KR102546867B1 - Organic light emitting device - Google Patents

Abstract

The present specification is an anode; cathode; In the organic light emitting device including a first organic material layer and a second organic material layer provided between the anode and the cathode, the first organic material layer includes a compound represented by Formula 1, and the second organic material layer is represented by Formula 2 It provides an organic light emitting device comprising a compound and a compound represented by Formula 3.

Description

Organic light emitting device {ORGANIC LIGHT EMITTING DEVICE}

This application claims the benefit of the filing date of Korean Patent Application No. 10-2020-0025074 filed with the Korean Intellectual Property Office on February 28, 2020, the entire contents of which are incorporated herein.

The present specification relates to an organic light emitting device.

The organic light emitting device has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to the organic light emitting device having such a structure, electrons and holes injected from the two electrodes are combined in the organic thin film to form a pair, and then emit light while disappearing. The organic thin film may be composed of a single layer or multiple layers as needed.

Most of the materials used in organic light emitting devices are pure organic materials or complex compounds in which organic materials and metals are complexed. can be distinguished. Here, as the hole injection material or the hole transport material, an organic material having a p-type property, that is, an organic material that is easily oxidized and has an electrochemically stable state when oxidized is mainly used. On the other hand, as an electron injection material or electron transport material, an organic material having an n-type property, that is, an organic material that is easily reduced and has an electrochemically stable state during reduction is mainly used. As the material of the light emitting layer, a material having both p-type and n-type properties, that is, a material having a stable form in both oxidation and reduction states is preferable, and excitons generated by recombination of holes and electrons in the light emitting layer are formed. A material with high luminous efficiency that converts it into light when it is damaged is preferred.

In order to improve the performance, lifespan or efficiency of an organic light emitting device, the development of organic thin film materials is continuously required.

KR 10-2015-0132795 A

In this specification, an organic light emitting device having low driving voltage, high efficiency or long lifespan characteristics is described.

An exemplary embodiment of the present specification

anode;

cathode;

In the organic light emitting device including a first organic material layer and a second organic material layer provided between the anode and the cathode,

The first organic material layer includes a compound represented by Formula 1, and the second organic material layer includes a compound represented by Formula 2 and a compound represented by Formula 3 below.

[Formula 1]

In Formula 1,

X is O; or S,

L, L1 and L2 are the same as or different from each other, and are each independently a direct bond; Or a substituted or unsubstituted arylene group,

Ar1 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

a is an integer from 0 to 8, b is an integer from 0 to 7, when a is 2 or more, 2 or more R1's are the same as or different from each other, and when b is 2 or more, 2 or more R2's are the same or different from each other,

[Formula 2]

In Formula 2,

L3 and L4 are the same as or different from each other, and are each independently a direct bond; Or a substituted or unsubstituted arylene group,

Ar3 and Ar4 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

R3 is hydrogen; heavy hydrogen; halogen group; cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

c is an integer from 0 to 8, and when c is 2 or more, 2 or more R3s are the same as or different from each other;

The compound represented by Formula 2 is at least 40% substituted with deuterium,

[Formula 3]

In Formula 3,

A1 to A3 are the same as or different from each other, and each independently represents a substituted or unsubstituted aromatic hydrocarbon ring; A substituted or unsubstituted aliphatic hydrocarbon ring; And one selected from the group consisting of a substituted or unsubstituted aromatic heterocyclic ring, or a ring in which two or more rings selected from the group are condensed,

R31 to R35 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; or a substituted or unsubstituted amine group, or bonded to adjacent substituents to form a substituted or unsubstituted ring;

r31 to r33 are integers greater than or equal to 1, and when r31 to r33 are 2 or more, the substituents in parentheses are the same as or different from each other.

The organic light emitting device of the present invention includes the compound represented by Formula 1 in the first organic material layer and the compound represented by Formula 2 and Formula 3 in the second organic material layer, thereby providing low driving voltage, high efficiency or long lifespan. An organic light emitting device having

1 shows an example of an organic light emitting device composed of a substrate 1, an anode 2, an electron blocking layer 5, a light emitting layer 6, and a cathode 10.
2 shows a substrate (1), an anode (2), a hole injection layer (3), a hole transport layer (4), an electron blocking layer (5), a light emitting layer (6), a hole blocking layer (7), an electron transport layer (8) , An example of an organic light emitting device composed of an electron injection layer 9 and a cathode 10 is shown.

Hereinafter, the present specification will be described in more detail.

The present specification is an anode; cathode; In the organic light emitting device including a first organic material layer and a second organic material layer provided between the anode and the cathode, the first organic material layer includes a compound represented by Formula 1, and the second organic material layer is represented by Formula 2 below It provides an organic light emitting device comprising a compound represented by the compound represented by Formula 3 below.

In Chemical Formula 1, N of the carbazole group and the amine group are bonded through the meta position of the phenylene group, and the amine group is substituted with dibenzofuran or dibenzothiophene.

When a compound in which meta-phenylene acts as a linker is used in a hole transport region such as a hole transport layer or an electron blocking layer, the efficiency of the device is increased compared to the case where a compound in which para-phenylene acts as a linker is used. there is

In addition, when using a compound having the structure of Chemical Formula 1 in which a dibenzofuran group or a dibenzothiophene group is bonded to a hole transport region, there is an effect of stabilizing generated holes. In addition, since it is more stable from electrons transferred from the light emitting layer than when a compound having a structure in which an aryl group is bonded instead of a dibenzofuran group or a dibenzothiophene group is used, the lifetime is increased.

In Chemical Formula 2, aryl groups or heterocyclic groups are connected to carbons 9 and 10 of anthracene. In addition, since Formula 1 contains at least 40% of deuterium, the efficiency and lifetime of the device are improved. Specifically, when hydrogen is replaced by deuterium, the chemical properties of the compound hardly change. However, since the atomic weight of deuterium is twice that of hydrogen, deuterated compounds may change their physical properties. For example, a compound substituted with deuterium lowers the vibrational energy level. A compound substituted with deuterium can prevent a decrease in quantum efficiency due to a decrease in intermolecular van der Waals force or a collision due to intermolecular vibration. C-D bonds can also improve the stability of compounds. Accordingly, the compound represented by Formula 2 can improve the efficiency and lifetime of the device by including 40% or more of deuterium.

The compound represented by Chemical Formula 2 containing deuterium can be prepared by a known deuteration reaction. According to an exemplary embodiment of the present specification, the compound represented by Formula 2 is formed using a deuterated compound as a precursor, or deuterium is introduced into the compound through a hydrogen-deuterium exchange reaction using a deuterated solvent under an acid catalyst. You may.

The compound represented by Chemical Formula 3 has a structure containing boron, and when the compound represented by Chemical Formula 3 is used as a dopant, the full width at half maximum is narrowed, thereby increasing color purity and increasing efficiency.

From the low voltage and high efficiency characteristics of Chemical Formula 1, long life and low voltage characteristics based on material stability of Chemical Formula 2, and color purity and efficiency characteristics based on a narrow half-width of Chemical Formula 3, an organic light emitting device with low voltage, high efficiency and long lifespan can be obtained. .

In the present specification, when a certain component is said to "include", it means that it may further include other components without excluding other components unless otherwise stated.

In this specification, when a member is said to be located “on” another member, this includes not only the case where a member is in contact with another member, but also the case where another member exists between the two members.

In the present specification, the "layer" means compatible with 'film' mainly used in the art, and means a coating covering a target area. The size of the 'layer' is not limited, and the size of each 'layer' may be the same or different. In one embodiment, the size of a 'layer' may be the same as the size of an entire device, may correspond to the size of a specific functional region, or may be as small as a single sub-pixel.

In this specification, the meaning that a specific material A is included in the B layer means that i) one or more types of material A are included in one layer B, and ii) the layer B is composed of one or more layers, and the material A is a multi-layer B All of the layers included in one or more layers are included.

In the present specification, the meaning that a specific material A is included in the C layer or the D layer means that i) included in one or more of the one or more C layers, ii) included in one or more of the one or more D layers, or iii ) means all of those included in one or more C layers and one or more D layers, respectively.

In the present specification, N% substitution with deuterium means that N% of hydrogen available in the structure is substituted with deuterium. For example, if 25% of dibenzofuran is substituted with deuterium, it means that 2 out of 8 hydrogens in dibenzofuran are substituted with deuterium.

In the present specification, the degree of deuteration can be confirmed by known methods such as nuclear magnetic resonance spectroscopy ( ¹ H NMR) or GC/MS.

" 또는 점선은 화학식 또는 화합물에 결합되는 위치를 의미한다.In this specification, "

" or the dotted line means the position of bonding to the chemical formula or compound.

Examples of substituents in the present specification are described below, but are not limited thereto.

The term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position to be substituted is not limited as long as the hydrogen atom is substituted, that is, a position where the substituent is substituted, and when two or more are substituted , Two or more substituents may be the same as or different from each other.

In this specification, the term "substituted or unsubstituted" means deuterium; halogen group; nitrile group; nitro group; imide group; amide group; carbonyl group; ether group; ester group; hydroxy group; an alkyl group; cycloalkyl group; alkoxy group; aryloxy group; Alkyl thioxy group; Arylthioxy group; an alkyl sulfoxy group; aryl sulfoxy group; alkenyl group; silyl group; boron group; amine group; Arylphosphine group; phosphine oxide group; aryl group; And it means that it is substituted with one or two or more substituents selected from the group consisting of a heterocyclic group, or is substituted with a substituent in which two or more substituents among the above exemplified substituents are connected, or does not have any substituents. For example, "a substituent in which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected.

In this specification, the term "substituted or unsubstituted" means deuterium; an alkyl group; cycloalkyl group; amine group; aryl group; And it means that it is substituted with one or two or more substituents selected from the group consisting of a heterocyclic group, or is substituted with a substituent in which two or more substituents from among the above exemplified substituents are connected, or does not have any substituents.

In this specification, the term "substituted or unsubstituted" means deuterium; an alkyl group; aryl group; And it means that it is substituted with one or two or more substituents selected from the group consisting of a heterocyclic group, or is substituted with a substituent in which two or more substituents from among the above exemplified substituents are linked, or does not have any substituents.

In this specification, the term "substituted or unsubstituted" means deuterium; an alkyl group; aryl group; And it means that it is substituted with one or two or more substituents selected from the group consisting of a heterocyclic group, or is substituted with a substituent in which two or more substituents from among the above exemplified substituents are linked, or does not have any substituents.

In this specification, the term "substituted or unsubstituted" means deuterium; an alkyl group; Or substituted with one or two or more substituents selected from the group consisting of an aryl group, or substituted with a substituent in which two or more substituents among the above exemplified substituents are linked, or without any substituents.

Examples of the substituents are described below, but are not limited thereto.

In the present specification, examples of the halogen group include fluorine (-F), chlorine (-Cl), bromine (-Br), or iodine (-I).

In the present specification, the silyl group may be represented by a chemical formula of -SiY _a Y _b Y _c , wherein Y _a , Y _b and Y _c are each hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. The silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like, but is not limited thereto. don't

In the present specification, the boron group may be represented by the chemical formula -BY _d Y _e , wherein Y _d and Y _e are each hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. The boron group specifically includes a trimethyl boron group, a triethyl boron group, a t-butyldimethyl boron group, a triphenyl boron group, a phenyl boron group, but is not limited thereto.

In the present specification, the alkyl group may be straight or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to one embodiment, the number of carbon atoms of the alkyl group is 1 to 30. According to another embodiment, the number of carbon atoms of the alkyl group is 1 to 20. According to another exemplary embodiment, the number of carbon atoms of the alkyl group is 1 to 10. Specific examples of the alkyl group include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, pentyl group, n-pentyl group, hexyl group, n -Hexyl group, heptyl group, n-heptyl group, octyl group, n-octyl group, etc., but is not limited thereto.

In the present specification, an arylalkyl group means an alkyl group substituted with an aryl group.

In the present specification, the alkoxy group may be straight chain, branched chain or cyclic chain. The number of carbon atoms in the alkoxy group is not particularly limited, but is preferably 1 to 20 carbon atoms. Specifically, methoxy, ethoxy, n-propoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, It may be n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, etc., but is not limited thereto.

In the present specification, the alkenyl group may be straight-chain or branched-chain, and the number of carbon atoms is not particularly limited, but is 2 to 30; 2 to 20; 2 to 10; or preferably 2 to 5. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, etc., but are not limited thereto.

In the present specification, an alkynyl group is a substituent containing a triple bond between carbon atoms and may be straight or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms.

Alkyl groups, alkoxy groups, and substituents containing other alkyl moieties described herein include both straight-chain and branched forms.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 20. According to another exemplary embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 6. Specifically, there are a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and the like, but are not limited thereto.

In the present specification, the amine group is -NH ₂ ; Alkylamine group; Arylalkylamine group; Arylamine group; Arylheteroarylamine group; It may be selected from the group consisting of an alkylheteroarylamine group and a heteroarylamine group, but is not limited thereto. The number of carbon atoms of the amine group is not particularly limited, but is preferably 1 to 60.

In the present specification, the number of carbon atoms of the alkylamine group is not particularly limited, but may be 1 to 40, and may be 1 to 20 according to one embodiment. Specific examples of the alkylamine group include, but are not limited to, a methylamine group, a dimethylamine group, an ethylamine group, and a diethylamine group.

In the present specification, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group including two or more aryl groups may include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time.

Specific examples of the arylamine group include phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, diphenylamine group, phenylnaphthylamine group, biphenylphenylamine group, dibiphenylamine group, fluorine but a phenylphenylamine group and the like, but is not limited thereto.

In the present specification, examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, a substituted or unsubstituted diheteroarylamine group, or a substituted or unsubstituted triheteroarylamine group. The heteroaryl group in the heteroarylamine group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group. The heteroarylamine group including two or more heteroaryl groups may include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group at the same time.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the number of carbon atoms of the aryl group is 6 to 30. According to one embodiment, the number of carbon atoms of the aryl group is 6 to 20. The aryl group may be a phenyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, etc. as a monocyclic aryl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, triphenyl group, chrysenyl group, fluorenyl group, triphenylenyl group, etc., but is not limited thereto no.

In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.

When the fluorenyl group is substituted, it may have a structure as shown below, but is not limited thereto.

In the present specification, the aryl group in the aryloxy group may be applied to the above description of the aryl group.

In the present specification, the heterocyclic group is a ring group containing one or more of elements such as N, O, P, S, Si, and Se as heteroatoms, and the number of carbon atoms is not particularly limited, but preferably has 2 to 60 carbon atoms. According to one embodiment, the carbon number of the heterocyclic group is 2 to 30. Examples of the heterocyclic group include a pyridine group, a pyrrole group, a pyrimidine group, a quinoline group, a pyridazinyl group, a furan group, a thiophene group, an imidazole group, a pyrazole group, a dibenzofuran group, a dibenzothiophene group, carba A sol group, a benzocarbazole group, a naphthobenzofuran group, a benzonaphthothiophene group, an indenocarbazole group, a triazinyl group, and the like, but are not limited thereto.

In the present specification, the heterocyclic group described above may be applied except that the heteroaryl group is aromatic.

In the present specification, in a substituted or unsubstituted ring formed by bonding with adjacent groups, "ring" refers to a hydrocarbon ring; or a heterocyclic ring.

The hydrocarbon ring may be an aromatic, aliphatic, or condensed ring of aromatic and aliphatic, and may be selected from examples of the cycloalkyl group or aryl group except for the divalent group.

In the present specification, the meaning of forming a ring by bonding with adjacent groups means a substituted or unsubstituted aliphatic hydrocarbon ring by bonding with adjacent groups; A substituted or unsubstituted aromatic hydrocarbon ring; A substituted or unsubstituted aliphatic heterocycle; A substituted or unsubstituted aromatic heterocycle; or to form a condensed ring thereof. The hydrocarbon ring means a ring composed of only carbon and hydrogen atoms. The heterocycle refers to a ring containing at least one selected from elements such as N, O, P, S, Si, and Se. In the present specification, the aliphatic hydrocarbon ring, aromatic hydrocarbon ring, aliphatic heterocycle and aromatic heterocycle may be monocyclic or polycyclic.

In the present specification, an aliphatic hydrocarbon ring is a non-aromatic ring and refers to a ring composed of only carbon and hydrogen atoms. Examples of the aliphatic hydrocarbon ring include cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, cyclooctene, etc. Not limited to this.

In the present specification, an aromatic hydrocarbon ring means an aromatic ring composed of only carbon and hydrogen atoms. Examples of aromatic hydrocarbon rings include benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, phenalene, pyrene, tetracene, chrysene, pentacene, fluorene, indene, acenaphthylene, Benzofluorene, spirofluorene and the like, but are not limited thereto. In the present specification, an aromatic hydrocarbon ring may be interpreted as the same meaning as an aryl group.

In the present specification, an aliphatic heterocycle means an aliphatic ring containing one or more of heteroatoms. Examples of aliphatic heterocycles include oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepane, azocaine , Thiocane, etc., but are not limited thereto.

In the present specification, an aromatic heterocycle means an aromatic ring containing one or more of heteroatoms. Examples of aromatic heterocycles include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, parasol, oxazole, isoxazole, thiazole, isothiazole, triazole, oxadiazole, thia Diazole, dithiazole, tetrazole, pyran, thiopyran, diazine, oxazine, thiazine, dioxin, triazine, tetrazine, isoquinoline, quinoline, quinone, quinazoline, quinoxaline, naphthyridine, acridine , phenanthridine, diazanaphthalene, driazainden, indole, indolizine, benzothiazole, benzooxazole, benzoimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzo carbazole, dibenzocarbazole, phenazine, imidazopyridine, phenoxazine, indolocarbazole, indenocarbazole, and the like, but are not limited thereto.

In the present specification, the description of the aryl group may be applied except that the arylene group is divalent.

In the present specification, a divalent heterocyclic group means a heterocyclic group having two bonding sites, that is, a divalent group. The above description of the heterocyclic group can be applied except that each is a divalent group.

Hereinafter, preferred embodiments of the present invention will be described in detail. However, the embodiments of the present invention may be modified in various forms, and the scope of the present invention is not limited to the embodiments described below.

Hereinafter, Formula 1 will be described in detail.

[Formula 1]

In Formula 1,

X is O; or S,

L, L1 and L2 are the same as or different from each other, and are each independently a direct bond; Or a substituted or unsubstituted arylene group,

Ar1 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

a is an integer from 0 to 8, b is an integer from 0 to 7, when a is 2 or more, two or more R1's are the same as or different from each other, and when b is 2 or more, two or more R2's are the same or different from each other.

In one embodiment of the present specification, Formula 1 is represented by any one of Formulas 1-1 to 1-4 below.

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

In Chemical Formulas 1-1 to 1-4, the definitions of X, L, L1, L2, Ar1, R1, R2, a and b are the same as those in Chemical Formula 1.

In one embodiment of the present specification, X is O.

In one embodiment of the present specification, X is S.

In one embodiment of the present specification, L, L1 and L2 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group.

In one embodiment of the present specification, L, L1 and L2 are the same as or different from each other, and each independently a direct bond; or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms.

In one embodiment of the present specification, L, L1 and L2 are the same as or different from each other, and each independently a direct bond; or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

In one embodiment of the present specification, L, L1 and L2 are the same as or different from each other, and each independently a direct bond; or a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.

In one embodiment of the present specification, L, L1 and L2 are the same as or different from each other, and each independently a direct bond; or an arylene group having 6 to 20 carbon atoms.

In one embodiment of the present specification, L, L1 and L2 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; A substituted or unsubstituted terphenylene group; A substituted or unsubstituted naphthylene group; A substituted or unsubstituted fluorenylene group; A substituted or unsubstituted phenanthrenylene group; Or a substituted or unsubstituted triphenylenylene group.

In one embodiment of the present specification, L, L1 and L2 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; A substituted or unsubstituted terphenylene group; Or a substituted or unsubstituted naphthylene group.

In one embodiment of the present specification, L, L1 and L2 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; Or a substituted or unsubstituted naphthylene group.

In one embodiment of the present specification, L is a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; Or a substituted or unsubstituted naphthylene group.

In one embodiment of the present specification, L is a direct bond; A substituted or unsubstituted phenylene group; Or a substituted or unsubstituted biphenylene group.

In one embodiment of the present specification, L is a direct bond; phenylene group; or a biphenylene group.

In one embodiment of the present specification, L is an arylene group.

In one embodiment of the present specification, L is an arylene group having 6 to 30 carbon atoms.

In one embodiment of the present specification, L is an arylene group having 6 to 20 carbon atoms.

In one embodiment of the present specification, L is a phenylene group.

In one embodiment of the present specification, L is a direct bond; Or it is represented by any one of the following structural formulas.

는 결합위치를 의미한다.In the above structural formula,

represents the binding position.

In one embodiment of the present specification, L is a direct bond; Or it is represented by any one of the following structural formulas.

는 결합위치를 의미한다.In the above structural formula,

represents the binding position.

'로 표시되고,

는 결합위치를 의미한다.In one embodiment of the present specification, L is

', and

represents the binding position.

In one embodiment of the present specification, Formula 1 is represented by any one of Formulas 101 to 103 below.

[Formula 101]

[Formula 102]

[Formula 103]

In Chemical Formulas 101 to 103, the definitions of L1, L2, Ar1, R1, R2, X, a and b are the same as those in Chemical Formula 1.

In one embodiment of the present specification, Chemical Formula 102 is represented by Chemical Formula 102-1, and Chemical Formula 103 is represented by Chemical Formula 103-1 or 103-2.

[Formula 102-1]

[Formula 103-1]

[Formula 103-2]

In Formulas 102-1, 103-1, and 103-2, L1, L2, Ar1, R1, R2, X, a, and b are defined as defined in Formulas 102 and 103.

In one embodiment of the present specification, L1 is a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; Or a substituted or unsubstituted naphthylene group.

In one embodiment of the present specification, L1 is a direct bond; phenylene group; biphenylene group; or a naphthylene group.

In one embodiment of the present specification, L1 is a direct bond; or a phenylene group.

In one embodiment of the present specification, L1 is an arylene group.

In one embodiment of the present specification, L1 is an arylene group having 6 to 30 carbon atoms.

In one embodiment of the present specification, L1 is an arylene group having 6 to 20 carbon atoms.

In one embodiment of the present specification, L1 is a phenylene group.

In one embodiment of the present specification, L2 is a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; Or a substituted or unsubstituted naphthylene group.

In one embodiment of the present specification, L2 is a direct bond; phenylene group; biphenylene group; or a naphthylene group.

In one embodiment of the present specification, L2 is a direct bond; or an arylene group.

In one embodiment of the present specification, L2 is a direct bond; or an arylene group having 6 to 30 carbon atoms.

In one embodiment of the present specification, L2 is a direct bond; or an arylene group having 6 to 20 carbon atoms.

In one embodiment of the present specification, L2 is a direct bond; phenylene group; or a biphenylene group.

In one embodiment of the present specification, L2 is a direct bond; or a phenylene group.

In one embodiment of the present specification, L2 is a phenylene group.

In one embodiment of the present specification, Ar1 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

In one embodiment of the present specification, Ar1 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

In one embodiment of the present specification, Ar1 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms.

In one embodiment of the present specification, Ar1 is an aryl group unsubstituted or substituted with an alkyl group or an aryl group; Or a heterocyclic group unsubstituted or substituted with an alkyl group or an aryl group.

In one embodiment of the present specification, Ar1 is a substituted or unsubstituted aryl group.

In one embodiment of the present specification, Ar1 is an aryl group unsubstituted or substituted with an alkyl group or an aryl group.

In one embodiment of the present specification, Ar1 is an aryl group having 6 to 30 carbon atoms unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 30 carbon atoms.

In one embodiment of the present specification, Ar1 is an aryl group having 6 to 20 carbon atoms unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, Ar1 is a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted phenanthrenyl group; Or a substituted or unsubstituted triphenylenyl group.

In one embodiment of the present specification, Ar1 is a phenyl group unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms; A biphenyl group unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms; A terphenyl group unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms; a naphthyl group unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms; A fluorenyl group unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 30 carbon atoms; A phenanthrenyl group unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms; Or a triphenylenyl group unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms.

In one embodiment of the present specification, Ar1 is a phenyl group unsubstituted or substituted with a naphthyl group or a phenanthrenyl group; biphenyl group; terphenyl group; naphthyl group; A fluorenyl group unsubstituted or substituted with a methyl group or a phenyl group; phenanthrenyl group; or a triphenylenyl group.

In one embodiment of the present specification, Ar1 is a phenyl group; biphenyl group; terphenyl group; naphthyl group; dimethyl fluorenyl group; Diphenyl fluorenyl group; phenanthrenyl group; or a triphenylenyl group.

In one embodiment of the present specification, Ar1 is a phenyl group; biphenyl group; terphenyl group; or a naphthyl group.

In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms; A substituted or unsubstituted aryloxy group having 6 to 60 carbon atoms; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms; A substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted phenyl group.

In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; or a phenyl group.

In one embodiment of the present specification, R1 is hydrogen; or deuterium.

In one embodiment of the present specification, R1 is hydrogen.

In one embodiment of the present specification, R2 is hydrogen; heavy hydrogen; or a phenyl group.

In one embodiment of the present specification, R2 is hydrogen; or a phenyl group.

In one embodiment of the present specification, R2 is hydrogen.

In one embodiment of the present specification, R2 is a phenyl group.

In one embodiment of the present specification, a is 0 or 1.

In one embodiment of the present specification, a is 1.

In one embodiment of the present specification, b is 0 or 1.

In one embodiment of the present specification, b is 1.

Formula 2 will be described in detail below.

[Formula 2]

In Formula 2,

L3 and L4 are the same as or different from each other, and are each independently a direct bond; Or a substituted or unsubstituted arylene group,

Ar3 and Ar4 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

R3 is hydrogen; heavy hydrogen; halogen group; cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

c is an integer from 0 to 8, and when c is 2 or more, 2 or more R3s are the same as or different from each other;

The compound represented by Formula 2 is at least 40% substituted with deuterium.

In one embodiment of the present specification, L3 and L4 are the same as or different from each other, and are each independently a direct bond; or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms.

In one embodiment of the present specification, L3 and L4 are the same as or different from each other, and are each independently a direct bond; or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

In one embodiment of the present specification, L3 and L4 are the same as or different from each other, and are each independently a direct bond; Or an arylene group having 6 to 30 carbon atoms unsubstituted or substituted with heavy hydrogen.

In one embodiment of the present specification, L3 and L4 are the same as or different from each other, and are each independently a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; A substituted or unsubstituted terphenylene group; Or a substituted or unsubstituted naphthylene group.

In one embodiment of the present specification, L3 and L4 are the same as or different from each other, and are each independently a direct bond; A phenylene group unsubstituted or substituted with heavy hydrogen; A biphenylene group unsubstituted or substituted with heavy hydrogen; A terphenylene group unsubstituted or substituted with heavy hydrogen; Or a naphthylene group unsubstituted or substituted with deuterium.

In one embodiment of the present specification, L3 and L4 are the same as or different from each other, and are each independently a direct bond; A substituted or unsubstituted phenylene group; Or a substituted or unsubstituted naphthylene group.

In one embodiment of the present specification, L3 and L4 are the same as or different from each other, and are each independently a direct bond; A phenylene group unsubstituted or substituted with heavy hydrogen; Or a naphthylene group unsubstituted or substituted with deuterium.

In one embodiment of the present specification, L3 and L4 are the same as or different from each other, and are each independently a direct bond; Or a substituted or unsubstituted phenylene group.

In one embodiment of the present specification, L3 and L4 are the same as or different from each other, and are each independently a direct bond; Or a phenylene group unsubstituted or substituted with heavy hydrogen.

In one embodiment of the present specification, L3 and L4 are the same as or different from each other, and are each independently a direct bond; Or any one of the following structural formulas.

The structural formula is unsubstituted or substituted with deuterium.

In one embodiment of the present specification, L3 and L4 are the same as or different from each other, and are each independently a direct bond; Or any one of the following structural formulas.

In one embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

In one embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

In one embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and each independently represents an aryl group having 6 to 30 carbon atoms unsubstituted or substituted with deuterium; or a heterocyclic group having 2 to 30 carbon atoms unsubstituted or substituted with heavy hydrogen.

In one embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and each independently represents a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted phenanthrenyl group; A substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted naphthobenzofuran group; or a substituted or unsubstituted naphthobenzothiophene group.

In one embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and each independently represents a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted phenanthrenyl group; A substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted naphthobenzofuran group.

In one embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and each independently represents a phenyl group unsubstituted or substituted with deuterium; A biphenyl group unsubstituted or substituted with heavy hydrogen; A naphthyl group unsubstituted or substituted with heavy hydrogen; A phenanthrenyl group unsubstituted or substituted with heavy hydrogen; A dibenzofuran group unsubstituted or substituted with heavy hydrogen; Or a naphthobenzofuran group unsubstituted or substituted with heavy hydrogen.

In one embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and each independently represents any one of the following structural formulas.

The structural formula is unsubstituted or substituted with deuterium.

In one embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and each independently represents any one of the following structural formulas.

The structural formula is unsubstituted or substituted with deuterium.

In one embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and each independently a naphthyl group unsubstituted or substituted with deuterium; or a dibenzofuran group unsubstituted or substituted with heavy hydrogen.

In one embodiment of the present specification, at least one of Ar3 and Ar4 is a substituted or unsubstituted naphthyl group; A substituted or unsubstituted phenanthrenyl group; A substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted naphthobenzofuran group.

In one embodiment of the present specification, at least one of Ar3 and Ar4 is a naphthyl group unsubstituted or substituted with deuterium; A phenanthrenyl group unsubstituted or substituted with heavy hydrogen; A dibenzofuran group unsubstituted or substituted with heavy hydrogen; Or a naphthobenzofuran group unsubstituted or substituted with heavy hydrogen.

In one embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and each independently represents a phenyl group unsubstituted or substituted with deuterium; A naphthyl group unsubstituted or substituted with heavy hydrogen; or a dibenzofuran group unsubstituted or substituted with heavy hydrogen.

In one embodiment of the present specification, at least one of Ar3 and Ar4 is a substituted or unsubstituted naphthyl group; A substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted naphthobenzofuran group.

In one embodiment of the present specification, at least one of Ar3 and Ar4 is a naphthyl group unsubstituted or substituted with deuterium; A dibenzofuran group unsubstituted or substituted with heavy hydrogen; Or a naphthobenzofuran group unsubstituted or substituted with heavy hydrogen.

In one embodiment of the present specification, at least one of Ar3 and Ar4 is a substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted naphthobenzofuran group.

In one embodiment of the present specification, at least one of Ar3 and Ar4 is a dibenzofuran group unsubstituted or substituted with deuterium; Or a naphthobenzofuran group unsubstituted or substituted with heavy hydrogen.

In one embodiment of the present specification, Ar3 is a substituted or unsubstituted naphthyl group; A substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted naphthobenzofuran group.

In one embodiment of the present specification, Ar3 is a naphthyl group unsubstituted or substituted with deuterium; A dibenzofuran group unsubstituted or substituted with heavy hydrogen; Or a naphthobenzofuran group unsubstituted or substituted with heavy hydrogen.

In one embodiment of the present specification, Ar3 is a naphthyl group unsubstituted or substituted with deuterium; or a dibenzofuran group unsubstituted or substituted with heavy hydrogen.

In one embodiment of the present specification, Ar3 is any one of the following structural formulas.

The structural formula is unsubstituted or substituted with deuterium.

In one embodiment of the present specification, Ar3 is any one of the following structural formulas.

In one embodiment of the present specification, Ar3 is a substituted or unsubstituted naphthyl group; Or a substituted or unsubstituted dibenzofuran group.

In one embodiment of the present specification, Ar3 is a naphthyl group unsubstituted or substituted with deuterium; or a dibenzofuran group unsubstituted or substituted with heavy hydrogen.

In one embodiment of the present specification, Ar3 is a naphthyl group unsubstituted or substituted with deuterium; or a dibenzofuran group.

In one embodiment of the present specification, Ar4 is a substituted or unsubstituted aryl group.

In one embodiment of the present specification, Ar4 is an aryl group unsubstituted or substituted with deuterium.

In one embodiment of the present specification, Ar4 is a substituted or unsubstituted phenyl group; A substituted or unsubstituted naphthyl group; Or a substituted or unsubstituted phenanthrenyl group.

In one embodiment of the present specification, Ar4 is a phenyl group unsubstituted or substituted with deuterium; A naphthyl group unsubstituted or substituted with heavy hydrogen; Or a phenanthrenyl group unsubstituted or substituted with deuterium.

In one embodiment of the present specification, Ar4 is a substituted or unsubstituted phenyl group; Or a substituted or unsubstituted naphthyl group.

In one embodiment of the present specification, Ar4 is a phenyl group unsubstituted or substituted with deuterium; Or a naphthyl group unsubstituted or substituted with deuterium.

In one embodiment of the present specification, Ar4 is a substituted or unsubstituted naphthyl group.

In one embodiment of the present specification, Ar4 is a naphthyl group unsubstituted or substituted with deuterium.

In one embodiment of the present specification, R3 is hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, R3 is hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

In one embodiment of the present specification, R3 is hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

In one embodiment of the present specification, R3 is hydrogen; heavy hydrogen; or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In one embodiment of the present specification, R3 is hydrogen; heavy hydrogen; Or an aryl group having 6 to 30 carbon atoms unsubstituted or substituted with heavy hydrogen.

In one embodiment of the present specification, R3 is hydrogen; heavy hydrogen; A substituted or unsubstituted phenyl group; Or a substituted or unsubstituted naphthyl group.

In one embodiment of the present specification, R3 is hydrogen; heavy hydrogen; A phenyl group unsubstituted or substituted with heavy hydrogen; Or a naphthyl group unsubstituted or substituted with deuterium.

In one embodiment of the present specification, R3 is hydrogen; or deuterium.

In one embodiment of the present specification, R3 is deuterium.

In one embodiment of the present specification, R3 is deuterium; A phenyl group unsubstituted or substituted with heavy hydrogen; Or a naphthyl group unsubstituted or substituted with deuterium.

In one embodiment of the present specification, R3 is a phenyl group unsubstituted or substituted with deuterium; Or a naphthyl group unsubstituted or substituted with deuterium.

In one embodiment of the present specification, c is an integer from 0 to 8.

In one embodiment of the present specification, c is 1.

In one embodiment of the present specification, c is 8.

In the following description, the meaning that only a specific substituent is substituted with deuterium means that other substituents other than the specific substituent in the chemical formula do not contain deuterium.

In one embodiment of the present specification, Ar3 is substituted with deuterium.

In one embodiment of the present specification, Ar4 is substituted with deuterium.

In one embodiment of the present specification, L3 is substituted with deuterium.

In one embodiment of the present specification, L4 is substituted with deuterium.

In one embodiment of the present specification, R3 is substituted with deuterium.

In one embodiment of the present specification, only Ar3 is substituted with deuterium.

In one embodiment of the present specification, only Ar4 is substituted with deuterium.

In one embodiment of the present specification, only L3 is substituted with deuterium.

In one embodiment of the present specification, only L4 is substituted with deuterium.

In one embodiment of the present specification, only R3 is substituted with deuterium.

In one embodiment of the present specification, R3 is deuterium, and Ar3, Ar4, L3 and L4 are unsubstituted with deuterium.

In one embodiment of the present specification, only L3 and L4 are substituted with deuterium.

In one embodiment of the present specification, only Ar3 and Ar4 are substituted with deuterium.

In one embodiment of the present specification, only R3 and Ar3 are substituted with deuterium.

In one embodiment of the present specification, R3 is deuterium, and only L3 is substituted with deuterium.

In one embodiment of the present specification, when R3 is selected from substituents other than hydrogen and deuterium, only R3 and L3 are substituted with deuterium.

In one embodiment of the present specification, R3 is deuterium, and only Ar3 is substituted with deuterium.

In one embodiment of the present specification, when R3 is selected from substituents other than hydrogen and deuterium, only R3 and Ar3 are substituted with deuterium.

In one embodiment of the present specification, R3 is deuterium, and only L3 and L4 are substituted with deuterium.

In one embodiment of the present specification, when R3 is selected from substituents other than hydrogen and deuterium, only R3, L3 and L4 are substituted with deuterium.

In one embodiment of the present specification, R3 is deuterium, and only Ar3 and Ar4 are substituted with deuterium.

In one embodiment of the present specification, when R3 is selected from substituents other than hydrogen and deuterium, only R3, Ar3 and Ar4 are substituted with deuterium.

In one embodiment of the present specification, R3 is deuterium, and only L3 and Ar3 are substituted with deuterium.

In one embodiment of the present specification, when R3 is selected from substituents other than hydrogen and deuterium, only R3, L3 and Ar3 are substituted with deuterium.

In one embodiment of the present specification, R3 is deuterium, and only L3 and Ar4 are substituted with deuterium.

In one embodiment of the present specification, when R3 is selected from substituents other than hydrogen and deuterium, only R3, L3 and Ar4 are substituted with deuterium.

In one embodiment of the present specification, R3 is deuterium, and only L3, L4 and Ar3 are substituted with deuterium.

In one embodiment of the present specification, when R3 is selected from substituents other than hydrogen and deuterium, only R3, L3, L4 and Ar3 are substituted with deuterium.

In one embodiment of the present specification, R3 is deuterium, and only L3, Ar3 and Ar4 are substituted with deuterium.

In one embodiment of the present specification, when R3 is selected from substituents other than hydrogen and deuterium, only R3, L3, Ar3 and Ar4 are substituted with deuterium.

In one embodiment of the present specification, R3 is deuterium, and only L3, L4 Ar3 and Ar4 are substituted with deuterium.

In one embodiment of the present specification, when R3 is selected from substituents other than hydrogen and deuterium, only R3, L3, L4, Ar3 and Ar4 are substituted with deuterium.

In one embodiment of the present specification, Ar3 is 100% substituted with deuterium.

In one embodiment of the present specification, Ar4 is 100% substituted with deuterium.

In one embodiment of the present specification, L3 is 25% substituted with deuterium.

In one embodiment of the present specification, L3 is 50% substituted with deuterium.

In one embodiment of the present specification, L3 is 75% substituted with deuterium.

In one embodiment of the present specification, L3 is 100% substituted with deuterium.

In one embodiment of the present specification, L4 is 25% substituted with deuterium.

In one embodiment of the present specification, L4 is 50% substituted with deuterium.

In one embodiment of the present specification, L4 is 75% substituted with deuterium.

In one embodiment of the present specification, L4 is 100% substituted with deuterium.

In one embodiment of the present specification, R3 is 100% substituted with deuterium.

In one embodiment of the present specification, the compound represented by Formula 2 contains 40 to 60% of deuterium.

In one embodiment of the present specification, the compound represented by Formula 2 contains 40 to 80% of deuterium.

In one embodiment of the present specification, the compound represented by Formula 2 contains 60 to 80% of deuterium.

In one embodiment of the present specification, Formula 2 is represented by any one of Formulas 2-1 to 2-3 below.

[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

In Formulas 2-1 to 2-3, the definitions of L3, L4, Ar4, R3 and c are the same as those in Formula 2,

R4 to R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

d is an integer from 0 to 7, and when d is 2 or more, 2 or more R4 are the same as or different from each other;

e is an integer from 0 to 9, and when e is 2 or more, 2 or more R5's are the same as or different from each other;

f is an integer from 0 to 7, and when f is 2 or more, 2 or more R6's are the same as or different from each other.

In one embodiment of the present specification, R4 to R6 are the same as or different from each other, and each independently hydrogen; or deuterium.

In one embodiment of the present specification, R4 to R6 are hydrogen.

In one embodiment of the present specification, R4 to R6 are deuterium.

In one embodiment of the present specification, d is an integer from 0 to 7.

In one embodiment of the present specification, d is 0.

In one embodiment of the present specification, d is 7.

In one embodiment of the present specification, e is an integer from 0 to 9.

In one embodiment of the present specification, e is 0.

In one embodiment of the present specification, e is 9.

In one embodiment of the present specification, f is an integer from 0 to 7.

In one embodiment of the present specification, f is 0.

In one embodiment of the present specification, f is 7.

In one embodiment of the present specification, Formula 2-1 is represented by any one of Formulas 2-1-1 to 2-1-4, and Formula 2-2 is represented by Formulas 2-2-1 to 2- 2-4, and Formula 2-3 is represented by any one of Formulas 2-3-1 to 2-3-2 below.

[Formula 2-1-1]

[Formula 2-1-2]

[Formula 2-1-3]

[Formula 2-1-4]

[Formula 2-2-1]

[Formula 2-2-2]

[Formula 2-2-3]

[Formula 2-2-4]

[Formula 2-3-1]

[Formula 2-3-2]

In Formulas 2-1-1 to 2-1-4, 2-2-1 to 2-2-4, and 2-3-1 to 2-3-2,

The definitions of L3, L4, Ar4, R3 to R6 and c to f are the same as those in Chemical Formulas 2-1 to 2-3.

In one embodiment of the present specification, Formula 2 is represented by Formula 2-a or 2-b below.

[Formula 2-a]

[Formula 2-b]

In Formulas 2-a and 2-b, the definitions of L3, L4, Ar4, R3 and c are the same as those in Formula 2,

R5 is hydrogen; heavy hydrogen; halogen group; cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

e is an integer of 0 to 9, and when e is 2 or more, 2 or more R5's are the same as or different from each other.

In one embodiment of the present specification, Formula 2 is represented by Formula 2-4 or 2-5 below.

[Formula 2-4]

[Formula 2-5]

In Formulas 2-4 and 2-5, the definitions of L3, L4 and Ar4 are the same as those in Formula 2,

Ar5 is a substituted or unsubstituted aryl group,

R4 and R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

G1 is hydrogen; heavy hydrogen; halogen group; cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

d is an integer from 0 to 7, and when d is 2 or more, 2 or more R4 are the same as or different from each other;

f is an integer from 0 to 7, and when f is 2 or more, 2 or more R6 are the same as or different from each other;

g1 is an integer from 0 to 7, and when g1 is 2 or more, 2 or more G1s are the same as or different from each other.

In one embodiment of the present specification, Ar5 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

In one embodiment of the present specification, Ar5 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In one embodiment of the present specification, Ar5 is an aryl group having 6 to 30 carbon atoms unsubstituted or substituted with deuterium.

In one embodiment of the present specification, Ar5 is a substituted or unsubstituted phenyl group; Or a substituted or unsubstituted naphthyl group.

In one embodiment of the present specification, Ar5 is a phenyl group unsubstituted or substituted with deuterium; Or a naphthyl group unsubstituted or substituted with deuterium.

In one embodiment of the present specification, Ar5 is a naphthyl group unsubstituted or substituted with deuterium.

In one embodiment of the present specification, R4 and R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, R4 and R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, R4 and R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

In one embodiment of the present specification, R4 and R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

In one embodiment of the present specification, R4 and R6 are the same as or different from each other, and each independently hydrogen; or deuterium.

In one embodiment of the present specification, R4 and R6 are hydrogen.

In one embodiment of the present specification, R4 and R6 are deuterium.

In one embodiment of the present specification, G1 is hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, G1 is hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

In one embodiment of the present specification, G1 is hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

In one embodiment of the present specification, G1 is hydrogen; or deuterium.

In one embodiment of the present specification, G1 is deuterium.

In one embodiment of the present specification, g1 is an integer of 0 to 7.

In one embodiment of the present specification, g1 is 7.

In one embodiment of the present specification, Chemical Formula 2-4 is represented by any one of Chemical Formulas 2-4-1 to 2-4-4, and Chemical Formula 2-5 is represented by Chemical Formulas 2-5-1 to 2- It is displayed as one of 5-2.

[Formula 2-4-1]

[Formula 2-4-2]

[Formula 2-4-3]

[Formula 2-4-4]

[Formula 2-5-1]

[Formula 2-5-2]

In Formulas 2-4-1 to 2-4-4 and 2-5-1 to 2-5-2, the definitions of L3, L4, Ar4, Ar5, G1, R4, R6, g1, d and f are It is the same as the definition in Chemical Formulas 2-4 and 2-5.

In one embodiment of the present specification, Ar5 is substituted with deuterium.

In one embodiment of the present specification, G1 is deuterium, and only L3 is substituted with deuterium.

In one embodiment of the present specification, G1 is deuterium, and only L4 is substituted with deuterium.

In one embodiment of the present specification, G1 is deuterium, and only Ar4 is substituted with deuterium.

In one embodiment of the present specification, G1 is deuterium, and only Ar5 is substituted with deuterium.

In one embodiment of the present specification, G1 is deuterium, and only L3 and L4 are substituted with deuterium.

In one embodiment of the present specification, G1 is deuterium, and only L3 and Ar4 are substituted with deuterium.

In one embodiment of the present specification, G1 is deuterium, and only L3 and Ar5 are substituted with deuterium.

In one embodiment of the present specification, G1 is deuterium, and only L4 and Ar4 are substituted with deuterium.

In one embodiment of the present specification, G1 is deuterium, and only L4 and Ar5 are substituted with deuterium.

In one embodiment of the present specification, G1 is deuterium, and only Ar4 and Ar5 are substituted with deuterium.

In one embodiment of the present specification, G1 is deuterium, and only L3, L4 and Ar4 are substituted with deuterium.

In one embodiment of the present specification, G1 is deuterium, and only L3, L4 and Ar5 are substituted with deuterium.

In one embodiment of the present specification, G1 is deuterium, and only L3, Ar4 and Ar5 are substituted with deuterium.

In one embodiment of the present specification, G1 is deuterium, and only L4, Ar4 and Ar5 are substituted with deuterium.

In one embodiment of the present specification, G1 is deuterium, and L3, L4, Ar4 and Ar5 are substituted with deuterium.

In one embodiment of the present specification, Formula 2 is represented by Formula A-1 or A-2 below.

[Formula A-1]

[Formula A-2]

In the above formulas A-1 and A-2,

D means deuterium, and the definitions of L3, L4, Ar3 and Ar4 are the same as those in Formula 2,

Ar5 is a substituted or unsubstituted aryl group.

In one embodiment of the present specification, Ar5 is defined as defined in Chemical Formulas 2-4 and 2-5 above.

In one embodiment of the present specification, the compound represented by Chemical Formula 2 is substituted by at least 40% with deuterium.

In one embodiment of the present specification, the compound represented by Chemical Formula 2 is substituted by 50% or more of deuterium. In another exemplary embodiment, the compound represented by Formula 2 is substituted by 60% or more of deuterium. In another exemplary embodiment, the compound represented by Formula 2 is 70% or more substituted with deuterium. In another exemplary embodiment, the compound represented by Formula 2 is 80% or more substituted with deuterium. In another exemplary embodiment, the compound represented by Formula 2 is substituted by 90% or more with deuterium. In another exemplary embodiment, the compound represented by Formula 2 is 100% substituted with deuterium.

Hereinafter, Formula 3 will be described in detail.

[Formula 3]

In Formula 3,

A1 to A3 are the same as or different from each other, and each independently represents a substituted or unsubstituted aromatic hydrocarbon ring; A substituted or unsubstituted aliphatic hydrocarbon ring; And one selected from the group consisting of a substituted or unsubstituted aromatic heterocyclic ring, or a ring in which two or more rings selected from the group are condensed,

R31 to R35 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; or a substituted or unsubstituted amine group, or bonded to adjacent substituents to form a substituted or unsubstituted ring;

r31 to r33 are integers greater than or equal to 1, and when r31 to r33 are 2 or more, the substituents in parentheses are the same as or different from each other.

In one embodiment of the present specification, A1 to A3 are the same as or different from each other, and each independently a substituted or unsubstituted aromatic hydrocarbon ring; A substituted or unsubstituted aliphatic hydrocarbon ring; And one selected from the group consisting of a substituted or unsubstituted aromatic heterocyclic ring, or a ring in which two or more rings selected from the above group are condensed.

In one embodiment of the present specification, A1 to A3 are the same as or different from each other, and each independently a monocyclic to polycyclic aromatic hydrocarbon ring; monocyclic to polycyclic aromatic heterocycle; Or an aromatic hydrocarbon ring in which an aliphatic hydrocarbon ring is condensed.

In one embodiment of the present specification, A1 to A3 are the same as or different from each other, and each independently a monocyclic to tricyclic aromatic hydrocarbon ring; monocyclic to tricyclic aromatic heterocyclic ring; or a monocyclic to tricyclic aromatic hydrocarbon ring in which an aliphatic hydrocarbon ring is condensed.

In one embodiment of the present specification, A1 to A3 are the same as or different from each other, and each independently a monocyclic to bicyclic aromatic hydrocarbon ring; monocyclic to bicyclic aromatic heterocycle; or a monocyclic to bicyclic aromatic hydrocarbon ring in which a monocyclic aliphatic hydrocarbon ring is condensed.

In one embodiment of the present specification, A1 to A3 are the same as or different from each other, and each independently a monocyclic aromatic hydrocarbon ring; monocyclic to bicyclic aromatic heterocycle; or a monocyclic aromatic hydrocarbon ring formed by condensation of a monocyclic aliphatic hydrocarbon ring.

In one embodiment of the present specification, A1 to A3 are the same as or different from each other, and each independently a monocyclic aromatic hydrocarbon ring; A bicyclic aromatic heterocycle; or a monocyclic aromatic hydrocarbon ring formed by condensation of a monocyclic aliphatic hydrocarbon ring.

In one embodiment of the present specification, A1 to A3 are the same as or different from each other, and each independently a benzene ring; benzofuran ring; benzothiophene ring; or a tetrahydronaphthalene ring.

In one embodiment of the present specification, A1 and A2 are the same as or different from each other, and each independently a benzene ring; benzofuran ring; benzothiophene ring; or a tetrahydronaphthalene ring.

In one embodiment of the present specification, A3 is a benzene ring.

In one embodiment of the present specification, R31 to R35 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted cycloalkyl group having 6 to 60 carbon atoms; A substituted or unsubstituted arylalkyl group having 6 to 60 carbon atoms; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; A substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms; A substituted or unsubstituted aryloxy group having 6 to 60 carbon atoms; A substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms; A substituted or unsubstituted arylthio group having 6 to 60 carbon atoms; or a substituted or unsubstituted amine group, or bonded to an adjacent substituent to form a substituted or unsubstituted ring having 2 to 60 carbon atoms.

In one embodiment of the present specification, R31 to R35 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted cycloalkyl group having 6 to 30 carbon atoms; A substituted or unsubstituted arylalkyl group having 6 to 30 carbon atoms; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms; A substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms; A substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms; A substituted or unsubstituted arylthio group having 6 to 30 carbon atoms; or a substituted or unsubstituted amine group, or bonded to an adjacent substituent to form a substituted or unsubstituted ring having 2 to 30 carbon atoms.

In one embodiment of the present specification, R31 to R35 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; or a substituted or unsubstituted amine group, or a substituted or unsubstituted aromatic hydrocarbon ring by bonding with adjacent substituents; or a substituted or unsubstituted aliphatic hydrocarbon ring.

In one embodiment of the present specification, R31 to R35 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; or a substituted or unsubstituted amine group, or a substituted or unsubstituted aromatic hydrocarbon ring by bonding with adjacent substituents; or a substituted or unsubstituted aliphatic hydrocarbon ring.

In one embodiment of the present specification, R31 to R35 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; An alkyl group unsubstituted or substituted with heavy hydrogen; An aryl group unsubstituted or substituted with one or more groups selected from the group consisting of heavy hydrogen, a halogen group, an alkyl group having 1 to 10 carbon atoms, and an aryl group having 6 to 20 carbon atoms, or a group in which two or more groups selected from the group are connected; A heterocyclic group unsubstituted or substituted with one or more groups selected from the group consisting of heavy hydrogen, a halogen group, an alkyl group having 1 to 10 carbon atoms and an aryl group having 6 to 20 carbon atoms, or a group connected by two or more groups selected from the group; Or a deuterium group, a halogen group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, and a heterocyclic group having 6 to 20 carbon atoms. Substituted or unsubstituted with one or more groups selected from the group consisting of two or more groups connected to each other. an amine group, or an aliphatic hydrocarbon ring unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms by bonding with an adjacent group; Alternatively, an aromatic hydrocarbon ring unsubstituted or substituted with heavy hydrogen or an alkyl group having 1 to 10 carbon atoms may be formed.

In one embodiment of the present specification, R31 to R35 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; fluoro group; methyl group; CD ₃ ; i-propyl group; t-butyl group; A phenyl group unsubstituted or substituted with one or more groups selected from the group consisting of heavy hydrogen, a fluoro group, an alkyl group having 1 to 10 carbon atoms, and an aryl group having 6 to 20 carbon atoms, or a group in which two or more groups selected from the group are connected; A biphenyl group unsubstituted or substituted with one or more groups selected from the group consisting of heavy hydrogen, a fluoro group, an alkyl group having 1 to 10 carbon atoms, and an aryl group having 6 to 20 carbon atoms, or a group in which two or more groups selected from the group are connected; A carbazole group unsubstituted or substituted with at least one group selected from the group consisting of heavy hydrogen, a fluoro group, an alkyl group having 1 to 10 carbon atoms, and an aryl group having 6 to 20 carbon atoms, or a group in which two or more groups selected from the group are connected; A dibenzofuran group unsubstituted or substituted with at least one group selected from the group consisting of heavy hydrogen, a fluoro group, an alkyl group having 1 to 10 carbon atoms, and an aryl group having 6 to 20 carbon atoms, or a group in which two or more groups selected from the group are connected; Or a deuterium, fluoro group, alkyl group having 1 to 10 carbon atoms, aryl group having 6 to 20 carbon atoms and heterocyclic group having 6 to 20 carbon atoms. Substituted with one or more groups selected from the group or two or more groups selected from the group connected. A cyclic amine group, or a cyclopentane ring unsubstituted or substituted with a methyl group by bonding with an adjacent group; A cyclohexane ring unsubstituted or substituted with a methyl group; benzene rings; Alternatively, a benzofuran ring may be formed, or a structure as shown below may be formed.

는 화학식 3의 B에 결합되는 위치를 의미한다.The above structures are unsubstituted or substituted with deuterium, and the dotted line indicates a position bonded to N in Formula 3,

Means a position bonded to B in Formula 3.

In one embodiment of the present specification, R31 to R33 are the same as or different from each other, and are each independently an alkyl group having 1 to 10 carbon atoms.

In one embodiment of the present specification, R31 to R33 are the same as or different from each other, and each independently a methyl group; or a t-butyl group.

In one embodiment of the present specification, R34 and R35 are the same as or different from each other, and each independently represents an aryl group having 6 to 20 carbon atoms unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms.

In one embodiment of the present specification, r31 and r32 are integers from 1 to 4.

In one embodiment of the present specification, r31 and r32 are 1 or 2.

In one embodiment of the present specification, r33 is an integer of 1 to 3.

In one embodiment of the present specification, at least one of A1 and A2 in Formula 3 is represented by Formula 3-C.

[Formula 3-C]

In Formula 3-C, * is a condensed position in Formula 3,

Y is N(Ra1); O; or S,

Ra1 is hydrogen; heavy hydrogen; halogen group; cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; or a substituted or unsubstituted amine group, or bonded to adjacent substituents to form a substituted or unsubstituted ring;

E1 is a substituted or unsubstituted aromatic hydrocarbon ring; A substituted or unsubstituted aliphatic hydrocarbon ring; or a condensed ring of a substituted or unsubstituted aromatic hydrocarbon ring and an aliphatic hydrocarbon ring.

In one embodiment of the present specification, Y is O; or S.

In one embodiment of the present specification, E1 is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms; or a condensed ring of a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms and an aliphatic hydrocarbon ring having 3 to 60 carbon atoms.

In one embodiment of the present specification, E1 is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms; or a condensed ring of a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms and an aliphatic hydrocarbon ring having 3 to 30 carbon atoms.

In one embodiment of the present specification, E1 is a substituted or unsubstituted benzene ring; Or a benzene ring in which a substituted or unsubstituted cyclohexane ring is condensed.

In one embodiment of the present specification, E1 is a benzene ring.

In one embodiment of the present specification, Formula 3 is represented by any one of Formulas 3-1 to 3-5 below.

[Formula 3-1]

[Formula 3-2]

[Formula 3-3]

[Formula 3-4]

[Formula 3-5]

In Formulas 3-1 to 3-5,

The definitions of R31 to R35, r31 and r32 are the same as those in Formula 3,

E1 and E2 are the same as or different from each other, and each independently an aromatic hydrocarbon ring; aliphatic hydrocarbon ring; Or a condensed ring of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring,

Y1 and Y2 are the same as or different from each other, and each independently N(Ra1); O; or S,

R31”, R32” and Ra1 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; or a substituted or unsubstituted amine group, or bonded to adjacent substituents to form a substituted or unsubstituted ring;

r33 is an integer from 0 to 3, and when r33 is 2 or more, two or more R33s are the same as or different from each other;

r31” and r32” are integers greater than or equal to 0, and when r31” and r32” are each 2 or more, the substituents in parentheses are the same as or different from each other.

In one embodiment of the present specification, R34 and R35 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or bonded to adjacent substituents to form a substituted or unsubstituted ring.

In one embodiment of the present specification, R34 and R35 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or combined with adjacent substituents to form a substituted or unsubstituted ring having 2 to 30 carbon atoms.

In one embodiment of the present specification, R34 and R35 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms, or combined with adjacent substituents to form a substituted or unsubstituted ring having 2 to 30 carbon atoms.

In one embodiment of the present specification, R34 and R35 are the same as or different from each other, and each independently a methyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; or a substituted or unsubstituted dibenzofuran group, or bonded to an adjacent substituent to form a substituted or unsubstituted ring having 2 to 30 carbon atoms.

In one embodiment of the present specification, R34 and R35 are the same as or different from each other, and each independently a methyl group; A phenyl group unsubstituted or substituted with one or more groups selected from the group consisting of heavy hydrogen, a halogen group, an alkyl group having 1 to 10 carbon atoms, and an aryl group having 6 to 20 carbon atoms, or a group in which two or more groups selected from the group are connected; A biphenyl group unsubstituted or substituted with one or more groups selected from the group consisting of heavy hydrogen, a halogen group, an alkyl group having 1 to 10 carbon atoms, and an aryl group having 6 to 20 carbon atoms, or a group connected with two or more groups selected from the group; A naphthyl group unsubstituted or substituted with at least one group selected from the group consisting of heavy hydrogen, a halogen group, an alkyl group having 1 to 10 carbon atoms, and an aryl group having 6 to 20 carbon atoms, or a group connected by two or more groups selected from the group; or a dibenzofuran group, or bonded to adjacent substituents to form a ring having 2 to 30 carbon atoms unsubstituted or substituted with deuterium.

구조를 형성할 수 있다. 상기 구조들은 중수소로 치환 또는 비치환되고, 점선은 화학식 3의 N에 결합되는 위치를 의미한다.In one embodiment of the present specification, R34 and R35 are the same as or different from each other, and each independently a methyl group; A phenyl group unsubstituted or substituted with at least one group selected from the group consisting of heavy hydrogen, fluoro group, methyl group, i-propyl group, t-butyl group and phenyl group, or a group connected by two or more groups selected from the group; A biphenyl group unsubstituted or substituted with at least one group selected from the group consisting of deuterium, fluoro group, methyl group, i-propyl group, t-butyl group and phenyl group, or a group in which two or more groups selected from the above group are linked; naphthyl group; Or a dibenzofuran group, or unsubstituted or substituted with deuterium by combining with adjacent substituents

structure can be formed. The above structures are unsubstituted or substituted with deuterium, and the dotted line indicates a position bonded to N in Formula 3.

In one embodiment of the present specification, R34 and R35 are the same as or different from each other, and each independently a methyl group; A phenyl group unsubstituted or substituted with at least one group selected from the group consisting of heavy hydrogen, fluoro group, methyl group, i-propyl group, t-butyl group and phenyl group, or a group connected by two or more groups selected from the group; A biphenyl group unsubstituted or substituted with at least one group selected from the group consisting of deuterium, fluoro group, methyl group, i-propyl group, t-butyl group and phenyl group, or a group in which two or more groups selected from the above group are linked; naphthyl group; or a dibenzofuran group.

In one embodiment of the present specification, R34 and R35 are the same as or different from each other, and each independently a methyl group; A phenyl group unsubstituted or substituted with heavy hydrogen, a fluoro group, a methyl group, an i-propyl group, a t-butyl group or a phenyl group; Deuterium, a fluoro group, a methyl group, a t-butyl group, or a biphenyl group unsubstituted or substituted with -CF ₃ ; naphthyl group; or a dibenzofuran group.

In one embodiment of the present specification, R34 and R35 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a t-butyl group; or a biphenyl group unsubstituted or substituted with a t-butyl group.

In one embodiment of the present specification, R34 and R35 are phenyl groups unsubstituted or substituted with t-butyl groups.

In one embodiment of the present specification, Chemical Formula 3 is represented by any one of Chemical Formulas 301 to 305 below.

[Formula 301]

[Formula 302]

[Formula 303]

[Formula 304]

[Formula 305]

In Formulas 301 to 305,

The definitions of R31 to R33, r31 and r32 are the same as those in Formula 3,

E1 and E2 are the same as or different from each other, and each independently an aromatic hydrocarbon ring; aliphatic hydrocarbon ring; Or a condensed ring of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring,

Y1 and Y2 are the same as or different from each other, and each independently N(Ra1); O; or S,

R36, R37, R31”, R32” and Ra1 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; or a substituted or unsubstituted amine group, or bonded to adjacent substituents to form a substituted or unsubstituted ring;

r31” and r32” are integers greater than or equal to 0, and when r31” and r32” are each 2 or more, the substituents in parentheses are the same as or different from each other,

r33 is an integer from 0 to 3, and when r33 is 2 or more, two or more R33s are the same as or different from each other;

r36 and r37 are integers from 0 to 5, and when r36 and r37 are 2 or more, the substituents in parentheses are the same as or different from each other.

In one embodiment of the present specification, E1 and E2 are the same as or different from each other, and each independently a monocyclic to tricyclic aromatic hydrocarbon ring; monocyclic to tricyclic aliphatic hydrocarbon ring; or a condensed ring of a monocyclic to tricyclic aromatic hydrocarbon ring and an aliphatic hydrocarbon ring.

In one embodiment of the present specification, E1 and E2 are the same as or different from each other, and each independently a monocyclic to tricyclic aromatic hydrocarbon ring; monocyclic to tricyclic aliphatic hydrocarbon ring; or a condensed ring of a bi- or tri-cyclic aromatic hydrocarbon ring and an aliphatic hydrocarbon ring.

In one embodiment of the present specification, E1 and E2 are the same as or different from each other, and each independently a monocyclic to bicyclic aromatic hydrocarbon ring; monocyclic to bicyclic aliphatic hydrocarbon ring; or a condensed ring of a bi- or tri-cyclic aromatic hydrocarbon ring and an aliphatic hydrocarbon ring.

In one embodiment of the present specification, E1 and E2 are the same as or different from each other, and each independently a benzene ring; or a condensed ring of a benzene ring and a cyclohexane ring.

In one embodiment of the present specification, E1 and E2 are the same as or different from each other, and each independently represents a benzene ring.

In one embodiment of the present specification, E1 and E2 are the same as or different from each other, and are each independently represented by any one of the following structures.

* means the condensation position.

In one embodiment of the present specification, Y1 and Y2 are the same as or different from each other, and each independently O; or S.

In one embodiment of the present specification, Y1 and Y2 are O.

In one embodiment of the present specification, Y1 and Y2 are S.

In one embodiment of the present specification, Ra1 is a substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, Ra1 is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

In one embodiment of the present specification, Ra1 is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms.

In one embodiment of the present specification, Ra1 is a substituted or unsubstituted phenyl group.

In one embodiment of the present specification, Ra1 is a phenyl group.

In one embodiment of the present specification, R31” and R32” are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or bonded to adjacent substituents to form a substituted or unsubstituted ring.

In one embodiment of the present specification, R31” and R32” are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or combined with adjacent substituents to form a substituted or unsubstituted ring having 2 to 30 carbon atoms.

In one embodiment of the present specification, R31” and R32” are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms, or combined with adjacent substituents to form a substituted or unsubstituted ring having 2 to 20 carbon atoms.

In one embodiment of the present specification, R31” and R32” are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms, or a substituted or unsubstituted aliphatic hydrocarbon ring having 3 to 20 carbon atoms by bonding with adjacent substituents; or a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 20 carbon atoms.

In one embodiment of the present specification, R31” and R32” are the same as or different from each other, and each independently hydrogen; heavy hydrogen; It is an alkyl group having 1 to 20 carbon atoms, or is bonded to an adjacent substituent to form an aliphatic hydrocarbon ring having 3 to 20 carbon atoms unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms.

In one embodiment of the present specification, R31” and R32” are the same as or different from each other, and each independently hydrogen; heavy hydrogen; methyl group; or a t-butyl group, or bonded to adjacent substituents to form a cyclohexane ring unsubstituted or substituted with a methyl group.

In one embodiment of the present specification, R31 and R32 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; or a substituted or unsubstituted amine group, or bonded to adjacent substituents to form a substituted or unsubstituted ring.

In one embodiment of the present specification, R31 and R32 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; or a substituted or unsubstituted amine group, or bonded to adjacent substituents to form a substituted or unsubstituted aliphatic hydrocarbon ring or a substituted or unsubstituted aromatic hydrocarbon ring.

In one embodiment of the present specification, R31 and R32 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms; or a substituted or unsubstituted amine group, or bonded to an adjacent substituent to form a substituted or unsubstituted C3-C30 aliphatic hydrocarbon ring or a substituted or unsubstituted C6-C30 aromatic hydrocarbon ring.

In one embodiment of the present specification, R31 and R32 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; A substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms; or a substituted or unsubstituted amine group, or bonded to an adjacent substituent to form a substituted or unsubstituted C3-C20 aliphatic hydrocarbon ring or a substituted or unsubstituted C6-C20 aromatic hydrocarbon ring.

In one embodiment of the present specification, R31 and R32 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; methyl group; propyl group; butyl group; A phenyl group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms; carbazole group; Or a deuterium group, a halogen group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, and a heterocyclic group having 6 to 20 carbon atoms. Substituted or unsubstituted with one or more groups selected from the group consisting of two or more groups connected to each other. is an amine group.

In one embodiment of the present specification, R31 and R32 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; methyl group; i-propyl group; t-butyl group; A phenyl group unsubstituted or substituted with a methyl group; carbazole group; or an amine group unsubstituted or substituted with at least one group selected from the group consisting of deuterium, fluoro group, methyl group, t-butyl group, phenyl group and dibenzofuran group, or a group connected by two or more groups selected from the above group.

In one embodiment of the present specification, R31 and R32 may combine with adjacent groups to form a substituted or unsubstituted ring.

In one embodiment of the present specification, R31 and R32 may combine with adjacent groups to form a substituted or unsubstituted aliphatic hydrocarbon ring or a substituted or unsubstituted aromatic hydrocarbon ring.

In one embodiment of the present specification, R31 and R32 are bonded to adjacent groups to form a substituted or unsubstituted cyclopentane ring; A substituted or unsubstituted cyclohexane ring; A substituted or unsubstituted benzene ring; Alternatively, a substituted or unsubstituted fluorene ring may be formed, or a structure as shown below may be formed.

는 화학식 3의 B에 결합되는 위치를 의미한다.The above structures are substituted or unsubstituted, and the dotted line indicates a position bonded to N in Formula 3,

Means a position bonded to B in Formula 3.

In one embodiment of the present specification, R31 and R32 are bonded to adjacent groups to form a cyclopentane ring unsubstituted or substituted with a methyl group; A cyclohexane ring unsubstituted or substituted with a methyl group; Alternatively, a benzene ring may be formed, or a structure as shown below may be formed.

는 화학식 3의 B에 결합되는 위치를 의미한다.The above structures are unsubstituted or substituted with deuterium, and the dotted line indicates a position bonded to N in Formula 3,

Means a position bonded to B in Formula 3.

In an exemplary embodiment of the present specification, when r31 is 2 or more, R31 may be bonded to another R31, bonded to R32, or bonded to R36 to form a ring structure.

In an exemplary embodiment of the present specification, when r32 is 2 or more, R32 may be bonded to another R32, bonded to R31, or bonded to R37 to form a ring structure.

In an exemplary embodiment of the present specification, when r31 and r32 are 2 or more, R31 is bonded to another R31 or R32 is bonded to another R32 to form a cyclopentane ring unsubstituted or substituted with a methyl group; A cyclohexane ring unsubstituted or substituted with a methyl group; or a benzene ring.

를 형성할 수 있다. 이때,

는 화학식 3의 B에 결합되는 위치를 의미한다.In one embodiment of the present specification, R31 is combined with R32

can form At this time,

Means a position bonded to B in Formula 3.

구조를 형성할 수 있다. 이때, 상기 구조에서, 점선은 화학식 3의 N에 결합되는 위치를 의미한다.In an exemplary embodiment of the present specification, R31 is bonded to R36 and R37 is unsubstituted or substituted with deuterium.

structure can be formed. At this time, in the above structure, the dotted line means a position bonded to N in Formula 3.

In one embodiment of the present specification, R31 and R32 are the same as or different from each other, and each independently may be a substituted or unsubstituted alkyl group, or may combine with an adjacent group to form a substituted or unsubstituted aliphatic hydrocarbon ring.

In one embodiment of the present specification, R31 and R32 may be a t-butyl group, or may combine with adjacent groups to form a substituted or unsubstituted cyclohexane ring.

In one embodiment of the present specification, R31 and R32 may be a t-butyl group, or may combine with adjacent groups to form a cyclohexane ring unsubstituted or substituted with a methyl group.

In one embodiment of the present specification, R36 and R37 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted aromatic hydrocarbon ring by bonding with adjacent substituents; or form an aliphatic hydrocarbon ring.

In one embodiment of the present specification, R36 and R37 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or bonded to an adjacent substituent to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms.

In one embodiment of the present specification, R36 and R37 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms, or bonded to adjacent substituents to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 20 carbon atoms.

In one embodiment of the present specification, R36 and R37 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; methyl group; butyl group; A phenyl group unsubstituted or substituted with one or more groups selected from the group consisting of heavy hydrogen, a halogen group, and an alkyl group having 1 to 10 carbon atoms, or a group connected with two or more groups selected from the group, or bonded to adjacent substituents to form a benzene ring; benzofuran ring; Or form the following structure.

The above structures are unsubstituted or substituted with deuterium, and the dotted line indicates a position bonded to N in Formula 3.

In one embodiment of the present specification, R36 and R37 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; methyl group; t-butyl group; A phenyl group unsubstituted or substituted with one or more groups selected from the group consisting of heavy hydrogen, a fluoro group, a methyl group, and a t-butyl group, or a group connected with two or more groups selected from the group, or bonded to adjacent substituents to form a benzene ring; benzofuran ring; Or form the following structure.

The above structures are unsubstituted or substituted with deuterium, and the dotted line indicates a position bonded to N in Formula 3.

In one embodiment of the present specification, R36 and R37 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; fluoro group; methyl group; i-propyl group; t-butyl group; A phenyl group unsubstituted or substituted with a deuterium, fluoro group, methyl group, CF ₃ or t-butyl group, or combined with R31 or R32 to form a benzene ring; benzofuran ring; Or form the following structure.

The above structures are unsubstituted or substituted with deuterium, and the dotted line indicates a position bonded to N in Formula 3.

In one embodiment of the present specification, R36 and R37 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; Or an aryl group unsubstituted or substituted with an alkyl group.

In one embodiment of the present specification, R36 and R37 are the same as or different from each other, and each independently a t-butyl group; Or a phenyl group unsubstituted or substituted with a t-butyl group.

In one embodiment of the present specification, R36 and R37 are t-butyl groups.

In one embodiment of the present specification, R33 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; or a substituted or unsubstituted amine group, or bonded to adjacent substituents to form a substituted or unsubstituted ring.

In one embodiment of the present specification, R33 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; or a substituted or unsubstituted amine group, or bonded to adjacent substituents to form a substituted or unsubstituted aliphatic hydrocarbon ring or a substituted or unsubstituted aromatic hydrocarbon ring.

In one embodiment of the present specification, R33 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms; or a substituted or unsubstituted amine group, or bonded to an adjacent substituent to form a substituted or unsubstituted C3-C30 aliphatic hydrocarbon ring or a substituted or unsubstituted C6-C30 aromatic hydrocarbon ring.

In one embodiment of the present specification, R33 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted aryl group having 6 to 20 carbon atoms; A substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms; or a substituted or unsubstituted amine group, or bonded to an adjacent substituent to form a substituted or unsubstituted C3-C20 aliphatic hydrocarbon ring or a substituted or unsubstituted C6-C20 aromatic hydrocarbon ring.

In one embodiment of the present specification, R33 is hydrogen; heavy hydrogen; An alkyl group having 1 to 20 carbon atoms unsubstituted or substituted with heavy hydrogen; a heterocyclic group having 2 to 20 carbon atoms unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms; Or an amine group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, an alkyl group having 1 to 20 carbon atoms, and an aryl group having 6 to 20 carbon atoms, or two or more groups selected from the group connected, or substituted by combining with adjacent substituents or an unsubstituted aromatic hydrocarbon ring having 6 to 20 carbon atoms.

In one embodiment of the present specification, R33 is hydrogen; heavy hydrogen; methyl group; CD ₃ ; butyl group; An amine group unsubstituted or substituted with one or more groups selected from the group consisting of heavy hydrogen, an alkyl group having 1 to 10 carbon atoms, and an aryl group having 6 to 20 carbon atoms, or a group connected with two or more groups selected from the group; Or a carbazole group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms, or bonded to an adjacent substituent to form a benzene ring; or form a benzofuran ring.

In one embodiment of the present specification, R33 is hydrogen; heavy hydrogen; methyl group; CD ₃ ; t-butyl group; An amine group unsubstituted or substituted with one or more groups selected from the group consisting of deuterium, methyl and phenyl groups, or a group connected with two or more groups selected from the group; Or a carbazole group unsubstituted or substituted with a t-butyl group, or a benzene ring by bonding with adjacent substituents; or form a benzofuran ring.

In one embodiment of the present specification, R33 is hydrogen; heavy hydrogen; methyl group; CD ₃ ; t-butyl group; A diphenylamine group unsubstituted or substituted with heavy hydrogen; Or a carbazole group, or a benzene ring by bonding with adjacent substituents; or form a benzofuran ring.

In one embodiment of the present specification, R33 is a substituted or unsubstituted alkyl group.

In one embodiment of the present specification, R33 is a substituted or unsubstituted methyl group.

In one embodiment of the present specification, R33 is a methyl group.

In one embodiment of the present specification, r31” and r32” are integers from 0 to 5.

In one embodiment of the present specification, r31” and r32” are integers from 1 to 5.

In one embodiment of the present specification, r36 and r37 are integers from 0 to 5.

In one embodiment of the present specification, r36 and r37 are integers from 1 to 5.

In one embodiment of the present specification, Chemical Formula 301 is represented by Chemical Formula 301-A or 301-B.

[Formula 301-A]

[Formula 301-B]

In Formulas 301-A and 301-B,

The definitions of R33, R36, R37, r33, r36 and r37 are the same as those in Formula 301,

Cy1 is an aliphatic hydrocarbon ring,

G31 and G32 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; or a substituted or unsubstituted amine group, or bonded to an adjacent substituent to form a substituted or unsubstituted aromatic hydrocarbon ring;

G32' is hydrogen; heavy hydrogen; halogen group; cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; Or a substituted or unsubstituted amine group,

g31 and g32 are integers from 0 to 4, g32' is an integer of 0 or greater, and when g31, g32 and g32' are 2 or more, the substituents in parentheses are the same as or different from each other.

In one embodiment of the present specification, Formula 3 is represented by Formula 301-B below.

[Formula 301-B]

In Formula 301-B, the definition of R33 is the same as the definition in Formula 3,

Cy1 is an aliphatic hydrocarbon ring,

R36 and R37 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; or a substituted or unsubstituted amine group, or bonded to adjacent substituents to form a substituted or unsubstituted ring;

G31 is hydrogen; heavy hydrogen; halogen group; cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; or a substituted or unsubstituted amine group, or bonded to an adjacent substituent to form a substituted or unsubstituted aromatic hydrocarbon ring;

G32' is hydrogen; heavy hydrogen; halogen group; cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; Or a substituted or unsubstituted amine group,

r33 is an integer from 0 to 3, and when r33 is 2 or more, two or more R33s are the same as or different from each other;

r36 and r37 are integers from 0 to 5, and when r36 and r37 are 2 or more, the substituents in parentheses are the same as or different from each other;

g31 is an integer of 0 to 4, g32' is an integer of 0 or more, and when g31 and g32' are 2 or more, the substituents in parentheses are the same as or different from each other.

In one embodiment of the present specification, Formula 3 is represented by any one of Formulas 301, 302, and 303.

In one embodiment of the present specification, Formula 3 is represented by any one of Formulas 301-B, 302, and 303.

In one embodiment of the present specification, Cy1 is a monocyclic or bicyclic aliphatic hydrocarbon ring.

In one embodiment of the present specification, Cy1 is a monocyclic aliphatic hydrocarbon ring.

In one embodiment of the present specification, Cy1 is a cyclopentane ring; or a cyclohexane ring.

In one embodiment of the present specification, the structure in which G32' is substituted for Cy1 is represented by any one of the following structures.

* means the condensation position.

In one embodiment of the present specification, the definitions of G31 and G32 are the same as the definitions of R31 and R32 described above, except that they may form an aromatic hydrocarbon ring by combining with adjacent substituents.

In one embodiment of the present specification, the definition of G32' is the same as the definition of R32 described above, except that it does not form a ring by bonding with an adjacent substituent.

In one embodiment of the present specification, G32' is a substituted or unsubstituted alkyl group.

In one embodiment of the present specification, G32' is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

In one embodiment of the present specification, G32' is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

In one embodiment of the present specification, G32' is a methyl group.

In one embodiment of the present specification, g31 and g32 are integers from 1 to 4.

In one embodiment of the present specification, g32' is an integer from 1 to 12.

In one embodiment of the present specification, g32' is an integer from 1 to 10.

In one embodiment of the present specification, g32' is an integer of 1 to 4.

In one embodiment of the present specification, Formula 1 is represented by any one of the following compounds.

In one embodiment of the present specification, Formula 2 is represented by any one of the following compounds.

In one embodiment of the present specification, Formula 3 is represented by any one of the following compounds.

According to an exemplary embodiment of the present specification, the compound represented by Chemical Formula 1 may be prepared by, for example, a preparation method such as the following Reaction Scheme 1, and other compounds may be similarly prepared.

[Scheme 1]

In Scheme 1, Ar1, L1, l2, R1, R2, a and b are as defined in Formula 1, Xa is a halogen group, preferably X is chloro (-Cl) or bromo (-Br )am.

Reaction Scheme 1 is an amine substitution reaction, which is preferably carried out in the presence of a palladium catalyst and a base, and the reactor for the amine substitution reaction can be changed as known in the art. The manufacturing method may be more specific in Preparation Examples to be described later.

According to an exemplary embodiment of the present specification, the compound of Formula 2 may be prepared according to Reaction Schemes 2 to 4 below, but is not limited thereto. In addition, compounds prepared according to Schemes 2 and 3 below may be substituted with deuterium through the same process as in Scheme 4. At this time, in Scheme 4, the deuterium substitution rate is 40% to 100%. In Schemes 2 to 4 below, the type and number of substituents can be determined by appropriately selecting known starting materials by those skilled in the art. Reaction type and reaction conditions may be used those known in the art.

[Scheme 2]

[Scheme 3]

[Scheme 4]

The deuteration level of the compound according to an exemplary embodiment of the present specification may be determined by NMR analysis and mass spectrometry.

According to an exemplary embodiment of the present specification, the compound represented by Chemical Formula 3 may be prepared by, for example, a preparation method such as the following Reaction Schemes 5 and 6, and other compounds may be similarly prepared.

[Scheme 5]

[Scheme 6]

In Reaction Schemes 5 and 6, the definitions of R ₁ and R ₃ are the same as those of A1 and A2 in Formula 1, and the definitions of R ₂ and R ₄ are the same as those of R34 and R35 in Formula 1.

Hereinafter, the organic light emitting element will be described.

In the present specification, compounds having various energy band gaps may be synthesized by introducing various substituents into the core structures of the compounds represented by Formulas 1, 2 and 3. In addition, in the present specification, the HOMO and LUMO energy levels of the compound can be controlled by introducing various substituents into the core structure of the above structure.

In addition, the organic light emitting device according to the present specification includes an anode; cathode; A first organic material layer and a second organic material layer provided between the anode and the cathode, wherein the first organic material layer contains the compound represented by Formula 1, and the second organic material layer contains the compound represented by Formula 2 described above. And it is characterized in that it comprises a compound represented by the above formula (3).

The organic light emitting device of the present specification is a typical organic light emitting device except that the first organic material layer is formed using the compound of Formula 1 and the second organic material layer is formed using the compounds of Formulas 2 and 3 described above. It can be manufactured by the manufacturing method and material of the device.

The compound may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device. Here, the solution coating method means spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited to these.

The organic material layer of the organic light emitting device of the present specification may have a single-layer structure, or may have a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention includes a hole transport layer, a hole injection layer, an electron blocking layer, a hole transport and hole injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron transport and injection layer simultaneously. It may have a structure including one or more layers among the layers to be. However, the structure of the organic light emitting device of the present specification is not limited thereto and may include fewer or more organic material layers.

In the organic light emitting device of the present specification, the second organic material layer of the organic light emitting device of the present specification is a light emitting layer, and the first organic material layer is provided between the light emitting layer and the anode.

In the organic light emitting device of the present specification, the first organic material layer of the organic light emitting device of the present specification includes a hole injection layer, a hole transport layer, a hole injection and transport layer, or an electron blocking layer, and the hole injection layer, the hole transport layer, the hole injection and The transport layer or the electron blocking layer may include the compound represented by Chemical Formula 1 described above.

In the organic light emitting device of the present specification, the second organic material layer includes a hole injection layer, a hole transport layer, a hole injection and transport layer, or an electron blocking layer, and the hole injection layer, the hole transport layer, the hole injection and transport layer, or the electron blocking layer may include the compound represented by Formula 2 above.

In another organic light emitting device of the present specification, the second organic material layer includes an electron transport layer or an electron injection layer, and the electron transport layer or electron injection layer contains a compound represented by Formula 2 and a compound represented by Formula 3. can include

In another organic light emitting device of the present specification, the first organic material layer may include an electron blocking layer, and the electron blocking layer may include the compound represented by Chemical Formula 1 described above.

In another organic light emitting device of the present specification, the second organic material layer includes an electron blocking layer, and the electron blocking layer may include the compound represented by Chemical Formula 2 and the compound represented by Chemical Formula 3.

According to one example, the thickness of the first organic material layer including the compound of Formula 1 is 10 Å to 200 Å, preferably 20 Å to 100 Å.

According to one example, the thickness of the second organic material layer including the compound of Formula 2 and the compound of Formula 3 is 100 Å to 500 Å, preferably 150 Å to 300 Å.

In the organic light emitting device of the present specification, the first organic material layer is an electron blocking layer, and the electron blocking layer may include the compound represented by Chemical Formula 1 described above.

In the organic light emitting device of the present specification, the second organic material layer is a light emitting layer, and the light emitting layer may include the compound represented by Formula 2 and the compound represented by Formula 3 described above.

According to another exemplary embodiment, the second organic material layer is a light emitting layer, and the light emitting layer may include the compound represented by Chemical Formula 2 as a host of the light emitting layer.

According to another exemplary embodiment, the second organic material layer is a light emitting layer, and the light emitting layer may include the compound represented by Chemical Formula 3 as a dopant of the light emitting layer.

According to another exemplary embodiment, the second organic material layer is a light emitting layer, and the light emitting layer may include the compound represented by Chemical Formula 3 as a host of the light emitting layer.

According to another exemplary embodiment, the second organic material layer is a light emitting layer, and the light emitting layer may include the compound represented by Chemical Formula 2 as a dopant of the light emitting layer.

In one embodiment of the present specification, the second organic material layer is a light emitting layer, the light emitting layer may include the compound represented by Chemical Formula 2 as a host of the light emitting layer, and may include the compound represented by Chemical Formula 3 as a dopant of the light emitting layer. there is. In this case, the content of the compound represented by Formula 3 may be included in 1 part by weight to 60 parts by weight based on 100 parts by weight of the host, and preferably included in 1 part by weight to 10 parts by weight.

In one embodiment of the present specification, the second organic material layer is a light emitting layer, the light emitting layer includes the compound represented by Chemical Formula 2 as a host of the light emitting layer, and the compound represented by Chemical Formula 3 as a dopant of the light emitting layer, Additional dopants may be further included.

At this time, the dopant is a phosphorescent material such as (4,6-F2ppy) ₂ Irpic, spiro-DPVBi, spiro-6P, distylbenzene (DSB), distryarylene (DSA), PFO-based polymer, PPV-based Fluorescent materials such as polymers, anthracene-based compounds, pyrene-based compounds, and boron-based compounds may be used, but are not limited thereto.

In another exemplary embodiment, the first organic compound layer may further include other organic compounds, metals, or metal compounds in addition to the compound represented by Chemical Formula 1.

In another exemplary embodiment, the second organic material layer may further include other organic compounds, metals, or metal compounds in addition to the compounds represented by Chemical Formula 2 and Chemical Formula 3.

In the organic light emitting device according to one embodiment of the present specification, the light emitting layer further includes a fluorescent dopant or a phosphorescent dopant. At this time, the dopant in the light emitting layer is included in 1 part by weight to 50 parts by weight based on 100 parts by weight of the host.

In the organic light emitting device according to an exemplary embodiment of the present specification, the maximum emission peak of the second organic material layer is 400 nm to 500 nm.

The organic light emitting device of the present specification may further include one or more organic material layers of a hole transport layer, a hole injection layer, an electron blocking layer, an electron transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and a hole transport and injection layer. can

According to an example, the second organic material layer is provided in contact with the first organic material layer. Here, contact means that no other organic material layer exists between the first organic material layer and the second organic material layer.

In the organic light emitting device of the present invention, the organic material layer may include an electron blocking layer, and materials known in the art may be used for the electron blocking layer.

The organic light emitting device may have, for example, a stacked structure as described below, but is not limited thereto.

(1) anode/hole transport layer/light emitting layer/cathode

(2) anode/hole injection layer/hole transport layer/light emitting layer/cathode

(3) anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/cathode

(4) anode/hole transport layer/light emitting layer/electron transport layer/cathode

(5) anode/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode

(6) anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / cathode

(7) anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode

(8) Anode / hole injection layer / hole buffer layer / hole transport layer / light emitting layer / electron transport layer / cathode

(9) Anode / hole injection layer / hole buffer layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode

(10) Anode / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / cathode

(11) Anode / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / electron injection layer / cathode

(12) Anode / hole injection layer / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / cathode

(13) Anode / hole injection layer / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / electron injection layer / cathode

(14) anode / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / cathode

(15) Anode / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode

(16) Anode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / cathode

(17) anode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode

(18) Anode / hole injection layer / hole transport layer / electron blocking layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode

The structure of the organic light emitting device of the present specification may have a structure as shown in FIGS. 1 and 2, but is not limited thereto.

1 illustrates a structure of an organic light emitting device in which a substrate 1, an anode 2, an electron blocking layer 5, an emission layer 6, and a cathode 10 are sequentially stacked. In such a structure, the compound may be included in the electron blocking layer 5 or the light emitting layer 6 .

2 shows a substrate (1), an anode (2), a hole injection layer (3), a hole transport layer (4), an electron blocking layer (5), a light emitting layer (6), a hole blocking layer (7), an electron transport layer (8) , the structure of the organic light emitting device in which the electron injection layer 9 and the cathode 10 are sequentially stacked is illustrated. In this structure, the compound is used in the hole injection layer 3, the hole transport layer 4, the electron blocking layer 5, the light emitting layer 6, the hole blocking layer 7, the electron transport layer 8, or the electron injection layer. layer 9 may be included.

For example, the organic light emitting device according to the present specification uses a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation to form a metal or conductive metal oxide or an alloy thereof on a substrate. It is prepared by depositing an anode, forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron blocking layer, an electron transport layer, and an electron injection layer thereon, and then depositing a material that can be used as a cathode thereon. It can be. In addition to this method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

The organic material layer may further include at least one of a hole transport layer, a hole injection layer, an electron blocking layer, an electron transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and a hole transport and injection layer.

The organic material layer may have a multilayer structure including a hole injection layer, a hole transport layer, a hole injection and transport layer, an electron blocking layer, a light emitting layer and an electron transport layer, an electron injection layer, and an electron transport and injection layer, but is not limited thereto and may have a single layer structure. can In addition, the organic material layer can be formed by a solvent process other than a deposition method using various polymer materials, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or a thermal transfer method. Can be made in layers.

The anode is an electrode for injecting holes, and the anode material is preferably a material having a high work function so that holes can be smoothly injected into the organic material layer. Specific examples of the anode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO: Al or SnO ₂ : Sb; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

The cathode is an electrode for injecting electrons, and it is preferable that the cathode material is a material having a small work function so as to easily inject electrons into the organic material layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; There are multi-layered materials such as LiF/Al or LiO ₂ /Al, but are not limited thereto.

The hole injection layer is a layer that serves to facilitate the injection of holes from the anode to the light emitting layer, and the hole injection material is a material that can receive holes well from the anode at a low voltage, HOMO (highest occupied) of the hole injection material molecular orbital) is preferably between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include metal porphyrine, oligothiophene, arylamine-based organic materials, hexanitrilehexaazatriphenylene-based organic materials, quinacridone-based organic materials, and perylene-based organic materials. of organic materials, anthraquinone, polyaniline, and polythiophene-based conductive polymers, but are not limited thereto. The hole injection layer may have a thickness of 1 nm to 150 nm. If the thickness of the hole injection layer is 1 nm or more, there is an advantage in preventing the hole injection characteristic from deteriorating, and if it is 150 nm or less, the thickness of the hole injection layer is too thick to increase the driving voltage to improve the movement of holes. There are advantages to avoiding this.

The hole transport layer may play a role of facilitating hole transport. As the hole transport material, a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer, and a material having high hole mobility is suitable. Specific examples include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers having both conjugated and non-conjugated parts.

A hole buffer layer may be additionally provided between the hole injection layer and the hole transport layer, and may include a hole injection or transport material known in the art.

An electron blocking layer may be provided between the hole transport layer and the light emitting layer. A compound represented by Chemical Formula 1 or a material known in the art may be used for the electron blocking layer.

The light emitting layer may emit red, green or blue light and may be made of a phosphorescent material or a fluorescent material. The light emitting material is a material capable of emitting light in the visible ray region by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; compounds of the benzoxazole, benzthiazole and benzimidazole series; poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; Polyfluorene, rubrene, etc., but are not limited thereto.

Host materials for the light emitting layer include compounds represented by the above formula (2), condensed aromatic ring derivatives or heterocyclic compounds. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type furan compounds, pyrimidine derivatives, etc., but are not limited thereto.

When the light emitting layer emits red light, PIQIr (acac) (bis (1-phenylisoquinoline) acetylacetonateiridium), PQIr (acac) (bis (1-phenylquinoline) acetylacetonate iridium), A phosphorescent material such as tris(1-phenylquinoline)iridium (PQIr) or octaethylporphyrin platinum (PtOEP) or a fluorescent material such as tris(8-hydroxyquinolino)aluminum (Alq ₃ ) may be used, but is not limited thereto. When the light emitting layer emits green light, phosphorescent materials such as Ir(ppy) ₃ (fac tris(2-phenylpyridine)iridium), Alq3 (tris(8-hydroxyquinolino)aluminum), anthracene-based compounds, and pyrene-based light emitting dopants are used. Fluorescent materials such as compounds and boron-based compounds may be used, but are not limited thereto. When the light emitting layer emits blue light, as the light emitting dopant, a phosphorescent material such as (4,6-F2ppy) ₂ Irpic, spiro-DPVBi, spiro-6P, distylbenzene (DSB), distryarylene (DSA), Fluorescent materials such as PFO-based polymers, PPV-based polymers, anthracene-based compounds, pyrene-based compounds, and boron-based compounds may be used, but are not limited thereto.

A hole blocking layer may be provided between the electron transport layer and the light emitting layer, and materials known in the art may be used.

The electron transport layer may serve to facilitate electron transport. As the electron transport material, a material capable of receiving electrons from the cathode and transferring them to the light emitting layer is suitable. Specific examples include Al complexes of the aforementioned compounds or 8-hydroxyquinoline; Complexes containing Alq ₃ ; organic radical compounds; hydroxyflavone-metal complexes and the like, but are not limited thereto. The electron transport layer may have a thickness of 1 nm to 50 nm. If the thickness of the electron transport layer is 1 nm or more, there is an advantage in preventing deterioration of electron transport properties, and if it is 50 nm or less, the thickness of the electron transport layer is too thick to prevent an increase in driving voltage to improve electron movement. There are advantages that can be

The electron injection layer may serve to smoothly inject electrons. The electron injecting material has the ability to transport electrons, has an excellent electron injecting effect from the cathode, a light emitting layer or a light emitting material, prevents movement of excitons generated in the light emitting layer to the hole injection layer, and also , compounds having excellent thin film forming ability are preferred. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preonylidene methane, anthrone, etc. and their derivatives, metals complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato) aluminum, tris(2-methyl-8-hydroxyquinolinato) aluminum, tris(8-hydroxyquinolinato) gallium, bis(10-hydroxybenzo[h] Quinolinato) beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)( There are o-cresolato) gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, and bis(2-methyl-8-quinolinato)(2-naphtolato)gallium. Not limited to this.

The hole blocking layer is a layer that blocks holes from reaching the cathode, and may be generally formed under the same conditions as the hole injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, and the like, but are not limited thereto.

The organic light emitting device according to the present invention may be a top emission type, a bottom emission type, or a double side emission type depending on the material used.

Hereinafter, examples will be described in detail in order to specifically describe the present specification. However, the embodiments according to the present specification may be modified in many different forms, and the scope of the present application is not construed as being limited to the embodiments detailed below. The embodiments of the present application are provided to more completely explain the present specification to those skilled in the art.

<Synthesis example>

Preparation Example 1-1: Preparation of Compound HT-1

Compound 4-bromo-N-(4-dibenzo[b,d]furan-4-yl)phenyl)-N-(4-(naphtalen-1-yl)phenyl)aniline( 4-bromo-N-(4-dibenzo[b,d]furan-4-yl)phenyl)-N-(4-(naphthalen-1-yl)phenyl)aniline) (8.57 g, 17.38 mmol), (3-(9H-carbazol-9-yl)phenyl)boronic acid ((3-(9H-carbazol-9-yl)phenyl)boronic acid) (5.49 g, 19.12 mmol) was completely dissolved in 240 ml of tetrahydrofuran. After dissolving, a 2M aqueous solution of potassium carbonate (120 ml) was added, and tetrakis-(triphenylphosphine)palladium (0.60 g, 0.52 mmol) was added thereto, followed by heating and stirring for 3 hours. After lowering the temperature to room temperature, removing the water layer, drying with anhydrous magnesium sulfate, concentrating under reduced pressure, and recrystallizing with 240 ml of ethyl acetate to prepare compound HT-1 (7.26g, 64%).

MS[M+H] ⁺ = 779

Preparation Example 1-2: Preparation of Compound HT-2

Compound 4-bromo-N-(4-dibenzo[b,d]furan-4-yl)phenyl)-N-phenylaniline(4-bromo-N-(4-dibenzo [b,d]furan-4-yl)phenyl)-N-phenylaniline) (10.80 g, 22.04 mmol), (3-(9H-carbazol-9-yl)phenyl)boronic acid((3-(9H- Carbazol-9-yl) phenyl) boronic acid) (6.96 g, 24.24 mmol) was completely dissolved in 240 ml of tetrahydrofuran, 2M potassium carbonate aqueous solution (120 ml) was added, and tetrakis- (triphenylphosphine) After adding palladium (0.76 g, 0.66 mmol), the mixture was heated and stirred for 3 hours. After lowering the temperature to room temperature, removing the water layer, drying with anhydrous magnesium sulfate, concentrating under reduced pressure, and recrystallizing with 250 ml of ethyl acetate to prepare compound HT-2 (9.81 g, 68%).

MS[M+H] ⁺ = 653

Preparation Example 1-3: Preparation of compound HT-3

Compound compound 4-bromo-N-(4-dibenzo[b,d]furan-4-yl)phenyl)-[1,1':4':1''-terphenyl] in a 500 ml round bottom flask under nitrogen atmosphere -4-amine (4-bromo-N- (4-dibenzo [b, d] furan-4-yl) phenyl) - [1,1': 4': 1''-terphenyl] -4- Amine) (7.26 g, 11.31 mmol), (2- (9H-carbazol-9-yl) phenyl) boronic acid ((2- (9H-carbazol-9-yl) phenyl) boronic acid) (3.57 g, 12.44 mmol) was completely dissolved in 240 ml of tetrahydrofuran, 2M potassium carbonate aqueous solution (120 ml) was added, tetrakis-(triphenylphosphine) palladium (0.39 g, 0.34 mmol) was added, and the mixture was heated and stirred for 3 hours. . After lowering the temperature to room temperature, removing the water layer, drying with anhydrous magnesium sulfate, concentrating under reduced pressure, and recrystallizing with 250 ml of ethyl acetate to prepare compound HT-3 (5.34 g, 72%).

MS[M+H] ⁺ = 806

Preparation Example 2-1: Preparation of Compound BH-1

(Preparation Example 2-1-1) Preparation of compound 1-3

Dissolve 9-bromoanthracene (50.0g, 194mmol) and naphthalene-1-boronic acid (36.79g, 214mmol) in 500ml of 1,4-dioxane in a three-necked flask, and K ₂ CO ₃ (80.6g, 583mmol) into H ₂ O was dissolved in 200ml. Pd(P(t-Bu) ₃ ) ₂ (1.98 g, 3.9 mmol) was added thereto, and the mixture was stirred for 5 hours under reflux conditions in an argon atmosphere. Upon completion of the reaction, after cooling to room temperature, the reaction solution was transferred to a separatory funnel and extracted with water and toluene. After drying the extract with MgSO ₄ , filtering and concentrating, the sample was purified by silica gel column chromatography to obtain 49.8 g of compound 1-3. (Yield 84%, MS[M+H]+=305)

(Preparation Example 2-1-2) Preparation of compound 1-2

Compound 1-3 (20.0g, 65.7mmol), N-bromosuccinimide (NBS) (11.8g, 65.7mmol), and 300ml of dimethylformamide (DMF) were put in a two-necked flask and incubated for 10 minutes at room temperature under an argon atmosphere. Stir for an hour. After completion of the reaction, the reaction solution was transferred to a separatory funnel, and the organic layer was extracted with water and ethyl acetate. After drying the extract with MgSO ₄ , filtering and concentrating, the sample was purified by silica gel column chromatography to obtain 18.5 g of compound 1-2. (Yield 74%, MS[M+H]+=383)

(Preparation Example 2-1-3) Preparation of compound 1-1

Compound 1-2 (20.0g, 52.2mmol) and naphthalene-2-boronic acid (9.9g, 57.4mmol) were dissolved in 300ml of 1,4-dioxane in a three-necked flask, and K ₂ CO ₃ (14.4g, 104mmol) was added. It was dissolved in 100 ml of H ₂ O. Pd(P(t-Bu) ₃ ) ₂ (0.27g, 0.52mmol) was added thereto, and the mixture was stirred for 5 hours under reflux conditions in an argon atmosphere. Upon completion of the reaction, after cooling to room temperature, the reaction solution was transferred to a separatory funnel and extracted with water and toluene. After drying the extract with MgSO ₄ , filtering and concentrating, the sample was purified by silica gel column chromatography to obtain 11.9 g of compound 1-1. (Yield 52%, MS[M+H]+=431)

(Preparation Example 2-1-4) Synthesis of Compound BH-1

Compound 1-1 (20g) and AlCl ₃ (4g) were put in C ₆ D ₆ (300ml) and stirred for 2 hours. After completion of the reaction, D ₂ O (50ml) was added, stirred for 30 minutes, and trimethylamine (6ml) was added dropwise. The reaction solution was transferred to a separatory funnel and extracted with water and toluene. The extract was dried with MgSO ₄ and recrystallized with ethyl acetate to obtain 15.2 g of compound BH-1. (Yield 72%, MS[M+H]+=452)

Preparation Example 2-2: Preparation of Compound BH-2

(Preparation Example 2-2-1) Preparation of compound 2-2

Compound 2- was synthesized in the same manner as in Preparation Example 2-1-4, except that 9- (naphthalen-1-yl) anthracene (9-naphthalen-1-yl) anthracene was used instead of Compound 1-1. 2 yielded 13.3 g. (Yield 63%, MS[M+H]+=321)

(Preparation Example 2-2-2) Preparation of compound 2-1

17.4 g of compound 2-1 was obtained by synthesizing in the same manner as in Preparation Example 2-1-2, except that compound 2-2 was used instead of compound 1-3. (Yield 70%, MS[M+H]+=398)

(Preparation Example 2-2-3) Preparation of compound BH-2

Compound 2-1 was used instead of Compound 1-2, and dibenzo[b,d]furan-2-ylboronic acid was used instead of naphthalene-2-boronic acid. Except, the synthesis was performed in the same manner as in Preparation Example 2-1-3 to obtain 16.6 g of compound BH-2. (Yield 79%, MS[M+H]+=493)

Preparation Example 2-3: Preparation of Compound BH-3

(Preparation Example 2-3-1) Preparation of compound 3-5

In a three-necked flask, 2-bromoanthracene (50.0 g, 194 mmol) and naphthylboronic acid (26.1 g, 214 mmol) were dissolved in 500 ml of 1,4-dioxane, and K ₂ CO ₃ (53.8 g, 389 mmol) was dissolved in H ₂ O dissolved in 200 ml. Pd(P(t-Bu) ₃ ) ₂ (0.99g, 1.9mmol) was added thereto, and the mixture was stirred for 5 hours under reflux conditions in an argon atmosphere. Upon completion of the reaction, after cooling to room temperature, the reaction solution was transferred to a separatory funnel and extracted with water and toluene. After drying the extract with MgSO ₄ , filtering and concentrating, the sample was purified by silica gel column chromatography to obtain 20.6 g of compound 3-5. (Yield 87%, MS[M+H]+=305)

(Preparation Example 2-3-2) Preparation of compound 3-4

17.2 g of compound 3-4 was obtained by synthesizing in the same manner as in Preparation Example 2-1-2, except that compound 3-5 was used instead of compound 1-2. (Yield 68%, MS[M+H]+=384)

(Preparation Example 2-3-3) Preparation of compound 3-3

19.1 g of compound 3-3 was obtained by synthesizing in the same manner as in Preparation Example 2-1-1, except that compound 3-4 was used instead of 9-bromoanthracene. (Yield 85%, MS[M+H]+=431)

(Preparation Example 2-3-4) Preparation of compound 3-2

18.4 g of compound 3-2 was obtained by synthesizing in the same manner as in Preparation Example 2-1-2, except that compound 3-3 was used instead of compound 1-2. (Yield 78%, MS[M+H]+=510)

(Preparation Example 2-3-5) Preparation of compound 3-1

Compound 3-2 (10-bromo-2,9-di (naphthalen-1-yl) anthracene, 10-bromo-2,9-di (naphthalen-1-yl) anthracene) (20.0 g, 60.2mmol) and naphthalene-2-ylboronic acid (14.0g, 66.2mmol) were dissolved in 300ml of 1,4-dioxane, and K ₂ CO ₃ (16.6g, 120mmol) was dissolved in H ₂ O was dissolved in 100 ml. Pd(P(t-Bu) ₃ ) ₂ (0.31 g, 0.60 mmol) was added thereto, and the mixture was stirred for 5 hours under reflux conditions in an argon atmosphere. Upon completion of the reaction, after cooling to room temperature, the reaction solution was transferred to a separatory funnel and extracted with water and toluene. After drying the extract with MgSO ₄ , filtering and concentrating, the sample was purified by silica gel column chromatography to obtain 11.4 g of compound 3-1. (Yield 52%, MS[M+H]+=557)

(Preparation Example 2-3-6) Preparation of compound BH-3

17.2 g of compound BH-3 was obtained by synthesizing in the same manner as in Preparation Example 1-4, except that compound 3-1 was used instead of compound 1-1. (Yield 82%, MS[M+H]+=585)

Preparation Example 2-4: Preparation of Compound BH-4

(Preparation Example 2-4-1) Preparation of compound 4-1

Dibenzofuran-2-boronic acid (20.0g, 94.3mmol) and 1-bromo-4-chlorobenzene (18.1g, 94.3mmol) were dissolved in 300ml of THF in a three-necked flask, and K ₂ CO ₃ (39.1g, 283mmol) ) was dissolved in 100 ml of H ₂ O. Pd(P(t-Bu) ₃ ) ₂ (0.96g, 1.9mmol) was added thereto, and stirred for 2 hours under reflux conditions in an argon atmosphere. Upon completion of the reaction, after cooling to room temperature, the reaction solution was transferred to a separatory funnel and extracted with water and toluene. After drying the extract with MgSO ₄ , filtering and concentrating, the next reaction was performed immediately.

The above 4-2 mixture, bis(pinacolato)diboron (28.7g, 113mmol), and KOAc (27.8g, 283mmol) were dissolved in 300ml of 1,4-dioxane in a three-necked flask, and Pd(dppf)Cl ₂ ( 1.38g, 1.89mmol) was added and stirred for 12 hours under reflux in an argon atmosphere. After the reaction was completed, the mixture was cooled to room temperature, concentrated, and then extracted with water and chloroform. After drying the extract with MgSO ₄ , filtering and concentrating, the sample was purified by silica gel column chromatography to obtain 23.3 g of compound 4-1. (total yield 67%, MS[M+H]+=371)

(Preparation Example 2-4-2) Preparation of compound BH-4

Synthesis proceeds in the same manner as in Preparation Example 2-2-3 except that Compound 4-1 was used instead of dibenzo[b,d]furan-2-ylboronic acid. Thus, 13.3 g of compound BH-4 was obtained. (Yield 47%, MS[M+H]+=562)

Preparation Example 3-1: Preparation of Compound BD-1

(Preparation Example 3-1-1) Preparation of compound BD-1-1

In a three-necked flask, 1,2,3-tribromo-5-methylbenzene (5 g), bis-(4-(tert-butyl)phenyl)amine (8 g), Pd(P-tBu ₃ ) ₂ (0.15 g) ), NaOBu (4.1 g) was dissolved in 50 ml of xylene and stirred for 3 hours. Upon completion of the reaction, after cooling to room temperature, the reaction solution was transferred to a separatory funnel and extracted with water and toluene. The extract was dried with MgSO ₄ , filtered and concentrated, and then purified by recrystallization (ethyl acetate/hexane) to obtain 7.2 g of compound BD-1-1. (Yield 67%, MS[M+H]+=730)

(Preparation Example 3-1-2) Preparation of compound BD-1

To a flask containing compound BD-1-1 (7.2g) and xylene (100ml), an n-butyllithium pentane solution (8ml, 2.5M in hexane) was added dropwise at 0°C under an argon atmosphere. After completion of the dropping, the temperature was raised to 50 ^° C. and stirred for 2 hours. After cooling to -40 ^° C, boron tribromide (2.80 ml) was added, and the mixture was heated to room temperature and stirred for 4 hours. Thereafter, the mixture was cooled to 0 ^° C., N,N-isopropylethylamine (8ml) was added, and the reaction mixture was further stirred at room temperature for 30 minutes. After adding and separating saturated NaCl solution and ethyl acetate, the solvent was distilled off under reduced pressure. Purification by silica gel column chromatography gave 1.5 g of compound BD-1. (Yield 23%, MS[M+H]+=660)

Preparation Example 3-2: Preparation of Compound BD-2

(Preparation Example 3-2-1) Preparation of compound BD-2-2

In a three-necked flask, 1-bromo-2,3-dichloro-5-methylbenzene (10 g), N-(4-(t-butyl)phenyl)-5,5,8,8-tetramethyl-5,6 ,7,8-tetrahydronaphthalen-2-amine (8 g), Pd(P-tBu ₃ ) ₂ (0.2 g), and NaOBu (4.0 g) were dissolved in 100 ml of xylene and stirred for 3 hours. Upon completion of the reaction, after cooling to room temperature, the reaction solution was transferred to a separatory funnel and extracted with water and toluene. The extract was dried with MgSO ₄ , filtered and concentrated, and then purified by recrystallization (ethyl acetate/hexane) to obtain 10.4 g of compound BD-2-2. (Yield 51%, MS[M+H]+=495)

(Preparation Example 3-2-2) Preparation of compound BD-2-1

Compound BD-2-2, N-(4-(t-butyl)phenyl)-5,5,8,8-tetramethyl-5,6 instead of 1-bromo-2,3-dichloro-5-methylbenzene Compound BD- 7.0 g of 2-1 was obtained. (Yield 45%, MS[M+H]+=740)

(Preparation Example 3-2-3) Preparation of compound BD-2

1.8 g of compound BD-2 was obtained by synthesizing in the same manner as in Preparation Example 3-1-2, except that compound BD-2-1 was used instead of compound BD-1-1. (Yield 27%, MS[M+H]+=713)

Preparation Example 3-3: Preparation of compound BD-3

(Preparation Example 3-3-1) Preparation of compound BD-3-2

In a three-necked flask, 1-bromo-3-chloro-5-methylbenzene (1 eq.) and bis(4-terbutylphenyl)amine (1 eq.) were dissolved in toluene (0.3 M) and sodium terbutoxide ( 1.2 eq.) and bis(tri-tertbutylphosphine)palladium(0) (0.01 eq.) were added thereto, followed by stirring for 2 hours under reflux conditions in an argon atmosphere. After the reaction was completed, after cooling to room temperature, H ₂ O was added and the reaction solution was transferred to a separatory funnel and extracted. The extract was dried over MgSO ₄ and concentrated, and the sample was purified by silica gel column chromatography to obtain compound BD-3-2. (Yield 86%, MS[M+H] ⁺ = 407)

(Preparation Example 3-3-2) Preparation of compound BD-3-1

Compound BD-3-1 was prepared from compound BD-3-2 and 5-terbutyl-N-(4-terbutylphenyl)benzo[b]thiophen-3-amine in the same manner as in Production Example 3-3-1. got (Yield 68%, MS[M+H] ⁺ = 707)

(Preparation Example 3-3-3) Preparation of compound BD-3

After dissolving compound BD-3-1 in 1,2-dichlorobenzene (0.1 M) in a three-necked flask and adding boron triiodide (2 eq.), the mixture was stirred for 5 hours at 160° C. in an argon atmosphere. The reaction mixture was cooled to 0 °C, N,N-diisopropylethylamine (20 eq.) was added, and the mixture was stirred for 1 hour. Extraction was performed in a separatory funnel using toluene and H ₂ O. The extract was dried over MgSO ₄ and concentrated, and the sample was purified by silica gel column chromatography to obtain compound BD-3. (Yield 22%, MS[M+H] ⁺ = 715)

<Example 1>

A glass substrate coated with ITO (Indium Tin Oxide) with a thickness of 1,400 Å was put in distilled water dissolved in detergent and washed with ultrasonic waves. At this time, Fischer Co.'s Decon™ CON705 product was used as a detergent, and distilled water filtered through a 0.22 μm sterilizing filter from Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, ultrasonic cleaning was performed twice with distilled water for 10 minutes. After washing with distilled water, ultrasonic cleaning was performed in isopropyl alcohol, acetone, and methanol solvents for 10 minutes each, dried, and transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transferred to a vacuum deposition machine.

The following HI-A compound and the following HAT-CN compound were sequentially thermally vacuum deposited to a thickness of 650 Å and a thickness of 50 Å, respectively, on the prepared ITO transparent electrode to form a hole injection layer. A hole transport layer was formed on the hole injection layer by vacuum depositing the following HTL compound to a thickness of 600 Å. On the hole transport layer, the previously prepared HT-1 compound was thermally vacuum deposited to a thickness of 50 Å to form an electron blocking layer. On the electron blocking layer, the previously prepared BH-1 and BD-1 compounds were vacuum deposited at a weight ratio of 96:4 to a thickness of 200 Å to form a light emitting layer. A hole blocking layer was formed by vacuum depositing the following ET-A compound on the light emitting layer to a thickness of 50 Å. On the hole blocking layer, the following ET-B compound and the following Liq compound were thermally vacuum deposited at a weight ratio of 1:1 to a thickness of 310 Å to form an electron transport layer. An electron injection layer was formed on the electron transport layer by vacuum depositing the following Liq compound to a thickness of 5 Å. On the electron injection layer, magnesium and silver were sequentially deposited at a weight ratio of 10:1 to a thickness of 120 Å and aluminum to a thickness of 1000 Å to form a cathode, thereby manufacturing an organic light emitting device.

<Examples 2 to 36>

An organic light emitting diode was manufactured in the same manner as in Example 1-1, except that the compounds shown in Table 1 were used instead of HT-1, BH-1, and BD-1 in Example 1.

The deuterium substitution rate of BH-1 is 100%, the deuterium substitution rate of BH-2 is about 68.2%, the deuterium substitution rate of BH-3 is 100%, and the deuterium substitution rate of BH-4 is about 57.7%.

<Comparative Examples 1 to 10>

An organic light emitting diode was manufactured in the same manner as in Example 1, except that the compounds listed in Table 1 were used instead of HT-1, BH-1 and BD-1 in Example 1.

An electric current was applied to the organic light emitting devices prepared in Examples and Comparative Examples to measure external quantum efficiency and lifetime (T95), and the results are shown in Table 1 below. T95 means the time from the current density of 20 mA/cm ² until the luminance decreases to 95% of the initial luminance.

electron blocking layer
ingredient light emitting layer
ingredient light emitting layer
ingredient external quantum efficiency
EQE (%) life span
(T95, hr)
(@20mA/cm ² ) Example 1 HT-1 BH-1 BD-1 10.2 96 Example 2 HT-1 BH-1 BD-2 11 98 Example 3 HT-1 BH-1 BD-3 11.4 100 Example 4 HT-1 BH-2 BD-1 10.1 94 Example 5 HT-1 BH-2 BD-2 11.2 97 Example 6 HT-1 BH-2 BD-3 11.4 102 Example 7 HT-1 BH-3 BD-1 10 93 Example 8 HT-1 BH-3 BD-2 10.9 98 Example 9 HT-1 BH-3 BD-3 11.3 101 Example 10 HT-1 BH-4 BD-1 10.2 94 Example 11 HT-1 BH-4 BD-2 11 99 Example 12 HT-1 BH-4 BD-3 11.4 103 Example 13 HT-2 BH-1 BD-1 10.1 96 Example 14 HT-2 BH-1 BD-2 11 107 Example 15 HT-2 BH-1 BD-3 11.3 107 Example 16 HT-2 BH-2 BD-1 10.2 91 Example 17 HT-2 BH-2 BD-2 10.9 95 Example 18 HT-2 BH-2 BD-3 11.2 99 Example 19 HT-2 BH-3 BD-1 9.9 92 Example 20 HT-2 BH-3 BD-2 10.8 94 Example 21 HT-2 BH-3 BD-3 11.4 96 Example 22 HT-2 BH-4 BD-1 9.8 91 Example 23 HT-2 BH-4 BD-2 10.6 100 Example 24 HT-2 BH-4 BD-3 11.2 102 Example 25 HT-3 BH-1 BD-1 10.2 93 Example 26 HT-3 BH-1 BD-2 10.3 98 Example 27 HT-3 BH-1 BD-3 11.1 100 Example 28 HT-3 BH-2 BD-1 9.8 95 Example 29 HT-3 BH-2 BD-2 10.5 95 Example 30 HT-3 BH-2 BD-3 11.3 99 Example 31 HT-3 BH-3 BD-1 9.9 94 Example 32 HT-3 BH-3 BD-2 10.2 98 Example 33 HT-3 BH-3 BD-3 11 100 Example 34 HT-3 BH-4 BD-1 10 93 Example 35 HT-3 BH-4 BD-2 10.8 96 Example 36 HT-3 BH-4 BD-3 11.3 101 Comparative Example 1 HT-1 BH-A BD-1 8,7 73 Comparative Example 2 HT-1 BH-B BD-1 8.5 81 Comparative Example 3 HT-1 BH-C BD-1 8.4 82 Comparative Example 4 HT-A BH-1 BD-1 7.2 87 Comparative Example 5 HT-B BH-1 BD-1 6.9 81 Comparative Example 6 HT-1 BH-1 BD-A 8.1 83 Comparative Example 7 HT-A BH-1 BD-A 6.7 72 Comparative Example 8 HT-1 BH-A BD-A 6.9 59 Comparative Example 9 HT-B BH-A BD-1 6.6 61 Comparative Example 10 HT-A BH-A BD-A 5.8 53

From the results of Table 1, one of the deuterium-substituted hosts of the BH-1 to BH-4 and one of the dopants of the BD-1 to BD-3 were meta-one of the HT-1 to HT-3 having a phenylene linker. The organic light emitting device used with is a host BH-A to BH-C not substituted with deuterium, HT-A and HT-B having a para-phenylene linker, or a pyrene structure dopant BD-A Compared to Comparative Examples 1 to 10 using , it can be seen that the efficiency is increased while exhibiting excellent life characteristics.

This is because when Formula 2 and Formula 3 of the present invention are used together in the light emitting layer and the compound of Formula 1 is used in the hole transport region, long lifespan and/or This is because the characteristics of high efficiency are enhanced.

Specifically, in the case of a device using the compound HT-1 to HT-3 of Formula 1 of the present invention having a meta-phenylene linker, the effect of increasing efficiency compared to a device using a material having a para-phenylene linker indicate

In addition, compared to BD-A, which is a pyrene-based dopant, boron-based dopants such as BD-1 to BD-3 have a narrower full width at half maximum, thereby increasing efficiency including color purity.

Hosts substituted with deuterium, such as BH-1 to BH-4, exhibit an effect of improving the overall lifetime of the device.

1: substrate
2: anode
3: hole injection layer
4: hole transport layer
5: electron blocking layer
6: light emitting layer
7: hole blocking layer
8: electron transport layer
9: electron injection layer
10: cathode

Claims (17)

anode;
cathode;
In the organic light emitting device including a first organic material layer and a second organic material layer provided between the anode and the cathode,
The first organic material layer includes a compound represented by Formula 1 below,
wherein the second organic material layer includes a compound represented by Formula 2 below and a compound represented by Formula 3-2 or 3-3 below:
[Formula 1]

In Formula 1,
X is O; or S,
L, L1 and L2 are the same as or different from each other, and are each independently a direct bond; Or a substituted or unsubstituted arylene group,
Ar1 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
a is an integer from 0 to 8, b is an integer from 0 to 7, when a is 2 or more, 2 or more R1's are the same as or different from each other, and when b is 2 or more, 2 or more R2's are the same or different from each other,
[Formula 2]

In Formula 2,
L3 and L4 are the same as or different from each other, and are each independently a direct bond; Or a substituted or unsubstituted arylene group,
Ar3 and Ar4 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
R3 is hydrogen; heavy hydrogen; halogen group; cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
c is an integer from 0 to 8, and when c is 2 or more, 2 or more R3s are the same as or different from each other;
The compound represented by Formula 2 is at least 40% substituted with deuterium,
[Formula 3-2]

[Formula 3-3]

In Chemical Formulas 3-2 and 3-3,
E1 is an aromatic hydrocarbon ring; aliphatic hydrocarbon ring; Or a condensed ring of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring,
Y1 is N(Ra1); O; or S,
R31 and R33 to R35 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; or a substituted or unsubstituted amine group, or bonded to adjacent substituents to form a substituted or unsubstituted ring;
R32” and Ra1 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; or a substituted or unsubstituted amine group, or bonded to adjacent substituents to form a substituted or unsubstituted ring;
r31 is an integer from 0 to 4, r33 is an integer from 0 to 3, and when r31 and r33 are each 2 or more, the substituents in parentheses are the same as or different from each other,
r32” is an integer of 0 to 5, and when r32” is 2 or more, the substituents in parentheses are the same as or different from each other. The organic light emitting device of claim 1, wherein the second organic material layer is a light emitting layer, and the first organic material layer is provided between the light emitting layer and the anode. The organic light emitting device of claim 1, wherein Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-4:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

In Chemical Formulas 1-1 to 1-4, the definitions of X, L, L1, L2, Ar1, R1, R2, a and b are the same as those in Chemical Formula 1. The organic light emitting device of claim 1, wherein Chemical Formula 2 is represented by any one of the following Chemical Formulas 2-1 to 2-3:
[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

In Formulas 2-1 to 2-3, the definitions of L3, L4, Ar4, R3 and c are the same as those in Formula 2,
R4 to R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
d is an integer from 0 to 7, and when d is 2 or more, 2 or more R4 are the same as or different from each other;
e is an integer from 0 to 9, and when e is 2 or more, 2 or more R5's are the same as or different from each other;
f is an integer from 0 to 7, and when f is 2 or more, 2 or more R6's are the same as or different from each other. The organic light emitting device of claim 1, wherein Chemical Formula 2 is represented by the following Chemical Formula 2-4 or 2-5:
[Formula 2-4]

[Formula 2-5]

In Formulas 2-4 and 2-5, the definitions of L3, L4 and Ar4 are the same as those in Formula 2,
Ar5 is a substituted or unsubstituted aryl group,
R4 and R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
G1 is hydrogen; heavy hydrogen; halogen group; cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
d is an integer from 0 to 7, and when d is 2 or more, 2 or more R4 are the same as or different from each other;
f is an integer from 0 to 7, and when f is 2 or more, 2 or more R6 are the same as or different from each other;
g1 is an integer from 0 to 7, and when g1 is 2 or more, 2 or more G1s are the same as or different from each other. The organic light emitting device of claim 1, wherein the compound represented by Chemical Formula 2 is substituted with deuterium by 60% or more. The organic light emitting device of claim 1, wherein the compound represented by Chemical Formula 2 is substituted by 80% or more with deuterium. The organic light emitting device of claim 1, wherein Chemical Formula 2 is represented by the following Chemical Formula A-1 or A-2:
[Formula A-1]

[Formula A-2]

In the above formulas A-1 and A-2,
D means deuterium, and the definitions of L3, L4, Ar3 and Ar4 are the same as those in Formula 2,
Ar5 is a substituted or unsubstituted aryl group. delete delete anode;
cathode;
In the organic light emitting device including a first organic material layer and a second organic material layer provided between the anode and the cathode,
The first organic material layer includes a compound represented by Formula 1 below,
wherein the second organic material layer includes a compound represented by Formula 2 and a compound represented by Formula 301-B below:
[Formula 1]

In Formula 1,
X is O; or S,
L, L1 and L2 are the same as or different from each other, and are each independently a direct bond; Or a substituted or unsubstituted arylene group,
Ar1 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
a is an integer from 0 to 8, b is an integer from 0 to 7, when a is 2 or more, 2 or more R1's are the same as or different from each other, and when b is 2 or more, 2 or more R2's are the same or different from each other,
[Formula 2]

In Formula 2,
L3 and L4 are the same as or different from each other, and are each independently a direct bond; Or a substituted or unsubstituted arylene group,
Ar3 and Ar4 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
R3 is hydrogen; heavy hydrogen; halogen group; cyano group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
c is an integer from 0 to 8, and when c is 2 or more, 2 or more R3s are the same as or different from each other;
The compound represented by Formula 2 is at least 40% substituted with deuterium,
[Formula 301-B]

In Formula 301-B,
Cy1 is a cyclohexane ring,
R33 is hydrogen; heavy hydrogen; halogen group; cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; or a substituted or unsubstituted amine group, or bonded to adjacent substituents to form a substituted or unsubstituted ring;
R36 and R37 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; or a substituted or unsubstituted amine group, or bonded to adjacent substituents to form a substituted or unsubstituted ring;
G31 is hydrogen; heavy hydrogen; halogen group; cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; or a substituted or unsubstituted amine group, or bonded to an adjacent substituent to form a substituted or unsubstituted aromatic hydrocarbon ring;
G32' is hydrogen; heavy hydrogen; halogen group; cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted arylalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heterocyclic group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; Or a substituted or unsubstituted amine group,
r33 is an integer from 0 to 3, and when r33 is 2 or more, two or more R33s are the same as or different from each other;
r36 and r37 are integers from 0 to 5, and when r36 and r37 are 2 or more, the substituents in parentheses are the same as or different from each other;
g31 is an integer of 0 to 4, g32' is an integer of 0 or more, and when g31 and g32' are 2 or more, the substituents in parentheses are the same as or different from each other. The organic light emitting device of claim 1, wherein Chemical Formula 1 is represented by any one of the following compounds:

. The organic light emitting device of claim 1, wherein Chemical Formula 2 is represented by any one of the following compounds:

. The organic light emitting device of claim 1, wherein the compound represented by Chemical Formula 3-2 or 3-3 is represented by one of the following compounds:

. The method of claim 1,
The second organic material layer is an organic light emitting device provided in contact with the first organic material layer. The method of claim 1,
The organic light emitting device further comprises one or more organic material layers of a hole transport layer, a hole injection layer, an electron blocking layer, an electron transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and a hole transport and injection layer. light emitting element. The method of claim 11,
Formula 301-B is an organic light emitting device represented by any one of the following compounds:

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