Heterocyclic compounds, and organic light-emitting devices containing them.

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. 10-2020-0180478, filed with the Korean Intellectual Property Office on December 22, 2020, and all of its content is incorporated herein.

[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 a 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 are combined in the organic thin film to form a pair, and then light is emitted 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 by itself alone may be used, or a compound that can serve as a host or a dopant in a host-dopant-based 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, etc. 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] Research is needed on organic light-emitting devices that include compounds having chemical structures capable of satisfying the requirements for materials usable in organic light-emitting devices, such as appropriate energy levels, electrochemical safety, and thermal stability, and that can perform diverse roles required in organic light-emitting devices through substituents. [Prior art documents] [Patent Documents]

[0008] [Patent Document 1] U.S. Patent No. 4,356,429 [Overview of the project] [Problems that the invention aims to solve]

[0009] This application relates to heterocyclic compounds and organic light-emitting devices containing the same. [Means for solving the problem]

[0010] In one embodiment of this application, a heterocyclic compound represented by the following chemical formula 1 is provided.

[0011] [ka] In the aforementioned chemical formula 1, X1 and X2 are either identical or different from each other, and independently of each other, O; or S. R1 and R2 are either identical or different from each other and independently selected from the group consisting of 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'; -SiRR'R''; and -NRR', or two or more adjacent groups bond 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. L1-L3 are identical or different from each other, and independently, they are directly bonded; substituted or unsubstituted C6-C60 arylene groups; or substituted or unsubstituted C2-C60 heteroarylene groups. Ar1 to Ar3 are either identical or different from each other, and each is independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group. r, p, and m are integers between 0 and 4. a, b, and q are integers between 0 and 3. If r, p, m, a, q, and b are each 2 or more, the substituents in parentheses are either identical or different from each other. The R, R', and R'' are identical or different from each other and are independently substituted or unsubstituted C1-C60 alkyl groups; substituted or unsubstituted C6-C60 aryl groups; or substituted or unsubstituted C2-C60 heteroaryl groups.

[0012] Furthermore, according to one embodiment of this application, an organic light-emitting element is provided, comprising a first electrode; a second electrode provided opposite the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers contain a heterocyclic compound represented by the chemical formula 1. [Effects of the Invention]

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

[0014] In particular, the heterocyclic compound according to this application has a ring fused to a benzofluorene skeleton as its core structure, and has amine substituents and -(L2)p-(Ar3)q substituents. When an amine derivative is used as a hole transport layer, the lone pair of electrons in the amine improves the flow of holes, thereby improving the hole transport capacity of the hole transport layer. When used as an electron blocking layer, it can suppress the degradation of the hole transport material caused by electrons entering the hole transport layer.

[0015] Furthermore, by attaching substituents that enhance hole properties, the hole transfer capability can be improved by adjusting the band gap and T1 (energy level value of the triplet state) value. This increases the planarity of the amine derivative and the glass transition temperature, thereby improving the thermal stability of the chemical and improving the lifespan of organic light-emitting devices containing it. In addition, the Ar3 substituent influences the spatial structure formation of the compound, suppressing intermolecular π-π stacking.

[0016] Therefore, when the heterocyclic compound of Chemical Formula 1 is used as a material for the hole transport layer or the electron blocking layer of the organic light-emitting device, the driving voltage of the device can be reduced, the light efficiency can be improved, and the lifetime characteristics of the device can be improved.

Brief Description of the Drawings

[0017] [Figure 1] It is a diagram schematically showing the stacked structure of an organic light-emitting device according to an embodiment of the present application. [Figure 2] It is a diagram schematically showing the stacked structure of an organic light-emitting device according to an embodiment of the present application. [Figure 3] It is a diagram schematically showing the stacked structure of an organic light-emitting device according to an embodiment of the present application.

Explanation of Reference Numerals

[0018] 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

Embodiments for Carrying Out the Invention

[0019] Hereinafter, the present application will be described in detail.

[0020] In the present specification, the halogen may be fluorine, chlorine, bromine, or iodine.

[0021] In this specification, the alkyl group includes a linear or branched chain having 1 to 60 carbon atoms and may be further substituted with other substituents. The number of carbon atoms in the alkyl group may be 1 to 60, specifically 1 to 40, and more specifically 1 to 20. Specific examples include 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, and Examples of but are limited to butyl 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, and 5-methylhexyl group.

[0022] In this specification, the alkenyl group includes a linear or branched chain having 2 to 60 carbon atoms and may be further substituted with other substituents. The number of carbon atoms in the alkenyl group may be 2 to 60, more specifically 2 to 40, and more specifically 2 to 20. Specific examples include, but are not limited to, 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, and styrenyl group.

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

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

[0025] In this specification, the cycloalkyl group includes a monocyclic or polycyclic group having 3 to 60 carbon atoms and may be further substituted with other substituents. Here, polycyclic means a group in which the cycloalkyl group is directly linked or fused with another cyclic group. Here, the other cyclic group may be a cycloalkyl group, but may also be other types of cyclic groups, such as a heterocycloalkyl group, an aryl group, a heteroaryl group, etc. The number of carbon atoms in the cycloalkyl group may be 3 to 60, more specifically 3 to 40, and more specifically 5 to 20. Specifically, examples include, but are not limited to, 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, and cyclooctyl group.

[0026] In this specification, the heterocycloalkyl group comprises O, S, Se, N, or Si as a heteroatom, and includes a monocyclic or polycyclic group having 2 to 60 carbon atoms, and may be further substituted with other substituents. Here, polycyclic means a group in which the heterocycloalkyl group is directly linked or fused with another cyclic group. Here, the other cyclic group may be a heterocycloalkyl group, but may also be other types of cyclic groups, such as a cycloalkyl group, an aryl group, or a heteroaryl group. The number of carbon atoms in the heterocycloalkyl group may be 2 to 60, more specifically 2 to 40, and more specifically 3 to 20.

[0027] In this specification, the aryl group includes monocyclic or polycyclic groups having 6 to 60 carbon atoms and may be further substituted with other substituents. Here, polycyclic means a group in which the aryl group is directly linked or fused 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 cycloalkyl groups, heterocycloalkyl groups, heteroaryl groups, etc. The number of carbon atoms in the aryl group may be 6 to 60, more specifically 6 to 40, and more specifically 6 to 25. Specific examples of the aryl group include, but are not limited to, phenyl, biphenyl, triphenyl, naphthyl, anthryl, crisenyl, phenantrenyl, perilenyl, fluoranthenyl, triphenylenyl, phenalenyl, pyrenyl, tetracenyl, pentacenyl, indenyl, acenaphthirenyl, 2,3-dihydro-1H-indenyl, and fused ring groups thereof.

[0028] In this specification, the fluorenyl group may be substituted, or adjacent substituents may bond to each other to form a ring.

[0029] When the aforementioned fluorenyl group is substituted, the resulting structure may be as shown below, but is not limited to these.

[0030] [ka]

[0031] In this specification, the heteroaryl group includes S, O, Se, N, or Si as a heteroatom, and includes a monocyclic or polycyclic group having 2 to 60 carbon atoms, and may be further substituted with other substituents. Here, polycyclic means a group in which the heteroaryl group is directly linked or fused with another cyclic group. Here, the other cyclic group may be a heteroaryl group, but may also be other types of cyclic groups, such as cycloalkyl groups, heterocycloalkyl groups, or aryl groups. The number of carbon atoms in the heteroaryl group may be 2 to 60, more specifically 2 to 40, and more specifically 3 to 25.Specific examples of the heteroaryl group include pyridyl group, pyrrolyl group, pyrimidyl group, pyridadinyl group, furanyl group, thiophene 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, thiadinyl group, dioxynyl group, tria Dinyl group, tetradinyl group, quinolyl group, isoquinolyl group, quinazolinyl group, isoquinazolinyl group, quinozolilyl group, naphthylidyl group, acridinyl group, phenantridinyl group, imidazopyridinyl group, diazanafthalenyl group, triazaidene group, indolyl group, indolidinyl group, benzothiazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiophene group, benzofuran group, dibenzothiophene group, dibenzofuran group, carbazolyl group, Benzocarbazolyl group, dibenzocarbazolyl group, phenazinyl group, dibenzosilol group, spirovi(dibenzosilol), dihydrophenazinyl group, phenoxadinyl group, phenanthridine group, imidazopyridinyl group, thienyl group, indro[2,3-a]carbazolyl group, indro[2,3-b]carbazolyl group, indolinyl group, 10,11-dihydro-dibenzo[b,f]azepine group, 9,10-dihydroacridinyl group, phenanthridineyl group, Examples include, but are not limited to, phenothiathiadinyl group, phthalazinyl group, naphthilidinyl group, phenanthrolinyl group, benzo[c][1,2,5]thiadiazolyl group, 5,10-dihydrodibenzo[b,e][1,4]azacylinyl, pyrazolo[1,5-c]quinazolinyl group, pyrido[1,2-b]indazolyl group, pyrido[1,2-a]imidazo[1,2-e]indolinyl group, and 5,11-dihydroindeno[1,2-b]carbazolyl group.

[0032] In this specification, the amine group may be selected from the group consisting of monoalkylamine group; monoarylamine group; monoheteroarylamine group; -NH2; dialkylamine group; diarylamine group; diheteroarylamine group; alkylarylamine group; alkylheteroarylamine group; and 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, but are not limited to, methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, dibiphenylamine group, anthracenylamine group, 9-methyl-anthracenylamine group, diphenylamine group, phenylnaphthylamine group, ditolylamine group, phenyltolylamine group, triphenylamine group, biphenylnaphthylamine group, phenylbiphenylamine group, biphenylfluorenylamine group, phenyltriphenylenylamine group, and biphenyltriphenylenylamine group.

[0033] In this specification, an arylene group means a group with two bonding positions on an aryl group, i.e., a divalent group. The description of the aryl group described above may apply to these groups, except that they are each divalent. Similarly, a heteroarylene group means a group with two bonding positions on a heteroaryl group, i.e., a divalent group. The description of the heteroaryl group described above may apply to these groups, except that they are each divalent.

[0034] In this specification, a phosphine oxide group is represented as -P(=O)R101R102, where R101 and R102 are identical or different, and each may independently be a substituent consisting of at least one of the following: hydrogen; deuterium; halogen group; alkyl group; alkenyl group; alkoxy group; cycloalkyl group; aryl group; and heterocyclic group. Specific examples of the phosphine oxide group include, but are not limited to, a diphenylphosphine oxide group and a dinaphthylphosphine oxide group.

[0035] In this specification, a silyl group is a substituent containing Si, wherein the Si atom is directly linked as a radical, and is represented as -SiR104R105R106, where R104 to R106 may be the same or different from each other, and each may independently consist of at least one of the following substituents: hydrogen; deuterium; halogen group; alkyl group; alkenyl group; alkoxy group; cycloalkyl group; aryl group; and heterocyclic group. Specific examples of silyl groups include, but are not limited to, trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, and phenylsilyl group.

[0036] In this specification, “adjacent” groups may mean a substituent substituted on an atom directly connected to the atom on which the substituent is substituted, a substituent that is stereochemically closest to the substituent, or another substituent substituted on the atom on which the substituent is substituted. For example, two substituents substituted at the ortho position in a benzene ring, and two substituents substituted on the same carbon in an aliphatic ring, can be interpreted as “adjacent” groups.

[0037] Aliphatic or aromatic hydrocarbon rings or heterocycles capable of forming adjacent groups may be subject to the structures exemplified above as cycloalkyl groups, cycloheteroalkyl groups, aryl groups, and heteroaryl groups, except that they are not monovalent groups.

[0038] In this specification, the term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is replaced by another substituent, and the position of substitution is not limited to any position where a hydrogen atom can be substituted, i.e., any position where a substituent can be substituted, and if two or more substituents are substituted, the two or more substituents may be the same or different from one another.

[0039] In this specification, "substituted or unsubstituted" means substituted or unsubstituted with one or more substituents selected from the group consisting of C1-C60 linear or branched alkyls; C2-C60 linear or branched alkenyls; C2-C60 linear or branched alkynyls; C3-C60 monocyclic or polycyclic cycloalkyls; C2-C60 monocyclic or polycyclic heterocycloalkyls; C6-C60 monocyclic or polycyclic aryls; C2-C60 monocyclic or polycyclic heteroaryls; -SiRR'R''; -P(=O)RR'; C1-C20 alkylamines; C6-C60 monocyclic or polycyclic arylamines; and C2-C60 monocyclic or polycyclic heteroarylamines, or substituted or unsubstituted with substituents in which two or more substituents selected from the exemplified substituents are linked together. R, R', and R'' may be the same or different from each other, and each may independently 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.

[0040] In this specification, "where a substituent is not indicated in the chemical formula or structure of a compound," it means that a hydrogen atom is bonded to a carbon atom. However, deuterium ( 2 Since H (Deuterium) is an isotope of hydrogen, some hydrogen atoms may be deuterium.

[0041] In one embodiment of this application, "when no substituent is indicated in the chemical formula or structure of the compound" may mean that all possible substituent positions are hydrogen or deuterium. That is, in the case of deuterium, it is an isotope of hydrogen, and some of the hydrogen atoms may be the isotope deuterium, in which case the deuterium content may be 0% to 100%.

[0042] In one embodiment of this application, in cases where "substituents are not indicated in the chemical formula or structure of the compound," hydrogen and deuterium may be used together in the compound if the deuterium content is 0%, the hydrogen content is 100%, and all substituents do not explicitly exclude deuterium, such as hydrogen.

[0043] In one embodiment of this application, deuterium is one of the isotopes of hydrogen, and is an element having a deuteron as its nucleus, which consists of one proton and one neutron, and may be represented as hydrogen-2, and its element symbol may be written as D or 2H.

[0044] In one embodiment of this application, isotopes can be interpreted as atoms having the same atomic number (Z) but different mass numbers (A), or as elements having the same number of protons but different numbers of neutrons.

[0045] In one embodiment of this application, the meaning of the content T% of a specific substituent can be defined as T2 / T1 × 100 = T%, where T1 is defined as the total number of substituents that the basic compound may have, and T2 is defined as the number of specific substituents among them.

[0046] In other words, in one example, [ka] In a phenyl group represented by , a deuterium content of 20% means that the total number of substituents that the phenyl group can have is 5 (T1 in the formula), and of these substituents, the number of deuterium atoms is 1 (T2 in the formula). In other words, a phenyl group with a deuterium content of 20% may also be represented by the following structural formula.

[0047] [ka] Furthermore, in one embodiment of this application, the term "phenyl group having a deuterium content of 0%" may mean a phenyl group that does not contain a deuterium atom, i.e., a phenyl group having five hydrogen atoms.

[0048] In one embodiment of this application, a compound represented by the chemical formula 1 is provided.

[0049] The heterocyclic compound of Chemical Formula 1 of this application has an amine substituent and a -(L2)p-(Ar3)q substituent with hole properties. When used later as a hole transport layer in an organic light-emitting device, the lone pair of electrons in the amine substituent improves the flow of holes, thereby improving the hole transport capability of the hole transport layer. When used as an electron blocking layer, it can suppress the degradation of the hole transport material caused by electrons entering the hole transport layer.

[0050] Furthermore, by attaching the -(L2)p-(Ar3)q substituent, which enhances the hole properties, the planarity and glass transition temperature of the amine derivative are increased, thereby improving the thermal stability of the heterocyclic compound and thus improving the lifetime of organic light-emitting devices containing it. In addition, the Ar3 substituent influences the spatial structure formation of the compound, suppressing intermolecular π-π stacking.

[0051] Furthermore, by adjusting the band gap and T1 value, the hole transfer capability is improved and the molecular stability is enhanced, which allows for a reduction in the device's driving voltage, improved optical efficiency, and enhanced device lifetime characteristics through improved thermal stability of the compound.

[0052] In one embodiment of this application, the heterocyclic compound according to chemical formula 1 may be substituted or unsubstituted with deuterium, in which case the deuterium content of the heterocyclic compound according to chemical formula 1 may be 0% to 100%, preferably 20% to 100%, and more preferably 40% to 100%.

[0053] In one embodiment of this application, the chemical formula 1 may be represented by any one of the following chemical formulas 2 to 5.

[0054] [ka] [ka] [ka] [ka] In the aforementioned chemical formulas 2 to 5, R1, R2, L1-L3, Ar1-Ar3, r, p, m, q, a, and b are defined as in the same way as in Chemical Formula 1.

[0055] In one embodiment of this application, the chemical formula 1 may be represented by any one of the following chemical formulas 6 to 9.

[0056] [ka] [ka] [ka] [ka] In the aforementioned chemical formulas 6 to 9, R1, R2, L1-L3, Ar1-Ar3, r, p, m, q, a, and b are defined as in the same way as in Chemical Formula 1.

[0057] In one embodiment of this application, the chemical formula 1 may be represented by any one of the following chemical formulas 10 to 13.

[0058] [ka] [ka] [ka] [ka] In the above chemical formulas 10 to 13, R1, R2, L1-L3, Ar1-Ar3, r, p, m, q, a, and b are defined as in the same way as in Chemical Formula 1.

[0059] In one embodiment of this application, one of the chemical formulas 2 to 5. [ka] It may be represented by any one of the following chemical formulas 1-1 to 1-4.

[0060] [ka] [ka] [ka] [ka] In the above chemical formulas 1-1 to 1-4, [ka] This refers to the position where condensation occurs. The definitions of L1, L3, Ar1, Ar2, m, r, R2, and b are the same as the definitions in chemical formulas 2-5 above.

[0061] In one embodiment of this application, R1 and R2 are identical or different from each other and independently selected from the group consisting of 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'; -SiRR'R'' and -NRR', or two or more adjacent groups may bond 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.

[0062] In another embodiment, R1 and R2 may be the same or different from each other and independently selected from the group consisting of hydrogen; deuterium; substituted or unsubstituted C1-C60 alkyl groups; substituted or unsubstituted C6-C60 aryl groups; substituted or unsubstituted C2-C60 heteroaryl groups; -P(=O)RR'; -SiRR'R''; and -NRR', or two or more adjacent groups may bond 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.

[0063] In another embodiment, R1 and R2 may be the same or different from each other and independently be hydrogen; deuterium; 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.

[0064] In another embodiment, R1 and R2 may be the same or different from each other and independently be hydrogen; deuterium; a substituted or unsubstituted C1-C40 alkyl group; a substituted or unsubstituted C6-C40 aryl group; or a substituted or unsubstituted C2-C40 heteroaryl group.

[0065] In another embodiment, R1 and R2 may be the same or different from each other and independently be hydrogen; deuterium; a substituted or unsubstituted C1-C20 alkyl group; a substituted or unsubstituted C6-C20 aryl group; or a substituted or unsubstituted C2-C20 heteroaryl group.

[0066] In another embodiment, R1 and R2 may be the same or different from each other and independently be hydrogen; deuterium; a C1-C20 alkyl group; a C6-C20 aryl group; or a C2-C20 heteroaryl group.

[0067] In another embodiment, R1 and R2 may be the same or different from each other, and each may independently be hydrogen; deuterium; or a C6-C20 aryl group.

[0068] In another embodiment, R1 and R2 may be the same or different from each other, and each may independently be a hydrogen; deuterium; or a phenyl group.

[0069] In another embodiment, R1 and R2 may be the same or different from each other, and each may be independently a hydrogen or a phenyl group.

[0070] In one embodiment of this application, L1 to L3 may be the same or different from each other and independently be directly bonded; substituted or unsubstituted C6 to C60 arylene groups; or substituted or unsubstituted C2 to C60 heteroarylene groups.

[0071] In another embodiment, L1 to L3 may be identical or different from each other and independently directly bonded; substituted or unsubstituted C6 to C40 arylene groups; or substituted or unsubstituted C2 to C40 heteroarylene groups.

[0072] In another embodiment, L1 to L3 may be identical or different from each other, and each may be independently directly bonded; or substituted or unsubstituted C6 to C40 arylene groups.

[0073] In another embodiment, L1 to L3 may be identical or different from each other, and each may be independently directly bonded; or substituted or unsubstituted C6 to C20 arylene groups.

[0074] In another embodiment, L1 to L3 may be identical or different from each other, and each may be directly bonded independently; or they may be C6 to C20 arylene groups.

[0075] In another embodiment, L1 to L3 may be the same or different from each other, and each may be directly bonded; a monocyclic C6 to C10 arylene group; or a polycyclic C10 to C20 arylene group.

[0076] In another embodiment, L1 to L3 may be identical or different from each other, and each may be directly bonded independently; or they may be phenylene groups.

[0077] In one embodiment of this application, Ar1 to Ar3 may be the same or different from each other and may be independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0078] In another embodiment, Ar1 to Ar3 may be the same or different from each other and may be independently substituted or unsubstituted C1 to C40 alkyl groups; substituted or unsubstituted C6 to C40 aryl groups; or substituted or unsubstituted C2 to C40 heteroaryl groups.

[0079] In another embodiment, Ar1 to Ar3 may be the same or different from each other, and each may independently be a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group.

[0080] In another embodiment, Ar1 to Ar3 may be the same or different from each other, and each may independently be a C6 to C40 aryl group substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, C1 to C10 alkyl groups, and C6 to C10 aryl groups; or a C2 to C40 heteroaryl group.

[0081] In another embodiment, Ar1 to Ar3 may be the same or different from each other, and each may independently be a C6 to C40 aryl group substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, C1 to C10 alkyl groups, and C6 to C10 aryl groups; or a C2 to C40 heteroaryl group.

[0082] In one embodiment of this application, Ar3 may be a C6-C40 aryl group substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, C1-C10 alkyl groups, and C6-C10 aryl groups; or a C2-C40 heteroaryl group.

[0083] In another embodiment, Ar3 may be a C6-C30 aryl group substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, C1-C10 alkyl groups, and C6-C10 aryl groups; or a C2-C30 heteroaryl group.

[0084] In another embodiment, Ar3 may be a deuterium-substituted or unsubstituted phenyl group; biphenyl group; naphthyl group; t-phenyl group; triphenylenyl group; dimethylfluorenyl group; dibenzofuran group; or dibenzothiophene group.

[0085] In one embodiment of this application, the deuterium content of the deuterium-substituted or unsubstituted phenyl group may be 0% to 100%, preferably 20% to 100%, and more preferably 40% to 100%.

[0086] In one embodiment of this application, Ar3 may be represented by either of the following chemical formulas 2-1 and 2-2.

[0087] [ka] [ka] In the above chemical formulas 2-1 and 2-2, [ka] This refers to the position that is linked to the aforementioned chemical formula 1. The definition of q is the same as the definition in Chemical Formula 1 above. Ar11 is a substituted or unsubstituted C6-C60 aryl group. X is O; or S, R11~R14 are either identical or different from each other and independently selected from the group consisting of 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'; -SiRR'R''; and -NRR', or two or more adjacent groups bond 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. The R, R', and R'' mentioned above are defined as in Chemical Formula 1.

[0088] In one embodiment of this application, Ar11 may be a substituted or unsubstituted C6-C60 aryl group.

[0089] In another embodiment, Ar11 may be a substituted or unsubstituted C6-C40 aryl group.

[0090] In another embodiment, Ar11 may be a C6-C40 aryl group substituted with or unsubstituted with one or more substituents selected from the group consisting of deuterium, C1-C10 alkyl groups, and C6-C10 aryl groups.

[0091] In another embodiment, Ar11 may be a deuterium-substituted or unsubstituted phenyl group; biphenyl group; naphthyl group; t-phenyl group; triphenylenyl group; or dimethylfluorenyl group.

[0092] In one embodiment of this application, R11 to R14 are identical or different from each other and are independently selected from the group consisting of 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'; -SiRR'R''; and -NRR'; or two or more adjacent groups may bond 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.

[0093] In another embodiment, R11 to R14 may be the same as or different from each other, and each may be hydrogen or deuterium independently.

[0094] In another embodiment, R11 to R14 may be hydrogen.

[0095] In one embodiment of this application, the chemical formula 2-2 may be represented by any one of the following chemical formulas 2-2-1 to 2-2-4.

[0096] [ka] [ka] [ka] [ka] In the aforementioned chemical formulas 2-2-1 to 2-2-4, The definitions of each substituent are the same as those in Chemical Formula 2-2 above.

[0097] In one embodiment of this application, the chemical formula 1 [ka] It may be represented by any one of the following chemical formulas 1-1-1 to 1-1-3.

[0098] [ka] [ka] [ka] In the above chemical formulas 1-1-1 to 1-1-3, The definitions of L1, m, L3, and r are the same as those in Chemical Formula 1 above. [ka] This refers to the position that is linked to the aforementioned chemical formula 1. Ar21 is a substituted or unsubstituted C6-C60 aryl group. Ar22 is a substituted or unsubstituted C6-C12 aryl group. X21 is O; or S, R21~R26 are either identical or different from each other and independently selected from the group consisting of 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'; -SiRR'R''; and -NRR', or two or more adjacent groups bond 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. The definitions of R, R', and R'' are the same as those in Chemical Formula 1.

[0099] In one embodiment of this application, Ar21 may be a substituted or unsubstituted C6-C60 aryl group.

[0100] In another embodiment, Ar21 may be a substituted or unsubstituted C6-C40 aryl group.

[0101] In another embodiment, Ar21 may be a C1-C40 alkyl group or an unsubstituted C6-C40 aryl group.

[0102] In another embodiment, Ar21 may be a C1-C20 alkyl group or an unsubstituted C6-C20 aryl group.

[0103] In another embodiment, Ar21 may be a phenyl group; a phenyl-substituted or unsubstituted biphenyl group; a naphthyl group; a t-phenyl group; a dimethylfluorenyl group; a diphenylfluorenyl group; or a spirobifluorenyl group.

[0104] In one embodiment of this application, Ar22 may be a substituted or unsubstituted C6-C12 aryl group.

[0105] In another embodiment, Ar22 may be a C6-C12 aryl group.

[0106] In another embodiment, Ar22 may be a monocyclic C6-C10 aryl group; or a polycyclic C10-C12 aryl group.

[0107] In another embodiment, Ar22 may be a phenyl group; a biphenyl group; or a naphthyl group.

[0108] In one embodiment of this application, R21 to R24 are identical or different from each other and are independently selected from the group consisting of 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'; -SiRR'R''; and -NRR'; or two or more adjacent groups may bond 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.

[0109] In another embodiment, R21 to R24 may be the same as or different from each other, and each may be hydrogen or deuterium independently.

[0110] In another embodiment, R21 to R24 may be hydrogen.

[0111] In one embodiment of this application, R25 and R26 may be the same or different from each other, and each independently be a substituted or unsubstituted C1-C60 alkyl group; or a substituted or unsubstituted C6-C60 aryl group; or two adjacent groups may be bonded to each other to form a substituted or unsubstituted C6-C60 aromatic hydrocarbon ring.

[0112] In one embodiment of this application, R25 and R26 may be the same or different from each other, and each independently be a substituted or unsubstituted C1-C40 alkyl group; or a substituted or unsubstituted C6-C40 aryl group; or two adjacent groups may be bonded to each other to form a substituted or unsubstituted C6-C40 aromatic hydrocarbon ring.

[0113] In one embodiment of this application, R25 and R26 may be the same or different from each other, and each independently be a C1-C40 alkyl group; or a C6-C40 aryl group; or two adjacent groups may be bonded to each other to form a C6-C40 aromatic hydrocarbon ring.

[0114] In one embodiment of this application, R25 and R26 may be the same or different from each other, independently being a methyl group or a phenyl group, or two adjacent groups may be bonded to each other to form a fluorenyl group.

[0115] In one embodiment of this application, the deuterium content of the chemical formula 1 may be 0% to 100%.

[0116] According to one embodiment of this application, the chemical formula 1 may be represented by any one of the following compounds, but is not limited thereto.

[0117] [ka] TIFF0007839567000036.tif168161 TIFF0007839567000037.tif168161 TIFF0007839567000038.tif168161 TIFF0007839567000039.tif165161 TIFF0007839567000040.tif176161 TIFF0007839567000041.tif190161 TIFF0007839567000042.tif199161 TIFF0007839567000043.tif155161 TIFF0007839567000044.tif164161 TIFF0007839567000045.tif155161 TIFF0007839567000046.tif162161 TIFF0007839567000047.tif155161 TIFF0007839567000048.tif164161 TIFF0007839567000049.tif180161 TIFF0007839567000050.tif189161 TIFF0007839567000051.tif167161 TIFF0007839567000052.tif178161 TIFF0007839567000053.tif180161 TIFF0007839567000054.tif192161 TIFF0007839567000055.tif188161 TIFF0007839567000056.tif197161 TIFF0007839567000057.tif216161 TIFF0007839567000058.tif217161 TIFF0007839567000059.tif171161 TIFF0007839567000060.tif182161 TIFF0007839567000061.tif190161 TIFF0007839567000062.tif201161 TIFF0007839567000063.tif185161 TIFF0007839567000064.tif196161 TIFF0007839567000065.tif219161 TIFF0007839567000066.tif218161 TIFF0007839567000067.tif150161 TIFF0007839567000068.tif167161 TIFF0007839567000069.tif97161

[0118] Furthermore, by introducing various substituents into the structure of chemical formula 1, compounds possessing the unique properties of the introduced substituents can be synthesized. For example, by introducing substituents mainly used in hole injection layer materials, hole transport materials, light-emitting layer materials, electron transport layer materials, and charge generation layer materials used in the manufacture of organic light-emitting devices into the core structure, materials that satisfy the requirements for each organic layer can be synthesized.

[0119] Furthermore, by introducing various substituents to the structure of chemical formula 1, the energy band gap can be finely adjusted, while the properties at the interface between organic substances can be improved, thereby diversifying the applications of the material.

[0120] Furthermore, in one embodiment of this application, an organic light-emitting element is provided, comprising a first electrode; a second electrode provided opposite the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers contain a heterocyclic compound represented by the chemical formula 1.

[0121] In another embodiment, an organic light-emitting element is provided, comprising a first electrode; a second electrode provided opposite the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers contain one heterocyclic compound represented by the chemical formula 1.

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

[0123] In one embodiment of this application, the first electrode may be a positive electrode, and the second electrode may be a negative electrode.

[0124] In another embodiment, the first electrode may be a negative electrode, and the second electrode may be a positive electrode.

[0125] In one embodiment of this application, the organic light-emitting element may be a blue organic light-emitting element, and the heterocyclic compound represented by chemical formula 1 may be used as a material for the blue organic light-emitting element. For example, the heterocyclic compound according to chemical formula 1 may be included in the host material of the blue light-emitting layer of the blue organic light-emitting element.

[0126] In one embodiment of this application, the organic light-emitting element may be a green organic light-emitting element, and the heterocyclic compound according to chemical formula 1 may be used as a material for the green organic light-emitting element. For example, the heterocyclic compound according to chemical formula 1 may be included in the host material of the green light-emitting layer of the green organic light-emitting element.

[0127] In one embodiment of this application, the organic light-emitting element may be a red organic light-emitting element, and the heterocyclic compound according to chemical formula 1 may be used as a material for the red organic light-emitting element. For example, the heterocyclic compound according to chemical formula 1 may be included in the host material of the red light-emitting layer of the red organic light-emitting element.

[0128] The organic light-emitting element of the present invention may be manufactured by conventional methods and materials for manufacturing organic light-emitting elements, except for forming one or more organic layers using the heterocyclic compound described above.

[0129] The heterocyclic compound may be formed on the organic layer during the manufacture of the organic light-emitting element not only by vacuum deposition but also by a solution coating method. Here, solution coating methods include, but are not limited to, spin coating, dip coating, inkjet printing, screen printing, spray coating, and roll coating.

[0130] The organic layer of the organic light-emitting element of the present invention may have a single-layer structure, or it may have a multilayer structure in which two or more organic layers are stacked. For example, the organic light-emitting element of the present invention may have a structure in which the organic layer includes a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and so on. However, the structure of the organic light-emitting element is not limited thereto and may include even fewer organic layers.

[0131] In the organic light-emitting device of the present invention, the organic material layer may include a light-emitting layer, and the light-emitting layer may include the heterocyclic compound.

[0132] In other organic light-emitting devices, the organic layer may include a light-emitting layer, the light-emitting layer may include a host substance, and the host substance may include the heterocyclic compound.

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

[0134] In the organic light-emitting element of the present invention, the organic layer includes an electron injection layer or an electron transport layer, and the electron transport layer or electron injection layer may include the heterocyclic compound.

[0135] In other organic light-emitting devices, the organic layer may include an electron blocking layer or a hole blocking layer, and the electron blocking layer or hole blocking layer may include the heterocyclic compound.

[0136] In other organic light-emitting devices, the organic layer may include a hole transport layer, and the hole transport layer may include the heterocyclic compound.

[0137] The organic light-emitting element of the present invention may further include one or more layers selected from the group consisting of a light-emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer.

[0138] Figures 1-3 illustrate the stacking order of electrodes and organic layers in an organic light-emitting element according to one embodiment of this application. However, these drawings are not intended to limit the scope of this application, and organic light-emitting element structures well known in the art may also be applied to this application.

[0139] Figure 1 shows an organic light-emitting element in which a positive electrode 200, an organic material layer 300, and a negative electrode 400 are sequentially stacked on a substrate 100. However, the structure is not limited to this, and an organic light-emitting element in which a negative electrode, an organic material layer, and a positive electrode are sequentially stacked on a substrate may also be realized, as shown in Figure 2.

[0140] Figure 3 illustrates a case where the organic layers are multilayered. The organic light-emitting element according to Figure 3 includes a hole injection layer 301, a hole transport layer 302, an emissive layer 303, a hole blocking layer 304, an electron transport layer 305, and an electron injection layer 306. However, the scope of this application is not limited by such a multilayer structure, and the remaining layers except for the emissive layer may be omitted as needed, and other necessary functional layers may be added.

[0141] The organic layer containing the compound of chemical formula 1 may further contain other substances as needed.

[0142] In an organic light-emitting device according to one embodiment of this application, materials other than the heterocyclic compound of chemical formula 1 are given below as examples, but these are for illustrative purposes only and are not intended to limit the scope of this application, and may be substituted with materials known in the art.

[0143] As the positive electrode material, a material with a relatively large work function may be used, and transparent conductive oxides, metals, or conductive polymers may be used. Specific examples of the positive electrode material include, but are not limited to, metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline.

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

[0145] 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-carbazoyl-9-ylphenyl)amine (TCTA), 4,4',4''-tri[phenyl(m-tolyl)amino]triphenylamine (m-MTDATA), 1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene (m-MTDAPB), or polyaniline / dodecylbenzenesulfonic acid, a soluble conductive polymer. You may also use poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate), polyaniline / camphor sulfonic acid, or polyaniline / poly(4-styrene-sulfonate).

[0146] As the hole transport material, pyrazoline derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, etc. may be used, and low molecular weight or high molecular weight materials may also be used.

[0147] As electron transport materials, metal complexes of 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, 8-hydroxyquinoline and its derivatives may be used, and not only low molecular weight substances but also high molecular weight substances may be used.

[0148] LiF (LiFuminescent Fiber) is a typical electron injection material used in this industry, but this application is not limited to it.

[0149] As the light-emitting material, red, green, or blue light-emitting materials may be used, and if necessary, two or more light-emitting materials may be mixed and used. In this case, the two or more light-emitting materials may be deposited as individual sources, or they may be pre-mixed and deposited as a single source. Furthermore, fluorescent materials may be used as the light-emitting material, or phosphorescent materials may be used. As the light-emitting material, a material that emits light by combining holes and electrons injected from the positive electrode and negative electrode, respectively, may be used, or a material in which both the host material and the dopant material are involved in light emission may be used.

[0150] When using a mixture of hosts for the light-emitting material, hosts from the same system may be mixed, or hosts from different systems may be mixed. For example, two or more types of host materials, either n-type or p-type, may be selected and used as the host material for the light-emitting layer.

[0151] An organic light-emitting element according to one embodiment of this application may be of the top-emission type, bottom-emission type, or double-sided emission type, depending on the material used.

[0152] A heterocyclic compound according to one embodiment of this application can also operate in organic electronic devices such as organic solar cells, organic photoreceptors, and organic transistors, using a principle similar to that applied to organic light-emitting devices. [Examples]

[0153] The following examples will provide a more detailed explanation of this specification, but these are merely illustrative and not intended to limit the scope of this application.

[0154] <Manufacturing Example 1> Manufacturing of Compound 33 [ka]

[0155] Preparation of Compound 1-2 2,5-diiodobenzene-1,4-diol (34.5g, 0.095mol, 1eq), (3-chloro-2-fluorophenyl)boronic acid (A) (18.3g, 0.105mol, 1.1q), K2CO3 (28.9g, 0.21mol, 2.2eq), and Pd(PPh3)4 (5.5g, 0.0047mol, 0.05eq) were mixed with 1,4-dioxane (360ml) and H2O (90ml), and stirred at 90°C for 8 hours. After adding water to terminate the reaction, the mixture was extracted with methylene chloride (MC) and water. Then, water was removed with MgSO4. Compounds 1-2, 23 g each, were separated using a silica gel column to obtain a yield of 66%.

[0156] Manufacturing of Compounds 1-3 Compounds 1-2 (23g, 0.063mol, 1eq) and Cs2CO3 (41g, 0.125mol, 2eq) were mixed with DMF (140ml) and stirred at 150°C for 12 hours. After adding water to terminate the reaction, the mixture was extracted with methylene chloride (MC) and water. Subsequently, water was removed with MgSO4. Separation by silica gel column analysis yielded 16.2g of compound 1-3 in 74% yield.

[0157] Preparation of Compounds 1-4 Compounds 1-3 (16.2g, 0.047mol, 1eq), (3-bromo-2-fluorophenyl)boronic acid (B) (11.3g, 0.051mol, 1.1q), K2CO3 (14.3g, 0.103mol, 2.2eq), and Pd(PPh3)4 (2.7g, 0.0023mol, 0.05eq) were mixed with 1,4-dioxane (144ml) and H2O (42ml) and stirred at 90°C for 8 hours. After adding water to terminate the reaction, the mixture was extracted using MC and water. Subsequently, water was removed with MgSO4. Separation by silica gel column analysis yielded 13.8g of compound 1-4 in 75% yield.

[0158] Manufacturing of Compounds 1-5 Compounds 1-4 (13.8g, 0.035mol, 1eq) and Cs2CO3 (23.3g, 0.071mol, 2eq) were mixed with DMF (140ml) and stirred at 150°C for 12 hours. After adding water to terminate the reaction, the mixture was extracted using MC and water. Subsequently, water was removed with MgSO4. Separation by silica gel column analysis yielded 10g each of compounds 1-5 in 75% yield.

[0159] Preparation of Compounds 1-6 1,4-Dioxane (120 ml) and H2O (30 ml) were added to 1.5 g (10 g, 0.027 ol, 1 eq), phenylboronic acid (C) (3.6 g, 0.029 mol, 1.1 eq), K2CO3 (8.2 g, 0.059 mol, 2.2 eq), and Pd(PPh3)4 (1.5 g, 0.0013 mol, 0.05 eq), and the mixture was stirred at 90°C for 8 hours. After adding water to terminate the reaction, the mixture was extracted using MC and water. Subsequently, water was removed with MgSO4. Separation by silica gel column was performed to obtain 1-6,9 g of the compound in 90% yield.

[0160] Manufacturing of Compound 1 1-6 (9g, 0.024mol, 1eq), diphenylamine (D) (4.3g, 0.025mol, 1.05eq), NaOt-Bu (3.5g, 0.036mol, 1.5eq), and Pd2(dba)3 (1.1g, 0.0012mol, 0.05eq) were mixed with P(t-Bu)3 (0.49g, 0.0024mol, 0.1eq) and toluene (90ml), and the mixture was stirred at 100°C for 8 hours. After adding water to terminate the reaction, the mixture was extracted using MC and water. Subsequently, water was removed with MgSO4. Separation by silica gel column analysis yielded 1.9g of the compound in 73% yield.

[0161] The compounds were synthesized in the same manner as in Production Example 1, except that intermediates A, B, C, and D from Table 1 were used instead of (A), (B), (C), and (D) in Production Example 1.

[0162] [Table 1] TIFF0007839567000072.tif197165 TIFF0007839567000073.tif146165

[0163] The compound was prepared using the same method as in the above-mentioned manufacturing example, and the results of its synthesis verification are shown in Tables 2 and 3. Table 2 is 1 Table 3 shows the measurements obtained by 1H NMR (CDCl3, 200 MHz), and the measurements obtained by FD-MS (Field Desorption Mass Spectrometry).

[0164] [Table 2] TIFF0007839567000075.tif229165 TIFF0007839567000076.tif180165

[0165] [Table 3]

[0166] <Experimental Example 1> - Fabrication of Organic Light-Emitting Devices 1) Fabrication of organic light-emitting devices A transparent electrode indium tin oxide (ITO) thin film obtained from OLED glass (manufactured by Samsung Corning) was ultrasonically cleaned for 5 minutes each using trichloroethylene, acetone, ethanol, and distilled water in sequence, and then stored in isopropanol before use. Next, the ITO substrate was placed in the substrate holder of the vacuum deposition apparatus, and the following 4,4',4''-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA) was placed in the cell in the vacuum mounting apparatus.

[0167] [ka]

[0168] Next, after evacuating the chamber until the vacuum reached 10⁻⁶ torr, an electric current was applied to the cell to evaporate 2-TNATA, and a 600 Å thick hole injection layer was deposited on the ITO substrate. In another cell in the vacuum mounting apparatus, N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) was placed, an electric current was applied to the cell to evaporate it, and a 300 Å thick hole transport layer was deposited on the hole injection layer.

[0169] [ka]

[0170] After forming the hole injection layer and hole transport layer in this manner, a blue light-emitting material with the following structure was deposited on top of them as a light-emitting layer. Specifically, H1 was vacuum-deposited to a thickness of 200 Å as a blue light-emitting host material into one cell in the vacuum mounting apparatus, and D1 was vacuum-deposited on top of it as a blue light-emitting dopant material at a density of 5% relative to the host material.

[0171] [ka]

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

[0173] [ka]

[0174] An OLED device was fabricated by depositing lithium fluoride (LiF) to a thickness of 10 Å as the electron injection layer and using an Al anode to a thickness of 1,000 Å. Meanwhile, all organic compounds necessary for the fabrication of the OLED device were purified by vacuum sublimation at 10⁻⁶ to 10⁻⁸ torr for each material and used for OLED fabrication. An organic electroluminescent device was fabricated in the same manner as in Experimental Example 1, except that the compounds shown in Table 4 below were used instead of the NPB used in the formation of the hole transport layer. The results of measuring the driving voltage, luminous efficiency, color coordinate (CIE), and lifetime of the blue organic electroluminescent device manufactured according to the present invention are shown in Table 4.

[0175] [Table 4] TIFF0007839567000083.tif214165

[0176] As can be seen from the results in Table 4, the organic light-emitting device using the hole transport layer material of the blue organic light-emitting device of the present invention showed a lower driving voltage and significantly improved luminous efficiency and lifetime compared to the comparative example. Comparing the comparative example in Table 4 with the compound of the present invention, they are similar in that they both have an arylamine group, but they differ in that they also have an aromatic ring. In this case, the aromatic ring affects the spatial structure formation of the compound and suppresses intermolecular π-π stacking. Therefore, it is possible to prevent the phenomenon in which the driving voltage of the organic light-emitting device increases and the device characteristics deteriorate. It is judged that the compound of the present invention using such a derivative has improved hole transport characteristics or safety, resulting in excellence in all aspects of driving, efficiency, and lifetime.

[0177] <Experimental Example 2> Fabrication of organic light-emitting diodes A transparent electrode indium tin oxide (ITO) thin film obtained from OLED glass (manufactured by Samsung Corning) was ultrasonically cleaned for 5 minutes each using trichloroethylene, acetone, ethanol, and distilled water in sequence, and then stored in isopropanol before use. Next, the ITO substrate was placed in the substrate holder of the vacuum deposition apparatus, and the following 4,4',4''-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA) was placed in the cell in the vacuum mounting apparatus.

[0178] [ka]

[0179] Next, after evacuating until the degree of vacuum 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 in the vacuum mounting apparatus, 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.

[0180]

Chemical formula

[0181] 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 a light-emitting layer. Specifically, H1 as a blue light-emitting host material was vacuum-deposited at a thickness of 200 Å in one cell in the vacuum mounting apparatus, and D1 as a blue light-emitting dopant material was vacuum-deposited at 5% relative to the host material thereon.

[0182]

Chemical formula

[0183] Next, a compound of the following structural formula E1 was deposited at a thickness of 300 Å as an electron transport layer.

[0184]

Chemical formula

[0185] An OLED device was fabricated by depositing lithium fluoride (LiF) to a thickness of 10 Å as an electron injection layer and using an Al anode to a thickness of 1,000 Å. Meanwhile, all organic compounds necessary for the fabrication of the OLED device were purified by vacuum sublimation at 10⁻⁶ to 10⁻⁸ torr for each material and used for OLED fabrication. An organic electroluminescent device was fabricated in the same manner as in Example 2, except that after forming a hole transport layer (NPB) to a thickness of 250 Å, an electron blocking layer was formed on top of the hole transport layer to a thickness of 50 Å of the compounds shown in Table 5 below. The results of measuring the driving voltage, luminous efficiency, color coordinate (CIE), and lifetime of the blue organic electroluminescent device manufactured according to the present invention are shown in Table 5 below.

[0186] [Table 5] TIFF0007839567000089.tif229165

[0187] As can be seen from the results in Table 5 above, the organic light-emitting element using the electron-blocking layer material of the blue organic light-emitting element of the present invention exhibited a lower driving voltage and significantly improved luminous efficiency and lifetime compared to the comparative example. In the case of electrons, if they proceed to the positive electrode via the hole transport layer without coupling in the light-emitting layer, a phenomenon occurs in which the efficiency and lifetime of the OLED element decrease. To prevent such a phenomenon, if a compound with a high LUMO level is used as the electron-blocking layer, electrons attempting to proceed to the positive electrode via the light-emitting layer are blocked by the energy barrier of the electron-blocking layer. Therefore, the probability of holes and electrons forming an exciton increases, and the possibility of light being emitted from the light-emitting layer increases, leading to the conclusion that the compound of the present invention has brought about excellence in all aspects of driving, efficiency, and lifetime.

[0188] In particular, when an amine derivative is used as a hole transport layer for the compound of chemical formula 1 of this application, the lone pair of electrons in the amine improves the flow of holes, thereby enhancing the hole transport capacity of the hole transport layer. When used as an electron blocking layer, it can suppress the degradation of the hole transport material caused by electrons entering the hole transport layer. Furthermore, it was confirmed that the bonding of substituents with enhanced hole properties to the amine moiety increases the planarity of the amine derivative and the glass transition temperature, thereby improving the thermal stability of the compound.

[0189] Furthermore, by adjusting the band gap and T1 value, the hole transfer capability is improved, and the molecular stability is also enhanced. This allows us to lower the device's driving voltage, improve optical efficiency, and enhance the device's lifetime characteristics through the thermal stability of the compound.

Claims

1. The heterocyclic compound represented by the following chemical formula 1: 【Chemistry 1】 In the aforementioned chemical formula 1, X1 and X2 are either identical or different from each other, and independently of each other, O; or S. R1 and R2 are either identical or different from each other, and each is independently an unsubstituted or deuterium-substituted C6-C12 aryl group. L1 to L3 are identical or different from each other, and each is independently directly bonded; or substituted or unsubstituted C6 to C60 arylene groups. Ar1 to Ar3 are either identical or different from each other, and each is independently an unsubstituted or C1-C60 alkyl group or a C6-C18 substituted C1-C60 alkyl group or phenyl group; a dibenzofuran group; or a dibenzothiophene group. r, p, m, b, and q are 0, a is 1.

2. The aforementioned chemical formula 1 is represented by any one of the following chemical formulas 2 to 5, wherein the heterocyclic compound is as described in claim 1: 【Chemistry 2】 【Transformation 3】 【Chemistry 4】 【Transformation 5】 In the aforementioned chemical formulas 2 to 5, R1, R2, L1-L3, Ar1-Ar3, r, p, m, q, a, and b are defined as in the same way as in Chemical Formula 1.

3. The aforementioned chemical formula 1 is represented by any one of the following chemical formulas 6 to 9, wherein the heterocyclic compound is as described in claim 1: 【Transformation 6】 【Transformation 7】 【Transformation 8】 【Chemistry 9】 In the aforementioned chemical formulas 6 to 9, R1, R2, L1-L3, Ar1-Ar3, r, p, m, q, a, and b are defined as in the same way as in Chemical Formula 1.

4. The chemical formula 1 【Chemistry 10】 The heterocyclic compound according to claim 1, which is represented by any one of the following chemical formulas 1-1-1 to 1-1-3: 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】 In the above chemical formulas 1-1-1 to 1-1-3, The definitions of L1, m, L3, and r are the same as those in the definitions in Chemical Formula 1 above. 【Chemistry 14】 This refers to the position that is linked to the aforementioned chemical formula 1. Ar21 is an unsubstituted C1-C30 alkyl group or a C6-C18 aryl group substituted with a phenyl group. Ar22 is an unsubstituted C1-C30 alkyl group or a C6-C12 aryl group substituted with a phenyl group. X21 is O; or S, R21-R24 are hydrogen. R25 and R26 are either the same as or different from each other, and are independently C1-C30 alkyl groups; or phenyl groups.

5. The heterocyclic compound according to claim 1, wherein the chemical formula 1 is represented by any one of the following compounds. 【Chemistry 15】 【Chemistry 16】 【Chemistry 17】 [Chemistry 18] 【Chemistry 19】 【Chemistry 20】 【Chemistry 21】 【Chemistry 22】 【Chemistry 23】 【Chemistry 24】 【Chemistry 25】 【Chemistry 26】 【Chemistry 27】 【Chemistry 28】 【Chemistry 29】 【Transformation 30】 【Chemistry 31】 【Chemistry 32】 【Transformation 33】 【Transformation 34】 【Chemistry 35】 【Transformation 36】 【Chemistry 37】 【Transformation 38】 【Chemistry 39】 【Chemistry 40】 【Chemistry 41】 【Chemistry 42】 【Chemistry 43】 【Chemistry 44】 【Chemistry 45】 【Chemistry 46】 【Chemistry 47】 【Chemistry 48】

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

7. The organic light-emitting element according to claim 6, wherein the organic layer includes a light-emitting layer, and the light-emitting layer includes the heterocyclic compound.

8. The organic light-emitting element according to claim 6, wherein the organic layer includes an electron blocking layer or a hole blocking layer, and the electron blocking layer or hole blocking layer includes the heterocyclic compound.

9. The organic light-emitting element according to claim 6, wherein the organic layer includes a hole transport layer, and the hole transport layer includes the heterocyclic compound.

10. The organic light-emitting element according to claim 6, further comprising one or more layers selected from the group consisting of an emissive 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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