KR102667151B1 - Organic light emitting device comprising organic compounds - Google Patents

Abstract

This specification relates to an organic light-emitting device including a light-emitting layer and a first organic material layer.

Description

Organic light-emitting device containing organic compounds {ORGANIC LIGHT EMITTING DEVICE COMPRISING ORGANIC COMPOUNDS}

This specification relates to an organic light-emitting device containing an organic compound.

This application claims the benefit of the filing date of Korean Patent Application No. 10-2020-0105382 filed with the Korea Intellectual Property Office on August 21, 2020, the entire contents of which are included in this specification.

In general, organic luminescence refers to a phenomenon that converts electrical energy into light energy using organic materials. Organic light-emitting devices that utilize the organic light-emitting phenomenon usually have a structure including an anode, a cathode, and an organic material layer between them. Here, the organic material layer is often composed of a multi-layer structure composed of different materials to increase the efficiency and stability of the organic light-emitting device, and may be composed of, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. In the structure of this organic light-emitting device, when a voltage is applied between two electrodes, holes are injected from the anode and electrons from the cathode into the organic material layer. When the injected holes and electrons meet, an exciton is formed, and this exciton When it falls back to the ground state, it glows.

The development of new materials for organic light-emitting devices as described above continues to be required.

Public Patent Publication 10-2015-0011347

The present specification seeks to provide an organic light-emitting device containing an organic compound.

This specification

anode; cathode; And an organic material layer provided between the anode and the cathode,

The organic material layer includes a light-emitting layer and a first organic material layer,

The first organic layer is provided between the cathode and the light emitting layer,

The light-emitting layer includes a compound of the following formula (1),

The first organic material layer provides an organic light-emitting device including a compound of the following formula (2).

[Formula 1]

In Formula 1,

L1 and L2 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,

Ar1 and Ar2 are the same or different from each other, and are each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

D is deuterium,

[Formula 2]

In Formula 2,

L3 to L5 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,

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

Ar5 is hydrogen; heavy hydrogen; Cyano group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

At least one of Ar3 to Ar5 is a cyano group or contains one or more cyano groups as a substituent,

n1 is an integer from 0 to 7.

The organic light emitting device described in this specification includes the compound of Formula 1 in the light emitting layer and the compound of Formula 2 in the first organic layer, thereby having a low driving voltage, excellent efficiency characteristics, and excellent lifespan. Specifically, low driving voltage, high efficiency, and lifetime can be improved by controlling the degree of electron transport through appropriate adjustment of HOMO energy level and LUMO energy level.

1, 2, and 8 show examples of organic light-emitting devices according to an exemplary embodiment of the present specification.
3 to 7 show examples of organic light-emitting devices including two or more stacks.

Hereinafter, this specification will be described in more detail.

Formula 1 of the present invention has deuterium connected to carbons 1 to 8 of anthracene, and is chemically more stable than hydrogen in the recombination region in the light-emitting layer, thereby improving the lifespan of the organic light-emitting device.

Formula 2 of the present invention has the effect of improving electron injection by increasing the intramolecular dipole moment by linking a substituent including a cyano group to anthracene.

When the compound of Formula 1 is used in the light emitting layer and the compound of Formula 2 is used in the first organic material layer (specifically, the electron transport region), the long life, low voltage, and high efficiency characteristics of the device are enhanced.

The compound of Formula 1 and the compound of Formula 2 satisfy the following Formula 1.

[Equation 1]

| DM ₂ - DM ₁ | ≥ 3 debye

In equation 1 above,

DM ₁ is the dipole moment of the compound of Formula 1,

DM ₂ is the dipole moment of the compound of Formula 2.

When the above equation 1 is satisfied, electron injection from the cathode to the compound of formula 2 occurs effectively, and electron transfer to the light-emitting layer can be properly maintained. Accordingly, the efficiency and lifespan of the organic light emitting device are improved.

In this specification, dipole moment is a physical quantity indicating the degree of polarity, and can be calculated using Equation 1 below.

[Equation 1]

By calculating the molecular density from Equation 1 above, the value of the dipole moment can be obtained. For example, molecular density can be obtained by calculating the charge and dipole of each atom using a method called Hirshfeld Charge Analysis and then calculating according to the formula below.

According to an exemplary embodiment of the present specification, the dipole moment value can be calculated using the quantum chemical calculation program Gaussian 03 manufactured by Gaussian, USA. Specifically, using density functional theory (DFT), the dipole moment can be calculated using time-dependent density functional theory (TD-DFT) for a structure optimized using B3LYP as the functional and 6-31G* as the basis function. You can get the calculated value.

In an exemplary embodiment of the present specification, the | DM ₂ - DM ₁ | is less than 6.5 debye.

In this specification, * or dotted lines refer to connected portions.

In this specification, Cn means n carbon atoms, and Cn-Cm means n to m carbon atoms.

Examples of substituents in this 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 changed to another substituent. The position to be substituted is not limited as long as it is the position where the hydrogen atom is substituted, that is, a position where the substituent can be substituted, and if two or more substituents are substituted. , two or more substituents may be the same or different from each other.

As used herein, the term “substituted or unsubstituted” refers to deuterium; halogen group; Cyano group; Alkyl group; Aryl group; and a heterocyclic group, or is substituted with a substituent in which two or more of the above-exemplified substituents are linked, or does not have any substituent.

In this specification, linking two or more substituents means that the hydrogen of one substituent is replaced with another substituent. For example, an isopropyl group and a phenyl group are connected to or It can be a substituent of .

In this specification, three substituents are connected not only by (substituent 1) - (substituent 2) - (substituent 3) being connected in succession, but also by (substituent 2) and (substituent 3) being connected to (substituent 1). It also includes being connected. For example, two phenyl groups and an isopropyl group are connected or It can be a substituent of . The same applies as above to those where 4 or more substituents are connected.

In this specification, N% deuterated means that N% of the hydrogen available in the structure is replaced with deuterium. For example, if 25% of dibenzofuran is replaced with deuterium, it means that 2 of the 8 hydrogens in dibenzofuran are replaced with deuterium.

The compound of Formula 1 containing deuterium can be prepared by a known deuteration reaction. According to an exemplary embodiment of the present specification, the compound of Formula 1 may be formed using a deuterated compound as a precursor, or deuterium may be introduced into the compound through a hydrogen-deuterium exchange reaction under an acid catalyst using a deuterated solvent. there is.

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

In this specification, examples of halogen groups include fluorine, chlorine, bromine, or iodine.

In the present specification, the alkyl group may be straight chain or branched, and the number of carbon atoms is not particularly limited, but is 1 to 30; 1 to 20; 1 to 10; Or it is preferably 1 to 5. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, t-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, iso Pentyl, neopentyl, t-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentyl Methyl, cyclohexylmethyl, octyl, n-octyl, t-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1 -Dimethylpropyl, isohexyl, 4-methylhexyl, 5-methylhexyl, etc., but are not limited thereto.

In the present specification, the silyl group may be an alkylsilyl group, an arylgilyl group, or the like. Specifically, it can be represented by the chemical formula -SiYaYbYc, where Ya, Yb, and Yc are each hydrogen; Substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. When Ya, Yb, and Yc are each an alkyl group, the silyl group is a trialkylsilyl group, and when each of Ya, Yb, and Yc is an aryl group, the silyl group is a trialylsilyl group. The silyl group specifically includes, but is not limited to, trimethylsilyl group, triethylsilyl group, tert-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, and phenylsilyl group. No.

In this specification, an aryl group refers to a monovalent group of a monovalent aromatic hydrocarbon or an aromatic hydrocarbon derivative. An aromatic hydrocarbon refers to a compound containing a planar ring in which pi electrons are completely conjugated, and a group derived from an aromatic hydrocarbon refers to a structure in which an aromatic hydrocarbon or a cyclic aliphatic hydrocarbon is condensed with an aromatic hydrocarbon. Additionally, in the present specification, the aryl group is intended to include a monovalent group in which two or more aromatic hydrocarbons or derivatives of aromatic hydrocarbons are linked together. The aryl group is not particularly limited, but has 6 to 50 carbon atoms; 6 to 30; 6 to 25; 6 to 20; 6 to 18; Or preferably 6 to 13, and the aryl group may be monocyclic or polycyclic. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, triphenyl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, etc., but is not limited thereto.

In the present specification, the fluorenyl group may be substituted, and adjacent substituents may combine with each other to form a ring.

In this specification, when it is said that a fluorenyl group can be substituted, the substituted fluorenyl group includes all compounds in which the substituents of the 5-membered fluorene ring are spiro bonded to each other to form an aromatic hydrocarbon ring. The substituted fluorenyl group includes 9,9'-spirobifluorene, spiro[cyclopentane-1,9'-fluorene], spiro[benzo[c]fluorene-7,9-fluorene], etc. However, it is not limited to this.

In the present specification, the substituted aryl group may also include a form in which an aliphatic ring is condensed with an aryl group.

In the present specification, a heterocyclic group refers to a monovalent aromatic heterocycle. Here, the aromatic heterocycle refers to a monovalent group of an aromatic ring or a derivative of an aromatic ring, and includes one or more of N, O, and S as heteroatoms in the ring. The derivatives of the aromatic ring include all structures in which an aromatic ring or an aliphatic ring is condensed with an aromatic ring. In addition, in the present specification, the heterocyclic group is intended to include a monovalent group in which aromatic rings containing two or more heteroatoms or derivatives of aromatic rings containing heteroatoms are linked together. The heterocyclic group has 2 to 50 carbon atoms; 2 to 30; 2 to 20; 2 to 18; Or it is preferably 2 to 13. Examples of heterocyclic groups include thiophene group, furanyl group, pyrrole group, imidazole group, thiazole group, oxazole group, pyridine group, pyrimidine group, triazine group, triazole group, acridine group, pyridazine group, pyrazine group, Quinoline group, quinazoline group, quinoxaline group, isoquinoline group, indole group, carbazole group, benzoxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzo These include, but are not limited to, furan groups, phenanthrolinyl groups, and dibenzofuran groups.

In the present specification, the heterocyclic group may be monocyclic or polycyclic, and may be an aromatic, aliphatic, or a condensed ring of aromatic and aliphatic.

In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the carbon number of the cycloalkyl group is 3 to 20. According to another embodiment, the carbon number of the cycloalkyl group is 3 to 6. Cycloalkyl groups include not only single ring groups but also double ring groups such as bridgeheads, fused rings, and spiro rings. Specifically, it includes cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, and adamantyl group, but is not limited thereto.

In the present specification, an aliphatic hydrocarbon ring refers to all hydrocarbon rings excluding aromatic hydrocarbon rings, and may include a cycloalkyl ring and a cycloalkene ring. The description of the cycloalkyl group described above can be applied except that the cycloalkyl ring is a divalent group, and the description of the cycloalkenyl group described above can be applied to the cycloalkene ring except that it is a divalent group. Additionally, substituted aliphatic hydrocarbon rings also include aliphatic hydrocarbon rings in which an aromatic ring is condensed.

In the present specification, an arylene group refers to an aryl group having two bonding positions, that is, a bivalent group. The description of the aryl group described above can be applied, except that each of these is a divalent group.

In the present specification, a heteroarylene group refers to a heterocyclic group having two bonding positions, that is, a bivalent group. The description of the heterocyclic group described above can be applied, except that each of these is a divalent group.

Hereinafter, the compound of Formula 1 below will be described in detail.

[Formula 1]

In an exemplary embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted arylene group; Or it is a substituted or unsubstituted divalent heterocyclic group.

In an exemplary embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted C6-C60 arylene group; Or it is a substituted or unsubstituted C2-C60 divalent heterocyclic group.

In an exemplary embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted C6-C30 arylene group; Or it is a substituted or unsubstituted C2-C30 divalent heterocyclic group.

In an exemplary embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted phenylene group; Substituted or unsubstituted biphenylene group; Or a substituted or unsubstituted naphthylene group.

In an exemplary embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently directly bonded; Or it is a C6-C30 arylene group substituted or unsubstituted with deuterium.

In an exemplary embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently directly bonded; Or it is a C6-C20 arylene group substituted or unsubstituted with deuterium.

In an exemplary embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently directly bonded; A phenylene group substituted or unsubstituted with deuterium; A biphenylene group substituted or unsubstituted with deuterium; Or it is a naphthylene group substituted or unsubstituted with deuterium.

In one embodiment of the present specification, L1 is a direct bond.

In one embodiment of the present specification, L2 is a direct bond.

In one embodiment of the present specification, one of L1 and L2 is a direct bond.

In an exemplary embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently directly bonded; or any one selected from the structures below.

In the above structure, D means deuterium, k1 is an integer from 0 to 4, and k2 is an integer from 0 to 6.

In one embodiment of the present specification, k1 is 1 or more. In another embodiment, k1 is 2 or more. In another embodiment, k1 is 3 or more. In another embodiment, k1 is 4.

In one embodiment of the present specification, k2 is 1 or more. In another embodiment, k2 is 2 or more. In another embodiment, k2 is 3 or more. In another embodiment, k2 is 4 or more. In another embodiment, k2 is 5 or more. In another embodiment, k2 is 6.

In an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group; Or it is a substituted or unsubstituted heterocyclic group.

In an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted C6-C60 aryl group; Or it is a substituted or unsubstituted C2-C60 heterocyclic group.

In an exemplary embodiment of the present specification, Ar1 and Ar2 are the same or different from each other, and are each independently a substituted or unsubstituted C6-C30 aryl group; Or it is a substituted or unsubstituted C2-C30 heterocyclic group.

In one embodiment of the present specification, the heterocyclic group of Ar1 and Ar2 includes O or S as a heteroelement.

In an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted tetraphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted phenanthrenyl group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted dibenzothiophene group; Substituted or unsubstituted naphthobenzofuran group; Or a substituted or unsubstituted naphthobenzothiophene group.

In an exemplary embodiment of the present specification, Ar1 and Ar2 are the same or different from each other, and are each independently an aryl group of C6-C30 substituted or unsubstituted with deuterium; Or, it is a C2-C30 heterocyclic group substituted or unsubstituted with deuterium, a C6-C30 aryl group, or a C6-C30 aryl group substituted with deuterium.

In an exemplary embodiment of the present specification, Ar1 and Ar2 are the same or different from each other, and are each independently a C6-C20 aryl group substituted or unsubstituted with deuterium; Or, it is a C2-C20 heterocyclic group substituted or unsubstituted with deuterium, a C6-C20 aryl group, or a C6-C20 aryl group substituted with deuterium.

In an exemplary embodiment of the present specification, Ar1 and Ar2 are the same or different from each other, and are each independently a phenyl group substituted or unsubstituted with deuterium; Biphenyl group substituted or unsubstituted with deuterium; Terphenyl group substituted or unsubstituted with deuterium; Naphthyl group substituted or unsubstituted with deuterium; A phenanthrenyl group substituted or unsubstituted with deuterium; Dibenzofuran group substituted or unsubstituted with deuterium, phenyl group, or phenyl-d5 group; Dibenzothiophene group substituted or unsubstituted with deuterium, phenyl group, or phenyl-d5 group; Naphthobenzofuran group substituted or unsubstituted with deuterium, phenyl group, or phenyl-d5 group; Or it is a naphthobenzothiophene group substituted or unsubstituted with deuterium, phenyl group, or phenyl-d5 group.

In an exemplary embodiment of the present specification, Ar1 and Ar2 are the same or different from each other, and are each independently a phenyl group substituted or unsubstituted with deuterium; 1-naphthyl group substituted or unsubstituted with deuterium; 2-naphthyl group substituted or unsubstituted with deuterium; 9-phenanthrenyl group substituted or unsubstituted with deuterium; 1-dibenzofuran group substituted or unsubstituted with deuterium, phenyl group, or phenyl-d5 group; 2-dibenzofuran group substituted or unsubstituted with deuterium, phenyl group, or phenyl-d5 group; 3-dibenzofuran group substituted or unsubstituted with deuterium, phenyl group, or phenyl-d5 group; Or it is a 4-dibenzofuran group substituted or unsubstituted with deuterium, phenyl group, or phenyl-d5 group.

In one embodiment of the present specification, Ar1 is a phenyl group unsubstituted or substituted with deuterium; 1-naphthyl group substituted or unsubstituted with deuterium; Or it is a 2-naphthyl group substituted or unsubstituted with deuterium.

In one embodiment of the present specification, Ar1 is a substituted or unsubstituted O-containing heterocyclic group; Or it is a substituted or unsubstituted S-containing heterocyclic group.

In one embodiment of the present specification, Ar1 is a 3- or 4-ring O-containing heterocyclic group unsubstituted or substituted with deuterium, an aryl group, or an aryl group substituted with deuterium; Or it is a 3- or 4-ring S-containing heterocyclic group substituted or unsubstituted with deuterium, an aryl group, or an aryl group substituted with deuterium.

In one embodiment of the present specification, Ar1 is a dibenzofuran group substituted or unsubstituted with deuterium, a phenyl group, or a phenyl-d5 group; Dibenzothiophene group substituted or unsubstituted with deuterium, phenyl group, or phenyl-d5 group; Naphthobenzofuran group substituted or unsubstituted with deuterium, phenyl group, or phenyl-d5 group; Or it is a naphthobenzothiophene group substituted or unsubstituted with deuterium, phenyl group, or phenyl-d5 group.

In one embodiment of the present specification, Ar1 is a 1-dibenzofuran group substituted or unsubstituted with deuterium, a phenyl group, or a phenyl-d5 group; 2-dibenzofuran group substituted or unsubstituted with deuterium, phenyl group, or phenyl-d5 group; 3-dibenzofuran group substituted or unsubstituted with deuterium, phenyl group, or phenyl-d5 group; Or it is a 4-dibenzofuran group substituted or unsubstituted with deuterium.

In one embodiment of the present specification, Ar1 is of the following formula A1. When Ar1 connected to anthracene has the following formula A1, the high efficiency and long life characteristics of the device are enhanced.

[Formula A1]

In Formula A1,

Y1 is O; or S,

R1 to R8 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or it is a substituted or unsubstituted heterocyclic group, or combines with adjacent substituents to form a substituted or unsubstituted ring,

One of R1 to R8 is connected to L1 of Formula 1 above.

In one embodiment of the present specification, Y1 is O.

In one embodiment of the present specification, Y1 is S.

In an exemplary embodiment of the present specification, R1 to R8 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Or, it is a C6-C30 aryl group substituted or unsubstituted with deuterium, or two adjacent substituents are combined with each other to form a benzene ring substituted or unsubstituted with deuterium.

In an exemplary embodiment of the present specification, R1 to R8 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Or, it is a C6-C20 aryl group substituted or unsubstituted with deuterium, or two adjacent substituents are combined with each other to form a benzene ring substituted or unsubstituted with deuterium.

In an exemplary embodiment of the present specification, R1 to R8 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; or a phenyl group substituted or unsubstituted with deuterium, or R1 and R2; R2 and R3; R3 and R4; R5 and R6; R6 and R7; Alternatively, R7 and R8 are combined with each other to form a benzene ring substituted or unsubstituted with deuterium.

In an exemplary embodiment of the present specification, Formula A1 is one selected from the following structures.

In the above structure,

Any one of a* to j* is connected to L1 of Formula 1 above,

D is deuterium,

k3 is an integer from 0 to 7, k4 is an integer from 0 to 9,

The structure is substituted or unsubstituted with an aryl group substituted or unsubstituted with deuterium.

In one embodiment of the present specification, the structure is substituted or unsubstituted with a C6-C20 aryl group substituted or unsubstituted with deuterium.

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

In one embodiment of the present specification, a* is connected to L1 of Formula 1 above. In another embodiment, b* is connected to L1 of Formula 1 above. In another embodiment, c* is connected to L1 of Formula 1 above. In another embodiment, d* is connected to L1 of Formula 1 above. In another embodiment, e* is connected to L1 of Formula 1 above. In another embodiment, f* is connected to L1 of Formula 1 above. In another embodiment, g* is connected to L1 of Formula 1 above. In another embodiment, h* is connected to L1 of Formula 1 above. In another embodiment, i* is connected to L1 of Formula 1 above. In another embodiment, j* is connected to L1 of Formula 1 above.

In one embodiment of the present specification, k3 is 1 or more. In another embodiment, k3 is 2 or more. In another embodiment, k3 is 3 or more. In another embodiment, k3 is 4 or more. In another embodiment, k3 is 5 or more. In another embodiment, k3 is 6 or more. In another embodiment, k3 is 7.

In one embodiment of the present specification, k4 is 1 or more. In another embodiment, k4 is 2 or more. In another embodiment, k4 is 3 or more. In another embodiment, k4 is 4 or more. In another embodiment, k4 is 5 or more. In another embodiment, k4 is 6 or more. In another embodiment, k4 is 7 or more. In another embodiment, k4 is 8 or more. In another embodiment, k4 is 9.

In one embodiment of the present specification, Ar2 is a C6-C30 aryl group substituted or unsubstituted with deuterium.

In one embodiment of the present specification, Ar2 is a C6-C20 aryl group substituted or unsubstituted with deuterium.

In one embodiment of the present specification, Ar2 is a phenyl group unsubstituted or substituted with deuterium; Biphenyl group substituted or unsubstituted with deuterium; Terphenyl group substituted or unsubstituted with deuterium; Naphthyl group substituted or unsubstituted with deuterium; Or it is a phenanthrenyl group substituted or unsubstituted with deuterium.

In one embodiment of the present specification, Ar2 is a phenyl group unsubstituted or substituted with deuterium; 1-naphthyl group substituted or unsubstituted with deuterium; 2-naphthyl group substituted or unsubstituted with deuterium; Or it is a 9-phenanthrenyl group substituted or unsubstituted with deuterium.

In one embodiment of the present specification, Ar1 is the formula A1, and L1 is a direct bond.

In one embodiment of the present specification, Ar1 is the formula A1, and Ar2 is a substituted or unsubstituted aryl group.

In one embodiment of the present specification, Ar1 is the formula A1, and Ar2 is a C6-C20 aryl group unsubstituted or substituted with deuterium.

In an exemplary embodiment of the present specification, Ar1 is the formula A1, Ar2 is a phenyl group unsubstituted or substituted with deuterium; Biphenyl group substituted or unsubstituted with deuterium; Terphenyl group substituted or unsubstituted with deuterium; Naphthyl group substituted or unsubstituted with deuterium; Or it is a phenanthrenyl group substituted or unsubstituted with deuterium.

In one embodiment of the present specification, Formula 1 is deuterated by more than 50%. In another embodiment, Formula 1 is deuterated by more than 60%. In another embodiment, Formula 1 is deuterated by more than 70%. In another embodiment, Formula 1 is deuterated by more than 80%. In another embodiment, Formula 1 is deuterated by more than 90%. In another embodiment, Formula 1 is 100% deuterated.

In an exemplary embodiment of the present specification, Formula 1 is one selected from the following compounds.

In another embodiment, Formula 1 is one selected from the following compounds. Specifically, it is a compound of Formula 1 including Formula A1.

Hereinafter, the compound of Formula 2 below will be described in detail.

[Formula 2]

In one embodiment of the present specification, D in Formula 2 is deuterium.

In one embodiment of the present specification, n1 is an integer from 0 to 7.

In one embodiment of the present specification, n1 is 0.

In an exemplary embodiment of the present specification, L3 to L5 are the same as or different from each other, and are each independently directly bonded; Substituted or unsubstituted arylene group; Or it is a substituted or unsubstituted divalent heterocyclic group.

In an exemplary embodiment of the present specification, L3 to L5 are the same as or different from each other, and are each independently directly bonded; Substituted or unsubstituted C6-C60 arylene group; Or it is a substituted or unsubstituted C2-C60 divalent heterocyclic group.

In an exemplary embodiment of the present specification, L3 to L5 are the same as or different from each other, and are each independently directly bonded; Substituted or unsubstituted C6-C30 arylene group; Or it is a substituted or unsubstituted C2-C30 divalent heterocyclic group.

In an exemplary embodiment of the present specification, L3 to L5 are the same as or different from each other, and are each independently directly bonded; Substituted or unsubstituted phenylene group; Substituted or unsubstituted biphenylene group; Or a substituted or unsubstituted naphthylene group.

In an exemplary embodiment of the present specification, L3 to L5 are the same as or different from each other, and are each independently directly bonded; Or it is a phenylene group.

In one embodiment of the present specification, L3 is a direct bond.

In one embodiment of the present specification, L4 is a direct bond.

In one embodiment of the present specification, L5 is a direct bond.

In an exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and are each independently a cyano group; Substituted or unsubstituted aryl group; Or it is a substituted or unsubstituted heterocyclic group.

In an exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and are each independently a cyano group; Substituted or unsubstituted C6-C60 aryl group; Or it is a substituted or unsubstituted C2-C60 heterocyclic group.

In an exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and are each independently a cyano group; Substituted or unsubstituted C6-C30 aryl group; Or it is a substituted or unsubstituted C2-C30 heterocyclic group.

In an exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and are each independently a cyano group; Substituted or unsubstituted C6-C20 aryl group; Or it is a substituted or unsubstituted C2-C20 heterocyclic group.

In an exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and are each independently a cyano group; A C6-C30 aryl group substituted or unsubstituted with a C1-C10 alkyl group or a C6-C30 aryl group; Or it is a C2-C30 heterocyclic group substituted or unsubstituted with a C1-C10 alkyl group or a C6-C30 aryl group.

In an exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and are each independently a cyano group; A C6-C20 aryl group substituted or unsubstituted with a C1-C6 alkyl group or a C6-C20 aryl group; Or it is a C2-C20 heterocyclic group substituted or unsubstituted with a C1-C6 alkyl group or a C6-C20 aryl group.

In an exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and are each independently a cyano group; Substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted fluorenyl group; Substituted or unsubstituted phenanthrenyl group; A substituted or unsubstituted fluoranthenyl group; Substituted or unsubstituted furan group; Substituted or unsubstituted thiophene group; Substituted or unsubstituted benzofuran group; Substituted or unsubstituted benzothiophene group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted dibenzothiophene group; Substituted or unsubstituted carbazole group; Substituted or unsubstituted triazine group; Substituted or unsubstituted pyrimidine group; Substituted or unsubstituted pyridyl group; Substituted or unsubstituted pyridazine group; Substituted or unsubstituted benzimidazole group; or substituted or unsubstituted am. At this time, Y3 and Y4 are the same or different from each other, and are each independently O; S; Or NR14.

In an exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and are each independently a cyano group; A phenyl group substituted or unsubstituted with a methyl group; Biphenyl group; Terphenyl group; naphthyl group; A fluorenyl group unsubstituted or substituted with a methyl group or phenyl group; phenanthrenyl group; fluoranthenyl group; furan group; thiophene group; benzofuran group; benzothiophene group; Dibenzofuran group; Dibenzothiophene group; Carbazole group substituted or unsubstituted with a phenyl group; A triazine group unsubstituted or substituted with a methyl group or phenyl group; A pyrimidine group unsubstituted or substituted with a methyl group or phenyl group; A pyridyl group substituted or unsubstituted with a methyl group or phenyl group; A pyridazine group unsubstituted or substituted with a methyl group or phenyl group; A benzimidazole group substituted or unsubstituted with an ethyl group or phenyl group; or am.

In an exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and are each independently a phenyl group; Biphenyl group; naphthyl group; dimethylfluorenyl group; Diphenyl fluorenyl group; Dibenzothiophene group; Or it is a carbazole group.

In one embodiment of the present specification, Ar3 is the above-mentioned substituent and may include one or more cyano groups as substituents connected to Ar3.

In one embodiment of the present specification, Ar4 is the above-described substituent and may include one or more cyano groups as substituents connected to Ar4.

In one embodiment of the present specification, Ar5 is hydrogen; heavy hydrogen; Cyano group; Substituted or unsubstituted aryl group; Or it is a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, Ar5 is hydrogen; heavy hydrogen; Cyano group; Substituted or unsubstituted C6-C60 aryl group; Or it is a substituted or unsubstituted C2-C60 heterocyclic group.

In one embodiment of the present specification, Ar5 is hydrogen; heavy hydrogen; Cyano group; Substituted or unsubstituted C6-C30 aryl group; Or it is a substituted or unsubstituted C2-C30 heterocyclic group.

In one embodiment of the present specification, Ar5 is hydrogen; heavy hydrogen; Cyano group; Substituted or unsubstituted C6-C20 aryl group; Or it is a substituted or unsubstituted C2-C20 heterocyclic group.

In one embodiment of the present specification, Ar5 is hydrogen; heavy hydrogen; Cyano group; Substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted fluorenyl group; Substituted or unsubstituted phenanthrenyl group; A substituted or unsubstituted fluoranthenyl group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted dibenzothiophene group; Substituted or unsubstituted carbazole group; Substituted or unsubstituted triazine group; Substituted or unsubstituted pyrimidine group; Substituted or unsubstituted pyridyl group; Substituted or unsubstituted pyridazine group; Substituted or unsubstituted benzimidazole group; or substituted or unsubstituted am. At this time, Y3 and Y4 are the same or different from each other, and are each independently O; S; Or N14.

In one embodiment of the present specification, Ar5 is hydrogen; heavy hydrogen; Cyano group; A phenyl group substituted or unsubstituted with a methyl group; Biphenyl group; Terphenyl group; naphthyl group; A fluorenyl group unsubstituted or substituted with a methyl group or phenyl group; phenanthrenyl group; fluoranthenyl group; furan group; thiophene group; benzofuran group; Benzothiophene group; Dibenzofuran group; Dibenzothiophene group; Carbazole group substituted or unsubstituted with a phenyl group; A triazine group unsubstituted or substituted with a methyl group or phenyl group; A pyrimidine group unsubstituted or substituted with a methyl group or phenyl group; A pyridyl group substituted or unsubstituted with a methyl group or phenyl group; A pyridazine group unsubstituted or substituted with a methyl group or phenyl group; A benzimidazole group substituted or unsubstituted with an ethyl group or phenyl group; or am.

In one embodiment of the present specification, Ar5 is hydrogen; phenyl group; Or it is a dimethylfluorenyl group.

In one embodiment of the present specification, Ar5 is the above-described substituent and may include one or more cyano groups as substituents connected to Ar5.

In an exemplary embodiment of the present specification, Ar3 and Ar4 are the same or different from each other, and are each independently selected from Group 1 or Group 2 below.

In one embodiment of the present specification, Ar5 is hydrogen; heavy hydrogen; Cyano group; One selected from group 1 or 2 below.

In an exemplary embodiment of the present specification, Ar3 and Ar4 are the same or different from each other and are each independently selected from Group 1 or 2 below, and Ar5 is hydrogen; heavy hydrogen; Cyano group; One selected from group 1 or 2 below.

[Group 1]

[Group 2]

In groups 1 and 2 above,

The dotted line is the position connected to Formula 2,

Y3 is O; S; or NR14,

X1 to X5 are the same or different from each other, and are each independently N; or CR15,

At least one of X1 to X5 is N,

R11 to R15 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

Cy1 is a monocyclic or polycyclic aromatic hydrocarbon ring; Or a monocyclic or polycyclic aromatic heterocycle,

The structures of groups 1 and 2 include deuterium; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or, it is substituted or unsubstituted with a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, Y3 is NR14.

In one embodiment of the present specification, Y3 is O; Or S.

In one embodiment of the present specification, Cy1 is a benzene ring; Naphthalene ring; Dibenzofuran ring; Dibenzothiophene ring; Or it is a carbazole ring.

In one embodiment of the present specification, Cy1 is a benzene ring; Naphthalene ring; Or it is a dibenzofuran ring.

In an exemplary embodiment of the present specification, R11 to R13 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group; Or it is a substituted or unsubstituted aryl group.

In an exemplary embodiment of the present specification, R11 to R13 are the same as or different from each other, and are each independently a substituted or unsubstituted C1-C10 alkyl group; Or it is a substituted or unsubstituted C6-C30 aryl group.

In an exemplary embodiment of the present specification, R11 to R13 are the same as or different from each other, and each independently represents a substituted or unsubstituted methyl group; Substituted or unsubstituted ethyl group; Or a substituted or unsubstituted phenyl group.

In one embodiment of the present specification, R11 and R12 are methyl groups.

In one embodiment of the present specification, R13 is an ethyl group; Or it is a phenyl group.

In one embodiment of the present specification, R14 is a substituted or unsubstituted aryl group.

In one embodiment of the present specification, R14 is a substituted or unsubstituted C6-C30 aryl group.

In one embodiment of the present specification, R14 is a substituted or unsubstituted phenyl group; Or a substituted or unsubstituted biphenyl group.

In one embodiment of the present specification, R14 is a phenyl group.

In one embodiment of the present specification, R15 is hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Or it is a substituted or unsubstituted aryl group.

In one embodiment of the present specification, R15 is hydrogen; heavy hydrogen; Substituted or unsubstituted C1-C10 alkyl group; Or it is a substituted or unsubstituted C6-C30 aryl group.

In one embodiment of the present specification, R15 is hydrogen; heavy hydrogen; Substituted or unsubstituted methyl group; Or a substituted or unsubstituted phenyl group.

In an exemplary embodiment of the present specification, at least one of the plurality of R15 is a substituted or unsubstituted alkyl group; Or it is a substituted or unsubstituted aryl group.

In one embodiment of the present specification, R15 is hydrogen; heavy hydrogen; methyl group; Or it is a phenyl group, and at least one of R15 is a methyl group or a phenyl group.

In an exemplary embodiment of the present specification, the structure of group 2 is one selected from group 2-1 below.

[Group 2-1]

In group 2-1 above,

The dotted line is the position connected to Formula 2,

Y3 and Y4 are the same as or different from each other and are each independently O; S; or NR14,

R13, R14 and R16 to R18 are the same or different from each other and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

r16 is an integer from 0 to 3, r16' is an integer from 0 to 4,

When r16 and r16' are each 2 or more, R16 is the same or different from each other.

In one embodiment of the present specification, Y3 is NR14.

In an exemplary embodiment of the present specification, Y3 and Y4 are the same as or different from each other and are each independently O; Or S.

In an exemplary embodiment of the present specification, the above-described description of R15 may be applied to R16 to R18.

In an exemplary embodiment of the present specification, R16 to R18 are the same as or different from each other, and are each independently a substituted or unsubstituted alkyl group; Or it is a substituted or unsubstituted aryl group.

In an exemplary embodiment of the present specification, R16 to R18 are the same or different from each other, and are each independently a substituted or unsubstituted C1-C10 alkyl group; Or it is a substituted or unsubstituted C6-C30 aryl group.

In an exemplary embodiment of the present specification, R16 to R18 are the same as or different from each other, and each independently represents a substituted or unsubstituted methyl group; Or a substituted or unsubstituted phenyl group.

In one embodiment of the present specification, R16 is a methyl group; Or it is a phenyl group.

In one embodiment of the present specification, r16 is 1 or more.

In one embodiment of the present specification, r16 is 1.

In one embodiment of the present specification, r16' is 1 or more.

In one embodiment of the present specification, r16' is 2.

In one embodiment of the present specification, R17 and R18 are phenyl groups.

In an exemplary embodiment of the present specification, at least one of Ar3 and Ar4 is selected from Group 1 above.

In one embodiment of the present specification, Ar3 is one selected from Group 1 above.

In one embodiment of the present specification, Ar4 is one selected from Group 1 above.

In an exemplary embodiment of the present specification, at least one of Ar3 to Ar5 is a cyano group or includes one or more cyano groups as a substituent. At this time, at least one of Ar3 to Ar5 is 1) a cyano group, or 2) an aryl group or a heterocyclic group, and includes one or more cyano groups as a substituent for the aryl group or heterocyclic group.

In this specification, even if the case where the above-mentioned substituent is substituted with a cyano group is not specified in the definition of Ar3 to Ar5, the case where the above-described substituent is substituted with a cyano group may be included.

In an exemplary embodiment of the present specification, at least one of Ar3 to Ar5 is a cyano group or has the formula 201 below.

[Formula 201]

In Formula 201,

Ar6 is a substituted or unsubstituted divalent to tetravalent aryl group; Or a substituted or unsubstituted divalent to tetravalent heterocyclic group,

m1 is an integer from 1 to 3,

The dotted line connects to Formula 2 above.

In one embodiment of the present specification, m1 is 1 or 2.

In one embodiment of the present specification, m1 is 1.

In one embodiment of the present specification, Ar6 is a substituted or unsubstituted divalent to tetravalent C6-C30 aryl group; Or it is a substituted or unsubstituted divalent to tetravalent C2-C30 heterocyclic group.

In one embodiment of the present specification, Ar6 is a substituted or unsubstituted divalent to tetravalent C6-C20 aryl group; Or it is a substituted or unsubstituted divalent to tetravalent C2-C20 heterocyclic group.

In one embodiment of the present specification, Ar6 is a substituted or unsubstituted divalent to tetravalent phenyl group; Substituted or unsubstituted divalent to tetravalent biphenyl groups; Substituted or unsubstituted divalent to tetravalent terphenyl groups; Substituted or unsubstituted divalent to tetravalent naphthyl groups; Substituted or unsubstituted divalent to tetravalent fluorenyl group; Substituted or unsubstituted divalent to tetravalent phenanthrenyl groups; Substituted or unsubstituted divalent to tetravalent fluoranthenyl group; Substituted or unsubstituted divalent to tetravalent furan groups; Substituted or unsubstituted divalent to tetravalent thiophene groups; Substituted or unsubstituted divalent to tetravalent benzofuran groups; Substituted or unsubstituted divalent to tetravalent benzothiophene groups; Substituted or unsubstituted divalent to tetravalent dibenzofuran groups; Substituted or unsubstituted divalent to tetravalent dibenzothiophene groups; Substituted or unsubstituted divalent to tetravalent carbazole groups; Substituted or unsubstituted divalent to tetravalent triazine groups; Substituted or unsubstituted divalent to tetravalent pyrimidine groups; Substituted or unsubstituted divalent to tetravalent pyridyl groups; Substituted or unsubstituted divalent to tetravalent pyridazine groups; Substituted or unsubstituted divalent to tetravalent benzimidazole groups; Or substituted or unsubstituted divalent to tetravalent am. At this time, Y3 and Y4 are the same or different from each other, and are each independently O; S; Or N14.

In an exemplary embodiment of the present specification, Ar6 may be a divalent or trivalent structure selected from Group 1 or Group 2 described above.

In one embodiment of the present specification, Ar6 is a substituted or unsubstituted divalent to trivalent phenyl group; Substituted or unsubstituted divalent to trivalent biphenyl groups; Substituted or unsubstituted divalent to trivalent terphenyl groups; Substituted or unsubstituted divalent to trivalent naphthyl groups; Substituted or unsubstituted divalent to trivalent fluorenyl group; Substituted or unsubstituted divalent to trivalent furan groups; Substituted or unsubstituted divalent to trivalent thiophene groups; Substituted or unsubstituted divalent to trivalent benzofuran groups; Substituted or unsubstituted divalent to trivalent benzothiophene groups; Substituted or unsubstituted divalent to trivalent dibenzofuran groups; Or it is a substituted or unsubstituted dibenzothiophene group.

In an exemplary embodiment of the present specification, Ar6 is a divalent to trivalent phenyl group; Divalent to trivalent biphenyl group; Bivalent to trivalent terphenyl group; divalent to trivalent naphthyl group; Bivalent to trivalent fluorenyl groups substituted or unsubstituted with methyl or phenyl groups; divalent to trivalent furan group; Divalent to trivalent thiophene group; divalent to trivalent benzofuran group; divalent to trivalent benzothiophene groups; divalent to trivalent dibenzofuran groups; Or it is a dibenzothiophene group of divalent to trivalent form.

In one embodiment of the present specification, Ar6 is a substituted or unsubstituted divalent to tetravalent C6-C30 aryl group.

In one embodiment of the present specification, Ar6 is a substituted or unsubstituted divalent to trivalent C6-C20 aryl group.

In an exemplary embodiment of the present specification, Ar6 is a divalent to trivalent phenyl group; Divalent to trivalent biphenyl group; Bivalent to trivalent terphenyl group; divalent to trivalent naphthyl group; Or it is a divalent to trivalent fluorenyl group substituted or unsubstituted with a methyl group or phenyl group.

In an exemplary embodiment of the present specification, at least one of Ar3 to Ar5 is a cyano group or one of the following formulas 202 to 204.

[Formula 202]

[Formula 203]

[Formula 204]

In Formulas 202 to 204,

m1 is an integer from 1 to 3,

Ar61 is directly bonded; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,

R21 is hydrogen; heavy hydrogen; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

R22 and R23 are the same or different from each other, and are each independently a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,

r21 is an integer from 0 to 4, r21' and r21'' are each an integer from 0 to 6,

When r21, r21' and r21'' are each 2 or more, R21 is the same or different from each other,

The dotted line connects to Formula 2 above.

In one embodiment of the present specification, R21 is hydrogen; heavy hydrogen; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or it is a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, R21 is hydrogen; heavy hydrogen; Cyano group; Substituted or unsubstituted C1-C10 alkyl group; Substituted or unsubstituted C6-C30 aryl group; Or it is a substituted or unsubstituted C2-C30 heterocyclic group.

In one embodiment of the present specification, R21 is hydrogen; heavy hydrogen; Cyano group; Or a substituted or unsubstituted phenyl group.

In one embodiment of the present specification, R21 is hydrogen; Or it is a phenyl group.

In an exemplary embodiment of the present specification, R22 and R23 are the same or different from each other, and are each independently a substituted or unsubstituted C1-C10 alkyl group; Or it is a substituted or unsubstituted C6-C30 aryl group.

In an exemplary embodiment of the present specification, R22 and R23 are the same or different from each other, and are each independently a substituted or unsubstituted methyl group; Or a substituted or unsubstituted phenyl group.

In an exemplary embodiment of the present specification, R22 and R23 are the same as or different from each other, and are each independently a methyl group; Or it is a phenyl group.

In one embodiment of the present specification, the above-described description of Ar6 applies to Ar61.

In one embodiment of the present specification, Ar61 is a direct bond; It is a substituted or unsubstituted C6-C30 arylene group.

In one embodiment of the present specification, Ar61 is a direct bond; It is a substituted or unsubstituted C6-C20 arylene group.

In one embodiment of the present specification, Ar61 is a direct bond; Substituted or unsubstituted phenyl group; Or a substituted or unsubstituted biphenylene group.

In one embodiment of the present specification, Ar61 is a direct bond; Or it is a phenylene group.

In one embodiment of the present specification, r21 is 1.

In one embodiment of the present specification, r21' and r21'' are 0.

In an exemplary embodiment of the present specification, Formula 202 is represented by any one of the following Formulas 202-1 to 202-5.

[Formula 202-1]

[Formula 202-2]

[Formula 202-3]

[Formula 202-4]

[Formula 202-5]

In the above formulas 202-1 to 202-5,

Ar61, R21, r21 and the dotted line are as defined in Formula 202 above,

r211 is an integer from 0 to 3, and when r211 is 2 or more, R21 is the same or different from each other.

In an exemplary embodiment of the present specification, Formula 202 is any one of Formulas 202-2 to 202-5.

In an exemplary embodiment of the present specification, Formula 202 is Formula 202-2 or 202-3.

In one embodiment of the present specification, Ar3 is a cyano group or includes one or more cyano groups as a substituent. In another embodiment, Ar3 is a cyano group or one of the above formulas 202 to 204.

In one embodiment of the present specification, Ar4 is a cyano group or includes one or more cyano groups as a substituent. In another embodiment, Ar4 is a cyano group or one of the above formulas 202 to 204.

In one embodiment of the present specification, Ar5 is a cyano group or includes one or more cyano groups as a substituent. In another embodiment, Ar5 is a cyano group or one of the formulas 202 to 204 above.

In an exemplary embodiment of the present specification, Formula 2 is one selected from the following compounds.

A compound according to an exemplary embodiment of the present specification may be produced by a production method described later. As needed, substituents can be added or excluded, and the positions of the substituents can be changed. Additionally, starting materials, reactants, reaction conditions, etc. can be changed based on techniques known in the art. The preparation method may be further detailed in the preparation examples described later, the reaction order may change depending on the compound, and the method for synthesizing the compounds of Formulas 1 and 2 is not limited to the above method.

This specification provides an organic light-emitting device containing the above-described compound.

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 this specification, when a part “includes” a certain element, this means that it may further include other elements rather than excluding other elements, unless specifically stated to the contrary.

In this specification, the “layer” is interchangeable with the “film” mainly used in the present technical field, and refers to a coating that covers the target area. The size of the “layer” is not limited, and each “layer” may have the same or different size. In one embodiment, the size of a “layer” may be the same as the entire device, may correspond to the size of a specific functional area, or may be as small as a single sub-pixel.

In this specification, the inclusion of a specific material A in the layer B means that i) one or more types of material A are included in one layer B, and ii) the layer B consists of one or more layers, and the material A is included in a multi-layer B. Includes everything on the first or higher floors.

In this specification, a specific material A is included in layer C or layer D, meaning i) it is included in one or more layers of one or more layers of C, ii) it is included in one or more layers of one or more layers of D, or iii) ) This means that it is included in each of the C floors above the first floor and the D floors above the first floor.

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, it may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, etc. However, the structure of the organic light emitting device is not limited to this.

The organic light emitting device of the present specification includes the compound of Formula 1 in the light emitting layer and the compound of Formula 2 in the first organic layer.

In one embodiment of the present specification, the first organic layer is provided between the light emitting layer and the cathode. That is, the first organic material layer is included in the electron transport region.

In one embodiment of the present specification, the first organic layer is provided in direct contact with the light-emitting layer. At this time, no additional organic material layer is included between the light emitting layer and the first organic material layer.

In one embodiment of the present specification, the first organic layer is provided between the light-emitting layer and the cathode, and is provided in direct contact with the light-emitting layer.

In one embodiment of the present specification, the first organic material layer is provided in direct contact with the cathode. At this time, no additional organic material layer is included between the cathode and the first organic material layer.

In one embodiment of the present specification, the light emitting layer includes a host and a dopant. In one embodiment, the host includes the compound of Formula 1 above.

In one embodiment of the present specification, the dopant includes a phosphorescent dopant or a fluorescent dopant. The fluorescent dopant may include an arylamine-based compound or a boron compound.

In one embodiment of the present specification, the dopant is an arylamine-based compound containing a pyrene group. Specifically, it is a compound of the following formula Z1.

[Formula Z1]

In the above formula Z1,

Ar31 to Ar34 are the same or different from each other, and are each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

R31 and R32 are the same or different from each other and are each independently hydrogen; heavy hydrogen; halogen group; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

r31 and r32 are integers from 0 to 4, and when 2 or more, the substituents in parentheses are the same or different from each other.

In an exemplary embodiment of the present specification, Ar31 to Ar34 are aryl groups unsubstituted or substituted with deuterium, an alkyl group, or a cyano group.

In an exemplary embodiment of the present specification, R31 and R32 are hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkylsilyl group.

In an exemplary embodiment of the present specification, Formula Z1 includes a cyano group or a silyl group. At least one of the above-mentioned R31, R32, Ar31 and Ar34 is a cyano group or a silyl group, or contains a cyano group or a silyl group as a substituent.

In an exemplary embodiment of the present specification, Formula Z1 is the following compound.

In one embodiment of the present specification, the dopant in the light emitting layer may be included in an amount of 0.01 parts by weight to 50 parts by weight based on 100 parts by weight of the host, preferably 0.1 parts by weight to 30 parts by weight, more preferably 1 part by weight to 10 parts by weight. It may be included by weight. When within the above range, energy transfer from host to dopant occurs efficiently.

In one embodiment of the present specification, the organic material layer includes two or more light-emitting layers, and one layer of the two or more light-emitting layers includes the compound of Formula 1.

In an exemplary embodiment of the present specification, the maximum emission peaks of the two or more light-emitting layers are different from each other. The light-emitting layer containing the compound of Formula 1 has a blue color, and the light-emitting layer that does not contain the compound of Formula 1 may include blue, red, or green light-emitting compounds known in the art.

In one embodiment of the present specification, the light-emitting layer containing the compound of Formula 1 includes a fluorescent dopant, and the light-emitting layer that does not contain the compound of Formula 1 includes a phosphorescent dopant.

In one embodiment of the present specification, the maximum emission peak of the light-emitting layer containing the compound of Formula 1 exists in the range of 400 nm to 500 nm. That is, the light-emitting layer containing the compound of Formula 1 emits blue light.

The organic material layer of the organic light-emitting device according to an embodiment of the present specification includes two or more light-emitting layers, the maximum emission peak of one light-emitting layer (light-emitting layer 1) is within the range of 400 nm to 500 nm, and the maximum emission peak of the other layer is within the range of 400 nm to 500 nm. The maximum emission peak of the light-emitting layer (light-emitting layer 2) is 510 nm to 580 nm; or within the range of 610 nm to 680 nm. At this time, light-emitting layer 1 includes the compound of Formula 1 above.

In one embodiment of the present specification, the first organic material layer is an electron transport region. Specifically, it is an electron injection layer, an electron transport layer, an electron injection and transport layer, or a hole blocking layer.

In an exemplary embodiment of the present specification, the first organic material layer further includes one or two or more types of n-type dopants selected from alkali metals and alkaline earth metals.

When an organic alkali metal compound or an organic alkaline earth metal compound is used as an n-type dopant, stability against holes in the light-emitting layer can be secured, thereby improving the lifespan of the organic light-emitting device. In addition, the electron mobility of the electron transport layer can be adjusted by adjusting the ratio of the organic alkali metal compound or the organic alkaline earth metal compound to maximize the balance between holes and electrons in the light emitting layer, thereby increasing luminous efficiency.

LiQ is more preferable as the n-type dopant used in the first organic material layer in this specification.

The first organic layer may include the compound of Formula 2 and the n-type dopant at a weight ratio of 1:9 to 9:1. Preferably, the compound of Formula 2 and the n-type dopant may be included in a ratio of 2:8 to 8:2, and more preferably, they may be included in a ratio of 3:7 to 7:3.

In one embodiment of the present specification, the first organic material layer is provided in direct contact with the light-emitting layer and includes the compound of Formula 2 and an n-type dopant.

In one embodiment of the present specification, the first organic material layer is provided in direct contact with the cathode and includes the compound of Formula 2. At this time, the first organic layer does not contain any other compounds other than the compound of Formula 2. Additionally, another organic material layer (specifically, a hole blocking layer) may be included between the first organic material layer and the light-emitting layer.

In one embodiment of the present specification, the organic material layer of the organic light-emitting device has a hole transport region between the anode and the light-emitting layer. At this time, the hole transport region includes one or more of a hole injection layer, a hole injection layer, a hole injection and transport layer, and an electron blocking layer.

In one embodiment of the present specification, the organic light emitting device may be a normal type organic light emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.

In one embodiment of the present specification, the organic light emitting device may be an inverted type organic light emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.

The structure of the organic light emitting device of the present specification may have the same structure as shown in FIGS. 1, 2, and 8, but is not limited thereto.

1 shows a substrate (1), an anode (2), a hole injection layer (3), a hole transport layer (4), a light emitting layer (6), a hole blocking layer (7), an electron injection and transport layer (8), and a cathode (11). The structure of this sequentially stacked organic light emitting device is illustrated. In this structure, the compound of Formula 1 may be included in the light-emitting layer (6), and the compound of Formula 2 may be included in the hole blocking layer (7) or the electron injection and transport layer (8).

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), an electron injection and transport layer (8), and a cathode (11). The structure of this sequentially stacked organic light emitting device is illustrated. In this structure, the compound of Formula 1 may be included in the light-emitting layer (6), and the compound of Formula 2 may be included in the electron injection and transport layer (8).

8 shows a substrate 1, an anode 2, a p-doped hole transport layer (4p), a red hole transport layer (4R), a green hole transport layer (4G), a blue hole transport layer (4B), and a red phosphorescent emitting layer (6RP). , a green phosphorescent light-emitting layer (6GP), a blue fluorescent light-emitting layer (6BF), a first electron transport layer (9a), a second electron transport layer (9b), an electron injection layer (10), a cathode (11), and a capping layer (14) sequentially. The structure of a stacked organic light emitting device is illustrated. In this structure, the compound of Formula 1 may be included in the red phosphorescent emitting layer (6RP), the green phosphorescent emitting layer (6GP), and the blue fluorescent emitting layer (6BF), and the compound of Formula 2 may be included in the first electron transport layer (9a). , may be included in one or more of the second electron transport layer 9b and the electron injection layer 10.

According to an exemplary embodiment of the present specification, the organic light emitting device may have a tandem structure in which two or more independent devices are connected in series. In one embodiment, the tandem structure may be in a form in which each organic light-emitting device is bonded to a charge generation layer. Tandem-structured devices can be driven at lower currents than unit devices based on the same brightness, which has the advantage of greatly improving the device's lifespan characteristics.

According to an exemplary embodiment of the present specification, the organic material layer includes a first stack including one or more light-emitting layers; a second stack including one or more light emitting layers; and one or more charge generation layers provided between the first stack and the second stack.

According to an exemplary embodiment of the present specification, the organic material layer includes a first stack including one or more light-emitting layers; a second stack including one or more light emitting layers; and a third stack including one or more light emitting layers, between the first stack and the second stack; and one or more charge generation layers between the second stack and the third stack.

In this specification, the charge generating layer refers to a layer in which holes and electrons are generated when a voltage is applied. The charge generation layer may be an N-type charge generation layer or a P-type charge generation layer. In this specification, an N-type charge generation layer refers to a charge generation layer located closer to the anode than a P-type charge generation layer, and a P-type charge generation layer refers to a charge generation layer located closer to the cathode than an N-type charge generation layer.

The N-type charge generation layer and the P-type charge generation layer may be provided in contact with each other, and in this case, form an NP junction. By NP junction, holes are easily formed in the P-type charge generation layer and electrons are easily formed in the N-type charge generation layer. Electrons are transported toward the anode through the LUMO level of the N-type charge generation layer, and holes are transported toward the cathode through the HOMO level of the P-type organic layer.

The first stack, the second stack, and the third stack each include one or more light emitting layers, and additionally include a hole injection layer, a hole transport layer, an electron blocking layer, an electron injection layer, an electron transport layer, a hole blocking layer, a hole transport layer, and a hole transport layer. It may further include one or more layers among a layer that performs simultaneous injection (hole injection and transport layer) and a layer that simultaneously performs electron transport and electron injection (electron injection and transport layer).

An organic light emitting device including the first stack and the second stack is illustrated in FIG. 3 .

3 shows a substrate 1, an anode 2, a hole injection layer 3, a first hole transport layer 4a, an electron blocking layer 5, a first light emitting layer 6a, a first electron transport layer 9a, An N-type charge generation layer 12, a P-type charge generation layer 13, a second hole transport layer 4b, a second light-emitting layer 6b, an electron injection and transport layer 8, and a cathode 11 are sequentially stacked. The structure of an organic light emitting device is illustrated. In this structure, the compound of formula 1 may be included in the first emitting layer (6a) or the second emitting layer (6b), and the compound of formula 2 may be included in the first electron transport layer (9a) or the electron injection and transport layer (8) ) can be included.

Organic light emitting devices including the first to third stacks are illustrated in FIGS. 4 to 7.

4 shows a substrate 1, an anode 2, a hole injection layer 3, a first hole transport layer 4a, an electron blocking layer 5, a first light emitting layer 6a, a first electron transport layer 9a, First N-type charge generation layer (12a), first P-type charge generation layer (13a), second hole transport layer (4b), second light-emitting layer (6b), second electron transport layer (9b), second N-type charge An organic layer in which a generation layer (12b), a second P-type charge generation layer (13b), a third hole transport layer (4c), a third light-emitting layer (6c), a third electron transport layer (9c), and a cathode (11) are sequentially stacked. The structure of the light emitting device is illustrated. In this structure, the compound of formula 1 may be included in the first emitting layer (6a), the second emitting layer (6b), and the third emitting layer (6c), and the compound of formula 2 may be included in the first electron transport layer (9a) , may be included in one or more of the second electron transport layer 9b and the third electron transport layer 9c.

5 shows a substrate 1, an anode 2, a hole injection layer 3, a first hole transport layer 4a, a second hole transport layer 4b, a first blue fluorescent light-emitting layer 6BFa, and a first electron transport layer ( 9a), first N-type charge generation layer (12a), first P-type charge generation layer (13a), third hole transport layer (4c), red phosphorescent emission layer (6RP), yellow green phosphorescence emission layer (6YGP), green phosphorescence Light emitting layer (6GP), second electron transport layer (9b), second N-type charge generation layer (12b), second P-type charge generation layer (13b), fourth hole transport layer (4d), fifth hole transport layer (4e) , the structure of an organic light emitting device in which a second blue fluorescent light emitting layer (6BFb), a third electron transport layer (9c), an electron injection layer (10), a cathode (11), and a capping layer (14) are sequentially stacked is illustrated. In this structure, the compound of Formula 1 may be included in the first blue fluorescent emission layer (6BFa) or the second blue fluorescent emission layer (6BFb), and the compound of Formula 2 may be included in the first electron transport layer (9a) and the second electron transport layer (9a). It may be included in one or more of the electron transport layer 9b, the third electron transport layer 9c, and the electron injection layer 10.

6 shows a substrate 1, an anode 2, a hole injection layer 3, a first hole transport layer 4a, a second hole transport layer 4b, a first blue fluorescent light-emitting layer 6BFa, and a first electron transport layer ( 9a), first N-type charge generation layer (12a), first P-type charge generation layer (13a), third hole transport layer (4c), red phosphorescent emission layer (6RP), green phosphorescence emission layer (6GP), second electron Transport layer (9b), second N-type charge generation layer (12b), second P-type charge generation layer (13b), fourth hole transport layer (4d), fifth hole transport layer (4e), second blue fluorescent light-emitting layer (6BFb) ), the structure of an organic light-emitting device in which the third electron transport layer 9c, the electron injection layer 10, the cathode 11, and the capping layer 14 are sequentially stacked is illustrated. In this structure, the compound of Formula 1 may be included in the first blue fluorescent emission layer (6BFa) or the second blue fluorescent emission layer (6BFb), and the compound of Formula 2 may be included in the first electron transport layer (9a) and the second electron transport layer (9a). It may be included in one or more of the electron transport layer 9b, the third electron transport layer 9c, and the electron injection layer 10.

7 shows a substrate 1, an anode 2, a first p-doped hole transport layer 4pa, a first hole transport layer 4a, a second hole transport layer 4b, a first blue fluorescent light emitting layer 6BFa, First electron transport layer (9a), first N-type charge generation layer (12a), first P-type charge generation layer (13a), third hole transport layer (4c), fourth hole transport layer (4d), second blue fluorescence Light-emitting layer (6BFb), second electron transport layer (9b), second N-type charge generation layer (12b), second P-type charge generation layer (13b), fifth hole transport layer (4e), sixth hole transport layer (4f) , the structure of an organic light emitting device in which a third blue fluorescent light emitting layer (6BFc), a third electron transport layer (9c), an electron injection layer (10), a cathode (11), and a capping layer (14) are sequentially stacked is illustrated. In this structure, the compound of Formula 1 may be included in one or more layers among the first blue fluorescent emitting layer (6BFa), the second blue fluorescent emitting layer (6BFb), and the third blue fluorescent emitting layer (6BFc), and the formula Compound 2 may be included in one or more of the first electron transport layer (9a), the second electron transport layer (9b), the third electron transport layer (9c), and the electron injection layer (10).

The N-type charge generation layer is 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4TCNQ), fluorine-substituted 3,4,9,10-phene Rylenetetracarboxylic dianhydride (PTCDA), cyano-substituted PTCDA, naphthalenetetracarboxylic dianhydride (NTCDA), fluorine-substituted NTCDA, cyano-substituted NTCDA, hexaazatriphenyline derivatives It may be, but is not limited to this. In one embodiment, the N-type charge generation layer may simultaneously include a benzoimidazophenanthrinine-based derivative and a Li metal.

The P-type charge generation layer may simultaneously include an arylamine-based derivative and a compound containing a cyano group.

The organic light emitting device of the present specification can be manufactured using materials and methods known in the art, except that the organic material layer includes the above compound.

When the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.

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

Additionally, the compound may be formed into 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 application method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited thereto.

In addition to this method, an organic light-emitting device can also be made by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate. However, the manufacturing method is not limited to this.

The anode material is generally preferably a material with a large work function to facilitate hole injection into the organic layer. For example, metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO:Al or SnO ₂ : Combination of metal and oxide such as Sb; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline are included, but are not limited thereto.

The cathode material is generally preferably a material with a small work function to facilitate electron injection into the organic layer. metals or alloys thereof, for example magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead; Examples include, but are not limited to, multi-layered materials such as LiF/Al or LiO ₂ /Al.

The light emitting layer may include a host material and a dopant material. Host materials include condensed aromatic ring derivatives or heterocyclic ring-containing compounds. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocycle-containing compounds include dibenzofuran derivatives, ladder-type furan compounds, These include, but are not limited to, pyrimidine derivatives.

The dopant materials include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, aromatic amine derivatives are condensed aromatic ring derivatives having a substituted or unsubstituted arylamine group, and include pyrene, anthracene, chrysene, periplanthene, etc. having an arylamine group. In addition, a styrylamine compound is a compound in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, and is one or two or more selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamine group. The substituent is substituted or unsubstituted. Specifically, styrylamine, styryldiamine, styryltriamine, styryltetraamine, etc. are included, but are not limited thereto. Additionally, metal complexes include, but are not limited to, iridium complexes and platinum complexes.

The hole injection layer is a layer that receives holes from the electrode. The hole injection material preferably has the ability to transport holes and has an excellent hole receiving effect from the anode and an excellent hole injection effect with respect to the light emitting layer or light emitting material. Additionally, a material that has an excellent ability to prevent the movement of excitons generated in the light-emitting layer to the electron injection layer or electron injection material is desirable. Additionally, materials with excellent thin film forming ability are desirable. Additionally, it is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of hole injection materials include metal porphyrin, oligothiophene, and arylamine-based organic materials; Hexanitrilehexaazatriphenylene series organic substances; Organic substances of the quinacridone series; Perylene-based organic substances; These include, but are not limited to, polythiophene-based conductive polymers such as anthraquinone and polyaniline.

The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light emitting layer, and may have a single-layer structure or a multi-layer structure of two or more layers. The hole transport material is preferably a material that can receive holes from the anode or hole injection layer and transfer them to the light emitting layer, and has high mobility for holes. Specific examples include, but are not limited to, arylamine-based organic materials, carbazole-based compounds, conductive polymers, and block copolymers with both conjugated and non-conjugated portions.

In one embodiment of the present specification, the hole transport layer has a multi-layer structure of two or more layers. Specifically, it has a two-layer structure, and each layer contains different materials.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer. The electron transport material is a material that can easily receive electrons from the cathode and transfer them to the light-emitting layer, and a material with high mobility for electrons is preferred. Specific examples include Al complex of 8-hydroxyquinoline; Complex containing Alq ₃ ; organic radical compounds; These include, but are not limited to, hydroxyflavone-metal complexes. The electron transport layer can be used with any desired cathode material, as used according to the prior art. In particular, suitable cathode materials are conventional materials with a low work function followed by an aluminum or silver layer. Specifically, there are cesium, barium, calcium, ytterbium, and samarium, and in each case, an aluminum layer or a silver layer follows.

The electron injection layer is a layer that receives electrons from the electrode. It is preferable that the electron injection material has excellent electron transport ability, has an electron receiving effect from the second electrode, and has an excellent electron injection effect with respect to the light emitting layer or light emitting material. In addition, a material that prevents excitons generated in the light-emitting layer from moving to the hole injection layer and has excellent thin film forming ability is desirable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc. and their derivatives, These include, but are not limited to, metal complex compounds and nitrogen-containing five-membered ring derivatives.

The metal complex compounds include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, and 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) (o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, etc. , but is not limited to this.

The electron blocking layer is a layer that can improve the lifespan and efficiency of the device by preventing electrons injected from the electron injection layer from passing through the light emitting layer and entering the hole injection layer. Known materials can be used without limitation, and can be formed between a light-emitting layer and a hole injection layer, or between a light-emitting layer and a layer that simultaneously performs hole injection and hole transport.

The hole blocking layer is a layer that prevents holes from reaching the cathode, and can generally be formed under the same conditions as the electron injection layer. Specifically, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, aluminum complexes, etc. are included, but are not limited thereto.

The organic light emitting device according to the present specification may be a front emitting type, a back emitting type, or a double-sided emitting type depending on the material used.

The organic light emitting device according to the present specification can be included and used in various electronic devices. For example, the electronic device may be a display panel, a touch panel, a solar module, a lighting device, etc., but is not limited thereto.

Hereinafter, in order to explain the present specification in detail, examples and comparative examples will be described in detail. However, the Examples and Comparative Examples according to the present specification may be modified in various other forms, and the scope of the present specification is not to be construed as being limited to the Examples and Comparative Examples detailed below. The examples and comparative examples of this specification are provided to more completely explain the present specification to those with average knowledge in the art.

Preparation Example 1-1: Preparation of Compound B1

Compound B1-P0 (26.5g, 87.1mmol) and AlCl ₃ (0.5g) were added to C ₆ D ₆ (400ml) and stirred for 2 hours. After completion of the reaction, D ₂ O (60ml) 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 anhydrous magnesium sulfate (MgSO ₄ ) and recrystallized with ethyl acetate to obtain compound B1-P1 (19.3 g, 69%).

MS: [M+H] ⁺ = 321

Compound B1-P1 (19.0 g, 59.3 mmol), N-bromosuccinimide (NBS) (11.6 g, 65.2 mmol), and 300 ml of dimethylformamide (DMF) were added, and stirred at room temperature under an argon atmosphere for 8 hours. After completion of the reaction, the organic layer was extracted with water and ethyl acetate. The extract was dried with anhydrous magnesium sulfate (MgSO ₄ ) and then filtered. After concentrating the filtrate under reduced pressure, the sample was purified by silica gel column chromatography to obtain compound B1-P2 (17.0 g, 72%).

MS: [M+H] ⁺ = 398

In a nitrogen atmosphere, B1-P2 (15 g, 37.7 mmol) and naphthalen-1-ylboronic acid (6.5 g, 37.7 mmol) were added to 300 ml of 1,4-dioxine, stirred and refluxed. Afterwards, potassium carbonate (15.6 g, 113 mmol) was dissolved in 16 ml of water, stirred sufficiently, and then tetrakistriphenyl-phosphinopalladium (1.3 g, 1.1 mmol) was added. After reacting for 2 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in 336 mL of 20 times chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate to prepare white solid compound B1 (9.9 g, 59%, MS: [M+H]+ = 446.6).

Preparation Example 1-2: Preparation of Compound B2

Compound B2 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was used according to the above reaction formula.

MS: [M+H] ⁺ = 526

Preparation Example 1-3: Preparation of Compound B3

Compound B3 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was used according to the above reaction formula.

MS: [M+H] ⁺ = 486

Preparation Example 1-4: Preparation of Compound B4

Compound B4 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was prepared according to the above reaction scheme.

MS: [M+H] ⁺ = 484

Preparation Example 1-5: Preparation of Compound B5

Compound B5 was prepared in the same manner as in Preparation Example 1-1, except that each starting material was used according to the above reaction scheme.

MS: [M+H] ⁺ = 592

Preparation Example 1-6: Preparation of Compound B6

Compound B6 was prepared in the same manner as the B1-P1 preparation method in Preparation Example 1-1, except that each starting material was used according to the above reaction scheme.

MS: [M+H] ⁺ = 453

Preparation Example 1-7: Preparation of Compound B7

Compound B7 was prepared in the same manner as the B1-P1 preparation method in Preparation Example 1-1, except that each starting material was used according to the above reaction scheme.

MS: [M+H] ⁺ = 533

Preparation Example 1-8: Preparation of Compound B8

Compound B8 was prepared in the same manner as the B1-P1 preparation method in Preparation Example 1-1, except that each starting material was used according to the above reaction scheme.

MS: [M+H] ⁺ = 493

Preparation Example 1-9: Preparation of Compound B9

Compound B9 was prepared in the same manner as the B1-P1 preparation method in Preparation Example 1-1, except that each starting material was used according to the above reaction scheme.

MS: [M+H] ⁺ = 493

Preparation Example 1-10: Preparation of Compound B10

Compound B10 was prepared in the same manner as the method for preparing compound B1-P1 in Preparation Example 1-1, except that each starting material was used according to the above reaction scheme.

MS: [M+H] ⁺ = 601

Preparation Example 2-1: Preparation of Compound E1

Compound E1 was prepared in the same manner as the method for preparing compound B1 in Preparation Example 1-1, except that each starting material was used according to the above reaction scheme.

MS: [M+H] ⁺ = 432

Preparation Example 2-2: Preparation of Compound E2

Compound E2 was prepared in the same manner as the method for preparing compound B1 in Preparation Example 1-1, except that each starting material was prepared according to the above reaction scheme.

MS: [M+H] ⁺ = 482

Preparation Example 2-3: Preparation of Compound E3

Compound E3 was prepared in the same manner as the method for preparing compound B1 in Preparation Example 1-1, except that each starting material was prepared according to the above reaction scheme.

MS: [M+H] ⁺ = 521

Preparation Example 2-4: Preparation of Compound E4

Compound E4 was prepared in the same manner as the method for preparing compound B1 in Preparation Example 1-1, except that each starting material was used according to the above reaction scheme.

MS: [M+H] ⁺ = 538

Preparation Example 2-5: Preparation of Compound E5

Compound E5 was prepared in the same manner as the method for preparing compound B1 in Preparation Example 1-1, except that each starting material was used according to the above reaction scheme.

MS: [M+H] ⁺ = 508

Preparation Example 2-6: Preparation of Compound E6

Compound E6 was prepared in the same manner as the method for preparing compound B1 in Preparation Example 1-1, except that each starting material was used according to the above reaction scheme.

MS: [M+H] ⁺ = 457

Preparation Example 2-7: Preparation of Compound E7

Compound E7 was prepared in the same manner as the method for preparing compound B1 in Preparation Example 1-1, except that each starting material was used according to the above reaction scheme.

MS: [M+H] ⁺ = 672

Preparation Example 2-8: Preparation of compound E8

Compound E8 was prepared in the same manner as the method for preparing compound B1 in Preparation Example 1-1, except that each starting material was used according to the above reaction scheme.

MS: [M+H] ⁺ = 548

Example 1-1.

A glass substrate coated with a thin film of ITO (indium tin oxide) to a thickness of 1000 Å was placed in distilled water with a detergent dissolved in it and washed with ultrasonic waves. At this time, a detergent from Fischer Co. was used, and distilled water that was filtered secondarily using a filter from Millipore Co. was used. After washing the ITO for 30 minutes, ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After washing with distilled water, it was ultrasonic washed with solvents of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. Additionally, the substrate was cleaned for 5 minutes using oxygen plasma and then transported to a vacuum evaporator.

On the ITO transparent electrode prepared in this way, the following HI-A compound was thermally vacuum deposited to a thickness of 600 Å to form a hole injection layer.

On the hole injection layer, 50Å of the following HAT compound and 60Å of the following compound HT-A were sequentially vacuum deposited to form a first hole transport layer and a second hole transport layer.

Next, the compounds B1 and BD prepared in Preparation Example 1-1 were vacuum deposited on the second hole transport layer with a film thickness of 200 Å at a weight ratio of 25:1 to form a light emitting layer.

Compound E1 prepared in Preparation Example 2-1 was vacuum deposited on the emitting layer to form an electron injection and transport layer with a thickness of 350 Å.

A cathode was formed by sequentially depositing lithium fluoride (LiF) to a thickness of 10 Å and aluminum to a thickness of 1000 Å on the electron injection and transport layer.

In the above process, the deposition rate of organic materials was maintained at 0.4 Å/sec to 0.9 Å/sec, the deposition rate of lithium fluoride of the cathode was maintained at 0.3 Å/sec, and aluminum was maintained at 2 Å/sec, and the vacuum level during deposition was An organic light emitting device was manufactured by maintaining 1×10 ^-7 torr to 5×10 ^-5 torr.

Examples 1-2 to 1-80.

An organic light emitting device was manufactured in the same manner as in Example 1-1, except that the compounds listed in Table 1 below were used instead of compounds B1 and E1 in Example 1-1.

Comparative Examples 1-1 to 1-90.

An organic light emitting device was manufactured in the same manner as in Example 1-1, except that the compounds listed in Table 1 below were used instead of compounds B1 and E1 in Example 1-1.

For the organic light-emitting devices manufactured in Examples 1-1 to 1-80 and Comparative Examples 1-1 to 1-90, the driving voltage and luminous efficiency were measured at a current density of 10 mA/cm ² and at a current density of 20 mA/cm ² The time (T90) for the current density to reach 90% of the initial luminance was measured. The results are shown in Table 1 below.

division luminescent layer Electron injection and transport layer Voltage (V@10 mA/cm ² ) Efficiency (cd/A@10 mA/cm ² ) Color coordinates (x, y) Lifespan (h)T90 @20 mA/cm ² ) Example 1-1 B1 E1 3.96 4.60 (0.134, 0.090) 180 Example 1-2 B1 E2 4.04 4.51 (0.135, 0.091) 194 Example 1-3 B1 E3 4.08 4.74 (0.135, 0.092) 157 Example 1-4 B1 E4 4.04 4.55 (0.134, 0.090) 167 Examples 1-5 B1 E5 3.92 4.69 (0.135, 0.091) 164 Example 1-6 B1 E6 4.16 4.32 (0.135, 0.092) 218 Example 1-7 B1 E7 4.00 4.65 (0.134, 0.090) 162 Examples 1-8 B1 E8 4.08 4.45 (0.135, 0.091) 185 Example 1-9 B2 E1 4.00 4.65 (0.135, 0.092) 176 Examples 1-10 B2 E2 4.08 4.55 (0.134, 0.090) 191 Example 1-11 B2 E3 4.12 4.79 (0.134, 0.090) 153 Examples 1-12 B2 E4 4.08 4.60 (0.135, 0.091) 164 Example 1-13 B2 E5 3.96 4.74 (0.135, 0.092) 161 Example 1-14 B2 E6 4.20 4.37 (0.134, 0.090) 213 Example 1-15 B2 E7 4.04 4.69 (0.135, 0.091) 159 Example 1-16 B2 E8 4.12 4.50 (0.135, 0.092) 182 Example 1-17 B3 E1 3.72 4.65 (0.134, 0.090) 205 Example 1-18 B3 E2 3.80 4.55 (0.135, 0.091) 222 Example 1-19 B3 E3 3.83 4.79 (0.135, 0.092) 179 Examples 1-20 B3 E4 3.80 4.60 (0.134, 0.090) 191 Example 1-21 B3 E5 3.69 4.74 (0.135, 0.091) 187 Example 1-22 B3 E6 3.91 4.37 (0.134, 0.090) 248 Example 1-23 B3 E7 3.76 4.69 (0.135, 0.091) 185 Example 1-24 B3 E8 3.83 4.50 (0.135, 0.092) 211 Example 1-25 B4 E1 3.68 4.65 (0.134, 0.090) 212 Example 1-26 B4 E2 3.76 4.55 (0.135, 0.091) 229 Example 1-27 B4 E3 3.79 4.79 (0.135, 0.092) 185 Example 1-28 B4 E4 3.76 4.60 (0.134, 0.090) 198 Example 1-29 B4 E5 3.65 4.74 (0.135, 0.091) 193 Example 1-30 B4 E6 3.87 4.37 (0.135, 0.092) 257 Example 1-31 B4 E7 3.72 4.69 (0.134, 0.090) 191 Example 1-32 B4 E8 3.79 4.50 (0.134, 0.090) 219 Example 1-33 B5 E1 3.64 4.67 (0.135, 0.091) 214 Example 1-34 B5 E2 3.72 4.58 (0.135, 0.092) 231 Example 1-35 B5 E3 3.75 4.81 (0.134, 0.090) 186 Example 1-36 B5 E4 3.72 4.62 (0.135, 0.091) 199 Example 1-37 B5 E5 3.61 4.76 (0.135, 0.092) 195 Example 1-38 B5 E6 3.83 4.39 (0.134, 0.090) 259 Example 1-39 B5 E7 3.68 4.72 (0.135, 0.091) 193 Example 1-40 B5 E8 3.75 4.52 (0.135, 0.092) 221 Example 1-41 B6 E1 3.96 4.60 (0.134, 0.090) 198 Example 1-42 B6 E2 4.04 4.51 (0.135, 0.091) 214 Example 1-43 B6 E3 4.08 4.74 (0.134, 0.090) 172 Example 1-44 B6 E4 4.04 4.55 (0.135, 0.091) 184 Example 1-45 B6 E5 3.92 4.69 (0.135, 0.092) 180 Example 1-46 B6 E6 4.16 4.32 (0.134, 0.090) 240 Example 1-47 B6 E7 4.00 4.65 (0.135, 0.091) 178 Example 1-48 B6 E8 4.08 4.45 (0.135, 0.092) 204 Example 1-49 B7 E1 4.00 4.65 (0.134, 0.090) 194 Example 1-50 B7 E2 4.08 4.55 (0.135, 0.091) 210 Example 1-51 B7 E3 4.12 4.79 (0.135, 0.092) 169 Example 1-52 B7 E4 4.08 4.60 (0.134, 0.090) 180 Example 1-53 B7 E5 3.96 4.74 (0.134, 0.090) 177 Example 1-54 B7 E6 4.20 4.37 (0.135, 0.091) 235 Example 1-55 B7 E7 4.04 4.69 (0.135, 0.092) 175 Example 1-56 B7 E8 4.12 4.50 (0.134, 0.090) 200 Example 1-57 B8 E1 3.72 4.65 (0.135, 0.091) 232 Example 1-58 B8 E2 3.80 4.55 (0.135, 0.092) 250 Example 1-59 B8 E3 3.83 4.79 (0.134, 0.090) 202 Example 1-60 B8 E4 3.80 4.60 (0.135, 0.091) 216 Example 1-61 B8 E5 3.69 4.74 (0.135, 0.092) 211 Example 1-62 B8 E6 3.91 4.37 (0.134, 0.090) 281 Example 1-63 B8 E7 3.76 4.69 (0.135, 0.091) 209 Example 1-64 B8 E8 3.83 4.50 (0.134, 0.090) 239 Example 1-65 B9 E1 3.68 4.65 (0.135, 0.091) 240 Example 1-66 B9 E2 3.76 4.55 (0.135, 0.092) 259 Example 1-67 B9 E3 3.79 4.79 (0.134, 0.090) 209 Example 1-68 B9 E4 3.76 4.60 (0.135, 0.091) 223 Example 1-69 B9 E5 3.65 4.74 (0.135, 0.092) 218 Example 1-70 B9 E6 3.87 4.37 (0.134, 0.090) 290 Example 1-71 B9 E7 3.72 4.69 (0.135, 0.091) 216 Example 1-72 B9 E8 3.79 4.50 (0.135, 0.092) 247 Example 1-73 B10 E1 3.64 4.67 (0.134, 0.090) 242 Example 1-74 B10 E2 3.72 4.58 (0.134, 0.090) 261 Example 1-75 B10 E3 3.75 4.81 (0.135, 0.091) 211 Example 1-76 B10 E4 3.72 4.62 (0.135, 0.092) 225 Example 1-77 B10 E5 3.61 4.76 (0.134, 0.090) 220 Example 1-78 B10 E6 3.83 4.39 (0.135, 0.091) 293 Example 1-79 B10 E7 3.68 4.72 (0.135, 0.092) 218 Example 1-80 B10 E8 3.75 4.52 (0.134, 0.090) 249 Comparative Example 1-1 B1 ET-A 4.75 2.81 (0.135, 0.091) 40 Comparative Example 1-2 B1 ET-B 4.85 2.75 (0.135, 0.092) 43 Comparative Example 1-3 B1 ET-C 4.89 2.89 (0.134, 0.090) 34 Comparative Example 1-4 B1 ET-D 4.85 2.78 (0.135, 0.091) 37 Comparative Example 1-5 B1 ET-E 4.70 2.86 (0.134, 0.090) 36 Comparative Example 1-6 B1 ET-F 4.99 2.64 (0.135, 0.091) 48 Comparative Example 1-7 B1 ET-G 4.80 2.83 (0.135, 0.092) 36 Comparative Example 1-8 B1 ET-H 4.89 2.72 (0.134, 0.090) 41 Comparative Example 1-9 B3 ET-A 4.47 2.83 (0.135, 0.091) 45 Comparative Example 1-10 B3 ET-B 4.56 2.78 (0.135, 0.092) 49 Comparative Example 1-11 B3 ET-C 4.60 2.92 (0.134, 0.090) 39 Comparative Example 1-12 B3 ET-D 4.56 2.81 (0.135, 0.091) 42 Comparative Example 1-13 B3 ET-E 4.42 2.89 (0.135, 0.092) 41 Comparative Example 1-14 B3 ET-F 4.69 2.66 (0.134, 0.090) 55 Comparative Example 1-15 B3 ET-G 4.51 2.86 (0.134, 0.090) 41 Comparative Example 1-16 B3 ET-H 4.60 2.74 (0.135, 0.091) 46 Comparative Example 1-17 BH-A E1 3.96 4.60 (0.135, 0.092) 122 Comparative Example 1-18 BH-A E2 4.04 4.51 (0.134, 0.090) 132 Comparative Example 1-19 BH-A E3 4.08 4.74 (0.135, 0.091) 106 Comparative Example 1-20 BH-A E4 4.04 4.55 (0.135, 0.092) 114 Comparative Example 1-21 BH-A E5 3.92 4.69 (0.134, 0.090) 111 Comparative Example 1-22 BH-A E6 4.16 4.32 (0.135, 0.091) 108 Comparative Example 1-23 BH-A E7 4.00 4.65 (0.135, 0.092) 110 Comparative Example 1-24 BH-A E8 4.08 4.45 (0.134, 0.090) 126 Comparative Example 1-25 BH-B E1 4.00 4.65 (0.135, 0.091) 122 Comparative Example 1-26 BH-B E2 4.08 4.55 (0.134, 0.090) 131 Comparative Example 1-27 BH-B E3 4.12 4.79 (0.135, 0.091) 106 Comparative Example 1-28 BH-B E4 4.08 4.60 (0.135, 0.092) 113 Comparative Example 1-29 BH-B E5 3.96 4.74 (0.134, 0.090) 111 Comparative Example 1-30 BH-B E6 4.20 4.37 (0.135, 0.091) 107 Comparative Example 1-31 BH-B E7 4.04 4.69 (0.135, 0.092) 110 Comparative Example 1-32 BH-B E8 4.12 4.50 (0.134, 0.090) 125 Comparative Example 1-33 BH-C E1 3.72 4.65 (0.135, 0.091) 104 Comparative Example 1-34 BH-C E2 3.80 4.55 (0.135, 0.092) 105 Comparative Example 1-35 BH-C E3 3.83 4.79 (0.134, 0.090) 125 Comparative Example 1-36 BH-C E4 3.80 4.60 (0.134, 0.090) 134 Comparative Example 1-37 BH-C E5 3.69 4.74 (0.135, 0.091) 131 Comparative Example 1-38 BH-C E6 3.91 4.37 (0.135, 0.092) 114 Comparative Example 1-39 BH-C E7 3.76 4.69 (0.134, 0.090) 129 Comparative Example 1-40 BH-C E8 3.83 4.50 (0.135, 0.091) 148 Comparative Example 1-41 BH-D E1 3.68 4.65 (0.135, 0.092) 149 Comparative Example 1-42 BH-D E2 3.76 4.55 (0.134, 0.090) 121 Comparative Example 1-43 BH-D E3 3.79 4.79 (0.135, 0.091) 129 Comparative Example 1-44 BH-D E4 3.76 4.60 (0.135, 0.092) 138 Comparative Example 1-45 BH-D E5 3.65 4.74 (0.134, 0.090) 135 Comparative Example 1-46 BH-D E6 3.87 4.37 (0.135, 0.091) 110 Comparative Example 1-47 BH-D E7 3.72 4.69 (0.134, 0.090) 134 Comparative Example 1-48 BH-D E8 3.79 4.50 (0.135, 0.091) 113 Comparative Example 1-49 BH-E E1 4.00 4.65 (0.135, 0.092) 106 Comparative Example 1-50 BH-E E2 4.08 4.55 (0.134, 0.090) 114 Comparative Example 1-51 BH-E E3 4.12 4.79 (0.135, 0.091) 92 Comparative Example 1-52 BH-E E4 4.08 4.60 (0.135, 0.092) 98 Comparative Example 1-53 BH-E E5 3.96 4.74 (0.134, 0.090) 96 Comparative Example 1-54 BH-E E6 4.20 4.37 (0.135, 0.091) 128 Comparative Example 1-55 BH-E E7 4.04 4.69 (0.135, 0.092) 95 Comparative Example 1-56 BH-E E8 4.12 4.50 (0.134, 0.090) 109 Comparative Example 1-57 BH-F E1 3.72 4.65 (0.134, 0.090) 123 Comparative Example 1-58 BH-F E2 3.80 4.55 (0.135, 0.091) 133 Comparative Example 1-59 BH-F E3 3.83 4.79 (0.135, 0.092) 107 Comparative Example 1-60 BH-F E4 3.80 4.60 (0.134, 0.090) 115 Comparative Example 1-61 BH-F E5 3.69 4.74 (0.135, 0.091) 112 Comparative Example 1-62 BH-F E6 3.91 4.37 (0.135, 0.092) 109 Comparative Example 1-63 BH-F E7 3.76 4.69 (0.134, 0.090) 111 Comparative Example 1-64 BH-F E8 3.83 4.50 (0.135, 0.091) 127 Comparative Example 1-65 BH-G E1 3.68 4.65 (0.135, 0.092) 127 Comparative Example 1-66 BH-G E2 3.76 4.55 (0.134, 0.090) 138 Comparative Example 1-67 BH-G E3 3.79 4.79 (0.135, 0.091) 111 Comparative Example 1-68 BH-G E4 3.76 4.60 (0.134, 0.090) 119 Comparative Example 1-69 BH-G E5 3.65 4.74 (0.135, 0.091) 116 Comparative Example 1-70 BH-G E6 3.87 4.37 (0.135, 0.092) 104 Comparative Example 1-71 BH-G E7 3.72 4.69 (0.134, 0.090) 115 Comparative Example 1-72 BH-G E8 3.79 4.50 (0.135, 0.091) 131 Comparative Example 1-73 BH-H E1 3.64 4.67 (0.135, 0.092) 129 Comparative Example 1-74 BH-H E2 3.72 4.58 (0.134, 0.090) 139 Comparative Example 1-75 BH-H E3 3.75 4.81 (0.135, 0.091) 112 Comparative Example 1-76 BH-H E4 3.72 4.62 (0.135, 0.092) 120 Comparative Example 1-77 BH-H E5 3.61 4.76 (0.134, 0.090) 117 Comparative Example 1-78 BH-H E6 3.83 4.39 (0.134, 0.090) 106 Comparative Example 1-79 BH-H E7 3.68 4.72 (0.135, 0.091) 116 Comparative Example 1-80 BH-H E8 3.75 4.52 (0.135, 0.092) 132 Comparative Example 1-81 B1 ET-I 4.57 3.46 (0.135, 0.091) 100 Comparative Example 1-82 B2 ET-I 4.66 3.49 (0.135, 0.092) 90 Comparative Example 1-83 B3 ET-I 4.39 3.43 (0.134, 0.090) 105 Comparative Example 1-84 B4 ET-I 4.41 3.45 (0.135, 0.091) 106 Comparative Example 1-85 B5 ET-I 4.30 3.49 (0.135, 0.092) 108 Comparative Example 1-86 B6 ET-I 4.57 3.46 (0.135, 0.091) 100 Comparative Example 1-87 B7 ET-I 4.66 3.49 (0.135, 0.092) 90 Comparative Example 1-88 B8 ET-I 4.39 3.43 (0.135, 0.091) 105 Comparative Example 1-89 B9 ET-I 4.41 3.45 (0.135, 0.091) 106 Comparative Example 1-90 B10 ET-I 4.30 3.49 (0.135, 0.091) 108

Comparing Examples 1-1 to 1-80 and Comparative Examples 1-1 to 1-16 in Table 1, organic light-emitting devices (Examples 1-1 to 1) applying the heterocyclic compound of Formula 2 according to the present specification It can be seen that -80) shows significantly superior characteristics in terms of voltage, efficiency, and lifespan than the organic light-emitting device (Comparative Examples 1-1 to 1-16) using a structure that does not contain a cyano group in the skeleton of Chemical Formula 2 (Comparative Examples 1-1 to 1-16).

Comparing Examples 1-1 to 1-80 and Comparative Examples 1-17 to 1-48 in Table 1, organic light-emitting devices (Examples 1-1 to 1) using the compound of Formula 1 according to the present specification -80) has the same skeleton as Formula 1, but shows significantly superior characteristics in terms of lifespan than the organic light-emitting device (Comparative Examples 1-17 to 1-48) using a structure in which deuterium is not connected to anthracene but is connected to other substituents. You can.

Comparing Examples 1-1 to 1-80 and Comparative Examples 1-49 to 1-80 in Table 1, organic light-emitting devices using the compound of Formula 1 according to the present specification (Examples 1-1 to 1-80 ) It can be seen that it shows significantly superior characteristics in terms of lifespan than the organic light-emitting device (Comparative Examples 1-49 to 1-80) using the same skeleton as Formula 1, but a structure without deuterium substitution.

Comparing Examples 1-1 to 1-80 and Comparative Examples 1-81 to 1-90 in Table 1, organic light-emitting devices using the compound of Formula 2 according to the present specification (Examples 1-1 to 1-80 ) can be confirmed to exhibit significantly superior characteristics in terms of voltage, efficiency, and lifespan than organic light-emitting devices using benzimidazole-based compounds (Comparative Examples 1-81 to 1-90).

In addition, when Formula 1 includes a dibenzofuran-based or naphthobenzofuran-based substituent represented by Formula A1 (Examples 1-17 to 1-40 and Examples 1-57 to 1-80), low voltage, It can be seen that high efficiency and long life characteristics are enhanced.

Example 2-1.

A glass substrate coated with a thin film of ITO (indium tin oxide) to a thickness of 1000 Å was placed in distilled water with a detergent dissolved in it and washed with ultrasonic waves. At this time, a detergent from Fischer Co. was used, and distilled water that was filtered secondarily using a filter from Millipore Co. was used. After washing the ITO for 30 minutes, ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After washing with distilled water, it was ultrasonic washed with solvents of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. Additionally, the substrate was cleaned for 5 minutes using oxygen plasma and then transported to a vacuum evaporator.

On the ITO transparent electrode prepared in this way, the following HI-A compound was thermally vacuum deposited to a thickness of 600 Å to form a hole injection layer.

On the hole injection layer, 50Å of the following HAT compound and 60Å of the following compound HT-A were sequentially vacuum deposited to form a first hole transport layer and a second hole transport layer.

Next, the compounds B1 and BD prepared in Preparation Example 1-1 were vacuum deposited on the second hole transport layer with a film thickness of 200 Å at a weight ratio of 25:1 to form a light emitting layer.

On the emitting layer, the following HB compound was vacuum deposited to a thickness of 50 Å to form a hole blocking layer, and compound E1 prepared in Preparation Example 2-1 was vacuum deposited to form an electron injection and transport layer to a thickness of 300 Å.

A cathode was formed by sequentially depositing lithium fluoride (LiF) to a thickness of 10 Å and aluminum to a thickness of 1000 Å on the electron injection and transport layer.

In the above process, the deposition rate of organic materials was maintained at 0.4 Å/sec to 0.9 Å/sec, the deposition rate of lithium fluoride of the cathode was maintained at 0.3 Å/sec, and aluminum was maintained at 2 Å/sec, and the vacuum level during deposition was An organic light emitting device was manufactured by maintaining 1×10 ^-7 torr to 5×10 ^-5 torr.

Examples 2-2 to 2-90.

An organic light-emitting device was manufactured in the same manner as in Example 2-1, except that the compounds listed in Table 2 below were used instead of compounds B1 and E1 in Example 2-1.

Comparative Examples 2-1 to 2-80.

An organic light-emitting device was manufactured in the same manner as in Example 2-1, except that the compounds listed in Table 2 below were used instead of compounds B1 and E1 in Example 2-1.

For the organic light-emitting devices manufactured in Examples 2-1 to 2-80 and Comparative Examples 2-1 to 2-90, the driving voltage and luminous efficiency were measured at a current density of 10 mA/cm ² and at a current density of 20 mA/cm ² The time (T90) for the current density to reach 90% of the initial luminance was measured. The results are shown in Table 2 below.

division luminescent layer Electron injection and transport layer Voltage (V@10 mA/cm ² ) Efficiency (cd/A@10 mA/cm ² ) Color coordinates (x, y) Lifespan (h)T90 @20 mA/cm ² ) Example 2-1 B1 E1 3.88 4.83 (0.134, 0.090) 122 Example 2-2 B1 E2 3.96 4.73 (0.135, 0.091) 132 Example 2-3 B1 E3 4.00 4.97 (0.135, 0.092) 106 Example 2-4 B1 E4 3.96 4.78 (0.134, 0.090) 114 Example 2-5 B1 E5 3.84 4.93 (0.135, 0.091) 111 Example 2-6 B1 E6 4.07 4.54 (0.135, 0.092) 148 Example 2-7 B1 E7 3.92 4.88 (0.134, 0.090) 110 Example 2-8 B1 E8 4.00 4.68 (0.135, 0.091) 126 Example 2-9 B2 E1 3.92 4.88 (0.135, 0.092) 120 Example 2-10 B2 E2 4.00 4.78 (0.134, 0.090) 130 Example 2-11 B2 E3 4.04 5.02 (0.134, 0.090) 104 Example 2-12 B2 E4 4.00 4.83 (0.135, 0.091) 112 Example 2-13 B2 E5 3.88 4.98 (0.135, 0.092) 109 Example 2-14 B2 E6 4.12 4.59 (0.134, 0.090) 145 Example 2-15 B2 E7 3.96 4.93 (0.135, 0.091) 108 Example 2-16 B2 E8 4.04 4.72 (0.135, 0.092) 124 Example 2-17 B3 E1 3.65 4.88 (0.134, 0.090) 140 Example 2-18 B3 E2 3.72 4.78 (0.135, 0.091) 151 Example 2-19 B3 E3 3.76 5.02 (0.135, 0.092) 121 Example 2-20 B3 E4 3.72 4.83 (0.134, 0.090) 130 Example 2-21 B3 E5 3.61 4.98 (0.135, 0.091) 127 Example 2-22 B3 E6 3.83 4.59 (0.134, 0.090) 169 Example 2-23 B3 E7 3.68 4.93 (0.135, 0.091) 126 Example 2-24 B3 E8 3.76 4.72 (0.135, 0.092) 144 Example 2-25 B4 E1 3.61 4.88 (0.134, 0.090) 144 Example 2-26 B4 E2 3.68 4.78 (0.135, 0.091) 156 Example 2-27 B4 E3 3.72 5.02 (0.135, 0.092) 126 Example 2-28 B4 E4 3.68 4.83 (0.134, 0.090) 134 Example 2-29 B4 E5 3.57 4.98 (0.135, 0.091) 131 Example 2-30 B4 E6 3.79 4.59 (0.135, 0.092) 175 Example 2-31 B4 E7 3.65 4.93 (0.134, 0.090) 130 Example 2-32 B4 E8 3.72 4.72 (0.134, 0.090) 149 Example 2-33 B5 E1 3.57 4.90 (0.135, 0.091) 146 Example 2-34 B5 E2 3.64 4.80 (0.135, 0.092) 157 Example 2-35 B5 E3 3.68 5.05 (0.134, 0.090) 127 Example 2-36 B5 E4 3.64 4.85 (0.135, 0.091) 135 Example 2-37 B5 E5 3.53 5.00 (0.135, 0.092) 133 Example 2-38 B5 E6 3.75 4.61 (0.134, 0.090) 176 Example 2-39 B5 E7 3.61 4.95 (0.135, 0.091) 131 Example 2-40 B5 E8 3.68 4.75 (0.135, 0.092) 150 Example 2-41 B6 E1 3.88 4.83 (0.134, 0.090) 135 Example 2-42 B6 E2 3.96 4.73 (0.135, 0.091) 145 Example 2-43 B6 E3 4.00 4.97 (0.134, 0.090) 117 Example 2-44 B6 E4 3.96 4.78 (0.135, 0.091) 125 Example 2-45 B6 E5 3.84 4.93 (0.135, 0.092) 123 Example 2-46 B6 E6 4.07 4.54 (0.134, 0.090) 163 Example 2-47 B6 E7 3.92 4.88 (0.135, 0.091) 121 Example 2-48 B6 E8 4.00 4.68 (0.135, 0.092) 139 Example 2-49 B7 E1 3.92 4.88 (0.134, 0.090) 132 Example 2-50 B7 E2 4.00 4.78 (0.135, 0.091) 143 Example 2-51 B7 E3 4.04 5.02 (0.135, 0.092) 115 Example 2-52 B7 E4 4.00 4.83 (0.134, 0.090) 123 Example 2-53 B7 E5 3.88 4.98 (0.134, 0.090) 120 Example 2-54 B7 E6 4.12 4.59 (0.135, 0.091) 160 Example 2-55 B7 E7 3.96 4.93 (0.135, 0.092) 119 Example 2-56 B7 E8 4.04 4.72 (0.134, 0.090) 136 Example 2-57 B8 E1 3.65 4.88 (0.135, 0.091) 158 Example 2-58 B8 E2 3.72 4.78 (0.135, 0.092) 170 Example 2-59 B8 E3 3.76 5.02 (0.134, 0.090) 137 Example 2-60 B8 E4 3.72 4.83 (0.135, 0.091) 147 Example 2-61 B8 E5 3.61 4.98 (0.135, 0.092) 143 Example 2-62 B8 E6 3.83 4.59 (0.134, 0.090) 191 Example 2-63 B8 E7 3.68 4.93 (0.135, 0.091) 142 Example 2-64 B8 E8 3.76 4.72 (0.134, 0.090) 162 Example 2-65 B9 E1 3.61 4.88 (0.135, 0.091) 163 Example 2-66 B9 E2 3.68 4.78 (0.135, 0.092) 176 Example 2-67 B9 E3 3.72 5.02 (0.134, 0.090) 142 Example 2-68 B9 E4 3.68 4.83 (0.135, 0.091) 152 Example 2-69 B9 E5 3.57 4.98 (0.135, 0.092) 149 Example 2-70 B9 E6 3.79 4.59 (0.134, 0.090) 197 Example 2-71 B9 E7 3.65 4.93 (0.135, 0.091) 147 Example 2-72 B9 E8 3.72 4.72 (0.135, 0.092) 168 Example 2-73 B10 E1 3.57 4.90 (0.134, 0.090) 165 Example 2-74 B10 E2 3.64 4.80 (0.134, 0.090) 178 Example 2-75 B10 E3 3.68 5.05 (0.135, 0.091) 143 Example 2-76 B10 E4 3.64 4.85 (0.135, 0.092) 153 Example 2-77 B10 E5 3.53 5.00 (0.134, 0.090) 150 Example 2-78 B10 E6 3.75 4.61 (0.135, 0.091) 199 Example 2-79 B10 E7 3.61 4.95 (0.135, 0.092) 148 Example 2-80 B10 E8 3.68 4.75 (0.134, 0.090) 170 Comparative Example 2-1 B1 ET-A 4.56 3.09 (0.135, 0.091) 17 Comparative Example 2-2 B1 ET-B 4.65 3.03 (0.135, 0.092) 18 Comparative Example 2-3 B1 ET-C 4.70 3.19 (0.134, 0.090) 14 Comparative Example 2-4 B1 ET-D 4.65 3.06 (0.135, 0.091) 15 Comparative Example 2-5 B1 ET-E 4.52 3.16 (0.134, 0.090) 15 Comparative Example 2-6 B1 ET-F 4.79 2.91 (0.135, 0.091) 20 Comparative Example 2-7 B1 ET-G 4.61 3.12 (0.135, 0.092) 15 Comparative Example 2-8 B1 ET-H 4.70 2.99 (0.134, 0.090) 17 Comparative Example 2-9 B1 ET-A 4.29 3.12 (0.135, 0.091) 19 Comparative Example 2-10 B1 ET-B 4.37 3.06 (0.135, 0.092) 20 Comparative Example 2-11 B1 ET-C 4.42 3.22 (0.134, 0.090) 17 Comparative Example 2-12 B1 ET-D 4.37 3.09 (0.135, 0.091) 18 Comparative Example 2-13 B1 ET-E 4.25 3.19 (0.135, 0.092) 17 Comparative Example 2-14 B1 ET-F 4.50 2.94 (0.134, 0.090) 23 Comparative Example 2-15 B1 ET-G 4.33 3.16 (0.134, 0.090) 17 Comparative Example 2-16 B1 ET-H 4.42 3.02 (0.135, 0.091) 20 Comparative Example 2-17 BH-A E1 3.80 5.07 (0.135, 0.092) 51 Comparative Example 2-18 BH-A E2 3.88 4.97 (0.134, 0.090) 56 Comparative Example 2-19 BH-A E3 3.92 5.22 (0.135, 0.091) 45 Comparative Example 2-20 BH-A E4 3.88 5.02 (0.135, 0.092) 48 Comparative Example 2-21 BH-A E5 3.76 5.17 (0.134, 0.090) 47 Comparative Example 2-22 BH-A E6 3.99 4.77 (0.135, 0.091) 62 Comparative Example 2-23 BH-A E7 3.84 5.12 (0.135, 0.092) 46 Comparative Example 2-24 BH-A E8 3.92 4.91 (0.134, 0.090) 53 Comparative Example 2-25 BH-B E1 3.84 5.12 (0.135, 0.091) 51 Comparative Example 2-26 BH-B E2 3.92 5.02 (0.134, 0.090) 55 Comparative Example 2-27 BH-B E3 3.96 5.28 (0.135, 0.091) 44 Comparative Example 2-28 BH-B E4 3.92 5.07 (0.135, 0.092) 48 Comparative Example 2-29 BH-B E5 3.80 5.22 (0.134, 0.090) 47 Comparative Example 2-30 BH-B E6 4.03 4.81 (0.135, 0.091) 62 Comparative Example 2-31 BH-B E7 3.88 5.17 (0.135, 0.092) 46 Comparative Example 2-32 BH-B E8 3.96 4.96 (0.134, 0.090) 53 Comparative Example 2-33 BH-C E1 3.57 5.12 (0.135, 0.091) 60 Comparative Example 2-34 BH-C E2 3.65 5.02 (0.135, 0.092) 65 Comparative Example 2-35 BH-C E3 3.68 5.28 (0.134, 0.090) 53 Comparative Example 2-36 BH-C E4 3.65 5.07 (0.134, 0.090) 56 Comparative Example 2-37 BH-C E5 3.54 5.22 (0.135, 0.091) 55 Comparative Example 2-38 BH-C E6 3.75 4.81 (0.135, 0.092) 73 Comparative Example 2-39 BH-C E7 3.61 5.17 (0.134, 0.090) 54 Comparative Example 2-40 BH-C E8 3.68 4.96 (0.135, 0.091) 62 Comparative Example 2-41 BH-D E1 3.54 5.12 (0.135, 0.092) 62 Comparative Example 2-42 BH-D E2 3.61 5.02 (0.134, 0.090) 67 Comparative Example 2-43 BH-D E3 3.64 5.28 (0.135, 0.091) 54 Comparative Example 2-44 BH-D E4 3.61 5.07 (0.135, 0.092) 58 Comparative Example 2-45 BH-D E5 3.50 5.22 (0.134, 0.090) 57 Comparative Example 2-46 BH-D E6 3.71 4.81 (0.135, 0.091) 76 Comparative Example 2-47 BH-D E7 3.57 5.17 (0.134, 0.090) 56 Comparative Example 2-48 BH-D E8 3.64 4.96 (0.135, 0.091) 64 Comparative Example 2-49 BH-E E1 3.84 5.12 (0.135, 0.092) 44 Comparative Example 2-50 BH-E E2 3.92 5.02 (0.134, 0.090) 48 Comparative Example 2-51 BH-E E3 3.96 5.28 (0.135, 0.091) 39 Comparative Example 2-52 BH-E E4 3.92 5.07 (0.135, 0.092) 41 Comparative Example 2-53 BH-E E5 3.80 5.22 (0.134, 0.090) 40 Comparative Example 2-54 BH-E E6 4.03 4.81 (0.135, 0.091) 54 Comparative Example 2-55 BH-E E7 3.88 5.17 (0.135, 0.092) 40 Comparative Example 2-56 BH-E E8 3.96 4.96 (0.134, 0.090) 46 Comparative Example 2-57 BH-F E1 3.57 5.12 (0.134, 0.090) 52 Comparative Example 2-58 BH-F E2 3.65 5.02 (0.135, 0.091) 56 Comparative Example 2-59 BH-F E3 3.68 5.28 (0.135, 0.092) 45 Comparative Example 2-60 BH-F E4 3.65 5.07 (0.134, 0.090) 48 Comparative Example 2-61 BH-F E5 3.54 5.22 (0.135, 0.091) 47 Comparative Example 2-62 BH-F E6 3.75 4.81 (0.135, 0.092) 63 Comparative Example 2-63 BH-F E7 3.61 5.17 (0.134, 0.090) 47 Comparative Example 2-64 BH-F E8 3.68 4.96 (0.135, 0.091) 53 Comparative Example 2-65 BH-G E1 3.54 5.12 (0.135, 0.092) 54 Comparative Example 2-66 BH-G E2 3.61 5.02 (0.134, 0.090) 58 Comparative Example 2-67 BH-G E3 3.64 5.28 (0.135, 0.091) 47 Comparative Example 2-68 BH-G E4 3.61 5.07 (0.134, 0.090) 50 Comparative Example 2-69 BH-G E5 3.50 5.22 (0.135, 0.091) 49 Comparative Example 2-70 BH-G E6 3.71 4.81 (0.135, 0.092) 65 Comparative Example 2-71 BH-G E7 3.57 5.17 (0.134, 0.090) 48 Comparative Example 2-72 BH-G E8 3.64 4.96 (0.135, 0.091) 55 Comparative Example 2-73 BH-H E1 3.50 5.15 (0.135, 0.092) 54 Comparative Example 2-74 BH-H E2 3.57 5.04 (0.134, 0.090) 58 Comparative Example 2-75 BH-H E3 3.60 5.30 (0.135, 0.091) 47 Comparative Example 2-76 BH-H E4 3.57 5.10 (0.135, 0.092) 50 Comparative Example 2-77 BH-H E5 3.46 5.25 (0.134, 0.090) 49 Comparative Example 2-78 BH-H E6 3.67 4.84 (0.134, 0.090) 65 Comparative Example 2-79 BH-H E7 3.53 5.20 (0.135, 0.091) 49 Comparative Example 2-80 BH-H E8 3.60 4.98 (0.135, 0.092) 56 Comparative Example 2-81 B1 ET-I 4.27 3.95 (0.135, 0.091) 62 Comparative Example 2-82 B2 ET-I 4.36 3.99 (0.135, 0.092) 56 Comparative Example 2-83 B3 ET-I 4.10 3.91 (0.134, 0.090) 65 Comparative Example 2-84 B4 ET-I 4.12 3.93 (0.135, 0.091) 66 Comparative Example 2-85 B5 ET-I 4.01 3.99 (0.135, 0.092) 67 Comparative Example 2-86 B6 ET-I 4.27 3.95 (0.135, 0.091) 62 Comparative Example 2-87 B7 ET-I 4.36 3.99 (0.135, 0.092) 56 Comparative Example 2-88 B8 ET-I 4.10 3.91 (0.135, 0.091) 65 Comparative Example 2-89 B9 ET-I 4.12 3.93 (0.135, 0.091) 66 Comparative Example 2-90 B10 ET-I 4.01 3.99 (0.135, 0.091) 67

Comparing Examples 2-1 to 2-80 and Comparative Examples 2-1 to 2-16 in Table 2, organic light-emitting devices (Examples 2-1 to 2) applying the heterocyclic compound of Formula 2 according to the present specification It can be confirmed that -80) exhibits significantly superior characteristics in terms of voltage, efficiency, and lifespan than the organic light-emitting device (Comparative Examples 2-1 to 2-16) using a structure that does not contain a cyano group in the skeleton of Chemical Formula 2 (Comparative Examples 2-1 to 2-16).

Comparing Examples 2-1 to 2-80 and Comparative Examples 2-17 to 2-48 in Table 2, organic light-emitting devices (Examples 2-1 to 2-80) applying the compound of Formula 1 according to the present specification ) It can be seen that it shows significantly superior characteristics in terms of lifespan than the organic light-emitting device (Comparative Examples 2-17 to 2-48) using the same skeleton as Formula 1, but a structure in which deuterium is not connected to anthracene.

Comparing Examples 2-1 to 2-80 and Comparative Examples 2-49 to 2-80 in Table 2, organic light-emitting devices using the compound of Formula 1 according to the present specification (Examples 2-1 to 2-80 ) It can be confirmed that it shows significantly superior characteristics in terms of lifespan than the organic light-emitting device (Comparative Examples 2-49 to 2-80) using the same skeleton as Formula 1, but a structure without deuterium substitution.

Comparing Examples 2-1 to 2-80 and Comparative Examples 2-81 to 2-90 in Table 2, organic light-emitting devices using the compound of Formula 2 according to the present specification (Examples 2-1 to 2-80 ) can be confirmed to exhibit significantly superior characteristics in terms of voltage, efficiency, and lifespan than organic light-emitting devices using benzimidazole-based compounds (Comparative Examples 2-81 to 2-90).

In addition, when Formula 1 includes a dibenzofuran-based or naphthobenzofuran-based substituent represented by Formula A1 (Examples 2-17 to 2-40 and Examples 2-57 to 2-80), low voltage, It can be seen that high efficiency and long life characteristics are strengthened.

Example 3

The Dipole Moment (Debye) values of compounds B1 to B4, B6 to B9, E1 to E5, and E8 according to an exemplary embodiment of the present specification are shown in Table 3 below.

compound Dipole Moment (Debye) B1 0.17 B2 0.29 B3 0.69 B4 1.03 B6 0.17 B7 0.29 B8 0.69 B9 1.03 E1 5.13 E2 5.17 E3 4.04 E4 5.2 E5 5.39 E8 6.49

The calculation of the Dipole Moment (Debye) was performed using the quantum chemical calculation program Gaussian 03 manufactured by Gaussian, USA, and using density functional theory (DFT), B3LYP as the functional and 6- as the basis function. For the structure optimized using 31G*, the dipole moment was calculated using time-dependent density functional theory (TD-DFT).

Based on the dipole moment value, the value of Equation 1 below was obtained and shown in Table 4 below.

[Equation 1]

| DM ₂ - DM ₁ | ≥ 3 debye

In equation 1 above,

DM ₁ is the dipole moment of the compound of Formula 1,

DM ₂ is the dipole moment of the compound of Formula 2.

Equation 1 Formula 2 E1 E2 E3 E4 E5 E8 Formula 1 B1 4.96 5 3.87 5.03 5.22 6.32 B2 4.84 4.88 3.75 4.91 5.1 6.2 B3 4.44 4.48 3.35 4.51 4.7 5.8 B4 4.1 4.14 3.01 4.17 4.36 5.46 B6 4.96 5 3.87 5.03 5.22 6.32 B7 4.84 4.88 3.75 4.91 5.1 6.2 B8 4.44 4.48 3.35 4.51 4.7 5.8 B9 4.1 4.14 3.01 4.17 4.36 5.46

Due to the high dipole moment value of Formula 2, electron injection from the cathode is smooth, and when the dipole moment value satisfies Formula 1, the efficiency and lifespan of the organic light-emitting device are improved.

1: Substrate/ 2: Anode/ 3: Hole injection layer/ 4: Hole transport layer/ 4a: First hole transport layer/ 4b: Second hole transport layer/ 4c: Third hole transport layer/ 4d: Fourth hole transport layer/ 4e: First 5 Hole transport layer/ 4f: 6th hole transport layer/ 4p: p-doped hole transport layer/ 4pa: 1st p-doped hole transport layer/4R: red hole transport layer/ 4G: green hole transport layer/ 4B: blue hole transport layer/ 5 : Electron blocking layer/ 6: Light-emitting layer/ 6a: First light-emitting layer/ 6b: Second light-emitting layer/ 6c: Third light-emitting layer/ 6BF: Blue fluorescent light-emitting layer/ 6BFa: First blue fluorescent light-emitting layer/ 6BFb: Second blue fluorescent light-emitting layer/6BFc ：Third blue fluorescent emitting layer/ 6YGP: Yellow green phosphorescent emitting layer/ 6RP: Red phosphorescent emitting layer/ 6GP: Green phosphorescent emitting layer/ 7: Hole blocking layer/ 8: Electron injection and transport layer/ 9: Electron transport layer/ 9a: First electron transport layer / 9b: second electron transport layer / 9c: third electron transport layer / 10: electron injection layer / 11: cathode / 12: N-type charge generation layer / 12a: first N-type charge generation layer / 12b: second N-type charge Generation layer/ 13: P-type charge generation layer/ 13a: First P-type charge generation layer/ 13b: Second P-type charge generation layer/ 14: Capping layer

Claims (14)

anode; cathode; And an organic material layer provided between the anode and the cathode,
The organic material layer includes a light-emitting layer and a first organic material layer,
The first organic layer is provided between the cathode and the light emitting layer,
The light-emitting layer includes a compound of the following formula (1),
An organic light-emitting device wherein the first organic material layer includes a compound of the following formula (2):
[Formula 1]

In Formula 1,
L1 and L2 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,
Ar1 and Ar2 are the same or different from each other, and are each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
D is deuterium,
[Formula 2]

In Formula 2,
L3 to L5 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,
Ar3 and Ar4 are the same as or different from each other, and are each independently a cyano group; Substituted or unsubstituted aryl group; A heterocyclic group substituted or unsubstituted with one or more substituents selected from the group consisting of an alkyl group and an aryl group and containing at least one of N and S; or ego,
Ar5 is hydrogen; heavy hydrogen; Cyano group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
At least one of Ar3 to Ar5 is a cyano group or contains one or more cyano groups as a substituent,
n1 is an integer from 0 to 7. The organic light-emitting device of claim 1, wherein the compound of Formula 1 and the compound of Formula 2 satisfy the following Formula 1:
[Equation 1]
| DM ₂ - DM ₁ | ≥ 3 debye
In equation 1 above,
DM ₁ is the dipole moment of the compound of Formula 1,
DM ₂ is the dipole moment of the compound of Formula 2. The method according to claim 1, wherein Ar1 and Ar2 are the same or different from each other, and are each independently a substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted tetraphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted phenanthrenyl group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted dibenzothiophene group; Substituted or unsubstituted naphthobenzofuran group; Or an organic light-emitting device that is a substituted or unsubstituted naphthobenzothiophene group. The organic light-emitting device according to claim 1, wherein Ar1 is of the following formula A1:
[Formula A1]

In Formula A1,
Y1 is O; or S,
R1 to R8 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; halogen group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or it is a substituted or unsubstituted heterocyclic group, or combines with adjacent substituents to form a substituted or unsubstituted ring,
One of R1 to R8 is connected to L1 of Formula 1 above. The organic light-emitting device according to claim 1, wherein at least one of Ar3 to Ar5 is a cyano group or has the following formula 201:
[Formula 201]

In Formula 201,
Ar6 is a substituted or unsubstituted divalent to tetravalent aryl group; or a divalent to tetravalent heterocyclic group that is substituted or unsubstituted with one or more substituents selected from the group consisting of an alkyl group and an aryl group and contains at least one of N and S,
m1 is an integer from 1 to 3,
The dotted line connects to Formula 2 above. The organic light-emitting device according to claim 1, wherein at least one of Ar3 to Ar5 is a cyano group or one of the following formulas 202 to 204:
[Formula 202]

[Formula 203]

[Formula 204]

In Formulas 202 to 204,
m1 is an integer from 1 to 3,
Ar61 is directly bonded; Substituted or unsubstituted arylene group; or a divalent heterocyclic group that is substituted or unsubstituted with one or more substituents selected from the group consisting of an alkyl group and an aryl group and contains at least one of N and S,
R21 is hydrogen; heavy hydrogen; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
R22 and R23 are the same or different from each other, and are each independently a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,
r21 is an integer from 0 to 4, r21' and r21'' are each an integer from 0 to 6,
When r21, r21' and r21'' are each 2 or more, R21 is the same or different from each other,
The dotted line connects to Formula 2 above. The method according to claim 1, wherein Ar3 and Ar4 are the same or different from each other and are each independently selected from Group 1 or 2 below, and Ar5 is hydrogen; heavy hydrogen; Cyano group; An organic light-emitting device selected from Group 1 or 2 below:
[Group 1]

[Group 2]

In groups 1 and 2 above,
The dotted line is the position connected to Formula 2,
Y3 is S; or NR14,
X1 to X5 are the same or different from each other, and are each independently N; or CR15,
At least one of X1 to X5 is N,
R11 to R15 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
Cy1 is a monocyclic or polycyclic aromatic hydrocarbon ring; or a monocyclic or polycyclic aromatic heterocycle containing one or more of N and S,
The structures of groups 1 and 2 include deuterium; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; or substituted or unsubstituted with one or more substituents selected from the group consisting of an alkyl group and an aryl group, and substituted or unsubstituted with a heterocyclic group containing at least one of N and S. The organic light emitting device according to claim 1, wherein Formula 1 is 100% deuterated. The organic light-emitting device according to claim 1, wherein Formula 1 is one selected from the following compounds:





















. The organic light-emitting device according to claim 1, wherein Formula 1 is one selected from the following compounds:




























. The organic light-emitting device according to claim 1, wherein Formula 2 is one selected from the following compounds:




. In claim 1,
The first organic material layer is an organic light-emitting device provided in direct contact with the cathode. In claim 1,
The organic material layer includes two or more light-emitting layers, and one layer of the two or more light-emitting layers includes the compound of Formula 1. In claim 13,
An organic light-emitting device wherein the maximum emission peaks of the two or more light-emitting layers are different from each other.