Heterocyclic compound, organic light emitting element, and composition for forming organic material layer

Abstract

The present invention relates to: a heterocyclic compound of formula 1; an organic light-emitting element and a composition for forming an organic material layer comprising the heterocyclic compound of formula 1.

Description

[0001] This specification claims priority and benefits to Korean Patent Application No. 10-2020-0134081, filed with the Korean Intellectual Property Office on October 16, 2020, the entire contents of which are incorporated herein by reference. Technical Field

[0002] This specification relates to a heterocyclic compound, an organic light-emitting element, and a composition for forming an organic material layer. Background Technology

[0003] Electroluminescent elements are a type of autoluminescent display element and have advantages such as wide viewing angle, high response speed, and excellent contrast.

[0004] Organic light-emitting elements (OLEDs) have a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to an OLED with such a structure, electrons and holes injected from the two electrodes combine and pair in the organic thin film, and emit light when these electrons and holes annihilate. The organic thin film can be formed as a single layer or multiple layers, depending on the desired effect.

[0005] Depending on the requirements, organic thin film materials can possess light-emitting capabilities. For example, as materials for organic thin films, compounds capable of forming their own light-emitting layers can be used alone, or compounds that can act as the host or dopant in a host-dopant type light-emitting layer can be used. Additionally, compounds capable of hole injection, hole transfer, electron blocking, and similar functions can also be used as materials for organic thin films.

[0006] The development of organic thin film materials has continuously demanded improvements in the performance, lifespan, or efficiency of organic light-emitting elements. Summary of the Invention

[0007] Technical issues

[0008] This specification relates to providing a heterocyclic compound, an organic light-emitting element, and a composition for forming an organic material layer.

[0009] Technical solutions

[0010] One embodiment of this specification provides a heterocyclic compound of the following chemical formula 1.

[0011] [Chemical Formula 1]

[0012]

[0013] In chemical formula 1,

[0014] X1 to X3 are each independently N or CH.

[0015] At least one of X1 to X3 is N, and

[0016] N-Het is represented by the following chemical formulas: N-1 or N-2.

[0017] [Chemical formula N-1]

[0018]

[0019] [Chemical formula N-2]

[0020]

[0021] In chemical formulas N-1 and N-2

[0022] R1 to R3 are each independently hydrogen, deuterium, halogroup, cyanogroup, substituted or unsubstituted silyl group, substituted or unsubstituted phosphoyl group, substituted or unsubstituted C1 to C60 alkyl group, substituted or unsubstituted C3 to C60 cycloalkyl group, substituted or unsubstituted bicyclic or low-carbon aryl group, substituted or unsubstituted triphenyl group, substituted or unsubstituted fluorenyl group, substituted or unsubstituted tetracyclic or high-carbon aryl group, or substituted or unsubstituted C2 to C60 heteroaryl group.

[0023] Ar is a substituted or unsubstituted C6 to C60 aryl group, or a substituted or unsubstituted C2 to C60 heteroaryl group, and

[0024] Het1 is represented by the chemical formula H-1, and Het2 is represented by the chemical formula H-2.

[0025] [Chemical formula H-1]

[0026]

[0027] [Chemical formula H-2]

[0028]

[0029] In chemical formulas H-1 and H-2,

[0030] Y1 and Y2 are each independently O or S.

[0031] A1 to A4 and B1 to B4 are each independently bonded to chemical formula 1, either as hydrogen or deuterium, and

[0032] Formula 1 is bonded to any of A1 to A4 of Formula H-1 and any of B1 to B4 of Formula H-2, denoted by Am-Bn, where m and n are 1, 2, 3 or 4 respectively, and m and n are different.

[0033] Another embodiment of this specification provides an organic light-emitting element comprising: a first electrode; a second electrode disposed opposite to the first electrode; and an organic material layer disposed between the first electrode and the second electrode, wherein the organic material layer comprises a heterocyclic compound of formula 1.

[0034] Another embodiment of this specification provides a composition for forming an organic material layer, the composition comprising a heterocyclic compound of formula 1 and a compound of formula 3 below.

[0035] [Chemical Formula 3]

[0036]

[0037] In chemical formula 3,

[0038] R31 and R32 are each independently hydrogen, deuterium, halogroup, substituted or unsubstituted C1 to C60 alkyl, substituted or unsubstituted C3 to C60 cycloalkyl, substituted or unsubstituted C6 to C60 aryl, or substituted or unsubstituted C2 to C60 heteroaryl.

[0039] Ar31 and Ar32 are each independently a substituted or unsubstituted C6 to C60 aryl group, or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0040] r31 is an integer from 0 to 4, and when it is 2 or greater than 2, R31 is either the same or different from each other.

[0041] r32 is an integer from 0 to 4, and when it is 2 or greater than 2, R32 is either the same or different from each other.

[0042] Beneficial effects

[0043] The compounds described in this specification can be used as materials for the organic material layer of an organic light-emitting element. These compounds can function as hole injection materials, hole transfer materials, light-emitting materials, electron transfer materials, electron injection materials, charge-generating materials, or the like. Specifically, the compounds can be used as materials for the light-emitting layer of an organic light-emitting element.

[0044] Using heterocyclic compounds of Formula 1 and compounds of Formula 3 together as the light-emitting layer of an organic light-emitting element can reduce the driving voltage, enhance luminous efficiency, and improve the lifespan of the element. Attached Figure Description

[0045] Figures 1 to 3 A diagram illustrating the laminated structure of an organic light-emitting element according to one embodiment of this specification is provided.

[0046] Explanation of icon numbers

[0047] 100: Base

[0048] 200: Anode

[0049] 300: Organic material layer

[0050] 301: Hole Injection Layer

[0051] 302: Hole Transfer Layer

[0052] 303: Emissive layer

[0053] 304: Cavity Blocking Layer

[0054] 305: Electron Transfer Layer

[0055] 306: Electron Injection Layer

[0056] 400: Cathode Detailed Implementation

[0057] This instruction manual will be described in more detail below.

[0058] In this specification, a description in which a part “contains” certain components means that it may also contain other components, and other components are not excluded unless specifically stated to the contrary.

[0059] The term “substitution” means that the hydrogen atom bonded to the carbon atom of a compound is replaced by another substituent, and the position of substitution is not limited, as long as the position is where the hydrogen atom is substituted, that is, the position where the substituent can be substituted. When two or more substituents are substituted, the two or more substituents may be the same as or different from each other.

[0060] In this specification, "substituted or unsubstituted" means substituted or unsubstituted by one or more substituents selected from the group consisting of: deuterium, halogen, cyano, C1 to C60 alkyl, C2 to C60 alkenyl, C2 to C60 alkynyl, C3 to C60 cycloalkyl, C2 to C60 heterocycloalkyl, C6 to C60 aryl, C2 to C60 heteroaryl, silyl, phosphine oxide, and amino, or substituted or unsubstituted by a substituent bonded to two or more substituents selected from the substituents shown above.

[0061] In this specification, "in the absence of substituents in the chemical formula or compound structure" means that hydrogen atoms are bonded to carbon atoms. However, due to deuterium ( 2 H) is an isotope of hydrogen, so some hydrogen atoms can be deuterium.

[0062] In one embodiment of this application, "the case where no substituent is indicated in the chemical formula or compound structure" can mean that all positions where substituents can appear can be hydrogen or deuterium. In other words, since deuterium is an isotope of hydrogen, some hydrogen atoms can be deuterium as an isotope, and in this document, the deuterium content can be from 0% to 100%.

[0063] In one embodiment of this application, in cases where "no substituents are indicated in the chemical formula or compound structure", hydrogen and deuterium may be mixed in the compound when deuterium is not explicitly excluded (e.g., the deuterium content is 0%, the hydrogen content is 100%, or all substituents are hydrogen).

[0064] In one embodiment of this application, deuterium is an isotope of hydrogen, an element having a deuterium nucleus formed by 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.

[0065] In one embodiment of this application, an isotope means an atom having the same number of atoms (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.

[0066] In one embodiment of this application, the content of a specific substituent, T%, can be defined as T2 / T1×100=T%, where the total number of substituents that the base compound may have is defined as T1, and the number of a specific substituent among these substituents is defined as T2.

[0067] In other words, in one instance, in the case of... The statement that a phenyl group has a deuterium content of 20% means that the phenyl group may have a total of 5 substituents (T1 in the formula), and that the number of deuterium substituents is 1 (T2 in the formula). In other words, a phenyl group having a deuterium content of 20% can be represented by the following structural formula.

[0068]

[0069] In addition, in one embodiment of this application, "phenyl with 0% deuterium content" can mean a phenyl that does not contain deuterium atoms, that is, a phenyl with 5 hydrogen atoms.

[0070] In this specification, halogen may be fluorine, chlorine, bromine or iodine.

[0071] In this specification, alkyl groups comprise straight or branched chains and may be further substituted with other substituents. The number of carbon atoms in an alkyl group may be from 1 to 60, specifically from 1 to 40, and more specifically from 1 to 20. Specific examples may include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tributyl, dibutyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tri-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, tri-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like.

[0072] In this specification, the alkenyl group comprises a straight chain or a branched chain and may be further substituted with other substituents. The alkenyl group may have 2 to 60 carbon atoms, specifically 2 to 40, and more specifically 2 to 20. Specific examples may include 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-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbene, styryl, and the like, but are not limited thereto.

[0073] In this specification, the alkynyl group comprises a straight chain or a branched chain and may be further substituted with other substituents. The number of carbon atoms in the alkynyl group may be 2 to 60, specifically 2 to 40, and more specifically 2 to 20.

[0074] In this specification, cycloalkyl comprises a monocyclic or polycyclic ring having 3 to 60 carbon atoms and may be further substituted with other substituents. Polycyclic here means a group in which the cycloalkyl group is directly bonded to or fused with other cyclic groups. Other cyclic groups may be cycloalkyl, but may also be different types of cyclic groups, such as heterocycloalkyl, aryl, and heteroaryl. The number of carbon groups in a cycloalkyl group may be 3 to 60, specifically 3 to 40, and more specifically 5 to 20. Specific examples may include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto.

[0075] In this specification, heterocyclic alkyl groups comprise 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 with other substituents. Herein, polycyclic means a group in which the heterocyclic alkyl group is directly bonded to or fused with other cyclic groups. Herein, the other cyclic groups may be heterocyclic alkyl groups, but may also be different types of cyclic groups, such as cycloalkyl, aryl, and heteroaryl. The number of carbon atoms in a heterocyclic alkyl group may be 2 to 60, specifically 2 to 40, and more specifically 3 to 20.

[0076] In this specification, an aryl group comprises a monocyclic or polycyclic ring having 6 to 60 carbon atoms, and may be further substituted with other substituents. Herein, polycyclic means a group in which the aryl group is directly bonded to or fused with other cyclic groups. Herein, the other cyclic group may be an aryl group, but may also be different types of cyclic groups, such as cycloalkyl, heterocycloalkyl, and heteroaryl. An aryl group comprises a spirocyclic group. The number of carbon atoms in an aryl group may be 6 to 60, specifically 6 to 40, and more specifically 6 to 25. When the aryl group is bicyclic or more, the number of carbon atoms may be 8 to 60, 8 to 40, or 8 to 30. Specific examples of aryl groups may include phenyl, biphenyl, triphenyl, naphthyl, anthracene, trunyl, phenanthrene, perylene, fluorenyl, triphenylene, propylene-naphthyl, pyrene, fused tetraphenyl, fused pentaphenyl, fluorenyl, indene, acenaphthyl, benzo[a]fluorenyl, spirofluorenyl, 2,3-dihydro-1H-indene, their fused ring groups, and the like, but are not limited thereto.

[0077] In this specification, triphenyl may be selected from the following structures.

[0078]

[0079] In this specification, the fluorene group may be substituted, and adjacent substituents may bond to each other to form a ring.

[0080] When the fluorene group is substituted, it may contain And similar structures, however, the structure is not limited to this.

[0081] In this specification, a heteroaryl group contains O, S, SO2, Se, N, or Si as a heteroatom, and may be monocyclic or polycyclic, and may be further substituted with other substituents. Polycyclic here means a group in which the heteroaryl group is directly bonded to or fused with other cyclic groups. Other cyclic groups may be heteroaryl groups, but may also be different types of cyclic groups, such as cycloalkyl, heterocycloalkyl, and aryl groups. The number of carbon atoms in a heteroaryl group may be 2 to 60, specifically 2 to 40, and more specifically 3 to 25. When the heteroaryl group is bicyclic or more, the number of carbon atoms may be 4 to 60, 4 to 40, or 4 to 25. Specific examples of heteroaryl groups may include pyridyl, pyrroloyl, pyrimidinyl, pyridazinyl, furanyl, thiopheneyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, furazolidyl, oxadiazolyl, thiazolyl, dithiazolyl, tetrazolyl, piperanyl, thiopiperanyl, diazinyl group, oxazinyl, thiazolyl, dioxynyl group, triazinyl, tetrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, isoquinazolinyl, quinazolinyl group, naphthyridyl group, acridineyl, phenidyl, imidazopyridyl, diazanaphthalenyl group, and triazaindene. (group), indole, indoleazinyl, benzothiazolyl, benzoxazolyl, benzoimidazolyl, benzothiophene, benzofuranyl, dibenzothiophene, dibenzofuranyl, carbazole, benzocarbazole, dibenzocarbazole, phenazinyl, dibenzothiophenolyl (dibenzosilole group), spirodi(dibenzothiophenol), dihydrophenazinyl (dihydrophenazinyl group), phenoxazinyl, phenanthridyl (phenanthridyl group), thiophene, indole[2,3-a]carbazole, indole[2,3-b]carbazole, dihydroindole, 10,11-dihydro-dibenzo[b,f]acoxazinyl, 9,10-dihydroacridinyl, phenanthrazinyl (phenanthrazinyl group), phenanthrazinyl, naphthylidinyl (naphthylidinyl) group), phenolinyl, benzo[c][1,2,5]thiadiazolyl, 5,10-dihydrobenzo[b,e][1,4]azasilolinyl, pyrazolo[1,5-c]quinazolinyl, pyrido[1,2-b]inzolyl, pyrido[1,2-a]imidazo[1,2-e]dihydroindoleyl, benzofuran[2,3-d]pyrimidinyl, benzothieno[2,3-d]pyrimidinyl, benzofuran[2,3-a]carbazoleyl, benzothieno[2,3-a]carbazoleyl, 1,3-dihydroindole[2,3-a]carbazolyl, benzofurano[3,2-a]carbazolyl, benzothieno[3,2-a]carbazolyl, 1,3-dihydroindole[3,2-a]carbazolyl, benzofurano[2,3-b]carbazolyl, benzothieno[2,3-b]carbazolyl, 1,3-dihydroindole[2,3-b]carbazolyl, benzofurano[3,2-b]carbazolyl, benzothieno[3,2-b]carbazolyl, 1,3-dihydroindole[3,2-b]carbazolyl, benzofurano[2,3-c]carbazolyl, benzothieno[2,3-c]carbazolyl, 1,3 -Dihydroindole[2,3-c]carbazole, benzofurano[3,2-c]carbazole, benzothieno[3,2-c]carbazole, 1,3-dihydroindole[3,2-c]carbazole, 1,3-dihydroindo[2,1-b]carbazole, 5,11-dihydroindo[1,2-b]carbazole, 5,12-dihydroindo[1,2-c]carbazole, 5,8-dihydroindo[2,1-c]carbazole, 7,12-dihydroindo[1,2-a]carbazole, 11,12-dihydroindo[2,1-a]carbazole, and similar, but not limited thereto.

[0082] In this specification, silane is a substituent containing Si, such that the Si atoms are directly bonded as free radicals, and is represented by -Si(R101)(R102)(R103). R101 to R103 may be the same as or different from each other, and may each be an independent substituent formed from at least one of the following: hydrogen, deuterium, halogroup, alkyl, alkenyl, alkoxy, cycloalkyl, aryl, and heteroaryl. Specific examples of silane may include, but are not limited to, trimethylsilane, triethylsilane, tributyldimethylsilane, vinyldimethylsilane, propyldimethylsilane, triphenylsilane, diphenylsilane, phenylsilane, and the like.

[0083] In this specification, phosphine oxide is represented by -P(=O)(R104)(R105), where R104 and R105 may be the same as or different from each other and may each be independently a substituent formed from at least one of the following: hydrogen, deuterium, halogroup, alkyl, alkenyl, alkoxy, cycloalkyl, aryl, and heteroaryl. Specifically, phosphine oxide may be substituted with an alkyl or aryl group, and the examples described above may be used as alkyl and aryl groups. Examples of phosphine oxide may include, but are not limited to, dimethylphosphine oxide, diphenylphosphine oxide, dinaphthylphosphine oxide, and the like.

[0084] In this specification, the amino group is represented by -N(R106)(R107), and R106 and R107 may be the same as or different from each other and may each be independently a substituent formed from at least one of the following: hydrogen, deuterium, halogroup, alkyl, alkenyl, alkoxy, cycloalkyl, 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 although not specifically limited thereto, the number of carbon atoms is preferably from 1 to 30. Specific examples of amino groups may include, but are not limited to, methylamino, dimethylamino, ethylamino, diethylamino, aniline, naphthylamino, benzidine, dibenzidine, anthraceneamino, 9-methyl-anthraminamino, diphenylamino, phenylnaphthylamino, xyleneamino, phenyltoluidine, triphenylamino, benzidine, phenylbenzidine, benzidinefluoreneamino, phenyltriphenylamino, benzidinetriphenylamino, and the like.

[0085] In this specification, except that the aryl group is a divalent group, the examples of aryl groups described above are applicable to aryl groups.

[0086] In this specification, except that the heteroaryl group described above is a divalent group, the examples of heteroaryl groups can be applied to heteroaryl groups.

[0087] In one embodiment of this specification, X1 to X3 of chemical formula 1 are each independently N or CH, and at least one of X1 to X3 is N.

[0088] In one embodiment of this specification, X1 to X3 are each independently N or CH, and two or more of X1 to X3 are N.

[0089] In one embodiment of this specification, X1 to X3 are N.

[0090] In one embodiment of this specification, N-Het of chemical formula 1 may be represented by the following chemical formula N-1.

[0091] [Chemical formula N-1]

[0092]

[0093] In chemical formula N-1,

[0094] R1 is hydrogen, deuterium, halogroup, cyanogroup, substituted or unsubstituted silyl group, substituted or unsubstituted phosphino group, substituted or unsubstituted C1 to C60 alkyl group, substituted or unsubstituted C3 to C60 cycloalkyl group, substituted or unsubstituted bicyclic or low-carbon aryl group, substituted or unsubstituted triphenyl group, substituted or unsubstituted fluorenyl group, substituted or unsubstituted tetracyclic or high-carbon aryl group, or substituted or unsubstituted C2 to C60 heteroaryl group, and

[0095] Ar is a substituted or unsubstituted C6 to C60 aryl group, or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0096] In one embodiment of this specification, R1 is hydrogen, a substituted or unsubstituted bicyclic or low-carbon aryl group, a substituted or unsubstituted triphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted tetracyclic or high-carbon aryl group, or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0097] In one embodiment of this specification, R1 is hydrogen, a substituted or unsubstituted bicyclic or low-carbon aryl group, a substituted or unsubstituted triphenyl group, a substituted or unsubstituted fluorenyl group, or a substituted or unsubstituted tetracyclic or high-carbon aryl group.

[0098] In one embodiment of this specification, R1 may be hydrogen, or a substituted or unsubstituted bicyclic or low-carbon aryl group.

[0099] In one embodiment of this specification, R1 may be hydrogen, a substituted or unsubstituted phenyl, or a substituted or unsubstituted biphenyl.

[0100] In one embodiment of this specification, R1 may be hydrogen, phenyl, or biphenyl.

[0101] In one embodiment of this specification, Ar is a substituted or unsubstituted C6 to C40 aryl group, or a substituted or unsubstituted C2 to C40 heteroaryl group.

[0102] In one embodiment of this specification, Ar is a substituted or unsubstituted C6 to C60 aryl group.

[0103] In one embodiment of this specification, Ar is a substituted or unsubstituted C6 to C40 aryl group.

[0104] In one embodiment of this specification, Ar is a substituted or unsubstituted C6 to C20 aryl group.

[0105] In one embodiment of this specification, Ar may be a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted triphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted phenanthyl, a substituted or unsubstituted triphenylene, or a substituted or unsubstituted pyrene.

[0106] In one embodiment of this specification, Ar may be an unsubstituted phenyl, a deuterated phenyl, a C1 to C10 alkyl-substituted phenyl, a deuterated C1 to C10 alkyl-substituted phenyl, an unsubstituted or deuterated biphenyl, a triphenyl, a naphthyl, a phenanthryl, a triphenylene, or a pyrene.

[0107] In one embodiment of this specification, Ar may be an unsubstituted or deuterated or t-Bu (tertiary butyl) phenyl, a deuterated C1 to C5 alkyl substituted phenyl, an unsubstituted or deuterated biphenyl, triphenyl, naphthyl, phenanthrene, triphenylene, or pyrene.

[0108] When chemical formula N-1 contains a bonding group instead of being directly bonded to chemical formula 1, the band gap decreases as the bonding length increases, which can lead to a decrease in efficiency.

[0109] In one embodiment of this specification, N-Het of chemical formula 1 may be represented by the following chemical formula N-2.

[0110] [Chemical formula N-2]

[0111]

[0112] In the chemical formula N-2,

[0113] R2 and R3 are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted silyl, substituted or unsubstituted phosphoyl, substituted or unsubstituted C1 to C60 alkyl, substituted or unsubstituted C3 to C60 cycloalkyl, substituted or unsubstituted bicyclic or low-carbon aryl, substituted or unsubstituted triphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted tetracyclic or high-carbon aryl, or substituted or unsubstituted C2 to C60 heteroaryl.

[0114] In one embodiment of this specification, R2 and R3 are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C60 alkyl, substituted or unsubstituted C3 to C60 cycloalkyl, substituted or unsubstituted bicyclic or low-carbon aryl, substituted or unsubstituted triphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted tetracyclic or high-carbon aryl, or substituted or unsubstituted C2 to C60 heteroaryl.

[0115] In one embodiment of this specification, R2 and R3 are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C3 to C30 cycloalkyl, substituted or unsubstituted bicyclic or low-carbon aryl, substituted or unsubstituted triphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted tetracyclic or high-carbon aryl, or substituted or unsubstituted C2 to C30 heteroaryl.

[0116] In one embodiment of this specification, R2 and R3 are each independently hydrogen, deuterium, substituted or unsubstituted bicyclic or low-carbon aryl, substituted or unsubstituted triphenyl, or substituted or unsubstituted tetracyclic or high-carbon aryl.

[0117] In one embodiment of this specification, R2 and R3 are each independently hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted naphthyl, or substituted or unsubstituted triphenylene.

[0118] In one embodiment of this specification, R2 and R3 are each independently hydrogen, deuterium, unsubstituted or deuterated or C1 to C10 alkyl-substituted phenyl, biphenyl, triphenyl, naphthyl, or triphenylene.

[0119] In one embodiment of this specification, R2 and R3 are each independently hydrogen, deuterium, unsubstituted or deuterated or t-Bu (tert-butyl) substituted phenyl, biphenyl, triphenyl, naphthyl, or triphenylene.

[0120] In one embodiment of this specification, R2 is hydrogen, deuterium, a substituted or unsubstituted bicyclic or low-carbon aryl group, a substituted or unsubstituted triphenyl group, or a substituted or unsubstituted tetracyclic or high-carbon aryl group.

[0121] In one embodiment of this specification, R2 is hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted naphthyl, or substituted or unsubstituted triphenylene.

[0122] In one embodiment of this specification, R2 is hydrogen, deuterium, unsubstituted or deuterated or C1 to C10 alkyl-substituted phenyl, biphenyl, triphenyl, naphthyl, or triphenylene.

[0123] In one embodiment of this specification, R3 is hydrogen, deuterium, or a substituted or unsubstituted bicyclic or low-carbon aryl group.

[0124] In one embodiment of this specification, R3 is hydrogen, deuterium, or a substituted or unsubstituted phenyl group.

[0125] In one embodiment of this specification, R3 is hydrogen, deuterium, or an unsubstituted or deuterated or C1 to C10 alkyl-substituted phenyl group.

[0126] When the nitrogen of carbazole is directly bonded to the structure of chemical formula 1 instead of chemical formula N-2, the band gap is reduced by enhancing the charge transfer between the donor and acceptor, and a weak bond dissociation energy (BDE) value is obtained, which leads to the problem of reduced lifetime.

[0127] In one embodiment of this specification, Het1 of chemical formula 1 is represented by the following chemical formula H-1, and Het2 of chemical formula 1 is represented by the following chemical formula H-2.

[0128] [Chemical formula H-1]

[0129]

[0130] [Chemical formula H-2]

[0131]

[0132] In chemical formulas H-1 and H-2,

[0133] Y1 and Y2 are each independently O or S.

[0134] A1 to A4 and B1 to B4 are each independently bonded to chemical formula 1, either as hydrogen or deuterium.

[0135] Formula 1 is bonded to any of A1 to A4 of Formula H-1 and any of B1 to B4 of Formula H-2, denoted by Am-Bn, where m and n are 1, 2, 3 or 4 respectively, and m and n are different.

[0136] In one embodiment of this specification, Y1 and Y2 may be 0.

[0137] In one embodiment of this specification, Y1 and Y2 may be S.

[0138] In one embodiment of this specification, either Y1 or Y2 is O, and the other may be S.

[0139] In one embodiment of this specification, A1 to A4 of chemical formula H-1 and B1 to B4 of chemical formula H-2 are each independently bonded to chemical formula 1, which may be hydrogen or deuterium.

[0140] In one embodiment of this specification, the unbonded portions of A1 to A4 and B1 to B4 to the remainder of Formula 1 are hydrogen or deuterium.

[0141] In one embodiment of this specification, chemical formula 1 is bonded to any of A1 to A4 of chemical formula H-1 and any of B1 to B4 of chemical formula H-2, denoted as Am-Bn, where m is different from n.

[0142] In one embodiment of this specification, when chemical formula 1 is bonded to A1 of chemical formula H-1 and to B2 of chemical formula H-2, it is represented as A1-B2.

[0143] In one embodiment of this specification, when chemical formula 1 is bonded to A1 of chemical formula H-1, chemical formula 1 may be bonded to B2, B3, or B4 of chemical formula H-2, which can be represented by A1-B2, A1-B3, or A1-B4, respectively. In other words, when chemical formula 1 is bonded to A1 of chemical formula H-1, chemical formula 1 cannot be bonded to B1 of chemical formula H-2.

[0144] In one embodiment of this specification, when chemical formula 1 is bonded to A2 of chemical formula H-1, chemical formula 1 can be bonded to B1, B3, or B4 of chemical formula H-2, which can be represented by A2-B1, A2-B3, or A2-B4, respectively. In other words, when chemical formula 1 is bonded to A2 of chemical formula H-1, chemical formula 1 cannot be bonded to B2 of chemical formula H-2.

[0145] In one embodiment of this specification, when chemical formula 1 is bonded to A3 of chemical formula H-1, chemical formula 1 can be bonded to B1, B2, or B4 of chemical formula H-2, which can be represented by A3-B1, A3-B2, or A3-B4, respectively. In other words, when chemical formula 1 is bonded to A3 of chemical formula H-1, chemical formula 1 cannot be bonded to B3 of chemical formula H-2.

[0146] In one embodiment of this specification, when chemical formula 1 is bonded to A4 of chemical formula H-1, chemical formula 1 can be bonded to B1, B2, or B3 of chemical formula H-2, which can be represented by A4-B1, A4-B2, or A4-B3, respectively. In other words, when chemical formula 1 is bonded to A4 of chemical formula H-1, chemical formula 1 cannot be bonded to B4 of chemical formula H-2.

[0147] When dibenzofuran or dibenzothiophene is bonded to Formula 1 at the same position, the LUMO orbitals become widely delocalized, thereby reducing electron mobility and potentially decreasing efficiency. Furthermore, deposition may occur in flat molecular structures, deriving crystallinity from them, which leads to fragility in terms of lifespan.

[0148] In one embodiment of this specification, chemical formula 1 may be represented by any of the following chemical formulas 2-1 to 2-4.

[0149] [Chemical Formula 2-1]

[0150]

[0151] [Chemical Formula 2-2]

[0152]

[0153] [Chemical Formula 2-3]

[0154]

[0155] [Chemical Formula 2-4]

[0156]

[0157] In chemical formulas 2-1 to 2-4

[0158] H1 to H4 are each independently hydrogen or deuterium, and

[0159] The remainder of the substituents have the same definition as in Formula 1.

[0160] In one embodiment of this specification, chemical formula 1 may be represented by any of the following compounds, but is not limited thereto.

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180] Furthermore, by introducing various substituents into the structure of Formula 1, compounds with the unique properties of the introduced substituents can be synthesized. For example, by introducing substituents commonly used as hole injection layer materials, hole transfer layer materials, light-emitting layer materials, electron transfer layer materials, and charge generation layer materials for manufacturing organic light-emitting elements into the core structure, materials that meet the requirements of each organic material layer can be synthesized.

[0181] Furthermore, by introducing various substituents into the structure of Formula 1, the band gap can be precisely controlled, and at the same time, the properties at the interface between organic materials can be enhanced, and the application of materials can be diversified.

[0182] One embodiment of this specification provides an organic light-emitting element comprising: a first electrode; a second electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein the one or more organic material layers comprise a heterocyclic compound of formula 1.

[0183] In one embodiment of this specification, the first electrode may be an anode and the second electrode may be a cathode.

[0184] In another embodiment of this specification, the first electrode may be a cathode, and the second electrode may be an anode.

[0185] In one embodiment of this specification, the organic light-emitting element may be a blue organic light-emitting element, and the heterocyclic compound of Formula 1 may be used as a material for the blue organic light-emitting element. For example, the heterocyclic compound of Formula 1 may be included in the light-emitting layer of the blue organic light-emitting element.

[0186] In one embodiment of this specification, the organic light-emitting element may be a green organic light-emitting element, and the heterocyclic compound of Formula 1 may be used as a material for the green organic light-emitting element. For example, the heterocyclic compound of Formula 1 may be contained in the light-emitting layer of the green organic light-emitting element.

[0187] In one embodiment of this specification, the organic light-emitting element may be a red organic light-emitting element, and the heterocyclic compound of Formula 1 may be used as a material for the red organic light-emitting element. For example, the heterocyclic compound of Formula 1 may be contained in the light-emitting layer of the red organic light-emitting element.

[0188] In addition to using the compounds described above to form one or more organic material layers, the organic light-emitting elements in this specification can also be manufactured using common organic light-emitting element manufacturing methods and materials.

[0189] When manufacturing organic light-emitting elements, solution coating and vacuum deposition methods can be used to form organic material layers from compounds. In this document, solution coating means spin coating, dip coating, inkjet printing, screen printing, spray coating, roller coating, and similar methods, but is not limited to these.

[0190] The organic material layer of the organic light-emitting element described in this specification can be formed as a single layer, but it can also be formed as a multilayer structure in which two or more organic material layers are laminated. For example, the organic light-emitting element of this disclosure may have a structure comprising a hole injection layer, a hole transfer layer, a light-emitting layer, an electron transfer layer, an electron injection layer, and the like as organic material layers. However, the structure of the organic light-emitting element is not limited to this, and it may contain a smaller number of organic material layers.

[0191] In the organic light-emitting element of this specification, the organic material layer includes a light-emitting layer, and the light-emitting layer may contain a heterocyclic compound of formula 1.

[0192] In the organic light-emitting element of this specification, the organic material layer includes a light-emitting layer, the light-emitting layer includes a host, and the host may include a heterocyclic compound of formula 1.

[0193] In the organic light-emitting element of this specification, the organic material layer includes a light-emitting layer, and the light-emitting layer may include a heterocyclic compound of chemical formula 1 and a compound of chemical formula 3 below.

[0194] [Chemical Formula 3]

[0195]

[0196] In chemical formula 3,

[0197] R31 and R32 are each independently hydrogen, deuterium, halogroup, substituted or unsubstituted C1 to C60 alkyl, substituted or unsubstituted C3 to C60 cycloalkyl, substituted or unsubstituted C6 to C60 aryl, or substituted or unsubstituted C2 to C60 heteroaryl.

[0198] Ar31 and Ar32 are each independently a substituted or unsubstituted C6 to C60 aryl group, or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0199] r31 is an integer from 0 to 4, and when it is 2 or greater than 2, R31 is either the same or different from each other.

[0200] r32 is an integer from 0 to 4, and when it is 2 or greater than 2, R32 is either the same or different from each other.

[0201] In one embodiment of this specification, R31 and R32 of Formula 3 are each independently hydrogen, deuterium, substituted or unsubstituted C6 to C60 aryl, or substituted or unsubstituted C2 to C60 heteroaryl.

[0202] In one embodiment of this specification, R31 and R32 are each independently hydrogen, deuterium, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heteroaryl.

[0203] In one embodiment of this specification, R31 and R32 are each independently hydrogen, or substituted or unsubstituted C6 to C30 aryl groups.

[0204] In one embodiment of this specification, R31 and R32 are each independently hydrogen or deuterium.

[0205] In one embodiment of this specification, Ar31 and Ar32 of Formula 3 are each independently a substituted or unsubstituted C6 to C40 aryl group, or a substituted or unsubstituted C2 to C40 heteroaryl group.

[0206] In one embodiment of this specification, Ar31 and Ar32 are each independently a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0207] In one embodiment of this specification, Ar31 and Ar32 are each independently a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heteroaryl group containing S.

[0208] In one embodiment of this specification, Ar31 and Ar32 are each independently a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted dibenzothiophene group.

[0209] In one embodiment of this specification, Ar31 and Ar32 are each independently a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted triphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted triphenylene, or a substituted or unsubstituted dibenzothiophene.

[0210] In one embodiment of this specification, Ar31 and Ar32 are each independently an unsubstituted or cyano, silyl or aryl substituted phenyl, biphenyl, triphenyl, naphthyl, unsubstituted or alkyl or aryl substituted fluorenyl, 9,9'-spirobis[fluorene], triphenylene, or unsubstituted or aryl substituted dibenzothiophene, wherein the aryl group is unsubstituted or alkyl or heteroaryl substituted.

[0211] In one embodiment of this specification, Ar31 and Ar32 may each be independently an unsubstituted or cyano, triphenylsilyl or aryl-substituted phenyl, biphenyl, triphenyl, naphthyl, unsubstituted or alkyl or aryl-substituted fluorenyl, 9,9'-spirodi[fluorene], or bitriphenylene.

[0212] In one embodiment of this specification, either Ar31 or Ar32 is a substituted or unsubstituted dibenzothiophene group, and the other may be a substituted or unsubstituted C6 to C30 aryl group.

[0213] In one embodiment of this specification, chemical formula 3 may be represented by the following chemical formula 4.

[0214] [Chemical Formula 4]

[0215]

[0216] In chemical formula 4,

[0217] Ar41 is an unsubstituted or alkyl-substituted C6 to C60 aryl group, or a C2 to C60 heteroaryl group, and

[0218] The remainder of the substituents have the same definition as in Formula 3.

[0219] In one embodiment of this specification, Ar41 of Formula 3 is a C6 to C40 aryl or a C2 to C40 heteroaryl.

[0220] In one embodiment of this specification, Ar41 of Formula 3 is a C6 to C40 aryl group, or a C2 to C40 heteroaryl group containing O or S.

[0221] In one embodiment of this specification, Ar41 of Formula 3 is a C6 to C20 aryl group, or a C2 to C20 heteroaryl group containing O or S.

[0222] In one embodiment of this specification, Ar41 of Formula 3 is phenyl, biphenyl, naphthyl, unsubstituted or alkyl-substituted fluorenyl, dibenzothiophene, or dibenzofuranyl.

[0223] In one embodiment of this specification, chemical formula 3 may be represented by any of the following compounds, but is not limited thereto.

[0224]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233] The organic light-emitting element disclosed herein may further comprise one, two, or more layers selected from the group consisting of: a light-emitting layer, a hole injection layer, a hole transfer layer, an electron injection layer, an electron transfer layer, an electron blocking layer, and a hole blocking layer.

[0234] Figures 1 to 3 The diagram illustrates the lamination sequence of electrodes and organic material layers in an organic light-emitting element according to one embodiment of this specification. However, the scope of this application is not limited to these figures, and structures of organic light-emitting elements known in the art can also be used in this application.

[0235] Figure 1 An organic light-emitting element is shown, wherein an anode 200, an organic material layer 300, and a cathode 400 are continuously laminated on a substrate 100. However, the structure is not limited to this structure, and other structures are also possible. Figure 2 As shown, an organic light-emitting element in which the cathode, organic material layer and anode are continuously laminated on the substrate can also be obtained.

[0236] Figure 3 This illustrates the case where the organic material layers are multiple. According to... Figure 3 The organic light-emitting element includes a hole injection layer 301, a hole transfer layer 302, a light-emitting layer 303, a hole blocking layer 304, an electron transfer layer 305, and an electron injection layer 306. However, the scope of this application is not limited to this laminated structure, and may exclude layers other than the light-emitting layer as needed, and may further add other required functional layers.

[0237] Depending on the requirements, the organic material layer containing the heterocyclic compound of formula 1 may also contain other materials.

[0238] In an organic light-emitting element according to one embodiment of this specification, materials other than heterocyclic compounds of Formula 1 are shown below. However, such materials are for illustrative purposes only and are not intended to limit the scope of this application, and may be replaced by materials known in the art.

[0239] As anode materials, materials with relatively large work functions can be used, and transparent conductive oxides, metals, conductive polymers, or the like can be used. Specific examples of anode materials include: metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxides (ITO), and indium zinc oxides (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, and the like, but not limited thereto.

[0240] Materials with relatively small work functions can be used as cathode materials, and metals, metal oxides, conductive polymers, or the like can be used. Specific examples of cathode materials include: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer materials such as LiF / Al or LiO2 / Al, and the like, but are not limited thereto.

[0241] As hole injection materials, known hole injection materials can be used, and for example, the following: phthalocyanine compounds, such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429; or starburst-type amine derivatives, such as tris(4-hydrazinoyl-9-ylphenyl)amine (TCTA), 4,4',4"-tris[phenyl(m-tolyl)amino]triphenylamine (m-MTDATA), or 1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene (m-MTDAPB) as described in the literature [Advanced Material, 6, p. 677 (1994)]; polyaniline / dodecylbenzenesulfonic acid, poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate), polyaniline / camphorsulfonic acid, or polyaniline / poly(4-styrenesulfonate) as conductive polymers with solubility; and the like.

[0242] As hole transfer materials, pyrazoline derivatives, aromatic amine derivatives, stilbene derivatives, triphenyldiamine derivatives and similar materials can be used, and low-molecular-weight or high-molecular-weight materials can also be used.

[0243] As electron transfer materials, metal complexes of oxadiazole derivatives, anthraquinone dimethyl ether and its derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, tetracyananthraquinone dimethyl ether and its derivatives, fluorenone derivatives, diphenyl dicyanoethylene and its derivatives, biphenylquinone derivatives, 8-hydroxyquinoline and its derivatives, and similar materials can also be used, as well as polymeric and low-molecular-weight materials.

[0244] LiF is commonly used in the field of electron injection materials, but this application is not limited thereto.

[0245] In addition to compounds of Formula 1 and Formula 3, materials emitting red, green, or blue light can also be used as luminescent materials, and two or more luminescent materials can be mixed and used as needed. In this document, when used, two or more luminescent materials can be deposited by individual supply sources or premixed and deposited by a single supply source. Furthermore, fluorescent materials can also be used as luminescent materials; however, phosphorescent materials can also be used. Materials that emit light by bonding holes and electrons injected from the anode and cathode can be used alone as luminescent materials; however, materials having a common host material and dopant material involved in luminescence can also be used.

[0246] In one embodiment of this specification, the phosphorescent dopant may be used as a dopant material.

[0247] In one embodiment of this specification, Ir(ppy)3, Ir(ppy)2(acac), Ir(mppy)3, Ir(ppy)2(bpmp), Ir(ppy)2(m-bppy) and the like may be used as phosphorescent dopants and the like, however, phosphorescent dopants are not limited thereto.

[0248] In one embodiment of this specification, Ir(ppy)3 can be used as a phosphorescent dopant.

[0249] When mixing luminescent material substrates, substrates from the same series or different series can be mixed. For example, any two or more types of N-type or P-type substrate materials can be selected and used as the substrate material for the luminescent layer.

[0250] In one embodiment of this specification, the compound of Formula 1 and the compound of Formula 3 may be mixed and used as the host material for the luminescent material. In this document, the compound of Formula 1 may be used as the N-type host material, and the compound of Formula 3 may be used as the P-type host material.

[0251] Depending on the materials used, an organic light-emitting element according to one embodiment of this specification may be a top-emitting, bottom-emitting, or bidirectional light-emitting type.

[0252] The compounds according to one embodiment of this specification can also be used in organic electronic components including organic solar cells, organic photoconductors, organic transistors and the like, based on similar principles used in organic light-emitting elements.

[0253] One embodiment of this specification provides a composition for forming an organic material layer, the composition comprising a heterocyclic compound of formula 1 and a compound of formula 3.

[0254] According to one embodiment of this specification, the composition for forming an organic material layer comprises a heterocyclic compound of Formula 1 and a compound of Formula 3 in a weight ratio of 1:10 to 10:1, 1:8 to 8:1, 1:5 to 5:1, or 1:2 to 2:1.

[0255] When a heterocyclic compound of Formula 1 and a compound of Formula 3 are included in the weight ratios within the range described above, an organic light-emitting element with low driving voltage and excellent luminous efficiency and lifespan can be provided. Specifically, when included in a weight ratio of 1:2 to 2:1, the organic light-emitting element exhibits significantly enhanced driving voltage, luminous efficiency, and lifespan properties.

[0256] The composition for forming an organic material layer according to one embodiment of this specification can be used as a light-emitting layer material for an organic light-emitting element.

[0257] In the following description, examples will be used to illustrate the invention in more detail; however, such descriptions are for illustrative purposes only and the scope of this application is not limited thereto.

[0258] <Preparation Example>

[0259] [Preparation Example 1] Preparation of Compound 1-1

[0260]

[0261] 1) Preparation of compound 1-1-1

[0262] In a round-bottom flask, a mixture of 2,4-dichloro-6-(dibenzo[b,d]furan-3-yl)-1,3,5-triazine (10 g, 31.6 mmol), dibenzo[b,d]furan-4-ylboronic acid (6.7 g, 31.6 mmol), Pd(PPh3)4(tetra(triphenylphosphine)palladium(0)) (1.8 g, 1.58 mmol), K2CO3 (potassium carbonate) (8.7 g, 63.2 mmol), and 1,4-dioxane / distilled water (100 mL / 20 mL) was refluxed at 120 °C for 4 h. The result was cooled to room temperature and filtered, followed by washing with 1,4-dioxane, distilled water, and methanol. The result was purified by column chromatography to obtain compound 1-1-1 (7.5 g, 53%).

[0263] 2) Preparation of compound 1-1

[0264] In a round-bottom flask, a mixture of compound 1-1-1 (7.5 g, 16.7 mmol), (9-phenyl-9H-carbazol-2-yl)coponic acid (5.75 g, 20.04 mmol), Pd(PPh3)4 (0.96 g, 0.835 mmol), K2CO3 (4.6 g, 33.4 mmol), and 1,4-dioxane / distilled water (75 mL / 15 mL) was refluxed at 120 °C for 4 hours. The result was cooled to room temperature and filtered, and then washed with 1,4-dioxane, distilled water, and methanol to obtain compound 1-1 (8.4 g, 77%).

[0265] Except for using intermediates A, B, and C from Table 1 below in place of 2,4-dichloro-6-(dibenzo[b,d]furan-3-yl)-1,3,5-triazine, dibenzo[b,d]furan-4-yl cyclopentanoic acid, and (9-phenyl-9H-carbazol-2-yl)cyclopentanoic acid in Preparation Example 1, the target compound D in Table 1 below was synthesized in the same manner as in Preparation Example 1.

[0266] [Table 1]

[0267]

[0268]

[0269] [Preparation Example 2] Preparation of Compounds 1-30

[0270]

[0271] 1) Preparation of compound 1-30-3

[0272] 2-Bromo-9H-carbazole (15 g, 60.95 mmol), 5'-iodo-1,1':3',1"-triphenyl (23.9 g, 67.04 mmol), CuI (copper iodide (I)) (11.6 g, 60.95 mmol), trans-1,2-diaminocyclohexane (7.0 g, 60.95 mmol), K3PO4 (tripotassium phosphate) (25.9 g, 121.9 mmol), and 1,4-dioxane (150 mL) were introduced into a round-bottom flask with a neck, and the mixture was stirred at 120 °C for 8 hours. The product was cooled to room temperature, and the organic layer was extracted with ethyl acetate. The organic layer was concentrated under vacuum and then separated by column chromatography to obtain compound 1-30-3 (22.6 g, 78%).

[0273] 2) Preparation of compound 1-30-2

[0274] Compound 1-30-3, B2(pin)2 (bis(pinacolyl)diboron) (24.1 g, 95.0 mmol), PdCl2(dppf) (dichloro[1,1'-bis(diphenylphosphino)ferrocene]palladium(II)) (3.5 g, 4.75 mmol), potassium acetate (9.3 g, 95.0 mmol), and 1,4-dioxane (230 mL) were introduced into a round-bottom flask with a neck, and the mixture was stirred at 120 °C for 8 hours. The product was extracted with dichloromethane (DCM) and concentrated, and then treated with dichloromethane / methanol to obtain compound 1-30-2 (16.1 g, 65%).

[0275] 3) Preparation of compound 1-30-1

[0276] Compound 1-30-1 (8.5 g, 60%) was obtained in the same manner as in the preparation of compound 1-1-1 of Preparation Example 1, except that 2-4-dichloro-6-(dibenzo[b,d]furan-2-yl)-1,3,5-triazine was used instead of 2-4-dichloro-6-(dibenzo[b,d]furan-3-yl)-1,3,5-triazine and dibenzo[b,d]furan-1-ylheptanic acid (10 g, 31.63 mmol) was used instead of dibenzo[b,d]furan-4-ylheptanic acid.

[0277] 4) Preparation of compound 1-30

[0278] Compound 1-30 (11.5 g, 75%) was obtained using the compounds 1-30-2 and 1-30-1 synthesized above in the same manner as in the preparation of compound 1-1 in Preparation Example 1.

[0279] Except for using intermediates A and B from Table 2 to replace 2,4-dichloro-6-(dibenzo[b,d]furan-3-yl)-1,3,5-triazine and dibenzo[b,d]furan-4-yl cyclopentanoic acid in Preparation Example 1, and using intermediates C-(1) and C-(2) from Table 2 to replace 2-bromo-9H-carbazole and 5'-iodine-1,1':3',1"-bitriphenyl in Preparation Example 2, the target compound D in Table 2 was synthesized in the same manner as in Preparation Example 1 and Preparation Example 2.

[0280] [Table 2]

[0281]

[0282] [Preparation Example 3] Preparation of Compound 2-1

[0283]

[0284] The target compound 2-1 (11.5 g, 55%) was obtained in the same manner as in Preparation Example 1, except that 9-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole was used instead of (9-phenyl-9H-carbazole-2-yl) cyclopentanoic acid.

[0285] Except for using intermediates A, B, and C from Table 3 below in place of 2,4-dichloro-6-(dibenzo[b,d]furan-3-yl)-1,3,5-triazine, dibenzo[b,d]furan-4-yl cyclopentanoic acid, and (9-phenyl-9H-carbazol-2-yl)cyclopentanoic acid in Preparation Example 1, target compound D in Table 3 below was synthesized in the same manner as in Preparation Example 1.

[0286] [Table 3]

[0287]

[0288]

[0289] [Preparation Example 4] Preparation of Compound 2-49

[0290]

[0291] 1) Preparation of compound 2-49-2

[0292] In a round-bottom flask, a mixture of 2-phenyl-9H-carbazole (15 g, 61.65 mmol), 1-chloro-4-fluorobenzene (9.7 g, 73.98 mmol), Cs₂CO₃ (cesium carbonate) (40.2 g, 123.3 mmol), and dimethylacetamide (DMA) (150 mL) was stirred at 120 °C for 8 hours. The product was cooled and then filtered. After removing the solvent from the filtrate, the product was purified by column chromatography to obtain compound 2-49-2 (19.6 g, 90%).

[0293] 2) Preparation of compound 2-49-1

[0294] In a round-bottom flask, a mixture of compounds 2-49-2 (19.6 g, 55.48 mmol), B2(pin)2 (28.2 g, 110.97 mmol), Pd2(dba)3 (2.54 g, 2.774 mmol), Xphos (2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl) (2.64 g, 5.55 mmol), KOAc (potassium acetate) (10.9 g, 110.97 mmol), and 1,4-dioxane (200 mL) was refluxed at 140 °C for 4 hours.

[0295] The extract was extracted with dichloromethane and concentrated, and then treated with dichloromethane / methanol to obtain compound 2-49-1 (17.8 g, 72%).

[0296] 3) Preparation of compound 2-49

[0297] The target compound 2-49 (9.8 g, 80%) was obtained in the same manner as in Preparation Example 1, except that compound 2-49-1 was used instead of (9-phenyl-9H-carbazole-2-yl) cyclopentanoic acid.

[0298] Except for using intermediates A and B from Table 4 below instead of 2,4-dichloro-6-(dibenzo[b,d]furan-3-yl)-1,3,5-triazine and dibenzo[b,d]furan-4-yl cyclopentanoic acid in Preparation Example 1, and using intermediates C-(1) and C-(2) from Table 4 below instead of 2-phenyl-9H-carbazole and 1-chloro-4-fluorobenzene in Preparation Example 4, the target compound D in Table 4 below was synthesized in the same manner as in Preparation Example 1 and Preparation Example 4.

[0299] [Table 4]

[0300]

[0301] [Preparation Example 5] Preparation of Compound 3-3

[0302]

[0303] 3-Bromo-1,1'-biphenyl (3.7 g, 15.8 mmol), 9-phenyl-9H,9'H-3,3'-dicarbazole (6.5 g, 15.8 mmol), CuI (3.0 g, 15.8 mmol), trans-1,2-diaminocyclohexane (1.9 mL, 15.8 mmol), and K3PO4 (3.3 g, 31.6 mmol) were dissolved in 1,4-dioxane (100 mL) and refluxed for 24 hours. After the reaction was complete, the product was extracted by introducing distilled water and DCM at room temperature, and the solvent was removed using a rotary evaporator after drying the organic layer with MgSO4. The reaction material was purified by column chromatography (DCM:hexane = 1:3) and recrystallized from methanol to obtain the target compound 3-3 (7.5 g, 85%).

[0304] Except for using intermediates E and F from Table 5 in place of 3-bromo-1,1'-biphenyl and 9-phenyl-9H,9'H-3,3'-dicarbazole in Preparation Example 5, the target compound G in Table 5 was synthesized in the same manner as in Preparation Example 5.

[0305] [Table 5]

[0306]

[0307]

[0308] [Preparation Example 6] Preparation of Compound 4-2

[0309]

[0310] 1) Preparation of compound 4-2-2

[0311] 2-Bromodibenzo[b,d]thiophene (4.2 g, 15.8 mmol), 9-phenyl-9H,9'H-3,3'-dicarbazole (6.5 g, 15.8 mmol), CuI (copper iodide) (3.0 g, 15.8 mmol), trans-1,2-diaminocyclohexane (1.9 mL, 15.8 mmol), and K3PO4 (tripotassium phosphate) (3.3 g, 31.6 mmol) were dissolved in 1,4-dioxane (100 mL) and refluxed for 24 hours. After the reaction was complete, the product was extracted by introducing distilled water and DCM at room temperature, and the solvent was removed using a rotary evaporator after drying the organic layer with MgSO4. The reaction material was purified by column chromatography (DCM:Hex = 1:3) and recrystallized from methanol to obtain the target compound 4-2-2 (7.9 g, 85%).

[0312] 2) Preparation of compound 4-2-1

[0313] 2.5 M n-BuLi (7.4 mL, 18.6 mmol) was added dropwise to a mixture of compound 4-2-1 (8.4 g, 14.3 mmol) and THF (100 mL) at -78 °C, and the mixture was stirred at room temperature for 1 h. Trimethyl borate (4.8 mL, 42.9 mmol) was added dropwise to the reaction mixture, and the result was stirred at room temperature for 2 h. After the reaction was complete, the result was extracted by introducing distilled water and DCM at room temperature, and the solvent was removed using a rotary evaporator after drying the organic layer with MgSO4. The reaction material was purified by column chromatography (DCM:MeOH = 100:3) and recrystallized with DCM to obtain compound 4-2-1 (3.9 g, 70%).

[0314] 3) Preparation of compound 4-2

[0315] Compound 4-2-1 (6.7 g, 10.5 mmol), iodobenzene (2.1 g, 10.5 mmol), Pd(PPh3)4 (606 mg, 0.52 mmol), and K2CO3 (2.9 g, 21.0 mmol) were dissolved in toluene / EtOH / H2O (100 mL / 20 mL / 20 mL) and refluxed for 12 hours. After the reaction was complete, the product was extracted by introducing distilled water and DCM at room temperature, and the solvent was removed using a rotary evaporator after drying the organic layer with MgSO4. The reaction material was purified by column chromatography (DCM:Hex = 1:3) and recrystallized from methanol to obtain the target compound 4-2 (4.9 g, 70%).

[0316] [Preparation Example 7] Preparation of Compound 4-3

[0317] The target compound 4-3 (83%) was obtained in the same manner as in the preparation of compound 4-2, except that 4-iodo-1,1'-biphenyl was used instead of iodobenzene in preparation example 6.

[0318] Compounds other than those described in Preparation Examples 1 to 7 and in Tables 1 to 5 were also prepared in the same manner as in the preparation examples described above.

[0319] The synthetic identification data of the compounds prepared above are described in Tables 6 and 7 below. Table 6 shows the measurements by FD-mass spectrometry (FD-mass field desorption mass spectrometry), and Table 7 shows... 1 Measurements of H NMR (CDCl3, 200 MHz).

[0320] [Table 6]

[0321]

[0322]

[0323]

[0324]

[0325] [Table 7]

[0326]

[0327] [Experimental Example 1]

[0328] 1) Manufacturing organic light-emitting elements

[0329] The glass substrate with a 1,500 angstrom ITO film coated on it was ultrasonically cleaned with distilled water. After cleaning with distilled water, the substrate was ultrasonically cleaned with solvents such as acetone, methanol, and isopropanol, then dried and treated with UVO for 5 minutes in a UV cleaner. The substrate was then transferred to a plasma cleaner (PT) and subjected to plasma treatment under vacuum to remove the ITO work function and residual film. Finally, the substrate was transferred to a thermal deposition apparatus for organic deposition.

[0330] On a transparent ITO electrode (anode), a hole injection layer 2-TNATA (4,4',4"-tris[2-naphthyl(phenyl)amino]triphenylamine) and a hole transfer layer NPB (N,N'-di(1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine) are formed as a common layer.

[0331] A light-emitting layer is then thermally vacuum-deposited on top of the light-emitting layer. As the light-emitting layer, the compounds listed in Table 8 are deposited to a thickness of 400 Å as the host, and the green phosphorescent dopant Ir(ppy)3 is doped to 7% of the deposited thickness of the light-emitting layer. Subsequently, BCP is deposited to a thickness of 60 Å as a hole-blocking layer, and Alq3 is deposited on top of it to a thickness of 200 Å as an electron transfer layer.

[0332] Finally, an electron injection layer is formed on the electron transfer layer by depositing lithium fluoride (LiF) to a thickness of 10 angstroms, and then an aluminum (Al) cathode is formed on the electron injection layer by depositing an aluminum (Al) cathode to a thickness of 1,200 angstroms, thus fabricating an organic electroluminescent element.

[0333] At the same time, in 10 -8 Up to 10 -6 The process involves vacuum sublimation purification of all organic compounds required for OLED manufacturing, for each material intended to be used in OLED production.

[0334] 2) Evaluation of organic light-emitting elements

[0335] For each of the organic electroluminescent elements manufactured as described above, the electroluminescence (EL) properties were measured using an M7000 manufactured by McScience Inc., and the measurement results were then used to measure the lifespan at a standard luminance of 6,000 candela per square meter (cd / m²) using a lifetime measurement system (M6000) manufactured by McScience Inc. 2 T at that time 90 .

[0336] The results of measurements of the driving voltage, luminous efficiency, color coordinates (CIE), and lifespan of the organic light-emitting element manufactured according to this disclosure are shown in Table 8 below.

[0337] [Comparative Example 1]

[0338]

[0339] [Comparative Example 2]

[0340]

[0341] [Comparative Example 3]

[0342]

[0343] [Comparative Example 4]

[0344]

[0345] [Comparative Example 5]

[0346]

[0347] [Comparative Example 6]

[0348]

[0349] [Comparative Example 7]

[0350]

[0351] [Comparative Example 8]

[0352]

[0353] [Comparative Example 9]

[0354]

[0355] [Table 8]

[0356]

[0357] As can be seen from the results in Table 8, it has been confirmed that, compared with Comparative Examples 1 to 15, the organic electroluminescent element using the compound of Chemical Formula 1 of this disclosure as the light-emitting layer material has significantly enhanced driving voltage, luminous efficiency and lifespan.

[0358] Specifically, when the heteroaryl group is bonded to Formula 1 at the same position as in Comparative Example 1, the LUMO orbital is broadened. Furthermore, when the ortho-heteroaryl amine is directly bonded, as in Comparative Examples 4 and 5, the HOMO / LUMO orbitals overlap. This is disadvantageous compared to the luminescent layer material of this disclosure, which is stable in charge balance through bonding at different positions.

[0359] [Experimental Example 2]

[0360] 1) Manufacturing organic light-emitting elements

[0361] The glass substrate with a 1,500 angstrom ITO film coated on it was ultrasonically cleaned with distilled water. After cleaning with distilled water, the substrate was ultrasonically cleaned with solvents such as acetone, methanol, and isopropanol, then dried, and treated with UVO 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. Finally, the substrate was transferred to a thermal deposition apparatus for organic deposition.

[0362] On a transparent ITO electrode (anode), a hole injection layer 2-TNATA (4,4',4"-tris[2-naphthyl(phenyl)amino]triphenylamine) and a hole transfer layer NPB (N,N'-di(1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine) are formed as a common layer.

[0363] The following describes the thermal vacuum deposition of a light-emitting layer. As the light-emitting layer, two types of compounds described in Table 9 below are premixed and then deposited to a thickness of 400 Å in a supply source as the host, and a green phosphorescent dopant Ir(ppy)3 is doped to 7% of the deposited thickness of the light-emitting layer. Subsequently, BCP is deposited to a thickness of 60 Å as a hole-blocking layer, and Alq3 is deposited to a thickness of 200 Å on top of it as an electron transfer layer. Finally, an electron injection layer is formed on the electron transfer layer by depositing lithium fluoride (LiF) to a thickness of 10 Å, and then a cathode is formed on the electron injection layer by depositing an aluminum (Al) cathode to a thickness of 1200 Å, thus fabricating an organic electroluminescent device.

[0364] At the same time, in 10 -8 Up to 10 -6The process involves vacuum sublimation purification of all organic compounds required for OLED manufacturing, for each material intended to be used in OLED production.

[0365] 2) Evaluation of organic light-emitting elements

[0366] For each of the organic electroluminescent elements manufactured as described above, the electroluminescence (EL) properties were measured using an M7000 manufactured by Microscience Corporation, and the To was measured using a lifetime measurement system (M6000) manufactured by Microscience Corporation at a standard luminance of 6,000 candela / m². 90 .

[0367] The driving voltage, luminous efficacy, color coordinates (CIE), and lifetime (T) of the organic light-emitting element manufactured according to this disclosure are measured. 90 The results are shown in Table 9 below.

[0368] [Table 9]

[0369]

[0370]

[0371] As can be seen from the results in Tables 8 and 9, a better effect on efficiency and lifespan is obtained when both compounds of Formula 1 and Formula 3 are contained. Such results lead to the prediction that the complexation phenomenon will occur when both compounds are contained.

[0372] Excitation complexation is the release of energy with the magnitudes of the HOMO level of the donor (p-host) and the LUMO level of the acceptor (n-host) due to electron exchange between two molecules. When excitation complexation occurs between two molecules, reverse intersystem crossing (RISC) occurs, and therefore, the internal quantum efficiency of fluorescence can be increased to up to 100%. When a donor (p-host) with good hole transfer capability and an acceptor (n-host) with good electron transfer capability are used as the hosts of the emitting layer, holes are injected into the p-host and electrons are injected into the n-host, and therefore, the driving voltage can be reduced, which ultimately helps to enhance the lifetime. In the disclosure of this application, a heterocyclic compound of Formula 1 and a compound of Formula 3 are used as the hosts of the emitting layer, and it is confirmed that when the compound of Formula 3 is used as the donor and the heterocyclic compound of Formula 1 is used as the acceptor, excellent device properties are obtained.

Claims

1. A heterocyclic compound having the following chemical formula 1: [Chemical Formula 1] In chemical formula 1, X1 to X3 are each independently N or CH. At least one of X1 to X3 is N, and N-Het is represented by the following chemical formulas: N-1 or N-2. [Chemical formula N-1] [Chemical formula N-2] In chemical formulas N-1 and N-2 R1 is hydrogen, deuterium, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group. R2 and R3 are each independently hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl. Ar can be a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted triphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted phenanthryl, a substituted or unsubstituted triphenylene, or a substituted or unsubstituted pyrene. The phrase "substituted or unsubstituted" means substituted with one or more substituents selected from the group consisting of: deuterium, or C1 to C20 alkyl, or unsubstituted, and Het1 is represented by the chemical formula H-1, and Het2 is represented by the chemical formula H-2. [Chemical formula H-1] [Chemical formula H-2] In chemical formulas H-1 and H-2, Y1 and Y2 are each independently O or S. A1 to A4 and B1 to B4 are each independently bonded to chemical formula 1, either as hydrogen or deuterium, and Formula 1 is bonded to any of A1 to A4 of Formula H-1 and any of B1 to B4 of Formula H-2, denoted by Am-Bn, where m and n are 1, 2, 3 or 4 respectively, and m and n are different.

2. The heterocyclic compound according to claim 1, wherein X1 to X3 are N.

3. A heterocyclic compound, represented by any of the following compounds:

4. An organic light-emitting element, comprising: First electrode; Second electrode; as well as An organic material layer is disposed between the first electrode and the second electrode. The organic material layer thereof comprises a heterocyclic compound as described in any one of claims 1 to 3.

5. The organic light-emitting element according to claim 4, wherein the organic material layer comprises a light-emitting layer, and the light-emitting layer comprises the heterocyclic compound.

6. The organic light-emitting element according to claim 4, wherein the organic material layer comprises a light-emitting layer, the light-emitting layer comprises a host, and the host comprises the heterocyclic compound.

7. The organic light-emitting element according to claim 5, wherein the light-emitting layer further comprises a compound of formula 3: [Chemical Formula 3] In chemical formula 3, R31 and R32 are each independently hydrogen, deuterium, halogroup, substituted or unsubstituted C1 to C60 alkyl, substituted or unsubstituted C3 to C60 cycloalkyl, substituted or unsubstituted C6 to C60 aryl, or substituted or unsubstituted C2 to C60 heteroaryl. Ar31 and Ar32 are each independently a substituted or unsubstituted C6 to C60 aryl group, or a substituted or unsubstituted C2 to C60 heteroaryl group. r31 is an integer from 0 to 4, and when it is 2 or greater than 2, R31 is either the same or different from each other. r32 is an integer from 0 to 4, and when it is 2 or greater than 2, R32 is either the same or different from each other. The term "substituted or unsubstituted" means substituted by one or more substituents selected from the group consisting of: deuterium, cyano, Si(R101)(R102)(R103), C1 to C20 alkyl, C6 to C25 aryl, or C3 to C25 heteroaryl containing O or S, or unsubstituted. R101 to R103 are independently hydrogen, deuterium, C1 to C20 alkyl, or C6 to C25 aryl.

8. The organic light-emitting element according to claim 7, wherein chemical formula 3 is represented by any of the following compounds:

9. A composition for forming an organic material layer, the composition comprising: The heterocyclic compound as described in claim 1; as well as The following compounds have chemical formula 3: [Chemical Formula 3] In chemical formula 3, R31 and R32 are each independently hydrogen, deuterium, halogroup, substituted or unsubstituted C1 to C60 alkyl, substituted or unsubstituted C3 to C60 cycloalkyl, substituted or unsubstituted C6 to C60 aryl, or substituted or unsubstituted C2 to C60 heteroaryl. Ar31 and Ar32 are each independently a substituted or unsubstituted C6 to C60 aryl group, or a substituted or unsubstituted C2 to C60 heteroaryl group; r31 is an integer from 0 to 4, and when it is 2 or greater than 2, R31 is the same or different from each other; r32 is an integer from 0 to 4, and when it is 2 or greater than 2, R32 is either the same or different from each other. The term "substituted or unsubstituted" means substituted by one or more substituents selected from the group consisting of: deuterium, cyano, Si(R101)(R102)(R103), C1 to C20 alkyl, C6 to C25 aryl, or C3 to C25 heteroaryl containing O or S, or unsubstituted. R101 to R103 are independently hydrogen, deuterium, C1 to C20 alkyl, or C6 to C25 aryl.

10. The composition for forming an organic material layer according to claim 9, wherein the heterocyclic compound has a weight ratio of 1:10 to 10:1 with the compound of formula 3.

Images