TWI888735B - Heterocyclic compound, organic light emitting device comprising same and composition for organic layer - Google Patents

Abstract

The present specification relates to a heterocyclic compound represented by Chemical Formula 1, an organic light emitting device including the same and a composition for an organic layer. In Chemical Formula 1, the definition of each substituents is the same as in the detailed description. [Chemical Formula 1]

Description

Heterocyclic compound, organic light-emitting device including the same, and organic layer composition

This application claims priority and benefits to Korean Patent Application No. 10-2021-0087120 filed on July 2, 2021 with the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference.

This specification relates to a heterocyclic compound, an organic light-emitting element containing the same, and an organic layer composition.

Organic electroluminescent elements are a type of self-emissive display element, and have the advantages of wide viewing angle, excellent contrast and fast response rate.

An organic light-emitting element has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to the organic light-emitting element having the structure, electrons and holes injected from the two electrodes combine with each other in the organic thin film to form a pair, and then emit light when turned off. The organic thin film may be composed of a single layer or multiple layers as necessary.

If necessary, the material used for the organic thin film may have a light-emitting function. For example, as for the material used for the organic thin film, it is also possible to use a compound that can constitute a light-emitting layer by itself or it is also possible to use a compound that can serve as a host or dopant of a host-dopant type light-emitting layer. In addition, as for the material used for the organic thin film, it is also possible to use a compound that can perform functions such as hole injection, hole transport, electron blocking, hole blocking, electron transport or electron injection.

In order to improve the performance, service life or efficiency of organic light-emitting devices, it is necessary to continuously develop materials for organic thin films.

It is necessary to study an organic light-emitting device including a compound having a chemical structure, which can satisfy the conditions required for a material that can be used for an organic light-emitting device, such as an appropriate energy level, electrochemical stability, thermal stability, and similar properties, and can perform various functions required for an organic light-emitting device according to a substituent.

[Prior Art Literature]

[Patent Literature]

US Patent No.4,356,429

This application relates to a heterocyclic compound, an organic light-emitting element containing the same, and an organic layer composition.

In an exemplary embodiment of the present application, a heterocyclic compound represented by the following chemical formula 1 is provided.

[Chemical formula 1]

In Formula 1, X1 and X2 are the same or different and are independently O; S; or CRaRb, R1 to R10 are the same or different and are independently selected from the group consisting of: hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C2 to C60 alkenyl; substituted or unsubstituted C2 to C60 alkynyl; substituted or unsubstituted C1 to C60 alkoxy; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; substituted or unsubstituted C2 to C60 heteroaryl; -P(=O)RR'; and -SiRR'R", or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6 to C substituted or unsubstituted C2 to C60 aliphatic or aromatic hydrocarbon ring, or a substituted or unsubstituted C2 to C60 aliphatic or aromatic heterocyclic ring, at least one of R1 to R6 is represented by -N-Hetlene-L1-Z1, N-Hetlene is a substituted or unsubstituted C2 to C60 heteroaryl group containing one or more -N= bonds, and L1 is a direct bond; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C 60 heteroaryl, Z1 is a substituted or unsubstituted C1 to C60 alkyl, a substituted or unsubstituted C2 to C60 heteroaryl or a substituted or unsubstituted amine, and Ra, Rb, R, R' and R" are the same or different from each other, and each is independently a substituted or unsubstituted C1 to C60 alkyl; a substituted or unsubstituted C6 to C60 aryl; or a substituted or unsubstituted C2 to C60 heteroaryl.

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

In addition, an exemplary embodiment of the present application provides an organic light-emitting element, wherein the organic layer containing the heterocyclic compound of Chemical Formula 1 further contains a heterocyclic compound represented by the following Chemical Formula A.

In chemical formula A, Rc1 and Rd1 are the same or different and are independently selected from the group consisting of: hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C2 to C60 alkenyl; substituted or unsubstituted C2 to C60 alkynyl; substituted or unsubstituted C1 to C60 alkoxy; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; substituted or unsubstituted C2 to C60 heteroaryl; -SiRR'R"; -P(=O)RR' and -NRR', or two or more adjacent groups bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring or Substituted or unsubstituted heterocyclic ring, L2 is a direct bond; substituted or unsubstituted C6 to C60 aryl group; or substituted or unsubstituted C2 to C60 heteroaryl group, Ra1 and Rb1 are the same or different from each other and are independently -CN; -SiRR'R"; -P(=O)RR'; substituted or unsubstituted C6 to C60 aryl group; or substituted or unsubstituted C2 to C60 heteroaryl group, R, R' and R" are the same or different from each other and are independently hydrogen; deuterium; substituted or unsubstituted C1 to C60 alkyl group; or substituted or unsubstituted C6 to C60 aryl group, a1 is an integer from 0 to 4, r and s are integers from 0 to 7, and when a1, s and r are 2 or more, the substituents in the brackets are the same or different from each other.

In addition, another exemplary embodiment of the present application provides a composition of an organic layer of an organic light-emitting element, which comprises a heterocyclic compound represented by Chemical Formula 1 and a heterocyclic compound represented by Chemical Formula A.

Finally, an exemplary embodiment of the present application provides a method for manufacturing an organic light-emitting element, the method comprising: preparing a substrate; forming a first electrode on the substrate; forming an organic layer having one or more layers on the first electrode; and forming a second electrode on the organic layer, wherein the formation of the organic layer comprises forming the organic layer having one or more layers by using a composition of an organic layer according to an exemplary embodiment of the present application.

The compounds described in this specification can be used as materials for the organic layer of an organic light-emitting element. The compounds can function as hole injection materials, hole transport materials, luminescent materials, electron transport materials, electron injection materials, electron blocking materials, hole blocking materials or similar materials in an organic light-emitting element. Specifically, the compounds can be used as hole transport materials, luminescent materials or electron blocking materials of an organic light-emitting element.

Specifically, the heterocyclic compound of the present application is connected to a core structure containing at least one or more C2 to C60 heteroaryl linkers with at least one or more -N= bonds, and Z1 has a specific substituent, and can enhance the ET characteristics of the core structure itself and adjust the band gap and high T1 value of the compound, so that when the compound is used as a hole transport material, luminescent material or electron blocking material of an organic light-emitting element, it exhibits excellent efficiency.

In addition, the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula A can be used simultaneously as materials for the light-emitting layer of an organic light-emitting element. When the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula A are used simultaneously in an organic light-emitting element, the driving voltage of the element can be reduced, the light efficiency of the element can be improved, and the life characteristics of the element can be improved due to the thermal stability of the compound.

100:Substrate

200: Positive electrode

300: Organic layer

301: Hole injection layer

302: hole transport layer

303: Luminous layer

304: Hole blocking layer

305:Electron transmission layer

306: Electron injection layer

400: Negative electrode

Figures 1 to 3 are each a schematic view showing a stacked structure of an organic light-emitting element according to an exemplary embodiment of the present application.

Hereinafter, this instruction manual will be described in more detail.

In this specification, when a component "includes" a component, unless otherwise specifically described, this does not mean to exclude another component, but means that it may further include another component.

意謂組成構件所鍵結的位置。 In this specification, the chemical formula

It means the location where components are bonded.

The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is changed to another substituent, and the substituted position is not limited as long as the position is a position where a hydrogen atom is substituted, that is, 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 or different from each other.

In the present specification, "substituted or unsubstituted" means unsubstituted or substituted with one or more substituents selected from the group consisting of: deuterium; halogen; -CN; C1 to C60 alkyl; C2 to C60 alkenyl; C2 to C60 alkynyl; C1 to C60 halogenalkyl; C1 to C60 alkoxy; C6 to C60 aryloxy; C1 to C60 alkylthiooxy; C6 to C60 arylthiooxy; C1 to C60 alkylsulfonyl; C6 to C60 arylsulfonyl; C3 to C60 C60 cycloalkyl; C2 to C60 heterocycloalkyl; C6 to C60 aryl; C2 to C60 heteroaryl; -SiRR'R"; -P(=O)RR'; and -NRR', a substituent connected by two or more substituents selected from the exemplary substituents, and R, R' and R" are each independently hydrogen; deuterium; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl.

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

In an exemplary embodiment of the present application, "when no substituent is indicated in the chemical formula or the structure of the 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 deuterium content may be 0% to 100%.

In an exemplary embodiment of the present application, when "no substituent is indicated in the chemical formula or the structure of the compound", when the deuterium content is 0%, the hydrogen content is 100%, and all substituents do not explicitly exclude deuterium, such as hydrogen, hydrogen and deuterium can be mixed and used in the compound.

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

In an exemplary embodiment of the present application, isotopes mean atoms having the same atomic number (Z) but different mass numbers (A), and isotopes can be interpreted as elements having the same number of protons but different numbers of neutrons.

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

表示的苯基中具有20%的氘含量可表示為苯基可具有的取代基的總數目為5(公式中的T1)，且所述取代基中氘的數目為1(公式中的T2)時的20%。亦即，苯基中具有20%的氘含量可由以下結構式表示。 That is, in one example,

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

In addition, in an exemplary embodiment of the present application, "phenyl group having 0% deuterium content" may mean that the phenyl group does not contain deuterium atoms, that is, has five hydrogen atoms.

In this specification, halogen can be fluorine, chlorine, bromine or iodine.

In the present specification, the alkyl group includes a straight chain or a branched chain having 1 to 60 carbon atoms, and may be substituted with another substituent. The number of carbon atoms in the alkyl group may be 1 to 60, specifically 1 to 40, and more specifically 1 to 20. Specific examples thereof include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tertiary butyl, secondary butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tertiary 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, tertiary 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.

In the present specification, alkenyl includes a straight chain or branched chain having 2 to 60 carbon atoms, and may be substituted by another substituent. The number of carbon atoms of the alkenyl group may be 2 to 60, specifically 2 to 40, and more specifically 2 to 20. Specific examples thereof 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, stilbene, styryl, and similar groups, but are not limited thereto.

In the present specification, the alkynyl group includes a straight chain or a branched chain having 2 to 60 carbon atoms, and may be further substituted by 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.

In the present specification, the halogenalkyl group means an alkyl group substituted with a halogen group, and specific examples thereof include -CF ₃ , -CF ₂ CF ₃ and the like, but are not limited thereto.

In this specification, an alkoxy group is represented by -O(R101), and the alkyl group examples described above can be applied to R101.

In this specification, the aryloxy group is represented by -O(R102), and the aryl group examples described above can be applied to R102.

In this specification, an alkylthiooxy group is represented by -S(R103), and the alkyl examples described above can be applied to R103.

In this specification, the arylthiooxy group is represented by -S(R104), and the aryl examples described above can be applied to R104.

In the present specification, an alkylsulfonyl group is represented by -S(=O) ₂ (R105), and the above-described examples of the alkyl group can be applied to R105.

In the present specification, the arylsulfonyl group is represented by -S(=O) ₂ (R106), and the above-described examples of the aryl group can be applied to R106.

In the present specification, cycloalkyl includes monocyclic or polycyclic groups 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 connected to another cyclic group or fused to another cyclic group. Here, the other 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 thereof 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.

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

In the present specification, aryl includes monocyclic or polycyclic rings having 6 to 60 carbon atoms, and may be additionally substituted by another substituent. Here, polycyclic means a group in which the aryl is directly connected to another cyclic group 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 a spirocyclic group. The number of carbon atoms of the aryl group may be 6 to 60, specifically 6 to 40, and more specifically 6 to 25. Specific examples of the aryl group include phenyl, biphenyl, terphenyl, naphthyl, anthryl, chrysenyl, phenanthrenyl, perylenyl, fluoranthenyl, triphenyl, phenalenyl, pyrenyl, tetraphenyl, pentaphenyl, fluorenyl, indenyl, acenaphthylenyl, benzofluorenyl, spirobifluorenyl, 2,3-dihydro-1H-indenyl, fused ring groups thereof, and the like, but are not limited thereto.

In this specification, terphenyl can be selected from the following structures.

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

、

、

、

、

、

以及類似基團，但不限於此。 When the fluorenyl group is substituted, the substituent may be

,

,

,

,

,

and similar groups, but are not limited thereto.

In the present specification, the heteroaryl group contains S, O, Se, N or Si as a hetero atom, contains a monocyclic or polycyclic group having 2 to 60 carbon atoms, and may be substituted by another substituent. Here, polycyclic means a group in which the heteroaryl group is directly connected to another cyclic group or fused to another cyclic group. Here, the other cyclic group may also be a heteroaryl group, but may also be another cyclic group, such as a cycloalkyl group, a heterocycloalkyl group, an aryl group and the like. The number of carbon atoms of the heteroaryl group may be 2 to 60, specifically 2 to 40, and more specifically 3 to 25. Specific examples of the heteroaryl group may include pyridyl, pyrrolyl, pyrimidinyl, oxazinyl, furanyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, furazan group, oxadiazolyl, thiadiazolyl, dithiazolyl, tetrazolyl, pyranyl, thiopyranyl, diazinyl, oxazinyl, thiazinyl, dioxin group, triazinyl, tetrazinyl, quinolyl, isoquinolyl, quinazolinyl, isoquinazolinyl, quinozolinyl, quinozolinyl, naphthyridinyl, acridinyl, phenanthridine group, imidazopyridine group, diazanaphthalene group, triazaindene group, group), indolyl, indolizinyl, benzothiazolyl, benzoxazolyl, benzimidazolyl, benzothienyl, benzofuranyl, dibenzothienyl, dibenzofuranyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenazine group, dibenzosilole group, spirobi(dibenzosilole), dihydrophenazinyl, phenoxazinyl, phenanthridine group, thienyl group, indolo[2,3-a]carbazolyl, indolo[2,3-b]carbazolyl, indolyl, 10,11-dihydro-dibenzo[b,f]azepine, 9,10-dihydroacridinyl, phenanthrazine group, phenothiathiazine group, phthalazine group group), phenanthroline group, naphthobenzofuran group, naphthobenzothiophene group, benzo[c][1,2,5]thiadiazolyl group, 2,3-dihydrobenzo[b]thienyl group, 2,3-dihydrobenzofuranyl group, 5,10-dihydrodibenzo[b,e][1,4]azinesilyl group, pyrazolo[1,5-c]quinazolinyl group, pyrido[1,2-b]indazolyl group, pyrido[1,2-a]imidazo[1,2-e]indolyl group, 5,11-dihydroindeno[1,2-b]carbazolyl group and similar groups, but not limited thereto.

In this specification, when the substituent is a carbazole group, it means that it is bonded to the nitrogen or carbon of carbazole.

In this specification, when the carbazole group is substituted, another substituent may be substituted on the nitrogen or carbon of the carbazole.

In this specification, the benzocarbazolyl group may be any of the following structures.

In this specification, dibenzocarbazolyl can be any of the following structures.

In this specification, naphthobenzofuranyl can be any of the following structures.

In this specification, naphthobenzothienyl can be any of the following structures.

(三甲基矽基)、

(三乙基矽基)、

(三級丁基二甲基矽基)、

(乙烯基二甲基矽基)、

(丙基二甲基矽基)、

(聯三苯基矽基)、

(聯二苯基烯基)、

(苯基矽基)以及類似基團，但不限於此。 In the present specification, a silicon group includes Si and is a substituent represented by -Si(R107)(R108)(R109) in which Si atoms are directly connected as a group, and R107 to R109 are the same as or different from each other, and each may independently be a substituent consisting of at least one of the following: hydrogen; deuterium; halogen; alkyl; alkenyl; alkoxy; cycloalkyl; heterocycloalkyl; aryl and heteroaryl. Specific examples of silicon groups include

(Trimethylsilyl),

(Triethylsilyl),

(tertiary butyl dimethyl silyl),

(vinyl dimethyl silyl),

(propyl dimethylsilyl),

(Triphenylsilyl),

(biphenylene group),

(phenylsilyl) and similar groups, but are not limited thereto.

In this 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 each independently be a substituent consisting of at least one of the following: hydrogen; deuterium; halogen; alkyl; alkenyl; alkoxy; cycloalkyl; heterocycloalkyl; aryl and heteroaryl. Specifically, the phosphine oxide group can be substituted by an alkyl or aryl group, and the examples described above can be applied to alkyl and aryl groups. Examples of the phosphine oxide group include dimethyl phosphine oxide, diphenyl phosphine oxide, dinaphthyl phosphine oxide, and similar groups, but are not limited thereto.

In the present specification, the amino group is represented by -N(R112)(R113), and R112 and R113 are the same or different and are each independently a substituent consisting of at least one of the following: hydrogen; deuterium; halogen; alkyl; alkenyl; alkoxy; cycloalkyl; heterocycloalkyl; aryl and heteroaryl. In the present specification, 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 is not particularly limited, but is preferably 1 to 30. Specific examples of the amino group include methylamino, dimethylamino, ethylamino, diethylamino, aniline, naphthylamino, benzidine, dibenzidine, anthracenyl, 9-methyl-anthridine, diphenylamine, phenylnaphthylamine, dimethylamino, phenyltoluidine, triphenylamine, diphenylnaphthylamine, phenylbenzidine, diphenylfluorenylamine, phenyltriphenylamine, diphenyltriphenylamine and the like, but are not limited thereto.

In this specification, the aryl group examples described above may be applied to aryl groups other than divalent aryl groups.

In this specification, the examples of heteroaryl groups described above may be applied to heteroaryl groups other than divalent heteroaryl groups.

In this specification, an "adjacent" group may mean a substituent substituted by an atom directly connected to the atom in which the corresponding substituent is substituted, a substituent placed closest to the corresponding substituent in space, or another substituent substituted by the atom in which the corresponding substituent is substituted. For example, two substituents substituted at adjacent positions 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.

The hydrocarbon ring and heterocyclic ring that can be formed by adjacent groups include aliphatic hydrocarbon rings, aromatic hydrocarbon rings, aliphatic heterocyclic rings, and aromatic heterocyclic rings, and the structures exemplified by the above-mentioned cycloalkyl groups, aryl groups, heterocycloalkyl groups, and heteroaryl groups can be applied to rings other than those groups that are not monovalent groups.

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

In an exemplary embodiment of the present application, the deuterium content of the heterocyclic compound represented by Chemical Formula 1 may be 0% or greater than 0% and 100% or less than 100%.

In another exemplary embodiment, the deuterium content of the heterocyclic compound represented by Chemical Formula 1 may be 0% or greater and 100% or less than 100%, 1% or greater and 100% or less than 100%, 10% or greater and 100% or less than 100%, or 20% or greater and 100% or less than 100%.

In another exemplary embodiment, the deuterium content of the heterocyclic compound represented by Chemical Formula 1 may be 0%; 1% or greater than 1% and 20% or less than 20%; or 100%.

In an exemplary embodiment of the present application, a C2 to C60 heteroaryl group containing at least one or more -N= bonds means that at least one or more nitrogen (N) having both single bonds and double bonds is contained in a substituent having a C2 to C60 heteroaryl group, and a heteroaryl group consisting only of a single bond is not included in the definition. That is, examples of C2 to C60 heteroaryl groups containing at least one or more -N= bonds may be pyridyl, pyrimidyl, triazine, quinolyl, isoquinolyl, hydroquinone (quinol group), benzimidazolyl, oxazine, tetrazine and similar groups, and are not particularly limited as long as they contain at least one or more -N= bonds.

In an exemplary embodiment of the present application, Chemical Formula 1 can be represented by any one of the following Formulas 2 to 7.

[Chemical formula 6]

In Chemical Formulae 2 to 7, the definitions of R1 to R10, X1, and X2 are the same as those in Chemical Formula 1.

In an exemplary embodiment of the present application, X1 and X2 are the same or different from each other, and can be independently O; S; or CRaRb.

In another embodiment, X1 may be O, and X2 may be O.

In yet another exemplary embodiment, X1 may be O, and X2 may be S.

In yet another exemplary embodiment, X1 may be O, and X2 may be CRaRb.

In yet another exemplary embodiment, X1 may be S, and X2 may be O.

In yet another exemplary embodiment, X1 may be S, and X2 may be S.

In yet another exemplary embodiment, X1 may be S, and X2 may be CRaRb.

In another exemplary embodiment, X1 may be CRaRb, and X2 may be O.

In another exemplary embodiment, X1 may be CRaRb, and X2 may be S.

In yet another exemplary embodiment, X1 may be CRaRb, and X2 may be CRaRb.

In an exemplary embodiment of the present application, Ra and Rb are the same or different from each other, and are each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

In another exemplary embodiment, Ra and Rb are the same or different from each other, and are each independently a substituted or unsubstituted C1 to C40 alkyl group; a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group.

In another exemplary embodiment, Ra and Rb are the same 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.

In another exemplary embodiment, Ra and Rb are the same or different from each other, and are each independently a C1 to C40 alkyl group; or a C6 to C40 aryl group.

In another exemplary embodiment, Ra and Rb are the same or different from each other, and are each independently a C1 to C40 alkyl group.

In another exemplary embodiment, Ra and Rb are the same or different from each other, and each is independently a C1 to C20 alkyl group.

In another exemplary embodiment, Ra and Rb are the same or different from each other, and each is independently a straight chain C1 to C20 alkyl group; or a branched chain C3 to C20 alkyl group.

In another exemplary embodiment, Ra and Rb may be methyl groups.

In an exemplary embodiment of the present application, Ra and Rb may be substituted again with deuterium.

In an exemplary embodiment of the present application, Chemical Formula 1 can be represented by the following Chemical Formula 8 or Chemical Formula 9.

In Chemical Formulae 8 and 9, X1, X2, R7 to R10, N-Hetlene, L1 and Z1 are defined the same as those in Chemical Formula 1, R11 to R16 are the same or different from each other and are each independently hydrogen; deuterium; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl, and a is an integer from 0 to 3, and when a is 2 or greater than 2, the substituents in the brackets are the same or different from each other.

In an exemplary embodiment of the present application, Chemical Formula 8 can be represented by any one of the following Chemical Formulas 8-1 to 8-4.

[Chemical formula 8-3]

In Chemical Formula 8-1 to Chemical Formula 8-4, the definition of each substituent is the same as that in Chemical Formula 8.

In an exemplary embodiment of the present application, Chemical Formula 9 can be represented by any one of the following Chemical Formulas 9-1 to 9-4.

[Chemical formula 9-1]

[Chemical formula 9-4]

In Chemical Formula 9-1 to Chemical Formula 9-4, the definition of each substituent is the same as that in Chemical Formula 9.

In an exemplary embodiment of the present application, R7 to R10 are the same as or different from each other, and are independently selected from the group consisting of: hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C2 to C60 alkenyl; substituted or unsubstituted C2 to C60 alkynyl; substituted or unsubstituted C1 to C60 alkoxy; substituted or unsubstituted C3 to C60 cyclohexyl; Alkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; substituted or unsubstituted C2 to C60 heteroaryl; -P(=O)RR'; and -SiRR'R", or two or more adjacent groups may be bonded to each other to form a substituted or unsubstituted C6 to C60 aliphatic or aromatic hydrocarbon ring, or a substituted or unsubstituted C2 to C60 aliphatic or aromatic heterocyclic ring.

In another exemplary embodiment, R7 to R10 are the same or different from each other and can be independently selected from the group consisting of: hydrogen; deuterium; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C6 to C60 aryl; substituted or unsubstituted C2 to C60 heteroaryl; -P(=O)RR'; and -SiRR'R".

In another exemplary embodiment, R7 to R10 are the same or different from each other, and can each independently be hydrogen; deuterium; or a substituted or unsubstituted C6 to C60 aryl group.

In another exemplary embodiment, R7 to R10 are the same as or different from each other, and can each independently be hydrogen; deuterium; or a substituted or unsubstituted C6 to C40 aryl group.

In another exemplary embodiment, R7 to R10 are the same as or different from each other, and can each independently be hydrogen; deuterium; or C6 to C40 aryl.

In another exemplary embodiment, R7 to R10 are the same as or different from each other, and can each independently be hydrogen; deuterium; or C6 to C20 aryl.

In another exemplary embodiment, R7 to R10 are the same as or different from each other, and can each independently be hydrogen; deuterium; a monocyclic C6 to C10 aryl group; or a polycyclic C10 to C20 aryl group.

In another exemplary embodiment, R7 to R10 are the same as or different from each other, and can each independently be hydrogen; deuterium; or phenyl.

In another exemplary embodiment, R7 to R10 are the same as or different from each other, and can each independently be hydrogen; or deuterium.

In an exemplary embodiment of the present application, at least one of R1 to R6 can be represented by -N-Hetlene-L1-Z1.

In an exemplary embodiment of the present application, one of R1 to R6 can be represented by -N-Hetlene-L1-Z1.

In an exemplary embodiment of the present application, one of R1 to R6 is represented by -N-Hetlene-L1-Z1, and the others may be defined the same as R7 to R10.

In an exemplary embodiment of the present application, R1 is represented by -N-Hetlene-L1-Z1, and R2 to R6 may have the same definition as R7 to R10.

In an exemplary embodiment of the present application, R2 is represented by -N-Hetlene-L1-Z1 , and R1 and R3 to R6 may have the same definition as R7 to R10.

In an exemplary embodiment of the present application, R3 is represented by -N-Hetlene-L1-Z1, and R1, R2 R4 to R6 may have the same definition as R7 to R10.

In an exemplary embodiment of the present application, R4 is represented by -N-Hetlene-L1-Z1, and R1 to R3, R5 and R6 may have the same definition as R7 to R10.

In an exemplary embodiment of the present application, R5 is represented by -N-Hetlene-L1-Z1, and R1 to R4 and R6 may have the same definition as R7 to R10.

In an exemplary embodiment of the present application, R6 is represented by -N-Hetlene-L1-Z1, and R1 to R5 may have the same definition as R7 to R10.

In an exemplary embodiment of the present application, L1 may be a direct bond; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

In another exemplary embodiment, L1 may be a direct bond; or a substituted or unsubstituted C6 to C60 aryl group.

In another embodiment, L1 may be a direct bond; a substituted or unsubstituted C6 to C40 aryl group.

In another exemplary embodiment, L1 may be a direct bond; or a substituted or unsubstituted C6 to C20 aryl group.

In another exemplary embodiment, L1 may be a direct bond; or a C6 to C20 aryl group.

In another exemplary embodiment, L1 may be a direct bond; a phenyl group; a biphenyl group; or a naphthyl group.

In another exemplary embodiment, L1 may be a direct bond; or a phenyl group.

In an exemplary embodiment of the present application, L1 may be substituted with deuterium again.

In an exemplary embodiment of the present application, N-Hetlene may be a substituted or unsubstituted C2 to C60 heteroaryl group containing at least one or more -N= bonds.

In another exemplary embodiment, N-Hetlene may be a substituted or unsubstituted C2 to C60 heteroaryl group containing one or more and three or less than three -N= bonds.

In another exemplary embodiment, N-Hetlene may be a substituted or unsubstituted C2 to C40 heteroaryl group containing one or more and three or less than three -N= bonds.

In another exemplary embodiment, N-Hetlene may be a substituted or unsubstituted C2 to C20 heteroaryl group containing one or more and three or less than three -N= bonds.

In another exemplary embodiment, N-Hetlene may be a C2 to C20 heteroaryl group that is unsubstituted or substituted with a C6 to C20 aryl group and contains one or more and three or less than three -N= bonds.

In another exemplary embodiment, N-Hetlene can be a substituted or unsubstituted divalent pyridyl group; a substituted or unsubstituted divalent pyrimidyl group; a substituted or unsubstituted divalent triazine group; a substituted or unsubstituted divalent quinolyl group; a substituted or unsubstituted quinazolinyl group; a substituted or unsubstituted divalent quinoxalinyl group; a substituted or unsubstituted divalent benzofurano[3,2-d]pyrimidinyl group; or a substituted or unsubstituted divalent benzo[4,5]thienyl[3,2-d]pyrimidinyl group.

In another exemplary embodiment, N-Hetlene can be a divalent pyridyl group, which is unsubstituted or substituted with one or more substituents selected from the group consisting of phenyl, biphenyl and naphthyl; a divalent pyrimidinyl group, which is unsubstituted or substituted with one or more substituents selected from the group consisting of phenyl, biphenyl and naphthyl; a divalent triazinyl group, which is unsubstituted or substituted with one or more substituents selected from the group consisting of phenyl, biphenyl and naphthyl; a divalent quinolyl group; a quinazolinyl group; a divalent quinoxalinyl group; a divalent benzofurano[3,2-d]pyrimidinyl group; or a divalent benzo[4,5]thienyl[3,2-d]pyrimidinyl group.

In an exemplary embodiment of the present application, N-Hetlene can be substituted with deuterium again.

In an exemplary embodiment of the present application, N-Hetlene can be represented by any one of the following chemical formulas 1-1 to 1-3.

意謂與化學式1的結構連接的位置，且

意謂與L1連接的位置，Y為O；或S，X1至X3為N；或CRc，且X1至X3中的至少一者為N，X4及X5中的一者為

，且其他者為N；或CRc，且Rc、R21以及R61至R64彼此相同或不同，且各自獨立地為氫；氘；經取代或未經取代的C1至C60烷基；或經取代或未經取代的C6至C60芳基。 In Chemical Formula 1-1 to Chemical Formula 1-3,

means the position connected to the structure of Chemical Formula 1, and

means the position connected to L1, Y is O; or S, X1 to X3 are N; or CRc, and at least one of X1 to X3 is N, and one of X4 and X5 is

, and the others are N; or CRc, and Rc, R21, and R61 to R64 are the same as or different from each other and are each independently hydrogen; deuterium; substituted or unsubstituted C1 to C60 alkyl; or substituted or unsubstituted C6 to C60 aryl.

In an exemplary embodiment of the present application, Rc, R21, and R61 to R64 are the same or different from each other, and are each independently hydrogen; deuterium; substituted or unsubstituted C1 to C60 alkyl; or substituted or unsubstituted C6 to C60 aryl.

In another exemplary embodiment, Rc, R21, and R61 to R64 are the same or different from each other, and are each independently hydrogen; deuterium; or a substituted or unsubstituted C6 to C60 aryl group.

In another exemplary embodiment, Rc, R21, and R61 to R64 are the same or different from each other, and are each independently hydrogen; deuterium; or a substituted or unsubstituted C6 to C40 aryl group.

In another exemplary embodiment, Rc, R21, and R61 to R64 are the same or different from each other, and are each independently hydrogen; deuterium; or C6 to C40 aryl.

In another exemplary embodiment, Rc, R21, and R61 to R64 are the same or different from each other, and are each independently hydrogen; deuterium; or C6 to C20 aryl.

In another exemplary embodiment, Rc, R21, and R61 to R64 are the same as or different from each other, and are each independently hydrogen; deuterium; or phenyl.

In an exemplary embodiment of the present application, Z1 is a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 heteroaryl group; or a substituted or unsubstituted amino group.

In another exemplary embodiment, Z1 may be a substituted or unsubstituted C2 to C60 heteroaryl group; or a substituted or unsubstituted amino group.

In another exemplary embodiment, Z1 may be a substituted or unsubstituted N-containing C2 to C60 heteroaryl group; or a substituted or unsubstituted amino group.

In another exemplary embodiment, Z1 may be a substituted or unsubstituted N-containing C2 to C40 heteroaryl group; or a substituted or unsubstituted amino group.

In another exemplary embodiment, Z1 may be a substituted or unsubstituted N-containing C2 to C20 heteroaryl group; or a substituted or unsubstituted amino group.

In another exemplary embodiment, Z1 may be an N-containing C2 to C20 heteroaryl group that is unsubstituted or substituted with a C1 to C20 alkyl group or a C6 to C20 aryl group; or an amine group that is unsubstituted or substituted with a C6 to C20 aryl group.

In an exemplary embodiment of the present application, Z1 may be substituted with deuterium again.

In an exemplary embodiment of the present application, Z1 may be a substituted or unsubstituted amine group, or may be represented by one of the following chemical formulas 2-1 to 2-5.

[Chemical formula 2-5]

In Formulae 2-1 to 2-5, R31 to R38, R41 to R46, R51 to R54, R71 to R78, and R81 to R87 are the same as or different from each other, and are each independently selected from the group consisting of: hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C2 to C60 alkenyl; substituted or unsubstituted C2 to C60 alkynyl; substituted or unsubstituted C1 to C60 Alkoxy; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; and substituted or unsubstituted C2 to C60 heteroaryl, X10 is O; S; NRd; or CReRf, and Rd, Re and Rf are the same or different and are each independently a substituted or unsubstituted C1 to C60 alkyl; or a substituted or unsubstituted C6 to C60 aryl.

In an exemplary embodiment of the present application, R31 to R38, R41 to R46, R51 to R54, R71 to R78 and R81 to R87 are the same or different from each other, and are each independently selected from the group consisting of: hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C2 to C60 alkenyl; substituted or unsubstituted C2 to C60 alkynyl; substituted or unsubstituted C1 to C60 alkoxy; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; and substituted or unsubstituted C2 to C60 heteroaryl.

In another exemplary embodiment, R31 to R38, R41 to R46, R51 to R54, R71 to R78, and R81 to R87 are the same as or different from each other, and can be independently selected from the group consisting of: hydrogen; deuterium; substituted or unsubstituted C6 to C60 aryl; and substituted or unsubstituted C2 to C60 heteroaryl.

In another exemplary embodiment, R31 to R38, R41 to R46, R51 to R54, R71 to R78, and R81 to R87 are the same or different from each other, and can be independently selected from the group consisting of: hydrogen; deuterium; substituted or unsubstituted C6 to C40 aryl; or substituted or unsubstituted C2 to C40 heteroaryl.

In another exemplary embodiment, R31 to R38, R41 to R46, R51 to R54, R71 to R78, and R81 to R87 are the same or different from each other, and can be independently selected from the group consisting of: hydrogen; deuterium; substituted or unsubstituted C6 to C20 aryl; or substituted or unsubstituted C2 to C20 heteroaryl.

In another exemplary embodiment, R31 to R38, R41 to R46, R51 to R54, R71 to R78, and R81 to R87 are the same or different from each other, and can be independently selected from the group consisting of: hydrogen; deuterium; C6 to C20 aryl; and C2 to C20 heteroaryl.

In another exemplary embodiment, R31 to R38, R41 to R46, R51 to R54, R71 to R78, and R81 to R87 are the same as or different from each other, and may each independently be hydrogen; deuterium; or phenyl.

In an exemplary embodiment of the present application, Rd, Re and Rf are the same or different from each other, and are each independently a substituted or unsubstituted C6 to C60 aryl group.

In an exemplary embodiment of the present application, Rd, Re and Rf are the same 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.

In another exemplary embodiment, Rd, Re and Rf are the same 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.

In another exemplary embodiment, Rd, Re and Rf are the same or different from each other, and each is independently a C1 to C40 alkyl group; or a C6 to C40 aryl group.

In another exemplary embodiment, Rd, Re and Rf are the same or different from each other, and each is independently a C1 to C20 alkyl group; or a C6 to C20 aryl group.

In another exemplary embodiment, Rd, Re and Rf are the same or different from each other, and are each independently a methyl group; or a phenyl group.

In an exemplary embodiment of the present application, Z1 is represented by one of the chemical formulas 2-1 to 2-5, or may be an amino group which is unsubstituted or substituted by one or more substituents selected from the group consisting of: phenyl, biphenyl and dimethylfluorenyl.

In an exemplary embodiment of the present application, R, R' and R" are the same or different from each other, and can be independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

In another exemplary embodiment, R, R' and R" are the same or different from each other, and can each independently be a substituted or unsubstituted C6 to C60 aryl group.

In another exemplary embodiment, R, R' and R" are the same or different from each other, and can each independently be a substituted or unsubstituted C6 to C60 monocyclic or polycyclic aromatic group.

In another exemplary embodiment, R, R' and R" are the same or different from each other, and can each independently be a substituted or unsubstituted C6 to C40 monocyclic aromatic group.

In another exemplary embodiment, R, R' and R" are the same or different from each other, and can each independently be a C6 to C20 monocyclic aromatic group.

In another exemplary embodiment, R, R' and R" may be phenyl.

According to an exemplary embodiment of the present application, Chemical Formula 1 can be represented by any one of the following compounds, but is not limited thereto.

In addition, various substituents can be introduced into the structure of Chemical Formula 1 to synthesize compounds having the inherent characteristics of the introduced substituents. For example, it is possible to synthesize materials that meet the required conditions of each organic layer by introducing substituents commonly used in the following into the core structure: hole injection layer materials, materials for transporting holes, light-emitting layer materials, electron transport layer materials, and charge generation layer materials, which are used to prepare organic light-emitting elements.

In addition, it is possible to finely tune the energy band gap by introducing various substituents into the structure of Chemical Formula 1, and at the same time, it is possible to improve the characteristics at the interface between organic materials and diversify the uses of the materials.

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 layer, which has one or more layers arranged between the first electrode and the second electrode, wherein one or more layers of the organic layer include a heterocyclic compound according to Chemical Formula 1.

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 layer having one or more layers disposed between the first electrode and the second electrode, wherein one or more layers of the organic layer comprises a heterocyclic compound according to Chemical Formula 1.

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 layer having one or more layers disposed between the first electrode and the second electrode, wherein one or more layers of the organic layer comprise two heterocyclic compounds according to Chemical Formula 1.

The specific content of the heterocyclic compound represented by Chemical Formula 1 is the same as the content described above.

According to an exemplary embodiment of the present application, the first electrode may be a positive electrode, and the second electrode may be a negative electrode.

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

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 of the blue organic light-emitting element. For example, the heterocyclic compound according to Chemical Formula 1 may be included in the main material of the blue light-emitting layer of the blue organic light-emitting element.

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 according to Chemical Formula 1 may be used as a material of the green organic light-emitting element. For example, the heterocyclic compound according to Chemical Formula 1 may be included in the main material of the green light-emitting layer of the green organic light-emitting element.

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 according to Chemical Formula 1 may be used as a material of the red organic light-emitting element. For example, the heterocyclic compound according to Chemical Formula 1 may be included in the main material of the red light-emitting layer of the red organic light-emitting element.

In addition to the heterocyclic compounds described above being used to form an organic layer having one or more layers, the organic light-emitting element of the present invention can be manufactured using typical manufacturing methods and materials of organic light-emitting elements.

When manufacturing an organic light-emitting element, a heterocyclic compound can be formed into an organic layer not only by vacuum deposition but also by solution coating. In this article, solution coating means spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating and similar methods, but is not limited thereto.

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

In the organic light-emitting element of the present invention, the organic layer may include a light-emitting layer, and the light-emitting layer may include a heterocyclic compound.

In another organic light-emitting element, the organic layer includes a light-emitting layer, the light-emitting layer includes a host material, and the host material may include a heterocyclic compound.

As another example, the organic layer including the heterocyclic compound includes the heterocyclic compound represented by Chemical Formula 1 as a main body, and the heterocyclic compound may be used together with an iridium-based dopant.

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

In another organic light-emitting element, the organic layer includes an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer may include a heterocyclic compound.

In the organic light-emitting element of the present invention, the organic layer includes a hole transport layer, and the hole transport layer may include a heterocyclic compound.

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

In an organic light-emitting element according to an exemplary embodiment of the present application, an organic light-emitting element is provided, wherein the organic layer containing the heterocyclic compound represented by Chemical Formula 1 further contains the heterocyclic compound represented by the following Chemical Formula A.

In Formula A, Rc1 and Rd1 are the same or different and are independently selected from the group consisting of: hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C2 to C60 alkenyl; substituted or unsubstituted C2 to C60 alkynyl; substituted or unsubstituted C1 to C60 alkoxy; substituted or unsubstituted substituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; substituted or unsubstituted C2 to C60 heteroaryl; -SiRR'R"; -P(=O)RR' and -NRR', or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring or Substituted or unsubstituted heterocyclic ring, L2 is a direct bond; substituted or unsubstituted C6 to C60 aryl group; or substituted or unsubstituted C2 to C60 heteroaryl group, Ra1 and Rb1 are the same or different from each other and are independently -CN; -SiRR'R"; -P(=O)RR'; substituted or unsubstituted C6 to C60 aryl group; or substituted or unsubstituted C2 to C60 heteroaryl group, R, R' and R" are the same or different from each other and are independently hydrogen; deuterium; substituted or unsubstituted C1 to C60 alkyl group; or substituted or unsubstituted C6 to C60 aryl group, a1 is an integer from 0 to 4, r and s are integers from 0 to 7, and when a1, s and r are 2 or more, the substituents in the brackets are the same or different from each other.

In an exemplary embodiment of the present application, L2 may be a direct bond; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

In another exemplary embodiment, L2 may be a direct bond, a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group.

In yet another exemplary embodiment, L2 may be a direct bond; a C6 to C40 aryl group; or a _C2 to _C40 heteroaryl group.

In another exemplary embodiment, L2 may be a direct bond; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted divalent dibenzothienyl group; or a substituted or unsubstituted divalent dibenzofuranyl group.

In another exemplary embodiment, L2 can be a direct bond; a phenyl group; a biphenyl group; a naphthyl group; a divalent dibenzothienyl group; a divalent dimethylfluorenyl group; or a divalent dibenzofuranyl group.

In an exemplary embodiment of the present application, L2 may be substituted with deuterium.

In an exemplary embodiment of the present application, Ra1 and Rb1 are the same or different from each other, and can be independently -CN; -SiRR'R"; -P(=O)RR'; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl.

In another exemplary embodiment, Ra1 may be -CN; -SiRR'R"; -P(=O)RR'; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

In another exemplary embodiment, Ra1 may be -CN; -SiRR'R"; -P(=O)RR'; C6 to C40 aryl group which is unsubstituted or substituted with C1 to C40 alkyl group or C6 to C40 aryl group; or C2 to C60 heteroaryl group which is unsubstituted or substituted with C6 to C40 aryl group and C2 to C40 heteroaryl group.

In another exemplary embodiment, Ra1 may be -CN; -SiRR'R"; -P(=O)RR'; phenyl; biphenyl; naphthyl; terphenyl; phenanthrenyl; dimethylfluorenyl; diphenylfluorenylspirobifluorenyl; dibenzothiophenyl unsubstituted or substituted with phenyl or dibenzofuranyl; or dibenzofuranyl unsubstituted or substituted with phenyl or dibenzofuranyl.

In an exemplary embodiment of the present application, Rb1 may be a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

In another exemplary embodiment, Rb1 may be a C6 to C60 aryl group which is unsubstituted or substituted with a C1 to C40 alkyl group, -CN, SiRR'R", or a C6 to C40 aryl group.

In another exemplary embodiment, Rb1 may be a C6 to C40 aryl group which is unsubstituted or substituted with a C1 to C40 alkyl group, -CN, SiRR'R" or a C6 to C40 aryl group.

In another exemplary embodiment, Rb1 may be unsubstituted or substituted phenyl group with -CN or SiRR'R"; unsubstituted or substituted biphenyl group with phenyl group; naphthyl; terphenyl group; phenanthrenyl; or dimethylfluorenyl.

In an exemplary embodiment of the present application, Ra1 and Rb1 may be substituted with deuterium.

In an exemplary embodiment of the present application, -(L2)a-Ra1 and Rb1 of chemical formula A may be different from each other.

In an exemplary embodiment of the present application, -(L2)a-Ra1 and Rb1 of chemical formula A may be identical to each other.

In another exemplary embodiment, R, R' and R" may be substituted or unsubstituted phenyl.

In another exemplary embodiment, R, R' and R" may be phenyl.

In an exemplary embodiment of the present application, the deuterium content of chemical formula A may be 0% or greater than 0% and 100% or less than 100%.

In another exemplary embodiment, the deuterium content of Chemical Formula A may be 10% or greater and 100% or less.

In another exemplary embodiment, the deuterium content of chemical formula A may be 0%, 100%, or 10% to 80%.

In an exemplary embodiment of the present application, Rc1 and Rd1 are the same or different from each other and are independently selected from the group consisting of: hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C2 to C60 alkenyl; substituted or unsubstituted C2 to C60 alkynyl; substituted or unsubstituted C1 to C60 alkoxy; substituted or unsubstituted substituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; substituted or unsubstituted C2 to C60 heteroaryl; -SiRR'R"; -P(=O)RR' and -NRR', or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted heterocyclic ring.

In another exemplary embodiment, Rc1 and Rd1 are the same or different from each other and can be independently selected from the group consisting of: hydrogen; deuterium; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C6 to C60 aryl; substituted or unsubstituted C2 to C60 heteroaryl; -SiRR'R"; -P(=O)RR'; and -NRR'.

In another exemplary embodiment, Rc1 and Rd1 are the same or different from each other and can be independently selected from the group consisting of: hydrogen; deuterium; substituted or unsubstituted C1 to C40 alkyl; substituted or unsubstituted C6 to C40 aryl; substituted or unsubstituted C2 to C40 heteroaryl; -SiRR'R"; -P(=O)RR'; and -NRR'.

In another exemplary embodiment, Rc1 and Rd1 are the same or different and can be independently selected from the group consisting of: hydrogen; deuterium; C1 to C40 alkyl; C6 to C40 aryl; C2 to C40 heteroaryl; -SiRR'R"; -P(=O)RR'; and -NRR'.

In another exemplary embodiment, Rc1 and Rd1 are the same or different from each other, and can be independently selected from the group consisting of: hydrogen; deuterium; C1 to C20 alkyl; C6 to C20 aryl; C2 to C20 heteroaryl; -SiRR'R"; -P(=O)RR'; and -NRR'.

In another exemplary embodiment, Rc1 and Rd1 are the same or different from each other, and can each independently be hydrogen; deuterium; substituted or unsubstituted phenyl; substituted or unsubstituted biphenyl; or substituted or unsubstituted naphthyl.

In another exemplary embodiment, Rc1 and Rd1 are the same or different from each other, and can each independently be hydrogen; deuterium; phenyl; biphenyl; or naphthyl.

In an exemplary embodiment of the present application, r is 7, and Rc1 may be hydrogen.

In an exemplary embodiment of the present application, r is 7, and Rc1 may be deuterium.

In an exemplary embodiment of the present application, r is 7, and Rc1 can be hydrogen; or deuterium.

In an exemplary embodiment of the present application, s is 7, and Rd1 may be hydrogen.

In an exemplary embodiment of the present application, s is 7, and Rd1 may be deuterium.

In an exemplary embodiment of the present application, s is 7, and Rd1 can be hydrogen; or deuterium.

When the compound of Chemical Formula 1 and the compound of Chemical Formula A are simultaneously included in the organic layer of an organic light-emitting element, better efficiency and service life effects are exhibited. Based on this result, it can be expected that when the two compounds are simultaneously included, an excitation recombination phenomenon will occur.

The excitation recombination phenomenon is a phenomenon in which energy having the magnitude of the donor (p-host) HOMO energy level and the acceptor (n-host) LUMO energy level is released as electrons are exchanged between two molecules. When a donor (p-host) having good hole transporting ability and an acceptor (n-host) having good electron transporting ability are used as the host of the light-emitting layer, holes are injected into the p-host and electrons are injected into the n-host, so that the driving voltage can be reduced, which can help to improve the service life.

In an exemplary embodiment of the present application, the heterocyclic compound of formula A can be represented by any of the following compounds.

In addition, another exemplary embodiment of the present application provides a composition of an organic layer of an organic light-emitting element, which comprises a heterocyclic compound represented by Chemical Formula 1 and a heterocyclic compound represented by Chemical Formula A.

The specific contents of the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula A are the same as those described above.

The weight ratio of the heterocyclic compound represented by Chemical Formula 1 to the heterocyclic compound represented by Chemical Formula A in the composition may be 1:10 to 10:1, 1:8 to 8:1, 1:5 to 5:1, and 1:2 to 2:1, but is not limited thereto.

The composition can be used when forming an organic material of an organic light-emitting element, and more preferably, when forming the main body of a light-emitting layer.

The composition is in the form of two or more compounds simply mixed therein, and materials in a powder state may also be mixed before forming an organic layer of an organic light-emitting element, and it is possible to mix liquid compounds at a temperature equal to or higher than a suitable temperature. The composition is solid at a temperature equal to or lower than the melting point of each material, and can be maintained in a liquid phase when the temperature is adjusted.

The composition may further contain materials known in the art, such as solvents and additives.

In addition to the organic layer having one or more layers being formed by using the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula A described above, the organic light-emitting element according to an exemplary embodiment of the present application can be manufactured by a typical method and material for manufacturing an organic light-emitting element.

When manufacturing an organic light-emitting element, the compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula A can be formed into an organic layer not only by vacuum deposition but also by solution coating. In this article, solution coating means spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating and the like, but is not limited thereto.

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

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 and the heterocyclic compound according to Chemical Formula A may be used as materials for the blue organic light-emitting element.

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 and the heterocyclic compound represented by Chemical Formula A may be used as materials for the green organic light-emitting element.

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 and the heterocyclic compound represented by Chemical Formula A may be used as materials for the red organic light-emitting element.

Figures 1 to 3 illustrate the stacking order of the electrodes and organic layers of an organic light-emitting device according to an exemplary embodiment of the present application. However, the scope of the present application is not intended to be limited by these figures, and the structure of the organic light-emitting device known in the art can also be applied to the present application.

According to FIG. 1 , an organic light-emitting element is shown in which a positive electrode 200, an organic 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 type of structure, and as shown in FIG. 2 , an organic light-emitting element in which a negative electrode, an organic layer, and a positive electrode are sequentially stacked on a substrate can also be realized.

FIG3 illustrates a case where the organic layer is multi-layered. The organic light-emitting element according to FIG3 includes a hole injection layer 301, a hole transport layer 302, a light-emitting layer 303, a hole blocking layer 304, an electron transport layer 305, and an electron injection layer 306. However, the scope of the present application is not limited to the stacking structure described above, and if necessary, other layers except the light-emitting layer can be omitted, and another required functional layer can be further added.

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 layer having one or more layers on the first electrode; and forming a second electrode on the organic layer, wherein the formation of the organic layer comprises forming the organic layer having one or more layers by using a composition for an organic layer according to an exemplary embodiment of the present application.

In an exemplary embodiment of the present application, a method for manufacturing an organic light-emitting element is provided, wherein an organic layer is formed by premixing a heterocyclic compound of Chemical Formula 1 and a compound of Chemical Formula A and forming the organic layer using a thermal vacuum deposition method.

Premixing means that before depositing the heterocyclic compound of Chemical Formula 1 and the heterocyclic compound of Chemical Formula A on the organic layer, the materials are first mixed and the mixture is contained in a common container and mixed.

The premixed material may be referred to as a composition of an organic layer according to an exemplary embodiment of the present application.

If necessary, the organic layer containing the compound of Chemical Formula 1 may further contain other materials.

In an organic light-emitting element in an exemplary embodiment of the present application, materials other than the heterocyclic compound of Chemical Formula 1 will be exemplified below, but these materials are only illustrative and are not intended to limit the scope of the present application, and can be replaced by materials publicly known in the art.

As the positive electrode material, a material having a relatively high work function may be used, and a transparent conductive oxide, a metal, a conductive polymer, and the like may 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 SnO ₂ :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.

As the negative electrode material, a material having a relatively low work function may be used, and metals, metal oxides, or conductive polymers 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 structured materials such as LiF/Al or LiO ₂ /Al and the like, but are not limited thereto.

As the hole injection material, a known hole injection material can be used, and for example, a phthalocyanine compound, such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429 or a phthalocyanine compound disclosed in the literature [Advanced Materials Starburst amine derivatives described in "Journal of Materials", 6, p. 677 (1994), such as tris(4-hydrazinemethylyl-9-ylphenyl)amine (TCTA), 4,4',4"-tris[phenyl(m-tolyl)amino]triphenylamine (m-MTDATA), 1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene (m-MTDAPB), polyaniline/dodecylbenzenesulfonic acid or poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (which is a soluble conductive polymer), polyaniline/camphorsulfonic acid or polyaniline/poly(4-styrene-sulfonate), and the like.

As hole transport materials, pyrazoline derivatives, aromatic amine derivatives, stilbene derivatives, triphenyldiamine derivatives and the like can be used, and low molecular weight materials or polymer materials can also be used.

As electron transmission 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, diphenoquinone derivatives, metal complexes of 8-hydroxyquinoline and its derivatives, and the like can be used, and low molecular weight materials and polymer materials can also be used.

As an electron injection material, LiF is typically used in this field, but this application is not limited to this.

As the luminescent material, a red luminescent material, a green luminescent material, or a blue luminescent material can be used, and two or more luminescent materials can be mixed and used as necessary. In this case, two or more luminescent materials are deposited or used as individual supply sources, or are pre-mixed to be deposited and used as supply sources. In addition, a fluorescent material can also be used as a luminescent material, but it can also be used as a phosphorescent material. As a luminescent material, it is also possible to use a material that emits light by combining holes and electrons injected from each of the positive electrode and the negative electrode alone, but it is also possible to use a material in which the main material and the doped material participate in luminescence together.

When mixing and using the host of the light-emitting material, the host of the same series may be mixed and used, and the host of different series may be mixed and used. For example, two or more materials selected from n-type host materials or p-type host materials may be used as the host material of the light-emitting layer.

Depending on the materials to be used, the organic light-emitting element according to an exemplary embodiment of the present application may be a top-emitting type, a bottom-emitting type, or a dual-emitting type.

Based on principles similar to those applied to organic light-emitting devices, the heterocyclic compound according to an exemplary embodiment of the present application may even function in organic electronic devices including organic solar cells, organic photoconductors, organic transistors, and the like.

Below, this specification will be described in more detail in examples, but these examples are provided only for the purpose of illustrating this application and are not intended to limit the scope of this application.

<Preparation Example 1> Preparation of Compound 5

Preparation of compound 5-2

1,4-Dioxane (250 mL) was placed in compound 5-1 (25 g, 0.085 mol, 1 eq), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborolane) (32.5 g, 0.128 mol, 1.5 eq), Pd(dba) ₂ (2.4 g, 0.004 mol, 0.05 eq) and P(Cy) ₃ (2.4 g, 0.008 mol, 0.1 eq), and the resulting mixture was stirred at 100° C. for 8 hours. After the reaction was terminated by adding water, extraction was performed using MC and water. Thereafter, water was removed using MgSO ₄ . The residue was separated by a silica gel column to obtain 24 g of compound 5-2 with a yield of 73%.

Preparation of compound 5-3

1,4-Dioxane (240 mL) and H ₂ O (60 mL) were placed in compound 5-2 (24 g, 0.062 mol, 1 eq), 2,4-dichloroquinazoline (B) (14.9 g, 0.075 mol, 1.2 eq), K ₂ CO ₃ (21.6 g, 0.156 mol, 2.5 eq) and Pd(PPh ₃ ) ₄ (3.6 g, 0.003 mol, 0.05 eq), and the resulting mixture was stirred at 90° C. for 8 hours. After the reaction was terminated by adding water, extraction was performed using MC and water. Thereafter, water was removed using MgSO _4. The residue was separated by a silica gel column to obtain 18 g of compound 5-3 with a yield of 68%.

Preparation of compound 5

Xylene (100 mL) was placed into compound 5-3 (10 g, 0.023 mol, 1 eq.), 9H-carbazole (4.7 g, 0.028 mol, 1.2 eq.), Pd ₂ (dba) ₃ (1.1 g, 0.011 mol, 0.05 eq.) and XPhos (1.1 g, 0.023 mol, 0.1 eq.), and the resulting mixture was stirred at 140° C. for 8 hours. After the reaction was terminated by adding water, extraction was performed using MC and water. Thereafter, water was removed using MgSO _4. The residue was separated by a silica gel column to obtain 7 g of compound 5 with a yield of 53%.

The compound was synthesized in the same manner as in Preparation Example 1, except that the intermediates A, B and C in Table 1 below were used instead of (A), (B) and (C) in Preparation Example 1.

<Preparation Example 2> Preparation of Compound PH3

Preparation of compound PH3

Xylene (150 mL) was placed in 9-phenyl-9H,9'H-3,3'-dicarbazole (D) (10 g, 0.024 mol, 1 eq), 3-bromo-1,1'-biphenyl (E) (6.8 g, 0.029 mol, 1.2 eq), NaOt-Bu (3.5 g, 0.037 mol, 1.5 eq), Pd ₂ (dba) ₃ (1.1 g, 0.012 mol, 0.05 eq) and XPhos (1.1 g, 0.023 mol, 0.1 eq), and the resulting mixture was stirred at 140° C. for 7 hours. After the reaction was terminated by adding water, extraction was performed using MC and water. Thereafter, water was removed using MgSO ₄ . The residue was separated by a silica gel column to obtain 8 g of compound PH3 with a yield of 58%.

The compound was synthesized in the same manner as in Preparation Example 2 except that intermediates D and intermediates E in Table 2 below were used instead of (D) and (E) in Preparation Example 2.

In addition to the compounds described in Preparation Example 1 and Preparation Example 2 and Table 1 and Table 2, heterocyclic compounds corresponding to Chemical Formula 1 and Chemical Formula A were also prepared in the same manner as in the Preparation Examples described above.

The compounds were prepared in the same manner as in Preparation Example, and the synthesis confirmation results thereof are shown in Table 3 and Table 4. Table 3 shows the measurement values of ¹ H NMR (CDCl ₃ , 200 MHz), and Table 4 shows the measurement values of field desorption mass spectrometry (FD-MS).

[Experimental example]

<Experimental Example 1> -Manufacturing of organic light-emitting devices

A glass substrate thinly coated with indium tin oxide (ITO) to a thickness of 1,500 angstroms was ultrasonically cleaned with distilled water. After washing with distilled water, the glass substrate was ultrasonically cleaned with solvents such as acetone, methanol, and isopropyl alcohol, dried, and then treated with ultraviolet ozone (UVO) using UV in an ultraviolet (UV) washer for 5 minutes. Thereafter, the substrate was transferred to a plasma washer (PT), and then plasma treated in a vacuum state for ITO work function and to facilitate removal of residual films, and transferred to a thermal deposition apparatus for organic deposition.

As a common layer, a hole injection layer 4,4',4"-tri[2-naphthyl(phenyl)amino]triphenylamine (2-TNATA) and a hole transport layer N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine (NPB) were formed on an ITO transparent electrode (positive electrode). A light-emitting layer was thermally vacuum deposited thereon as follows. The light-emitting layer was deposited to a thickness of 400 angstroms by depositing a compound of a type described in Table 5 below as a red host, and using (piq) ₂ (Ir)(acac) as a red phosphorescent dopant, 3 wt% of an Ir compound was doped into the host. Thereafter, Bphen was deposited to a thickness of 30 angstroms as a hole blocking layer, and Alq ₃ is deposited thereon to a thickness of 250 angstroms as an electron transport layer. Finally, lithium fluoride (LiF) is 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 is deposited on the electron injection layer to a thickness of 1,200 angstroms to form a negative electrode, thereby manufacturing an organic electroluminescent device.

Meanwhile, all organic compounds required for manufacturing OLED devices were subjected to vacuum sublimation purification at ^10-6 to ^10-8 torr for each material, and used for manufacturing OLED. For the organic electroluminescent device manufactured as described above, electroluminescent (EL) characteristics were measured by M7000 manufactured by McScience Inc., and based on the measurement results thereof, T90 was measured by a life measurement device (M6000) manufactured by McScience Inc. when the reference brightness was 6,000 candela/square meter (cd/ ^m2 ). The results of measuring the driving voltage, luminous efficiency, color coordinates (CIE), and life of the organic light-emitting device manufactured according to the present invention are shown in Table 5.

As can be seen from the results in Table 5, it can be confirmed that the organic light-emitting element using the host material of the present invention has a low driving voltage and significantly improved light-emitting efficiency and service life compared to the comparative example. The heterocyclic compound according to the present application has a molecular weight and a band gap suitable for the light-emitting layer of the organic light-emitting element and has high thermal stability. The appropriate molecular weight helps to form the light-emitting layer of the organic light-emitting element, and the appropriate band gap prevents the flow of electrons and holes in the light-emitting layer to help form an effective recombination zone. In addition, compared with compounds substituted at other positions, heterocyclic compounds with substituted electron transfer characteristics at appropriate positions solve the hole blocking phenomenon caused by dopants, and as can be seen from the above device evaluation, it is determined that the compounds of the present invention have achieved superiority over the comparative examples in all aspects of drive, efficiency and service life.

<Experimental Example 2> -Manufacturing of organic light-emitting devices

A glass substrate thinly coated with indium tin oxide (ITO) to a thickness of 1,500 angstroms was ultrasonically cleaned with distilled water. After washing with distilled water, the glass substrate was ultrasonically cleaned with solvents such as acetone, methanol, and isopropyl alcohol, dried, and then treated with ultraviolet ozone (UVO) using UV in an ultraviolet (UV) washer for 5 minutes. Thereafter, the substrate was transferred to a plasma washer (PT), and then plasma treated in a vacuum state for ITO work function and to facilitate removal of residual films, and transferred to a thermal deposition apparatus for organic deposition.

As common layers, the hole injection layer 4,4',4"-tri[2-naphthyl(phenyl)amino]triphenylamine (2-TNATA), the hole transport layer N,N'-di(1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine (NPB), and the electron blocking layer cyclohexylenebis[N,N-bis(4-methylphenyl)aniline] (TAPC) or the exciton blocking layer tris(4-hydrazinomethyl-9-ylphenyl)amine (TCTA) are formed on the ITO transparent electrode (positive electrode).

A light-emitting layer was thermally vacuum deposited thereon as follows. The light-emitting layer was deposited to a thickness of 400 angstroms by depositing two types of compounds from a single source as described in Table 6 below as a red host, and using (piq) ₂ (Ir)(acac) as a red phosphorescent dopant, doping the host with 3 wt % of an Ir compound. Thereafter, Bphen was deposited to a thickness of 30 angstroms as a hole blocking layer, and TPBI was deposited thereon to a thickness of 250 angstroms as an electron transport layer. Finally, lithium fluoride (LiF) is 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 is deposited on the electron injection layer to a thickness of 1,200 angstroms to form a negative electrode, thereby manufacturing an organic electroluminescent device.

Meanwhile, all organic compounds required for manufacturing OLED elements were purified by vacuum sublimation at ^10-6 to ^10-8 torr for each material, and used to manufacture OLED. For the organic electroluminescent element manufactured as described above, the electroluminescent (EL) characteristics were measured by M7000 manufactured by Micro Scientific, and based on the measurement results thereof, when the reference brightness was 6,000 candelas/m2, T90 was measured by a service life measurement device (M6000) manufactured by Micro Scientific. The results of measuring the driving voltage, luminous efficiency, color coordinates (CIE) and service life of the organic light-emitting element manufactured according to the present invention are shown in Table 6.

As can be seen from the results in Table 6, it can be confirmed that when the heterocyclic compound of the present invention is used as an N-type host and mixed with a P-type host and deposited, the drive, efficiency and service life of the organic light-emitting element are improved. When a donor (p-host) with good hole transport ability and an acceptor (n-host) with good electron transport ability are used as the host of the light-emitting layer, the charge balance in the element can be adjusted because holes are injected into the p-host and electrons are injected into the n-host due to the excited recombination phenomenon of the N+P compound. It can be seen that the combination of an N-type host compound with appropriate electron transfer characteristics and a P-type host compound with appropriate hole transfer characteristics in an appropriate ratio helps to improve the drive efficiency and service life.

100: Substrate 200: Positive electrode 300: Organic layer 400: Negative electrode

Claims (15)

A heterocyclic compound is represented by the following chemical formula 1:

Wherein, in Chemical Formula 1, X1 and X2 are the same or different and are each independently O; S; or CRaRb, R1 to R10 are the same or different and are each independently selected from the group consisting of: hydrogen; deuterium; halogen; cyano; substituted or unsubstituted substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C2 to C60 alkenyl; substituted or unsubstituted C2 to C60 alkynyl; substituted or unsubstituted C1 to C60 alkoxy; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 C6 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; substituted or unsubstituted C2 to C60 heteroaryl; -P(=O)RR'; and -SiRR'R", or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted C6 to C60 aliphatic or aromatic hydrocarbon ring, or a substituted or unsubstituted C2 to C60 aliphatic or aromatic heterocycle, at least one of R1 to R6 is represented by -N-Hetlene-L1-Z1, N-Hetlene is a substituted or unsubstituted C2 to C60 heterocycloalkyl containing one or more -N= bonds to C60 heteroaryl, L1 is a direct bond; a substituted or unsubstituted C6 to C60 heteroaryl; or a substituted or unsubstituted C2 to C60 heteroaryl, Z1 is a substituted or unsubstituted amine, or is represented by one of the following Chemical Formulae 2-1 to 2-5:

[Chemical formula 2-4]

In Formulae 2-1 to 2-5, R31 to R38, R41 to R46, R51 to R54, R71 to R78, and R81 to R87 are the same as or different from each other, and are each independently selected from the group consisting of: hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C2 to C60 alkenyl; substituted or unsubstituted C2 to C60 alkynyl; substituted or unsubstituted C1 to C60 alkoxy; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; and substituted or unsubstituted C2 to C60 heteroaryl, X10 is O; S; NRd; or CReRf, and Rd, Re and Rf are the same 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, and Ra, Rb, R, R' and R" are the same or different from each other and are each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group. The heterocyclic compound as described in claim 1, wherein Chemical Formula 1 is represented by any one of the following Chemical Formulas 2 to 7:

[Chemical formula 7]

In Chemical Formulae 2 to 7, R1 to R10, X1 and X2 are defined the same as those in Chemical Formula 1. The heterocyclic compound as described in claim 1, wherein Chemical Formula 1 is represented by the following Chemical Formula 8 or Chemical Formula 9:

[Chemical formula 9]

In Chemical Formulae 8 and 9, X1, X2, R7 to R10, N-Hetlene, L1 and Z1 are defined the same as those in Chemical Formula 1, R11 to R16 are the same as or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, and a is an integer from 0 to 3, and when a is 2 or greater, the substituents in the brackets are the same as or different from each other. The heterocyclic compound as described in claim 1, wherein the N-Hetlene is represented by any one of the following Chemical Formulas 1-1 to 1-3:

[Chemical formula 1-2]

In Chemical Formula 1-1 to Chemical Formula 1-3,

means the position connected to the structure of Chemical Formula 1, and

means the position connected to L1, Y is O; or S, X1 to X3 are N; or CRc, and at least one of X1 to X3 is N, and one of X4 and X5 is

, and the other is N; or CRc, and Rc, R21 and R61 to R64 are the same as or different from each other and are each independently hydrogen; deuterium; substituted or unsubstituted C1 to C60 alkyl; or substituted or unsubstituted C6 to C60 aryl. A heterocyclic compound as described in claim 1, wherein the deuterium content of the heterocyclic compound represented by chemical formula 1 is 20% or greater and 100% or less. The heterocyclic compound as described in claim 1, wherein Chemical Formula 1 is represented by any one of the following compounds:

An organic light-emitting element comprises: a first electrode; a second electrode disposed to face the first electrode; and an organic layer having one or more layers disposed between the first electrode and the second electrode, wherein the one or more layers of the organic layer comprise the heterocyclic compound as described in any one of claims 1 to 6. The organic light-emitting device as described in claim 7, wherein the organic layer comprising the heterocyclic compound of Chemical Formula 1 further comprises a heterocyclic compound represented by the following Chemical Formula A:

In Formula A, Rc1 and Rd1 are the same or different and are each independently selected from the group consisting of: hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C2 to C60 alkenyl; substituted or unsubstituted C2 to C60 alkynyl; substituted or unsubstituted C1 to C60 alkoxy; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C -60 aryl; substituted or unsubstituted C2 to C60 heteroaryl; -SiRR'R";-P(=O)RR' and -NRR', or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted heterocyclic ring, L2 is a direct bond; substituted or unsubstituted C6 to C60 aryl extension; or substituted or unsubstituted C2 to C60 heteroaryl extension, Ra1 and Rb1 are the same or different and are each independently -CN; -SiRR'R";-P(=O)RR'; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl, R, R' and R" are the same as or different from each other and are each independently hydrogen; deuterium; substituted or unsubstituted C1 to C60 alkyl; or substituted or unsubstituted C6 to C60 aryl, a1 is an integer from 0 to 4, r and s are integers from 0 to 7, and when a1, s and r are 2 or more, the substituents in the brackets are the same as or different from each other. The organic light-emitting device as described in claim 8, wherein the heterocyclic compound of chemical formula A is represented by any one of the following compounds:

An organic light-emitting element as described in claim 7, wherein the organic layer includes a light-emitting layer, and the light-emitting layer includes the heterocyclic compound. An organic light-emitting element as described in claim 7, wherein the organic layer includes an electron injection layer or an electron transport layer, and the electron transport layer or the electron injection layer includes the heterocyclic compound. An organic light-emitting element as described in claim 7, wherein the organic layer includes an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer includes the heterocyclic compound. An organic light-emitting element as described in claim 7, wherein the organic layer includes a hole transport layer, and the hole transport layer includes the heterocyclic compound. The organic light-emitting element as described in claim 7 further includes one or two or more layers selected from the group consisting of: a light-emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer. A composition of an organic layer of an organic light-emitting device, comprising a heterocyclic compound represented by Chemical Formula 1 as described in any one of Claims 1 to 6, and a heterocyclic compound represented by the following Chemical Formula A:

In Formula A, Rc1 and Rd1 are the same or different and are independently selected from the group consisting of: hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C2 to C60 alkenyl; substituted or unsubstituted C2 to C60 alkynyl; substituted or unsubstituted C1 to C60 alkoxy; substituted or unsubstituted substituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; substituted or unsubstituted C2 to C60 heteroaryl; -SiRR'R";-P(=O)RR' and -NRR', or two or more adjacent groups are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted heterocyclic ring, L2 is a direct bond; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, Ra1 and Rb1 are the same or different from each other and are each independently -CN; -SiRR'R";-P(=O)RR'; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, R, R' and R" are the same or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl group; or a substituted or unsubstituted C6 to C60 aryl group, a1 is an integer from 0 to 4, r and s are integers from 0 to 7, and when a1, s and r are 2 or more, the substituents in the brackets are the same or different from each other.