2O (80 mL / 16 mL), and the mixture was stirred at 110 °C for 2 hours. After cooling to room temperature, the resulting solid was filtered to obtain intermediate C24-1 (11 g, 86.23%).

[0304] 2) Preparation of compound C24 Intermediate C24-1 (11.0 g, 20.9 mmol), (4-(naphthyl-2-yl)phenyl)boronic acid (C) (6.25 g, 25.19 mmol), Pd2(dba)3 (0.6 g, 1.15 mmol), XPhos (1.0 g, 2.1 mmol), and NaOH (2.52 g, 62.98 mmol) were added to 1,4-dioxane / H2O (110 mL / 22 mL), and the mixture was stirred at 120 °C for 2 hours. After cooling to room temperature, the resulting solid was filtered. Purification by silica gel column chromatography yielded the desired compound C24 (12 g, 83%).

[0305] The following compounds were synthesized in the same manner as those prepared for compound C24, except that (A), (B), and (C) of Table 10 below were used instead of (A), (B), and (C) in Preparation Example 6.

[0306] [Table 10]

[0307]

[0308]

[0309] [Preparation Example 7] Preparation of compound C131 and compounds in Table 11

[0310] 2-(dibenzo[b,d]furan-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxacycloborane (A) (8 g, 27.20 mmol), 2-([1,1':4',1''-terphenyl]-4-yl)-4-chloro-6-(naphth-2-yl)-1,3,5-triazine (B) (12.50 g, 65.65 mmol), Pd(PPh3)4 (1.57 g, 1.36 mmol), and K2CO3 (11.28 g, 81.59 mmol) were added to 1,4-dioxane / H2O (80 mL / 16 mL), and the mixture was stirred at 110 °C for 2 hours. After cooling to room temperature, the resulting solid was filtered to obtain the target compound C131 (14.59 g, 89.23%).

[0311] The following compounds were synthesized in the same manner as those for the preparation of compound C131, except that (A) and (B) of Table 11 below were used instead of (A) and (B) in preparation example 7.

[0312] [Table 11]

[0313] The compounds were prepared in the same manner as in the preparation examples above, and the confirmation results of their synthesis are shown in Tables 12 and 13 below. Table 12 shows... 1 The measurements were obtained by H NMR (CDCl3, 400 MHz), and Table 13 shows the measurements obtained by FD mass spectrometry (FD-MS: field desorption mass spectrometry).

[0314] [Table 12]

[0315] [Table 13]

[0316] [Experimental Example] [Experiment Example 1] 1) Production of Organic Light Emitting Device A glass substrate coated with an indium tin oxide (ITO) film to a thickness of 1,500 Å was cleaned in an ultrasonic bath using distilled water. After distilled water cleaning, it was ultrasonically cleaned using solvents such as acetone, methanol, and isopropanol, followed by drying, and then UVO (ultraviolet ozone) treatment in a UV cleaner for 5 minutes. Subsequently, the substrate was transferred to a plasma cleaner (PT) and subjected to plasma treatment under vacuum to remove the ITO work function and residual film, and then transferred to a thermal evaporation apparatus for organic deposition.

[0317] On an ITO transparent electrode (anode), a common layer is formed comprising a hole injection layer of 2-TNATA (4,4',4''-tris[2-naphthyl(phenyl)amino]triphenylamine) and a hole transport layer of NPB (N,N'-di(1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine).

[0318] The emitter layer was thermally vacuum deposited on top of the hole injection layer and the hole transport layer, as follows. Specifically, as the red host of the emitter layer, the compounds listed in Table 14 below were used alone, or the two compounds listed in Table 15 below or the three compounds listed in Table 16 below were used together, and the red phosphorescent dopant (piq)2(Ir)(acac) was doped into the red host at 3 wt%, thereby depositing an emitter layer with a thickness of 500 Å. Subsequently, copper bath (hereinafter, BCP) was deposited to a thickness of 60 Å as a hole blocking layer, and Alq3 was deposited on the hole blocking layer to a thickness of 200 Å as an electron transport layer.

[0319] Finally, lithium fluoride (LiF) is deposited to a thickness of 10 Å on the electron transport layer to form an electron injection layer, and then an aluminum (Al) cathode is deposited to a thickness of 1,200 Å on the electron injection layer to form a cathode, thereby fabricating an organic light-emitting device.

[0320] Meanwhile, all the organic compounds required to manufacture OLED devices are each in 10 -8 Up to 10 -6 The material is purified by vacuum sublimation under pressure and then used in OLED manufacturing.

[0321] The structures of the compounds used as comparative example compounds in Tables 14 and 16 below are as follows.

[0322] [Compare example compounds]

[0323] 2) Driving Voltage and Emission Efficiency of Organic Light Emitting Device The electroluminescence (EL) characteristics of the organic light-emitting devices of the examples and comparative examples in Tables 14 to 16, manufactured as described above, were measured using an M7000 device manufactured by McScience Co., and based on the measurement results, the electroluminescence (EL) characteristics of the devices were measured using an M6000 (lifetime measurement device) manufactured by McScience Co., at 6,000 cd / m². 2 T measured under reference brightness 90 T 90 Lifespan (unit: h, hour) refers to the time it takes for the brightness to return to 90% of its initial brightness.

[0324] The characteristics of the measured organic light-emitting devices are shown in Tables 14 to 16 below.

[0325] [Table 14]

[0326] [Table 15]

[0327] [Table 16]

[0328] As can be seen from the results in Tables 14 to 16, when the organic material layer of the organic light-emitting device is formed by co-depositing a mixture of three compounds according to this application, the efficiency and / or lifetime of the organic light-emitting device are confirmed to be improved.

[0329] Specifically, among the compounds of formulas 1 to 3, the compound of formula 1 is characterized by a relatively long lifetime, the compound of formula 2 provides high efficiency, and the compound of formula 3 is a unipolar N-host with high electron mobility. When these three types of compounds are mixed in appropriate ratios and used as materials for the device, improvements in the device's efficiency and lifetime can be confirmed.

[0330] The core structure of the comparative example compound N is obtained by bonding R3 and R4 in Formula 1 of the present invention to form a benzene ring, and unlike the present invention, it has a substituent at R1. In the case of comparative example 52 in which this compound is used as a material for a device, it can be seen that not only is the driving voltage very high, but the lifetime is also significantly poor.

[0331] Furthermore, when compounds comprising azazine and amine groups (such as comparative example compounds O to Z) are used in combination with compounds of formula 3 of the present invention, the charge balance is disrupted, thereby reducing efficiency and shortening lifetime.

Claims

1. A composition for an organic material layer in an organic light-emitting device, the composition comprising: The following compounds of chemical formula 1; The following compounds have chemical formula 2; as well as The following compounds have chemical formula 3: [Chemical Formula 1] In chemical formula 1, X is O or S. R1 and R2, R2 and R3, or R3 and R4 bond to each other to form substituted or unsubstituted benzene rings. When R3 and R4 are bonded to each other to form a substituted or unsubstituted benzene ring, R1 is hydrogen or deuterium. The remaining groups from R1 to R4 and any one of R5 to R8 are -(L1)l1-N(Ar1)(Ar2), and the other is -(L2)l2-Ar3. The remaining groups in R1 to R8 are each independently: hydrogen; deuterium; halogen group; cyano; substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms. L1 and L2 are each independently a direct bond or a substituted or unsubstituted aryl group with 6 to 60 carbon atoms. l1 and l2 are each integers from 1 to 3, and when l1 and l2 are each 2 or greater, the substituents in each pair of parentheses are either the same or different from each other. Ar1 and Ar2 are each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms. Ar3 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms. [Chemical Formula 2] In chemical formula 2, L11 is a direct bond, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms. l11 is an integer from 1 to 3, and when l11 is 2 or greater, L11 is the same or different. R11 is: a halogen group; a cyano group; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; or a substituted or unsubstituted silyl group. Any one of R12 to R19 is a substituted or unsubstituted carbazole group, or two adjacent groups of R12 to R19 are bonded to each other to form a substituted or unsubstituted heterocycle having 2 to 30 carbon atoms. The remaining groups in R12 to R19 are each independently: hydrogen; deuterium; halogen group; cyano; substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms. [Chemical Formula 3] In chemical formula 3, Y is O or S, and any one of R21 to R28 is -(L21)l21-(N-Het). L21 is a direct bond or a substituted or unsubstituted aryl group with 6 to 60 carbon atoms. l21 is an integer from 1 to 3, and when l21 is 2 or greater, L21 is the same or different. N-Het is a substituted or unsubstituted heteroaryl group including a C=N bond, and the remaining groups among R21 to R28 are each independently: hydrogen; deuterium; halogen group; cyano; substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; substituted or unsubstituted aryl group having 6 to 60 carbon atoms; substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; substituted or unsubstituted silyl group; or substituted or unsubstituted phosphine oxide group.

2. The composition for the organic material layer of an organic light-emitting device according to claim 1, in, Chemical formula 1 is represented by any one of the following chemical formulas 1-1 to 1-3: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formulas 1-3] Among them, in chemical formulas 1-1 to 1-3, Either S1 or S2 is -(L1)l1-N(Ar1)(Ar2), and the other is -(L2)l2-Ar3. H1 to H3 are each independently hydrogen or deuterium. m is an integer from 1 to 3, n is an integer from 1 to 5, o is 1 or 2, p is an integer from 1 to 4, and q is an integer from 1 to 6. Furthermore, when o is 2, or when each of m, n, p, and q is 2 or greater, the substituents in each pair of parentheses are either the same or different from each other. X, L1, L2, l1, l2 and Ar1 to Ar3 are as defined in the above chemical formula 1.

3. The composition for the organic material layer of an organic light-emitting device according to claim 1, in, Ar3 is an aryl group with 6 to 20 carbon atoms, either deuterated or unsubstituted.

4. The composition for an organic material layer in an organic light-emitting device according to claim 1, in, The weight ratio of the compound of chemical formula 1 to the compound of chemical formula 3 and the weight ratio of the compound of chemical formula 2 to the compound of chemical formula 3 are each 1:1 to 1:

5.

5. The composition for an organic material layer in an organic light-emitting device according to claim 1, in, The deuterium substitution rate of each of the compounds of chemical formulas 1 to 3 is 0% or greater than 0% and is 100% or less.

6. The composition for an organic material layer in an organic light-emitting device according to claim 1, in, Chemical Formula 1 is represented by any of the following compounds: 。 7. The composition for an organic material layer in an organic light-emitting device according to claim 1, in, Chemical formula 2 is represented by any of the following compounds: 。。 8. The composition for an organic material layer in an organic light-emitting device according to claim 1, in, Chemical formula 3 is represented by any of the following compounds: 。 9. An organic light-emitting device, comprising: First electrode; Second electrode; as well as At least one organic material layer is provided between the first electrode and the second electrode. Wherein, at least one of the organic material layers comprises a composition for an organic light-emitting device according to any one of claims 1 to 8.

10. The organic light-emitting device according to claim 9, in, The organic material layer includes an emitting layer, and the emitting layer includes the composition of the organic material layer for the organic light-emitting device.

11. A method for manufacturing an organic light-emitting device, the method comprising: Preparation of substrate; A first electrode is formed on the substrate; At least one organic material layer is formed on the first electrode; as well as A second electrode is formed on the organic material layer. The step of forming the organic material layer includes forming at least one organic material layer by using the composition for an organic material layer of an organic light-emitting device according to claim 1.

12. The method for manufacturing an organic light-emitting device according to claim 11, in, The step of forming the organic material layer includes initially mixing the composition of the organic material layer for the organic light-emitting device and depositing the initially mixed composition from a single source.

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