Organic light emitting element and composition for forming organic material layer

Abstract

The present specification relates to an organic light emitting element and a composition for forming an organic material layer. The organic light emitting element includes a first electrode, a second electrode, and an organic material layer disposed between the first electrode and the second electrode. The organic material layer includes a compound of the following Chemical Formula 1 and a compound of the following Chemical Formula 2.[Chemical Formula 1][Chemical Formula 2]

Description

[0001] This specification claims priority and benefits to Korean Patent Application No. 10-2020-0102343, filed on August 14, 2020, with the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference. Technical Field

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

[0003] Electroluminescent elements are self-emissive display elements with 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 this structure, electrons and holes injected from the two electrodes combine and pair in the organic thin film, and emit light as they annihilate. The organic thin film can be formed as a single layer or multiple layers as needed.

[0005] Organic thin film materials can possess light-emitting properties as needed. For example, as materials for organic thin films, compounds capable of forming a light-emitting layer independently can be used, or compounds capable of functioning as the host or dopant of a light-emitting layer based on a host dopant can be used. In addition, compounds capable of functioning as hole injection, hole transport, electron blocking, and electron transport can also be used as materials for organic thin films.

[0006] To improve the performance, lifespan, or efficiency of organic light-emitting elements, there has always been a need to develop organic thin film materials. Summary of the Invention

[0007] Technical issues

[0008] This specification aims to provide an organic light-emitting element and a composition for forming an organic material layer.

[0009] Technical solutions

[0010] One embodiment of this specification provides an organic light-emitting element, the organic light-emitting element comprising: a first electrode; a second electrode; and an organic material layer disposed between the first electrode and the second electrode, wherein the organic material layer comprises a compound of chemical formula 1 and a compound of chemical formula 2.

[0011] [Chemical Formula 1]

[0012]

[0013] In chemical formula 1,

[0014] L1 to L3 may be identical or different from each other, and each is independently a direct bond; C6 to C60 arylene; monocyclic heteroarylene containing N; or tricyclic or higher heteroarylene containing O.

[0015] Ar1 and Ar2 may be the same as or different from each other, and each is independently a substituted or unsubstituted C1 to C60 alkyl; a substituted or unsubstituted C3 to C60 cycloalkyl; a substituted or unsubstituted C6 to C60 aryl; or a substituted or unsubstituted C2 to C60 heteroaryl, and

[0016] N-Het is a C2 to C60 heteroaryl group, either substituted or unsubstituted, containing N.

[0017] [Chemical Formula 2]

[0018]

[0019] In chemical formula 2,

[0020] L21 and L22 may be the same as or different from each other, and each is an independent direct bond; C6 to C60 arylene; or C2 to C60 heteroarylene.

[0021] Z21 and Z22 may be identical or different from each other, and each is independently a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0022] At least one of Z21 and Z22 is a C2 to C60 heteroaryl group, either substituted or unsubstituted, containing N.

[0023] R21 and R22 may be the same as or different from each other, and each is independently hydrogen; deuterium; halogen group; cyano group; substituted or unsubstituted C1 to C60 alkyl group; substituted or unsubstituted C6 to C60 aryl group; or substituted or unsubstituted C2 to C60 heteroaryl group.

[0024] r21 is an integer from 0 to 4.

[0025] r22 is an integer from 0 to 6, and

[0026] When r21 and r22 are each 2 or greater than 2, the substituents in the parentheses are the same or different from each other.

[0027] Another embodiment of this specification provides a composition for forming an organic material layer, the composition comprising a compound of chemical formula 1 and a compound of chemical formula 2.

[0028] Beneficial effects

[0029] The organic light-emitting element described in this specification includes an organic material layer containing compounds of Formula 1 and Formula 2, and the organic material layer containing the compounds can be a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, a charge generation layer, etc. In particular, the organic material layer containing the compounds can be the light-emitting layer of the organic light-emitting element.

[0030] When compounds of Formula 1 and Formula 2 are used together as materials for the light-emitting layer of an organic light-emitting element, the driving voltage can be reduced, the luminous efficiency can be improved, and the lifespan characteristics of the element can be enhanced.

[0031] Specifically, by using compounds of Formula 1 containing N-heteroaryl and amine groups and compounds of Formula 2 having naphthobenzofuran as the core structure and being replaced by N-heteroaryl groups as the host materials of the luminescent layer, the driving voltage, luminous efficiency and lifetime characteristics are improved by enhancing the mobility of electrons and holes and enhancing the charge balance. Attached Figure Description

[0032] Figures 1 to 3 These are diagrams illustrating the stacked structure of an organic light-emitting element according to one embodiment of this specification.

[0033] Explanation of icon numbers

[0034] 100: substrate;

[0035] 200: Anode;

[0036] 300: Organic material layer;

[0037] 301: Hole injection layer;

[0038] 302: Hole transport layer;

[0039] 303: Emissive layer;

[0040] 304: Hole-blocking layer;

[0041] 305: Electron transport layer;

[0042] 306: Electron injection layer;

[0043] 400: Cathode. Detailed Implementation

[0044] This instruction manual will be described in more detail below.

[0045] In this specification, the description of a particular part "including" a particular component means that it may further include other components, and does not exclude other components, unless specifically stated to the contrary.

[0046] The term "substitution" refers to the replacement of a hydrogen atom bonded to a carbon atom of a compound with another substituent, and the position of substitution is not limited, as long as it is the position where the hydrogen atom is substituted (i.e., the position where the substituent can substitute), and when two or more substituents are substituted, the two or more substituents may be the same as or different from each other.

[0047] In this specification, "substituted or unsubstituted" means substituted with 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 unsubstituted, or substituted with a substituent connected to two or more substituents selected from the above substituents, or unsubstituted.

[0048] In this specification, "where no substituent is specified in the chemical formula or compound structure" refers to the bond between hydrogen and carbon atoms. However, due to deuterium ( 2 H is an isotope of hydrogen, therefore some hydrogen atoms can be deuterium.

[0049] In one embodiment of this application, "where no substituent is specified in the chemical formula or compound structure" may mean that all positions that can serve as substituents may be hydrogen or deuterium. In other words, since deuterium is an isotope of hydrogen, some hydrogen atoms may be deuterium as an isotope, and in this document, the deuterium content may be 0% to 100%.

[0050] In one embodiment of this application, when "no substituents are specified in the chemical formula or compound structure", hydrogen and deuterium can 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).

[0051] 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, and can be represented as hydrogen-2, and its element symbol can also be written as D or 2 H.

[0052] 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.

[0053] In one embodiment of this application, when the total number of substituents that a basic compound may have is defined as T1, and the number of a particular substituent is defined as T2, the meaning of the content T% of the particular substituent can be defined as T2 / T1×100=T.

[0054] In other words, in one instance, in the case of... The 20% deuterium content in a phenyl group indicates that the total number of substituents that the phenyl group may have is 5 (T1 in the formula), and the number of deuterium substituents is 1 (T2 in the formula). In other words, a 20% deuterium content in a phenyl group can be represented by the following structural formula.

[0055]

[0056] Furthermore, in one embodiment of this application, "the deuterium content of the phenyl is 0%" may refer to a phenyl that does not contain deuterium atoms, that is, a phenyl with 5 hydrogen atoms.

[0057] In this specification, halogen may be fluorine, chlorine, bromine or iodine.

[0058] In this specification, alkyl groups include straight-chain or branched alkyl groups 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 methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tributyl, dibutyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, tripentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, octyl, n-octyl, trioctyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1-dimethylpropyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, etc., but are not limited to these.

[0059] In this specification, alkenyl groups include straight-chain or branched alkenyl groups and may be further substituted with other substituents. The number of carbon atoms in an alkenyl group may be 2 to 60, 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, styrene, etc., but are not limited thereto.

[0060] In this specification, the alkynyl group includes straight-chain or branched alkynyl groups 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.

[0061] In this specification, cycloalkyl includes monocyclic or polycyclic cycloalkyl groups having 3 to 60 carbon atoms, and may be further substituted with other substituents. Polycyclic refers to a group in which the cycloalkyl group is directly attached 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, etc., but are not limited thereto.

[0062] In this specification, heterocyclic alkyl groups include O, S, Se, N, or Si as heteroatoms, and include monocyclic or polycyclic heterocyclic alkyl groups having 2 to 60 carbon atoms, and may be further substituted with other substituents. Polycyclic refers to a group in which the heterocyclic alkyl group is directly attached to or fused with other cyclic groups. 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.

[0063] In this specification, aryl groups include monocyclic or polycyclic aryl groups having 6 to 60 carbon atoms, and may be further substituted with other substituents. Polycyclic refers to a group in which the aryl group is directly attached to or fused with other cyclic groups. Other cyclic groups may be aryl, but may also be different types of cyclic groups, such as cycloalkyl, heterocycloalkyl, and heteroaryl. Aryl groups include spirocyclic groups. 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 higher, 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, terphenyl, naphthyl, anthracene, etc. The group includes, but is not limited to, phenanthrene, perylene, fluoranthracene, dithionylene, fenylene, pyrene, fused tetraphenyl, fused pentaphenyl, fluorenyl, indene, acenaphthene, benzofluorenyl, spirodifluorenyl, 2,3-dihydro-1H-indene, and its fused cyclic groups.

[0064] In this specification, terphenyl may be selected from the following structures.

[0065]

[0066] In this specification, the fluorene group may be substituted, and adjacent substituents may bond to each other to form a ring.

[0067] When the fluorene group is substituted, it may include However, the structure is not limited to this.

[0068] In this specification, benzo[a]fluorenyl is a group in which a benzene ring is fused to a fluorenyl group, and may be further substituted by other substituents.

[0069] In this specification, heteroaryl groups include O, S, SO2, Se, N, or Si as heteroatoms, and include monocyclic or polycyclic heteroaryl groups, which may be further substituted with other substituents. Polycyclic here means a group in which the heteroaryl group is directly attached to or fused with other cyclic groups. Other cyclic groups here 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 higher, 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, furazolyl, oxadiazolyl, thiazolyl, dithiazolyl, tetrazolyl, pyranyl, thiaranyl, diazinyl, oxazinyl, thiazolyl, dioxinyl group, triazinyl, tetrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, isoquinazolinyl, quinazolinyl, quinazolinyl group), naphthidyl, acridineyl, phenanthridineyl, imidazopyridyl, diazanaphthyl, triazaindyl, indoleyl, benzothiazolyl, benzoxazolyl, benzoimidazolyl, benzothiopheneyl, benzofuranyl, dibenzothiopheneyl, dibenzofuranyl, benzonaphthiopheneyl, naphthobenzofuranyl, carbazoleyl, benzocarbazoleyl, dibenzocarbazoleyl, phenazinyl, dibenzosiloxanediyl, spirocyclodibenzosiloxanediyl, dihydrophenazinyl, phenanthridineyl, imidazopyridyl, thiopheneyl, indole[2,3- a] Carbazolyl, indolo[2,3-b]carbazolyl, indololinyl, 10,11-dihydro-dibenzo[b,f]azacycloheptenyl, 9,10-dihydroacridyl, phenazinyl, phenazinyl, phthalazinyl, naphridinyl, 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]dihydroindolyl, benzofuran[2,3-d]pyrimidinyl; benzothieno[2,3-d]pyrimidinyl;Benzofurano[2,3-a]carbazole, benzothieno[2,3-a]carbazole, 1,3-dihydroindolo[2,3-a]carbazole, benzofurano[3,2-a]carbazole, benzothieno[3,2-a]carbazole, 1,3-dihydroindolo[3,2-a]carbazole, benzofurano[2,3-b]carbazole, benzothieno[2,3-b]carbazole, 1,3-dihydroindolo[2,3-b]carbazole, benzofurano[3,2-b]carbazole, benzothieno[3,2-b]carbazole, 1,3-dihydroindolo[3,2-b]carbazole, benzofurano[2,3-c] Carbazolyl, benzothieno[2,3-c]carbazolyl, 1,3-dihydroindolo[2,3-c]carbazolyl, benzofurano[3,2-c]carbazolyl, benzothieno[3,2-c]carbazolyl, 1,3-dihydroindolo[3,2-c]carbazolyl, 1,3-dihydroindo[2,1-b]carbazolyl, 5,11-dihydroindo[1,2-b]carbazolyl, 5,12-dihydroindo[1,2-c]carbazolyl, 5,8-dihydroindo[2,1-c]carbazolyl, 7,12-dihydroindo[1,2-a]carbazolyl, 11,12-dihydroindo[2,1-a]carbazolyl, etc., but not limited to these.

[0070] In this specification, the naphthobenzofuranyl group is represented by any of the following structures.

[0071]

[0072] In this specification, silyl is a substituent comprising Si atoms directly linked as a free radical, 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; halogen; alkyl; alkenyl; alkoxy; cycloalkyl; aryl; and heteroaryl. Specific examples of silyl groups may include, but are not limited to, trimethylsilyl, triethylsilyl, tributyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, etc.

[0073] In this specification, phosphine oxide is represented by -P(=O)(R104)(R105), and R104 and R105 may each be independently a substituent formed from at least one of the following: alkyl; alkenyl; alkoxy; cycloalkyl; aryl; and heteroaryl. Examples of phosphine oxide may include, but are not limited to, dimethylphosphine oxide, diphenylphosphine oxide, and dinaphthylphosphine oxide.

[0074] In this specification, the amino group may be selected from the group consisting of monoalkylamino; monoarylamino; monoheteroarylamino; -NH2; dialkylamino; diarylamino; diheteroarylamino; alkylarylamino; alkylheteroarylamino; and arylheteroarylamino, and although not particularly limited thereto, the number of carbon atoms is preferably from 1 to 30. Specific examples of the amino group may include methylamino, dimethylamino, ethylamino, diethylamino, phenylamino, naphthylamino, biphenylamino, diphenylamino, anthraceneamino, 9-methyl-anthraylamino, diphenylamino, phenylnaphthylamino, xylylamino, phenyltolylamino, triphenylamino, biphenylnaphthylamino, phenylbiphenylamino, biphenylfluorenylamino, phenylbitriphenylamino, biphenylbitriphenylamino, etc., but are not limited thereto.

[0075] In this specification, except that the aryl group is a divalent group, the above examples of aryl groups can be applied to aryl groups.

[0076] In this specification, except that the heteroaryl group is a divalent group, the above examples of heteroaryl groups can be applied to heteroaryl groups.

[0077] In this specification, the examples of aryl and heteroaryl groups described above can be applied to aryl rings and heterocycles, respectively.

[0078] An organic light-emitting element according to one embodiment of this specification includes an organic material layer comprising a compound of chemical formula 1 and a compound of chemical formula 2.

[0079] In one embodiment of this specification, L1 to L3 of Formula 1 may be the same as or different from each other, and each is independently a direct bond; C6 to C60 arylene; monocyclic heteroarylene containing N; or tricyclic or higher heteroarylene containing O.

[0080] In one embodiment of this specification, L1 to L3 may be the same as or different from each other, and each is independently a direct bond; C6 to C60 arylene; C2 to C5 monocyclic heteroarylene containing N; or C12 to C60 tricyclic or higher heteroarylene containing O.

[0081] In one embodiment of this specification, L1 to L3 may be the same as or different from each other, and each is independently a direct bond; C6 to C30 arylene; a monocyclic heteroarylene containing N; or a tricyclic or higher heteroarylene containing O.

[0082] In one embodiment of this specification, L1 to L3 may be the same as or different from each other, and may each be independently a direct bond; phenylene; biphenylene; divalent pyridyl; divalent dibenzofuranyl; or divalent naphthobenzofuranyl.

[0083] In one embodiment of this specification, L1 to L3 may all be direct keys.

[0084] In one embodiment of this specification, L1 and L3 may be the same as or different from each other, and may each be a direct bond; a C6 to C60 arylene; or a monocyclic heteroarylene containing N.

[0085] In one embodiment of this specification, L1 and L3 may be the same as or different from each other, and may each be a direct bond; a C6 to C30 arylene; or a monocyclic heteroarylene containing N.

[0086] In one embodiment of this specification, L1 and L3 may be the same as or different from each other, and may each be a direct bond; phenylene; biphenylene; or divalent pyridyl.

[0087] In one embodiment of this specification, L2 may be a direct bond; or a tricyclic or higher heteroaryl group containing O.

[0088] In one embodiment of this specification, L2 may be a direct bond; a divalent dibenzofuranyl; or a divalent naphthobenzofuranyl.

[0089] In one embodiment of this specification, when L2 is a divalent dibenzofuranyl or a divalent naphthobenzofuranyl, chemical formula 1 may be represented by any of the following chemical formulas 1-A to 1-C.

[0090] [Chemical Formula 1-A]

[0091]

[0092] [Chemical Formula 1-B]

[0093]

[0094] [Chemical Formula 1-C]

[0095]

[0096] In chemical formulas 1-A to 1-C,

[0097] Each substituent has the same definition as in Formula 1.

[0098] In one embodiment of this specification, when chemical formula 1 is represented by chemical formula 1-C, the two substituents may substitute for each other at the meta position.

[0099] In one embodiment of this specification, Ar1 and Ar2 of Formula 1 may be the same as or different from each other, and each is independently a substituted or unsubstituted C1 to C60 alkyl; a substituted or unsubstituted C3 to C60 cycloalkyl; a substituted or unsubstituted C6 to C60 aryl; or a substituted or unsubstituted C2 to C60 heteroaryl.

[0100] In one embodiment of this specification, Ar1 and Ar2 may be the same as or different from each other, and each is independently a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0101] In one embodiment of this specification, Ar1 and Ar2 may be the same as or different from each other, and each is independently 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, Ar1 and Ar2 may be the same as or different from each other, and each is independently a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0103] In one embodiment of this specification, Ar1 and Ar2 may be the same as or different from each other, and each may independently be a substituted or unsubstituted phenyl; a substituted or unsubstituted biphenyl; a substituted or unsubstituted terphenyl; a substituted or unsubstituted naphthyl; a substituted or unsubstituted fluorenyl; a substituted or unsubstituted dibenzofuranyl; a substituted or unsubstituted dibenzothiophenyl; or a substituted or unsubstituted carbazoleyl.

[0104] In one embodiment of this specification, Ar1 and Ar2 may be the same as or different from each other, and each is independently an unsubstituted or aryl- or heteroaryl-substituted phenyl; biphenyl; terphenyl; naphthyl; dimethylfluorenyl; dibenzofuranyl; dibenzothiopheneyl; or an unsubstituted or aryl-substituted carbazoleyl.

[0105] In one embodiment of this specification, N-Het of Formula 1 is a C2 to C60 heteroaryl group that is substituted or unsubstituted and contains N.

[0106] In one embodiment of this specification, N-Het is a C2 to C40 heteroaryl group that is substituted or unsubstituted and contains N.

[0107] In one embodiment of this specification, N-Het is a C2 to C20 heteroaryl group that is substituted or unsubstituted and contains N.

[0108] In one embodiment of this specification, N-Het is a substituted or unsubstituted C2 to C40 heteroaryl group containing -N=.

[0109] In one embodiment of this specification, N-Het of Formula 1 is a substituted or unsubstituted C2 to C60 heteroaryl group containing -N=.

[0110] In one embodiment of this specification, N-Het is a substituted or unsubstituted C2 to C20 heteroaryl group containing -N=.

[0111] In one embodiment of this specification, N-Het is a substituted or unsubstituted C2 to C40 heteroaryl group containing -N=.

[0112] In one embodiment of this specification, -N= specifically refers to a double bond comprising carbon and nitrogen (C=N). For example, pyrimidines, pyridines, triazines, etc., contain -N=, while carbazole does not contain -N=.

[0113] In one embodiment of this specification, N-Het may be represented by any of the following chemical formulas 1-1 to 1-4.

[0114] [Chemical Formula 1-1]

[0115]

[0116] [Chemical Formula 1-2]

[0117]

[0118] [Chemical Formulas 1-3]

[0119]

[0120] [Chemical Formulas 1-4]

[0121]

[0122] In chemical formulas 1-1 to 1-4

[0123] X1 to X4 are each N or CR.

[0124] At least one of X1 to X3 is N.

[0125] A through C may be identical or different from each other, and each is independently a substituted or unsubstituted monocyclic or polycyclic C6 to C60 aryl ring; or a substituted or unsubstituted monocyclic or polycyclic C2 to C60 heterocyclic ring, and

[0126] R and R1 to R4 may be the same as or different from each other, and each is independently hydrogen; deuterium; halogen group; cyano group; substituted or unsubstituted C1 to C60 alkyl group; substituted or unsubstituted C6 to C60 aryl group; or substituted or unsubstituted C2 to C60 heteroaryl group.

[0127] In one embodiment of this specification, X1 to X3 of chemical formula 1-1 are each N or CR, and at least one of X1 to X3 is N.

[0128] In one embodiment of this specification, at least two of X1 to X3 are N.

[0129] In one embodiment of this specification, X1 and X2 are N, X3 is CR, and R may be hydrogen.

[0130] In one embodiment of this specification, X1 and X3 are N, X2 is CR, and R may be hydrogen.

[0131] In one embodiment of this specification, X1 to X3 may all be N.

[0132] In one embodiment of this specification, R1 and R2 of Formula 1-1 may be the same as or different from each other, and each is independently a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0133] In one embodiment of this specification, R1 and R2 may be the same as or different from each other, and each is independently a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group.

[0134] In one embodiment of this specification, R1 and R2 may be the same as or different from each other, and each is independently a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0135] In one embodiment of this specification, R1 and R2 may be the same as or different from each other, and may each be independently a substituted or unsubstituted phenyl; a substituted or unsubstituted biphenyl; a substituted or unsubstituted naphthyl; a substituted or unsubstituted fluorenyl; a substituted or unsubstituted dibenzofuranyl; or a substituted or unsubstituted dibenzothiopheneyl.

[0136] In one embodiment of this specification, R1 and R2 may be the same as or different from each other, and may each be independently an unsubstituted or aryl- or heteroaryl-substituted phenyl; a substituted or unsubstituted biphenyl; a substituted or unsubstituted naphthyl; an unsubstituted or alkyl-substituted fluorenyl; a substituted or unsubstituted dibenzofuranyl; or a substituted or unsubstituted dibenzothiopheneyl.

[0137] In one embodiment of this specification, R1 and R2 may be the same as or different from each other, and may each be independently an unsubstituted or naphthyl- or carbazolyl-substituted phenyl; biphenyl; naphthyl; dimethylfluorenyl; dibenzofuranyl; or dibenzothiopheneyl.

[0138] In one embodiment of this specification, X4 in chemical formulas 1-2 is N or CR.

[0139] In one embodiment of this specification, X4 may be N.

[0140] In one embodiment of this specification, X4 may be CR, and R may be hydrogen.

[0141] In one embodiment of this specification, A in chemical formulas 1-2 is a substituted or unsubstituted monocyclic aryl ring; or a substituted or unsubstituted polycyclic heterocycle.

[0142] In one embodiment of this specification, A may be a substituted or unsubstituted benzene ring; a substituted or unsubstituted quinoline ring; a substituted or unsubstituted indole ring; a substituted or unsubstituted benzofuran ring; or a substituted or unsubstituted benzothiophene ring.

[0143] In one embodiment of this specification, A may be a benzene ring; a quinoline ring; an aryl-substituted indole ring; a benzofuran ring; or a benzothiophene ring.

[0144] In one embodiment of this specification, R3 in formulas 1-2 is hydrogen; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0145] In one embodiment of this specification, R3 is hydrogen; a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0146] In one embodiment of this specification, R3 may be hydrogen; a substituted or unsubstituted phenyl; a substituted or unsubstituted biphenyl; a substituted or unsubstituted naphthyl; a substituted or unsubstituted dibenzofuranyl; a substituted or unsubstituted dibenzothiophenyl; or a substituted or unsubstituted naphthobenzofuranyl.

[0147] In one embodiment of this specification, R3 may be hydrogen; an unsubstituted or aryl-substituted phenyl; a substituted or unsubstituted biphenyl; a substituted or unsubstituted naphthyl; a substituted or unsubstituted dibenzofuranyl; a substituted or unsubstituted dibenzothiophenyl; or a substituted or unsubstituted naphthobenzofuranyl.

[0148] In one embodiment of this specification, R3 may be hydrogen; an unsubstituted or aryl-substituted phenyl group; a biphenyl group; a naphthyl group; a dibenzofuranyl group; a dibenzothiophenyl group; or a naphthobenzofuranyl group.

[0149] In one embodiment of this specification, R3 may be hydrogen; an unsubstituted or naphthyl-substituted phenyl group; biphenyl; naphthyl; dibenzofuranyl; dibenzothiophenyl; or naphthobenzofuranyl.

[0150] In one embodiment of this specification, B in chemical formulas 1-3 may be a substituted or unsubstituted monocyclic aryl ring.

[0151] In one embodiment of this specification, B may be a substituted or unsubstituted benzene ring.

[0152] In one embodiment of this specification, B may be a benzene ring.

[0153] In one embodiment of this specification, R4 of chemical formulas 1-3 may be hydrogen; deuterium; or a substituted or unsubstituted C6 to C60 aryl group.

[0154] In one embodiment of this specification, R4 may be hydrogen; deuterium; or a substituted or unsubstituted C6 to C40 aryl group.

[0155] In one embodiment of this specification, R4 may be hydrogen; deuterium; or a substituted or unsubstituted C6 to C20 aryl group.

[0156] In one embodiment of this specification, R4 may be hydrogen; deuterium; substituted or unsubstituted phenyl; or substituted or unsubstituted biphenyl.

[0157] In one embodiment of this specification, R4 may be hydrogen; deuterium; phenyl; or biphenyl.

[0158] In one embodiment of this specification, the C in chemical formulas 1-4 may be a substituted or unsubstituted monocyclic aryl ring.

[0159] In one embodiment of this specification, C may be a substituted or unsubstituted benzene ring.

[0160] In one embodiment of this specification, C may be a benzene ring.

[0161] In one embodiment of this specification, chemical formula 1 may be represented by any of the following compounds, but is not limited thereto.

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182] In one embodiment of this specification, L21 and L22 of Formula 2 may be the same as or different from each other, and each is independently a direct bond; C6 to C60 arylene; or C2 to C60 heteroarylene.

[0183] In one embodiment of this specification, L21 and L22 may be the same as or different from each other, and each is independently a direct bond; C6 to C40 arylene; or C2 to C40 heteroarylene.

[0184] In one embodiment of this specification, L21 and L22 may be the same as or different from each other, and each is independently a direct bond; C6 to C20 arylene; or C2 to C20 heteroarylene.

[0185] In one embodiment of this specification, L21 and L22 may be the same as or different from each other, and may each be a direct bond; or a C6 to C40 arylene group.

[0186] In one embodiment of this specification, L21 and L22 may be the same as or different from each other, and may each be a direct bond; or a C6 to C20 arylene group.

[0187] In one embodiment of this specification, L21 and L22 may be the same as or different from each other, and may each be a direct bond; phenylene; or naphthylene.

[0188] In one embodiment of this specification, Z21 and Z22 of Formula 2 may be the same as or different from each other, and each is independently a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, and at least one of Z21 and Z22 is a substituted or unsubstituted C2 to C60 heteroaryl group containing N.

[0189] In one embodiment of this specification, Z21 and Z22 may be the same as or different from each other, and each is independently a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group, and at least one of Z21 and Z22 is a substituted or unsubstituted C2 to C40 heteroaryl group containing N.

[0190] In one embodiment of this specification, Z21 and Z22 may be the same as or different from each other, and each is independently a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group, and at least one of Z21 and Z22 is a substituted or unsubstituted C2 to C20 heteroaryl group containing N.

[0191] In one embodiment of this specification, Z21 and Z22 may be the same as or different from each other, and may each independently be a substituted or unsubstituted phenyl; a substituted or unsubstituted biphenyl; a substituted or unsubstituted naphthyl; a substituted or unsubstituted fluorenyl; a substituted or unsubstituted dibenzofuranyl; a substituted or unsubstituted dibenzothiopheneyl; a substituted or unsubstituted pyrimidinyl; a substituted or unsubstituted triazineyl; a substituted or unsubstituted quinazolineyl; a substituted or unsubstituted benzofuranopyrimidinyl; or a substituted or unsubstituted benzothiophenopyrimidinyl, and at least one of Z21 and Z22 may be a substituted or unsubstituted pyrimidinyl; a substituted or unsubstituted triazineyl; a substituted or unsubstituted quinazolineyl; a substituted or unsubstituted benzofuranopyrimidinyl; or a substituted or unsubstituted benzothiophenopyrimidinyl.

[0192] In one embodiment of this specification, Z21 may be a substituted or unsubstituted pyrimidinyl group; a substituted or unsubstituted triazine group; a substituted or unsubstituted quinazoline group; a substituted or unsubstituted benzofuranopyrimidinyl group; or a substituted or unsubstituted benzothiophenopyrimidinyl group.

[0193] In one embodiment of this specification, Z21 may be an unsubstituted or aryl-substituted pyrimidinyl group; an unsubstituted or substituted triazine group; an unsubstituted or substituted quinazolinyl group; an unsubstituted or substituted benzofuran-pyrimidinyl group; or an unsubstituted or substituted benzothiophene-pyrimidinyl group.

[0194] In one embodiment of this specification, Z22 may be a substituted or unsubstituted phenyl; a substituted or unsubstituted biphenyl; a substituted or unsubstituted naphthyl; a substituted or unsubstituted fluorenyl; a substituted or unsubstituted dibenzofuranyl; or a substituted or unsubstituted dibenzothiopheneyl.

[0195] In one embodiment of this specification, Z22 may be an unsubstituted or aryl-substituted phenyl; biphenyl; an unsubstituted or aryl-substituted naphthyl; an unsubstituted or alkyl-substituted fluorenyl; dibenzofuranyl; or dibenzothiopheneyl.

[0196] In one embodiment of this specification, R21 and R22 of Formula 2 may be the same as or different from each other, and each is independently hydrogen; deuterium; halogen group; cyano group; substituted or unsubstituted C1 to C60 alkyl group; substituted or unsubstituted C6 to C60 aryl group; or substituted or unsubstituted C2 to C60 heteroaryl group, or adjacent groups may be bonded to each other to form a substituted or unsubstituted C2 to C60 ring.

[0197] In one embodiment of this specification, R21 may be hydrogen; deuterium; halogen group; cyano group; substituted or unsubstituted C1 to C20 alkyl group; substituted or unsubstituted C6 to C30 aryl group; or substituted or unsubstituted C2 to C30 heteroaryl group.

[0198] In one embodiment of this specification, R22 is hydrogen; deuterium; halogen group; cyano group; substituted or unsubstituted C1 to C20 alkyl group; substituted or unsubstituted C6 to C20 aryl group; or substituted or unsubstituted C2 to C20 heteroaryl group, or adjacent groups may be bonded to each other to form a substituted or unsubstituted C2 to C20 ring.

[0199] In one embodiment of this specification, R22 is hydrogen; deuterium; halogen group; cyano group; substituted or unsubstituted C1 to C20 alkyl group; substituted or unsubstituted C6 to C20 aryl group; or substituted or unsubstituted C2 to C20 heteroaryl group, or adjacent groups may be bonded to each other to form a C2 to C20 ring.

[0200] In one embodiment of this specification, R22 is hydrogen; deuterium; halogen group; cyano group; substituted or unsubstituted C1 to C20 alkyl group; substituted or unsubstituted C6 to C20 aryl group; or substituted or unsubstituted C2 to C20 heteroaryl group, or adjacent groups may be bonded to each other to form a benzene ring.

[0201] In one embodiment of this specification, R21 and R22 may be the same as or different from each other, and may each be hydrogen or deuterium independently.

[0202] In one embodiment of this specification, in chemical formula 2, r21 is an integer from 0 to 4, and r22 is an integer from 0 to 6.

[0203] In one embodiment of this specification, in chemical formula 2, r21 is an integer from 1 to 4, and r22 is an integer from 1 to 6.

[0204] In one embodiment of this specification, chemical formula 2 is represented by the following chemical formula 2-1.

[0205] [Chemical Formula 2-1]

[0206]

[0207] In chemical formula 2-1,

[0208] Each substituent has the same definition as in Formula 2.

[0209] In one embodiment of this specification, chemical formula 2 may be represented by the following chemical formula 2-2.

[0210] [Chemical Formula 2-2]

[0211]

[0212] In chemical formula 2-2,

[0213] Each substituent has the same definition as in Formula 2.

[0214] In one embodiment of this specification, chemical formula 2 may be represented by any of the following compounds, but is not limited thereto.

[0215]

[0216]

[0217]

[0218]

[0219] Furthermore, by introducing various substituents into the structure of Formula 1, compounds possessing the unique properties of the introduced substituents can be synthesized. For example, by introducing substituents commonly used as hole injection layer materials, hole transport layer materials, light-emitting layer materials, electron transport 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.

[0220] Furthermore, by introducing various substituents into the structure of Formula 1, the band gap can be precisely controlled, while simultaneously enhancing the properties at the interface between organic materials, and the application of the materials can be diversified.

[0221] In one embodiment of this specification, the organic material layer includes a light-emitting layer, and the light-emitting layer comprises a compound of formula 1 and a compound of formula 2.

[0222] In one embodiment of this specification, the organic material layer includes a light-emitting layer, the light-emitting layer comprising a host material, and the host material comprising a compound of formula 1 and a compound of formula 2.

[0223] In one embodiment of this specification, the first electrode may be an anode and the second electrode may be a cathode.

[0224] In another embodiment of this specification, the first electrode may be a cathode, and the second electrode may be an anode.

[0225] According to one embodiment of this specification, the organic light-emitting element may be a blue organic light-emitting element, and the compounds of Formula 1 and Formula 2 may be used as materials for the blue organic light-emitting element. For example, the compounds of Formula 1 and Formula 2 may be included in the light-emitting layer of the blue organic light-emitting element.

[0226] According to one embodiment of this specification, the organic light-emitting element can be a green organic light-emitting element, and the compounds of Formula 1 and Formula 2 can be used as materials for the green organic light-emitting element. For example, the compounds of Formula 1 and Formula 2 can be included in the light-emitting layer of the green organic light-emitting element.

[0227] According to one embodiment of this specification, the organic light-emitting element may be a red organic light-emitting element, and the compounds of Formula 1 and Formula 2 may be used as materials for the red organic light-emitting element. For example, the compounds of Formula 1 and Formula 2 may be included in the light-emitting layer of the red organic light-emitting element.

[0228] In addition to using the above-mentioned compounds to form one or more organic material layers, the organic light-emitting elements in this specification can be manufactured using common organic light-emitting element manufacturing methods and materials.

[0229] When manufacturing organic light-emitting elements, solution coating and vacuum deposition methods can be used to form organic material layers from compounds. In this article, solution coating methods refer to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc., but are not limited to these.

[0230] The organic material layer of the organic light-emitting element in this specification 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 element of this disclosure may have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc., as organic material layers. However, the structure of the organic light-emitting element is not limited to this, and may include fewer organic material layers.

[0231] The organic light-emitting element disclosed herein may further include one, two or more layers selected from the group consisting of a light-emitting 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.

[0232] In one embodiment of this specification, the organic material layer may further include an electron transport layer and a hole transport layer.

[0233] In one embodiment of this specification, the organic material layer includes an electron transport layer, and the electron transport layer may comprise a compound of the following chemical formula 3.

[0234] [Chemical Formula 3]

[0235]

[0236] In chemical formula 3,

[0237] Y1 to Y3 may be the same as or different from each other, and each is independently N or CH.

[0238] At least one of Y1 to Y3 is N.

[0239] L31 to L33 may be identical or different from each other, and each is independently a direct bond; C6 to C60 arylene; or C2 to C60 heteroarylene.

[0240] R31 to R33 may be the same as or different from each other, and each is independently a cyano group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, and

[0241] r31 to r33 are each an integer from 0 to 5, and when each is 2 or greater than 2, the substituents in the parentheses are the same or different from each other.

[0242] In one embodiment of this specification, Y1 to Y3 of chemical formula 3 may be the same as or different from each other, and each is independently N or CH, and two or more of Y1 to Y3 are preferably N.

[0243] In one embodiment of this specification, Y1 to Y3 may be the same as or different from each other, and each is independently N or CH, and both of Y1 to Y3 may be N.

[0244] In one embodiment of this specification, Y1 to Y3 may all be N.

[0245] In one embodiment of this specification, L31 to L33 of Formula 3 may be the same as or different from each other, and each is independently a direct bond; C6 to C30 arylene; or C2 to C30 heteroarylene.

[0246] In one embodiment of this specification, L31 to L33 may be the same as or different from each other, and each is independently a direct bond; or C6 to C30 arylene.

[0247] In one embodiment of this specification, L31 to L33 may be the same as or different from each other, and each is independently a direct bond; phenylene; biphenylene; or naphthylene.

[0248] In one embodiment of this specification, R31 to R33 of Formula 3 may be the same as or different from each other, and each is independently a cyano group; a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0249] In one embodiment of this specification, R31 to R33 may be the same as or different from each other, and may each be independently cyano; substituted or unsubstituted phenyl; substituted or unsubstituted biphenyl; substituted or unsubstituted terphenyl; substituted or unsubstituted naphthyl; substituted or unsubstituted phenanthryl; substituted or unsubstituted fluorenyl; substituted or unsubstituted benzofluorenyl; substituted or unsubstituted pyridyl; substituted or unsubstituted quinolinyl; substituted or unsubstituted phenanthryl; substituted or unsubstituted dibenzofuranyl; or substituted or unsubstituted dibenzothiopheneyl.

[0250] In one embodiment of this specification, R31 to R33 may be the same as or different from each other, and may each be independently a cyano; an unsubstituted or substituted phenyl group selected from the group consisting of cyano, aryl, and heteroaryl; an unsubstituted or heteroaryl-substituted biphenyl; an unsubstituted or heteroaryl-substituted terphenyl; an unsubstituted or aryl-substituted naphthyl; a substituted or unsubstituted phenanthryl; an unsubstituted or substituted fluorenyl group selected from the group consisting of cyano, alkyl, and aryl; an unsubstituted or alkyl-substituted benzofluorenyl; a substituted or unsubstituted pyridyl; a substituted or unsubstituted quinolinyl; a substituted or unsubstituted phenanthryl; a substituted or unsubstituted dibenzofuranyl; or a substituted or unsubstituted dibenzothiopheneyl.

[0251] In one embodiment of this specification, R31 to R33 may be the same as or different from each other, and may each be independently cyano; an unsubstituted or substituted phenyl group selected from the group consisting of cyano, aryl, and heteroaryl; an unsubstituted or pyridyl-substituted biphenyl; an unsubstituted or pyridyl-substituted terphenyl; an unsubstituted or phenyl-substituted naphthyl; phenanthrene; an unsubstituted or cyano-substituted dimethylfluorenyl; diphenylfluorenyl; spirodifluorenyl; dimethylbenzofluorenyl; pyridyl; quinolinyl; phenanthreneyl; dibenzofuranyl; or dibenzothiopheneyl.

[0252] In one embodiment of this specification, r31 to r33 are each an integer from 1 to 5, and when each is 2 or greater than 2, the substituents in parentheses are the same or different from each other.

[0253] In one embodiment of this specification, chemical formula 3 may be represented by any of the following compounds, but is not limited thereto.

[0254]

[0255]

[0256]

[0257]

[0258] In one embodiment of this specification, the organic material layer includes a hole transport layer, and the hole transport layer may contain a compound of the following chemical formula 4.

[0259] [Chemical Formula 4]

[0260]

[0261] In chemical formula 4,

[0262] L41 to L43 may be identical or different from each other, and each is independently a direct bond; or C6 to C60 arylene, and

[0263] Ar41 to Ar43 may be the same as or different from each other, and each is independently a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0264] In one embodiment of this specification, L41 to L43 of Formula 4 may be the same as or different from each other, and each is independently a direct bond; or a C6 to C30 arylene group.

[0265] In one embodiment of this specification, L41 to L43 may be the same as or different from each other, and each is independently a direct bond; phenylene; biphenylene; or naphthylene.

[0266] In one embodiment of this specification, Ar41 to Ar43 of Formula 4 may be the same as or different from each other, and each is independently a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0267] In one embodiment of this specification, Ar41 to Ar43 may be the same as or different from each other, and may each be independently a substituted or unsubstituted phenyl; a substituted or unsubstituted biphenyl; a substituted or unsubstituted terphenyl; a substituted or unsubstituted naphthyl; a substituted or unsubstituted phenanthyl; a substituted or unsubstituted fluorenyl; a substituted or unsubstituted benzofluorenyl; a substituted or unsubstituted carbazolyl; a substituted or unsubstituted dibenzofuranyl; or a substituted or unsubstituted dibenzothiophene.

[0268] In one embodiment of this specification, Ar41 to Ar43 may be the same as or different from each other, and may each independently be an unsubstituted or aryl-substituted phenyl; a substituted or unsubstituted biphenyl; a substituted or unsubstituted terphenyl; a substituted or unsubstituted naphthyl; a substituted or unsubstituted phenanthyl; an unsubstituted or substituted fluorenyl or substituted with one or more substituents selected from the group consisting of alkyl and aryl; an unsubstituted or alkyl-substituted benzofluorenyl; an unsubstituted or aryl-substituted carbazolyl; a substituted or unsubstituted dibenzofuranyl; or a substituted or unsubstituted dibenzothiopheneyl.

[0269] In one embodiment of this specification, Ar41 to Ar43 may be the same as or different from each other, and may each independently be an unsubstituted or aryl-substituted phenyl; biphenyl; terphenyl; naphthyl; phenanthrene; dimethylfluorenyl; diphenylfluorenyl; unsubstituted or alkyl-substituted spirodifluorenyl; dimethylbenzofluorenyl; unsubstituted or aryl-substituted carbazole; dibenzofuranyl; or dibenzothiopheneyl.

[0270] In one embodiment of this specification, chemical formula 4 may be represented by any of the following compounds, but is not limited thereto.

[0271]

[0272]

[0273]

[0274]

[0275]

[0276] Figures 1 to 3 The diagram illustrates the stacking 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 this art can also be used in this application.

[0277] Figure 1 This illustrates an organic light-emitting element in which an anode 200, an organic material layer 300, and a cathode 400 are continuously stacked on a substrate 100. However, the structure is not limited to this one, 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 stacked on the substrate can also be obtained.

[0278] 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 transport layer 302, a light-emitting 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 layered structure, and layers other than the light-emitting layer may be excluded as needed, and other required functional layers may be added.

[0279] The organic material layer containing the compound of chemical formula 1 may further contain other materials as needed.

[0280] In an organic light-emitting element according to one embodiment of this specification, materials other than compounds of chemical formula 1 are shown below; however, these 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.

[0281] As anode materials, materials with relatively large work functions can be used, and transparent conductive oxides, metals, conductive polymers, etc., 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 oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides, such as ZnO:Al or SnO2:Sb; conductive polymers, such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, etc., but are not limited to these.

[0282] Materials with relatively small work functions can be used as cathode materials, including metals, metal oxides, and conductive polymers. Specific examples of cathode materials include: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or their alloys; multilayer materials such as LiF / Al or LiO2 / Al, but are not limited to these.

[0283] As hole injection materials, known hole injection materials can be used, and for example, phthalocyanine compounds, such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429; or star-shaped catalytic amine derivatives, such as tris(4-carbazolyl-9-ylphenyl)amine (TCTA), 4,4',4”-tris[phenyl(m-tolyl)amino]triphenylamine (m-MTDATA) or 1,3,5-tris[4-(3-methylphenylanilino)phenyl]benzene (m-MTDAPB) as described in the literature [Advanced Materials, 6, p. 677 (1994)], polyaniline / dodecylbenzenesulfonic acid, poly(3,4-ethylenedioxythiophene) / poly(4-styrene sulfonate), polyaniline / camphor sulfonic acid, or polyaniline / poly(4-styrene sulfonate), etc., as conductive polymers with solubility.

[0284] In addition to compounds of chemical formula 4, pyrazoline derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, etc., can also be used as hole transport materials, and low-molecular-weight or high-molecular-weight materials can also be used.

[0285] In addition to compounds of formula 3, metal complexes of 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, dibenzoquinone derivatives, 8-hydroxyquinoline and its derivatives, etc., can also be used as electron transport materials, as well as polymeric and low molecular weight materials.

[0286] As an example of an electron-injected material, LiF is commonly used in this technology; however, this application is not limited to this.

[0287] Red, green, or blue luminescent materials can be used, and two or more luminescent materials can be mixed and used as needed. In this document, two or more luminescent materials can be used either by deposition as individual supply sources or by premixing and deposition as a single supply source. Furthermore, fluorescent materials can also be used as luminescent materials; however, phosphorescent materials can also be used. As luminescent materials, materials that emit light by combining electrons and holes injected from the anode and cathode respectively can be used alone; however, materials having a host material and a dopant material that participate in luminescence together can also be used.

[0288] When mixing luminescent material substrates, substrates from the same series or different series can be mixed. For example, any two or more N-type or P-type substrate materials can be selected as the substrate material for the luminescent layer.

[0289] In this specification, compounds of Formula 1 and Formula 2 are used as host materials, and phosphorescent dopants are used as dopant materials.

[0290] In this specification, the phosphorescent dopant may be (piq)2(Ir)(acac).

[0291] In this specification, the compound of chemical formula 1 may be a P-type host material.

[0292] In this specification, the compound of chemical formula 2 may be an N-type host material.

[0293] An organic light-emitting element according to one embodiment of this specification may be a top-emitting, bottom-emitting, or dual-emitting type, depending on the material used.

[0294] 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, etc., based on similar principles used in organic light-emitting elements.

[0295] One embodiment of this specification provides a composition for forming an organic material layer, the composition comprising a compound of formula 1 and a compound of formula 2.

[0296] According to one embodiment of this specification, the composition for forming an organic material layer may include compounds of formula 1 and compounds of formula 2 in a weight ratio of 1:10 to 10:1, and more specifically, in a weight ratio of 1:5 to 5:1 and 1:3 to 3:1.

[0297] The composition used to form an organic material layer according to one embodiment of this specification can be used as a material for the light-emitting layer of an organic light-emitting element.

[0298] The present specification will be described in more detail below with reference to examples; however, these are for illustrative purposes only, and the scope of this application is not limited thereto.

[0299] [Synthesis Method]

[0300] Synthetic Method 1. Synthesis of Compound 1-1

[0301]

[0302] (4-([1,1'-biphenyl]-4-yl(phenyl)amino)phenyl)boronic acid (10.0 g, 27.4 mmol / L (mM)), 2-chloro-4,6-diphenyl-1,3,5-triazine (8.1 g, 30.1 mM), Pd(PPh3)4(tetra(triphenylphosphine)palladium(0)) (1.6 g, 1.4 mM) and K2CO3 (9.5 g, 68.5 mM) were dissolved in 1,4-dioxane / H2O (100 mL / 20 mL) and refluxed for 1 h. After the reaction was complete, the results were extracted at room temperature, and the solvent was removed from the filtrate by rotary evaporator. The reaction material was purified by column chromatography (dichloromethane (DCM):hexane (Hex) = 1:1) and recrystallized from methanol to obtain the target compound 1-1 (13.5 g, 89.1%).

[0303] The target compound was prepared in the same manner as in Synthesis Method 1, except that intermediates A and B from Table 1 were used instead of (4-([1,1'-biphenyl]-4-yl(phenyl)amino)phenyl)boronic acid and 2-chloro-4,6-diphenyl-1,3,5-triazine.

[0304] [Table 1]

[0305]

[0306]

[0307] Synthetic Method 2. Synthesis of Compounds 1-28

[0308]

[0309] The following substances were prepared: 4-([1,1'-biphenyl]-4-yl)-2-chloroquinazoline (10.0 g, 31.6 mM), di([1,1'-biphenyl]-4-yl)amine (10.2 g, 31.6 mM), Pd2(dba)3(tris(dibenzylideneacetone)dipalladium(0)) (1.5 g, 1.6 mM), Xphos(2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl) (1.5 g, 3.2 mM), and NaO. t Bu (9.1 g, 94.8 mM) was dissolved in xylene (100 mL) and refluxed for 1 hour. After the reaction was complete, the results were filtered through diatomaceous earth at room temperature, and the solvent was removed from the filtrate using a rotary evaporator. The reaction material was purified by column chromatography (DCM:Hex = 1:1) and recrystallized from methanol to obtain the target compound 1-28 (18.1 g, 94.9%).

[0310] The target compound was prepared in the same manner as in Synthesis Method 2, except that intermediates C and D from Table 2 were used instead of 4-([1,1'-biphenyl]-4-yl)-2-chloroquinazoline and di([1,1'-biphenyl]-4-yl)amine.

[0311] [Table 2]

[0312]

[0313]

[0314] Synthetic Method 3. Synthesis of Compounds 1-82

[0315]

[0316] 3-1) Synthesis of compound 1-2-82

[0317] 5-Bromo-7-chloronaphtho[1,2-b]benzofuran (10.0 g, 30.2 mM), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxane)borane (11.5 g, 45.3 mM), PdCl2(dppf))([1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II)) (1.1 g, 1.5 mM), and potassium acetate (KOAc) (5.9 g, 60.4 mM) were dissolved in 1,4-dioxane (100 mL) and refluxed for 1 hour. After the reaction was complete, the results were filtered through diatomaceous earth at room temperature, and the solvent was removed from the filtrate using a rotary evaporator. The reaction material was purified by column chromatography (DCM:Hex = 1:5) and recrystallized with methanol to obtain compound 1-2-82 (10.1 g, 88.4%).

[0318] 3-2) Synthesis of compound 1-1-82

[0319] Compound 1-2-82 (10.0 g, 26.4 mM), 2-chloro-4,6-diphenyl-1,3,5-triazine (7.8 g, 29.0 mM), Pd(PPh3)4 (1.5 g, 1.3 mM), and K2CO3 (9.1 g, 66.0 mM) were dissolved in 1,4-dioxane / H2O (100 mL / 20 mL) and refluxed for 1 hour. After the reaction was complete, the results were filtered under vacuum at room temperature. The results were then stirred in distilled water for 30 minutes and then dried to obtain compound 1-1-82 (11.5 g, 90.1%).

[0320] 3-3) Synthesis of compound 1-82

[0321] Compound 1-1-82 (10.0 g, 20.7 mM), (4-([1,1'-biphenyl]-4-yl(phenyl)amino)phenyl)boronic acid (8.3 g, 22.8 mM), Pd(PPh3)4 (1.2 g, 1.0 mM), and K2CO3 (7.2 g, 51.8 mM) were dissolved in 1,4-dioxane / H2O (100 mL / 20 mL) and refluxed for 1 hour. After the reaction was complete, the results were filtered through diatomaceous earth at room temperature, and the solvent was removed from the filtrate using a rotary evaporator. The reaction material was purified by column chromatography (DCM:Hex = 1:5) and recrystallized from methanol to obtain the target compound 1-82 (14.3 g, 89.9%).

[0322] The target compound was prepared in the same manner as in Synthesis Method 3, except that intermediates E and F from Table 3 were used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine and (4-([1,1'-biphenyl]-4-yl(phenyl)amino)phenyl)boronic acid.

[0323] [Table 3]

[0324]

[0325] Synthetic Method 4. Synthesis of Compounds 1-80

[0326]

[0327] Compound 1-1-82 (10.0 g, 20.7 mM), N-phenyl-[1,1'-biphenyl]-4-amine (5.6 g, 22.8 mM), Pd2(dba)3 (0.9 g, 1.0 mM), Xphos (1.0 g, 2.1 mM), and NaO were added. t Bu (6.0 g, 62.1 mM) was dissolved in xylene (100 mL) and refluxed for 1 hour. After the reaction was complete, the results were filtered through diatomaceous earth at room temperature, and the solvent was removed from the filtrate using a rotary evaporator. The reaction material was purified by column chromatography (DCM:Hex = 1:1) and recrystallized from methanol to obtain the target compound 1-80 (13.5 g, 94.2%).

[0328] The target compound was prepared in the same manner as in synthetic methods 3 and 4, except that intermediate G from Table 4 was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine in synthetic method 3, and intermediate H from Table 4 was used instead of N-phenyl-[1,1'-biphenyl]-4-amine in synthetic method 4.

[0329] [Table 4]

[0330]

[0331] Synthetic Method 5. Synthesis of Compounds 1-136

[0332]

[0333] 5-1) Synthesis of compound 1-2-136

[0334] 5-bromo-7-chloronaphtho[1,2-b]benzofuran (10.0 g, 30.2 mM), N-phenyl-[1,1'-biphenyl]-4-amine (7.4 g, 30.2 mM), Pd2(dba)3 (1.4 g, 1.5 mM), Xphos (1.4 g, 3.0 mM) and NaO were added. tBu (5.8 g, 60.4 mM) was dissolved in toluene (100 mL) and refluxed for 1 hour. After the reaction was complete, the results were filtered through diatomaceous earth at room temperature, and the solvent was removed from the filtrate using a rotary evaporator. The reaction material was purified by column chromatography (DCM:Hex = 1:5) and recrystallized from methanol to obtain compound 1-2-136 (12.3 g, 82.1%).

[0335] 5-2) Synthesis of compound 1-1-136

[0336] Compound 1-2-136 (10.0 g, 20.2 mM), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxane) (7.7 g, 30.3 mM), Pd2(dba)3 (0.9 g, 1.0 mM), Xphos (1.0 g, 2.0 mM), and KOAc (4.0 g, 40.4 mM) were dissolved in 1,4-dioxane (100 mM) and refluxed for 1 hour. After the reaction was complete, the results were filtered through diatomaceous earth at room temperature, and the solvent was removed from the filtrate using a rotary evaporator. The reaction material was purified by column chromatography (DCM:Hex = 1:3) and recrystallized from methanol to obtain compound 1-1-136 (10.5 g, 88.6%).

[0337] 5-3) Synthesis of compound 1-136

[0338] Compound 1-1-136 (10.0 g, 17.0 mM), 2-chloro-4,6-diphenyl-1,3,5-triazine (5.0 g, 18.7 mM), Pd(PPh3)4 (1.0 g, 0.9 mM), and K2CO3 (5.9 g, 42.5 mM) were dissolved in 1,4-dioxane / H2O (100 mL / 20 mL) and refluxed for 1 hour. After the reaction was complete, the results were extracted at room temperature, and the solvent was removed from the filtrate using a rotary evaporator. The reaction material was purified by column chromatography (DCM:Hex = 1:1) and recrystallized from methanol to obtain the target compound 1-136 (10.5 g, 88.8%).

[0339] The target compound was prepared in the same manner as in synthetic method 5, except that intermediates I and J from Table 5 were used instead of N-phenyl-[1,1'-biphenyl]-4-amine and 2-chloro-4,6-diphenyl-1,3,5-triazine.

[0340] [Table 5]

[0341]

[0342] Synthetic Method 6. Synthesis of Compounds 1-177

[0343]

[0344] 6-1) Synthesis of compound 1-2-177

[0345] 1-Bromo-3-chlorodibenzo[b,d]furan (10.0 g, 35.5 mM), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxane), 13.5 g, 53.3 mM, PdCl2(dppf), 1.3 g, 1.8 mM, and KOAc (7.0 g, 71.0 mM) were dissolved in 1,4-dioxane (100 mL) and refluxed for 1 hour. After the reaction was complete, the results were filtered through diatomaceous earth at room temperature, and the solvent was removed from the filtrate using a rotary evaporator. The reaction material was purified by column chromatography (DCM:Hex = 1:5) and recrystallized from methanol to obtain compound 1-2-177 (10.3 g, 88.2%).

[0346] 6-2) Synthesis of compound 1-1-177

[0347] Compound 1-2-177 (10.0 g, 30.4 mM), 2-chloro-4,6-diphenyl-1,3,5-triazine (8.9 g, 33.4 mM), Pd(PPh3)4 (1.7 g, 1.5 mM), and K2CO3 (10.5 g, 76.0 mM) were dissolved in 1,4-dioxane / H2O (100 mL / 20 mL) and refluxed for 1 hour. After the reaction was complete, the results were filtered under vacuum at room temperature. The results were then stirred in distilled water for 30 minutes and then dried to obtain compound 1-1-177 (11.5 g, 87.2%).

[0348] 6-3) Synthesis of compound 1-177

[0349] Compound 1-1-177 (10.0 g, 23.0 mM), (4-(naphth-2-yl(phenyl)amino)phenyl)boronic acid (8.6 g, 25.3 mM), Pd(PPh3)4 (1.4 g, 1.2 mM), and K2CO3 (7.9 g, 57.5 mM) were dissolved in 1,4-dioxane / H2O (100 mL / 20 mL) and refluxed for 1 hour. After the reaction was complete, the results were filtered through diatomaceous earth at room temperature, and the solvent was removed from the filtrate using a rotary evaporator. The reaction material was purified by column chromatography (DCM:Hex = 1:1) and recrystallized from methanol to obtain the target compound 1-177 (14.1 g, 88.7%).

[0350] The target compound was prepared in the same manner as in synthetic method 6, except that intermediates K and L from Table 6 were used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine and (4-(naphth-2-yl(phenyl)amino)phenyl)boronic acid.

[0351] [Table 6]

[0352]

[0353]

[0354]

[0355] Synthetic Method 7. Synthesis of Compound 1-201

[0356]

[0357] 7-1) Synthesis of compound 1-2-201

[0358] 1-Bromo-3-chlorodibenzo[b,d]furan (10.0 g, 35.5 mM), N-phenyl-[1,1'-biphenyl]-4-amine (8.7 g, 35.5 mM), Pd2(dba)3 (1.6 g, 1.8 mM), Xphos (1.7 g, 3.6 mM) and NaO were added. t Bu (6.8 g, 71.0 mM) was dissolved in toluene (100 mL) and refluxed for 1 hour. After the reaction was complete, the results were filtered through diatomaceous earth at room temperature, and the solvent was removed from the filtrate using a rotary evaporator. The reaction material was purified by column chromatography (DCM:Hex = 1:5) and recrystallized from methanol to obtain compound 1-2-201 (14.9 g, 94.1%).

[0359] 7-2) Synthesis of compound 1-1-201

[0360] Compound 1-2-201 (10.0 g, 22.4 mM), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxane) (8.5 g, 33.6 mM), Pd2(dba)3 (1.0 g, 1.1 mM), Xphos (1.0 g, 2.2 mM), and KOAc (4.4 g, 44.8 mM) were dissolved in 1,4-dioxane (100 mL) and refluxed for 1 h. After the reaction was complete, the results were filtered through diatomaceous earth at room temperature, and the solvent was removed from the filtrate using a rotary evaporator. The reaction material was purified by column chromatography (DCM:Hex = 1:3) and recrystallized from methanol to obtain compound 1-1-201 (11.3 g, 93.8%).

[0361] 7-3) Synthesis of compound 1-201

[0362] Compound 1-1-201 (10.0 g, 18.6 mM), 2-chloro-4,6-diphenyl-1,3,5-triazine (5.5 g, 20.5 mM), Pd(PPh3)4 (1.0 g, 0.9 mM), and K2CO3 (6.4 g, 46.5 mM) were dissolved in 1,4-dioxane / H2O (100 mL / 20 mL) and refluxed for 1 hour. After the reaction was complete, the results were extracted at room temperature, and the solvent was removed from the filtrate using a rotary evaporator. The reaction material was purified by column chromatography (DCM:Hex = 1:1) and recrystallized from methanol to obtain the target compound 1-201 (10.9 g, 91.4%).

[0363] The target compound was prepared in the same manner as in Synthesis Method 7, except that intermediates M and N from Table 7 were used instead of N-phenyl-[1,1'-biphenyl]-4-amine and 2-chloro-4,6-diphenyl-1,3,5-triazine.

[0364] [Table 7]

[0365]

[0366] Synthetic Methods 8. Synthesis of Compounds 1-229

[0367]

[0368] 8-1) Synthesis of compound 1-2-229

[0369] 1-Bromo-4-chlorodibenzo[b,d]furan (20.0 g, 71.0 mM), di([1,1'-biphenyl]-4-yl)amine (22.8 g, 71.0 mM), Pd2(dba)3 (3.3 g, 3.6 mM), Xphos (3.4 g, 7.1 mM) and NaO were added. t Bu (13.6 g, 142.0 mM) was dissolved in toluene (200 mL) and refluxed for 1 hour. After the reaction was complete, the results were filtered through diatomaceous earth at room temperature, and the solvent was removed from the filtrate using a rotary evaporator. The reaction material was purified by column chromatography (DCM:Hex = 1:5) and recrystallized from methanol to obtain compound 1-2-229 (34.1 g, 92.0%).

[0370] 8-2) Synthesis of compound 1-1-229

[0371] Compound 1-2-229 (20.0 g, 38.3 mM), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxane) (14.6 g, 57.5 mM), Pd2(dba)3 (1.7 g, 1.9 mM), Xphos (1.8 g, 3.8 mM), and KOAc (7.5 g, 76.6 mM) were dissolved in 1,4-dioxane (200 mL) and refluxed for 1 h. After the reaction was complete, the results were filtered through diatomaceous earth at room temperature, and the solvent was removed from the filtrate using a rotary evaporator. The reaction material was purified by column chromatography (DCM:Hex = 1:3) and recrystallized from methanol to obtain compound 1-1-229 (21.5 g, 91.4%).

[0372] 8-3) Synthesis of compound 1-229

[0373] Compound 1-1-229 (10.0 g, 16.3 mM), 2-chloro-4,6-diphenyl-1,3,5-triazine (4.8 g, 17.9 mM), Pd(PPh3)4 (0.9 g, 0.8 mM), and K2CO3 (5.6 g, 40.8 mM) were dissolved in 1,4-dioxane / H2O (100 mL / 20 mL) and refluxed for 1 hour. After the reaction was complete, the results were extracted at room temperature, and the solvent was removed from the filtrate using a rotary evaporator. The reaction material was purified by column chromatography (DCM:Hex = 1:1) and recrystallized from methanol to obtain the target compound 1-229 (10.1 g, 86.5%).

[0374] The target compound was prepared in the same manner as in Synthesis Method 8, except that intermediates O and P from Table 8 were used instead of di([1,1'-biphenyl]-4-yl)amine and 2-chloro-4,6-diphenyl-1,3,5-triazine.

[0375] [Table 8]

[0376]

[0377]

[0378] Synthetic Methods 9. Synthesis of Compounds 1-236

[0379]

[0380] 9-1) Synthesis of compound 1-2-236

[0381] 1-Bromo-4-chlorodibenzo[b,d]furan (10.0 g, 35.5 mM), (4-((9,9-dimethyl-9H-fluoren-2-yl)(phenyl)amino)phenyl)boronic acid (14.4 g, 35.5 mM), Pd(PPh3)4 (2.1 g, 1.8 mM) and K2CO3 (12.3 g, 88.8 mM) were dissolved in 1,4-dioxane / H2O (100 mL / 20 mL) and refluxed for 1 hour. After the reaction was complete, the results were filtered through diatomaceous earth at room temperature, and the solvent was removed from the filtrate using a rotary evaporator. The reaction material was purified by column chromatography (DCM:Hex = 1:4) and recrystallized from methanol to obtain compound 1-2-236 (17.3 g, 86.8%).

[0382] 9-2) Synthesis of compound 1-1-236

[0383] Compound 1-2-236 (17.0 g, 30.2 mM), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxane) (11.5 g, 45.3 mM), Pd2(dba)3 (1.4 g, 1.5 mM), Xphos (1.4 g, 3.0 mM), and KOAc (5.9 g, 60.4 mM) were dissolved in 1,4-dioxane (200 mL) and refluxed for 1 h. After the reaction was complete, the results were filtered through diatomaceous earth at room temperature, and the solvent was removed from the filtrate using a rotary evaporator. The reaction material was purified by column chromatography (DCM:Hex = 1:3) and recrystallized from methanol to obtain compound 1-1-236 (18.5 g, 93.7%).

[0384] 9-3) Synthesis of compound 1-236

[0385] Compound 1-1-236 (10.0 g, 15.3 mM), 2-chloro-4,6-diphenyl-1,3,5-triazine (4.5 g, 16.8 mM), Pd(PPh3)4 (0.9 g, 0.8 mM), and K2CO3 (5.3 g, 38.3 mM) were dissolved in 1,4-dioxane / H2O (100 mL / 20 mL) and refluxed for 1 hour. After the reaction was complete, the results were extracted at room temperature, and the solvent was removed from the filtrate using a rotary evaporator. The reaction material was purified by column chromatography (DCM:Hex = 1:1) and recrystallized from methanol to obtain the target compound 1-236 (10.1 g, 86.9%).

[0386] The target compound was prepared in the same manner as in Synthesis Method 9, except that intermediates Q and R from Table 9 were used instead of (4-((9,9-dimethyl-9H-fluoren-2-yl)(phenyl)amino)phenyl)boronic acid and 2-chloro-4,6-diphenyl-1,3,5-triazine.

[0387] [Table 9]

[0388]

[0389] Synthetic Method 10. Synthesis of Compounds 1-266

[0390]

[0391] 10-1) Synthesis of compound 1-2-266

[0392] 1-Bromo-4-chlorodibenzo[b,d]furan (20.0 g, 71.0 mM), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxane) (27.0 g, 106.5 mM), PdCl2(dppf) (2.6 g, 3.6 mM), and KOAc (13.9 g, 142.0 mM) were dissolved in 1,4-dioxane (200 mL) and refluxed for 1 h. After the reaction was complete, the results were filtered through diatomaceous earth at room temperature, and the solvent was removed from the filtrate using a rotary evaporator. The reaction material was purified by column chromatography (DCM:Hex = 1:5) and recrystallized from methanol to obtain compound 1-2-266 (21.5 g, 92.1%).

[0393] 10-2) Synthesis of compound 1-1-266

[0394] Compound 1-2-266 (20.0 g, 60.9 mM), 2-chloro-4,6-diphenyl-1,3,5-triazine (17.9 g, 67.0 mM), Pd(PPh3)4 (3.5 g, 3.0 mM), and K2CO3 (21.0 g, 152.3 mM) were dissolved in 1,4-dioxane / H2O (200 mL / 40 mL) and refluxed for 1 hour. After the reaction was complete, the results were filtered under vacuum at room temperature. The results were then stirred in distilled water for 30 minutes and then dried to obtain compound 1-1-266 (24.5 g, 92.8%).

[0395] 10-3) Synthetic compound 1-266

[0396] Compound 1-1-266 (15.0 g, 34.6 mM), (3-([1,1'-biphenyl]-4-yl(phenyl)amino)phenyl)boronic acid (13.9 g, 38.1 mM), Pd(PPh3)4 (2.0 g, 1.7 mM), and K2CO3 (12.0 g, 86.5 mM) were dissolved in 1,4-dioxane / H2O (150 mL / 30 mL) and refluxed for 1 h. After the reaction was complete, the results were extracted at room temperature, and the solvent was removed from the filtrate using a rotary evaporator. The reaction material was purified by column chromatography (DCM:Hex = 1:1) and recrystallized from methanol to obtain the target compound 1-266 (22.0 g, 88.4%).

[0397] The target compound was prepared in the same manner as in synthetic method 10, except that intermediates S and T from Table 10 were used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine and (3-([1,1'-biphenyl]-4-yl(phenyl)amino)phenyl)boronic acid.

[0398] [Table 10]

[0399]

[0400]

[0401] Synthetic Methods 11. Synthesis of Compounds 1-263

[0402]

[0403] Compound 1-1-266 (15.0 g, 34.6 mM), di([1,1'-biphenyl]-4-yl)amine (12.2 g, 38.1 mM), Pd2(dba)3 (1.6 g, 1.7 mM), Xphos (1.7 g, 3.5 mM), and NaO were added. tBu (6.7 g, 69.2 mM) was dissolved in xylene (150 mL) and refluxed for 1 hour. After the reaction was complete, the results were filtered through diatomaceous earth at room temperature, and the solvent was removed from the filtrate using a rotary evaporator. The reaction material was purified by column chromatography (DCM:Hex = 1:1) and recrystallized from methanol to obtain the target compound 1-263 (22.1 g, 88.7%).

[0404] Synthetic Method 12. Synthesis of Compound 1-301

[0405]

[0406] 12-1) Synthesis of compound 1-2-301

[0407] 1-Bromo-3-chloronaphtho[2,3-b]benzofuran (20.0 g, 60.3 mM), N-phenyl-[1,1'-biphenyl]-4-amine (14.8 g, 60.3 mM), Pd2(dba)3 (2.7 g, 3.0 mM), Xphos (2.9 g, 6.0 mM), and NaO were added. t Bu (11.6 g, 120.6 mM) was dissolved in toluene (200 mL) and refluxed for 1 hour. After the reaction was complete, the results were filtered through diatomaceous earth at room temperature, and the solvent was removed from the filtrate using a rotary evaporator. The reaction material was purified by column chromatography (DCM:Hex = 1:5) and recrystallized from methanol to obtain compound 1-2-301 (27.5 g, 91.9%).

[0408] 12-2) Synthesis of compound 1-1-301

[0409] Compound 1-2-301 (27.0 g, 54.4 mM), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxane) (20.7 g, 81.6 mM), Pd2(dba)3 (2.5 g, 2.7 mM), Xphos (2.6 g, 5.4 mM), and KOAc (10.7 g, 108.8 mM) were dissolved in 1,4-dioxane (300 mL) and refluxed for 1 h. After the reaction was complete, the results were filtered through diatomaceous earth at room temperature, and the solvent was removed from the filtrate using a rotary evaporator. The reaction material was purified by column chromatography (DCM:Hex = 1:3) and recrystallized from methanol to obtain compound 1-1-301 (29.8 g, 93.2%).

[0410] 12-3) Synthesis of compound 1-301

[0411] Compound 1-1-301 (15.0 g, 25.5 mM), 2-chloro-4,6-diphenyl-1,3,5-triazine (7.5 g, 28.1 mM), Pd(PPh3)4 (1.5 g, 1.3 mM), and K2CO3 (8.8 g, 63.8 mM) were dissolved in 1,4-dioxane / H2O (150 mL / 30 mL) and refluxed for 1 hour. After the reaction was complete, the results were extracted at room temperature, and the solvent was removed from the filtrate using a rotary evaporator. The reaction material was purified by column chromatography (DCM:Hex = 1:1) and recrystallized from methanol to obtain the target compound 1-301 (15.1 g, 85.5%).

[0412] The target compound was prepared in the same manner as in synthetic method 12, except that intermediates U and V from Table 11 were used instead of N-phenyl-[1,1'-biphenyl]-4-amine and 2-chloro-4,6-diphenyl-1,3,5-triazine.

[0413] [Table 11]

[0414]

[0415]

[0416] Synthetic Method 13. Synthesis of Compounds 1-327

[0417]

[0418] 13-1) Synthesis of compound 1-2-327

[0419] 1-Bromo-3-chloronaphtho[2,3-b]benzofuran (20.0 g, 60.3 mM), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxane) (23.0 g, 90.5 mM), PdCl2(dppf) (2.2 g, 3.0 mM), and KOAc (14.8 g, 150.8 mM) were dissolved in 1,4-dioxane (200 mL) and refluxed for 1 h. After the reaction was complete, the results were filtered through diatomaceous earth at room temperature, and the solvent was removed from the filtrate using a rotary evaporator. The reaction material was purified by column chromatography (DCM:Hex = 1:5) and recrystallized from methanol to obtain compound 1-2-327 (20.1 g, 88.1%).

[0420] 13-2) Synthesis of compound 1-1-327

[0421] Compound 1-2-327 (10.0 g, 26.4 mM), 2-chloro-4,6-diphenyl-1,3,5-triazine (7.8 g, 29.0 mM), Pd(PPh3)4 (1.5 g, 1.3 mM), and K2CO3 (9.1 g, 66.0 mM) were dissolved in 1,4-dioxane / H2O (100 mL / 20 mL) and refluxed for 1 hour. After the reaction was complete, the results were filtered under vacuum at room temperature. The results were then stirred in distilled water for 30 minutes and then dried to obtain compound 1-1-327 (11.5 g, 90.2%).

[0422] 13-3) Synthesis of compound 1-327

[0423] Compound 1-1-327 (11.0 g, 22.7 mM), N-phenyl-[1,1'-biphenyl]-4-amine (6.1 g, 25.0 mM), Pd2(dba)3 (1.0 g, 1.1 mM), Xphos (1.1 g, 2.3 mM), and NaO were added. t Bu (5.5 g, 56.8 mM) was dissolved in xylene (150 mL) and refluxed for 1 hour. After the reaction was complete, the results were filtered through diatomaceous earth at room temperature, and the solvent was removed from the filtrate using a rotary evaporator. The reaction material was purified by column chromatography (DCM:Hex = 1:1) and recrystallized from methanol to obtain the target compound 1-327 (14.0 g, 89.0%).

[0424] The target compound was prepared in the same manner as in synthetic method 13, except that intermediates W and X from Table 12 were used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine and N-phenyl-[1,1'-biphenyl]-4-amine.

[0425] [Table 12]

[0426]

[0427] Synthetic Method 14. Synthetic Compounds 1-345

[0428]

[0429] Compound 1-1-327 (11.0 g, 22.7 mM), (4-([1,1'-biphenyl]-4-yl(phenyl)amino)phenyl)boronic acid (9.1 g, 25.0 mM), Pd(PPh3)4 (1.3 g, 1.1 mM), and K2CO3 (7.9 g, 56.8 mM) were dissolved in 1,4-dioxane / H2O (150 mL / 30 mL) and refluxed for 1 hour. After the reaction was complete, the results were extracted at room temperature, and the solvent was removed from the filtrate using a rotary evaporator. The reaction material was purified by column chromatography (DCM:Hex = 1:1) and recrystallized from methanol to obtain the target compound 1-345 (15.1 g, 86.3%).

[0430] Synthetic Method 15. Synthesis of Compounds 1-422

[0431]

[0432] 15-1) Synthesis of compound 1-2-422

[0433] 1-Bromo-7-chlorodibenzo[b,d]furan (20.0 g, 71.0 mM), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxane) (27.0 g, 106.5 mM), PdCl2(dppf) (2.6 g, 3.6 mM), and KOAc (17.4 g, 177.5 mM) were dissolved in 1,4-dioxane (200 mL) and refluxed for 1 hour. After the reaction was complete, the results were filtered through diatomaceous earth at room temperature, and the solvent was removed from the filtrate using a rotary evaporator. The reaction material was purified by column chromatography (DCM:Hex = 1:5) and recrystallized from methanol to obtain compound 1-2-422 (22.1 g, 94.5%).

[0434] 15-2) Synthesis of compound 1-1-422

[0435] Compound 1-2-422 (22.0 g, 67.0 mM), 2-chloro-4,6-diphenyl-1,3,5-triazine (19.7 g, 73.7 mM), Pd(PPh3)4 (3.9 g, 3.4 mM), and K2CO3 (23.2 g, 167.5 mM) were dissolved in 1,4-dioxane / H2O (200 mL / 40 mL) and refluxed for 1 hour. After the reaction was complete, the results were filtered under vacuum at room temperature. The results were then stirred in distilled water for 30 minutes and then dried to obtain compound 1-1-422 (26.3 g, 90.4%).

[0436] 15-3) Synthesis of compound 1-422

[0437] Compound 1-1-422 (20.0 g, 46.1 mM), N-phenyl-[1,1'-biphenyl]-4-amine (12.4 g, 50.7 mM), Pd2(dba)3 (2.1 g, 2.3 mM), Xphos (2.2 g, 4.6 mM), and NaO were used. t Bu (11.1 g, 115.3 mM) was dissolved in xylene (150 mL) and refluxed for 1 hour. After the reaction was complete, the results were filtered through diatomaceous earth at room temperature, and the solvent was removed from the filtrate using a rotary evaporator. The reaction material was purified by column chromatography (DCM:Hex = 1:1) and recrystallized from methanol to obtain the target compound 1-422 (27.1 g, 91.5%).

[0438] The target compound was prepared in the same manner as in synthetic method 15, except that intermediates Y and Z from Table 13 were used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine and N-phenyl-[1,1'-biphenyl]-4-amine.

[0439] [Table 13]

[0440]

[0441]

[0442]

[0443] Synthetic Method 16. Synthesis of Compounds 1-430

[0444]

[0445] 16-1) Synthesis of compound 1-2-430

[0446] 1-Bromo-7-chlorodibenzo[b,d]furan (20.0 g, 71.0 mM), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxane) (27.0 g, 106.5 mM), PdCl2(dppf) (2.6 g, 3.6 mM), and KOAc (17.4 g, 177.5 mM) were dissolved in 1,4-dioxane (200 mL) and refluxed for 1 hour. After the reaction was complete, the results were filtered through diatomaceous earth at room temperature, and the solvent was removed from the filtrate using a rotary evaporator. The reaction material was purified by column chromatography (DCM:Hex = 1:5) and recrystallized from methanol to obtain compound 1-2-430 (22.1 g, 94.5%).

[0447] 16-2) Synthesis of compound 1-1-430

[0448] Compound 1-2-430 (22.0 g, 67.0 mM), 4-chloro-2,6-diphenylpyrimidine (19.7 g, 73.7 mM), Pd(PPh3)4 (3.9 g, 3.4 mM), and K2CO3 (23.2 g, 167.5 mM) were dissolved in 1,4-dioxane / H2O (200 mL / 40 mL) and refluxed for 1 hour. After the reaction was complete, the results were filtered under vacuum at room temperature. The results were then stirred in distilled water for 30 minutes and then dried to obtain compound 1-1-430 (25.1 g, 86.6%).

[0449] 16-3) Synthetic compound 1-430

[0450] Compound 1-1-430 (15.0 g, 34.6 mM), N-phenyl-N-(3-(4,4,5,5-tetramethyl-1,3,2-dioxane-2-yl)phenyl)naphth-1-amine (16.1 g, 38.1 mM), Pd(PPh3)4 (2.0 g, 1.7 mM), and K2CO3 (12.0 g, 86.5 mM) were dissolved in 1,4-dioxane / H2O (150 mL / 30 mL) and refluxed for 1 hour. After the reaction was complete, the results were extracted at room temperature, and the solvent was removed from the filtrate using a rotary evaporator. The reaction material was purified by column chromatography (DCM:Hex = 1:1) and recrystallized from methanol to obtain the target compound 1-430 (21.0 g, 87.6%).

[0451] The target compound was prepared in the same manner as in synthetic methods 15 and 16, except that intermediate A1 from Table 14 was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine in synthetic method 15, and intermediate B1 from Table 14 was used instead of N-phenyl-N-(3-(4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane-2-yl)phenyl)naphthyl-1-amine in synthetic method 16.

[0452] [Table 14]

[0453]

[0454] Synthetic Method 17. Synthesizing Compounds 2-5

[0455]

[0456] 17-1) Preparation of compound 2-5-2

[0457] 1-Bromo-4-chloronaphtho[2,3-b]benzofuran (30.0 g, 90.5 mM), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxane) (34.5 g, 135.8 mM), PdCl2(dppf) (3.3 g, 4.5 mM), and KOAc (26.6 g, 271.5 mM) were dissolved in 1,4-dioxane (300 mL) and refluxed for 24 hours. After the reaction was complete, the results were filtered under vacuum at room temperature, and the solvent was removed from the filtrate by rotary evaporator. The reaction material was purified by column chromatography (DCM:Hex = 1:4) to obtain compound 2-5-2 (31.2 g, 91.0%).

[0458] 17-2) Preparation of compound 2-5-1

[0459] Compound 2-5-2 (30 g, 79.2 mM), 2-chloro-4,6-diphenyl-1,3,5-triazine (23.3 g, 87.1 mM), Pd(PPh3)4 (4.6 g, 4.0 mM), and K2CO3 (32.8 g, 237.6 mM) were dissolved in 1,4-dioxane / H2O (300 mL / 60 mL) and refluxed for 1 hour. After the reaction was complete, the results were filtered under vacuum at room temperature and purified by DCB silica. The results were purified by recrystallization from methanol (MeOH) to obtain compound 2-5-1 (35.3 g, 92.0%).

[0460] 17-3) Preparation of compound 2-5

[0461] Compound 2-5-1 (10.0 g, 20.7 mM), (4-(naphthyl-1-yl)phenyl)boronic acid (6.2 g, 24.8 mM), Pd2(dba)3 (0.9 g, 1.0 mM), Xphos (1.0 g, 2.1 mM), and NaOH (2.5 g, 62.1 mM) were dissolved in 1,4-dioxane / H2O (100 mL / 20 mL) and refluxed for 2 hours. After the reaction was complete, the results were filtered under vacuum at room temperature and purified by DCB silica. The results were purified by recrystallization from methanol to obtain the target compound 2-5 (12.5 g, 92.8%).

[0462] The target compound was prepared in the same manner as in synthetic method 17, except that intermediates C1 and D1 from Table 15 were used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine and (4-(naphth-1-yl)phenyl)boronic acid.

[0463] [Table 15]

[0464]

[0465]

[0466] Synthetic methods 18. Synthetic compounds 2-67

[0467]

[0468] 18-1) Preparation of compound 2-67-2

[0469] 1-Bromo-4-chloronaphtho[2,3-b]benzofuran (30.0 g, 90.5 mM), [1,1'-biphenyl]-4-ylboronic acid (17.9 g, 90.5 mM), Pd(PPh3)4 (5.2 g, 4.5 mM) and K2CO3 (31.3 g, 226.3 mM) were dissolved in 1,4-dioxane / H2O (300 mL / 60 mL) and refluxed for 2 h. After the reaction was complete, the results were extracted with DCM at room temperature, and the solvent was removed using a rotary evaporator. The reaction material was purified by column chromatography (DCM:Hex = 1:5) to obtain compound 2-67-2 (29.7 g, 81.1%).

[0470] 18-2) Preparation of compound 2-67-1

[0471] Compound 2-67-2 (29.0 g, 71.6 mM), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxane) (27.3 g, 107.4 mM), Pd2(dba)3 (3.3 g, 3.6 mM), Sphos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl) (3.0 g, 7.2 mM), and KOAc (21.1 g, 214.8 mM) were dissolved in 1,4-dioxane (300 mL) and refluxed for 1 h. After the reaction was complete, the results were filtered under vacuum at room temperature, and the solvent was removed from the filtrate by rotary evaporator. The reaction material was purified by column chromatography (DCM:Hex = 1:2) to obtain compound 2-67-1 (32.7 g, 92.0%).

[0472] 18-3) Preparation of compound 2-67

[0473] Compound 2-67-1 (10.0 g, 20.1 mM), 2-chloro-4,6-diphenyl-1,3,5-triazine (5.9 g, 22.1 mM), Pd2(dba)3 (0.9 g, 1.0 mM), Xphos (1.0 g, 2.0 mM), and NaOH (2.4 g, 60.3 mM) were dissolved in 1,4-dioxane / H2O (100 mL / 20 mL) and refluxed for 1 hour. After the reaction was complete, the results were extracted at room temperature, and the solvent was removed from the filtrate using a rotary evaporator. The reaction material was purified by column chromatography (DCM:Hex = 1:2) and recrystallized with MeOH to obtain the target compound 2-67 (10.3 g, 85.1%).

[0474] The target compound was prepared in the same manner as in synthetic method 18, except that intermediates E1 and F1 from Table 16 were used instead of [1,1'-biphenyl]-4-ylboronic acid and 2-chloro-4,6-diphenyl-1,3,5-triazine.

[0475] [Table 16]

[0476]

[0477] Synthetic Methods 19. Synthesis of Compounds 3-57

[0478]

[0479] 19-1) Preparation of compound 3-1-57

[0480] 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (20.0 g, 58.2 mM), (3'-chloro-[1,1'-biphenyl]-3-yl)boronic acid (14.9 g, 64.0 mM), Pd(PPh3)4 (3.4 g, 2.9 mM) and K2CO3 (20.1 g, 145.5 mM) were dissolved in 1,4-dioxane / H2O (200 mL / 40 mL) and refluxed for 1 hour. After the reaction was complete, the results were filtered under vacuum at room temperature to obtain compound 3-1-57 (25.7 g, 89.0%).

[0481] 19-2) Preparation of compound 3-57

[0482] Compound 3-1-57 (15.0 g, 30.2 mM), (9,9-dimethyl-9H-fluorene-2-yl)boronic acid (7.9 g, 33.2 mM), Pd(PPh3)4 (1.7 g, 1.5 mM), and K2CO3 (12.5 g, 90.6 mM) were dissolved in 1,4-dioxane / H2O (200 mL / 40 mL) and refluxed for 1 hour. The reaction material was purified by column chromatography (DCM:Hex = 1:1) and recrystallized from methanol to obtain compound 3-57 (15.9 g, 80.5%).

[0483] The target compound was prepared in the same manner as in synthetic method 19, except that intermediate G1 from Table 17 was used instead of (9,9-dimethyl-9H-fluoren-2-yl)boronic acid.

[0484] [Table 17]

[0485]

[0486] Synthetic methods 20. Synthetic compounds 4-79

[0487]

[0488] N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluorene-2-amine (15.0 g, 41.5 mM), 2-bromo-11,11-dimethyl-11H-benzo[b]fluorene (14.1 g, 43.6 mM), Pd2dba3 (1.9 g, 2.1 mM), Xphos (2.0 g, 4.2 mM), and NaOtBu (8.0 g, 83.0 mM) were dissolved in xylene (150 mL) and refluxed for 1 hour. After the reaction was complete, the results were filtered through diatomaceous earth at room temperature, and the filtrate was concentrated. The reaction material was purified by column chromatography (DCM:Hex = 1:2) and recrystallized from methanol to obtain compound 4-79 (10.3 g, 88.2%).

[0489] The target compound was prepared in the same manner as in synthetic method 20, except that intermediate H1 from Table 18 was used instead of N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluorene-2-amine and intermediate I1 from Table 18 was used instead of 2-bromo-11,11-dimethyl-11H-benzo[b]fluorene.

[0490] [Table 18]

[0491]

[0492] Compounds other than those described in synthetic methods 1 to 20 were also prepared in the same manner as described above, and the results are shown in Tables 19 and 20 below.

[0493] [Table 19]

[0494]

[0495]

[0496]

[0497] [Table 20]

[0498]

[0499]

[0500]

[0501]

[0502]

[0503] <Experimental Example 1>

[0504] 1) Manufacturing organic light-emitting elements (red single-body & hybrid-body)

[0505] The glass substrate with ITO coated as a thin film to a thickness of 1,500 angstroms was cleaned using distilled water ultrasonic cleaning. After cleaning with distilled water, the substrate was ultrasonically cleaned with solvents such as acetone, methanol, and isopropanol, then dried, and treated with ultraviolet ozone (UVO) for 5 minutes using an ultraviolet (UV) cleaner. The substrate was then transferred to a plasma cleaner (PT) and subjected to plasma treatment under vacuum to achieve the ITO work function and remove residual film. Finally, the substrate was transferred to a thermal deposition apparatus for organic deposition.

[0506] On a transparent ITO electrode (anode), a hole injection layer (2-TNATA(4,4',4”-tris[2-naphthyl(phenyl)amino]triphenylamine)) is formed to a thickness of 100 Å, and a hole transport layer is formed to a thickness of 1100 Å using the compounds described in Table 21 below.

[0507] A light-emitting layer was thermally vacuum deposited on it as follows. The light-emitting layer was deposited to a thickness of 500 Å as the host using compounds described in Table 21 below. When using two types of compounds, these compounds were premixed and then deposited in a single supply source. (piq)₂(Ir)(acac) was used as a red phosphorescent dopant and doped into the host at a ratio of 3%. Subsequently, BCP was deposited to a thickness of 60 Å as a hole-blocking layer, and compounds described in Table 21 below were deposited on it to a thickness of 200 Å as an electron transport layer. Finally, an electron injection layer was formed on the electron transport layer by depositing lithium fluoride (LiF) to a thickness of 10 Å, and then a cathode was formed on the electron injection layer by depositing an aluminum (Al) cathode to a thickness of 1,200 Å. Thus, an organic electroluminescent device was fabricated.

[0508] At the same time, for each material that will be used in OLED manufacturing, all the organic compounds required to manufacture OLEDs are within 10 -8 Up to 10 -6 Vacuum sublimation purification was carried out under a support.

[0509] 2) Evaluation of organic light-emitting elements (red single-host & mixed-host)

[0510] For each organic electroluminescent element manufactured as described above, the electroluminescence (EL) characteristics were measured using an M7000 system manufactured by McScience Inc., and using the measurement results, the lifetime measurement time (T) was measured using a lifetime measurement system (M6000) manufactured by McScience Inc. at a standard luminance of 6,000 candela / m². 90 The characteristics of the organic electroluminescent element disclosed herein are shown in Table 22 below.

[0511]

[0512] [Table 21]

[0513]

[0514] [Table 22]

[0515]

[0516]

[0517] The compound of [Chemical Formula 1] disclosed herein possesses an appropriate molecular weight and band gap, while also exhibiting high thermal stability. The appropriate band gap of the luminescent layer prevents the loss of electrons and holes, thereby facilitating the effective formation of recombination regions. Therefore, as shown in the device evaluation, the compound of this disclosure exhibits improved performance compared to the compounds of the comparative examples. Improved drive and lifetime characteristics are obtained when using a combination of [Chemical Formula 1] and [Chemical Formula 2] in the luminescent layer, and improved lifetime characteristics are obtained when using a combination of a hole transport layer [Chemical Formula 4], an electron transport layer [Chemical Formula 3], and a luminescent layer [a combination of Chemical Formula 1 and Chemical Formula 2]. When a donor (p-host) with good hole transport capability and an acceptor (n-host) with good electron transport capability are used as the hosts of the hole transport layer, electron transport layer, and luminescent layer, respectively, the drive voltage for injected electrons and holes can be reduced, and efficiency and lifetime are improved by effectively forming recombination regions.

Claims

1. 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 includes a light-emitting layer, and the light-emitting layer comprises a compound of chemical formula 1 and a compound of chemical formula 2, and The organic material layer includes an electron transport layer, and the electron transport layer comprises a compound of the following chemical formula 3: [Chemical Formula 1] In chemical formula 1, L1 to L3 may be identical or different from each other, and each is independently a direct bond; C6 to C60 arylene; monocyclic heteroarylene containing N; or tricyclic or higher heteroarylene containing O. Ar1 and Ar2 may be the same as or different from each other, and each is independently a substituted or unsubstituted C1 to C60 alkyl; a substituted or unsubstituted C3 to C60 cycloalkyl; a substituted or unsubstituted C6 to C60 aryl; or a substituted or unsubstituted C2 to C60 heteroaryl, and N-Het is a C2 to C60 heteroaryl group, either substituted or unsubstituted, containing N. [Chemical Formula 2] In chemical formula 2, L21 and L22 may be the same or different from each other, and each is independently a direct bond; C6 to C60 arylene; or C2 to C60 heteroarylene. Z21 and Z22 are distinct from each other and are each independently a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group. One of Z21 and Z22 is a C2 to C60 heteroaryl group, either substituted or unsubstituted, containing N; the remaining one of Z21 and Z22 is a C6 to C60 aryl group, either substituted or unsubstituted; or a C2 to C60 heteroaryl group, either substituted or unsubstituted, containing O or S. R21 and R22 may be the same as or different from each other, and each is independently hydrogen; deuterium; halogen group; cyano group; substituted or unsubstituted C1 to C60 alkyl group; substituted or unsubstituted C6 to C60 aryl group; or substituted or unsubstituted C2 to C60 heteroaryl group. r21 is an integer from 0 to 4. r22 is an integer from 0 to 6. When r21 and r22 are each 2 or greater, the substituents in the parentheses may be the same or different from each other. [Chemical Formula 3] In chemical formula 3, Y1 to Y3 may be the same as or different from each other, and each is independently N or CH. At least one of Y1 to Y3 is N. L31 to L33 may be identical or different from each other, and each is independently a direct bond; C6 to C60 arylene; or C2 to C60 heteroarylene. R31 to R33 may be the same as or different from each other, and each is independently a cyano group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, and r31 to r33 are each an integer from 0 to 5, and when each is 2 or greater than 2, the substituents in the parentheses are the same or different from each other.

2. The organic light-emitting element according to claim 1, wherein N-Het is represented by any one of the following chemical formulas 1-1 to 1-4: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formulas 1-3] [Chemical Formulas 1-4] In chemical formulas 1-1 to 1-4 X1 to X4 are each N or CR. At least one of X1 to X3 is N. A through C may be identical or different from each other, and each is independently a substituted or unsubstituted monocyclic or polycyclic C6 to C60 aryl ring; or a substituted or unsubstituted monocyclic or polycyclic C2 to C60 heterocyclic ring, and R and R1 to R4 may be the same as or different from each other, and each is independently hydrogen; deuterium; halogen group; cyano group; substituted or unsubstituted C1 to C60 alkyl group; substituted or unsubstituted C6 to C60 aryl group; or substituted or unsubstituted C2 to C60 heteroaryl group.

3. The organic light-emitting element according to claim 1, wherein chemical formula 2 is represented by the following chemical formula 2-1: [Chemical Formula 2-1] In chemical formula 2-1, Each substituent has the same definition as in Formula 2.

4. The organic light-emitting element according to claim 1, wherein chemical formula 1 is represented by any of the following compounds: 。 5. The organic light-emitting element according to claim 1, wherein chemical formula 2 is represented by any of the following compounds: 。 6. The organic light-emitting element according to claim 1, wherein chemical formula 3 is represented by any of the following compounds: 。 7. The organic light-emitting element according to claim 1, wherein the organic material layer comprises a hole transport layer, and the hole transport layer comprises a compound of formula 4: [Chemical Formula 4] In chemical formula 4, L41 to L43 may be identical or different from each other, and each is an independent direct bond; or C6 to C60 arylene, and Ar41 to Ar43 may be the same as or different from each other, and each is independently a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

8. The organic light-emitting element according to claim 7, wherein chemical formula 4 is represented by any of the following compounds: 。

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