Heterocyclic compound and organic light-emitting device containing the same

Abstract

The present application provides a heterocyclic compound, and an organic light-emitting device and a composition for an organic layer in which the heterocyclic compound is contained in an organic layer.

Description

[Technical Field]

[0001] This application claims the benefit of the filing date of Korean Patent Application No. 10-2020-0103402, filed with the Korean Intellectual Property Office on August 18, 2020, the entire contents of which are incorporated herein by reference.

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

[0003] Electroluminescent devices are a type of self-luminous display device, and have the advantages of 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 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 annihilate, emitting light. The organic thin film may be configured as a single layer or multiple layers as needed.

[0005] The material of the organic thin film may have a light-emitting function as needed. For example, the material of the organic thin film may be a compound that can constitute an emitting layer by itself, or a compound that can function as a host or dopant in a host-dopant emitting layer. In addition, the material of the organic thin film may be a compound that can perform functions such as hole injection, hole transport, electron blocking, hole blocking, electron transport, and electron injection.

[0006] To improve the performance, lifetime, or efficiency of organic light-emitting devices, there is a continuing need to develop materials for organic thin films. [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 invention provides a heterocyclic compound and an organic light-emitting device including the heterocyclic compound. [Means for solving the problem]

[0009] One embodiment of the present application provides a heterocyclic compound represented by the following chemical formula 1:

[0010] [ka] In the above Chemical Formula 1, L1 to L5 are the same or different and each independently represent a direct bond; a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms; a, b, c, d, and e are each an integer of 0 to 3, and when a, b, c, d, and e are each 2 or more, the substituents in parentheses are the same or different; Ar1 to Ar5 are the same or different and each independently represent a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; at least one of Ar1 to Ar5 is a substituted or unsubstituted monocyclic or polycyclic heteroaryl group containing one or more N atoms and having 2 to 60 carbon atoms; or an aryl group substituted with one or more cyano groups and having 6 to 60 carbon atoms; Rp is hydrogen; deuterium; a halogen group; or a substituted or unsubstituted alkyl group having 6 to 60 carbon atoms, and p is an integer of 0 to 4, and when p is 2 or greater, the substituents in the parentheses may be the same or different.

[0011] Another embodiment of the present application provides an organic light-emitting device including a first electrode, a second electrode, and one or more organic material layers disposed between the first electrode and the second electrode, wherein at least one of the organic material layers contains a heterocyclic compound represented by Chemical Formula 1. [Effects of the Invention]

[0012] A heterocyclic compound according to one embodiment of the present application can be used as a material for an organic layer of an organic light-emitting device. The heterocyclic compound can be used as a material for a hole injection layer, a hole transport layer, an emission layer, an electron transport layer, an electron injection layer, a charge generation layer, etc. in an organic light-emitting device. In particular, the heterocyclic compound represented by Chemical Formula 1 can be used as a material for the emission layer of an organic light-emitting device. Furthermore, when the heterocyclic compound represented by Chemical Formula 1 is used in an organic light-emitting device, the driving voltage of the device can be reduced, the light efficiency can be improved, and the thermal stability of the compound can improve the life characteristics of the device. [Brief explanation of the drawings]

[0013] [Figure 1] 1 to 4 are diagrams each schematically showing a layered structure of an organic light-emitting device according to an embodiment of the present application. [Figure 2] 1 to 4 are diagrams each schematically showing a layered structure of an organic light-emitting device according to an embodiment of the present application. [Figure 3] 1 to 4 are diagrams each schematically showing a layered structure of an organic light-emitting device according to an embodiment of the present application. [Figure 4] 1 to 4 are diagrams each schematically showing a layered structure of an organic light-emitting device according to an embodiment of the present application. DETAILED DESCRIPTION OF THE INVENTION

[0014] The present application will be described in detail below.

[0015] One embodiment of the present application provides a heterocyclic compound represented by the following chemical formula 1:

[0016] [ka] In the above Chemical Formula 1, L1 to L5 are the same or different and each independently represent a direct bond; a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms; a, b, c, d, and e are each an integer of 0 to 3, and when a, b, c, d, and e are each 2 or more, the substituents in parentheses are the same or different; Ar1 to Ar5 are the same or different and each independently represent a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; at least one of Ar1 to Ar5 is a substituted or unsubstituted monocyclic or polycyclic heteroaryl group containing one or more N atoms and having 2 to 60 carbon atoms; or an aryl group substituted with one or more cyano groups and having 6 to 60 carbon atoms; Rp is hydrogen; deuterium; a halogen group; or a substituted or unsubstituted alkyl group having 6 to 60 carbon atoms, and p is an integer of 0 to 4, and when p is 2 or greater, the substituents in the parentheses may be the same or different.

[0017] The compound of Chemical Formula 1 has a monocyclic or polycyclic heterocyclic group containing one or more N atoms or an aryl group substituted with a cyano group as a substituent in the dibenzofuran structure, which improves the electron transport ability. Therefore, when the compound of Chemical Formula 1 is used in a device, it has the effect of improving current flow and lowering the driving voltage.

[0018] As used herein, the term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position of the substitution is not limited as long as it is a position at which a hydrogen atom is substituted, i.e., a position at which a substituent can be substituted, and when two or more substituents are substituted, the two or more substituents may be the same or different.

[0019] In this specification, the term "substituted or unsubstituted" includes deuterium; a cyano group; a halogen group; a linear or branched alkyl having 1 to 60 carbon atoms; a linear or branched alkenyl having 2 to 60 carbon atoms; a linear or branched alkynyl having 2 to 60 carbon atoms; a monocyclic or polycyclic cycloalkyl having 3 to 60 carbon atoms; a monocyclic or polycyclic heterocycloalkyl having 2 to 60 carbon atoms; a monocyclic or polycyclic aryl having 6 to 60 carbon atoms; a monocyclic or polycyclic heteroaryl having 2 to 60 carbon atoms; -SiRR'R''; -P(=O)RR'; an alkylamine having 1 to 20 carbon atoms; a monocyclic or polycyclic arylamine; and monocyclic or polycyclic heteroarylamine having 2 to 60 carbon atoms, or substituted or unsubstituted by a substituent formed by linking two or more substituents selected from the above-mentioned substituents, and R, R', and R'' may be the same or different and each independently represent a substituted or unsubstituted alkyl having 1 to 60 carbon atoms; a substituted or unsubstituted aryl having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms.

[0020] In this specification, when "no substituent is shown in the chemical formula or compound structure," it means that a hydrogen atom is bonded to a carbon atom. However, deuterium ( 2 H, Deuterium) is an isotope of hydrogen, so some hydrogen atoms may be deuterium.

[0021] In one embodiment of the present application, "when no substituent is shown in the chemical formula or compound structure," may mean that all positions available as substituents are hydrogen or deuterium. In other words, in the case of deuterium, it is an isotope of hydrogen, and some hydrogen atoms may be deuterium, which is an isotope, and in this case, the content of deuterium may be 0% to 100%.

[0022] In one embodiment of the present application, when "substituents are not shown in the chemical formula or compound structure," if 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.

[0023] 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.

[0024] In one embodiment of the present application, isotopes, which refer to atoms with the same atomic number (Z) but different mass numbers (A), can be interpreted as elements with the same number of protons but different numbers of neutrons.

[0025] 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.

[0026] That is, in one example: [ka] A phenyl group represented by the formula (I) having a deuterium content of 20% can be expressed as 20% when the total number of substituents that the phenyl group can have is 5 (T1 in the formula), of which the number of deuterium is 1 (T2 in the formula). In other words, a phenyl group having a deuterium content of 20% may be represented by the following structural formula:

[0027] [ka] In addition, in one embodiment of the present application, a "phenyl group having a deuterium content of 0%" may refer to a phenyl group that does not contain a deuterium atom, that is, a phenyl group that has five hydrogen atoms.

[0028] As used herein, the halogen may be fluorine, chlorine, bromine, or iodine.

[0029] 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, more specifically 1 to 20. Specific examples include a methyl group, an ethyl group, a propyl group, an n-propyl group, an isopropyl group, a butyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a sec-butyl group, a 1-methylbutyl group, a 1-ethylbutyl group, a pentyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, a hexyl group, an n-hexyl group, a 1-methylpentyl group, a 2-methylpentyl group, a 4-methyl-2-pentyl group, a 3,3-dimethylbutyl group, a 2-ethylbutyl group, Examples include, but are not limited to, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1-dimethylpropyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like.

[0030] 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 to these.

[0031] 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.

[0032] In this specification, the alkoxy group may be a straight chain, branched chain, or cyclic chain. The number of carbon atoms in the alkoxy group is not particularly limited, but preferably has 1 to 20 carbon atoms. Specific examples include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, 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.

[0033] 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, "polycyclic" refers to a group in which a cycloalkyl group is directly linked to or condensed with another cyclic group. Here, the other cyclic group may be a cycloalkyl group, but may also be other types of cyclic groups, such as a heterocycloalkyl group, an aryl group, or a heteroaryl group. The number of carbon atoms in the cycloalkyl group may be 3 to 60, specifically 3 to 40, and more specifically 5 to 20. Specific examples include, but are not limited to, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a 3-methylcyclopentyl group, a 2,3-dimethylcyclopentyl group, a cyclohexyl group, a 3-methylcyclohexyl group, a 4-methylcyclohexyl group, a 2,3-dimethylcyclohexyl group, a 3,4,5-trimethylcyclohexyl group, a 4-tert-butylcyclohexyl group, a cycloheptyl group, and a cyclooctyl group.

[0034] In this specification, the heterocycloalkyl group contains O, S, Se, N, or Si as a heteroatom, and includes a monocyclic or polycyclic group having 2 to 60 carbon atoms, which may be further substituted with other substituents. Here, the term "polycyclic" refers to a group in which a heterocycloalkyl group is directly linked to or condensed with another cyclic group. Here, the other cyclic group may be a heterocycloalkyl group, but may also be other types of cyclic groups, such as a cycloalkyl group, an aryl group, or a heteroaryl group. The number of carbon atoms in the heterocycloalkyl group may be 2 to 60, specifically 2 to 40, more specifically 3 to 20.

[0035] 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 aryl group includes a spiro group. The number of carbon atoms in the aryl group may be 6 to 60, specifically 6 to 40, more specifically 6 to 25. Specific examples of the aryl group include, but are not limited to, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthryl group, a chrysenyl group, a phenanthrenyl group, a perylenyl group, a fluoranthenyl group, a triphenylenyl group, a phenalenyl group, a pyrenyl group, a tetracenyl group, a pentacenyl group, a fluorenyl group, an indenyl group, an acenaphthylenyl group, a benzofluorenyl group, a spirobifluorenyl group, a 2,3-dihydro-1H-indenyl group, and fused ring groups thereof.

[0036] In this specification, the phosphine oxide group is represented by -P(=O)R101R102, where R101 and R102 may be the same or different and each independently represent at least one substituent selected from the group consisting 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, diphenylphosphine oxide and dinaphthylphosphine oxide.

[0037] In this specification, a silyl group is a substituent containing Si and 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 independently represent 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.

[0038] In this specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.

[0039] 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 have a structure in which a 2,3-dihydro-1H-indene group or a cyclohexane group is spiro-bonded to a fluorenyl group. Specifically, the following spiro group may include any one of groups represented by the following structural formulas:

[0040] [ka]

[0041] In this specification, the heteroaryl group contains S, O, Se, N, or Si as a heteroatom, and includes a monocyclic or polycyclic ring having 2 to 60 carbon atoms, which may be further substituted with other substituents. Here, the polycyclic ring refers to a group in which the heteroaryl group is directly linked to or condensed with another cyclic group. Here, the other cyclic group may be a heteroaryl group, but may also be other types of cyclic groups, such as a cycloalkyl group, a heterocycloalkyl group, or an aryl group. The number of carbon atoms in the heteroaryl group may be 2 to 60, specifically 2 to 40, 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 triazolyl group, a Azinyl group, tetrazinyl group, quinolyl group, isoquinolyl group, quinazolinyl group, isoquinazolinyl group, quinozolyl group, naphthyridyl group, acridinyl group, phenanthridinyl group, imidazopyridinyl group, diazanaphthalenyl group, triazaindene group, indolyl group, indolizinyl group, benzothiazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiophene group, benzofuran group, dibenzothiophene group, dibenzofuran group, carbazolyl group , 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.

[0042] 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 preferably is 1 to 30. Specific examples of the amine group include, but are not limited to, a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, a dibiphenylamine group, an anthracenylamine group, a 9-methylanthracenylamine group, a diphenylamine group, a phenylnaphthylamine group, a ditolylamine group, a phenyltolylamine group, a triphenylamine group, a biphenylnaphthylamine group, a phenylbiphenylamine group, a biphenylfluorenylamine group, a phenyltriphenylenylamine group, and a biphenyltriphenylenylamine group.

[0043] In this specification, an arylene group refers to an aryl group having two bonding positions, i.e., a divalent group. The above-mentioned explanation of the aryl group may be applied to these groups, except that they are both divalent groups. Furthermore, a heteroarylene group refers to a heteroaryl group having two bonding positions, i.e., a divalent group. The above-mentioned explanation of the heteroaryl group may be applied to these groups, except that they are both divalent groups.

[0044] As used herein, 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 ortho positions on a benzene ring and two substituents substituted on the same carbon atom on an aliphatic ring can be interpreted as groups "adjacent" to each other.

[0045] A heterocyclic compound according to one embodiment of the present application is characterized by being represented by Chemical Formula 1. More specifically, the heterocyclic compound represented by Chemical Formula 1 can be used as a material for an organic layer of an organic light-emitting device due to the structural features of the core structure and the substituents as described above.

[0046] In one embodiment of the present application, L1 to L5 in Chemical Formula 1 may be the same or different and may each independently represent a direct bond; a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms.

[0047] In one embodiment of the present application, L1 to L5 may be the same or different and each independently represent a direct bond; a substituted or unsubstituted arylene group having 6 to 40 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 40 carbon atoms.

[0048] In one embodiment of the present application, L1 to L5 may be the same or different and each independently represent a direct bond; a substituted or unsubstituted arylene group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms.

[0049] In another embodiment, L1 is a direct bond.

[0050] In another embodiment, L1 is a phenylene group.

[0051] In another embodiment, L1 is a naphthylene group.

[0052] In another embodiment, L2 is a direct bond.

[0053] In another embodiment, L2 is a phenylene group.

[0054] In another embodiment, L2 is a naphthylene group.

[0055] In another embodiment, L3 is a direct bond.

[0056] In another embodiment, L3 is a phenylene group.

[0057] In another embodiment, L3 is a naphthylene group.

[0058] In another embodiment, L4 is a direct bond.

[0059] In another embodiment, L4 is a phenylene group.

[0060] In another embodiment, L4 is a naphthylene group.

[0061] In another embodiment, L5 is a direct bond.

[0062] In another embodiment, L5 is a phenylene group.

[0063] In another embodiment, L5 is a naphthylene group.

[0064] In one embodiment of the present application, a, b, c, d, and e in Chemical Formula 1 are each an integer of 0 to 3, and when a, b, c, d, and e are each 2 or more, the substituents in parentheses may be the same or different.

[0065] In one embodiment of the present application, Ar1 to Ar5 in Chemical Formula 1 are the same or different and each independently represent a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, and at least one of Ar1 to Ar5 may be a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 60 carbon atoms and containing one or more N; or an aryl group having 6 to 60 carbon atoms substituted with one or more cyano groups.

[0066] In one embodiment of the present application, Ar1 to Ar5 are the same or different and each independently represent a substituted or unsubstituted aryl group having 6 to 40 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 40 carbon atoms, and at least one of Ar1 to Ar5 may be a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 40 carbon atoms and containing one or more N; or an aryl group having 6 to 40 carbon atoms substituted with one or more cyano groups.

[0067] In one embodiment of the present application, Ar1 to Ar5 are the same or different and each independently represent a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms, and at least one of Ar1 to Ar5 may be a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms and containing one or more N; or an aryl group having 6 to 20 carbon atoms substituted with one or more cyano groups.

[0068] In one embodiment of the present application, Ar1 to Ar5 are the same or different and each independently represent a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 60 carbon atoms and containing one or more N; or an aryl group having 6 to 60 carbon atoms and substituted with one or more cyano groups, and at least one of Ar1 to Ar5 may be a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 60 carbon atoms and containing one or more N; or an aryl group having 6 to 60 carbon atoms and substituted with one or more cyano groups.

[0069] In one embodiment of the present application, the monocyclic or polycyclic heteroaryl group containing one or more N, having 2 to 60 carbon atoms, may be a group represented by the following chemical formula 3.

[0070] [ka] In the above Chemical Formula 3, X1 is CR1 or N, X2 is CR2 or N, X3 is CR3 or N, X4 is CR4 or N, and X5 is CR5 or N, and at least one of X1 to X5 is N; R1 to R5 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 alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms; a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; -P(=O)RR; and NRRR, or two or more adjacent groups may be bonded to each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring or heterocycle, and R12 to R14 are the same or different and each independently represent hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; [ka] is a site that is linked to Chemical Formula 1.

[0071] In one embodiment of the present application, the chemical formula 3 may be represented by one of the following chemical formulas 3-1 to 3-4, wherein: [ka] is a site that is linked to Chemical Formula 1.

[0072] [ka] [ka] [ka] [ka] In Chemical Formula 3-1, one or more of X1, X3, and X5 is N, and the rest are the same as defined in Chemical Formula 3; In Chemical Formula 3-2, one or more of X1, X2, and X5 is N, and the rest are the same as defined in Chemical Formula 3; In Chemical Formula 3-3, at least one of X1 to X3 is N, and the rest are the same as defined in Chemical Formula 3; In Chemical Formula 3-4, one or more of X1, X2, and X5 is N, and the rest are the same as defined in Chemical Formula 3; Z1 is O; or S; R2, R4, and R6 to R9 are the same or different and each independently represent hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms; substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms; substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms; substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; substituted or unsubstituted aryl group having 6 to 60 carbon atoms; substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; -P(=O)RR; and NRRR, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring or heterocycle, and said R, and R12 to R14 are the same or different and each independently represent hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0073] In one embodiment of the present application, the chemical formula 3 may be represented by any one of the following group 1:

[0074] [ka] R1 to R5 of Group 1 and [ka] is defined as in Chemical Formula 3.

[0075] In another embodiment, Rp in Chemical Formula 1 is hydrogen; deuterium; a halogen group; or a substituted or unsubstituted alkyl group having 6 to 60 carbon atoms, and p is an integer of 0 to 4, and when p is 2 or more, the substituents in the parentheses may be the same or different.

[0076] In yet another embodiment, Rp may be hydrogen or deuterium.

[0077] In yet another embodiment, Rp is hydrogen.

[0078] In one embodiment of the present application, the chemical formula 1 may be represented by the following chemical formula 1-1 or chemical formula 1-2.

[0079] [ka] [ka] In the above Chemical Formula 1-1, Ar1 and Ar4 are the same or different and each independently represent a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, at least one of Ar1 and Ar4 being a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 60 carbon atoms and containing one or more N; or an aryl group having 6 to 60 carbon atoms substituted with one or more cyano groups, and the remainder are the same as defined in Chemical Formula 1, In the above Chemical Formula 1-2, Ar2 and Ar4 are the same or different and each independently represent a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, and at least one of Ar2 and Ar4 is a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 60 carbon atoms and containing one or more N; or an aryl group having 6 to 60 carbon atoms substituted with one or more cyano groups, and the remainder are the same as defined in Chemical Formula 1.

[0080] The heterocyclic compound represented by Chemical Formula 1-1 has a linear and planar shape, and the overlap between the compounds is increased, which further accelerates electron transport. Therefore, when the heterocyclic compound represented by Chemical Formula 1-1 is used in a device, the efficiency of the device can be further improved.

[0081] In addition, the heterocyclic compound represented by Chemical Formula 1-2 has a structure that is very effective in separating the electron distributions of HOMO and LUMO, which allows the compound to have an appropriate band gap. Therefore, when the heterocyclic compound represented by Chemical Formula 1-2 is used in a device, the device can have a more excellent driving effect.

[0082] In one embodiment of the present application, the chemical formula 1 may be represented by any one of the following chemical formulas 1-3 to 1-5.

[0083] [ka] [ka] [ka] In the above Chemical Formula 1-3, Ar1 and Ar5 are the same or different and each independently represent a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, at least one of Ar1 and Ar5 being a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 60 carbon atoms and containing one or more N; or an aryl group having 6 to 60 carbon atoms substituted with one or more cyano groups, and the remainder are the same as defined in Chemical Formula 1, In the above Chemical Formula 1-4, Ar2 and Ar5 are the same or different and each independently represent a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, at least one of Ar2 and Ar5 being a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 60 carbon atoms and containing one or more N; or an aryl group having 6 to 60 carbon atoms substituted with one or more cyano groups, and the remainder are the same as defined in Chemical Formula 1, In Chemical Formula 1-5, Ar3 and Ar5 are the same or different and each independently represent a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, provided that at least one of Ar3 and Ar5 is a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 60 carbon atoms and containing one or more N; or an aryl group having 6 to 60 carbon atoms substituted with one or more cyano groups, and the remainder are the same as defined in Chemical Formula 1.

[0084] The heterocyclic compound represented by Chemical Formula 1-3 has a linear and planar shape, and the overlap between the compounds is increased, which further accelerates electron transport. Therefore, when the heterocyclic compound represented by Chemical Formula 1-3 is used in a device, the efficiency of the device can be further improved.

[0085] The heterocyclic compound represented by Chemical Formula 1-4 has little structural interference due to peripheral functional groups, and has suitable linearity and planarity, so that the deposition temperature is not high and the heterocyclic compound has a relatively thermally stable structure. Therefore, when the heterocyclic compound represented by Chemical Formula 1-4 is applied to a device, the device can have a longer life.

[0086] In addition, the heterocyclic compound represented by Chemical Formula 1-5 has a structure that is very effective in separating the electron distributions of HOMO and LUMO, which allows the compound to have an appropriate band gap. Therefore, when the heterocyclic compound represented by Chemical Formula 1-5 is used in a device, the device can have a more excellent driving effect.

[0087] 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:

[0088] [ka] TIFF0007788168000021.tif146165 TIFF0007788168000022.tif209165 TIFF0007788168000023.tif232165 TIFF0007788168000024.tif231165 TIFF0007788168000025.tif130165 TIFF0007788168000026.tif134165 TIFF0007788168000027.tif222165 TIFF0007788168000028.tif200165 TIFF0007788168000029.tif214165 TIFF0007788168000030.tif42165 Furthermore, by introducing various substituents into the structure of Chemical Formula 1, it is possible to synthesize compounds having the specific properties of the introduced substituents. For example, by introducing into the core structure substituents that are primarily used in hole injection layer materials, hole transport materials, light emitting layer materials, electron transport layer materials, and charge generation layer materials used in the manufacture of organic light emitting devices, it is possible to synthesize materials that satisfy the requirements for each organic layer.

[0089] In addition, by introducing various substituents into the structure of Chemical Formula 1, it is possible to finely adjust the energy band gap and improve the properties at the interface between organic materials, thereby diversifying the uses of the material.

[0090] On the other hand, the heterocyclic compounds have a high glass transition temperature (Tg) and excellent thermal stability, which is an important factor in providing the device with operational stability.

[0091] The heterocyclic compound according to one embodiment of the present application can be prepared by a multi-step chemical reaction. Some intermediate compounds are prepared first, and the compound of Chemical Formula 1 can be prepared from these intermediate compounds. More specifically, the heterocyclic compound according to one embodiment of the present application can be prepared according to the preparation examples described below.

[0092] Another embodiment of the present application provides an organic light-emitting device including a heterocyclic compound represented by Chemical Formula 1. The "organic light-emitting device" may be expressed as terms such as "organic light-emitting diode," "OLED (Organic Light Emitting Diodes)," "OLED element," "organic electroluminescent device," etc.

[0093] The heterocyclic compound may be formed in the organic layer by a solution coating method, such as a vacuum deposition method, during fabrication of the organic light emitting device, including, but not limited to, spin coating, dip coating, inkjet printing, screen printing, spraying, and roll coating.

[0094] Specifically, an organic light emitting device according to one embodiment of the present application includes a first electrode, a second electrode, and one or more organic material layers disposed between the first and second electrodes, at least one of the organic material layers including the heterocyclic compound represented by Chemical Formula 1. When the organic material layer includes the heterocyclic compound represented by Chemical Formula 1, the organic light emitting device has excellent luminous efficiency and life span.

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

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

[0097] In one embodiment of the present application, the organic light-emitting device may be a red organic light-emitting device, and the heterocyclic compound of Chemical Formula 1 may be used as a material for the red organic light-emitting device.

[0098] In one embodiment of the present application, the heterocyclic compound according to Chemical Formula 1 may be used as an N-type host.

[0099] In addition, the organic material layer includes one or more light-emitting layers, and the light-emitting layers include the heterocyclic compound represented by Chemical Formula 1. When the light-emitting layer of the organic material layer includes the heterocyclic compound represented by Chemical Formula 1, the luminous efficiency and lifespan of the organic light-emitting device are further improved.

[0100] In the organic light-emitting device of the present application, the organic material layer may further contain one or more of any one of the compounds of Groups A to C below.

[0101] [ka] [ka] [ka] TIFF0007788168000034.tif209165 The organic material layer may include one or more light-emitting layers, each of which contains the heterocyclic compound represented by Chemical Formula 1 as a first compound and one of the compounds of Groups A to C as a second compound. When the light-emitting layer of the organic material layer contains the heterocyclic compound represented by Chemical Formula 1 and the compound of Groups A to C, the luminous efficiency and lifetime of the organic light-emitting device are further improved.

[0102] In one embodiment of the present application, the heterocyclic compounds according to Groups A to C may be used as a P-type host.

[0103] In addition, the organic material layer includes one or more light-emitting layers, and the light-emitting layers further include the heterocyclic compound represented by Chemical Formula 1 and one of the compounds of Groups A to C. When the light-emitting layer of the organic material layer simultaneously includes the heterocyclic compound represented by Chemical Formula 1 and one of the compounds of Groups A to C, the organic light-emitting device has better luminous efficiency and lifespan due to an exciplex phenomenon.

[0104] In the organic light-emitting device of the present application, the organic material layer may include a light-emitting layer, and the light-emitting layer may include the heterocyclic compound as a host substance of a light-emitting material.

[0105] In the organic light-emitting device of the present application, the light-emitting layer may include two or more host materials, and at least one of the host materials may include the heterocyclic compound as a host material of a light-emitting material.

[0106] In the organic light-emitting device of the present application, the light-emitting layer may be formed by pre-mixing two or more host materials, and at least one of the two or more host materials may contain the heterocyclic compound as a host material of the light-emitting material.

[0107] The term "pre-mixed" means that the light-emitting layer is prepared by mixing two or more host materials in a single source before depositing the materials on the organic layer.

[0108] In the organic light emitting device of the present application, the light emitting layer may include two or more host materials, each of which may include one or more p-type host materials and one or more n-type host materials, and at least one of the host materials may include the heterocyclic compound as a host material for light emitting materials. In this case, the organic light emitting device may have excellent operation, efficiency, and lifespan.

[0109] 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, a hole-auxiliary layer, and a hole-blocking layer.

[0110] The organic light emitting device according to one embodiment of the present application may be manufactured using a conventional method and materials for manufacturing an organic light emitting device, except that the organic material layer is formed using the heterocyclic compound described above.

[0111] Another embodiment of the present application provides a composition for an organic material layer of an organic light-emitting device, which comprises the heterocyclic compound represented by Chemical Formula 1 and one of the compounds of Groups A to C.

[0112] In another embodiment of the present application, the weight ratio of the heterocyclic compound represented by Chemical Formula 1 to one of the compounds of Groups A to C in the composition may be, but is not limited to, 1:10 to 10:1, 1:8 to 8:1, 1:5 to 5:1, or 1:2 to 2:1.

[0113] The heterocyclic compound represented by Chemical Formula 1 and the compounds of Groups A to C contained in the composition for organic layer are as described above.

[0114] 1 to 3 show examples of the stacking order of electrodes and organic layers of an organic light-emitting device according to one embodiment of the present application. However, these drawings do not limit the scope of the present application, and structures of organic light-emitting devices known in the technical field may be applied to the present application.

[0115] 1 shows an organic light-emitting device in which an anode 200, an organic layer 300, and a cathode 400 are sequentially stacked on a substrate 100. However, the present invention is not limited to this structure, and an organic light-emitting device in which a cathode, an organic layer, and an anode are sequentially stacked on a substrate, as shown in FIG.

[0116] Figure 3 illustrates an example in which the organic material layer is multilayered. The organic light-emitting device of Figure 3 includes a hole injection layer 301, a hole transport layer 302, an emitting layer 303, a hole blocking layer 304, an electron transport layer 305, and an electron injection layer 306. However, such a stacked structure does not limit the scope of the present application, and the remaining layers except for the emitting layer may be omitted as necessary, and other necessary functional layers may be further added.

[0117] Also, an organic light-emitting device according to one embodiment of the present application includes a first electrode; a first stack provided on the first electrode and including a first light-emitting layer; a charge generation layer provided on the first stack; a second stack provided on the charge generation layer and including a second light-emitting layer; and a second electrode provided on the second stack.

[0118] In this case, the charge generation layer may include a heterocyclic compound represented by Chemical Formula 1. When the heterocyclic compound is used in the charge generation layer, the organic light emitting device may have excellent drivability, efficiency, and lifespan.

[0119] The first stack and the second stack may each independently further include one or more of the above-mentioned hole injection layer, hole transport layer, hole blocking layer, electron transport layer, electron injection layer, and the like.

[0120] As an organic light-emitting device according to one embodiment of the present application, an organic light-emitting device having a two-stack tandem structure is exemplarily shown in FIG.

[0121] In this case, the first electron blocking layer, the first hole blocking layer, and the second hole blocking layer shown in FIG. 4 may be omitted in some cases.

[0122] In an organic light-emitting device according to one embodiment of the present application, materials other than the heterocyclic compound of Chemical Formula 1 are exemplified below. However, these are for illustrative purposes only and are not intended to limit the scope of the present application. Materials known in the art may be substituted.

[0123] The anode material may be a material with a relatively large work function, such as a transparent conductive oxide, a metal, or a conductive polymer. Specific examples of the anode material include, but are not limited to, metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, and polyaniline.

[0124] The cathode material may be a material with a relatively low work function, such as a metal, a metal oxide, or a conductive polymer. Specific examples of the cathode material include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; and multilayer structures such as LiF / Al or LiO / Al.

[0125] As the hole injection material, known hole injection materials may be used, for example, phthalocyanine compounds such as copper phthalocyanine disclosed in U.S. Pat. No. 4,356,429, or starburst-type amine derivatives described in the literature [Advanced Material, 6, p. 677 (1994)], such as tris(4-carbazoyl-9-ylphenyl)amine (TCTA), 4,4′,4″-tri[phenyl(m-tolyl)amino]triphenylamine (m-MTDATA), 1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene (m-MTDAPB), or soluble conductive polymer polyaniline / dodecylbenzenesulfonic acid (Polyaniline / Dodecylbenzenesulfonic acid). Poly(3,4-ethylenedioxythiophene) / Poly(4-styrenesulfonate), Polyaniline / Camphor sulfonic acid, or Polyaniline / Poly(4-styrenesulfonate) may also be used.

[0126] 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.

[0127] Examples of electron transport materials that can be used include oxadiazole derivatives, anthraquinodimethane and its derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, tetracyanoanthraquinodimethane and its derivatives, fluorenone derivatives, diphenyldicyanoethylene and its derivatives, diphenoquinone derivatives, and metal complexes of 8-hydroxyquinoline and its derivatives. Not only low molecular weight substances but also high molecular weight substances can be used.

[0128] As the electron injection material, for example, LiF is typically used in the industry, but the present application is not limited to this.

[0129] The light-emitting material may be a red, green, or blue light-emitting material, or a mixture of two or more light-emitting materials may be used if necessary. The light-emitting material may be a fluorescent material or a phosphorescent material. The light-emitting material may be a material that emits light by combining holes and electrons injected from the anode and cathode, respectively, or a material in which both the host material and the dopant material contribute to light emission.

[0130] The organic light emitting device according to one embodiment of the present application may be top-emitting, bottom-emitting, or dual-sided emitting, depending on the materials used.

[0131] 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 principle similar to that applied to organic light-emitting devices. [Example]

[0132] The present specification will be described in more detail below with reference to examples, but these are merely for the purpose of illustrating the present application and are not intended to limit the scope of the present application.

[0133] <Production Example 1> Production of target compound 1 (1) Preparation of Compound F1 [ka]

[0134] 1) Preparation of Compound D Compound A (20 g, 89.68 mmol), compound B (15.6 g, 89.68 mmol), Pd(PPh3)4 (5.1 g, 4.48 mmol), and NaOH (7.2 g, 179.36 mmol) were dissolved in 1,4-dioxane / water (200 mL / 50 mL) and stirred at 100 °C for 8 h. The reaction mixture was dissolved in methylene chloride (MC) and extracted with water. The organic layer was dried over anhydrous MgSO4 and filtered through a silica gel filter. The filtrate was evaporated using a rotary evaporator to remove the solvent, affording 11.7 g of compound D as a yellow oil in 48% yield.

[0135] 2) Preparation of Compound E Compound D (11.7 g, 44.05 mmol) was dissolved in CHCl3 (150 mL), and Br2 (1.2 mL, 44.05 mmol) was added dropwise at 0 °C and stirred at room temperature for 2 hours. Methanol (MeOH) was added to the reaction mixture, which was stirred for 30 minutes and then filtered to obtain 14.3 g of compound E as a white solid in 93% yield.

[0136] 3) Preparation of Compound F1 Compound E (14.3 g, 40.89 mmol) was dissolved in dimethylacetamide (DMA) (150 mL), and then Cs2CO3 (26.5 g, 81.79 mmol) was added and stirred at 160 °C for 3 hours. The reaction mixture was filtered, and the filtrate was evaporated to remove the solvent, yielding 11.5 g of compound F1 as a white solid in 85% yield.

[0137] (2) Preparation of target compound 1 [ka]

[0138] 1) Preparation of Compound G Compound F1 (20 g, 60.31 mmol), bis(pinacolato)diboron (30.6 g, 120.63 mmol), PdCl2dppf (2.2 g, 3.02 mmol), and KOAc (18 g, 180.93 mmol) were dissolved in 1,4-dioxane (250 mL) and stirred at 100 °C for 4 h. The reaction mixture was concentrated, dissolved in MC, extracted with water, and the organic layer was dried over anhydrous MgSO4 and filtered through a silica gel filter. The filtrate was evaporated to remove the solvent on a rotary evaporator, affording 20 g of crude compound G as a brown solid without further purification.

[0139] 2) Preparation of Compound I Compound G (20 g, 52.83 mmol), compound H (14 g, 52.83 mmol), Pd(PPh3)4 (3 g, 2.64 mmol), and K2CO3 (14.5 g, 105.66 mmol) were dissolved in 1,4-dioxane / water (1,4-dioxane / HO) (250 mL / 50 mL) and stirred at 100 °C for 6 h. After the reaction was completed, the precipitated solid was filtered and washed with water (HO), methanol (MeOH), and acetone to obtain 13.8 g of compound I as a white solid in 54% yield.

[0140] 3) Preparation of Compound J Compound I (13.8 g, 28.53 mmol), bis(pinacolato)diboron (14.5 g, 57.06 mmol), Pd(dba)2 (1.6 g, 2.85 mmol), XPhos (2.7 g, 5.71 mmol), and KOAc (8.4 g, 85.59 mmol) were dissolved in 1,4-dioxane (150 mL) and stirred at 100 °C for 14 h. The reaction mixture was concentrated, dissolved in methylene chloride (MC), extracted with water, and the organic layer was dried over anhydrous MgSO4 and filtered through a silica gel filter. The filtrate was then evaporated to remove the solvent, affording 14 g of crude compound J as a brown solid without further purification.

[0141] 4) Production of target compound 1 Compound J (14 g, 24.35 mmol), compound K (6.9 g, 24.35 mmol), Pd(PPh3)4 (1.4 g, 1.22 mmol), and K2CO3 (6.7 g, 48.69 mmol) were dissolved in 1,4-dioxane / water (1,4-dioxane / HO) (200 mL / 40 mL) and stirred at 100 °C for 5 h. After completion of the reaction, the precipitated solid was filtered and washed with HO, MeOH, and acetone to obtain 11.7 g of the target compound 1(K) as a white solid in 74% yield.

[0142] Compound F1 in Table 1 below was prepared in the same manner as in the preparation of Compound F1, except that Intermediate A and Intermediate B in Table 1 below were used instead of Compounds A and B, respectively.

[0143] [Table 1] In addition, the target compounds in Table 2 below were prepared in the same manner as in the preparation of target compound 1, except that intermediates F1, H, and K in Table 2 below were used instead of compounds F1, H, and K, respectively.

[0144] [Table 2] TIFF0007788168000039.tif107169

[0145] <Production Example 2> Production of target compound 43 (1) Preparation of Compound F2 [ka] Compound C (10 g, 39.57 mmol) was dissolved in CHCl3 (100 mL), and Br2 (2.04 mL, 39.57 mmol) was added dropwise at 0 °C and stirred at room temperature for 2 hours. Methanol (MeOH) was added to the reaction mixture, which was stirred for 30 minutes and then filtered to obtain 11.8 g of compound F2 as a white solid in 90% yield.

[0146] Compound F2 in Table 3 below was prepared in the same manner as in the preparation of Compound F2, except that Intermediate C in Table 2 below was used instead of Compound C.

[0147] [Table 3]

[0148] (2) Preparation of target compound 43 The same procedure as in Preparation Example 1 for preparing target compound 1 was followed, except that compound F2 was used instead of compound F1, to obtain 13.7 g of target compound 43 in a 59% yield.

[0149] In addition, the target compounds in Table 4 below were prepared in the same manner as in the preparation of target compound 43, except that intermediates F2, H, and K in Table 4 below were used instead of compounds F2, H, and K, respectively.

[0150] [Table 4] TIFF0007788168000043.tif213169 TIFF0007788168000044.tif228169 TIFF0007788168000045.tif228169 Compounds were prepared using the same methods as in Preparation Examples 1 and 2, and all compounds other than those in the Preparation Examples were also synthesized. The synthesis confirmation results are shown in Tables 5 and 6 below. Table 5 below shows the measured values ​​of FD-MS (Field desorption mass spectrometry), and Table 6 below shows the measured values ​​of FD-MS (Field desorption mass spectrometry). 1 H NMR (CDCl3, 200 MHz) measurements.

[0151] [Table 5] TIFF0007788168000047.tif220169 TIFF0007788168000048.tif221169 TIFF0007788168000049.tif220169 TIFF0007788168000050.tif221169 TIFF0007788168000051.tif221169 TIFF0007788168000052.tif220169 TIFF0007788168000053.tif221169 TIFF0007788168000054.tif221169 TIFF0007788168000055.tif221169 TIFF0007788168000056.tif221169 TIFF0007788168000057.tif221169 TIFF0007788168000058.tif221169 TIFF0007788168000059.tif221169 TIFF0007788168000060.tif221169 TIFF0007788168000061.tif222169 TIFF0007788168000062.tif221169 TIFF0007788168000063.tif222169 TIFF0007788168000064.tif76169

[0152] [Table 6] TIFF0007788168000066.tif204169 TIFF0007788168000067.tif221169 TIFF0007788168000068.tif228169 TIFF0007788168000069.tif213169 TIFF0007788168000070.tif45169

[0153] <Experimental Example 1> 1) Preparation of organic light-emitting device - Red single host A glass substrate coated with a 1,500 Å thick indium tin oxide (ITO) thin film was ultrasonically cleaned in distilled water. After the distilled water cleaning, the substrate was ultrasonically cleaned with solvents such as acetone, methanol, and isopropyl alcohol, dried, and then treated with UVO (Ultraviolet Ozone) for 5 minutes using UV in a UV (Ultraviolet) cleaning machine. The substrate was then transferred to a plasma cleaning machine (PT) and plasma treated in a vacuum to remove the ITO work function and residual film, before being transferred to a thermal evaporation system for organic deposition.

[0154] On the ITO transparent electrode (anode), a hole injection layer made of 2-TNATA (4,4',4''-Tris[2-naphthyl(phenyl)amino]triphenylamine) and a hole transport layer made of TAPC (4,4'-Cyclohexylidenebis[N,N-bis(4-methylphenyl)benzenamine]) were formed as common layers.

[0155] An emitting layer was formed thereon by thermal vacuum deposition as follows. The emitting layer was formed using the compounds listed in Table 7 below as a red host and (piq)2(Ir)(acac) as a red phosphorescent dopant. The host was doped with (piq)2(Ir)(acac) at 3 wt% based on the total weight of the emitting layer and deposited to a thickness of 500 Å. Then, bathocuproine (BCP) was deposited to a thickness of 60 Å as a hole-blocking layer, and Alq3 was deposited to a thickness of 200 Å as an electron-transporting layer. Finally, lithium fluoride (LiF) was deposited to a thickness of 10 Å on the electron-transporting layer to form an electron-injecting layer. An aluminum (Al) cathode was then deposited to a thickness of 1,200 Å on the electron-injecting layer to form a cathode, thereby producing organic light-emitting devices of Comparative Examples 1 to 10 and Examples 1 to 16.

[0156] On the other hand, all the organic compounds required for manufacturing OLED elements are 10 -6 ~10 -8 The resulting material was purified by vacuum sublimation under torr and used for fabricating OLEDs.

[0157] Compounds A to J used in Comparative Examples 1 to 10 are as follows.

[0158] [ka]

[0159] 2) Driving voltage and luminous efficiency of organic light-emitting devices The electroluminescence (EL) characteristics of the organic light-emitting devices of Comparative Examples 1 to 4 and Examples 1 to 16 fabricated as described above were measured using an M7000 manufactured by Mac Science, and the measurement results were used to measure the luminance of the devices with a reference brightness of 6,000 cd / m 2 or less using a lifetime measurement device (M6000) manufactured by Mac Science. 2 T when 90 The T 90 means the lifetime (unit: h), which is the time it takes for the brightness to reach 90% of the initial brightness.

[0160] The measured characteristics of the organic light emitting device are shown in Table 7 below.

[0161] [Table 7] TIFF0007788168000073.tif230169 As can be seen from Table 7, when the compound corresponding to Chemical Formula 1 of the present application was used as the sole host in the emission layer of the organic light-emitting device as in Examples 1 to 16, the device exhibited improved performance and efficiency compared to Comparative Examples 1 to 4 in which Comparative Compounds A to D, which do not correspond to Chemical Formula 1 of the present application, were used as the sole host in the emission layer of the organic light-emitting device.

[0162] This is because when unipolar N-type compounds such as comparative compounds A to J are used as a single host in the emission layer of an organic light-emitting device, they have a dibenzofuran linker and have almost no hole injection ability, which is thought to result in high driving voltage and generally low lifespan and efficiency characteristics.

[0163] In contrast, the compound of the present application, which corresponds to Chemical Formula 1, is believed to be useful for improving the efficiency and driving voltage of devices because it has a suitable T1 value and band gap for the red host by introducing naphthobenzofuran, which has an extended π-conjugation to the dibenzofuran linker. Here, the T1 value refers to the energy level value of the triplet state.

[0164] In addition, since the substituent is substituted at a specific position of the naphthobenzofuran linker, it is believed that the structure is more thermally stable and has improved electron mobility characteristics, which will help improve the efficiency and driving voltage of devices.

[0165] Furthermore, compared to comparative compounds that simply have a dibenzofuran linker or have substituents formed in one direction, the compound of the present application corresponding to Chemical Formula 1, in which the substituents extend in both directions, has more extended conjugation than the comparative compounds, and therefore has the advantage of being able to have fast electron transport ability and more thermal stability when applied to devices.

[0166] In the case of a compound with a substituent located at a position such as Comparative Compound B, intermolecular interactions are hindered due to strong steric hindrance and shielding of the oxygen atom, which can cause defects in the packing structure of the compound when the compound such as Comparative Compound B is applied to a device, resulting in reduced efficiency and lifetime of the device.

[0167] In addition, when the substituents are located at positions such as those of comparative compounds A and C to J, the overlap of the HOMO / LUMO electron distribution clouds is greater than that of the compound corresponding to Chemical Formula 1 of the present application, resulting in a larger difference in the S1 and T1 energy gaps, making it difficult to expect an increase in efficiency due to exciton ISC (intersystem crossing).

[0168] <Experimental Example 2> 1) Preparation of organic light-emitting device - Red N+P mixed host Organic light-emitting devices of Comparative Examples 5 and 6 and Examples 17 to 32 were prepared in the same manner as in Experimental Example 1, except that the compound represented by Chemical Formula 1 of the present invention was mixed with a P-type host or a bipolar arylamine compound having strong hole transfer (HT) properties as shown in Table 8 below as a red host when forming the light-emitting layer.

[0169] The N+P mixture means that an N-type host and a P-type host are mixed.

[0170] 2) Driving voltage and luminous efficiency of organic light-emitting devices The electroluminescence (EL) characteristics of the organic light-emitting devices of Comparative Examples 11 and 12 and Examples 17 to 32 prepared as described above were measured using an M7000 manufactured by Mac Science, and the measurement results were used to measure the luminance of the organic light-emitting devices with a reference luminance of 6,000 cd / m 2 or less using a lifetime measurement device (M6000) manufactured by Mac Science. 2 T when 90 was measured.

[0171] The measured characteristics of the organic light emitting device are shown in Table 8 below.

[0172] [Table 8] TIFF0007788168000075.tif117169 The P-type host or bipolar arylamine compound in Table 8 was selected from the compounds in the following groups A to C.

[0173] [ka] [ka] [ka] TIFF0007788168000079.tif194165 As can be seen from Table 8, when a unipolar N-type compound having a naphthobenzofuran linker corresponding to Chemical Formula 1 of the present application is mixed with a unipolar P-type compound or a bipolar arylamine compound corresponding to Groups A to C and used as a host in the emission layer of an organic light emitting device as in Examples 17 to 32, it was confirmed that the mixture exhibits excellent lifetime, efficiency, and driving voltage characteristics compared to when a unipolar N-type compound having a naphthobenzofuran linker corresponding to Chemical Formula 1 of the present application is used as a single host.

[0174] This is believed to be because when a unipolar N-type compound corresponding to Chemical Formula 1 of the present application is mixed with a unipolar P-type compound or a bipolar arylamine compound, an exciplex phenomenon occurs due to the strong hole transport (HT) characteristics of the arylamine.In addition, it is believed that excellent results are also shown in terms of driving voltage due to a low hole injection barrier.

[0175] The exciplex phenomenon is a phenomenon in which electron exchange between two molecules releases energy equivalent to the HOMO level of the donor (p-host) and the LUMO level of the acceptor (n-host). When an exciplex phenomenon occurs between two molecules, reverse intersystem crossing (RISC) occurs, which can increase the internal quantum efficiency of fluorescence to 100%.

[0176] In general, arylamine bipolar compounds have strong hole transport (HT) and electron transfer (ET) properties due to the low hole and electron injection barrier of bipolar compounds, which allows them to have a narrow band gap and low T1 energy value, and they can show excellent efficiency in phosphorescent red devices even with a single host. However, due to their fast hole mobility, they tend to show a slight decrease in lifespan due to degradation within the device.

[0177] However, this problem can be solved by mixing a unipolar N-type compound having a naphthobenzofuran linker, such as that represented by Chemical Formula 1 of the present application. This means that mixing two compounds in the light-emitting layer achieves an appropriate charge velocity balance, thereby reducing degradation and expanding the recombination zone, thereby increasing the lifetime without reducing the excellent efficiency that is an advantage of arylamine bipolar compounds. [Explanation of symbols]

[0178] 100... Substrate 200...Anode 300...organic layer 301: Hole injection layer 302 Hole transport layer 303 Light-emitting layer 304 Hole blocking layer 305...electron transport layer 306...electron injection layer 400...Cathode

Claims

1. A heterocyclic compound represented by any one of the following chemical formulas 1-1 to 1-3: 【Chemistry 32】 【Transformation 33】 【Transformation 34】 In the above chemical formulas 1-1 to 1-3, L1, L2, L4, and L5 are the same or different and each independently represent a direct bond; a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms; a, b, d, and e each represent an integer of 0 to 3, and when a, b, d, and e each represent 2 or more, the substituents in parentheses may be the same or different; In the above Chemical Formula 1-1, Ar1 and Ar4 are the same or different and each independently represent an aryl group having 6 to 60 carbon atoms; or a heteroaryl group having 2 to 60 carbon atoms, wherein the aryl group and heteroaryl group may be substituted or unsubstituted; at least one of Ar1 and Ar4 is a monocyclic or polycyclic heteroaryl group having 2 to 60 carbon atoms and containing one or more N; or an aryl group having 6 to 60 carbon atoms and substituted with one or more cyano groups, wherein the monocyclic or polycyclic heteroaryl group may be substituted or unsubstituted; In the above Chemical Formula 1-2, Ar2 and Ar4 are the same or different and each independently represent an aryl group having 6 to 60 carbon atoms; or a heteroaryl group having 2 to 60 carbon atoms, wherein the aryl group and heteroaryl group may be substituted or unsubstituted; at least one of Ar2 and Ar4 is a monocyclic or polycyclic heteroaryl group having 2 to 60 carbon atoms and containing one or more N; or an aryl group having 6 to 60 carbon atoms and substituted with one or more cyano groups, wherein the monocyclic or polycyclic heteroaryl group may be substituted or unsubstituted; In the above Chemical Formula 1-3, Ar1 and Ar5 are the same or different and each independently represent an aryl group having 6 to 60 carbon atoms; or a heteroaryl group having 2 to 60 carbon atoms, wherein the aryl group and heteroaryl group may be substituted or unsubstituted; at least one of Ar1 and Ar5 is a monocyclic or polycyclic heteroaryl group having 2 to 60 carbon atoms and containing one or more N; or an aryl group having 6 to 60 carbon atoms and substituted with one or more cyano groups, wherein the monocyclic or polycyclic heteroaryl group may be substituted or unsubstituted; Rp represents hydrogen, deuterium, a halogen group, or a substituted or unsubstituted alkyl group having 6 to 60 carbon atoms, and p represents an integer of 0 to 4, and when p is 2 or greater, the substituents in the parentheses may be the same or different.

2. The substituted or unsubstituted groups include deuterium, a cyano group, a halogen group, a linear or branched alkyl group having 1 to 60 carbon atoms, a linear or branched alkenyl group having 2 to 60 carbon atoms, a linear or branched alkynyl group having 2 to 60 carbon atoms, a monocyclic or polycyclic cycloalkyl group having 3 to 60 carbon atoms, a monocyclic or polycyclic heterocycloalkyl group having 2 to 60 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 60 carbon atoms, a monocyclic or polycyclic heteroaryl group having 2 to 60 carbon atoms, -SiRR'R'', -P(=O)RR', an alkylamine having 1 to 20 carbon atoms, and a monocyclic or polycyclic aryl group having 6 to 60 carbon atoms. and monocyclic or polycyclic heteroarylamines having 2 to 60 carbon atoms, or substituted with a substituent formed by linking two or more substituents selected from the above-mentioned exemplified substituents, and R, R', and R'' are the same or different and each independently represent a substituted or unsubstituted alkyl having 1 to 60 carbon atoms; a substituted or unsubstituted aryl having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl having 2 to 60 carbon atoms.

3. The heterocyclic compound according to claim 1, wherein the monocyclic or polycyclic heteroaryl group containing one or more N atoms and having 2 to 60 carbon atoms is a group represented by the following chemical formula 3: 【Chemistry 37】 In the above Chemical Formula 3, X1 is CR1 or N, X2 is CR2 or N, X3 is CR3 or N, X4 is CR4 or N, and X5 is CR5 or N, and at least one of X1 to X5 is N; R1 to R5 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 alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms; a substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms; a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; a substituted or unsubstituted heterocycloalkyl group having 2 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; -P(=O)RR; and NRRR, or two or more adjacent groups may be bonded to each other to form a substituted or unsubstituted aliphatic or aromatic hydrocarbon ring or heterocycle, and R12 to R14 are the same or different and each independently represent hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; 【Transformation 38】 is a moiety that connects to the above-mentioned Chemical Formulas 1-1 to 1-3.

4. A heterocyclic compound represented by the following chemical formula 1-4: 【Chemistry 35】 In the above Chemical Formula 1-4, L2 and L5 are each independently a direct bond; b and e are each an integer equal to 0; one of Ar2 and Ar5 is a group represented by any one of the following chemical formulas 3-1 to 3-4, and the other of Ar2 and Ar5 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group containing O or S and having 2 to 60 carbon atoms, 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 In Chemical Formula 3-1, X1 is CR1 or N, X3 is CR3 or N, X5 is CR5 or N, and one or more of X1, X3, and X5 is N; In Chemical Formula 3-2, X1 is CR1 or N, X2 is CR2 or N, X5 is CR5 or N, and one or more of X1, X2, and X5 is N; In Chemical Formula 3-3, X1 is CR1 or N, X2 is CR2 or N, X3 is CR3 or N, and at least one of X1 to X3 is N; In Chemical Formula 3-4, X1 is CR1 or N, X2 is CR2 or N, X5 is CR5 or N, one or more of X1, X2, and X5 is N, Z1 is O; or S, R1 to R3 and R5 to R9 are the same or different and each independently represent hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; Rp is hydrogen; or deuterium, p is an integer of 0 to 4, and when p is 2 or more, the substituents in the parentheses are the same or different; Here, the term "substituted or unsubstituted" means that the group is substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium; a cyano group; a halogen group; a linear or branched alkyl group having 1 to 60 carbon atoms; a monocyclic or polycyclic aryl group having 6 to 60 carbon atoms; and a monocyclic or polycyclic heteroaryl group having up to three condensed rings and having 2 to 60 carbon atoms. 【Transformation 38】 is a site that is linked to Formula 1-4.

5. A heterocyclic compound represented by any one of the following compounds: 【Chemistry 39】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】

6. An organic light-emitting device comprising a first electrode, a second electrode, and one or more organic material layers provided between the first electrode and the second electrode, wherein one or more of the organic material layers comprises the heterocyclic compound according to any one of claims 1 to 5.

7. The organic light-emitting element according to claim 6 , wherein the organic material layer includes one or more light-emitting layers, and the light-emitting layers include the heterocyclic compound.

8. The organic light-emitting device according to claim 7 , wherein the light-emitting layer includes two or more host materials, and at least one of the host materials includes the heterocyclic compound as a host material of a light-emitting material.

9. The organic light-emitting device according to claim 6 , further comprising one or more layers selected from the group consisting of an emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, a hole auxiliary layer, and a hole blocking layer.

10. The organic light-emitting device according to claim 6, comprising the heterocyclic compound as a first compound and further comprising one of the compounds of the following groups A to C as a second compound: 【Chemistry 40】 【Chemistry 41】 【Chemistry 42】 【change】

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