Heterocyclic compound and organic light-emitting device comprising the same

Abstract

The present specification provides a heterocyclic compound represented by Chemical Formula 1 and an organic light-emitting device including the same. The present invention can improve the service life of the device. [Chemical Formula 1] #imgabs0# In Chemical Formula 1, the definition of each substituent is the same as that in the specification.

Description

[0001] This application claims priority to and the benefit of Korean Patent Application No. 10-2019-0140381 filed on November 5, 2019, with the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference. Technical Field

[0002] The present invention relates to a heterocyclic compound and an organic light-emitting device including the same. Background Art

[0003] An organic electroluminescent device is a type of self-luminous display device and has the following advantages: a wide viewing angle, a fast response speed, and 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 needed.

[0005] The material of the organic thin film may have a light-emitting function as required. For example, as the material of the organic thin film, 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. In addition, a compound capable of 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 thin film.

[0006] The development of organic thin film materials is constantly demanding to enhance the performance, lifespan or efficiency of organic light emitting devices.

[0007] <Prior Art Literature>

[0008] U.S. Patent No. 4,356,429 Summary of the invention

[0009] Technical issues

[0010] One embodiment of the present application relates to a heterocyclic compound represented by Chemical Formula 1 and an organic light-emitting device including the same.

[0011] Technical Solutions

[0012] One embodiment of the present application provides a heterocyclic compound represented by the following Chemical Formula 1.

[0013] [Chemical formula 1]

[0014]

[0015] In Chemical Formula 1,

[0016] N-Het is a substituted or unsubstituted monocyclic or polycyclic C2 to C60 heterocyclic group including one or more N,

[0017] L1 and L2 are direct bonds; substituted or unsubstituted C6 to C60 arylene groups; or substituted or unsubstituted C2 to C60 heteroarylene groups, a and d are each an integer from 1 to 3, and when a is 2 or more, L1 are the same or different from each other, and when d is 2 or more, L2 are the same or different from each other,

[0018] Rm and Rn are the same as or different from each other and are each independently selected from the group consisting of: hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C2 to C60 alkenyl; substituted or unsubstituted C2 to C60 alkynyl; substituted or unsubstituted C1 to C60 alkoxy; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted substituted C6 to C60 aryl; substituted or unsubstituted C2 to C60 heteroaryl; -P(=O)RR'; and -NRR'; or two or more groups adjacent to each other are combined with each other to form a substituted or unsubstituted C6 to C60 aliphatic or aromatic hydrocarbon ring or a C2 to C60 heterocycle, b and c are each an integer of 1 to 3, and when b is 2 or more, Rm is the same or different, and when c is 2 or more, Rn is the same or different, and

[0019] Ar1 is represented by the following Chemical Formula 2 or Chemical Formula 3,

[0020] [Chemical formula 2]

[0021]

[0022] [Chemical formula 3]

[0023]

[0024] In Chemical Formula 2 and Chemical Formula 3,

[0025] means a site connected to L2 of Chemical Formula 1,

[0026] R1 to R13 are the same as or different from each other and are each independently selected from the group consisting of: hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C2 to C60 alkenyl; substituted or unsubstituted C2 to C60 alkynyl; substituted or unsubstituted C1 to C60 alkoxy; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; substituted or unsubstituted C2 to C60 heteroaryl; -P(=O)RR'; and -NRR'; or two or more adjacent groups are combined to form a substituted or unsubstituted C6 to C60 aliphatic or aromatic hydrocarbon ring or C2 to C60 heterocycle, e is an integer from 1 to 3, and when e is 2 or more than 2, R13 are the same as or different from each other,

[0027] A1 and A2 are the same or different from each other and are each independently O; S; CRaRb; NRc; or SiRdRe,

[0028] A3 is a direct bond; O; S; CRaRb; NRc; or SiRdRe, and

[0029] R, R' and Ra to Re are the same as or different from each other and are each independently hydrogen; 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 combined with each other to form a substituted or unsubstituted C6 to C60 aliphatic or aromatic hydrocarbon ring or a C2 to C60 heterocycle.

[0030] Another embodiment of the present application provides an organic light-emitting device, which includes: 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 include a heterocyclic compound represented by Chemical Formula 1.

[0031] Beneficial effects

[0032] The compounds described in this specification can be used as materials of an organic material layer of an organic light-emitting device. In an organic light-emitting device, the compound can function as a hole injection material, a hole transport material, a light-emitting material, an electron transport material, an electron injection material, or the like. Specifically, the compound can be used as a light-emitting layer material of an organic light-emitting device. For example, the compound can be used only as a light-emitting material, or can be used as a host material of a light-emitting layer.

[0033] Specifically, by substituting the position of carbon No. 3 of the dibenzofuran structure with an N-containing ring and substituting the benzene in the dibenzofuran ring that is not substituted with the N-containing ring with a substituent represented by Chemical Formula 2 or Chemical Formula 3, Chemical Formula 1 has a more electronically stable structure, and therefore, the device life can be improved.

[0034] In addition, when Ar1 of Chemical Formula 1 is represented by Chemical Formula 2 or Chemical Formula 3, electron distribution is widely diffused from the dibenzofuran core to the substituent of Ar1, thereby generating a wide band gap and a high T1 value. Therefore, due to the characteristics of a wide band gap and a high T1 compared to the case of having carbazole, when Chemical Formula 1 is used as a phosphorescent host material of an organic light-emitting device, an organic light-emitting device with excellent efficiency and low driving voltage is obtained in the present application. BRIEF DESCRIPTION OF THE DRAWINGS

[0035] 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.

[0036] <Description of symbols>

[0037] 100:Substrate

[0038] 200: Anode

[0039] 300: organic material layer

[0040] 301: hole injection layer

[0041] 302: hole transport layer

[0042] 303: Luminous layer

[0043] 304: Hole blocking layer

[0044] 305: electron transport layer

[0045] 306: electron injection layer

[0046] 400: cathode DETAILED DESCRIPTION

[0047] Hereinafter, the present application will be described in detail.

[0048] 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, since deuterium ( 2 H (Deuterium) is an isotope of hydrogen, so some of the hydrogen atoms may be deuterium.

[0049] In one embodiment of the present application, "in the case 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%.

[0050] In one embodiment of the present application, in the case where “a substituent is not indicated in a chemical formula or a compound structure”, when deuterium is not explicitly excluded (such as a deuterium content of 0% or a hydrogen content of 100%), hydrogen and deuterium may be mixed in the compound. In other words, the expression “the substituent X is hydrogen” does not exclude deuterium, such as a hydrogen content of 100% or a deuterium content of 0%, and thus may mean a state where hydrogen and deuterium are mixed.

[0051] In one embodiment of the present application, deuterium is one of the isotopes of hydrogen, an element having a deuterium nucleus formed by one proton and one neutron as an atomic nucleus, and can be represented as hydrogen-2, and the element symbol can also be written as D or 2 H.

[0052] 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 but different neutron numbers.

[0053] In one embodiment of the present application, the content T% of a specific substituent may be defined as T2 / T1×100=T%, wherein the total number of substituents that the base compound may have is defined as T1, and the number of specific substituents among these substituents is defined as T2.

[0054] 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 in these substituents 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.

[0055]

[0056] 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 include a deuterium atom, that is, a phenyl group having 5 hydrogen atoms.

[0057] The term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is changed to another substituent, and the substitution position is not limited as long as it is a position where a hydrogen atom is substituted, that is, a position where a substituent can replace, and when two or more substituents are substituted, the two or more substituents may be the same as or different from each other.

[0058] 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 aromatic amine; and C2 to C60 monocyclic or polycyclic heteroaromatic amine, or is unsubstituted, or is substituted with a substituent connecting two or more substituents selected from the substituents shown above, or is unsubstituted.

[0059] In the present application, R, R' and R" are the same as or different from each other, and may be each independently hydrogen; substituted or unsubstituted alkyl; substituted or unsubstituted aryl; or substituted or unsubstituted heteroaryl.

[0060] In the present specification, halogen may be fluorine, chlorine, bromine or iodine.

[0061] 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, t-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, t-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, t-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.

[0062] 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 may be 2 to 60, specifically 2 to 40 and more specifically 2 to 20. Its specific examples may include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbene, styryl and the like, but are not limited thereto.

[0063] 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.

[0064] 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 preferably 1 to 20. Its specific examples may include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy and the like, but are not limited thereto.

[0065] In this specification, cycloalkyl includes monocyclic or polycyclic rings with 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 connected 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 group 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-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and similar groups, but are not limited thereto.

[0066] In this specification, heterocycloalkyl includes O, S, Se, N or Si as heteroatoms, including 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 connected 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 in heterocycloalkyl may be 2 to 60, specifically 2 to 40 and more specifically 3 to 20.

[0067] In this specification, aryl includes monocyclic or polycyclic rings having 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 connected 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 of aryl groups may include phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, chrysene, phenanthryl, peryl, fluorenyl, 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.

[0068] In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be combined with each other to form a ring.

[0069] When the fluorenyl group is substituted, the following structures may be included, however, the structure is not limited thereto.

[0070]

[0071] In this specification, heteroaryl includes S, O, Se, N or Si as heteroatoms, including 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 the heteroaryl is directly connected 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 of heteroaryl groups may include pyridyl, pyrrolyl, pyrimidinyl, pyridazinyl, furanyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, furazolyl, oxadiazolyl, thiadiazolyl, dithiazolyl, tetrazolyl, pyranyl, thiopyranyl, diazinyl, oxazinyl, thiazinyl, dioxinyl, triazinyl, tetrazinyl, quinolyl, isocyanol, pyraz ... Quinolyl, quinazolinyl, isoquinazolinyl, quinolizinyl, naphthyridinyl, acridinyl, phenanthridinyl, imidazopyridinyl, naphthyridinyl, triazindenyl, indolyl, indolizinyl, benzothiazolyl, benzoxazolyl, benzimidazolyl, benzothienyl, benzofuranyl, dibenzothienyl, dibenzofuranyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenanthrazinyl, dibenzosilanol alkenyl, spirobis(dibenzosilylene), dihydrophenanthrazinyl, phenanthridinyl, imidazopyridinyl, thienyl, indolo[2,3-a]carbazolyl, indolo[2,3-b]carbazolyl, dihydroindole, 10,11-dihydro-dibenzo[b,f]azepinyl, 9,10-dihydroacridinyl, phenanthrazinyl, phenathiazinyl, phthalazinyl, naphthoindole, phenanthroline quinazolyl, pyrido[1,2-b]indazolyl, pyrido[1,2-a]imidazo[1,2-e]dihydroindole, 5,11-dihydroindeno[1,2-b]carbazolyl, and the like, but are not limited thereto.

[0072] In the present specification, the amino group may be selected from the group consisting of a monoalkylamino group, a monoarylamino group, a monoheteroarylamino group, -NH2, a dialkylamino group, a diarylamino group, a diheteroarylamino group, an alkylarylamino group, an alkylheteroarylamino group, and an arylheteroarylamino group, and although the number of carbon atoms is not particularly limited thereto, it is preferably 1 to 30. Specific examples of the amino group may include a methylamino group, a dimethylamino group, an ethylamino group, a diethylamino group, an anilino group, a naphthylamino group, a benzidine group, a dibenzidine group, an anthracene group, a 9-methyl-anthracene group, a diphenylamino group, a phenylnaphthylamino group, a ditoluidine group, a phenyltoluidine group, a triphenylamino group, a diphenylnaphthylamino group, a phenylbenzidine group, a diphenylfluorenylamino group, a phenyltriphenyleneamine group, a biphenyltriphenyleneamine group, and the like, but are not limited thereto.

[0073] In this specification, arylene means an aryl group having two binding 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 binding 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.

[0074] In this specification, the phosphine oxide group is represented by -P(=O)R 101 R 102 Indicates that R 101 and R 102 The substituents may be the same as or different from each other and may be each independently formed from at least one of the following: hydrogen; deuterium; halogen; alkyl; alkenyl; alkoxy; cycloalkyl; aryl; and heterocyclic group. Specific examples of the phosphine oxide group may include oxidized diphenylphosphino, oxidized dinaphthylphosphino, and the like, but are not limited thereto.

[0075] In this specification, a silicon group is a substituent group including Si, in which Si atoms are directly connected as free radicals, and is composed of -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; halogen; alkyl; alkenyl; alkoxy; cycloalkyl; aryl; and heterocyclic groups. Specific examples of the silyl group may include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, and the like, but are not limited thereto.

[0076] In the present specification, an "adjacent" group may mean a substituent that replaces an atom directly connected to the atom replaced by the corresponding substituent, a substituent that is closest in space to the corresponding substituent, or another substituent that replaces the atom replaced 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.

[0077] As an aliphatic or aromatic hydrocarbon ring or heterocyclic ring which the adjacent groups may form, the structures shown as the cycloalkyl group, cycloheteroalkyl group, aryl group and heteroaryl group described above are applicable except for those groups which are not monovalent groups.

[0078] One embodiment of the present application provides a compound represented by Chemical Formula 1.

[0079] In one embodiment of the present application, Chemical Formula 1 may be represented by any one of the following Chemical Formulas 4 to 7.

[0080] [Chemical formula 4]

[0081]

[0082] [Chemical formula 5]

[0083]

[0084] [Chemical formula 6]

[0085]

[0086] [Chemical formula 7]

[0087]

[0088] In Chemical Formulae 4 to 7,

[0089] Each substituent has the same definition as in Chemical Formula 1.

[0090] In one embodiment of the present application, Rm and Rn are the same as or different from each other and are each independently selected from the group consisting of: hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C2 to C60 alkenyl; substituted or unsubstituted C2 to C60 alkynyl; substituted or unsubstituted C1 to C60 alkoxy; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; substituted or unsubstituted C2 to C60 heteroaryl; -P(=O)RR'; and -NRR', or two or more adjacent groups may be combined with each other to form a substituted or unsubstituted C6 to C60 aliphatic or aromatic hydrocarbon ring or a C2 to C60 heterocycle.

[0091] In another embodiment, Rm and Rn are the same as or different from each other and are each 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, or two or more adjacent groups may be combined with each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a C2 to C60 heterocycle.

[0092] In another embodiment, Rm and Rn may be hydrogen.

[0093] In one embodiment of the present application, L1 and L2 may be a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group.

[0094] In another embodiment, L1 and L2 may be a direct bond; a substituted or unsubstituted C6 to C40 arylene group; or a substituted or unsubstituted C2 to C40 heteroarylene group.

[0095] In another embodiment, L1 and L2 may be a direct bond; or a substituted or unsubstituted C6 to C40 arylene group.

[0096] In another embodiment, L1 and L2 may be a direct bond; or a C6 to C40 arylene group.

[0097] In another embodiment, L1 and L2 may be a direct bond; or a C6 to C40 monocyclic arylene group.

[0098] In another embodiment, L1 and L2 may be a direct bond; or a C6 to C20 monocyclic arylene group.

[0099] In another embodiment, L1 and L2 may be a direct bond; or a phenylene group.

[0100] In one embodiment of the present application, N-Het may be a substituted or unsubstituted monocyclic or polycyclic C2 to C60 heterocyclic group including one or more N.

[0101] In another embodiment, N-Het may be a substituted or unsubstituted monocyclic or polycyclic C2-C60 heterocyclic group including one or more and three or less than three N groups.

[0102] In another embodiment, N-Het may be a substituted or unsubstituted monocyclic C2-C60 heterocyclyl group including one or more and three or less than three N groups.

[0103] In another embodiment, N-Het may be a monocyclic C2-C60 heterocyclic group which is unsubstituted or substituted with one or more substituents selected from the group consisting of C6-C60 aryl groups and C2-C60 heteroaryl groups and includes one or more and three or less N groups.

[0104] In another embodiment, N-Het may be a monocyclic C2-C60 heterocyclic group which is unsubstituted or substituted with one or more substituents selected from the group consisting of C6-C40 aryl groups and C2-C40 heteroaryl groups and includes one or more and three or less N groups.

[0105] In another embodiment, N-Het may be a triazinyl group which is unsubstituted or substituted with one or more substituents selected from the group consisting of C6 to C40 aryl groups and C2 to C40 heteroaryl groups; a pyrimidinyl group which is unsubstituted or substituted with one or more substituents selected from the group consisting of C6 to C40 aryl groups and C2 to C40 heteroaryl groups; or a pyridinyl group which is unsubstituted or substituted with one or more substituents selected from the group consisting of C6 to C40 aryl groups and C2 to C40 heteroaryl groups.

[0106] In another embodiment, N-Het may be represented by the following Chemical Formula 8.

[0107] [Chemical formula 8]

[0108]

[0109] In Chemical Formula 8,

[0110] means a site connected to L1 of Chemical Formula 1,

[0111] X1 is CR21 or N, X2 is CR22 or N, X3 is CR23 or N, X4 is CR24 or N, and X5 is CR25 or N,

[0112] At least one of X1 to X5 is N, and

[0113] R21 to R25 are the same as or different from each other and are each independently selected from the group consisting of: hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C2 to C60 alkenyl; substituted or unsubstituted C2 to C60 alkynyl; substituted or unsubstituted C1 to C60 alkoxy; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; substituted or unsubstituted C2 to C60 heteroaryl; -P(=O)RR'; and -NRR'; or two or more adjacent groups are combined to form a substituted or unsubstituted C6 to C60 aliphatic or aromatic hydrocarbon ring or a C2 to C60 heterocyclic ring.

[0114] In one embodiment of the present application, R21 to R25 are the same as or different from each other, and may be each independently hydrogen; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0115] In another embodiment, R21 to R25 are the same as or different from each other, and may each independently be a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group.

[0116] In another embodiment, R21 to R25 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 C6 to C40 aryl group and a C2 to C40 heteroaryl group; or a C2 to C40 heteroaryl group which is unsubstituted or substituted with one or more substituents selected from the group consisting of a C6 to C40 aryl group and a C2 to C40 heteroaryl group.

[0117] In another embodiment, R21 to R25 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 a C2 to C40 heteroaryl group; or a C2 to C40 heteroaryl group which is unsubstituted or substituted with a C6 to C40 aryl group.

[0118] In another embodiment, R21 to R25 are the same as or different from each other, and may be each independently a phenyl group which is unsubstituted or substituted with a carbazolyl group; a biphenyl group; a naphthyl group; a carbazolyl group which is unsubstituted or substituted with a phenyl group; a dibenzofuranyl group; or a dibenzothienyl group.

[0119] In one embodiment of the present application, Chemical Formula 8 can be selected from the following structural formulas.

[0120]

[0121] In the structural formula,

[0122] R21 to R25 have the same meanings as in Chemical Formula 8.

[0123] In one embodiment of the present application, Ar1 may be represented by the following Chemical Formula 2 or Chemical Formula 3.

[0124] [Chemical formula 2]

[0125]

[0126] [Chemical formula 3]

[0127]

[0128] In Chemical Formula 2 and Chemical Formula 3,

[0129] means a site connected to L2 of Chemical Formula 1,

[0130] R1 to R13 are the same as or different from each other and are each independently selected from the group consisting of: hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C2 to C60 alkenyl; substituted or unsubstituted C2 to C60 alkynyl; substituted or unsubstituted C1 to C60 alkoxy; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; substituted or unsubstituted C2 to C60 heteroaryl; -P(=O)RR'; and -NRR'; or two or more adjacent groups are combined to form a substituted or unsubstituted C6 to C60 aliphatic or aromatic hydrocarbon ring or C2 to C60 heterocycle, e is an integer from 1 to 3, and when e is 2 or more than 2, R13 are the same as or different from each other,

[0131] A1 and A2 are the same or different from each other and are each independently O; S; CRaRb; NRc; or SiRdRe,

[0132] A3 is a direct bond; O; S; CRaRb; NRc; or SiRdRe, and

[0133] R, R' and Ra to Re are the same as or different from each other and are each independently hydrogen; 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 combined with each other to form a substituted or unsubstituted C6 to C60 aliphatic or aromatic hydrocarbon ring or a C2 to C60 heterocycle.

[0134] In one embodiment of the present application, R1 to R13 are the same as or different from each other, and are each independently selected from the group consisting of: hydrogen; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C6 to C60 aryl; substituted or unsubstituted C2 to C60 heteroaryl; -P(=O)RR'; and -NRR'; or two or more adjacent groups may be combined with each other to form a substituted or unsubstituted C6 to C60 aliphatic or aromatic hydrocarbon ring or a C2 to C60 heterocyclic ring.

[0135] In another embodiment, R1 to R13 are the same as or different from each other, and are each independently selected from the group consisting of: hydrogen; substituted or unsubstituted C6 to C60 aryl; and substituted or unsubstituted C2 to C60 heteroaryl.

[0136] In another embodiment, R1 to R13 are the same as or different from each other, and are independently selected from the group consisting of: hydrogen; C6 to C60 aryl; and C2 to C60 heteroaryl.

[0137] In another embodiment, R1 to R13 may be hydrogen.

[0138] In one embodiment of the present application, A1 and A2 are the same as or different from each other, and may be each independently O; S; CRaRb; NRc; or SiRdRe.

[0139] In one embodiment of the present application, A3 may be a direct bond; O; S; CRaRb; NRc; or SiRdRe.

[0140] In one embodiment of the present application, Ra to Re are the same as or different from each other, and are each independently hydrogen; 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 groups adjacent to each other may be combined with each other to form a substituted or unsubstituted C6 to C60 aliphatic or aromatic hydrocarbon ring or a C2 to C60 heterocyclic ring.

[0141] In another embodiment, Ra to Re are the same as or different from each other and are each independently hydrogen; 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 groups adjacent to each other may be combined with each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a C2 to C60 heterocycle.

[0142] In another embodiment, Ra to Re are the same as or different from each other and are each independently 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, or two or more groups adjacent to each other may be combined with each other to form a substituted or unsubstituted C6 to C40 aromatic hydrocarbon ring or a C2 to C40 heterocyclic ring.

[0143] In another embodiment, Ra to Re are the same as or different from each other and are each independently a C1 to C40 alkyl group; or a C6 to C40 aryl group, or two or more adjacent groups may be combined with each other to form a C6 to C40 aromatic hydrocarbon ring or a C2 to C40 heterocyclic ring.

[0144] In another embodiment, Ra to Re are the same as or different from each other and are each independently a methyl group; or a phenyl group, or two or more adjacent groups may be combined with each other to form a dibenzopyran ring; a fluorene ring; or a 9,10-dihydroanthracene ring.

[0145] In one embodiment of the present application, when A3 is a direct bond, A2 may be CRaRb, and Ra and Rb may be combined with each other to form a dibenzopyran ring.

[0146] In one embodiment of the present application, Chemical Formula 3 may be represented by the following Chemical Formula 3-1 to Chemical Formula 3-4.

[0147] [Chemical formula 3-1]

[0148]

[0149] [Chemical formula 3-2]

[0150]

[0151] [Chemical formula 3-3]

[0152]

[0153] [Chemical formula 3-4]

[0154]

[0155] In Chemical Formula 3-1 to Chemical Formula 3-4,

[0156] Each substituent has the same definition as in Chemical Formula 3.

[0157] In one embodiment of the present application, Ar1 of Chemical Formula 1 is represented by Chemical Formula 2 or Chemical Formula 3, and the electron distribution is widely diffused from the dibenzofuran core to the substituent of Ar1, thereby generating a wide band gap and a high T1 value. In addition, Ar1 of Chemical Formula 1 having a substituent of Chemical Formula 2 or Chemical Formula 3 can maintain a stable molecular structure, thereby promoting an enhancement of the service life.

[0158] Therefore, due to the characteristics of a wide band gap and a high T1 compared with the case of carbazole, when Chemical Formula 1 is used as a phosphorescent host material of an organic light-emitting device, an organic light-emitting device with excellent efficiency and low driving voltage is obtained in the present application.

[0159] According to one embodiment of the present application, Chemical Formula 1 may be represented by any one of the following compounds, but is not limited thereto.

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168] 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.

[0169] In addition, by introducing various substituents into the structure of Chemical Formula 1, the energy band gap can be finely controlled, and at the same time, characteristics at the interface between organic materials are enhanced, and material applications can become diversified.

[0170] In addition, one embodiment of the present application provides an organic light-emitting device, which includes 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 include a heterocyclic compound according to Chemical Formula 1.

[0171] The specific description about the heterocyclic compound represented by Chemical Formula 1 is the same as the description provided above.

[0172] In one embodiment of the present application, the first electrode may be an anode, and the second electrode may be a cathode.

[0173] In another embodiment, the first electrode may be a cathode and the second electrode may be an anode.

[0174] In one embodiment of the present application, the organic light-emitting device may be a blue organic light-emitting device, and the heterocyclic compound according to Chemical Formula 1 may be used as a material of the blue organic light-emitting device. For example, the heterocyclic compound according to Chemical Formula 1 may be included in a host material of a blue light-emitting layer of the blue organic light-emitting device.

[0175] In one embodiment of the present application, the organic light-emitting device may be a green organic light-emitting device, and the heterocyclic compound according to Chemical Formula 1 may be used as a material of the green organic light-emitting device. For example, the heterocyclic compound according to Chemical Formula 1 may be included in a host material of a green light-emitting layer of the green organic light-emitting device.

[0176] 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 material of the red organic light-emitting device. For example, the heterocyclic compound according to Chemical Formula 1 may be included in a host material of a red light-emitting layer of the red organic light-emitting device.

[0177] In addition to using the heterocyclic compounds described above to form one or more of the organic material layers, the organic light-emitting devices of the present disclosure may be manufactured using common organic light-emitting device manufacturing methods and materials.

[0178] 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, spray coating, roll coating and the like, but is not limited thereto.

[0179] The organic material layer of the organic light-emitting device of the present disclosure may be formed in a single-layer structure, but may be formed in a multi-layer structure in which two or more organic material layers are laminated. For example, the organic light-emitting device 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.

[0180] In the organic light-emitting device of the present disclosure, the organic material layer may include a light-emitting layer, and the light-emitting layer may include a heterocyclic compound.

[0181] In another organic light-emitting device, the organic material layer includes a light-emitting layer, the light-emitting layer includes a host material, and the host material may include a heterocyclic compound.

[0182] As another example, the organic material layer including the heterocyclic compound includes the heterocyclic compound represented by Chemical Formula 1 as a host, and an iridium-based dopant may be used therewith.

[0183] 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 transport layer or the electron injection layer may include a heterocyclic compound.

[0184] 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.

[0185] 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.

[0186] 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.

[0187] 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 this 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.

[0188] 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 necessary functional layers may be further added.

[0189] The organic material layer including the compound of Chemical Formula 1 may further include other materials as needed.

[0190] In an organic light-emitting device according to one embodiment of the present application, materials other than the compound of Chemical Formula 1 are shown below, however, these materials are only for illustrative purposes and are not intended to limit the scope of the present application, and may be replaced by materials known in the art.

[0191] 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.

[0192] 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.

[0193] As the hole injection material, a known hole injection material can be used, and for example, a phthalocyanine compound such as copper phthalocyanine disclosed in U.S. Pat. No. 4,356,429 can be used; or a star-shaped amine derivative such as tris(4-hydrazinoyl-9-ylphenyl)amine (TCTA), 4,4',4"-tris[phenyl(m-tolyl)amino]triphenylamine (m-MTDATA) or 1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene (m-MTDAPB) described in the literature [Advanced Material, 6, p. 677 (1994)]; polyaniline / dodecylbenzene sulfonic acid (polyaniline / dodecylbenzene sulfonic acid) as a conductive polymer having solubility can be used. acid), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate), polyaniline / camphor sulfonic acid, or polyaniline / poly(4-styrene-sulfonate); and similar materials.

[0194] 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.

[0195] 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 similar materials can be used as electron transport materials, and polymer materials and low molecular weight materials can also be used as electron transport materials.

[0196] As an example of the electron injection material, LiF is generally used in the art, however, the present application is not limited thereto.

[0197] As the luminescent material, a red, green or blue luminescent material may be used, and two or more luminescent materials may be mixed and used as necessary. Herein, two or more luminescent materials may be used by depositing as individual supply sources or by premixing and depositing as one supply source. In addition, a fluorescent material may also be used as a luminescent material, however, a phosphorescent material may also be used. A material that emits light by combining electrons and holes injected from an anode and a cathode, respectively, may be used alone as a luminescent material, however, a material having a host material and a doping material that participate in luminescence together may also be used as a luminescent material.

[0198] When mixing the light emitting material host, the same series of hosts may be mixed, or different series of hosts may be mixed. For example, any two or more types of materials in n-type host materials or p-type host materials may be selected and used as host materials for the light emitting layer.

[0199] 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 depending on the materials used.

[0200] 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 under similar principles as those used in organic light-emitting devices.

[0201] Mode for Carrying Out the Invention

[0202] Hereinafter, the present specification will be described in more detail with reference to examples, however, these are only for illustrative purposes, and the scope of the present application is not limited thereto.

[0203] [Preparation Example 1] Preparation of Compound 1 (C)

[0204]

[0205] Preparation of compound 1-1

[0206] In a single-necked round-bottom flask (single-necked rbf), a mixture of 1,3-dibromo-2-fluorobenzene (50 g, 197 mmol), (4-chloro-2-methoxyphenyl)boric acid (44 g, 236.4 mmol), tetrakis(triphenylphosphine)palladium(0) (22.7 g, 19.7 mmol), potassium carbonate (5.4 g, 39.4 mmol) and toluene / ethanol / water (800 ml / 160 ml / 160 ml) was refluxed at 110° C. The resultant was extracted with dichloromethane and dried over MgSO 4 . The resultant was filtered on silica gel and then concentrated to obtain compound 1-1 (63 g, 98%).

[0207] Preparation of compound 1-2

[0208] In a single-necked round-bottom flask (single-necked rbf), a mixture of 3-bromo-4'-chloro-2-fluoro-2'-methoxy-1,1'-biphenyl (63 g, 200 mmol) and methylene chloride (MC) (1000 ml) was cooled to a temperature of 0°C, BBr3 (38 ml, 400 mmol) was added dropwise thereto, and after the temperature was raised to room temperature, the resultant was stirred for 2 hours. The reaction was terminated with distilled water, and the resultant was extracted with methylene chloride and dried with MgSO4. The resultant was subjected to column purification (MC:HX=1:2) to obtain compound 1-2 (75 g, 80%).

[0209] Preparation of Compound 1-3

[0210] In a single-necked round-bottom flask (single-necked rbf), a mixture of 3'-bromo-4-chloro-2'-fluoro-[1,1'-biphenyl]-2-ol (75 g, 248.7 mmol), Cs2CO3 (438.7 g, 1243.5 mmol) and dimethylacetamide (750 ml) was stirred at 120° C. The resultant was cooled, then filtered, and after removing the solvent of the filtrate, column purification (HX:MC=5:1) was performed to obtain compound 1-3 (79.5 g, 88%).

[0211] Preparation of Compound 1-4

[0212] In a single-necked round-bottom flask (single-necked rbf), a mixture of 6-bromo-3-chlorodibenzo[b,d]furan) (79.5 g, 282 mmol), bis(pinacol)diboron (143 g, 564 mmol), Pd(dppf)Cl2 (20 g, 28.2 mmol), potassium acetate (83 g, 846 mmol) and 1,4-dioxane (800 ml) was refluxed at 140°C. The resultant was extracted with dichloromethane, concentrated and then treated with dichloromethane / MeOH to obtain compound 1-4 (95.5 g, 97%).

[0213] Preparation of Compound 1-5

[0214] In a single-necked round-bottom flask (single-necked rbf), 2-(7-chlorodibenzo[b,d]furan-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (10 g, 30 mmol), 3-bromo-9,9-dimethyl-9H-dibenzopyran (10 g, 36 mmol), tetrakis(triphenylphosphine)palladium(0) (3.5 g, 3 mmol), potassium carbonate (12.4 g, 90 mmol) and 1,4-dioxane / water (150 ml / 30 ml) were refluxed at 120° C. for 3 hours. The resultant was filtered at 120° C. and then washed with 1,4-dioxane, distilled water and MeOH to obtain compound 1-5 (13.4 g, 92%).

[0215] Preparation of Compound 1-6

[0216] In a single-necked round-bottom flask (single-necked rbf), a mixture of 3-(7-chlorodibenzo[b,d]furan-4-yl)-9,9-dimethyl-9H-dibenzopyran (10 g, 24.3 mmol), bis(pinacol)diboron (12.3 g, 48 mmol), XPhos (2.3 g, 4.8 mmol), potassium acetate (7.1 g, 73 mmol), Pd2(dba)3 (2.2 g, 2.4 mmol) and 1,4-dioxane (100 ml) was refluxed at 140° C. The resultant was extracted with dichloromethane, concentrated and then treated with dichloromethane / MeOH to obtain compound 1-6 (12.7 g, 96%).

[0217] Preparation of compound 1

[0218] In a single-necked round-bottom flask (single-necked rbf), a mixture of 2-(6-(9,9-dimethyl-9H-dibenzopyran-3-yl)dibenzo[b,d]furan-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (10 g, 20 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (6.4 g, 24 mmol), tetrakis(triphenylphosphine)palladium(0) (2.3 g, 2 mmol), potassium carbonate (8.2 g, 60 mmol) and 1,4-dioxane / water (150 ml / 30 ml) was refluxed at 120° C. for 3 hours. The resultant was filtered at 120° C. and then washed with 1,4-dioxane, distilled water and MeOH to obtain Compound 1 (12.7 g, 95%).

[0219] The following compounds were synthesized in the same manner as in Preparation Example 1, except that Intermediates A and B of the following Table 1 were used instead of A and B.

[0220] [Table 1]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228] [Preparation Example 2] Preparation of Compound 5 (F)

[0229]

[0230] Preparation of compound 5-1

[0231] In a single-necked round-bottom flask (single-necked rbf), a mixture of 1-bromo-2,3-difluorobenzene (50 g, 259 mmol), (4-chloro-2-methoxyphenyl)boric acid (57.7 g, 310 mmol), tetrakis(triphenylphosphine)palladium(0) (29 g, 25.9 mmol), potassium carbonate (71.5 g, 51.8 mmol) and toluene / ethanol / water (800 ml / 160 ml / 160 ml) was refluxed at 110° C. The resultant was extracted with dichloromethane and dried over MgSO 4 . The resultant was filtered on silica gel and then concentrated to obtain compound 5-1 (65 g, 99%).

[0232] Preparation of compound 5-2

[0233] In a single-necked round-bottom flask (single-necked rbf), a mixture of 4'-chloro-2,3-difluoro-2'-methoxy-1,1'-biphenyl (65 g, 255 mmol) and MC (1000 mL) was cooled to a temperature of 0°C, BBr3 (48 mL, 500 mmol) was added dropwise thereto, and after the temperature was raised to room temperature, the resultant was stirred for 2 hours.

[0234] The reaction was terminated with distilled water, and the resultant was extracted with dichloromethane and dried over MgSO 4. The resultant was subjected to column purification (MC:HX=1:2) to obtain compound 5-2 (49 g, 80%).

[0235] Preparation of compound 5-3

[0236] In a single-necked round-bottom flask (single-necked rbf), a mixture of 4-chloro-2',3'-difluoro-[1,1'-biphenyl]-2-ol (49 g, 203 mmol), Cs2CO3 (331 g, 1018 mmol) and dimethylacetamide (500 ml) was stirred at 120° C. The resultant was cooled, then filtered, and after removing the solvent of the filtrate, column purification (HX:MC=5:1) was performed to obtain compound 5-3 (50.1 g, 88%).

[0237] Preparation of compound 5-4

[0238] In a single-necked round-bottom flask (single-necked rbf), a mixture of 3-chloro-6-fluorodibenzo[b,d]furan (10 g, 45 mmol), 9,9-dimethyl-9,10-dihydroacridine (11.4 g, 54.3 mmol), Cs2CO3 (31.7 g, 90 mmol) and dimethylacetamide (100 ml) was refluxed at 170° C. for 12 hours. The resultant was cooled, then filtered, and after removing the solvent of the filtrate, column purification (HX:MC=4:1) was performed to obtain compound 5-4 (27.5 g, 67%).

[0239] Preparation of compound 5-5

[0240] In a single-necked round bottom flask (single-necked rbf), a mixture of 10-(7-chlorodibenzo[b,d]furan-4-yl)-9,9-dimethyl-9,10-dihydroacridine (10 g, 24.4 mmol), bis(pinacol)diboron (12.3 g, 48.8 mmol), XPhos (2.3 g, 4.8 mmol), potassium acetate (7.1 g, 73.2 mmol), Pd2(dba)3 (2.2 g, 2.4 mmol) and 1,4-dioxane (100 ml) was refluxed at 140° C. The resultant was extracted with dichloromethane, concentrated and then treated with dichloromethane / MeOH to obtain compound 5-5 (12.5 g, 98%).

[0241] Preparation of compound 5

[0242] In a single-necked round bottom flask (single-necked rbf), a mixture of 9,9-dimethyl-10-(7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)dibenzo[b,d]furan-4-yl)-9,10-dihydroacridine (10 g, 20 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (6.4 g, 24 mmol), tetrakis(triphenylphosphine)palladium(0) (2.3 g, 2 mmol), potassium carbonate (8.3 g, 60 mmol) and 1,4-dioxane / water (150 ml / 30 ml) was refluxed at 120° C. for 3 hours. The resultant was filtered at 120° C., and then washed with 1,4-dioxane, distilled water and MeOH to obtain compound 5 (14.8 g, 82%).

[0243] The following compounds were synthesized in the same manner as in Preparation Example 2, except that Intermediates D and E of the following Table 2 were used instead of D and E.

[0244] [Table 2]

[0245]

[0246]

[0247]

[0248] [Preparation Example 3] Preparation of Compound 49 (G)

[0249]

[0250] The target compound 49(G) (12.7 g, 95%) was obtained in the same manner as in the preparation of Compound 1 of Preparation Example 1, except that 1,4-dibromo-2-fluorobenzene was used instead of 1,3-dibromo-2-fluorobenzene.

[0251] The following compounds were synthesized in the same manner as in Preparation Example 3, except that Intermediates A and B of the following Table 3 were used instead of A and B.

[0252] [Table 3]

[0253]

[0254] [Preparation Example 4] Preparation of Compound 97 (H)

[0255]

[0256] The target compound 97(H) (12.7 g, 95%) was obtained in the same manner as in the preparation of Compound 1 of Preparation Example 1, except that 2,4-dibromo-1-fluorobenzene was used instead of 1,3-dibromo-2-fluorobenzene.

[0257] The following compounds were synthesized in the same manner as in Preparation Example 4, except that Intermediates A and B of the following Table 4 were used instead of A and B.

[0258] [Table 4]

[0259]

[0260]

[0261] [Preparation Example 5] Preparation of Compound 145 (I)

[0262]

[0263] The target compound 145(I) (12.7 g, 95%) was obtained in the same manner as in the preparation of Compound 1 of Preparation Example 1, except that 1,2-dibromo-3-fluorobenzene was used instead of 1,3-dibromo-2-fluorobenzene.

[0264] The following compounds were synthesized in the same manner as in Preparation Example 5, except that Intermediates A and B of the following Table 5 were used instead of A and B.

[0265] [Table 5]

[0266]

[0267]

[0268] [Preparation Example 6] Preparation of Compound 53 (J)

[0269]

[0270] The target compound 53(J) was obtained in the same manner as in Preparation Example 2, except that 1-bromo-2,4-difluorobenzene was used instead of 1-bromo-2,3-difluorobenzene.

[0271] The following compounds were synthesized in the same manner as in Preparation Example 6, except that Intermediates D and E of the following Table 6 were used instead of D and E.

[0272] [Table 6]

[0273]

[0274] [Preparation Example 7] Preparation of Compound 101 (K)

[0275]

[0276] The target compound 101(K) was obtained in the same manner as in Preparation Example 2, except that 2-bromo-1,4-difluorobenzene was used instead of 1-bromo-2,3-difluorobenzene.

[0277] The following compounds were synthesized in the same manner as in Preparation Example 7, except that Intermediates D and E of the following Table 7 were used instead of D and E.

[0278] [Table 7]

[0279]

[0280] [Preparation Example 8] Preparation of Compound 149 (L)

[0281]

[0282] The target compound 149(L) was obtained in the same manner as in Preparation Example 2, except that 2-bromo-1,3-difluorobenzene was used instead of 1-bromo-2,3-difluorobenzene.

[0283] The following compounds were synthesized in the same manner as in Preparation Example 8, except that Intermediates D and E of the following Table 8 were used instead of D and E.

[0284] [Table 8]

[0285]

[0286] Compound 1 to Compound 200 other than the compounds described in Table 1 to Table 8 were also prepared using the same method described in the Preparation Examples described above.

[0287] The synthetic identification information of the compounds prepared above are described in the following [Table 9] and [Table 10].

[0288] [Table 9]

[0289]

[0290]

[0291] [Table 10]

[0292]

[0293]

[0294] <Example>

[0295] 1) Manufacturing of organic light-emitting devices

[0296] A glass substrate on which a 1,500 angstrom thick indium tin oxide (ITO) thin film is coated is ultrasonically cleaned with distilled water. After the cleaning with distilled water is completed, the substrate is ultrasonically cleaned with a solvent such as acetone, methanol, and isopropyl alcohol, then dried, and UVO treated for 5 minutes using UV in a UV cleaner. Thereafter, the substrate is transferred to a plasma cleaner (PT), and after plasma treatment is performed under vacuum for ITO work function and residual film removal, the substrate is transferred to a thermal deposition device for organic deposition.

[0297] 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.

[0298] A light-emitting layer was thermally vacuum deposited thereon as follows. A 400 angstrom light-emitting layer was deposited as a host using the compounds described in Table 11 below, and 7% of Ir(ppy)3 (tris(2-phenylpyridine)iridium) as a green phosphorescent dopant was doped into the host. Thereafter, 60 angstroms of BCP were deposited as a hole blocking layer, and 200 angstroms of Alq3 were deposited thereon as an electron transport layer. Finally, an electron injection layer was formed on the electron transport layer by depositing lithium fluoride (LiF) having a thickness of 10 angstroms, and then a cathode was formed on the electron injection layer by depositing an aluminum (Al) cathode having a thickness of 1,200 angstroms, and thus, an organic electroluminescent device was manufactured.

[0299] 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 OLED manufacturing.

[0300] 2) Driving voltage and luminous efficiency of organic electroluminescent devices

[0301] For each of the organic electroluminescent devices manufactured as above, electroluminescent (EL) characteristics were measured using M7000 manufactured by McScience Inc., and through the measurement results, T was measured via a service life measurement system (M6000) manufactured by McScience Inc. when the standard brightness was 6,000 cd / m2. 90 The characteristics of the organic electroluminescent device of the present disclosure are shown in Table 11.

[0302] [Table 11]

[0303]

[0304]

[0305] [Comparative Example 1]

[0306]

[0307] [Comparative Example 2]

[0308]

[0309] [Comparative Example 3]

[0310]

[0311] [Comparative Example 4]

[0312]

[0313] [Comparative Example 5]

[0314]

[0315] [Comparative Example 6]

[0316]

[0317] [Comparative Example 7]

[0318]

[0319] As can be seen from Table 11, it has been confirmed that by Ar1 of Chemical Formula 1 being represented by Chemical Formula 2 or Chemical Formula 3 in the compound according to the present application, electron distribution is widely diffused from the dibenzofuran core to the substituent of Ar1, thereby generating a wide energy band gap and a high T1 value. In addition, it has been confirmed that by Ar1 of Chemical Formula 1 having a substituent of Chemical Formula 2 or Chemical Formula 3, a stable molecular structure can be maintained, thereby promoting enhancement of service life.

[0320] Therefore, it has been determined that the organic light-emitting device has excellent efficiency and low driving voltage in the present application when Chemical Formula 1 is used as a phosphorescent host material of the organic light-emitting device due to the characteristics of a wide energy band gap and a high T1 compared with the case of carbazole.

[0321] In Table 11, Comparative Examples 1 and 2 have a dimethyl dibenzopyranyl group having a symmetrical structure as a substituent, and Comparative Examples 3, 4, and 5 are compounds having an azine substituent, a carbazole group, and a dibenzopyranyl group at different positions of dibenzofuran. Comparative Example 6 of Table 10 has both an azine substituent and a dibenzofuranyl group at the 2nd and 4th positions of a single side benzene ring of dibenzofuran, and Comparative Example 7 has an azine substituent at the 3rd position of dibenzofuran while introducing a carbazole group into another benzene ring, and it has been determined that the compounds of Comparative Examples 1 to 7 have lower T1 and narrower energy band gaps than the compound of Chemical Formula 1 of the present disclosure.

[0322] Therefore, it was found that Comparative Examples 1 to 7 of Table 11 had characteristics of high driving voltage and low efficiency compared to when the compound corresponding to Chemical Formula 1 of the present application was used.

Claims

1. A heterocyclic compound represented by the following chemical formula 1: [Chemical formula 1] in, In Chemical Formula 1, N-Het is represented by the following chemical formula 8; In Chemical Formula 8, It means the site of connection to L1 of Chemical Formula 1; X1 is CR21 or N, X2 is CR22 or N, X3 is CR23 or N, X4 is CR24 or N, and X5 is CR25 or N; At least one of X1 to X5 is N; R21 to R25 are the same as or different from each other and are independently selected from the group consisting of: substituted or unsubstituted C6 to C40 aryl; or substituted or unsubstituted C2 to C40 heteroaryl; L1 and L2 are direct bonds; or C6 to C20 arylene groups; a and d are each an integer from 1 to 3, and when a is 2 or more, L1 are the same or different from each other, and when d is 2 or more, L2 are the same or different from each other; Rm and Rn are hydrogen; or deuterium; b and c are each an integer from 1 to 3, and when b is 2 or more, Rm is the same as or different from each other, and when c is 2 or more, Rn is the same as or different from each other; and Ar1 is represented by the following Chemical Formula 2 or Chemical Formula 3, [Chemical formula 2] [Chemical formula 3] In Chemical Formula 2 and Chemical Formula 3, It means the site of connection to L2 of Chemical Formula 1; R1 to R13 are the same or different from each other and are independently selected from the group consisting of: hydrogen; and deuterium, e is an integer from 1 to 3, and when e is 2 or greater than 2, R13 are the same or different from each other; A1 and A2 are the same or different from each other and are each independently O; S; CRaRb; NRc; or SiRdRe; A3 is O; S; CRaRb; NRc; or SiRdRe; and Ra to Re are the same as or different from each other, and are each independently a C1 to C40 alkyl group; or a C6 to C40 aryl group, or two or more groups adjacent to each other may be combined with each other to form a C6 to C40 aromatic hydrocarbon ring or a C2 to C40 heterocyclic ring.

2. The heterocyclic compound according to claim 1, wherein Chemical Formula 1 is represented by any one of the following Chemical Formulas 4 to 7: [Chemical formula 4] [Chemical formula 5] [Chemical formula 6] [Chemical formula 7] In Chemical Formulae 4 to 7, Each substituent has the same definition as in Chemical Formula 1.

3. The heterocyclic compound according to claim 1, wherein Chemical Formula 8 is any one selected from the following structural formulas: In the structural formula, R21 to R25 have the same meanings as in Chemical Formula 8.

4. The heterocyclic compound according to claim 1, wherein Chemical Formula 3 is represented by any one of the following Chemical Formulas 3-1 to 3-4: [Chemical formula 3-1] [Chemical formula 3-2] [Chemical formula 3-3] [Chemical formula 3-4] In Chemical Formula 3-1 to Chemical Formula 3-4, Each substituent has the same definition as in Chemical Formula 3.

5. The heterocyclic compound according to claim 1, wherein Chemical Formula 1 is represented by any one of the following compounds:

6. An organic light-emitting device, comprising: a first electrode; a second electrode, arranged to be 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 include the heterocyclic compound as claimed in any one of claims 1 to 5. 7 . The organic light-emitting device according to claim 6 , wherein the organic material layer comprises a light-emitting layer, and the light-emitting layer comprises the heterocyclic compound. 8 . The organic light-emitting device according to claim 6 , wherein 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. 9 . The organic light-emitting device according to claim 6 , wherein the organic material layer comprises an electron injection layer or an electron transport layer, and the electron transport layer or the electron injection layer comprises the heterocyclic compound. 10 . The organic light-emitting device according to claim 6 , wherein the organic material layer comprises an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer comprises the heterocyclic compound.

11. The organic light-emitting device according to claim 6, further comprising 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.

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