KR20240020458A - Organic light emitting device - Google Patents

Abstract

The present specification provides an organic light-emitting device including a compound represented by Formula 1 and a compound represented by Formula 2.

Description

Organic light emitting device {ORGANIC LIGHT EMITTING DEVICE}

This specification relates to organic light emitting devices.

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 made 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 the 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 is 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.

Korean Patent Publication No. 10-2017-0036641

This application seeks to provide an organic light emitting device.

An exemplary embodiment of the present specification includes an anode; cathode; Comprising a first organic material layer and a second organic material layer provided between the anode and the cathode, wherein the first organic material layer includes a compound represented by the following formula (1), and the second organic layer includes a compound represented by the following formula (2) Provides an organic light emitting device that does this.

[Formula 1]

In Formula 1,

L1 to L3 are the same or different from each other and are each independently a substituted or unsubstituted phenylene group,

One of Ar1 and Ar2 is a substituted or unsubstituted phenanthrenyl group, and the other is a substituted or unsubstituted naphthyl group,

Ra is hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group, or combined with adjacent groups to form a substituted or unsubstituted ring,

a is an integer from 0 to 9, and when a is 2 or more, Ra of 2 or more is the same or different from each other,

[Formula 2]

R1 is hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,

m is an integer from 0 to 9, and when m is 2 or more, 2 or more R1 are the same as or different from each other,

D is deuterium, n is an integer from 0 to 8,

R2 to R6 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; or the following formula A,

At least one of R2 and R6 is of formula A below,

[Formula A]

In Formula A,

R7 to R11 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group, or adjacent substituents combine with each other to form a substituted or unsubstituted ring,

The dotted line (---) is the part connected to Chemical Formula 2.

The organic light emitting device described in this specification includes a compound represented by Formula 1 in the first organic material layer and a compound represented by Formula 2 in the second organic material layer, thereby providing the effects of low driving voltage, high efficiency, and/or long lifespan.

Figure 1 shows an example of an organic light-emitting device in which a substrate 1, an anode 2, a second organic layer 22, a first organic layer 21, and a cathode 10 are sequentially stacked.
2 shows a substrate (1), anode (2), hole injection layer (3), hole transport layer (4), electron blocking layer (5), light emitting layer (6), hole blocking layer (7), and electron transport layer (8). , shows an example of an organic light emitting device in which the electron injection layer 9 and the cathode 10 are sequentially stacked.
Figure 3 shows a substrate (1), anode (2), hole injection layer (3), hole transport layer (4), electron blocking layer (5), light emitting layer (6), hole blocking layer (7), electron injection and transport layer ( 11) and the cathode 10 are sequentially stacked.

Hereinafter, this specification will be described in more detail.

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

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, “dotted line (---)” refers to a chemical formula or a position bonded to a compound.

In this specification, the deuterium substitution rate of the compound is determined by using TLC-MS (Thin-Layer Chromatography/Mass Spectrometry), and is determined by maximizing the distribution of molecular weights at the end of the reaction. A method of calculating the substitution rate based on the value or a quantitative analysis method using NMR can be determined by adding DMF as an internal standard and calculating the D-substitution rate from the integral amount of the total peak using the integration rate on 1H NMR. You can.

In this specification, “energy level” means energy level. Therefore, the energy level is interpreted to mean the absolute value of the corresponding energy value. For example, a low or deep energy level means that the absolute value increases in the minus direction from the vacuum level.

In this specification, HOMO (highest occupied molecular orbital) refers to the molecular orbital (highest occupied molecular orbital) in the region with the highest energy in the region where electrons can participate in bonding, and LUMO (lowest unoccupied molecular orbital) refers to the molecular orbital function (lowest unoccupied molecular orbital) in which an electron is in the lowest energy region of the antibonding region, and the HOMO energy level refers to the distance from the vacuum level to HOMO. Additionally, the LUMO energy level refers to the distance from the vacuum level to the LUMO.

In this specification, bandgap refers to the energy level difference between HOMO and LUMO, that is, the HOMO-LUMO gap (Gap).

In this specification, the HOMO energy level can be measured using an atmospheric photoelectron spectroscopy device (manufactured by RIKEN KEIKI Co., Ltd.: AC3), and the LUMO energy level can be calculated from the wavelength value measured through photoluminescence (PL). You can.

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 (-CN); nitro group; hydroxyl group; Alkyl group; Cycloalkyl group; Alkoxy group; Phosphine oxide group; Aryloxy group; Alkylthioxy group; Arylthioxy group; Alkyl sulphoxy group; Aryl sulfoxy group; alkenyl group; silyl group; boron group; amine group; Aryl group; Alternatively, it means that it is substituted with one or two or more substituents selected from the group consisting of heterocyclic groups, or is substituted with a substituent in which two or more of the above-exemplified substituents are linked, or does not have any substituents. For example, “a substituent group in which two or more substituents are connected” may be a biphenyl group. That is, the biphenyl group may be an aryl group, or it may be interpreted as a substituent in which two phenyl groups are connected.

As used herein, the term “substituted or unsubstituted” refers to deuterium; halogen group; Cyano group; silyl group; Alkoxy group; Aryloxy 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.

As used herein, the term “substituted or unsubstituted” refers to deuterium; 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.

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

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

In the present specification, the silyl group may be represented by the 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. The silyl group specifically includes, but is not limited to, trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, and phenylsilyl group. No.

In the present specification, the boron group may be represented by the chemical formula -BYdYe, where Yd and Ye are each hydrogen; Substituted or unsubstituted alkyl group; Or, it may be a substituted or unsubstituted aryl group. The boron group specifically includes, but is not limited to, trimethyl boron group, triethyl boron group, t-butyldimethyl boron group, triphenyl boron group, and phenyl boron group.

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 preferably 1 to 60. According to one embodiment, the carbon number of the alkyl group is 1 to 30. According to another embodiment, the carbon number of the alkyl group is 1 to 20. According to another embodiment, the carbon number of the alkyl group is 1 to 10. Specific examples of alkyl groups include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, pentyl group, n-pentyl group, hexyl group, n -Hexyl group, heptyl group, n-heptyl group, octyl group, n-octyl group, etc., but are not limited to these.

In the present specification, the description of the alkyl group described above may be applied, except that the arylalkyl group is substituted with an aryl group.

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

Substituents containing alkyl groups, alkoxy groups, and other alkyl group moieties described in this specification include both straight-chain or branched forms.

In the present specification, the alkenyl group may be straight chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( Naphthyl-1-yl) vinyl-1-yl, 2,2-bis (diphenyl-1-yl) vinyl-1-yl, stilbenyl group, styrenyl group, etc., but are not limited to these.

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

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. Specifically, it includes cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, etc., but is not limited thereto.

In the present specification, the amine group is -NH ₂ , and the amine group may be substituted with the above-described alkyl group, aryl group, heterocyclic group, alkenyl group, cycloalkyl group, and combinations thereof. The number of carbon atoms of the substituted amine group is not particularly limited, but is preferably 1 to 30. According to one embodiment, the carbon number of the amine group is 1 to 20. According to one embodiment, the carbon number of the amine group is 1 to 10. Specific examples of substituted amine groups include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, 9,9-dimethylfluorenylphenylamine group, pyridylphenylamine group, and diphenylamine. group, phenylpyridylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, dibenzofuranylphenylamine group, 9-methylanthracenylamine group, diphenylamine group, phenylnaphthylamine group, Ditolylamine group, phenyltolylamine group, diphenylamine group, etc., but are not limited to these.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group, such as a phenyl group, biphenyl group, terphenyl group, or quarterphenyl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, triphenylenyl group, etc., but is not limited thereto.

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

When the fluorenyl group is substituted, , Spirofluorenyl groups such as (9,9-dimethylfluorenyl group), and It may be a substituted fluorenyl group such as (9,9-diphenylfluorenyl group). However, it is not limited to this.

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

In the present specification, the heterocyclic group is a cyclic group containing one or more of N, O, P, S, Si, and Se as heteroatoms, and the number of carbon atoms is not particularly limited, but it is preferably 2 to 60 carbon atoms. According to one embodiment, the carbon number of the heterocyclic group is 2 to 30. According to one embodiment, the carbon number of the heterocyclic group is 2 to 20. Examples of heterocyclic groups include pyridine group, pyrrole group, pyrimidine group, quinoline group, pyridazinyl group, furan group, thiophene group, imidazole group, pyrazole group, dibenzofuran group, dibenzothiophene group, and carboxymethyl group. Examples include sol group, benzocarbazole group, naphthobenzofuran group, benzonaphthothiophene group, indenocarbazole group, and triazinyl group, but are not limited to these.

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

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

In the present specification, the description of the above heterocyclic group can be applied, except that the divalent heterocyclic group is divalent.

In the present specification, the description of the aryl group above can be applied, except that the n+1 valent aryl group is n+1 valent.

In the present specification, the description of the above heterocyclic group can be applied, except that the n+1 valent heterocyclic group is n+1 valent.

In the present specification, in a substituted or unsubstituted ring formed by combining adjacent groups, “ring” is a hydrocarbon ring; Or refers to a heterocycle.

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

In the present specification, forming a ring by bonding with adjacent groups means a substituted or unsubstituted aliphatic hydrocarbon ring by bonding with adjacent groups; Substituted or unsubstituted aromatic hydrocarbon ring; Substituted or unsubstituted aliphatic heterocycle; Substituted or unsubstituted aromatic heterocycle; Or it means forming a condensation ring thereof. The hydrocarbon ring refers to a ring consisting only of carbon and hydrogen atoms. The heterocycle refers to a ring containing one or more elements selected from N, O, P, S, Si, and Se. In the present specification, the aliphatic hydrocarbon ring, aromatic hydrocarbon ring, aliphatic heterocycle, and aromatic heterocycle may be monocyclic or polycyclic.

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

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

As used herein, an aliphatic heterocycle refers to an aliphatic ring containing one or more heteroatoms. Examples of aliphatic heterocycles include oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepane, and azocaine. , thiocane, etc., but is not limited thereto.

As used herein, an aromatic heterocycle refers to an aromatic ring containing one or more heteroatoms. Examples of aromatic heterocycles include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, parazole, oxazole, isoxazole, thiazole, isothiazole, triazole, oxadiazole, and thiazole. Diazole, dithiazole, tetrazole, pyran, thiopyran, diazine, oxazine, thiazine, dioxin, triazine, tetrazine, isoquinoline, quinoline, quinone, quinazoline, quinoxaline, naphthyridine, acridine , phenanthridine, diazanaphthalene, driazindene, indole, indolizine, benzothiazole, benzoxazole, benzoimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzoyl Examples include, but are not limited to, carbazole, dibenzocarbazole, phenazine, imidazopyridine, phenoxazine, indolocarbazole, and indenocarbazole.

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

The organic light emitting device of the present invention is characterized by containing both a compound represented by the following formula (1) and a compound represented by the following formula (2). The organic light emitting device of the present invention exhibits low voltage, high efficiency, and/or long life effects.

Hereinafter, Chemical Formula 1 will be described in detail.

[Formula 1]

In Formula 1,

L1 to L3 are the same or different from each other and are each independently a substituted or unsubstituted phenylene group,

One of Ar1 and Ar2 is a substituted or unsubstituted phenanthrenyl group, and the other is a substituted or unsubstituted naphthyl group,

Ra is hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group, or combined with adjacent groups to form a substituted or unsubstituted ring,

a is an integer from 0 to 9, and when a is 2 or more, Ra of 2 or more is the same or different from each other.

In an exemplary embodiment of the present specification, L1 to L3 are the same as or different from each other, and each independently represents a substituted or unsubstituted phenylene group.

In an exemplary embodiment of the present specification, L1 to L3 are the same or different from each other, and are each independently deuterium; Substituted or unsubstituted alkyl group; Or it is a phenylene group substituted or unsubstituted with a substituted or unsubstituted aryl group.

In an exemplary embodiment of the present specification, L1 to L3 are the same or different from each other, and each independently represents a phenylene group substituted or unsubstituted with deuterium.

In one embodiment of the present specification, L1 to L3 are phenylene groups.

In one embodiment of the present specification, L1 to L3 are phenylene groups substituted with deuterium.

In an exemplary embodiment of the present specification, one of Ar1 and Ar2 is a substituted or unsubstituted phenanthrenyl group, and the other is a substituted or unsubstituted naphthyl group.

In one embodiment of the present specification, one of Ar1 and Ar2 is deuterium; Substituted or unsubstituted alkyl group; or a substituted or unsubstituted phenanthrenyl group with a substituted or unsubstituted aryl group, and the other one is deuterium; Substituted or unsubstituted alkyl group; Or it is a naphthyl group substituted or unsubstituted by a substituted or unsubstituted aryl group.

In one embodiment of the present specification, one of Ar1 and Ar2 is a phenanthrenyl group substituted or unsubstituted with deuterium, and the other is a naphthyl group substituted or unsubstituted with deuterium.

In an exemplary embodiment of the present specification, one of Ar1 and Ar2 is a phenanthrenyl group, and the other is a naphthyl group.

In an exemplary embodiment of the present specification, Ar1 is a substituted or unsubstituted phenanthrenyl group, and Ar2 is a substituted or unsubstituted naphthyl group.

In one embodiment of the present specification, Ar1 is a phenanthrenyl group substituted or unsubstituted with deuterium, and Ar2 is a naphthyl group substituted or unsubstituted with deuterium.

In one embodiment of the present specification, Ar1 is a phenanthrenyl group, and Ar2 is a naphthyl group.

In an exemplary embodiment of the present specification, Ar1 is a substituted or unsubstituted naphthyl group, and Ar2 is a substituted or unsubstituted phenanthrenyl group.

In one embodiment of the present specification, Ar1 is a naphthyl group substituted or unsubstituted with deuterium, and Ar2 is a phenanthrenyl group substituted or unsubstituted with deuterium.

In one embodiment of the present specification, Ar1 is a naphthyl group, and Ar2 is a phenanthrenyl group.

In one embodiment of the present specification, Ra is hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Or it is a substituted or unsubstituted aryl group, or it combines with adjacent groups to form a substituted or unsubstituted ring.

In one embodiment of the present specification, Ra is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; Or, it is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or it combines with adjacent groups to form a substituted or unsubstituted ring.

In one embodiment of the present specification, Ra is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Or, it is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or it combines with adjacent groups to form a substituted or unsubstituted ring.

In one embodiment of the present specification, Ra is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or, it is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or it combines with adjacent groups to form a substituted or unsubstituted ring.

In one embodiment of the present specification, Ra is hydrogen; heavy hydrogen; An alkyl group substituted or unsubstituted with deuterium; Or, it is an aryl group substituted or unsubstituted with deuterium, or it combines with adjacent groups to form a substituted or unsubstituted ring.

In one embodiment of the present specification, Ra is hydrogen; heavy hydrogen; An alkyl group having 1 to 60 carbon atoms substituted or unsubstituted with deuterium; Or, it is an aryl group having 6 to 60 carbon atoms that is substituted or unsubstituted with deuterium, or is bonded to an adjacent group to form a ring substituted or unsubstituted with deuterium.

In one embodiment of the present specification, Ra is hydrogen; heavy hydrogen; An alkyl group having 1 to 30 carbon atoms substituted or unsubstituted with deuterium; Or, it is an aryl group having 6 to 30 carbon atoms that is substituted or unsubstituted with deuterium, or is bonded to an adjacent group to form a ring substituted or unsubstituted with deuterium.

In one embodiment of the present specification, Ra is hydrogen; heavy hydrogen; An alkyl group having 1 to 20 carbon atoms substituted or unsubstituted with deuterium; Or, it is an aryl group having 6 to 20 carbon atoms that is substituted or unsubstituted with deuterium, or is bonded to an adjacent group to form a ring substituted or unsubstituted with deuterium.

In one embodiment of the present specification, Ra is hydrogen; Or it is deuterium.

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

In one embodiment of the present specification, a is an integer from 1 to 9.

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

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

In one embodiment of the present specification, a is 2.

In one embodiment of the present specification, a is 3.

In one embodiment of the present specification, a is 4.

In one embodiment of the present specification, a is 5.

In one embodiment of the present specification, a is 6.

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

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

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

In one embodiment of the present specification, a is 9, and Ra is all deuterium.

In one embodiment of the present specification, a is 9, and 8 of the 9 Ra are deuterium.

In one embodiment of the present specification, a is 9, and 7 out of 9 Ra are deuterium.

In one embodiment of the present specification, a is 9, and 6 of the 9 Ra are deuterium.

In one embodiment of the present specification, a is 9, and 5 of the 9 Ra are deuterium.

In one embodiment of the present specification, a is 9, and 4 out of 9 Ra are deuterium.

In one embodiment of the present specification, a is 9, and 3 of the 9 Ra are deuterium.

In one embodiment of the present specification, a is 9, and two of the nine Ra are deuterium.

In one embodiment of the present specification, a is 9, and one of the nine Ra is deuterium.

In an exemplary embodiment of the present specification, Formula 1 is represented by the following Formula 1-1.

[Formula 1-1]

In Formula 1-1,

The definitions of Ar1, Ar2, Ra and a are the same as those in Formula 1 above,

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

b to d are each independently an integer of 0 to 4, and when b to d are each independently 2 or more, 2 or more Rb to Rd are the same or different from each other.

In an exemplary embodiment of the present specification, Rb to Rd are the same or different from each other, and are each independently hydrogen; Or it is deuterium.

In an exemplary embodiment of the present specification, Formula 1 is represented by the following Formula 1-1-1 or 1-1-2.

[Formula 1-1-1]

[Formula 1-1-2]

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

The definitions of L1 to L3, Ra and a are the same as those in Formula 1 above,

Re and Rf are the same or different from each other and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,

e is an integer from 0 to 7, and when e is 2 or more, 2 or more Re are the same or different from each other,

f is an integer from 0 to 9, and when f is 2 or more, Rf of 2 or more is the same or different from each other.

In an exemplary embodiment of the present specification, Re and Rf are the same or different from each other, and are each independently hydrogen; Or deuterium.

In one embodiment of the present specification, the compound represented by Formula 1 is at least 40% substituted with deuterium. In another exemplary embodiment, the compound represented by Formula 1 is substituted by more than 50% with deuterium. In another exemplary embodiment, the compound represented by Formula 1 is substituted by more than 60% with deuterium. In another exemplary embodiment, the compound represented by Formula 1 is substituted by more than 70% with deuterium. In another exemplary embodiment, the compound represented by Formula 1 is substituted by more than 80% with deuterium. In another exemplary embodiment, the compound represented by Formula 1 is substituted by more than 90% with deuterium. In another exemplary embodiment, the compound represented by Formula 1 is 100% substituted with deuterium.

In one embodiment of the present specification, the compound represented by Formula 1 contains 40% to 60% of deuterium. In another exemplary embodiment, the compound represented by Formula 1 contains 40% to 80% of deuterium. In another exemplary embodiment, the compound represented by Formula 1 contains 60% to 80% of deuterium. In another exemplary embodiment, the compound represented by Formula 1 contains 80% to 100% of deuterium.

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

.

.

Hereinafter, Chemical Formula 2 will be described in detail.

[Formula 2]

R1 is hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,

m is an integer from 0 to 9, and when m is 2 or more, 2 or more R1 are the same as or different from each other,

D is deuterium, n is an integer from 0 to 8,

R2 to R6 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; or the following formula A,

At least one of R2 and R6 is of formula A below,

[Formula A]

In Formula A,

R7 to R11 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group, or adjacent substituents combine with each other to form a substituted or unsubstituted ring,

The dotted line (---) is the part connected to Chemical Formula 2.

In one embodiment of the present specification, R1 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, R1 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; Or it is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

In one embodiment of the present specification, R1 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Or it is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In one embodiment of the present specification, R1 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or it is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

In one embodiment of the present specification, R1 is hydrogen; heavy hydrogen; An alkyl group substituted or unsubstituted with deuterium; Or it is an aryl group substituted or unsubstituted with deuterium.

In one embodiment of the present specification, R1 is hydrogen; heavy hydrogen; An alkyl group having 1 to 60 carbon atoms substituted or unsubstituted with deuterium; Or, it is an aryl group having 6 to 60 carbon atoms that is unsubstituted or substituted with deuterium.

In one embodiment of the present specification, R1 is hydrogen; heavy hydrogen; An alkyl group having 1 to 30 carbon atoms substituted or unsubstituted with deuterium; Or, it is an aryl group having 6 to 30 carbon atoms that is unsubstituted or substituted with deuterium.

In one embodiment of the present specification, R1 is hydrogen; heavy hydrogen; An alkyl group having 1 to 20 carbon atoms substituted or unsubstituted with deuterium; or an aryl group having 6 to 20 carbon atoms substituted or unsubstituted with deuterium.

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

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

In one embodiment of the present specification, m is an integer from 1 to 9.

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

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

In one embodiment of the present specification, m is 2.

In one embodiment of the present specification, m is 3.

In one embodiment of the present specification, m is 4.

In one embodiment of the present specification, m is 5.

In one embodiment of the present specification, m is 6.

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

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

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

In one embodiment of the present specification, m is 9 and R1 is all deuterium.

In one embodiment of the present specification, m is 9, and 8 out of 9 R1 are deuterium.

In one embodiment of the present specification, m is 9, and 7 out of 9 R1 are deuterium.

In one embodiment of the present specification, m is 9, and 6 of the 9 R1 are deuterium.

In one embodiment of the present specification, m is 9, and 5 of the 9 R1 are deuterium.

In one embodiment of the present specification, m is 9, and 4 out of 9 R1 are deuterium.

In one embodiment of the present specification, m is 9, and 3 of the 9 R1 are deuterium.

In one embodiment of the present specification, m is 9, and two of the nine R1 are deuterium.

In one embodiment of the present specification, m is 9, and one of the nine R1 is deuterium.

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

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

In one embodiment of the present specification, n is an integer from 1 to 8.

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

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

In one embodiment of the present specification, n is 2.

In one embodiment of the present specification, n is 3.

In one embodiment of the present specification, n is 4.

In one embodiment of the present specification, n is 5.

In one embodiment of the present specification, n is 6.

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

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

In an exemplary embodiment of the present specification, R2 to R6 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Or it is the formula A below.

In an exemplary embodiment of the present specification, R2 to R6 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; Or it is the formula A below.

In an exemplary embodiment of the present specification, R2 to R6 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Or it is the formula A below.

In an exemplary embodiment of the present specification, R2 to R6 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or it is the formula A below.

In an exemplary embodiment of the present specification, R2 to R6 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; Or it is the formula A below.

In an exemplary embodiment of the present specification, R2 to R6 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; An alkyl group substituted or unsubstituted with deuterium; Or it is the formula A below.

In an exemplary embodiment of the present specification, R2 to R6 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; An alkyl group having 1 to 60 carbon atoms substituted or unsubstituted with deuterium; Or it is the formula A below.

In an exemplary embodiment of the present specification, R2 to R6 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; An alkyl group having 1 to 30 carbon atoms substituted or unsubstituted with deuterium; Or it is the formula A below.

In an exemplary embodiment of the present specification, R2 to R6 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; An alkyl group having 1 to 20 carbon atoms substituted or unsubstituted with deuterium; Or it is the formula A below.

In an exemplary embodiment of the present specification, R2 to R6 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; An alkyl group having 1 to 10 carbon atoms substituted or unsubstituted with deuterium; Or it is the formula A below.

In an exemplary embodiment of the present specification, R2 to R6 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; Or it is the formula A below.

In an exemplary embodiment of the present specification, at least one of R2 and R6 is of formula A below.

In an exemplary embodiment of the present specification, one of R2 and R6 is of formula A below.

In an exemplary embodiment of the present specification, R2 is the formula A below.

In one embodiment of the present specification, R6 is the formula A below.

In an exemplary embodiment of the present specification, R2 is the formula A below, R3 to R6 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Or it is a substituted or unsubstituted alkyl group.

In an exemplary embodiment of the present specification, R2 is the formula A below, R3 to R6 are the same as or different from each other, and are each independently hydrogen; Or deuterium.

In an exemplary embodiment of the present specification, R6 is the formula A below, R2 to R5 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Or it is a substituted or unsubstituted alkyl group.

In an exemplary embodiment of the present specification, R6 is the formula A below, R2 to R5 are the same as or different from each other, and are each independently hydrogen; Or deuterium.

[Formula A]

In Formula A,

R7 to R11 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group, or adjacent substituents combine with each other to form a substituted or unsubstituted ring,

The dotted line (---) is the part connected to Chemical Formula 2.

In an exemplary embodiment of the present specification, R7 to R11 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Or, it is a substituted or unsubstituted aryl group, or adjacent substituents combine with each other to form a substituted or unsubstituted ring.

In an exemplary embodiment of the present specification, R7 to R11 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; Or, it is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or it combines with adjacent groups to form a substituted or unsubstituted ring.

In an exemplary embodiment of the present specification, R7 to R11 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Or, it is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or it combines with adjacent groups to form a substituted or unsubstituted ring.

In an exemplary embodiment of the present specification, R7 to R11 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or, it is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or it combines with adjacent groups to form a substituted or unsubstituted ring.

In an exemplary embodiment of the present specification, R7 to R11 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; An alkyl group substituted or unsubstituted with deuterium; Or, it is an aryl group substituted or unsubstituted with deuterium, or it combines with adjacent groups to form a substituted or unsubstituted ring.

In an exemplary embodiment of the present specification, R7 to R11 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; An alkyl group having 1 to 60 carbon atoms substituted or unsubstituted with deuterium; Or, it is an aryl group having 6 to 60 carbon atoms that is substituted or unsubstituted with deuterium, or is bonded to an adjacent group to form a ring substituted or unsubstituted with deuterium.

In an exemplary embodiment of the present specification, R7 to R11 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; An alkyl group having 1 to 30 carbon atoms substituted or unsubstituted with deuterium; Or, it is an aryl group having 6 to 30 carbon atoms that is substituted or unsubstituted with deuterium, or is bonded to an adjacent group to form a ring substituted or unsubstituted with deuterium.

In an exemplary embodiment of the present specification, R7 to R11 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; An alkyl group having 1 to 20 carbon atoms substituted or unsubstituted with deuterium; Or, it is an aryl group having 6 to 20 carbon atoms that is substituted or unsubstituted with deuterium, or is bonded to an adjacent group to form a ring substituted or unsubstituted with deuterium.

In an exemplary embodiment of the present specification, R7 to R11 are the same or different from each other, and are each independently hydrogen; Or deuterium.

In an exemplary embodiment of the present specification, the remainders other than Formula A among R1 to R11 are the same as or different from each other, and are each independently hydrogen; Or deuterium.

In one embodiment of the present specification, Formula 2 includes at least one deuterium.

In an exemplary embodiment of the present specification, Formula 2 is represented by the following Formula 2-1.

[Formula 2-1]

In Formula 2-1, the definitions of R1, m, D, n, and R3 to R11 are the same as those in Formula 2.

In one embodiment of the present specification, the compound represented by Formula 2 is at least 40% substituted with deuterium. In another exemplary embodiment, the compound represented by Formula 2 is substituted by more than 50% with deuterium. In another exemplary embodiment, the compound represented by Formula 2 is substituted by more than 60% with deuterium. In another exemplary embodiment, the compound represented by Formula 2 is substituted by more than 70% with deuterium. In another exemplary embodiment, the compound represented by Formula 2 is substituted by more than 80% with deuterium. In another exemplary embodiment, the compound represented by Formula 2 is substituted by more than 90% with deuterium. In another exemplary embodiment, the compound represented by Formula 2 is 100% substituted with deuterium.

In one embodiment of the present specification, the compound represented by Formula 2 contains 40% to 60% of deuterium. In another exemplary embodiment, the compound represented by Formula 2 contains 40% to 80% of deuterium. In another exemplary embodiment, the compound represented by Formula 2 contains 60% to 80% of deuterium. In another exemplary embodiment, the compound represented by Formula 2 contains 80% to 100% of deuterium.

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

.

.

The core structure of the compounds represented by Formula 1 and Formula 2 according to an exemplary embodiment of the present specification can be manufactured as in the method of the production example described later. Substituents may be combined by methods known in the art, and the type, position, or number of substituents may be changed according to techniques known in the art.

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

Hereinafter, the organic light emitting device will be described.

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 component, this means that it may further include other components rather than excluding other components, unless specifically stated to the contrary.

The organic light emitting device according to the present specification includes an anode; cathode; Comprising a first organic material layer and a second organic material layer provided between the anode and the cathode, wherein the first organic material layer includes a compound represented by Formula 1, and the second organic layer includes a compound represented by Formula 2 It is characterized by:

The organic light-emitting device of the present invention can be manufactured using conventional organic light-emitting device manufacturing methods and materials, except that the organic material layer is formed using the compound represented by the above-described formula (1) and the compound of the above-described formula (2). .

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, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited to these.

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

In one embodiment of the present specification, the first organic material layer includes an electron blocking layer, and the electron blocking layer may include the compound represented by Formula 1.

In one embodiment of the present specification, the first organic material layer is an electron blocking layer, and the electron blocking layer may include the compound represented by Formula 1.

In one embodiment of the present specification, the second organic layer includes a light-emitting layer, and the light-emitting layer may include the compound represented by Formula 2.

In one embodiment of the present specification, the second organic material layer is a light-emitting layer, and the light-emitting layer may include the compound represented by Formula 2.

In one embodiment of the present specification, the second organic layer is a light-emitting layer, and the light-emitting layer may include the compound represented by Formula 2 as a host.

In the organic light emitting device according to an exemplary embodiment of the present specification, the organic material layer may include two or more layers of a hole injection layer, a hole transport layer, or an electron blocking layer.

In the organic light emitting device according to an exemplary embodiment of the present specification, the organic material layer may include two or more layers of an electron injection layer, an electron transport layer, or a hole blocking layer.

In one embodiment of the present specification, the thickness of the first organic layer containing the compound represented by Formula 1 and the second organic layer including the compound represented by Formula 2 is 10 Å to 600 Å, preferably 50 Å. Å to 500 Å, more preferably 200 Å to 400 Å.

In another embodiment, the first organic layer and the second organic layer may further include other organic compounds, metals, or metal compounds in addition to the compound represented by Formula 1 and the compound represented by Formula 2.

In another embodiment, the first organic layer and the second organic layer do not contain any organic compounds, metals, or metal compounds other than the compound represented by the above-described formula (1) and the compound represented by the above-described formula (2).

In one embodiment of the present specification, the first organic material layer and the second organic material layer may be provided in contact with each other.

In one embodiment of the present specification, the first organic material layer and the second organic material layer may not be provided in contact with each other.

In one embodiment of the present specification, one or more organic layers are located between the first organic layer and the second organic layer.

In the organic light-emitting device according to an exemplary embodiment of the present specification, the compound represented by the above-described Formula 1 and the compound represented by the above-described Formula 2 are different from each other.

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

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

In one embodiment of the present specification, the organic light emitting device includes an anode; cathode; and two or more organic layers provided between the anode and the cathode, wherein at least one of the two or more organic layers includes a compound represented by Formula 1 and a compound represented by Formula 2.

In one embodiment of the present specification, the two or more organic layers may be selected from the group consisting of a light emitting layer, a hole transport layer, a hole injection layer, a hole transport and injection layer, and an electron blocking layer.

In one embodiment of the present specification, the two or more organic layers may be selected from the group consisting of a light emitting layer, an electron transport layer, an electron injection layer, an electron transport and injection layer, an electron control layer, and a hole blocking layer.

In one embodiment of the present specification, the organic material layer includes two or more electron transport layers, and at least one of the two or more electron transport layers includes the compound represented by Formula 1 and the compound represented by Formula 2. Specifically, in one embodiment of the present specification, the compound represented by Formula 1 and the compound represented by Formula 2 may be included in one layer of the two or more electron transport layers, and may be included in each of the two or more electron transport layers. You can.

In addition, in one embodiment of the present specification, when the compound is included in each of the two or more electron transport layers, other materials except the compound represented by Formula 1 and the compound represented by Formula 2 are the same or may be different.

When the organic material layer containing the compound represented by Formula 1 or the compound represented by Formula 2 is an electron transport layer, an electron injection layer, or an electron transport and injection layer, the electron transport layer, an electron injection layer, or an electron transport and injection layer may further include an n-type dopant. The n-type dopant may be one known in the art, for example, a metal or a metal complex. For example, the electron transport layer including the compound represented by Formula 1 and the compound represented by Formula 2 may further include LiQ (Lithium Quinolate). According to one example, the entire compound represented by Formula 1 and Formula 2 and the n-type dopant may be included in a weight ratio of 2:8 to 8:2, for example, 4:6 to 6:4.

According to one example, the entire compound represented by Formula 1 and Formula 2 and the n-type dopant may be included in a weight ratio of 1:1.

The organic light emitting device according to an embodiment of the present specification is further provided with one or more organic material layers between the anode and the cathode, and the organic material layer includes a hole transport layer, a hole injection layer, a hole transport and injection layer, an electron blocking layer, and a light emitting layer. , it may further include one or more layers among an electron transport layer, an electron injection layer, an electron transport and injection layer, and a hole blocking layer.

The organic light emitting device according to an exemplary embodiment of the present specification may further include one or more light emitting layers.

The organic light-emitting device according to an exemplary embodiment of the present specification further includes one or more light-emitting layers in addition to the light-emitting layer, and each light-emitting layer may include the host compound described above.

The organic light-emitting device according to an exemplary embodiment of the present specification further includes one or more light-emitting layers in addition to the light-emitting layer, and each light-emitting layer further includes a fluorescent dopant or a phosphorescent dopant. At this time, the dopant in the light emitting layer is included in an amount of 1 to 50 parts by weight based on 100 parts by weight of the host.

The organic light emitting device according to an exemplary embodiment of the present specification may include two or more light emitting layers.

An organic light emitting device according to an exemplary embodiment of the present specification includes two or more light emitting layers, at least one light emitting layer includes a fluorescent dopant, and at least one other light emitting layer includes a phosphorescent dopant.

An organic light emitting device according to an exemplary embodiment of the present specification may include three or more light emitting layers.

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

The organic light-emitting device according to an exemplary embodiment of the present specification includes two or more light-emitting layers, and the maximum emission peaks of the two or more light-emitting layers are each 400 nm to 500 nm.

The organic light-emitting device according to an exemplary embodiment of the present specification further includes one or more light-emitting layers, and each light-emitting layer exhibits a different wavelength band.

The organic light-emitting device according to an embodiment of the present specification includes three or more layers of light-emitting layers, the maximum emission peak of one light-emitting layer (light-emitting layer 1) is 400 nm to 500 nm, and the peak of the light-emitting layer of another layer (light-emitting layer 2) is 400 nm to 500 nm. Maximum emission peak is 510 nm to 580 nm; Alternatively, it may exhibit a maximum emission peak of 610 nm to 680 nm, and the maximum emission peak of another layer of the light-emitting layer (emission layer 3) may have a maximum emission peak of 400 nm to 500 nm.

Additionally, according to an exemplary embodiment of the present application, the two or more light-emitting layers may be positioned vertically or horizontally between the anode and the cathode.

According to an exemplary embodiment of the present application, the three or more light-emitting layers are positioned vertically from the anode to the cathode. At this time, all three or more light-emitting layers may be blue fluorescent light-emitting layers.

When the organic light-emitting device according to an embodiment of the present specification includes a plurality of light-emitting layers, one or more organic material layers are additionally provided between the plurality of light-emitting layers, and the organic material layer includes a hole transport layer, a hole injection layer, and hole transport and injection. It may further include one or more of the following layers, an electron blocking layer, a charge generation layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron transport and injection layer, and a hole 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 a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

(18) Anode/hole injection layer/first hole transport layer/second hole transport layer/light-emitting layer/electron transport and injection layer/cathode

The structure of the organic light emitting device of the present specification may have the same structure as shown in FIGS. 1 to 3, but is not limited thereto.

Figure 1 illustrates the structure of an organic light-emitting device in which a substrate 1, an anode 2, a second organic layer 22, a first organic layer 21, and a cathode 10 are sequentially stacked. In this structure, the compound represented by Formula 1 may be included in the first organic layer 21 and the compound represented by Formula 2 may be included in the second organic layer 22.

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

3 shows a substrate (1), anode (2), hole injection layer (3), hole transport layer (4), electron blocking layer (5), light emitting layer (6), hole blocking layer (7), electron injection and transport layer ( The structure of an organic light emitting device in which 11) and the cathode 10 are sequentially stacked is illustrated. In this structure, the compound represented by Formula 1 may be included in the electron blocking layer 5 and the compound represented by Formula 2 may be included in the light-emitting layer 6.

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.

In one embodiment of the present specification, the electron transport and injection layer and the light emitting layer may be provided adjacent to each other. For example, the electron transport and injection layer and the light emitting layer may be provided in physical contact with each other.

In one embodiment of the present specification, the electron transport layer and the light emitting layer may be provided adjacent to each other. For example, the electron transport layer and the light emitting layer may be provided in physical contact.

In one embodiment of the present specification, the hole blocking layer and the light emitting layer may be provided adjacent to each other. For example, the hole blocking layer and the light emitting layer may be provided in physical contact.

In one embodiment of the present specification, the electron blocking layer and the light emitting layer may be provided adjacent to each other. For example, the electron blocking layer and the light emitting layer may be provided in physical contact.

The organic light emitting device of the present specification is manufactured using materials and methods known in the art, except that at least one layer of the organic material layer contains the above compound, that is, the compound represented by Formula 1 and the compound represented by Formula 2. It can be.

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 according to the present specification uses a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation to deposit a metal, a conductive metal oxide, or an alloy thereof on a substrate. Manufactured by depositing an anode, forming an organic material layer including a hole injection layer, a hole transport layer, a light-emitting layer, an electron blocking layer, an electron transport layer, and an electron injection layer thereon, and then depositing a material that can be used as a cathode on it. It can be. 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.

The organic layer may further include one or more of a hole transport layer, a hole injection layer, an electron blocking layer, an electron transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and a hole transport and injection layer.

The organic material layer may have a multi-layer structure including a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, or an electron transport and injection layer, but is not limited to this and may have a single-layer structure. there is. In addition, the organic material layer uses a variety of polymer materials to form a smaller number of layers by using a solvent process rather than a deposition method, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer. It can be manufactured in layers.

The anode is an electrode that injects holes, and the anode material is generally preferably a material with a large work function to ensure smooth hole injection into the organic layer. Specific examples of anode materials that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); Combination of metal and oxide such as ZnO:Al or SnO ₂ :Sb; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline are included, but are not limited to these.

The cathode is an electrode that injects electrons, and the cathode material is generally preferably a material with a small work function to facilitate electron injection into the organic layer. Specific examples of cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; There are multi-layer structure materials such as LiF/Al or LiO ₂ /Al, but they are not limited to these.

The hole injection layer is a layer that serves to facilitate the injection of holes from the anode to the light emitting layer, and the hole injection material is a material that can well inject holes from the anode at a low voltage. The hole injection material is HOMO (highest occupied). It is preferable that the molecular orbital is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of hole injection materials include the above-mentioned compounds or metal porphyrine, oligothiophene, arylamine-based organic material, hexanitrilehexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene. (perylene)-based organic materials, anthraquinone, and polyaniline- and polythiophene-based conductive polymers, etc., but are not limited to these. The thickness of the hole injection layer may be 1 to 150 nm. If the thickness of the hole injection layer is 1 nm or more, there is an advantage in preventing the hole injection characteristics from deteriorating, and if it is 150 nm or less, the thickness of the hole injection layer is so thick that the driving voltage is increased to improve the movement of holes. There is an advantage to preventing this.

The hole transport layer may play a role in facilitating the transport of holes. The hole transport material is a material that can transport holes from the anode or hole injection layer and transfer them to the light emitting layer, and a material with high mobility for holes is suitable. Specific examples include, but are not limited to, the above-mentioned compounds or arylamine-based organic materials, conductive polymers, and block copolymers having both conjugated and non-conjugated portions.

An additional hole buffer layer may be provided between the hole injection layer and the hole transport layer, and may include the above-described compound or a hole injection or transport material known in the art.

An electron blocking layer may be provided between the hole transport layer and the light emitting layer. The above-described compounds or materials known in the art may be used in the electron blocking layer.

The light-emitting layer may emit red, green, or blue light and may be made of a phosphorescent material or a fluorescent material. The light-emitting material is a material that can emit light in the visible light range by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, and is preferably a material with good quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Compounds of the benzoxazole, benzthiazole and benzimidazole series; Poly(p-phenylenevinylene) (PPV) series polymer; Spiro compounds; Polyfluorene, rubrene, etc., but are not limited to these.

Host materials for the light-emitting layer include condensed aromatic ring derivatives or heterocycle-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 carbazole derivatives, dibenzofuran derivatives, and ladder-type compounds. These include, but are not limited to, furan compounds and pyrimidine derivatives.

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

In one embodiment of the present specification, the light-emitting layer may include a compound according to the present invention as a host, and a pyrene compound substituted with an amine group or a polycyclic compound containing boron as a dopant. The host and the dopant may be included in an appropriate weight ratio. According to one example, the host and the dopant may be included in a weight ratio of 100:1 to 100:10, respectively.

In one embodiment of the present specification, the light-emitting layer may include the compound represented by Formula 2 of the present invention as a host and a polycyclic compound containing boron as a dopant.

In one embodiment of the present specification, the light-emitting layer may include the compound represented by Formula 2 of the present invention as a host, and may include the compound represented by Formula D below as a dopant.

[Formula D]

In Formula D,

X1 and X2 are the same or different from each other and are each independently CR"; or NR",

At least one of X1 and X2 is NR",

R1' to R3' and R" are the same or different from each other, and are each independently hydrogen; deuterium; halogen group; cyano group; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted alkoxy group ; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted silyl group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl group; Substituted or unsubstituted condensed ring of aromatic hydrocarbon ring and aliphatic hydrocarbon ring ; or a substituted or unsubstituted heterocyclic group, or combines with an adjacent group to form a substituted or unsubstituted ring,

r1 and r3 are integers from 0 to 4, r2 is each an integer from 0 to 3,

When r1 to r3 are each 2 or more, the substituents in parentheses are the same or different from each other.

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

The electron transport layer may play a role in facilitating the transport of electrons. 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 suitable. Specific examples include the Al complex of 8-hydroxyquinoline; Complex containing Alq ₃ ; organic radical compounds; Hydroxyflavone-metal complexes, etc., but are not limited to these. The thickness of the electron transport layer may be 1 to 50 nm. If the thickness of the electron transport layer is 1 nm or more, there is an advantage in preventing the electron transport characteristics from deteriorating, and if it is 50 nm or less, the thickness of the electron transport layer is too thick to prevent the driving voltage from increasing to improve the movement of electrons. There are benefits to this.

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

Examples of the metal complex compounds include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato)aluminum, Tris(2-methyl-8-hydroxyquinolinato)aluminum, Tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)( o-cresolato) gallium, bis(2-methyl-8-quinolinato)(1-naphtolato) aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato) gallium, etc. It is not limited to this.

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 hole injection layer. Specifically, it includes oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complex, etc., but is not limited thereto.

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

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

<Manufacturing Example 1>

Compounds 4-bromo-N-(4-bromophenyl)-N-(4-(naphthalen-1-yl)phenyl)aniline (9.50 g, 17.96 mmol) and phenanthrene-9- were added to a 500 ml round bottom flask in a nitrogen atmosphere. After completely dissolving monoboronic acid (4.39 g, 19.75 mmol) in 240 ml of tetrahydrofuran, 2M aqueous potassium carbonate solution (120 ml) was added, and tetrakis-(triphenylphosphine)palladium (0.62 g, 0.54 mmol) was added. Then, it was heated and stirred for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried with anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 320 ml of ethyl acetate to prepare Compound 1-1 (7.84 g, 60%).

MS[M+H] ⁺ = 724

<Production Example 2>

Compounds N,N-bis(4-bromophenyl)-3-(naphthalen-1-yl)aniline (9.50 g, 17.96 mmol), phenanthrene-9-ylboronic acid (4.39g, 19.75 mmol) was completely dissolved in 240 ml of tetrahydrofuran, then 2M potassium carbonate aqueous solution (120 ml) was added, tetrakis-(triphenylphosphine)palladium (0.62 g, 0.54 mmol) was added, and then heated and stirred for 4 hours. did. The temperature was lowered to room temperature, the water layer was removed, dried with anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 250 ml of ethyl acetate to prepare Compound 1-2 (8.23 g, 63%).

MS[M+H] ⁺ = 724

<Production Example 3>

Compounds N,N-bis(4-bromophenyl)-3-(naphthalen-2-yl)aniline (9.50 g, 17.96 mmol), phenanthrene-9-ylboronic acid (4.39g, 19.75 mmol) was completely dissolved in 240 ml of tetrahydrofuran, then 2M potassium carbonate aqueous solution (120 ml) was added, tetrakis-(triphenylphosphine)palladium (0.62 g, 0.54 mmol) was added, and then heated and stirred for 7 hours. did. The temperature was lowered to room temperature, the water layer was removed, dried with anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 410 ml of ethyl acetate to prepare Compound 1-3 (8.77 g, 67%).

MS[M+H] ⁺ = 724

<Production Example 4>

Compound 9-bromo-10-(phenyl-d5)anthracene in a 500 ml round bottom flask under nitrogen atmosphere. (6.50g, 15.57 mmol) and naphthalen-1-ylboronic acid (5.90g, 17.13 mmol) were completely dissolved in 240ml of tetrahydrofuran, then 2M potassium carbonate aqueous solution (120ml) was added, and tetrakis-(triphenylphosphine) Palladium (0.54 g, 0.47 mmol) was added, followed by heating and stirring for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried with anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 320 ml of ethyl acetate to prepare Compound 2-1 (5.91 g, 68%).

MS[M+H] ⁺ = 555

<Production Example 5>

9-([1,1'-biphenyl]-2-yl-d9)-10-bromoanthracene-1,2,3,4,5,6,7,8-d8 (6.50) in a 500 ml round bottom flask under nitrogen atmosphere. g, 15.26 mmol) and dibenzo[b,d]furan-2-ylboronic acid (5.78g, 16.78 mmol) were completely dissolved in 240ml of tetrahydrofuran, then 2M potassium carbonate aqueous solution (120ml) was added, and tetrakis-(tri Phenylphosphine) palladium (0.53 g, 0.46 mmol) was added, and then heated and stirred for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried with anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 340 ml of ethyl acetate to prepare Compound 2-2 (6.67 g, 78%).

MS[M+H] ⁺ = 564

<Production Example 6>

Compounds 9-([1,1'-biphenyl]-2-yl-d9)-10-bromoanthracene (6.50 g, 15.55 mmol) and phenanthren-9-ylboronic acid (5.89 g, 17.11) were added to a 500 ml round bottom flask in a nitrogen atmosphere. mmol) was completely dissolved in 220 ml of tetrahydrofuran, 2M potassium carbonate aqueous solution (110 ml) was added, tetrakis-(triphenylphosphine)palladium (0.54 g, 0.47 mmol) was added, and the mixture was heated and stirred for 5 hours. The temperature was lowered to room temperature, the water layer was removed, dried with anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 250 ml of ethyl acetate to prepare compound 2-3 (6.34 g, 73%).

Comparative Example 1

A glass substrate coated with a thin film of ITO (indium tin oxide) with a thickness of 1,000 Å was placed in distilled water with a detergent dissolved in it and washed ultrasonically. At this time, a detergent manufactured by Fischer Co. was used, and distilled water filtered secondarily using a filter manufactured by Millipore Co. was used as distilled water. 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, compounds of the following formula [HI-1] and the following formula [HI-2] were thermally vacuum deposited to a thickness of 100 Å at a ratio of 98:2 (molar ratio) to form a hole injection layer.

The following compound [HT-1] (1150 Å), a material that transports holes, was vacuum deposited on the hole injection layer to form a hole transport layer.

Subsequently, the following compound [EB-1] (150 Å) was vacuum deposited on the hole transport layer to a film thickness of 50 Å to form an electron blocking layer.

Next, [BH-1] and [BD-1] as shown below were vacuum deposited on the electron blocking layer to a film thickness of 200 Å at a weight ratio of 40:1 to form a light emitting layer.

The compound [HB-1] was vacuum deposited on the light emitting layer to a film thickness of 50 Å to form a hole blocking layer.

Next, compound [ET-1] and the compound LiQ (Lithium Quinolate) were vacuum deposited on the hole blocking layer at a weight ratio of 1:1 to form an electron transport and injection layer with a thickness of 300 Å.

A cathode was formed by sequentially depositing lithium fluoride (LiF) to a thickness of 12 Å and aluminum to a thickness of 2,000 Å on the electron transport and injection layer.

In the above process, the deposition rate of organic matter was maintained at 0.4~0.7Å/sec, the deposition rate of lithium fluoride of the cathode was maintained at 0.3Å/sec, and the deposition rate of aluminum was maintained at 2Å/sec, and the vacuum degree during deposition was 2ⅹ10-7. An organic light emitting device was manufactured by maintaining ~5 x 10-6 torr.

Comparative Examples 2 to 9

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

Experimental Example 1-1 to Experimental Example 1-9

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

Comparative Examples 10 to 27

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

When a current of 20 mA/cm ² was applied to the organic light-emitting device manufactured in the above experimental and comparative examples, the driving voltage, luminous efficiency, and color coordinates were measured, and the initial luminance was 95% compared to the initial luminance at a current density of 20 mA/cm ² . The time to reach % (T95) was measured. The results are shown in Table 1 below. T95 refers to the time it takes for the luminance to decrease from the initial luminance (1600 nit) to 95%.

compound
(electron blocking layer) compound
(Emitting layer) Voltage
(V
@10mA
/cm ² ) efficiency
(cd/A
@10mA
/cm ² ) Color coordinates
(x,y) T95
(hr) Comparative Example 1 EB-1 BH-1 4.41 4.67 (0.145, 0.046) 230 Comparative Example 2 EB-1 BH-2 4.32 4.65 (0.145, 0.047) 181 Comparative Example 3 EB-1 BH-3 4.43 4.68 (0.146, 0.045) 208 Comparative Example 4 EB-2 BH-1 4.44 4.67 (0.145, 0.044) 203 Comparative Example 5 EB-2 BH-2 4.35 4.64 (0.146, 0.046) 207 Comparative Example 6 EB-2 BH-3 4.42 4.73 (0.144, 0.045) 207 Comparative Example 7 EB-3 BH-1 4.45 4.68 (0.144, 0.046) 204 Comparative Example 8 EB-3 BH-2 4.33 4.67 (0.145, 0.047) 173 Comparative Example 9 EB-3 BH-3 4.36 4.62 (0.146, 0.045) 191 Experimental Example 1-1 1-1 2-1 3.58 5.76 (0.145, 0.047) 366 Experimental Example 1-2 1-1 2-2 3.64 5.72 (0.145, 0.045) 368 Experimental Example 1-3 1-1 2-3 3.69 5.77 (0.144, 0.047) 334 Experimental Example 1-4 1-2 2-1 3.60 5.68 (0.146, 0.047) 346 Experimental Example 1-5 1-2 2-2 3.77 5.63 (0.146, 0.046) 347 Experimental Example 1-6 1-2 2-3 3.74 5.64 (0.146, 0.045) 316 Experimental Example 1-7 1-3 2-1 3.73 5.68 (0.144, 0.047) 357 Experimental Example 1-8 1-3 2-2 3.71 5.66 (0.145, 0.046) 354 Experimental Example 1-9 1-3 2-3 3.72 5.62 (0.144, 0.045) 326 Comparative Example 10 1-1 BH-1 4.06 5.33 (0.144, 0.047) 273 Comparative Example 11 1-2 BH-1 4.15 5.34 (0.145, 0.045) 259 Comparative Example 12 1-3 BH-1 4.18 5.36 (0.146, 0.046) 266 Comparative Example 13 1-1 BH-2 4.02 5.49 (0.147, 0.047) 238 Comparative Example 14 1-2 BH-2 4.13 5.30 (0.145, 0.045) 211 Comparative Example 15 1-3 BH-2 4.14 5.44 (0.146, 0.046) 225 Comparative Example 16 1-1 BH-3 4.12 5.33 (0.146, 0.047) 246 Comparative Example 17 1-2 BH-3 4.13 5.36 (0.145, 0.045) 229 Comparative Example 18 1-3 BH-3 4.25 5.37 (0.146, 0.046) 239 Comparative Example 19 EB-1 2-1 4.23 5.13 (0.144, 0.047) 308 Comparative Example 20 EB-1 2-2 4.27 5.25 (0.144, 0.045) 309 Comparative Example 21 EB-1 2-3 4.14 5.13 (0.145, 0.046) 307 Comparative Example 22 EB-2 2-1 4.15 5.19 (0.146, 0.047) 304 Comparative Example 23 EB-2 2-2 4.18 5.27 (0.145, 0.045) 278 Comparative Example 24 EB-2 2-3 4.10 5.26 (0.147, 0.046) 266 Comparative Example 25 EB-3 2-1 4.03 5.34 (0.146, 0.047) 223 Comparative Example 26 EB-3 2-2 4.04 5.35 (0.145, 0.045) 209 Comparative Example 27 EB-3 2-3 4.00 5.49 (0.146, 0.046) 221

As shown in Table 1, Experimental Examples 1-1 to 1-9 used the compound of Formula 1 and the compound of Formula 2 as materials for the electron blocking layer and the light-emitting layer, respectively, and the compounds represented by Formula 1 and Formula 2 Shows the characteristics of the device applied together. Comparative Examples 1 to 9 are the results when any one of EB-1 to EB-3 is used as the electron blocking layer and any one of BH-1 to BH-3 is used as the light emitting layer. Indicates device characteristics.

Comparative Examples 10 to 27 are those in which the compound of Formula 1 was used instead of any one of EB-1 to EB-3, or the compound of Formula 2 was used instead of any one of BH-1 to BH-3, and Comparative Examples 1 and 2 Shows the characteristics of a device using a separate compound indicated by .

Accordingly, in comparison with the comparative example, it can be confirmed that the organic light emitting device of the experimental example exhibits the characteristics of low voltage, high efficiency, and long lifespan.

Comparative Examples 10 to 12 are cases where a compound (BH-1) in which an aryl group is connected to an anthracene core is used, and Comparative Examples 13 to 15 are cases in which a compound (BH-2) in which dibenzofuran and a phenyl group are connected to an anthracene core is used. . Comparing Experimental Examples 1-1 to 1-9 and Comparative Examples 10 to 15, Experimental Examples 1-1 to 1-9 using the compound of formula 2 in which naphthobenzofuran is linked to an anthracene core are used in Comparative Example 10. It can be seen that the driving voltage is lower than that of 15, the luminous efficiency is high, and the lifespan is long.

Comparative Examples 16 to 18 are cases where a compound (BH-3) whose connection position of naphthobenzofuran is different from that of Chemical Formula 2 herein was used. Comparing Experimental Examples 1-1 to 1-9 and Comparative Examples 16 to 18, Experimental Examples 1-1 to 1-9 using the compound of Formula 2 herein have a connection position of naphthobenzofuran that is different from Formula 2 of the present application. It can be confirmed that the driving voltage is lower, the luminous efficiency is higher, and the lifespan is longer than in Comparative Examples 16 to 18 using the compound.

Comparative Examples 19 to 21 are cases where a compound (EB-1) in which the Ar1 or Ar2 position of Chemical Formula 1 is not a naphthalene group was used, and Comparative Examples 22 to 24 are compounds in which the Ar1 or Ar2 position of Chemical Formula 1 is not a phenanthrenyl group. (EB-2) is used, and Comparative Examples 25 to 27 are cases of using a compound (EB-3) in which positions L1 to L3 of Chemical Formula 1 are not phenylene groups. Comparing Experimental Examples 1-1 to 1-9 and Comparative Examples 19 to 27, L1 to L3 are phenylene groups, one of Ar1 and Ar2 is a phenanthrenyl group, and the other is a naphthyl group. It can be seen that Experimental Examples 1-1 to 1-9 used have a lower driving voltage, higher luminous efficiency, and longer lifespan than Comparative Examples 19 to 21. Through this, the compound of Formula 1 of the present invention can be used to block electrons. It can be confirmed that when used as a layer material and the compound of Formula 2 of the present invention in combination as a light-emitting layer material, it is possible to have high efficiency characteristics while maintaining the long life characteristics of the organic light-emitting device.

Although the preferred embodiment of the present invention (experiment of combination of hole blocking layer and light emitting layer) has been described above, the present invention is not limited thereto and can be implemented with various modifications within the scope of the claims and detailed description of the invention. It is possible and this also falls under the category of invention.

1: substrate
2: anode
3: Hole injection layer
4: Hole transport layer
5: Electronic blocking layer
6: Light-emitting layer
7: Hole blocking layer
8: Electron transport layer
9: Electron injection layer
10: cathode
11: Electron injection and transport layer
21: first organic layer
22: second organic layer

Claims (14)

anode;
cathode;
Comprising a first organic material layer and a second organic material layer provided between the anode and the cathode,
The first organic layer includes a compound represented by the following formula (1),
The second organic material layer is an organic light-emitting device comprising a compound represented by the following formula (2):
[Formula 1]

In Formula 1,
L1 to L3 are the same or different from each other and are each independently a substituted or unsubstituted phenylene group,
One of Ar1 and Ar2 is a substituted or unsubstituted phenanthrenyl group, and the other is a substituted or unsubstituted naphthyl group,
Ra is hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group, or combined with adjacent groups to form a substituted or unsubstituted ring,
a is an integer from 0 to 9, and when a is 2 or more, Ra of 2 or more is the same or different from each other,
[Formula 2]

R1 is hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,
m is an integer from 0 to 9, and when m is 2 or more, 2 or more R1 are the same as or different from each other,
D is deuterium, n is an integer from 0 to 8,
R2 to R6 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; or the following formula A,
At least one of R2 and R6 is of formula A below,
[Formula A]

In Formula A,
R7 to R11 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group, or adjacent substituents combine with each other to form a substituted or unsubstituted ring,
The dotted line (---) is the part connected to Chemical Formula 2. In claim 1,
The above Chemical Formula 1 is an organic light-emitting device represented by the following Chemical Formula 1-1:
[Formula 1-1]

In Formula 1-1,
The definitions of Ar1, Ar2, Ra and a are the same as those in Formula 1 above,
Rb to Rd are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,
b to d are each independently an integer of 0 to 4, and when b to d are each independently 2 or more, 2 or more Rb to Rd are the same or different from each other. In claim 1,
Formula 1 is an organic light-emitting device represented by the following formula 1-1-1 or 1-1-2:
[Formula 1-1-1]

[Formula 1-1-2]

In the above formulas 1-1-1 and 1-1-2,
The definitions of L1 to L3, Ra and a are the same as those in Formula 1 above,
Re and Rf are the same or different from each other and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,
e is an integer from 0 to 7, and when e is 2 or more, 2 or more Re are the same or different from each other,
f is an integer from 0 to 9, and when f is 2 or more, Rf of 2 or more is the same or different from each other. In claim 1,
The above Chemical Formula 2 is an organic light-emitting device represented by the following Chemical Formula 2-1:
[Formula 2-1]

In Formula 2-1, the definitions of R1, m, D, n, and R3 to R11 are the same as those in Formula 2. In claim 1,
L1 to L3 are the same or different from each other, and are each independently a phenylene group substituted or unsubstituted with deuterium,
One of Ar1 and Ar2 is a phenanthrenyl group substituted or unsubstituted with deuterium, and the other is a naphthyl group substituted or unsubstituted with deuterium,
Ra is hydrogen; Or an organic light-emitting device that is deuterium. In claim 1,
Among R1 to R11, the remainders other than Formula A are the same or different from each other, and are each independently hydrogen; Or an organic light-emitting device that is deuterium. In claim 1,
The organic light-emitting device of Formula 2 includes at least one deuterium. In claim 1,
An organic light-emitting device in which Formula 1 is represented by any one of the following compounds:

. In claim 1,
Formula 2 is an organic light-emitting device represented by any one of the following compounds:

. In claim 1,
The first organic material layer is an organic light emitting device located between the second organic material layer and the anode. In claim 1,
An organic light emitting device wherein the first organic material layer is an electron blocking layer. In claim 1,
An organic light-emitting device wherein the second organic material layer is a light-emitting layer. The organic light emitting device of claim 12, wherein the light emitting layer includes the compound represented by Formula 2 as a host and further includes a dopant. In claim 1,
One or more organic layers are additionally provided between the anode and the cathode, and the organic layer includes a hole transport layer, a hole injection layer, a hole transport and injection layer, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, and an electron transport and injection layer. An organic light-emitting device further comprising at least one layer of a layer and a hole blocking layer.