Heterocyclic compound and organic light-emitting device containing the same

Abstract

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

Description

Technical Field

[0001] This application claims the benefit of the filing date of Korean Patent Application No. 10-2020-0113307, filed with the Korean Intellectual Property Office on September 4, 2020, and all of its contents are incorporated herein by reference.

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

Background Art

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

[0004] An organic light-emitting device has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to 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 a pair, and then emit light while disappearing. The organic thin film can be composed of a single layer or multiple layers as required.

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

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

[0007] There is a need for research on an organic light-emitting device including a compound having a chemical structure that can satisfy the conditions required for a substance usable in an organic light-emitting device, such as suitable energy levels, electrochemical stability, and thermal stability, and can play various roles required for an organic light-emitting device depending on substituents.

Summary of the Invention

Problems to be Solved by the Invention

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

Means for Solving the Problems

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

[0010]

Chem.

[0011] Further, according to one embodiment of the present application, there is provided an organic light-emitting device including a first electrode; a second electrode provided opposite to the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers contain a heterocyclic compound represented by Chemical Formula 1.

Advantages of the Invention

[0012] The compounds described in this specification can be used as materials for the organic layer of an organic light-emitting device. In the organic light-emitting device, the compounds can serve roles such as a hole injection material, a hole transport material, a light-emitting material, an electron transport material, an electron injection material, an electron blocking material, a hole blocking material, etc. In particular, the compounds can be used as a hole transport material, a light-emitting material, or an electron blocking material of an organic light-emitting device.

[0013] In particular, the heterocyclic compound according to this application has an amine-based substituent and a -(L1)m-(Z1)n substituent on the naphthobenzofuran structure which is the core structure, and can strengthen hole characteristics on the naphthobenzofuran skeleton which is the core structure, and adjust a wide band gap and a high T1 value. Therefore, when the compound is used as a hole transport material, a light-emitting material, or an electron blocking material of an organic light-emitting device, it is characterized by showing excellent efficiency.

Brief Description of the Drawings

[0014]

Figure 1

Figure 2

Figure 3

Explanation of Reference Numerals

[0015] 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

Best Mode for Carrying Out the Invention

[0016] Hereinafter, the present application will be described in detail.

[0017] In the present specification, the halogen may be fluorine, chlorine, bromine, or iodine.

[0018] In the present specification, the alkyl group includes a straight-chain or branched-chain having 1 to 60 carbon atoms and may be further substituted by other substituents. The number of carbon atoms of the alkyl group may be 1 to 60, specifically 1 to 40, and more specifically 1 to 20. Specific examples include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methyl-butyl group, 1-ethyl-butyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl-2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, cyclopentylmethyl group, cyclohexylmethyl group, octyl group, n-octyl group, tert-octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2,2-dimethylheptyl group, 1-ethyl-propyl group, 1,1-dimethyl-propyl group, isohexyl group, 2-methylpentyl group, 4-methylhexyl group, 5-methylhexyl group, etc., but are not limited thereto.

[0019] In this specification, the alkenyl group includes a straight-chain or branched-chain having 2 to 60 carbon atoms, and may be further substituted with other substituents. The number of carbon atoms of the alkenyl group may be 2 to 60, specifically 2 to 40, and more specifically 2 to 20. Specific examples include a vinyl group, 1-propenyl group, isopropenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 3-methyl-1-butenyl group, 1,3-butadienyl group, allyl group, 1-phenylvinyl-1-yl group, 2-phenylvinyl-1-yl group, 2,2-diphenylvinyl-1-yl group, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl group, 2,2-bis(diphenyl-1-yl)vinyl-1-yl group, stilbenyl group, styrenyl group, etc., but are not limited thereto.

[0020] In this specification, the alkynyl group includes a straight-chain or branched-chain having 2 to 60 carbon atoms, and may be further substituted with other substituents. The number of carbon atoms of the alkynyl group may be 2 to 60, specifically 2 to 40, and more specifically 2 to 20.

[0021] In this specification, the alkoxy group may be a straight-chain, branched-chain or cyclic chain. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 20. Specifically, 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, p-methylbenzyloxy, etc. are included, but are not limited thereto.

[0022] In this specification, the cycloalkyl group includes a monocyclic or polycyclic group having 3 to 60 carbon atoms, and may be further substituted with other substituents. Here, the polycyclic group means a group in which the cycloalkyl group is directly linked or condensed with another cyclic group. Here, the other cyclic group may be a cycloalkyl group, but may also be another type of cyclic group, for example, a heterocycloalkyl group, an aryl group, a heteroaryl group, etc. The number of carbon atoms of the cycloalkyl group may be 3 to 60, specifically 3 to 40, and more specifically 5 to 20. Specifically, cyclopropyl group, cyclobutyl group, cyclopentyl group, 3-methylcyclopentyl group, 2,3-dimethylcyclopentyl group, cyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 2,3-dimethylcyclohexyl group, 3,4,5-trimethylcyclohexyl group, 4-tert-butylcyclohexyl group, cycloheptyl group, cyclooctyl group, etc. may be mentioned, but not limited thereto.

[0023] In this specification, the heterocycloalkyl group contains O, S, Se, N, or Si as a heteroatom, includes a monocyclic or polycyclic group having 2 to 60 carbon atoms, and may be further substituted with other substituents. Here, the polycyclic group means a group in which the heterocycloalkyl group is directly linked or condensed with another cyclic group. Here, the other cyclic group may be a heterocycloalkyl group, but may also be another type of cyclic group, for example, a cycloalkyl group, an aryl group, a heteroaryl group, etc. The number of carbon atoms of the heterocycloalkyl group may be 2 to 60, specifically 2 to 40, and more specifically 3 to 20.

[0024] In this specification, the aryl group includes a monocyclic or polycyclic group having 6 to 60 carbon atoms, and may be further substituted with other substituents. Here, the polycyclic group means a group in which the aryl group is directly linked or condensed with another cyclic group. Here, the other cyclic group may be an aryl group, but may also be other types of cyclic groups, such as a cycloalkyl group, a heterocycloalkyl group, a heteroaryl group, etc. The number of carbon atoms of the aryl group may be 6 to 60, specifically 6 to 40, and more specifically 6 to 25. Specific examples of the aryl group include a phenyl group, a biphenyl group, a triphenyl group, a naphthyl group, an anthryl group, a chrysenyl group, a phenanthrenyl group, a perylenyl group, a fluoranthenyl group, a triphenylenyl group, a phenalenyl group, a pyrenyl group, a tetracenyl group, a pentacenyl group, an indenyl group, an acenaphthylenyl group, a 2,3-dihydro-1H-indenyl group, and condensed ring groups thereof, but are not limited thereto.

[0025] In this specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.

[0026] When the fluorenyl group is substituted,

Chemical formula

[0027] In this specification, the heteroaryl group contains S, O, Se, N, or Si as a heteroatom, includes a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may be further substituted with other substituents. Here, the polycyclic ring means a group in which the heteroaryl group is directly linked or condensed with another cyclic group. Here, the other cyclic group may be a heteroaryl group, but may also be other types of cyclic groups, for example, a cycloalkyl group, a heterocycloalkyl group, an aryl group, and the like. The carbon number of the heteroaryl group may be 2 to 60, specifically 2 to 40, and more specifically 3 to 25.Specific examples of the heteroaryl group include, but are not limited to, pyridyl group, pyrrolyl group, pyrimidyl group, pyridazinyl group, furanyl group, thiophenyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, triazolyl group, furazanyl group, oxadiazolyl group, thiadiazolyl group, dithiazolyl group, tetrazolyl group, pyranyl group, thiopyranyl group, diazinyl group, oxazinyl group, thiazinyl group, dioxinyl group, triazinyl group, tetrazinyl group, quinolyl group, isoquinolyl group, quinazolinyl group, isoquinazolinyl group, quinoxalyl group, naphthyridyl group, acridinyl group, phenanthridinyl group, imidazopyridinyl group, diazaphenalenyl group, triazaindenyl group, indolyl group, indolizinyl group, benzothiazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiophenyl group, benzofuranyl group, dibenzothiophenyl group, dibenzofuranyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, phenazinyl group, dibenzosilolyl group, spirobi(dibenzosilol), 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]azepinyl group, 9,10-dihydroacridinyl group, phenanthradinyl group, phenothiatiazinyl group, phthalazinyl group, naphthyridinyl group, phenanthrolinyl group, benzo[c][1,2,5]thiadiazolyl group, 5,10-dihydrodibenzo[b,e][1,4]azasilinyl, pyrazolo[1,5-c]quinazolinyl group, pyrido[1,2-b]indazolyl group, pyrido[1,2-a]imidazo[1,2-e]indolinyl group, 5,11-dihydroindenol[1,2-b]carbazolyl group, etc.

[0028] In this specification, the amine group may be selected from the group consisting of a monoalkylamine group; a monoarylamine group; a monoheteroarylamine group; -NH2; a dialkylamine group; a diarylamine group; a diheteroarylamine group; an alkylarylamine group; an alkylheteroarylamine group; and an arylheteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, a dibiphenylamine group, an anthracenylamine group, a 9-methyl-anthracenylamine group, a diphenylamine group, a phenylnaphthylamine group, a ditolylamine group, a phenyltolylamine group, a triphenylamine group, a biphenylnaphthylamine group, a phenylbiphenylamine group, a biphenylfluorenylamine group, a phenyltriphenylenylamine group, a biphenyltriphenylenylamine group, etc., but are not limited thereto.

[0029] In this specification, the arylene group means a group having two bonding positions to an aryl group, that is, a divalent group. These may be applied with the description of the aryl group mentioned above, except that each is a divalent group. Further, the heteroarylene group means a group having two bonding positions to a heteroaryl group, that is, a divalent group. These may be applied with the description of the heteroaryl group mentioned above, except that each is a divalent group.

[0030] In this specification, the phosphine oxide group is represented by -P(=O)R101R102, and R101 and R102 may be the same as or different from each other and each independently be a substituent consisting of at least one of hydrogen; deuterium; a halogen group; an alkyl group; an alkenyl group; an alkoxy group; a cycloalkyl group; an aryl group; and a heterocyclic group. Specific examples of the phosphine oxide group include a diphenylphosphine oxide group, a dinaphthylphosphine oxide, etc., but are not limited thereto.

[0031] In this specification, a silyl group contains Si and is a substituent in which the Si atom is directly linked as a radical, represented by -SiR104R105R106, where R104 to R106 may be the same as or different from each other and are each independently a substituent composed of at least one of hydrogen; deuterium; a halogen group; an alkyl group; an alkenyl group; an alkoxy group; a cycloalkyl group; an aryl group; and a heterocyclic group. Specific examples of the silyl group include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, and a phenylsilyl group.

[0032] In this specification, an "adjacent" group can mean a substituent substituted on an atom directly linked to the atom on which the said substituent is substituted, a substituent located closest in steric structure to the said substituent, or another substituent substituted on the atom on which the said substituent is substituted. For example, two substituents substituted at the ortho position in a benzene ring and two substituents substituted on the same carbon in an aliphatic ring can be interpreted as "adjacent" groups to each other.

[0033] For an aliphatic or aromatic hydrocarbon ring or heterocyclic ring that can be formed by adjacent groups, the structures exemplified as the cycloalkyl group, cycloheteroalkyl group, aryl group, and heteroaryl group described above may be applied, except that it is not a monovalent group.

[0034] In this specification, the term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is replaced by another substituent, and the position to be substituted is not limited as long as it is the position where a hydrogen atom can be substituted, that is, the position where a substituent can be substituted. When two or more substitutions occur, the two or more substituents may be the same as or different from each other.

[0035] As used herein, "substituted or unsubstituted" means substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium; a halogen group; a cyano group; C1-C60 linear or branched alkyl; C2-C60 linear or branched alkenyl; C2-C60 linear or branched alkynyl; C3-C60 monocyclic or polycyclic cycloalkyl; C2-C60 monocyclic or polycyclic heterocycloalkyl; C6-C60 monocyclic or polycyclic aryl; C2-C60 monocyclic or polycyclic heteroaryl; -SiRR’R’’; -P(=O)RR’; and -NRR’, or substituted or unsubstituted with a substituent formed by linking two or more substituents selected from the exemplified substituents. Each of R, R’, and R’’ is the same as or different from one another and is independently a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group.

[0036] As used herein, "when no substituent is shown in the chemical formula or the structure of the compound" means that a hydrogen atom is bonded to a carbon atom. However, since deuterium ( 2 H, Deuterium) is an isotope of hydrogen, some of the hydrogen atoms may be deuterium.

[0037] In one embodiment of the present application, "when no substituent is shown in the chemical formula or the structure of the compound" may mean that all positions that can come as substituents are hydrogen or deuterium. That is, in the case of deuterium, which is an isotope of hydrogen, some of the hydrogen atoms may be deuterium, which is an isotope, and in this case, the deuterium content may be 0% to 100%.

[0038] In one embodiment of the present application, in the case where "no substituent is shown in the chemical formula or the structure of the compound", if deuterium content is not explicitly excluded, such as when the deuterium content is 0% and the hydrogen content is 100%, hydrogen and deuterium may be used mixedly in the compound. That is, when expressing "substituent X is hydrogen", it does not exclude deuterium such as when the hydrogen content is 100% and the deuterium content is 0%, and it may mean a state where hydrogen and deuterium are mixed.

[0039] In one embodiment of the present application, deuterium is one of the isotopes of hydrogen, and it is an element having a deuteron composed of 1 proton and 1 neutron as its nucleus. It may be represented by hydrogen-2, and the element symbol may be denoted as D or 2H.

[0040] In one embodiment of the present application, isotopes, which mean atoms having the same atomic number (Z) but different mass numbers (A), can also be interpreted as elements having the same number of protons but different numbers of neutrons.

[0041] In one embodiment of the present application, the meaning of the content T% of a specific substituent can be defined as T2 / T1×100 = T% when the total number of substituents that the basic compound may have is defined as T1 and the number of a specific substituent among them is defined as T2.

[0042] That is, in one example,

Chemical formula

[0043] [Chem.] Also, in one embodiment of the present application, in the case of a "phenyl group with a deuterium content of 0%", it may mean a phenyl group that does not contain deuterium atoms, that is, a phenyl group having 5 hydrogen atoms.

[0044] In this specification, a structure represented in the form of -(La)m1-(Za)n1 in a chemical formula may mean a substituent. La is a linker, Za is a substituent, and when m1 is 2 or more, it can be interpreted that the linkers La are connected to each other. For example, when m1 is 3, it can be interpreted as -(La)-(La)-(La)-(Za)n1.

[0045] In one embodiment of the present application, a compound represented by the chemical formula 1 is provided.

[0046] The heterocyclic compound of Chemical Formula 1 of the present application has an amine-based substituent and a substituent of -(L1)m-(Z1)n having hole characteristics. When it is used as a hole transport layer, a hole transport auxiliary layer, or a light-emitting layer of an organic light-emitting device in the future, the lone pair electrons of the amine substituent can improve the flow of holes and enhance the hole transport ability of the hole transport layer. When it is used as an electron blocking layer, it can suppress the deterioration of the hole transport material generated by electrons invading the hole transport layer.

[0047] Also, by bonding the amine moieties of the substituent of -(L1)m-(Z1)n with enhanced hole characteristics and the amine-based substituent to each other, the planarity and glass transition temperature of the amine derivative are increased to enhance the thermal stability of the heterocyclic compound, thereby having the characteristic of improving the lifespan of the organic light-emitting device including this.

[0048] In addition, by adjusting the band gap and T1 value, the hole transport ability is improved and the molecular stability is also enhanced. Therefore, the driving voltage of the device can be lowered, the light efficiency can be improved, and the lifetime characteristics of the device can be improved by the thermal stability of the compound.

[0049] In one embodiment of the present application, the chemical formula 1 may be represented by any one of the following chemical formulas 2 to 5.

[0050]

Chem.

Chem.

Chem.

Chem.

[0051] In one embodiment of the present application, R1 to R6 are the same as or different from each other, and each independently is hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1-C60 alkyl group; substituted or unsubstituted C2-C60 alkenyl group; substituted or unsubstituted C2-C60 alkynyl group; substituted or unsubstituted C1-C60 alkoxy group; substituted or unsubstituted C3-C60 cycloalkyl group; substituted or unsubstituted C2-C60 heterocycloalkyl group; substituted or unsubstituted C6-C60 aryl group; substituted or unsubstituted C2-C60 heteroaryl group; -P(=O)RR'; and -SiRR'R'', or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6-C60 aliphatic or aromatic hydrocarbon ring, or a substituted or unsubstituted C2-C60 aliphatic or aromatic heterocycle.

[0052] In another embodiment, R1 to R6 are the same as or different from each other, and each independently is hydrogen; deuterium; substituted or unsubstituted C1-C60 alkyl group; substituted or unsubstituted C6-C60 aryl group; substituted or unsubstituted C2-C60 heteroaryl group; -P(=O)RR'; or -SiRR'R''.

[0053] In yet another embodiment, R1 to R6 are the same as or different from each other, and each independently is hydrogen; deuterium; substituted or unsubstituted C1-C40 alkyl group; substituted or unsubstituted C6-C40 aryl group; substituted or unsubstituted C2-C40 heteroaryl group; -P(=O)RR'; or -SiRR'R''.

[0054] In still another embodiment, R1 to R6 are the same as or different from each other, and each independently is hydrogen; deuterium; C1-C40 alkyl group; C6-C40 aryl group; C2-C40 heteroaryl group; -P(=O)RR'; or -SiRR'R''.

[0055] In yet another embodiment, R1 to R6 may be hydrogen; or deuterium.

[0056] In one embodiment of the present application, R, R', and R'' may be the same as or different from each other, and each independently may be a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group.

[0057] In another embodiment, R, R', and R'' may be the same as or different from each other, and each independently may be a substituted or unsubstituted C6-C60 aryl group.

[0058] In yet another embodiment, R, R', and R'' may be the same as or different from each other, and each independently may be a substituted or unsubstituted C6-C60 monocyclic or polycyclic aryl group.

[0059] In still another embodiment, R, R', and R'' may be the same as or different from each other, and each independently may be a substituted or unsubstituted C6-C40 monocyclic aryl group.

[0060] In still another embodiment, R, R', and R'' may be the same as or different from each other, and each independently may be a C6-C20 monocyclic aryl group.

[0061] In still another embodiment, R, R', and R'' may be a phenyl group.

[0062] In one embodiment of the present application, L1 and L2 may be the same as or different from each other, and each independently may be a direct bond; a substituted or unsubstituted C6-C60 arylene group; or a substituted or unsubstituted C2-C60 heteroarylene group.

[0063] In another embodiment, L1 and L2 may be the same as or different from each other, and each independently may be a direct bond; or an optionally substituted C6-C60 arylene group.

[0064] In yet another embodiment, L1 and L2 may be the same as or different from each other, and each independently may be a direct bond; or an optionally substituted C6-C40 arylene group.

[0065] In still another embodiment, L1 and L2 may be the same as or different from each other, and each independently may be a direct bond; or a C6-C20 arylene group.

[0066] In still another embodiment, L1 and L2 may be the same as or different from each other, and each independently may be a direct bond; a monocyclic C6-C10 arylene group; or a polycyclic C10-C20 arylene group.

[0067] In still another embodiment, L1 and L2 may be the same as or different from each other, and each independently may be a direct bond; a phenylene group; or a biphenylene group.

[0068] In one embodiment of the present application, Z1 may be an optionally substituted C1-C60 alkyl group; an optionally substituted C2-C60 alkenyl group; an optionally substituted C2-C60 alkynyl group; an optionally substituted C1-C60 alkoxy group; an optionally substituted C3-C60 cycloalkyl group; an optionally substituted C2-C60 heterocycloalkyl group; an optionally substituted C6-C60 aryl group; an optionally substituted fluorenyl group; an optionally substituted C2-C60 heteroaryl group; -P(=O)RR'; or -SiRR'R''.

[0069] In another embodiment, Z1 may be a substituted or unsubstituted C6-C60 aryl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted C2-C60 heteroaryl group; -P(=O)RR'; or -SiRR'R''.

[0070] In yet another embodiment, Z1 may be a substituted or unsubstituted C6-C60 aryl group; a substituted or unsubstituted fluorenyl group; or a substituted or unsubstituted C2-C60 heteroaryl group.

[0071] In still yet another embodiment, Z1 may be a substituted or unsubstituted C6-C40 aryl group; a substituted or unsubstituted fluorenyl group; or a substituted or unsubstituted C2-C40 heteroaryl group.

[0072] In still yet another embodiment, Z1 may be a C6-C40 aryl group; a fluorenyl group substituted or unsubstituted with one or more substituents selected from the group consisting of a C1-C10 alkyl group and a C6-C20 aryl group; or a C2-C40 heteroaryl group.

[0073] In still yet another embodiment, Z1 may be a C6-C40 aryl group; a fluorenyl group substituted or unsubstituted with one or more substituents selected from the group consisting of a C1-C10 alkyl group and a C6-C20 aryl group; or a C2-C40 heteroaryl group containing one or more of O, S, and N as heteroatoms.

[0074] In still yet another embodiment, Z1 may be a phenyl group; a biphenyl group; a naphthyl group; a dimethylfluorenyl group; a diphenylfluorenyl group; a spirobifluorenyl group; a phenanthrenyl group; a triphenylenyl group; a terphenyl group; a dibenzofuran group; a dibenzothiophene group, or a carbazole group.

[0075] In one embodiment of the present application, the chemical formula 1 may be represented by any one of the following chemical formulas 6 to 9.

[0076]

Chem.

Chem.

Chem.

Chem.

[0077] In one embodiment of the present application, R11 to R18 are the same as or different from each other, and each independently is hydrogen; deuterium; halogen; cyano group; substituted or unsubstituted C1-C60 alkyl group; substituted or unsubstituted C2-C60 alkenyl group; substituted or unsubstituted C2-C60 alkynyl group; substituted or unsubstituted C1-C60 alkoxy group; substituted or unsubstituted C3-C60 cycloalkyl group; substituted or unsubstituted C2-C60 heterocycloalkyl group; substituted or unsubstituted C6-C60 aryl group; substituted or unsubstituted C2-C60 heteroaryl group; -P(=O)RR'; and -SiRR'R'', or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6-C60 aliphatic or aromatic hydrocarbon ring, or a substituted or unsubstituted C2-C60 aliphatic or aromatic heterocyclic ring.

[0078] In another embodiment, R11 to R18 may be the same as or different from each other, and each independently may be selected from the group consisting of hydrogen; deuterium; substituted or unsubstituted C6-C60 aryl group; substituted or unsubstituted C2-C60 heteroaryl group; -P(=O)RR'; and -SiRR'R''.

[0079] In yet another embodiment, R11 to R18 may be the same as or different from each other, and each independently may be hydrogen; deuterium; a substituted or unsubstituted C6-C40 aryl group; a substituted or unsubstituted C2-C40 heteroaryl group; -P(=O)RR'; and -SiRR'R'', and may be selected from the group consisting of them.

[0080] In still another embodiment, R11 to R18 may be hydrogen; or deuterium.

[0081] In one embodiment of the present application, R21 and R22 may be the same as or different from each other, and each independently may be a substituted or unsubstituted C1-C60 alkyl group; or a substituted or unsubstituted C6-C60 aryl group, or two or more adjacent groups may be bonded to each other to form a substituted or unsubstituted C6-C60 aliphatic or aromatic hydrocarbon ring, or a substituted or unsubstituted C2-C60 aliphatic or aromatic heterocyclic ring.

[0082] In another embodiment, R21 and R22 may be the same as or different from each other, and each independently may be a substituted or unsubstituted C1-C40 alkyl group; or a substituted or unsubstituted C6-C40 aryl group, or two or more adjacent groups may be bonded to each other to form a substituted or unsubstituted C6-C40 aliphatic or aromatic hydrocarbon ring.

[0083] In yet another embodiment, R21 and R22 may be the same as or different from each other, and each independently may be a C1-C40 alkyl group; or a C6-C40 aryl group, or two or more adjacent groups may be bonded to each other to form a C6-C40 aliphatic or aromatic hydrocarbon ring.

[0084] In still another embodiment, R21 and R22 may be the same as or different from each other, and each independently may be a C1-C10 alkyl group; or a C6-C10 aryl group, or two or more adjacent groups may be bonded to each other to form a C6-C30 aliphatic or aromatic hydrocarbon ring.

[0085] In yet another embodiment, R21 and R22 are the same as or different from each other, and each independently is a methyl group; or a phenyl group, or two or more adjacent groups to each other may be bonded to each other to form a fluorenyl ring.

[0086] In yet another embodiment, R21 and R22 may be the same as each other.

[0087] In one embodiment of the present application, Ar1 and Ar2 are the same as or different from each other, and each independently is a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C6-C60 aryl group; a substituted or unsubstituted fluorenyl group; or a substituted or unsubstituted C2-C60 heteroaryl group.

[0088] In another embodiment, Ar1 and Ar2 are the same as or different from each other, and each independently is a substituted or unsubstituted C1-C40 alkyl group; a substituted or unsubstituted C6-C40 aryl group; a substituted or unsubstituted fluorenyl group; or a substituted or unsubstituted C2-C40 heteroaryl group.

[0089] In still another embodiment, Ar1 and Ar2 are the same as or different from each other, and each independently is a substituted or unsubstituted C6-C40 aryl group substituted with one or more substituents selected from the group consisting of a C6-C40 aryl group and a C2-C40 heteroaryl group; a substituted or unsubstituted fluorenyl group substituted with one or more substituents selected from the group consisting of a C6-C40 aryl group and a C1-C20 alkyl group; or a C2-C40 heteroaryl group.

[0090] In yet another embodiment, Ar1 and Ar2 may be the same as or different from each other, and each independently may be a biphenyl group; a terphenyl group; a phenanthrenyl group; a naphthyl group; a triphenylenyl group; a dimethylfluorenyl group; a diphenylfluorenyl group; a spirobifluorenyl group; a dibenzofuran group; a dibenzothiophene group; or a phenyl group which is unsubstituted or substituted with one or more substituents selected from the group consisting of a dibenzofuran group, a dibenzothiophene group, and a biphenyl group.

[0091] In one embodiment of the present application, the

Chemical formula

[0092]

Chemical formula

Chemical formula

Chemical formula

Chemical formula

[0093] In one embodiment of the present application, the definitions of R41 and R42 are the same as those of R21 and R22.

[0094] In one embodiment of the present application, the definitions of R31 to R34 are the same as those of R11 to R18.

[0095] In one embodiment of the present application, L11 may be a direct bond; a substituted or unsubstituted C6-C60 arylene group; or a substituted or unsubstituted C2-C60 heteroarylene group.

[0096] In other embodiments, L11 may be a direct bond; a substituted or unsubstituted C6-C40 arylene group; or a substituted or unsubstituted C2-C40 heteroarylene group.

[0097] In still other embodiments, L11 may be a direct bond; or a substituted or unsubstituted C6-C40 arylene group.

[0098] In yet other embodiments, L11 may be a direct bond; or a C6-C40 arylene group.

[0099] In yet other embodiments, L11 may be a direct bond; or a C6-C30 arylene group.

[0100] In yet other embodiments, L11 may be a direct bond; or a phenylene group.

[0101] In one embodiment of the present application, Ar11 may be a substituted or unsubstituted C6-C60 aryl group.

[0102] In another embodiment, Ar11 may be a substituted or unsubstituted C6-C40 aryl group.

[0103] In still another embodiment, Ar11 may be a substituted or unsubstituted C6-C20 aryl group.

[0104] In yet another embodiment, Ar11 may be a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted naphthyl group; or a substituted or unsubstituted triphenylenyl group.

[0105] In still other embodiments, Ar11 may be a phenyl group which is unsubstituted or substituted with one or more substituents selected from the group consisting of a biphenyl group, a terphenyl group, a phenanthrenyl group, a naphthyl group, a triphenylenyl group, or a dibenzofuran group, a dibenzothiophene group, and a biphenyl group.

[0106] In one embodiment of the present application, the chemical formula 7 may be represented by any one of the following chemical formulas 7-1 to 7-4.

[0107]

Chem.

Chem.

Chem.

Chem.

[0108] In one embodiment of the present application, the chemical formula 8 may be represented by any one of the following chemical formulas 8-1 to 8-4.

[0109]

Chem.

Chem.

Chem.

Chem.

[0110] According to one embodiment of the present application, the above chemical formula 1 may be represented by any one of the following compounds, but is not limited thereto.

[0111]

Chemical formula

[0112] Also, by introducing various substituents into the structure of Chemical Formula 1, while enabling fine adjustment of the energy band gap, the properties at the interface between organic substances can be improved, and the uses of the substances can be diversified.

[0113] Also, in one embodiment of the present application, there is provided an organic light-emitting device including a first electrode; a second electrode provided opposite to the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers contain a heterocyclic compound represented by Chemical Formula 1.

[0114] In another embodiment, there is provided an organic light-emitting device including a first electrode; a second electrode provided opposite to the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers contain one kind of the heterocyclic compound represented by Chemical Formula 1.

[0115] In still another embodiment, there is provided an organic light-emitting device including a first electrode; a second electrode provided opposite to the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers contain two kinds of the heterocyclic compound represented by Chemical Formula 1.

[0116] Specific details regarding the heterocyclic compound represented by Chemical Formula 1 are as described above.

[0117] In one embodiment of the present application, the first electrode may be an anode, and the second electrode may be a cathode.

[0118] In another embodiment, the first electrode may be a cathode, and the second electrode may be an anode.

[0119] In one embodiment of the present application, the organic light-emitting device may be a blue organic light-emitting device, and the heterocyclic compound represented by Chemical Formula 1 may be used as a material for the blue organic light-emitting device. For example, the heterocyclic compound represented by Chemical Formula 1 may be included in the host material of the blue light-emitting layer of the blue organic light-emitting device.

[0120] In one embodiment of the present application, the organic light-emitting device may be a green organic light-emitting device, and the heterocyclic compound represented by Chemical Formula 1 may be used as a material for the green organic light-emitting device. For example, the heterocyclic compound represented by Chemical Formula 1 may be included in the host material of the green light-emitting layer of the green organic light-emitting device.

[0121] In one embodiment of the present application, the organic light-emitting device may be a red organic light-emitting device, and the heterocyclic compound represented by Chemical Formula 1 may be used as a material for the red organic light-emitting device. For example, the heterocyclic compound represented by Chemical Formula 1 may be included in the host material of the red light-emitting layer of the red organic light-emitting device.

[0122] The organic light-emitting device of the present invention may be manufactured by the manufacturing methods and materials of ordinary organic light-emitting devices, except that one or more organic layers are formed using the above-mentioned heterocyclic compound.

[0123] The heterocyclic compound may be formed in the organic layer not only by vacuum deposition but also by solution coating during the manufacture of the organic light-emitting device. Here, the solution coating method means spin coating, dip coating, inkjet printing, screen printing, spraying method, roll coating, etc., but is not limited thereto.

[0124] The organic layer of the organic light-emitting device of the present invention may have a single-layer structure, or may have a multilayer structure in which two or more organic layers are stacked. For example, the organic light-emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. as the organic layer. However, the structure of the organic light-emitting device is not limited thereto, and it may further include a smaller number of organic layers.

[0125] In the organic light-emitting device of the present invention, the organic layer may include a light-emitting layer, and the light-emitting layer may include the heterocyclic compound.

[0126] In other organic light-emitting devices, the organic layer includes a light-emitting layer, the light-emitting layer includes a host material, and the host material may include the heterocyclic compound.

[0127] Also, as an example, the organic layer containing the heterocyclic compound may contain the heterocyclic compound represented by Chemical Formula 1 as a host and may be used together with an iridium-based dopant.

[0128] In the organic light-emitting device of the present invention, the organic layer includes an electron injection layer or an electron transport layer, and the electron transport layer or the electron injection layer may include the heterocyclic compound.

[0129] In other organic light-emitting devices, the organic layer includes an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer may include the heterocyclic compound.

[0130] In the organic light-emitting device of the present invention, the organic layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer may include the heterocyclic compound.

[0131] The organic light-emitting device of the present invention may further include one layer or two or more layers selected from the group consisting of a light-emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer.

[0132] Figures 1 to 3 illustrate the stacking order of the electrodes and organic layers of an organic light-emitting device according to an embodiment of the present application. However, the scope of the present application is not limited by these drawings, and the structures of organic light-emitting devices well-known in the art may be applied to the present application.

[0133] According to Figure 1, 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 is shown. However, the present application is not limited to such a structure only, and as shown in Figure 2, an organic light-emitting device in which a cathode, an organic layer, and an anode are sequentially stacked on a substrate may be realized.

[0134] Figure 3 illustrates a case where the organic layer is multilayer. The organic light-emitting device according to Figure 3 includes a hole injection layer 301, a hole transport layer 302, a light-emitting layer 303, a hole blocking layer 304, an electron transport layer 305, and an electron injection layer 306. However, the scope of the present application is not limited by such a stacking structure, and if necessary, the remaining layers except the light-emitting layer may be omitted, and other necessary functional layers may be further added.

[0135] The organic layer containing the compound of Chemical Formula 1 may further contain other substances as necessary.

[0136] In the organic light-emitting device according to an embodiment of the present application, materials other than the heterocyclic compound of Chemical Formula 1 are exemplified below, but these are merely for illustration and not for limiting the scope of the present application, and may be replaced by materials known in the art.

[0137] As the anode material, a material with a relatively large work function may be used, or a transparent conductive oxide, a metal, or a conductive polymer may be used. Specific examples of the anode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

[0138] As the cathode material, a material with a relatively low work function may be used, or a metal, a metal oxide, or a conductive polymer may be used. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; substances with a multilayer structure such as LiF / Al or LiO2 / Al, but are not limited thereto.

[0139] As the hole injection material, known hole injection materials may be used. For example, phthalocyanine compounds such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429, or starburst-type amine derivatives described in the literature [Advanced Material, 6, p.677 (1994)], such as tris(4-carbazolyl-9-ylphenyl)amine (TCTA), 4,4’,4’’-tri[phenyl(m-tolyl)amino]triphenylamine (m-MTDATA), 1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene (m-MTDAPB), polyaniline / dodecylbenzenesulfonic acid which is a soluble conductive polymer or poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate), polyaniline / camphor sulfonic acid, or polyaniline / poly(4-styrene-sulfonate) may also be used.

[0140] As the hole transport material, pyrazoline derivatives, arylamine-based derivatives, stilbene derivatives, triphenyldiamine derivatives, etc. may be used, and low-molecular or high-molecular materials may also be used.

[0141] As the electron transport material, oxadiazole derivatives, anthraquinodimethane and its derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, tetracyanoanthraquinodimethane and its derivatives, fluorenone derivatives, diphenyldicyanoethylene and its derivatives, diphenoquinone derivatives, metal complexes of 8-hydroxyquinoline and its derivatives, etc. may be used, and not only low-molecular substances but also high-molecular substances may be used.

[0142] As an electron injection material, for example, LiF is typically used in the art, but the present application is not limited thereto.

[0143] As the light-emitting material, a red, green, or blue light-emitting material may be used, and if necessary, two or more light-emitting materials may be mixed and used. At this time, two or more light-emitting materials may be vapor-deposited and used as individual supply sources, or may be pre-mixed and vapor-deposited and used as one supply source. Further, as the light-emitting material, a fluorescent material may be used, or a phosphorescent material may be used. As the light-emitting material, a material that emits light by combining holes and electrons injected from the anode and the cathode, respectively, alone may be used, or a material in which both the host material and the dopant material are involved in light emission may be used.

[0144] When mixing and using the hosts of the light-emitting material, hosts of the same system may be mixed and used, or hosts of different systems may be mixed and used. For example, two or more materials selected from either an n-type host material or a p-type host material may be used as the host material of the light-emitting layer.

[0145] The organic light-emitting device according to an embodiment of the present application may be a top emission type, a bottom emission type, or a double-sided emission type depending on the materials used.

[0146] The heterocyclic compound according to an embodiment of the present application can also act on the same principle as applied to the organic light-emitting device in organic electronic devices such as organic solar cells, organic photoreceptors, and organic transistors.

Example

[0147] Hereinafter, the present specification will be described in more detail by way of examples, but these are merely for illustrating the present application and not for limiting the scope of the present application.

[0148] <Production Example 1> Production of Compound 0002

Chemical formula

[0149] 1) Production of Compound 0002-P3 The compound 1-bromonaphthalen-2-ol (100 g, 448.29 mmol) and phenylboronic acid (57.39 g, 470.70 mmol) were dissolved in 1000 ml of toluene, 200 ml of ethanol and 200 ml of distilled water. Then, Pd(PPh3)4 (10.36 g, 8.97 mmol) and K2CO3 (154.90 g, 1120.72 mmol) were added, and the mixture was refluxed and stirred for 12 hours. After the reaction was completed, ethyl acetate was added to the reaction solution to dissolve it, and then it was extracted with distilled water. The organic layer was dried over anhydrous MgSO4, and then the solvent was removed by a rotary evaporator. Subsequently, it was purified by column chromatography using dichloromethane and hexane as the developing solvents to obtain compound 0002-P3 (86 g, 87%).

[0150] 2) Production of Compound 0002-P2 Compound 0002-P3 (86 g, 390.43 mmol) and 1-bromo-3-chloro-2-fluorobenzene (89.95 g, 429.47 mmol) were dissolved in 1000 ml of N,N-dimethylacetamide and heated to 150 °C. Then, Cs2CO3 (254.42 g, 780.86 mmol) was added, and the mixture was refluxed and stirred for 30 minutes. After the reaction was completed, it was extracted with dichloromethane and distilled water. The organic layer was dried over anhydrous MgSO4, and then the solvent was removed by a rotary evaporator. Subsequently, it was purified by column chromatography using dichloromethane and hexane as the developing solvents to obtain compound 0002-P2 (134 g, 84%).

[0151] 3) Production of Compound 0002-P1 Compound 0002-P2 (134 g, 327.07 mmol) was dissolved in 1000 ml of 1-methyl-2-pyrrolidinone. Then, Pd(OAc)2 (3.67 g, 16.35 mmol), PPh3 (8.58 g, 32.71 mmol), and Cs2CO3 (213.13 g, 654.14 mmol) were added, and the mixture was refluxed and stirred for 12 hours. After completion of the reaction, extraction was performed with dichloromethane and distilled water. The organic layer was dried over anhydrous MgSO4, and then the solvent was removed using a rotary evaporator. Subsequently, purification was carried out by column chromatography using dichloromethane and hexane as the developing solvents to obtain Compound 0002-P1 (79 g, 73%).

[0152] 4) Production of Compound 0002 Compound 0002-P1 (10 g, 30.41 mmol) and N-phenyl-[1,1’-biphenyl]-4-amine (7.83 g, 31.94 mmol) were dissolved in 100 ml of xylene. Then, Pd2(dba)3 (1.39 g, 1.52 mmol), P(t-Bu)3 (1.42 ml, 3.04 mmol), and t-BuONa (7.31 g, 76.04 mmol) were added, and the mixture was refluxed and stirred for 3 hours. After completion of the reaction, MC was added to the reaction solution to dissolve it, followed by extraction with distilled water. The organic layer was dried over anhydrous MgSO4, and then the solvent was removed using a rotary evaporator. Subsequently, purification was carried out by column chromatography using dichloromethane and hexane as the developing solvents to obtain Compound 0002 (13 g, 79%).

[0153] Table 1 below shows that in Preparation Example 1, Compound A was used instead of phenylboronic acid, Compound B was used instead of 1-bromo-3-chloro-2-fluorobenzene, and Compound C was used instead of N-phenyl-[1,1’-biphenyl]-4-amine. The target compound was synthesized by a method similar to that of Preparation Example 1 except for these substitutions.

[0154]

Table 1

[0155] The synthesis confirmation materials of the compounds produced above are as described in Table 2 and Table 3 below. Table 2 is 1 the measured values of 1H NMR (CDCl3, 300 MHz), and Table 3 is the measured values of FD-MS (Field desorption mass spectrometry).

[0156]

Table 2

[0157]

Table 3

[0158] <Experimental Example 1> (1) Fabrication of Organic Light-Emitting Device A glass substrate with a 1,500 Å-thick ITO thin film coating was ultrasonically cleaned with distilled water. After the distilled water cleaning was completed, it was ultrasonically cleaned with solvents such as acetone, methanol, and isopropyl alcohol and dried, and then subjected to UVO treatment using UV for 5 minutes by a UV cleaner. Then, the substrate was transferred to a plasma cleaner (PT), and after that, plasma treatment was performed in a vacuum state for the work function of ITO and removal of the residual film, and then transferred to a thermal evaporation apparatus for organic vapor deposition.

[0159]

Chemical formula

[0160]

Chemical formula

[0161] On the other hand, all the organic compounds required for the fabrication of the OLED device were vacuum sublimation purified at 10 -6 ~10 -8 torr and used for the fabrication of the OLED.

[0162] In Experimental Example 1, an organic light-emitting device was produced in the same manner except that the compound shown in Table 4 below was used instead of the compound NPB used in the formation of the hole transport layer. The driving voltage and luminous efficiency of the organic electroluminescent device according to Experimental Example 1 are as shown in Table 4 below.

[0163] (2) Driving voltage and luminous efficiency of the organic light-emitting device For the organic electroluminescent device fabricated as described above, the electroluminescence (EL) characteristics were measured via M7000 manufactured by Mac Science Co., Ltd. Using the measurement results, the lifetime measurement device (M6000) manufactured by Mac Science Co., Ltd. was used to measure T when the reference luminance was 6,000 cd / m 2 is 90 measured.

[0164] The characteristics of the organic electroluminescent device of the present invention are as shown in Table 4 below.

[0165]

Table 4

[0166]

Chemical formula

[0167] <Experimental Example 2> (1) Fabrication of the organic light-emitting device The transparent electrode ITO thin film obtained from glass for OLED (manufactured by SAMSUNG-CORNING) was ultrasonically cleaned sequentially with trichloroethylene, acetone, ethanol, and distilled water for over 5 minutes each, and then stored in isopropanol and used later. Next, the ITO substrate was placed on the substrate holder of the vacuum evaporation apparatus, and 4,4’,4’’-tris(N,N-(2-naphthyl)-phenylamino)triphenyl amine (2-TNATA) was placed in the cell inside the vacuum evaporation apparatus.

[0168] [Chemical formula] Next, after evacuating until the vacuum degree in the chamber reached 10 -6 torr, a current was applied to the cell to evaporate 2-TNATA, and a hole injection layer with a thickness of 600 Å was deposited on the ITO substrate. N,N’-bis(α-naphthyl)-N,N’-diphenyl-4,4’-diamine (NPB) was placed in another cell inside the vacuum evaporation apparatus, and a current was applied to the cell to evaporate it, and a hole transport layer with a thickness of 300 Å was deposited on the hole injection layer.

[0169] [Chemical formula] After forming the hole injection layer and the hole transport layer in this way, a blue light-emitting material with the following structure was deposited thereon as the light-emitting layer. Specifically, the blue light-emitting host material H1 was vacuum-deposited to a thickness of 200 Å in one cell inside the vacuum evaporation apparatus, and then the blue light-emitting dopant material D1 was vacuum-deposited at 5% with respect to the host material on top of it.

[0170] [Chemical formula] Next, a compound of the following structural formula E1 was vapor-deposited to a thickness of 300 Å as the electron transport layer.

[0171] [Chemical formula] Lithium fluoride (LiF) was vapor-deposited to a thickness of 10 Å as the electron injection layer, and an Al cathode was made to a thickness of 1,000 Å to fabricate an OLED device. On the other hand, all the organic compounds required for the fabrication of the OLED device were vacuum sublimation purified at 10 -6 ~10 -8 torr and used for the fabrication of the OLED.

[0172] In the said Experimental Example 2, after forming the hole transport layer NPB to a thickness of 150 Å, an organic electroluminescent device was fabricated in the same manner as in Experimental Example 2 except that an electron blocking layer was formed to a thickness of 50 Å of the compound shown in Table 5 below on top of the hole transport layer. The results of measuring the driving voltage, luminous efficiency, and lifetime of the blue organic light-emitting device manufactured according to the present invention are as shown in Table 5 below.

[0173] [Table 5] TIFF0007705669000107.tif30169

[0174] [Chemical formula]

[0175] [Experimental Example 3] (1) Fabrication of an organic light-emitting device A glass substrate coated with indium tin oxide (ITO) with a thickness of 1,500 Å was ultrasonically cleaned with distilled water. After the distilled water cleaning was completed, it was ultrasonically cleaned with solvents such as acetone, methanol, and isopropyl alcohol and dried, and then subjected to UVO treatment for 5 minutes using UV by a UV cleaner. Then, after the substrate was transferred to a plasma cleaner (PT), plasma treatment was performed in a vacuum for the work function of ITO and removal of the remaining film, and it was transferred to a thermal evaporation apparatus for organic vapor deposition.

[0176] On the ITO transparent electrode (anode), as a common layer, a hole injection layer 2-TNATA (4,4’,4’’-Tris[2-naphthyl(phenyl)amino]triphenylamine) and a hole transport layer NPB (N,N’-diphenyl-(1,1’-biphenyl)-4,4’-diamine) were formed.

[0177] On top of that, the light-emitting layer was thermally vacuum-evaporated as follows. The light-emitting layer uses the compound described in Table 7 below as a single host or an n-Host (n-type host) with good electron transport ability as the first host, and a p-Host (p-type host) with good hole transport ability as the second host, and the two host compounds are used in a deposition method with one supply source, and (piq)2(Ir)(acac) is used as a red phosphorescent dopant in the host and doped at 3% with respect to the weight of the host material, or Ir(ppy)3 is used as a green phosphorescent dopant in the host and doped at 7% with respect to the weight of the host material and deposited to a thickness of 500 Å.

[0178] Then, BCP was deposited to a thickness of 60 Å as a hole blocking layer, and on top of that, Alq3 was deposited to a thickness of 200 Å as an electron transport layer.

[0179] At this time, when two hosts are used, the compounds X, Y, and Z used as n-Host (the first host in Table 7 below) are as follows.

[0180]

Chemical formula

[0181] Specifically, the compounds used as hosts in Examples 70 to 94 and Comparative Examples 8 to 13 are as shown in Table 7 below.

[0182] At this time, Compounds M1 to M3 used as the single host or the second host in Comparative Examples 8 to 13 of Table 7 below are as follows.

[0183]

Chemical formula

[0184] (2) Driving voltage and luminous efficiency of the organic light-emitting device For the organic light-emitting device fabricated as described above, the electroluminescence (EL) characteristics were measured via M7000 manufactured by Mac Science Co., Ltd. Using the measurement results, the lifetime measurement device (M6000) manufactured by Mac Science Co., Ltd. was used to measure T when the reference luminance was 6,000 cd / m 2 is. The measured results of the driving voltage, luminous efficiency, emission color, and lifetime of the organic light-emitting device manufactured according to the present invention are as shown in Table 7 below. 95

[0185]

Table 6

[0186] Also, from Experimental Example 3, in the case of the organic light-emitting devices of Examples 80 to 94 in which the first host material corresponding to n-Host and the compound according to the present application were simultaneously used as the second host material corresponding to p-Host to form the light-emitting layer, it was confirmed that the light-emitting efficiency and lifetime were superior to those of the organic light-emitting devices of Comparative Examples 9, 11, and 13 in which a compound other than the compound according to the present application was simultaneously used as the second host material corresponding to p-Host when forming the light-emitting layer.

[0187] Also, it was confirmed that the light-emitting efficiency and lifetime of the organic light-emitting devices of Examples 70 to 79 in which the compound according to the present application was used as a single host material to form the light-emitting layer were sometimes similar to or superior to those of the organic light-emitting devices of Comparative Examples 9, 11, and 13 in which the first host material corresponding to n-Host and a compound other than the compound according to the present application were simultaneously used as the second host material corresponding to p-Host to form the light-emitting layer.

[0188] This means that, generally, when considering that using an n-Host (n-type host) with good electron transport ability as the first host and a p-Host (p-type host) with good hole transport ability as the second host is superior in terms of light-emitting efficiency and lifetime, when the compound according to the present application is used as the host material, the light-emitting efficiency and lifetime of the organic light-emitting device can be significantly improved.

[0189] This is determined to be because when the compound according to the present application is used as a host material, holes and electrons can be efficiently injected from each charge transport layer into the light-emitting layer. This is also determined to be because, as described above, it is affected by the orientation and spatial size formed by the interaction of substances during vapor deposition.

[0190] This is because the efficient injection of holes and electrons into the light-emitting layer is also affected by the orientation and spatial size formed by the interaction of substances during vapor deposition, and is determined to be the effect caused by the difference in the orientation characteristics and spatial size of the compound of the present application and the above-mentioned M1 to M3 as described above.

[0191] The present invention is not limited to the above embodiments and can be manufactured in various different forms. Those with ordinary knowledge in the technical field to which the present invention belongs can understand that it can be implemented in other specific forms without changing the technical idea and essential features of the present invention. Therefore, it must be understood that the embodiments described above are illustrative in all respects and not restrictive.

Claims

1. A heterocyclic compound represented by the following Chemical Formula 1: 【Chemical 38】 In the Chemical Formula 1, R1 to R6 are the same as or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C6-C60 aryl group; and a substituted or unsubstituted C2-C60 heteroaryl group, and are selected from the group consisting of, L1 and L2 are the same as or different from each other and are each independently a direct bond; a substituted or unsubstituted C6-C60 arylene group; or a substituted or unsubstituted C2-C60 heteroarylene group, Ar1 and Ar2 are the same as or different from each other and are each independently a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C6-C60 aryl group; a substituted or unsubstituted fluorenyl group; or a substituted or unsubstituted C2-C60 heteroaryl group, Z1 is an unsubstituted C6-C40 aryl group; a fluorenyl group substituted or unsubstituted with one or more substituents selected from the group consisting of a C1-C10 alkyl group and a C6-C20 aryl group; or an unsubstituted C2-C40 heteroaryl group containing one or more of O, S, and N as heteroatoms, p and m are integers from 0 to 4, n is an integer from 1 to 6, and a is an integer from 0 to 3, "Substituted or unsubstituted" means substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium; a linear or branched C1-C60 alkyl; a monocyclic or polycyclic C6-C60 aryl; and a monocyclic or polycyclic C2-C60 heteroaryl.

2. The heterocyclic compound according to Claim 1, wherein the Chemical Formula 1 is represented by any one of the following Chemical Formulas 2 to 5: 【Chemical Formula 39】 【Chemical Formula 40】 【Chemical 41】 【Chemical 42】 In the Chemical Formulas 2 to 5, the definitions of R1 to R6, L1, L2, Z1, Ar1, Ar2, p, m, n, and a are the same as those in the Chemical Formula 1.

3. The heterocyclic compound according to Claim 1, wherein the Chemical Formula 1 is represented by any one of the following Chemical Formulas 6 to Chemical Formula 9: 【Chemical 43】 【Chemical 44】 【Chemical 45】 【Chemical Formula 46】 In the Chemical Formulas 6 to 9, the definitions of R1 to R6, L1, L2, Ar1, Ar2, p, m, n, and a are the same as those in the Chemical Formula 1, Z11 is an unsubstituted C6-C40 aryl group, and X is O; or S. R11 to R18 are the same as or different from each other, and each independently selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted C6-C60 aryl group; and a substituted or unsubstituted C2-C60 heteroaryl group, R21 and R22 are the same as or different from each other, and each independently a substituted or unsubstituted C1-C60 alkyl group; or a substituted or unsubstituted C6-C60 aryl group, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6-C60 aliphatic or aromatic hydrocarbon ring, or a substituted or unsubstituted C2-C60 aliphatic or aromatic heterocyclic ring, b is an integer from 0 to 3.

4. The 【Chemical 47】 in Chemical Formula 1 is the heterocyclic compound according to Claim 1, represented by any one of the following Chemical Formulas 1-1 to 1-3: 【Chemical 48】 【Chemical 49】 【Chemical Formula 50】 In the above Chemical Formulas 1-1 to 1-3, the definitions of L2, p, and Ar2 are the same as those in Chemical Formula 1, 【Chemical Formula 51】 means the position linked to Chemical Formula 1, X1 is O; or S, L11 is a direct bond; a substituted or unsubstituted C6-C60 arylene group; or a substituted or unsubstituted C2-C60 heteroarylene group, Ar11 is an unsubstituted C6-C40 aryl group, R31 to R34 are the same as or different from each other, and each independently selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted C6-C60 aryl group; and a substituted or unsubstituted C2-C60 heteroaryl group, R41 and R42 are the same as or different from each other, and each independently a substituted or unsubstituted C1-C60 alkyl group; or a substituted or unsubstituted C6-C60 aryl group, or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6-C60 aliphatic or aromatic hydrocarbon ring, or a substituted or unsubstituted C2-C60 aliphatic or aromatic heterocyclic ring, r is an integer from 0 to 3.

5. The heterocyclic compound according to Claim 1, wherein R1 to R6 are hydrogen; or deuterium.

6. The heterocyclic compound according to Claim 1, wherein Chemical Formula 1 is represented by any one of the following compounds: [Chemical Formula 52] 【Chem.】 【Chemistry】 [Chemical] 【Chem.】 【Chem.】 【Chem.】 [Chemical] [Chemical] 【Chem.】 【Chem.】 【Chem.】 【Chem.】 [Chemical] 【Chem.】 【Chem.】 【Chem.】 【Chem.】 【Chem.】 【Chem.】 【Chem.】 【Chem.】 【Chem.】 【Chem.】 【Chem.】 【Chem.】 [Chemical] 【Chem.】 【Chem.】 【Chem.】 【Chem.】 【Chem.】 【Chem.】 【Chem.】 【Chem.】 【Chem.】 [Chemical] 【Chem.】 【Chem.】 [Chemical] 【Chem.】 【Chem.】

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

8. The organic light-emitting device according to claim 7, wherein the organic layer includes a light-emitting layer, and the light-emitting layer contains the heterocyclic compound.

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

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

11. The organic light-emitting device according to claim 7, wherein the organic layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer contains the heterocyclic compound.

12. The organic light-emitting device according to claim 7, further including one or more layers selected from the group consisting of a light-emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer.

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