TW202323498A - Heterocyclic compound, organic light emitting device comprising same, and composition for organic material layer of organic light emitting device - Google Patents

Abstract

The present specification relates to a heterocyclic compound represented by Chemical Formula 1, an organic light emitting device comprising the same, and a composition for an organic material layer of the organic light emitting device.

Description

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

This application claims priority based on Korean Patent Application No. 10-2021-0122791 filed with the Korea Intellectual Property Office on September 14, 2021, the entire contents of which are incorporated as part of this specification into this case.

The disclosure relates to a heterocyclic compound, an organic light-emitting element including the heterocyclic compound, and a composition of an organic material layer of the organic light-emitting element.

The organic light-emitting element is a self-emissive display element, and has the advantages of not only having a wide viewing angle and excellent contrast, but also having a fast response speed.

An organic light emitting element has a structure in which an organic thin film is provided between two electrodes. When a voltage is applied to the organic light emitting element having such a structure, electrons and holes injected from the two electrodes combine to form pairs in the organic thin film, and then emit light when the electrons and holes disappear. The organic thin film may consist of a single layer or a multilayer as required.

The material of the organic thin film may have a light emitting function as required. For example, as a material of the organic thin film, a compound capable of forming a light-emitting layer by itself, or a compound capable of functioning as a host or a dopant of a light-emitting layer based on a host-dopant may be used. In addition, compounds capable of performing functions such as hole injection, hole transport, electron blocking, hole blocking, electron transport, electron injection, and the like can also be used as materials for organic thin films.

In order to improve the efficacy, lifetime or efficiency of organic light-emitting devices, there is a continuous need to develop organic thin film materials. Prior Technical Documents patent documents (Patent Document 1) US Patent No. 4,356,429

[technical problem]

The purpose of the present disclosure is to provide a composition of a heterocyclic compound, an organic light-emitting device including the same, and an organic material layer of the organic light-emitting device. [Technical solution]

在化學式1中， R1至R12彼此相同或不同，且各自獨立地選自由以下組成的群組：氫；氘；鹵素；氰基；經取代或未經取代的C1至C60烷基；經取代或未經取代的C2至C60烯基；經取代或未經取代的C2至C60炔基；經取代或未經取代的C1至C60烷氧基；經取代或未經取代的C3至C60環烷基；經取代或未經取代的C2至C60雜環烷基；經取代或未經取代的C6至C60芳基；以及經取代或未經取代的C2至C60雜芳基，且R1至R12中的至少一者為氘， X1、X2及X3彼此相同或不同，且各自獨立地為NAr1、O、S或CR13R14，且X1、X2及X3中的至少一者為NAr1， Ar1為由以下化學式1-1表示的基團， [化學式1-1]

在化學式1-1中， L1與L2彼此相同或不同，且各自獨立地為單鍵；經取代或未經取代的C6至C60伸芳基；或者經取代或未經取代的C2至C60伸雜芳基， Ar2與Ar3彼此相同或不同，且各自獨立地選自由以下組成的群組：氫；氘；鹵素；氰基；經取代或未經取代的C1至C60烷基；經取代或未經取代的C2至C60烯基；經取代或未經取代的C2至C60炔基；經取代或未經取代的C1至C60烷氧基；經取代或未經取代的C3至C60環烷基；經取代或未經取代的C2至C60雜環烷基；經取代或未經取代的C6至C60芳基；以及經取代或未經取代的C2至C60雜芳基， a與b彼此相同或不同，且各自獨立地為0至3的整數，且 R13與R14彼此相同或不同，且各自獨立地選自由以下組成的群組：氫；氘；鹵素；氰基；經取代或未經取代的C1至C60烷基；經取代或未經取代的C2至C60烯基；經取代或未經取代的C2至C60炔基；經取代或未經取代的C1至C60烷氧基；經取代或未經取代的C3至C60環烷基；經取代或未經取代的C2至C60雜環烷基；經取代或未經取代的C6至C60芳基；以及經取代或未經取代的C2至C60雜芳基。 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 or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C60 alkyl; substituted or Unsubstituted C2 to C60 alkenyl; substituted or unsubstituted C2 to C60 alkynyl; substituted or unsubstituted C1 to C60 alkoxy; substituted or unsubstituted C3 to C60 cycloalkyl ; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; and substituted or unsubstituted C2 to C60 heteroaryl, and in R1 to R12 At least one is deuterium, X1, X2 and X3 are the same or different from each other, and each independently is NAr1, O, S or CR13R14, and at least one of X1, X2 and X3 is NAr1, and Ar1 is represented by the following chemical formula 1- The group represented by 1, [chemical formula 1-1]

In Chemical Formula 1-1, L1 and L2 are the same or different from each other, and each is independently a single bond; a substituted or unsubstituted C6 to C60 aryl; or a substituted or unsubstituted C2 to C60 hetero Aryl, Ar2 and Ar3 are the same or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted Substituted 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, a and b are the same or different from each other, And each independently is an integer of 0 to 3, and R13 and R14 are the same or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C2 to C60 alkenyl; substituted or unsubstituted C2 to C60 alkynyl; substituted or unsubstituted C1 to C60 alkoxy; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; and substituted or unsubstituted C2 to C60 heteroaryl .

In addition, the present disclosure provides an organic light-emitting device, the organic light-emitting device includes: a first electrode; a second electrode disposed to face the first electrode; and one or more organic material layers disposed between the first electrode and the second electrode. Between the two electrodes, one or more layers of the organic material layer includes the heterocyclic compound represented by the above Chemical Formula 1.

在化學式2中， R21至R34彼此相同或不同，且各自獨立地選自由以下組成的群組：氫；氘；鹵素；氰基；經取代或未經取代的C1至C60烷基；經取代或未經取代的C2至C60烯基；經取代或未經取代的C2至C60炔基；經取代或未經取代的C1至C60烷氧基；經取代或未經取代的C3至C60環烷基；經取代或未經取代的C2至C60雜環烷基；經取代或未經取代的C6至C60芳基；以及經取代或未經取代的C2至C60雜芳基， L3與L4彼此相同或不同，且各自獨立地為單鍵；經取代或未經取代的C6至C60伸芳基；或者經取代或未經取代的C2至C60伸雜芳基， Ar11與Ar12彼此相同或不同，且各自獨立地選自由以下組成的群組：氫；氘；鹵素；氰基；經取代或未經取代的C1至C60烷基；經取代或未經取代的C2至C60烯基；經取代或未經取代的C2至C60炔基；經取代或未經取代的C1至C60烷氧基；經取代或未經取代的C3至C60環烷基；經取代或未經取代的C2至C60雜環烷基；經取代或未經取代的C6至C60芳基；經取代或未經取代的C2至C60雜芳基；-P(=O)R101R102；以及–SiR101R102R103，且R101、R102及R103彼此相同或不同，且各自獨立地為經取代或未經取代的C1至C60烷基；經取代或未經取代的C6至C60芳基；或者經取代或未經取代的C2至C60雜芳基，且 m與n彼此相同或不同，且各自獨立地為0至3的整數。 In addition, the present disclosure provides an organic light-emitting device, wherein the organic material layer further includes a heterocyclic compound represented by the following chemical formula 2: [chemical formula 2]

In Chemical Formula 2, R21 to R34 are the same or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C60 alkyl; substituted or Unsubstituted C2 to C60 alkenyl; substituted or unsubstituted C2 to C60 alkynyl; substituted or unsubstituted C1 to C60 alkoxy; substituted or unsubstituted C3 to C60 cycloalkyl ; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; and substituted or unsubstituted C2 to C60 heteroaryl, L3 and L4 are identical to each other or Different, and each independently is a single bond; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl, Ar11 and Ar12 are the same or different from each other, and each independently selected from the group consisting of: hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C2 to C60 alkenyl; substituted or unsubstituted Substituted 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; and -SiR101R102R103, and R101, R102 and R103 are the same or different , and are each independently substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl, and m and n are the same or different from each other, and each independently represents an integer of 0 to 3.

In addition, the present disclosure provides a composition of an organic material layer of an organic light-emitting device, the composition including the heterocyclic compound represented by the above Chemical Formula 1 and the heterocyclic compound represented by the above Chemical Formula 2. [beneficial effect]

The heterocyclic compound according to one embodiment may be used as a material of an organic material layer of an organic light emitting element. The compound can be used as hole injection layer material, electron blocking layer material, hole transport layer material, light emitting layer material, electron transport layer material, hole blocking layer material, electron injection layer material and similar materials in organic light emitting elements . Specifically, the compound can be used as a light-emitting layer material of an organic light-emitting element.

Specifically, the heterocyclic compound can be used alone or mixed with a P-type host as a light-emitting material, and can be used as a host material or a dopant material of a light-emitting layer. When the compound represented by the above Chemical Formula 1 is used in the organic material layer, it may reduce the driving voltage of the organic light emitting element, improve luminous efficiency, and improve lifetime properties.

More specifically, when the heterocyclic compound according to one embodiment is used as a light-emitting layer, it can enhance hole transport properties and electron transport properties by adjusting band gap and triplet energy level ) (T ₁ energy level) value to improve the hole transport ability, reduce the driving voltage of the organic light-emitting device and improve the light efficiency by improving the stability of the molecule, and improve the thermal stability of the compound by improving Lifetime Properties of Organic Light Emitting Elements.

Hereinafter, 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 becomes another substituent, and the substituted position is not limited as long as it is a position where a hydrogen atom is substituted ( That is, the position where the substituent can be substituted) is sufficient, 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 deuterium, halogen, cyano, C1 to C60 straight or branched chain alkyl, C2 to C60 straight or branched chain alkenyl, C2 to C60 straight chain or branched chain 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 alkylamine, C6 to C60 monocyclic or polycyclic arylamine and C2 to C60 monocyclic or one or more substituents of the group consisting of polycyclic heteroarylamine groups may be substituted or unsubstituted, or substituted by a substituent that connects two or more substituents selected from the substituents shown above, or Not replaced.

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

In the present specification, the alkyl group may include straight or branched chains having 1 to 60 carbon atoms, and may be further substituted with 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, second-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, third octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl propyl-propyl, 1,1-dimethyl-propyl, isohexyl, 4-methylhexyl, 5-methylhexyl and the like, but not limited thereto.

In the present specification, the alkenyl group may include straight or branched chains having 2 to 60 carbon atoms, and may be further substituted with other substituents. The number of carbon atoms of the alkenyl group may be 2 to 60, specifically 2 to 40, and more specifically 2 to 20. Specific examples of alkenyl 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-phenylethenyl-1-yl, 2-phenylethenyl-1 -yl, 2,2-diphenylethenyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)ethenyl-1-yl, 2,2-bis(diphenyl-1 -yl) vinyl-1-yl, stilbenyl (stilbenyl group), styryl and the like, but not limited thereto.

In the present specification, the alkynyl group may include straight or branched chains having 2 to 60 carbon atoms, and may be further substituted with other substituents. The number of carbon atoms of the alkynyl group may be 2 to 60, specifically 2 to 40, and more specifically 2 to 20.

In this specification, an alkoxy group may be a linear, branched or cyclic chain. The number of carbon atoms in the alkoxy group is not particularly limited, but is preferably 1-20. Specific examples of alkoxy 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 not limited thereto.

In the present specification, the cycloalkyl group may include a monocyclic or polycyclic ring having 3 to 60 carbon atoms, and may be further substituted with other substituents. Herein, a polycyclic ring refers to a group in which a cycloalkyl group is directly linked or condensed with other cyclic groups. Herein, the other cyclic group may be a cycloalkyl group, but may also be a different type of cyclic group, such as a heterocycloalkyl group, an aryl group, a heteroaryl group, and the like. The number of carbon atoms of the cycloalkyl group may be 3 to 60, specifically 3 to 40, and more specifically 5 to 20. Specific examples of cycloalkyl 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 Not limited to this.

In the present specification, the heterocycloalkyl group may contain O, S, Se, N or Si as a heteroatom, may include a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may be further substituted with other substituents. Herein, a polycyclic ring refers to a group in which a heterocycloalkyl group is directly linked or condensed with other cyclic groups. Herein, the other cyclic group may be a heterocycloalkyl group, but may also be a different type of cyclic group, such as cycloalkyl, aryl, heteroaryl and the like. 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 the present specification, the aryl group may include a monocyclic or polycyclic ring having 6 to 60 carbon atoms, and may be further substituted with other substituents. Herein, polycyclic means a group in which an aryl group is directly linked or condensed with other cyclic groups. Herein, the other cyclic group may be an aryl group, but may also be a different type of cyclic group, such as cycloalkyl, heterocycloalkyl, heteroaryl and the like. Aryl includes spirocyclyl. The number of carbon atoms of the aryl group may be 6 to 60, specifically 6 to 40, and more specifically 6 to 25. Specific examples of aryl may include phenyl, biphenyl, triphenyl, naphthyl, anthracenyl, phenanthryl, phenanthrenyl, perylenyl, fluoranthracenyl, biterphenylenyl, phenanthryl, pyrenyl, fused Tetraphenyl, fused pentaphenyl, fluorenyl, indenyl, acenaphthyl, benzofluorenyl, spirobifluorenyl, 2,3-dihydro-1H-indenyl, their ring-condensing groups and similar groups, But not limited to this.

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

、

、

、

、

、

或類似基團，但不限於此。 When fluorenyl is substituted, the substituted fluorenyl can become

,

,

,

,

,

or similar groups, but not limited thereto.

In the present specification, the heteroaryl group may contain S, O, Se, N or Si as a heteroatom, may include a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may be further substituted with other substituents. Herein, polycyclic refers to a group in which a heteroaryl group is directly linked or condensed with other cyclic groups. Herein, other cyclic groups may be heteroaryl groups, but may also be different types of cyclic groups, such as cycloalkyl, heterocycloalkyl, aryl and the like. The number of carbon atoms of the heteroaryl group may be 2 to 60, specifically 2 to 40, and more specifically 3 to 25. Specific examples of heteroaryl may include pyridyl, pyrrolyl, pyrimidinyl, pyridazinyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, Triazolyl, furanyl, oxadiazolyl, thiadiazolyl, bithiazolyl, tetrazolyl, pyryl, thiopyranyl, diazinyl, oxazinyl, thiazinyl, dioxinyl ( dioxinyl group), triazine, tetrazine, quinolinyl, isoquinolinyl, quinazolinyl group, isoquinazolinyl, quinozolilyl group, naphthyridinyl, acridine Pyridyl, phenanthridinyl (phenanthridinyl group), imidazopyridyl, naphthyl, triazindenyl, indolyl, indolizyl, benzothiazolyl, benzoxazolyl, benzo Imidazolyl, benzothienyl, benzofuryl, dibenzothienyl, dibenzofuryl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenazinyl, dibenzosilyl Heterocyclopentadienyl (dibenzosilole group), spirobis (dibenzosilyl) base, dihydrophenanthazinyl, phenanthoxazinyl, phenanthridyl group (phenanthridyl group), thienyl, indyl Indolo[2,3-a]carbazolyl, Indolo[2,3-b]carbazolyl, Indolinyl, 10,11-dihydro-dibenzo[b,f]nitrogen 9,10-dihydroacridinyl, phenthiazinyl, phenothiazinyl group, phthalazinyl, naphthyridinyl, phenanthrolinyl, benzo[c][1,2,5] Thiadiazolyl, 5,10-dihydrodibenzo[b,e][1,4]azasilinyl, pyrazolo[1,5-c]quinazolinyl, pyrido[1, 2-b]indazolyl, pyrido[1,2-a]imidazo[1,2-e]indolinyl, 5,11-dihydroindeno[1,2-b]carbazolyl and similar groups, but not limited thereto.

In this specification, the amine group can be selected from the group consisting of: monoalkylamine group; monoarylamine group; monoheteroarylamine group; -NH ₂ ; ; diheteroarylamine group; alkylarylamine group; alkylheteroarylamine group; 30. Specific examples of the amine group may include methylamine, dimethylamine, ethylamine, diethylamine, phenylamine, naphthylamine, biphenylamine, biphenylamine Base, anthracenylamine, 9-methyl-anthrylamine, diphenylamine, phenylnaphthylamine, xylylamine, phenylcresylamine, triphenylamine, biphenyl Phenylnaphthylamino, phenylbiphenylylamino, biphenylfluorenylamino, phenylbisphenylylamino, biphenylbiphenylylamino and similar groups, but not limited to this.

In this specification, the aryl group means a group having two bonding positions in the aryl group, that is, a divalent group. Except that each of these groups is a divalent group, the description of the aryl group above applies. In addition, the heteroaryl group means a group having two bonding positions in the heteroaryl group, that is, a divalent group. Except that each of these groups is a divalent group, the above description of heteroaryl applies.

In this specification, an "adjacent" group may mean a substituent that is substituted on an atom that is directly attached to the atom to which the corresponding substituent is substituted, a substituent that is spatially closest to the corresponding substituent, or a substituent that is at the corresponding Substituent Another substituent that is substituted on the atom being substituted. 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 construed as being "adjacent" to each other.

In the present disclosure, "the case 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 ( ² H) is an isotope of hydrogen, some hydrogen atoms may be deuterium.

In one embodiment of the present disclosure, "the case where no substituent is specified in the chemical formula or compound structure" may mean that the positions that can be used as substituents are all hydrogen or deuterium. In other words, since deuterium is an isotope of hydrogen, some hydrogen atoms may be deuterium as an isotope, and the deuterium content may be 0% to 100% at this time.

In one embodiment of the present disclosure, in "the situation 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 "The substituents are all hydrogen"), hydrogen and deuterium can be mixed and used in the compound.

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

In one embodiment of the present disclosure, isotopes refer to 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 may have is defined as T1, and the number of specific substituents among these substituents is defined as T2, the content of the specific substituent T% The meaning of can be defined as T2/T1×100=T%.

表示的苯基中具有20%的氘含量可意指苯基可具有的取代基的總數是5（方程式中的T1）且所述取代基之中氘的數目是1（方程式中的T2）的情形。換言之，在苯基中具有20%的氘含量可由以下結構式表示。

In other words, in one instance, after the

A deuterium content of 20% in the indicated phenyl group may mean that the total number of substituents that the phenyl group may have is 5 (T1 in the equation) and the number of deuterium in said substituents is 1 (T2 in the equation) situation. 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 with 0% deuterium content" may mean a phenyl group without deuterium atoms, ie, a phenyl group with 5 hydrogen atoms.

In the present disclosure, a C6 to C60 aromatic hydrocarbon ring means a compound including an aromatic ring composed of C6 to C60 carbons and hydrogen. Examples of the C6 to C60 aromatic hydrocarbon ring may include phenyl, biphenyl, terphenyl, biterphenyl, naphthalene, anthracene, anthracene, phenanthrene, fluorene, pyrene, perylene, perylene, azulene and similar compounds, but not It is limited thereto, and includes all aromatic hydrocarbon ring compounds known in the art that satisfy the above-mentioned number of carbon atoms.

在化學式1中， R1至R12彼此相同或不同，且各自獨立地選自由以下組成的群組：氫；氘；鹵素；氰基；經取代或未經取代的C1至C60烷基；經取代或未經取代的C2至C60烯基；經取代或未經取代的C2至C60炔基；經取代或未經取代的C1至C60烷氧基；經取代或未經取代的C3至C60環烷基；經取代或未經取代的C2至C60雜環烷基；經取代或未經取代的C6至C60芳基；以及經取代或未經取代的C2至C60雜芳基，且R1至R12中的至少一者為氘， X1、X2及X3彼此相同或不同，且各自獨立地為NAr1、O、S或CR13R14，且X1、X2及X3中的至少一者為NAr1， Ar1為由以下化學式1-1表示的基團， [化學式1-1]

在化學式1-1中， L1與L2彼此相同或不同，且各自獨立地為單鍵；經取代或未經取代的C6至C60伸芳基；或者經取代或未經取代的C2至C60伸雜芳基， Ar2與Ar3彼此相同或不同，且各自獨立地選自由以下組成的群組：氫；氘；鹵素；氰基；經取代或未經取代的C1至C60烷基；經取代或未經取代的C2至C60烯基；經取代或未經取代的C2至C60炔基；經取代或未經取代的C1至C60烷氧基；經取代或未經取代的C3至C60環烷基；經取代或未經取代的C2至C60雜環烷基；經取代或未經取代的C6至C60芳基；以及經取代或未經取代的C2至C60雜芳基， a與b彼此相同或不同，且各自獨立地為0至3的整數，且 R13與R14彼此相同或不同，且各自獨立地選自由以下組成的群組：氫；氘；鹵素；氰基；經取代或未經取代的C1至C60烷基；經取代或未經取代的C2至C60烯基；經取代或未經取代的C2至C60炔基；經取代或未經取代的C1至C60烷氧基；經取代或未經取代的C3至C60環烷基；經取代或未經取代的C2至C60雜環烷基；經取代或未經取代的C6至C60芳基；以及經取代或未經取代的C2至C60雜芳基。 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 or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C60 alkyl; substituted or Unsubstituted C2 to C60 alkenyl; substituted or unsubstituted C2 to C60 alkynyl; substituted or unsubstituted C1 to C60 alkoxy; substituted or unsubstituted C3 to C60 cycloalkyl ; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; and substituted or unsubstituted C2 to C60 heteroaryl, and in R1 to R12 At least one is deuterium, X1, X2 and X3 are the same or different from each other, and each independently is NAr1, O, S or CR13R14, and at least one of X1, X2 and X3 is NAr1, and Ar1 is represented by the following chemical formula 1- The group represented by 1, [chemical formula 1-1]

In Chemical Formula 1-1, L1 and L2 are the same or different from each other, and each is independently a single bond; a substituted or unsubstituted C6 to C60 aryl; or a substituted or unsubstituted C2 to C60 hetero Aryl, Ar2 and Ar3 are the same or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted Substituted 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, a and b are the same or different from each other, And each independently is an integer of 0 to 3, and R13 and R14 are the same or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C2 to C60 alkenyl; substituted or unsubstituted C2 to C60 alkynyl; substituted or unsubstituted C1 to C60 alkoxy; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; and substituted or unsubstituted C2 to C60 heteroaryl .

In an embodiment of the present disclosure, X1 may be NAr1, and X2 and X3 may be the same or different from each other, and each independently is O, S or CR13R14.

In another embodiment of the present disclosure, X2 can be NAr1, and X1 and X3 can be the same or different from each other, and each independently is O, S or CR13R14.

In another embodiment of the present disclosure, X3 may be NAr1, and X1 and X2 may be the same or different from each other, and each independently is O, S or CR13R14.

在化學式1-a中， X3是O、S或CR13R14，且 R1至R14及Ar1如以上化學式1及化學式1-1中所定義， [化學式1-b]

在化學式1-b中， X3是O、S或CR13R14，且 R1至R14及Ar1如以上化學式1及以上化學式1-1中所定義， [化學式1-c]

在化學式1-c中， X3是O、S或CR13R14，且 R1至R14及Ar1如以上化學式1及以上化學式1-1中所定義， [化學式1-d]

在化學式1-d中， X3是O、S或CR13R14，且 R1至R14及Ar1如以上化學式1及以上化學式1-1中所定義， [化學式1-e]

在化學式1-e中， X3是O、S或CR13R14，且 R1至R14及Ar1如以上化學式1及以上化學式1-1中所定義， [化學式1-f]

在化學式1-f中， X3是O、S或CR13R14，且 R1至R14及Ar1如以上化學式1及以上化學式1-1中所定義。 In one embodiment of the present disclosure, the heterocyclic compound represented by Chemical Formula 1 may be any one of the following Chemical Formula 1-a to Chemical Formula 1-f, but not limited to these examples: [Chemical Formula 1-a]

In Chemical Formula 1-a, X3 is O, S or CR13R14, and R1 to R14 and Ar1 are as defined above in Chemical Formula 1 and Chemical Formula 1-1, [Chemical Formula 1-b]

In Chemical Formula 1-b, X3 is O, S or CR13R14, and R1 to R14 and Ar1 are as defined in the above Chemical Formula 1 and the above Chemical Formula 1-1, [Chemical Formula 1-c]

In Chemical Formula 1-c, X3 is O, S or CR13R14, and R1 to R14 and Ar1 are as defined in the above Chemical Formula 1 and the above Chemical Formula 1-1, [Chemical Formula 1-d]

In Chemical Formula 1-d, X3 is O, S or CR13R14, and R1 to R14 and Ar1 are as defined in the above Chemical Formula 1 and the above Chemical Formula 1-1, [Chemical Formula 1-e]

In Chemical Formula 1-e, X3 is O, S or CR13R14, and R1 to R14 and Ar1 are as defined in the above Chemical Formula 1 and the above Chemical Formula 1-1, [Chemical Formula 1-f]

In Chemical Formula 1-f, X3 is O, S or CR13R14, and R1 to R14 and Ar1 are as defined in the above Chemical Formula 1 and the above Chemical Formula 1-1.

In one embodiment of the present disclosure, R1 to R12 may be the same or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C30 alkane 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, and At least one of R1 to R12 may be deuterium,

In another embodiment of the present disclosure, R1 to R12 may be the same or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to 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, And at least one of R1 to R12 can be deuterium,

In another embodiment of the present disclosure, R1 to R12 may be hydrogen or deuterium, and at least one of R1 to R12 may be deuterium.

In another embodiment of the present disclosure, R1 to R12 may be deuterium.

In one embodiment of the present disclosure, L1 and L2 in Chemical Formula 1-1 may be the same or different from each other, and each independently is a single bond; a substituted or unsubstituted C6 to C30 aryl group; or a substituted or An unsubstituted C2 to C30 heteroaryl group, and a and b may be the same or different from each other, and each independently may be an integer of 0 to 3.

In another embodiment of the present disclosure, L1 and L2 in Chemical Formula 1-1 may be the same or different from each other, and each is independently a single bond; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or an unsubstituted C2 to C20 heteroaryl group, and a and b may be the same or different from each other, and may each independently be an integer of 0 to 3.

、

、

。 In another embodiment of the present disclosure, L1 and L2 in Chemical Formula 1-1 may be the same or different from each other, and may each independently be the following structures, but are not limited to these examples:

,

,

.

In one embodiment of the present disclosure, Ar2 and Ar3 in Chemical Formula 1-1 may be the same or different from each other, and may each be independently substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl.

In another embodiment of the present disclosure, Ar2 and Ar3 in Chemical Formula 1-1 may be the same or different from each other, and may each be independently substituted or unsubstituted C6 to C30 aryl; or substituted or unsubstituted Substituted C2 to C30 heteroaryl.

In another embodiment of the present disclosure, Ar2 and Ar3 in Chemical Formula 1-1 may be the same or different from each other, and may each be independently substituted or unsubstituted C6 to C20 aryl; or substituted or unsubstituted Substituted C2 to C20 heteroaryl.

、

、

、

、

、

、

、

。 In another embodiment of the present disclosure, Ar2 and Ar3 in Chemical Formula 1-1 may be the same or different from each other, and may each independently have the following structures, but are not limited to these examples:

,

,

,

,

,

,

,

.

In one embodiment of the present disclosure, R13 and R14 may be the same or different from each other, and may 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, R13 and R14 may be the same or different from each other, and may 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; and substituted or unsubstituted C1 to C10 alkoxy.

In another embodiment of the present disclosure, R13 and R14 may be the same or different from each other, and may be each independently methyl, ethyl, propyl or similar groups.

In one embodiment of the present disclosure, the heterocyclic compound represented by the above Chemical Formula 1 may not contain deuterium as a substituent, or the content of deuterium may be 1% to 100% based on the sum of hydrogen atoms and deuterium atoms.

In another embodiment of the present disclosure, the heterocyclic compound represented by the above Chemical Formula 1 may not contain deuterium as a substituent, or the content of deuterium may be 5% to 100% based on the sum of hydrogen atoms and deuterium atoms.

In another embodiment of the present disclosure, the heterocyclic compound represented by the above Chemical Formula 1 may not contain deuterium as a substituent, or the content of deuterium may be 10% to 100% based on the sum of hydrogen atoms and deuterium atoms.

In another embodiment of the present disclosure, the heterocyclic compound represented by the above Chemical Formula 1 may not contain deuterium as a substituent, or the deuterium content may be 20% to 100% based on the sum of hydrogen atoms and deuterium atoms.

For example, the heterocyclic compound represented by the above Chemical Formula 1 may not contain deuterium as a substituent, or the deuterium content may be more than 0%, may be 5% or more, 10% or more based on the total number of hydrogen atoms and deuterium atoms Greater than 10%, 15% or greater, 20% or greater, 25% or greater, 30% or greater, 35% or greater, 40% or greater, 45% or greater 45% or 50% or more than 50%, and can be 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 than 75%, 70% or less, 65% or less, or 60% or less.

In one embodiment of the present disclosure, the heterocyclic compound represented by the above Chemical Formula 1 may not contain deuterium as a substituent, or the deuterium content of _R1 to _R12 may be 1% to 100% based on the total number of hydrogen atoms and deuterium atoms %.

In another embodiment of the present disclosure, the heterocyclic compound represented by the above chemical formula 1 may not contain deuterium as a substituent, or the deuterium content of R ₁ to R ₁₂ may be 5% to 5% based on the total number of hydrogen atoms and deuterium atoms. 95%.

In another embodiment of the present disclosure, the heterocyclic compound represented by the above Chemical Formula 1 may not contain deuterium as a substituent, or the deuterium content of R ₁ to R ₁₂ may be 10% to 10% based on the total number of hydrogen atoms and deuterium atoms. 90%.

For example, the heterocyclic compound represented by the above Chemical Formula 1 may not contain deuterium as a substituent, or the deuterium content of _R1 to _R12 may be greater than 0%, may be 5% or greater, based on the total number of hydrogen atoms and deuterium atoms 5%, 10% or more than 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, or 50% or more, and may be 100% or less, 95% or less, 90% or less, 85% or less, 80% or Less than 80%, 75% or less, 70% or less, 65% or less, or 60% or less.

In one embodiment of the present disclosure, Ar2 and Ar3 in the above Chemical Formula 1-1 may be deuterium-substituted C6-C30 aryl or deuterium-substituted C2-C30 heteroaryl. In this case, the deuterium content may be 1% to 100% based on the sum of hydrogen atoms and deuterium atoms.

In another embodiment of the present disclosure, Ar2 and Ar3 in the above Chemical Formula 1-1 may be deuterium-substituted C6-C30 aryl or deuterium-substituted C2-C30 heteroaryl. In this case, the deuterium content may be 5% to 95% based on the sum of hydrogen atoms and deuterium atoms.

In another embodiment of the present disclosure, Ar2 and Ar3 in the above Chemical Formula 1-1 may be deuterium-substituted C6-C30 aryl or deuterium-substituted C2-C30 heteroaryl. In this case, the deuterium content may be 10% to 90% based on the sum of hydrogen atoms and deuterium atoms.

For example, when Ar2 and Ar3 in the above chemical formula 1-1 can be a C6 to C30 aryl group substituted by deuterium or a C2 to C30 heteroaryl group substituted by deuterium, based on the total number of hydrogen atoms and deuterium atoms, the substitution The deuterium content of the group can be 0% or greater, 5% or greater, 10% or greater, 15% or greater, 20% or greater, 25% or greater, 30% or greater than 30%, 35% or greater, 40% or greater, 45% or greater, or 50% or greater, and may be 100% or less, 95% or less, 90% or less, 85% or less, 85% or less, 80% or less, 75% or less, 70% or less, 65% or less, 65% or less, or 60% or less.

。 In one embodiment of the present disclosure, the heterocyclic compound represented by the above 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 the above Chemical Formula 1, compounds having unique properties of the introduced substituents can be synthesized. For example, by using hole injection layer materials, hole transport layer materials, electron blocking layer materials, light emitting layer materials, electron transport layer materials, hole blocking layer materials mainly used during the manufacture of organic light emitting elements And the substituents of the material of the electron injection layer are introduced into the core structure, and materials satisfying the conditions required in each organic material layer can be synthesized.

In addition, various substituents are introduced into the structure of the above Chemical Formula 1, so that the energy band gap can be finely controlled, so that the properties in the interface between organic materials can be improved, and the use of the material can be diversified.

In addition, the present disclosure provides an organic light-emitting device, the organic light-emitting device includes: a first electrode; a second electrode disposed to face the first electrode; and one or more organic material layers disposed between the first electrode and the second electrode. Between the two electrodes, one or more of the organic material layers includes the 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 device may be a red organic light emitting device, and the heterocyclic compound represented by the above Chemical Formula 1 may be used as a material of the red organic light emitting device.

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

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

Specific details of the heterocyclic compound represented by the above Chemical Formula 1 are the same as those described above.

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

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

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

Specific details of the heterocyclic compound represented by the above Chemical Formula 1 are the same as those described above.

In addition to using the aforementioned heterocyclic compounds to form one or more organic material layers, the organic light emitting device according to the present disclosure can be manufactured by conventional methods and materials used for manufacturing organic light emitting devices.

When manufacturing an organic light-emitting device, the heterocyclic compound can form an organic material layer by a solution coating method and a vacuum deposition method. Herein, the solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spray method, Roll coating or the like, but not limited thereto.

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

In an embodiment of the present disclosure, the organic light-emitting device may further include a layer 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 or more layers, and the one or more layers may include the heterocyclic compound.

In one embodiment of the present disclosure, the organic light emitting device 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 the heterocyclic compound represented by the above 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.

在化學式2中， R21至R34彼此相同或不同，且各自獨立地選自由以下組成的群組：氫；氘；鹵素；氰基；經取代或未經取代的C1至C60烷基；經取代或未經取代的C2至C60烯基；經取代或未經取代的C2至C60炔基；經取代或未經取代的C1至C60烷氧基；經取代或未經取代的C3至C60環烷基；經取代或未經取代的C2至C60雜環烷基；經取代或未經取代的C6至C60芳基；以及經取代或未經取代的C2至C60雜芳基， L3與L4彼此相同或不同，且各自獨立地為單鍵；經取代或未經取代的C6至C60伸芳基；或者經取代或未經取代的C2至C60伸雜芳基， Ar11與Ar12彼此相同或不同，且各自獨立地選自由以下組成的群組：氫；氘；鹵素；氰基；經取代或未經取代的C1至C60烷基；經取代或未經取代的C2至C60烯基；經取代或未經取代的C2至C60炔基；經取代或未經取代的C1至C60烷氧基；經取代或未經取代的C3至C60環烷基；經取代或未經取代的C2至C60雜環烷基；經取代或未經取代的C6至C60芳基；經取代或未經取代的C2至C60雜芳基；-P(=O)R101R102；以及–SiR101R102R103，且R101、R102及R103彼此相同或不同，且各自獨立地為經取代或未經取代的C1至C60烷基；經取代或未經取代的C6至C60芳基；或者經取代或未經取代的C2至C60雜芳基，且 m與n彼此相同或不同，且各自獨立地為0至3的整數。 In one embodiment of the present disclosure, the organic light-emitting device may include a heterocyclic compound represented by the above Chemical Formula 1, and may further include a heterocyclic compound represented by the following Chemical Formula 2: [Chemical Formula 2]

In Chemical Formula 2, R21 to R34 are the same or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C60 alkyl; substituted or Unsubstituted C2 to C60 alkenyl; substituted or unsubstituted C2 to C60 alkynyl; substituted or unsubstituted C1 to C60 alkoxy; substituted or unsubstituted C3 to C60 cycloalkyl ; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; and substituted or unsubstituted C2 to C60 heteroaryl, L3 and L4 are identical to each other or Different, and each independently is a single bond; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl, Ar11 and Ar12 are the same or different from each other, and each independently selected from the group consisting of: hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C2 to C60 alkenyl; substituted or unsubstituted Substituted 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; and -SiR101R102R103, and R101, R102 and R103 are the same or different , and are each independently substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl, and m and n are the same or different from each other, and each independently represents an integer of 0 to 3.

In another embodiment of the present disclosure, R ₂₁ to R ₃₄ in Chemical Formula 2 may be the same or different from each other, and may 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; and substituted or unsubstituted C1 to C30 alkoxy .

In another embodiment of the present disclosure, R ₂₁ to R ₃₄ in Chemical Formula 2 may be the same or different from each other, and may 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; and substituted or unsubstituted C1 to C10 alkoxy .

In another embodiment of the present disclosure, R ₂₁ to R ₃₄ in Chemical Formula 2 may be the same or different from each other, and may be each independently selected from the group consisting of hydrogen; deuterium; halogen; and cyano.

In another embodiment of the present disclosure, R ₂₁ to R ₃₄ in Chemical Formula 2 may be the same or different from each other, and may each independently be hydrogen or deuterium.

In another embodiment of the present disclosure, L3 and L4 in Chemical Formula 2 may be the same or different from each other, and each independently may be a single bond; a substituted or unsubstituted C6 to C30 aryl; or a substituted or An unsubstituted C2 to C30 heteroaryl group, and m and n may be the same or different from each other, and each independently may be an integer of 0 to 3.

In another embodiment of the present disclosure, L3 and L4 in Chemical Formula 2 may be the same or different from each other, and each independently may be a single bond; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or An unsubstituted C2 to C20 heteroaryl group, and m and n may be the same or different from each other, and may each independently be an integer of 0 to 3.

In another embodiment of the present disclosure, Ar11 and Ar12 in Chemical Formula 2 may be the same or different from each other, and may be independently selected from the group consisting of hydrogen; deuterium; halogen; cyano; substituted or unsubstituted Substituted 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; and -SiR101R102R103, and R101, R102 and R103 may be the same or different from each other, and may each be independently substituted or unsubstituted C1 to C30 alkyl; substituted or unsubstituted C6 to C30 aryl; or substituted or unsubstituted C2 to C30 heteroaryl.

In another embodiment of the present disclosure, Ar ₁₁ and Ar ₁₂ in Chemical Formula 2 may be the same or different from each other, and may each be independently selected from the group consisting of hydrogen; deuterium; halogen; cyano; substituted or Unsubstituted C6 to C20 aryl; substituted or unsubstituted C2 to C20 heteroaryl; -P(=O)R101R102; and -SiR101R102R103, and R101, R102 and R103 may be the same or different from each other, and may Each is independently a substituted or unsubstituted C6 to C10 aryl group; or a substituted or unsubstituted C2 to C10 heteroaryl group.

In an embodiment of the present disclosure, the heterocyclic compound represented by the above Chemical Formula 2 may not contain deuterium as a substituent, or the deuterium content may be 0% to 100% based on the total number of hydrogen atoms and deuterium atoms.

In another embodiment of the present disclosure, the heterocyclic compound represented by the above chemical formula 2 may not contain deuterium as a substituent, or the deuterium content may be 10% to 100% based on the total of hydrogen atoms and deuterium atoms.

In another embodiment of the present disclosure, the heterocyclic compound represented by the above chemical formula 2 may not contain deuterium as a substituent, or the deuterium content may be 20% to 90% based on the total number of hydrogen atoms and deuterium atoms.

In another embodiment of the present disclosure, the heterocyclic compound represented by the above chemical formula 2 may not contain deuterium as a substituent, or the deuterium content may be 30% to 80% based on the total of hydrogen atoms and deuterium atoms.

For example, the heterocyclic compound represented by the above Chemical Formula 2 may not contain deuterium as a substituent, or the deuterium content may be more than 0%, may be 10% or more, 20% or more based on the total number of hydrogen atoms and deuterium atoms Greater than 20%, 30% or greater, 40% or greater than 40%, or 50% or greater than 50%, and may be 100% or less, 90% or less, 80% or less, 70% % or less than 70% or 60% or less than 60%.

。 In one embodiment of the present disclosure, the heterocyclic compound represented by the above Chemical Formula 2 may be any one selected from the group consisting of the following compounds:

.

When manufacturing the organic light emitting device according to the present disclosure, it may include the heterocyclic compound represented by the above Chemical Formula 1 and the heterocyclic compound represented by the above Chemical Formula 2.

When the organic light-emitting element according to the present disclosure is manufactured, when the heterocyclic compound represented by the above Chemical Formula 1 and the heterocyclic compound represented by the above Chemical Formula 2 are mixed and contained, the excellent driving voltage, luminous efficiency, and life. From this, it can be expected that when the two heterocyclic compounds are mixed and contained at the same time, an exciplex phenomenon will occur.

The excited complex phenomenon is the emission of the donor (donor) (p-subject) highest occupied molecular orbital (highest occupied molecular orbital, HOMO) energy level and the acceptor (acceptor) (n -Main) The phenomenon of the energy difference between the lowest unoccupied molecular orbital (LUMO) energy levels. When excitation complexes occur between two molecules, reverse intersystem crossing (RISC) occurs, and thus, the internal quantum efficiency of fluorescence can be increased to 100%. When a donor (p-host) with good hole transport capability and an acceptor (n-host) with good electron transport capability are used as the host of the light-emitting layer, since holes are injected into the p-host and electrons Implanted into the n-body, so the driving voltage can be reduced, thereby helping to improve lifetime. That is, when the compound represented by the above Chemical Formula 1 is used as an acceptor and the compound represented by the above Chemical Formula 2 is used as a donor, excellent properties of the organic light emitting element are exhibited.

In one embodiment of the present disclosure, when the organic light-emitting element includes a mixture of a heterocyclic compound represented by the above Chemical Formula 1 and a heterocyclic compound represented by the above Chemical Formula 2, at least one of the heterocyclic compounds may have more than 0% and a deuterium content of 100% or less.

In another embodiment of the present disclosure, when the organic light-emitting element includes a mixture of a heterocyclic compound represented by the above Chemical Formula 1 and a heterocyclic compound represented by the above Chemical Formula 2, at least one of the heterocyclic compounds may have a value of 10 % to 100% deuterium content.

In another embodiment of the present disclosure, when the organic light-emitting element includes a mixture of a heterocyclic compound represented by the above Chemical Formula 1 and a heterocyclic compound represented by the above Chemical Formula 2, at least one of the heterocyclic compounds may have 15 % to 95% deuterium content.

In another embodiment of the present disclosure, when the organic light-emitting element includes a mixture of a heterocyclic compound represented by the above Chemical Formula 1 and a heterocyclic compound represented by the above Chemical Formula 2, at least one of the heterocyclic compounds may have a value of 20 % to 80% deuterium content.

For example, when the organic light-emitting element includes a mixture of a heterocyclic compound represented by the above Chemical Formula 1 and a heterocyclic compound represented by the above Chemical Formula 2, at least one of the heterocyclic compounds may have 0% or more, 5% or more, 10% or more than 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 greater than 40%, 45% or greater than 45%, or 50% or greater than 50% deuterium content, and may be 100% or less, 95% or less, 90% or less, 85% or Less than 85%, 80% or less, 75% or less, 70% or less, 65% or less, or 60% or less.

In addition, an embodiment of the present disclosure provides a composition of an organic material layer of an organic light-emitting device, the composition including the heterocyclic compound represented by the above Chemical Formula 1 and the heterocyclic compound represented by the above Chemical Formula 2.

Specific details of the heterocyclic compound represented by the above Chemical Formula 1 and the heterocyclic compound represented by the above Chemical Formula 2 are the same as those described above.

In an embodiment of the present disclosure, in the composition of the organic material layer of the organic light-emitting device, the heterocyclic compound represented by the above chemical formula 1 and the heterocyclic compound represented by the above chemical formula 2 may have a ratio of 1:10 to 10 :1, 1:8 to 8:1, 1:6 to 6:1, 1:4 to 4:1, 1:3 to 3:1 or 1:2 to 2:1 weight ratios, but not limited to .

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

In one embodiment of the present disclosure, the organic material layer may include the heterocyclic compound represented by the above Chemical Formula 1 and the heterocyclic compound represented by the above Chemical Formula 2, and may be used together with a phosphorescent dopant.

As a material for the phosphorescent dopant, 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 can be used, but the scope of the present disclosure is not limited to these instance.

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

L can be an anionic bidentate ligand coordinated to M through sp2 carbon and heteroatoms, and X can play the role of trapping electrons or holes. Non-limiting examples of L, L' and L'' include 2-(1-naphthyl)benzoxazole, 2-phenylbenzoxazole, 2-phenylbenzothiazole, 7,8-benzo Quinoline, phenylpyridine, benzothienylpyridine, 3-methoxy-2-phenylpyridine, thienylpyridine, tolylpyridine, and similar materials. Non-limiting examples of X' and X'' include acetylacetonate (acac), hexafluoroacetylacetonate, salicylidene, picolinate, 8-hydroxyquinolinic acid Salt and similar materials.

。 Specific examples of phosphorescent dopants are shown below, but are not limited to these examples.

.

In one embodiment of the present disclosure, the organic material layer may include the heterocyclic compound represented by the above Chemical Formula 1 and the heterocyclic compound represented by the above Chemical Formula 2, and may be used together with an iridium-based dopant.

In one embodiment of the present disclosure, Ir(ppy) _{3 ,} which is a green phosphorescent dopant, can be used as an iridium-based dopant.

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

In the organic light emitting element according to one embodiment of the present disclosure, the organic material layer may include 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 the above Chemical Formula 1 .

In an organic light emitting element according to another embodiment of the present disclosure, the organic material layer may include an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer may include Heterocyclic compounds.

In the organic light emitting device according to another embodiment of the present disclosure, the organic material layer may include 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 A heterocyclic compound represented by the above Chemical Formula 1 may be included.

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

In an organic light emitting device according to 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 represented by Chemical Formula 1 above.

An organic light-emitting device according to an embodiment of the present disclosure may further include one or more materials 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.

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

According to FIG. 1 , 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 is shown. However, it 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 may also be implemented.

FIG. 3 illustrates a case where the organic material layer is a multilayer. The organic light emitting device 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 to such a laminated structure, and if necessary, layers other than the light emitting layer may be omitted, and other necessary functional layers may be further added.

In one embodiment of the present disclosure, a method for manufacturing an organic light-emitting element is provided, the method including the following steps: preparing a substrate; forming a first electrode on the substrate; forming one or more organic materials on the first electrode layer; and forming a second electrode on the organic material layer, wherein the step of forming the organic material layer includes the step of forming one or more organic material layers using the organic material layer composition according to an embodiment of the present disclosure.

In one embodiment of the present disclosure, the step of forming the organic material layer may be to premix the heterocyclic compound represented by the above Chemical Formula 1 with the heterocyclic compound represented by the above Chemical Formula 2, and form the organic material layer using a thermal vacuum deposition method.

Premixing refers to mixing the premixed material in the source after premixing the materials, and mixing the premixed material before depositing the heterocyclic compound represented by the above Chemical Formula 1 and the heterocyclic compound represented by the above Chemical Formula 2 on the organic material layer. Mixed materials are put into one source.

According to one embodiment of the present application, the premixed material may be referred to as an organic material layer composition.

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

The organic material layer including both the heterocyclic compound represented by the above Chemical Formula 1 and the heterocyclic compound represented by the above Chemical Formula 2 may further contain 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 the above Chemical Formula 1 or the heterocyclic compound represented by the above Chemical Formula 2 are exemplified below, but these are only for illustration, and It is not intended to limit the scope of the application, and materials known in the art may be substituted.

As the positive electrode material, a material having a relatively large work function may be used, and a transparent conductive oxide, metal, 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); ZnO: Al or SnO ₂ : combination of metal (such as Sb) and oxide; conductive polymer (conductive polymer), such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy)thiophene] (poly[3,4-(ethylene-1,2-dioxy)thiophene], PEDOT), polypyrrole, and polyaniline; and similar materials, but not limited thereto.

As the negative electrode material, a material having a relatively low work function can be used, and a metal, a metal oxide, a 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, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer materials such as LiF/Al or LiO ₂ /Al; and similar materials, but not limited thereto.

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

As the hole transport layer material, pyrazoline derivatives, arylamine-based derivatives, stilbene derivatives, triphenyldiamine derivatives, and the like can be used, and low-molecular-weight or high-molecular-weight materials can also be used.

As materials for the electron transport layer, oxadiazole derivatives, anthraquinone dimethane and its derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, tetracyanoanthraquinone di Metal complexes of methane and its derivatives, fluorenone derivatives, diphenyldicyanoethylene and its derivatives, dibenzoquinone derivatives, 8-hydroxyquinoline and its derivatives and similar materials, and also Use high molecular weight materials as well as low molecular weight materials.

As an electron injection layer material, for example, LiF is generally used in this art, but the present application is not limited thereto.

As the light emitting layer material, red, green or blue light emitting materials can be used, and if necessary, two or more kinds of light emitting materials can be mixed and used. At this point, two or more luminescent materials may be deposited and used as separate sources, or may be premixed to be deposited and used as one source. In addition, as the light emitting layer material, a fluorescent material can be used, but a phosphorescent material can also be used. As the light-emitting layer material, a material that emits light by combining holes and electrons respectively injected from the positive electrode and the negative electrode may be used alone, but a material in which a host material participates in light emission together with a dopant material may 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 of n-type host material or p-type host material 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 an embodiment of the present disclosure may be a top emission type, a back emission type, or a double side emission type. .

The heterocyclic compound according to an embodiment of the present disclosure can work on a principle similar to that applied to organic light-emitting devices, even in organic solar cells, organic photoreceptors, organic transistors, and similar components. The same is true in electronic components. [Mode of Carrying Out the Invention]

1 ）化合物 1-1-6 的製備 Hereinafter, preferred examples are given to help understand the present disclosure, but the following examples are provided only for easier understanding of the present disclosure, and the present disclosure is not limited thereto. < Preparation example > Preparation example 1. Preparation of compound 1-1

1 ) Preparation of compound 1-1-6

2,3-Difluoro-1,4-diiodobenzene (22.8 g, 62.3 mmol/L (mM)), (2-fluorophenyl)boronic acid (7.3 g, 51.9 mmol/L), Tetrakis(triphenylphosphine) palladium (Pd(PPh ₃ ) ₄ ) (3.0 g, 2.6 mmol/L) and potassium carbonate (K ₂ CO ₃ ) (14.3 g, 103.8 mmol/L) were put into and Dissolved in 1,4-dioxane (250 mL) and water (H ₂ O) (50 mL), and then refluxed for 12 hours. After the reaction was completed, distilled water and dichloromethane (dichloromethane, DCM) were added and extracted at room temperature. Thereafter, moisture was removed from the organic layer with magnesium sulfate (MgSO ₄ ), and then the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:hexane=1:3) to obtain 13.9 g of target compound 1-1-6 (yield 80%). 2 ) Preparation of compound 1-1-5

Compound 1-1-6 (17.3 g, 51.9 mmol/L), (3-bromo-2-fluorophenyl) boronic acid (13.6 g, 62.3 mmol/L), tetrakis(triphenylphosphine) Palladium (Pd(PPh ₃ ) ₄ ) (3.0 g, 2.6 mmol/L) and potassium carbonate (K ₂ CO ₃ ) (14.3 g, 103.8 mmol/L) were added and dissolved in 1,4-di Oxane (250ml) and water ( _H2O ) (50ml), and then refluxed for 12 hours. After the reaction was completed, distilled water and dichloromethane (DCM) were added and extracted at room temperature. Thereafter, moisture was removed from the organic layer with magnesium sulfate (MgSO ₄ ), and then the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:hexane=1:3) to obtain 16.8 g of target compound 1-1-5 (yield 85%). 3 ) Preparation of compound 1-1-4

Compound 1-1-5 (16.8 g, 44.1 mmol/L) and potassium t-butoxide ( t -BuOK) (29.7 g, 264.6 mmol/L) were put into and dissolved in hexamethylphosphorus After adding hexamethylphosphoramide (HMPA) (160 ml), the mixture was stirred at 120 °C in a microwave reactor. After the reaction was completed, distilled water and dichloromethane (DCM) were added and extracted at room temperature. Thereafter, moisture was removed from the organic layer with magnesium sulfate (MgSO ₄ ), and then the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:hexane=1:3) to obtain 13.8 g of target compound 1-1-4 (yield 93%). 4 ) Preparation of compound 1-1-3

Compound 1-1-4 (17.5 g, 51.9 mmol/L), 2-chloroaniline (7.9 g, 62.3 mmol/L), palladium(II) acetate (Pd(OAc) ₂ ) (0.58 g , 2.6 mmol/L), 9,9-Dimethyl-4,5-bis(diphenylphosphino)-xanthene (9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene, XantPhos ) (3 g, 5.2 mmol/L) and sodium tert-butoxide (t-BuONa) (10.0 g, 103.8 mmol/L) were put into and dissolved in 1,4-dioxane (200 mL) , and then refluxed for 12 hours. After the reaction was completed, distilled water and dichloromethane (DCM) were added and extracted at room temperature. Thereafter, moisture was removed from the organic layer with magnesium sulfate (MgSO ₄ ), and then the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:hexane=1:3) to obtain 15.9 g of target compound 1-1-3 (yield 80%). 5 ) Preparation of compound 1-1-2

Compound 1-1-3 (15.9 g, 41.5 mmol/L), palladium (II) acetate (Pd(OAc) ₂ ) (0.47 g, 2.1 mmol/L), 50% tributyl Phosphine (P( t -Bu) ₃ ) (2 ml, 4.2 mmol/L) and 1,8-diazabicyclo[5.4.0]undec-7-ene (1,8-diazabicyclo[ 5.4.0] undec-7-ene, DBU) (9.3 ml, 62.3 mmol/l) was put into and dissolved in xylene (400 ml), and then refluxed for 4 hours. After the reaction was completed, distilled water and dichloromethane (DCM) were added and extracted at room temperature. Thereafter, moisture was removed from the organic layer with magnesium sulfate (MgSO ₄ ), and then the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:hexane=1:3) to obtain 12.5 g of target compound 1-1-2 (yield 87%). 6 ) Preparation of compound 1-1-1

Compound 1-1-2 (12.5 g, 36.2 mmol/L) and trifluoromethanesulfonic acid (80.1 mL, 905.0 mmol/L) were put into and dissolved in benzene-d6 (150 mL), and Reflux was then performed at 40°C. After the reaction was completed, distilled water and dichloromethane (DCM) were added and extracted at room temperature. Thereafter, moisture was removed from the organic layer with magnesium sulfate (MgSO ₄ ), and then the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:hexane=1:3) to obtain 10.1 g of the target compound 1-1-1 (yield 78%). 7 ) Preparation of compound 1-1

Compound 1-1-1 (10.1 g, 28.2 mmol/L), 2-chloro-4,6-diphenyl-1,3,5-triazine (9.1 g, 33.9 mmol/L) , tris(dibenzylideneacetone)dipalladium (Pd ₂ (dba) ₃ ) (1.3 g, 1.4 mmol/L), XPhos (1.3 g, 2.8 mmol/L) and sodium tert-butoxide ( t -BuONa) (5.4 g, 56.4 mmol/l) was put into and dissolved in xylene (200 ml), and then refluxed for 12 hours. After the reaction was completed, distilled water and dichloromethane (DCM) were added and extracted at room temperature. Thereafter, moisture was removed from the organic layer with magnesium sulfate (MgSO ₄ ), and then the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:hexane=1:3) to obtain 12.2 g of target compound 1-1 (yield 73%).

1-4

1-26

1-32

1-56

   製備例 2 ：化合物 1-61 的製備

1 ）化合物 1-61-5 的製備 By replacing 2-chloro-4,6-diphenyl-1,3,5-triazine in the above Preparation Example 1 by using Intermediate A of Table 1 below, in the same manner as in the preparation of the above Preparation Example 1 The target compounds in Table 1 below were synthesized. [Table 1] Compound number Intermediate A target compound Compound number Intermediate A target compound 1-3

1-4

1-26

1-32

1-56

Preparation Example 2 : Preparation of Compound 1-61

1 ) Preparation of compound 1-61-5

4,6-Dibromodibenzo[b,d]furan (5.2 g, 15.8 mmol/L), 2-aminobenzenethiol (2.0 g, 15.8 mmol/L), iodide Copper(I) (CuI) (3.0 g, 15.8 mmol/L), trans-1,2-diaminocyclohexane (1.9 mL, 15.8 mmol/L) and tripotassium phosphate (K ₃ PO ₄ ) (3.3 g, 31.6 mmol/l) was put into and dissolved in 1,4-dioxane (100 ml), and then refluxed for 24 hours. After the reaction was completed, distilled water and dichloromethane (DCM) were added and extracted at room temperature. Thereafter, moisture was removed from the organic layer with magnesium sulfate (MgSO ₄ ), and then the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:hexane=1:3) to obtain 5.0 g of the target compound 1-61-5 (yield 85%). 2 ) Preparation of Compound 1-61-4

Compound 1-61-5 (5.2 g, 15.8 mmol/L) and tert-butyl nitrite ( t -BuONO) (2.4 g, 23.7 mmol/L) were dissolved in acetonitrile (MeCN ) (100 ml), the mixture was stirred at 0°C for 1 hour, and copper (Cu) (2.0 g, 31.6 mmol/L) was put into it at 0°C, and then at 80°C Stirred for 3 hours. After the reaction was completed, distilled water and dichloromethane (DCM) were added and extracted at room temperature. Thereafter, moisture was removed from the organic layer with magnesium sulfate (MgSO ₄ ), and then the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:hexane=1:3) and recrystallized from methanol to obtain 2.9 g of target compound 1-61-4 (yield 52%). 3 ) Preparation of compound 1-61

1-114

1-241

1-243

1-244

1-264

1-265

1-272

1-294

1-295

1-296

製備例 3 ：化合物 1-121 的製備

1 ）化合物 1-121-4 的製備 Compound 1-61-3, Compound 1 were prepared in the same manner as in the preparation of Compound 1-1-3, Compound 1-1-2, Compound 1-1-1 and Compound 1-1 in Preparation Example 1 above. -61-2, compound 1-61-1 and compound 1-61, and by using the intermediate A of the following table 2 in the above preparation example 2 to replace 4,6-dibromodibenzo[b,d] furan and use the intermediate B of the following table 2 to replace 2-chloro-4,6-diphenyl-1,3,5-triazine, and synthesized the following table 2 in the same way as in the preparation of the preparation example 2 target compound. [Table 2] Compound number Intermediate A Intermediate B target compound 1-64

1-114

1-241

1-243

1-244

1-264

1-265

1-272

1-294

1-295

1-296

Preparation Example 3 : Preparation of Compound 1-121

1 ) Preparation of compound 1-121-4

12,12-Dimethyl-12H-fluorenone[1,2-b]benzofuran (11.8 g, 41.5 mmol/L) was added and dissolved in tetrahydrofuran (THF) (260 mL ), the mixture was substituted with nitrogen at -78°C and slowly added to 2.5 mol/L (M) n-butyllithium (n-BuLi) (20.0 ml, 49.8 ml mol/L), and stirred to room temperature. Thereafter, iodine (15.8 g, 62.3 mmol/L) was put thereinto and stirred for 1 hour. After the reaction was completed, distilled water and dichloromethane (DCM) were added and extracted. Thereafter, moisture was removed from the organic layer with magnesium sulfate (MgSO ₄ ), and then the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:hexane=1:3) to obtain 11.7 g of target compound 1-121-4 (yield 69%). 2 ) Preparation of compound 1-121

1-156

1-175

1-301

1-304

1-356

製備例 4 ：化合物 1-181 的製備

1 ）化合物 1-181-3 的製備 Compound 1-121-3, Compound 1 were prepared in the same manner as in the preparation of Compound 1-1-3, Compound 1-1-2, Compound 1-1-1 and Compound 1-1 in Preparation Example 1 above. -121-2, compound 1-121-1 and compound 1-121, and by using the intermediate A of the following table 3 in the above preparation example 3 to replace 12,12-dimethyl-12H-fluorenone[1 , 2-b] benzofuran and use intermediate B of the following table 3 instead of 2-chloro-4,6-diphenyl-1,3,5-triazine in the same manner as in the preparation of Preparation Example 3 The target compounds in Table 3 below were synthesized. [table 3] Compound number Intermediate A Intermediate B target compound 1-123

1-156

1-175

1-301

1-304

1-356

Preparation Example 4 : Preparation of Compound 1-181

1 ) Preparation of Compound 1-181-3

Compound 1-181-4 (8.2 g, 28.2 mmol/L), 2-chloroaniline (4.3 g, 33.9 mmol/L) and potassium tert-butoxide ( t -BuOK) (6.3 g, 56.4 mmol/L) was put into and dissolved in dimethyl sulfoxide (DMSO) (200 ml), and then refluxed. After the reaction was completed, distilled water and dichloromethane (DCM) were added and extraction was performed at room temperature. Thereafter, moisture was removed from the organic layer with magnesium sulfate (MgSO ₄ ), and then the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:hexane=1:3) to obtain 8.2 g of target compound 1-181-3 (yield 73%). 2 ) Preparation of compound 1-181

1-184

1-238

   製備例 5 ：化合物 1-361 的製備

1 ）化合物 1-361-3 的製備 Compound 1 was prepared in the same manner as in the preparation of Compound 1-61-5, Compound 1-61-4, Compound 1-61-2, Compound 1-61-1 and Compound 1-61 in Preparation 2 above -181-5, compound 1-181-4, compound 1-181-2, compound 1-181-1 and compound 1-181, and by using intermediate A of the following table 4 in the above preparation example 4 to replace 2 - Chloro-4,6-diphenyl-1,3,5-triazine, the target compound in the following Table 4 was synthesized in the same manner as in the preparation of Preparation Example 4. [Table 4] Compound number Intermediate A target compound Compound number Intermediate A target compound 1-183

1-184

1-238

Preparation Example 5 : Preparation of Compound 1-361

1 ) Preparation of compound 1-361-3

4-Bromo-3-chlorodibenzo[b,d]furan (14.6 g, 51.9 mmol/L), dibenzo[b,d]furan-4-amine (11.4 g, 62.3 mmol /L), palladium(II) acetate (Pd(OAc) ₂ ) (0.58 g, 2.6 mmol/L), XantPhos (3 g, 5.2 mmol/L) and sodium tert-butoxide ( t -BuONa ) (10.0 g, 103.8 mmol/L) was put into and dissolved in 1,4-dioxane (200 ml), and then refluxed for 12 hours. After the reaction was completed, distilled water and dichloromethane (DCM) were added and extraction was performed at room temperature. Thereafter, moisture was removed from the organic layer with magnesium sulfate (MgSO ₄ ), and then the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:hexane=1:3) to obtain 16.5 g of the target compound 1-361-3 (yield 83%). 2 ) Preparation of compound 1-361

1-379

1-381

1-383

1-398

1-401

1-408

1-416

1-421

1-423

1-436

1-441

1-442

1-455

1-461

1-477

製備例 6 ：化合物 2-3 的製備

1 ）化合物 2-3 的製備 Compound 1-361-2, Compound 1-361-1 and Compound 1 were prepared in the same manner as in the preparation of Compound 1-1-2, Compound 1-1-1 and Compound 1-1 in Preparation Example 1 above -361, and by replacing 4-bromo-3-chlorodibenzo[b,d]furan with Intermediate A in Table 5 below and using Intermediate B in Table 5 below in Preparation 5 above to replace dibenzo [b,d] Furan-4-amine and use the intermediate C of the following table 5 instead of 2-chloro-4,6-diphenyl-1,3,5-triazine, to be the same as in the preparation of Preparation Example 5 The target compound of following table 5 has been synthesized by the method. [table 5] Compound number Intermediate A Intermediate B Intermediate C target compound 1-372

1-379

1-381

1-383

1-398

1-401

1-408

1-416

1-421

1-423

1-436

1-441

1-442

1-455

1-461

1-477

Preparation Example 6 : Preparation of Compound 2-3

1 ) Preparation of compound 2-3

3-Bromo-1,1'-biphenyl (3.7 g, 15.8 mmol/L), 9-phenyl-9H,9'H-3,3'-biscarbazole (6.5 g, 15.8 mmol mol/L), copper(I) iodide (CuI) (3.0 g, 15.8 mmol/L), trans-1,2-diaminocyclohexane (1.9 mL, 15.8 mmol/L) and Tripotassium phosphate (K ₃ PO ₄ ) (3.3 g, 31.6 mmol/l) was put into and dissolved in 1,4-dioxane (100 ml), and then refluxed for 24 hours. After the reaction was completed, distilled water and dichloromethane (DCM) were added and extraction was performed at room temperature. Thereafter, moisture was removed from the organic layer with magnesium sulfate (MgSO ₄ ), and then the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:hexane=1:3) and recrystallized from methanol to obtain 7.5 g of target compound 2-3 (yield 85%).

2-7

2-9

2-31

2-32

2-42

製備例 7 ：化合物 2-73 的製備

1 ）化合物 2-73-2 的製備 By using intermediate A in Table 6 below in place of 3-bromo-1,1'-biphenyl and intermediate B in Table 6 below in place of 9-phenyl-9H,9'-H- in Preparation 6 above 3,3'-Biscarbazole, the target compound in the following Table 6 was synthesized in the same manner as in the preparation of Preparation Example 6. [Table 6] Compound number Intermediate A Intermediate B target compound 2-4

2-7

2-9

2-31

2-32

2-42

Preparation Example 7 : Preparation of Compound 2-73

1 ) Preparation of compound 2-73-2

2-Bromodibenzo[b,d]thiophene (4.2 g, 15.8 mmol/L), 9-phenyl-9H,9'H-3,3'-biscarbazole (6.5 g, 15.8 mmol/L), copper(I) iodide (CUI) (3.0 g, 15.8 mmol/L), trans-1,2-diaminocyclohexane (1.9 mL, 15.8 mmol/L ) and tripotassium phosphate (K ₃ PO ₄ ) (3.3 g, 31.6 mmol/l) were put into and dissolved in 1,4-dioxane (100 ml), and then refluxed for 24 hours. After the reaction was completed, distilled water and dichloromethane (DCM) were added and extraction was performed at room temperature. Thereafter, moisture was removed from the organic layer with magnesium sulfate (MgSO ₄ ), and then the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:hexane=1:3) and recrystallized from methanol to obtain 7.9 g of the target compound 2-73-2 (yield 85%). 2 ) Preparation of Compound 2-73-1

Compound 2-73-2 (8.4 g, 14.3 mmol) was dissolved in tetrahydrofuran (THF) (100 ml), and the mixture was substituted with nitrogen at -78°C, and slowly placed in 2.5 mol/L n-butyllithium (n-BuLi) (7.4 ml, 18.6 mmol) and stirred at room temperature for 1 hour. Trimethyl borate (B(OMe) ₃ ) (4.8 mL, 42.9 mmol) was slowly added to the reaction mixture and stirred at room temperature for 2 hours. After the reaction was completed, distilled water and dichloromethane (DCM) were added and extraction was performed at room temperature. Thereafter, moisture was removed from the organic layer with magnesium sulfate (MgSO ₄ ), and then the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:MeOH=100:3) and recrystallized from DCM to obtain 3.9 g of the target compound 2-73-1 (yield 70%). 3 ) Preparation of compound 2-73

1 ）化合物 3-2-1 的製備 Compound 2-73-1 (6.7 g, 10.5 mmol/L), iodobenzene (2.1 g, 10.5 mmol/L), tetrakis(triphenylphosphine) palladium (Pd(PPh ₃ ) ₄ ) ( 606 mg, 0.52 mmol/L) and potassium carbonate (K ₂ CO ₃ ) (2.9 g, 21.0 mmol/L) were put into and dissolved in toluene (100 ml), ethanol (EtOH) (20 ml) and water (H ₂ O) (20 ml), and then refluxed for 12 hours. After the reaction was completed, distilled water and dichloromethane (DCM) were added and extraction was performed at room temperature. Thereafter, moisture was removed from the organic layer with magnesium sulfate (MgSO ₄ ), and then the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:hexane=1:3) and recrystallized from methanol to obtain 4.9 g of target compound 2-73 (yield 70%). Preparation Example 8 : Preparation of Compound 3-2

1 ) Preparation of compound 3-2-1

9H,9'H-3,3'-biscarbazole (10 g, 30.0 mmol/L), 4-bromo-1,1'-biphenyl-2,2',3,3',4 ',5,5',6,6'-D ₉ [A] (7.26 g, 30 mmol/L), copper(I) iodide (CuI) (0.57 g, 3.0 mmol/L), Trans-1,2-diaminocyclohexane (0.34 g, 3.0 mmol/L) and tripotassium phosphate (K ₃ PO ₄ ) (12.7 g, 60.0 mmol/L) were put into and dissolved in 1 , 4-dioxane (100 ml), and then refluxed at 125°C for 8 hours. After the reaction was completed, distilled water and dichloromethane (DCM) were added and extraction was performed at room temperature. Thereafter, moisture was removed from the organic layer with magnesium sulfate (MgSO ₄ ), and then the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:hexane=1:3) and recrystallized from methanol to obtain 13.9 g of target compound 3-2-1 (yield 94%). 2 ) Preparation of Compound 3-2

Compound 3-2-1 (13.9 g, 28.0 mmol/L), 4-bromo-1,1'-biphenyl-2,2',3,3',4',5,5',6, 6'-D ₉ [A'] (6.8 g, 28.0 mmol/L), copper(I) iodide (CuI) (0.53 g, 2.8 mmol/L), trans-1,2-diamine Cyclohexane (0.32 g, 2.8 mmol/L) and tripotassium phosphate (K ₃ PO ₄ ) (11.9 g, 56.0 mmol/L) were put into and dissolved in 1,4-dioxane (140 ml), and then refluxed at 125 °C for 8 h. After the reaction was completed, distilled water and dichloromethane (DCM) were added and extraction was performed at room temperature. Thereafter, moisture was removed from the organic layer with magnesium sulfate (MgSO ₄ ), and then the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:hexane=1:3) and recrystallized from methanol to obtain 16.1 g of target compound 3-2 (yield 88%).

When compound A is the same as compound A', the target compound can be directly synthesized by adding more than 2 equivalents of compound A in Preparation Example 8. That is, when Compound A is the same as Compound A', the preparation of Compound 3-2-1 can be omitted.

3-5

3-6

3-8

3-19

3-22

製備例 9 ：化合物 3-26 的製備

1 ）化合物 3-26-2 的製備 By using intermediate A of Table 7 below in place of 4-bromo-1,1'-biphenyl-2,2',3,3',4',5,5',6 in Preparation 8 above, 6'-D ₉ [A], and use intermediate A' of Table 7 below instead of 4-bromo-1,1'-biphenyl-2,2',3,3',4 in Preparation 8 above ',5,5',6,6'-D ₉ [A'], the target compound in the following Table 7 was synthesized in the same manner as in the preparation of Preparation Example 8. [Table 7] Compound number Intermediate A Intermediate A' target compound 3-3

3-5

3-6

3-8

3-19

3-22

Preparation Example 9 : Preparation of Compound 3-26

1 ) Preparation of compound 3-26-2

9H,9'H-3,3'-biscarbazole (12.0 g, 36.2 mmol/L) and trifluoromethanesulfonic acid (CF ₃ CO ₃ H) (80.1 mL, 905.0 mmol/L) Put and dissolved in benzene-d6 (100 ml), and then refluxed at 40°C. After the reaction was completed, distilled water and dichloromethane (DCM) were added and extraction was performed at room temperature. Thereafter, moisture was removed from the organic layer with magnesium sulfate (MgSO ₄ ), and then the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:hexane=1:3) to obtain 8.9 g of the target compound 3-26-2 (yield 71%). 2 ) Preparation of compound 3-26-1

Compound 3-26-2 (5.5 g, 15.8 mmol/L), 4-bromo-1,1'-biphenyl [B] (3.7 g, 15.8 mmol/L), copper iodide (I )(CuI) (3.0 g, 15.8 mmol/L), trans-1,2-diaminocyclohexane (1.9 mL, 15.8 mmol/L) and tripotassium phosphate (K ₃ PO ₄ ) ( 3.3 g, 31.6 mmol/L) was put into and dissolved in 1,4-dioxane (100 mL), and then refluxed for 24 hours. After the reaction was completed, distilled water and dichloromethane (DCM) were added and extraction was performed at room temperature. Thereafter, moisture was removed from the organic layer with magnesium sulfate (MgSO ₄ ), and then the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:hexane=1:3) and recrystallized from methanol to obtain 6.5 g of the target compound 3-26-1 (yield 83%). 3 ) Preparation of compound 3-26

Compound 3-26-1 (14.0 g, 28.0 mmol/L), 4-bromo-1,1'-biphenyl [B'] (6.8 g, 28.0 mmol/L), copper iodide ( I) (CuI) (0.53 g, 2.8 mmol/L), trans-1,2-diaminocyclohexane (0.32 g, 2.8 mmol/L) and tripotassium phosphate (K ₃ PO ₄ ) (11.9 g, 56.0 mmol/l) was put into and dissolved in 1,4-dioxane (140 ml), and then refluxed at 125°C for 8 hours. After the reaction was completed, distilled water and dichloromethane (DCM) were added and extraction was performed at room temperature. Thereafter, moisture was removed from the organic layer with magnesium sulfate (MgSO ₄ ), and then the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:hexane=1:3) and recrystallized from methanol to obtain 15.8 g of target compound 3-26 (yield 87%).

When compound B is the same as compound B', the target compound can be directly synthesized by adding more than 2 equivalents of compound B in Preparation Example 9. That is, when compound B is the same as compound B', the preparation of the above compound 3-26-1 can be omitted.

3-27

3-29

3-32

3-33

3-36

3-39

3-44

製備例 10 ：化合物 3-50 的製備

1 ）化合物 3-50-1 的製備 By using intermediate B of Table 8 below in place of 4-bromo-1,1'-biphenyl [B] and intermediate B' of Table 8 below in place of 4-bromo-1,1' in Preparation 9 above - Biphenyl [B'], the target compound in Table 8 below was synthesized in the same manner as in the preparation of Preparation Example 9. [Table 8] Compound number Intermediate B Intermediate B' target compound 3-26

3-27

3-29

3-32

3-33

3-36

3-39

3-44

Preparation Example 10 : Preparation of Compound 3-50

1 ) Preparation of compound 3-50-1

9-([1,1'-biphenyl]-4-yl)-9H,9'H-3,3'-biscarbazole (13.6 g, 28.0 mmol/L), 4-bromo- 1,1'-biphenyl (6.8 g, 28.0 mmol/L), copper(I) iodide (CuI) (0.53 g, 2.8 mmol/L), trans-1,2-diaminocyclo Hexane (0.32 g, 2.8 mmol/L) and tripotassium phosphate (K ₃ PO ₄ ) (11.9 g, 56.0 mmol/L) were put into and dissolved in 1,4-dioxane (140 mL) and reflux at 125°C for 8 hours. After the reaction was completed, distilled water and dichloromethane (DCM) were added and extraction was performed at room temperature. Thereafter, moisture was removed from the organic layer with magnesium sulfate (MgSO ₄ ), and then the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:hexane=1:3) and recrystallized from methanol to obtain 15.9 g of the target compound 3-50-1 (yield 89%). 2 ) Preparation of compound 3-50

Compound 3-50-1 (23.0 g, 36.2 mmol/L) and trifluoromethanesulfonic acid (CF ₃ CO ₃ H) (80.1 mL, 905.0 mmol/L) were put into and dissolved in benzene-d6 (100 ml), and then refluxed at 40 °C. After the reaction was completed, distilled water and dichloromethane (DCM) were added and extraction was performed at room temperature. Thereafter, moisture was removed from the organic layer with magnesium sulfate (MgSO ₄ ), and then the solvent was removed using a rotary evaporator. The reaction product was purified by column chromatography (DCM:hexane=1:3) to obtain 16.9 g of target compound 3-50 (yield 70%).

3-51

3-53

3-56

3-57

3-58

3-60

3-62

3-63

3-67

3-68

By replacing 9-([1,1'-biphenyl]-4-yl)-9H,9'H-3,3'-biscarbazole in the above Preparation 10 by using Intermediate C of Table 9 below And using the intermediate C' in Table 9 below instead of 4-bromo-1,1'-biphenyl, the target compound in Table 9 below was synthesized in the same manner as in Preparation Example 10. [Table 9] Compound number Intermediate C Intermediate C' target compound 3-50

3-51

3-53

3-56

3-57

3-58

3-60

3-62

3-63

3-67

3-68

Compounds other than those described in the above Preparation Examples 1 to 10 and Tables 1 to 9 were also prepared in the same manner as in the above Preparation Examples, and the synthesis results are shown in Table 10 and Table 11 below. Table 10 below is the measured value of ¹ H nuclear magnetic resonance (nuclear magnetic resonance, NMR) (CDCl ₃ , 200Mz), and Table 11 below is the measured value of field desorption mass spectrometry (FD-MS). [Table 10] Compound number ¹ H NMR ( CDCl ₃ , 200 Mz ) 1-1 δ= 8.36 (4H, d), 7.50 (6H, m) 1-3 δ= 8.38~8.36 (3H, m), 7.94 (1H, s), 7.75~7.73 (3H, m), 7.61 (1H, d), 7.50~7.41(6H, m) 1-4 δ= 8.36 (2H, d), 7.96 (2H, d), 7.75 (2H, m), 7.50~7.41(6H, m), 7.25(2H, d) 1-26 δ= 7.96 (4H, d), 7.75 (4H, m), 7.49~7.41(6H, m), 7.25(4H, d) 1-32 δ= 8.36 (2H, d), 8.03~7.98 (2H, m), 7.82~7.76 (2H, m), 7.54~7.50(4H, m), 7.39~7.31 (2H, m) 1-56 δ = 100% deuterium content, no peaks 1-61 δ= 8.36 (4H, d), 7.50 (6H, m) 1-64 δ= 8.36 (2H, d), 7.96 (2H, d), 7.75 (2H, m), 7.50~7.41(6H, m), 7.25(2H, d) 1-114 δ = 100% deuterium content, no peaks 1-121 δ= 8.36 (4H, d), 7.50 (6H, m), 1.69 (6H, s) 1-123 δ= 8.38~8.36 (3H, m), 7.94 (1H, s), 7.75~7.73 (3H, m), 7.61 (1H, d), 7.50~7.41(6H, m), 1.69 (6H, s) 1-156 δ= 8.45 (1H, d), 8.38 (2H, d), 8.24~8.20 (2H, m), 7.94 (1H, d), 7.56~7.49 (5H, m), 1.69 (6H, s) 1-175 δ = 100% deuterium content, no peaks 1-181 δ= 8.36 (4H, d), 7.50 (6H, m) 1-183 δ= 8.38~8.36 (3H, m), 7.94 (1H, s), 7.75~7.73 (3H, m), 7.61 (1H, d), 7.50~7.41(6H, m) 1-184 δ= 8.36 (2H, d), 7.96 (2H, d), 7.75 (2H, m), 7.50~7.41(6H, m), 7.25(2H, d) 1-238 δ = 100% deuterium content, no peaks 1-241 δ= 8.36 (4H, d), 7.50 (6H, m) 1-243 δ= 8.38~8.36 (3H, m), 7.94 (1H, s), 7.75~7.73 (3H, m), 7.61 (1H, d), 7.50~7.41(6H, m) 1-244 δ= 8.36 (2H, d), 7.96 (2H, d), 7.75 (2H, m), 7.50~7.41(6H, m), 7.25(2H, d) 1-264 δ= 8.38 (2H, d), 7.94 (2H, s), 7.75~7.73 (6H, m), 7.61 (2H, d), 7.49~7.41(6H, m) 1-265 δ= 8.38 (1H, d), 7.96~7.94 (3H, m), 7.75~7.73 (5H, m), 7.61 (1H, d), 7.49~7.41(6H, m), 7.25 (2H, d) 1-272 δ= 8.36 (2H, d), 8.03~7.98 (2H, m), 7.82~7.76 (2H, m), 7.54~7.50(4H, m), 7.39~7.31 (2H, m) 1-294 δ = 100% deuterium content, no peaks 1-295 δ = 100% deuterium content, no peaks 1-296 δ = 100% deuterium content, no peaks 1-301 δ= 8.36 (4H, d), 7.50 (6H, m), 1.69 (6H, s) 1-304 δ= 8.36 (2H, d), 7.96 (2H, d), 7.75 (2H, m), 7.50~7.41(6H, m), 7.25(2H, d) 1-356 δ = 100% deuterium content, no peaks 1-361 δ= 8.36 (4H, d), 7.50 (6H, m) 1-372 δ= 8.36 (2H, d), 8.03~7.98 (2H, m), 7.82~7.76 (2H, m), 7.54~7.50(4H, m), 7.39~7.31 (2H, m) 1-379 δ = 100% deuterium content, no peaks 1-381 δ= 8.36 (4H, d), 7.50 (6H, m) 1-383 δ= 8.36 (2H, d), 7.96 (2H, d), 7.75 (2H, m), 7.50~7.41(6H, m), 7.25(2H, d) 1-398 δ = 100% deuterium content, no peaks 1-401 δ= 8.36 (4H, d), 7.50 (6H, m), 1.69 (6H, s) 1-408 δ= 9.27 (1H, s), 8.79 (1H, d), 8.36~8.30 (5H, m), 8.15 (1H, d), 7.70~7.64 (4H, m), 7.52~7.50 (4H, m), 1.69 (6H, s) 1-416 δ = 100% deuterium content, no peaks 1-421 δ= 8.36 (4H, d), 7.50 (6H, m) 1-423 δ= 8.36 (2H, d), 7.96 (2H, d), 7.75 (2H, m), 7.50~7.41(6H, m), 7.25(2H, d) 1-436 δ = 100% deuterium content, no peaks 1-441 δ= 8.36 (4H, d), 7.50 (6H, m), 1.69 (6H, s) 1-442 δ= 8.38~8.36 (3H, m), 7.94 (1H, s), 7.75~7.73 (3H, m), 7.61 (1H, d), 7.50~7.41(6H, m), 1.69 (6H, s) 1-455 δ = 100% deuterium content, no peaks 1-461 δ= 8.36 (4H, d), 7.50 (6H, m), 1.69 (12H, s) 1-477 δ= 8.38~8.36 (3H, m), 7.94 (1H, s), 7.75~7.73 (3H, m), 7.61 (1H, d), 7.50~7.41(6H, m), 1.69 (12H, s) 2-42 δ= 8.55 (1H, d), 8.30 (1H, d), 8.19~8.13 (2H, m), 7.99~7.89 (12H, m), 7.77~7.75 (5H, m), 7.50~7.35 (8H, m ), 7.20~7.16 (2H, m) 3-2 δ= 8.55 (1H, d), 8.30 (1H, d), 8.19~8.13 (2H, m), 7.99~7.89 (4H, m), 7.77 (1H, d), 7.58~7.50 (2H, m), 7.35 (1H, m), 7.20~7.16 (2H, m) 3-26 δ= 7.92 (4H, d), 7.91 (4H, d), 7.75 (2H, d), 7.49~7.41 (6H, m) 3-50 δ = 100% deuterium content, no peaks [Table 11] compound FD-MS compound FD-MS 1-1 Chemical formula: C ₃₉ H ₁₀ D ₁₂ N ₄ O ₂ Exact mass: 590.250 Molecular weight: 590.704 1-3 Chemical formula: C ₄₅ H ₁₄ D ₁₂ N ₄ O ₂ Exact mass: 666.281 Molecular weight: 666.802 1-4 Chemical formula: C ₄₅ H ₁₄ D ₁₂ N ₄ O ₂ Exact mass: 666.281 Molecular weight: 666.802 1-26 Chemical formula: C ₅₁ H ₁₈ D ₁₂ N ₄ O ₂ Exact mass: 742.312 Molecular weight: 742.900 1-32 Chemical formula: C ₄₅ H ₁₂ D ₁₂ N ₄ O ₃ Exact mass: 680.260 Molecular weight: 680.785 1-56 Chemical formula: C ₅₁ D ₃₀ N ₄ O ₂ Exact mass: 760.425 Molecular weight: 761.010 1-61 Chemical formula: C ₃₉ H ₁₀ D ₁₂ N ₄ OS Exact mass: 606.227 Molecular weight: 606.765 1-64 Chemical formula: C ₄₅ H ₁₄ D ₁₂ N ₄ OS Exact mass: 682.258 Molecular weight: 682.863 1-114 Chemical formula: C ₄₅ D ₂₆ N ₄ OS Exact mass: 696.346 Molecular weight: 696.949 1-121 Chemical formula: C ₄₂ H ₁₆ D ₁₂ N ₄ O Exact mass: 616.302 Molecular weight: 616.786 1-123 Chemical formula: C ₄₈ H ₂₀ D ₁₂ N ₄ O Exact mass: 692.333 Molecular weight: 692.884 1-156 Chemical formula: C ₄₈ H ₁₈ D ₁₂ N ₄ OS Exact mass: 722.289 Molecular weight: 722.928 1-175 Chemical formula: C ₅₄ H ₆ D ₃₀ N ₄ O Exact mass: 786.477 Molecular weight: 787.092 1-181 Chemical formula: C ₃₉ H ₁₀ D ₁₂ N ₄ OS Exact mass: 606.227 Molecular weight: 606.765 1-183 Chemical formula: C ₄₅ H ₁₄ D ₁₂ N ₄ OS Exact mass: 682.258 Molecular weight: 682.863 1-184 Chemical formula: C ₄₅ H ₁₄ D ₁₂ N ₄ OS Exact mass: 682.258 Molecular weight: 682.863 1-238 Chemical formula: C ₄₅ D ₂₄ N ₄ O ₂ S Exact mass: 708.313 Molecular weight: 708.919 1-241 Chemical formula: C ₃₉ H ₁₀ D ₁₂ N ₄ S ₂ Exact mass: 622.204 Molecular weight: 622.826 1-243 Chemical formula: C ₄₅ H ₁₄ D ₁₂ N ₄ S ₂ Exact mass: 698.235 Molecular weight: 698.924 1-244 Chemical formula: C ₄₅ H ₁₄ D ₁₂ N ₄ S ₂ Exact mass: 698.235 Molecular weight: 698.924 1-264 Chemical formula: C ₅₁ H ₁₈ D ₁₂ N ₄ S ₂ Exact mass: 774.267 Molecular weight: 775.022 1-265 Chemical formula: C ₅₁ H ₁₈ D ₁₂ N ₄ S ₂ Exact mass: 774.267 Molecular weight: 775.022 1-272 Chemical formula: C ₄₅ H ₁₂ D ₁₂ N ₄ OS ₂ Exact mass: 712.214 Molecular weight: 712.907 1-294 Chemical formula: C ₄₅ D ₂₆ N ₄ S ₂ Exact mass: 712.323 Molecular weight: 713.010 1-295 Chemical formula: C ₅₁ D ₃₀ N ₄ S ₂ Exact mass: 792.379 Molecular weight: 793.132 1-296 Chemical formula: C ₅₁ D ₃₀ N ₄ S ₂ Exact mass: 792.379 Molecular weight: 793.132 1-301 Chemical formula: C ₄₂ H ₁₆ D ₁₂ N ₄ S Exact mass: 632.279 Molecular weight: 632.847 1-304 Chemical formula: C ₄₈ H ₂₀ D ₁₂ N ₄ S Exact mass: 708.310 Molecular weight: 708.945 1-356 Chemical formula: C ₅₄ H ₆ D ₃₀ N ₄ S Exact mass: 802.454 Molecular weight: 803.153 1-361 Chemical formula: C ₃₉ H ₁₀ D ₁₂ N ₄ O ₂ Exact mass: 590.250 Molecular weight: 590.704 1-372 Chemical formula: C ₄₅ H ₁₂ D ₁₂ N ₄ O ₃ Exact mass: 680.260 Molecular weight: 680.785 1-379 Chemical formula: C ₄₅ D ₂₄ N ₄ O ₃ Exact mass: 692.335 Molecular weight: 692.858 1-381 Chemical formula: C ₃₉ H ₁₀ D ₁₂ N ₄ OS Exact mass: 606.227 Molecular weight: 606.765 1-383 Chemical formula: C ₄₅ H ₁₄ D ₁₂ N ₄ OS Exact mass: 682.258 Molecular weight: 682.863 1-398 Chemical formula: C ₅₁ D ₂₈ N ₄ OS Exact mass: 772.374 Molecular weight: 773.043 1-401 Chemical formula: C ₄₂ H ₁₆ D ₁₂ N _4O Exact mass: 616.302 Molecular weight: 616.786 1-408 Chemical formula: C ₅₄ H ₂₂ D ₁₂ N ₄ O Exact mass: 766.349 Molecular weight: 766.966 1-416 Chemical formula: C ₄₈ H ₆ D ₂₆ N ₄ O Exact mass: 706.421 Molecular weight: 706.970 1-421 Chemical formula: C ₃₉ H ₁₀ D ₁₂ N ₄ S ₂ Exact mass: 622.204 Molecular weight: 622.826 1-423 Chemical formula: C ₄₅ H ₁₄ D ₁₂ N ₄ S ₂ Exact mass: 698.235 Molecular weight: 698.924 1-436 Chemical formula: C ₄₅ D ₂₆ N ₄ S ₂ Exact mass: 712.323 Molecular weight: 713.010 1-441 Chemical formula: C ₄₂ H ₁₆ D ₁₂ N ₄ S Exact mass: 632.279 Molecular weight: 632.847 1-442 Chemical formula: C ₄₈ H ₂₀ D ₁₂ N ₄ S Exact mass: 708.310 Molecular weight: 708.945 1-455 Chemical formula: C ₄₈ H ₆ D ₂₆ N ₄ S Exact mass: 722.398 Molecular weight: 723.031 1-461 Chemical formula: C ₄₅ H ₂₂ D ₁₂ N ₄ Exact mass: 642.354 Molecular weight: 642.868 1-477 Chemical formula: C ₅₇ H ₁₂ D ₃₀ N ₄ Exact mass: 812.529 Molecular weight: 813.174 2-42 Chemical formula: C ₄₈ H ₃₂ N ₂ Exact mass: 636.257 Molecular weight: 636.798 3-2 Chemical formula: C ₄₈ H ₁₄ D ₁₈ N ₂ Exact mass: 654.370 Molecular weight: 654.908 3-26 Chemical formula: C ₄₈ H ₁₈ D ₁₄ N ₂ Exact mass: 650.344 Molecular weight: 650.883 3-50 Chemical formula: C ₄₈ D ₃₂ N ₂ Exact mass: 668.457 Molecular weight: 668.993 < Experimental example > < Experimental example 1> ( 1 ) Production of organic light-emitting element

A glass substrate coated with a 1,500 angstrom thick film of indium tin oxide (ITO) was ultrasonically cleaned with distilled water. After cleaning with distilled water, the substrates were ultrasonically cleaned with solvents such as acetone, methanol, and isopropanol, dried, and then treated with UV in an ultraviolet (UV) cleaner for 5 minutes Ultraviolet ozone (UVO) treatment. Thereafter, the substrate was transferred to a plasma cleaner (PT), and then, in order to improve the work function of ITO and remove the residual film in a vacuum state, the substrate was subjected to plasma treatment so that the substrate was transferred to a thermal deposition equipment for organic deposition.

On the transparent ITO electrode (positive electrode), 4,4',4''-tris[2-naphthyl(phenyl)amino]triphenylamine (4,4',4''-tris[ 2-naphthyl(phenyl)amino]triphenylamine, 2-TNATA) as the hole injection layer (which is a common layer), and deposited N,N'-bis(1-naphthyl)-N,N'-diphenyl Base-(1,1'-biphenyl)-4,4'-diamine (N,N'-di(1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4 ,4'-diamine, NPB) as the hole transport layer.

After forming the hole injection layer and the hole transport layer in this way, a light emitting layer was thermally vacuum deposited thereon as described below. The light-emitting layer was host by depositing the compounds set forth in Table 10 below to a thickness of 400 angstroms and utilized Ir(ppy ₎ as a green phosphorescent dopant at 7% by weight of the deposited thickness of the light-emitting layer An amount of doped Ir(ppy) ₃ is deposited on the host.

Thereafter, bathocuproine (BCP) was deposited as a hole blocking layer to a thickness of 60 angstroms, and tris(8-hydroxyquinoline) aluminum (Alq ₃ ) was deposited thereon as an electron transport layer to a thickness of 200 angstroms. Angstrom thickness.

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

Meanwhile, all organic compounds required for manufacturing an organic light emitting element were subjected to vacuum sublimation and purification at 10 ⁻⁸ Torr to 10 ⁻⁶ Torr for each material, respectively, and used to manufacture the organic light emitting element. ( 2 ) Driving voltage and luminous efficiency of organic light-emitting devices

The electroluminescence (EL) properties of the organic light-emitting element manufactured as described above were measured using M7000 of McScience Inc., and were used by a lifetime measurement system (M6000) manufactured by McScience Inc. Measurement Results The T ₉₀ value was measured at a reference luminance of 6,000 candela/square meter (cd/m ² ). Table 12 shows the results of measuring the driving voltage, luminous efficiency, color (EL color) and lifetime of the organic light emitting device manufactured according to the present disclosure. [Table 12] Light-emitting layer compound Driving Voltage (Volts) Luminous efficiency (cd / area) Color EL color Lifetime ( T ₉₀ ) Example 1 1-1 4.54 73.7 green 331 Example 2 1-3 4.53 74.9 green 338 Example 3 1-4 4.53 73.5 green 347 Example 4 1-26 4.56 73.2 green 352 Example 5 1-32 4.50 75.5 green 340 Example 6 1-56 4.86 82.1 green 440 Example 7 1-61 4.63 73.5 green 368 Example 8 1-64 4.65 73.6 green 370 Example 9 1-114 4.81 82.1 green 471 Example 10 1-121 4.62 73.1 green 363 Example 11 1-123 4.57 77.3 green 368 Example 12 1-156 4.69 74.4 green 366 Example 13 1-175 4.97 86.2 green 455 Example 14 1-181 4.35 75.8 green 390 Example 15 1-183 4.59 76.7 green 394 Example 16 1-184 4.70 76.3 green 402 Example 17 1-238 4.90 85.1 green 509 Example 18 1-241 4.38 75.7 green 431 Example 19 1-243 4.25 76.6 green 424 Example 20 1-244 4.63 73.3 green 441 Example 21 1-264 4.33 75.7 green 427 Example 22 1-265 4.41 74.5 green 435 Example 23 1-272 4.53 74.1 green 439 Example 24 1-294 4.94 82.1 green 550 Example 25 1-295 4.77 84.6 green 532 Example 26 1-296 4.99 80.1 green 588 Example 27 1-301 4.40 75.9 green 405 Example 28 1-304 4.53 74.6 green 415 Example 29 1-356 4.79 83.3 green 519 Example 30 1-361 4.33 74.0 green 260 Example 31 1-372 4.20 73.5 green 266 Example 32 1-379 4.51 82.3 green 353 Example 33 1-381 4.45 74.7 green 291 Example 34 1-383 4.35 75.1 green 297 Example 35 1-398 4.62 83.0 green 888 Example 36 1-401 4.55 72.8 green 272 Example 37 1-408 4.53 74.9 green 277 Example 38 1-416 4.84 83.1 green 353 Example 39 1-421 4.50 74.9 green 320 Example 40 1-423 4.51 73.9 green 326 Example 41 1-436 4.81 82.0 green 416 Example 42 1-441 4.45 74.7 green 303 Example 43 1-442 4.47 74.4 green 311 Example 44 1-455 4.69 83.8 green 423 Example 45 1-461 4.56 73.2 green 282 Example 46 1-477 4.77 83.5 green 395 Example 47 1-481 4.65 73.9 green 382 Example 48 1-484 4.32 82.7 green 486 Example 49 1-485 4.55 78.2 green 374 Example 50 1-488 4.91 87.1 green 481 Example 51 1-489 4.58 77.6 green 382 Example 52 1-492 4.91 86.8 green 489 Comparative example 1 Ref. 1 5.57 64.8 green 160 Comparative example 2 Ref. 2 5.83 61.2 green 170 Comparative example 3 Ref. 3 5.65 63.7 green 164 Comparative example 4 Ref. 4 5.66 61.0 green 188 Comparative Example 5 Ref. 5 5.81 64.3 green 198 Comparative Example 6 Ref. 6 5.62 62.5 green 193 Comparative Example 7 Ref. 7 5.62 64.3 green 130 Comparative Example 8 Ref. 8 5.41 65.5 green 149 Comparative Example 9 Ref. 9 5.62 64.6 green 138 Comparative Example 10 Ref. 10 5.62 65.1 green 157 Comparative Example 11 Ref. 11 5.33 64.2 green 153 Comparative Example 12 Ref. 12 5.52 64.4 green 142 Comparative Example 13 Ref. 13 5.63 62.5 green 183 Comparative Example 14 Ref. 14 5.82 61.2 green 181 Comparative Example 15 Ref. 15 5.55 63.5 green 176 Comparative Example 16 Ref. 16 5.63 62.1 green 185

Ref. 1 Ref. 2 Ref. 3 Ref. 4

Ref. 5 Ref. 6 Ref. 7 Ref. 8

Ref. 9 Ref. 10 Ref.11 Ref. 12

Ref. 13 Ref. 14 Ref.15 Ref. 16 In Table 12, the compounds of Comparative Example 1 to Comparative Example 16 are the same as the following compounds Ref. 1 to Ref. 16.

Ref. 1 Ref. 2 Ref. 3 Ref. 4

Ref. 5 Ref. 6 Ref. 7 Ref. 8

Ref. 9 Ref. 10 Ref.11 Ref. 12

Ref. 13 Ref. 14 Ref.15 Ref. 16

From the results of Table 12 above, it can be confirmed that, compared with the organic light-emitting elements of Comparative Example 1 to Comparative Example 16, in the organic light-emitting element using the heterocyclic compound according to the present disclosure as the light-emitting layer material, the driving voltage is low, and The luminous efficiency and life are significantly improved.

The heterocyclic compound according to the present disclosure is a deuterium-substituted compound, and the compounds of Comparative Example 1 to Comparative Example 16 are hydrogen-substituted compounds. Compounds substituted with deuterium (whose atomic mass is twice that of hydrogen) are in the ground state due to lower zero point energy and vibration energy than hydrogen-substituted compounds. It has lower energy, and collisions caused by intermolecular vibrations are reduced, and thus the thin film can be made in an amorphous state, thereby enabling to improve the lifetime of the organic light emitting element.

The deuterium-substituted compound has low ground state energy to improve the stability of the compound, and high dissociation energy of the C-D bond to improve the stability of the molecule, thereby enabling to increase the lifetime of the organic light-emitting device.

Specifically, it can be confirmed that, compared with Comparative Example Compound Ref. 1 to Comparative Example Compound Ref. Sex and amorphousness (amorphousness) have improved driving voltage and lifetime. Due to the low vibrational energy of the deuterium-substituted heterocyclic compound, energy loss is minimized and energy transfer to the dopant is facilitated, so that the luminous efficiency of the organic light emitting device can be improved.

Generally, when free radical cations are generated in carbazole, the 3-position of carbazole is activated to form a dimer, thereby inhibiting the efficiency and lifetime of the device.

On the other hand, when radical cations are generated in the deuterium-substituted condensed carbazole, deuterium stabilizes the radical cations to improve the lifetime of the organic light emitting element.

Specifically, it was demonstrated that deuterium-substituted heterocycles 1-1 to 1-492 according to the present disclosure are effective by effectively stabilizing radical cations due to deuterium substitution in condensed carbazoles. The life of the organic light-emitting device is greatly improved, and the comparative example compound Ref. 1 to the comparative example compound Ref. 16 do not contribute to the stabilization of free radical cations due to hydrogen substitution. Accordingly, it was confirmed that organic light-emitting elements using Compound 1-1 to Compound 1-492 in which the condensed carbazole was substituted with deuterium as the material of the light-emitting layer had improved lifetime.

In addition, the deuterium-substituted heterocyclic compound 1-294 according to the present disclosure can improve the luminous efficiency of organic light-emitting devices by reducing the vibrational energy of the compound to reduce energy loss, and can improve organic light emission by reducing the energy in the ground state component life.

In addition, compound 1-241, in which only the condensed carbazole is deuterium-substituted, increases intermolecular interactions compared to compound 1-294, thereby reducing the molecular distance and increasing mobility, thereby enabling The driving voltage of the organic light emitting element can be increased. < Experimental example 2> ( 1 ) Manufacture of organic light-emitting device

A glass substrate coated with a 1,500 Å thick film of indium tin oxide (ITO) was cleaned ultrasonically with distilled water. After cleaning with distilled water, the substrates were ultrasonically cleaned with solvents such as acetone, methanol, and isopropanol, dried, and then exposed to UV light for 5 minutes in an ultraviolet (UV) cleaner Ozone (UVO) disposal. Thereafter, the substrate was transferred to a plasma cleaner (PT), and then, in order to improve the work function of ITO and remove the residual film in a vacuum state, the substrate was subjected to plasma treatment so that the substrate was transferred to a thermal deposition equipment for organic deposition.

On the transparent ITO electrode (positive electrode), 4,4',4''-tris[2-naphthyl(phenyl)amino]triphenylamine (2-TNATA) was deposited as a hole injection layer ( which is a common layer), and N,N'-bis(1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine was deposited ( NPB) as the hole transport layer.

After forming the hole injection layer and the hole transport layer in this way, a light emitting layer was thermally vacuum deposited thereon as described below. The light-emitting layer was deposited by premixing one of the compounds (N type) shown in Table 11 below with one of the compounds represented by the above Chemical Formula 2 (P type) and then auto- One source deposited a premix as a host to a thickness of 400 Angstroms and doped on the host in an amount of 7% by weight of the deposited thickness of the emissive layer using Ir(ppy) as a green phosphorescent _dopant Ir(ppy) ₃ .

Thereafter, bathocuproine (BCP) was deposited to a thickness of 60 Å as a hole blocking layer, and tris(8-quinolinolato)aluminum (Alq ₃ ) was deposited thereon as an electron transport layer to a thickness of 200 Å. thickness.

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

Meanwhile, all organic compounds required for manufacturing an organic light emitting element were subjected to vacuum sublimation and purification at 10 ⁻⁸ Torr to 10 ⁻⁶ Torr for each material, respectively, and used to manufacture the organic light emitting element. ( 2 ) Driving voltage and luminous efficiency of organic light-emitting elements

The electroluminescence (EL) properties of the organic light-emitting element manufactured as described above were measured using M7000 of Micro Scientific Corporation, and the measurement results were used to measure when Reference T ₉₀ value at 6,000 cd/m². Table 13 shows the results of measuring the driving voltage, luminous efficiency, color (EL color) and lifetime of the organic light emitting device manufactured according to the present disclosure. [Table 13] Light-emitting layer compound ratio Driving Voltage (Volts) Luminous efficiency (cd / area) Color EL color Lifetime ( T ₉₀ ) Example 53 1-1 : 2-42 1 : 8 4.53 53.7 green 415 Example 54 1-1 : 2-42 1 : 5 4.49 56.1 green 524 Example 55 1-1 : 2-42 1 : 2 4.32 82.3 green 666 Example 56 1-1 : 2-42 1 : 1 4.38 70.1 green 612 Example 57 1-1 : 2-42 twenty one 4.29 69.4 green 589 Example 58 1-1 : 2-42 5:1 4.22 68.1 green 520 Example 59 1-1 : 2-42 8 : 1 4.21 67.4 green 437 Example 60 1-181 : 3-2 1 : 2 4.25 82.7 green 651 Example 61 1-181 : 3-2 1 : 1 4.43 80.1 green 612 Example 62 1-181 : 3-2 twenty one 4.48 78.5 green 588 Example 63 1-241 : 3-26 1 : 2 4.29 81.4 green 715 Example 64 1-241 : 3-26 1 : 1 4.46 79.8 green 662 Example 65 1-241 : 3-26 twenty one 4.49 78.4 green 629 Example 66 1-294 : 3-50 1 : 2 4.70 94.5 green 742 Example 67 1-294 : 3-50 1 : 1 4.83 92.8 green 722 Example 68 1-294 : 3-50 twenty one 4.95 90.1 green 699 Comparative Example 17 Ref.5 : 3-2 1 : 2 5.60 71.5 green 302 Comparative Example 18 Ref.5 : 3-2 1 : 1 5.73 69.8 green 292 Comparative Example 19 Ref.5 : 3-2 twenty one 5.95 67.4 green 247

In the results of Table 13, when the two compounds were mixed and by using the compound represented by the above Chemical Formula 1, which is the heterocyclic compound according to the present disclosure, as the N-type host and using the compound represented by the above Chemical Formula 2 according to the present disclosure When the indicated compounds are deposited as P-type hosts, it can be confirmed that the luminous efficiency and lifetime of the organic light-emitting device are improved. Accordingly, when the two compounds are mixed and deposited, it is expected that an excited complex phenomenon may occur.

The exciplex phenomenon is a phenomenon in which energy having the magnitude of a donor (p-host) HOMO level and an acceptor (n-host) LUMO level is emitted by electron exchange between two molecules. Reverse intersystem crossing (RISC) occurs when excited complexes occur between two molecules, and as a result, the internal quantum efficiency of fluorescence can be increased up to 100%. When a donor (p-host) with good hole transport capability and an acceptor (n-host) with good electron transport capability are used as the host of the light-emitting layer, since holes are injected into the p-host and electrons It is injected into the n-body, so the driving voltage of the organic light-emitting element can be reduced, thereby helping to improve the lifetime of the organic light-emitting element.

In the case of the compound represented by Chemical Formula 2, it is a compound substituted with hydrogen or partially or entirely substituted with deuterium. Compounds substituted with deuterium (whose atomic mass is twice that of hydrogen) have lower energy in the ground state due to lower zero-point and vibrational energies than hydrogen-substituted compounds, and vibrations caused by intermolecular vibrations Collisions are reduced, and thus the thin film can be made in an amorphous state, thereby making it possible to increase the lifetime of the organic light emitting element.

The deuterium-substituted compound has low ground state energy to improve the stability of the compound, and high dissociation energy of the C-D bond to improve the stability of the molecule, thereby enabling to increase the lifetime of the organic light-emitting device.

In the present disclosure, when the compound represented by the above Chemical Formula 2 is used as a donor and the compound represented by the above Chemical Formula 1 is used as an acceptor so that the compound is used as a host of the light emitting layer, it can be confirmed that the organic light emitting element exhibits extremely good nature.

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 schematically illustrating a stacked structure of an organic light emitting device according to an embodiment of the present disclosure.

100: Substrate

200: positive electrode

300: organic material layer

400: negative electrode

Claims (18)

A heterocyclic compound represented by the following Chemical Formula 1: [Chemical Formula 1]

Wherein, R1 to R12 are the same or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C2 to C60 alkenyl; substituted or unsubstituted C2 to C60 alkynyl; substituted or unsubstituted C1 to C60 alkoxy; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; and substituted or unsubstituted C2 to C60 heteroaryl, and at least one of R1 to R12 For deuterium, X1, X2 and X3 are the same or different from each other, and each independently is NAr1, O, S or CR13R14, and at least one of X1, X2 and X3 is NAr1, and Ar1 is represented by the following chemical formula 1-1 group, [chemical formula 1-1]

Wherein, L1 and L2 are the same or different from each other, and each independently is a single bond; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl, Ar2 and Ar3 are the same or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C2 to C60 Alkenyl; substituted or unsubstituted C2 to C60 alkynyl; substituted or unsubstituted C1 to C60 alkoxy; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted A C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; and a substituted or unsubstituted C2 to C60 heteroaryl group, a and b are the same or different from each other, and are each independently An integer of 0 to 3, and R13 and R14 are the same or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C60 alkyl; Substituted or unsubstituted C2 to C60 alkenyl; substituted or unsubstituted C2 to C60 alkynyl; substituted or unsubstituted C1 to C60 alkoxy; substituted or unsubstituted C3 to C60 ring alkyl; 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 as claimed in item 1, wherein the heterocyclic compound represented by the above chemical formula 1 is any one of the following chemical formula 1-a to chemical formula 1-f: [chemical formula 1-a]

[chemical formula 1-b]

[chemical formula 1-c]

[chemical formula 1-d]

[chemical formula 1-e]

[chemical formula 1-f]

Wherein, X3 is O, S or CR13R14, and R1 to R14 and Ar1 are as defined in the above chemical formula 1 and chemical formula 1-1. The heterocyclic compound as claimed in claim 1, wherein R1 to R12 are deuterium. The heterocyclic compound according to claim 1, wherein the deuterium content of R1 to R12 in the heterocyclic compound represented by the above chemical formula 1 is 1% to 100% based on the total number of hydrogen atoms and deuterium atoms. The heterocyclic compound as described in claim 1, wherein Ar2 and Ar3 in the above chemical formula 1-1 are deuterium-substituted C6 to C30 aryl or deuterium-substituted C2 to C30 heteroaryl, and in this case, Based on the total number of hydrogen atoms and deuterium atoms, the deuterium content is 1% to 100%. The heterocyclic compound according to claim 1, wherein the heterocyclic compound represented by the above chemical formula 1 does not contain deuterium as a substituent, or the deuterium content is 1% to 100% based on the total number of hydrogen atoms and deuterium atoms. The heterocyclic compound according to claim 6, wherein the deuterium content in the heterocyclic compound represented by the above chemical formula 1 is 20% to 100% based on the total number of hydrogen atoms and deuterium atoms. The heterocyclic compound as claimed in item 1, wherein the heterocyclic compound represented by the above chemical formula 1 is any one selected from the group consisting of the following compounds:

. An organic light emitting element, comprising: first electrode; a second electrode disposed facing said first electrode; and one or more layers of organic material disposed between the first electrode and the second electrode, Wherein the organic material layer comprises the heterocyclic compound as described in any one of Claim 1 to Claim 8. The organic light-emitting element as claimed in item 9, wherein the organic light-emitting element comprises 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 or more layers of the group, and the one or more layers comprise the heterocyclic compound. The organic light-emitting device according to claim 9, wherein the organic material layer includes a light-emitting layer, and the light-emitting layer includes the heterocyclic compound. The organic light-emitting device according to claim 9, 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 as claimed in item 9, wherein the organic material layer further comprises a heterocyclic compound represented by the following chemical formula 2: [chemical formula 2]

Wherein, R21 to R34 are the same or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C2 to C60 alkenyl; substituted or unsubstituted C2 to C60 alkynyl; substituted or unsubstituted C1 to C60 alkoxy; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; and substituted or unsubstituted C2 to C60 heteroaryl, L3 and L4 are the same or different from each other, and Each independently is a single bond; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl, Ar11 and Ar12 are the same or different from each other, and each independently selected 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; and -SiR101R102R103, and R101, R102 and R103 are the same or different from each other, and each independently substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl, and m and n are the same as each other or different, each independently being an integer of 0 to 3. The organic light-emitting device according to claim 13, wherein the heterocyclic compound represented by the above chemical formula 2 does not contain deuterium as a substituent, or the deuterium content is 1% to 100% based on the total number of hydrogen atoms and deuterium atoms. The organic light-emitting element as claimed in item 13, wherein the heterocyclic compound represented by the above chemical formula 2 is any one selected from the group consisting of the following compounds:

. The organic light-emitting element according to claim 13, wherein at least one of the heterocyclic compound represented by the above chemical formula 1 and the heterocyclic compound represented by the above chemical formula 2 does not contain deuterium as a substituent, or is replaced by hydrogen The deuterium content ranges from 1% to 100% based on the total number of atoms and deuterium atoms. A composition of an organic material layer of an organic light-emitting element, comprising a heterocyclic compound represented by Chemical Formula 1 and a heterocyclic compound represented by the following Chemical Formula 2 as described in any one of Claim 1 to Claim 8: [Chemical Formula 2 ]

Wherein, R21 to R34 are the same or different from each other, and are each independently selected from the group consisting of hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C2 to C60 alkenyl; substituted or unsubstituted C2 to C60 alkynyl; substituted or unsubstituted C1 to C60 alkoxy; substituted or unsubstituted C3 to C60 cycloalkyl; substituted or unsubstituted C2 to C60 heterocycloalkyl; substituted or unsubstituted C6 to C60 aryl; and substituted or unsubstituted C2 to C60 heteroaryl, L1 and L2 are the same or different from each other, and Each independently is a single bond; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl, Ar11 and Ar12 are the same or different from each other, and each independently selected 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; and -SiR101R102R103, and R101, R102 and R103 are the same or different from each other, and each independently substituted or unsubstituted C1 to C60 alkyl; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl, and m and n are the same as each other or different, each independently being an integer of 0 to 3. The composition according to claim 17, wherein the heterocyclic compound represented by the above Chemical Formula 1 and the heterocyclic compound represented by the above Chemical Formula 2 have a weight ratio of 1:10 to 10:1.

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