Complex ring compound and organic light-emitting device containing the same

Abstract

The present invention 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 priority based on Korean Patent Application No. 10-2022-0054355, filed on May 2, 2022, and includes all the contents disclosed in the document of the Korean Patent Application as part of this specification.

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

Background Art

[0003] An organic light-emitting device is a type of self-emitting display device, which has advantages such as a wide viewing angle, excellent contrast, and fast response speed.

[0004] 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 the organic light-emitting device having such a structure, electrons and holes injected from the two electrodes combine in the organic thin film to form a pair and emit light while disappearing. The organic thin film may be composed of a single layer or multiple layers as required.

[0005] The material of the organic thin film can have a light-emitting function as required. For example, as the material of the organic thin film, a compound that can itself constitute a light-emitting layer alone may be used, or a compound that can serve as a host or a dopant of a host-dopant type light-emitting layer may be used. In addition, as the material of the organic thin film, a compound that can serve roles such as hole injection, hole transport, electron blocking, hole blocking, electron transport, and electron injection may be used.

[0006] In order to improve the performance, lifespan, or efficiency of the organic light-emitting device, the development of materials for the organic thin film has been continuously demanded.

Prior Art Documents

Patent Documents

[0007]

Patent Document 1

Summary of the Invention

Problems to be Solved by the Invention

[0008] An object of the present invention is to provide a heterocyclic compound and an organic light-emitting device containing the same.

Means for Solving the Problems

[0009] To achieve the above object, the present invention provides a heterocyclic compound represented by the following Chemical Formula 1.

Chemical Formula

[0010] In the Chemical Formula 1, R1 to R3 are the same as or different from each other, and each independently is 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)R101R102; -SiR101R102R103; and -NR101R102, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6-C60 aromatic hydrocarbon ring; or a substituted or unsubstituted C2-C60 heterocyclic ring, and R101, R102 and R103 are the same as or different from each other, and each independently is a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group, a is an integer of 0 to 4, and when a is 2 or more, R1 are the same as or different from each other, b is an integer from 0 to 4, and when b is 2 or more, R2s are the same as or different from each other. Ar1 to Ar3 are the same as or different from each other, and each independently is a substituted or unsubstituted C6 - C60 aryl group; or a substituted or unsubstituted C2 - C60 heteroaryl group. L1 is a substituted or unsubstituted C6 - C60 arylene group; or a substituted or unsubstituted C2 - C60 heteroarylene group. c is an integer from 1 to 5, and when c is 2 or more, L1s are the same as or different from each other. L2 and L3 are the same as or different from each other, and each independently is a direct bond; a substituted or unsubstituted C6 - C60 arylene group; or a substituted or unsubstituted C2 - C60 heteroarylene group. d is an integer from 0 to 5, and when d is 2 or more, L2s are the same as or different from each other. e is an integer from 0 to 5, and when e is 2 or more, L3s are the same as or different from each other.

[0011] Also, the present invention provides 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; and is an organic light - emitting device, wherein one or more of the organic layers contain a heterocyclic compound represented by Chemical Formula 1.

[0012] Also, the present invention provides an organic light - emitting device in which the organic layer includes a hole - transporting layer, and the hole - transporting layer contains the heterocyclic compound.

[0013] Also, the present invention provides an organic light - emitting device in which the organic layer includes an electron - blocking layer, and the electron - blocking layer contains the heterocyclic compound.

Advantages of the Invention

[0014] The compounds described in this specification can be used as materials for the organic layer of an organic light-emitting device. The said compounds can serve as hole injection layer materials, electron blocking layer materials, hole transport layer materials, light-emitting layer materials, electron transport layer materials, hole blocking layer materials, electron injection layer materials, etc. in an organic light-emitting device. In particular, the said compounds can be used as hole transport layer materials, electron blocking layer materials, or light-emitting layer materials of an organic light-emitting device.

[0015] Specifically, the heterocyclic compound represented by Chemical Formula 1 has a high hole mobility, appropriate HOMO (Highest Occupied Molecular Orbital) level and high LUMO (Lowest Unoccupied Molecular Orbital) level, and can reduce the driving voltage and improve the luminous efficiency and lifetime characteristics.

Brief Description of the Drawings

[0016]

Figure 1

Figure 2

Figure 3

Modes for Carrying Out the Invention

[0017] Hereinafter, the present invention will be described in more detail.

[0018] In this specification, the term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is substituted by another substituent, and the position of substitution is not limited as long as it is the position where the hydrogen atom is substituted, that is, the position where the substituent can be substituted. When two or more substitutions occur, the two or more substituents may be the same or different from each other.

[0019] As used herein, "substituted or unsubstituted" means substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium; halogen; cyano group; C1-C60 straight-chain or branched alkyl group; C2-C60 straight-chain or branched alkenyl group; C2-C60 straight-chain or branched alkynyl group; C3-C60 monocyclic or polycyclic cycloalkyl group; C2-C60 monocyclic or polycyclic heterocycloalkyl group; C6-C60 monocyclic or polycyclic aryl group; C2-C60 monocyclic or polycyclic heteroaryl group; -SiRR'R"; -P(=O)RR'; C1-C20 alkylamine group; C6-C60 monocyclic or polycyclic arylamine group; and C2-C60 monocyclic or polycyclic heteroarylamine group, or substituted with a substituent in which two or more substituents selected from the exemplified substituents are linked, or unsubstituted.

[0020] As used herein, the halogen may be fluorine, chlorine, bromine or iodine.

[0021] In this specification, the alkyl group includes a linear or branched chain having 1 to 60 carbon atoms and may be further substituted by other substituents. The number of carbon atoms of the alkyl group may be 1 to 60, specifically 1 to 40, and more specifically 1 to 20. Specific examples include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methyl-butyl group, 1-ethyl-butyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl-2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, cyclopentylmethyl group, cyclohexylmethyl group, octyl group, n-octyl group, tert-octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2,2-dimethylheptyl group, 1-ethyl-propyl group, 1,1-dimethyl-propyl group, isohexyl group, 2-methylpentyl group, 4-methylhexyl group, 5-methylhexyl group, etc., but are not limited thereto.

[0022] In this specification, the alkenyl group includes a linear or branched chain having 2 to 60 carbon atoms and may be further substituted by other substituents. The number of carbon atoms of the alkenyl group may be 2 to 60, specifically 2 to 40, and more specifically 2 to 20. Specific examples include vinyl group, 1-propenyl group, isopropenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 3-methyl-1-butenyl group, 1,3-butadienyl group, allyl group, 1-phenylvinyl-1-yl group, 2-phenylvinyl-1-yl group, 2,2-diphenylvinyl-1-yl group, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl group, 2,2-bis(diphenyl-1-yl)vinyl-1-yl group, stilbenyl group, styrenyl group, etc., but are not limited thereto.

[0023] In this specification, the alkynyl group includes a linear or branched chain having 2 to 60 carbon atoms and may be further substituted by other substituents. The number of carbon atoms of the alkynyl group may be 2 to 60, specifically 2 to 40, and more specifically 2 to 20.

[0024] In this specification, the alkoxy group may be a linear, branched or cyclic chain. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 20. Specifically, methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, isobutoxy group, tert-butoxy group, sec-butoxy group, n-pentyloxy group, neopentyloxy group, isopentyloxy group, n-hexyloxy group, 3,3-dimethylbutyloxy group, 2-ethylbutyloxy group, n-octyloxy group, n-nonyloxy group, n-decyloxy group, benzyloxy group, p-methylbenzyloxy group, etc. may be mentioned, but are not limited thereto.

[0025] In this specification, the cycloalkyl group includes a monocyclic or polycyclic ring having 3 to 60 carbon atoms and may be further substituted by other substituents. Here, the polycyclic ring 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, a heteroaryl group, etc. The number of carbon atoms of the cycloalkyl group may be 3 to 60, specifically 3 to 40, and more specifically 5 to 20. Specifically, cyclopropyl group, cyclobutyl group, cyclopentyl group, 3-methylcyclopentyl group, 2,3-dimethylcyclopentyl group, cyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 2,3-dimethylcyclohexyl group, 3,4,5-trimethylcyclohexyl group, 4-tert-butylcyclohexyl group, cycloheptyl group, cyclooctyl group, etc. may be mentioned, but are not limited thereto.

[0026] As used herein, a heterocycloalkyl group contains O, S, Se, N, or Si as a heteroatom, contains 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 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, a heteroaryl group, etc. The carbon number of the heterocycloalkyl group may be 2 to 60, specifically 2 to 40, and more specifically 3 to 20.

[0027] As used herein, an aryl group contains 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 the aryl group is directly linked 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, a heteroaryl group, etc. The aryl group may contain a spiro group. The carbon number of 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, but are not limited to, 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, a fluorenyl group, an indenyl group, an acenaphthylenyl group, a benzofluorenyl group, a spirobifluorenyl group, a 2,3-dihydro-1H-indenyl group, and condensed rings thereof.

[0028] In this specification, the phosphine oxide group is represented by -P(=O)R101R102, and R101 and R102 may be the same as or different from each other, and each independently may be a substituent composed 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. Specifically, it may be substituted with an aryl group, and the above-described examples can be applied to the aryl group. For example, examples of the phosphine oxide group include, but are not limited to, a diphenylphosphine oxide group, a dinaphthylphosphine oxide group, and the like.

[0029] In this specification, the silyl group contains Si and is a substituent in which the Si atom is directly linked as a radical, and is represented by -SiR101R102R103, and R101 to R103 may be the same as or different from each other, and each independently may be a substituent composed 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, a phenylsilyl group, and the like.

[0030] In this specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.

[0031] When the fluorenyl group is substituted,

Chemical formula

[0032] In this specification, the spiro group is a group containing a spiro structure and may have 15 to 60 carbon atoms. For example, the spiro group may include a structure in which a 2,3-dihydro-1H-indenyl group or a cyclohexane group is spiro-bonded to a fluorenyl group. Specifically, the spiro group may include any one of the groups represented by the following structural formulas. [Chemical formula]

[0033] In this specification, the heteroaryl group contains, as heteroatoms, S, O, Se, N, or Si, contains a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may be further substituted by 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, for example, 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 thiophenyl 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 triazinyl group, a tetrazinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, an isoquinazolinyl group, a quinoxalinyl group, a naphthyridyl group, an acridinyl group, a phenanthridinyl group, an imidazopyridinyl group, a diazanaphthalenyl group, a triazaindenyl group, a 2-indolyl group, an indolizinyl group, a benzothiazolyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiophenyl group, a benzofuranyl group, a dibenzothiophenyl group, a dibenzofuranyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a phenazinyl group, a dibenzosilolyl group, a spirobi(dibenzosilol) group, a dihydrophenazinyl group, a phenoxazinyl group, a phenanthridyl group, a thienyl group, an indolo[2,3-a]carbazolyl group, an indolo[2,3-b]carbazolyl group, an indolinyl group, a 10,11-dihydro-dibenzo[b,f]azepinyl group, a 9,10-dihydroacridinyl group, a phenanthradinyl group, 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, a 5,11-dihydroindenol[1,2-b]carbazolyl group, etc., but are not limited thereto.

[0034] In this specification, the amine group is a monoalkylamine group; a monoarylamine group; a monoheteroarylamine group; -NH 2; It may be selected from the group consisting of a dialkylamine group, a diarylamine group, a diheteroarylamine group, an alkylarylamine group, an alkylheteroarylamine group, and an arylheteroarylamine group. 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, a biphenyltriphenylenylamine group, etc., but are not limited thereto.

[0035] In the present specification, an arylene group means a group having two bonding positions on an aryl group, that is, a divalent group. Except that these are each divalent groups, the description of the aryl group described above is applicable. Further, a heteroarylene group means a group having two bonding positions on a heteroaryl group, that is, a divalent group. Except that these are each divalent groups, the description of the heteroaryl group described above is applicable.

[0036] In the present invention, the "adjacent" group may mean a substituent substituted on an atom directly connected to the atom substituted with the said substituent, a substituent located closest in steric structure to the said substituent, or another substituent substituted on the atom substituted with the said substituent. For example, two substituents substituted at the ortho position on a benzene ring and two substituents substituted at the same carbon on an aliphatic ring can be interpreted as "adjacent" groups to each other.

[0037] In the present invention, "when no substituent is shown in the chemical formula or compound structure" means that a hydrogen atom is bonded to a carbon atom. However, deuterium ( 2Since hydrogen (H, deuterium) is an isotope of hydrogen, some of the hydrogen atoms may be deuterium.

[0038] In one embodiment of the present invention, "when no substituent is shown in the chemical formula or compound structure" may mean that all the substituents are hydrogen or deuterium. That is, in the case of deuterium, as an isotope of hydrogen, some of the hydrogen atoms may be deuterium, which is an isotope, and at this time, the content of deuterium may be 0% to 100%.

[0039] In one embodiment of the present invention, in the case of "when no substituent is shown in the chemical formula or compound structure", when deuterium is not explicitly excluded, such as "the content of deuterium is 0%", "the content of hydrogen is 100%", and "all substituents are hydrogen", hydrogen and deuterium may be mixed in the compound.

[0040] In one embodiment of the present invention, deuterium is one of the isotopes of hydrogen, and is an element having a deuteron composed of 1 proton and 1 neutron as its nucleus, which can be represented as hydrogen-2, and the element symbol can be D or 2 H.

[0041] In one embodiment of the present invention, isotopes can also be interpreted as elements that have the same atomic number (Z) but different mass numbers (A), and have the same number of protons but different numbers of neutrons.

[0042] In one embodiment of the present invention, the meaning of the content T% of a specific substituent can be defined as follows: when the total number of substituents that the basic compound can have is defined as T1, and the number of a specific substituent is defined as T2, then T2 / T1×100 = T%.

[0043] That is, in one example,

Chem.

Chem.

[0044] Also, in one embodiment of the present invention, in the case of "a phenyl group with a deuterium content of 0%", it may mean a phenyl group that does not contain deuterium atoms, that is, a phenyl group having 5 hydrogen atoms.

[0045] In the present invention, the C6 - C60 aromatic hydrocarbon ring means a compound containing an aromatic ring composed of C6 - C60 carbon and hydrogen atoms. For example, phenyl, biphenyl, terphenyl, triphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chrysene, perylene, azulene, etc. can be mentioned, but it is not limited to these, and as long as the carbon number is satisfied, all aromatic hydrocarbon ring compounds known in this field are included.

[0046] The present invention provides a heterocyclic compound represented by the following Chemical Formula 1.

Chem.

[0047] In the Chemical Formula 1, R1 to R3 are the same as or different from each other, and each independently is 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)R101R102; -SiR101R102R103; and -NR101R102, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6-C60 aromatic hydrocarbon ring; or a substituted or unsubstituted C2-C60 heterocyclic ring, where R101, R102 and R103 are the same as or different from each other, and each independently is a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group, a is an integer from 0 to 4, and when a is 2 or more, R1s are the same as or different from each other, b is an integer from 0 to 4, and when b is 2 or more, R2s are the same as or different from each other, Ar1 to Ar3 are the same as or different from each other, and each independently is a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group, L1 is a substituted or unsubstituted C6-C60 arylene group; or a substituted or unsubstituted C2-C60 heteroarylene group, c is an integer from 1 to 5, and when c is 2 or more, L1s are the same as or different from each other, L2 and L3 are the same as or different from each other, and each independently is a direct bond; a substituted or unsubstituted C6-C60 arylene group; or a substituted or unsubstituted C2-C60 heteroarylene group, d is an integer from 0 to 5, and when d is 2 or more, L2s are the same as or different from each other, The e is an integer from 0 to 5, and when e is 2 or more, L3s are the same as or different from each other.

[0048] In one embodiment of the present invention, the R1 to R3 are the same as or different from each other, and each independently is hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1-C30 alkyl group; substituted or unsubstituted C2-C30 alkenyl group; substituted or unsubstituted C2-C30 alkynyl group; substituted or unsubstituted C1-C30 alkoxy group; substituted or unsubstituted C3-C30 cycloalkyl group; substituted or unsubstituted C2-C30 heterocycloalkyl group; substituted or unsubstituted C6-C30 aryl group; substituted or unsubstituted C2-C30 heteroaryl group; -P(=O)R101R102; -SiR101R102R103; or -NR101R102, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6-C30 aromatic hydrocarbon ring; or a substituted or unsubstituted C2-C30 heterocyclic ring, and the R101, R102 and R103 are the same as or different from each other, and each independently may be a C1-C30 alkyl group; a substituted or unsubstituted C6-C30 aryl group; or a substituted or unsubstituted C2-C30 heteroaryl group.

[0049] In another embodiment of the present invention, R1 to R3 are the same as or different from each other, and each independently is hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1-C20 alkyl group; substituted or unsubstituted C2-C20 alkenyl group; substituted or unsubstituted C2-C20 alkynyl group; substituted or unsubstituted C1-C20 alkoxy group; substituted or unsubstituted C3-C20 cycloalkyl group; substituted or unsubstituted C2-C20 heterocycloalkyl group; substituted or unsubstituted C6-C20 aryl group; substituted or unsubstituted C2-C20 heteroaryl group; -P(=O)R101R102; -SiR101R102R103; or -NR101R102, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6-C20 aromatic hydrocarbon ring; or a substituted or unsubstituted C2-C20 heterocyclic ring, and R101, R102 and R103 are the same as or different from each other, and each independently may be a C1-C20 alkyl group; a substituted or unsubstituted C6-C20 aryl group; or a substituted or unsubstituted C2-C20 heteroaryl group.

[0050] In another embodiment of the present invention, R1 to R3 are the same as or different from each other, and each independently is hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1-C20 alkyl group; substituted or unsubstituted C2-C20 alkenyl group; substituted or unsubstituted C2-C20 alkynyl group; substituted or unsubstituted C1-C20 alkoxy group; substituted or unsubstituted C3-C20 cycloalkyl group; substituted or unsubstituted C2-C20 heterocycloalkyl group; substituted or unsubstituted C6-C20 aryl group; substituted or unsubstituted C2-C20 heteroaryl group; -P(=O)R101R102; -SiR101R102R103; or -NR101R102, and R101, R102 and R103 are the same as or different from each other, and each independently may be a C1-C20 alkyl group; a substituted or unsubstituted C6-C20 aryl group; or a substituted or unsubstituted C2-C20 heteroaryl group.

[0051] In another embodiment of the present invention, R1 to R3 may be the same as or different from each other, and each independently may be hydrogen; deuterium; a halogen; a cyano group; a substituted or unsubstituted C1-C20 alkyl group; a substituted or unsubstituted C6-C20 aryl group; or a substituted or unsubstituted C2-C20 heteroaryl group.

[0052] In another embodiment of the present invention, R1 to R3 may be the same as or different from each other, and each independently may be hydrogen; deuterium; a substituted or unsubstituted C6-C20 aryl group; or a substituted or unsubstituted C2-C20 heteroaryl group.

[0053] In another embodiment of the present invention, R1 may be hydrogen; deuterium; a substituted or unsubstituted C6-C30 aryl group; or a substituted or unsubstituted C2-C30 heteroaryl group.

[0054] In another embodiment of the present invention, R1 may be hydrogen; deuterium; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted triphenylenyl group; a substituted or unsubstituted dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophenyl group.

[0055] In another embodiment of the present invention, R2 and R3 may be the same as or different from each other, and each independently may be hydrogen; or deuterium.

[0056] In one embodiment of the present invention, Ar1 to Ar3 may be the same as or different from each other, and each independently may be a substituted or unsubstituted C6-C30 aryl group; or a substituted or unsubstituted C2-C30 heteroaryl group.

[0057] In another embodiment of the present invention, Ar1 to Ar3 may be the same as or different from each other, and each independently may be a substituted or unsubstituted C6-C20 aryl group; or a substituted or unsubstituted C2-C20 heteroaryl group.

[0058] In another embodiment of the present invention, Ar1 to Ar3 may be the same as or different from each other, and each independently may be a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted triphenylenyl group; a substituted or unsubstituted dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophenyl group.

[0059] In one embodiment of the present invention, L1 may be a substituted or unsubstituted C6-C30 arylene group; or a substituted or unsubstituted C2-C30 heteroarylene group.

[0060] In another embodiment of the present invention, L1 may be a substituted or unsubstituted C6-C20 arylene group; or a substituted or unsubstituted C2-C20 heteroarylene group.

[0061] In another embodiment of the present invention, L1 may be a substituted or unsubstituted C6-C20 arylene group.

[0062] In another embodiment of the present invention, L1 may be a substituted or unsubstituted phenylene group; or a substituted or unsubstituted non-phenylene group.

[0063] In one embodiment of the present invention, L2 and L3 may be the same as or different from each other, and each independently may be a direct bond; a substituted or unsubstituted C6-C30 arylene group; or a substituted or unsubstituted C2-C30 heteroarylene group.

[0064] In another embodiment of the present invention, L2 and L3 may be the same as or different from each other, and each independently may be a direct bond; a substituted or unsubstituted C6-C20 arylene group; or a substituted or unsubstituted C2-C20 heteroarylene group.

[0065] In another embodiment of the present invention, L2 and L3 may be the same as or different from each other, and each independently may be a direct bond or a substituted or unsubstituted C6-C20 arylene group.

[0066] In another embodiment of the present invention, L2 and L3 may be the same as or different from each other, and each independently may be a direct bond or a substituted or unsubstituted phenylene group.

[0067] In one embodiment of the present invention, the heterocyclic compound represented by Chemical Formula 1 may not contain deuterium as a substituent, or the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms may be, for example, more than 0%, 1% or more, 10% or more, 20% or more, 30% or more, 40% or more, or 50% or more, and may also be 100% or less, 90% or less, 80% or less, 70% or less, or 60% or less.

[0068] In another embodiment of the present invention, the heterocyclic compound represented by Chemical Formula 1 may not contain deuterium as a substituent, or the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms may be 1% to 100%.

[0069] In another embodiment of the present invention, the heterocyclic compound represented by Chemical Formula 1 may not contain deuterium as a substituent, or the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms may be 20% to 90%.

[0070] In another embodiment of the present invention, the heterocyclic compound represented by Chemical Formula 1 may not contain deuterium as a substituent, or the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms may be 30% to 80%.

[0071] In another embodiment of the present invention, the heterocyclic compound represented by Chemical Formula 1 may not contain deuterium as a substituent, or the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms may be 50% to 70%.

[0072] In one embodiment of the present invention, the heterocyclic compound represented by Chemical Formula 1 may be represented by any one of the following compounds.

[0073]

Chemical Formula

[0074]

Chemical Formula

[0075]

Chemical Formula

[0076]

Chemical Formula

[0077]

Chemical Formula

[0078]

Chemical Formula

[0079]

Chemical Formula

[0080]

Chemical Formula

[0081]

Chemical Formula

[0082]

Chem.

[0083]

Chem.

[0084]

Chem.

[0085]

Chem.

[0086]

Chem.

[0087]

Chem.

[0088]

Chem.

[0089]

Chem.

[0090]

Chem.

[0091]

Chem.

[0092] [Chemical formula]

[0093] Moreover, by introducing various substituents into the structure of Chemical Formula 1, compounds having the unique properties of the introduced substituents can be synthesized. For example, by introducing the substituents mainly used for the hole injection layer material, hole transport layer material, light emitting layer material, electron transport layer material, electron blocking layer material, and charge generation layer material used during the manufacture of an organic light emitting device into the core structure, substances that meet the requirements for each organic layer can be synthesized.

[0094] Moreover, by introducing various substituents into the structure of Chemical Formula 1, fine adjustment of the energy band gap can be enabled, while improving the properties at the interface between organic substances and diversifying the uses of the substance.

[0095] On the other hand, the heterocyclic compound represented by Chemical Formula 1 has a high glass transition temperature (Tg) and excellent thermal stability. Such improvement in thermal stability is an important factor providing driving stability to the device.

[0096] The heterocyclic compound according to an embodiment of the present invention may be produced by a multi-step chemical reaction. Some intermediate compounds may be produced first, and then the heterocyclic compound represented by Chemical Formula 1 may be produced from the intermediate compounds. More specifically, the heterocyclic compound according to an embodiment of the present invention may be produced based on the production examples described later.

[0097] Another embodiment of the present invention provides an organic light emitting device including the heterocyclic compound represented by Chemical Formula 1. The "organic light emitting device" can be expressed by terms such as "organic light emitting diode", "OLED (Organic Light Emitting Diodes)", "OLED device", and "organic electroluminescent device".

[0098] Moreover, the present invention a first electrode; A second electrode provided to face the first electrode; and One or more organic layers provided between the first electrode and the second electrode; An organic light-emitting device comprising: Provided is an organic light-emitting device in which one or more of the organic layers contain a heterocyclic compound represented by Chemical Formula 1.

[0099] In one embodiment of the present invention, the first electrode may be an anode, and the second electrode may be a cathode.

[0100] In another embodiment, the first electrode may be a cathode, and the second electrode may be an anode.

[0101] In one embodiment of the present invention, the organic layer may include one or more selected from the group consisting of an electron injection layer, an electron transport layer, a hole blocking layer, a light-emitting layer, a light-emitting auxiliary layer, an electron blocking layer, a hole transport layer, and a hole injection layer, and one or more layers selected from the group consisting of an electron injection layer, an electron transport layer, a hole blocking layer, a light-emitting layer, a light-emitting auxiliary layer, an electron blocking layer, a hole transport layer, and a hole injection layer may contain a heterocyclic compound represented by Chemical Formula 1.

[0102] In another embodiment of the present invention, the organic layer may include a hole transport layer, and the hole transport layer may contain a heterocyclic compound represented by Chemical Formula 1. When the heterocyclic compound is used in the hole transport layer, the heterocyclic compound has a high hole mobility and an appropriate HOMO level. When the heterocyclic compound is used as the hole transport layer, hole transport to the light-emitting layer is easy, the driving voltage of the organic light-emitting device can be reduced, and the driving efficiency and lifetime can be improved.

[0103] In another embodiment of the present invention, the organic layer may include an electron blocking layer, and the electron blocking layer may include the heterocyclic compound represented by Chemical Formula 1. Since the heterocyclic compound has a high LUMO level, when the heterocyclic compound is used as the electron blocking layer, the probability of holes and electrons forming an exciton can be increased, and the possibility of being emitted as light from the light emitting layer can be increased. Therefore, the electron blocking ability is improved, holes and electrons balance the charge, and the driving efficiency and lifespan of the organic light emitting device may be improved.

[0104] In another embodiment of the present invention, the organic layer may include an electron injection layer or an electron transport layer, and the electron injection layer or the electron transport layer may include the heterocyclic compound represented by Chemical Formula 1. In another embodiment of the present invention, 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 represented by Chemical Formula 1.

[0105] In another embodiment of the present invention, the organic layer may include an electron transport layer, a light emitting layer or a hole blocking layer, and the electron transport layer, the light emitting layer or the hole blocking layer may include the heterocyclic compound represented by Chemical Formula 1.

[0106] In another embodiment of the present invention, the organic layer may include a hole transport layer, an electron blocking layer or a light emitting auxiliary layer, and the hole transport layer, the electron blocking layer or the light emitting auxiliary layer may include the heterocyclic compound represented by Chemical Formula 1.

[0107] In another embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer may include the heterocyclic compound represented by Chemical Formula 1.

[0108] In another embodiment of the present invention, the organic layer includes a light emitting layer, the light emitting layer includes a host material, and the host material may include the heterocyclic compound represented by Chemical Formula 1.

[0109] In one embodiment of the present invention, 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 for a red organic light-emitting material.

[0110] In another embodiment of the present invention, the organic light-emitting device may be a blue organic light-emitting device, and the heterocyclic compound represented by Chemical Formula 1 may be used as a material for a blue organic light-emitting material.

[0111] In another embodiment of the present invention, 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 for a green organic light-emitting material.

[0112] In one embodiment of the present invention, 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 light-emitting layer material of the red organic light-emitting device.

[0113] In another embodiment of the present invention, the organic light-emitting device may be a blue organic light-emitting device, and the heterocyclic compound represented by Chemical Formula 1 may be used as a light-emitting layer material of the blue organic light-emitting device.

[0114] In another embodiment of the present invention, the organic light-emitting device may be a green organic light-emitting device, and the heterocyclic compound represented by Chemical Formula 1 may be used as a light-emitting layer material of the green organic light-emitting device.

[0115] In one embodiment of the present invention, the organic light-emitting device may further include one layer or two or more layers selected from the group consisting of a light-emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer.

[0116] The specific content of the heterocyclic compound represented by Chemical Formula 1 is as described above.

[0117] Figures 1 to 3 illustrate the stacking order of the electrodes and organic layers of an organic light-emitting device according to an embodiment of the present invention. However, the scope of this application is not intended to be limited by these drawings, and the structures of organic light-emitting devices known in the art can also be applied to this application.

[0118] According to Figure 1, an organic light-emitting device in which a positive electrode (200), an organic layer (300), and a negative electrode (400) are sequentially stacked on a substrate (100) is shown. However, it is not limited to such a structure, and as shown in Figure 2, an organic light-emitting device in which a negative electrode (400), an organic layer (300), and a positive electrode (200) are sequentially stacked on the substrate can also be realized.

[0119] Figure 3 illustrates a case where the organic layer is multilayered. The organic light-emitting device according to Figure 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, the scope of this application is not limited by such a stacking structure, and the remaining layers except the light-emitting layer may be omitted as necessary, and other necessary functional layers may be further added. For example, a light-emitting auxiliary layer may be added (not shown in Figure 3).

[0120] The organic light-emitting device of the present invention can be manufactured by the manufacturing methods and materials of ordinary organic light-emitting devices, except that one or more organic layers are formed using the heterocyclic compound represented by Chemical Formula 1 described above.

[0121] In the manufacture of the organic light-emitting device, the heterocyclic compound can be formed as an organic layer not only by a vacuum evaporation method but also by a solution coating method. Here, the solution coating method means spin coating, dip coating, inkjet printing, screen printing, spraying method, roll coating, etc., but is not limited thereto.

[0122] The organic layer of the organic light-emitting device of the present invention may be configured in a single-layer structure, or may be configured in a multilayer structure in which two or more organic layers are stacked. For example, the organic light-emitting device of the present invention may have a structure including an electron injection layer, an electron transport layer, a hole blocking layer, a light-emitting layer, a light-emitting auxiliary layer, an electron blocking layer, a hole transport layer, a hole injection layer, etc. as the organic layer. However, the structure of the organic light-emitting device is not limited thereto, and it may include a smaller number of organic layers.

[0123] Further, the present invention provides a composition for an organic layer containing the heterocyclic compound represented by Chemical Formula 1.

[0124] The specific content of the heterocyclic compound represented by Chemical Formula 1 is as described above.

[0125] The composition for an organic layer can be used when forming the organic layer of the organic light-emitting device, and particularly, it can be preferably used when forming a hole transport layer, an electron blocking layer, or a light-emitting auxiliary layer.

[0126] In one embodiment of the present invention, the organic layer contains the heterocyclic compound represented by Chemical Formula 1 and may be used in combination with a phosphorescent dopant.

[0127] As the phosphorescent dopant material, those known in the art may be used. For example, phosphorescent dopant materials represented by LL'MX', LL'L"M, LMX'X", L 2 MX' and L 3 M may be used, but the scope of the present invention is not limited by these examples.

[0128] The M may be iridium, platinum, osmium, etc.

[0129] The L is sp 2An anionic bidentate ligand that coordinates to the M by carbon and heteroatoms, and X can function to trap electrons or holes. Non-limiting examples of L include 2-(1-naphthyl)benzoxazole, 2-phenylbenzoxazole, 2-phenylbenzothiazole, 7,8-benzoquinoline, phenylpyridine, benzothiophenylpyridine, 3-methoxy-2-phenylpyridine, thiophenylpyridine, tolylpyridine, and the like. Non-limiting examples of X' and X" include acetylacetonate (acac), hexafluoroacetylacetonate, salicylidene, picolinate, 8-hydroxyquinolinate, and the like.

[0130] Specific examples of the phosphorescent dopant are shown below, but are not limited thereto.

Chemical formula

[0131] In one embodiment of the present invention, the organic layer contains the heterocyclic compound represented by the chemical formula 1 and may be used in combination with an iridium-based dopant.

[0132] In one embodiment of the present invention, the iridium-based dopant may be (piq) 2 (Ir)(acac) as a red phosphorescent dopant or Ir(ppy) 3 as a green phosphorescent dopant.

[0133] In one embodiment of the present invention, the content of the dopant may be 1% to 15%, preferably 2% to 10%, more preferably 3% to 7% based on the total weight of the light-emitting layer.

[0134] The present invention The step of preparing a substrate; The step of forming a first electrode on the substrate; The step of forming one or more organic layers on the first electrode; and A method for manufacturing an organic light-emitting device, comprising the step of forming a second electrode on the above-mentioned organic layer(s) of one or more layers, wherein the step of forming the organic layer(s) of one or more layers includes the step of forming the organic layer(s) of one or more layers using a composition for an organic layer of an organic light-emitting device according to an embodiment of the present invention.

[0135] In one embodiment of the present invention, the step of forming the organic layer may be to form the heterocyclic compound represented by Chemical Formula 1 by thermal vacuum evaporation.

[0136] The organic layer containing the heterocyclic compound represented by Chemical Formula 1 may further contain other substances as necessary.

[0137] In an organic light-emitting device according to an embodiment of the present invention, materials other than the heterocyclic compound represented by Chemical Formula 1 are exemplified below. However, these are for illustrative purposes only and do not limit the scope of the present application, and may be replaced with materials known in the art.

[0138] As the positive electrode material, a material with a relatively large work function may be used, or a transparent conductive oxide, a metal, a conductive polymer, etc. may be used. Specific examples of the positive electrode material include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO 2 :Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

[0139] As the negative electrode material, a material with a relatively low work function may be used, and metals, metal oxides, conductive polymers, etc. may also be used. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer structured materials such as LiF / Al or LiO 2 / Al, etc., but are not limited thereto.

[0140] As the hole injection layer material, a known hole injection layer material may be used. For example, phthalocyanine compounds such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429, or starburst-type amine derivatives described in the literature [Advanced Material, 6, p.677(1994)], such as tris(4-carbazolyl-9-ylphenyl)amine (TCTA), 4,4',4"-tris[phenyl(m-tolyl)amino]triphenylamine (m-MTDATA), 1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene (m-MTDAPB), polyaniline / dodecylbenzenesulfonic acid, which is a soluble conductive polymer, or poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate), polyaniline / camphor sulfonic acid, or polyaniline / poly(4-styrenesulfonate), etc. may be used.

[0141] As the hole transport layer material, pyrazoline derivatives, arylamine-based derivatives, stilbene derivatives, triphenyldiamine derivatives, etc. may be used, and low molecular weight or high molecular weight materials may also be used.

[0142] As the electron transport layer 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 substances but also high molecular substances may be used.

[0143] As the electron injection layer material, for example, LiF is typically used in the art, but the present application is not limited thereto.

[0144] As the light-emitting layer material, a red, green or blue light-emitting material may be used, and if necessary, two or more light-emitting materials may be mixed and used. At this time, two or more light-emitting materials may be vapor-deposited and used as individual supply sources, or may be pre-mixed and vapor-deposited and used as one supply source. Further, a fluorescent material may be used as the light-emitting layer material, but a phosphorescent material may also be used. As the light-emitting layer material, a material that emits light by combining holes and electrons injected from the anode and the cathode, respectively, alone may be used, or a material in which a host material and a dopant material are involved in light emission together may also be used.

[0145] When mixing and using the host of the light-emitting layer material, hosts of the same series may be mixed and used, or hosts of different series may be mixed and used. For example, any two or more materials of an n-type host material or a p-type host material may be selected and used as the host material of the light-emitting layer.

[0146] The organic light-emitting device according to an embodiment of the present invention may be a front light-emitting type, a back light-emitting type, or a double-sided light-emitting type depending on the materials used.

[0147] The heterocyclic compound according to an embodiment of the present invention can also act on the same principle as that applied to the organic light-emitting device in organic electronic devices including organic solar cells, organic photoreceptors, organic transistors, etc.

[0148] Examples are shown below to facilitate the understanding of the present invention. However, the following examples are provided to more easily understand the present invention, and the present invention is not limited thereto.

Example

[0149] <Production Example> Production Example 1. Preparation of Compound 002

Chemical Formula

[0150] Production Example 1-1. Preparation of Compound 002-P4 50 g (161.24 mmol) of 1-iododibenzo[b,d]furan-2-ol and 21.63 g (177.37 mmol) of phenylboronic acid were dissolved in 500 mL of 1,4-dioxane and 100 mL of distilled water, and 5.59 g (4.84 mmol) of tetrakis(triphenylphosphine)palladium(0), Pd(PPh 3 ) 4 ) and 55.71 g (403.11 mmol) of potassium carbonate, K 2 CO 3 ) were added, and the mixture was refluxed and stirred for 10 hours.

[0151] After completion of the reaction, the reaction solution was extracted with dichloromethane and distilled water, the organic layer was dried over anhydrous MgSO 4 , and the solvent was removed using a rotary evaporator. Then, using dichloromethane and hexane as developing solvents, purification by column chromatography gave 35 g (yield 83%) of Compound 002-P4.

[0152] Production Example 1-2. Preparation of Compound 002-P3 35 g (134.47 mmol) of compound 002-P4 was dissolved in 500 mL of dichloromethane, and then 16.33 g (161.36 mmol) of triethylamine was added. After that, 45.53 g (161.36 mmol) of triflic anhydride was slowly added at 0 °C, and the mixture was stirred for 1 hour.

[0153] After completion of the reaction, distilled water was slowly added to the reaction solution to terminate the reaction, and then extracted with dichloromethane and distilled water. The organic layer was dried over anhydrous MgSO 4 and then the solvent was removed by a rotary evaporator. Then, using dichloromethane and hexane as developing solvents, purification by column chromatography gave 47 g (yield 89%) of compound 002-P3.

[0154] Production Example 1-3. Preparation of Compound 002-P2 47 g (119.79 mmol) of compound 002-P3 and 22 g (131.77 mmol) of (2-nitrophenyl)boronic acid were dissolved in 500 mL of 1,4-dioxane and 100 mL of distilled water, and 6.92 g (5.99 mmol) of tetrakis(triphenylphosphine)palladium(0), Pd(PPh 3 ) 4 ) and 41.39 g (299.48 mmol) of potassium carbonate (K 2 CO 3 ) were added, and the mixture was refluxed and stirred for 10 hours.

[0155] After completion of the reaction, the reaction solution was extracted with dichloromethane and distilled water, and the organic layer was dried over anhydrous MgSO 4After drying, the solvent was removed using a rotary evaporator. Then, dichloromethane and hexane were used as the developing solvents, and purification by column chromatography yielded 36 g (82% yield) of compound 002-P2.

[0156] Production Example 1-4. Preparation of Compound 002-P1 36 g (98.53 mmol) of compound 002-P2 and 64.61 g (246.32 mmol) of triphenylphosphine were placed in 400 mL of 1,2-dichlorobenzene and refluxed with stirring for 7 hours.

[0157] After completion of the reaction, the reaction mixture was extracted with dichloromethane and distilled water, and the organic layer was dried over anhydrous MgSO 4 After drying, the solvent was removed using a rotary evaporator. Then, dichloromethane and hexane were used as the developing solvents, and purification by column chromatography yielded 28 g (85% yield) of compound 002-P1.

[0158] Production Example 1-5. Preparation of Compound 002 10 g (30 mmol) of compound 002-P1 and 12.61 g (31.5 mmol) of N-(4-bromophenyl)-N-phenyl-[1,1'-biphenyl]-4-amine were dissolved in 100 mL of toluene, and tris(dibenzylideneacetone)dipalladium(0) (Pd 2 (dba) 3 ) 1.37 g (1.5 mmol), Xphos 1.43 g (3 mmol), and sodium tert-butoxide (NaOtBu) 5.77 g (59.99 mmol) were added, and the mixture was refluxed with stirring for 2 hours.

[0159] After the reaction was completed, the reaction solution was extracted with dichloromethane and distilled water, and the organic layer was dried over anhydrous MgSO 4 and then the solvent was removed using a rotary evaporator. Thereafter, dichloromethane and hexane were used as the developing solvents, and purification by column chromatography gave 15 g (yield 77%) of Compound 002.

[0160] In the production of the above Compound 002, Compound A in Table 1 below was used instead of phenylboronic acid, Compound B in Table 1 below was used instead of (2-nitrophenyl)boronic acid, and Compound C in Table 1 below was used instead of N-(4-bromophenyl)-N-phenyl-[1,1'-biphenyl]-4-amine, and the target compound was produced in the same manner as in Production Example 1 above as shown in Table 1 below.

[0161]

Table 1

[0162]

Table 2

[0163]

Table 3

[0164]

Table 4

[0165]

Table 5

[0166]

Table 6

[0167]

Table 7

[0168] Production Example 2. Preparation of Compound 231

Chem.

[0169] Production Example 2-1. Preparation of Compound 231-P5 50 g (161.24 mmol) of 1-iododibenzo[b,d]furan-2-ol and 21.63 g (177.37 mmol) of phenylboronic acid were dissolved in 500 mL of 1,4-dioxane and 100 mL of distilled water, and 5.59 g (4.84 mmol) of tetrakis(triphenylphosphine)palladium(0), Pd(PPh 3 ) 4 ) and 55.71 g (403.11 mmol) of potassium carbonate, K 2 CO 3 ) were added, and the mixture was refluxed and stirred for 10 hours.

[0170] After completion of the reaction, the reaction solution was extracted with dichloromethane and distilled water, the organic layer was dried over anhydrous MgSO 4 , and the solvent was removed using a rotary evaporator. Then, using dichloromethane and hexane as developing solvents, purification by column chromatography gave 35 g (yield 83%) of Compound 231-P5.

[0171] Production Example 2-2. Preparation of Compound 231-P4 35 g (134.47 mmol) of Compound 231-P5 was dissolved in 500 mL of dichloromethane, and then 16.33 g (161.36 mmol) of triethylamine was added. After that, 45.53 g (161.36 mmol) of triflic anhydride was slowly added at 0 °C, and the mixture was stirred for 1 hour.

[0172] After completion of the reaction, distilled water was slowly added to the reaction solution to terminate the reaction, and then extracted with dichloromethane and distilled water. The organic layer was dried over anhydrous MgSO 4 and then the solvent was removed using a rotary evaporator. Then, dichloromethane and hexane were used as developing solvents, and purification by column chromatography gave 47 g (yield 89%) of Compound 231-P4.

[0173] Production Example 2-3. Preparation of Compound 231-P3 47 g (119.79 mmol) of Compound 231-P4 and 26.53 g (131.77 mmol) of (4-chloro-2-nitrophenyl)boronic acid were dissolved in 500 mL of 1,4-dioxane and 100 mL of distilled water, and then 6.92 g (5.99 mmol) of tetrakis(triphenylphosphine)palladium(0), Pd(PPh 3 ) 4 ) and 41.39 g (299.48 mmol) of potassium carbonate (K 2 CO 3 ) were added, and the mixture was refluxed and stirred for 10 hours.

[0174] After completion of the reaction, the reaction solution was extracted with dichloromethane and distilled water, and the organic layer was dried over anhydrous MgSO 4After drying, the solvent was removed using a rotary evaporator. Then, dichloromethane and hexane were used as the developing solvents, and purification by column chromatography gave 37 g (yield 77%) of Compound 231-P3.

[0175] Production Example 2-4. Preparation of Compound 231-P2 37 g (92.54 mmol) of Compound 231-P3 and 60.68 g (231.35 mmol) of triphenylphosphine were added to 500 mL of 1,2-dichlorobenzene, and the mixture was refluxed with stirring for 7 hours.

[0176] After completion of the reaction, the reaction solution was extracted with dichloromethane and distilled water, and the organic layer was dried over anhydrous MgSO 4 After drying, the solvent was removed using a rotary evaporator. Then, dichloromethane and hexane were used as the developing solvents, and purification by column chromatography gave 30 g (yield 88%) of Compound 231-P2.

[0177] Production Example 2-5. Preparation of Compound 231-P1 30 g (81.56 mmol) of Compound 231-P2 and 10.94 g (89.72 mmol) of phenylboronic acid were dissolved in 300 mL of 1,4-dioxane and 60 mL of distilled water, and then 0.94 g (1.63 mmol) of tris(dibenzylideneacetone)dipalladium(0), Pd 2 (dba) 3 ) 1.94 g (4.08 mmol) of Xphos and 28.18 g (203.9 mmol) of potassium carbonate (K 2 CO 3 ) were added, and the mixture was refluxed with stirring for 4 hours.

[0178] After the reaction was completed, the reaction solution was extracted with dichloromethane and distilled water, and the organic layer was dried over anhydrous MgSO 4 and then the solvent was removed using a rotary evaporator. Thereafter, dichloromethane and hexane were used as developing solvents, and purification by column chromatography gave 25 g (yield 75%) of compound 231-P1.

[0179] Production Example 2-6. Preparation of Compound 231 8 g (19.54 mmol) of compound 231-P1 and 6.65 g (20.51 mmol) of 4-bromo-N,N-diphenylaniline were dissolved in 100 mL of toluene, and then tris(dibenzylideneacetone)dipalladium(0), Pd 2 (dba) 3 ) 0.89 g (0.98 mmol), Xphos 0.93 g (1.95 mmol), and sodium tert-butoxide (NaOtBu) 3.76 g (39.07 mmol) were added, and the mixture was refluxed and stirred for 2 hours.

[0180] After the reaction was completed, the reaction solution was extracted with dichloromethane and distilled water, and the organic layer was dried over anhydrous MgSO 4 and then the solvent was removed using a rotary evaporator. Thereafter, dichloromethane and hexane were used as developing solvents, and purification by column chromatography gave 9 g (yield 71%) of compound 231.

[0181] In the production of the compound 231, the compound D in Table 2 below was used instead of the phenylboronic acid in Production Example 2-1, the compound E in Table 2 below was used instead of (4-chloro-2-nitrophenyl)boronic acid, the compound F in Table 2 below was used instead of the phenylboronic acid in Production Example 2-5, and the compound G in Table 2 below was used instead of 4-bromo-N,N-diphenylaniline. The target compound was produced in the same manner as in Production Example 2 except for the above substitutions, as shown in Table 2 below.

[0182]

Table 8

[0183]

Table 9

[0184]

Table 10

[0185] Production Example 3. Preparation of Compound 361

Chemical formula

[0186] 9 g (13.79 mmol) of Compound 002, 3.10 g (20.68 mmol) of trifluoromethanesulfonic acid, and D 6 -benzene (D 6 -benzene) 100 mL were placed in a reaction flask and refluxed with stirring for 5 hours.

[0187] After completion of the reaction, distilled water was slowly added to the reaction solution to terminate the reaction, followed by extraction with dichloromethane and distilled water. The organic layer was dried over anhydrous MgSO 4After drying, the solvent was removed using a rotary evaporator. Then, dichloromethane and hexane were used as developing solvents, and purification by column chromatography yielded 8 g (yield 85%) of Compound 361.

[0188] The synthesis results of the compounds described in Production Examples 1 to 3 and Tables 1 to 2 are shown in Tables 3 and 4 below.

[0189] Table 3 below is 1 the measurement value of 1H NMR (CDCl 3 , 300 MHz), and Table 4 below is the measurement value of FD - mass spectrometer (FD - MS: Field desorption mass spectrometry).

[0190]

Table 11

[0191]

Table 12

[0192]

Table 13

[0193]

Table 14

[0194]

Table 15

[0195] <Experimental Example> Experimental Example 1. Experimental Example 1 - 1. Fabrication of Organic Light - Emitting Device A glass substrate coated with ITO with a thickness of 1,500 Å was cleaned by ultrasonic cleaning with distilled water. After the distilled water cleaning was completed, it was ultrasonically cleaned with solvents such as acetone, methanol, and isopropyl alcohol and dried, and then treated with UVO (Ultraviolet Ozone) using UV in a UV (Ultraviolet) cleaner for 5 minutes. Then, after transferring the substrate to a plasma cleaner (PT), plasma treatment was performed in a vacuum state for increasing the work function of ITO and removing the residual film, and it was transferred to a thermal evaporation apparatus for organic vapor deposition.

[0196] 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenyl amine (2-TNATA) was placed in a cell in the vacuum evaporation apparatus.

[0197] [Chemical formula]

[0198] Next, after evacuating until the vacuum degree in the chamber reached 10 -6 torr, a current was applied to the cell to evaporate 2-TNATA, and a hole injection layer with a thickness of 600 Å was deposited on the ITO substrate. A compound represented by Chemical formula 1 shown in Table 5 below or a comparative compound was placed in another cell in the vacuum evaporation apparatus, a current was applied to the cell to evaporate it, and a hole transport layer with a thickness of 1,000 Å was deposited on the hole injection layer.

[0199] After forming the hole injection layer and the hole transport layer as described above, an emission layer was thermally vacuum-deposited thereon as follows. The emission layer was deposited with 9-[4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]-9'-phenyl-3,3'-Bi-9H-carbazole as a host with a thickness of 400 Å, and the green fluorescent dopant was Ir(ppy) 3It was doped with 7% and then vapor-deposited. Then, BCP was vapor-deposited at 60 Å as a hole-blocking layer, and E1 was vapor-deposited at 300 Å thereon as an electron transport layer.

[0200]

Chemical formula

[0201] Thereafter, lithium fluoride (LiF) was vapor-deposited at a thickness of 10 Å as an electron injection layer, and Al was vapor-deposited at a thickness of 1200 Å to form a negative electrode, thereby fabricating an organic light-emitting device.

[0202] On the other hand, all the organic compounds required for fabricating the organic light-emitting device were vacuum sublimation purified under 10 -6 ~10 -8 torr and used for fabricating the organic light-emitting device.

[0203] At this time, the comparative compounds used as the hole transport layer are as follows.

[0204]

Chemical formula

[0205] Experimental Example 1-2. Driving Voltage and Luminescence Efficiency of Organic Light-Emitting Device Regarding the organic electroluminescent device fabricated as described above, the electroluminescence (EL) characteristics were measured with M7000 of McScience, and with the measurement results, the lifetime T 2 , which is the time when the initial luminance ratio becomes 95% when the reference luminance is 20,000 cd / m 95 , was measured by a lifetime measuring device (M6000) manufactured by McScience.

[0206] The measured results of the driving voltage, luminous efficiency, and lifetime (T 95 ) of the green organic light-emitting device manufactured by the above manufacturing method are as shown in Table 5.

[0207]

Table 16

[0208]

Table 17

[0209]

Table 18

[0210] From the results of Table 5 above, Examples 1 to 42, which are organic light-emitting devices using the heterocyclic compound represented by Chemical Formula 1 of the present invention as a hole transport layer material, showed that compared with Comparative Examples 1 to 4, which are organic light-emitting devices not using the heterocyclic compound represented by Chemical Formula 1 of the present invention as a hole transport layer material, the driving voltage was lower, and the luminous efficiency and lifespan were significantly improved.

[0211] The compounds M1 to M3 used in Comparative Examples 2 to 4 are similar to the compounds of the present invention in that they have a benzofluorocarbazole-type 5-ring skeleton, but the introduced substituents are different from those of the compounds of the present invention. By introducing an arylamine group as a substituent, the heterocyclic compound of the present invention has the characteristics of fast hole mobility and appropriate physical properties of the HOMO (highest occupied molecular orbital) level. For these reasons, when the heterocyclic compound of the present invention is used as a hole transport layer, it can transport holes to the light-emitting layer more easily than M1 to M3 used in Comparative Examples 2 to 4, resulting in a lower driving voltage, improved luminous efficiency, and extended lifespan.

[0212] Experimental Example 2. Experimental Example 2-1. Fabrication of Organic Light-Emitting Device The transparent electrode ITO thin film obtained from glass for OLED (manufactured by Samsung Corning) was ultrasonically cleaned for more than 5 minutes each using trichloroethylene, acetone, ethanol, and distilled water in sequence, then stored in isopropanol and used later.

[0213] 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenyl amine (2-TNATA) was placed in a cell inside a vacuum evaporation device.

[0214]

Chem.

[0215] Next, after evacuating until the degree of vacuum inside the chamber reached 10 -6 torr, a current was applied to the cell to evaporate 2-TNATA, and a 600 Å thick hole injection layer was deposited on the ITO substrate. N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) was placed in another cell inside the vacuum evaporation device, a current was applied to the cell to evaporate it, and a 1000 Å thick hole transport layer was deposited on the hole injection layer.

[0216]

Chem.

[0217] Next, as an electron blocking layer, the compound represented by Chemical Formula 1 shown in Table 6 or a comparative compound was deposited to a thickness of 1000 Å.

[0218] On top of that, a blue light-emitting material having the following structure was deposited as a light-emitting layer. Specifically, H1, which is a blue light-emitting host material, was vacuum-deposited to a thickness of 300 Å in one cell inside the vacuum evaporation device, and on top of that, D1, which is a blue light-emitting dopant material, was vacuum-deposited at 5% with respect to the host material.

[0219]

Chem.

[0220] Thereafter, a compound of the following structural formula E1 was deposited at a thickness of 300 Å as the electron transport layer.

[0221]

Chemical formula

[0222] Thereafter, lithium fluoride (LiF) was deposited at a thickness of 10 Å as the electron injection layer, and Al was deposited at a thickness of 1000 Å to form the cathode, thereby fabricating an organic light-emitting device.

[0223] On the other hand, all the organic compounds required for fabricating the organic light-emitting device were vacuum sublimation purified under 10 -6 ~10 -8 torr and used for fabricating the organic light-emitting device.

[0224] At this time, the comparative compounds used as the electron blocking layer are as follows.

[0225]

Chemical formula

[0226] Experimental Example 2-2. Driving Voltage and Luminescence Efficiency of Organic Light-Emitting Device Regarding the organic electroluminescent device fabricated as described above, the electroluminescence (EL) characteristics were measured with an M7000 from McScience, and with the measurement results, the lifetime T 2 which is the time when the initial luminance ratio becomes 95% at a reference luminance of 20,000 cd / m 95 was measured through a lifetime measurement device (M6000) manufactured by McScience.

[0227] The measurement results of the driving voltage, luminous efficiency, and lifetime (T 95 ) of the green organic light-emitting device manufactured by the above manufacturing method are as shown in Table 6.

[0228]

Table 19

[0229] From the results in Table 6 above, Examples 43 to 58, which are organic light-emitting devices using the heterocyclic compound represented by Chemical Formula 1 of the present invention as a material for the electron blocking layer, showed that compared with Comparative Examples 5 to 8, which are organic light-emitting devices not using the heterocyclic compound represented by Chemical Formula 1 of the present invention as a material for the electron blocking layer, the driving voltage was lower, and the luminous efficiency and lifespan were significantly improved.

[0230] Generally, when electrons are not combined in the light-emitting layer and pass through the hole transport layer to reach the anode, a phenomenon occurs in which the efficiency and lifespan of the organic light-emitting device decrease. At this time, when a compound having a high LUMO (Lowest Unoccupied Molecular Orbital) level is used as the electron blocking layer, electrons attempting to reach the anode after passing through the light-emitting layer are blocked by the energy barrier of the electron blocking layer, and the phenomenon of a decrease in the efficiency and lifespan of the organic light-emitting device can be prevented. That is, when a compound having a high LUMO (Lowest Unoccupied Molecular Orbital) level is used as the electron blocking layer, the probability of holes and electrons forming an exciton increases, and the probability of being emitted as light from the light-emitting layer increases.

[0231] Therefore, since the heterocyclic compound of the present invention has a higher LUMO level than the compounds of Comparative Examples 5 to 8, when the heterocyclic compound of the present invention is used as the electron blocking layer of an organic light-emitting device, it is found that it is superior in electron blocking ability, holes and electrons achieve charge balance, and it is excellent in all of the driving voltage, luminous efficiency, and lifespan characteristics.

Explanation of Reference Numerals

[0232] 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: Negative electrode

Claims

1. A heterocyclic compound represented by the following chemical formula 1: 【Chemical 1】 In the chemical formula 1, the R1 to R3 are the same as or different from each other, and each independently is 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)R101R102; -SiR101R102R103; and -NR101R102, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6-C60 aromatic hydrocarbon ring; or a substituted or unsubstituted C2-C60 heterocyclic ring, and the R101, R102 and R103 are the same as or different from each other, and each independently is a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group, the a is an integer of 0 to 4, and when a is 2 or more, the R1s are the same as or different from each other, the b is an integer of 0 to 4, and when b is 2 or more, the R2s are the same as or different from each other, the Ar1 to Ar3 are the same as or different from each other, and each independently is a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group, the L1 is a substituted or unsubstituted C6-C60 arylene group; or a substituted or unsubstituted C2-C60 heteroarylene group, the c is an integer of 1 to 5, and when c is 2 or more, the L1s are the same as or different from each other, the L2 and L3 are the same as or different from each other, and each independently is a direct bond; a substituted or unsubstituted C6-C60 arylene group; or a substituted or unsubstituted C2-C60 heteroarylene group, the d is an integer of 0 to 5, and when d is 2 or more, the L2s are the same as or different from each other, the e is an integer of 0 to 5, and when e is 2 or more, the L3s are the same as or different from each other.

2. The R1 in claim 1 is hydrogen; deuterium; a substituted or unsubstituted C6-C30 aryl group; or a substituted or unsubstituted C2-C30 heteroaryl group. The heterocyclic compound according to claim 1.

3. The Ar1 to Ar3 are the same as or different from each other, and each independently is a substituted or unsubstituted C6-C30 aryl group; or a substituted or unsubstituted C2-C30 heteroaryl group. The heterocyclic compound according to claim 1, characterized in that.

4. The L1 is a substituted or unsubstituted C6-C30 arylene group; or a substituted or unsubstituted C2-C30 heteroarylene group, The L2 and L3 are the same as or different from each other, and each independently is a direct bond; a substituted or unsubstituted C6-C30 arylene group; or a substituted or unsubstituted C2-C30 heteroarylene group. The heterocyclic compound according to claim 1, characterized in that.

5. The heterocyclic compound represented by Chemical Formula 1 does not contain deuterium as a substituent, or the content of deuterium relative to the total number of hydrogen atoms and deuterium atoms is 1% to 100%. The heterocyclic compound according to claim 1, characterized in that.

6. The heterocyclic compound represented by Chemical Formula 1 is represented by any one of the following compounds. The heterocyclic compound according to claim 1, characterized in that: [Chemical 2] [Chemical 3] [Chemical Formula 4] 【Chemical Formula 5】 【Chemical Formula 6】 【Chemical Formula 7】 【Chemical Formula 8】 【Chemical Formula 9】 【Chemical Formula 10】 【Chemical 11】 【Chemical 12】 【Chemical 13】 【Chemical 14】 【Chemical Formula 15】 【Chemical 16】 【Chemical 17】 【Chemical 18】 【Chemical Formula 19】 【Chemical 20】 【Chemical 21】

7. The 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; An organic light-emitting device comprising: One or more of the organic layers contain the heterocyclic compound according to any one of claims 1 to 6. An organic light-emitting device, characterized in that.

8. The organic layer includes a hole transport layer, The hole transport layer contains the heterocyclic compound. The organic light-emitting device according to claim 7, characterized in that.

9. The organic layer includes an electron blocking layer, The electron blocking layer contains the heterocyclic compound. The organic light-emitting device according to claim 7, characterized in that.

10. The organic layer includes a light-emitting layer, The light-emitting layer contains the heterocyclic compound. The organic light-emitting device according to claim 7, characterized in that.

11. The organic layer includes a light-emitting layer, The light-emitting layer contains a host material, The host material contains the heterocyclic compound. The organic light-emitting device according to claim 7, characterized in that.

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 light-emitting auxiliary 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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