Heterocyclic compounds and organic light emitting devices comprising the same

Abstract

This specification relates to heterocyclic compounds and organic light-emitting devices comprising the same.

Description

TECHNICAL FIELD

[0001] This application claims priority to Korean Patent Application No. 10-2020-0078171, filed on June 26, 2020, in the Korean Intellectual Property Office, the entire contents of which are incorporated herein.

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

[0003] An organic light emitting device has a structure in which an organic thin film is disposed between two electrodes. If a voltage is applied to the organic light emitting device of such a structure, electrons and holes injected from the two electrodes combine in the organic thin film to form pairs and then quench and emit light. The organic thin film can be composed of a single layer or multiple layers as necessary.

[0004] As a substance used in an organic light emitting device, a pure organic substance or a coordination compound of an organic substance and a metal forming a complex occupies the majority, and can be classified into a hole injection substance, a hole transport substance, a light emitting substance, an electron transport substance, an electron injection substance, and the like according to the use. Here, as a hole injection substance or a hole transport substance, an organic substance having p-type properties, i.e., an organic substance that is easily oxidized and has an electrochemically stable state upon oxidation, is mainly used. On the other hand, as an electron injection substance or an electron transport substance, an organic substance having n-type properties, i.e., an organic substance that is easily reduced and has an electrochemically stable state upon reduction, is mainly used. As a light emitting layer substance, a substance having both p-type properties and n-type properties, i.e., a substance having a stable form in both oxidation and reduction states, is preferred, and a substance having high light emitting efficiency in which excitons generated by recombination of holes and electrons in a light emitting layer are converted into light is preferred.

[0005] In order to improve the performance, lifespan, or efficiency of an organic light emitting device, there is a continuous demand for the development of materials for an organic thin film. SUMMARY

[0006] TECHNICAL PROBLEM

[0007] The present specification provides a heterocyclic compound and an organic light emitting device including the same.

[0008] SOLUTION TO PROBLEM

[0009] One embodiment of the present specification provides a heterocyclic compound represented by the following Chemical Formula 1.

[0010] [Chemical Formula 1]

[0011]

[0012] In the above Chemical Formula 1,

[0013] Z is O or S,

[0014] R1and R2are the same as or different from each other, and are a substituted or unsubstituted alkyl group, or bind to each other to form an aliphatic ring,

[0015] L is a direct bond, or a substituted or unsubstituted arylene group,

[0016] a is an integer of 1 to 3, and when a is 2 or more, 2 or more of L are the same as or different from each other,

[0017] b is an integer of 1 to 4, and when b is 2 or more, the structures in the parentheses are the same as or different from each other,

[0018] Ar1is selected from any one of the following structures,

[0019]

[0020] In the above structures,

[0021] is a moiety connected to L,

[0022] c is an integer of 1 to 5, and when c is 2 or more, 2 or more of G17are the same as or different from each other,

[0023] X1to X4are the same as or different from each other, and are each independently N or CR3, but 2 or more of X1to X4are N,

[0024] R3, G1to G15, and G17are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

[0025] Another embodiment of the present specification provides an organic light emitting device, including: a first electrode, a second electrode disposed opposite to the first electrode, and one or more organic layers disposed between the first electrode and the second electrode, one or more of the organic layers containing the heterocyclic compound.

[0026] Effects of the Invention

[0027] The heterocyclic compound according to an embodiment of the present specification can be used as a material for an organic layer of an organic light emitting device, and by using the compound, improvement in efficiency, a lower driving voltage, and / or improvement in lifespan characteristics can be achieved in an organic light emitting device. BRIEF DESCRIPTION OF DRAWINGS

[0028] Figures 1 to 4 An organic light emitting device according to an embodiment of the present specification is illustrated.

[0029] 1: substrate

[0030] 2: first electrode

[0031] 3: light-emitting layer

[0032] 4: second electrode

[0033] 5: hole injection layer

[0034] 6: hole transport layer

[0035] 6-1: first hole transport layer

[0036] 6-2: second hole transport layer

[0037] 7: electron transport layer

[0038] 8: electron injection layer

[0039] 9: electron injection and transport layer

[0040] 10: hole blocking layer DETAILED DESCRIPTION

[0041] Hereinafter, the present specification will be described in more detail.

[0042] The present specification provides a heterocyclic compound represented by Chemical Formula 1 below.

[0043] [Chemical Formula 1]

[0044]

[0045] In Chemical Formula 1 above,

[0046] Z is O or S,

[0047] R1and R2are the same as or different from each other, and are a substituted or unsubstituted alkyl group, or are combined with each other to form an aliphatic ring,

[0048] L is a direct bond, or a substituted or unsubstituted arylene group,

[0049] a is an integer of 1 to 3, and when a is 2 or more, 2 or more Ls are the same as or different from each other,

[0050] b is an integer of 1 to 4, and when b is 2 or more, the structures within the parentheses are the same as or different from each other,

[0051] Ar1is selected from any one of the following structures,

[0052]

[0053] In the above structures,

[0054] is a moiety connected to L,

[0055] c is an integer of 1 to 5, and when c is 2 or more, two or more G17s are the same or different from each other,

[0056] X1to X4are the same or different from each other, and each independently N or CR3, but two or more of X1to X4are N,

[0057] R3, G1to G15, and G17are the same or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

[0058] In the organic light emitting device, if the dipole moment of the organic matter is increased, the effect that the lifetime of the device is improved is exhibited.

[0059] The compound represented by Chemical Formula 1 of the present application forms polarization by including a substituent on one side of the xanthene group or thioxanthene group in which Z is O or S, and thus the dipole moment is increased, and the effect that the lifetime is improved is exhibited. In addition, R1and R2include an alkyl group to increase the polarization effect between the xanthene group and the substituent (Ar1), and the substituent includes the Ar1structure to improve the electron migration property, and thus the effect that the efficiency of the organic light emitting device is improved is exhibited.

[0060] In the present specification, when a certain part is said to "include" a certain component, unless particularly stated otherwise, it means that other components can be further included, rather than excluding other components.

[0061] In the present specification, when a certain member is said to be "on" another member, it includes not only the case where the certain member is in contact with the other member, but also the case where other members are present between the two members.

[0062] In the present specification, examples of the substituent are described below, but are not limited thereto.

[0063] The term "substituted" above means that a hydrogen atom bonded to a carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited as long as it is a position where a hydrogen atom can be substituted, i.e., a position where a substituent can be substituted, and when two or more are substituted, the two or more substituents can be the same or different from each other.

[0064] In the present specification, the term "substituted or unsubstituted" means substituted with 1 or 2 or more substituents selected from deuterium, a halogen group, a cyano group (-CN), an ester group, an imide group, an amine group, an alkoxy group, an alkyl group, a cycloalkyl group, an aryl group, and a heterocyclic group, or substituted with substituents each of which is 2 or more of the above exemplified substituents, or non-substituted. For example, the "substituent in which 2 or more substituents are linked" can be a biphenyl group. That is, the biphenyl group can be an aryl group, or can be interpreted as a substituent in which 2 phenyl groups are linked.

[0065] In the present specification, the above-described alkyl group can be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. As specific examples, there are 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 t-butyl group, a sec-butyl group, a 1-methyl-butyl group, a 1-ethyl-butyl group, a pentyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a t-pentyl group, a hexyl group, an n-hexyl group, a 1-methylpentyl group, a 2-methylpentyl group, a 4-methyl-2-pentyl group, a 3,3-dimethylbutyl group, a 2-ethylbutyl group, a heptyl group, an n-heptyl group, a 1-methylhexyl group, a cyclopentylmethyl group, a cyclohexylmethyl group, an octyl group, an n-octyl group, a t-octyl group, a 1-ethyl-propyl group, a 1,1-dimethyl-propyl group, an iso-hexyl group, a 4-methylhexyl group, a 5-methylhexyl group, and the like, but is not limited thereto.

[0066] In the present specification, the above-described aryl group is not particularly limited, but is preferably an aryl group having 6 to 50 carbon atoms, for example, an aryl group having 6 to 30 carbon atoms, and the above-described aryl group can be a monocyclic ring or a polycyclic ring.

[0067] When the above-described aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 30. Specifically, as the monocyclic aryl group, there can be a phenyl group, a biphenyl group, a terphenyl group, and the like, but is not limited thereto.

[0068] When the above-described aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 10 to 30. Specifically, as the polycyclic aryl group, there can be a naphthyl group, an anthryl group, a phenanthryl group, a triphenylene group, a pyrenyl group, a perylenyl group, a fluorenyl group, a fluoranthenyl group, and the like, but is not limited thereto.

[0069] In the present specification, the above-described fluorenyl group can be substituted, and adjacent groups can be combined with each other to form a ring.

[0070] In the case where the above-described fluorenyl group is substituted, it can be and and the like, but is not limited thereto.

[0071] In the present specification, the above-mentioned aryl group can be exemplified by the above-mentioned aryl group except that it is divalent.

[0072] In the present specification, the above-mentioned heterocyclic group contains one or more non-carbon atoms, i.e., heteroatoms, and specifically, the above-mentioned heteroatoms can contain one or more atoms selected from O, N, S, P, and the like. The number of carbon atoms is not particularly limited, but preferably, the number of carbon atoms is 1 to 50, and further preferably, 2 to 30. The above-mentioned heterocyclic group can be a monocyclic or polycyclic ring. The above-mentioned heterocyclic group can be an aromatic ring, an aliphatic ring, and a ring in which they are fused. As the above-mentioned heterocyclic group, there are, for example, a thienyl group, a furyl group, a pyrrolyl group, an imidazolyl group, a thiazolyl group, an oxazolyl group, a dioxazolyl group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazinyl group, a triazolyl group, an acridyl group, a pyridazyl group, a pyrazyl group, a quinolyl group, a quinazolyl group, a quinoxalyl group, a phtalazyl group, a pyridopyrimidyl group, a pyridopyrazyl group, a pyrazopyrazyl group, an isoquinolyl group, an indolyl group, a carbazolyl group, a benz oxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzocarbazolyl group, a benzothiophenyl group, a dibenzothiophenyl group, a benzofuranyl group, a phenanthroline group, an iso xazolyl group, a thiazolyl group, a benzothiazolyl group, a benzocarbazolyl group, a benzothiophenyl group, a dibenzothiophenyl group, a benzofuranyl group, a phenanthroline group, an iso

[0073] In the present specification, the above-mentioned halogen group can be fluorine, chlorine, bromine, or iodine.

[0074] In the present specification, the above-mentioned cycloalkyl group is not particularly limited, but preferably, the number of carbon atoms is 3 to 30, and specifically, there are 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, a cyclooctyl group, an adamantyl group, and the like, but is not limited thereto.

[0075] In the present specification, the above-mentioned aliphatic ring can be exemplified by the above-mentioned cycloalkyl group.

[0076] In the present specification, the above-mentioned alkoxy group can be linear, branched, or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but preferably, the number of carbon atoms is 1 to 30. Specifically, there are a methoxy group, an ethoxy group, a n-propoxy group, an i-propoxy group, a n-butoxy group, an i-butoxy group, a t-butoxy group, a s-butoxy group, a n-pentoxy group, a neopentoxy group, an i-pentoxy group, a n-hexyloxy group, a 3,3-dimethylbutoxy group, a 2-ethylbutoxy group, a n-octyloxy group, a n-nonyloxy group, a n-decyloxy group, and the like, but is not limited thereto.

[0077] In the present specification, the amine group can be selected from the group consisting of -NH2, alkylamine group, N-alkyl arylamine group, arylamine group, N-aryl heteroarylamine group, N-alkyl heteroarylamine group, and heteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably from 0 to 30. As specific examples of the amine group, there are methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthrylamine group, 9-methyl-anthrylamine group, diphenylamine group, N-phenyl naphthylamine group, ditolylamine group, N-phenyl tolylamine group, triphenylamine group, N-phenyl biphenylamine group, N-biphenyl naphthylamine group, N-naphthyl fluorenylamine group, N-phenyl phenanthrylamine group, N-biphenyl phenanthrylamine group, N-phenyl fluorenylamine group, N-phenyl terphenylamine group, N-phenanthryl fluorenylamine group, N-biphenyl fluorenylamine group, and the like, but is not limited thereto.

[0078] In the present specification, the N-alkyl arylamine group means an amine group in which alkyl and aryl are substituted on N of the amine group.

[0079] In the present specification, the N-aryl heteroarylamine group means an amine group in which aryl and heteroaryl are substituted on N of the amine group.

[0080] In the present specification, the N-alkyl heteroarylamine group means an amine group in which alkyl and heteroaryl are substituted on N of the amine group.

[0081] In the present specification, the alkyl group in the alkylamine group, N-aryl alkylamine group, and N-alkyl heteroarylamine group is the same as the examples of the alkyl group described above.

[0082] In one embodiment of the present specification, the above a is 1 or 2.

[0083] In one embodiment of the present specification, the above L is a direct bond, or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

[0084] In one embodiment of the present specification, the above L is a direct bond, a substituted or unsubstituted monocyclic arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted polycyclic arylene group having 10 to 30 carbon atoms.

[0085] In one embodiment of the present specification, the above L is a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted naphthylene group.

[0086] In one embodiment of the present specification, the above L is a direct bond, or an arylene group substituted or unsubstituted with 1 or more substituents selected from the group consisting of deuterium, cyano, alkyl group, and aryl group.

[0087] In one embodiment of the present specification, the above L is a direct bond; or an arylene group having 6 to 30 carbon atoms, which is substituted with one or more substituents selected from the group consisting of deuterium, a cyano group, an alkyl group, and an aryl group, or is unsubstituted.

[0088] In one embodiment of the present specification, the above L is a direct bond; phenylene, which is substituted with one or more substituents selected from the group consisting of deuterium, a cyano group, an alkyl group, and an aryl group, or is unsubstituted; biphenylene, which is substituted with one or more substituents selected from the group consisting of deuterium, a cyano group, an alkyl group, and an aryl group, or is unsubstituted; or naphthylene, which is substituted with one or more substituents selected from the group consisting of deuterium, a cyano group, an alkyl group, and an aryl group, or is unsubstituted.

[0089] In one embodiment of the present specification, the above L is a direct bond; or an arylene group, which is substituted with deuterium, a cyano group, an alkyl group, or an aryl group, or is unsubstituted.

[0090] In one embodiment of the present specification, the above L is a direct bond; phenylene, which is substituted with deuterium, a cyano group, an alkyl group, or an aryl group, or is unsubstituted; biphenylene, which is substituted with deuterium, a cyano group, an alkyl group, or an aryl group, or is unsubstituted; or naphthylene, which is substituted with deuterium, a cyano group, an alkyl group, or an aryl group, or is unsubstituted.

[0091] In one embodiment of the present specification, the above L is a direct bond; phenylene, which is substituted with deuterium, a cyano group, an alkyl group, or an aryl group, or is unsubstituted; biphenylene, which is substituted with deuterium, a cyano group, an alkyl group, or an aryl group, or is unsubstituted; or naphthylene, which is substituted with deuterium, a cyano group, an alkyl group, or an aryl group, or is unsubstituted.

[0092] In one embodiment of the present specification, the above R1and R2are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or are combined to each other to form an aliphatic ring.

[0093] In one embodiment of the present specification, the above R1and R2are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or are combined to each other to form an aliphatic ring.

[0094] In one embodiment of the present specification, the above R1and R2are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

[0095] In one embodiment of the present specification, the above R1and R2are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

[0096] In one embodiment of the present specification, the above R1and R2are the same as or different from each other, and each independently an alkyl group having 1 to 10 carbon atoms.

[0097] In one embodiment of the present specification, the above R1and R2are the same as or different from each other, and each independently an alkyl group having 1 to 5 carbon atoms.

[0098] In one embodiment of the present specification, the above R1and R2are the same as or different from each other, and each is independently a methyl group, an ethyl group, a propyl group, or a butyl group.

[0099] In one embodiment of the present specification, the above R1and R2are each a methyl group or an ethyl group.

[0100] In one embodiment of the present specification, the above R1and R2are each a methyl group or an ethyl group.

[0101] In one embodiment of the present specification, the above R1and R2are each a methyl group or an ethyl group.

[0102] In one embodiment of the present specification, the above R1and R2are each a methyl group or an ethyl group.

[0103] In one embodiment of the present specification, the above R1and R2are each a methyl group or an ethyl group.

[0104] In one embodiment of the present specification, the above R1and R2are each a methyl group or an ethyl group.

[0105] In one embodiment of the present specification, the above Ar1is any one of the following structures.

[0106]

[0107] In the above structure,

[0108] is a moiety to be linked to L,

[0109] c is an integer of 1 to 5, and when c is 2 or more, 2 or more G17s are the same as or different from each other,

[0110] X1to X4are the same as or different from each other, and each is independently N or CR3, but 2 or more of X1to X4are N,

[0111] R3, G1to G15, and G17are the same as or different from each other, and each is independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

[0112] In one embodiment of the present specification, the above Ar1is any one of the following structures.

[0113]

[0114] In the above structure, c, X1to X4, G1to G15, and G17are the same as defined above.

[0115] In one embodiment of the present specification, two of the above-described X1to X4are N, and the other two are CR3, and R3is hydrogen, deuterium, a substituted or unsubstituted alkyl, a substituted or unsubstituted aryl, or a substituted or unsubstituted heterocyclic group.

[0116] In one embodiment of the present specification, two of the above-described X1to X4are N, and the other two are CR3, and R3is hydrogen.

[0117] In one embodiment of the present specification, two of the above-described X1to X4are N, and the other two are CR3, and R3is hydrogen, deuterium, a substituted or unsubstituted alkyl, a substituted or unsubstituted aryl, or a substituted or unsubstituted heterocyclic group.

[0118] In one embodiment of the present specification, two of the above-described X1to X4are N, and the other two are CR3, and R3is hydrogen.

[0119] In one embodiment of the present specification, the above-described G1to G15and G17are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl, a substituted or unsubstituted aryl, or a substituted or unsubstituted heterocyclic group.

[0120] In one embodiment of the present specification, the above-described G1to G15and G17are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl, a substituted or unsubstituted aryl, or a substituted or unsubstituted heterocyclic group.

[0121] In one embodiment of the present specification, the above-described G1to G15and G17are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl, a substituted or unsubstituted aryl, or a substituted or unsubstituted heterocyclic group.

[0122] In one embodiment of the present specification, the above-described G1to G15and G17are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl, a substituted or unsubstituted aryl, or a substituted or unsubstituted heterocyclic group.

[0123] In one embodiment of the present specification, G1to G15and G17are the same as or different from each other, and each independently hydrogen; deuterium; phenyl substituted or unsubstituted with deuterium, cyano, alkyl, aryl, alkoxy, or heterocyclic group; biphenyl substituted or unsubstituted with deuterium, cyano, alkyl, aryl, alkoxy, or heterocyclic group; naphthyl substituted or unsubstituted with deuterium, cyano, alkyl, aryl, alkoxy, or heterocyclic group; fluoranthene substituted or unsubstituted with deuterium, cyano, alkyl, aryl, alkoxy, or heterocyclic group; dibenzothiophene substituted or unsubstituted with deuterium, cyano, alkyl, aryl, alkoxy, or heterocyclic group; or dibenzofuran substituted or unsubstituted with deuterium, cyano, alkyl, aryl, alkoxy, or heterocyclic group.

[0124] In one embodiment of the present specification, G1to G15and G17are the same as or different from each other, and each independently hydrogen; deuterium; phenyl substituted or unsubstituted with deuterium, cyano, alkyl, aryl, alkoxy, or heterocyclic group; biphenyl substituted or unsubstituted with deuterium, cyano, alkyl, aryl, alkoxy, or heterocyclic group; naphthyl substituted or unsubstituted with deuterium, cyano, alkyl, aryl, alkoxy, or heterocyclic group; fluoranthene substituted or unsubstituted with deuterium, cyano, alkyl, aryl, alkoxy, or heterocyclic group; dibenzothiophene substituted or unsubstituted with deuterium, cyano, alkyl, aryl, alkoxy, or heterocyclic group; or dibenzofuran substituted or unsubstituted with deuterium, cyano, alkyl, aryl, alkoxy, or heterocyclic group.

[0125] In one embodiment of the present specification, G1to G15and G17are the same as or different from each other, and each independently hydrogen; deuterium; phenyl substituted or unsubstituted with deuterium, cyano, alkyl, aryl, alkoxy, or heterocyclic group; biphenyl substituted or unsubstituted with deuterium, cyano, alkyl, aryl, alkoxy, or heterocyclic group; naphthyl substituted or unsubstituted with deuterium, cyano, alkyl, aryl, alkoxy, or heterocyclic group; fluoranthene substituted or unsubstituted with deuterium, cyano, alkyl, aryl, alkoxy, or heterocyclic group; dibenzothiophene substituted or unsubstituted with deuterium, cyano, alkyl, aryl, alkoxy, or heterocyclic group; or dibenzofuran substituted or unsubstituted with deuterium, cyano, alkyl, aryl, alkoxy, or heterocyclic group.

[0126] In one embodiment of the present specification, G1to G15and G17described above are the same as or different from each other, and each is independently hydrogen; deuterium; phenyl substituted or unsubstituted with deuterium, cyano, alkyl, pyridyl, alkoxy, or naphthyl; biphenyl substituted or unsubstituted with cyano; naphthyl; fluoranthene; dibenzothiophenyl; or dibenzofuranyl.

[0127] In one embodiment of the present specification, b is an integer of 1 to 3.

[0128] In one embodiment of the present specification, b is 1.

[0129] In one embodiment of the present specification, the above Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-4.

[0130] [Chemical Formula 1-1]

[0131]

[0132] [Chemical Formula 1-2]

[0133]

[0134] [Chemical Formula 1-3]

[0135]

[0136] [Chemical Formula 1-4]

[0137]

[0138] In the above Chemical Formulas 1-1 to 1-4,

[0139] Z, R1, R2, a, L, and Ar1are the same as defined in the above Chemical Formula 1.

[0140] In one embodiment of the present specification, the above Chemical Formula 1 is represented by the above Chemical Formula 1-1.

[0141] In one embodiment of the present specification, the above Chemical Formula 1 is represented by the above Chemical Formula 1-2.

[0142] In one embodiment of the present specification, the above Chemical Formula 1 is represented by the above Chemical Formula 1-3.

[0143] In one embodiment of the present specification, the above Chemical Formula 1 is represented by the above Chemical Formula 1-4.

[0144] In one embodiment of the present specification, b is 2.

[0145] In one embodiment of the present specification, the above Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-5 to 1-10.

[0146] [Chemical Formula 1-5]

[0147]

[0148] [Chemical Formula 1-6]

[0149]

[0150] [Chemical Formula 1-7]

[0151]

[0152] [Chemical Formula 1-8]

[0153]

[0154] [Chemical Formula 1-9]

[0155]

[0156] [Chemical Formula 1-10]

[0157]

[0158] In the above Chemical Formulas 1-5 to 1-10,

[0159] Z, R1, and R2 are the same as the definitions in Chemical Formula 1 above,

[0160] L1and L2are the same as or different from each other, and each is independently a direct bond, or a substituted or unsubstituted arylene group,

[0161] a1and a2are each an integer of 1 to 3,

[0162] When a1is 2 or more, 2 or more L1are the same as or different from each other,

[0163] When a2is 2 or more, 2 or more L2are the same as or different from each other,

[0164] Ar2and Ar3are the same as or different from each other, and each is independently selected from any one of the following structures,

[0165]

[0166] In the above structures,

[0167] is a moiety connected to L1or L2,

[0168] c is an integer of 1 to 5, and when c is 2 or more, 2 or more G17are the same as or different from each other,

[0169] X1to X4are the same as or different from each other, and each independently N or CR3, but 2 or more of X1to X4are N,

[0170] R3, G1to G15, and G17are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

[0171] In one embodiment of the present specification, the above L1and L2are the same as or different from each other, and each independently a direct bond, or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

[0172] In one embodiment of the present specification, the above L1and L2are the same as or different from each other, and each independently a direct bond, or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

[0173] In one embodiment of the present specification, the above L1and L2are the same as or different from each other, and each independently a direct bond, or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

[0174] In one embodiment of the present specification, the above L1and L2are the same as or different from each other, and each independently a direct bond, or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

[0175] In one embodiment of the present specification, the above L1and L2are the same as or different from each other, and each independently a direct bond, or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

[0176] In one embodiment of the present specification, the above L1and L2are the same as or different from each other, and each independently a direct bond, or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

[0177] In one embodiment of the present specification, the above L1and L2are the same as or different from each other, and each independently a direct bond, or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

[0178] In an embodiment of the present specification, the above L1and L2are the same as or different from each other, and each is independently a direct bond; phenylene substituted or unsubstituted with deuterium, a cyano group, an alkyl group, or an aryl group; biphenylene substituted or unsubstituted with deuterium, a cyano group, an alkyl group, or an aryl group; or naphthylene substituted or unsubstituted with deuterium, a cyano group, an alkyl group, or an aryl group.

[0179] In an embodiment of the present specification, the above L1and L2are the same as or different from each other, and each is independently a direct bond; phenylene substituted or unsubstituted with a cyano group or an alkyl group; biphenylene substituted or unsubstituted with a cyano group or an alkyl group; or naphthylene substituted or unsubstituted with a cyano group or an alkyl group.

[0180] In an embodiment of the present specification, the above heterocyclic compound of Chemical Formula 1 is any one of the following structures.

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204] The core structure of Chemical Formula 1 according to an embodiment of the present specification can be manufactured as shown in the following reaction formula, the substituents can be combined by a method known in the art, and the kind, position, or number of the substituents can be changed according to a technique known in the art.

[0205] <Reaction Formula>

[0206]

[0207] In the above reaction formula,

[0208] Z, L, a, R1, R2, Ar1, and b are the same as defined in Chemical Formula 1.

[0209] A is Cl or Br.

[0210] An embodiment of the present specification provides an organic light emitting device, including: a first electrode, a second electrode disposed opposite to the first electrode, and one or more organic layers disposed between the first electrode and the second electrode, one or more of the organic layers including the heterocyclic compound.

[0211] In the organic light emitting device of the present specification, one or more of the organic layers includes the heterocyclic compound of the present specification, that is, includes the heterocyclic compound represented by Chemical Formula 1, and can be manufactured using a manufacturing method and materials known in the art, except for the above.

[0212] For example, the organic light emitting device of the present specification can be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. At this time, it can be manufactured by forming the first electrode by evaporating a metal or a metal oxide having conductivity or an alloy thereof on a substrate using a physical evaporation method (PVD: physical vapor deposition) such as sputtering or e-beam evaporation, then forming the organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer on the first electrode, and then evaporating a substance that can be used as a second electrode on the organic layer. In addition to this method, the organic light emitting device can be manufactured by sequentially evaporating a second electrode substance, an organic layer, and a first electrode substance on a substrate. In addition, the heterocyclic compound represented by Chemical Formula 1 above can be used to form the organic layer in the manufacture of the organic light emitting device not only by a vacuum evaporation method but also by a solution coating method. Here, the solution coating method refers to a spin coating method, a dip coating method, a blade coating method, an inkjet printing method, a screen printing method, a spray method, a roll coating method, and the like, but is not limited thereto.

[0213] When the organic light emitting device includes a plurality of organic layers, the organic layers can be formed of the same substance or different substances.

[0214] The organic layer can be a multilayer structure including a hole injection layer, a hole transport layer, a layer that simultaneously performs hole injection and hole transport, an electron suppression layer, a light emitting layer, and an electron transport layer, an electron injection layer, a layer that simultaneously performs electron injection and electron transport, and the like, but is not limited thereto, and can be a single layer structure. In addition, the organic layer can be manufactured to have a smaller number of layers using various polymer materials and by a solvent process that is not an evaporation method, such as a spin coating method, a dip coating method, a blade coating method, a screen printing method, an inkjet printing method, or a thermal transfer method.

[0215] In an embodiment of the present specification, the organic layer includes an electron injection layer, an electron transport layer, or a layer that simultaneously performs electron injection and electron transport, and the electron injection layer, the electron transport layer, or the layer that simultaneously performs electron injection and electron transport includes the heterocyclic compound.

[0216] In an embodiment of the present specification, the organic layer includes a hole blocking layer, and the hole blocking layer includes the heterocyclic compound.

[0217] According to an embodiment of the present specification, the organic layer can further include 1 layer or more selected from a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.

[0218] In one embodiment of the present specification, the first electrode described above is an anode, and the second electrode is a cathode.

[0219] According to another embodiment, the first electrode described above is a cathode, and the second electrode is an anode.

[0220] For example, the structure of the organic light emitting device of the present specification can have a structure as shown in Figures 1 to 4 but is not limited thereto.

[0221] Figure 1 In the above embodiment, a structure of an organic light emitting device 10 in which a first electrode 2, a light emitting layer 3, and a second electrode 4 are sequentially stacked on a substrate 1 is exemplified. The above Figure 1 is an exemplary structure of an organic light emitting device according to one embodiment of the present specification, and can further include other organic layers.

[0222] Figure 2 In the above embodiment, a structure of an organic light emitting device in which a first electrode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 3, an electron transport layer 7, an electron injection layer 8, and a second electrode 4 are sequentially stacked on a substrate 1 is exemplified. The above Figure 2 is an exemplary structure of an organic light emitting device according to one embodiment of the present specification, and can further include other organic layers.

[0223] Figure 3 In the above embodiment, a structure of an organic light emitting device in which a first electrode 2, a hole injection layer 5, a first hole transport layer 6-1, a second hole transport layer 6-2, a light emitting layer 3, an electron injection and transport layer 9, and a second electrode 4 are sequentially stacked on a substrate 1 is exemplified. The above Figure 3 is an exemplary structure of an organic light emitting device according to one embodiment of the present specification, and can further include other organic layers.

[0224] Figure 4 In the above embodiment, a structure of an organic light emitting device in which a first electrode 2, a hole injection layer 5, a first hole transport layer 6-1, a second hole transport layer 6-2, a light emitting layer 3, a hole blocking layer 10, an electron injection and transport layer 9, and a second electrode 4 are sequentially stacked on a substrate 1 is exemplified. The above Figure 4 is an exemplary structure of an organic light emitting device according to one embodiment of the present specification, and can further include other organic layers.

[0225] Specifically, the above organic light emitting device can have a stacked structure as shown below, in addition to the structure explicitly indicated in the above drawings, but is not limited thereto.

[0226] (1) Anode / Hole transport layer / Light emitting layer / Cathode

[0227] (2) Anode / Hole injection layer / Hole transport layer / Light emitting layer / Cathode

[0228] (3) anode / hole injection layer / hole buffer layer / hole transport layer / light emitting layer / cathode

[0229] (4) anode / hole transport layer / light emitting layer / electron transport layer / cathode

[0230] (5) anode / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode

[0231] (6) anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / cathode

[0232] (7) anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode

[0233] (8) anode / hole injection layer / hole buffer layer / hole transport layer / light emitting layer / electron transport layer / cathode

[0234] (9) anode / hole injection layer / hole buffer layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode

[0235] (10) anode / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / cathode

[0236] (11) anode / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / electron injection layer / cathode

[0237] (12) anode / hole injection layer / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / cathode

[0238] (13) anode / hole injection layer / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / electron injection layer / cathode

[0239] (14) anode / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / cathode

[0240] (15) anode / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode

[0241] (16) anode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / cathode

[0242] (17) anode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode

[0243] (18) anode / hole injection layer / hole transport layer / electron blocking layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode

[0244] In one embodiment of the present specification, the hole-transporting layer described above can be configured of a multi-layer structure. For example, it can be configured of a first hole-transporting layer and a second hole-transporting layer containing different substances from each other.

[0245] The anode described above is an electrode that injects holes, and as an anode material, a substance having a large work function is generally preferred in order to enable holes to be smoothly injected into the organic layer. As specific examples of the anode material that can be used in the present application, there are 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), or the like; combinations of a metal and an oxide such as ZnO:Al or SnO2:Sb; and electrically conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, polyaniline, or the like, but the present application is not limited thereto.

[0246] The cathode described above is an electrode that injects electrons, and as a cathode material, a substance having a small work function is generally preferred in order to enable electrons to be easily injected into the organic layer. As specific examples of the cathode material, there are metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multi-layered structure materials such as LiF / Al or LiO2 / Al, or the like, but the present application is not limited thereto.

[0247] The hole-injection layer described above is a layer that functions to enable the injection of holes from the anode to the light-emitting layer to proceed smoothly, and the hole-injection material is a material that enables holes to be favorably injected from the anode at low voltage, and it is preferred that the HOMO (highest occupied molecular orbital) of the hole-injection material be between the work function of the anode material and the HOMO of the surrounding organic layer. As examples of the hole-injection material, there are metal porphyrine, oligothiophene, arylamine-based organic material, hexacyno hexaazatriphenylene-based organic material, quinacridone-based organic material, perylene-based organic material, carbazole-based organic material, fluorene-based organic material, anthraquinone, and electrically conductive polymers such as polyaniline and polythiophene, but the present application is not limited thereto. Specifically, as the hole-injection material described above, a compound containing a substituted or unsubstituted carbazole and a substituted or unsubstituted fluorene can be used, but the present application is not limited thereto.

[0248] In one embodiment of the present specification, the thickness of the hole-injection layer described above can be from 1 nm to 150 nm. When the thickness of the hole-injection layer described above is 1 nm or more, it has the advantage that the hole-injection characteristics can be prevented from being reduced, and when it is 150 nm or less, it has the advantage that the driving voltage can be prevented from rising in order to improve the mobility of holes when the thickness of the hole-injection layer is too thick.

[0249] The hole transport layer described above can function to smoothly transport holes. The hole transport substance is a substance that can receive holes from the anode or the hole injection layer and transfer them to the light emitting layer, and a substance having a large mobility of holes is suitable. As examples of the hole transport substance, there are arylamine-based organic compounds, carbazole-based organic compounds, quinoxaline-based organic compounds, fluorene-based organic compounds, electrically conductive polymers, and block copolymers having both a conjugated portion and a non-conjugated portion, but are not limited thereto. Specifically, the hole transport substance described above includes quinazoline-based compounds and arylamine-based compounds, but is not limited thereto.

[0250] A hole buffer layer can be further provided between the hole injection layer and the hole transport layer, and can include a material known in the art for hole injection or transport.

[0251] An electron suppression layer can be provided between the hole transport layer and the light emitting layer. The electron suppression layer described above can use the compound described above or a material known in the art.

[0252] The light emitting layer described above can emit red, green, or blue light, and can be composed of a phosphorescent substance or a fluorescent substance. The light emitting substance described above is a substance that can receive holes and electrons from the hole transport layer and the electron transport layer, respectively, and emit light in the visible region by combining them, and is preferably a substance having a high quantum efficiency for fluorescence or phosphorescence. As specific examples, there are 8-hydroxy-quinoline aluminum complex (Alq3), carbazole-based compounds, dimerized styryl compounds, BAlq, 10-hydroxybenzoquinoline-metal compounds, benzoxazole-based compounds, benzothiazole-based compounds, benzimidazole-based compounds, poly(p-phenylenevinylene) (PPV)-based polymers, spiro compounds, polyfluorene, rubrene, and the like, but are not limited thereto.

[0253] In one embodiment of the present specification, the light emitting layer described above includes a host and a dopant. The host described above can include the compound described above, an aromatic condensed ring derivative, a heterocycle-containing compound, and the like. Specifically, as the aromatic condensed ring derivative, there are anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and as the heterocycle-containing compound, there are carbazole derivatives, diphenylfuran derivatives, ladder-type furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

[0254] ​​As the above-mentioned dopant, a phosphorescent substance such as PIQIr(acac) (bis(1-phenylisoquinoline)acetylacetonate iridium), PQIr(acac) (bis(1-phenylquinoline)acetylacetonate iridium), PQIr (tris(1-phenylquinoline) iridium), PtOEP (octaethylporphyrin platinum), or the like, or a fluorescent substance such as Alq3 (tris(8-hydroxyquinolino) aluminum), or the like, but not limited thereto, can be used. When the light-emitting layer emits green light, as the light-emitting dopant, a phosphorescent substance such as Ir(ppy)3 (fac tris(2-phenylpyridine) iridium), or the like, or a fluorescent substance such as Alq3 (tris(8-hydroxyquinolino) aluminum), or the like, but not limited thereto, can be used. When the light-emitting layer emits blue light, as the light-emitting dopant, (4,6-F2ppy)2Irpic, spiro-DPVBi, spiro-6P, distyrylbenzene (DSB), distyrylarylene (DSA), a PFO-based polymer, a PPV-based, a pyrene-based, an arylamine-based compound, or the like, but not limited thereto, can be used.

[0255] In one embodiment of the present specification, a hole-blocking layer can be provided between the above-mentioned electron-transporting layer and the light-emitting layer, and the hole-blocking layer can use a material known in the technical field.

[0256] The above-mentioned electron-transporting layer can function to smoothly transport electrons. The electron-transporting substance is a substance capable of receiving electrons from the cathode and transferring them to the light-emitting layer, and a substance having a large mobility of electrons is suitable. As specific examples, there are an Al complex of 8-hydroxyquinoline, a complex including Alq3, an organic radical compound, an anthracene-based compound, an imidazole-based compound, a hydroxyflavone-metal complex, or the like, but not limited thereto. The thickness of the electron-transporting layer can be 1 nm to 50 nm. When the thickness of the electron-transporting layer is 1 nm or more, it has an advantage that the decrease in electron-transporting properties can be prevented, and when it is 50 nm or less, it has an advantage that the increase in driving voltage to improve the mobility of electrons when the thickness of the electron-transporting layer is too thick can be prevented.

[0257] The above-described electron injection layer can function to smoothly inject electrons. As the electron injection substance, a compound having an ability to transport electrons, an effect of injecting electrons from a cathode, an excellent electron injection effect to a light-emitting layer or a light-emitting material, a function to prevent excitons generated in the light-emitting layer from migrating to a hole injection layer, and an excellent film formation ability is preferable. Specifically, there are fluorenone, anthraquinone dimethane, diphenylquinone, thiopyran dioxide, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidenemethane, anthrone, anthracene, imidazole, and the like, and derivatives thereof, metal complex compounds, nitrogen-containing five-membered ring derivatives, and lithium quinolate (LiQ), but are not limited thereto.

[0258] In one embodiment of the present specification, the organic layer containing the heterocyclic compound of Chemical Formula 1 is an electron injection layer, an electron transport layer, or a layer that simultaneously performs electron injection and electron transport, and the electron injection layer, the electron transport layer, or the layer that simultaneously performs electron injection and electron transport further contains a metal complex.

[0259] In one embodiment of the present specification, as examples of the metal complex, there are an Al complex of 8-hydroxyquinoline (Alq3), LiQ, a metal complex compound, and the like, but are not limited thereto.

[0260] As the metal complex compound, there are lithium 8-hydroxyquinolate, zinc bis(8-hydroxyquinolate), copper bis(8-hydroxyquinolate), manganese bis(8-hydroxyquinolate), aluminum tris(8-hydroxyquinolate), aluminum tris(2-methyl-8-hydroxyquinolate), gallium tris(8-hydroxyquinolate), beryllium bis(10-hydroxybenzo[h]quinoline), zinc bis(10-hydroxybenzo[h]quinoline), gallium bis(2-methyl-8-quinolinate) chloride, gallium bis(2-methyl-8-quinolinate)(o-cresol), aluminum bis(2-methyl-8-quinolinate)(1-naphthol), and gallium bis(2-methyl-8-quinolinate)(2-naphthol), and the like, but are not limited thereto.

[0261] In one embodiment of the present specification, in the electron injection layer, the electron transport layer, or the layer that simultaneously performs electron injection and electron transport, the heterocyclic compound of Chemical Formula 1 and the metal complex can be contained in a mass ratio of 0.5:1.5 to 1.5:0.5.

[0262] The above-described hole blocking layer is a layer that prevents holes from reaching a cathode, and can be formed under the same conditions as a hole injection layer. Specifically, there are oxadiazole derivatives or triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, and the like, but are not limited thereto.

[0263] ​​​One embodiment of the present specification provides a compound represented by the above Chemical Formula 1, and a composition including a metal complex.

[0264] The description of the metal complex included in the above composition is the same as that in the electron injection layer, the electron transport layer, or the layer simultaneously performing electron injection and electron transport.

[0265] In one embodiment of the present specification, in the above composition, the heterocyclic compound of Chemical Formula 1 and the metal complex can be included in a mass ratio of 0.5:1.5 to 1.5:0.5.

[0266] The organic light emitting device according to the present specification can be a top emission type, a bottom emission type, or a bidirectional emission type, depending on the materials used.

[0267] Mode for carrying out the invention

[0268] Hereinafter, in order to specifically describe the present specification, examples will be cited to be described in detail. However, the examples according to the present specification can be transformed into various different forms, and it is not explained that the scope of the present specification is limited to the examples described below. The examples of the present specification are provided in order to more completely describe the present specification to those skilled in the art.

[0269] Preparation Example 1-1: Preparation of Compound E1

[0270]

[0271] E1-A (20 g, 78.7 mmol) and E1-B (18.9 g, 78.7 mmol) were added to 400 mL of tetrahydrofuran under a nitrogen atmosphere, stirred and refluxed. Then, potassium carbonate (32.6 g, 236.1 mmol) was dissolved in 33 mL of water and added, and after sufficient stirring, tetrakis(triphenylphosphine)palladium (2.7 g, 2.4 mmol) was added. After 2 hours of reaction, after cooling to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. This was again added to 20 times 653 mL of chloroform and dissolved, washed with water 2 times, and the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to manufacture a white solid compound E1 (22.5 g, 69%, MS: [M+H] = 415). +

[0272] Preparation Example 1-4: Preparation of Compound E4

[0273]

[0274] ​Using each starting material as in the above reaction formula, the above compound E4 was produced by the same method as the production method of the above Production Example 1-1, except for this.

[0275] MS: [M+H] + = 515

[0276] Production Example 1-5: Production of Compound E5

[0277]

[0278] Using each starting material as in the above reaction formula, the above compound E5 was produced by the same method as the production method of the above Production Example 1-1, except for this.

[0279] MS: [M+H] + = 567

[0280] Production Example 1-7: Production of Compound E7

[0281]

[0282] Using each starting material as in the above reaction formula, the above compound E7 was produced by the same method as the production method of the above Production Example 1-1, except for this.

[0283] MS: [M+H] + = 615

[0284] Production Example 1-8: Production of Compound E8

[0285]

[0286] Using each starting material as in the above reaction formula, the above compound E8 was produced by the same method as the production method of the above Production Example 1-1, except for this.

[0287] MS: [M+H] + = 505

[0288] Production Example 1-9: Production of Compound E9

[0289]

[0290] Using each starting material as in the above reaction formula, the above compound E9 was produced by the same method as the production method of the above Production Example 1-1, except for this.

[0291] MS: [M+H] + = 520

[0292] Production Example 1-10: Production of Compound E10

[0293]

[0294] The above compound E10 was produced by the same method as the production method of Production Example 1-1, using each starting material as in the above reaction formula.

[0295] MS: [M+H] + = 632

[0296] Production Example 1-12: Production of Compound E12

[0297]

[0298] The above compound E12 was produced by the same method as the production method of Production Example 1-1, using each starting material as in the above reaction formula.

[0299] MS: [M+H] + = 573

[0300] Production Example 1-13: Production of Compound E13

[0301]

[0302] The above compound E13 was produced by the same method as the production method of Production Example 1-1, using each starting material as in the above reaction formula.

[0303] MS: [M+H] + = 507

[0304] Example 1-1.

[0305] ITO (indium tin oxide) was coated onto a glass substrate in a thin film at a thickness of 1500 A. The glass substrate on which ITO was coated in a thin film at a thickness of 1500 A was put into distilled water in which a detergent was dissolved, and washed using ultrasonic waves. At this time, the detergent was a product of Fischer Co., and the distilled water was distilled water filtered twice using a filter manufactured by Millipore Co. After the ITO was washed for 30 minutes, ultrasonic washing was repeated twice for 10 minutes using distilled water. After the distilled water washing was completed, ultrasonic washing was performed using solvents of isopropyl alcohol, acetone, and methanol, and drying was performed, and then the substrate was transported to a plasma cleaning machine. Further, the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transported to a vacuum vapor deposition machine.

[0306] On the ITO transparent electrode thus prepared, the following HI-A compound was coated at a thickness of 1000 A. A hole injection layer is formed by thermal vacuum evaporation to a thickness of [amount missing]. The following HAT compound is then sequentially vacuum-deposited onto the hole injection layer. and the following HT-A compounds This forms the first hole transport layer and the second hole transport layer.

[0307] Next, on the second hole transport layer, a light-emitting layer is formed by vacuum evaporation of the following BH compound and BD compound at a weight ratio of 25:1 with a film thickness of 20 nm.

[0308] On the aforementioned light-emitting layer, compound E1 manufactured in Manufacturing Example 1-1 and the following LiQ compound were vacuum-deposited in a 1:1 weight ratio, thereby achieving... The thickness forms an electron injection and transport layer. On this electron injection and transport layer, lithium fluoride (LiF) is sequentially applied... The thickness, using aluminum The cathode is formed by vapor deposition of a certain thickness.

[0309] During the above process, the evaporation rate of organic matter is maintained. to Lithium fluoride maintenance of the cathode The evaporation rate of aluminum maintains The evaporation rate is such that the vacuum level is maintained at 1×10⁻⁶ during evaporation. -7 Up to 5×10 -5 This led to the creation of organic light-emitting devices.

[0310]

[0311] Examples 1-4, 1-5, 1-7 to 1-10, 1-12 and 1-13.

[0312] Organic light-emitting devices were manufactured by replacing compound E1 in Examples 1-1 with compounds E4, E5, E7 to E10, E12 and E13 as described in Table 1 below, except that organic light-emitting devices were manufactured by the same method as in Examples 1-1.

[0313] Comparative Examples 1-1 to 1-14.

[0314] Organic light-emitting devices were manufactured by the same method as in Examples 1-1, except that compounds ET-A to ET-N, which are listed in Table 1 below, were used instead of compound E1 in Examples 1-1.

[0315]

[0316] The organic light emitting devices manufactured in Examples 1-1, 1-4, 1-5, 1-7 to 1-10, 1-12 and 1-13 and Comparative Examples 1-1 to 1-14 described above were measured for driving voltage and luminous efficiency at a current density of 10 mA / cm 2 The time (T90) until the initial luminance became 90% was measured at a current density of 20 mA / cm 2 The results described above are shown in Table 1 below.

[0317] [Table 1]

[0318]

[0319]

[0320] As shown in the description of Table 1 above, the compound represented by Chemical Formula 1 according to the present specification can be used in an organic material layer of an organic light emitting device which simultaneously performs electron injection and transport. Comparing Examples 1-1, 1-4, 1-5, 1-7 to 1-10, 1-12 and 1-13 of Table 1 above with Comparative Example 1-1, it can be confirmed that the organic light emitting device to which the heterocyclic compound of Chemical Formula 1 according to the present specification is applied exhibits significantly superior characteristics in terms of lifespan compared to the organic light emitting device to which the compound in which R1and R2combine with each other to form an aromatic ring is applied.

[0321] Comparing Examples 1-1, 1-4, 1-5, 1-7 to 1-10, 1-12 and 1-13 of Table 1 above with Comparative Examples 1-2 to 1-4, it can be confirmed that the organic light emitting device to which the heterocyclic compound of Chemical Formula 1 according to the present specification is applied exhibits significantly superior characteristics in terms of lifespan compared to the organic light emitting device to which the compound substituted with a fluorene group is applied.

[0322] Comparing Examples 1-1, 1-4, 1-5, 1-7 to 1-10, 1-12 and 1-13 of Table 1 above with Comparative Examples 1-5 and 1-7, it can be confirmed that the organic light emitting device to which the heterocyclic compound of Chemical Formula 1 according to the present specification is applied exhibits significantly superior characteristics in terms of efficiency and lifespan compared to the organic light emitting device to which the compound in which the linker group (L) contains a heterocyclic group is applied.

[0323] Comparing Examples 1-1, 1-4, 1-5, 1-7 to 1-10, 1-12 and 1-13 of Table 1 above with Comparative Examples 1-8 and 1-9, it can be confirmed that the organic light emitting device to which the heterocyclic compound of Chemical Formula 1 according to the present specification is applied exhibits significantly superior characteristics in terms of efficiency and lifespan compared to the organic light emitting device to which the compound in which xanthene or thioxanthene is included on both sides of the substituent is applied.

[0324] Comparing Examples 1-1, 1-4, 1-5, 1-7 to 1-10, 1-12 and 1-13 in Table 1 above with Comparative Examples 1-6 and 1-14, it can be confirmed that organic light-emitting devices using heterocyclic compounds of Formula 1 according to this specification exhibit significantly superior characteristics in terms of efficiency and lifetime compared to organic light-emitting devices using compounds where Z is N.

[0325] Comparing Examples 1-1, 1-4, 1-5, 1-7 to 1-10, 1-12 and 1-13 in Table 1 above with Comparative Examples 1-10 to 1-13, it can be confirmed that organic light-emitting devices using heterocyclic compounds of Formula 1 according to this specification exhibit significantly superior characteristics in terms of efficiency and lifetime compared to organic light-emitting devices using compounds containing substituted or unsubstituted benzimidazole groups of Ar1.

[0326] Example 2-1.

[0327] ITO (Indium Tin Oxide) A glass substrate coated with a thin film of ITO was immersed in distilled water containing detergent and washed using ultrasound. The detergent used was from Fischer, and the distilled water was filtered twice using a Millipore filter. After washing the ITO for 30 minutes, the process was repeated twice with distilled water for 10 minutes of ultrasonic washing. After the distilled water washing, the substrate was ultrasonically washed with a solvent of isopropanol, acetone, and methanol, dried, and then transferred to a plasma cleaner. Furthermore, the substrate was cleaned with oxygen plasma for 5 minutes before being transferred to a vacuum evaporation machine.

[0328] On the ITO transparent electrode prepared in this way, the following HI-A compound is applied... A hole injection layer is formed by thermal vacuum evaporation to a thickness of [amount missing]. The following HAT compound is then sequentially vacuum-deposited onto the hole injection layer. and the following HT-A compounds This forms the first hole transport layer and the second hole transport layer.

[0329] Next, on the second hole transport layer, a light-emitting layer is formed by vacuum evaporation of the following BH compound and BD compound at a weight ratio of 25:1 with a film thickness of 20 nm.

[0330] On the aforementioned light-emitting layer, compound E1 manufactured in Manufacturing Example 1-1 is applied... A hole-blocking layer is formed by vacuum evaporation of a material to a thickness of [amount missing]. ET-O and the following LiQ compound are vacuum-evaporated in a 1:1 weight ratio to achieve [the desired effect]. The thickness forms an electron injection and transport layer. On this electron injection and transport layer, lithium fluoride (LiF) is sequentially applied... The thickness, using aluminum The cathode is formed by vapor deposition of a certain thickness.

[0331] During the above process, the evaporation rate of organic matter is maintained. to Lithium fluoride maintenance of the cathode The evaporation rate of aluminum maintains The evaporation rate is such that the vacuum level is maintained at 1×10⁻⁶ during evaporation. -7 Up to 5×10 -5 This led to the creation of organic light-emitting devices.

[0332]

[0333] Examples 2-4, 2-5, 2-7 to 2-9, 2-11 and 2-12.

[0334] Organic light-emitting devices were manufactured by replacing compound E1 in Example 2-1 with compounds E4, E5, E7 to E9, E12 and E13 as described in Table 2 below, except that organic light-emitting devices were manufactured by the same method as in Example 2-1.

[0335] Comparative examples 2-1 to 2-14.

[0336] Organic light-emitting devices were manufactured by replacing compound E1 in Example 2-1 with compounds ET-A to ET-N from Table 2 below, except that the method was the same as that used in Example 2-1.

[0337]

[0338] The organic light-emitting devices manufactured in Examples 2-1, 2-4, 2-5, 2-7 to 2-9, 2-11 and 2-12 and Comparative Examples 2-1 to 2-14, at 10 mA / cm 2 The driving voltage and luminous efficiency were measured at a current density of 20 mA / cm². 2 The time (T90) at the given current density was measured relative to the initial brightness, which was 90%. The results are shown in Table 2 below.

[0339] [Table 2]

[0340]

[0341]

[0342] As shown in Table 2 above, the compound represented by chemical formula 1 according to this specification can be used in organic layers that can be used as hole blocking layers in organic light-emitting devices.

[0343] Comparing Example 2-1, 2-4, 2-5, 2-7 to 2-9, 2-11 and 2-12 of the above Table 2 with Comparative Example 2-1, it can be confirmed that the organic light emitting device to which the heterocyclic compound of Chemical Formula 1 according to the present specification is applied shows remarkably superior characteristics in terms of lifespan compared to the organic light emitting device to which the compound in which R1 and R2 combine with each other to form an aromatic ring is applied.

[0344] Comparing Example 2-1, 2-4, 2-5, 2-7 to 2-9, 2-11 and 2-12 of the above Table 2 with Comparative Examples 2-2 to 2-4, it can be confirmed that the organic light emitting device to which the heterocyclic compound of Chemical Formula 1 according to the present specification is applied shows remarkably superior characteristics in terms of lifespan compared to the organic light emitting device to which the compound substituted with a fluorenyl group is applied.

[0345] Comparing Example 2-1, 2-4, 2-5, 2-7 to 2-9, 2-11 and 2-12 of the above Table 2 with Comparative Examples 2-5 and 2-7, it can be confirmed that the organic light emitting device to which the heterocyclic compound of Chemical Formula 1 according to the present specification is applied shows remarkably superior characteristics in terms of efficiency and lifespan compared to the organic light emitting device to which the compound in which the linker group (L) contains a heterocyclic group is applied.

[0346] Comparing Example 2-1, 2-4, 2-5, 2-7 to 2-9, 2-11 and 2-12 of the above Table 2 with Comparative Examples 2-8 and 2-9, it can be confirmed that the organic light emitting device to which the heterocyclic compound of Chemical Formula 1 according to the present specification is applied shows remarkably superior characteristics in terms of efficiency and lifespan compared to the organic light emitting device to which the compound in which both sides of xanthene or thioxanthene contain a substituent is applied.

[0347] Comparing Example 2-1, 2-4, 2-5, 2-7 to 2-9, 2-11 and 2-12 of the above Table 2 with Comparative Examples 2-6 and 2-14, it can be confirmed that the organic light emitting device to which the heterocyclic compound of Chemical Formula 1 according to the present specification is applied shows remarkably superior characteristics in terms of efficiency and lifespan compared to the organic light emitting device to which the compound in which Z is N is applied.

[0348] Comparing Example 2-1, 2-4, 2-5, 2-7 to 2-9, 2-11 and 2-12 of the above Table 2 with Comparative Examples 2-10 to 2-13, it can be confirmed that the organic light emitting device to which the heterocyclic compound of Chemical Formula 1 according to the present specification is applied shows remarkably superior characteristics in terms of efficiency and lifespan compared to the organic light emitting device to which the compound in which Ar1 contains a substituted or unsubstituted benzimidazolyl group is applied.

Claims

1. A heterocyclic compound of the following formula 1: ###0001### Formula 1 Formula 1 In the formula 1, Z is O or S, R1 and R2 are the same as or different from each other, and are an alkyl group having 1 to 10 carbon atoms, or are bonded to each other to form a six-membered ring, L is a direct bond, a phenylene group, a biphenylene group, or a naphthylene group, a is an integer of 1 to 3, and when a is 2 or more, two or more L's are the same as or different from each other, b is 1, Ar1 is selected from any one of the following structures, In the structure, for the moiety to be linked to L, c is an integer of 1 to 5, and when c is 2 or more, two or more G17's are the same as or different from each other, X1 to X4 are the same as or different from each other, and are each independently N or CR3, but two or more of X1 to X4 are N, R3 is hydrogen, G1 to G15 and G17 are the same as or different from each other, and are each independently hydrogen, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted fluoranthenyl group, or a substituted or unsubstituted dibenzofuranyl group, wherein the substituted or unsubstituted means substituted with one or two or more substituents selected from a cyano group, an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, and a heterocyclic group having 2 to 30 carbon atoms, or a substituent connected with two or more substituents of the above-mentioned substituents, or not having any substituent.

2. The heterocyclic compound according to claim 1, wherein, The formula 1 is any one of the following formulas 1-1 to 1-4: Formula 1-1 Formula 1-2 Formula 1-3 Formula 1-4 In the formulas 1-1 to 1-4, Z, R1, R2, a, L, and Ar1 are the same as the definitions in the formula 1.

3. The heterocyclic compound according to claim 1, wherein, The heterocyclic compound of the formula 1 is any one of the following structures:

4. An organic light emitting device, wherein, including: a first electrode, a second electrode disposed opposite to the first electrode, and one or more organic layers disposed between the first electrode and the second electrode, one or more of the organic layers containing the heterocyclic compound according to any one of claims 1 to 3.

5. The organic light emitting device according to claim 4, wherein, The organic layer includes an electron injection layer, an electron transport layer, or a layer that simultaneously performs electron injection and electron transport, the electron injection layer, the electron transport layer, or the layer that simultaneously performs electron injection and electron transport containing the heterocyclic compound.

6. The organic light emitting device according to claim 5, wherein, The electron injection layer, the electron transport layer, or the layer that simultaneously performs electron injection and electron transport further contains a metal complex.

7. The organic light emitting device according to claim 4, wherein, The organic layer includes a hole blocking layer, the hole blocking layer containing the heterocyclic compound.

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