Compound, light-emitting device containing the same, preparation method thereof, and composition for organic layer

Abstract

The present specification relates to a heterocyclic compound represented by Chemical Formula 1, an organic light-emitting device including the same, a method for manufacturing the same, and a composition for an organic material layer.

Description

Technical Field

[0001] The present invention relates to a heterocyclic compound, an organic light-emitting device including the same, a method for manufacturing the same, and a composition for an organic material layer.

[0002] This specification claims priority to and the benefit of Korean Patent Application No. 10-2020-0048060 filed on April 21, 2020, in the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference. Background Art

[0003] An electroluminescent device is a type of self-luminous display device and has advantages of having a wide viewing angle and a faster response speed and having an excellent contrast ratio.

[0004] An organic light-emitting device has a structure in which an organic thin film is disposed between two electrodes. When voltage is applied to an organic light-emitting device having such a structure, electrons and holes injected from the two electrodes are combined and paired in the organic thin film, and light is emitted when the electrons and holes are annihilated. The organic thin film may be formed in a single layer or a multilayer as necessary.

[0005] If necessary, the material of the organic film may have a light-emitting function. For example, a compound capable of forming the light-emitting layer itself may be used alone, or a compound capable of acting as a host or dopant of a host-dopant type light-emitting layer may be used as the material of the organic film. In addition, a compound capable of performing hole injection, hole transport, electron blocking, hole blocking, electron transport, electron injection, and the like may also be used as the material of the organic film.

[0006] The development of organic thin film materials has been continuously required to enhance the performance, lifespan or efficiency of organic light emitting devices. Summary of the invention

[0007] Technical issues

[0008] The present disclosure provides a heterocyclic compound, an organic light-emitting device comprising the same, a method for manufacturing the same, and a composition for an organic material layer.

[0009] Technical Solutions

[0010] One embodiment of the present application provides a heterocyclic compound represented by the following Chemical Formula 1.

[0011] [Chemical formula 1]

[0012]

[0013] In Chemical Formula 1,

[0014] Ar1 to Ar4 are the same as or different from each other and are each independently hydrogen; deuterium; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl,

[0015] L1 is a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group,

[0016] Z1 is selected from the group consisting of: halogen; -CN; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C10 to C60 aryl; substituted or unsubstituted C2 to C60 heteroaryl containing O or S as a heteroatom; -p(=O)RR'; -SiRR'R"; and substituted or unsubstituted amine,

[0017] When Z1 is a substituted or unsubstituted bicyclic or tetracyclic C15 to C60 aryl group having 9 or less protons, L1 is a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group,

[0018] R, R' and R" are the same as or different from each other, and are each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0019] a is an integer from 1 to 4,

[0020] b is an integer from 1 to 6, and

[0021] When a and b are each 2 or more, the substituents in the parentheses are the same as or different from each other.

[0022] In addition, one embodiment of the present application provides an organic light-emitting device, comprising: a first electrode; a second electrode, arranged opposite to the first electrode; and one or more organic material layers, arranged between the first electrode and the second electrode, wherein one or more layers of the organic material layer comprise a heterocyclic compound represented by Chemical Formula 1.

[0023] In addition, in an organic light-emitting device provided in one embodiment of the present application, the organic material layer including the heterocyclic compound of Chemical Formula 1 further includes a heterocyclic compound represented by the following Chemical Formula 2.

[0024] [Chemical formula 2]

[0025]

[0026] In chemical formula 2,

[0027] Rc and Rd are the same as or different from each other and are each independently selected from the group consisting of hydrogen, deuterium, a halogen group, -CN, a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C2 to C60 alkenyl group, a substituted or unsubstituted C2 to C60 alkynyl group, a substituted or unsubstituted C1 to C60 alkoxy group, a substituted or unsubstituted C3 to C60 cycloalkyl group, a substituted or unsubstituted C2 to C60 heterocycloalkyl group, a substituted or unsubstituted C6 to C60 aryl group, a substituted or unsubstituted C2 to C60 heteroaryl group, -Si(R10)(R11)(R12), -P(=O)(R10)(R11), and a substituted or unsubstituted amino group, or two or more adjacent groups bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocyclic ring,

[0028] R10, R11 and R12 are the same as or different from each other and are each independently hydrogen; deuterium; -CN; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl,

[0029] Ra and Rb are the same as or different 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,

[0030] r and s are each an integer from 0 to 7, and

[0031] When r and s are each 2 or more, the substituents in the parentheses are the same as or different from each other.

[0032] In addition, another embodiment of the present application provides a composition for an organic material layer of an organic light-emitting device, wherein the composition includes a heterocyclic compound represented by Chemical Formula 1 and a heterocyclic compound represented by Chemical Formula 2.

[0033] Finally, one embodiment of the present application provides a method for manufacturing an organic light-emitting device, the method comprising: preparing a substrate; forming a first electrode on the substrate; forming one or more organic material layers on the first electrode; and forming a second electrode on the organic material layer, wherein forming the organic material layer comprises forming one or more organic material layers using a composition for an organic material layer according to one embodiment of the present application.

[0034] Beneficial effects

[0035] The compounds described in this specification can be used as materials for the organic material layer of an organic light-emitting device. In an organic light-emitting device, the compounds can function as hole injection materials, hole transport materials, light-emitting materials, electron transport materials, electron injection materials, or the like. Specifically, the compounds can be used as materials for the light-emitting layer of an organic light-emitting device.

[0036] Specifically, the compound can be used alone as a light-emitting material, or as a host material or dopant material of a light-emitting layer. Using the compound represented by Chemical Formula 1 in an organic material layer can reduce driving voltage, enhance light efficiency, and enhance the lifespan characteristics of a device through the thermal stability of the compound.

[0037] In addition, by the heterocyclic compound represented by Chemical Formula 1 having a substituent of -(L1)a-(Z1)b, the LUMO orbital is delocalized to the triazine group as a core structure long enough, and the substituent and electrons of -(L1)a-(Z1)b are effectively stabilized, and therefore, the organic light-emitting device including the heterocyclic compound has excellent service life characteristics.

[0038] Specifically, the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2 can be used as materials of the light-emitting layer of the organic light-emitting device at the same time. In this case, the driving voltage of the device can be reduced, the light efficiency can be enhanced, and the service life characteristics of the device can be enhanced by the thermal stability of the compound. BRIEF DESCRIPTION OF THE DRAWINGS

[0039] Figures 1 to 3 1 and 2 are diagrams each schematically illustrating a laminate structure of an organic light-emitting device according to one embodiment of the present application.

[0040]

Explanation of symbols

[0041] 100: Base

[0042] 200: Anode

[0043] 300: organic material layer

[0044] 301: hole injection layer

[0045] 302: hole transport layer

[0046] 303: Luminous layer

[0047] 304: Hole blocking layer

[0048] 305: electron transport layer

[0049] 306: electron injection layer

[0050] 400: cathode DETAILED DESCRIPTION

[0051] Hereinafter, the present application will be described in detail.

[0052] In the present specification, the term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is changed into another substituent, and as long as the substitution position is a position where a hydrogen atom is substituted, that is, a position where a substituent can replace, the substitution position is not limited, and when two or more substituents are substituted, the two or more substituents may be the same as or different from each other.

[0053] In the present specification, "substituted or unsubstituted" means substituted with one or more substituents selected from the group consisting of: C1 to C60 straight or branched alkyl; C2 to C60 straight or branched alkenyl; C2 to C60 straight or branched alkynyl; C3 to C60 monocyclic or polycyclic cycloalkyl; C2 to C60 monocyclic or polycyclic heterocycloalkyl; C6 to C60 monocyclic or polycyclic aryl; C2 to C60 monocyclic or polycyclic heteroaryl; -SiRR'R"; -P(=O)RR'; C1 to C20 alkylamine; C6 to C60 monocyclic or polycyclic arylamine; and C2 to C60 monocyclic or polycyclic heteroarylamine, or unsubstituted, or substituted with a substituent connecting two or more substituents selected from the substituents shown above, or unsubstituted, and

[0054] R, R' and R" are the same as or different from each other, and are each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0055] In the present specification, "substituted or unsubstituted" means substituted with one or more substituents selected from the group consisting of: deuterium; halogen; cyano; C1 to C60 straight or branched alkyl; C2 to C60 straight or branched alkenyl; C2 to C60 straight or branched alkynyl; C3 to C60 monocyclic or polycyclic cycloalkyl; C2 to C60 monocyclic or polycyclic heterocycloalkyl; C6 to C60 monocyclic or polycyclic aryl; C2 to C60 monocyclic or polycyclic heteroaryl; -SiRR'R"; -P(=O)RR'; C1 to C20 alkylamine; C6 to C60 monocyclic or polycyclic arylamine; and C2 to C60 monocyclic or polycyclic heteroarylamine, or unsubstituted, or substituted with a substituent connecting two or more substituents selected from the substituents shown above, or unsubstituted, and

[0056] R, R' and R" are the same as or different from each other, and are each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0057] In the present specification, "proton number" means the number of substituents that a specific compound may have, and specifically, the proton number may mean the number of hydrogen. For example, the number of protons in unsubstituted benzene may be expressed as 5, the number of protons in unsubstituted naphthyl may be expressed as 7, the number of protons in naphthyl substituted with phenyl may be expressed as 6, and the number of protons in unsubstituted biphenyl may be expressed as 9.

[0058] In the present specification, "a case where no substituent is indicated in a chemical formula or compound structure" means that a hydrogen atom is bonded to a carbon atom. However, due to the presence of deuterium ( 2 H (Deuterium) is an isotope of hydrogen, so some of the hydrogen atoms may be deuterium.

[0059] In one embodiment of the present application, "the situation where no substituent is indicated in the chemical formula or compound structure" may mean that the positions where the substituent may appear may all be hydrogen or deuterium. In other words, since deuterium is an isotope of hydrogen, some hydrogen atoms may be deuterium as an isotope, and herein, the content of deuterium may be 0% to 100%.

[0060] In one embodiment of the present application, in the case where no substituent is indicated in the chemical formula or compound structure, when deuterium is not explicitly excluded (such as the deuterium content is 0%, the hydrogen content is 100% or the substituents are all hydrogen), hydrogen and deuterium may be mixed in the compound.

[0061] In one embodiment of the present application, deuterium is one of the isotopes of hydrogen, an element having a deuteron formed by one proton and one neutron as a nucleus, and can be expressed as hydrogen-2, and the element symbol can also be written as D or 2 H.

[0062] In one embodiment of the present application, isotopes refer to atoms having the same atomic number (atomic number, Z) but different mass numbers (mass number, A), and can also be interpreted as elements having the same proton number (proton) but different neutron numbers (neutron).

[0063] In one embodiment of the present application, when the total number of substituents that a base compound may have is defined as T1 and the number of specific substituents therein is defined as T2, the content T% of the specific substituent may be defined as T2 / T1×100=T%.

[0064] In other words, in one example, The phenyl group represented by has a deuterium content of 20% means that the total number of substituents that the phenyl group may have is 5 (T1 in the formula), and the number of deuterium among these is 1 (T2 in the formula). In other words, the phenyl group having a deuterium content of 20% can be represented by the following structural formula.

[0065]

[0066] In addition, in one embodiment of the present application, “a phenyl group having a deuterium content of 0%” may mean a phenyl group that does not contain a deuterium atom, that is, a phenyl group having 5 hydrogen atoms.

[0067] In the present specification, halogen may be fluorine, chlorine, bromine or iodine.

[0068] In the present specification, the alkyl group includes a straight chain or branched chain having 1 to 60 carbon atoms, and may be further substituted with other substituents. The number of carbon atoms of the alkyl group may be 1 to 60, specifically 1 to 40, and more specifically 1 to 20. Specific examples thereof may include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tertiary butyl, secondary butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tertiary pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tertiary octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like, but are not limited thereto.

[0069] In the present specification, alkenyl includes a straight chain or branched chain having 2 to 60 carbon atoms, and may be further substituted with other substituents. The number of carbon atoms of the alkenyl group may be 2 to 60, specifically 2 to 40, and more specifically 2 to 20. Specific examples thereof 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, stilbenyl group, styryl and the like, but are not limited thereto.

[0070] In the present specification, the alkynyl group includes a straight chain or branched chain having 2 to 60 carbon atoms, and may be further substituted with other substituents. The number of carbon atoms of the alkynyl group may be 2 to 60, specifically 2 to 40, and more specifically 2 to 20.

[0071] In the present specification, the alkoxy group may be straight chain, branched chain or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 20. Specific examples thereof may include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tertiary butoxy, secondary butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexoxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy and the like, but are not limited thereto.

[0072] In this specification, cycloalkyl includes monocyclic or polycyclic rings having 3 to 60 carbon atoms, and may be further substituted with other substituents. In this article, polycyclic means a group in which the cycloalkyl is directly bonded to other cyclic groups or fused with other cyclic groups. In this article, other cyclic groups may be cycloalkyl, but may also be different types of cyclic groups, such as heterocycloalkyl, aryl and heteroaryl. The carbon number of the cycloalkyl may be 3 to 60, specifically 3 to 40, and more specifically 5 to 20. Its 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-tertiary butylcyclohexyl, cycloheptyl, cyclooctyl and similar groups, but are not limited thereto.

[0073] In this specification, heterocycloalkyl includes O, S, Se, N or Si as heteroatoms, includes monocyclic or polycyclic rings with 2 to 60 carbon atoms, and may be further substituted with other substituents. In this article, polycyclic means a group in which heterocycloalkyl is directly bonded to other cyclic groups or fused with other cyclic groups. In this article, other cyclic groups may be heterocycloalkyl, but may also be different types of cyclic groups, such as cycloalkyl, aryl and heteroaryl. The number of carbon atoms of heterocycloalkyl may be 2 to 60, specifically 2 to 40, and more specifically 3 to 20.

[0074] In this specification, aryl includes monocyclic or polycyclic rings with 6 to 60 carbon atoms, and may be further substituted with other substituents. In this article, polycyclic means a group in which the aryl is directly bonded to other cyclic groups or fused with other cyclic groups. In this article, other cyclic groups may be aryl, but may also be different types of cyclic groups, such as cycloalkyl, heterocycloalkyl and heteroaryl. Aryl includes spirocyclic groups. The number of carbon atoms of the aryl may be 6 to 60, specifically 6 to 40, and more specifically 6 to 25. Specific examples thereof may include phenyl, biphenyl, terphenyl, quarter, quinque, naphthyl, anthracenyl, chrysene, phenanthryl, peryl, fluorenanthryl, triphenylene, phenanthrenyl, pyrenyl, fused tetraphenyl, fused pentaphenyl, fluorenyl, indenyl, acenaphthenyl, benzofluorenyl, spirobifluorenyl, 2,3-dihydro-1H-indenyl, fused rings thereof and the like, but are not limited thereto.

[0075] In this specification, the phosphine oxide group is represented by -P(=O)R 101 R 102 Indicates that R 101 With R 102 The phosphine oxide group may be the same as or different from each other, and each may be independently a substituent formed by at least one of the following: hydrogen; deuterium; a halogen group; an alkyl group; an alkenyl group; an alkoxy group; a cycloalkyl group; an aryl group; and a heterocyclic group. Specifically, the phosphine oxide group may be substituted with an aryl group, and the examples described above may be used as the aryl group. Examples of the phosphine oxide group may include a diphenyl phosphine oxide group, a dinaphthyl phosphine oxide group, and the like, but are not limited thereto.

[0076] In this specification, a silicon group is a substituent group of Si containing a Si atom as a radical directly attached, and is represented by -SiR 104 R 105 R 106 Indicates. 104 To R 106 The silyl groups may be the same as or different from each other and may each independently be a substituent formed from at least one of the following: hydrogen; deuterium; a halogen group; an alkyl group; an alkenyl group; an alkoxy group; a cycloalkyl group; an aryl group; and a heterocyclic group. Specific examples of the silyl group may include trimethylsilyl, triethylsilyl, tertiary butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, and the like, but are not limited thereto.

[0077] In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.

[0078] When the fluorenyl group is substituted, it may include and the like, however, the structure is not limited thereto.

[0079] In this specification, heteroaryl includes O, S, Se, N or Si as heteroatoms, including monocyclic or polycyclic heteroaryl groups with 2 to 60 carbon atoms, and may be further substituted with other substituents. In this article, polycyclic means a group in which the heteroaryl is directly bonded to other cyclic groups or fused with other cyclic groups. In this article, other cyclic groups may be heteroaryl, but may also be different types of cyclic groups, such as cycloalkyl, heterocycloalkyl and aryl. The number of carbon atoms of the heteroaryl may be 2 to 60, specifically 2 to 40, and more specifically 3 to 25. Specific examples thereof may include pyridyl, pyrrolyl, pyrimidinyl, pyridazinyl, furanyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, furazanyl, oxadiazolyl, thiadiazolyl, dithiazolyl, tetrazolyl, pyranyl, thiopyranyl, diazinyl, oxazinyl, thiazinyl, dioxoalkynyl, triazinyl, tetrazinyl, quinolyl, isoquinolyl, quinolinyl, quinazolinyl, isoquinazolinyl, quinolizinyl, naphthyridinyl, acridinyl, phenanthridinyl, imidazopyridinyl, diazonaphthyl, triazindenyl, indolyl, indolizinyl, benzothiazolyl, benzoxazolyl, benzimidazolyl, benzothienyl, benzofuranyl, dibenzothienyl, dibenzofuranyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenanthrazinyl, dibenzosilole yl, spirobi(dibenzosilole), dihydrophenazinyl, phenanthridinyl, imidazopyridinyl, thienyl, indolo[2,3-a]carbazolyl, indolo[2,3-b]carbazolyl, indolyl, 10,11-dihydro-dibenzo[b,f]azepine, 9,10-dihydroacridinyl, phenazinyl, phenathiazinyl, phenazinyl, naphthoindinidinyl, phenanthridinyl, phenyl 1,2-a]imidazo[1,2-e]indolyl, 5,11-dihydroindeno[1,2-b]carbazolyl, and the like, but are not limited thereto.

[0080] In this specification, the amine group is represented by -NR 107 R 108 Indicates that R 107 With R 108The substituents are the same as or different from each other and may be independently a substituent formed by at least one of the following: hydrogen; deuterium; a halogen group; an alkyl group; an alkenyl group; an alkoxy group; a cycloalkyl group; an aryl group; and a heterocyclic group. The amino group may be selected from the group consisting of: -NH2; a monoalkylamino group; a monoarylamino group; a monoheteroarylamino group; a dialkylamino group; a diarylamino group; a diheteroarylamino group; an alkylarylamino group; an alkylheteroarylamino group; and an arylheteroarylamino group, and although not particularly limited thereto, the number of carbon atoms is preferably 1 to 30. Specific examples thereof may include methylamino, dimethylamino, ethylamino, diethylamino, aniline, naphthylamino, benzidine, dibenzidine, anthracenidine, 9-methyl-anthridine, diphenylamine, phenylnaphthylamine, ditoluidine, phenyltoluidine, triphenylamine, diphenylnaphthylamine, phenylbenzidine, diphenylfluorenylamine, phenyltriphenylamine, biphenyltriphenylamine and the like, but are not limited thereto.

[0081] In this specification, arylene means an arylene group having two bonding sites, i.e., a divalent group. Except for those groups each being a divalent group, the description of aryl provided above can be applied here. In addition, heteroarylene means a heteroaryl group having two bonding sites, i.e., a divalent group. Except for those groups each being a divalent group, the description of heteroaryl provided above can be applied here.

[0082] In the present specification, an "adjacent" group may mean a substituent that replaces an atom directly connected to the atom substituted by the corresponding substituent, a substituent that is closest in space to the corresponding substituent, or another substituent that replaces the atom substituted by the corresponding substituent. For example, two substituents that replace the ortho position in a benzene ring and two substituents that replace the same carbon in an aliphatic ring can be interpreted as groups that are "adjacent" to each other.

[0083] One embodiment of the present application provides a heterocyclic compound represented by Chemical Formula 1.

[0084] When Z1 in Chemical Formula 1 is a substituted or unsubstituted bicyclic or tetracyclic C15 to C60 aryl group having 9 or less protons, L1 may be a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group.

[0085] In other words, when Z1 in Chemical Formula 1 is a substituted or unsubstituted bicyclic or tetracyclic C15 to C60 aryl group having 9 or less protons, it is connected via a linking group (L1), and the substituted or unsubstituted bicyclic or tetracyclic C15 to C60 aryl group having 9 or less protons may be a biphenyl group or a pyrene group.

[0086] In the present application, when the pyrenyl group, which is a substituted or unsubstituted bicyclic or tetracyclic C15 to C60 aryl group having 9 or less protons, is directly bonded to the triazine group, light energy (about 2.4 electron volts) emitted from the green dopant is reabsorbed due to the low T1 energy level (energy level value in the triplet state), and thus the device efficiency and service life may be reduced. Therefore, in the present application, the device efficiency and service life may be increased because the substituted or unsubstituted bicyclic or tetracyclic C15 to C60 aryl group having 9 or less protons is connected to the triazine via the linking group (L1).

[0087] In other words, when Z1 is a biphenyl group or a pyrenyl group in Chemical Formula 1, L1 may be a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group.

[0088] In one embodiment of the present application, Chemical Formula 1 may be represented by any one of the following Chemical Formulas 3 to 8.

[0089] [Chemical formula 3]

[0090]

[0091] [Chemical formula 4]

[0092]

[0093] [Chemical formula 5]

[0094]

[0095] [Chemical formula 6]

[0096]

[0097] [Chemical formula 7]

[0098]

[0099] [Chemical formula 8]

[0100]

[0101] In Chemical Formulae 3 to 8,

[0102] Ar1 to Ar4, L1 and a have the same definitions as in Chemical Formula 1,

[0103] X is O; S; or C(R21)(R22),

[0104] R1 to R5 are the same as or different from each other and are each independently hydrogen; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl,

[0105] R6 to R9 are the same as or different from each other and are each independently hydrogen; deuterium; a halogen group; -CN; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group containing O or S as a heteroatom,

[0106] Z11 is -P(=O)RR'; -SiRR'R"; or a substituted or unsubstituted amine group,

[0107] Z12 and Z13 are the same as or different from each other, and are each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group containing O or S as a heteroatom,

[0108] R, R' and R" have the same definitions as in Chemical Formula 1,

[0109] R21 and R22 are the same as or different from each other, and are each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocyclic ring,

[0110] a1 to d1 are each an integer from 1 to 4,

[0111] e1 is an integer from 1 to 5,

[0112] When a1 to e1 are each 2 or more, the substituents in the brackets are the same as or different from each other.

[0113] r1 and r2 are each an integer of 0 or 1, and

[0114] r1+r2<2.

[0115] Specifically, as in Chemical Formulae 3 to 8, the heterocyclic compound according to the present application has a sufficiently long substituent or a substituent having a large molecular weight, which can effectively stabilize electrons since LUMO is delocalized from the triazine core to the substituent, and therefore, the organic light-emitting device including the heterocyclic compound has excellent service life characteristics.

[0116] In addition, the dipole moment is different depending on the type of the terminal substituent of the triazine as the core structure, and the molecular mobility can be adjusted. This allows the appropriate triazine terminal substituent to be selected depending on the charge balance of the device and allows the sublimation temperature to be adjusted by affecting the molecular rigidity depending on the terminal substituent, and therefore, the organic light-emitting device including the heterocyclic compound has excellent service life characteristics. In other words, too high a sublimation temperature causes molecular degradation before the molecules sublimate, which inhibits the efficiency and service life of the device.

[0117] In one embodiment of the present application, Chemical Formula 1 may be represented by any one of the following Chemical Formulas 9 to 14.

[0118] [Chemical formula 9]

[0119]

[0120] [Chemical formula 10]

[0121]

[0122] [Chemical formula 11]

[0123]

[0124] [Chemical formula 12]

[0125]

[0126] [Chemical formula 13]

[0127]

[0128] [Chemical formula 14]

[0129]

[0130] In Chemical Formula 9 to Chemical Formula 14,

[0131] L1, Z1, a and b have the same definitions as in Chemical Formula 1, and

[0132] Ar11 to Ar14 are the same as or different from each other, and are each independently deuterium; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0133] In one embodiment of the present application, Ar1 to Ar4 are the same as or different from each other, and may be each independently hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0134] In another embodiment, Ar1 to Ar4 are the same as or different from each other, and may each independently be hydrogen; deuterium; substituted or unsubstituted C1 to C40 alkyl; substituted or unsubstituted C6 to C40 aryl; or substituted or unsubstituted C2 to C40 heteroaryl.

[0135] In another embodiment, Ar1 to Ar4 are the same as or different from each other, and are each independently hydrogen; deuterium; or a substituted or unsubstituted C6 to C40 aryl group.

[0136] In another embodiment, Ar1 to Ar4 are the same as or different from each other, and are each independently hydrogen; deuterium; or a substituted or unsubstituted C6 to C20 aryl group.

[0137] In another embodiment, Ar1 to Ar4 are the same as or different from each other, and may each independently be hydrogen; deuterium; or a substituted or unsubstituted C6 to C20 monocyclic or polycyclic aromatic group.

[0138] In another embodiment, Ar1 to Ar4 are the same as or different from each other, and may each independently be hydrogen; deuterium; or a substituted or unsubstituted C6 to C20 monocyclic aromatic group.

[0139] In another embodiment, Ar1 to Ar4 are the same as or different from each other, and may each independently be hydrogen; deuterium; or phenyl.

[0140] In one embodiment of the present application, Ar11 to Ar14 are the same as or different from each other, and may each independently be deuterium; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0141] In another embodiment, Ar11 to Ar14 are the same as or different from each other, and are each independently deuterium; or a substituted or unsubstituted C6 to C60 aryl group.

[0142] In another embodiment, Ar11 to Ar14 are the same as or different from each other, and are each independently deuterium; or a substituted or unsubstituted C6 to C20 monocyclic aromatic group.

[0143] In another embodiment, Ar11 to Ar14 may be deuterium; or a phenyl group.

[0144] In one embodiment of the present application, L1 may be a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group.

[0145] In another embodiment, L1 may be a direct bond; a substituted or unsubstituted C6 to C40 arylene group; or a substituted or unsubstituted C2 to C40 heteroarylene group.

[0146] In another embodiment, L1 may be a direct bond; a C6 to C40 arylene group; or a C2 to C40 heteroarylene group.

[0147] In another embodiment, L1 may be a direct bond; or a C6 to C40 arylene group.

[0148] In another embodiment, L1 may be a direct bond; or a C6 to C40 monocyclic or polycyclic arylene group.

[0149] In another embodiment, L1 can be a direct bond; a phenylene group; or a biphenylene group.

[0150] In one embodiment of the present application, Z1 can be selected from the group consisting of: halogen; -CN; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C10 to C60 aryl; substituted or unsubstituted C2 to C60 heteroaryl containing O or S as a heteroatom; P(=O)RR'; -SiRR'R"; and substituted or unsubstituted amine.

[0151] In another embodiment, Z1 may be selected from the group consisting of: a substituted or unsubstituted C10 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group containing O or S as a heteroatom; and -SiRR'R".

[0152] In another embodiment, Z1 may be selected from the group consisting of: a substituted or unsubstituted C10 to C40 aryl group; a substituted or unsubstituted C2 to C40 heteroaryl group containing O or S as a heteroatom; and -SiRR'R".

[0153] In another embodiment, Z1 can be selected from the group consisting of: C10 to C40 aryl which is unsubstituted or substituted with C1 to C20 alkyl or C6 to C20 aryl; C2 to C40 heteroaryl containing O or S as a heteroatom; and -SiRR'R".

[0154] In another embodiment, Z1 may be a biphenyl group; a terphenyl group which is unsubstituted or substituted with a C6 to C20 aryl group; a quaterphenyl group which is unsubstituted or substituted with a C6 to C20 aryl group; a pentaphenyl group; a dimethylfluorenyl group; a diphenylfluorenyl group; a spirobifluorenyl group; a triphenylene group; a dibenzofuranyl group; a dibenzothiophenyl group; or -SiRR'R".

[0155] In another embodiment, Z1 can be biphenyl; terphenyl; dimethylfluorenyl; diphenylfluorenyl; spirobifluorenyl; triphenylene; dibenzofuranyl; dibenzothienyl; or -SiRR'R".

[0156] In one embodiment of the present application, X may be O.

[0157] In one embodiment of the present application, X may be S.

[0158] In one embodiment of the present application, X may be C(R21)(R22).

[0159] In one embodiment of the present application, R1 to R5 are the same as or different from each other, and may be each independently hydrogen; a substituted or unsubstituted C1 to C60 alkyl; a substituted or unsubstituted C6 to C60 aryl; or a substituted or unsubstituted C2 to C60 heteroaryl.

[0160] In another embodiment, R1 to R5 are the same as or different from each other, and may be each independently hydrogen; or a substituted or unsubstituted C6 to C60 aryl group.

[0161] In another embodiment, R1 to R5 are the same as or different from each other, and may be each independently hydrogen; or a substituted or unsubstituted C6 to C40 aryl group.

[0162] In another embodiment, R1 to R5 are the same as or different from each other, and may be each independently hydrogen; or a substituted or unsubstituted C6 to C20 aryl group.

[0163] In another embodiment, R1 to R5 are the same as or different from each other, and may be each independently hydrogen; or C6 to C20 aryl.

[0164] In another embodiment, R1 to R5 are the same as or different from each other, and may be each independently hydrogen; or a biphenyl group.

[0165] In another embodiment, R3 of Chemical Formula 3 may be hydrogen.

[0166] In another embodiment, R4 of Chemical Formula 4 may be hydrogen.

[0167] In one embodiment of the present application, R6 to R9 are the same as or different from each other, and may each independently be hydrogen; deuterium; a halogen group; -CN; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group containing O or S as a heteroatom.

[0168] In another embodiment, R6 to R9 are the same as or different from each other, and may each independently be hydrogen; a substituted or unsubstituted C1 to C40 alkyl group; a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group containing O or S as a heteroatom.

[0169] In another embodiment, R6 to R9 may be hydrogen.

[0170] In one embodiment of the present application, Z11 may be -P(=O)RR'; -SiRR'R"; or a substituted or unsubstituted amine group.

[0171] In another embodiment, Z11 may be -SiRR'R".

[0172] In one embodiment of the present application, R, R' and R" are the same as or different from each other, and may each independently be a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0173] In another embodiment, R, R' and R" are the same as or different from each other, and may each independently be a substituted or unsubstituted C1 to C60 alkyl group; or a substituted or unsubstituted C6 to C60 aryl group.

[0174] In another embodiment, R, R' and R" are the same as or different from each other, and may be each independently a C1 to C60 alkyl group; or a C6 to C60 aryl group.

[0175] In another embodiment, R, R' and R" are the same as or different from each other, and can each independently be a methyl group; or a phenyl group.

[0176] In another embodiment, R, R' and R" may be phenyl.

[0177] In one embodiment of the present application, R21 and R22 are the same as or different from each other, and are each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, or two or more adjacent groups may be bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocycle.

[0178] In another embodiment, R21 and R22 are the same as or different from each other and are each independently a substituted or unsubstituted C1 to C40 alkyl group; or a substituted or unsubstituted C6 to C40 aryl group, or two or more adjacent groups may be bonded to each other to form a substituted or unsubstituted C6 to C40 aromatic hydrocarbon ring.

[0179] In another embodiment, R21 and R22 are the same as or different from each other and are each independently a substituted or unsubstituted C1 to C10 alkyl group; or a substituted or unsubstituted C6 to C20 aryl group, or two or more adjacent groups may be bonded to each other to form a substituted or unsubstituted C6 to C30 aromatic hydrocarbon ring.

[0180] In another embodiment, R21 and R22 are the same as or different from each other and are each independently a C1 to C10 alkyl group; or a C6 to C20 aryl group, or two or more adjacent groups may be bonded to each other to form a C6 to C30 aromatic hydrocarbon ring.

[0181] In another embodiment, R21 and R22 are the same as or different from each other and are independently methyl or phenyl, or two or more adjacent groups may be bonded to form a fluorene ring.

[0182] In one embodiment of the present application, R21 and R22 are the same as or different from each other, and are each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, or R21 and R22 may be bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocyclic ring.

[0183] In another embodiment, R21 and R22 are the same as or different from each other, and are each independently a substituted or unsubstituted C1 to C10 alkyl group; or a substituted or unsubstituted C6 to C20 aryl group, or R21 and R22 may be bonded to each other to form a substituted or unsubstituted C6 to C30 aromatic hydrocarbon ring.

[0184] In another embodiment, R21 and R22 are the same as or different from each other and are independently a methyl group or a phenyl group, or R21 and R22 may be bonded to each other to form a fluorene ring.

[0185] In the heterocyclic compound provided in one embodiment of the present application, Chemical Formula 1 may be represented by any one of the following compounds.

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206] In addition, by introducing various substituents into the structure of Chemical Formula 1, a compound having unique characteristics 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 devices into the core structure, a material that meets the conditions required for each organic material layer can be synthesized.

[0207] In addition, by introducing various substituents into the structure of Chemical Formula 1, the energy band gap may be finely controlled, and at the same time, characteristics at the interface between organic materials are enhanced, and material applications may become diversified.

[0208] At the same time, the compound has a high glass transition temperature (Tg) and has excellent thermal stability. Such improvement in thermal stability becomes an important factor in providing driving stability to the device.

[0209] In addition, one embodiment of the present application provides an organic light-emitting device, comprising: a first electrode; a second electrode, arranged opposite to the first electrode; and one or more organic material layers, arranged between the first electrode and the second electrode, wherein one or more layers of the organic material layer comprise a heterocyclic compound represented by Chemical Formula 1.

[0210] According to one embodiment of the present specification, the first electrode may be an anode, and the second electrode may be a cathode.

[0211] In another embodiment, the first electrode may be a cathode and the second electrode may be an anode.

[0212] In one embodiment of the present application, the organic light-emitting device may be a blue organic light-emitting device, and the heterocyclic compound represented by Chemical Formula 1 may be used as a material of the blue organic light-emitting device.

[0213] In one embodiment of the present application, the organic light-emitting device may be a green organic light-emitting device, and the heterocyclic compound represented by Chemical Formula 1 may be used as a material of the green organic light-emitting device.

[0214] In one embodiment of the present application, the organic light-emitting device may be a red organic light-emitting device, and the heterocyclic compound represented by Chemical Formula 1 may be used as a material of the red organic light-emitting device.

[0215] In one embodiment of the present application, the organic light-emitting device may be a blue organic light-emitting device, and the heterocyclic compound represented by Chemical Formula 1 may be used as a light-emitting layer material of the blue organic light-emitting device.

[0216] In one embodiment of the present application, the organic light-emitting device may be a green organic light-emitting device, and the heterocyclic compound represented by Chemical Formula 1 may be used as a light-emitting layer material of the green organic light-emitting device.

[0217] In one embodiment of the present application, the organic light-emitting device may be a red organic light-emitting device, and the heterocyclic compound according to Chemical Formula 1 may be used as a light-emitting layer material of the red organic light-emitting device.

[0218] Specific details of the heterocyclic compound represented by Chemical Formula 1 are the same as the description provided above.

[0219] In addition to using the heterocyclic compounds described above to form one or more organic material layers, the organic light-emitting device of the present disclosure may be manufactured using commonly used organic light-emitting device manufacturing methods and materials.

[0220] When manufacturing an organic light-emitting device, the heterocyclic compound can be formed into an organic material layer via a solution coating method and a vacuum deposition method. Herein, the solution coating method means spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating and the like, but is not limited thereto.

[0221] The organic material layer of the organic light-emitting device of the present disclosure may be formed in a single-layer structure, or may also be formed in a multi-layer structure in which two or more organic material layers are laminated. For example, the organic light-emitting device according to one embodiment of the present 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, and the like as organic material layers. However, the structure of the organic light-emitting device is not limited thereto, and may include a small number of organic material layers.

[0222] In the organic light-emitting device of the present disclosure, the organic material layer includes a light-emitting layer, and the light-emitting layer may include a heterocyclic compound.

[0223] In an organic light-emitting device provided in one embodiment of the present application, the organic material layer including the heterocyclic compound represented by Chemical Formula 1 further includes a heterocyclic compound represented by the following Chemical Formula 2.

[0224] [Chemical formula 2]

[0225]

[0226] In chemical formula 2,

[0227] Rc and Rd are the same as or different from each other and are each independently selected from the group consisting of hydrogen, deuterium, a halogen group, -CN, a substituted or unsubstituted C1 to C60 alkyl group, a substituted or unsubstituted C2 to C60 alkenyl group, a substituted or unsubstituted C2 to C60 alkynyl group, a substituted or unsubstituted C1 to C60 alkoxy group, a substituted or unsubstituted C3 to C60 cycloalkyl group, a substituted or unsubstituted C2 to C60 heterocycloalkyl group, a substituted or unsubstituted C6 to C60 aryl group, a substituted or unsubstituted C2 to C60 heteroaryl group, -Si(R10)(R11)(R12), -P(=O)(R10)(R11), and a substituted or unsubstituted amino group, or two or more adjacent groups bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocyclic ring,

[0228] R10, R11 and R12 are the same as or different from each other and are each independently hydrogen; deuterium; -CN; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl,

[0229] Ra and Rb are the same as or different 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,

[0230] r and s are each an integer from 0 to 7, and

[0231] When r and s are each 2 or more, the substituents in the parentheses are the same as or different from each other.

[0232] When the organic material layer of the organic light-emitting device includes the heterocyclic compound of Chemical Formula 1 and the heterocyclic compound of Chemical Formula 2, more excellent efficiency and lifespan are obtained. Such results may predict that when the two compounds are included at the same time, an exciplex phenomenon occurs.

[0233] The exciplex phenomenon is a phenomenon in which energy having the size of the donor (p host) HOMO energy level and the acceptor (n host) LUMO energy level is released due to electron exchange between two molecules. When the exciplex phenomenon occurs between two molecules, reverse intersystem crossing (RISC) occurs, and thus, the internal quantum efficiency of fluorescence can be increased up to 100%. When a donor (p host) having good hole transporting ability and an acceptor (n host) having good electron transporting ability are used as hosts of the light-emitting layer, holes are injected into the p host and electrons are injected into the n host, and thus, the driving voltage can be reduced, which ultimately helps to enhance the service life.

[0234] In one embodiment of the present application, Chemical Formula 2 may be represented by the following Chemical Formula 2-1 or Chemical Formula 2-2.

[0235] [Chemical formula 2-1]

[0236]

[0237] [Chemical formula 2-2]

[0238]

[0239] In Chemical Formula 2-1 and Chemical Formula 2-2,

[0240] Rc, Rd, r and s have the same definitions as in Chemical Formula 2,

[0241] Ra1, Rb1 and Rc1 are the same as or different from each other, and are each independently a substituted or unsubstituted C6 to C60 aryl group,

[0242] R1' and R2' are the same as or different from each other and are independently selected from the group consisting of: hydrogen; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C6 to C60 aryl; and substituted or unsubstituted C2 to C60 heteroaryl,

[0243] L1' is a direct bond; or a substituted or unsubstituted C6 to C60 arylene group,

[0244] Ar1′ is a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group containing at least one of S and O,

[0245] m' is an integer from 0 to 4,

[0246] n' is an integer from 0 to 2, and

[0247] When m' is 2 or more, the substituents in the respective brackets are the same as or different from each other.

[0248] In one embodiment of the present application, Rc and Rd of Chemical Formula 2 may be hydrogen.

[0249] In one embodiment of the present application, Ra1 and Rb1 of Chemical Formula 2-1 are the same as or different from each other, and may each independently be a substituted or unsubstituted C6 to C60 aryl group.

[0250] In another embodiment, Ra1 and Rb1 of Chemical Formula 2-1 are the same as or different from each other, and may each independently be a substituted or unsubstituted C6 to C40 aryl group.

[0251] In another embodiment, Ra1 and Rb1 of Chemical Formula 2-1 are the same as or different from each other, and may each independently be a C6 to C40 aryl group which is unsubstituted or substituted with one or more substituents selected from the group consisting of a C1 to C40 alkyl group, a C6 to C40 aryl group, -CN, and Si(R104)(R105)(R106).

[0252] In another embodiment, Ra1 and Rb1 of Chemical Formula 2-1 are the same as or different from each other, and may each independently be a phenyl group which is unsubstituted or substituted with phenyl, -CN or -Si(R104)(R105)(R106); a biphenyl group which is unsubstituted or substituted with phenyl; a naphthyl group; a fluorenyl group which is unsubstituted or substituted with methyl or phenyl; a spirobifluorenyl group; or a triphenylene group.

[0253] In one embodiment of the present application, R104, R105, and R106 of Chemical Formula 2-1 may be a phenyl group.

[0254] In one embodiment of the present application, Rc1 of Chemical Formula 2-2 may be a substituted or unsubstituted C6 to C60 aryl group.

[0255] In another embodiment, Rc1 of Chemical Formula 2-2 may be a substituted or unsubstituted C6 to C40 aryl group.

[0256] In another embodiment, Rc1 of Chemical Formula 2-2 may be a C6 to C40 aryl group.

[0257] In another embodiment, Rc1 of Chemical Formula 2-2 may be a phenyl group.

[0258] In one embodiment of the present application, R1' and R2' of Chemical Formula 2-2 are the same as or different from each other, and can be independently selected from the group consisting of: hydrogen; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C6 to C60 aryl; and substituted or unsubstituted C2 to C60 heteroaryl.

[0259] In another embodiment, R1' and R2' of Chemical Formula 2-2 are the same as or different from each other and can be independently selected from the group consisting of: hydrogen; substituted or unsubstituted C1 to C40 alkyl; substituted or unsubstituted C6 to C40 aryl; and substituted or unsubstituted C2 to C40 heteroaryl.

[0260] In another embodiment, R1′ and R2′ of Chemical Formula 2-2 are the same as or different from each other and can be independently selected from the group consisting of: hydrogen; C1 to C40 alkyl; C6 to C40 aryl; and C2 to C40 heteroaryl.

[0261] In another embodiment, R1′ and R2′ of Chemical Formula 2-2 may be hydrogen.

[0262] In one embodiment of the present application, L1′ of Chemical Formula 2-2 may be a direct bond; or a substituted or unsubstituted C6 to C60 arylene group.

[0263] In another embodiment, L1′ of Chemical Formula 2-2 may be a direct bond; or a substituted or unsubstituted C6 to C40 arylene group.

[0264] In another embodiment, L1′ of Chemical Formula 2-2 may be a direct bond; or a substituted or unsubstituted C6 to C20 arylene group.

[0265] In another embodiment, L1′ of Chemical Formula 2-2 may be a direct bond; or a C6 to C20 arylene group.

[0266] In another embodiment, L1′ of Chemical Formula 2-2 may be a direct bond; or a phenylene group.

[0267] In one embodiment of the present application, Ar1′ of Chemical Formula 2-2 may be a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group including at least one of S and O.

[0268] In another embodiment, Ar1′ of Chemical Formula 2-2 may be a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group including at least one of S and O.

[0269] In another embodiment, Ar1′ of Chemical Formula 2-2 may be an unsubstituted or C1 to C10 alkyl-substituted C6 to C40 aryl group; or an unsubstituted or substituted C2 to C40 heteroaryl group including at least one of S and O.

[0270] In another embodiment, Ar1′ of Chemical Formula 2-2 may be a phenyl group, a biphenyl group, a naphthyl group, a dimethylfluorenyl group, a dibenzothienyl group, or a dibenzofuranyl group.

[0271] In one embodiment of the present application, Chemical Formula 2 may be represented by any one of the following compounds.

[0272]

[0273]

[0274]

[0275]

[0276]

[0277]

[0278]

[0279]

[0280]

[0281]

[0282] In addition, another embodiment of the present application provides a composition for an organic material layer of an organic light-emitting device, wherein the composition includes a heterocyclic compound represented by Chemical Formula 1 and a heterocyclic compound represented by Chemical Formula 2.

[0283] Detailed descriptions about the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2 are the same as those provided above.

[0284] In the composition, the heterocyclic compound represented by Chemical Formula 1:the heterocyclic compound represented by Chemical Formula 2 may have a weight ratio of 1:10 to 10:1, 1:8 to 8:1, 1:5 to 5:1, or 1:2 to 2:1, however, the weight ratio is not limited thereto.

[0285] The composition may be used when forming an organic material of an organic light-emitting device, and may more preferably be used when forming a main body of a light-emitting layer.

[0286] In one embodiment of the present application, the organic material layer includes a heterocyclic compound represented by Chemical Formula 1 and a heterocyclic compound represented by Chemical Formula 2, and a phosphorescent dopant may be used together with the heterocyclic compounds.

[0287] In one embodiment of the present application, the organic material layer includes a heterocyclic compound represented by Chemical Formula 1 and a heterocyclic compound represented by Chemical Formula 2, and an iridium-based dopant may be used together with the heterocyclic compounds.

[0288] As the material of the phosphorescent dopant, those materials known in the art can be used.

[0289] For example, phosphorescent dopant materials represented by LL'MX', LL'L'M, LMX'X', L2MX', and L3M may be used, however, the scope of the present disclosure is not limited to these examples.

[0290] Herein, L, L′, L′, X′, and X′ are bidentate ligands different from each other, and M is a metal that forms an octahedral complex.

[0291] M may include iridium, platinum, osmium, and the like.

[0292] L is an anionic bidentate ligand coordinated to M as an iridium-based dopant through sp2 carbon and heteroatoms, and X can act on trapped electrons or holes. Non-limiting examples of L may include 2-(1-naphthyl)benzoxazole, (2-phenylbenzoxazole), (2-phenylbenzothiazole), (2-phenylbenzothiazole), (7,8-benzoquinoline), (thienylpyridine), phenylpyridine, benzothienylpyridine, 3-methoxy-2-phenylpyridine, thienylpyrazine, tolylpyridine, and the like. Non-limiting examples of X' and X' may include acetylacetonate (acac), hexafluoroacetylacetonate, o-hydroxybenzylidene, picolinate, 8-hydroxyquinoline, and the like.

[0293] More specific examples thereof are described below, however, the phosphorescent dopant is not limited to these examples.

[0294]

[0295] In one embodiment of the present application, as an iridium-based dopant, Ir(ppy) 3 may be used as a green phosphorescent dopant.

[0296] In one embodiment of the present application, the content of the dopant may be 1% to 15%, preferably 3% to 10%, and more preferably 5% to 10%, based on the entire light-emitting layer.

[0297] In the organic light-emitting device of the present disclosure, the organic material layer includes an electron injection layer or an electron transport layer, and the electron injection layer or the electron transport layer may include a heterocyclic compound.

[0298] In another organic light-emitting device, the organic material layer includes an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer may include a heterocyclic compound.

[0299] In another organic light-emitting device, the organic material layer includes an electron transport layer, an emission layer, or a hole blocking layer, and the electron transport layer, the emission layer, or the hole blocking layer may include a heterocyclic compound.

[0300] The organic light-emitting device of the present disclosure 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.

[0301] Figures 1 to 3 The lamination sequence of electrodes and organic material layers of an organic light-emitting device according to one embodiment of the present application is shown. However, the scope of the present application is not limited to these drawings, and the structure of an organic light-emitting device known in the art can also be used in the present application.

[0302] Figure 1 1 shows an organic light emitting device in which an anode 200, an organic material layer 300, and a cathode 400 are sequentially laminated on a substrate 100. However, the structure is not limited to such a structure, and as Figure 2 As shown in , an organic light-emitting device can also be obtained in which a cathode, an organic material layer, and an anode are sequentially laminated on a substrate.

[0303] Figure 3 The case where the organic material layer is multi-layered is shown. Figure 3 The organic light-emitting device 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 the present application is not limited to such a laminated structure, and if necessary, the layer other than the light-emitting layer may not be included, and other desired functional layers may be further added.

[0304] One embodiment of the present application provides a method for manufacturing an organic light-emitting device, the method comprising: preparing a substrate; forming a first electrode on the substrate; forming one or more organic material layers on the first electrode; and forming a second electrode on the organic material layer, wherein forming the organic material layer comprises forming one or more organic material layers using a composition for an organic material layer according to one embodiment of the present application.

[0305] In a method of manufacturing an organic light-emitting device provided in one embodiment of the present application, the organic material layer is formed by pre-mixing the heterocyclic compound of Chemical Formula 1 and the heterocyclic compound of Chemical Formula 2 using a thermal vacuum deposition method.

[0306] Pre-mixed means that the heterocyclic compound of Chemical Formula 1 and the heterocyclic compound of Chemical Formula 2 are first mixed in one supply source before being deposited on the organic material layer.

[0307] The premixed material may be referred to as a composition for an organic material layer according to one embodiment of the present application.

[0308] If necessary, the organic material layer comprising Chemical Formula 1 may further comprise other materials.

[0309] If necessary, the organic material layer including both Chemical Formula 1 and Chemical Formula 2 may further include other materials.

[0310] In an organic light-emitting device according to one embodiment of the present application, materials other than the compound of Chemical Formula 1 or Chemical Formula 2 are shown below, however, these materials are only for illustrative purposes and are not used to limit the scope of the present application, and may be replaced by materials known in the art.

[0311] A material having a relatively large work function may be used as the anode material, and a transparent conductive oxide, metal, conductive polymer, or the like may be used as the anode material. Specific examples of the anode material include: metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline; and the like, but are not limited thereto.

[0312] A material having a relatively small work function may be used as the cathode material, and a metal, a metal oxide, a conductive polymer, or the like may be used as the cathode material. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer structure materials such as LiF / Al or LiO2 / Al; and the like, but are not limited thereto.

[0313] As the hole injection material, a known hole injection material can be used, and for example, the following can be used: a phthalocyanine compound such as copper phthalocyanine disclosed in U.S. Pat. No. 4,356,429; or a starburst amine derivative such as tris(4-carboxamidoyl-9-ylphenyl)amine (TCTA), 4,4',4"-tris[phenyl(m-tolyl)amino]triphenylamine (m-MTDATA) or 1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene (m-MTDAPB) described in the literature [Advanced Materials, 6, p. 677 (1994)]; polyaniline / dodecylbenzenesulfonic acid (Polyaniline / Dodecylbenzenesulfonic Acid) as a conductive polymer having solubility; acid), Poly(3,4-ethylenedioxythiophene) / Poly(4-styrenesulfonate), Polyaniline / Camphor sulfonic acid, or Polyaniline / Poly(4-styrene-sulfonate); and the like.

[0314] As the hole transport material, pyrazoline derivatives, aromatic amine derivatives, stilbene derivatives, triphenyldiamine derivatives and the like can be used, and low molecular weight or high molecular weight materials can also be used as the hole transport material.

[0315] Metal complexes of oxadiazole derivatives, anthraquinone dimethane and its derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, tetracyanoanthraquinone dimethane and its derivatives, fluorenone derivatives, diphenyl dicyanoethylene and its derivatives, diphenoquinone derivatives, 8-hydroxyquinoline and its derivatives and the like can be used as electron transport materials, and polymer materials and low molecular weight materials can also be used as electron transport materials.

[0316] As an example of the electron injection material, LiF is generally used in the art, however, the present application is not limited thereto.

[0317] As the luminescent material, a material emitting red, green or blue light can be used, and two or more luminescent materials can be mixed and used as needed. Herein, two or more luminescent materials can be used by depositing as individual supply sources or by premixing and depositing as one supply source. In addition, a fluorescent material can also be used as the luminescent material, however, a phosphorescent material can also be used. A material that emits light by bonding electrons and holes injected from the anode and cathode, respectively, can be used alone as the luminescent material, however, a material having a host material and a doping material that participate in luminescence can also be used as the luminescent material.

[0318] When mixing the light emitting material host, the same series of hosts may be mixed, or hosts of different series may be mixed. For example, any two or more types of materials among n-type host materials or p-type host materials may be selected and used as host materials of the light emitting layer.

[0319] Depending on the materials used, the organic light-emitting device according to one embodiment of the present application may be a top emission type, a bottom emission type, or a double-sided emission type.

[0320] The heterocyclic compound according to one embodiment of the present application may also be used in organic electronic devices including organic solar cells, organic photoconductors, organic transistors, and the like according to similar principles as used in organic light-emitting devices.

[0321] Experimental example

[0322] Hereinafter, the present specification will be described in more detail with reference to examples, however, these are for illustrative purposes only, and the scope of the present application is not limited thereto.

[0323] <Preparation Example>

[0324] <Preparation Example 1> Preparation of Compound 1-1

[0325]

[0326] 1 Preparation of intermediate 1-1-1

[0327] After 9H-carbazole (10.0 g, 59.8 mmol) was dissolved in THF, the flask was substituted with nitrogen at -78°C. 2.5M n-BuLi (28.7 ml, 71.8 mmol) was slowly introduced thereinto at -78°C, and the resultant was stirred for 30 minutes. 2,4,6-trichloro-1,3,5-triazine (5.5 g, 29.9 mmol) was introduced thereinto, and the resultant was stirred at room temperature for 2 hours. After the reaction was completed, the resultant was extracted by introducing distilled water and DCM thereinto at room temperature, and after the organic layer was dried with MgSO4, the solvent was removed using a rotary evaporator. The reaction material was recrystallized with methanol to obtain intermediate 1-1-1 (10.9 g, 82%).

[0328] 2) Preparation of compound 1-1

[0329] After the intermediate 1-1-1 (10 g, 22.42 mmol), [1,1':2',1"-terphenyl]-2-ylboronic acid (6.8 g, 24.67 mmol), Pd(PPh3)4 (1.3 g, 1.1 mmol) and K2CO3 (6.2 g, 44.84 mmol) were dissolved in 1,4-dioxane / H2O (250 ml / 50 ml), the mixture was refluxed for 24 hours. After the reaction was completed, the resultant was extracted by introducing distilled water and DCM therein at room temperature, and after the organic layer was dried with MgSO4, the solvent was removed using a rotary evaporator. The reaction material was purified by column chromatography (DCM:Hex=1:3), and recrystallized with methanol to obtain the target compound 1-1 (12.3 g, 86%).

[0330] The target compound was synthesized in the same manner as in Preparation Example 1, except that Compound A of the following Table 1 was used instead of [1,1':2',1"-terphenyl]-2-ylboronic acid.

[0331] [Table 1]

[0332]

[0333]

[0334] <Preparation Example 2> Preparation of Compound 1-177

[0335]

[0336] 1) Preparation of intermediate 1-177-2

[0337] After 9H-carbazole (10.0 g, 59.8 mmol) was dissolved in THF, the flask was substituted with nitrogen at -78°C. 2.5M n-BuLi (28.7 ml, 71.8 mmol) was slowly introduced thereinto at -78°C, and the resultant was stirred for 30 minutes. 2,4,6-trichloro-1,3,5-triazine (10.9 g, 59.8 mmol) was introduced thereinto, and the resultant was stirred at room temperature for 2 hours. After the reaction was completed, the resultant was extracted by introducing distilled water and DCM thereinto at room temperature, and after the organic layer was dried with MgSO4, the solvent was removed using a rotary evaporator. The reaction material was recrystallized with methanol to obtain intermediate 1-177-2 (15.6 g, 83%).

[0338] 2) Preparation of intermediate 1-177-1

[0339] After 2-phenyl-9H-carbazole (14.5 g, 59.8 mmol) was dissolved in THF, the flask was substituted with nitrogen at -78°C. 2.5M n-BuLi (28.7 ml, 71.8 mmol) was slowly introduced thereto at -78°C, and the resultant was stirred for 30 minutes. Intermediate 1-177-2 (18.8 g, 59.8 mmol) was introduced thereto, and the resultant was stirred at room temperature for 2 hours. After the reaction was completed, the resultant was extracted by introducing distilled water and DCM thereto at room temperature, and after the organic layer was dried with MgSO4, the solvent was removed using a rotary evaporator. The reaction material was recrystallized with methanol to obtain intermediate 1-177-1 (25.6 g, 82%).

[0340] 2) Preparation of Compound 1-177

[0341] After the intermediate 1-177-1 (11.7 g, 22.42 mmol), [1,1':2',1"-terphenyl]-4-ylboronic acid (6.8 g, 24.67 mmol), Pd(PPh3)4 (1.3 g, 1.1 mmol) and K2CO3 (6.2 g, 44.84 mmol) were dissolved in 1,4-dioxane / H2O (250 mL / 50 mL), the mixture was refluxed for 24 hours. After the reaction was completed, the resultant was extracted by introducing distilled water and DCM therein at room temperature, and after the organic layer was dried with MgSO4, the solvent was removed using a rotary evaporator. The reaction material was purified by column chromatography (DCM:Hex=1:3), and recrystallized with methanol to obtain the target compound 1-177 (13.6 g, 85%).

[0342] The target compound was synthesized in the same manner as in Preparation Example 2, except that Compound B of the following Table 2 was used instead of [1,1':2',1"-terphenyl]-4-ylboronic acid.

[0343] [Table 2]

[0344]

[0345] The target compound was synthesized in the same manner as in Preparation Example 1, except that Compound C in Table 3 below was used instead of 9H-carbazole, and Compound D in Table 3 below was used instead of [1,1':2',1"-terphenyl]-2-ylboronic acid.

[0346] [Table 3]

[0347]

[0348] <Preparation Example 3> Preparation of Compound 2-2

[0349]

[0350] 1) Preparation of intermediate 2-2-2

[0351] After dissolving 2-bromodibenzo[b,d]thiophene (4.2 g, 15.8 mmol), 9-phenyl-9H,9'H-3,3'-dicarbazole (6.5 g, 15.8 mmol), CuI (3.0 g, 15.8 mmol), trans-1,2-diaminocyclohexane (1.9 ml, 15.8 mmol) and K3PO4 (3.3 g, 31.6 mmol) in 1,4-oxane (100 ml), the mixture was refluxed for 24 hours. After the reaction was completed, the resultant was extracted by introducing distilled water and DCM therein at room temperature, and after drying the organic layer with MgSO4, the solvent was removed using a rotary evaporator. The reaction material was purified by column chromatography (DCM:Hex=1:3) and recrystallized with methanol to obtain intermediate 2-2-2 (7.9 g, 85%).

[0352] 2) Preparation of intermediate 2-2-1

[0353] To a mixed solution of intermediate 2-2-2 (8.4 g, 14.3 mmol) and THF (100 ml) was added dropwise 2.5 M n-BuLi (7.4 ml, 18.6 mmol) at -78 ° C, and the resultant was stirred at room temperature for 1 hour. Trimethyl borate (4.8 ml, 42.9 mmol) was added dropwise to the reaction mixture, and the resultant was stirred at room temperature for 2 hours. After the reaction was completed, the resultant was extracted by introducing distilled water and DCM therein at room temperature, and after the organic layer was dried with MgSO4, the solvent was removed using a rotary evaporator. The reaction material was purified by column chromatography (DCM: MeOH = 100: 3) and recrystallized with DCM to obtain intermediate 2-2-1 (3.9 g, 70%).

[0354] 3) Preparation of compound 2-2

[0355] After the intermediate 2-2-1 (6.7 g, 10.5 mmol), iodobenzene (2.1 g, 10.5 mmol), Pd(PPh3)4 (606 mg, 0.52 mmol) and K2CO3 (2.9 g, 21.0 mmol) were dissolved in toluene / EtOH / H2O (100 ml / 20 ml / 20 ml), the mixture was refluxed for 12 hours. After the reaction was completed, the resultant was extracted by introducing distilled water and DCM therein at room temperature, and after the organic layer was dried with MgSO4, the solvent was removed using a rotary evaporator. The reaction material was purified by column chromatography (DCM:Hex=1:3), and recrystallized with methanol to obtain the target compound 2-2 (4.9 g, 70%).

[0356] <Preparation Example 4> Synthesis of Compound 2-3

[0357] The target compound 2-3 (83%) was obtained in the same manner as in the preparation of the compound 2-2 of Preparation Example 3, except that 4-iodo-1,1′-biphenyl was used instead of iodobenzene.

[0358] <Preparation Example 5> Synthesis of Compound 2-12

[0359] The target compound 2-12 (80%) was obtained in the same manner as in the preparation of the compound 2-2 of Preparation Example 3, except that 4-iododibenzo[b,d]furan was used instead of iodobenzene.

[0360] <Preparation Example 6> Synthesis of Compound 3-3

[0361]

[0362] After dissolving 3-bromo-1,1'-biphenyl (3.7 g, 15.8 mmol), 9-phenyl-9H,9'H-3,3'-dicarbazole (6.5 g, 15.8 mmol), CuI (3.0 g, 15.8 mmol), trans-1,2-diaminocyclohexane (1.9 ml, 15.8 mmol) and K3PO4 (3.3 g, 31.6 mmol) in 1,4-oxane (100 ml), the mixture was refluxed for 24 hours. After the reaction was completed, the resultant was extracted by introducing distilled water and DCM therein at room temperature, and after drying the organic layer with MgSO4, the solvent was removed using a rotary evaporator. The reaction material was purified by column chromatography (DCM: Hex = 1:3) and recrystallized with methanol to obtain the target compound 3-3 (7.5 g, 85%).

[0363] The target compound was synthesized in the same manner as Preparation Example 6, except that Compound E of Table 4 below was used instead of 3-bromo-1,1′-biphenyl, and Compound F of Table 4 below was used instead of 9-phenyl-9H,9′H-3,3′-dicarbazole.

[0364] [Table 4]

[0365]

[0366]

[0367] The remaining compounds except the compounds described in Table 1 to Table 4 were also prepared in the same manner as in the Preparation Examples described above.

[0368] The 1H NMR data and FD-MS data of the synthesized compounds are shown in Tables 5 and 6 below, and the synthesis of the target compound was identified through the following data.

[0369] [Table 5]

[0370]

[0371]

[0372] [Table 6]

[0373]

[0374]

[0375] <Experimental Example 1>

[0376] -Manufacturing of organic light-emitting devices

[0377] A glass substrate on which indium tin oxide was coated in the form of a thin film to a thickness of 1,500 angstroms was ultrasonically cleaned with distilled water. After the cleaning with distilled water was completed, the substrate was ultrasonically cleaned with a solvent such as acetone, methanol, and isopropyl alcohol, then dried, and subjected to ultraviolet ozone treatment using UV in an ultraviolet cleaner for 5 minutes. Thereafter, the substrate was transferred to a plasma cleaner (PT), and after plasma treatment was performed under vacuum for ITO work function and residual film removal, the substrate was transferred to a thermal deposition apparatus for organic deposition.

[0378] On the transparent ITO electrode (anode), a hole injection layer 2-TNATA (4,4',4"-tri[2-naphthyl(phenyl)amino]triphenylamine) and a hole transport layer NPB (N,N'-di(1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine) were formed as common layers.

[0379] A light-emitting layer was thermally vacuum deposited thereon as follows. As a light-emitting layer, the compound of Chemical Formula 1 described in Table 6 below was deposited to 400 angstroms, and a green phosphorescent dopant [Ir(ppy)3] was doped and deposited at 7% relative to the deposition thickness of the light-emitting layer. Thereafter, BCP (bathocuproine) was deposited to 60 angstroms as a hole blocking layer, and Alq3 was deposited to 200 angstroms thereon 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 angstroms, and then a cathode was formed on the electron injection layer by depositing an aluminum (Al) cathode to a thickness of 1,200 angstroms, and thus, an organic electroluminescent device was manufactured.

[0380] At the same time, in 10 -8 Support up to 10 -6 Under the support, all organic compounds required for the manufacture of OLEDs are purified by vacuum sublimation for each material used in the manufacture of OLEDs.

[0381] For each of the organic electroluminescent devices manufactured as above, electroluminescent (EL) characteristics were measured using M7000 manufactured by MicroScience, and according to the measurement results, when the standard brightness was 6,000 cd / m2, T was measured via a service life measurement system (M6000) manufactured by MicroScience. 90 .

[0382] The driving voltage, luminous efficiency, color (EL color), and lifespan of the organic light-emitting device manufactured according to the present disclosure were measured and are shown in Table 7 below.

[0383] [Table 7]

[0384]

[0385]

[0386] As can be seen from the results of Table 7, compared with Comparative Examples 1 to 18, the organic electroluminescent device using the organic electroluminescent device light-emitting layer material of the present disclosure has a lower driving voltage, enhanced luminous efficiency, and significantly improved service life.

[0387] Specifically, in the following Table 8, the LUMO orbital of compound 1-298 (Example 17) is delocalized to triazine and terphenyl substituents. However, it was identified that when the triazine group does not have a sufficiently long aryl substituent as in the compounds of Ref. 4, Ref. 7, Ref. 8, Ref. 11, Ref. 14, Ref. 16, and Ref. 19, the LUMO orbital of the triazine is localized to the short aryl substituent, thereby failing to effectively stabilize the electrons and thus reducing the service life.

[0388] [Table 8]

[0389]

[0390]

[0391] In the following Table 9, it was identified that when the triazine group was substituted with carbazole as in the compounds of Ref. 1, Ref. 9 and Ref. 10, the LUMO orbital of the triazine was delocalized to the carbazole. It was identified that the triazine having an electron-pulling property effectively stabilized the electrons, however, the carbazole having an electron-pushing property could not effectively stabilize the electrons and thus reduced the service life.

[0392] [Table 9]

[0393]

[0394] It was identified that when the triazine group was substituted with a pyrimidinyl group, a cyano group or a pyridyl group as in the compounds of Ref. 2, Ref. 3, Ref. 6, Ref. 17 and Ref. 18, the electron mobility increased excessively and the balance between holes and electrons was broken in the light-emitting layer, and thus, the service life was reduced.

[0395] When the No. 3 and No. 4 positions of carbazole are substituted with phenyl groups as in the compounds of Ref. 11, Ref. 12, Ref. 13, Ref. 15, and Ref. 16, the sublimation temperature increases by having a larger molecular weight than unsubstituted carbazole, and a relatively planar structure is formed by having a smaller structural distortion than carbazole having phenyl groups substituted at the No. 2 position, and the sublimation temperature increases. It was identified that when exposed to a higher sublimation temperature for a long time, the organic compound deteriorates and the service life decreases.

[0396] It was identified that when carbazole was substituted with amine or carbazole as in the compounds of Ref. 6, Ref. 7, and Ref. 8, hole mobility excessively increased and the balance between holes and electrons was broken in the light emitting layer, and thus, the service life decreased.

[0397] In the compound of Ref. 10, a pyridine bond replaces triazine. It is identified that this reduces electron mobility, and the balance between holes and electrons is broken in the light-emitting layer, and therefore, the service life is reduced.

[0398] In Table 10 below, the compound of Ref.5 has a pyrene group directly bonded to triazine. It was identified that the pyrene substituted with a substituent group reabsorbs light energy (about 2.4 electron volts) emitted from a green dopant due to a low T1 energy level, and the device has reduced efficiency and service life. Pyrene with a low T1 energy level is mainly used as a dopant for fluorescent OLED devices rather than phosphorescent OLED devices, and its principle is to drive the device by preventing T1 energy transfer and targeting S1 energy transfer.

[0399] [Table 10]

[0400]

[0401] <Experimental Example 2>

[0402] -Manufacturing of organic light-emitting devices

[0403] A glass substrate on which indium tin oxide was coated in a thin film form to a thickness of 1,500 angstroms was ultrasonically cleaned with distilled water. After the cleaning with distilled water was completed, the substrate was ultrasonically cleaned with a solvent such as acetone, methanol, and isopropyl alcohol, then dried, and treated with ultraviolet ozone for 5 minutes using UV in an ultraviolet cleaner. Thereafter, the substrate was transferred to a plasma cleaner (PT), and after plasma treatment under vacuum for ITO work function and residual film removal, the substrate was transferred to a thermal deposition device for organic deposition.

[0404] On the transparent ITO electrode (anode), a hole injection layer 2-TNATA (4,4',4"-tri[2-naphthyl(phenyl)amino]triphenylamine) and a hole transport layer NPB (N,N'-di(1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine) were formed as common layers.

[0405] A light-emitting layer was thermally vacuum deposited thereon as follows. As a light-emitting layer, a compound of one type of chemical formula 1 described in Table 11 below and a compound of one type of chemical formula 2 were premixed in a weight ratio as described in Table 11 below, and deposited to 400 angstroms in a supply source as a host, and a green phosphorescent dopant [Ir(ppy)3] was doped and deposited in an amount of 7% relative to the deposition thickness of the light-emitting layer. Thereafter, BCP (bathocuproine) was deposited to 60 angstroms as a hole blocking layer, and Alq3 was deposited to 200 angstroms thereon 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 angstroms, and then a cathode was formed on the electron injection layer by depositing an aluminum (Al) cathode to a thickness of 1,200 angstroms, and thus, an organic electroluminescent device was manufactured.

[0406] At the same time, in 10 -8 Support up to 10 -6 Under the support, all organic compounds required for the manufacture of OLEDs are purified by vacuum sublimation for each material used in the manufacture of OLEDs.

[0407] For each of the organic electroluminescent devices manufactured as above, electroluminescent (EL) characteristics were measured using M7000 manufactured by MicroScience, and according to the measurement results, when the standard brightness was 6,000 cd / m2, T was measured via a service life measurement system (M6000) manufactured by MicroScience. 90 .

[0408] The driving voltage, luminous efficiency, color coordinates (CIE), and lifespan of the organic light-emitting device manufactured according to the present disclosure were measured and are shown in Table 11 below.

[0409] [Table 11]

[0410]

[0411] Based on the results of Table 11, when the compound of Chemical Formula 1 (n-type) and the compound of Chemical Formula 2 are simultaneously included, more excellent effects of efficiency and service life are obtained. Such results may lead to prediction of the occurrence of an exciplex phenomenon when both compounds are simultaneously included.

[0412] The exciplex phenomenon is a phenomenon in which energy having the size of the HOMO energy level of the donor (p host) and the LUMO energy level of the acceptor (n host) is released due to the exchange of electrons between two molecules. When the exciplex phenomenon occurs between two molecules, reverse intersystem crossing (RISC) occurs, and thus, the internal quantum efficiency of fluorescence can be increased up to 100%. When a donor (p host) having good hole transporting ability and an acceptor (n host) having good electron transporting ability are used as the host of the light-emitting layer, holes are injected into the p host and electrons are injected into the n host, and thus, the driving voltage can be reduced, which ultimately helps to enhance the service life. In the disclosure of the present application, it is identified that the compound of Chemical Formula 2 acts as a donor and the compound of Chemical Formula 1 acts as an acceptor, and excellent device characteristics are obtained when used together with the host of the light-emitting layer.

Claims

1. A heterocyclic compound, characterized in that It is represented by any one of the following Chemical Formulas 3 to 5 and 7: [Chemical formula 3] [Chemical formula 4] [Chemical formula 5] [Chemical formula 7] Among them, in Chemical Formulae 3 to 5 and 7, Ar1 to Ar4 are the same as or different from each other and are each independently hydrogen; deuterium; or phenyl; L1 is a direct bond; phenylene; or biphenylene; a is an integer from 1 to 4; When a is 2 or more, the substituents in each bracket are the same or different from each other; X is O; S; or C(R21)(R22); R1 to R5 are the same as or different from each other and are each independently hydrogen; phenyl; or biphenyl; R6 to R9 are the same as or different from each other, and are each independently hydrogen; or deuterium; R21 and R22 are the same or different from each other and are each independently a methyl group; or a phenyl group, or two or more adjacent groups are bonded to each other to form a fluorene ring; a1 to d1 are each an integer from 1 to 4; e1 is an integer from 1 to 5; and When a1 to e1 are each 2 or more, the substituents in each bracket are the same as or different from each other.

2. The heterocyclic compound according to claim 1, characterized in that Any one of Chemical Formulae 3 to 5 and Chemical Formula 7 is represented by any one of the following compounds:

3. An organic light-emitting device, characterized in that: include: a first electrode; a second electrode, arranged opposite to the first electrode; as well as One or more organic material layers are disposed between the first electrode and the second electrode, One or more layers of the organic material layer comprises the heterocyclic compound as claimed in claim 1 or 2.

4. The organic light-emitting device according to claim 3, characterized in that: The organic material layer including the heterocyclic compound further includes a heterocyclic compound represented by the following Chemical Formula 2: [Chemical formula 2] In chemical formula 2, Rc and Rd are the same as or different from each other and are each independently selected from the group consisting of: hydrogen; deuterium; a halogen group; -CN; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -Si(R10)(R11)(R12); -P(=O)(R10)(R11); and a substituted or unsubstituted amino group, or two or more adjacent groups bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocyclic ring; R10, R11 and R12 are the same as or different from each other and are each independently hydrogen; deuterium; -CN; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl; Ra and Rb are the same as or different 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; The "substituted or unsubstituted" means substituted with one or more substituents selected from the group consisting of: deuterium; halogen; cyano; C1 to C60 straight or branched alkyl; C2 to C60 straight or branched alkenyl; C2 to C60 straight or branched alkynyl; C3 to C60 monocyclic or polycyclic cycloalkyl; C2 to C60 monocyclic or polycyclic heterocycloalkyl; C6 to C60 monocyclic or polycyclic aryl; C2 to C60 monocyclic or polycyclic heteroaryl; -SiRR'R"; -P(=O)RR'; C1 to C20 alkylamine; C6 to C60 monocyclic or polycyclic arylamine; and C2 to C60 monocyclic or polycyclic heteroarylamine, or unsubstituted, R, R' and R" are the same as or different from each other, and are each independently an unsubstituted C1 to C60 alkyl group; an unsubstituted C6 to C60 aryl group; or an unsubstituted C2 to C60 heteroaryl group, r and s are each an integer from 0 to 7; and When r and s are each 2 or more, the substituents in the parentheses are the same as or different from each other.

5. The organic light-emitting device according to claim 4, characterized in that: Chemical formula 2 is represented by the following Chemical formula 2-1 or Chemical formula 2-2: [Chemical formula 2-1] [Chemical formula 2-2] In Chemical Formula 2-1 and Chemical Formula 2-2, Rc, Rd, r and s have the same definitions as in Chemical Formula 2; Ra1, Rb1 and Rc1 are the same as or different from each other, and are each independently a substituted or unsubstituted C6 to C60 aryl group; R1' and R2' are the same as or different from each other and are independently selected from the group consisting of: hydrogen; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C6 to C60 aryl; and substituted or unsubstituted C2 to C60 heteroaryl; L1' is a direct bond; or a substituted or unsubstituted C6 to C60 arylene group; Ar1' is a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group comprising at least one of S and O; m' is an integer from 0 to 4; n' is an integer from 0 to 2; and When m' is 2 or more, the substituents in the respective brackets are the same as or different from each other.

6. The organic light-emitting device according to claim 4, characterized in that: The heterocyclic compound represented by Chemical Formula 2 is any one selected from the following compounds:

7. The organic light-emitting device according to claim 4, characterized in that: Rc and Rd are hydrogen.

8. The organic light-emitting device according to claim 5, characterized in that: The organic material layer includes a light-emitting layer, and the light-emitting layer includes the heterocyclic compound according to any one of claims 1 or 2.

9. The organic light-emitting device according to claim 5, characterized in that: The organic material layer comprises a light-emitting layer, the light-emitting layer comprises a host material, and the host material comprises the heterocyclic compound according to any one of claims 1 or 2.

10. The organic light emitting device according to claim 5, characterized in that: It also includes one, two or more than two 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.

11. A composition for an organic material layer of an organic light-emitting device, characterized in that: The composition comprises: The heterocyclic compound according to any one of claims 1 or 2; and A heterocyclic compound represented by the following chemical formula 2: [Chemical formula 2] In chemical formula 2, Rc and Rd are the same as or different from each other and are each independently selected from the group consisting of: hydrogen; deuterium; a halogen group; -CN; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -Si(R10)(R11)(R12); -P(=O)(R10)(R11); and a substituted or unsubstituted amino group, or two or more adjacent groups bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C60 heterocyclic ring; R10, R11 and R12 are the same as or different from each other and are each independently hydrogen; deuterium; -CN; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl; Ra and Rb are the same as or different 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; The "substituted or unsubstituted" means substituted with one or more substituents selected from the group consisting of: deuterium; halogen; cyano; C1 to C60 straight or branched alkyl; C2 to C60 straight or branched alkenyl; C2 to C60 straight or branched alkynyl; C3 to C60 monocyclic or polycyclic cycloalkyl; C2 to C60 monocyclic or polycyclic heterocycloalkyl; C6 to C60 monocyclic or polycyclic aryl; C2 to C60 monocyclic or polycyclic heteroaryl; -SiRR'R"; -P(=O)RR'; C1 to C20 alkylamine; C6 to C60 monocyclic or polycyclic arylamine; and C2 to C60 monocyclic or polycyclic heteroarylamine, or unsubstituted, R, R' and R" are the same as or different from each other, and are each independently an unsubstituted C1 to C60 alkyl group; an unsubstituted C6 to C60 aryl group; or an unsubstituted C2 to C60 heteroaryl group, r and s are each an integer from 0 to 7; and When r and s are each 2 or more, the substituents in the parentheses are the same as or different from each other.

12. The composition for an organic material layer of an organic light-emitting device according to claim 11, characterized in that: The heterocyclic compound: the heterocyclic compound represented by Chemical Formula 2 has a weight ratio of 1:10 to 10:1 in the composition.

13. A method for manufacturing an organic light-emitting device, characterized in that: The method comprises: preparing a substrate; forming a first electrode on the substrate; forming one or more organic material layers on the first electrode; and forming a second electrode on the organic material layer, The forming of the organic material layer comprises forming one or more organic material layers using the composition for an organic material layer as claimed in claim 11 .

14. The method for manufacturing an organic light-emitting device according to claim 13, characterized in that: The organic material layer is formed by premixing the heterocyclic compound with the heterocyclic compound of Chemical Formula 2 using a thermal vacuum deposition method.

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