TW202404948A - Heterocyclic compound and organic light emitting device comprising the same - Google Patents

Abstract

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

Description

Heterocyclic compounds and organic light-emitting devices including the same

This application claims the priority and rights of Korean Patent Application No. 10-2022-0065252, which was filed with the Korean Intellectual Property Office on May 27, 2022. The entire content of the Korean patent application is incorporated into this case for reference.

The present disclosure relates to a heterocyclic compound and an organic light-emitting device including the same.

Organic light-emitting elements are self-emitting display elements and have the advantages of wide viewing angle, high response speed and excellent contrast.

The organic light-emitting element has a structure in which an organic thin film is provided between two electrodes. When a voltage is applied to an organic light-emitting element having such a structure, electrons and holes injected from the two electrodes are combined into pairs in the organic thin film, and then emit light when the electrons and holes are annihilated. The organic thin film can be formed in a single layer or multiple layers as necessary.

The material of the organic film can have a light-emitting function as needed. For example, as the material of the organic thin film, compounds that can each form a light-emitting layer by themselves can be used, or compounds that can each function as a host or a dopant of a light-emitting layer based on a host-dopant can be used. In addition, compounds that can play the roles of hole injection, hole transport, electron blocking, hole blocking, electron transport, electron injection and similar functions can also be used as materials for organic thin films.

In order to enhance the performance, lifetime or efficiency of organic light-emitting devices, there is a continuing need to develop organic thin film materials. Previous technical documents Patent documents (Patent document 1) U.S. Patent No. 4,356,429

[Technical Issue]

The present disclosure relates to providing a heterocyclic compound and an organic light-emitting device including the same. [Technical solutions]

One embodiment of the present disclosure provides a heterocyclic compound represented by the following Chemical Formula 1: [Chemical Formula 1] In Chemical Formula 1, R1 to R12 are the same as or different from each other, and each is 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)R101R102 ;-SiR101R102R103; and a group represented by the following Chemical Formula 2, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted Substituted C2 to C60 heterocycle, and R101, R102 and R103 are the same or different from each other, and each is independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group ; Or a substituted or unsubstituted C2 to C60 heteroaryl group, at least one of R2 to R12 is a group represented by the following Chemical Formula 2, and R13 and R14 are -CRaRbRc, and Ra to Rc are the same as or different from each other , and each is 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; and substituted or unsubstituted C2 to C60 Heterocycloalkyl, [Chemical Formula 2] In Chemical Formula 2, L1 and L2 are the same as or different from each other, and each is independently a single bond; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group , Ar1 and Ar2 are the same or different from each other, and are each independently a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, m and n are the same as or different from each other, and are each independently an integer of 0 to 3, and * represents a bonding site to the compound of Chemical Formula 1.

In addition, an embodiment of the present disclosure provides an organic light-emitting element. The organic light-emitting element includes: a first electrode; a second electrode disposed opposite to the first electrode; and one or more organic material layers disposed on the first electrode. Between an electrode and a second electrode, wherein one or more of the organic material layers includes a heterocyclic compound according to the present disclosure. [Beneficial effect]

The heterocyclic compound according to one embodiment can be used as an organic material layer material of an organic light-emitting element. The heterocyclic compound can serve as a hole injection layer material, an electron blocking layer material, a hole transport layer material, a light emitting layer material, an electron transport layer material, a hole blocking layer material, an electron injection layer material, and a material in an organic light-emitting element. Similar material effects. In particular, the heterocyclic compound can be used as a hole transport layer material, a hole transport auxiliary layer material or an electron blocking layer material of an organic light-emitting element.

By using the compound represented by Chemical Formula 1 in the organic material layer, the driving voltage can be reduced, the luminous efficiency can be enhanced, and the lifetime properties can be enhanced in the organic light-emitting element.

In the following, the present disclosure will be explained in more detail.

In this specification, the term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is changed to another substituent, and the position of substitution is not limited as long as it is the position where the hydrogen atom is substituted (also That is, the position at which the substituent can be substituted) suffices, and when two or more substituents are substituted, the two or more substituents may be the same as or different from each other.

In this specification, the term "substituted or unsubstituted" means a group selected from the group consisting of deuterium, halogen, cyano, C1 to C60 linear or branched alkyl, C2 to C60 linear or branched alkenyl, C2 to C60 linear or branched alkynyl, C3 to C60 monocyclic or polycyclic cycloalkyl, C2 to C60 monocyclic or polycyclic heterocycloalkyl, C6 to C60 monocyclic or polycyclic aryl, C2 to C60 monocyclic Cyclic or polycyclic heteroaryl, -SiRR'R'', -P(=O)RR', C1 to C20 alkylamino, C6 to C60 monocyclic or polycyclic arylamine and C2 to C60 monocyclic Or one or more substituents of a group consisting of polycyclic heteroarylamino groups are substituted or unsubstituted, or substituted by two or more substituents selected from the substituents exemplified above are linked. Substituted or unsubstituted.

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

In this specification, an alkyl group includes a straight chain or branched chain form having 1 to 60 carbon atoms, and may be further substituted by other substituents. The number of carbon atoms of the alkyl group may be 1 to 60, specifically 1 to 40, and more specifically 1 to 20. Specific examples of the alkyl group may include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-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, cyclopentylmethyl, cyclohexylmethyl , octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl Propyl, 1,1-dimethyl-propyl, isohexyl, 4-methylhexyl, 5-methylhexyl and similar groups, but are not limited thereto.

In this specification, alkenyl includes straight-chain or branched-chain forms having 2 to 60 carbon atoms, and may be further substituted with other substituents. The number of carbon atoms of the alkenyl group may be from 2 to 60, specifically from 2 to 40, and more specifically from 2 to 20. Specific examples of the alkenyl group may 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, stilbenyl group (stilbenyl group), styryl group and similar groups, but are not limited to these.

In the present specification, the alkynyl group includes straight-chain or branched-chain forms having 2 to 60 carbon atoms, and may be further substituted by other substituents. The number of carbon atoms of the alkynyl group may be 2 to 60, specifically 2 to 40, and more specifically 2 to 20.

In this specification, the alkoxy group may be a linear, branched or cyclic alkoxy group. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 20. Specific examples of the alkoxy group may include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy Oxygen, neopentyloxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-octyloxy, n-nonyloxy, n-decyloxy , benzyloxy, p-methylbenzyloxy and similar groups, but are not limited to these.

In this specification, cycloalkyl groups include monocyclic or polycyclic groups having 3 to 60 carbon atoms, and may be further substituted with other substituents. As used herein, polycyclic group means a group in which a cycloalkyl group is directly linked or fused to another cyclic group. Herein, the other cyclic group may be a cycloalkyl group, but may also be different types of cyclic groups, such as heterocycloalkyl, aryl and heteroaryl. The number of carbon atoms of the cycloalkyl group may be from 3 to 60, specifically from 3 to 40, and more specifically from 5 to 20. Specific examples of the cycloalkyl group may 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 similar groups, but It doesn't stop there.

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

In this specification, an aryl group includes a monocyclic group or a polycyclic group having 6 to 60 carbon atoms, and may be further substituted by other substituents. As used herein, polycyclic group means a group in which an aryl group is directly linked or fused to another cyclic group. In this context, the other cyclic group may be an aryl group, but may also be different types of cyclic groups, such as cycloalkyl, heterocycloalkyl and heteroaryl. Aryl groups may include spirocyclyl groups. The aryl group may have a carbon number of 6 to 60, specifically 6 to 40, and more specifically 6 to 25. Specific examples of the aryl group may include phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, pyrenyl, phenanthrenyl, perylene, fluoranthryl, terphenylene, pyrenyl, pyrenyl, pyrenyl, Tetraphenyl, fused pentaphenyl, fluorenyl, indenyl, acenaphthylenyl, benzofluorenyl, spirocyclic difluorenyl, 2,3-dihydro-1H-indenyl, its fused ring groups and similar groups, But it doesn't stop there.

In this specification, the phosphine oxide group is represented by -P(=O)R101R102, and R101 and R102 are the same or different from each other, and can each independently be a substituent formed by at least one of the following: hydrogen; deuterium; halogen alkyl; alkenyl; alkoxy; cycloalkyl; aryl; and heterocyclyl. Specifically, the phosphine oxide group may be substituted by an aryl group, and as the aryl group, the above-mentioned examples may be applied. Examples of the phosphine oxide group may include diphenylphosphine oxide group, dinaphthylphosphine oxide group and similar groups, but are not limited thereto.

In this specification, a silyl group is a substituent containing Si and directly connecting a Si atom as a radical, and is represented by -SiR101R102R103. R101 to R103 are the same or different from each other, and may each independently be a substituent formed from at least one of the following: hydrogen; deuterium; halogen group; alkyl group; alkenyl group; alkoxy group; cycloalkyl group; aryl group; and heterocyclyl. Specific examples of the silyl group may include trimethylsilyl group, triethylsilyl group, tert-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group , diphenylsilyl group, phenylsilyl group and similar groups, but are not limited to these.

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

When the fluorenyl group is substituted, it may include , , , , , and similar groups, however, the structure is not limited thereto.

In this specification, a spirocyclic group is a group including a spirocyclic structure, and may have 15 to 60 carbon atoms. For example, the spirocyclic group may include a structure in which a 2,3-dihydro-1H-indenyl or cyclohexanyl spirocyclic group is bonded to a fluorenyl group. Specifically, the spirocyclic group may include any of the groups of the following structural formulas.

In this specification, the heteroaryl group contains S, O, Se, N or Si as a heteroatom, includes a monocyclic group or a polycyclic group having 2 to 60 carbon atoms, and may be further substituted by other substituents. As used herein, polycyclic group means a group in which a heteroaryl group is directly linked or fused to another cyclic group. Herein, the other cyclic group may be a heteroaryl group, but may also be different types of cyclic groups, such as cycloalkyl, heterocycloalkyl and aryl groups. The number of carbon atoms of the heteroaryl group may be from 2 to 60, specifically from 2 to 40, and more specifically from 3 to 25. Specific examples of the heteroaryl group may include pyridyl, pyrrolyl, pyrimidinyl, pyridazinyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, Triazolyl, furfuryl, oxadiazolyl, thiadiazolyl, dithiazolyl, tetrazolyl, pyranyl, thiopyranyl, diazinyl, oxazinyl, thiazinyl, dioxinyl ( dioxynyl group), triazinyl, tetrazinyl, quinolinyl, isoquinolinyl, quinazolinyl (quinazolinyl group), isoquinazolinyl, quinozolinyl (quinozolinyl group), naphthyridinyl, acridine Alkyl, phenanthridinyl (phenanthridinyl group), imidazopyridyl, naphthyldiaza, indenyl, 2-indolyl, indenyl, benzothiazolyl, benzoxazolyl, Benzimidazolyl, benzothienyl, benzofuranyl, dibenzothienyl, dibenzofuranyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenanthienyl, diphenyl Dibenzosilole group, spirobis(dibenzosilole) group, dihydrophoranazinyl group, phenanthridyl group, phenanthridyl group, thienyl group (thienyl group), indolo[2,3-a]carbazolyl, indolo[2,3-b]carbazolyl, indolinyl, 10,11-dihydro-dibenzo[ b,f]azazinyl, 9,10-dihydroacridinyl, thiazinyl, thiazinyl, phthalazinyl, naphthyridinyl, phenanthrolinyl, benzo[c][1,2, 5]thiadiazolyl, 5,10-dihydrodibenzo[b,e][1,4]azasilyl, pyrazolo[1,5-c]quinazolinyl, pyrido[ 1,2-b]indazolyl, pyrido[1,2-a]imidazo[1,2-e]indolyl, 5,11-dihydroindeno[1,2-b]carb Azolyl and similar groups, but are not limited to these.

In this specification, the amine group may be selected from the group consisting of: monoalkylamino group; monoarylamino group; monoheteroarylamino group; -NH ₂ ; dialkylamino group; diarylamine group ; Diheteroarylamine group; alkylarylamine group; alkylheteroarylamine group; and arylheteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group may include methylamino group, dimethylamino group, ethylamine group, diethylamine group, phenylamine group, naphthylamino group, diphenylamine group, diphenylamine group base, anthracenylamino group, 9-methyl-anthracenylamino group, diphenylamino group, phenylnaphthylamine group, ditolylamino group, phenyltolylamino group, triphenylamine group, bis- Phenylnaphthylamino, phenylbiphenylamine, biphenylfluorenylamino, phenyltriphenylamino, biphenyltriphenylamino and similar groups, but not That's all.

In this specification, an aryl group means an aryl group having two bonding sites, that is, a divalent group. In addition to aryl groups, each of which is a divalent group, the description provided above for aryl groups may apply to aryl groups. In addition, heteroaryl means a heteroaryl group having two bonding sites, that is, a divalent group. In addition to heteroaryl groups, each of which is a divalent group, the description provided above for heteroaryl groups may apply to heteroaryl groups.

In this specification, an "adjacent" group may mean a substituent that replaces an atom directly linked to the atom replaced by the corresponding substituent, a substituent that is spatially closest to the corresponding substituent, or a substituent that replaces the atom that is replaced by the corresponding substituent. Another substituent for the substituted atom. For example, two substituents substituted at ortho positions in a benzene ring and two substituents substituted at the same carbon in an aliphatic ring may be interpreted as groups that are "adjacent" to each other.

In this disclosure, "where no substituent is specified in the chemical formula or compound structure" means that a hydrogen atom is bonded to a carbon atom. However, since deuterium ( ^2H ) is an isotope of hydrogen, some hydrogen atoms can be deuterium.

In one embodiment of the present disclosure, "the case where the substituent is not specified in the chemical formula or compound structure" may mean that all positions accessible to the substituent are hydrogen or deuterium. In other words, since deuterium is an isotope of hydrogen, some hydrogen atoms may be deuterium as an isotope, and as used herein, the deuterium content may range from 0% to 100%.

In one embodiment of the present disclosure, in "the case where no substituent is specified in the chemical formula or compound structure", when deuterium is not explicitly excluded (for example, "the deuterium content is 0%", "the hydrogen content is 100%" or " When the substituents are all hydrogen"), hydrogen and deuterium can be used interchangeably in the compound.

In one embodiment of the present disclosure, deuterium is one of the isotopes of hydrogen, an element having a deuterium nucleus formed of one proton and one neutron as a nucleus, and can be expressed as hydrogen-2, and its element symbol Can also be written as D or ² H.

In one embodiment of the present disclosure, isotopes mean atoms with the same atomic number (Z) but different mass numbers (A), and can also be interpreted as elements with the same number of protons but different numbers of neutrons.

In one embodiment of the present disclosure, when the total number of substituents that the base compound can have is defined as T1, and the number of specific substituents among these substituents is defined as T2, the content of the specific substituent is T% It can be defined as T2/T1×100=T%.

In other words, in one instance, by Having a deuterium content of 20% in a phenyl group means that the total number of substituents that the phenyl group can have is 5 (T1 in the formula), and the number of deuterium among these substituents is 1 (T2 in the formula) . In other words, having a deuterium content of 20% in the phenyl group can be represented by the following structural formula.

In addition, in one embodiment of the present disclosure, "phenyl group with 0% deuterium content" may mean a phenyl group that does not contain deuterium atoms, that is, a phenyl group with 5 hydrogen atoms.

In the present disclosure, C6 to C60 aromatic hydrocarbon ring means a compound including an aromatic ring formed of C6 to C60 carbon and hydrogen. Examples of C6 to C60 aromatic hydrocarbon rings may include benzene, biphenyl, terphenyl, terphenylene, naphthalene, anthracene, pyrene, phenanthrene, fluorene, pyrene, perylene, azulene and similar compounds, but are not limited thereto. , and includes all aromatic hydrocarbon ring compounds known in the art and satisfying the above number of carbon atoms.

One embodiment of the present disclosure provides a heterocyclic compound represented by the following Chemical Formula 1: [Chemical Formula 1] In Chemical Formula 1, R1 to R12 are the same as or different from each other, and each is 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)R101R102 ;-SiR101R102R103; and a group represented by the following Chemical Formula 2, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted Substituted C2 to C60 heterocycle, and R101, R102 and R103 are the same or different from each other, and each is independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group ; Or a substituted or unsubstituted C2 to C60 heteroaryl group, at least one of R2 to R12 is a group represented by the following Chemical Formula 2, and R13 and R14 are -CRaRbRc, and Ra to Rc are the same as or different from each other , and each is 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; and substituted or unsubstituted C2 to C60 Heterocycloalkyl, [Chemical Formula 2] In Chemical Formula 2, L1 and L2 are the same as or different from each other, and each is independently a single bond; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group , Ar1 and Ar2 are the same or different from each other, and are each independently a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, m and n are the same as or different from each other, and are each independently an integer of 0 to 3, and * represents a bonding site to the compound of Chemical Formula 1.

In one embodiment of the present disclosure, R1 to R12 are the same as or different from each other, and each is independently selected from the group consisting of: hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C30 alkyl ; Substituted or unsubstituted C2 to C30 alkenyl; Substituted or unsubstituted C2 to C30 alkynyl; Substituted or unsubstituted C1 to C30 alkoxy; Substituted or unsubstituted C3 to C30 cycloalkyl; substituted or unsubstituted C2 to C30 heterocycloalkyl; substituted or unsubstituted C6 to C30 aryl; substituted or unsubstituted C2 to C30 heteroaryl; -P( =O)R101R102; -SiR101R102R103; and a group represented by Chemical Formula 2, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C30 aromatic hydrocarbon ring or Substituted or unsubstituted C2 to C30 heterocycle, R101, R102 and R103 are the same or different from each other, and each is independently a substituted or unsubstituted C1 to C30 alkyl; substituted or unsubstituted C6 to C30 an aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, and at least one of R2 to R12 may be a group represented by Chemical Formula 2.

In another embodiment of the present disclosure, R1 to R12 are the same or different from each other, and each is independently selected from the group consisting of: hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C20 alkane base; substituted or unsubstituted C2 to C20 alkenyl; substituted or unsubstituted C2 to C20 alkynyl; substituted or unsubstituted C1 to C20 alkoxy; substituted or unsubstituted C3 to C20 cycloalkyl; substituted or unsubstituted C2 to C20 heterocycloalkyl; substituted or unsubstituted C6 to C20 aryl; substituted or unsubstituted C2 to C20 heteroaryl; -P (=O)R101R102; -SiR101R102R103; and a group represented by Chemical Formula 2, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C20 aromatic hydrocarbon ring, or Substituted or unsubstituted C2 to C20 heterocycle, R101, R102 and R103 are the same or different from each other, and each is independently a substituted or unsubstituted C1 to C20 alkyl; substituted or unsubstituted C6 to C20 aryl group; or substituted or unsubstituted C2 to C20 heteroaryl group, and at least one of R2 to R12 may be a group represented by Chemical Formula 2.

In another embodiment of the present disclosure, R1 to R12 are the same or different from each other, and each is independently selected from the group consisting of: hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C20 alkane base; substituted or unsubstituted C2 to C20 alkenyl; substituted or unsubstituted C2 to C20 alkynyl; substituted or unsubstituted C1 to C20 alkoxy; substituted or unsubstituted C3 to C20 cycloalkyl; substituted or unsubstituted C2 to C20 heterocycloalkyl; substituted or unsubstituted C6 to C20 aryl; substituted or unsubstituted C2 to C20 heteroaryl; and from A group represented by Chemical Formula 2, and at least one of R2 to R12 may be a group represented by Chemical Formula 2.

In one embodiment of the present disclosure, R1 can be hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C30 alkyl; substituted or unsubstituted C2 to C30 alkenyl; substituted or Unsubstituted C2 to C30 alkynyl; substituted or unsubstituted C1 to C30 alkoxy; substituted or unsubstituted C3 to C30 cycloalkyl; substituted or unsubstituted C2 to C30 heterocycle Alkyl; substituted or unsubstituted C6 to C30 aryl; or substituted or unsubstituted C2 to C30 heteroaryl.

In another embodiment of the present disclosure, R1 can be hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C20 alkyl; substituted or unsubstituted C2 to C20 alkenyl; substituted Or unsubstituted C2 to C20 alkynyl; substituted or unsubstituted C1 to C20 alkoxy; substituted or unsubstituted C3 to C20 cycloalkyl; substituted or unsubstituted C2 to C20 hetero Cycloalkyl; substituted or unsubstituted C6 to C20 aryl; or substituted or unsubstituted C2 to C20 heteroaryl.

In another embodiment of the present disclosure, R1 can be hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C6 to C20 aryl; or substituted or unsubstituted C2 to C20 heteroaryl.

In another embodiment of the present disclosure, R1 can be hydrogen; deuterium; halogen; cyano; substituted or unsubstituted phenyl; substituted or unsubstituted biphenyl; substituted or unsubstituted terphenyl; substituted or unsubstituted dibenzofuranyl; substituted or unsubstituted dibenzothienyl; or substituted or unsubstituted dibenzocarbazolyl.

In one embodiment of the present disclosure, at least one of R2 to R8 may be a group represented by the following Chemical Formula 2: [Chemical Formula 2] Chemical formula 2 is the same as defined above.

In another embodiment of the present disclosure, any one of R2 to R4 is a group represented by Chemical Formula 2, and R1 and R5 to R8 can each be independently selected from the group consisting of: hydrogen; deuterium; halogen ; Cyano; substituted or unsubstituted C1 to C30 alkyl; substituted or unsubstituted C2 to C30 alkenyl; substituted or unsubstituted C2 to C30 alkynyl; substituted or unsubstituted C1 to C30 alkoxy; substituted or unsubstituted C3 to C30 cycloalkyl; substituted or unsubstituted C2 to C30 heterocycloalkyl; substituted or unsubstituted C6 to C30 aryl; and Substituted or unsubstituted C2 to C30 heteroaryl.

In another embodiment of the present disclosure, any one of R2 to R4 is a group represented by Chemical Formula 2, and R1 and R5 to R8 can each be independently selected from the group consisting of: hydrogen; deuterium; halogen ; Cyano; substituted or unsubstituted C1 to C20 alkyl; substituted or unsubstituted C2 to C20 alkenyl; substituted or unsubstituted C2 to C20 alkynyl; substituted or unsubstituted C1 to C20 alkoxy; substituted or unsubstituted C3 to C20 cycloalkyl; substituted or unsubstituted C2 to C20 heterocycloalkyl; substituted or unsubstituted C6 to C20 aryl; and Substituted or unsubstituted C2 to C20 heteroaryl.

In another embodiment of the present disclosure, any one of R2 to R4 is a group represented by Chemical Formula 2, and R1 and R5 to R8 may each independently be hydrogen; deuterium; halogen; cyano; substituted or Unsubstituted phenyl; substituted or unsubstituted biphenyl; substituted or unsubstituted terphenyl; substituted or unsubstituted naphthyl; substituted or unsubstituted phenanthrenyl; Substituted or unsubstituted terphenylene; substituted or unsubstituted dibenzofuryl; substituted or unsubstituted dibenzothienyl; or substituted or unsubstituted dibenzocarb Azolyl.

In another embodiment of the present disclosure, any one of R5 to R8 is a group represented by Chemical Formula 2, and R1 to R4 may each be independently selected from the group consisting of: hydrogen; deuterium; halogen; cyanide base; substituted or unsubstituted C1 to C30 alkyl; substituted or unsubstituted C2 to C30 alkenyl; substituted or unsubstituted C2 to C30 alkynyl; substituted or unsubstituted C1 to C30 alkoxy; substituted or unsubstituted C3 to C30 cycloalkyl; substituted or unsubstituted C2 to C30 heterocycloalkyl; substituted or unsubstituted C6 to C30 aryl; and substituted Or unsubstituted C2 to C30 heteroaryl.

In another embodiment of the present disclosure, any one of R5 to R8 is a group represented by Chemical Formula 2, and R1 to R4 may each be independently selected from the group consisting of: hydrogen; deuterium; halogen; cyanide base; substituted or unsubstituted C1 to C20 alkyl; substituted or unsubstituted C2 to C20 alkenyl; substituted or unsubstituted C2 to C20 alkynyl; substituted or unsubstituted C1 to C20 alkoxy; substituted or unsubstituted C3 to C20 cycloalkyl; substituted or unsubstituted C2 to C20 heterocycloalkyl; substituted or unsubstituted C6 to C20 aryl; and substituted or unsubstituted C2 to C20 heteroaryl.

In another embodiment of the present disclosure, any one of R5 to R8 is a group represented by Chemical Formula 2, and R1 to R4 can each independently be hydrogen; deuterium; halogen; cyano; substituted or unsubstituted Substituted phenyl; substituted or unsubstituted biphenyl; substituted or unsubstituted terphenyl; substituted or unsubstituted naphthyl; substituted or unsubstituted phenanthrenyl; substituted or Unsubstituted terphenylene; substituted or unsubstituted dibenzofuranyl; substituted or unsubstituted dibenzothienyl; or substituted or unsubstituted dibenzocarbazolyl .

In one embodiment of the present disclosure, R13 and R14 are -CRaRbRc, and Ra to Rc are the same or different from each other, and can each be independently selected from the group consisting of: hydrogen; deuterium; halogen; cyano; substituted or Unsubstituted C1 to C30 alkyl; substituted or unsubstituted C2 to C30 alkenyl; substituted or unsubstituted C2 to C30 alkynyl; substituted or unsubstituted C1 to C30 alkoxy; Substituted or unsubstituted C3 to C30 cycloalkyl; and substituted or unsubstituted C2 to C30 heterocycloalkyl.

In another embodiment of the present disclosure, R13 and R14 are -CRaRbRc, and Ra to Rc are the same or different from each other, and can each be independently selected from the group consisting of: hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C10 alkyl; substituted or unsubstituted C2 to C10 alkenyl; substituted or unsubstituted C2 to C10 alkynyl; substituted or unsubstituted C1 to C10 alkoxy ; Substituted or unsubstituted C3 to C10 cycloalkyl; and substituted or unsubstituted C2 to C10 heterocycloalkyl.

In another embodiment of the present disclosure, R13 and R14 are -CRaRbRc, and Ra to Rc are the same or different from each other, and can each be independently selected from the group consisting of hydrogen, deuterium, halogen and cyano.

In one embodiment of the present disclosure, L1 and L2 are the same as or different from each other, and can each independently be a single bond; a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 aryl group. C30 extended heteroaryl.

In another embodiment of the present disclosure, L1 and L2 are the same as or different from each other, and can each independently be a single bond; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 To C20 extension heteroaryl.

In another embodiment of the present disclosure, L1 and L2 are the same or different from each other, and can each independently be a single bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; Or substituted or unsubstituted triphenyl.

In one embodiment of the present disclosure, Ar1 and Ar2 are the same as or different from each other, and can each independently be a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group .

In another embodiment of the present disclosure, Ar1 and Ar2 are the same as or different from each other, and can each independently be a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group. base.

In another embodiment of the present disclosure, Ar1 and Ar2 are the same or different from each other, and can each independently be a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted biphenyl group; Substituted terphenyl; substituted or unsubstituted naphthyl; substituted or unsubstituted phenanthrenyl; substituted or unsubstituted terphenylene; substituted or unsubstituted fluorenyl; Substituted or unsubstituted dibenzofuranyl; substituted or unsubstituted dibenzothienyl; or substituted or unsubstituted dibenzocarbazolyl.

In another embodiment of the present disclosure, Ar1 and Ar2 are the same as or different from each other, and the case where Ar1 or Ar2 is 9,9-diphenylfluorenyl can be excluded. More specifically, exclude the case where Ar1 or Ar2 includes a compound represented by any of the following compounds: , , , , , , .

In one embodiment of the present disclosure, the compound represented by Chemical Formula 1 may not include deuterium as a substituent, or may have, for example, greater than 0%, 1%, or greater than 1%, relative to the total number of hydrogen atoms and deuterium atoms. 10% or more, 20% or more, 30% or more, 40% or more, or 50% or more and 100% or less, 90% or less than 90% , 80% or less, 70% or less, or 60% or less deuterium content.

In another embodiment of the present disclosure, the compound represented by Chemical Formula 1 may not include deuterium, or may have a deuterium content of 1% to 100% relative to the total number of hydrogen atoms and deuterium atoms.

In another embodiment of the present disclosure, the compound represented by Chemical Formula 1 may not include deuterium, or may have a deuterium content of 20% to 90% relative to the total number of hydrogen atoms and deuterium atoms.

In another embodiment of the present disclosure, the compound represented by Chemical Formula 1 may not include deuterium, or may have a deuterium content of 30% to 80% relative to the total number of hydrogen atoms and deuterium atoms.

In another embodiment of the present disclosure, the compound represented by Chemical Formula 1 may not include deuterium, or may have a deuterium content of 40% to 70% relative to the total number of hydrogen atoms and deuterium atoms.

For example, based on the total number of hydrogen atoms and deuterium atoms, the heterocyclic compound represented by Chemical Formula 1 may have 0% or more, 1% or more, 5% or more, 10% or more. 10%, 15% or more than 15%, 20% or more than 20%, 25% or more than 25%, 30% or more than 30%, 35% or more than 35%, 40% or more than 40%, 45% or more than 45 %, or 50% or more than 50% and 100% or less than 100%, 95% or less than 95%, 90% or less than 90%, 85% or less than 85%, 80% or less than 80%, 75% or less Deuterium content of 75%, 70% or less, 65% or less, or 60% or less.

In one embodiment of the present disclosure, the heterocyclic compound represented by Chemical Formula 1 may be any one selected from the group consisting of the following compounds: .

In addition, by introducing various substituents into the structure of Chemical Formula 1, compounds having unique properties of the introduced substituents can be synthesized. For example, by combining hole injection layer materials, hole transport layer materials, hole transport auxiliary layer materials, electron blocking layer materials, light emitting layer materials, and electron transport layer materials that are commonly used to manufacture organic light-emitting devices. , the substituents of the hole blocking layer material and the electron injection layer material are introduced into the core structure, and materials that meet the requirements of each organic material layer can be synthesized.

In addition, by introducing various substituents into the structure of Chemical Formula 1, the energy bandgap can be finely controlled, and at the same time, the properties at the interface between organic materials can be enhanced, and material applications can become diversified.

Another embodiment of the present disclosure provides an organic light-emitting element including the heterocyclic compound represented by Chemical Formula 1. "Organic light-emitting element" can be expressed by terms such as "organic light emitting diode (OLED)", "OLED", "OLED element" and "organic electroluminescent (EL) element".

In addition, an embodiment of the present disclosure provides an organic light-emitting element. The organic light-emitting element includes: a first electrode; a second electrode disposed opposite to the first electrode; and one or more organic material layers disposed on the first electrode. between an electrode and a second electrode, wherein one or more of the organic material layers includes a heterocyclic compound represented by Chemical Formula 1.

In one embodiment of the present disclosure, the first electrode may be a positive electrode, and the second electrode may be a negative electrode.

In another embodiment of the present disclosure, the first electrode may be a negative electrode, and the second electrode may be a positive electrode.

In one embodiment of the present disclosure, the organic light-emitting element may be a red organic light-emitting element, and the heterocyclic compound represented by Chemical Formula 1 may be used as a material of the red organic light-emitting element.

In another embodiment of the present disclosure, the organic light-emitting element may be a green organic light-emitting element, and the heterocyclic compound represented by Chemical Formula 1 may be used as a material of the green organic light-emitting element.

In another embodiment of the present disclosure, the organic light-emitting element may be a blue organic light-emitting element, and the heterocyclic compound represented by Chemical Formula 1 may be used as a material of the blue organic light-emitting element.

In one embodiment of the present disclosure, the organic light-emitting element may be a red organic light-emitting element, and the heterocyclic compound represented by Chemical Formula 1 may be used as a light-emitting layer material of the red organic light-emitting element.

In another embodiment of the present disclosure, the organic light-emitting element may be a green organic light-emitting element, and the heterocyclic compound represented by Chemical Formula 1 may be used as a light-emitting layer material of the green organic light-emitting element.

In another embodiment of the present disclosure, the organic light-emitting element may be a blue organic light-emitting element, and the heterocyclic compound represented by Chemical Formula 1 may be used as a light-emitting layer material of the blue organic light-emitting element.

Specific explanations about the heterocyclic compound represented by Chemical Formula 1 are the same as those provided above.

In addition to using the above-mentioned heterocyclic compounds to form one or more organic material layers, common organic light-emitting device manufacturing methods and materials can be used to manufacture the organic light-emitting device of the present disclosure.

When manufacturing an organic light-emitting element, the heterocyclic compound can be formed into an organic material layer using a solution coating method and a vacuum deposition method. In this article, the solution coating method means spin coating, dip coating, inkjet printing, screen printing, spray method, Roll coating and similar methods, but not limited to these.

The organic material layer of the organic light-emitting element of the present disclosure can be formed in a single-layer structure, or can also be formed in a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light-emitting element of the present disclosure may have a hole injection layer, a hole transport layer, a hole transport auxiliary layer, a light-emitting layer, an electron injection layer, an electron transport layer, an electron blocking layer, a hole blocking layer and the like. Layer as a structure of layers of organic material. However, the structure of the organic light-emitting element is not limited to this, but may include a smaller number of organic material layers.

In the organic light-emitting element of the present disclosure, the organic material layer includes a light-emitting layer, and the light-emitting layer may include a heterocyclic compound represented by Chemical Formula 1. The use of the heterocyclic compound in the emissive layer enables strong charge to be achieved by spatially separating the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) transfer, and therefore the organic light-emitting element can have excellent driving efficiency and lifetime.

In one embodiment of the present disclosure, the organic light-emitting element may include one or more organic material layers, the organic material layer may include a light-emitting layer, and the light-emitting layer may include a heterocyclic compound represented by Chemical Formula 1.

In another embodiment of the present disclosure, the organic material layer may include a light-emitting layer, the light-emitting layer may include a host material, and the host material may include the heterocyclic compound.

In another embodiment of the present disclosure, the organic light-emitting element may further include a group 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. One, two, or more layers of the group.

In one embodiment of the present disclosure, the organic light-emitting element may include one or more organic material layers, the organic material layer may include a hole transport layer, and the hole transport layer may include a heterocyclic ring represented by Chemical Formula 1 compound.

In another embodiment of the present disclosure, the organic light-emitting element may further include a layer selected from the group consisting of a light-emitting layer, a hole injection layer, a hole transport auxiliary layer, an electron injection layer, an electron transport layer, an electron blocking layer and a hole blocking layer. One, two, or more layers of a group.

In one embodiment of the present disclosure, the organic light-emitting element may include one or more organic material layers, the organic material layer may include a hole transport auxiliary layer, and the hole transport auxiliary layer may include a Heterocyclic compounds.

In another embodiment of the present disclosure, the organic light-emitting element may further include a group 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. One, two, or more layers of the group.

In one embodiment of the present disclosure, the organic light-emitting element may include one or more organic material layers, the organic material layer may include an electron blocking layer, and the electron blocking layer may include a heterocyclic compound represented by Chemical Formula 1.

In another embodiment of the present disclosure, the organic light-emitting element may further include a light-emitting layer, a hole injection layer, a hole transport layer, a hole transport auxiliary layer, an electron injection layer, an electron transport layer and a hole blocking layer. One layer, two layers, or more layers of the group.

In one embodiment of the present disclosure, the organic material layer includes a heterocyclic compound represented by Chemical Formula 1, and a phosphorescent dopant may be used therewith.

As the phosphorescent dopant material, materials known in the art can be used. For example, phosphorescent dopant materials represented by LL'MX', LL'L''M, LMX'X'', _L2MX ', and _L3M may be used, however, the scope of the present disclosure is not limited to this limited by some instances.

M can be iridium, platinum, osmium or similar materials.

L is an anionic bidentate ligand coordinated with M through sp ² carbon and heteroatoms, and X can play the role of trapping electrons or holes. Non-limiting examples of L, L' and L'' may include 2-(1-naphthyl)benzoxazole, 2-phenylbenzoxazole, 2-phenylbenzothiazole, 7,8-benzene Quinoline, phenylpyridine, benzothienylpyridine, 3-methoxy-2-phenylpyridine, thienylpyridine, tolylpyridine and similar materials. Non-limiting examples of X' and X'' may include acetylacetonate (acac), hexafluoroacetylacetonate, salicylidene, picolinate, 8-hydroxyquinoline acid salts and similar materials.

Specific examples of the phosphorescent dopant are as follows, however, the phosphorescent dopant is not limited to these examples: .

In one embodiment of the present disclosure, the organic material layer includes a heterocyclic compound represented by Chemical Formula 1, and an iridium-based dopant may be used therewith.

In one embodiment of the present disclosure, as the iridium-based dopant, Ir(ppy) ₃ can be used as a green phosphorescent dopant or a red phosphorescent dopant.

In one embodiment of the present disclosure, the content of the dopant may be 1% to 15%, preferably 2% to 10%, and more preferably 3% to 7% based on the total weight of the light emitting layer.

In the organic light-emitting element according to one embodiment of the present disclosure, the organic material layer includes a hole transport layer or a hole transport auxiliary layer, and the hole transport layer or the hole transport auxiliary layer may include a hybrid compound represented by Chemical Formula 1 cyclic compounds.

In an organic light-emitting element according to another embodiment of the present disclosure, the organic material layer includes an electron injection layer or an electron transport layer, and the electron injection layer or the electron transport layer may include a heterocyclic compound represented by Chemical Formula 1.

In an organic light-emitting element according to another embodiment of the present disclosure, the organic material 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 represented by Chemical Formula 1.

In an organic light-emitting element according to another embodiment of the present disclosure, the organic material layer includes an electron transport layer, a light-emitting layer or a hole blocking layer, and the electron transport layer, the light-emitting layer or the hole blocking layer may include the chemical formula 1 represents heterocyclic compounds.

In an organic light-emitting element according to another embodiment of the present disclosure, the organic material layer includes a light-emitting layer, and the light-emitting layer may include a heterocyclic compound represented by Chemical Formula 1.

In an organic light-emitting element according to another embodiment of the present disclosure, the organic material layer includes a light-emitting layer, the light-emitting layer includes a host material, and the host material may include a heterocyclic compound represented by Chemical Formula 1.

In an organic light-emitting element according to yet another embodiment, the light-emitting layer may include two or more host materials, and at least one of the host materials may include a heterocyclic compound represented by Chemical Formula 1.

In an organic light-emitting element according to yet another embodiment, two or more host materials may be premixed and used in the light-emitting layer, and at least one of the two or more host materials may include: of heterocyclic compounds.

Premixing means first mixing the two or more host materials in a supply before depositing the materials on the layer of organic material.

The organic light-emitting element according to an embodiment of the present disclosure may further include one layer, two 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 blocking layer and a hole blocking layer. layer or more.

1 to 3 illustrate a stacking sequence of electrodes and organic material layers of an organic light-emitting element according to an embodiment of the present disclosure. However, the scope of the present application is not intended to be limited by these drawings, and the structures of organic light-emitting devices known in the art may also be applied to the present application.

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

Figure 3 shows a case where the organic material layer is multiple layers. The organic light-emitting element according to FIG. 3 includes a hole injection layer 301, a hole transport layer 302, a light emitting layer 303, a hole blocking layer 304, an electron transport layer 305 and an electron injection layer 306. However, the scope of the present application is not limited by such a stacked structure, and if necessary, layers other than the light-emitting layer may not be included, and other necessary functional layers may be further added.

One embodiment of the present disclosure provides a method for manufacturing an organic light-emitting element, the method including: preparing a substrate; forming a first electrode on the substrate; forming one or more organic material layers on the first electrode; and A second electrode is formed on the organic material layer, wherein forming the organic material layer includes using a heterocyclic compound according to an embodiment of the present disclosure to form one or more organic material layers.

In one embodiment of the present disclosure, the forming the organic material layer may be using a thermal vacuum deposition method after premixing the heterocyclic compound represented by Chemical Formula 1 to form the organic material layer.

Premixing means that the heterocyclic compound represented by Chemical Formula 1 is first mixed in a supply source before depositing the material on the organic material layer.

The premixed material may be referred to as a heterocyclic compound according to one embodiment of the present application.

The organic material layer including the heterocyclic compound represented by Chemical Formula 1 may further include other materials as needed.

In the organic light-emitting element according to one embodiment of the present disclosure, materials other than the heterocyclic compound represented by Chemical Formula 1 are shown below. However, these materials are only for illustrative purposes and are not used to limit the application. within the scope of the project, and these materials may be replaced by materials known in the art.

As the positive electrode material, materials each having a relatively large work function may be used, and a transparent conductive oxide, a metal, a conductive polymer, or the like may be used. Specific examples of positive electrode materials 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 (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-( Poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole and polyaniline; and similar materials, but are not limited to these.

As the negative electrode material, materials each having a relatively small work function can be used, and metal, metal oxide, conductive polymer or the like can be used. Specific examples of negative electrode materials include: metals, such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, yttrium, aluminum, silver, tin and lead, or alloys thereof; multilayer structure materials, such as LiF/Al or LiO ₂ /Al; and similar materials, but not limited to these.

As the hole injection layer material, known hole injection layer materials can be used, and for example, a phthalocyanine compound can be used, such as copper phthalocyanine disclosed in US Patent No. 4,356,429; or the literature [Advanced Materials] ), 6, page 677 (1994)] star-shaped burst amine derivatives, such as tris(4-carbazoyl-9-ylphenyl)amine (tris(4-carbazoyl-9-ylphenyl) amine, TCTA), 4,4',4''-tri[phenyl(m-tolyl)amino]triphenylamine (4,4',4''-tri[phenyl(m-tolyl)amino] triphenylamine, m-MTDATA) or 1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene , m-MTDAPB); conductive polymers with soluble properties, such as polyaniline/dodecylbenzenesulfonic acid or poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate), polyaniline /camphorsulfonic acid or polyaniline/poly(4-styrenesulfonate); and similar materials.

As the hole transport layer material, pyrazoline derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives and similar materials can be used, and low molecular materials or polymer materials can also be used. .

As the electron transport layer material, oxadiazole derivatives, anthraquinone dimethane and its derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, tetracyanoanthraquinone dimethane and its derivatives can be used. Methane and its derivatives, fluorenone derivatives, diphenyldicyanoethylene and its derivatives, diphenylquinone derivatives, 8-hydroxyquinoline and its derivatives and metal complexes of similar materials, and can also Use polymer materials as well as low molecular materials.

As an example of the electron injection layer material, LiF is commonly used in this technology, however, the present application is not limited thereto.

As the light-emitting layer material, a red, green or blue light-emitting material can be used, and as necessary, two or more light-emitting materials can be mixed and used. As used herein, the two or more luminescent materials may be deposited as separate supplies, or may be premixed and deposited as one supply. In addition, a fluorescent material may also be used as the light-emitting layer material, however, a phosphorescent material may also be used. As the light-emitting layer material, a material that emits light alone by combining holes and electrons injected from the positive electrode and the negative electrode, respectively, can be used. However, a material having a host material and a dopant material that both participate in light emission can also be used. .

When the hosts of the light emitting layer materials are mixed and used, hosts of the same series may be mixed and used, or hosts of different series may be mixed and used. For example, any two or more types of materials among n-type host materials and p-type host materials can be selected and used as the host material of the light-emitting layer.

Depending on the materials used, the organic light-emitting device according to one embodiment of the present disclosure may be a top-emission type, a bottom-emission type, or a dual-emission type. ).

The heterocyclic compound according to an embodiment of the present disclosure can also be used in organic electronics including organic solar cells, organic photoconductors, organic transistors and similar components based on principles similar to those in organic light-emitting devices. component.

In the following, preferred examples are provided to help understand the disclosure. However, the following examples are only provided to make it easier to understand the disclosure, and the disclosure is not limited thereto. < Preparation Example > Preparation Example 1 : Preparation of Compound 001 1 ) Preparation of compound 001-P5

Dissolve 1-bromonaphth-2-ol (50 g, 224.14 mmol) and (5-chloro-2-fluorophenyl)boronic acid (42.99 g, 246.56 mmol) in 1,4-dioxane (500 ml) and distilled water (100 ml), tetrakis(triphenylphosphine)palladium (Pd(PPh ₃ ) ₄ ) (12.95 g, 11.21 mmol) and potassium carbonate (K ₂ CO ₃ ) (77.45 g, 560.36 mmol) and the mixture was stirred under reflux for 12 hours. After the reaction was completed, the reaction solution was extracted with dichloromethane (DCM) and distilled water, and after the organic layer was dried with anhydrous magnesium sulfate (MgSO ₄ ), the solvent was removed using a rotary evaporator. After that, the resultant was purified by column chromatography using dichloromethane and hexane as developing solvents to obtain compound 001-P5 (45 g, yield 74 %). 2 ) Preparation of compound 001-P4

Compound 001-P5 (45 g, 165.02 mmol) and N-bromosuccinimide (32.31 g, 181.52 mmol) were introduced into dimethylformamide (1000 ml) and incubated at room temperature. The mixture was stirred for 12 hours. After the reaction was completed, distilled water (1000 ml) was introduced into the reaction solution, and after the resultant was stirred for 30 minutes, the resulting solid was filtered to obtain compound 001-P4 (53 g, yield 91%) . 3 ) Preparation of compound 001-P3

Compound 001-P4 (53 g, 150.74 mmol) was dissolved in N,N-dimethylacetamide (600 ml), and after heating the mixture to 150 °C, cesium carbonate (Cs) was introduced ₂ CO ₃ ) (147.34 g, 452.22 mmol) and the resultant was stirred at reflux for 30 min. After the reaction was completed, the resultant was extracted with dichloromethane and distilled water, and after the organic layer was dried with anhydrous magnesium sulfate (MgSO ₄ ), the solvent was removed using a rotary evaporator. After that, the resultant was purified by column chromatography using dichloromethane and hexane as developing solvents to obtain compound 001-P3 (42 g, yield 84%). 4 ) Preparation of compound 001-P2

Compound 001-P3 (42 g, 126.66 mmol) and (2-(methoxycarbonyl)phenyl)boronic acid (25.07 g, 139.33 mmol) were dissolved in 1,4-dioxane (500 ml). ) and distilled water (100 ml), tetrakis(triphenylphosphine)palladium (Pd(PPh ₃ ) ₄ ) (7.32 g, 6.33 mmol) and potassium carbonate (K ₂ CO ₃ ) (43.77 g, 316.66 mmol) and the mixture was stirred under reflux for 12 hours. After the reaction was completed, the reaction solution was extracted with dichloromethane (DCM) and distilled water, and after the organic layer was dried with anhydrous magnesium sulfate (MgSO ₄ ), the solvent was removed using a rotary evaporator. After that, the resultant was purified by column chromatography using dichloromethane and hexane as developing solvents to obtain compound 001-P2 (40 g, yield 82%). 5 ) Preparation of compound 001-P1

After compound 001-P2 (40 g, 103.40 mmol) was dissolved in tetrahydrofuran (400 ml), methylmagnesium bromide (3 mol/L (M) diethyl ether solution was slowly added thereto at 0°C , 103 ml, 310.21 mmol), and the mixture was then stirred at 60°C for 6 hours. After the reaction was completed, water was added to the reaction solution to terminate the reaction, and the resultant was extracted with dichloromethane and distilled water. The organic layer was dried using anhydrous magnesium sulfate ( _MgSO4 ), and the solvent was then removed using a rotary evaporator. After that, the resultant was dissolved in methylene chloride, boron trifluoride diethyl ether was added to the reaction material, and then the resultant was stirred at room temperature for 4 hours. After the reaction was completed, the resultant was purified by column chromatography using dichloromethane and hexane as developing solvents to obtain compound 001-P1 (27 g, yield 70%). 6 ) Preparation of compound 001

Compound 001-P1 (10 g, 27.11 mmol) and N-phenyl-[1,1'-biphenyl]-4-amine (6.98 g, 28.47 mmol) were dissolved in toluene (100 ml ), tris(dibenzylideneacetone)dipalladium (Pd ₂ (dba) ₃ ) (1.24 g, 1.36 mmol), dicyclohexyl (2',4',6'-tris dicyclohexyl(2',4',6'-triisopropyl-[1,1'-biphenyl]-2-yl)phosphine, Xphos ) (1.29 g, 2.71 mmol) and sodium tert-butoxide (t-BuONa) (5.21 g, 54.22 mmol), and the mixture was stirred under reflux for 2 hours. After the reaction was completed, the reaction solution was extracted with dichloromethane and distilled water, and after the organic layer was dried with anhydrous magnesium sulfate (MgSO ₄ ), the solvent was removed using a rotary evaporator. After that, the resultant was purified by column chromatography using dichloromethane and hexane as developing solvents to obtain compound 001 (13 g, yield 83%).

Except using compound A in Table 1 below instead of (5-chloro-2-fluorophenyl)boronic acid, using compound B in Table 1 below instead of (2-(methoxycarbonyl)phenyl)boronic acid, and using compounds in Table 1 below. The target compound was synthesized in the same manner as in Preparation Example 1 except that C was substituted for N-phenyl-[1,1′-biphenyl]-4-amine. [Table 1] Compound number Compound A Compound B Compound C target compound Yield 006 72% 016 78% 023 79% 030 71% 052 80% 058 75% 062 75% 073 73% 084 72% 088 79% 113 75% 119 73% 122 74% 135 70% Preparation Example 2 : Preparation of Compound 141 1 ) Preparation of compound 141-P5

Dissolve 1-bromonaphth-2-ol (50 g, 224.14 mmol) and (5-chloro-2-fluorophenyl)boronic acid (42.99 g, 246.56 mmol) in 1,4-dioxane (500 ml) and distilled water (100 ml), tetrakis(triphenylphosphine)palladium (Pd(PPh ₃ ) ₄ ) (12.95 g, 11.21 mmol) and potassium carbonate (K ₂ CO ₃ ) (77.45 g, 560.36 mmol) and the mixture was stirred at reflux for 12 hours. After the reaction was completed, the reaction solution was extracted with dichloromethane (DCM) and distilled water, and after the organic layer was dried with anhydrous magnesium sulfate (MgSO ₄ ), the solvent was removed using a rotary evaporator. After that, the resultant was purified by column chromatography using dichloromethane and hexane as developing solvents to obtain compound 141-P5 (45 g, yield 74%). 2 ) Preparation of compound 141-P4

Compound 141-P5 (45 g, 165.02 mmol) and N-bromosuccinimide (32.31 g, 181.52 mmol) were introduced into dimethylformamide (1000 ml) and incubated at room temperature. The mixture was stirred for 12 hours. After the reaction was completed, distilled water (1000 ml) was introduced into the reaction solution, and after the resultant was stirred for 30 minutes, the resulting solid was filtered to obtain compound 141-P4 (53 g, yield 91%) . 3 ) Preparation of compound 141-P3

Compound 141-P4 (53 g, 150.74 mmol) was dissolved in N,N-dimethylacetamide (600 ml), and after heating the mixture to 150 °C, cesium carbonate (Cs) was introduced ₂ CO ₃ ) (147.34 g, 452.22 mmol) and the resultant was stirred at reflux for 30 min. After the reaction was completed, the resultant was extracted with dichloromethane and distilled water, and after the organic layer was dried with anhydrous magnesium sulfate (MgSO ₄ ), the solvent was removed using a rotary evaporator. After that, the resultant was purified by column chromatography using dichloromethane and hexane as developing solvents to obtain compound 141-P3 (42 g, yield 84%). 4 ) Preparation of compound 141-P2

After combining compound 141-P3 (42 g, 126.66 mmol) and 2-(4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl)-[1 ,1'-biphenyl]-3-carboxylic acid methyl ester (47.12 g, 139.33 mmol) was dissolved in 1,4-dioxane (500 ml) and distilled water (100 ml), and then introduced Tetrakis(triphenylphosphine)palladium (Pd(PPh ₃ ) ₄ ) (7.32 g, 6.33 mmol) and potassium carbonate (K ₂ CO ₃ ) (43.77 g, 316.66 mmol) were added, and the mixture was refluxed Stirred for 12 hours. After the reaction was completed, the reaction solution was extracted with dichloromethane and distilled water, and after the organic layer was dried with anhydrous magnesium sulfate (MgSO ₄ ), the solvent was removed using a rotary evaporator. After that, the resultant was purified by column chromatography using dichloromethane and hexane as developing solvents to obtain compound 141-P2 (45 g, yield 77%). 5 ) Preparation of compound 141-P1

After compound 141-P2 (45 g, 97.21 mmol) was dissolved in tetrahydrofuran (500 ml), methylmagnesium bromide (3 mol/l ether solution, 97 ml) was slowly added at 0°C. , 291.63 mmol), and the mixture was then stirred at 60°C for 6 hours. After the reaction was completed, water was added to the reaction solution to terminate the reaction, and the resultant was extracted with dichloromethane and distilled water. The organic layer was dried using anhydrous magnesium sulfate ( _MgSO4 ), and the solvent was then removed using a rotary evaporator. After that, the resultant was dissolved in methylene chloride, boron trifluoride diethyl ether was added to the reaction material, and then the resultant was stirred at room temperature for 4 hours. After the reaction was completed, the resultant was purified by column chromatography using dichloromethane and hexane as developing solvents to obtain compound 141-P1 (30 g, yield 69%). 6 ) Preparation of compound 141

Compound 141-P1 (10 g, 22.47 mmol) and bis([1,1'-biphenyl]-4-yl)amine (7.58 g, 23.60 mmol) were dissolved in toluene (100 ml). After neutralization, tris(dibenzylideneacetone)dipalladium (Pd ₂ (dba) ₃ ) (1.03 g, 1.12 mmol), dicyclohexyl (2',4',6'-triiso Propyl-[1,1'-biphenyl]-2-yl)phosphine (Xphos) (1.07 g, 2.25 mmol) and sodium tert-butoxide (t-BuONa) (4.32 g, 44.95 mmol) ) and the mixture was stirred under reflux for 2 hours. After the reaction was completed, the reaction solution was extracted with dichloromethane and distilled water, and after the organic layer was dried with anhydrous magnesium sulfate (MgSO ₄ ), the solvent was removed using a rotary evaporator. After that, the resultant was purified by column chromatography using dichloromethane and hexane as developing solvents to obtain compound 141 (13 g, yield 79%).

In addition to using compound D in Table 2 below instead of (5-chloro-2-fluorophenyl)boronic acid, and using compound E in Table 2 below instead of 2-(4,4,5,5-tetramethyl-1,3,2 -Dioxaboran-2-yl)-[1,1'-biphenyl]-3-carboxylic acid methyl ester and use of compound F from Table 2 below instead of bis([1,1'-biphenyl] The target compound was synthesized in the same manner as in Preparation Example 2 except for -4-yl)amine. [Table 2] Compound number Compound D Compound E Compound F target compound Yield 155 77% 167 79% 173 69% 185 73% 191 71% 210 74% 212 75% 237 68% 239 65% 248 70% 255 73% 274 78% 275 71% 281 68% 287 70% 303 66% 314 74% 330 71% 332 71% 346 73% 354 69% 363 79% 374 77% 390 71% 397 72% 410 76% 413 70% 433 69% 442 79% 450 80% 461 74% 473 77% 485 78% 494 71% 510 68% 514 74% 526 75% 532 73% 542 71% 562 77% 589 72% Preparation Example 3 : Preparation of Compound 584

Compound 113 (10 g, 16.45 mmol), trifluoromethanesulfonic acid (3.70 g, 24.68 mmol) and D6-benzene (100 mL) were introduced into the reaction flask, and the mixture was then stirred under reflux for 5 hours. After the reaction was completed, water was introduced thereto to terminate the reaction, and the resultant was extracted with dichloromethane and distilled water. The organic layer was dried using anhydrous magnesium sulfate ( _MgSO4 ), and the solvent was then removed using a rotary evaporator. After that, the resultant was purified by column chromatography using dichloromethane and hexane as developing solvents to obtain compound 584 (9 g, yield 87%).

Compounds other than the compounds described in Preparation Examples 1 to 3 were also prepared in the same manner as in the above Preparation Examples, and the synthesis results are shown in Tables 3 and 4 below. Table 3 below shows ^{the 1} H nuclear magnetic resonance (NMR) (CDCl ₃ , 300 MHz) measurement values of the compounds, and Table 4 below shows the field desorption mass spectrometry (FD- MS) (FD-MS: Field Desorption Mass Spectrometry) measurements. [table 3] compound ¹ H NMR ( CDCl ₃ , 300 MHz ) 001 δ=8.55 (1H, d), 8.09 (1H, d), 8.08 (1H, d), 7.65-7.41 (13H, m), 7.24 (1H, t), 7.20 (2H, t), 6.81 (1H, t), 6.69 (2H, d), 6.63 (2H, d), 6.39 (1H, d), 1.85 (6H, s) 006 δ=8.55 (1H, d), 8.09 (1H, d), 8.08 (1H, d), 7.87 (1H, d), 7.65-7.38 (16H, m), 7.28 (1H, t), 7.24 (1H, t), 6.75 (1H, s), 6.69 (2H, d), 6.58 (1H, d), 6.39 (1H, d), 1.85 (6H, s), 1.72 (6H, s) 016 δ=8.55 (1H, d), 8.45 (1H, d), 8.09 (1H, d), 8.08 (1H, d), 7.98 (1H, d), 7.80 (1H, d), 7.65-7.41 (8H, m), 7.24 (1H, t), 7.20 (2H, t), 7.06 (1H, s), 6.88 (1H, d), 6.81 (1H, t), 6.63 (2H, d), 6.39 (1H, d ), 1.85 (6H, s) 023 δ=8.55 (1H, d), 8.09 (1H, d), 8.08 (1H, d), 7.64-7.41 (20H, m), 7.24 (1H, t), 6.69 (4H, d), 6.33 (1H, d), 1.85 (6H, s) 030 δ=8.93 (2H, d), 8.55 (1H, d), 8.13 (1H, s), 8.12 (2H, d), 8.09 (1H, d), 8.08 (1H, d), 7.88-7.82 (5H, m), 7.64 (1H, d), 7.61 (1H, d), 7.55 (2H, t), 7.44 (1H, t), 7.43 (1H, s), 7.24 (1H, t), 7.20 (2H, t ), 7.02 (1H, d), 6.81 (1H, t), 6.63 (2H, d), 6.33 (1H, d), 1.85 (6H, s) 052 δ=8.55 (1H, d), 8.45 (1H, d), 8.09 (1H, d), 8.08 (1H, d), 7.98 (1H, d), 7.87 (1H, d), 7.73 (1H, d) , 7.62-7.38 (10H, m), 7.28-7.24 (3H, m), 7.07 (1H, t), 6.86 (1H, d), 6.75 (1H, s), 6.58 (1H, d), 6.39 (1H , d), 1.85 (6H, s), 1.72 (6H, s) 058 δ=8.55 (1H, d), 8.09 (1H, d), 8.08 (1H, d), 7.89 (1H, d), 7.66 (1H, d), 7.61 (1H, d), 7.55 (2H, t) , 7.44-7.20 (8H, m), 7.07 (2H, t), 6.81 (1H, t), 6.63 (2H, d), 6.39 (2H, d), 1.85 (6H, s) 062 δ=8.55 (1H, d), 8.08 (1H, d), 7.89 (1H, d), 7.66 (1H, d), 7.55-7.32 (17H, m), 6.99 (1H, d), 6.97 (1H, d), 6.89 (1H, s), 6.88 (1H, d), 6.69 (2H, d), 6.64 (1H, d), 6.59 (1H, d), 1.85 (6H, s) 073 δ=8.55 (1H, d), 8.45 (1H, d), 8.08 (1H, d), 7.98 (1H, d), 7.89 (1H, d), 7.73 (1H, d), 7.66 (1H, d) , 7.55 (2H, t), 7.52 (1H, t), 7.50 (1H, t), 7.40-7.32 (3H, m), 7.20 (2H, t), 6.99 (1H, d), 6.97 (1H, d ), 6.86 (1H, d), 6.81 (1H, t), 6.64 (1H, d), 6.63 (2H, d), 1.85 (6H, s) 084 δ=8.55 (1H, d), 8.08 (1H, d), 7.89 (1H, d), 7.66 (1H, d), 7.55-7.26 (17H, m), 7.16 (1H, t), 7.08 (2H, d), 6.87 (1H, t), 6.69 (3H, d), 6.44 (1H, d), 1.85 (6H, s) 088 δ=8.55 (1H, d), 8.08 (1H, d), 7.89-7.74 (5H, m), 7.66 (1H, d), 7.55-7.26 (16H, m), 6.69 (2H, d), 6.44 ( 1H, d), 1.85 (6H, s) 113 δ=8.55 (1H, d), 8.45 (1H, d), 8.08 (1H, d), 7.98 (1H, d), 7.89 (1H, d), 7.84 (1H, d), 7.73 (1H, d) , 7.66 (1H, d), 7.55 (2H, t), 7.52 (1H, t), 7.50 (1H, t), 7.40 (1H, s), 7.38 (1H, t), 7.32 (1H, t), 7.20 (2H, t), 6.86-6.81 (3H, m), 6.64-6.63 (3H, m), 1.85 (6H, s) 119 δ=8.55 (1H, d), 8.08 (1H, d), 8.89 (2H, d), 8.84 (1H, d), 7.66-7.65 (3H, m), 7.55 (2H, t), 7.41 (1H, d), 7.38 (2H, t), 7.32 (2H, t), 7.20 (2H, t), 6.81 (2H, m), 6.64-6.63 (3H, m), 6.39 (1H, d), 1.85 (6H , s) 122 δ=8.55 (1H, d), 8.08 (1H, d), 7.89 (1H, d), 7.66 (1H, d), 7.55-7.32 (18H, m), 7.19 (1H, t), 6.98 (1H, s), 6.88 (1H, d), 6.69 (2H, d), 6.59 (1H, d), 6.44 (1H, d), 1.85 (6H, s) 135 δ=8.55 (1H, d), 8.45 (1H, d), 8.08 (1H, d), 7.98 (1H, d), 7.89 (1H, d), 7.66 (1H, d), 7.55-7.19 (12H, m), 6.88 (1H, d), 6.81 (1H, t), 6.63 (2H, d), 6.44 (1H, d), 1.85 (6H, s) 141 δ=8.55 (1H, d), 8.08 (1H, d), 7.79 (2H, d), 7.69 (1H, d), 7.65 (1H, s), 7.57-7.41 (21H, m), 7.30 (1H, t), 6.69 (4H, d), 6.39 (1H, d), 1.85 (6H, s) 155 δ=8.55 (1H, d), 8.28 (1H, s), 8.08 (1H, d), 7.87 (1H, d), 7.67-7.38 (14H, m), 7.28 (1H, t), 7.20 (2H, t), 6.81 (1H, t), 6.75 (1H, s), 6.63 (2H, d), 6.58 (1H, d), 6.39 (1H, d), 1.85 (6H, s), 1.72 (6H, s ) 167 δ=8.55 (1H, d), 8.45 (1H, d), 8.15 (1H, d), 8.08 (1H, d), 7.98 (1H, d), 7.83 (1H, s), 7.73 (1H, d) , 7.69 (1H, d), 7.65 (1H, s), 7.55-7.40 (11H, m), 7.20 (2H, t), 6.86 (1H, d), 6.81 (1H, t), 6.63 (2H, d ), 6.39 (1H, d), 1.85 (6H, s) 173 δ=8.55 (1H, d), 8.08 (1H, d), 8.05 (1H, d), 7.65 (1H, s), 7.55-7.41 (23H, m), 6.89 (1H, s), 6.88 (1H, d), 6.69 (2H, d), 6.59 (1H, d), 6.39 (1H, d), 1.85 (6H, s) 185 δ=8.55 (1H, d), 8.08 (1H, d), 7.87 (1H, d), 7.79 (2H, d), 7.69-7.51 (9H, m), 7.43-7.20 (7H, m), 6.81 ( 1H, t), 6.75 (1H, s), 6.63 (2H, d), 6.58 (1H, d), 6.33 (1H, d), 1.85 (6H, s), 1.72 (6H, s) 191 δ=8.55 (1H, d), 8.28 (1H, s), 8.08 (1H, d), 7.67 (1H, d), 7.64 (1H, d), 7.55-7.41 (23H, m), 6.69 (4H, d), 6.33 (1H, d), 1.85 (6H, s) 210 δ=8.93 (2H, d), 8.55 (1H, d), 8.15 (1H, d), 8.12 (2H, d), 8.08 (1H, d), 7.93-7.82 (6H, m), 7.69 (1H, d), 7.64 (1H, d), 7.55-7.43 (10H, m), 7.20 (2H, t), 6.81 (1H, t), 6.69 (2H, d), 6.63 (2H, d), 6.33 (1H , d), 1.85 (6H, s) 212 δ=8.55 (1H, d), 8.08 (1H, d), 8.05 (1H, d), 7.64 (1H, d), 7.55-7.43 (21H, m), 7.16 (1H, t), 7.08 (2H, d), 6.87 (1H, t), 6.69 (3H, d), 6.33 (1H, d), 1.85 (6H, s) 237 δ=8.55 (1H, d), 8.45 (1H, d), 7.73 (1H, s), 8.08 (1H, d), 7.98 (1H, d), 7.73 (1H, d), 7.67 (1H, d) , 7.55-7.41 (11H, m), 7.25 (1H, d), 7.20 (2H, t), 7.07 (1H, t), 6.86 (1H, d), 6.81 (1H, t), 6.63 (2H, d ), 6.39 (1H, d), 1.85 (6H, s) 239 δ=8.55 (1H, d), 8.28 (1H, s), 8.08 (1H, d), 7.89 (1H, d), 7.67-7.64 (3H, m), 7.55-7.20 (14H, m), 7.07 ( 1H, t), 6.81 (1H, t), 6.63 (2H, d), 6.39 (1H, d), 6.33 (1H, d), 1.85 (6H, s) 248 δ=8.55 (1H, d), 8.45 (1H, d), 8.15 (1H, d), 8.08 (1H, d), 7.98 (1H, d), 7.83 (1H, s), 7.81 (1H, d) , 7.69 (1H, d), 7.55-7.40 (9H, m), 7.27-7.20 (4H, m), 7.07 (1H, t), 6.86 (1H, d), 6.81 (1H, t), 6.63 (2H , d), 6.39 (1H, d), 1.85 (6H, s) 255 δ=8.55 (1H, d), 8.08 (1H, d), 8.05 (1H, d), 7.87 (1H, d), 7.62-7.38 (12H, m), 7.28-7.20 (4H, m), 7.07 ( 1H, t), 6.81 (1H, t), 6.75 (1H, s), 6.63 (2H, d), 6.58 (1H, d), 6.39 (1H, d), 1.85 (6H, s), 1.72 (6H , s) 274 δ=8.55 (1H, d), 8.08 (1H, d), 7.81 (1H, d), 7.72-7.71 (2H, m), 7.55-7.41 (14H, m), 7.20 (2H, t), 6.99 ( 1H, d), 6.67 (1H, d), 6.81 (1H, t), 6.69-6.63 (5H, m), 1.85 (6H, s) 275 δ=8.55 (1H, d), 8.08 (1H, d), 7.87 (1H, d), 7.81 (1H, d), 7.72-7.71 (2H, m), 7.62-7.38 (10H, m), 7.28 ( 1H, t), 7.20 (2H, t), 6.99 (1H, d), 6.97 (1H, d), 6.81 (1H, t), 6.75 (1H, s), 6.64-6.58 (4H, m), 1.85 (6H, s), 1.72 (6H, s) 281 δ=8.55 (1H, d), 8.08 (1H, d), 7.95 (1H, d), 7.75 (1H, d), 7.64 (1H, s), 7.55-7.41 (21H, m), 6.99 (H, d), 6.97 (1H, d), 6.69 (4H, d), 6.64 (1H, d), 1.85 (6H, s) 287 δ=8.55 (1H, d), 8.45 (1H, d), 8.08 (1H, d), 7.98 (1H, d), 7.95 (1H, d), 7.75 (1H, d), 7.73 (1H, d) , 7.64 (1H, s), 7.55-7.40 (10H, m), 7.20 (2H, t), 6.99 (1H, d), 6.97 (1H, d), 6.86 (1H, d), 6.81 (1H, t ), 6.64 (1H, d), 6.63 (2H, d), 1.85 (6H, s) 303 δ=8.55 (1H, d), 8.08 (1H, d), 7.79 (2H, d), 7.75 (1H, d), 7.62-7.36 (21H, m), 7.26 (1H, s), 6.89 (1H, s), 6.88 (1H, d), 6.69 (2H, d), 6.59 (1H, d), 6.44 (1H, d), 1.85 (6H, s) 314 δ=8.55 (1H, d), 8.08 (1H, d), 7.81 (1H, d), 7.72 (1H, d), 7.71 (1H, s), 7.55-7.3.6 (15H, m), 7.26 ( 1H, s), 7.20 (2H, t), 6.81 (1H, t), 6.69 (2H, d), 6.63 (2H, d), 6.44 (1H, d), 1.85 (6H, s) 330 δ=8.93 (2H, d), 8.55 (1H, d), 8.12 (2H, d), 8.08 (1H, d), 7.95-7.75 (7H, m), 7.64 (1H, s), 7.55-7.36 ( 10H, m), 7.26 (1H, s), 7.20 (2H, t), 6.81 (1H, t), 6.69 (2H, d), 6.63 (2H, d), 6.44 (1H, d), 1.85 (6H , s) 332 δ=8.55 (1H, d), 8.08 (1H, d), 7.85 (1H, d), 7.81 (1H, d), 7.55-7.36 (20H, m), 7.26 (1H, s), 7.16 (1H, t), 7.08 (2H, d), 6.87 (1H, t), 6.69 (3H, d), 6.44 (1H, d), 1.85 (6H, s) 346 δ=8.55 (1H, d), 8.08 (1H, d), 7.88-7.74 (8H, m), 7.62-7.36 (17H, m), 6.81 (1H, s), 6.69 (2H, d), 6.64 ( 1H, d), 1.85 (6H, s) 354 δ=8.55 (1H, d), 8.08 (1H, d), 7.84 (1H, d), 7.81 (1H, d), 7.72 (1H, d), 7.71 (1H, s), 7.55-7.41 (14H, m), 7.20 (2H, t), 6.81 (2H, m), 6.69 (2H, d), 6.64 (1H, d), 6.63 (2H, d), 1.85 (6H, s) 363 δ=8.55 (1H, d), 8.08 (1H, d), 7.95 (1H, d), 7.84 (1H, d), 7.75 (1H, d), 7.64 (1H, s), 7.55-7.41 (20H, m), 6.89 (1H, s), 6.88 (1H, d), 6.81 (1H, s), 6.69 (2H, d), 6.64 (1H, d), 6.59 (1H, d), 1.85 (6H, s ) 374 δ=8.55 (1H, d), 8.08 (1H, d), 7.85 (1H, d), 7.84 (1H, d), 7.81 (1H, d), 7.55-7.38 (15H, m), 7.20 (2H, t), 6.81 (2H, m), 6.69 (2H, d), 6.64 (1H, d), 6.63 (2H, d), 1.85 (6H, s) 390 δ=8.93 (2H, d), 8.55 (1H, d), 8.12 (2H, d), 8.08 (1H, d), 7.93-7.75 (8H, m), 7.62-7.44 (10H, m), 7.20 ( 2H, t), 7.19 (1H, t), 6.81 (1H, t), 6.69 (2H, d), 6.63 (2H, d), 6.44 (1H, d), 1.85 (6H, s) 397 δ=8.55 (1H, d), 8.45 (1H, d), 8.08 (1H, d), 7.98 (1H, d), 7.81 (1H, d), 7.73-7.71 (3H, m), 7.55-7.40 ( 11H, m), 7.20 (2H, t), 7.19 (1H, t), 6.86 (1H, d), 6.81 (1H, t), 6.63 (2H, d), 6.44 (1H, d), 1.85 (6H , s) 410 δ=8.93 (2H, d), 8.55 (1H, d), 8.12 (2H, d), 8.08 (1H, d), 7.95-7.75 (7H, m), 7.64 (1H, s), 7.55-7.41 ( 10H, m), 7.20 (2H, t), 7.19 (1H, t), 6.81 (1H, t), 6.69 (2H, d), 6.63 (2H, d), 6.44 (1H, d), 1.85 (6H , s) 413 δ=8.55 (1H, d), 8.08 (1H, d), 7.85 (1H, d), 7.81 (1H, d), 7.55-7.38 (22H, m), 7.19 (1H, t), 6.89 (1H, s), 6.88 (1H, d), 6.69 (2H, d), 6.59 (1H, d), 6.44 (1H, d), 1.85 (6H, s) 433 δ=8.55 (2H, d), 8.42 (1H, d), 8.08 (2H, d), 8.04 (1H, d), 7.89 (1H, d), 7.69-7.55 (10H, m), 7.43 (2H, d), 7.38 (1H, t), 7.32 (1H, t), 7.30 (1H, t) 7.20 (2H, t), 6.81 (1H, t), 6.63 (2H, d), 6.33 (2H, d) , 1.85 (6H, s) 442 δ=8.55 (1H, d), 8.28 (1H, s), 8.08 (1H, d), 8.00 (2H, d), 7.92 (1H, d), 7.73-7.41 (17H, m), 7.20 (2H, t), 6.81 (1H, t), 6.69 (2H, d), 6.63 (2H, d), 6.33 (1H, d), 1.85 (6H, s) 450 δ=8.55 (1H, d), 8.45 (1H, d), 8.28 (1H, s), 8.08 (1H, d), 8.00 (2H, d), 7.98 (1H, d), 7.92 (1H, d) , 7.73-7.49 (12H, m), 7.41 (1H, d), 7.40 (1H, s), 7.20 (2H, t), 6.86 (1H, d), 6.81 (1H, t), 6.63 (2H, d ), 6.39 (1H, d), 1.85 (6H, s) 461 δ=8.55 (1H, d), 8.15 (1H, d), 8.08 (1H, d), 7.83 (1H, s), 7.69 (1H, d), 7.65 (1H, s), 7.55-7.41 (8H, m), 7.25 (4H, d), 7.20 (4H, t), 6.81 (2H, t), 6.63 (4H, d), 6.39 (1H, d), 1.85 (6H, s) 473 δ=8.55 (1H, d), 8.15 (1H, d), 8.08 (1H, d), 7.89 (1H, d), 7.83 (1H, s), 7.69-7.64 (4H, m), 7.55-7.20 ( 17H, m), 6.81 (1H, t), 6.63 (2H, d), 6.39 (1H, d), 6.63 (1H, d), 1.85 (6H, s) 485 δ=8.93 (2H, d), 8.55 (1H, d), 8.12 (2H, d), 8.08 (1H, d), 8.05 (1H, d), 7.93-7.82 (6H, m), 7.64-7.38 ( 9H, m), 7.28 (1H, t), 7.20 (2H, t), 6.81 (1H, t), 6.75 (1H, s), 6.58 (1H, d), 6.63 (2H, d), 6.33 (1H , d), 1.85 (6H, s), 1.72 (6H, s) 494 δ=8.93 (2H, d), 8.55 (1H, d), 8.12 (2H, d), 8.08 (1H, d), 8.05 (1H, d), 7.93-7.82 (6H, m), 7.66-7.64 ( 3H, m), 7.55-7.32 (8H, m), 7.20 (2H, t), 6.81 (1H, t), 6.63 (2H, d), 6.39 (1H, d), 6.33 (1H, d), 1.85 (6H, s) 510 δ=8.55 (1H, d), 8.45 (1H, d), 8.41 (1H, d), 8.20 (1H, d), 8.08 (1H, d), 7.98 (2H, d), 7.75 (1H, d) , 7.73 (1H, d), 7.62-7.36 (11H, m), 7.26 (1H, s), 7.20 (2H, t), 6.86 (1H, d), 6.81 (1H, t), 6.63 (2H, d ), 6.44 (1H, d), 1.85 (6H, s) 514 δ=8.55 (1H, d), 8.45 (1H, d), 8.41 (1H, d), 8.20 (1H, d), 8.08 (1H, d), 7.98 (1H, d), 7.89 (1H, d) , 7.75 (1H, d), 7.66-7.20 (16H, m), 6.81 (1H, t), 6.63 (2H, d), 6.44 (1H, d), 6.39 (1H, d), 1.85 (6H, s ) 526 δ=8.55 (1H, d), 8.08 (1H, d), 7.89-7.66 (11H, m), 7.55 (2H, t), 7.50 (1H, t), 7.49 (1H, d), 7.38-7.20 ( 8H, m), 6.81 (1H, t), 6.63 (2H, d), 6.44 (1H, d), 1.85 (6H, s) 532 δ=8.55 (1H, d), 8.08 (1H, d), 7.89-7.81 (5H, m), 7.72-7.66 (4H, m), 7.55 (2H, t), 7.45-7.19 (10H, m), 7.07 (1H, t), 6.81 (1H, t), 6.63 (2H, d), 6.44 (1H, d), 6.39 (1H, d), 1.85 (6H, s) 542 δ=9.15 (1H, s), 8.93 (2H, d), 8.55 (1H, d), 8.18 (1H, d), 8.12 (2H, d), 8.08 (1H, d), 8.08 (1H, d) , 7.95-7.75 (6H, m), 7.64 (1H, s), 7.55-7.36 (10H, m), 7.26 (1H, s), 7.20 (2H, t), 6.81 (1H, t), 6.63 (2H , d), 6.63 (2H, d), 6.44 (1H, d), 1.85 (6H, s) 562 δ=8.55 (1H, d), 8.08-7.81 (6H, m), 7.73 (1H, d), 7.59-7.38 (14H, m), 7.26 (1H, s), 7.20 (2H, t), 6.81 ( 1H, t), 6.69 (2H, d), 6.63 (2H, d), 6.44 (1H, d), 1.85 (6H, s) 584 δ=7.95 (1H, s), 7.80 (1H, s), 7.49 (1H, s), 7.19 (1H, s), 6.64 (1H, s), 1.85 (6H, s) 589 δ=8.55 (1H, d), 8.08 (1H, d), 7.81 (1H, d), 7.72 (1H, d), 7.71 (1H, s), 7.55-7.51 (6H, m), 7.41 (1H, t), 7.36 (1H, d), 7.26 (1H, d), 6.44 (1H, d), 1.85 (6H, s) [Table 4] compound FD-MS compound FD-MS 001 m/z=577.71 (C ₄₃ H ₃₁ NO=577.24) 281 m/z=729.90 (C ₅₅ H ₃₉ NO=729.30) 006 m/z=693.87 (C ₅₂ H ₃₉ NO=693.30) 287 m/z=683.86 (C ₄₉ H ₃₃ NOS=683.23) 016 m/z=607.76 (C ₄₃ H ₂₉ NOS=607.20) 303 m/z=729.90 (C ₅₅ H ₃₉ NO=729.30) 023 m/z=653.81 (C ₄₉ H ₃₅ NO=653.27) 314 m/z=653.81 (C ₄₉ H ₃₅ NO=653.27) 030 m/z=651.79 (C ₄₉ H ₃₃ NO=651.26) 330 m/z=753.93 (C ₅₇ H ₃₉ NO=753.30) 052 m/z=723.92 (C ₅₂ H ₃₇ NOS=723.26) 332 m/z=729.90 (C ₅₅ H ₃₉ NO=729.30) 058 m/z=591.70 (C ₄₃ H ₂₉ NO ₂ =591.22) 346 m/z=703.87 (C ₅₃ H ₃₇ NO=703.29) 062 m/z=653.81 (C ₄₉ H ₃₅ NO=653.27) 354 m/z=653.81 (C ₄₉ H ₃₅ NO=653.27) 073 m/z=607.76 (C ₄₃ H ₂₉ NOS=607.20) 363 m/z=729.90 (C ₅₅ H ₃₉ NO=729.30) 084 m/z=653.81 (C ₄₉ H ₃₅ NO=653.27) 374 m/z=653.81 (C ₄₉ H ₃₅ NO=653.27) 088 m/z=627.77 (C ₄₇ H ₃₃ NO=627.26) 390 m/z=753.93 (C ₅₇ H ₃₉ NO=753.30) 113 m/z=607.76 (C ₄₃ H ₂₉ NOS=607.20) 397 m/z=683.86 (C ₄₉ H ₃₃ NOS=683.23) 119 m/z=591.70 (C ₄₃ H ₂₉ NO ₂ =591.22) 410 m/z=753.93 (C ₅₇ H ₃₉ NO=753.30) 122 m/z=653.81 (C ₄₉ H ₃₅ NO=653.27) 413 m/z=729.90 (C ₅₅ H ₃₉ NO=729.30) 135 m/z=607.76 (C ₄₃ H ₂₉ NOS=607.20) 433 m/z=717.85 (C ₅₃ H ₃₅ NO ₂ =717.27) 141 m/z=729.90 (C ₅₅ H ₃₉ NO=729.30) 442 m/z=703.87 (C ₅₃ H ₃₇ NO=703.29) 155 m/z=693.87 (C ₅₂ H ₃₉ NO=693.30) 450 m/z=733.92 (C ₅₃ H ₃₅ NOS=733.24) 167 m/z=683.86 (C ₄₉ H ₃₃ NOS=683.23) 461 m/z=653.81 (C ₄₉ H ₃₅ NO=653.27) 173 m/z=729.90 (C ₅₅ H ₃₉ NO=729.30) 473 m/z=743.89 (C ₅₅ H ₃₇ NO ₂ =743.28) 185 m/z=693.87 (C ₅₂ H ₃₉ NO=693.30) 485 m/z=793.99 (C ₆₀ H ₄₃ NO=793.33) 191 m/z=729.90 (C ₅₅ H ₃₉ NO=729.30) 494 m/z=767.91 (C ₅₇ H ₃₇ NO ₂ =767.28) 210 m/z=753.93 (C ₅₇ H ₃₉ NO=753.30) 510 m/z=790.00 (C ₅₅ H ₃₅ NOS ₂ =789.22) 212 m/z=729.90 (C ₅₅ H ₃₉ NO=729.30) 514 m/z=773.94 (C ₅₅ H ₃₅ NO ₂ S=773.24) 237 m/z=683.86 (C ₄₉ H ₃₃ NOS=683.23) 526 m/z=717.85 (C ₅₃ H ₃₅ NO ₂ =717.27) 239 m/z=667.79 (C ₄₉ H ₃₃ NO ₂ =667.25) 532 m/z=757.87 (C ₅₅ H ₃₅ NO ₃ =757.26) 248 m/z=683.86 (C ₄₉ H ₃₃ NOS=683.23) 542 m/z=803.98 (C ₆₁ H ₄₁ NO=803.32) 255 m/z=693.87 (C ₅₂ H ₃₉ NO=693.30) 562 m/z=703.87 (C ₅₃ H ₃₇ NO=703.29) 274 m/z=653.81 (C ₄₉ H ₃₅ NO=653.27) 584 m/z=625.87 (C ₄₃ H ₁₁ D ₁₈ NOS=625.31) 275 m/z=693.87 (C ₅₂ H ₃₉ NO=693.30) 589 m/z=667.89 (C ₄₉ H ₂₁ D ₁₄ NO=667.36) < Experimental Example > Experimental Example 1 ( 1 ) Production of organic light-emitting element

Glass substrates coated with a 1,500 angstrom thick indium tin oxide (ITO) film were ultrasonically cleaned with distilled water. When cleaning with distilled water was completed, the substrate was ultrasonically cleaned with solvents such as acetone, methanol, and isopropyl alcohol, dried, and then subjected to UV in an ultraviolet (UV) cleaner. 5 minutes of ultraviolet ozone (UVO) treatment. After this, the substrate is transferred to a plasma cleaner (PT), then subjected to plasma treatment under vacuum to improve the ITO work function and remove residual films, and transferred to a thermal deposition device for organic deposition.

Subsequently, the chamber was evacuated until the vacuum in the chamber reached 10 ^-6 Torr, and then the 4,4',4''-tri[2 -Naphthyl(phenyl)amino]triphenylamine (4,4',4''-tris[2-naphthyl(phenyl)amino]triphenylamine, 2-TNATA) was evaporated to deposit on the ITO substrate with a Hole injection layer with a thickness of 600 Angstroms. The following N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (N,N'-bis( α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB), and NPB was evaporated by applying an electric current to the cell to deposit on the hole injection layer a layer having a Angstrom-thick hole transport layer.

After the hole injection layer and the hole transport layer are formed as above, the light-emitting layer is thermally vacuum deposited on the hole injection layer and the hole transport layer as follows. As the light-emitting layer, 9-[4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]-9'-phenyl-3,3'-bis-9H - A compound of carbazole was deposited to 400 Angstroms as a host, and Ir(ppy) ₃ was doped and deposited in an amount of 7% as a green phosphorescent dopant. After that, bathocuproine (BCP) was deposited to 60 angstroms as the hole blocking layer, and E1 was deposited to 300 angstroms on the hole blocking layer as the electron transport layer.

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

At the same time, for each material used to manufacture organic light-emitting elements, all organic compounds required to manufacture organic light-emitting elements were subjected to vacuum sublimation purification at 10 ^-8 Torr to 10 ^-6 Torr.

The driving voltage and luminous efficiency of the organic light-emitting element according to Experimental Example 1 were as follows, except that the compounds listed in Table 5 below were used instead of the compound NPB used when forming the hole transport layer in Experimental Example 1.

Here, the compounds of Comparative Examples 2 to 4 other than NPB are as follows. ( 2 ) Driving voltage and luminous efficiency of organic light-emitting elements

For each of the organic light-emitting elements manufactured as above, the electroluminescence (EL) properties were measured using M7000 manufactured by McScience Inc., and using the measurement results, The life measurement system (M6000) measured the life T ₉₅ (unit: h, hours) when the standard brightness is 20,000 candelas/square meter (cd/m ² ), that is, the brightness becomes 95 relative to the initial brightness % of the time spent.

The results of measuring the driving voltage, luminous efficiency and lifetime of the organic light-emitting device manufactured according to the present disclosure are shown in Table 5 below. [table 5] compound Drive voltage (volts) Luminous efficiency (candela/area) Lifespan (T ₉₅ ) Example 1 001 4.32 122.78 132 Example 2 006 4.35 119.54 126 Example 3 016 4.37 120.04 138 Example 4 023 4.20 121.30 132 Example 5 030 4.13 115.51 127 Example 6 052 4.15 115.07 134 Example 7 058 4.27 113.09 131 Example 8 062 4.57 119.91 136 Example 9 073 4.52 121.15 137 Example 10 084 4.18 118.53 141 Example 11 088 4.04 116.78 133 Example 12 113 4.26 120.17 132 Example 13 119 4.29 122.18 127 Example 14 122 4.31 118.56 135 Example 15 135 4.39 120.34 128 Example 16 141 4.35 118.77 136 Example 17 155 4.28 118.92 128 Example 18 167 4.17 120.10 130 Example 19 173 4.23 121.30 140 Example 20 185 4.20 117.74 132 Example 21 191 4.23 119.59 134 Example 22 210 4.31 117.67 130 Example 23 212 4.35 120.38 137 Example 24 237 4.24 121.17 142 Example 25 239 4.13 119.19 131 Example 26 248 4.30 118.00 128 Example 27 255 4.32 121.37 137 Example 28 274 4.60 122.25 133 Example 29 275 4.58 119.39 132 Example 30 281 4.63 118.82 124 Example 31 287 4.51 119.66 132 Example 32 303 4.26 120.16 139 Example 33 314 4.22 119.05 132 Example 34 330 4.36 118.74 131 Example 35 332 4.31 118.32 134 Example 36 346 4.30 120.55 137 Example 37 354 4.12 119.71 135 Example 38 363 4.24 121.68 139 Example 39 374 4.18 119.08 132 Example 40 390 4.22 120.33 140 Example 41 397 4.13 118.70 135 Example 42 410 4.27 119.36 134 Example 43 413 4.17 120.62 137 Example 44 433 4.27 118.92 128 Example 45 442 4.25 119.71 132 Example 46 450 4.36 118.98 129 Example 47 461 4.26 119.96 131 Example 48 473 4.21 120.28 135 Example 49 485 4.32 118.37 132 Example 50 494 4.35 117.24 134 Example 51 510 4.30 117.77 135 Example 52 514 4.24 119.31 137 Example 53 526 4.36 120.29 140 Example 54 532 4.21 121.10 137 Example 55 542 4.17 121.04 134 Example 56 552 4.22 117.99 129 Example 57 584 4.27 119.88 175 Example 58 589 4.25 119.14 166 Comparative example 1 NPB 5.46 87.16 96 Comparative example 2 M1 5.03 102.05 105 Comparative example 3 M2 5.24 97.48 104 Comparative example 4 M3 5.05 99.54 101

As can be seen from the results in Table 5, compared to organic light-emitting devices using the compounds of Comparative Examples 1 to 4 as hole transport layer materials, the compound represented by Chemical Formula 1 of the present disclosure is used as the hole transport layer. The organic light-emitting devices of the materials (Examples 1 to 58) have lower driving voltage and significantly improved luminous efficiency and lifetime.

The compounds M1 to M3 used in Comparative Examples 2 to 4 are similar to the compound of Chemical Formula 1 of the present disclosure in that the compound has a dimethylfluorenobenzofuran-type five-membered ring skeleton (dimethylfluorenobenzofuran-type five-ring skeleton), however, the difference is that in the compounds of M1 and M3, the arylamine substituent is introduced to the 4th position of dimethylfluorenobenzofuran, while in the compound of the present disclosure, the arylamine substituent is The amine substituent is not introduced into the 4th position of dimethylfluorenebenzofuran. Compared with other positions, the introduction of an arylamine group into the 4th position of dimethylfluorenebenzofuran has the disadvantage of reducing the electron hole mobility. It was identified that the compound of the present disclosure has an arylamine group introduced to other positions than the No. 4 position of the mother nucleus, and as the hole mobility properties become excellent, the device properties become excellent.

The compound of M2 used in Comparative Example 3 is similar to the compound of Chemical Formula 1 of the present disclosure in that the compound has a dimethylfluorenobenzofuran type five-membered ring skeleton, but has an arylamine group disubstitution Structure (disubstituted structure). When there is a disubstituted structure with a diarylamine group in the dimethylfluorene benzofuran type skeleton structure, the HOMO energy level is increased. Compared with the compound of M2 used in Comparative Example 3, the compound of Chemical Formula 1 of the present disclosure has a lower HOMO energy level due to having a single arylamine substituent. As the HOMO energy level decreases, the difference in HOMO energy level between the hole transport layer and the light-emitting layer decreases, thereby further promoting hole transport, and therefore, the discerned device properties become excellent. < Experimental Example 2> ( 1 ) Production of organic light-emitting element

The transparent electrode ITO film obtained from the glass used for OLED (manufactured by Samsung Corning Advanced Glass) was ultrasonically cleaned using trichlorethylene, acetone, ethanol and distilled water for 5 minutes each, and then The transparent electrode ITO film was stored in isopropyl alcohol before use. Then, the ITO substrate was mounted in the substrate folder of the vacuum deposition apparatus, and the following 4,4',4''-tri(N,N-(2- Naphthyl)-phenylamino)triphenylamine (4,4',4''-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine, 2-TNATA).

Subsequently, the chamber was evacuated until the vacuum in the chamber reached 10 ^-6 Torr, and 2-TNATA was then evaporated by applying current to the cell to deposit on the ITO substrate a structure with Hole injection layer with a thickness of 600 Angstroms. The following N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) was introduced into another cell in the vacuum deposition device, and by The cell evaporated the NPB by applying an electric current to deposit a hole transport layer having a thickness of 1000 Angstroms on the hole injection layer.

After forming the hole injection layer and the hole transport layer as above, a compound of the following structural formula M1 with a thickness of 100 angstroms was deposited on the hole injection layer and the hole transport layer as an electron blocking layer.

A blue light-emitting material having the following structure was deposited on the electron blocking layer as a light-emitting layer. Specifically, a compound of H1 as a blue luminescent host material was vacuum deposited to a thickness of 300 angstroms on one unit cell in a vacuum deposition device, and the compound of H1 was added in an amount of 5% relative to the host material. A compound of D1 as a blue light-emitting dopant material is doped and deposited on.

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

Finally, lithium fluoride (LiF) with a thickness of 10 angstroms was deposited on the electron transport layer as an electron injection layer, and then an aluminum (Al) negative electrode with a thickness of 1,000 angstroms was deposited on the electron injection layer. negative electrode, and as a result, an organic light-emitting element was manufactured.

At the same time, for each material used to manufacture organic light-emitting elements, all organic compounds required to manufacture organic light-emitting elements were subjected to vacuum sublimation purification at 10 ^-8 Torr to 10 ^-6 Torr.

The driving voltage and luminous efficiency of the organic light-emitting element according to Experimental Example 2 were as follows, except that the compounds listed in Table 6 below were used instead of the compound M1 used when forming the electron blocking layer in Experimental Example 2.

Here, the compounds of Comparative Examples 5 to 7 other than NPB are as follows. ( 2 ) Driving voltage and luminous efficiency of organic light-emitting elements

For each of the organic light-emitting elements manufactured as above, the electroluminescence (EL) properties were measured using M7000 manufactured by Micro Scientific Corporation, and the measurement results were used by a lifetime measurement system manufactured by Micro Scientific Corporation (M6000) measured the life T ₉₅ (unit: h, hours) when the standard brightness is 20,000 candelas/square meter, that is, the time it takes for the brightness to become 95% relative to the initial brightness.

The results of measuring the driving voltage, luminous efficiency and lifetime of the organic light-emitting element manufactured according to the present disclosure are shown in Table 6 below. [Table 6] compound Drive voltage (volts) Luminous efficiency (candela/area) Lifespan (T ₉₅ ) Example 59 016 5.31 6.92 72 Example 60 123 5.42 7.27 69 Example 61 058 5.26 6.99 79 Example 62 062 5.58 7.19 75 Example 63 073 5.50 6.98 76 Example 64 088 5.25 7.12 80 Example 65 113 5.30 7.04 71 Example 66 122 5.35 6.84 73 Example 67 155 5.37 6.78 74 Example 68 167 5.38 6.90 69 Example 69 185 5.32 6.97 78 Example 70 191 5.29 6.76 68 Example 71 210 5.22 7.21 81 Example 72 212 5.27 6.88 74 Example 73 237 5.19 6.86 75 Example 74 255 5.31 6.96 72 Example 75 275 5.56 6.80 76 Example 76 281 5.62 6.94 79 Example 77 314 5.33 7.14 68 Example 78 332 5.38 6.61 82 Example 79 346 5.21 7.20 74 Example 80 374 5.31 7.12 79 Example 81 390 5.26 6.87 69 Example 82 410 5.18 6.78 75 Example 83 442 5.23 6.97 72 Example 84 473 5.27 7.09 67 Example 85 494 5.30 6.80 71 Example 86 514 5.29 6.89 76 Example 87 562 5.24 7.14 70 Example 88 584 5.32 7.09 107 Example 89 589 5.34 7.12 97 Comparative example 5 M1 5.92 5.89 48 Comparative example 6 M2 5.98 6.17 52 Comparative example 7 M3 6.04 5.79 46 Comparative example 8 NPB 6.20 5.98 49

As can be seen from the results in Table 6, compared with Comparative Examples 5 to 8, which are organic light-emitting devices using compounds of M1 to M3 and NPB as electron blocking layer materials, as compared to Comparative Examples 5 to 8 using the compound of Chemical Formula 1 of the present disclosure. Examples 59 to 89 of organic light-emitting devices in which the compounds represented as electron blocking layer materials have lower driving voltages and significantly improved luminous efficiency and lifetime.

100:Substrate 200: Positive electrode 300: Organic material layer 301: Hole injection layer 302: Hole transport layer 303: Luminous layer 304: Hole blocking layer 305:Electron transport layer 306:Electron injection layer 400: Negative electrode

1 to 3 are diagrams each schematically showing a stacked structure of an organic light-emitting element according to one embodiment of the present disclosure.

100:Substrate

200: Positive electrode

300: Organic material layer

400: Negative electrode

Claims (12)

A heterocyclic compound represented by the following Chemical Formula 1: [Chemical Formula 1] In Chemical Formula 1, R1 to R12 are the same as or different from each other, and each is 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)R101R102 ;-SiR101R102R103; and a group represented by the following Chemical Formula 2, or two or more groups adjacent to each other are bonded to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring or a substituted or unsubstituted Substituted C2 to C60 heterocycle, and R101, R102 and R103 are the same or different from each other, and each is independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group ; Or a substituted or unsubstituted C2 to C60 heteroaryl group; At least one of R2 to R12 is the group represented by the following Chemical Formula 2; and R13 and R14 are -CRaRbRc, and Ra to Rc are the same as each other Or different, and each is 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; and substituted or unsubstituted C2 to C60 heterocycloalkyl, [Chemical Formula 2] In Chemical Formula 2, L1 and L2 are the same as or different from each other, and each is independently a single bond; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group ; Ar1 and Ar2 are the same or different from each other, and are each independently a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group; m and n are the same as or different from each other, and are each independently an integer of 0 to 3; and * represents a bonding site to the heterocyclic compound of Chemical Formula 1. The heterocyclic compound of claim 1, wherein at least one of R2 to R8 is the group represented by the following Chemical Formula 2: [Chemical Formula 2] Chemical formula 2 is the same as defined in claim 1. The heterocyclic compound of claim 1, wherein R1 is 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. The heterocyclic compound of claim 1, wherein Ar1 and Ar2 are the same or different from each other, and each is independently a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heterocyclic compound. Aryl, however, excludes the case where Ar1 or Ar2 is 9,9-diphenylfluorenyl. The heterocyclic compound of claim 1, wherein the heterocyclic compound represented by Chemical Formula 1 does not contain deuterium as a substituent, or the heterocyclic compound represented by Chemical Formula 1 is less than the total number of hydrogen atoms and deuterium atoms. The cyclic compounds have a deuterium content of 1% to 100%. The heterocyclic compound as claimed in claim 1, wherein the heterocyclic compound represented by Chemical Formula 1 is any one selected from the group consisting of the following compounds: . An organic light-emitting element including: first electrode; a second electrode disposed opposite the first electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein one or more of the organic material layers comprise the heterocyclic compound according to any one of claims 1 to 6. The organic light-emitting element according to claim 7, wherein the organic material layer includes a light-emitting layer, and the light-emitting layer contains the heterocyclic compound. The organic light-emitting element according to claim 7, wherein the organic material layer includes a light-emitting layer, the light-emitting layer includes a host material, and the host material includes the heterocyclic compound. The organic light-emitting element according to claim 7, wherein the organic material layer includes a hole transport layer or a hole transport auxiliary layer, and the hole transport layer or the hole transport auxiliary layer contains the heterocyclic compound . The organic light-emitting element according to claim 7, wherein the organic material layer includes an electron blocking layer, and the electron blocking layer includes the heterocyclic compound. The organic light-emitting element as claimed in claim 7, further comprising a layer selected from the group consisting of a light-emitting layer, a hole injection layer, a hole transport layer, a hole transport auxiliary layer, an electron injection layer, an electron transport layer, an electron blocking layer and a hole blocking layer. One layer, two layers, or more layers of a group.

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