Heterocyclic compound and organic light-emitting element comprising same

Abstract

The present specification provides a heterocyclic compound and an organic light-emitting element including the same.

Description

Technical Field

[0001] The present invention relates to a heterocyclic compound and an organic light-emitting element including the heterocyclic compound.

[0002] This application claims priority to and the benefits of Korean Patent Application No. 10-2022-0074274 filed on June 17, 2022 in the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference. Background Art

[0003] An electroluminescence (EL) element is a self-emissive display element and has advantages in that it has a wide viewing angle, an excellent contrast ratio, and a fast response speed.

[0004] The organic light-emitting element is composed of a structure in which an organic thin film is provided between two electrodes. When a voltage is applied to the organic light-emitting element having such a structure, electrons and holes injected from the two electrodes are combined with each other into pairs in the organic thin film, and then the paired electrons and holes emit light while being annihilated. The organic thin film may be composed of a single layer or multiple layers as required.

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

[0006] In order to improve the performance, efficiency and service life of organic light emitting devices, there is a continuous need to develop materials for organic thin films. Summary of the invention

[0007] Technical issues

[0008] The present invention is directed to providing a heterocyclic compound and an organic light-emitting element comprising the same.

[0009] Technical Solutions

[0010] In an exemplary embodiment of the present application, a heterocyclic compound represented by the following Chemical Formula 1 is provided.

[0011] [Chemical formula 1]

[0012]

[0013] In Chemical Formula 1,

[0014] L1 to L3 are the same as or different from each other and are each independently a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group,

[0015] R1 is a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0016] R2 and R3 are the same as or different from each other and are each independently substituted or unsubstituted C6 to C60 aryl; substituted or unsubstituted C2 to C60 heteroaryl; or -N(Ra)(Rb), and at least one of R2 and R3 is -N(Ra)(Rb),

[0017] Ra and Rb are the same as or different from each other, and are each independently a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0018] R4 to R5 are the same as or different from each other and are each independently hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl,

[0019] a is an integer from 0 to 3, b is an integer from 0 to 5, and when a and b are each an integer of 2 or greater, the substituents in the brackets are the same as or different from each other, and

[0020] p, q and r are each an integer of 0 to 4, and when p, q and r are each an integer of 2 or greater, the substituents in the brackets are the same as or different from each other.

[0021] In addition, in an exemplary embodiment of the present application, an organic light-emitting element is provided, which includes: a first electrode; a second electrode, which is arranged to face the first electrode; and an organic material layer having one or more layers, which is arranged between the first electrode and the second electrode, wherein one or more layers of the organic material layer contain a heterocyclic compound represented by Chemical Formula 1.

[0022] Beneficial effects

[0023] The heterocyclic compound described in this specification can be used as a material of an organic material layer of an organic light-emitting element. That is, the heterocyclic compound can be used as a light-emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material, and the like in an organic light-emitting element. Specifically, the heterocyclic compound can be used as a material of a light-emitting layer of an organic light-emitting element.

[0024] Specifically, one or two or more of the heterocyclic compounds represented by Chemical Formula 1 may be used, and the heterocyclic compound represented by Chemical Formula 1 may be used as a material for a light-emitting layer. Specifically, the heterocyclic compound may be used as a host material for a light-emitting layer of an organic light-emitting element by introducing various substituents and changing the binding position of the substituents to adjust the band gap.

[0025] Since the heterocyclic compound of the present invention has a disubstituted structure in which an arylamine group is introduced into the core skeleton and an aryl group or a heteroaryl group is additionally introduced into the core skeleton, the structural stability is better than that of the monosubstituted structure and the hole mobility becomes faster than that of the monosubstituted structure.

[0026] In particular, when the heterocyclic compound of the present invention is used in a hole transport layer, an electron blocking layer or a light emitting layer of an organic light emitting device, the driving voltage of the device can be reduced, the efficiency of the device can be improved, and the service life of the device can be extended. BRIEF DESCRIPTION OF THE DRAWINGS

[0027] Figures 1 to 4 1 and 2 are diagrams each schematically showing a stack structure of an organic light emitting element according to an exemplary embodiment of the present application.

[0028] [Explanation of symbols]

[0029] 100:Substrate

[0030] 200: Positive electrode

[0031] 300: organic material layer

[0032] 301: hole injection layer

[0033] 302: hole transport layer

[0034] 303: Luminous layer

[0035] 304: Hole blocking layer

[0036] 305: electron transport layer

[0037] 306: electron injection layer

[0038] 307:Electron blocking layer

[0039] 400: Negative electrode DETAILED DESCRIPTION

[0040] Hereinafter, the present specification will be explained in more detail.

[0041] In the present specification, when a component “comprises” a constituent element, unless otherwise specifically stated, this does not mean that another constituent element is excluded but means that another constituent element may be further included.

[0042] In this specification, in the chemical formula It means the position to which the constituent elements are bonded.

[0043] The term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is changed to another substituent, and the position to be substituted is not limited as long as the position is a position where a hydrogen atom is substituted (i.e., a position where a substituent can be substituted), and when two or more substituents are substituted, the two or more substituents may be the same as or different from each other.

[0044] In the present specification, “substituted or unsubstituted” means unsubstituted or substituted by a group selected from deuterium, a halogen group, —CN, a C1 to C60 alkyl group, a C2 to C60 alkenyl group, a C2 to C60 alkynyl group, a C1 to C60 haloalkyl group, a C1 to C60 alkoxy group, a C6 to C60 aryloxy group, a C1 to C60 alkylthiooxy group, a C6 to C60 arylthiooxy group, a C1 to C60 alkylsulfonyloxy group, a C6 to C60 arylsulfonyloxy group, a C3 to C60 cycloalkyl group, a C2 to C60 cycloalkyl ... The invention further comprises a substituent selected from the group consisting of: a C6 to C60 heterocycloalkyl group, a C6 to C60 aryl group, a C2 to C60 heteroaryl group, -SiRR'R", -P(=O)RR' and -NRR', or a substituent to which two or more substituents selected from the enumerated substituents are linked, and R, R' and R" are each independently 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, a heterocycloalkyl group, an aryl group and a heteroaryl group.

[0045] In this specification, "when no substituent is specified in a chemical formula or a structure of a compound" means that a hydrogen atom is bonded to a carbon atom. However, since deuterium ( 2 H) is an isotope of hydrogen, so some of the hydrogen atoms may be deuterium.

[0046] In an exemplary embodiment of the present application, "when no substituent is specified in a chemical formula or a structure of a compound" may mean that all positions accessible to the substituent are hydrogen or deuterium. That is, deuterium is an isotope of hydrogen, and some hydrogen atoms may be deuterium as an isotope, and in this case, the content of deuterium may be 0% to 100%.

[0047] In an exemplary embodiment of the present application, in the case where “substituents are not specified in the chemical formula or the structure of the compound”, when deuterium is not explicitly excluded from all substituents (for example, the deuterium content is 0% and the hydrogen content is 100%), hydrogen and deuterium can be mixed and used in the compound.

[0048] In the exemplary embodiment of the present application, deuterium is one of the isotopes of hydrogen, is an element having a deuteron consisting of one proton and one neutron as a nucleus, and can be represented by hydrogen-2, and the element symbol can also be expressed as D or 2 H.

[0049] In the exemplary embodiments of the present application, isotopes refer to atoms having the same atomic number (Z) but different mass numbers (A), and isotopes may also be interpreted as elements having the same proton number but different neutron numbers.

[0050] In an exemplary embodiment of the present application, when the total number of substituents of the base compound is defined as T1, and the number of specific substituents among the substituents is defined as T2, the content T% of the specific substituent may be defined as T2 / T1×100=T%.

[0051] That is, in the example, when the total number of substituents that the phenyl group may have is 5 (T1 in the formula) and the number of deuterium in the substituent is 1 (T2 in the formula), The deuterium content of 20% in the phenyl group represented by can be represented by 20%. That is, the deuterium content of 20% in the phenyl group can be represented by the following structural formula.

[0052]

[0053] Furthermore, in an exemplary embodiment of the present application, “a phenyl group having a deuterium content of 0%” may mean a phenyl group not including a deuterium atom (ie, having five hydrogen atoms).

[0054] In the present specification, halogen may be fluorine, chlorine, bromine or iodine.

[0055] 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 with another substituent. 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 of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, t-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, t-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, octyl, n-octyl, t-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like, but are not limited thereto.

[0056] In the present specification, alkenyl includes a straight chain or branched chain having 2 to 60 carbon atoms, and may be substituted with another substituent. The number of carbon atoms of the alkenyl may be 2 to 60, specifically 2 to 40, and more specifically 2 to 20. Specific examples of alkenyl include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, distyryl, styryl and the like, but are not limited thereto.

[0057] In the present specification, the alkynyl group includes a straight chain or branched chain having 2 to 60 carbon atoms, and may be further substituted with another substituent. The number of carbon atoms of the alkynyl group may be 2 to 60, specifically 2 to 40, and more specifically 2 to 20.

[0058] In the present specification, a haloalkyl group means an alkyl group substituted with a halogen group, and specific examples of the haloalkyl group include -CF3, -CF2CF3 and the like, but are not limited thereto.

[0059] In the present specification, the alkoxy group is represented by -O(R101), and the above-mentioned examples of the alkyl group can be applied to R101.

[0060] In the present specification, the aryloxy group is represented by -O(R102), and the above-mentioned examples of the aryl group can be applied to R102.

[0061] In the present specification, the alkylthioxy group is represented by -S(R103), and the above-mentioned examples of the alkyl group can be applied to R103.

[0062] In the present specification, the arylthiooxy group is represented by -S(R104), and the above-mentioned examples of the aryl group can be applied to R104.

[0063] In the present specification, the alkylsulfonic acid oxygen group is represented by -S(=0)2(R105), and the above-mentioned examples of the alkyl group can be applied to R105.

[0064] In the present specification, the arylsulfonic acidoxy group is represented by -S(=0)2(R106), and the above-mentioned examples of the aryl group can be applied to R106.

[0065] In the present specification, cycloalkyl includes monocyclic or polycyclic rings having 3 to 60 carbon atoms, and may be substituted with another substituent. Here, polycyclic means a group in which a cycloalkyl group is directly linked or fused to another cyclic group. Here, another cyclic group may also be a cycloalkyl group, but may also be another cyclic group, such as a heterocycloalkyl group, an aryl group, a heteroaryl group, and the like. The number of carbon atoms in the cycloalkyl group may be 3 to 60, specifically 3 to 40, and more specifically 5 to 20. Specific examples of cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto.

[0066] In this specification, heterocycloalkyl contains O, S, Se, N or Si as a heteroatom, including monocyclic or polycyclic rings having 2 to 60 carbon atoms, and may be substituted by another substituent. Here, polycyclic means a group in which heterocycloalkyl is directly linked or fused to another cyclic group. Here, the other cyclic group may also be heterocycloalkyl, but may also be another cyclic group, such as cycloalkyl, aryl, heteroaryl and the like. The number of carbon atoms in heterocycloalkyl may be 2 to 60, specifically 2 to 40, and more specifically 3 to 20.

[0067] In the present specification, aryl includes monocyclic or polycyclic rings having 6 to 60 carbon atoms, and may be substituted with another substituent. Here, polycyclic means a group in which an aryl group is directly linked or fused to another cyclic group. Here, the other cyclic group may also be an aryl group, but may also be another cyclic group, such as a cycloalkyl group, a heterocycloalkyl group, a heteroaryl group, and the like. Aryl includes spirocyclic groups. 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 aryl groups include phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, The invention also includes, but is not limited to, 1,2-dihydro-1H-indenyl, 2,3-dihydro-1H-indenyl, 2,4 ...

[0068] In the present specification, the terphenyl group may be selected from the following structures.

[0069]

[0070] In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.

[0071] When the fluorenyl group is substituted, the substituent may be and similar groups, but are not limited thereto.

[0072] In this specification, heteroaryl includes S, O, Se, N or Si as a heteroatom, including monocyclic or polycyclic rings having 2 to 60 carbon atoms, and may be substituted by another substituent. Here, polycyclic means a group in which the heteroaryl is directly linked or fused to another cyclic group. Here, the other cyclic group may also be a heteroaryl, but may also be another cyclic group, such as a cycloalkyl, a heterocycloalkyl, an aryl and the like. The number of carbon atoms of the heteroaryl may be 2 to 60, specifically 2 to 40, and more specifically 3 to 25. Specific examples of the heteroaryl group include pyridyl, pyrrolyl, pyrimidinyl, pyridazinyl, furanyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, furazanyl, oxadiazolyl, thiadiazolyl, dithiazolyl, tetrazolyl, pyranyl, thiopyranyl, diazinyl, oxazinyl, thiazinyl, dioxin group, triazinyl, tetrazinyl, quinolyl, isoquinolyl, quinazoline group, isoquinazolinyl, quinozoline group, naphthyridinyl, acridinyl, phenanthridine group, group), imidazopyridyl, naphthazinyl, triazaindenyl, indolyl, indolizinyl, benzothiazolyl, benzoxazolyl, benzimidazolyl, benzothienyl, benzofuranyl, dibenzothienyl, dibenzofuranyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenazinyl, dibenzosilole group, spirobis(dibenzosilole) group, dihydrophenazinyl, phenoxazinyl, phenanthridinyl, thienyl, indolo[2,3-a]carbazolyl, indolo[2,3-b]carbazolyl, dihydroindole, 10,11-dihydro-dibenzo[b,f]azepine, 9,10-dihydroacridinyl, phenazinyl, phenothiazine group), phthalazinyl, phenanthroline, naphthiobenzofuranyl, naphthiobenzothiophene, benzo[c][1,2,5]thiadiazolyl, 2,3-dihydrobenzo[b]thiophene, 2,3-dihydrobenzofuranyl, 5,10-dihydrodibenzo[b,e][1,4]azasilyl, pyrazolo[1,5-c]quinazolinyl, pyrido[1,2-b]indazolyl, pyrido[1,2-a]imidazo[1,2-e]dihydroindole, 5,11-dihydroindeno[1,2-b]carbazolyl and the like, but are not limited thereto.

[0073] In the present specification, when the substituent is a carbazolyl group, it means a group bonded to nitrogen or carbon of carbazole.

[0074] In the present specification, when the carbazole group is substituted, another substituent may be substituted on the nitrogen or carbon of the carbazole.

[0075] In the present specification, the benzocarbazolyl group may be any of the following structures.

[0076]

[0077] In the present specification, the dibenzocarbazolyl group may be any of the following structures.

[0078]

[0079] In the present specification, the naphthobenzofuranyl group may be any of the following structures.

[0080]

[0081] In the present specification, the naphthobenzothienyl group may be any of the following structures.

[0082]

[0083] In the present specification, the silyl group includes Si and is a substituent to which the Si atom is directly bonded as a free radical, and is represented by -Si(R107)(R108)(R109), and R107 to R109 are the same as or different from each other, and may 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, a heterocycloalkyl group, an aryl group, and a heteroaryl group. Specific examples of the silyl group include (trimethylsilyl), (triethylsilyl), (tert-butyldimethylsilyl), (vinyldimethylsilyl), (propyldimethylsilyl), (triphenylsilyl), (diphenylsilyl), (phenylsilyl) and the like, but are not limited thereto.

[0084] In the present specification, the phosphine oxide group is represented by -P(=O)(R110)(R111), and R110 and R111 are the same or different from each other, and can be each independently 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, a heterocycloalkyl group, an aryl group, and a heteroaryl group. Specifically, the phosphine oxide group can be substituted with an alkyl group or an aryl group, and the above examples can be applied to the alkyl group and the aryl group. Examples of the phosphine oxide group include a dimethyl phosphine oxide group, a diphenyl phosphine oxide group, a dinaphthyl phosphine oxide group, and the like, but are not limited thereto.

[0085] In the present specification, the amino group is represented by -N(R112)(R113), and R112 and R113 are the same or different from each other, and can be independently a substituent consisting of at least one of hydrogen, deuterium, halogen, alkyl, alkenyl, alkoxy, cycloalkyl, heterocycloalkyl, aryl and heteroaryl. The amino group can be selected from the group consisting of -NH2, monoalkylamino, monoarylamino, monoheteroarylamino, dialkylamino, diarylamino, diheteroarylamino, alkylarylamino, alkylheteroarylamino and arylheteroarylamino, and the number of carbon atoms in the amino group is not particularly limited, but is preferably 1 to 30. Specific examples of amine groups include methylamine, dimethylamine, ethylamine, diethylamine, phenylamine, naphthylamine, biphenylamine, dibiphenylamine, anthracenylamine, 9-methyl-anthrylamine, diphenylamine, phenylnaphthylamine, ditolylamine, phenyltolylamine, triphenylamine, biphenylnaphthylamine, phenylbiphenylamine, biphenylfluorenylamine, phenyltriphenylamine, biphenyltriphenylamine and the like, but are not limited thereto.

[0086] In the present specification, the above-mentioned examples of the arylene group can be applied to an arylene group other than a divalent arylene group.

[0087] In the present specification, the above-mentioned examples of the heteroarylene group can be applied to heteroarylene groups other than the divalent heteroarylene group.

[0088] In the present specification, an "adjacent" group may mean a substituent substituted with an atom directly linked to the atom in which the corresponding substituent is substituted, a substituent located closest to the corresponding substituent in space, or another substituent substituted with an atom in which the corresponding substituent is substituted. For example, two substituents substituted at the ortho position in a benzene ring and two substituents substituted at the same carbon in an aliphatic ring may be interpreted as groups "adjacent" to each other.

[0089] The hydrocarbon ring and heterocyclic ring that adjacent groups may form include an aliphatic hydrocarbon ring, an aromatic hydrocarbon ring, an aliphatic heterocyclic ring, and an aromatic heterocyclic ring, and the structures exemplified by the above-mentioned cycloalkyl group, aryl group, heterocycloalkyl group, and heteroaryl group may be applied to rings other than the ring that is not a monovalent group.

[0090] In an exemplary embodiment of the present application, a heterocyclic compound represented by Chemical Formula 1 is provided.

[0091] In the exemplary embodiments of the present application, a group not represented by a substituent or a group represented by hydrogen may mean that all may be substituted with deuterium. That is, it may indicate that hydrogen or deuterium may be substituted with each other.

[0092] In general, compounds bonded to hydrogen and compounds substituted with deuterium show differences in thermodynamic behavior. This is because deuterium is characterized by having even lower vibration energy due to the mass of the deuterium atom being twice as high as that of the hydrogen atom.

[0093] In addition, the single bond dissociation energy of carbon and deuterium is higher than that of carbon and hydrogen. Therefore, the deuterium-substituted structure has the effect of improving the thermal stability of the molecule and improving the service life of the element by utilizing the improved thermal stability.

[0094] When the compound is deposited on a silicon wafer, the deuterium-containing material tends to pack so that the distance between molecules is reduced. In addition, when the surface of the film is observed using an atomic force microscope (AFM), it can be confirmed that the film made of the deuterium-containing compound is deposited with a more uniform surface without any aggregated portion.

[0095] The deuterium content of the heterocyclic compound of Chemical Formula 1 of the present application may be greater than 0% and 100% or less than 100%. The deuterium-substituted compound is characterized in that the ground state energy is lower than the ground state energy of the hydrogen-substituted compound, and the shorter the bond length between carbon and deuterium, the smaller the molecular hardcore volume. Therefore, the electrical polarizability can be reduced, and the intermolecular interaction can be weakened, so that when the device is manufactured, the device has a more stable stacking structure.

[0096] These characteristics cause the effect of reducing crystallinity by generating an amorphous state of the thin film. That is, the heterocyclic compound represented by Chemical Formula 1 can effectively improve the heat resistance of an organic light emitting diode (OLED) device, thereby improving the service life and driving characteristics.

[0097] In this specification, the deuterium content means the deuterium content relative to the total amount of hydrogen and deuterium included in Chemical Formula 1.

[0098] In an exemplary embodiment of the present application, the deuterium content of the heterocyclic compound of Chemical Formula 1 may be 0%, or 30% to 100%.

[0099] In an exemplary embodiment of the present application, the deuterium content of the heterocyclic compound of Chemical Formula 1 may be 0%, or 50% to 100%.

[0100] In an exemplary embodiment of the present application, the deuterium content of the heterocyclic compound of Chemical Formula 1 may be 0%, or 70% to 100%.

[0101] In an exemplary embodiment of the present application, the deuterium content of the heterocyclic compound of Chemical Formula 1 may be 0%, or 90% to 100%.

[0102] In an exemplary embodiment of the present application, the deuterium content of the heterocyclic compound of Chemical Formula 1 may be 0%.

[0103] In an exemplary embodiment of the present application, the deuterium content of the heterocyclic compound of Chemical Formula 1 may be 30% to 100%.

[0104] In an exemplary embodiment of the present application, the deuterium content of the heterocyclic compound of Chemical Formula 1 may be 50% to 100%.

[0105] In an exemplary embodiment of the present application, the deuterium content of the heterocyclic compound of Chemical Formula 1 may be 70% to 100%.

[0106] In an exemplary embodiment of the present application, the deuterium content of the heterocyclic compound of Chemical Formula 1 may be 90% to 100%.

[0107] In an exemplary embodiment of the present application, L1 to L3 are the same as or different from each other, and may each independently be a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group.

[0108] In another exemplary embodiment, L1 to L3 are the same as or different from each other, and may each independently be a direct bond; a substituted or unsubstituted C6 to C40 arylene group; or a substituted or unsubstituted C2 to C40 heteroarylene group.

[0109] In yet another exemplary embodiment, L1 to L3 are the same as or different from each other, and may each independently be a direct bond; a substituted or unsubstituted C6 to C20 arylene group; or a substituted or unsubstituted C2 to C20 heteroarylene group.

[0110] In yet another exemplary embodiment, L1 to L3 are the same as or different from each other, and may each independently be a direct bond; or a substituted or unsubstituted C6 to C20 arylene group.

[0111] In still another exemplary embodiment, L1 to L3 are the same as or different from each other, and may each independently be a direct bond; or a substituted or unsubstituted phenylene group.

[0112] In further exemplary embodiments, L1 to L3 are the same as or different from each other, and may each independently be a direct bond; or an unsubstituted or deuterium-substituted phenylene group.

[0113] In an exemplary embodiment of the present application, R1 may be a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0114] In another exemplary embodiment, R1 may be a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group.

[0115] In yet another exemplary embodiment, R1 may be a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0116] In yet another exemplary embodiment, R1 may be a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthryl group; a substituted or unsubstituted triphenylene group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophenyl group.

[0117] In yet another exemplary embodiment, R1 may be an unsubstituted or deuterium-substituted phenyl group; a biphenyl group; an unsubstituted or deuterium-substituted naphthyl group; a phenanthryl group; a triphenylene group; a methyl-substituted fluorenyl group; a dibenzofuranyl group; or a dibenzothienyl group.

[0118] In an exemplary embodiment of the present application, R2 and R3 are the same as or different from each other, and are each independently a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; or -N(Ra)(Rb), and at least one of R2 and R3 may be -N(Ra)(Rb).

[0119] In another exemplary embodiment, R2 and R3 are the same as or different from each other and are each independently a substituted or unsubstituted C6 to C40 aryl group; a substituted or unsubstituted C2 to C40 heteroaryl group; or -N(Ra)(Rb), and at least one of R2 and R3 may be -N(Ra)(Rb).

[0120] In another exemplary embodiment, R2 and R3 are the same as or different from each other and are each independently a substituted or unsubstituted C6 to C20 aryl group; a substituted or unsubstituted C2 to C20 heteroaryl group; or -N(Ra)(Rb), and at least one of R2 and R3 may be -N(Ra)(Rb).

[0121] In another exemplary embodiment, R2 and R3 are the same as or different from each other, and are each independently substituted or unsubstituted phenyl; substituted or unsubstituted biphenyl; substituted or unsubstituted naphthyl; substituted or unsubstituted phenanthryl; substituted or unsubstituted triphenylene; substituted or unsubstituted fluorenyl; substituted or unsubstituted dibenzofuranyl; substituted or unsubstituted dibenzothiophenyl; or -N(Ra)(Rb), and any one of R2 and R3 may be -N(Ra)(Rb).

[0122] In another exemplary embodiment, R2 and R3 are the same as or different from each other, and are each independently substituted or unsubstituted phenyl; substituted or unsubstituted biphenyl; substituted or unsubstituted naphthyl; substituted or unsubstituted phenanthryl; substituted or unsubstituted triphenylene; substituted or unsubstituted dibenzofuranyl; substituted or unsubstituted dibenzothiophenyl; or -N(Ra)(Rb), and any one of R2 and R3 may be -N(Ra)(Rb).

[0123] In another exemplary embodiment, R2 and R3 are the same as or different from each other and are each independently unsubstituted or deuterium-substituted phenyl; biphenyl; naphthyl; phenanthrenyl; triphenylene; dibenzofuranyl; dibenzothienyl; or -N(Ra)(Rb), and at least one of R2 and R3 may be -N(Ra)(Rb).

[0124] In an exemplary embodiment of the present application, R2 is a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, and R3 may be -N(Ra)(Rb).

[0125] In an exemplary embodiment of the present application, R3 is a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, and R2 may be -N(Ra)(Rb).

[0126] In the exemplary embodiments of the present application, Ra and Rb are the same as or different from each other, and may be each independently a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0127] In another exemplary embodiment, Ra and Rb are the same as or different from each other, and may each independently be a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group.

[0128] In yet another exemplary embodiment, Ra and Rb are the same as or different from each other, and may each independently be a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0129] In yet another exemplary embodiment, Ra and Rb are the same as or different from each other, and may each independently be a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0130] In yet another exemplary embodiment, Ra and Rb are the same as or different from each other, and may each independently be a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthryl group; a substituted or unsubstituted triphenylene group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophenyl group.

[0131] In further exemplary embodiments, Ra and Rb are the same as or different from each other and may each independently be an unsubstituted or deuterium-substituted phenyl group or an unsubstituted or deuterium-substituted phenanthryl group; an unsubstituted or deuterium-substituted biphenyl group; an unsubstituted or deuterium-substituted naphthyl group; a phenanthryl group; a triphenylene group; a fluorenyl group which is unsubstituted or substituted with deuterium, phenyl or methyl; a spirobifluorenyl group; a dibenzofuranyl group; or a dibenzothiophenyl group.

[0132] In another further exemplary embodiment, Ra and Rb are the same as or different from each other and may each independently be an unsubstituted or deuterium-substituted phenyl group or an unsubstituted or deuterium-substituted phenanthryl group; an unsubstituted or deuterium-substituted biphenyl group; an unsubstituted or deuterium-substituted naphthyl group; a phenanthryl group; a triphenylene group; a fluorenyl group which is unsubstituted or substituted with deuterium, phenyl or methyl; a dibenzofuranyl group; or a dibenzothiophenyl group.

[0133] In an exemplary embodiment of the present application, R4 and R5 are the same as or different from each other, and may each independently be hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0134] In another exemplary embodiment, R4 and R5 are the same as or different from each other and may each independently be hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C40 alkyl; substituted or unsubstituted C3 to C40 cycloalkyl; substituted or unsubstituted C2 to C40 heterocycloalkyl; substituted or unsubstituted C6 to C40 aryl; or substituted or unsubstituted C2 to C40 heteroaryl.

[0135] In another exemplary embodiment, R4 and R5 are the same as or different from each other and may each independently be hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C20 alkyl; substituted or unsubstituted C3 to C20 cycloalkyl; substituted or unsubstituted C2 to C20 heterocycloalkyl; substituted or unsubstituted C6 to C20 aryl; or substituted or unsubstituted C2 to C20 heteroaryl.

[0136] In yet another exemplary embodiment, R4 and R5 are the same as or different from each other, and may each independently be hydrogen; deuterium; substituted or unsubstituted C1 to C20 alkyl; substituted or unsubstituted C6 to C20 aryl; or substituted or unsubstituted C2 to C20 heteroaryl.

[0137] In yet another exemplary embodiment, R4 and R5 are the same as or different from each other, and may each independently be hydrogen; deuterium; or a substituted or unsubstituted C6 to C20 aryl group.

[0138] In yet another exemplary embodiment, R4 and R5 are the same as or different from each other, and may each independently be hydrogen; or deuterium.

[0139] In an exemplary embodiment of the present application, a is an integer from 0 to 3, b is an integer from 0 to 5, and when a and b are each an integer of 2 or higher, the substituents in brackets are the same as or different from each other.

[0140] In another exemplary embodiment, a is an integer of 1 to 3, b is an integer of 1 to 5, and when a and b are each an integer of 2 or greater, the substituents in brackets are the same as or different from each other.

[0141] In yet another exemplary embodiment, a is an integer from 2 to 3, b is an integer from 3 to 5, and the substituents in brackets are the same as or different from each other.

[0142] In an exemplary embodiment of the present application, p, q and r are each an integer of 0 to 4, and when p, q and r are each an integer of 2 or higher, the substituents in brackets are the same as or different from each other.

[0143] In another exemplary embodiment, p, q and r are each an integer from 0 to 3, and when p, q and r are each an integer of 2 or higher, the substituents in the brackets are the same as or different from each other.

[0144] In yet another exemplary embodiment, p, q and r are each an integer from 0 to 2, and when p, q and r are each 2, the substituents in brackets are the same as or different from each other.

[0145] In yet another exemplary embodiment, p, q, and r are each 0 or 1.

[0146] In yet another exemplary embodiment, p, q, and r are 1.

[0147] In yet another exemplary embodiment, p, q, and r are zero.

[0148] In an exemplary embodiment of the present application, Chemical Formula 1 may be represented by any one of the following Chemical Formulas 1-1 to 1-5.

[0149] [Chemical formula 1-1]

[0150]

[0151] [Chemical formula 1-2]

[0152]

[0153] [Chemical formula 1-3]

[0154]

[0155] [Chemical formula 1-4]

[0156]

[0157] [Chemical formula 1-5]

[0158]

[0159] In Chemical Formula 1-1 to Chemical Formula 1-5,

[0160] The definitions of L1 to L3, R1, R4, R5, Ra, Rb, a, b, p, q, and r are the same as those in Chemical Formula 1, and

[0161] R6 and R7 are the same as or different from each other, and are each independently a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0162] In another exemplary embodiment, R6 and R7 are the same as or different from each other, and may each independently be a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group.

[0163] In yet another exemplary embodiment, R6 and R7 are the same as or different from each other, and may each independently be a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0164] In another exemplary embodiment, R6 and R7 are the same as or different from each other, and may each independently be a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthryl group; a substituted or unsubstituted triphenylene group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophenyl group.

[0165] In yet another exemplary embodiment, R6 and R7 are the same as or different from each other, and may be each independently an unsubstituted or deuterium-substituted phenyl group; a biphenyl group; a naphthyl group; a phenanthrenyl group; a triphenylene group; a dibenzofuranyl group; or a dibenzothienyl group.

[0166] In an exemplary embodiment of the present application, Chemical Formula 1 may be represented by any one of the following Chemical Formulas 1-10 to 1-15.

[0167] [Chemical formula 1-10]

[0168]

[0169] [Chemical formula 1-11]

[0170]

[0171] [Chemical formula 1-12]

[0172]

[0173] [Chemical formula 1-13]

[0174]

[0175] [Chemical formula 1-14]

[0176]

[0177] [Chemical formula 1-15]

[0178]

[0179] In Chemical Formula 1-10 to Chemical Formula 1-15,

[0180] The definitions of L1 to L3, R1, R4, R5, a, b, p, q and r are the same as those in Chemical Formula 1,

[0181] R8 is a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0182] R100 and R200 are the same as or different from each other, and are each independently a substituted or unsubstituted C6 to C60 aryl group,

[0183] X is O, S, N or C(Rc)(Rd),

[0184] R101 to R104 are the same as or different from each other and are each independently hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl,

[0185] Rc and Rd are the same as or different from each other, and are each independently a substituted or unsubstituted C1 to C60 alkyl group or a substituted or unsubstituted C6 to C60 aryl group, or are bonded to each other to form a substituted or unsubstituted ring, and

[0186] c is an integer of 0 to 3, d, e and f are each an integer of 0 to 4, and when c, d, e and f are each an integer of 2 or higher, the substituents in the brackets may be the same as or different from each other.

[0187] In another exemplary embodiment, R8 may be a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group.

[0188] In yet another exemplary embodiment, R8 may be a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0189] In yet another exemplary embodiment, R8 may be a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthryl group; a substituted or unsubstituted triphenylene group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted dibenzofuranyl group; or a substituted or unsubstituted dibenzothienyl group.

[0190] In yet another exemplary embodiment, R8 may be a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthryl group; a substituted or unsubstituted triphenylene group; a substituted or unsubstituted dibenzofuranyl group; or a substituted or unsubstituted dibenzothienyl group.

[0191] In further exemplary embodiments, R8 may be unsubstituted or deuterium-substituted phenyl; biphenyl; naphthyl; phenanthrenyl; triphenylene; dibenzofuranyl; or dibenzothienyl.

[0192] In another further exemplary embodiment, R100 and R200 are the same as or different from each other, and may each independently be a substituted or unsubstituted C6 to C40 aryl group.

[0193] In yet a further exemplary embodiment, R100 and R200 are the same as or different from each other, and may each independently be a substituted or unsubstituted C6 to C20 aryl group.

[0194] In yet a further exemplary embodiment, R100 and R200 are the same as or different from each other, and may each independently be a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted triphenylene group; or a substituted or unsubstituted fluorenyl group.

[0195] In yet a further exemplary embodiment, R100 and R200 are the same as or different from each other and may each independently be an unsubstituted or deuterium-substituted phenyl, a phenyl-substituted fluorenyl, or an unsubstituted or deuterium-substituted phenanthryl; an unsubstituted or deuterium-substituted biphenyl; an unsubstituted or deuterium-substituted naphthyl; a phenanthryl; a triphenylene; or an unsubstituted or deuterium-, phenyl- or methyl-substituted fluorenyl.

[0196] In yet a further exemplary embodiment, R100 and R200 are the same as or different from each other and may each independently be an unsubstituted or deuterium-substituted phenyl group or an unsubstituted or deuterium-substituted phenanthryl group; an unsubstituted or deuterium-substituted biphenyl group; an unsubstituted or deuterium-substituted naphthyl group; a phenanthryl group; a triphenylene group; or an unsubstituted or deuterium-, phenyl- or methyl-substituted fluorenyl group.

[0197] In yet a further exemplary embodiment, R100 is a substituted or unsubstituted phenyl group; or a substituted or unsubstituted biphenyl group, and R200 may be a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted triphenylene group; or a substituted or unsubstituted fluorenyl group.

[0198] In another exemplary embodiment, R101 to R104 are the same as or different from each other and may each independently be hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C40 alkyl group; a substituted or unsubstituted C3 to C40 cycloalkyl group; a substituted or unsubstituted C2 to C40 heterocycloalkyl group; a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group.

[0199] In another exemplary embodiment, R101 to R104 are the same as or different from each other and may each independently be hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C3 to C20 cycloalkyl group; a substituted or unsubstituted C2 to C20 heterocycloalkyl group; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0200] In yet another exemplary embodiment, R101 to R104 are the same as or different from each other, and may each independently be hydrogen; deuterium; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0201] In yet another exemplary embodiment, R101 to R104 are the same as or different from each other, and may each independently be hydrogen; deuterium; or a substituted or unsubstituted C6 to C20 aryl group.

[0202] In further exemplary embodiments, R101 to R104 are the same as or different from each other, and may each independently be hydrogen; or deuterium.

[0203] In another further exemplary embodiment, Rc and Rd are the same as or different from each other, and are each independently a substituted or unsubstituted C1 to C40 alkyl group; or a substituted or unsubstituted C6 to C40 aryl group, or may be bonded to each other to form a substituted or unsubstituted C6 to C40 ring.

[0204] In yet a further exemplary embodiment, Rc and Rd are the same as or different from each other, and are each independently a substituted or unsubstituted C1 to C20 alkyl group; or a substituted or unsubstituted C60 to C20 aryl group, or may be bonded to each other to form a substituted or unsubstituted C6 to C20 ring.

[0205] In yet a further exemplary embodiment, Rc and Rd are the same as or different from each other, and are each independently a C1 to C20 alkyl group or a C6 to C20 aryl group, or may be bonded to each other to form a fluorene ring.

[0206] In yet a further exemplary embodiment, Rc and Rd are the same as or different from each other, and are each independently a methyl group or a phenyl group, or may be bonded to each other to form a fluorene ring.

[0207] In yet a further exemplary embodiment, Rc and Rd are the same as or different from each other, and may each independently be a substituted or unsubstituted C1 to C40 alkyl group or a substituted or unsubstituted C6 to C40 aryl group.

[0208] In yet a further exemplary embodiment, Rc and Rd are the same as or different from each other, and may each independently be a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C6 to C20 aryl group.

[0209] In another exemplary embodiment, Rc and Rd are the same as or different from each other, and may each independently be a C1 to C20 alkyl group or a substituted or unsubstituted C6 to C20 aryl group.

[0210] In yet another exemplary embodiment, Rc and Rd are the same as or different from each other, and may each independently be a methyl group, a phenyl group, or a fluorenyl group.

[0211] In an exemplary embodiment of the present application, a heterocyclic compound is provided, in which Chemical Formula 1 is represented by any one of the following compounds.

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233]

[0234]

[0235]

[0236]

[0237] In the exemplary embodiments of the present application, the compound is only an example and is not limited thereto, and may include other compounds including additional substituents included in Chemical Formula 1. In addition, the deuterium substitution position of the compound may exist, while a specific position is excluded, and hydrogen and deuterium are mixed during the process of deuterium substitution and synthesis.

[0238] In addition, various substituents may be introduced into the structure of Chemical Formula 1 to synthesize compounds having inherent characteristics of the introduced substituents. For example, substituents commonly used in hole injection materials, hole transport materials, light-emitting materials, electron transport materials, and electron injection materials used when manufacturing an organic light-emitting element may be introduced into the core structure to synthesize a material that satisfies the conditions required for each organic material layer.

[0239] In addition, by introducing various substituents into the structure of Chemical Formula 1 or changing the bonding position, the band gap may be finely adjusted, and at the same time, the characteristics at the interface between organic material layers may be improved.

[0240] In addition, the compound of Chemical Formula 1 has excellent thermal stability, and such thermal stability provides driving stability and improves lifespan characteristics for an organic light emitting element.

[0241] In an exemplary embodiment of the present application, an organic light-emitting element is provided, comprising: a first electrode; a second electrode, arranged to face the first electrode; and an organic material layer having one or more layers, arranged between the first electrode and the second electrode, wherein one or more layers of the organic material layer contain a heterocyclic compound represented by Chemical Formula 1.

[0242] In another exemplary embodiment, an organic light-emitting element is provided, comprising: a first electrode; a second electrode disposed to face the first electrode; and an organic material layer having one or more layers disposed between the first electrode and the second electrode, wherein one or more layers of the organic material layer contain a heterocyclic compound represented by Chemical Formula 1.

[0243] In another exemplary embodiment, an organic light-emitting element is provided, comprising: a first electrode; a second electrode disposed to face the first electrode; and an organic material layer having one or more layers disposed between the first electrode and the second electrode, wherein the one or more layers of the organic material layer contain two or more heterocyclic compounds represented by Chemical Formula 1.

[0244] In yet another exemplary embodiment, the heterocyclic compound represented by Chemical Formula 1 may be used as a light-emitting material of a light-emitting layer of an organic light-emitting element.

[0245] In still another exemplary embodiment, the heterocyclic compound represented by Chemical Formula 1 may be used as a host material of a light emitting layer of an organic light emitting element.

[0246] In an exemplary embodiment of the present application, the first electrode may be a positive electrode, and the second electrode may be a negative electrode.

[0247] In another exemplary embodiment, the first electrode may be a negative electrode, and the second electrode may be a positive electrode.

[0248] In an exemplary embodiment of the present application, the organic light emitting element may be a blue organic light emitting element, and the heterocyclic compound according to Chemical Formula 1 may be used as a material for the blue organic light emitting element.

[0249] In an exemplary embodiment of the present application, the organic light emitting element may be a green organic light emitting element, and the heterocyclic compound represented by Chemical Formula 1 may be used as a material for the green organic light emitting element.

[0250] In an exemplary embodiment of the present application, the organic light emitting element may be a red organic light emitting element, and the heterocyclic compound represented by Chemical Formula 1 may be used as a material for the red organic light emitting element.

[0251] In an exemplary embodiment of the present application, the organic light emitting element may be a blue organic light emitting element, and the heterocyclic compound according to Chemical Formula 1 may be used as a material for a light emitting layer of the blue organic light emitting element.

[0252] In an exemplary embodiment of the present application, the organic light emitting element may be a green organic light emitting element, and the heterocyclic compound represented by Chemical Formula 1 may be used as a material for a light emitting layer of the green organic light emitting element.

[0253] In an exemplary embodiment of the present application, the organic light emitting element may be a red organic light emitting element, and the heterocyclic compound represented by Chemical Formula 1 may be used as a material for a light emitting layer of the red organic light emitting element.

[0254] In the exemplary embodiment of the present application, the specific contents about the heterocyclic compound represented by Chemical Formula 1 are the same as those described above.

[0255] In addition to using the above-mentioned heterocyclic compound to form an organic material layer having one or more layers, the organic light-emitting device of the present invention can be manufactured using typical manufacturing methods and materials of an organic light-emitting device.

[0256] When manufacturing an organic light emitting element, the heterocyclic compound can be formed into an organic material layer not only by a vacuum deposition method but also by a solution application method. Here, the solution application method means spin coating, dip coating, inkjet printing, screen printing, spray method, roll coating and the like, but is not limited thereto.

[0257] The organic material layer of the organic light-emitting element of the present invention may be composed of a single-layer structure, but may also be composed of a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light-emitting element 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, and the like as organic material layers. However, the structure of the organic light-emitting element is not limited thereto, but may include a smaller number of organic material layers.

[0258] In an exemplary embodiment of the present application, as the iridium-based dopant, Ir(ppy) 3 as a green phosphorescent dopant may be used.

[0259] In an exemplary embodiment of the present application, as an iridium-based dopant, (piq)2(Ir)(acac) which is a red phosphorescent dopant may be used.

[0260] In an exemplary embodiment of the present application, an organic light-emitting element is provided, wherein an organic material layer of the organic light-emitting element includes a light-emitting layer, and the light-emitting layer contains the heterocyclic compound.

[0261] In an exemplary embodiment of the present application, an organic light-emitting element is provided, wherein an organic material layer of the organic light-emitting element includes a light-emitting layer, and the light-emitting layer contains a host material, and the host material includes the heterocyclic compound.

[0262] In the organic light emitting element of the present invention, the organic material layer includes an electron injection layer or an electron transport layer, and the electron injection layer or the electron transport layer may contain the heterocyclic compound.

[0263] In another organic light emitting element, the organic material layer includes a hole blocking layer, and the hole blocking layer may contain the heterocyclic compound.

[0264] In yet another organic light emitting element, the organic material layer includes an electron blocking layer, and the electron blocking layer may contain the heterocyclic compound.

[0265] In yet another organic light emitting element, the organic material layer includes a hole transport layer, a light emitting layer or an electron blocking layer, and the hole transport layer, the light emitting layer or the electron blocking layer may contain the heterocyclic compound.

[0266] In still another organic light emitting element, the organic material layer includes a hole transport layer or a hole transport auxiliary layer, and the hole transport layer or the hole transport auxiliary layer may contain the heterocyclic compound.

[0267] In the organic light-emitting element of the present application, as a positive electrode material, a material having a relatively high work function can be used, and a transparent conductive oxide, a metal or a conductive polymer and the like can be used. Specific examples of the positive electrode 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; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole and polyaniline; and the like, but are not limited thereto.

[0268] As the negative electrode material, a material having a relatively low work function may be used, and a metal, a metal oxide, a conductive polymer, and the like may be used. Specific examples of the negative electrode material include: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer structure materials such as LiF / Al or LiO2 / Al; and the like, but are not limited thereto.

[0269] As the hole injection material, known hole injection materials can also be used, and for example, phthalocyanine compounds such as copper phthalocyanine disclosed in U.S. Pat. No. 4,356,429, or star-shaped sudden-action amine derivatives described in the document [Advanced Material, 6, p. 677 (1994)] such as tris(4-carbazoyl-9-ylphenyl)amine (TCTA), 4,4',4"-tri[phenyl(m-tolyl)amino]triphenylamine (4,4',4"-tri[p-tolyl]amino]triphenylamine henyl(m-tolyl)amino]triphenylamine, m-MTDATA), 1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene (1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene, m-MTDAPB), polyaniline / dodecylbenzenesulfonic acid or poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (which are soluble conductive polymers), polyaniline / camphorsulfonic acid or polyaniline / poly(4-styrenesulfonate), and similar materials.

[0270] As the hole transport material, pyrazoline derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, and the like can be used, and low molecular weight materials or polymer materials can also be used.

[0271] As electron transport materials, oxadiazole derivatives, anthraquinone dimethane and its derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, tetracyanoanthraquinone dimethane and its derivatives, fluorenone derivatives, diphenyl dicyanoethylene and its derivatives, dibenzoquinone derivatives, metal complexes of 8-hydroxyquinoline and its derivatives, and similar materials can be used, and low molecular weight materials and polymer materials can also be used.

[0272] As the electron injection material, for example, LiF is typically used in this technology, but the present application is not limited thereto.

[0273] As the light-emitting material, a red, green or blue light-emitting material can be used, and two or more light-emitting materials can be mixed and used as needed. In this case, two or more light-emitting materials are deposited as or used as separate supply sources, or are pre-mixed to be deposited as and used as one supply source. In addition, a fluorescent material can also be used as the light-emitting material, but a phosphorescent material can also be used. As the light-emitting material, a material that emits light by combining holes and electrons injected from the positive electrode and the negative electrode can also be used alone, but a material in which a host material and a dopant material participate in light emission together can also be used.

[0274] When the host of the light-emitting material is mixed and used, the hosts of the same series may be mixed and used, or hosts of different series may be mixed and used. For example, two or more types of materials selected from n-type host materials or p-type host materials may be used as the host material of the light-emitting layer.

[0275] The organic light emitting element according to the exemplary embodiment of the present application may be a top emission type, a bottom emission type, or a dual emission type according to materials to be used.

[0276] The heterocyclic compound according to the exemplary embodiment of the present application may function even in organic electronic elements including organic solar cells, organic photoconductors, organic transistors, and the like based on a principle similar to that applied to organic light emitting elements.

[0277] The organic light emitting element 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, a hole transport auxiliary layer, an electron blocking layer, a hole blocking layer, an electron transport layer and an electron injection layer.

[0278] The organic light emitting element 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 blocking layer, a hole blocking layer, an electron transport layer and an electron injection layer.

[0279] Figures 1 to 4 The stacking order of the electrodes and the organic material layers of the organic light emitting device according to the exemplary embodiment of the present application is illustrated. However, the scope of the present application is not intended to be limited by these drawings, and the structure of the organic light emitting device known in the art can also be applied to the present application.

[0280] according to Figure 1 , showing 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 organic light emitting element is not limited to this structure, and as Figure 2 As in the embodiment of the present invention, 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 implemented.

[0281] Figure 3 and Figure 4 An example is a case where the organic material layer is a multi-layered layer.

[0282] according to Figure 3The organic light-emitting element comprises 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).

[0283] according to Figure 4 The organic light-emitting element includes a hole injection layer (301), a hole transport layer (302), an electron blocking layer (307), a light-emitting layer (303), an electron transport layer (305) and an electron injection layer (306). However, the scope of the present application is not limited to the stacking structure described above, and other layers except the light-emitting layer can be omitted as needed, and another necessary functional layer can be further added.

[0284] In an exemplary embodiment of the present application, a method for manufacturing an organic light-emitting element is provided, the method comprising: preparing a substrate; forming a first electrode on the substrate; forming an organic material layer having one or more layers on the first electrode; and forming a second electrode on the organic material layer, wherein the forming of the organic material layer comprises using an organic material layer composition comprising the heterocyclic compound according to an exemplary embodiment of the present application to form an organic material layer having one or more layers.

[0285] Hereinafter, the present specification will be described in more detail through examples, but these examples are provided only to illustrate the present application and are not intended to limit the scope of the present application.

[0286] <Synthesis example>

[0287] [Preparation Example 1] Preparation of Compound 003

[0288]

[0289] 1) Preparation of compound 003-P6

[0290] After (3-methoxynaphthalen-2-yl)boronic acid (50 g, 247.51 mmol) and 1-bromo-4-chloro-2-nitrobenzene (61.45 g, 259.89 mmol) were dissolved in 500 ml of 1,4-dioxane and 100 ml of distilled water, Pd(PPh3)4 (14.30 g, 12.38 mmol) and K2CO3 (85.52 g, 618.78 mmol) were added thereto, and the resulting mixture was stirred under reflux for 12 hours. After the reaction was completed, the reaction solution 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, and then the residue was purified by column chromatography using dichloromethane and hexane as an eluting solvent, thereby obtaining compound 003-P6 (64 g, 82%).

[0291] 2) Preparation of compound 003-P5

[0292] Compound 003-P6 (64 g, 203.99 mmol) and triphenylphosphine (133.76 g, 509.98 mmol) were added to 700 ml of 1,2-dichlorobenzene, and the resulting mixture was stirred under reflux for 7 hours. After the reaction was completed, dichloromethane was added to the reaction solution for dissolution, and then the resulting solution was extracted with distilled water, the organic layer was dried over anhydrous MgSO4, and then the solvent was removed by a rotary evaporator, and then the residue was purified by column chromatography using dichloromethane and hexane as elution solvents, thereby obtaining compound 003-P5 (48 g, 86%).

[0293] 3) Preparation of Compound 003-P4

[0294] After compound 003-P5 (48 g, 170.37 mmol) and bromobenzene (32.1 g, 204.44 mmol) were dissolved in 500 ml of toluene, Pd2(dba)3 (7.80 g, 8.52 mmol), 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (xphos) (8.12 g, 17.04 mmol) and NaOtBu (32.75 g, 340.74 mmol) were added thereto, and the resulting mixture was stirred under reflux for 3 hours. After completion of the reaction, the reaction solution was extracted with dichloromethane and distilled water, the organic layer was dried over anhydrous MgSO4, and the solvent was removed by a rotary evaporator, and the residue was purified by column chromatography using dichloromethane and hexane as eluents to obtain compound 003-P4 (45 g, 74%).

[0295] 4) Preparation of Compound 003-P3

[0296] After dissolving compound 003-P4 (45 g, 125.76 mmol) in 500 ml of dichloromethane, boron tribromide (47.26 g, 188.64 mmol) was slowly added thereto at 0° C., and the resulting mixture was then stirred for 3 hours. After the reaction was completed, the reaction was then terminated by slowly adding distilled water to the reaction solution, extraction was performed using dichloromethane and distilled water, the organic layer was dried over anhydrous MgSO4, and the solvent was then removed by a rotary evaporator, and the residue was then purified by column chromatography using dichloromethane and hexane as eluting solvents, thereby obtaining compound 003-P3 (39 g, 90%).

[0297] 5) Preparation of Compound 003-P2

[0298] After dissolving compound 003-P3 (39 g, 74.85 mmol) in 400 ml of dichloromethane, triethylamine (13.77 g, 136.12 mmol) was added thereto, and then trifluoromethanesulfonic anhydride (38.41 g, 136.12 mmol) was slowly added thereto at 0° C., and then the resulting mixture was stirred for 1 hour. After the reaction was completed, the reaction was then terminated by slowly adding distilled water to the reaction solution, extraction was performed using dichloromethane and distilled water, the organic layer was dried over anhydrous MgSO4, and then the solvent was removed by a rotary evaporator, and then the residue was purified by column chromatography using dichloromethane and hexane as eluting solvents, thereby obtaining compound 003-P2 (48 g, 89%).

[0299] 6) Preparation of Compound 003-P1

[0300] After dissolving compound 003-P2 (48 g, 100.87 mmol) and phenylboronic acid (13.53 g, 110.95 mmol) in 500 ml of 1,4-dioxane and 100 ml of distilled water, Pd(PPh3)4 (5.83 g, 5.04 mmol) and K2CO3 (34.85 g, 252.17 mmol) were added thereto, and the resulting mixture was stirred under reflux for 10 hours. After the reaction was completed, the reaction solution 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, and then the residue was purified by column chromatography using dichloromethane and hexane as eluting solvents, thereby obtaining compound 003-P1 (33 g, 81%).

[0301] 7) Preparation of Compound 003

[0302] After dissolving compound 003-P1 (10 g, 24.76 mmol) and di([1,1'-biphenyl]-4-yl)amine (8.36 g, 26.00 mmol) in 100 ml of toluene, Pd2(dba)3 (1.13 g, 1.24 mmol), xphos (1.18 g, 2.48 mmol) and NaOtBu (4.76 g, 49.52 mmol) were added thereto, and the resulting mixture was stirred under reflux for 2 hours. After the reaction was completed, the reaction solution 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, and then the residue was purified by column chromatography using dichloromethane and hexane as eluting solvents, thereby obtaining compound 003 (13 g, 76%).

[0303] In the following Table 1, the target compound was synthesized by carrying out the preparation in the same manner as in Preparation Example 1, except that Compound A was used instead of 1-bromo-4-chloro-2-nitrobenzene, Compound B was used instead of bromobenzene, Compound C was used instead of phenylboronic acid, and Compound D was used instead of di([1,1'-biphenyl]-4-yl)amine.

[0304] [Table 1

[0305]

[0306]

[0307]

[0308]

[0309] [Preparation Example 2] Preparation of Compound 248

[0310] 1) Preparation of compound 248-P6

[0311] After (3-methoxynaphthalen-2-yl)boronic acid (50 g, 247.51 mmol) and 1-bromo-4-chloro-2-nitrobenzene (61.45 g, 259.89 mmol) were dissolved in 500 ml of 1,4-dioxane and 100 ml of distilled water, Pd(PPh3)4 (14.30 g, 12.38 mmol) and K2CO3 (85.52 g, 618.78 mmol) were added thereto, and the resulting mixture was stirred under reflux for 10 hours. After the reaction was completed, the reaction solution 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, and then the residue was purified by column chromatography using dichloromethane and hexane as an eluting solvent, thereby obtaining compound 248-P6 (64 g, 82%).

[0312] 2) Preparation of compound 248-P5

[0313] Compound 248-P6 (64 g, 203.99 mmol) and triphenylphosphine (133.76 g, 509.98 mmol) were added to 700 ml of 1,2-dichlorobenzene, and the resulting mixture was stirred under reflux for 7 hours. After the reaction was completed, dichloromethane was added to the reaction solution for dissolution, and then the resulting solution was extracted with distilled water, the organic layer was dried over anhydrous MgSO4, and then the solvent was removed by a rotary evaporator, and then the residue was purified by column chromatography using dichloromethane and hexane as eluting solvents, thereby obtaining compound 248-P5 (48 g, 86%).

[0314] 3) Preparation of compound 248-P4

[0315] After compound 248-P5 (48 g, 170.37 mmol) and bromobenzene (32.1 g, 204.44 mmol) were dissolved in 500 ml of toluene, Pd2(dba)3 (7.80 g, 8.52 mmol), xphos (8.12 g, 17.04 mmol) and NaOtBu (32.75 g, 340.74 mmol) were added thereto, and the resulting mixture was stirred under reflux for 2 hours. After the reaction was completed, the reaction solution 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, and then the residue was purified by column chromatography using dichloromethane and hexane as an eluting solvent, thereby obtaining compound 248-P4 (45 g, 74%).

[0316] 4) Preparation of compound 248-P3

[0317] After compound 248-P4 (45 g, 125.76 mmol) and phenylboronic acid (16.87 g, 138.33 mmol) were dissolved in 500 ml of 1,4-dioxane and 100 ml of distilled water, Pd(dba)2 (1.45 g, 2.52 mmol), xphos (3 g, 6.29 mmol) and K2CO3 (43.45 g, 314.40 mmol) were added thereto, and the resulting mixture was stirred under reflux for 12 hours. After the reaction was completed, the reaction solution 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, and then the residue was purified by column chromatography using dichloromethane and hexane as eluting solvents, thereby obtaining compound 248-P3 (41 g, 82%).

[0318] 5) Preparation of compound 248-P2

[0319] After dissolving compound 248-P3 (41 g, 102.63 mmol) in 500 ml of dichloromethane, boron tribromide (38.57 g, 153.95 mmol) was slowly added thereto at 0° C., and the resulting mixture was then stirred for 3 hours. After the reaction was completed, the reaction was then terminated by slowly adding distilled water to the reaction solution, extraction was performed using dichloromethane and distilled water, the organic layer was dried over anhydrous MgSO4, and the solvent was then removed by a rotary evaporator, and the residue was then purified by column chromatography using dichloromethane and hexane as eluting solvents, thereby obtaining compound 248-P2 (35 g, 88%).

[0320] 6) Preparation of Compound 248-P1

[0321] After compound 248-P2 (35 g, 90.80 mmol) was dissolved in 400 ml of dichloromethane, triethylamine (11.03 g, 108.96 mmol) was added thereto, and then trifluoromethanesulfonic anhydride (30.74 g, 108.96 mmol) was slowly added thereto at 0° C., and then the resulting mixture was stirred for 1 hour. After the reaction was completed, the reaction was then terminated by slowly adding distilled water to the reaction solution, extraction was performed using dichloromethane and distilled water, the organic layer was dried over anhydrous MgSO4, and then the solvent was removed by a rotary evaporator, and then the residue was purified by column chromatography using dichloromethane and hexane as eluting solvents, thereby obtaining compound 248-P1 (41 g, 87%).

[0322] 7) Preparation of Compound 248

[0323] After dissolving compound 248-P1 (10 g, 19.32 mmol) and N-([1,1'-biphenyl]-4-yl)naphthalene-2-amine (5.99 g, 20.29 mmol) in 100 ml of toluene, Pd2(dba)3 (0.88 g, 0.97 mmol), xphos (0.92 g, 1.93 mmol) and NaOtBu (3.71 g, 38.65 mmol) were added thereto, and the resulting mixture was stirred under reflux for 2 hours. After the reaction was completed, the reaction solution 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, and then the residue was purified by column chromatography using dichloromethane and hexane as eluting solvents, thereby obtaining compound 248 (11 g, 86%).

[0324] In the following Table 2, the target compound was synthesized by carrying out the preparation in the same manner as in Preparation Example 2, except that Compound E was used instead of 1-bromo-4-chloro-2-nitrobenzene, Compound F was used instead of bromobenzene, Compound G was used instead of phenylboronic acid, and Compound H was used instead of N-([1,1'-biphenyl]-4-yl)naphthalene-2-amine.

[0325] [Table 2]

[0326]

[0327]

[0328]

[0329] [Preparation Example 3] Preparation of Compound 039

[0330]

[0331] 1) Preparation of Compound 039

[0332] After dissolving compound 007-P1 (10 g, 24.76 mmol) and (4-(diphenylamino)phenyl)boronic acid (7.87 g, 27.23 mmol) in 100 ml of 1,4-dioxane and 20 ml of distilled water, Pd(dba)2 (0.28 g, 0.50 mol), xphos (0.59 g, 1.24 mmol) and K2CO3 (8.55 g, 61.90 mmol) were added thereto, and the resulting mixture was stirred under reflux for 6 hours. After the reaction was completed, the reaction solution 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, and then the residue was purified by column chromatography using dichloromethane and hexane as eluting solvents, thereby obtaining compound 039 (12 g, 79%).

[0333] In the following Table 3, the target compound was synthesized by performing the preparation in the same manner as in Preparation Example 3, except that Compound I was used instead of Compound 007-P1 and Compound J was used instead of (4-(diphenylamino)phenyl)boronic acid.

[0334] [Table 3]

[0335]

[0336] [Preparation Example 4] Preparation of Compound 461

[0337]

[0338] After compound 003 (10 g, 14.52 mmol), trifluoromethanesulfonic acid (3.27 g, 21.78 mmol) and 100 ml of D6-benzene were placed in a reaction flask, the resulting mixture was stirred under reflux for 5 hours. After the reaction was completed, the reaction was terminated by adding water thereto, extracted with dichloromethane and distilled water, the organic layer was dried over anhydrous MgSO4, and then the solvent was removed by a rotary evaporator, and then the residue was purified by column chromatography using dichloromethane and hexane as eluting solvents, thereby obtaining compound 461 (9 g, 86%).

[0339] pass 1 H nuclear magnetic resonance (NMR) and field desorption-mass spectrometry (FD-MS) confirmed the compounds synthesized in the preparation examples. 1Table 5 shows the measured values ​​of HNMR (CDCl 3 , 300 MHz), and Table 5 shows the measured values ​​of field desorption mass spectrometry (FD-MS).

[0340] [Table 4]

[0341]

[0342]

[0343] [Table 5]

[0344] Compound FD-MS Compound FD-MS 003 <![CDATA[m / z=688.86(C 52 H 36 N2=688.29)]]> 175 <![CDATA[m / z=676.80(C 50 H 32 N2O=676.25)]]> 006 <![CDATA[m / z=652.82(C 49 H 36 N2=652.29)]]> 184 <![CDATA[m / z=764.95(C 58 H 40 N2=764.32)]]> 007 <![CDATA[m / z=728.92(C 55 H 40 N2=728.32)]]> 199 <![CDATA[m / z=688.86(C 52 H 36 N2=688.29)]]> 016 <![CDATA[m / z=776.96(C 59 H 40 N2=776.32)]]> 200 <![CDATA[m / z=805.02(C 61 H 44 N2=804.35)]]> 017 <![CDATA[m / z=774.95(C 59 H 38 N2=774.30)]]> 202 <![CDATA[m / z=718.90(C 52 H 34 N2S=718.24)]]> 018 <![CDATA[m / z=776.96(C 59 H 40 N2=776.32)]]> 221 <![CDATA[m / z=686.84(C 52 H 34 N2=686.27)]]> 023 <![CDATA[m / z=688.86(C 52 H 36 N2=688.29)]]> 248 <![CDATA[m / z=662.82(C 50 H 34 N2=662.27)]]> 031 <![CDATA[m / z=712.88(C 54 H 36 N2=712.29)]]> 266 <![CDATA[m / z=652.82(C 49 H 36 N2=652.29)]]> 039 <![CDATA[m / z=612.76(C 46 H 32 N2=612.26)]]> 296 <![CDATA[m / z=776.96(C 59 H 40 N2=776.32)]]> 040 <![CDATA[m / z=728.92(C 55 H 40 N2=728.32)]]> 302 <![CDATA[m / z=688.86(C 52 H 36 N2=688.29)]]> 042 <![CDATA[m / z=612.76(C 46 H 32 N2=612.26)]]> 318 <![CDATA[m / z=778.94(C 58 H 38 N2O=778.30)]]> 073 <![CDATA[m / z=718.90(C 52 H 34 N2S=718.24)]]> 323 <![CDATA[m / z=738.91(C 56 H 38 N2=738.30)]]> 076 <![CDATA[m / z=853.06(C 65 H 44 N2=852.35)]]> 341 <![CDATA[m / z=642.81(C 46 H 30 N2S=642.21)]]> 079 <![CDATA[m / z=688.86(C 52 H 36 N2=688.29)]]> 361 <![CDATA[m / z=686.84(C 52 H 34 N2=686.27)]]> 089 <![CDATA[m / z=736.90(C 56 H 36 N2=736.29)]]> 381 <![CDATA[m / z=612.76(C 46 H 32 N2=612.26)<!-- 58 --> ]]> 095 <![CDATA[m / z=676.80(C 50 H 32 N2O=676.25)]]> 403 <![CDATA[m / z=738.91(C 56 H 38 N2=738.30)]]> 105 <![CDATA[m / z=738.91(C 56 H 38 N2=738.30)]]> 405 <![CDATA[m / z=738.91(C 56 H 38 N2=738.30)]]> 108 <![CDATA[m / z=712.88(C 54 H 36 N2=712.29)]]> 435 <![CDATA[m / z=732.89(C 52 H 32 N2OS=732.22)]]> 122 <![CDATA[m / z=702.84(C 52 H 34 N2O=702.27)]]> 442 <![CDATA[m / z=712.88(C 54 H 36 N2=712.29)]]> 144 <![CDATA[m / z=788.97(C 60 H 40 N2=788.32)]]> 461 <![CDATA[m / z=719.04(C 52 H6D 30 N2=718.48)]]> 163 <![CDATA[m / z=738.91(C 56 H 38 N2=738.30)]]> 468 <![CDATA[m / z=757.03(C 56 H 20 D 18 N2=756.42)]]> 474 <![CDATA[m / z=612.76(C 46 H 32 N2=612.26)]]> 488 <![CDATA[m / z=652.82(C 49 H 36 N2=652.29)]]>

[0345] <Experimental example>

[0346] [Experimental Example 1]

[0347] (1) Manufacturing of organic light-emitting devices

[0348] A glass substrate on which indium tin oxide (ITO) was thinly coated to a thickness of 1,500 angstroms was ultrasonically cleaned with distilled water. When the washing with distilled water was completed, the glass substrate was ultrasonically cleaned with a solvent (such as acetone, methanol, and isopropyl alcohol), dried, and then subjected to ultraviolet ozone (UVO) treatment for 5 minutes using UV in an ultraviolet (UV) cleaning machine. Thereafter, the substrate was transferred to a plasma cleaning machine (PT), and then subjected to plasma treatment in a vacuum state to achieve the ITO work function and remove the residual film, and the substrate was transferred to a thermal deposition device for organic deposition.

[0349]

[0350] Then, the air in the chamber was evacuated until the vacuum level in the chamber reached 10 -6 The vacuum deposition apparatus was placed in another cell of the vacuum deposition apparatus and a hole transport layer having a thickness of 1000 angstroms was deposited on the hole injection layer by applying an electric current to the cell to evaporate 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenyl amine (2-TNATA). The hole transport layer having a thickness of 1000 angstroms was deposited on the hole injection layer by placing the following N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) in another cell of the vacuum deposition apparatus and applying an electric current to the cell to evaporate NPB.

[0351]

[0352] As described below, a light emitting layer was thermally vacuum deposited on the hole transport layer. The light emitting layer was deposited by depositing a 400 angstrom thick compound of 9-[4-(4,6-diphenyl-1,3,5-triazine-2-yl)phenyl]-9'-phenyl-3,3'-bi-9H-carbazole as a host and doping the deposited layer with a green phosphorescent dopant Ir(ppy)3 at 7%. Thereafter, 60 angstroms of bathocuproine (BCP) was deposited on the light emitting layer as a hole blocking layer, and 300 angstroms of E1 was deposited as an electron transport layer.

[0353]

[0354] Finally, lithium fluoride (LiF) was deposited on the electron transport layer to a thickness of 10 angstroms to form an electron injection layer, and then an aluminum (Al) negative electrode was deposited on the electron injection layer to a thickness of 1,200 angstroms to form a negative electrode, thereby manufacturing an organic electroluminescent element.

[0355] At the same time, for each material, -6 ~10 -8 All organic compounds required for manufacturing OLED elements undergo vacuum sublimation purification under the support and are used to manufacture OLEDs.

[0356] The driving voltage and luminous efficiency of the organic electroluminescent element according to Experimental Example 1 are shown in Table 6 below, except that the compounds shown in Table 6 below were used instead of the compound NPB used when the hole transport layer was formed in Experimental Example 1.

[0357] In this case, the hole transport compounds (excluding NPB) of Comparative Examples 2 to 4 are as follows.

[0358]

[0359] (2) Driving voltage and luminous efficiency of organic light-emitting elements

[0360] For the organic electroluminescent element manufactured as described above, electroluminescent (EL) characteristics were measured by M7000 manufactured by McScience Inc., and based on the measurement results thereof, T 0 when the reference luminance was 20,000 cd / m 2 was measured by a lifetime measurement device (M6000) manufactured by McScience Inc. 95 (The time taken for the brightness to decrease to 95% from the reference brightness).

[0361] The properties of the organic electroluminescent element of the present invention are shown in Table 6 below.

[0362] [Table 6]

[0363]

[0364] As can be seen from the results shown in Table 6, in Examples 1 to 42 (which are organic light-emitting elements using the compound represented by Chemical Formula 1 of the present invention as a hole transport layer material), compared with Comparative Examples 1 to 4 (which are organic light-emitting elements that do not use the compound represented by Chemical Formula 1 of the present invention as a material for a hole transport layer), the driving voltage is low, and the luminous efficiency and service life are improved.

[0365] Compounds M1 to M3 used in Comparative Examples 2 to 4 are similar to the present invention in that an arylamine group is introduced as a substituent into a benzocarbazole-type five-ring skeleton, but the present invention has a disubstituted structure (for example, a structure in which two substituents are substituted) in which not only an arylamine group is introduced into the skeleton but also an aryl or heteroaryl group is additionally introduced.

[0366] The advantage of this double-substituted structure is that the structural stability is excellent compared to the single-substituted structures of Comparative Examples 2 to 4, and the hole mobility becomes faster than the hole mobility of the single-substituted structure. Therefore, it can be confirmed that the compound of the present invention has a low driving voltage and improved efficiency and service life compared to the compounds of Comparative Examples 2 to 4.

[0367] [Experimental Example 2]

[0368] (1) Manufacturing of organic light-emitting devices

[0369] The transparent electrode ITO thin films obtained from glass for OLED (manufactured by Samsung-Corning Co., Ltd.) were ultrasonically cleaned for 5 minutes using trichloroethylene, acetone, ethanol, and distilled water in sequence, and then placed in isopropyl alcohol, stored, and then used. Next, the ITO substrate was placed in a substrate folder of a vacuum deposition device, and the following 4,4',4"-tris[N,N-(2-naphthyl)-phenylamino]triphenylamine (2-TNATA) was placed in a cell of the vacuum deposition device.

[0370]

[0371] Then, the air in the chamber was evacuated until the vacuum level in the chamber reached 10 -6 A hole injection layer having a thickness of 600 angstroms was deposited on the ITO substrate by applying an electric current to the cell to evaporate 2-TNATA. A hole transport layer having a thickness of 1000 angstroms was deposited on the hole injection layer by placing the following N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) in another cell of the vacuum deposition apparatus and applying an electric current to the cell to evaporate NPB.

[0372]

[0373] Subsequently, an electron blocking layer was deposited to a thickness of 100 angstroms using a compound having the following structural formula M1.

[0374]

[0375] A blue light-emitting material having the following structure is deposited on the electron blocking layer as a light-emitting layer. Specifically, a blue light-emitting host material H1 having a thickness of 300 angstroms is vacuum-deposited on a unit cell in a vacuum deposition device, and a blue light-emitting dopant material D1 is vacuum-deposited on the blue light-emitting host material H1 in an amount of 5% based on the host material.

[0376]

[0377] Subsequently, a compound having the following structural formula E1 was deposited to a thickness of 300 angstroms as an electron transport layer.

[0378]

[0379] The OLED element was manufactured by depositing lithium fluoride (LiF) with a thickness of 10 angstroms as an electron injection layer and allowing the Al negative electrode to have a thickness of 1,000 angstroms. At the same time, all organic compounds required for manufacturing the OLED element were made to have a thickness of 10 angstroms for each material. -6 ~10 -8 The substrate was purified by vacuum sublimation and used to make OLEDs.

[0380] (2) Driving voltage and luminous efficiency of organic light-emitting elements

[0381] The driving voltage and luminous efficiency of the organic electroluminescent element according to Experimental Example 2 are shown in Table 7 below, except that the compounds shown in Table 7 below were used instead of Compound M1 used when forming the electron blocking layer in Experimental Example 2.

[0382] [Table 7]

[0383]

[0384] As can be seen from the results shown in Table 7, in the organic light-emitting elements of Examples 43 to 63 using the compound represented by Chemical Formula 1 of the present invention as the electron blocking layer material, compared with the organic light-emitting elements of Comparative Examples 5 to 8 using M1 to M3 and NPB compounds as the electron blocking layer material, the driving voltage is low, and the luminous efficiency and service life are significantly improved.

[0385] [Experimental Example 3]

[0386] (1) Manufacturing of organic light-emitting devices

[0387] A glass substrate on which indium tin oxide (ITO) was thinly coated to a thickness of 1,500 angstroms was ultrasonically cleaned with distilled water. When the washing with distilled water was completed, the glass substrate was ultrasonically cleaned with a solvent such as acetone, methanol, and isopropyl alcohol, dried, and then subjected to UVO treatment for 5 minutes using UV in a UV cleaning machine. Thereafter, the substrate was transferred to a plasma cleaning machine (PT), and then subjected to plasma treatment in a vacuum state to achieve an ITO work function and remove a residual film, and the substrate was transferred to a thermal deposition device for organic deposition.

[0388] Then, the air in the chamber was evacuated until the vacuum level in the chamber reached 10 -6 A hole injection layer having a thickness of 600 angstroms was deposited on the ITO substrate by applying an electric current to the cell to evaporate 2-TNATA. A hole transport layer having a thickness of 1000 angstroms was deposited on the hole injection layer by placing the following N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) in another cell of the vacuum deposition apparatus and applying an electric current to the cell to evaporate NPB.

[0389] As described below, the light-emitting layer was thermally vacuum deposited on the hole transport layer. The compounds shown in Table 8 below were used as hosts for the light-emitting layer by a vapor deposition method, and the hosts were doped with (piq)2(Ir)(acac) as a red phosphorescent dopant in an amount of 3% based on the weight of the host material and deposited to a thickness of 500 angstroms.

[0390] Thereafter, bathocuproin (BCP) was deposited on the light emitting layer to a thickness of 60 angstroms as a hole blocking layer, and Alq3 was deposited to a thickness of 200 angstroms as an electron transporting layer.

[0391] Finally, an organic light emitting element was manufactured by depositing lithium fluoride (LiF) with a thickness of 10 angstroms on the electron transport layer to form an electron injection layer, and then depositing an aluminum (Al) negative electrode with a thickness of 1,200 angstroms on the electron injection layer to form a negative electrode.

[0392] Specifically, the compounds used as hosts in Examples 64 to 77 and Comparative Examples 9 to 12 are shown in Table 8 below.

[0393] In this case, Compound M1 to Compound M3 used as hosts in Comparative Examples 9 to 11 of Table 8 below are as follows.

[0394]

[0395] At the same time, for each material, all organic compounds required to manufacture organic light-emitting elements are made within 10 -6 ~10 -8 The substrate was purified by vacuum sublimation and used to manufacture organic light-emitting elements.

[0396] (2) Driving voltage and luminous efficiency of organic light-emitting elements

[0397] For the organic light emitting element manufactured as described above, electroluminescence (EL) characteristics were measured by M7000 manufactured by Micro Scientific, and based on the measurement results thereof, T when the reference luminance was 6,000 cd / m² was measured by a lifetime measurement device (M6000) manufactured by Micro Scientific. 95 The results of measuring the driving voltage, luminous efficiency, luminous color and service life of the organic light-emitting element manufactured according to the present invention are shown in Table 8 below.

[0398] [Table 8]

[0399]

[0400] As can be seen from the results shown in Table 8, in the organic light-emitting elements of Examples 64 to 77 using the compound represented by Chemical Formula 1 of the present invention as the main material for the light-emitting layer, compared with the organic light-emitting elements of Comparative Examples 9 to 12 using M1 to M3 and NPB compounds as the main material for the light-emitting layer, the driving voltage is low, and the luminous efficiency and service life are significantly improved.

Claims

1. A heterocyclic compound represented by the following chemical formula 1, characterized in that: include: [Chemical formula 1] Wherein, in Chemical Formula 1, L1 to L3 are the same as or different from each other and are each independently a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group, R1 is a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, R2 and R3 are the same as or different from each other and are each independently substituted or unsubstituted C6 to C60 aryl; substituted or unsubstituted C2 to C60 heteroaryl; or -N(Ra)(Rb), and at least one of R2 and R3 is -N(Ra)(Rb), Ra and Rb are the same as or different from each other, and are each independently a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, R4 to R5 are the same as or different from each other and are each independently hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl, a is an integer from 0 to 3, b is an integer from 0 to 5, and when a and b are each an integer of 2 or greater, the substituents in the brackets are the same as or different from each other, and p, q and r are each an integer of 0 to 4, and when p, q and r are each an integer of 2 or greater, the substituents in the brackets are the same as or different from each other.

2. The heterocyclic compound according to claim 1, characterized in that Wherein Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-5: [Chemical formula 1-1] [Chemical formula 1-2] [Chemical formula 1-3] [Chemical formula 1-4] [Chemical formula 1-5] In Chemical Formula 1-1 to Chemical Formula 1-5, The definitions of L1 to L3, R1, R4, R5, Ra, Rb, a, b, p, q and r are the same as those in Chemical Formula 1, and R6 and R7 are the same as or different from each other and are each independently a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

3. The heterocyclic compound according to claim 1, characterized in that wherein Ra and Rb are the same as or different from each other, and are each independently a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group.

4. The heterocyclic compound according to claim 1, characterized in that wherein R2 and R3 are the same as or different from each other and are each independently substituted or unsubstituted C6 to C40 aryl; substituted or unsubstituted C2 to C40 heteroaryl; or -N(Ra)(Rb), and at least one of R2 and R3 is -N(Ra)(Rb).

5. The heterocyclic compound according to claim 1, characterized in that wherein R4 and R5 are the same as or different from each other and are independently hydrogen; or deuterium.

6. The heterocyclic compound according to claim 1, characterized in that The deuterium content of the heterocyclic compound of Chemical Formula 1 is 0%, or 30% to 100%.

7. The heterocyclic compound according to claim 1, characterized in that Wherein Chemical Formula 1 is represented by any one of the following compounds:

8. An organic light emitting element, characterized in that: include: a first electrode; a second electrode, arranged to face the first electrode; and an organic material layer having one or more layers, disposed between the first electrode and the second electrode, wherein the one or more layers of the organic material layer comprises the heterocyclic compound as claimed in any one of claims 1 to 7.

9. The organic light emitting element according to claim 8, characterized in that: The organic material layer includes a light-emitting layer, and the light-emitting layer includes the heterocyclic compound represented by Chemical Formula 1.

10. The organic light emitting element according to claim 8, characterized in that: The organic material layer includes a light-emitting layer, the light-emitting layer includes a host material, and the host material includes the heterocyclic compound represented by Chemical Formula 1.

11. The organic light emitting element according to claim 8, characterized in that: The organic material layer includes an electron blocking layer, and the electron blocking layer includes the heterocyclic compound represented by Chemical Formula 1.

12. The organic light emitting element according to claim 8, characterized in that: The organic material layer includes a hole transport layer or a hole transport auxiliary layer, and the hole transport layer or the hole transport auxiliary layer includes the heterocyclic compound represented by Chemical Formula 1.

13. The organic light emitting element according to claim 8, characterized in that: It also includes 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, a hole transport auxiliary layer, an electron blocking layer, a hole blocking layer, an electron transport layer and an electron injection layer.

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