KR102629147B1 - Compound and organic light emitting device comprising same - Google Patents

Abstract

This specification provides a compound represented by Formula 1 and an organic light-emitting device containing the same.

Description

Compound and organic light-emitting device containing the same {COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING SAME}

This specification relates to compounds and organic light-emitting devices containing the same.

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.

KR 20160026661 A

This specification provides compounds and organic light-emitting devices containing the same.

An exemplary embodiment of the present specification provides a compound represented by the following formula (1).

[Formula 1]

In Formula 1,

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

Ra to Rc, R1, R4, R5 and R8 to R10 are the same or different from each other and are each independently hydrogen; heavy hydrogen; Nitrile group; nitro group; hydroxyl group; carbonyl group; ester group; imide group; amide group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted arylsulfoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted amine group; Substituted or unsubstituted arylphosphine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

R2, R3, R6 and R7 are the same or different from each other and are each independently hydrogen; or deuterium,

n9 is an integer from 0 to 3, and when n9 is 2 or more, 2 or more R9 are the same or different from each other,

n10 is an integer from 0 to 4, and when n10 is 2 or more, 2 or more R10 are the same or different from each other.

In addition, an exemplary embodiment of the present specification includes an anode; cathode; and an organic light emitting device comprising at least one organic material layer provided between the anode and the cathode, wherein at least one layer of the organic material layer includes the compound represented by Formula 1.

The compounds described in this specification can be used as a material for the organic layer of an organic light-emitting device. The compound according to at least one embodiment can improve efficiency, low driving voltage, and/or improve lifespan characteristics in organic light-emitting devices. In particular, the compounds described herein can be used as hole injection, hole transport, hole injection and hole transport, electron blocking, light emission, hole blocking, electron transport, or electron injection materials. In addition, compared to existing organic light emitting devices, it has 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 light emitting layer 5, and a cathode 8 are sequentially stacked.
Figure 2 shows the substrate (1), anode (2), hole injection layer (3), hole transport layer (4), light emitting layer (5), electron transport layer (6), electron injection layer (7), and cathode (8) sequentially. An example of a stacked organic light emitting device is shown.

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.

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; Nitrile group (-CN); nitro group; hydroxyl group; amino group; silyl group; boron group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; and substituted or unsubstituted 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; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; and substituted or unsubstituted 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.

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 -SiY _a Y _b Y _c , where Y _a , Y _b and Y _c 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 -BY _{dY e} , where Y _d and Y _e 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 include a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, triphenyl group, chrysenyl group, fluorenyl group, triphenylenyl group, etc., but is not limited thereto. no.

In the present specification, the fluorenyl group may be substituted, and two substituents may be 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, and dibenzothiophene group. , carbazole group, benzocarbazole group, naphthobenzofuran group, benzonaphthothiophene group, indenocarbazole group, triazinyl group, etc., but is 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, in a substituted or unsubstituted ring formed by combining adjacent groups, “ring” refers to a hydrocarbon ring; Or it means 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 combining with adjacent groups means a substituted or unsubstituted aliphatic hydrocarbon ring by combining 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 compound represented by Formula 1 of the present invention can improve injection and movement of carriers by increasing the dipole moment by including a four-ring condensed ring containing N and C in the anthracene structure.

In particular, when anthracene is bonded to a benzene ring that is directly condensed with an N-containing ring, the electron donating ability for anthracene is greater than when it is not, so injection and movement of holes are improved, and driving voltage and lifespan are improved accordingly. Shows effect.

Additionally, when the compound represented by Formula 1 of the present invention contains deuterium, the efficiency and lifespan of the device are improved. Specifically, when hydrogen is replaced with deuterium, the chemical properties of the compound rarely change, but the physical properties of the deuterated compound change and the vibrational energy level is lowered. Compounds substituted with deuterium can prevent a decrease in quantum efficiency due to a decrease in intermolecular van der Waals forces or collisions due to intermolecular vibrations. Additionally, C-D bonds can improve the stability of compounds.

Therefore, when the compound represented by the above-described formula 1 is applied to an organic light-emitting device, an organic light-emitting device having high efficiency, low voltage, and/or long lifespan characteristics can be obtained.

Hereinafter, Chemical Formula 1 will be described in detail.

[Formula 1]

In Formula 1,

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

Ra to Rc, R1, R4, R5 and R8 to R10 are the same or different from each other and are each independently hydrogen; heavy hydrogen; Nitrile group; nitro group; hydroxyl group; carbonyl group; ester group; imide group; amide group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted arylsulfoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted amine group; Substituted or unsubstituted arylphosphine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

R2, R3, R6 and R7 are the same or different from each other and are each independently hydrogen; or deuterium,

n9 is an integer from 0 to 3, and when n9 is 2 or more, 2 or more R9 are the same or different from each other,

n10 is an integer from 0 to 4, and when n10 is 2 or more, 2 or more R10 are the same or different from each other.

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

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

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

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

In an exemplary embodiment of the present specification, Ar1 is a substituted or unsubstituted phenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted phenanthrenyl group; Substituted or unsubstituted triphenylene group; Substituted or unsubstituted fluorenyl group; Substituted or unsubstituted pyrene group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted dibenzothiophene group; Substituted or unsubstituted naphthobenzofuran group; Substituted or unsubstituted naphthobenzothiophene group; Or a substituted or unsubstituted carbazole group.

In an exemplary embodiment of the present specification, Ar1 is a substituted or unsubstituted phenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted phenanthrenyl group; Substituted or unsubstituted triphenylene group; Substituted or unsubstituted fluorenyl group; Substituted or unsubstituted pyrene group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted dibenzothiophene group; Substituted or unsubstituted naphthobenzofuran group; Or a substituted or unsubstituted carbazole group.

In one embodiment of the present specification, Ar1 is a phenyl group substituted or unsubstituted by deuterium, an alkyl group, or an aryl group; A naphthyl group substituted or unsubstituted with deuterium, an alkyl group, or an aryl group; Biphenyl group substituted or unsubstituted with deuterium, alkyl group, or aryl group; A phenanthrenyl group substituted or unsubstituted with deuterium, an alkyl group, or an aryl group; A triphenylene group substituted or unsubstituted with deuterium, an alkyl group, or an aryl group; A fluorenyl group unsubstituted or substituted with deuterium, an alkyl group, or an aryl group; A pyrene group substituted or unsubstituted with deuterium, an alkyl group, or an aryl group; Dibenzofuran group substituted or unsubstituted with deuterium, alkyl group, or aryl group; Dibenzothiophene group substituted or unsubstituted with deuterium, alkyl group, or aryl group; A naphthobenzofuran group substituted or unsubstituted with deuterium, an alkyl group, or an aryl group; Or it is a carbazole group substituted or unsubstituted with deuterium, an alkyl group, or an aryl group.

In one embodiment of the present specification, Ar1 is a phenyl group substituted or unsubstituted with deuterium, a methyl group, a phenyl group, or a naphthyl group; Naphthyl group substituted or unsubstituted with deuterium, methyl group, phenyl group, or naphthyl group; Biphenyl group substituted or unsubstituted with deuterium, methyl group, phenyl group, or naphthyl group; Phenanthrenyl group substituted or unsubstituted with deuterium, methyl group, phenyl group, or naphthyl group; A triphenylene group substituted or unsubstituted with deuterium, methyl group, phenyl group, or naphthyl group; A fluorenyl group unsubstituted or substituted with deuterium, methyl group, phenyl group, or naphthyl group; Pyrene group substituted or unsubstituted with deuterium, methyl group, phenyl group, or naphthyl group; Dibenzofuran group substituted or unsubstituted with deuterium, methyl group, phenyl group, or naphthyl group; Dibenzothiophene group substituted or unsubstituted with deuterium, methyl group, phenyl group, or naphthyl group; Naphthobenzofuran group substituted or unsubstituted with deuterium, methyl group, phenyl group, or naphthyl group; Or it is a carbazole group substituted or unsubstituted with deuterium, methyl group, phenyl group, or naphthyl group.

In an exemplary embodiment of the present specification, Ar1 is a phenyl group substituted or unsubstituted with any one of the group consisting of deuterium, a phenyl group, and a naphthyl group, or a group in which two or more of the above-mentioned groups are linked; A naphthyl group substituted or unsubstituted with any one of the group consisting of deuterium, phenyl group, and naphthyl group, or a group in which two or more of the foregoing groups are linked; Biphenyl group; A phenanthrenyl group substituted or unsubstituted with any one of the group consisting of a phenyl group and a naphthyl group, or a group in which two or more of the above-mentioned groups are linked; triphenylene group; Fluorenyl group substituted or unsubstituted with a methyl group; Pyrene group; Dibenzofuran group; Dibenzothiophene group; Naphthobenzofuran group; Or it is a carbazole group substituted or unsubstituted with a phenyl group.

In one embodiment of the present specification, Ar1 is a phenyl group substituted or unsubstituted by deuterium, a phenyl group, or a naphthyl group; Naphthyl group substituted or unsubstituted with deuterium, phenyl group, or naphthyl group; Biphenyl group; A phenanthrenyl group substituted or unsubstituted by a phenyl group or a naphthyl group; triphenylene group; Fluorenyl group substituted or unsubstituted with a methyl group; Pyrene group; Dibenzofuran group; Dibenzothiophene group; Naphthobenzofuran group; Or it is a carbazole group substituted or unsubstituted with a phenyl group.

In an exemplary embodiment of the present specification, Ar1 is a substituted or unsubstituted phenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted dibenzofuran group.

In one embodiment of the present specification, Ar1 is a phenyl group substituted or unsubstituted by deuterium or a naphthyl group; Naphthyl group substituted or unsubstituted with deuterium; Biphenyl group; Or it is a dibenzofuran group.

In an exemplary embodiment of the present specification, Ar1 is a substituted or unsubstituted phenyl group; Or a substituted or unsubstituted naphthyl group.

In one embodiment of the present specification, Ar1 is a phenyl group; Or it is a naphthyl group.

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

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

In Formulas 1-1 to 1-4, the definitions of Ar1, R1 to R10, n9, and n10 are the same as those in Formula 1.

In an exemplary embodiment of the present specification, Ra to Rc, R1, R4, R5 and R8 to R10 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or it is a substituted or unsubstituted heterocyclic group.

In an exemplary embodiment of the present specification, Ra to Rc, R1, R4, R5 and R8 to R10 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; Substituted or unsubstituted 6 to 60 aryl groups; Or it is a substituted or unsubstituted 2 to 60 heterocyclic group.

In an exemplary embodiment of the present specification, Ra to Rc, R1, R4, R5 and R8 to R10 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; Substituted or unsubstituted 6 to 30 aryl groups; Or it is a substituted or unsubstituted 2 to 30 heterocyclic group.

In an exemplary embodiment of the present specification, Ra to Rc, R1, R4, R5 and R8 to R10 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; Substituted or unsubstituted 6 to 20 aryl groups; Or it is a substituted or unsubstituted 2 to 20 heterocyclic group.

In an exemplary embodiment of the present specification, Ra to Rc, R1, R4, R5 and R8 to R10 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.

In an exemplary embodiment of the present specification, Ra to Rc, R1, R4, R5 and R8 to R10 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted methyl group; Substituted or unsubstituted phenyl group; Or a substituted or unsubstituted naphthyl group.

In an exemplary embodiment of the present specification, Ra to Rc, R1, R4, R5 and R8 to R10 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; methyl group; phenyl group; Or it is a naphthyl group.

In an exemplary embodiment of the present specification, Ra to Rc, R1, R4, R5 and R8 to R10 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; methyl group; Or it is a phenyl group.

In one embodiment of the present specification, Ra and Rb are a substituted or unsubstituted alkyl group; Or it is a substituted or unsubstituted aryl group.

In one embodiment of the present specification, Ra and Rb are substituted or unsubstituted alkyl groups.

In one embodiment of the present specification, Ra and Rb are substituted or unsubstituted methyl groups.

In one embodiment of the present specification, Ra and Rb are methyl groups.

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

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

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

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

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

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

In an exemplary embodiment of the present specification, R1, R4, R5, and R8 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; Or it is a substituted or unsubstituted aryl group.

In an exemplary embodiment of the present specification, R1, R4, R5, and R8 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; Or it is a substituted or unsubstituted aryl group.

In an exemplary embodiment of the present specification, R1, R4, R5, and R8 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; Or it is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In an exemplary embodiment of the present specification, R1, R4, R5, and R8 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; Or it is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

In an exemplary embodiment of the present specification, R1, R4, R5, and R8 are the same or different from each other, and are each independently hydrogen; Or deuterium.

In one embodiment of the present specification, R1, R4, R5, and R8 are hydrogen.

In one embodiment of the present specification, R1, R4, R5, and R8 are deuterium.

In an exemplary embodiment of the present specification, R2, R3, R6, and R7 are the same or different from each other, and are each independently hydrogen; Or it is deuterium.

In one embodiment of the present specification, R2, R3, R6 and R7 are hydrogen.

In one embodiment of the present specification, R2, R3, R6, and R7 are deuterium.

In an exemplary embodiment of the present specification, R9 and R10 are the same or different from each other, and are each independently hydrogen; Or it is deuterium.

In one embodiment of the present specification, R9 and R10 are hydrogen.

In one embodiment of the present specification, R9 and R10 are deuterium.

In one embodiment of the present specification, all hydrogen in Formula 1 may be replaced with deuterium.

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

[Formula 2-1]

[Formula 2-2]

In Formulas 2-1 and 2-2, the definitions of Ar1, R1 to R10, n9, and n10 are the same as those in Formula 1.

In an exemplary embodiment of the present specification, the formula 1 is represented by one of the structural formulas below. At this time, means the binding position.

In the above structural formula, Rc is as defined in Formula 1 above.

In an exemplary embodiment of the present specification, the formula 1 is represented by one of the structural formulas below. At this time, means the binding position.

In the above structural formula, Rc is as defined in Formula 1 above.

In the above structural formula, Rc is a substituted or unsubstituted aryl group.

In the above structural formula, Rc is a phenyl group.

In one embodiment of the present specification, n9 is 0.

In one embodiment of the present specification, n9 is an integer of 1 to 3.

In one embodiment of the present specification, n9 is 1.

In one embodiment of the present specification, n9 is 3.

In one embodiment of the present specification, n10 is 0.

In one embodiment of the present specification, n10 is an integer of 1 to 4.

In one embodiment of the present specification, n10 is 1.

In one embodiment of the present specification, n10 is 4.

In one embodiment of the present specification, Ar1 is substituted with at least one deuterium. In another embodiment, Ar1 is substituted by more than 40% with deuterium. In another exemplary embodiment, Ar1 is substituted by more than 50% with deuterium. In another embodiment, Ar1 is substituted by more than 60% with deuterium. In another exemplary embodiment, Ar1 is substituted by more than 70% with deuterium. In another exemplary embodiment, Ar1 is substituted by more than 80% with deuterium. In another embodiment, Ar1 is more than 90% substituted with deuterium. In another embodiment, Ar1 is 100% substituted with deuterium.

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

In an exemplary embodiment of the present specification, Ra to Rc and R1 to R10 are each substituted with at least one deuterium. In another embodiment, Ra to Rc and R1 to R10 are each substituted by 40% or more with deuterium. In another embodiment, Ra to Rc and R1 to R10 are each substituted by more than 50% with deuterium. In another exemplary embodiment, Ra to Rc and R1 to R10 are each substituted by more than 60% with deuterium. In another exemplary embodiment, Ra to Rc and R1 to R10 are each substituted by more than 70% with deuterium. In another exemplary embodiment, Ra to Rc and R1 to R10 are each substituted by more than 80% with deuterium. In another embodiment, Ra to Rc and R1 to R10 are each substituted by more than 90% of deuterium. In another exemplary embodiment, Ra to Rc and R1 to R10 are each 100% substituted with deuterium.

In one embodiment of the present specification, the compound represented by Formula 1 is substituted with at least one deuterium. In another exemplary embodiment, the compound represented by Formula 1 is substituted with deuterium by more than 20%. In another exemplary embodiment, the compound represented by Formula 1 is substituted by more than 30% with deuterium. In another exemplary embodiment, the compound represented by Formula 1 is substituted by more than 40% 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 an exemplary embodiment of the present specification, four or more of R1 to R8 are deuterium, and the remainder are hydrogen. In another embodiment, five or more of R1 to R8 are deuterium, and the remainder are hydrogen. In another embodiment, six or more of R1 to R8 are deuterium, and the remainder are hydrogen. In another embodiment, 7 or more of R1 to R8 are deuterium, and the remainder are hydrogen. In another embodiment, R1 to R8 are all deuterium. At this time, the remaining substituents (Ra to Rc, Ar1, R9, and R10) other than R1 to R8 are substituted or unsubstituted with deuterium.

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

The compound represented by Chemical Formula 1 according to an exemplary embodiment of the present specification may have a core structure prepared as shown in Scheme 1 below. 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.

<Scheme 1>

In Scheme 1, X1 is N-Rc, X2 is CRaRb, and the definitions of the remaining substituents are the same as those in Formula 1 described above.

Although Scheme 1 illustrates the process of synthesizing a compound in which a specific substituent is bonded to a specific position, the method of formula 1 above can be obtained by a synthetic method known in the art using starting materials, intermediates, etc. known in the art. Compounds that fall within the range can be synthesized.

In the present specification, compounds having various energy band gaps can be synthesized by introducing various substituents into the core structure of the compound represented by Formula 1 above. 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.

Additionally, the present specification provides an organic light-emitting device containing the above-mentioned compound.

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

In this specification, when a part “includes” a certain 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; And an organic light-emitting device comprising at least one organic material layer provided between the anode and the cathode, wherein at least one layer of the organic material layer includes a compound represented by the above-mentioned formula (1).

The organic light-emitting device of the present specification can be manufactured using conventional organic light-emitting device manufacturing methods and materials, except that the organic material layer is formed using the compound of Formula 1 described above.

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 one or more of the organic material layers, a hole transport layer, a hole injection layer, an electron blocking layer, a hole transport and injection 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 that includes 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 the organic light emitting device of the present specification, the organic material layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, the hole transport layer, or the hole injection and transport layer is a compound represented by the above-mentioned formula 1. It can be included.

In the organic light emitting device of the present specification, the organic material layer includes a hole transport layer or a hole injection layer, and the hole transport layer or the hole injection layer may include a compound represented by the above-described formula (1).

In one embodiment of the present specification, the organic material layer includes an electron injection layer, an electron transport layer, an electron injection and transport layer, or a hole blocking layer, and the electron injection layer, the electron transport layer, the electron injection and transport layer, or the hole blocking layer is as described above. It may include a compound represented by Formula 1.

In the organic light emitting device of the present specification, the organic material layer includes an electron transport layer, an electron injection layer, or an electron transport and injection layer, and the electron transport layer, an electron injection layer, or an electron transport and injection layer is represented by the above-mentioned formula (1) It may contain compounds.

In one embodiment of the present specification, the organic material layer includes an electron control layer, and the electron control layer may include a compound represented by the above-described Chemical Formula 1.

In one embodiment of the present specification, the organic material layer includes a light-emitting layer, and the light-emitting layer includes the compound represented by the above-described formula (1).

In one embodiment of the present specification, the organic material layer includes a light-emitting layer, and the light-emitting layer includes the compound represented by the above-described formula 1 as a host.

In one embodiment of the present specification, the organic material layer includes a light-emitting layer, and the light-emitting layer includes the compound represented by the above-described formula (1) as a dopant.

In one embodiment of the present specification, the organic light-emitting device is a green organic light-emitting device in which the light-emitting layer includes the compound represented by Formula 1 as a host.

According to an exemplary embodiment of the present specification, the organic light-emitting device is a red organic light-emitting device in which the light-emitting layer includes the compound represented by Formula 1 as a host.

In another exemplary embodiment, the organic light emitting device is a blue organic light emitting device in which the light emitting layer includes the compound represented by Formula 1 as a host.

In one embodiment of the present specification, the organic material layer includes a light-emitting layer, and the light-emitting layer includes the compound represented by Formula 1 as a host and may further include a dopant. At this time, the content of the dopant may be 1 part by weight to 60 parts by weight based on 100 parts by weight of the host, and is preferably included in 1 part by weight to 10 parts by weight.

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 to these.

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

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.

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

As another example, the organic layer includes a light-emitting layer, and the light-emitting layer includes the compound represented by Formula 1 as a host, and may further include an additional host.

In one embodiment of the present specification, the dopant includes an arylamine-based compound, a heterocyclic compound containing boron and nitrogen, or an Ir complex.

In one embodiment of the present specification, the fluorescent dopant may be selected from the following structures, but is not limited thereto.

In one embodiment of the present specification, an Ir complex may be used as the phosphorescent dopant, and as an example, any one of the following structures may be used, but is not limited thereto.

In one embodiment of the present specification, the light-emitting layer containing the compound represented by Formula 1 has a blue color.

According to one example, the content of the compound represented by Formula 1 is 70 parts by weight to 99.99 parts by weight, based on 100 parts by weight of the total of the host and dopant of the light emitting layer; Preferably, 80 to 99.9 parts by weight; More preferably, it is 90 to 99.5 parts by weight.

The organic light emitting device of the present specification may further include one or more organic material layers among 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. You can.

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 the compound represented by Formula 1.

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. Specifically, in one embodiment of the present specification, the compound represented by Formula 1 may be included in one of the two or more electron transport layers, and may be included in each of the two or more electron transport layers.

Additionally, in an exemplary 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 may be the same or different from each other.

When the organic layer containing the compound represented by Formula 1 is an electron transport layer, the electron transport 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 may further include Lithium Quinolate (LiQ).

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

In addition, in an exemplary embodiment of the present specification, when the compound represented by Formula 1 is included in each of the two or more hole transport layers, materials other than the compound represented by Formula 1 may be the same or different from each other. there is.

In one embodiment of the present specification, the organic material layer further includes a hole injection layer or a hole transport layer including a compound including an arylamine group, carbazolyl group, or benzocarbazolyl group in addition to the organic material layer including the compound represented by Formula 1. It can be included.

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.

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

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

The structure of the organic light emitting device of this specification may have the same structure as shown in FIGS. 1 and 2, 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 light emitting layer 5, and a cathode 8 are sequentially stacked. In this structure, the compound may be included in the light-emitting layer 6.

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

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 injection and transport layer, an electron blocking layer, a light emitting layer and an electron transport layer, an electron injection layer, an electron transport and injection layer, etc., but is not limited to this and may have a single-layer structure. You can. 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, but are not limited to, multi-layered materials such as LiF/Al or LiO ₂ /Al.

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 metal porphyrine, oligothiophene, arylamine-based organic substances, hexanitrilehexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based organic substances. organic substances, anthraquinone, polyaniline, and polythiophene series 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 arylamine-based organic materials, conductive polymers, and block copolymers with both conjugated and non-conjugated portions, but are not limited to these.

An additional hole buffer layer may be provided between the hole injection layer and the hole transport layer, and may include hole injection or transport materials 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 capable of emitting light in the visible range by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and is preferably a material with good quantum efficiency for fluorescence or phosphorescence. Specific examples include the compounds of Formula 1 described above; 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-phenylquinoline)acetylacetonate iridium), 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, a phosphor such as Ir(ppy) ₃ (fac tris(2-phenylpyridine)iridium) or a fluorescent material such as Alq3 (tris(8-hydroxyquinolino)aluminum) can be used as the light-emitting dopant. However, it is not limited to this. When 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 and PPV-based polymers may be used, but are not limited to these.

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 above-mentioned compounds or 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.

Synthesis Example 1: Synthesis of intermediate a

Synthesis Example 1-1) Synthesis of intermediate a-1

3,3-Dimethyl-2,3-dihydro-1H-inden-1-one (30g, 187mmol) and (4-bromophenyl)hydrazine (35g, 187mmol) were added to 300ml of acetic acid and incubated at 80°C for 12 hours. It was stirred for a while. After removing the acetic acid, put it in chloroform and extract it with water several times. The organic layer is treated with anhydrous magnesium sulfate, distilled under reduced pressure to remove chloroform, and purified by column chromatography to obtain intermediate a-1. (32g, yield 55%)

Synthesis Example 1-2) Synthesis of intermediate a-2

Intermediate a-1 (32g, 102mmol) and iodobenzene (20.9g, 102mml) were dissolved in 300ml of DMF (Dimethylformamide), then CS ₂ CO ₃ (66.8g, 205mmol) and CuI (3.90g, 20mmol) ) is added. Raise the temperature to 120℃ and stir for 16 hours. After cooling the reaction solution, add 1L of ethyl acetate, transfer to a separatory funnel, and extract once with an aqueous ammonia solution and three times in total with 1L of distilled water. The organic layer was collected, treated with anhydrous magnesium sulfate to remove water, and then distilled under reduced pressure. Purify using column chromatography (eluent EA:Hex) to obtain intermediate a-2. (25g, yield 63%)

Synthesis Example 1-3) Synthesis of intermediate a

Intermediate a-2 (25g, 64mmol), bis(pinacolato)diborone (19.6g, 77mmol), and KOAc (12.6g, 128mmol) were added to the flask with 200ml of dioxane and dispersed. Pd(dba) ₂ (0.74g, 1.3mmol) and PCy ₃ (0.72g, 2.6mmol) were added and stirred under reflux for 24 hours. After completion of the reaction, dioxane is removed by distillation under reduced pressure. After dissolving in chloroform and extracting with distilled water three times, the organic layer is distilled under reduced pressure to remove chloroform and purified using column chromatography to obtain intermediate a. (20g, yield 71%)

Synthesis Example 2: Synthesis of intermediates b and c

Synthesis Example 2-1) Synthesis of intermediates b-1 and c-1

Synthesized in the same manner as in Synthesis Example 1-1 except that (3-bromophenyl)hydrazine was used instead of (4-bromophenyl)hydrazine, and purified through column chromatography to produce intermediates b-1 and c-1. Obtained in a ratio of approximately 5:1.

Synthesis Example 2-2) Synthesis of intermediate b-2

Intermediate b-2 was obtained in the same manner as in Synthesis Example 1-2, except that b-1 was used instead of intermediate a-1.

Synthesis Example 2-3) Synthesis of intermediate b

Intermediate b was obtained in the same manner as in Synthesis Example 1-3, except that b-2 was used instead of intermediate a-2.

Synthesis Example 2-4) Synthesis of intermediate c-2

Intermediate c-2 was obtained in the same manner as in Synthesis Example 1-2, except that c-1 was used instead of intermediate a-1.

Synthesis Example 2-5) Synthesis of intermediate c

Intermediate c was obtained in the same manner as in Synthesis Example 1-3, except that c-2 was used instead of intermediate a-2.

Synthesis Example 3: Synthesis of intermediate d

Synthesis Example 3-1) Synthesis of intermediate d-1

Intermediate d-1 was obtained in the same manner as in Synthesis Example 1-1, except that (2-bromophenyl)hydrazine was used instead of (4-bromophenyl)hydrazine.

Synthesis Example 3-2) Synthesis of intermediate d-2

Intermediate d-2 was obtained in the same manner as in Synthesis Example 1-2, except that d-1 was used instead of intermediate a-1.

Synthesis Example 3-3) Synthesis of intermediate d

Intermediate d was obtained in the same manner as in Synthesis Example 1-3, except that d-2 was used instead of intermediate a-2.

Synthesis Example 4: Synthesis of intermediate e

Synthesis Example 4-1) Synthesis of intermediate e-1

In Synthesis Example 1-1, except that 1,1-dimethyl-1,3-dihydro-2H-inden-2-one was used instead of 3,3-dimethyl-2,3-dihydro-1H-inden-1-one. And then synthesized in the same manner to obtain intermediate e-1.

Synthesis Example 4-2) Synthesis of intermediate e-2

Intermediate e-2 was obtained in the same manner as in Synthesis Example 1-2, except that e-1 was used instead of intermediate a-1.

Synthesis Example 4-3) Synthesis of intermediate e

Intermediate e was obtained through the same synthesis in Synthesis Example 1-3, except that e-2 was used instead of intermediate a-2.

Synthesis Example 5: Synthesis of intermediates f and g

Synthesis Example 5-1) Synthesis of intermediates f-1 and g-1

In Synthesis Example 1-1, 1,1-dimethyl-1,3-dihydro-2H-inden-2-one was used instead of 3,3-dimethyl-2,3-dihydro-1H-inden-1-one, ( Intermediate f-1 and intermediate g-1, which were synthesized in the same manner except that (3-bromophenyl)hydrazine was used instead of 4-bromophenyl)hydrazine, were obtained by separating them through column chromatography.

Synthesis Example 5-2) Synthesis of intermediate f-2

Intermediate f-2 was obtained in the same manner as in Synthesis Example 1-2, except that f-1 was used instead of intermediate a-1.

Synthesis Example 5-3) Synthesis of intermediate f

Intermediate f was obtained in the same manner as in Synthesis Example 1-3, except that f-2 was used instead of intermediate a-2.

Synthesis Example 5-4) Synthesis of intermediate g-2

Intermediate g-2 was obtained in the same manner as in Synthesis Example 1-2, except that g-1 was used instead of intermediate a-1.

Synthesis Example 5-5) Synthesis of intermediate g

Intermediate g was obtained in the same manner as in Synthesis Example 1-3, except that g-2 was used instead of intermediate a-2.

Synthesis Example 6: Synthesis of intermediate h

Synthesis Example 6-1) Synthesis of intermediate h-1

In Synthesis Example 1-1, 1,1-dimethyl-1,3-dihydro-2H-inden-2-one was used instead of 3,3-dimethyl-2,3-dihydro-1H-inden-1-one, ( Intermediate h-1 was obtained through the same synthesis except that (2-bromophenyl)hydrazine was used instead of 4-bromophenyl)hydrazine.

Synthesis Example 6-2) Synthesis of intermediate h-2

Intermediate h-2 was obtained in the same manner as in Synthesis Example 1-2, except that h-1 was used instead of intermediate a-1.

Synthesis Example 6-3) Synthesis of intermediate h

Intermediate h was obtained through the same synthesis in Synthesis Example 1-3, except that h-2 was used instead of intermediate a-2.

Synthesis Example 7: Synthesis of Compound 1

After dissolving 9-bromo-10-phenylanthracene (15 g, 45mmol) and intermediate a (19.6g, 45mmol) in Dioxane (200ml), Pd(PPh ₃ ) ₄ (1.04g, 0.7mmol) and 2M K ₂ 50ml of CO ₃ aqueous solution was added and stirred under reflux for 24 hours. The reaction solution was cooled, and the organic layer was extracted with ethyl acetate and dried over anhydrous magnesium sulfate. The organic solvent was removed under reduced pressure and purified using column chromatography to obtain Compound 1 (19g, yield 75%). [M+H ⁺ ]= 562.3

Synthesis Example 8: Synthesis of Compound 2

Compound 2 was obtained by the same synthesis in Synthesis Example 7, except that 9-bromo-10-(naphthalen-1-yl)anthracene was used instead of 9-bromo-10-phenylanthracene, and intermediate b was used instead of intermediate a. . [M+H ⁺ ]= 612.3

Synthesis Example 9: Synthesis of Compound 3

Compound 3 was obtained by the same synthesis in Synthesis Example 7, except that 9-bromo-10-(naphthalen-2-yl)anthracene was used instead of 9-bromo-10-phenylanthracene, and intermediate c was used instead of intermediate a. . [M+H ⁺ ]= 612.3

Synthesis Example 10: Synthesis of Compound 4

In Synthesis Example 7, except that 9-([1,1'-biphenyl]-4-yl)-10-bromoanthracene was used instead of 9-bromo-10-phenylanthracene, and intermediate d was used instead of intermediate a. Compound 4 was obtained by the same synthesis. [M+H ⁺ ]= 638.3

Synthesis Example 11: Synthesis of Compound 5

In Synthesis Example 7, except that 9-([1,1'-biphenyl]-3-yl)-10-bromoanthracene was used instead of 9-bromo-10-phenylanthracene, and intermediate e was used instead of intermediate a. Compound 5 was obtained by the same synthesis. [M+H ⁺ ]= 638.3

Synthesis Example 12: Synthesis of Compound 6

In Synthesis Example 7, except that 9-([1,1'-biphenyl]-2-yl)-10-bromoanthracene was used instead of 9-bromo-10-phenylanthracene, and intermediate f was used instead of intermediate a. Compound 6 was obtained by the same synthesis. [M+H ⁺ ]= 638.3

Synthesis Example 13: Synthesis of Compound 7

Synthesis Example 13-1) Synthesis of compound 7-1

After dissolving 9-bromoanthracene (30 g, 117mmol) and (3-(naphthalen-1-yl)phenyl)boronic acid (28.9g, 117mmol) in Dioxane (600ml), Pd(PPh3)4 (2.69g, 2.33mmol) and 150ml of 2M K2CO3 aqueous solution were added and stirred under reflux for 24 hours. The reaction solution was cooled, and the organic layer was extracted with ethyl acetate and dried over anhydrous magnesium sulfate. The organic solvent was removed under reduced pressure and purified using column chromatography to obtain compound 7-1 (31 g, yield 74%).

Synthesis Example 13-2) Synthesis of Compound 7-2

Compound 7-1 (31g, 86mmol) was dissolved in 400ml of DMF, and N-bromosuccinimide (15.3g, 86mmol) dissolved in 50ml of DMF was slowly added dropwise. After stirring at room temperature for 2 hours, 300ml of water was added dropwise. When a solid is formed, it is filtered, dissolved in chloroform, and extracted several times with distilled water. Compound 7-2 was obtained by recrystallization from ethyl acetate. (27g, yield 68%)

Synthesis Example 13-3) Synthesis of Compound 7

Compound 7 was obtained in the same manner as in Synthesis Example 7, except that Compound 7-2 was used instead of 9-bromo-10-phenylanthracene, and Intermediate g was used instead of Intermediate a. [M+H ⁺ ]= 688.3

Synthesis Example 14: Synthesis of Compound 8

Synthesis Example 14-1) Synthesis of compound 8-1

Compound 8-1 was obtained in the same manner as in Synthesis Example 13-1, except that dibenzo[b,d]furan-2-ylboronic acid was used instead of (3-(naphthalen-1-yl)phenyl)boronic acid.

Synthesis Example 14-2) Synthesis of compound 8-2

Compound 8-2 was obtained by the same synthesis in Synthesis Example 13-2, except that compound 8-1 was used instead of compound 7-1.

Synthesis Example 14-3) Synthesis of Compound 8

Compound 8 was obtained in the same manner as in Synthesis Example 7, except that Compound 8-2 was used instead of 9-bromo-10-phenylanthracene, and Intermediate h was used instead of Intermediate a. [M+H ⁺ ]= 652.3

Synthesis Example 15: Synthesis of Compound 9

Compound 1 (10g) and AlCl ₃ (2g) were added to C ₆ D ₆ (200ml) and stirred for 2 hours. After completion of the reaction, D ₂ O (15 ml) was added, stirred for 30 minutes, and trimethylamine (1.2 ml) was added dropwise. The reaction solution was transferred to a separatory funnel and extracted with water and toluene. The extract was dried with MgSO ₄ and recrystallized with ethyl acetate to obtain compound 9. (7.8g, yield 78%) [M+H ⁺ ]=587.4

Synthesis Example 16: Synthesis of Compound 10

Compound 10 was obtained by the same synthesis in Synthesis Example 15, except that Compound 2 was used instead of Compound 1. [M+H ⁺ ]=639.4

Example 1

A glass substrate coated with a thin film of ITO (indium tin oxide) with a thickness of 150 nm was placed in distilled water with a detergent dissolved in it and washed ultrasonically. At this time, a detergent from Fischer Co. was used, and distilled water filtered secondarily using a filter from 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 nitrogen plasma and then transported to a vacuum evaporator. On the ITO transparent electrode prepared in this way, the following HAT-CN compound was thermally vacuum deposited to a thickness of 5 nm to form a hole injection layer. Next, HTL1 was thermally vacuum deposited to a thickness of 100 nm, and then HTL2 was thermally vacuum deposited to a thickness of 10 nm to form a hole transport layer. Subsequently, Compound 1 as a host and BD-A (weight ratio 95:5) as a dopant were simultaneously vacuum deposited to form a 20 nm thick light emitting layer. Next, ETL was vacuum deposited to a thickness of 20 nm to form an electron transport layer. Subsequently, LiF was vacuum deposited to a thickness of 0.5 nm to form an electron injection layer. Next, aluminum was deposited to a thickness of 100 nm to form a cathode, thereby manufacturing an organic light emitting device.

The structures of the compounds used in the examples are as follows.

Examples 2 to 10 and Comparative Examples 1 to 4

An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compounds listed in Table 1 below were used instead of Compound 1 as the host of the light-emitting layer. At this time, the compound represented by Formula 1 of the present invention among the structures below was prepared through the same process as the above-described Synthesis Examples 1 to 16.

In the organic light emitting devices manufactured in Examples 1 to 10 and Comparative Examples 1 to 4, the driving voltage and luminous efficiency were measured at a current density of 10 mA/cm ² , and the initial luminance was measured at a current density of 20 mA/cm ² The time to reach 95% of the comparison (LT) was measured, and the results are shown in Table 1 below.

compound
(Emissive layer host) 10 mA/cm ² measured value LT (T95%) Vop Cd/A Example 1 Compound 1 4.02 6.60 181 Example 2 compound 2 4.01 6.80 183 Example 3 Compound 3 4.09 6.77 175 Example 4 Compound 4 4.15 6.72 190 Example 5 Compound 5 4.03 6.75 169 Example 6 Compound 6 4.10 6.67 180 Example 7 Compound 7 4.13 6.80 188 Example 8 Compound 8 3.99 6.90 167 Example 9 Compound 9 4.03 6.58 270 Example 10 Compound 10 4.02 6.82 263 Comparative Example 1 BH-A 4.61 6.12 112 Comparative Example 2 BH-B 4.40 5.51 125 Comparative Example 3 BH-C 4.22 6.40 129 Comparative Example 4 BH-D 4.21 6.37 122

Examples 1 to 10 using the compound represented by Formula 1 of the present invention all exhibited characteristics of low voltage and high efficiency, and also showed superior lifespan compared to Comparative Examples 1 to 4. In particular, Examples 11 and 12 showed that lifespan was further improved by deuterium substitution.

Comparative Example 1, which used a host compound consisting only of aryl, had a high driving voltage and was not advantageous in terms of efficiency and lifespan, and Comparative Example 2, which used a host compound containing a dibenzofuran group, had anthracene on a benzene ring that was not directly condensed with the N-containing ring. It was confirmed that Comparative Examples 3 and 4 using the combined compound had a higher driving voltage and were not advantageous in terms of efficiency and lifespan compared to Examples 1 to 10.

Although the preferred embodiment (host) of the present invention 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 the detailed description of the invention, and this is also part of the invention. belongs to the category

1: substrate
2: anode
3: Hole injection layer
4: Hole transport layer
5: Light-emitting layer
6: Electron transport layer
7: Electron injection layer
8: cathode

Claims (12)

A compound represented by the following formula (1):
[Formula 1]

In Formula 1,
Ar1 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms,
Ra and Rb are the same or different from each other and are each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms,
Rc is an aryl group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium,
R1 to R10 are the same or different from each other, and are each independently hydrogen; or deuterium,
n9 is an integer from 0 to 3, and when n9 is 2 or more, 2 or more R9 are the same or different from each other,
n10 is an integer from 0 to 4, and when n10 is 2 or more, 2 or more R10 are the same or different from each other. The method according to claim 1, wherein the formula 1 is a compound represented by any one of the following formulas 1-1 to 1-4:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

In Formulas 1-1 to 1-4, the definitions of Ar1, Ra to Rc, R1 to R10, n9, and n10 are the same as those in Formula 1. The compound according to claim 1, wherein Formula 1 is represented by the following Formula 2-1 or 2-2:
[Formula 2-1]

[Formula 2-2]

In Formulas 2-1 and 2-2, the definitions of Ar1, Ra to Rc, R1 to R10, n9, and n10 are the same as those in Formula 1. The compound according to claim 1, wherein Ra and Rb are substituted or unsubstituted methyl groups. delete delete The compound according to claim 1, wherein Formula 1 is represented by any one of the following compounds:

. anode; cathode; and an organic light-emitting device comprising at least one organic material layer provided between the anode and the cathode, wherein at least one layer of the organic material layer includes the compound according to any one of claims 1 to 4 and 7. . In claim 8,
An organic light-emitting device wherein the organic material layer includes a light-emitting layer, and the light-emitting layer includes the compound. The organic light-emitting device of claim 9, wherein the light-emitting layer includes the compound as a host and further includes a dopant. In claim 8,
The organic material layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, the hole transport layer, or the hole injection and transport layer includes the compound. In claim 8,
The organic material layer includes an electron transport layer, an electron injection layer, or an electron transport and injection layer, and the electron transport layer, an electron injection layer, or an electron transport and injection layer includes the compound.