Heterocyclic compound, organic light-emitting device containing the same, composition for organic layer of organic light-emitting device, and method for manufacturing organic light-emitting device

Abstract

The present specification provides a heterocyclic compound represented by Chemical Formula 1, an organic light-emitting device containing the heterocyclic compound, a composition for an organic material layer of the organic light-emitting device, and a method for manufacturing the organic light-emitting device.

Description

[Technical Field]

[0001] This application claims the benefit of the filing date of Korean Patent Application No. 10-2019-0140749, filed with the Korean Intellectual Property Office on November 6, 2019, the entire contents of which are incorporated herein by reference. The present specification relates to a heterocyclic compound, an organic light-emitting device containing the heterocyclic compound, a composition for an organic material layer of the organic light-emitting device, and a method for producing the organic light-emitting device. [Background technology]

[0002] An organic electroluminescent device is a type of self-luminous display device, and has the advantages of a wide viewing angle, excellent contrast, and fast response speed. An organic light-emitting device has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to an organic light-emitting device with this structure, electrons and holes injected from the two electrodes combine in the organic thin film to form pairs, and then annihilate, emitting light. The organic thin film may be configured as a single layer or multiple layers as required.

[0003] The organic thin film material may have a light-emitting function as needed. For example, the organic thin film material may be a compound that can form an emitting layer by itself, or a compound that functions as a host or dopant in a host-dopant emitting layer. In addition, the organic thin film material may be a compound that functions as a hole injection, hole transport, electron block, hole block, electron transport, electron injection, etc.

[0004] To improve the performance, lifetime or efficiency of organic light-emitting devices, there is a continuing need to develop materials for organic thin films. Research is needed into organic light-emitting devices that contain compounds that can satisfy the requirements for materials that can be used in organic light-emitting devices, such as appropriate energy levels, electrochemical stability, and thermal stability, and that have chemical structures that can perform the various roles required in organic light-emitting devices depending on the substituents. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] U.S. Patent No. 4,356,429 Summary of the Invention [Problem to be solved by the invention]

[0006] The present application relates to a heterocyclic compound, an organic light-emitting device containing the heterocyclic compound, a composition for an organic layer of the organic light-emitting device, and a method for producing the organic light-emitting device. [Means for solving the problem]

[0007] In one embodiment of the present application, there is provided a heterocyclic compound represented by the following Chemical Formula 1: [ka] In the above Chemical Formula 1, N-Het is a substituted or unsubstituted, monocyclic or polycyclic C2 to C60 heterocyclic group containing one or more N atoms, L and L1 are the same or different and each independently represent a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group; Ar is a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group; R1 to R11 are the same or different and each independently represent a hydrogen atom; a deuterium atom; a halogen atom; a cyano group; 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; -P(=O)RR'; -SiRR'R" and -NRR'; 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 heterocycle; wherein R, R', and R" are the same or different and each independently represent 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; a and c are integers from 0 to 4, b is an integer of 0 to 2.

[0008] Furthermore, according to one embodiment of the present application, there is provided an organic light-emitting device including a first electrode, a second electrode provided opposite to the first electrode, and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes a heterocyclic compound represented by Chemical Formula 1.

[0009] Furthermore, in one embodiment of the present application, there is provided a composition for an organic layer of an organic light-emitting device, comprising a heterocyclic compound represented by Chemical Formula 1 above and a heterocyclic compound represented by Chemical Formula 2 below. [ka] In the above Chemical Formula 2, Ra and Rb are the same or different and each independently represent a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group; Rc and Rd are the same or different and are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C60 alkyl, substituted or unsubstituted C2-C60 alkenyl, substituted or unsubstituted C2-C60 alkynyl, substituted or unsubstituted C1-C60 alkoxy, substituted or unsubstituted C3-C60 cycloalkyl, substituted or unsubstituted C2-C60 heterocycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, and substituted or unsubstituted amine; r and s are integers of 0 to 7.

[0010] Finally, in one embodiment of the present application, there is provided a method for manufacturing an organic light-emitting element, comprising the steps of: preparing a substrate; forming a first electrode on the substrate; forming one or more organic material layers on the first electrode; and forming a second electrode on the organic material layers, wherein the step of forming the organic material layers comprises forming one or more organic material layers using a composition for an organic material layer according to one embodiment of the present application. [Effects of the Invention]

[0011] The compounds described herein can be used as organic layer materials in organic light-emitting devices. The compounds can serve as hole injection materials, hole transport materials, light-emitting materials, electron transport materials, electron injection materials, and the like in organic light-emitting devices. In particular, the compounds can be used as light-emitting layer materials in organic light-emitting devices. For example, the compounds can be used alone as light-emitting materials, or two of the compounds can be used together as light-emitting materials, and can be used as host materials in the light-emitting layer.

[0012] In particular, the compound of Formula 1 has an N-containing ring substituted at a specific position on one benzene ring of the dibenzofuran structure, and a carbazole substituent and a specific substituent substituted on the other benzene ring of the dibenzofuran structure where the N-containing ring is not substituted. In this case, the linearity of the overall material is increased, and the dipole moment of the material is further strengthened. As a result, the electron-withdrawing effect, a characteristic of the strong ET unit containing the N-containing ring, is further enhanced, and the non-uniformly distributed electrons of the dibenzofuran are more strongly attracted to the ET unit. The compound of Formula 1 can be used to prepare an organic light emitting device having improved lifetime, driving stability, and efficiency. [Brief explanation of the drawings]

[0013] [Figure 1] 1 is a diagram schematically illustrating a stacked structure of an organic light-emitting device according to an embodiment of the present application. [Figure 2] 1 is a diagram schematically illustrating a stacked structure of an organic light-emitting device according to an embodiment of the present application. [Figure 3] 1 is a diagram schematically illustrating a stacked structure of an organic light-emitting device according to an embodiment of the present application. DETAILED DESCRIPTION OF THE INVENTION

[0014] The present application will be described in detail below. In this specification, when "no substituent is shown in the chemical formula or compound structure," it means that a hydrogen atom is bonded to a carbon atom. However, deuterium ( 2 Since H (Deuterium) is an isotope of hydrogen, some hydrogen atoms may be deuterium.

[0015] In one embodiment of the present application, "when no substituent is shown in the chemical formula or compound structure," can mean that all positions corresponding to the substituents are hydrogen or deuterium. That is, in the case of deuterium, it is an isotope of hydrogen, and some hydrogen atoms may be deuterium, which is an isotope, and in this case, the content of deuterium may be 0% to 100%.

[0016] In one embodiment of the present application, in the case where "no substituent is represented in the chemical formula or compound structure," hydrogen and deuterium can be used together in the compound if deuterium is not explicitly excluded, such as when the deuterium content is 0% or the hydrogen content is 100%. That is, when it is expressed as "substituent X is hydrogen," it can mean a state in which hydrogen and deuterium are mixed together, without excluding deuterium, such as when the hydrogen content is 100% or the deuterium content is 0%.

[0017] In one embodiment of the present application, deuterium is one of the isotopes of hydrogen and is an element having a deuteron consisting of one proton and one neutron as an atomic nucleus, and may be represented as hydrogen-2, or its atomic symbol may be written as D or 2H.

[0018] In one embodiment of the present application, isotopes refer to atoms with the same atomic number (Z) but different mass numbers (A). Isotopes can also be interpreted as elements with the same number of protons but different numbers of neutrons.

[0019] In one embodiment of the present application, the content T% of a specific substituent can be defined as T2 / T1×100=T%, where T1 is the total number of substituents that the base compound may have and T2 is the number of specific substituents among them. That is, in one example: [ka] A phenyl group having a deuterium content of 20% is represented by the following structural formula when the total number of substituents that the phenyl group can have is 5 (T1 in the formula), of which the number of deuterium is 1 (T2 in the formula). That is, a phenyl group having a deuterium content of 20% may be represented by the following structural formula: [ka]

[0020] In addition, in one embodiment of the present application, a "phenyl group having a deuterium content of 0%" can mean a phenyl group that does not contain a deuterium atom, that is, a phenyl group that has 5 hydrogen atoms.

[0021] As used herein, the halogen may be fluorine, chlorine, bromine, or iodine.

[0022] In this specification, the alkyl group includes a straight or branched chain having 1 to 60 carbon atoms, and may be additionally substituted with other substituents. The number of carbon atoms in the alkyl group may be 1 to 60, specifically 1 to 40, and more specifically 1 to 20. Specific examples include a methyl group, an ethyl group, a propyl group, an n-propyl group, an isopropyl group, a butyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a sec-butyl group, a 1-methylbutyl group, a 1-ethylbutyl group, a pentyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, a hexyl group, an n-hexyl group, a 1-methylpentyl group, a 2-methylpentyl group, a 4-methyl-2-pentyl group, a 3,3-dimethylbutyl group, a 2-ethylbutyl group, a heptyl group, a methyl group, an ethyl group, a propyl ... Examples of alkyl groups include, but are not limited to, cyclohexyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1-dimethylpropyl, isohexyl, 2-methylpentyl, 4-methylhexyl, and 5-methylhexyl.

[0023] In this specification, the alkenyl group includes a straight or branched chain having 2 to 60 carbon atoms and may be additionally substituted with other substituents. The number of carbon atoms in the alkenyl group may be 2 to 60, specifically 2 to 40, and more specifically 2 to 20. Specific examples include, but are not limited to, a vinyl group, a 1-propenyl group, an isopropenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-pentenyl group, a 2-pentenyl group, a 3-pentenyl group, a 3-methyl-1-butenyl group, a 1,3-butadienyl group, an allyl group, a 1-phenylvinyl-1-yl group, a 2-phenylvinyl-1-yl group, a 2,2-diphenylvinyl-1-yl group, a 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl group, a 2,2-bis(diphenyl-1-yl)vinyl-1-yl group, a stilbenyl group, and a styrenyl group.

[0024] In this specification, the alkynyl group includes a straight or branched chain having 2 to 60 carbon atoms, and may be additionally substituted with other substituents. The number of carbon atoms in the alkynyl group may be 2 to 60, specifically 2 to 40, and more specifically 2 to 20.

[0025] In this specification, the alkoxy group may be linear, branched, or cyclic. The number of carbon atoms in the alkoxy group is not particularly limited, but those having 1 to 20 carbon atoms are preferred. Specifically, the alkoxy group may be, but is not limited to, methoxy, ethoxy, n-propoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc.

[0026] In this specification, the cycloalkyl group includes a monocyclic or polycyclic group having 3 to 60 carbon atoms and may be additionally substituted with other substituents. Here, polycyclic means a group in which the cycloalkyl group is directly linked or condensed with another cyclic group. Here, the other cyclic group may be a cycloalkyl group, but may also be other types of cyclic groups, such as a heterocycloalkyl group, an aryl group, or a heteroaryl group. The number of carbon atoms in the cycloalkyl group may be 3 to 60, specifically 3 to 40, and more specifically 5 to 20. Specific examples include, but are not limited to, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a 3-methylcyclopentyl group, a 2,3-dimethylcyclopentyl group, a cyclohexyl group, a 3-methylcyclohexyl group, a 4-methylcyclohexyl group, a 2,3-dimethylcyclohexyl group, a 3,4,5-trimethylcyclohexyl group, a 4-tert-butylcyclohexyl group, a cycloheptyl group, and a cyclooctyl group.

[0027] In this specification, the heterocycloalkyl group contains O, S, Se, N, or Si as a heteroatom, and includes a monocyclic or polycyclic group having 2 to 60 carbon atoms, which may be additionally substituted with other substituents. Here, the term "polycyclic group" refers to a group in which the heterocycloalkyl group is directly linked to or condensed with another cyclic group. Here, the other cyclic group may be a heterocycloalkyl group, but may also be other types of cyclic groups, such as a cycloalkyl group, an aryl group, or a heteroaryl group. The number of carbon atoms in the heterocycloalkyl group may be 2 to 60, specifically 2 to 40, and more specifically 3 to 20.

[0028] In this specification, the aryl group includes a monocyclic or polycyclic ring having 6 to 60 carbon atoms and may be additionally substituted with other substituents. Here, polycyclic refers to a group in which an aryl group is directly linked to or fused with another cyclic group. Here, the other cyclic group may be an aryl group, but it may also be other types of cyclic groups, such as a cycloalkyl group, a heterocycloalkyl group, or a heteroaryl group. The number of carbon atoms in the aryl group may be 6 to 60, specifically 6 to 40, and more specifically 6 to 25. Specific examples of the aryl group include a phenyl group, a biphenyl group, a triphenyl group (terphenyl group), a naphthyl group, an anthryl group, a chrysenyl group, a phenanthrenyl group, a perylenyl group, a fluoranthenyl group, a triphenylenyl group, a phenalenyl group, a pyrenyl group, a tetracenyl group, a pentacenyl group, an indenyl group, an acenaphthylenyl group, a 2,3-dihydro-1H-indenyl group, and fused cyclic groups thereof, but are not limited to these.

[0029] In this specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.

[0030] When the fluorenyl group is substituted, it may have the following structure, but is not limited to this. [ka]

[0031] In this specification, the heteroaryl group contains S, O, Se, N, or Si as a heteroatom, and includes a monocyclic or polycyclic ring having 2 to 60 carbon atoms, which may be additionally substituted with other substituents. Here, the polycyclic ring refers to a group in which the heteroaryl group is directly linked to or condensed with another cyclic group. Here, the other cyclic group may be a heteroaryl group, but may also be other types of cyclic groups, such as a cycloalkyl group, a heterocycloalkyl group, or an aryl group. The number of carbon atoms in the heteroaryl group may be 2 to 60, specifically 2 to 40, and more specifically 3 to 25.Specific examples of the heteroaryl group include a pyridyl group, a pyrrolyl group, a pyrimidyl group, a pyridazinyl group, a furanyl group, a thiophene group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, a furazanyl group, an oxadiazolyl group, a thiadiazolyl group, a dithiazolyl group, a tetrazolyl group, a pyranyl group, a thiopyranyl group, a diazinyl group, an oxazinyl group, a thiazinyl group, a dioxinyl group, and a triazinyl group. group, tetrazinyl group, quinolyl group, isoquinolyl group, quinazolinyl group, isoquinazolinyl group, quinozolyl group, naphthyridyl group, acridinyl group, phenanthridinyl group, imidazopyridinyl group, diazanaphthalenyl group, triazaindene group, indolyl group, indolizinyl group, benzothiazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiophene group, benzofuran group, dibenzothiophene group, dibenzofuran group, carbazolyl group, benzocathionyl group, carbazolyl group, dibenzocarbazolyl group, phenazinyl group, dibenzosilole group, spirobi(dibenzosilole), dihydrophenazinyl group, phenoxazinyl group, phenanthridyl group, imidazopyridinyl group, thienyl group, indolo[2,3-a]carbazolyl group, indolo[2,3-b]carbazolyl group, indolinyl group, 10,11-dihydro-dibenzo[b,f]azepine group, 9,10-dihydroacridinyl group, phenanthrazinyl group, phenothiazinyl group, Examples of such alkyl groups include, but are not limited to, azinyl, phthalazinyl, naphthyridinyl, phenanthrolinyl, benzo[c][1,2,5]thiadiazolyl, 5,10-dihydrodibenzo[b,e][1,4]azasilinyl, pyrazolo[1,5-c]quinazolinyl, pyrido[1,2-b]indazolyl, pyrido[1,2-a]imidazo[1,2-e]indolinyl, and 5,11-dihydroindeno[1,2-b]carbazolyl.

[0032] In this specification, the amine group may be selected from the group consisting of a monoalkylamine group, a monoarylamine group, a monoheteroarylamine group, —NH2, a dialkylamine group, a diarylamine group, a diheteroarylamine group, an alkylarylamine group, an alkylheteroarylamine group, and an arylheteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, a dibiphenylamine group, an anthracenylamine group, a 9-methylanthracenylamine group, a diphenylamine group, a phenylnaphthylamine group, a ditolylamine group, a phenyltolylamine group, a triphenylamine group, a biphenylnaphthylamine group, a phenylbiphenylamine group, a biphenylfluorenylamine group, a phenyltriphenylenylamine group, and a biphenyltriphenylenylamine group, but are not limited to these.

[0033] In this specification, an arylene group refers to an aryl group having two bonding positions, i.e., a divalent group. The above-mentioned explanation of the aryl group is applicable to these groups, except that they are both divalent groups. Furthermore, a heteroarylene group refers to a heteroaryl group having two bonding positions, i.e., a divalent group. The above-mentioned explanation of the heteroaryl group is applicable to these groups, except that they are both divalent groups.

[0034] As used herein, a phosphine oxide group is defined as -P(=O)R 101 R 102 and R 101 and R 102 are the same or different and may each independently be a substituent consisting of at least one of 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 phosphine oxide group include, but are not limited to, a diphenylphosphine oxide group and a dinaphthylphosphine oxide group.

[0035] As used herein, a silyl group is a substituent that contains Si and is directly linked to the Si atom as a radical, and is represented by -SiR 104 R 105 R 106 and R 104 ~R 106 are the same or different and may each independently be a substituent consisting of at least one of 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 silyl groups include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, and a phenylsilyl group.

[0036] As used herein, the term "adjacent" refers to a substituent substituted on an atom directly connected to the atom on which the substituent is substituted, a substituent sterically closest to the substituent, or another substituent substituted on the atom on which the substituent is substituted. For example, two substituents substituted at ortho positions on a benzene ring and two substituents substituted on the same carbon atom on an aliphatic ring are considered to be "adjacent" groups.

[0037] The aliphatic or aromatic hydrocarbon ring or heterocycle that can form the adjacent group can have the structures exemplified above as the cycloalkyl group, cycloheteroalkyl group, aryl group, and heteroaryl group, except that it is not a monovalent group.

[0038] As used herein, the term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position of the substitution is not limited as long as it is a position at which a hydrogen atom is substituted, i.e., a position at which a substituent can be substituted. When two or more substituents are substituted, the two or more substituents may be the same or different.

[0039] In this specification, the term "substituted or unsubstituted" means being substituted or unsubstituted with one or more substituents selected from the group consisting of C1 to C60 straight-chain or branched-chain alkyl; C2 to C60 straight-chain or branched-chain alkenyl; C2 to C60 straight-chain or branched-chain 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 being substituted or unsubstituted with a substituent in which two or more substituents selected from the above-mentioned exemplary substituents are linked together, The R, R', and R" may be the same or different, and each independently represent 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.

[0040] In one embodiment of the present application, there is provided a compound represented by Chemical Formula 1.

[0041] In one embodiment of the present application, the above-mentioned Chemical Formula 1 may be represented by the following Chemical Formula 3 or 4: [ka] [ka] In the above Chemical Formulas 3 and 4, The definitions of R1 to R11, N-Het, L, L1, Ar, a, b, and c are the same as those in Chemical Formula 1 above.

[0042] In the case of Formula 3, when an N-Het substituent is substituted at position 3 of dibenzofuran, the linearity of the overall material increases and the dipole moment of the material is strengthened. As a result, the electron-withdrawing effect, which is a characteristic of the strong ET unit containing the N-Het substituent, is further enhanced, and the non-uniformly distributed electrons of dibenzofuran are more attracted to the ET unit. In this case, the LUMO site of the host material is located around the N-Het substituent, which is the ET unit. When electrons are strongly attracted, the overlapping area with the HOMO site around the dibenzofuran is greatly reduced. In addition, as the electrons present in the area are concentrated toward the LUMO site, the electron density within the HOMO site decreases. As a result, the charge transfer within the molecule caused by the LUMO-HOMO overlap also decreases, resulting in increased stability of the molecular structure and significantly increased device lifespan.

[0043] In the case of Formula 4, when an N-Het substituent is substituted at the first position of the dibenzofuran, the linearity is relatively slightly reduced, but the linearity can be increased or decreased to a certain level depending on the position of the carbazole-based substituent or Ar substituent on the opposite side of the dibenzofuran. Therefore, although there is a slight electron-withdrawing effect, the degree of electron non-uniformity is higher, resulting in more active charge transfer within the molecule. In other words, the driving voltage and current efficiency within the device are particularly excellent in the case of Formula 4 due to the presence of non-uniformly distributed electrons and their active charge transfer effect.

[0044] In one embodiment of the present application, the chemical formula 3 may be represented by any one of the following chemical formulas 3-1 to 3-6. [ka] [ka] [ka] [ka] [ka] [ka] In the chemical formulas 3-1 to 3-6, The definitions of R1 to R11, N-Het, L, L1, Ar, a, b, and c are the same as those in Chemical Formula 3.

[0045] In one embodiment of the present application, the chemical formula 4 may be represented by any one of the following chemical formulas 4-1 to 4-6. [ka] [ka] [ka] [ka] [ka] [ka] In the chemical formulas 4-1 to 4-6, The definitions of R1 to R11, N-Het, L, L1, Ar, a, b, and c are the same as those in Chemical Formula 4.

[0046] In one embodiment of the present application, L and L1 are the same or different and may each independently represent a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group.

[0047] In other embodiments, L and L1 are the same or different and may each independently be a direct bond; a substituted or unsubstituted C6 to C40 arylene group; or a substituted or unsubstituted C2 to C40 heteroarylene group.

[0048] In still other embodiments, L and L1 are the same or different and may each independently be a direct bond; or a substituted or unsubstituted C6 to C40 arylene group.

[0049] In still another embodiment, L and L1 are the same or different and may each independently be a direct bond; or a substituted or unsubstituted C6 to C40 monocyclic or polycyclic arylene group.

[0050] In still other embodiments, L and L1 are the same or different and may each independently represent a direct bond; a substituted or unsubstituted C6 to C20 monocyclic arylene group; or a substituted or unsubstituted C10 to C30 polycyclic arylene group.

[0051] In still other embodiments, L and L1 are the same or different and may each independently be a direct bond; a C6 to C20 monocyclic arylene group; or a C10 to C30 polycyclic arylene group.

[0052] In still other embodiments, L and L1 are the same or different and may each independently be a direct bond; a phenylene group; or a biphenylene group.

[0053] In still other embodiments, L may be a direct bond.

[0054] In still other embodiments, L1 can be a direct bond; a phenylene group; or a biphenylene group.

[0055] In one embodiment of the present application, Ar may 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.

[0056] In other embodiments, Ar may be a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group.

[0057] In still other embodiments, Ar can be a C1 to C20 alkyl group or a C6 to C40 aryl group, substituted or unsubstituted with deuterium; or a C2 to C40 heteroaryl group.

[0058] In still other embodiments, Ar can be a C1-C20 alkyl group or a C6-C40 aryl group substituted or unsubstituted with deuterium; or a C2-C40 O- or S-containing heteroaryl group.

[0059] In still other embodiments, Ar can be a C1-C20 alkyl group or a C6-C30 aryl group substituted or unsubstituted with deuterium; or a C2-C30 O- or S-containing heteroaryl group.

[0060] In still other embodiments, Ar can be a methyl group or a phenyl group unsubstituted or substituted with deuterium; a biphenyl group; a naphthyl group; a terphenyl group; a dibenzothiophene group; or a dibenzofuran group.

[0061] In still other embodiments, Ar can be any one of the following structures: [ka] In the structural formula: [ka] means the position linked to L1, X1 is O; or S.

[0062] In one embodiment of the present application, R1 to R11 are the same or different and each independently selected from the group consisting of hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1 to C60 alkyl group; substituted or unsubstituted C2 to C60 alkenyl group; substituted or unsubstituted C2 to C60 alkynyl group; substituted or unsubstituted C1 to C60 alkoxy group; substituted or unsubstituted C3 to C60 cycloalkyl group; substituted or unsubstituted C2 to C60 heterocycloalkyl group; substituted or unsubstituted C6 to C60 aryl group; substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)RR'; -SiRR'R" and a substituted or unsubstituted amine 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.

[0063] In another embodiment, R1 to R11 are the same or different and each independently selected from the group consisting of hydrogen; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)RR'; -SiRR'R" and a substituted or unsubstituted amine 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.

[0064] In still another embodiment, R1 to R11 are the same or different and each independently selected from the group consisting of hydrogen and a substituted or unsubstituted C6 to C60 aryl 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.

[0065] In still another embodiment, R1 to R11 are the same or different and each independently selected from the group consisting of hydrogen and 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 or a substituted or unsubstituted C2 to C40 heterocycle.

[0066] In still another embodiment, R1 to R11 are the same or different and each independently selected from the group consisting of hydrogen and a C6 to C40 aryl group substituted or unsubstituted with deuterium, or two or more adjacent groups may be bonded to each other to form a C6 to C40 aromatic hydrocarbon ring substituted or unsubstituted with a C1 to C20 alkyl group, or a C2 to C40 heterocycle substituted or unsubstituted with a C6 to C30 aryl group.

[0067] In still another embodiment, R1 to R11 are the same or different and each independently represent hydrogen or a phenyl group substituted or unsubstituted with deuterium, or two or more adjacent groups may be bonded to each other to form an indene ring substituted or unsubstituted with a methyl group; a benzene ring; a benzofuran ring; a benzothiophene ring; or an indole ring substituted or unsubstituted with a phenyl group.

[0068] In one embodiment of the present application, R9 to R11 may be hydrogen.

[0069] In one embodiment of the present application, R1 to R8 are the same or different and each independently represent hydrogen; or a phenyl group substituted or unsubstituted with deuterium; or two or more adjacent groups may be bonded to each other to form an indene ring substituted or unsubstituted with a methyl group; a benzene ring; a benzofuran ring; a benzothiophene ring; or an indole ring substituted or unsubstituted with a phenyl group.

[0070] In one embodiment of the present application, N-Het may be a substituted or unsubstituted monocyclic or polycyclic C2 to C60 heterocyclic group containing one or more N atoms.

[0071] In another embodiment, N-Het may be a substituted or unsubstituted monocyclic or polycyclic C2 to C60 heterocyclic group containing 1 to 3 N atoms.

[0072] In still other embodiments, N-Het may be a substituted or unsubstituted monocyclic or polycyclic C2 to C60 heterocyclic group containing 1 to 2 N atoms.

[0073] In still other embodiments, N-Het may be a substituted or unsubstituted monocyclic or polycyclic C2 to C40 heterocyclic group containing 1 to 3 N atoms.

[0074] In still another embodiment, N-Het may be a substituted or unsubstituted monocyclic C2 to C40 heterocyclic group containing 1 to 3 N atoms.

[0075] In still another embodiment, N-Het may be a monocyclic C2-C40 heterocyclic group containing 1 to 3 N and substituted or unsubstituted with one or more substituents selected from the group consisting of a C1 to C20 alkyl group, a C6 to C40 aryl group, a C2 to C40 heteroaryl group, -P(=)ORR', and -SiRR'R'', or a substituent in which two or more of the above substituents are linked together.

[0076] In still other embodiments, N-Het may be a pyridine group, a pyrimidine group, or a triazine group, substituted or unsubstituted 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 substituent formed by linking two or more of the above-mentioned substituents.

[0077] In still other embodiments, N-Het may be a pyridine group, substituted or unsubstituted with one or more substituents selected from the group consisting of a phenyl group, a biphenyl group, a naphthyl group, a dibenzofuran group, and a dibenzothiophene group; a pyrimidine group; or a triazine group.

[0078] In one embodiment of the present application, N-Het may be selected from the following structural formulas: [ka] In the structural formula: [ka] means the position where it is connected to L in Chemical Formula 1; R41 to R45 are the same or different and each independently represent a hydrogen atom; 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.

[0079] In one embodiment of the present application, R41 to R45 are the same or different and may each independently represent 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.

[0080] In other embodiments, R41 to R45 are the same or different and may each independently represent 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.

[0081] In still another embodiment, R41 to R45 may be the same or different and each independently represent an aryl group of C6 to C40; or a heteroaryl group of C2 to C40.

[0082] In still another embodiment, R41 to R45 may be the same or different and may each independently be a phenyl group; a biphenyl group; a naphthyl group; a dibenzofuran group; or a dibenzothiophene group.

[0083] In one embodiment of the present application, R, R', and R" are the same or different 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.

[0084] In other embodiments, R, R', and R'' may be the same or different and may each independently be a substituted or unsubstituted C6 to C60 aryl group.

[0085] In still other embodiments, R, R', and R'' may be the same or different and may each independently be a substituted or unsubstituted C6 to C60 monocyclic or polycyclic aryl group.

[0086] In still another embodiment, R, R', and R'' may be the same or different and each independently represent a substituted or unsubstituted C6 to C40 monocyclic aryl group.

[0087] In still another embodiment, R, R', and R'' may be the same or different and each independently represent a C6 to C20 monocyclic aryl group.

[0088] In yet other embodiments, R, R', and R'' may be phenyl groups.

[0089] According to one embodiment of the present application, the above-mentioned Chemical Formula 1 may be represented by any one of the following compounds, but is not limited thereto: [ka] TIFF0007737719000025.tif181161 TIFF0007737719000026.tif165161 TIFF0007737719000027.tif164161 TIFF0007737719000028.tif164161 TIFF0007737719000029.tif181161 TIFF0007737719000030.tif120161 TIFF0007737719000031.tif174161 TIFF0007737719000032.tif179161 TIFF0007737719000033.tif187161 TIFF0007737719000034.tif170161 TIFF0007737719000035.tif164161 TIFF0007737719000036.tif155161 TIFF0007737719000037.tif133161

[0090] Furthermore, by introducing various substituents into the structure of Chemical Formula 1, it is possible to synthesize compounds having the unique properties of the introduced substituents. For example, by introducing into the core structure substituents that are primarily used in hole injection layer materials, hole transport layer materials, light emitting layer materials, electron transport layer materials, and charge generation layer materials used in the manufacture of organic light emitting devices, it is possible to synthesize materials that meet the requirements of each organic material layer.

[0091] Furthermore, by introducing various substituents into the structure of Chemical Formula 1, the energy band gap can be finely adjusted, while the properties at the interface between organic materials can be improved, thereby diversifying the uses of the material.

[0092] In addition, one embodiment of the present application provides an organic light-emitting device including a first electrode, a second electrode provided opposite to the first electrode, and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes a heterocyclic compound represented by Chemical Formula 1.

[0093] In another embodiment, there is provided an organic light-emitting device comprising a first electrode, a second electrode provided opposite the first electrode, and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises one heterocyclic compound represented by Chemical Formula 1.

[0094] The specific details regarding the heterocyclic compound represented by Chemical Formula 1 are the same as those described above.

[0095] In one embodiment of the present application, the first electrode may be an anode and the second electrode may be a cathode.

[0096] In other embodiments, the first electrode may be a cathode and the second electrode may be an anode.

[0097] 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 for the blue organic light emitting device. For example, the heterocyclic compound represented by Chemical Formula 1 may be included in a host material of a blue light emitting layer of the blue organic light emitting device.

[0098] 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. For example, the heterocyclic compound represented by Chemical Formula 1 may be included in a host material of a green light emitting layer of the green organic light emitting device.

[0099] 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. For example, the heterocyclic compound represented by Chemical Formula 1 may be included in a host material of a red light emitting layer of the red organic light emitting device.

[0100] The organic light-emitting device of the present invention can be manufactured by a conventional method and material for manufacturing an organic light-emitting device, except that one or more organic layers are formed using the heterocyclic compound described above.

[0101] The heterocyclic compound may be formed in an organic layer by a solution coating method, such as a vacuum deposition method, or a solution coating method, including, but not limited to, spin coating, dip coating, inkjet printing, screen printing, spraying, and roll coating, during the manufacture of an organic light emitting device.

[0102] The organic material layer of the organic light-emitting device of the present invention may have a single-layer structure or a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light-emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, an emitting layer, an electron transport layer, an electron injection layer, etc. as the organic material layer. However, the structure of the organic light-emitting device is not limited thereto and may include fewer organic material layers.

[0103] In the organic light-emitting device of the present invention, the organic material layer may include a light-emitting layer, and the light-emitting layer may include the heterocyclic compound.

[0104] In another organic light-emitting device, the organic material layer may include a light-emitting layer, the light-emitting layer may include a host material, and the host material may include the heterocyclic compound.

[0105] As another example, the organic layer containing the heterocyclic compound includes the heterocyclic compound represented by Chemical Formula 1 as a host, and can be used together with an iridium-based dopant.

[0106] In the organic light-emitting device of the present invention, the organic material layer may include an electron injection layer or an electron transport layer, and the electron transport layer or the electron injection layer may include the heterocyclic compound.

[0107] In another organic light-emitting device, the organic material layer may include an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer may include the heterocyclic compound.

[0108] The organic light-emitting device of the present invention may further include one 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.

[0109] 1 to 3 show examples of the stacking order of electrodes and organic layers of an organic light-emitting device according to one embodiment of the present application. However, these figures are not intended to limit the scope of the present application, and structures of organic light-emitting devices known in the art are also applicable to the present application.

[0110] 1 shows an organic light emitting device in which an anode 200, an organic material layer 300, and a cathode 400 are sequentially stacked on a substrate 100. However, the present invention is not limited to this structure, and an organic light emitting device in which a cathode, an organic material layer, and an anode are sequentially stacked on a substrate, as shown in FIG.

[0111] Figure 3 illustrates an example of a multi-layer organic material layer. The organic light-emitting device of Figure 3 includes a hole injection layer 301, a hole transport layer 302, an 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 stacked structure. If necessary, the remaining layers except for the emitting layer may be omitted, and other necessary functional layers may be further added.

[0112] The organic layer containing the compound of Formula 1 may further contain other materials as needed.

[0113] In the organic light emitting device according to one embodiment of the present application, the organic material layer may further include a heterocyclic compound represented by the following Chemical Formula 2: [ka] In the above Chemical Formula 2, Ra and Rb are the same or different and each independently represent a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group; Rc and Rd are the same or different and are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C60 alkyl, substituted or unsubstituted C2-C60 alkenyl, substituted or unsubstituted C2-C60 alkynyl, substituted or unsubstituted C1-C60 alkoxy, substituted or unsubstituted C3-C60 cycloalkyl, substituted or unsubstituted C2-C60 heterocycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, and substituted or unsubstituted amine; r and s are integers of 0 to 7.

[0114] When the compound of Formula 1 and the compound of Formula 2 are simultaneously contained in the organic material layer of an organic light-emitting device, better efficiency and lifespan effects are exhibited. This result suggests that an exciplex phenomenon occurs when the two compounds are simultaneously contained.

[0115] The exciplex phenomenon is a phenomenon in which electron exchange between two molecules releases energy at the HOMO level of the donor (p-host) and the LUMO level of the acceptor (n-host). When the exciplex phenomenon occurs between two molecules, reverse intersystem crossing (RISC) occurs, which can increase the internal quantum efficiency of fluorescence to 100%. When a donor (p-host) with good hole transporting ability and an acceptor (n-host) with good electron transporting ability are used as hosts in the emitting layer, holes are injected into the p-host and electrons are injected into the n-host, which can reduce the driving voltage and thereby improve the lifetime.

[0116] In one embodiment of the present application, the chemical formula 2 may be represented by any one of the following chemical formulas 5 to 12. [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] In the above chemical formulas 5 to 12, The definitions of Ra, Rb, Rc, Rd, r, and s are the same as those in Chemical Formula 2 above.

[0117] In the organic light-emitting device according to one embodiment of the present application, Ra and Rb in Chemical Formula 2 may be the same or different and may each independently represent a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C6 to C60 heteroaryl group.

[0118] In another embodiment of the organic light-emitting device, Ra and Rb in Formula 2 may be the same or different and each independently represent a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C6 to C40 heteroaryl group.

[0119] In an organic light-emitting device according to still another embodiment, Ra and Rb in Chemical Formula 2 may be the same or different and each independently represent a C6-C40 aryl group substituted or unsubstituted with one or more substituents selected from the group consisting of a C1-C40 alkyl group, a C6-C40 aryl group, -CN, and -SiR101R102R103; or a C2-C40 heteroaryl group substituted or unsubstituted with one or more substituents selected from the group consisting of a C6-C40 aryl group and a C2-C40 heteroaryl group.

[0120] In yet another embodiment of the organic light-emitting device, Ra and Rb in Chemical Formula 2 may be the same or different and each independently represent a phenyl group, a phenyl group substituted or unsubstituted with -CN, or -SiR101R102R103; a biphenyl group substituted or unsubstituted with a phenyl group; a naphthyl group; a fluorene group substituted or unsubstituted with a methyl group or a phenyl group; a spirobifluorene group; a dibenzothiophene group substituted or unsubstituted with one or more substituents selected from the group consisting of a phenyl group, a biphenyl group, a naphthyl group, a dimethylfluorene group, a dibenzothiophene group, and a dibenzofuran group; or a triphenylene group.

[0121] In the organic light-emitting device according to one embodiment of the present application, R101, R102, and R103 in Chemical Formula 2 may be a C6 to C20 monocyclic aryl group.

[0122] In the organic light emitting device according to one embodiment of the present application, R101, R102, and R103 in Chemical Formula 2 may be a phenyl group.

[0123] In one embodiment of the present application, Rc and Rd may be hydrogen.

[0124] In one embodiment of the present application, the Chemical Formula 2 may be represented by any one of the following compounds, but is not limited thereto: [ka] TIFF0007737719000048.tif204161 TIFF0007737719000049.tif200161 TIFF0007737719000050.tif210161 TIFF0007737719000051.tif210161 TIFF0007737719000052.tif211161 TIFF0007737719000053.tif211161 TIFF0007737719000054.tif211161 TIFF0007737719000055.tif96161

[0125] In the organic light emitting device according to one embodiment of the present application, the compound of Chemical Formula 2 may be contained in the light emitting layer of the organic material layer.

[0126] In the organic light emitting device according to one embodiment of the present application, the compound of Chemical Formula 2 may be included in the light emitting layer of the organic material layer, and specifically, may be used as a host material of the light emitting layer.

[0127] In one embodiment of the present application, the host material of the light-emitting layer of the organic light-emitting device may include the heterocyclic compound of Chemical Formula 1 and the heterocyclic compound of Chemical Formula 2 simultaneously.

[0128] In one embodiment of the present application, there is provided a composition for an organic layer of an organic light-emitting device, comprising the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2.

[0129] The weight ratio of the heterocyclic compound represented by Chemical Formula 1 to the heterocyclic compound represented by Chemical Formula 2 in the composition may be, but is not limited to, 1:10 to 10:1, 1:8 to 8:1, 1:5 to 5:1, or 1:2 to 2:1.

[0130] In one embodiment of the present application, there is provided a method for manufacturing an organic light-emitting device, comprising the steps of: preparing a substrate; forming a first electrode on the substrate; forming one or more organic material layers on the first electrode; and forming a second electrode on the organic material layers, wherein the step of forming the organic material layers comprises forming one or more organic material layers using a composition for an organic material layer according to one embodiment of the present application.

[0131] In one embodiment of the present application, there is provided a method for manufacturing an organic light emitting device, wherein the step of forming the organic material layer comprises forming the heterocyclic compound represented by Chemical Formula 1 by a thermal vacuum deposition method.

[0132] In one embodiment of the present application, there is provided a method for manufacturing an organic light-emitting device, wherein the step of forming the organic material layer comprises pre-mixing two kinds of heterocyclic compounds represented by Chemical Formula 1 and Chemical Formula 2 and forming the organic material layer using a thermal vacuum deposition method.

[0133] The term "pre-mixed" means that the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2 are first mixed and placed in a single source before being deposited on an organic layer.

[0134] The premixed materials are referred to as an organic layer composition according to one embodiment of the present application.

[0135] In the organic light-emitting device according to one embodiment of the present application, materials other than the heterocyclic compound of Chemical Formula 1 are exemplified below. However, these are merely examples and are not intended to limit the scope of the present application. They may be replaced with materials known in the art.

[0136] The anode material may be a material with a relatively large work function, such as a transparent conductive oxide, a metal, or a conductive polymer. Specific examples of the anode material include, but are not limited to, metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline.

[0137] The cathode material may be a material with a relatively low work function, such as a metal, a metal oxide, or a conductive polymer. Specific examples of the cathode material include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; and multilayer structures such as LiF / Al or LiO / Al.

[0138] As the hole injection material, known hole injection materials can be used, for example, phthalocyanine compounds such as copper phthalocyanine disclosed in U.S. Pat. No. 4,356,429, or starburst-type amine derivatives described in the literature [Advanced Material, 6, p. 677 (1994)], such as tris(4-carbazoyl-9-ylphenyl)amine (TCTA), 4,4′,4″-tri[phenyl(m-tolyl)amino]triphenylamine (m-MTDATA), 1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene (m-MTDAPB), and soluble conductive polymers such as polyaniline / dodecylbenzenesulfonic acid (Polyaniline / Dodecylbenzenesulfonic acid). Poly(3,4-ethylenedioxythiophene) / Poly(4-styrenesulfonate), polyaniline / Camphor sulfonic acid, or polyaniline / Poly(4-styrenesulfonate), etc. can be used.

[0139] As the hole transport material, pyrazoline derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, etc. can be used, and low-molecular or high-molecular materials may also be used.

[0140] Examples of electron transport materials that can be used include oxadiazole derivatives, anthraquinodimethane and its derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, tetracyanoanthraquinodimethane and its derivatives, fluorenone derivatives, diphenyldicyanoethylene and its derivatives, diphenoquinone derivatives, and metal complexes of 8-hydroxyquinoline and its derivatives. Not only low molecular weight substances but also high molecular weight substances may be used.

[0141] As the electron injection material, for example, LiF is typically used in the industry, but the present application is not limited thereto.

[0142] The light-emitting material may be a red, green, or blue light-emitting material, and two or more light-emitting materials may be mixed if necessary. The two or more light-emitting materials may be deposited as separate sources or premixed and deposited as a single source. The light-emitting material may be a fluorescent material or a phosphorescent material. The light-emitting material may be a material that emits light by combining holes and electrons injected from the anode and cathode, respectively, or a material in which both the host material and the dopant material contribute to light emission.

[0143] When a mixture of hosts of light-emitting materials is used, the mixture may be of the same type or different types. For example, two or more of n-type host materials or p-type host materials may be selected and used as the host material of the light-emitting layer.

[0144] The organic light emitting device according to an embodiment of the present application may be a front-emitting type, a back-emitting type, or a dual-side emitting type, depending on the materials used.

[0145] The heterocyclic compound according to one embodiment of the present application can also function in organic electronic devices including organic solar cells, organic photoreceptors, organic transistors, etc., based on a principle similar to that applied to organic light-emitting devices. [Example]

[0146] The present invention will be described in more detail below through examples, but these examples are merely for the purpose of illustrating the present application and are not intended to limit the scope of the present application.

[0147] <Production Example 1> Synthesis of intermediate 1-1-iv [ka]

[0148] Preparation of Compound 1-1-vi A single-neck round-bottom flask was charged with (4-chloro-2-fluorophenyl)boronic acid (100 g / 573.49 mmol), 2-bromo-4-fluorophenol (131.4 g / 688.19 mmol), Pd(PPh3)4 (33.13 g / 28.67 mmol), Na2CO3 (121.57 / 1146.99 mmol), and THF / HO (1200 ml / 200 ml) and stirred at reflux for 10 hours at 70 °C. After the reaction was completed, the mixture was extracted with dichloromethane, dried over MgSO4, purified using a column, and the filtrate was concentrated to give compound 1-1-vi (138 g, 100%).

[0149] Preparation of Compound 1-1-v Compound 1-1-vi (138 g / 573.49 mmol) and dichloromethane (1400 ml) were placed in a one-neck round-bottom flask and stirred at room temperature. NBS (107.18 g / 602.16 mmol) was then added dropwise and stirred for 1 hour. The reaction was terminated with distilled water, and the organic layer was separated and extracted, then dried over MgSO4. The column was then purified, and the filtrate was concentrated to obtain compound 1-1-v (134.2 g, 73%).

[0150] Preparation of Compound 1-1-iv Compound 1-1-v (134.2 g / 420.00 mmol), Cs2CO3 (273.68 g / 839.99 mmol), and DMAc (1400 ml) were placed in a one-neck round-bottom flask (one-neck RBF) and stirred under reflux at 170°C for 3 hours. After cooling to room temperature (25°C), the mixture was filtered to remove salts, and the solvent was removed from the filtrate. After washing with distilled water, the mixture was extracted with dichloromethane and dried over MgSO4. After column purification, the filtrate was concentrated to obtain intermediate compound 1-1-iv (45 g, 40%). The following target compound C was prepared in the same manner as in the preparation example 1-1-vi, except that A and B in Table 1 below were used as intermediates.

[0151] [Table 1]

[0152] <Production Example 2> Synthesis of intermediate 1-121-iv [ka]

[0153] Preparation of Compound 1-121-vi A single-necked round-bottom flask was charged with 1-bromo-2,4-difluoro-3-iodobenzene (40 g / 125.44 mmol), (4-chloro-2-methoxyphenyl)boronic acid (30.40 g / 163.07 mmol), Pd(PPh3)2Cl2 (7.04 g / 10.03 mmol), Na2CO3 (26.59 g / 250.87 mmol), and THF / HO (400 ml / 120 ml). The mixture was refluxed at 70 °C for 10 hours and stirred. After the reaction was complete, the mixture was extracted with dichloromethane, dried over MgSO4, and then purified using a column. The filtrate was concentrated to give compound 1-121-vi (27.2 g, 65%).

[0154] Preparation of compound 1-121-v Compound 1-121-vi (27.20 g / 81.54 mmol) and dichloromethane (300 ml) were placed in a one-neck round-bottom flask and stirred at room temperature. Then, BBr3 (40.85 g / 163.08 mmol) was added dropwise and stirred for 1 hour. The reaction was terminated with distilled water and filtered to remove salts. The organic layer was then separated and extracted, dried over MgSO4, and purified using a column. The filtrate was concentrated to give compound 1-121-v (24 g, 92%).

[0155] Preparation of Compound 1-121-iv Compound 1-121-v (24.0 g / 75.02 mmol), Cs2CO3 (48.87 g / 150.04 mmol), and DMAc (250 ml) were placed in a one-neck round-bottom flask (one-neck RBF) and stirred under reflux at 170 °C for 3 hours. After cooling to room temperature, the mixture was filtered to remove salts, and the solvent was removed from the filtrate. After washing with distilled water, the mixture was extracted with dichloromethane and dried over MgSO4. After column purification, the filtrate was concentrated to obtain compound 1-121-iv (20 g, 89%). The following target compound C was prepared in the same manner as in the above-mentioned compound 1-121-vi, except that in the above-mentioned Preparation Example 2, A and B in the following Table 2 were used as intermediates.

[0156] [Table 2]

[0157] <Production Example 3> Synthesis of Compound 1-1 [ka]

[0158] Preparation of Compound 1-1-iii Compound 1-1-iv (20 g / 66.77 mmol), phenylboronic acid (A) (8.96 g / 73.45 mmol), Pd(PPh3)4 (3.86 g / 3.34 mmol), K2CO3 (18.46 g / 133.55 mmol), and 1,4-dioxane / HO (200 mL / 40 mL) were placed in a one-neck round-bottom flask and stirred at reflux for 3 hours at 110 °C. The organic layer was extracted with dichloromethane, dried over MgSO4, and purified using a column. The filtrate was concentrated to give compound 1-1-iii (14 g, 71%).

[0159] Preparation of Compound 1-1-ii Compound 1-1-iii (12 g / 40.44 mmol), bispinacolatodiboron (17.46 g / 68.75 mmol), Pd2(dba)3 (3.70 g / 4.04 mmol), P(cy)3 (3.40 g / 12.13 mmol), KOAc (9.92 g / 101.10 mmol), and 1,4-dioxane (120 mL) were placed in a one-neck round-bottom flask and stirred at reflux at 110 °C for 1 hour. The reaction was quenched with distilled water, and the organic layer was extracted with dichloromethane and dried over MgSO4. Column purification and concentration of the filtrate gave compound 1-1-ii (14.6 g, 93%).

[0160] Preparation of Compound 1-1-i Compound 1-1-ii (14.6 g / 37.60 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (B) (11.08 g / 41.37 mmol), Pd(PPh3)4 (2.17 g / 1.88 mmol), K2CO3 (10.39 g / 75.21 mmol), and 1,4-dioxane / HO (150 mL / 30 mL) were placed in a one-neck round-bottom flask and refluxed at 110 °C for 6 hours. After cooling to room temperature and filtering, the solid was stirred in distilled water and MeOH for 1 hour. The solid was then dissolved in DCB and filtered through silica gel. The filtrate was concentrated to give compound 1-1-i (14.7 g, 80%).

[0161] Preparation of Compound 1-1 Compound 1-1-i (5.0 g / 10.13 mmol), 9H-carbazole (C) (2.20 g / 13.17 mmol), Cs2CO3 (13.20 g / 40.53 mmol), and DMAc (50 ml) were placed in a one-neck round-bottom flask and stirred at 170 °C for 72 hours under reflux. After cooling to room temperature and filtering, the solid was stirred in distilled water and MeOH for 1 hour. Next, it was dissolved in DCB and filtered through silica gel. The filtrate was concentrated to give compound 1-1 (4.54 g, 76%). The following target compound E was prepared in the same manner as in Preparation Example 3, except that A in Table 3 below was used as a starting material and B, C, and D were used as substituents.

[0162] [Table 3] TIFF0007737719000062.tif211169 TIFF0007737719000063.tif213169 TIFF0007737719000064.tif203169 TIFF0007737719000065.tif211169 TIFF0007737719000066.tif186169 TIFF0007737719000067.tif186169 TIFF0007737719000068.tif204169 TIFF0007737719000069.tif211169 TIFF0007737719000070.tif211169 TIFF0007737719000071.tif212169 TIFF0007737719000072.tif207169

[0163] <Production Example 4> Synthesis of Compound 3-3 [ka]

[0164] 1) Preparation of Compound 3-3 3.7 g (15.8 mM) of 3-bromo-1,1'-biphenyl, 6.5 g (15.8 mM) of 9-phenyl-9H,9'H-3,3'-bicarbazole, 3.0 g (15.8 mM) of CuI, 1.9 mL (15.8 mM) of trans-1,2-diaminocyclohexane, and 3.3 g (31.6 mM) of KPO were dissolved in 100 mL of 1,4-oxane and refluxed for 24 hours. After completion of the reaction, the mixture was extracted with distilled water and DCM at room temperature. The organic layer was dried over MgSO and the solvent was removed on a rotary evaporator. The reaction mixture was purified by column chromatography (DCM:Hex = 1:3) and recrystallized from methanol to yield 7.5 g (85%) of the target compound 3-3. Target compound A was synthesized in the same manner as in Production Example 3, except that intermediate A in Table 4 below was used instead of 3-bromo-1,1'-biphenyl and intermediate B in Table 4 below was used instead of 9-phenyl-9H,9'H-3,3'-bicarbazole.

[0165] [Table 4]

[0166] <Production Example 5> Synthesis of Compound 4-2 [ka]

[0167] 1) Preparation of Compound 4-2-2 4.2 g (15.8 mM) of 2-bromodibenzo[b,d]thiophene, 6.5 g (15.8 mM) of 9-phenyl-9H,9'H-3,3'-bicarbazole, 3.0 g (15.8 mM) of CuI, 1.9 mL (15.8 mM) of trans-1,2-diaminocyclohexane, and 3.3 g (31.6 mM) of KPO were dissolved in 100 mL of 1,4-oxane and refluxed for 24 hours. After completion of the reaction, the mixture was extracted with distilled water and DCM at room temperature. The organic layer was dried over MgSO and the solvent was removed on a rotary evaporator. The reaction mixture was purified by column chromatography (DCM:Hex = 1:3) and recrystallized from methanol to yield 7.9 g (85%) of the target compound 4-2-2.

[0168] 2) Preparation of Compound 4-2-1

[0169] To a mixture of 8.4 g (14.3 mmol) of compound 4-2-1 and 100 mL of THF, 7.4 mL (18.6 mmol) of 2.5 M n-BuLi was added dropwise at -78 °C and stirred at room temperature for 1 hour. 4.8 mL (42.9 mmol) of trimethylborate was added dropwise to the reaction mixture and stirred at room temperature for 2 hours. After the reaction was complete, the mixture was extracted with distilled water and DCM at room temperature. The organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:MeOH = 100:3) and recrystallized from DCM to obtain 3.9 g (70%) of the desired compound 4-2-1.

[0170] 3) Preparation of Compound 4-2 Compound 4-2-1 (6.7 g, 10.5 mM), iodobenzene (2.1 g, 10.5 mM), Pd(PPh) (606 mg, 0.52 mM), and KCO (2.9 g, 21.0 mM) were dissolved in toluene / EtOH / H2O (100:20:20 mL) and refluxed for 12 hours. After completion of the reaction, the mixture was extracted with distilled water and DCM at room temperature. The organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:Hex = 1:3) and recrystallized from methanol to yield 4.9 g (70%) of the target compound 4-2. The following target compound B was obtained in the same manner as in Preparation Example 5, except that compound A in Table 5 below was used instead of iodobenzene.

[0171] [Table 5]

[0172] Heterocyclic compounds corresponding to Chemical Formula 1 and Chemical Formula 2 other than the compounds described in Preparation Examples 1 to 5 and Tables 1 to 5 were also produced in the same manner as in the above-mentioned Preparation Examples. The synthesis confirmation data for the compounds prepared above are as shown in Tables 6 and 7 below.

[0173] [Table 6] TIFF0007737719000078.tif91169

[0174] [Table 7] TIFF0007737719000080.tif239169 TIFF0007737719000081.tif238169 TIFF0007737719000082.tif238169 TIFF0007737719000083.tif238169 TIFF0007737719000084.tif55169

[0175] <Experimental Example 1-1> - Preparation of organic light-emitting device (green, single host) A glass substrate coated with a 1,500 Å thick indium tin oxide (ITO) thin film was ultrasonically cleaned in distilled water. After the distilled water cleaning, it was ultrasonically cleaned with solvents such as acetone, methanol, and isopropyl alcohol, dried, and then treated with UVO in a UV cleaner for 5 minutes. The substrate was then transferred to a plasma cleaner (PT) and plasma treated in a vacuum to adjust the ITO work function and remove any remaining film, before being transferred to a thermal evaporation system for organic deposition. On the ITO transparent electrode (anode), a common layer consisting of a hole injection layer 2-TNATA (4,4',4"-Tris[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) was formed. An emitting layer was then formed thereon by thermal vacuum deposition as follows: The compound represented by Formula 1 in Table 8 below was deposited as a host to a thickness of 400 Å, and a green phosphorescent dopant, Ir(ppy)3, was deposited to a thickness of 7% of the deposition thickness of the emitting layer. Then, BCP was deposited to a thickness of 60 Å as a hole-blocking layer, and Alq3 was deposited to a thickness of 200 Å as an electron-transporting layer on top of that. Finally, lithium fluoride (LiF) was deposited to a thickness of 10 Å on the electron-transporting layer to form an electron-injecting layer, and then an aluminum (Al) cathode was deposited to a thickness of 1,200 Å on the electron-injecting layer to form a cathode, thereby completing the fabrication of an organic electroluminescent device. On the other hand, all the organic compounds required for manufacturing OLED elements are 10 -6 ~10 -8 It was purified by vacuum sublimation under torr and used for the fabrication of OLEDs. The electroluminescence (EL) characteristics of the organic electroluminescent device fabricated as described above were measured using a Mac Science M7000, and the measurement results were used to determine whether the reference luminance was 6,000 cd / m or less using a Mac Science M6000 lifespan measurement device. 2 The driving voltage, luminous efficiency, color coordinate (CIE), and lifetime of the fabricated organic light emitting device were measured, and the results are shown in Table 8 below.

[0176] [Table 8] TIFF0007737719000086.tif239169 TIFF0007737719000087.tif174169

[0177] [ka]

[0178] <Experimental Example 1-2> - Preparation of organic light-emitting device (green, pre-mixed host) A glass substrate coated with a 1,500Å thick ITO film was ultrasonically cleaned with distilled water. After the distilled water cleaning, it was ultrasonically cleaned with solvents such as acetone, methanol, and isopropyl alcohol, dried, and then treated with UVO for 5 minutes in a UV cleaner. The substrate was then transferred to a plasma cleaner (PT) and plasma treated in a vacuum to determine the ITO work function and remove any remaining film, before being transferred to a thermal evaporation device for organic deposition. On the ITO transparent electrode (anode), a common layer consisting of a hole injection layer 2-TNATA (4,4',4"-Tris[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) was formed. An emitting layer was then formed thereon by thermal vacuum deposition as follows. The emitting layer was formed by premixing one compound represented by Formula 1 in Table 9 below and one compound represented by Formula 2 in Table 9 below as the host, and then depositing the premixed mixture to a thickness of 400 Å from a single source. The green phosphorescent dopant, Ir(ppy)3, was deposited at a thickness of 7% of the deposition thickness of the emitting layer. Next, BCP was deposited to a thickness of 60 Å as a hole-blocking layer, and Alq3 was deposited to a thickness of 200 Å as an electron-transporting layer. Finally, lithium fluoride (LiF) was deposited to a thickness of 10 Å on the electron-transporting layer to form an electron-injecting layer. An aluminum (Al) cathode was then deposited to a thickness of 1,200 Å on the electron-injecting layer to form a cathode, completing the fabrication of an organic electroluminescent device. On the other hand, all the organic compounds required for manufacturing OLED elements are 10 -6 ~10 -8 It was purified by vacuum sublimation under torr and used for the fabrication of OLEDs. The electroluminescence (EL) characteristics of the organic electroluminescent device fabricated as described above were measured using a Mac Science M7000, and the measurement results were used to determine whether the reference luminance was 6,000 cd / m or less using a Mac Science M6000 lifespan measurement device. 2 The T90 was measured at this time. The driving voltage, luminous efficiency, color coordinate (CIE), and lifespan of the organic light emitting device manufactured according to the present invention were measured, and the results are shown in Table 9 below.

[0179] [Table 9] TIFF0007737719000090.tif45169

[0180] <Experimental Example 2-1> - Preparation of organic light-emitting device (red, single host) A glass substrate coated with a 1,500Å thick indium tin oxide (ITO) thin film was ultrasonically cleaned in distilled water. After the distilled water cleaning, the substrate was ultrasonically cleaned with solvents such as acetone, methanol, and isopropyl alcohol, dried, and then treated with UVO (Ultraviolet Ozone) for 5 minutes in a UV (Ultraviolet) cleaning machine. The substrate was then transferred to a plasma cleaning machine (PT) and plasma treated in a vacuum to determine the work function of the ITO and remove any remaining film, before being transferred to a thermal evaporation system for organic deposition. On the ITO transparent electrode (anode), a common layer consisting of a hole injection layer 2-TNATA (4,4',4"-Tris[2-naphthyl(phenyl)amino]triphenylamine) and a hole transport layer NPB (N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine) was formed. An emitting layer was then formed thereon by thermal vacuum deposition as follows. The emitting layer was formed using a compound corresponding to Formula 1 in Table 10 below as a red host and (piq)2(Ir)(acac) as a red phosphorescent dopant, doping the host with 3% (piq)2(Ir)(acac). A 500 Å thick layer was deposited. A 60 Å thick layer of BCP was then deposited as a hole-blocking layer, and a 200 Å thick layer of Alq3 was deposited on top of that as an electron-transporting layer. Finally, lithium fluoride (LiF) was deposited on the electron-transporting layer to a thickness of 10 Å to form an electron-injecting layer. An aluminum (Al) cathode was then deposited on the electron-injecting layer to a thickness of 1,200 Å to form a cathode, completing the fabrication of an organic electroluminescent device. On the other hand, all the organic compounds required for manufacturing OLED elements are 10 -6 ~10 -8 It was purified by vacuum sublimation under torr and used for the fabrication of OLEDs. The electroluminescence (EL) characteristics of the organic electroluminescent device fabricated as described above were measured using a Mac Science M7000, and the measurement results were used to determine whether the reference luminance was 6,000 cd / m or less using a Mac Science M6000 lifespan measurement device. 2The T90 was measured at this time. The properties of the organic electroluminescent device of the present invention are shown in Table 10 below.

[0181] [Table 10] TIFF0007737719000092.tif114169

[0182] [ka]

[0183] <Experimental Example 2-2> - Preparation of organic light-emitting device (red, pre-mixed host) A glass substrate coated with a 1,500 Å thick indium tin oxide (ITO) thin film was ultrasonically cleaned in distilled water. After the distilled water cleaning, it was ultrasonically cleaned with solvents such as acetone, methanol, and isopropyl alcohol, dried, and then treated with UVO in a UV cleaner for 5 minutes. The substrate was then transferred to a plasma cleaner (PT) and plasma treated in a vacuum to adjust the ITO work function and remove any remaining film, before being transferred to a thermal evaporation system for organic deposition. On the ITO transparent electrode (anode), a common layer consisting of a hole injection layer 2-TNATA (4,4',4"-Tris[2-naphthyl(phenyl)amino]triphenylamine) and a hole transport layer NPB (N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine) was formed. An emitting layer was then formed thereon by thermal vacuum deposition as follows. The emitting layer was formed by premixing two compounds corresponding to Compound 1 and Compound 2 (see Table 11 below) as a red host and depositing them to a thickness of 400 Å from a single source. The red phosphorescent dopant was deposited by doping with 3% (piq)2(Ir)(acac). Next, BCP was deposited to a thickness of 60 Å as a hole-blocking layer, and Alq3 was deposited to a thickness of 200 Å on top of that as an electron-transporting layer. Finally, lithium fluoride (LiF) was deposited to a thickness of 10 Å on the electron-transporting layer to form an electron-injecting layer. An aluminum (Al) cathode was then deposited to a thickness of 1,200 Å on the electron-injecting layer to form a cathode, completing the fabrication of an organic electroluminescent device. On the other hand, all the organic compounds required for manufacturing OLED elements are 10 -6 ~10 -8 It was purified by vacuum sublimation under torr and used for the fabrication of OLEDs. The electroluminescence (EL) characteristics of the organic electroluminescent device fabricated as described above were measured using a Mac Science M7000, and the measurement results were used to determine whether the reference luminance was 6,000 cd / m or less using a Mac Science M6000 lifespan measurement device. 2 The T90 was measured at this time. The properties of the organic electroluminescent device of the present invention are shown in Table 11 below.

[0184] [Table 11] TIFF0007737719000095.tif44169

[0185] The compounds of Examples 1 to 32 in Table 8 are materials in which triazine is bonded to the third position of the dibenzofuran core. In this case, the linearity of the overall material is increased, and the dipole moment of the material is further strengthened. As a result, the electron-withdrawing effect, which is a characteristic of the strong ET unit containing triazine, is further enhanced, and the decentralized electrons of the dibenzofuran core structure are more strongly attracted to the ET unit. In this case, the LUMO site of the host material is located at the center of the triazine ET unit, and when electrons are strongly attracted, the overlapping area with the HOMO site around the core is greatly reduced. In addition, as the electrons present in the area are concentrated toward the LUMO site, the electron density within the HOMO site decreases. As a result, the charge transfer within the molecule caused by the LUMO-HOMO overlap also decreases, resulting in a greater stability of the molecular structure and a dramatic increase in the device lifespan. However, materials with triazine bonded to position 3 of the dibenzofuran core have a lower degree of electron decentralization and tend to have a slightly higher driving voltage than those substituted at position 1 of the dibenzofuran core. This can be adjusted to a certain level depending on the position of the carbazole-based substituent on the opposite side of the core structure or the Ar in Formula 1 and the strength of the Donor effect.

[0186] Carbazole-based substituents, another substituent that constitutes the bipolar host system, are good host materials with a high T1 energy level due to their strong donor effect (T1=3.00eV). The main HOMO site is located here, and the donor effect can be adjusted by the substitution / non-substitution of the carbazole group itself. In addition, the substitution of the carbazole group increases the molecular weight, which contributes to improving the stability and thermal properties (Tg, Tm) of the molecule itself.

[0187] In particular, in maintaining charge balance, which is the most important factor in OLED devices, the substitution of carbazole groups plays an important role in the host structure to regulate the flow of holes, which have faster mobility than electrons, thereby enabling various changes in device structure, and the HOMO level of the material can be adjusted to a certain level even when the work function changes due to changes in device thickness and hole injection layer / hole transport layer. As a result, it was confirmed that by eliminating the energy barrier with the hole transport layer, the flow of holes within the device can be improved and the driving voltage can be effectively maintained low.

[0188] Comparing the substitution of Ar in Formula 1 with a carbazole-based substituent, it was confirmed that the overall driving voltage is lower when the carbazole group is substituted at the same position. This is because the HOMO level, which is the work function of the carbazole group, is similar to the HOMO level of the adjacent hole transport layer, which relatively reduces the resistance at the interface. This improves the flow of holes, lowering the turn-on voltage and driving voltage.

[0189] The compounds of Examples 33 to 65 in Table 8 are materials in which triazine is bonded to position 1 of the dibenzofuran core. In this case, the linearity is relatively slightly reduced, but the linearity can be increased or decreased to a certain level depending on the carbazole group on the opposite side of the dibenzofuran or the position of Ar in Formula 1.

[0190] Therefore, although there is a slight electron-withdrawing effect, the degree of electron non-uniformity is higher, resulting in more active charge transfer within the molecule. From the above experimental results, it was confirmed that the color coordinate also has a more red shifted form with the same device structure, which may mean that the bandgap of the material narrows due to the occurrence of charge transfer. It was also confirmed that the presence of non-uniformly distributed electrons and their active charge transfer effect resulted in better driving voltage and current efficiency within the device.

[0191] Table 10 shows the results of measurements made on red light-emitting devices. In the case of red devices, both the metal complex and the organic host material have lower T1 energy levels than the green devices. Therefore, the red devices have lower current efficiency and longer life than the green devices.

[0192] In order to create a material with the appropriate energy level for use in a red device centered on the same core, it was necessary to adjust the conjugation region of the material. The previously used carbazole-based substituent of the HT unit and the triazine substituent of the ET unit were respectively changed to polycyclic fused ring groups to expand the conjugation region of the material, thereby enabling the design of a red phosphorescent host material with relatively identical long life and high efficiency properties.

[0193] In particular, the polycyclic condensation introduced into the carbazole group maintains the fast hole transport properties of the carbazole group and allows for tuning to the T1 energy level, which allows for red phosphorescence. At the same time, the condensed ring structure allows for a wider conjugation area, thereby increasing the stability of the molecule. In addition, by substituting around the carbazole group, the energy level of the HOMO level can be adjusted to a certain level. Therefore, it was confirmed that adjusting the work function to be close to the hole transport layer has the advantage of further reducing the driving voltage of the entire device.

[0194] In addition, fused substituents such as dibenzofuran, dibenzothiophene, and triphenylene groups introduced into the triazine group can further enhance the strong electron withdrawal properties of triazine. Regardless of the presence or absence of heteroatoms, the introduction of multiple fused rings with stable structures can ensure a wide conjugation region and expand the LUMO level. This strengthens electron mobility, allowing sufficient current efficiency to be maintained even at low voltages, and also adjusts the T1 energy level to the appropriate level required for red emission.

[0195] Based on the existing structure, various hues can be realized with the same structure by introducing or not introducing fused rings of substituents, so the expandability of the structure is limitless, and there is an advantage that it is possible to construct devices with similar shapes even when various device structures such as RGB method, 2-stack, and 3-stack are introduced.

[0196] Since it is possible to produce materials with appropriate work functions depending on the position of the substituent, they can be used to adjust not only the energy level but also the electron mobility of the entire element when constructing new elements in the future.

[0197] In Tables 9 and 11, the heterocyclic compound of Formula 1 and the heterocyclic compound of Formula 2 are premixed in a single source before being deposited on an organic layer. Premixing has the advantage of simplifying the process by using a single deposition source instead of two or three deposition sources.

[0198] When premixing the materials, the inherent thermal properties of each material must be considered before mixing them. When premixed host materials are deposited from a single deposition source, the inherent thermal properties of the materials can have a significant impact on deposition conditions, including the deposition rate. If the thermal properties of two or more premixed materials are not similar or different, repeatability and reproducibility in the deposition process cannot be maintained, which means that uniform OLED devices cannot be fabricated in a single deposition process.

[0199] To overcome this, the electrical properties of the material can be adjusted by utilizing an appropriate combination of the basic structure and substituents of each material, and the thermal properties can also be adjusted by the molecular structure. Therefore, by utilizing various substituents in Chemical Formula 2 in addition to the bond between the carbon bonded to the carbazole N as in Chemical Formula 2, in addition to the basic skeleton, it is possible to improve the performance of the device and also to adjust the thermal properties of each material, ensuring the versatility of various pre-mixed deposition processes between hosts. This has the advantage of ensuring the versatility of pre-mixed deposition processes using not only two compounds as hosts, but also three to four or more host materials.

[0200] The mixing of the heterocyclic compound of Chemical Formula 1 with the heterocyclic compound of Chemical Formula 2 means that two or more substances can be mixed, and the above experimental examples are merely representative examples and are not limiting.

[0201] As can be seen from Tables 9 and 11, mixing the heterocyclic compound of Chemical Formula 1 with the heterocyclic compound of Chemical Formula 2 not only partially improved the current efficiency of the light-emitting layer, but also enabled the construction of a device with long life. The results in Tables 9 and 11 confirmed that the simultaneous use of the heterocyclic compound of Chemical Formula 1 and the heterocyclic compound of Chemical Formula 2 resulted in better efficiency and life. This is due to the exciplex phenomenon that occurs when two or more materials are mixed. The exciplex phenomenon is a phenomenon in which electron exchange between two molecules releases energy at the HOMO level of the donor (p-host) and the LUMO level of the acceptor (n-host).

[0202] When an exciplex phenomenon occurs between two molecules, reverse intersystem crossing (RISC) occurs, which can increase the internal quantum efficiency of fluorescence to 100%. When a donor (p-host) with good hole transport ability and an acceptor (n-host) with good electron transport ability are used as hosts in the emission layer, holes are injected into the p-host and electrons are injected into the n-host. During this process, excitons are not quenched due to intermolecular electron exchange, increasing their lifetime. This improves overall current efficiency and helps extend device life. In the present invention, it was confirmed that excellent device characteristics were achieved when the heterocyclic compound of Formula 2 above acts as the donor and the heterocyclic compound of Formula 1 above acts as the acceptor. [Explanation of symbols]

[0203] 100: Substrate 200:Anode 300:Organic layer 301: Hole injection layer 302: Hole transport layer 303: Light-emitting layer 304: Hole blocking layer 305: Electron transport layer 306: Electron injection layer 400: Cathode

Claims

1. Represented by any one of the following chemical formulas 3-1 to 3-6 and 4-1 to 4-6: Heterocyclic compounds represented by the formula: 【Chemistry 45】 【Chemistry 46】 【Chemistry 47】 【Chemistry 48】 【Chemistry 49】 【Chemistry 50】 【Chemistry 51】 【Chemistry 52】 【Chemistry 53】 【Chemical 54】 【Chemistry 55】 【Chemical Formula 56】 In the chemical formulas 3-1 to 3-6 and 4-1 to 4-6, N-Het is represented by the following structural formula: 【Chemistry 63】 In the structural formula: 【Chemical 23】 means the position where it is linked to L, R42 is a phenyl group, a biphenyl group, or a naphthyl group; R44 is a phenyl group, a biphenyl group, a naphthyl group, a dibenzofuran group, or a dibenzothiophene group; L and L1 are the same or different and each independently represent a direct bond; or a substituted or unsubstituted C6 to C40 arylene group; Ar is a substituted or unsubstituted C6-C40 aryl group; or a substituted or unsubstituted C2-C40 O- or S-containing heteroaryl group; R9 to R11 are the same or different and are each independently selected from the group consisting of hydrogen and deuterium; R1 to R8 are the same or different and are each independently selected from the group consisting of hydrogen; deuterium; and a substituted or unsubstituted C6 to C60 aryl 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 heterocycle; a and c are integers of 0 or 1; b is an integer of 0 to 2.

2. The heterocyclic compound according to claim 1, wherein Ar in the chemical formulae 3-1 to 3-6 and 4-1 to 4-6 has any one of the following structures: 【Chemical 57】 In the structural formula: 【Chemistry 58】 means the position linked to L1, X1 is O; or S.

3. The heterocyclic compound according to claim 1, wherein the chemical formulas 3-1 to 3-6 and 4-1 to 4-6 are represented by any one of the following compounds: 【Chemical Formula 59】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】

4. An organic light-emitting device comprising a first electrode, a second electrode provided opposite the first electrode, and one or more organic material layers provided between the first electrode and the second electrode, wherein one or more of the organic material layers comprises the heterocyclic compound according to any one of claims 1 to 3.

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

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

7. The organic light-emitting device according to claim 4 , wherein the organic layer includes an electron injection layer or an electron transport layer, and the electron transport layer or the electron injection layer includes the heterocyclic compound.

8. The organic light-emitting device according to claim 4 , 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.

9. 5. The organic light-emitting device according to claim 4, further comprising one or more layers selected from the group consisting of an 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.

10. The organic light-emitting device according to claim 4 , wherein the organic material layer further comprises a heterocyclic compound represented by the following Chemical Formula 2: 【Chemistry 60】 In the above Chemical Formula 2, Ra and Rb are the same or different and each independently represent a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group; Rc and Rd are the same or different and are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C60 alkyl, substituted or unsubstituted C2-C60 alkenyl, substituted or unsubstituted C2-C60 alkynyl, substituted or unsubstituted C1-C60 alkoxy, substituted or unsubstituted C3-C60 cycloalkyl, substituted or unsubstituted C2-C60 heterocycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, and substituted or unsubstituted amine; r and s are integers from 0 to 7.

11. The organic light-emitting device according to claim 10, wherein the Chemical Formula 2 is represented by any one of the following compounds: 【Hua 61】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】

12. A composition for an organic layer of an organic light-emitting device, comprising the heterocyclic compound represented by any one of Chemical Formulas 3-1 to 3-6 and Chemical Formulas 4-1 to 4-6 according to claim 1 and a heterocyclic compound represented by Chemical Formula 2 below: 【Hua 62】 In the above Chemical Formula 2, Ra and Rb are the same or different and each independently represent a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group; Rc and Rd are the same or different and are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C60 alkyl, substituted or unsubstituted C2-C60 alkenyl, substituted or unsubstituted C2-C60 alkynyl, substituted or unsubstituted C1-C60 alkoxy, substituted or unsubstituted C3-C60 cycloalkyl, substituted or unsubstituted C2-C60 heterocycloalkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C2-C60 heteroaryl, and substituted or unsubstituted amine; r and s are integers from 0 to 7.

13. 13. The composition for an organic material layer of an organic light-emitting device according to claim 12, wherein a weight ratio of the heterocyclic compound represented by any one of Chemical Formulas 3-1 to 3-6 and Chemical Formulas 4-1 to 4-6 to the heterocyclic compound represented by Chemical Formula 2 in the composition is 1:10 to 10:

1.

14. providing a substrate; forming a first electrode on the substrate; forming one or more organic layers on the first electrode; forming a second electrode on the organic layer; The method for manufacturing an organic light-emitting device, wherein the step of forming an organic material layer comprises forming one or more organic material layers using the composition for an organic material layer according to claim 12.

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