Heterocyclic compound and organic light-emitting device including the same

Abstract

The present specification relates to a heterocyclic compound represented by Chemical Formula 1 and an organic light-emitting device including the same.

Description

[Technical field]

[0001] This application claims the benefit of the filing date of Korean Patent Application No. 10-2020-0105342, filed with the Korean Intellectual Property Office on August 21, 2020, the entire contents of which are incorporated herein by reference. The present specification relates to a heterocyclic compound and an organic light-emitting device including the same. [Background technology]

[0002] An organic electroluminescent device is a type of self-luminous display device, and has advantages such as a wide viewing angle, excellent contrast, and fast response speed.

[0003] 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 necessary.

[0004] The material of the organic thin film may have a light-emitting function as necessary. For example, the material of the organic thin film may be a compound that can form a light-emitting layer by itself, or a compound that can act as a host or dopant in a host-dopant light-emitting layer. In addition, the material of the organic thin film may be a compound that can inject holes, transport holes, block electrons, transport electrons, inject electrons, etc.

[0005] There is a continuing need to develop materials for organic thin films to improve the performance, lifetime, or efficiency of organic light-emitting devices.

[0006] There is a need for research into organic light-emitting devices that contain compounds having chemical structures that can satisfy 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 of organic light-emitting devices depending on the substituents. [Prior art documents] [Patent documents]

[0007] [Patent Document 1] U.S. Patent No. 4,356,429 Summary of the Invention [Problem to be solved by the invention]

[0008] The present application relates to a heterocyclic compound and an organic light-emitting device including the same. [Means for solving the problem]

[0009] In one embodiment of the present application, there is provided a heterocyclic compound represented by the following Chemical Formula 1:

[0010] [ka]

[0011] In the above Chemical Formula 1, R1 and R2 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; R3 to R8 are the same or different and each independently represent a hydrogen atom; a deuterium atom; a halogen atom; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)RR'; -SiRR'R'', and -NRR'; or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6 to C60 aliphatic or aromatic hydrocarbon ring, or a substituted or unsubstituted C2 to C60 aliphatic or aromatic heterocycle; L1 and L2 are the same or different and each independently represents a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group; Ar1 to Ar3 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; p and m are integers from 0 to 4; n is an integer from 1 to 6; a is an integer of 0 or 1, b is an integer from 0 to 2; The R, R', and R'' are the same or different and each independently represent a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0012] According to one embodiment of the present application, there is provided 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 at least one of the organic layers contains a heterocyclic compound represented by Chemical Formula 1. Effect of the Invention

[0013] The compounds described herein can be used as materials for the organic layer of an organic light-emitting device. The compounds can act as hole injection materials, hole transport materials, light-emitting materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials, etc. in the organic light-emitting device. In particular, the compounds can be used as hole transport materials or electron blocking materials in the organic light-emitting device.

[0014] In particular, the heterocyclic compound according to the present application has an amine-based substituent and a -(L1)m-(Ar1)n substituent on the benzofluorene core structure. When the amine derivative is used as a hole transport layer, the unshared electron pair of the amine can improve the flow of holes to improve the hole transport ability of the hole transport layer, and when used as an electron blocking layer, the deterioration of the hole transport material caused by electrons entering the hole transport layer can be suppressed. In addition, by combining a substituent with enhanced hole characteristics, the band gap and T1 (triplet state energy level value) value can be adjusted to improve the hole transport ability, and the planarity and glass transition temperature of the amine derivative can be increased to improve the thermal stability of the compound. When the heterocyclic compound of Chemical Formula 1 is used as a material for the hole transport layer or electron blocking layer of an organic light emitting device, the driving voltage of the device can be reduced, the light efficiency can be improved, and the life characteristics of the device can be improved. [Brief description of the drawings]

[0015] [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. [Explanation of symbols]

[0016] 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 DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0017] The present application will be described in detail below. In this specification, the halogen may be fluorine, chlorine, bromine, or iodine. In this specification, the alkyl group includes a straight or branched chain having 1 to 60 carbon atoms, and may be further 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 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 hexyl group, a 2-methylpentyl ... Examples of alkyl groups include, but are not limited to, butyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, and 5-methylhexyl groups.

[0018] In this specification, the alkenyl group includes a straight or branched chain having 2 to 60 carbon atoms, and may be further 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 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, but are not limited thereto.

[0019] In this specification, the alkynyl group includes a straight or branched chain having 2 to 60 carbon atoms and may be further substituted with other substituents. The alkynyl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, and more specifically 2 to 20 carbon atoms.

[0020] In this 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 preferable that the number of carbon atoms is 1 to 20. Specific examples include, but are not limited to, 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, and p-methylbenzyloxy.

[0021] In this specification, the cycloalkyl group includes a monocyclic or polycyclic group having 3 to 60 carbon atoms, and may be further 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 of the cycloalkyl group may be 3 to 60, specifically 3 to 40, and more specifically 5 to 20. Specific examples of the cycloalkyl group 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.

[0022] In this 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 further 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, more specifically 3 to 20.

[0023] In this specification, the aryl group includes a monocyclic or polycyclic ring having 6 to 60 carbon atoms, and may be further substituted with other substituents. Here, the polycyclic ring means a group in which an aryl group is directly linked to or condensed with another cyclic group. Here, the other cyclic group may be an aryl group, but may also be other types of cyclic groups, such as a cycloalkyl group, a heterocycloalkyl group, or a heteroaryl group. The number of carbon atoms in the aryl group may be 6 to 60, specifically 6 to 40, and more specifically 6 to 25. Specific examples of the aryl group include a phenyl group, a biphenyl group, a triphenyl group, 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.

[0024] As used herein, fluorenyl groups may be optionally substituted, and adjacent substituents may be bonded to each other to form a ring.

[0025] When the fluorenyl group is substituted, it may be represented by the following structures, but is not limited to these: [ka]

[0026] 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 further substituted with other substituents. Here, the polycyclic ring means a group in which the heteroaryl group is directly linked or condensed with another cyclic group. Here, the other cyclic group may be a heteroaryl group, but may also be other types of cyclic groups, such as a cycloalkyl group, a heterocycloalkyl group, an aryl group, etc. The number of carbon atoms of the heteroaryl group may be 2 to 60, specifically 2 to 40, 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, a triazol ... a diphenyl group, a tetraphenyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, an isoquinazolinyl group, a quinozolyl group, a naphthyridyl group, an acridinyl group, a phenanthridinyl group, an imidazopyridinyl group, a diazanaphthalenyl group, a triazaindene group, an indolyl group, an indolizinyl group, a benzothiazolyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiophene group, a benzofuran group, a dibenzothiophene group, a dibenzofuran group, a carbazolyl group, Benzocarbazolyl 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, Examples of such groups include, but are not limited to, a phenothiazinyl 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.

[0027] In this specification, the amine group may be selected from the group consisting of a monoalkylamine group, a monoarylamine group, a monoheteroarylamine group, -NH2, a dialkylamine group, a diarylamine group, a diheteroarylamine group, an alkylarylamine group, an alkylheteroarylamine group, and an arylheteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, a dibiphenylamine group, an anthracenylamine group, a 9-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.

[0028] 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 may be applied 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 may be applied to these groups, except that they are each divalent groups.

[0029] 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.

[0030] 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.

[0031] 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 can be interpreted as "adjacent" groups to each other.

[0032] The aliphatic or aromatic hydrocarbon ring or hetero ring which can form the adjacent group may have the structures exemplified as the cycloalkyl group, cycloheteroalkyl group, aryl group, and heteroaryl group described above, except that the aliphatic or aromatic hydrocarbon ring or hetero ring is not a monovalent group.

[0033] In this specification, the term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position of the substitution is not limited as long as it is a position at which a hydrogen atom is substituted, i.e., a position at which a substituent can be substituted, and when two or more substituents are substituted, the two or more substituents may be the same or different from each other.

[0034] 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 in which two or more substituents selected from the above-mentioned substituents are linked together, The R, R', and R'' are the same or different and each independently represent a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0035] In this specification, when "no substituent is shown in the chemical formula or compound structure," it means that a hydrogen atom is bonded to the carbon atom. However, deuterium ( 2 H, Deuterium) is an isotope of hydrogen, so some hydrogen atoms may be deuterium.

[0036] In one embodiment of the present application, "when no substituent is shown in the chemical formula or compound structure", it may mean that all positions available as a substituent are hydrogen or deuterium. That is, in the case of deuterium, which is an isotope of hydrogen, some hydrogen atoms may be deuterium, which is an isotope, and in this case, the content of deuterium may be 0% to 100%.

[0037] In one embodiment of the present application, in the case where "substituents are not shown in the chemical formula or compound structure", when deuterium is not explicitly excluded, such as when the deuterium content is 0%, the hydrogen content is 100%, or the substituents are all hydrogen, hydrogen and deuterium may be used together in the compound.

[0038] 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, and its atomic symbol may be D or 2H.

[0039] In one embodiment of the present application, isotopes, meaning atoms with the same atomic number (Z) but different mass numbers (A), can also be interpreted as elements with the same number of protons but different numbers of neutrons.

[0040] In one embodiment of the present application, the content T% of a specific substituent can be defined as T2 / T1×100=T%, where T1 is the total number of substituents that the base compound may have and T2 is the number of specific substituents among them.

[0041] That is, in one example: [ka] In a phenyl group represented by the formula, the deuterium content is 20% when 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). In other words, a phenyl group with a deuterium content of 20% may be represented by the following structural formula. [ka]

[0042] In addition, in one embodiment of the present application, a "phenyl group having a deuterium content of 0%" may mean a phenyl group that does not contain a deuterium atom, that is, a phenyl group that has five hydrogen atoms.

[0043] In one embodiment of the present application, there is provided a compound represented by Chemical Formula 1.

[0044] The heterocyclic compound of Chemical Formula 1 of the present application has an amine-based substituent and a -(L1)m-(Ar1)n substituent having hole characteristics. When the compound is used as a hole transport layer of an organic light emitting device in the future, the unshared electron pair of the amine substituent can improve the flow of holes and improve the hole transport ability of the hole transport layer. When the compound is used as an electron blocking layer, the compound can suppress the deterioration of the hole transport material caused by electrons entering the hole transport layer.

[0045] In addition, the bond of the -(L1)m-(Ar1)n substituent that strengthens the hole properties increases the planarity and glass transition temperature of the amine derivative, thereby enhancing the thermal stability of the heterocyclic compound, thereby improving the life span of the organic light-emitting device containing the same.

[0046] In addition, by adjusting the band gap and T1 value, the hole transport ability and molecular stability are improved, which reduces the driving voltage of the device and improves the light efficiency. Furthermore, the thermal stability of the compound improves the life characteristics of the device.

[0047] In one embodiment of the present application, the above-mentioned Chemical Formula 1 may be represented by the following Chemical Formula 2 or 3. [ka] [ka]

[0048] In the above Chemical Formulas 2 and 3, The definitions of R1 to R8, L1, L2, Ar1 to Ar3, p, m, n, a, and b are the same as those in Chemical Formula 1 above.

[0049] In one embodiment of the present application, the chemical formula 2 may be represented by the following chemical formula 2-1 or 2-2. [ka] [ka]

[0050] In the above Chemical Formulas 2-1 and 2-2, The definitions of R1 to R8, L1, L2, Ar1 to Ar3, p, m, n, a, and b are the same as those in Chemical Formula 2 above.

[0051] In one embodiment of the present application, the above-mentioned Chemical Formula 3 may be represented by the following Chemical Formula 3-1 or Chemical Formula 3-2. [ka] [ka]

[0052] In the above Chemical Formulas 3-1 and 3-2, The definitions of R1 to R8, L1, L2, Ar1 to Ar3, p, m, n, a, and b are the same as those in Chemical Formula 3.

[0053] In one embodiment of the present application, the chemical formula 2-1 may be represented by any one of the following chemical formulas 2-1-1 to 2-1-4. [ka] [ka] [ka] [ka]

[0054] In the above Chemical Formulas 2-1-1 to 2-1-4, The definitions of R1 to R8, L1, L2, Ar1 to Ar3, p, m, n, a, and b are the same as those in Chemical Formula 2-1.

[0055] In one embodiment of the present application, the chemical formula 2-2 may be represented by any one of the following chemical formulas 2-2-1 to 2-2-4. [ka] [ka] [ka] [ka]

[0056] In the above Chemical Formulas 2-2-1 to 2-2-4, The definitions of R1 to R8, L1, L2, Ar1 to Ar3, p, m, n, a, and b are the same as those in Chemical Formula 2-2.

[0057] In one embodiment of the present application, the chemical formula 3-1 may be represented by any one of the following chemical formulas 3-1-1 to 3-1-4. [ka] [ka] [ka] [ka]

[0058] In the above Chemical Formulas 3-1-1 to 3-1-4, The definitions of R1 to R8, L1, L2, Ar1 to Ar3, p, m, n, a, and b are the same as those in Chemical Formula 3-1.

[0059] In one embodiment of the present application, the chemical formula 3-2 may be represented by any one of the following chemical formulas 3-2-1 to 3-2-4. [ka] [ka] [ka] [ka]

[0060] In the above Chemical Formulas 3-2-1 to 3-2-4, The definitions of R1 to R8, L1, L2, Ar1 to Ar3, p, m, n, a, and b are the same as those in Chemical Formula 3-2.

[0061] In one embodiment of the present application, R1 and R2 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.

[0062] In another embodiment, R1 and R2 are the same or different and may each independently be a substituted or unsubstituted C1 to C60 alkyl group; or a substituted or unsubstituted C6 to C60 aryl group.

[0063] In yet another embodiment, R1 and R2 may be the same or different and each independently may be a substituted or unsubstituted C1 to C50 alkyl group; or a substituted or unsubstituted C6 to C50 aryl group.

[0064] In yet another embodiment, R1 and R2 are the same or different and may each independently be a substituted or unsubstituted C1 to C40 alkyl group; or a substituted or unsubstituted C6 to C40 aryl group.

[0065] In yet another embodiment, R1 and R2 may be the same or different and each independently be a C1 to C40 alkyl group; or a C6 to C40 aryl group.

[0066] In yet another embodiment, R1 and R2 may be the same or different and each independently be a C1 to C20 alkyl group; or a C6 to C20 aryl group.

[0067] In yet another embodiment, R1 and R2 are the same or different and may each independently be a linear C1 to C20 alkyl group; or a C6 to C20 monocyclic or polycyclic aryl group.

[0068] In yet another embodiment, R1 and R2 are the same or different and may each independently be a methyl group; or a phenyl group.

[0069] In one embodiment of the present application, R3 to R8 are the same or different and each independently selected from the group consisting of hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1 to C60 alkyl group; substituted or unsubstituted C2 to C60 alkenyl group; substituted or unsubstituted C2 to C60 alkynyl group; substituted or unsubstituted C1 to C60 alkoxy group; substituted or unsubstituted C3 to C60 cycloalkyl group; substituted or unsubstituted C2 to C60 heterocycloalkyl group; substituted or unsubstituted C6 to C60 aryl group; substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)RR'; -SiRR'R'', and -NRR', or two or more groups adjacent to each other may be 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 aliphatic or aromatic heterocycle.

[0070] In another embodiment, R3 to R8 are the same or different and may each be independently selected from the group consisting of hydrogen; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)RR'; -SiRR'R'', and -NRR'.

[0071] In yet another embodiment, R3 to R8 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.

[0072] In yet another embodiment, R3 to R8 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.

[0073] In still another embodiment, R3 to R8 are the same or different and may each independently be hydrogen; a C1 to C40 alkyl group; a C6 to C40 aryl group; or a C2 to C40 heteroaryl group.

[0074] In yet another embodiment, R3 to R8 may be hydrogen.

[0075] In one embodiment of the present application, L1 and L2 are the same or different and may each independently be a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group.

[0076] In another embodiment, L1 and L2 are the same or different and may each independently be a direct bond; a substituted or unsubstituted C6 to C40 arylene group; or a substituted or unsubstituted C2 to C40 heteroarylene group.

[0077] In yet another embodiment, L1 and L2 are the same or different and may each independently be a direct bond; a substituted or unsubstituted C6 to C20 arylene group; or a substituted or unsubstituted C2 to C20 heteroarylene group.

[0078] In still another embodiment, L1 and L2 are the same or different and may each independently be a direct bond; a C6 to C20 arylene group; or a C2 to C20 heteroarylene group.

[0079] In yet another embodiment, L1 and L2 are the same or different and may each independently be a direct bond; or a C6 to C20 arylene group.

[0080] In still another embodiment, L1 and L2 are the same or different and may each independently be a direct bond; or a C6 to C20 monocyclic or polycyclic arylene group.

[0081] In still another embodiment, L1 and L2 are the same or different and may each independently be a direct bond; a C6 to C10 monocyclic arylene group; or a C10 to C20 polycyclic arylene group.

[0082] In yet another embodiment, L1 and L2 are the same or different and may each independently be a direct bond; a phenylene group; a biphenylene group; or a naphthalene group.

[0083] In one embodiment of the present application, L1 may be a direct bond; or a phenylene group.

[0084] In one embodiment of the present application, L2 may be a direct bond; a phenylene group; or a biphenylene group.

[0085] In one embodiment of the present application, Ar1 may be a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0086] In another embodiment, Ar1 may be a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0087] In yet another embodiment, Ar1 may be a C6 to C60 aryl group, substituted or unsubstituted with one or more substituents selected from the group consisting of a C1 to C30 alkyl group, deuterium, and a halogen group; or a C2 to C60 heteroaryl group.

[0088] In yet another embodiment, Ar1 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 C30 alkyl group, deuterium, and a halogen group; or a C2 to C40 heteroaryl group.

[0089] In yet another embodiment, Ar1 may be a C6-C40 aryl group unsubstituted or substituted with one or more substituents selected from the group consisting of a C1-C30 alkyl group, deuterium, and a halogen group; or a C2-C40 heteroaryl group containing at least one of N, O, and S as a heteroatom.

[0090] In yet another embodiment, Ar1 may be a C6-C20 aryl group unsubstituted or substituted with one or more substituents selected from the group consisting of a C1-C30 alkyl group, deuterium, and a halogen group; or a C2-C20 heteroaryl group containing at least one of N, O, and S as a heteroatom.

[0091] In yet another embodiment, Ar1 may be a phenyl group substituted with a deuterium group; a phenyl group substituted with a fluoro group (-F); a phenyl group substituted with a t-butyl group; a phenyl group substituted with a methyl group; an unsubstituted phenyl group; a biphenyl group; a naphthyl group; a dimethylfluorenyl group; or a dibenzofuran group.

[0092] In one embodiment of the present application, Ar2 and Ar3 are the same or different, and each may be independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0093] In another embodiment, Ar2 and Ar3 are the same or different and may each independently be a C6 to C60 aryl group substituted or unsubstituted with one or more substituents selected from the group consisting of a C1 to C30 alkyl group, a C2 to C40 heteroaryl group, and a C6 to C40 aryl group; or a C2 to C60 heteroaryl group.

[0094] In yet another embodiment, Ar2 and Ar3 are the same or different and may each independently be a phenyl group substituted with a dimethylfluorenyl group; a phenyl group substituted with a dibenzofuran group; a phenyl group substituted with a dibenzothiophene group; a phenyl group substituted with a biphenyl group; a phenyl group substituted with a dimethylbenzo[a]fluorenyl group; an unsubstituted phenyl group; a biphenyl group; a naphthyl group; a terphenyl group; a dimethylfluorenyl group; a diphenylfluorenyl group; a spirobifluorenyl group; a dimethylbenzo[a]fluorenyl group; a dibenzofuran group; or a dibenzothiophene group.

[0095] In one embodiment of the present application, the dimethylbenzo[a]fluorenyl group may be represented by the following structural formula: [ka]

[0096] In one embodiment of the present application, the compound represented by formula 1 [ka] may be represented by the following chemical formula A-1 or A-2. [ka] [ka]

[0097] In the above chemical formulas A-1 and A-2, The definitions of L2 and p are the same as those in Chemical Formula 1. [ka] means the position at which the group is linked to Chemical Formula 1; L11 is a direct bond; or a substituted or unsubstituted C6 to C60 arylene group; Ar12 and Ar13 are the same or different and each independently represents a substituted or unsubstituted C6 to C60 aryl group; Ar14 is a substituted or unsubstituted C2 to C60 heteroaryl group; r is an integer from 0 to 3.

[0098] In one embodiment of the present application, L11 may be a direct bond; or a substituted or unsubstituted C6 to C60 arylene group.

[0099] In another embodiment, L11 may be a direct bond; or a substituted or unsubstituted C6 to C40 arylene group.

[0100] In yet another embodiment, L11 may be a direct bond; or a substituted or unsubstituted C6 to C20 arylene group.

[0101] In yet another embodiment, L11 can be a direct bond; a phenylene group; or a biphenylene group.

[0102] In one embodiment of the present application, Ar12 and Ar13 may be the same or different and each independently be a substituted or unsubstituted C6 to C60 aryl group.

[0103] In another embodiment, Ar12 and Ar13 may be the same or different and each independently be a substituted or unsubstituted C6 to C40 aryl group.

[0104] In still another embodiment, Ar12 and Ar13 may be the same or different and each independently be a substituted or unsubstituted C6 to C20 aryl group.

[0105] In yet another embodiment, Ar12 and Ar13 are the same or different and may each independently be a phenyl group; a biphenyl group; a naphthyl group; a terphenyl group; a dimethylfluorenyl group; a diphenylfluorenyl group; a spirobifluorenyl group; or a dimethylbenzo[a]fluorenyl group.

[0106] In one embodiment of the present application, Ar14 may be a substituted or unsubstituted C2 to C60 heteroaryl group.

[0107] In another embodiment, Ar14 can be a substituted or unsubstituted C2 to C40 heteroaryl group.

[0108] In yet another embodiment, Ar14 may be a C2 to C40 heteroaryl group.

[0109] In yet another embodiment, Ar14 may be a dibenzofuran group; or a dibenzothiophene group.

[0110] 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.

[0111] In another embodiment, R, R', and R'' may be the same or different and each independently be a substituted or unsubstituted C6 to C60 aryl group.

[0112] In another embodiment, 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.

[0113] In yet another embodiment, R, R', and R'' may be the same or different and each independently be a substituted or unsubstituted C6 to C40 monocyclic aryl group.

[0114] In yet another embodiment, R, R', and R'' may be the same or different and each independently be a C6 to C20 monocyclic aryl group.

[0115] In yet another embodiment, R, R', and R'' can be phenyl groups.

[0116] In one embodiment of the present application, R31 is as defined above for R.

[0117] 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] TIFF0007632914000033.tif190165 TIFF0007632914000034.tif165165 TIFF0007632914000035.tif165165 TIFF0007632914000036.tif196165 TIFF0007632914000037.tif205165 TIFF0007632914000038.tif185165 TIFF0007632914000039.tif185165 TIFF0007632914000040.tif218165 TIFF0007632914000041.tif218165 TIFF0007632914000042.tif210165 TIFF0007632914000043.tif216165 TIFF0007632914000044.tif185165 TIFF0007632914000045.tif185165 TIFF0007632914000046.tif205165 TIFF0007632914000047.tif181165 TIFF0007632914000048.tif181165 TIFF0007632914000049.tif165165 TIFF0007632914000050.tif201165 TIFF0007632914000051.tif181165 TIFF0007632914000052.tif181165 TIFF0007632914000053.tif176165 TIFF0007632914000054.tif201165 TIFF0007632914000055.tif201165 TIFF0007632914000056.tif210165 TIFF0007632914000057.tif218165 TIFF0007632914000058.tif201165 TIFF0007632914000059.tif201165 TIFF0007632914000060.tif201165 TIFF0007632914000061.tif201165 TIFF0007632914000062.tif190165 TIFF0007632914000063.tif181165 TIFF0007632914000064.tif176165 TIFF0007632914000065.tif236165

[0118] 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 for each organic layer by introducing into the core structure substituents that are mainly used in hole injection layer materials, hole transport materials, light emitting layer materials, electron transport layer materials, and charge generation layer materials used in the manufacture of organic light emitting devices.

[0119] In addition, by introducing various substituents into the structure of Formula 1, the energy band gap can be finely adjusted, and the properties at the interface between organic materials can be improved, thereby diversifying the uses of the material.

[0120] In addition, in one embodiment of the present application, there is provided 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 at least one of the organic layers comprises a heterocyclic compound represented by Chemical Formula 1.

[0121] In another embodiment, there is provided an organic light-emitting device comprising: a first electrode; a second electrode provided opposite the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein at least one of the organic layers comprises one heterocyclic compound represented by Chemical Formula 1.

[0122] The specific details regarding the heterocyclic compound represented by Chemical Formula 1 are as described above.

[0123] In one embodiment of the present application, the first electrode may be an anode and the second electrode may be a cathode.

[0124] In another embodiment, the first electrode may be a cathode and the second electrode may be an anode.

[0125] 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.

[0126] 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.

[0127] In one embodiment of the present application, the organic light emitting device may be a red organic light emitting device, and the heterocyclic compound of Chemical Formula 1 may be used as a material of the red organic light emitting device. For example, the heterocyclic compound of Chemical Formula 1 may be included in a host material of a red light emitting layer of the red organic light emitting device.

[0128] The organic light-emitting device of the present invention may be manufactured by a typical manufacturing method and material for an organic light-emitting device, except that one or more organic layers are formed using the above-mentioned heterocyclic compound.

[0129] In manufacturing an organic light emitting device, the heterocyclic compound may be 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.

[0130] 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.

[0131] 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.

[0132] 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.

[0133] As another example, the organic layer containing the heterocyclic compound may contain the heterocyclic compound represented by Chemical Formula 1 as a host and may be used together with an iridium-based dopant.

[0134] 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.

[0135] 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.

[0136] In the organic light-emitting device of the present invention, the organic layer may include a hole transport layer, and the hole transport layer may include the heterocyclic compound.

[0137] 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.

[0138] 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, the scope of the present application is not limited to these drawings, and any structure of an organic light-emitting device known in the art may be applied to the present application.

[0139] 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 such a 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.

[0140] Fig. 3 illustrates an example in which the organic layer is multi-layered. The organic light-emitting device according to Fig. 3 includes a hole injection layer 301, a hole transport layer 302, a light-emitting layer 303, a hole blocking layer 304, an electron transport layer 305, and an electron injection layer 306. However, such a laminated structure does not limit the scope of the present application, and the remaining layers except for the light-emitting layer may be omitted as necessary, and other necessary functional layers may be further added.

[0141] The organic layer containing the compound of Formula 1 may further contain other materials, if necessary.

[0142] In an organic light-emitting device according to an 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, and may be replaced with materials known in the art.

[0143] 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.

[0144] The cathode material may be a material with a relatively low work function, such as a metal, a metal oxide, or a conductive polymer. Specific examples of the cathode material include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; and materials with a multilayer structure such as LiF / Al or LiO2 / Al.

[0145] The hole injection material may be a known hole injection material, 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. Alternatively, poly(3,4-ethylenedioxythiophene) / Poly(4-styrenesulfonate), polyaniline / Camphor sulfonic acid, or polyaniline / Poly(4-styrenesulfonate) may be used.

[0146] As the hole transport material, a pyrazoline derivative, an arylamine derivative, a stilbene derivative, a triphenyldiamine derivative, or the like may be used, and a low molecular weight or high molecular weight material may also be used.

[0147] 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. may be used, and not only low molecular weight substances but also polymeric substances may be used.

[0148] As the electron injection material, for example, LiF is typically used in the industry, but the present application is not limited thereto.

[0149] The light-emitting material may be a red, green, or blue light-emitting material, or may be a mixture of two or more light-emitting materials if necessary. In this case, the two or more light-emitting materials may be evaporated as individual supply sources, or may be premixed and evaporated 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.

[0150] When the hosts of the light-emitting materials are mixed, the hosts may be of the same type or different types. For example, two or more of n-type host materials or p-type host materials may be selected and used as the host material of the light-emitting layer.

[0151] The organic light emitting device according to one embodiment of the present application may be a top-emitting, bottom-emitting, or dual-sided emitting device depending on the materials used.

[0152] The heterocyclic compound according to one embodiment of the present application can also function in organic electronic devices such as organic solar cells, organic photoreceptors, and organic transistors, based on a similar principle to that applied to organic light-emitting devices. EXAMPLES

[0153] The present specification will be described in more detail below with reference to examples. However, these are merely for illustrating the present application and are not intended to limit the scope of the present application.

[0154] <Production Example 1> Production of Compound 2 [ka]

[0155] Preparation of Compound 2-2

[0156] 2-bromo-3-iodonaphthalene (A) (20g, 0.060mol, 1eq), phenylboronic acid (B) (8g, 0.066mol, 1.1eq), K3PO4 (38g, 0.18mol, 3eq), Pd(PPh3)4 (3.4g, 0.003mol, 0.05eq), 1,4-dioxane (400ml), and H2O (100ml) were added and stirred at 100℃ for 6h. After adding water to terminate the reaction, extraction was performed using MC and water. Then, moisture was removed with MgSO4. Separation was performed using a silica gel column to obtain 15g of compound 2-2 with a yield of 88%.

[0157] Preparation of Compound 2-3

[0158] Compound 2-2 (15g, 0.053mol, 1eq), (4-chloro-2-(methoxycarbonyl)phenyl)boronic acid (C) (12.5g, 0.058mol, 1.1eq), K3PO4 (33.7g, 0.159mol, 3eq), Pd(PPh3)4 (3g, 0.003mol, 0.0026eq), 1,4-dioxane (300ml), and H2O (750ml) were added and stirred at 100℃ for 6h. After adding water to terminate the reaction, extraction was performed using MC and water. Then, moisture was removed with MgSO4. Separation was performed using a silica gel column to obtain 15g of compound 2-3 with a yield of 76%.

[0159] Preparation of Compound 2-4

[0160] Compound 2-3 (15g, 0.040mol, 1eq) was dissolved in tetrahydrofuran (150ml), and methylmagnesium bromide (3M solution in ether) (D) (40ml, 0.120mol, 3eq) was gradually added at 0℃, and the mixture was stirred at 60℃ for 6h. Water was added to terminate the reaction, and the mixture was extracted with MC and water. Water was then removed with MgSO4. Boron trifluoride diethyl etherate was added to the reactant dissolved in MC, and the mixture was stirred at RT for 4h. The mixture was separated using a silica gel column to obtain 10g of compound 2-4 with a yield of 70%.

[0161] Preparation of compound 2

[0162] Compound 2-4 (10g, 0.028mol, 1eq), N-phenyl-[1,1'-biphenyl]-4-amine (7.2g, 0.029mol, 1.05eq), NaOt-Bu (4g, 0.042mol, 1.5eq), Pd(dba2)3 (1.3g, 0.0014mol, 0.05eq), P(t-Bu)3 (0.57g, 0.0028mol, 0.1eq), and toluene (150ml) were added and stirred at 100℃ for 8h. After adding water to terminate the reaction, extraction was performed using MC and water. Then, moisture was removed using MgSO4. Separation was performed using a silica gel column to obtain 11g of compound 2 with a yield of 69%.

[0163] Compounds were synthesized in the same manner as in Preparation Example 1, except that intermediates A, B, C, D, and E in Table 1 below were used instead of 2-bromo-3-iodonaphthalene (A), phenylboronic acid (B), (4-chloro-2-(methoxycarbonyl)phenyl)boronic acid (C), methylmagnesium bromide (3M solution in ether) (D), and N-phenyl-[1,1'-biphenyl]-4-amine (E) in Preparation Example 1.

[0164] [Table 1] TIFF0007632914000068.tif216170 TIFF0007632914000069.tif210170 TIFF0007632914000070.tif210170 TIFF0007632914000071.tif90170

[0165] Heterocyclic compounds corresponding to the above Chemical Formula 1 other than the compounds described in Preparation Example 1 and Table 1 were also prepared in the same manner as described in the above Preparation Examples.

[0166] The synthesis confirmation data of the compounds prepared above are as shown in Tables 2 and 3 below. Table 2 shows: 1 The results are those of H NMR (CDCl3, 200 Mz), and Table 3 shows those of FD-MS (Field desorption mass spectrometry).

[0167] [Table 2] TIFF0007632914000073.tif245170 TIFF0007632914000074.tif222170 TIFF0007632914000075.tif222170 TIFF0007632914000076.tif101170

[0168] [Table 3]

[0169] <Experimental Example 1> - Fabrication of organic light-emitting device 1) Preparation of organic light-emitting devices A transparent electrode indium tin oxide (ITO) thin film obtained from OLED glass (manufactured by SAMSUNG-CORNING) was ultrasonically cleaned using trichloroethylene, acetone, ethanol, and distilled water in that order for 5 minutes each, and then stored in isopropanol before use. Next, an ITO substrate was placed on the substrate holder of a vacuum deposition device, and the following 4,4',4''-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (4,4',4''-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA) was placed in the cell inside the vacuum deposition device. [ka]

[0170] Next, the vacuum level in the chamber is 10 -6 After evacuating the cell to 100 MPa (torr), a current was applied to the cell to evaporate 2-TNATA, depositing a hole injection layer with a thickness of 600 Å on the ITO substrate. N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) was placed in another cell in the vacuum deposition apparatus, and a current was applied to the cell to evaporate it, depositing a hole transport layer with a thickness of 300 Å on the hole injection layer. [ka]

[0171] After the hole injection layer and the hole transport layer were formed in this way, a blue light-emitting material having the following structure was deposited thereon as an emitting layer: Specifically, a blue light-emitting host material H1 was vacuum-deposited in one cell of the vacuum deposition apparatus to a thickness of 200 Å, and a blue light-emitting dopant material D1 was vacuum-deposited thereon at 5% relative to the host material. [ka]

[0172] Next, a compound represented by the following structural formula E1 was deposited to a thickness of 300 Å as an electron transport layer. [ka]

[0173] The OLED device was fabricated by depositing lithium fluoride (LiF) to a thickness of 10 Å as the electron injection layer and depositing an Al cathode to a thickness of 1,000 Å. Meanwhile, all organic compounds required for the fabrication of the OLED device were deposited in layers of 1000 Å each. -6 ~10 -8The organic electroluminescent device was fabricated in the same manner as in Experimental Example 1, except that the compound shown in Table 4 below was used instead of NPB used in forming the hole transport layer in Experimental Example 1.

[0174] The driving voltage, luminous efficiency, color coordinate (CIE), and lifetime of the blue organic light emitting device manufactured according to the present invention were measured, and the results are shown in Table 4 below.

[0175] [Table 4] TIFF0007632914000083.tif246170 TIFF0007632914000084.tif102170

[0176] As can be seen from the results in Table 4, the organic light-emitting device using the material of the hole transport layer of the blue organic light-emitting device of the present invention had a lower driving voltage and significantly improved luminous efficiency and lifetime compared to Comparative Examples 1 to 5.

[0177] Comparing the comparative examples in Table 4 with the compounds of the present invention, they are similar in that they have an arylamine group, but differ in that the fluorene group is substituted. In the case of a fluorene group with a substituent, it has the property of suppressing pi-pi stacking of aromatic rings, thereby preventing the phenomenon in which the driving voltage of an organic light-emitting device increases and the device characteristics deteriorate. Therefore, it was found that the compounds of the present invention using such derivatives are excellent in all aspects of driving, efficiency, and lifespan by improving hole transport properties or stability.

[0178] <Experimental Example 2> - Fabrication of organic light-emitting device 1) Preparation of organic light-emitting devices A transparent electrode indium tin oxide (ITO) thin film obtained from OLED glass (manufactured by SAMSUNG-CORNING) was ultrasonically cleaned using trichloroethylene, acetone, ethanol, and distilled water in that order for 5 minutes each, and then stored in isopropanol before use. Next, an ITO substrate was placed on the substrate holder of a vacuum deposition device, and the following 4,4',4''-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (4,4',4''-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA) was placed in the cell inside the vacuum deposition device. [ka]

[0179] Next, the vacuum level in the chamber is 10 -6 After evacuating the cell to 100 MPa (torr), a current was applied to the cell to evaporate 2-TNATA, depositing a hole injection layer with a thickness of 600 Å on the ITO substrate. N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) was placed in another cell in the vacuum deposition apparatus, and a current was applied to the cell to evaporate it, depositing a hole transport layer with a thickness of 300 Å on the hole injection layer. [ka]

[0180] After the hole injection layer and the hole transport layer were formed in this way, a blue light-emitting material having the following structure was deposited thereon as an emitting layer: Specifically, a blue light-emitting host material H1 was vacuum-deposited in one cell of the vacuum deposition apparatus to a thickness of 200 Å, and a blue light-emitting dopant material D1 was vacuum-deposited thereon at 5% relative to the host material. [ka]

[0181] Next, a compound represented by the following structural formula E1 was deposited to a thickness of 300 Å as an electron transport layer. [ka] The OLED device was fabricated by depositing lithium fluoride (LiF) to a thickness of 10 Å as the electron injection layer and depositing an Al cathode to a thickness of 1,000 Å. Meanwhile, all organic compounds required for the fabrication of the OLED device were deposited in layers of 1000 Å each. -6 ~10 -8 The organic electroluminescent device was fabricated in the same manner as in Example 2, except that a hole transport layer NPB was formed to a thickness of 250 Å, and an electron blocking layer was formed on the hole transport layer with a thickness of 50 Å using the compound shown in Table 5 below. The driving voltage, luminous efficiency, color coordinate (CIE), and lifetime of the blue organic light emitting device fabricated according to the present invention were measured, and the results are shown in Table 5 below.

[0182] [Table 5] TIFF0007632914000090.tif246170 TIFF0007632914000091.tif103170

[0183] As can be seen from the results in Table 5, the organic light emitting device using the material of the electron blocking layer of the blue organic light emitting device of the present invention has a lower driving voltage and significantly improved luminous efficiency and lifetime compared to the Comparative Example. When electrons do not combine in the emitting layer but travel to the anode via the hole transport layer, a phenomenon occurs in which the efficiency and lifetime of the OLED device are reduced.

[0184] In order to prevent this phenomenon, if a compound with a high LUMO level is used as the electron blocking layer, the electrons that pass through the light emitting layer and go to the anode are blocked by the energy barrier of the electron blocking layer. Therefore, the probability that holes and electrons form excitons increases, and the probability that they are emitted as light from the light emitting layer increases, and it was found that the compound of the present invention is excellent in all aspects of operation, efficiency, and life.

[0185] In particular, when the amine derivative of the compound of Chemical Formula 1 of the present application is used as a hole transport layer, the unshared electron pair of the amine can improve the flow of holes and improve the hole transport ability of the hole transport layer, and when it is used as an electron blocking layer, it can suppress the deterioration of the hole transport material caused by electrons that have entered the hole transport layer. In addition, it has been confirmed that the planarity and glass transition temperature of the amine derivative are increased by combining a substituent that strengthens the hole characteristics with an amine moiety, thereby increasing the thermal stability of the compound.

[0186] In addition, it was confirmed that the adjustment of the band gap and T1 value improves the hole transport ability and molecular stability, thereby lowering the driving voltage of the device and improving the light efficiency, and that the thermal stability of the compound improves the life characteristics of the device.

Claims

1. A compound represented by the following chemical formula 1: 【Chemistry 42】 In the above Chemical Formula 1, R1 and R2 are the same or different, and each independently represents a substituted or unsubstituted C1 to C60 alkyl group; or a substituted or unsubstituted C6 to C60 aryl group; R3 to R8 are the same or different and each independently represents hydrogen or deuterium; L1 and L2 are the same or different and each independently represent a direct bond; or a substituted or unsubstituted C6 to C60 arylene group; Ar1 is a C6-C60 aryl group or a C2-C60 heteroaryl group, which is substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium; halogen; C1-C60 linear or branched alkyl, C6-C60 monocyclic or polycyclic aryl, and C2-C60 monocyclic or polycyclic heteroaryl, or is substituted or unsubstituted with a substituent in which two or more substituents selected from the above-listed substituents are linked together; Ar2 and Ar3 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; p and m are integers from 0 to 4, n is an integer from 1 to 6, a is an integer of 0 or 1, and b is an integer from 0 to 2; With regard to R1, R2, L1, L2, Ar2, and Ar3, "substituted or unsubstituted" means that the group is substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium; C1-C60 linear or branched alkyl; C6-C60 monocyclic or polycyclic aryl; and C2-C60 monocyclic or polycyclic heteroaryl, or is substituted or unsubstituted with a substituent in which two or more substituents selected from the above-listed substituents are linked.

2. The compound according to claim 1 , wherein the formula 1 is represented by the following formula 2 or 3: 【Chemistry 43】 【Chemistry 44】 In Chemical Formulae 2 and 3, the definitions of R1 to R8, L1, L2, Ar1 to Ar3, p, m, n, a, and b are the same as those in Chemical Formula 1.

3. Formula 1 【Chemistry 45】 The compound according to claim 1, represented by the following chemical formula A-1 or A-2: 【Chemistry 46】 【Chemistry 47】 In the above chemical formulas A-1 and A-2, The definitions of L2 and p are the same as those in Chemical Formula 1. 【Chemistry 48】 means a position connected to Chemical Formula 1; L11 is a direct bond; or a substituted or unsubstituted C6-C60 arylene group; Ar12 and Ar13 are the same or different and each independently represents a substituted or unsubstituted C6 to C60 aryl group; Ar14 is a substituted or unsubstituted C2-C60 heteroaryl group; and r is an integer from 0 to 3.

4. The compound according to claim 1, wherein R1 and R2 are the same or different and each independently represents an alkyl group having 1 to 20 carbon atoms; or an aryl group having 6 to 20 carbon atoms.

5. The compound according to claim 1, wherein R3 to R8 are hydrogen.

6. The compound according to claim 1 , wherein the formula 1 is represented by any one of the following compounds: 【Chemistry 49】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】

7. An organic light-emitting device comprising: a first electrode; a second electrode provided opposite to the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein one or more of the organic material layers comprises the compound according to any one of claims 1 to 6.

8. The organic light-emitting element according to claim 7 , wherein the organic layer includes a light-emitting layer, the light-emitting layer including the compound.

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

10. The organic light-emitting device according to claim 7 , wherein the organic layer comprises an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer comprises the compound.

11. The organic light-emitting element according to claim 7 , wherein the organic layer includes a hole transport layer, and the hole transport layer includes the compound.

12. The organic light-emitting device according to claim 7 , 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.

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