Heterocyclic compound, organic light-emitting device containing the same, composition for organic layer of organic light-emitting device, and method for producing 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. 10-2019-0124521, filed with the Korean Intellectual Property Office on October 8, 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 same, a composition for an organic layer of the organic light-emitting device, and a method for producing the organic light-emitting device. [Background technology]

[0002] An 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 having such a structure, electrons and holes injected from the two electrodes combine in the organic thin film to form pairs, and then disappear, emitting light. The organic thin film may be configured as a single layer or multiple layers as required. The material of the organic thin film may have a light-emitting function as necessary. For example, the organic thin film material may be a compound that can form a light-emitting layer by itself, or a compound that plays the role of a host or dopant in a host-dopant light-emitting layer. In addition, the organic thin film material may be a compound that plays the role of hole injection, hole transport, electron block, hole block, electron transport, electron injection, etc.

[0003] In order to improve the performance, lifetime or efficiency of organic light emitting devices, there is a continuing need to develop materials for organic thin films. There is a need for research into organic light-emitting devices that contain compounds having chemical structures that can fulfill the requirements for materials that can be used in organic light-emitting devices, such as suitable energy levels, electrochemical stability, and thermal stability, and that can perform the various roles required in organic light-emitting devices depending on the substituents. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] U.S. Patent No. 4,356,429 Summary of the Invention [Problem to be solved by the invention]

[0005] The present application relates to a heterocyclic compound, an organic light-emitting device containing the same, 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]

[0006] 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; 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; Ar1 and Ar2 are the same or different and each independently represents hydrogen; deuterium; -CN; or a substituted or unsubstituted C1 to C60 alkyl group; Z1 is a substituted or unsubstituted C6 to C60 aryl group; or is represented by the following chemical formula A: [ka] X1 is O; S; CR11R12; or NR13; R1 to R4 are the same or different and 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, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6 to C60 aliphatic or aromatic hydrocarbon ring, or a substituted or unsubstituted C2 to C60 heterocycle; R5 and R6 are the same or different and are each independently selected from the group consisting of hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1-C60 alkyl group; substituted or unsubstituted C2-C60 alkenyl group; substituted or unsubstituted C2-C60 alkynyl group; substituted or unsubstituted C1-C60 alkoxy group; substituted or unsubstituted C3-C60 cycloalkyl group; substituted or unsubstituted C2-C60 heterocycloalkyl group; substituted or unsubstituted C6-C60 aryl group; substituted or unsubstituted C2-C60 heteroaryl group; -P(=O)RR'; -SiRR'R" and -NRR'; wherein R11 to R13, R, R' and R" are the same or different and each independently represents 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; c and d are integers from 0 to 3; a and e are integers from 0 to 5.

[0007] According to one embodiment of the present application, there is provided an organic light-emitting device including a first electrode, a second electrode facing the first electrode, and one or more organic layers between the first electrode and the second electrode, wherein at least one of the organic layers includes a heterocyclic compound represented by Chemical Formula 1.

[0008] Further, 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 represents 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 group; substituted or unsubstituted C1-C60 alkyl group; substituted or unsubstituted C2-C60 alkenyl group; substituted or unsubstituted C2-C60 alkynyl group; substituted or unsubstituted C1-C60 alkoxy group; substituted or unsubstituted C3-C60 cycloalkyl group; substituted or unsubstituted C2-C60 heterocycloalkyl group; substituted or unsubstituted C6-C60 aryl group; substituted or unsubstituted C2-C60 heteroaryl group; and substituted or unsubstituted amine group; r and s are integers from 0 to 7.

[0009] 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. Effect of the Invention

[0010] The compounds described herein can be used as organic layer materials of organic light-emitting devices. The compounds can play the role of hole injection materials, hole transport materials, light-emitting materials, electron transport materials, electron injection materials, etc. in organic light-emitting devices. In particular, the compounds can be used as light-emitting layer materials of organic light-emitting devices. For example, the compounds can be used alone as light-emitting materials, and the two compounds can be used together as light-emitting materials and can be used as host materials for light-emitting layers.

[0011] In particular, the compound of formula 1 has an N-containing ring substituted at the third position of one benzene ring of the dibenzofuran structure, and a specific substituent is substituted on the other benzene ring of the dibenzofuran structure where the N-containing ring is not substituted, thereby decentralizing the electrons of the LUMO on the N-containing ring side, resulting in a more stable structure and providing the device with appropriate energy levels and thermal stability. By using the compound of formula 1, an organic light emitting device with improved lifetime, driving stability, and efficiency can be manufactured. [Brief description of the drawings]

[0012] [Figure 1] 1 is a diagram illustrating a stacked structure of an organic light-emitting device according to an embodiment of the present application. [Diagram 2] 1 is a diagram illustrating a stacked structure of an organic light-emitting device according to an embodiment of the present application. [Diagram 3] 1 is a diagram illustrating a stacked structure of an organic light-emitting device according to an embodiment of the present application. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0013] 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 H, Deuterium) is an isotope of hydrogen, so some hydrogen atoms may be deuterium.

[0014] In one embodiment of the present application, "when no substituent is shown in the chemical formula or compound structure", it can mean that all positions that can be substituted are hydrogen or deuterium. In other words, 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%.

[0015] In one embodiment of the present application, in the case where "substituents are not shown 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%. In other words, 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%.

[0016] 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.

[0017] 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.

[0018] 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 the total number of substituents. That is, in one example, [ka] In the case where the total number of substituents that the phenyl group may have is 5 (T1 in the formula), of which the number of deuterium is 1 (T2 in the formula), the deuterium content of 20% in the phenyl group represented by the following structural formula may be expressed as 20%. [ka]

[0019] 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 five hydrogen atoms.

[0020] In this specification, the halogen may be fluorine, chlorine, bromine, or iodine.

[0021] 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-methyl-butyl group, a 1-ethyl-butyl 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 pent ... Examples of such alkyl groups include, but are not limited to, 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.

[0022] In the present 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.

[0023] 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.

[0024] In the present specification, the alkoxy group may be a straight chain, a branched chain, or a cyclic chain. The number of carbon atoms of the alkoxy group is not particularly limited, but it is preferably one having 1 to 20 carbon atoms. Specifically, it may be methoxy, ethoxy, n-propoxy, isopropoxy, 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., but is not limited thereto.

[0025] 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, the polycyclic group 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.

[0026] In the present specification, the heterocycloalkyl group includes O, S, Se, N, or Si as a heteroatom, includes a monocyclic or polycyclic group having 2 to 60 carbon atoms, and may be additionally substituted with other substituents. Here, the polycyclic group means a group in which the heterocycloalkyl group is directly linked 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.

[0027] 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, the polycyclic ring means a group in which the aryl group is directly linked to or condensed with another ring group. Here, the other ring group may be an aryl group, but may also be other types of ring 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, 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 condensed ring groups thereof, but are not limited thereto.

[0028] As used herein, a fluorenyl group may be optionally substituted, and adjacent substituents may be bonded to each other to form a ring.

[0029] When the fluorenyl group is substituted, it may be represented by the following structure, but is not limited thereto. [ka]

[0030] In this specification, the heteroaryl group includes S, O, Se, N, or Si as a heteroatom, includes a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may be additionally substituted with other substituents. Here, the polycyclic ring means a group in which the heteroaryl group is directly linked or condensed with another ring group. Here, the other ring group may be a heteroaryl group, but may also be other types of ring groups, such as a cycloalkyl group, a heterocycloalkyl group, an aryl group, etc. The number of carbon atoms of 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, benzocathyl 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 an alkyl group include, but are not limited to, an azinyl group, a phthalazinyl group, a naphthyridinyl group, a phenanthrolinyl group, a benzo[c][1,2,5]thiadiazolyl group, a 5,10-dihydrodibenzo[b,e][1,4]azasilinyl group, a pyrazolo[1,5-c]quinazolinyl group, a pyrido[1,2-b]indazolyl group, a pyrido[1,2-a]imidazo[1,2-e]indolinyl group, and a 5,11-dihydroindeno[1,2-b]carbazolyl group.

[0031] In the present 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-methyl-anthracenylamine 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 thereto.

[0032] In this specification, the arylene group means 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 each divalent groups. In addition, the heteroarylene group means 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 each divalent groups.

[0033] In the present specification, the phosphine oxide group is represented by -P(=O)R101R102, where R101 and R102 may be the same or different and each independently may 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.

[0034] In this specification, a silyl group is a substituent that contains Si and is directly linked to the Si atom as a radical, and is represented by -SiR104R105R106, where R104 to R106 may be the same or different and each may be independently 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 silyl group 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.

[0035] In this specification, the term "adjacent" may refer 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 the ortho positions on a benzene ring and two substituents substituted on the same carbon atom on an aliphatic ring are interpreted as "adjacent" groups to each other.

[0036] The aliphatic or aromatic hydrocarbon ring or hetero ring capable of forming the adjacent group may have the structures exemplified as the above-mentioned cycloalkyl group, cycloheteroalkyl group, aryl group, and heteroaryl group, except that the ring or hetero ring is not a monovalent group.

[0037] In the present specification, the term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is changed to 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, and when two or more substituents are substituted, the two or more substituents may be the same or different from each other.

[0038] In the present specification, the term "substituted or unsubstituted" means that the group is substituted or unsubstituted with one or more substituents selected from the group consisting of C1-C60 linear or branched alkyl; C2-C60 linear or branched alkenyl; C2-C60 linear or branched alkynyl; C3-C60 monocyclic or polycyclic cycloalkyl; C2-C60 monocyclic or polycyclic heterocycloalkyl; C6-C60 monocyclic or polycyclic aryl; C2-C60 monocyclic or polycyclic heteroaryl; -SiRR'R"; -P(=O)RR'; C1-C20 alkylamine; C6-C60 monocyclic or polycyclic arylamine; and C2-C60 monocyclic or polycyclic heteroarylamine, or is substituted or unsubstituted with a substituent to which two or more substituents selected from the above-mentioned substituents are linked, The R, R' and R" are the same or different and each independently represents a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0039] In one embodiment of the present application, there is provided a compound represented by Chemical Formula 1.

[0040] In one embodiment of the present application, the above-mentioned Chemical Formula 1 may be represented by the following Chemical Formula 1-A or 1-B. [ka] [ka] In the above Chemical Formulas 1-A and 1-B, The definitions of R1 to R6, N-Het, L, L1, X1, Ar1, Ar2, a, c, d, and e are the same as those in Chemical Formula 1. Z2 is a substituted or unsubstituted C6 to C60 aryl group.

[0041] In particular, in one embodiment of the present application, as shown in Chemical Formula 1-B, an aryl group is substituted on another benzene ring in the dibenzofuran structure in which the N-containing ring is not substituted, and thus the dibenzofuran has a high T1 energy level of about 2.5 eV or more, and thus facilitates energy transfer from the host to the dopant. As with a chemical formula substituted with an arylene group or a heteroarylene group, the dibenzofuran has excellent luminous efficiency.

[0042] In one embodiment of the present application, the chemical formula 1-A may be represented by the following chemical formula 3-A or 4-A. [ka] [ka] In the chemical formulae 3-A and 4-A, the definitions of N-Het, L, L1, R1 to R6, X1, a, and c to e are the same as those in the chemical formula 1-A.

[0043] In one embodiment of the present application, the chemical formula 1-B may be represented by any one of the following chemical formulas 3-B and 4-B: [ka] [ka] In the chemical formulae 3-B and 4-B, the definitions of N-Het, L, L1, R6, Z2, a, c and e are the same as those in the chemical formula 1-B.

[0044] In one embodiment of the present application, as in the case of formulas 3-A and 3-B, when N-Het is substituted at position 3 of one benzene ring of dibenzofuran and a specific substituent is present at position 4 of the other benzene ring, the dibenzofuran has better current density, lower driving voltage, and higher triplet energy than when substituted at other positions.

[0045] In one embodiment of the present application, as in the case of formulas 4-A and 4-B, when N-Het is substituted at position 3 of one benzene ring of dibenzofuran and a specific substituent is present at position 1 of the other benzene ring, the dibenzofuran has a lower Td and excellent thermal stability compared to the cases where the dibenzofuran is substituted at other positions, and thus has particularly excellent lifetime characteristics of the organic light-emitting device.

[0046] In other words, in the case of a compound according to one embodiment of the present application, by having an N-Het substituent at the 3rd position of the dibenzofuran and a substituent at a specific position of the other benzene ring, each has the characteristic of providing excellent effects.

[0047] In one embodiment of the present application, R5 and R6 are the same or different and may each be independently selected from the group consisting of hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1-C60 alkyl group; substituted or unsubstituted C2-C60 alkenyl group; substituted or unsubstituted C2-C60 alkynyl group; substituted or unsubstituted C1-C60 alkoxy group; substituted or unsubstituted C3-C60 cycloalkyl group; substituted or unsubstituted C2-C60 heterocycloalkyl group; substituted or unsubstituted C6-C60 aryl group; substituted or unsubstituted C2-C60 heteroaryl group; -P(=O)RR'; -SiRR'R" and -NRR'.

[0048] In other embodiments, R5 and R6 are the same or different and may each be independently selected from the group consisting of hydrogen; halogen; a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C6-C60 aryl group; a substituted or unsubstituted C2-C60 heteroaryl group; -P(=O)RR'; -SiRR'R" and -NRR'.

[0049] In yet another embodiment, R5 and R6 are the same or different and may each be independently selected from the group consisting of hydrogen; halogen; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C40 aryl group; a substituted or unsubstituted C2 to C40 heteroaryl group; -P(=O)RR'; -SiRR'R" and -NRR'.

[0050] In yet other embodiments, R5 and R6 can be hydrogen.

[0051] In one embodiment of the present application, Ar1 and Ar2 are the same or different and each independently represent hydrogen; deuterium; -CN; or a substituted or unsubstituted C1 to C60 alkyl group.

[0052] In other embodiments, Ar1 and Ar2 are the same or different and are each independently hydrogen; or a substituted or unsubstituted C1-C60 alkyl group.

[0053] In still other embodiments, Ar1 and Ar2 are the same or different from each other and are each independently hydrogen; or a substituted or unsubstituted C1-C20 alkyl group.

[0054] In still other embodiments, Ar1 and Ar2 are the same or different from each other and are each independently hydrogen; or a C1-C20 alkyl group.

[0055] In still other embodiments, Ar1 and Ar2 are hydrogen.

[0056] In one embodiment of the present application, L may be a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group.

[0057] In other embodiments, L can be a direct bond; a substituted or unsubstituted C6 to C40 arylene group; or a substituted or unsubstituted C2 to C40 heteroarylene group.

[0058] In still other embodiments, L may be a direct bond; a substituted or unsubstituted C6 to C40 monocyclic or polycyclic arylene group; or a substituted or unsubstituted C2 to C40 heteroarylene group.

[0059] In still other embodiments, L may be a direct bond; a substituted or unsubstituted C6 to C40 monocyclic arylene group; or a substituted or unsubstituted C10 to C40 polycyclic arylene group.

[0060] In still other embodiments, L may be a direct bond; a C6 to C40 monocyclic arylene group; or a C10 to C40 polycyclic arylene group.

[0061] In still other embodiments, L can be a direct bond; a phenylene group; a biphenylene group; or a naphthylene group.

[0062] In yet other embodiments, L may be a direct bond.

[0063] In one embodiment of the present application, L1 may be a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group.

[0064] In other embodiments, L1 may be a direct bond; a substituted or unsubstituted C6 to C40 arylene group; or a substituted or unsubstituted C2 to C40 heteroarylene group.

[0065] In still other embodiments, L1 may be a direct bond; a substituted or unsubstituted C6 to C40 monocyclic or polycyclic arylene group; or a substituted or unsubstituted C2 to C40 heteroarylene group.

[0066] In still other embodiments, L1 may be a direct bond; a substituted or unsubstituted C6 to C40 monocyclic arylene group; or a substituted or unsubstituted C10 to C40 polycyclic arylene group.

[0067] In still other embodiments, L1 may be a direct bond; a C6 to C40 monocyclic arylene group; or a C10 to C40 polycyclic arylene group.

[0068] In still other embodiments, L1 can be a direct bond; a phenylene group; a biphenylene group; or a naphthylene group.

[0069] In one embodiment of the present application, R1 to R4 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, or two or more adjacent groups may be bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring.

[0070] In another embodiment, R1 to R4 are the same or different and each independently represent a hydrogen atom; a substituted or unsubstituted C1 to C40 alkyl group; a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group, or two or more adjacent groups may be bonded to each other to form a substituted or unsubstituted C6 to C40 aromatic hydrocarbon ring.

[0071] In still another embodiment, R1 to R4 are the same or different and each independently represent a hydrogen atom; a C1 to C40 alkyl group; a C6 to C40 aryl group; or a C2 to C40 heteroaryl group, or two or more adjacent groups may be bonded to each other to form a C6 to C40 aromatic hydrocarbon ring.

[0072] In still another embodiment, R1 to R4 are the same or different and each independently represent hydrogen; a C6 to C40 monocyclic aryl group; or a C10 to C40 polycyclic aryl group, or two or more adjacent groups may be bonded to each other to form a C6 to C40 monocyclic aromatic hydrocarbon ring.

[0073] In still another embodiment, R1 to R4 are the same or different and each independently represent a hydrogen atom; a phenyl group; a biphenyl group; or a triphenylenyl group, or two or more adjacent groups may be bonded to each other to form a benzene ring.

[0074] In one embodiment of the present application, R1 to R4 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, or two or more adjacent groups may be bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring.

[0075] In another embodiment, R1 to R4 are the same or different and each independently represent a hydrogen atom; a substituted or unsubstituted C1 to C40 alkyl group; a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group, or two or more adjacent groups may be bonded to each other to form a substituted or unsubstituted C6 to C40 aromatic hydrocarbon ring.

[0076] In still another embodiment, R1 to R4 are the same or different and each independently represent a hydrogen atom; a C1 to C40 alkyl group; a C6 to C40 aryl group; or a C2 to C40 heteroaryl group, or two or more adjacent groups may be bonded to each other to form a C6 to C40 aromatic hydrocarbon ring.

[0077] In still another embodiment, R1 to R4 are the same or different and each independently represent hydrogen; a C6 to C40 monocyclic aryl group; or a C10 to C40 polycyclic aryl group, or two or more adjacent groups may be bonded to each other to form a C6 to C40 monocyclic aromatic hydrocarbon ring.

[0078] In still another embodiment, R1 to R4 are the same or different and each independently represent a hydrogen atom; a phenyl group; a biphenyl group; or a triphenylenyl group, or two or more adjacent groups may be bonded to each other to form a benzene ring.

[0079] In one embodiment of the present application, X1 may be O; S; CR11R12; or NR13.

[0080] In one embodiment of the present application, X1 may be O.

[0081] In one embodiment of the present application, X1 may be S.

[0082] In one embodiment of the present application, X1 may be CR11R12.

[0083] In one embodiment of the present application, X1 may be NR13.

[0084] In particular, when X1 has a substituent of NR13, the HOMO energy level is unevenly distributed to one side, whereas when X1 has O, S, etc., the HOMO energy level is unevenly distributed compared to the above, and has a more stable electronic structure, and thus has the characteristic that an organic light-emitting device having improved lifetime, driving stability, and efficiency can be manufactured.

[0085] In one embodiment of the present application, R11 to R13 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.

[0086] In another embodiment, R11 to R13 may be the same or different and each independently represent an alkyl group of C1 to C60; an aryl group of C6 to C60; or a heteroaryl group of C2 to C60.

[0087] In still another embodiment, R11 to R13 may be the same or different and each independently be a C6 to C60 aryl group.

[0088] In still another embodiment, R11 to R13 may be the same or different and each independently be a C6 to C40 monocyclic aryl group.

[0089] In still other embodiments, R11 to R13 may be phenyl groups.

[0090] In one embodiment of the present application, R13 may be a phenyl group.

[0091] In one embodiment of the present application, Chemical Formula A in Chemical Formula 1 may be represented by any one of Chemical Formulas 1-1 to 1-6 below. [ka] [ka] [ka] [ka] [ka] [ka] In the above Chemical Formulas 1-1 to 1-6, The definitions of X1, R5 and d are the same as those in Chemical Formula 1. [ka] means a position at which L1 is linked to the above-mentioned formula 1; R31 to R34 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; R35 and R36 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.

[0092] In one embodiment of the present application, Z1 may be a substituted or unsubstituted C6 to C60 aryl group or may be represented by the above-mentioned chemical formula A, and specifically, Z1 may be a substituted or unsubstituted C6 to C60 aryl group.

[0093] In other embodiments, Z1 may be a substituted or unsubstituted C6 to C40 aryl group.

[0094] In still other embodiments, Z1 may be a substituted or unsubstituted monocyclic or polycyclic C6 to C40 aryl group.

[0095] In still other embodiments, Z1 may be a substituted or unsubstituted monocyclic C6-C40 aryl group.

[0096] In still other embodiments, Z1 may be a substituted or unsubstituted polycyclic C10 to C40 aryl group.

[0097] In still other embodiments, Z1 may be a monocyclic C6-C40 aryl group.

[0098] In still other embodiments, Z1 may be a polycyclic C10-C40 aryl group.

[0099] In still other embodiments, Z1 may be a phenyl group; or a triphenylenyl group.

[0100] In one embodiment of the present application, Z2 may be a substituted or unsubstituted C6 to C60 aryl group.

[0101] In other embodiments, Z2 may be a substituted or unsubstituted C6 to C40 aryl group.

[0102] In still other embodiments, Z2 may be a substituted or unsubstituted monocyclic or polycyclic C6 to C40 aryl group.

[0103] In still other embodiments, Z2 may be a substituted or unsubstituted monocyclic C6-C40 aryl group.

[0104] In still other embodiments, Z2 may be a substituted or unsubstituted polycyclic C10 to C40 aryl group.

[0105] In still other embodiments, Z2 may be a monocyclic C6-C40 aryl group.

[0106] In yet other embodiments, Z2 may be a polycyclic C10-C40 aryl group.

[0107] In still other embodiments, Z2 may be a phenyl group; or a triphenylenyl group.

[0108] In one embodiment of the present application, R31 to R34 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.

[0109] In another embodiment, R31 to R34 may be the same or different and each independently be a substituted or unsubstituted C6 to C60 aryl group.

[0110] In still another embodiment, R31 to R34 may be the same or different and each independently be a substituted or unsubstituted C6 to C40 aryl group.

[0111] In still another embodiment, R31 to R34 may be the same or different and each independently be a substituted or unsubstituted C6 to C40 monocyclic or polycyclic aryl group.

[0112] In still another embodiment, R31 to R34 may be the same or different and each independently represent a C6 to C40 monocyclic aryl group; or a C10 to C40 polycyclic aryl group.

[0113] In still another embodiment, R31 to R34 may be the same or different and each independently represent a phenyl group; or a triphenylenyl group.

[0114] In one embodiment of the present application, R35 and R36 may be hydrogen.

[0115] 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.

[0116] 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.

[0117] In still another embodiment, N-Het may be a substituted or unsubstituted monocyclic or polycyclic C2 to C60 heterocyclic group containing 1 to 3 N atoms.

[0118] In still another embodiment, N-Het may be a substituted or unsubstituted, monocyclic or polycyclic C2 to C40 heterocyclic group containing 1 to 3 N atoms.

[0119] In still another embodiment, N-Het may be a substituted or unsubstituted monocyclic C2-C40 heterocyclic group containing 1 to 3 N atoms.

[0120] In still another embodiment, N-Het may be a monocyclic C2-C40 heterocyclic group containing 1 to 3 N and unsubstituted or substituted 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-mentioned substituents are linked together.

[0121] In still other embodiments, N-Het may be a pyridine group; a pyrimidine group; or a triazine group, which is 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-mentioned substituents are linked together.

[0122] In yet other embodiments, N-Het may be a pyridine group substituted or unsubstituted with a phenyl group; a pyrimidine group substituted or unsubstituted with a phenyl group; or a triazine group substituted or unsubstituted with one or more substituents selected from the group consisting of a triphenylenyl group, a diphenylfluorene group, a phenyl group substituted or unsubstituted with -P(=)ORR' or -SiRR'R", a biphenyl group, a dibenzofuran group, a dimethylfluorene group, and a dibenzothiophene group.

[0123] In one embodiment of the present application, N-Het may be selected from the following structures: [ka] In the above structural formula, [ka] means a position at which the group is linked 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.

[0124] In one embodiment of the present application, R41 to R45 are the same or different and may each independently be 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.

[0125] In other embodiments, R41 to R45 are the same or different and may each independently be hydrogen; a substituted or unsubstituted C1 to C40 alkyl group; a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group.

[0126] In still another embodiment, R41 to R45 are the same or different and each independently may be hydrogen; a C1 to C20 alkyl group, a C6 to C40 aryl group, a C2 to C40 heteroaryl group, a C6 to C40 aryl group unsubstituted or substituted with one or more substituents selected from the group consisting of -P(=)ORR' and -SiRR'R''; or a C2 to C40 heteroaryl group.

[0127] In still another embodiment, R41 to R45 are the same or different and may each independently be a hydrogen atom; a phenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of a phenyl group, a triphenylenyl group, a diphenylfluorenyl group, -P(=)ORR' and -SiRR'R''; a biphenyl group; a dibenzofuran group; a dibenzothiophene group; or a dimethylfluorenyl group.

[0128] 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.

[0129] In other embodiments, R, R' and R'' may be the same or different and each independently be a substituted or unsubstituted C6 to C60 aryl group.

[0130] In still other embodiments, R, R' and R'' may be the same or different and each independently be a substituted or unsubstituted C6 to C60 monocyclic or polycyclic aryl group.

[0131] In still other embodiments, R, R' and R'' may be the same or different and each independently be a substituted or unsubstituted C6 to C40 monocyclic aryl group.

[0132] In still other embodiments, R, R' and R'' may be the same or different and each independently be a C6 to C20 monocyclic aryl group.

[0133] In yet other embodiments, R, R' and R'' can be phenyl groups.

[0134] 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] TIFF0007671506000023.tif179161 TIFF0007671506000024.tif198161 TIFF0007671506000025.tif199161 TIFF0007671506000026.tif198161 TIFF0007671506000027.tif98161 TIFF0007671506000028.tif188161 TIFF0007671506000029.tif173161 TIFF0007671506000030.tif181161 TIFF0007671506000031.tif188161 TIFF0007671506000032.tif185161

[0135] In addition, it is possible to synthesize compounds having the inherent properties of the introduced substituents by introducing various substituents into the structure of Chemical Formula 1. For example, it is possible to synthesize materials that satisfy the requirements of each organic layer by introducing into the core structure substituents that are mainly 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.

[0136] 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, and the applications of the material can be diversified.

[0137] In addition, in 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 layers provided between the first electrode and the second electrode, wherein at least one of the organic layers includes a heterocyclic compound represented by Chemical Formula 1.

[0138] In yet another embodiment, an organic light-emitting device is provided that includes a first electrode, a second electrode facing the first electrode, and one or more organic layers between the first electrode and the second electrode, wherein at least one of the organic layers includes one heterocyclic compound represented by Chemical Formula 1.

[0139] The specific details regarding the heterocyclic compound represented by Chemical Formula 1 are the same as those described above.

[0140] In one embodiment of the present application, the first electrode may be an anode and the second electrode may be a cathode.

[0141] In other embodiments, the first electrode may be a cathode and the second electrode may be an anode.

[0142] In one embodiment of the present application, the organic light emitting device may be a blue organic light emitting device, and the heterocyclic compound represented by Chemical Formula 1 may be used as a material of the blue organic light emitting device. 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.

[0143] 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.

[0144] 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.

[0145] The organic light-emitting device of the present invention can be manufactured by a typical manufacturing method and materials for an organic light-emitting device, except that one or more organic layers are formed using the above-mentioned heterocyclic compound.

[0146] In the manufacture of an organic light emitting device, the heterocyclic compound is formed in an organic layer by a solution coating method as well as a vacuum deposition method, where the solution coating method refers to, but is not limited to, spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc.

[0147] The organic layer of the organic light-emitting device of the present invention may have a single-layer structure, or may have a multi-layer structure in which two or more organic layers are laminated. For example, the organic light-emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. as the organic layer. However, the structure of the organic light-emitting device is not limited thereto, and may include a smaller number of organic layers.

[0148] In the organic light-emitting device of the present invention, the organic layer may include a light-emitting layer, and the light-emitting layer may include the heterocyclic compound.

[0149] In another organic light-emitting device, the organic 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.

[0150] As another example, the organic layer including 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.

[0151] In the organic light-emitting device of the present invention, the organic 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.

[0152] In another organic light-emitting device, the organic 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.

[0153] 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.

[0154] 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.

[0155] 1 shows an organic light emitting device in which an anode 200, an organic 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 layer, and an anode are sequentially stacked on a substrate as shown in FIG.

[0156] Fig. 3 illustrates an example in which the organic layer is multi-layered. The organic light-emitting device in Fig. 3 includes a hole injection layer 301, a hole transport layer 302, an emission layer 303, a hole blocking layer 304, an electron transport layer 305, and an electron injection layer 306. However, the scope of the present application is not limited to such a laminated structure, and the remaining layers except for the emission layer may be omitted as necessary, and other necessary functional layers may be further added.

[0157] The organic layer containing the compound of Formula 1 may further contain other materials as necessary.

[0158] In the organic light emitting device according to an 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 represents 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 group; substituted or unsubstituted C1-C60 alkyl group; substituted or unsubstituted C2-C60 alkenyl group; substituted or unsubstituted C2-C60 alkynyl group; substituted or unsubstituted C1-C60 alkoxy group; substituted or unsubstituted C3-C60 cycloalkyl group; substituted or unsubstituted C2-C60 heterocycloalkyl group; substituted or unsubstituted C6-C60 aryl group; substituted or unsubstituted C2-C60 heteroaryl group; and substituted or unsubstituted amine group; r and s are integers from 0 to 7.

[0159] When the compound of Formula 1 and the compound of Formula 2 are simultaneously contained in an organic layer of an organic light-emitting device, the organic light-emitting device shows better efficiency and life effects. This result suggests that an exciplex phenomenon occurs when the two compounds are simultaneously contained.

[0160] The exciplex phenomenon is a phenomenon in which energy is released with the magnitude of the HOMO level of the donor (p-host) and the LUMO level of the acceptor (n-host) due to electron exchange between two molecules. When 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 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, which can reduce the driving voltage and thereby help improve the life span.

[0161] In one embodiment of the present application, Rc and Rd may be hydrogen.

[0162] In one embodiment of the present application, Ra and Rb in the above Chemical Formula 2 may be the same or different, and each may independently be a substituted or unsubstituted C6 to C60 aryl group.

[0163] In another embodiment, Ra and Rb in the above Chemical Formula 2 may be the same or different and each independently may be a substituted or unsubstituted C6 to C40 aryl group.

[0164] In still another embodiment, Ra and Rb in the above chemical formula 2 may be the same or different, and each independently may be a C6 to C40 aryl group substituted or unsubstituted with one or more substituents selected from the group consisting of a C1 to C40 alkyl group, a C6 to C40 aryl group, -CN, and -SiR201R202R203.

[0165] In yet another embodiment, Ra and Rb in the above formula 2 may be the same or different, and each independently may be a phenyl group, a phenyl group substituted or unsubstituted with -CN or -SiR201R202R203; 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; or a triphenylene group.

[0166] In one embodiment of the present application, R201, R202, and R203 in the above Chemical Formula 2 may be a C6 to C60 aryl group.

[0167] In another embodiment, R201, R202, and R203 in the above Chemical Formula 2 may be a C6 to C40 aryl group.

[0168] In one embodiment of the present application, R201, R202, and R203 in the above Chemical Formula 2 may be a phenyl group.

[0169] In one embodiment of the present application, the above Chemical Formula 2 may be represented by any one of the following compounds, but is not limited thereto: [ka] TIFF0007671506000035.tif214161 TIFF0007671506000036.tif209161 TIFF0007671506000037.tif214161

[0170] In the organic light emitting device according to an embodiment of the present application, the compound of Chemical Formula 2 may be included in the light emitting layer of the organic material layer.

[0171] 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.

[0172] 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.

[0173] 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 above.

[0174] 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.

[0175] 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.

[0176] 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.

[0177] In one embodiment of the present application, there is provided a method for manufacturing an organic light-emitting device, in which the step of forming the organic layer comprises pre-mixing two kinds of heterocyclic compounds represented by Chemical Formula 1 and Chemical Formula 2 and forming the organic layer using a thermal vacuum deposition method.

[0178] The term "pre-mixed" means that the heterocyclic compound represented by Chemical Formula 1 and the two heterocyclic compounds represented by Chemical Formula 2 are mixed in one source before being deposited on an organic layer.

[0179] The premixed materials may be referred to as an organic layer composition according to one embodiment of the present application.

[0180] 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.

[0181] 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 SnO2:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline.

[0182] The cathode material may be a material having 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 materials with multilayer structures such as LiF / Al or LiO2 / Al.

[0183] As the hole injection material, a known hole injection material can be used, for example, a phthalocyanine compound such as copper phthalocyanine disclosed in U.S. Pat. No. 4,356,429, or a starburst type amine derivative described in the literature [Advanced Material, 6, p. 677 (1994)], for example, 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), a soluble conductive polymer polyaniline / dodecylbenzenesulfonic acid (Polyaniline / Dodecylbenzenesulfonic acid), etc. Poly(3,4-ethylenedioxythiophene) / Poly(4-styrenesulfonate), Polyaniline / Camphor sulfonic acid or Polyaniline / Poly(4-styrenesulfonate), etc. can be used.

[0184] As the hole transport material, pyrazoline derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, etc. can be used, and low molecular or high molecular weight materials may also be used.

[0185] As the electron transport material, 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, metal complexes of 8-hydroxyquinoline and its derivatives, etc. can be used, and not only low molecular weight substances but also polymeric substances can be used.

[0186] As the electron injection material, for example, LiF is typically used in the industry, but the present application is not limited thereto.

[0187] The light-emitting material may be a red, green, or blue light-emitting material, and if necessary, two or more light-emitting materials may be mixed and used. In this case, two or more light-emitting materials may be deposited as individual supply sources, or may be premixed and deposited as one supply 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 are involved in light emission may be used.

[0188] When the hosts of the light-emitting materials are mixed, the same type of hosts may be mixed and used, or different types of hosts may be mixed and used. For example, two or more types of n-type host materials or p-type host materials may be selected and used as the host material of the light-emitting layer.

[0189] The organic light emitting device according to one 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.

[0190] The heterocyclic compound according to an embodiment of the present application can also function in organic electronic devices, including organic solar cells, organic photoreceptors, organic transistors, etc., based on a similar principle to that applied to organic light-emitting devices. EXAMPLES

[0191] The present invention will be described in more detail with reference to the following examples, which are merely for illustrating the present application and are not intended to limit the scope of the present application.

[0192] <Production Example 1> Production of Compound 1-1 [ka]

[0193] 1) Preparation of Compound 1-1-6 200.0g (664.7mM) of 4-bromo-2-fluoro-1-iodobenzene, 148.7g (794.6mM) of (2-chloro-6-methoxyphenyl)boronic acid, 38.4g (33.2mM) of Pd(PPh), and 183.7g (1329.4mM) of K2CO3 were dissolved in 1,4-dioxane / H2O1L / 200mL and refluxed for 24 hours. After the reaction was completed, the mixture was extracted with distilled water and dichloromethane (DCM) at room temperature, and 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) to obtain 178 g (85%) of the target compound 1-1-6.

[0194] 2) Preparation of Compound 1-1-5 Compound 1-1-6 (178 g, 564.1 mM) and BBr3 (107 mL, 1128.2 mM) were dissolved in DCM (800 mL) and refluxed for 1 hour. After the reaction was completed, the mixture was extracted with distilled water and DCM at room temperature, and the organic layer was dried with MgSO4 and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (DCM:Hex=1:1) to obtain the target compound 1-1-5 (153.1 g, 90%).

[0195] 3) Preparation of Compound 1-1-4 Compound 1-1-5 (153g, 507.4mM) and K2CO3 (140.3g, 1014.8mM) were dissolved in dimethylformamide (DMF) (800mL) and refluxed for 4 hours. After the reaction was completed, the mixture was extracted with distilled water and DCM at room temperature, and the organic layer was dried with MgSO4 and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (DCM:Hex=1:9) and recrystallized from methanol to obtain the target compound 1-1-4 (88.5g, 62%).

[0196] 4) Preparation of Compound 1-1-3 Compound 1-1-4 88.5g (314.4mM), bis(pinacolato)diboron 159.7g (628.8mM), PdCl2(dppf) 23.0g (31.4mM), KOAc 92.6g (943.2mM) were dissolved in 1,4-dioxane 500mL and refluxed for 24 hours. After the reaction was completed, it was extracted with distilled water and DCM at room temperature, and the organic layer was dried with MgSO4 and the solvent was removed with a rotary evaporator. The reactant was purified by column chromatography (DCM:Hex=1:5) to obtain the target compound 1-1-3 85.7g (83%).

[0197] 5) Preparation of Compound 1-1-2 Compound 1-1-3 85.0g (258.7mM), 2-chloro-4,6-diphenyl-1,3,5-triazine 69.3g (258.7mM), Pd(PPh) 414.9g (12.9mM), and K2CO3 71.5g (517.4mM) were dissolved in 1,4-dioxane / H2O1000 / 200mL and refluxed for 24 hours. After the reaction was completed, it was extracted with distilled water and DCM at room temperature, and the organic layer was dried with MgSO4 and the solvent was removed with a rotary evaporator. The reactant was purified by column chromatography (DCM:Hex=1:4) and recrystallized with methanol to obtain the target compound 1-1-2 79.7g (71%).

[0198] 6) Preparation of Compound 1-1-1 Compound 1-1-2 79.0g (182.1mM), bis(pinacolato)diboron 92.5g (364.2mM), Pd(dba)2 10.5g (18.2mM), XPhos 17.4g (36.4mM), KOAc 53.6g (546.3mM) were dissolved in 1,4-dioxane 800mL and refluxed for 24 hours. After the reaction was completed, it was extracted with distilled water and DCM at room temperature, the organic layer was dried with MgSO4, and the solvent was removed with a rotary evaporator. The reactant was purified by column chromatography (DCM:Hex=1:5) to obtain the target compound 1-1-1 84.2g (88%).

[0199] 7) Preparation of Compound 1-1 Compound 1-1-1 15.0g (28.5mM), 2-bromodibenzo[b,d]furan 7.8g (31.4mM), Pd(PPh) 41.6g (1.4mM), and K2CO3 7.9g (57.0mM) were dissolved in 1,4-dioxane / H2O200 / 40mL and refluxed for 24 hours. After the reaction was completed, it was extracted with distilled water and DCM at room temperature, and the organic layer was dried with MgSO4 and the solvent was removed with a rotary evaporator. The reactant was purified by column chromatography (DCM:Hex=1:3) and recrystallized with methanol to obtain the target compound 1-1, 13.2g (82%).

[0200] Target compound A was synthesized in the same manner as in Production Example 1, except that intermediate A in Table 1 below was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine and intermediate B in Table 1 below was used instead of 2-bromodibenzo[b,d]furan in Production Example 1.

[0201] [Table 1] TIFF0007671506000040.tif216165 TIFF0007671506000041.tif97165

[0202] <Production Example 2> Production of Compound 4-1 [ka]

[0203] 1) Preparation of Compound 4-1-6 200.0g (664.7mM) of 4-bromo-2-fluoro-1-iodobenzene, 148.7g (794.6mM) of (3-chloro-2-methoxyphenyl)boronic acid, 438.4g (33.2mM) of Pd(PPh), and 183.7g (1329.4mM) of K2CO3 were dissolved in 1,4-dioxane / H2O1L / 200mL and refluxed for 24 hours. After the reaction was completed, the mixture was extracted with distilled water and DCM at room temperature, and the organic layer was dried with MgSO4 and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (DCM:Hex=1:4) to obtain 169g (81%) of the target compound 4-1-6.

[0204] 2) Preparation of Compound 4-1-5 Compound 4-1-6 (169 g, 535.5 mM) and BBr3 (1071.0 mM) were dissolved in dichloromethane (DCM) (800 mL) and refluxed for 1 hour. After the reaction was completed, the mixture was extracted with distilled water and DCM at room temperature, and the organic layer was dried with MgSO4 and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (DCM:Hex=1:1) to obtain the target compound 4-1-5 (145.3 g, 90%).

[0205] 3) Preparation of Compound 4-1-4 Compound 4-1-5 (145.3g, 481.9mM) and K2CO3 (133.2g, 963.9mM) were dissolved in DMF (800mL) and refluxed for 4 hours. After the reaction was completed, the mixture was extracted with distilled water and DCM at room temperature, and the organic layer was dried with MgSO4 and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (DCM:Hex=1:8) and recrystallized from methanol to obtain the target compound 4-1-4 (74.6g, 57%).

[0206] 4) Preparation of Compound 4-1-3 Compound 4-1-4 74.6g (265.1mM), bis(pinacolato)diboron 134.6g (530.2mM), PdCl2(dppf) 19.4g (26.5mM), KOAc 78.1g (795.3mM) were dissolved in 1,4-dioxane 500mL and refluxed for 24 hours. After the reaction was completed, it was extracted with distilled water and DCM at room temperature, and the organic layer was dried with MgSO4 and the solvent was removed with a rotary evaporator. The reactant was purified by column chromatography (DCM:Hex=1:5) to obtain the target compound 4-1-3 76.7g (88%).

[0207] 5) Preparation of Compound 4-1-2 Compound 4-1-3 (76.7g, 233.28mM), 2-chloro-4,6-diphenyl-1,3,5-triazine (67.7g, 233.28mM), Pd(PPh) (413.5g, 11.7mM), and K2CO3 (64.5g, 466.6mM) were dissolved in 1,4-dioxane / H2O (800 / 160mL) and refluxed for 24 hours. After the reaction was completed, the mixture was extracted with distilled water and DCM at room temperature, and the organic layer was dried with MgSO4 and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (DCM:Hex=1:5) and recrystallized with methanol to obtain the target compound 4-1-2 (70.9g, 70%).

[0208] 6) Preparation of Compound 4-1-1 Compound 4-1-2 74.0g (163.3mM), bis(pinacolato)diboron 29.4g (16.3mM), XPhos 15.6g (32.7mM), KOAc 48.1g (489.9mM) were dissolved in 1,4-dioxane 740mL and refluxed for 24 hours. After the reaction was completed, it was extracted with distilled water and DCM at room temperature, and the organic layer was dried with MgSO4 and the solvent was removed with a rotary evaporator. The reactant was purified by column chromatography (DCM:Hex=1:4) to obtain the target compound 4-1-1 72.9g (85%).

[0209] 7) Preparation of Compound 4-1 Compound 4-1-1 (15.0g, 28.5mM), 2-bromodibenzo[b,d]furan (7.8g, 31.4mM), Pd(PPh) (41.6g, 1.4mM), and K2CO3 (7.9g, 57.0mM) were dissolved in 1,4-dioxane / H2O200 / 40mL and refluxed for 24 hours. After the reaction was completed, the mixture was extracted with distilled water and DCM at room temperature, and the organic layer was dried with MgSO4 and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (DCM:Hex=1:3) and recrystallized from methanol to obtain the target compound 4-1 (12.9g, 80%).

[0210] Target compound A was synthesized in the same manner as in Production Example 2, except that intermediate A in Table 2 below was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine and intermediate B in Table 2 below was used instead of 2-bromodibenzo[b,d]furan in Production Example 2.

[0211] [Table 2] TIFF0007671506000044.tif141165

[0212] <Production Example 3> Synthesis of Compound 5-3 [ka]

[0213] 1) Preparation of Compound 5-3 3.7g (15.8mM) of 3-bromo-1,1'-biphenyl, 6.5g (15.8mM) of 9-phenyl-9H,9'H-3,3'-bicarbazole, 3.0g (15.8mM) of CuI, 1.9mL (15.8mM) of trans-1,2-diaminocyclohexane, and 3.3g (31.6mM) of K3PO4 were dissolved in 100mL of 1,4-oxane and refluxed for 24 hours. After the reaction was completed, the mixture was extracted with distilled water and DCM at room temperature, and the organic layer was dried with MgSO4 and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (DCM:Hex=1:3) and recrystallized from methanol to obtain 7.5g (85%) of the target compound 5-3.

[0214] Target compound A was synthesized in the same manner as in Production Example 3, except that in Production Example 3, intermediate A in Table 3 below was used instead of 3-bromo-1,1'-biphenyl, and intermediate B in Table 3 below was used instead of 9-phenyl-9H,9'H-3,3'-bicarbazole.

[0215] [Table 3]

[0216] The heterocyclic compounds corresponding to the above Chemical Formula 1 and Chemical Formula 2 other than the compounds shown in the above Production Examples 1 to 3 and Tables 1 to 3 were also produced in the same manner as in the above Production Examples. The synthesis confirmation data of the compounds prepared above are as shown in Tables 4 and 5 below.

[0217] [Table 4] TIFF0007671506000048.tif90165

[0218] [Table 5]

[0219] <Experimental Example 1> - Fabrication of organic light-emitting device A glass substrate coated with a thin film of indium tin oxide (ITO) to a thickness of 1,500 Å was ultrasonically cleaned with distilled water. After the distilled water cleaning was completed, 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 using UV in a UV cleaner. The substrate was then transferred to a plasma cleaner (PT) and plasma treated in a vacuum state to determine the work function of the ITO and remove residual film, before being transferred to a thermal evaporation device for organic deposition. A common layer, 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), were formed on the ITO transparent electrode (anode). An emission layer was formed thereon by thermal vacuum deposition as follows. The emission layer was formed by depositing the compound in Table 6 below as a host to a thickness of 400 Å, and depositing a green phosphorescent dopant, Ir(ppy)3, at a thickness of 7% of the deposition thickness of the emission 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 thereon as an electron transport layer. Finally, lithium fluoride (LiF) was deposited to a thickness of 10 Å on the electron transport layer to form an electron injection layer, and then an aluminum (Al) cathode was deposited to a thickness of 1,200 Å on the electron injection layer to form a cathode, thereby manufacturing an organic electroluminescent device. On the other hand, all the organic compounds required for the production of OLED elements cost about 10 -6 ~10-8 The resulting material was purified by vacuum sublimation under torr and used for the fabrication of OLEDs.

[0220] The electroluminescence (EL) characteristics of the organic electroluminescence device fabricated as described above were measured using a Mac Science M7000. Based on the measurement results, a reference luminance of 6,000 cd / m was determined using a Mac Science M6000 lifetime measurement device. 2 At the time, T 90 was measured. The driving voltage, luminous efficiency, color coordinate (CIE), and life span of the manufactured organic light emitting device were measured, and the results are shown in Table 6 below.

[0221] [Table 6]

[0222] [ka]

[0223] <Experimental Example 2> - Fabrication of organic light-emitting device A glass substrate coated with a thin ITO film to a thickness of 1,500 Å was ultrasonically cleaned with distilled water. After the distilled water cleaning was completed, the substrate was ultrasonically cleaned with solvents such as acetone, methanol, and isopropyl alcohol, dried, and then treated with UVO for 5 minutes using UV in a UV cleaner. The substrate was then transferred to a plasma cleaner (PT) and plasma treated in a vacuum state to determine the work function of the ITO and remove residual film, before being transferred to a thermal evaporation device for organic deposition. A common layer, 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), were formed on the ITO transparent electrode (anode). An emission layer was formed thereon by thermal vacuum deposition as follows. The emission layer was formed by premixing one compound represented by Chemical Formula 1 and one compound represented by Chemical Formula 2 as shown in Table 7 below as a host, and then depositing the host with a thickness of 400 Å from one source, and depositing a green phosphorescent dopant, Ir(ppy)3, at a thickness of 7% of the deposition thickness of the emission layer. Then, BCP was deposited with a thickness of 60 Å as a hole blocking layer, and Alq3 was deposited with a thickness of 200 Å thereon as an electron transport layer. Finally, lithium fluoride (LiF) was deposited with a thickness of 10 Å on the electron transport layer to form an electron injection layer, and then an aluminum (Al) cathode was deposited with a thickness of 1,200 Å on the electron injection layer to form a cathode, thereby manufacturing an organic electroluminescent device. On the other hand, all the organic compounds required for the production of OLED elements cost about 10 -6 ~10 -8 The resulting material was purified by vacuum sublimation under torr and used for the fabrication of OLEDs.

[0224] The electroluminescence (EL) characteristics of the organic electroluminescence device fabricated as described above were measured using a Mac Science M7000. Based on the measurement results, a reference luminance of 6,000 cd / m was determined using a Mac Science M6000 lifetime measurement device. 2 At the time, T 90 was measured. The driving voltage, luminous efficiency, color coordinate (CIE), and life span of the organic light emitting device manufactured according to the present invention were measured, and the results are shown in Table 7 below.

[0225] [Table 7]

[0226] As can be seen from the results in Table 6, the organic electroluminescent device using the light-emitting layer material of the organic electroluminescent device of the present invention not only had a lower driving voltage and improved luminous efficiency compared to Comparative Examples 7 to 14, but also had a significantly improved lifespan.

[0227] In the case of Examples 11 and 12 in which an aryl group is substituted on another benzene ring in which the N-containing ring in the dibenzofuran structure is not substituted, it was confirmed that the T1 energy level is high at about 2.5 eV or more, so that the energy transfer from the host to the dopant is easy and the luminescence efficiency is excellent like that of the chemical formulas in which an arylene group or a heteroarylene group is substituted.

[0228] In particular, when X1 has a substituent of NR13, the HOMO energy level is unevenly distributed to one side, whereas when X1 has O, S, etc., it is unevenly distributed compared to the above, and it has been confirmed that an organic light emitting device having a more stable electronic structure and improved lifetime, driving stability, and efficiency can be manufactured.

[0229] It was confirmed that when N-Het is substituted at the 3rd position of one benzene ring of dibenzofuran and a specific substituent is present at the 4th position of the other benzene ring, it has better current density, lower driving voltage and higher triplet energy than when substituted at other positions.It was confirmed that when N-Het is substituted at the 3rd position of one benzene ring of dibenzofuran and a specific substituent is present at the 1st position of the other benzene ring, it has better thermal stability with lower Td than when substituted at other positions, and it has excellent lifetime characteristics of organic light emitting devices.

[0230] In addition, the results of Tables 6 and 7 show that the compound of Chemical Formula 1 and the compound of Chemical Formula 2 are contained simultaneously, and show better efficiency and lifespan effects. This result suggests that the exciplex phenomenon occurs when the two compounds are contained simultaneously.

[0231] The exciplex phenomenon is a phenomenon in which energy of the magnitude of the HOMO level of the donor (p-host) and the LUMO level of the acceptor (n-host) is released by electron exchange between two molecules. When the exciplex phenomenon between two molecules occurs, Reverse Intersystem Crossing (RISC) occurs, and the internal quantum efficiency of fluorescence can be increased 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 emission layer, holes are injected into the p-host and electrons are injected into the n-host, so that the driving voltage can be reduced, which can help improve the lifespan. In the present invention, it has been confirmed that excellent device characteristics are exhibited when the compound of Formula 2 is used as the donor and the compound of Formula 1 is used as the acceptor host in the emission layer.

[0232] The compounds of Comparative Examples 7, 8, and 9 have different substitution positions from the compounds of the present invention, and the compounds of Comparative Examples 10 and 11 have one of the two substituents of the dibenzofuran structure of Chemical Formula 1 of the present invention missing, and in this case, it was confirmed that the balance of holes and electrons in the light-emitting layer is lost, resulting in a shortened lifetime. Also, it was confirmed that when the N moiety of carbazole is bonded to dibenzofuran as in the compound of Comparative Example 14, the movement of holes becomes faster, resulting in a shortened lifetime. [Explanation of symbols]

[0233] 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. A heterocyclic compound represented by any one of the following chemical formulas 3-A, 3-B, 4-A, and 4-B: 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 In the above chemical formulas 3-A, 3-B, 4-A and 4-B, N-Het is any one selected from the following structural formulas: 【Chemistry 20】 In the above structural formula, 【Chemistry 21】 means a position connected to L in Formulae 3-A, 3-B, 4-A, and 4-B; R41 to R45 are the same or different and each independently represents hydrogen; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group; Z2 is a C6 to C60 aryl group; L is a direct bond; a substituted or unsubstituted C6-C60 arylene group; L1 is a substituted or unsubstituted C6 to C60 arylene group; X1 is O; S; CR11R12; or NR13; R1 to R4 are the same or different and 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; or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6 to C60 aliphatic or aromatic hydrocarbon ring, or a substituted or unsubstituted C2 to C60 heterocycle; R5 and R6 are the same or different and are each independently selected from the group consisting of hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1-C60 alkyl group; substituted or unsubstituted C2-C60 alkenyl group; substituted or unsubstituted C2-C60 alkynyl group; substituted or unsubstituted C1-C60 alkoxy group; substituted or unsubstituted C3-C60 cycloalkyl group; substituted or unsubstituted C2-C60 heterocycloalkyl group; substituted or unsubstituted C6-C60 aryl group; substituted or unsubstituted C2-C60 heteroaryl group; -P(=O)RR'; -SiRR'R" and -NRR'; R11 to R13, R, R' and R" are the same or different, and each independently represents 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; c and d are integers from 0 to 3; a and e are integers from 1 to 5; In Chemical Formulae 3-A and 4-A, when X1 is NR13 and R1 to R5 are all hydrogen, at least one of R41 to R45 of N-Het is a substituted or unsubstituted C10 to C60 aryl group or a substituted or unsubstituted C2 to C60 heteroaryl group.

2. The heterocyclic compound according to claim 1 , wherein R5 and R6 are hydrogen.

3. The heterocyclic compound according to claim 1, wherein the chemical formulas 3-A, 3-B, 4-A and 4-B are represented by any one of the following compounds: 【Chemistry 42】 【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 to the first electrode, and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic 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 layer includes a light-emitting layer, the light-emitting layer including the heterocyclic compound.

6. The organic light-emitting element according to claim 4 , wherein the organic 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 layer includes an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer includes 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 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.

10. The organic light-emitting device according to claim 4 , wherein the organic layer further comprises a compound represented by the following Chemical Formula 2: 【Chemistry 43】 In the above Chemical Formula 2, Ra and Rb are the same or different, and each independently represents 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 group; substituted or unsubstituted C1-C60 alkyl group; substituted or unsubstituted C2-C60 alkenyl group; substituted or unsubstituted C2-C60 alkynyl group; substituted or unsubstituted C1-C60 alkoxy group; substituted or unsubstituted C3-C60 cycloalkyl group; substituted or unsubstituted C2-C60 heterocycloalkyl group; substituted or unsubstituted C6-C60 aryl group; substituted or unsubstituted C2-C60 heteroaryl group; and substituted or unsubstituted amine group; 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: 【Chemistry 44】 【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-A, 3-B, 4-A and 4-B according to claim 1, and a heterocyclic compound represented by Chemical Formula 2 below: 【Chemistry 45】 In the above Chemical Formula 2, Ra and Rb are the same or different, and each independently represents 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 group; substituted or unsubstituted C1-C60 alkyl group; substituted or unsubstituted C2-C60 alkenyl group; substituted or unsubstituted C2-C60 alkynyl group; substituted or unsubstituted C1-C60 alkoxy group; substituted or unsubstituted C3-C60 cycloalkyl group; substituted or unsubstituted C2-C60 heterocycloalkyl group; substituted or unsubstituted C6-C60 aryl group; substituted or unsubstituted C2-C60 heteroaryl group; and substituted or unsubstituted amine group; r and s are integers from 0 to 7.

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-A, 3-B, 4-A, and 4-B 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 layer comprises the step of forming one or more organic layers using the composition for an organic layer according to claim 12.

15. 15. The method of claim 14, wherein the step of forming the organic layer comprises pre-mixing any one of the heterocyclic compounds of Chemical Formulae 3-A, 3-B, 4-A, and 4-B and the heterocyclic compound of Chemical Formula 2, and forming the organic layer using a thermal vacuum deposition method.

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