KR20200107854A - Compound and organic light emitting device comprising the same - Google Patents

Abstract

The present invention relates to a compound represented by chemical formula 1, and to an organic light-emitting device comprising the same. The organic light-emitting device having low driving voltage, excellent efficiency, and excellent service life characteristics is obtained by including the compound in an organic material layer of the organic light-emitting device.

Description

Compound and organic light-emitting device comprising the same TECHNICAL FIELD

This application claims the benefit of the filing date of Korean Patent Application No. 10-2019-0026895 filed with the Korean Intellectual Property Office on March 8, 2019, the entire contents of which are incorporated herein.

The present specification relates to a compound and an organic light emitting device including the same.

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

Materials used in organic light-emitting devices are pure organic materials or complex compounds in which organic materials and metals form a complex, and depending on the use, hole injection materials, hole transport materials, light-emitting materials, electron transport materials, electron injection materials, etc. It can be classified as Here, as the hole injection material or the hole transport material, an organic material having a p-type property, that is, an organic material that is easily oxidized and has an electrochemically stable state upon oxidation is mainly used. Meanwhile, as an electron injection material or an electron transport material, an organic material having an n-type property, that is, an organic material that is easily reduced and has an electrochemically stable state upon reduction is mainly used. As the light-emitting layer material, a material having both p-type and n-type properties, that is, a material that is stable in both oxidation and reduction states, is preferable, and excitons generated by recombination of holes and electrons in the emission layer are formed. A material having high luminous efficiency that converts it to light when it is formed is preferable.

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

Korean Patent Publication No. 10-2014-103007

In the present specification, a compound and an organic light emitting device including the same are described.

An exemplary embodiment of the present specification provides a compound represented by Formula 1 below.

[Formula 1]

In Formula 1,

A and B are the same as or different from each other, and each independently a substituted or unsubstituted aromatic hydrocarbon ring; Or a substituted or unsubstituted aromatic heterocycle,

X is a single bond; C(R1)(R2); Si(R3)(R4); N(R5); O; S; Or SO ₂ ,

R1 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitrile group; Nitro group; Hydroxy group; Carbonyl group; Ester group; Imide group; Amide group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkyl thioxy group; A substituted or unsubstituted arylthioxy group; A substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, and may be combined with an adjacent group, A or B to form a substituted or unsubstituted ring,

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

Ar is hydrogen; heavy hydrogen; Nitrile group; Nitro group; Hydroxy group; Carbonyl group; Ester group; Imide group; Amide group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkyl thioxy group; A substituted or unsubstituted arylthioxy group; A substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, provided that diphenylfluorene is excluded,

m1 is 1 or 2, m3 is an integer from 0 to 2,

When m1 is 1, m2 is 2 or 3, when m1 is 2, m2 is 1, and m2+m3 is 3,

When m1 to m3 are each 2 or more, the substituents in parentheses are the same or different from each other,

* Combines with any one of A, B and R1 to R5.

In addition, the present specification is a positive electrode; cathode; And at least one organic material layer provided between the anode and the cathode, and at least one of the organic material layers includes a compound represented by Formula 1 above.

The compound described in the present specification may be included in the organic material layer in the organic light-emitting device, and by including the compound in the organic material layer of the organic light-emitting device, it is possible to obtain an organic light-emitting device having a low driving voltage, excellent efficiency and excellent lifespan characteristics.

1 shows an example of an organic light emitting device comprising a substrate 1, an anode 2, a hole transport layer 3, an electron blocking layer 4, a light emitting layer 5, an electron transport layer 6, and a cathode 7 I did it.
2 is an example of an organic light-emitting device comprising an anode 2, a hole injection layer 8, a hole transport layer 3, a light-emitting layer 5, an electron injection and transport layer 9, and a cathode 7 on a substrate 1 Is shown.

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

The present specification provides a compound represented by Chemical Formula 1. The compound represented by Formula 1 contains two or more condensed rings in which adamantane is condensed in the compound, so that the three-dimensional size is larger than that of a compound containing no or only one condensed ring in which adamantane is condensed. It is robust and has the advantage of having high thermal stability due to excellent sublimation and chemical structural stability.

In the present specification, when a part "includes" a certain component, it means that other components may be further included rather than excluding other components unless otherwise stated.

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

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

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

In the present specification, the term "substituted or unsubstituted" refers to deuterium; Halogen group; Cyano group (-CN); Nitro group; Hydroxy group; Alkyl group; Alkenyl group; Alkynyl group; Alkoxy group; Silyl group; Aryloxy group; Cycloalkyl group; Aryl group; Amine group; And it is substituted with one or two or more substituents selected from the group consisting of a heterocyclic group, two or more of the substituents exemplified above are substituted with a connected substituent, or it means that no substituents are present.

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

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

In the present specification, the alkyl group includes a linear or branched chain, and the number of carbon atoms is not particularly limited, but is 1 to 60, 1 to 30, or 1 to 20. Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, and the like, and the alkyl group may be a straight chain or a branched chain. According to an example, propyl The group includes an n-propyl group and an isopropyl group, and the butyl group includes an n-butyl group, an isobutyl group and a ter-butyl group.

In the present specification, the number of carbon atoms of the cycloalkyl group is not particularly limited, but is 3 to 60, 3 to 30, or 3 to 20. Specifically, there are a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and the like, but are not limited thereto.

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

In the present specification, the description of the above-described alkyl group may be applied to the alkyl group of the alkoxy group.

In the present specification, the aryl group may be a monocyclic aryl group or a polycyclic aryl group, and the number of carbon atoms is not particularly limited, but 6 to 60, 6 to 30, or 6 to 20. The monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, or a quarterphenyl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, triphenyl group, chrysenyl group, fluorenyl group, fluoranthenyl group, triphenylenyl group, etc. , But is not limited thereto.

In the present specification, carbon atom 9 (C) of the fluorenyl group may be substituted with an alkyl group, an aryl group, etc., and two substituents may be bonded to each other to form a spiro structure such as cyclopentane and fluorene.

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

In the present specification, the amine group may be represented by -NRaRb, wherein Ra and Rb are each hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or it may be a substituted or unsubstituted heteroaryl group, but is not limited thereto. The amine group is selected from the group consisting of an alkylamine group, an alkylarylamine group, an arylamine group, a heteroarylamine group, an alkylheteroarylamine group, and an arylheteroarylamine group, depending on the type of the substituent (Ra, Rb) to be bonded. Can be.

In the present specification, the alkylamine group refers to an amine group substituted with an alkyl group, and the number of carbon atoms is not particularly limited, but may be 1 to 40 or 1 to 20. Specific examples of the alkylamine group include a methylamine group, a dimethylamine group, an ethylamine group, and a diethylamine group, but are not limited thereto.

In the present specification, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, and a substituted or unsubstituted diarylamine group. The aryl group in the arylamine group may be a monocyclic or polycyclic aryl group. Specific examples of the arylamine group include, but are not limited to, a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, a diphenylamine group, and a phenylnaphthylamine group.

In the present specification, examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, and a substituted or unsubstituted diheteroarylamine group.

In the present specification, the heterocyclic group is a cyclic group including one or more of N, O, S, and Si as a hetero atom, and the number of carbon atoms is not particularly limited, but is 2 to 60, or 2 to 30. Examples of the heterocyclic group include a pyridyl group; Quinoline group; Thiophene group; Dibenzothiophene group; Furan group; Dibenzofuran group; Naphthobenzofuran group; Carbazole; Benzocarbazole group; Naphthobenzothiophene group and the like, but are not limited thereto.

In the present specification, the description of the aforementioned heterocyclic group may be applied except that the heteroaryl group is aromatic.

In the present specification, the hydrocarbon ring may be an aromatic, aliphatic, or condensed ring of aromatic and aliphatic, and the description of the aryl group described above may be applied except that the aromatic hydrocarbon ring is not monovalent, and the aliphatic hydrocarbon ring is Except for those that are not monovalent, the above description of the cycloalkyl group may apply.

In this specification, "adjacent" The group may mean a substituent substituted on an atom directly connected to the atom where the corresponding substituent is substituted, a substituent positioned three-dimensionally close to the corresponding substituent, or another substituent substituted on the atom where the corresponding substituent is substituted.

In the present specification, in "the ring formed by bonding with an adjacent group, A or B", "ring" is a hydrocarbon ring; Or it means a heterocycle.

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

In the present specification, the description of the aryl group may be applied except that the aromatic hydrocarbon ring is not a monovalent group.

The description of the heterocyclic group may be applied, except that the heterocycle is not a monovalent group.

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

In the present specification, the description of the aforementioned heteroaryl group may be applied except that the heteroarylene group is a divalent group.

In the exemplary embodiment of the present specification, * is combined with any one of A, B, and R1 to R5. Specifically, in Formula 1, L is bonded to any one of an atom constituting A, an atom constituting B, and an atom constituting R1 to R5.

According to the exemplary embodiment of the present specification, m1 is 1 or 2, m3 is an integer of 0 to 2, when m1 is 1, m2 is 2 or 3, when m1 is 2, m2 is 1, and m2+ m3 is 3.

According to another exemplary embodiment, m1 is 1, m2 is 2, and m3 is 1.

In another exemplary embodiment, m1 is 1, m2 is 3, and m3 is 0.

According to another exemplary embodiment, m1 is 2, m2 is 1, and m3 is 2.

When m1 to m3 are each an integer of 2 or 2 or more, the substituents in the parentheses of 2 or 2 or more are the same or different from each other.

According to an exemplary embodiment of the present specification, A and B are the same as or different from each other, and each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms; Or a substituted or unsubstituted aromatic heterocycle having 2 to 60 carbon atoms containing at least one hetero element selected from the group consisting of O, S and N.

According to another exemplary embodiment, A and B are the same as or different from each other, and each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms; Or a substituted or unsubstituted aromatic heterocycle having 2 to 30 carbon atoms containing at least one hetero element selected from the group consisting of O, S and N.

In another exemplary embodiment, A and B are the same as or different from each other, and each independently substituted or unsubstituted benzene; Substituted or unsubstituted naphthalene; Substituted or unsubstituted dibenzofuran; Or substituted or unsubstituted dibenzothiophene.

According to another exemplary embodiment, A and B are the same as or different from each other, and each independently benzene; naphthalene; Dibenzofuran; Or dibenzothiophene.

According to an exemplary embodiment of the present specification, L, L1, and L2 are the same as or different from each other, and each independently a single bond; A substituted or unsubstituted arylene group having 6 to 60 carbon atoms; Or a substituted or unsubstituted C2 to C60 heteroarylene group.

According to another exemplary embodiment, the L, L1 and L2 are the same as or different from each other, and each independently a single bond; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2 to C30 heteroarylene group.

In another exemplary embodiment, L, L1, and L2 are the same as or different from each other, and each independently a single bond; Or an arylene group having 6 to 30 carbon atoms.

In another exemplary embodiment, L, L1, and L2 are the same as or different from each other, and each independently a single bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylylene group; A substituted or unsubstituted terphenylene group; Or a substituted or unsubstituted naphthylene group.

According to another exemplary embodiment, the L, L1 and L2 are the same as or different from each other, and each independently a single bond; Phenylene group; Biphenylylene group; Terphenylene group; Or it is a naphthylene group.

According to another exemplary embodiment, the L, L1 and L2 are the same as or different from each other, and each independently a single bond; Phenylene group; Biphenylylene group; Or it is a naphthylene group.

According to an exemplary embodiment of the present specification, Ar is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted C3 to C30 cycloalkyl group; A substituted or unsubstituted silyl group having 1 to 40 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, except for diphenylfluorene.

According to another exemplary embodiment, Ar is a substituted or unsubstituted silyl group having 1 to 40 carbon atoms; An aryl group having 6 to 30 carbon atoms unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms; Or a C 2 to C 30 heterocyclic group unsubstituted or substituted with a C 6 to C 30 aryl group.

In another exemplary embodiment, Ar is a substituted or unsubstituted arylsilyl group having 6 to 40 carbon atoms; An aryl group having 6 to 30 carbon atoms unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms; Or, it is a C2-C30 heterocyclic group substituted or unsubstituted with a C6-C30 aryl group.

According to another exemplary embodiment, Ar is a substituted or unsubstituted triphenylsilyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted phenanthrenyl group; A substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted carbazole group; Or a substituted or unsubstituted naphthobenzofuran group.

According to another exemplary embodiment, Ar is a triphenylsilyl group; Phenyl group; Biphenyl group; Naphthyl group; A fluorenyl group substituted with an alkyl group having 1 to 20 carbon atoms; Terphenyl group; Phenanthrenyl group; Dibenzofuran group; Dibenzothiophene group; A carbazole group substituted with an aryl group having 6 to 30 carbon atoms; Or a naphthobenzofuran group.

According to another exemplary embodiment, Ar is a triphenylsilyl group; Phenyl group; Biphenyl group; Naphthyl group; A fluorenyl group substituted with a methyl group; Terphenyl group; Phenanthrenyl group; Dibenzofuran group; Dibenzothiophene group; A carbazole group substituted with a phenyl group; Or a naphthobenzofuran group.

According to an exemplary embodiment of the present specification, Chemical Formula 1 is represented by any one of the following Chemical Formulas 2 to 4.

[Formula 2]

[Formula 3]

[Formula 4]

In Formulas 2 to 4,

*, A, B and X are defined as in Formula 1,

X1 is a single bond; C(R6)(R7); Si(R8)(R9); N(R10); O; S; Or SO ₂ ,

R6 to R10 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or may be combined with an adjacent group, A or B to form a substituted or unsubstituted ring,

L11 to L15 are the same as or different from each other, and each independently a single bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

Ar1 to Ar3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitrile group; Nitro group; Hydroxy group; Carbonyl group; Ester group; Imide group; Amide group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkyl thioxy group; A substituted or unsubstituted arylthioxy group; A substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, provided that diphenylfluorene is excluded,

The structures within the two [] are the same or different.

According to an exemplary embodiment of the present specification, X1 is a single bond; C(R6)(R7); Si(R8)(R9); N(R10); O; S; Or SO ₂ .

According to another exemplary embodiment, the R6 to R10 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C20 alkyl group; A substituted or unsubstituted C3 to C30 cycloalkyl group; A substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2 to C30 heterocyclic group.

According to an exemplary embodiment of the present specification, the L11 to L15 are the same as or different from each other, and the contents of L, L1 and L2 described above are applied independently.

According to an exemplary embodiment of the present specification, Ar1 to Ar3 are the same as or different from each other, and each independently the above-described contents of Ar are applied.

According to an exemplary embodiment of the present specification, X is a single bond; C(R1)(R2); Si(R3)(R4); N(R5); O; S; Or SO ₂ .

According to another exemplary embodiment, the R1 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C20 alkyl group; A substituted or unsubstituted C3 to C30 cycloalkyl group; A substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, and may be bonded to an adjacent group, A or B to form a substituted or unsubstituted 3 to 30 ring.

가 하기

구조를 형성한다.According to another exemplary embodiment, the R1 to R5 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group, or by bonding with an adjacent group, A or B

To go

Form a structure

가 하기

구조를 형성한다.According to another exemplary embodiment, the R1 to R5 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group, or combined with A or B

To go

Form a structure

가 하기

구조를 형성한다.According to another exemplary embodiment, the R1 to R5 are the same as or different from each other, and each independently a phenyl group, or combined with A or B

To go

Form a structure

According to another exemplary embodiment, R1 to R5 are phenyl groups.

According to another exemplary embodiment, R5 is a substituted or unsubstituted phenyl group, and may be combined with A or B to form a substituted or unsubstituted ring.

In another exemplary embodiment, R5 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and may be combined with A or B to form a substituted or unsubstituted ring.

가 하기

구조를 형성한다.According to another exemplary embodiment, R5 is a substituted or unsubstituted phenyl group, or by combining with A or B

To go

Form a structure

가 하기

구조를 형성한다.According to another exemplary embodiment, R5 is a phenyl group, or by combining with A or B

To go

Form a structure

In another exemplary embodiment, R1 and R2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and may be bonded to each other to form a substituted or unsubstituted ring. have.

According to another exemplary embodiment, R1 and R2 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group, and may be bonded to each other through a single bond to form a fluorene ring.

According to another exemplary embodiment, R1 and R2 may be the same as or different from each other, each independently a phenyl group, and may be bonded to each other through a single bond to form a fluorene ring.

According to another exemplary embodiment, R1 and R2 may be a phenyl group, or may be bonded to each other through a single bond to form a fluorene ring.

'는 하기 구조들 중 어느 하나로 표시된다.According to an exemplary embodiment of the present specification, in Chemical Formula 1, '

'Is represented by any of the following structures.

In the above structures,

W1 is O or S,

W2 is Si or C,

Y is O, S or NR,

R is a substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

The structures are alkyl groups; Aryl group; Or it may be further substituted with a heterocyclic group.

According to an exemplary embodiment of the present specification, the structures are an alkyl group having 1 to 20 carbon atoms; Aryl group having 6 to 30 carbon atoms; Or it may be further substituted with a heterocyclic group having 2 to 30 carbon atoms.

'는 하기 구조들 중 어느 하나로 표시된다.According to an exemplary embodiment of the present specification, in Chemical Formula 1, '

'Is represented by any of the following structures.

In the above structures, the definition of R5 is as described above,

The structures are substituted with one or two or more substituents selected from the group consisting of an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, and a heterocyclic group having 2 to 30 carbon atoms, or a substituent connected with two or more substituents among the exemplified substituents It may be substituted with or may not have any substituent.

According to an exemplary embodiment of the present specification, Formula 1 is represented by any one of the following Formulas 1-1 to 1-7.

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

[Formula 1-6]

[Formula 1-7]

In Formulas 1-1 to 1-7,

Y is O, S or NR,

R is a substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

L12, L13, L15, and L101 to L110 are the same as or different from each other, and each independently a single bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

Ar1 to Ar3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitrile group; Nitro group; Hydroxy group; Carbonyl group; Ester group; Imide group; Amide group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkyl thioxy group; A substituted or unsubstituted arylthioxy group; A substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, provided that diphenylfluorene is excluded,

The structures within 2 or 3 [] are the same or different from each other,

The structures are alkyl groups; Aryl group; Or it may be further substituted with a heterocyclic group.

According to an exemplary embodiment of the present specification, in Formulas 1-1 to 1-7, the L12, L13, L15, and L101 to L101 are the same as or different from each other, and each independently relates to the aforementioned L, L1 and L2. The content applies.

According to an exemplary embodiment of the present specification, in Formulas 1-1 to 1-7, Ar1 to Ar3 are the same as or different from each other, and each independently the above-described contents of Ar are applied.

According to an exemplary embodiment of the present specification, structures of Formulas 1-1 to 1-7 may include an alkyl group having 1 to 20 carbon atoms; Aryl group having 6 to 30 carbon atoms; Or it may be further substituted with a heterocyclic group having 2 to 30 carbon atoms.

In the exemplary embodiment of the present specification, Y is O, S, or NR, and R is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2 to C30 heterocyclic group.

According to another exemplary embodiment, R is an aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, the compound represented by Formula 1 is represented by any one of the following compounds.

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

The organic light-emitting device according to the present specification includes an anode; cathode; And at least one organic material layer provided between the anode and the cathode, and at least one of the organic material layers includes the above-described compound.

The organic light-emitting device of the present specification may be manufactured by a conventional method and material for manufacturing an organic light-emitting device, except for forming one or more organic material layers using the compound represented by Formula 1 described above.

The organic material layer including the compound represented by Formula 1 may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spray method, roll coating, and the like, but is not limited thereto.

The organic material layer of the organic light emitting device of the present specification may have a single-layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. For example, the organic light-emitting device of the present specification is an organic material layer, which includes a hole injection layer, a hole transport layer, a layer for simultaneously transporting and injecting holes, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, and electron transport and electron injection. It may have a structure including a layer at the same time. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number or a larger number of organic material layers.

In the organic light emitting device of the present specification, the organic material layer includes an emission layer, and includes one or more organic material layers including the compound represented by Formula 1 between the anode and the emission layer. At this time, the one or more organic material layers containing the compound represented by Formula 1 are selected from the group consisting of a hole transport layer, a hole injection layer, a layer for simultaneously transporting and injecting holes, and an electron blocking layer.

In the organic light emitting device of the present specification, at least one organic material layer including the compound represented by Formula 1 is 1 selected from the group consisting of a hole transport layer, a hole injection layer, a layer for simultaneously transporting and injecting holes, and an electron blocking layer. More than a layer

In the organic light emitting device of the present specification, the compound represented by Formula 1 is included in the hole transport layer.

In the organic light emitting device of the present specification, the organic material layer includes an emission layer, and includes one or more organic material layers including the compound represented by Formula 1 between the cathode and the emission layer. At this time, the one or more organic material layers containing the compound represented by Formula 1 are selected from the group consisting of an electron transport layer, an electron injection layer, a layer that simultaneously transports electrons and injects electrons, and a hole blocking layer.

In the organic light emitting device of the present specification, at least one organic material layer including the compound represented by Formula 1 is an emission layer.

According to another exemplary embodiment, the organic material layer includes an emission layer, and the emission layer includes the compound represented by Formula 1 as a dopant of the emission layer.

In another exemplary embodiment, the organic material layer includes an emission layer, and the emission layer includes a compound represented by Formula 1 as a dopant of the emission layer, includes a fluorescent host or a phosphorescent host, and other organic compounds, metals, or metals The compound may be included as a dopant.

As another example, the organic material layer includes an emission layer, the emission layer includes a compound represented by Formula 1 as a dopant of the emission layer, includes a fluorescent host or a phosphorescent host, and is used with an iridium-based (Ir) dopant. I can.

According to another exemplary embodiment, the organic material layer may include an emission layer, and the emission layer may include the compound represented by Formula 1 as a host of the emission layer.

As another example, the organic material layer includes an emission layer, and the emission layer includes a compound represented by Formula 1 as a host of the emission layer, and may further include a dopant.

The emission layer may include a host and a dopant, and the content of the dopant may be included in an amount of 1 to 20 parts by weight, and more preferably 1 to 5 parts by weight, based on 100 parts by weight of the host.

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

(1) Anode/Hole Transport Layer/Light-Emitting Layer/Anode

(2) Anode/Hole Injection Layer/Hole Transport Layer/Light-Emitting Layer/Anode

(3) Anode/Hole Transport Layer/Light-Emitting Layer/Electron Transport Layer/Anode

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

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

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

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

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

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

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

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

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

(13) Anode/Hole injection layer/Hole transport layer/Light emitting layer/Hole blocking layer/Electron transport layer/Anode

(14) 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 the present specification may have a structure as shown in FIGS. 1 and 2, but is not limited thereto.

FIG. 1 shows an organic light emitting diode in which an anode 2, a hole transport layer 3, an electron blocking layer 4, a light emitting layer 5, an electron transport layer 6, and a cathode 7 are sequentially stacked on a substrate 1. The structure is illustrated. In such a structure, the compound represented by Formula 1 may be included in the hole transport layer 3 and/or the electron blocking layer 4.

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

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, and uses a metal or a conductive metal oxide or an alloy thereof on a substrate. Deposited to form an anode, formed by forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron blocking layer, an electron transport layer and an electron injection layer thereon, and then depositing a material that can be used as a cathode thereon. Can be. In addition to this method, an organic electronic device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

The organic material layer includes a hole injection layer, a hole transport layer, a layer that simultaneously injects and transports electrons, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, a layer that simultaneously injects and transports electrons, and a hole blocking layer. Although it may have a multilayer structure, it is not limited thereto and may have a single layer structure. In addition, the organic material layer is made of a variety of polymer materials, and is used in a smaller number of solvent processes, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer. It can be made in layers.

The anode is an electrode for injecting holes, and a material having a large work function is preferable so that holes can be smoothly injected into the organic material layer as the anode material. Specific examples of the cathode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO _2: a combination of a metal and an oxide such as Sb; Poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), conductive polymers such as polypyrrole and polyaniline, and the like, but are not limited thereto.

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

The hole injection layer is a layer that facilitates injection of holes from the anode to the light emitting layer, and the hole injection material is a material capable of injecting holes well from the anode at a low voltage, and the HOMO (highest occupied material) of the hole injection material It is preferable that molecular orbital) is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of hole injection materials include metal porphyrine, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based organic substances. Organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers, etc., but are not limited thereto.

The hole transport layer may serve to facilitate transport of holes. When the organic light-emitting device according to an exemplary embodiment of the present specification includes an additional hole transport layer other than the hole transport layer containing the compound represented by Formula 1, the hole transport material is transported from the anode or the hole injection layer. As a material that can be transferred to the light emitting layer, a material having high mobility for holes is suitable. Specific examples include an arylamine-based organic material, a conductive polymer, and a block copolymer including a conjugated portion and a non-conjugated portion, but are not limited thereto.

The hole transport layer material and/or hole injection layer material known in the art may be used as the layer for simultaneously transporting and injecting holes.

The electron transport layer material and/or the electron injection layer material known in the art may be used as the layer for simultaneous electron transport and electron injection.

An electron blocking layer may be provided between the hole transport layer and the emission layer. Materials known in the art may be used for the electron blocking layer.

The emission layer may emit red, green, or blue light, and may be made of a phosphorescent material or a fluorescent material. As the light-emitting material, a material capable of emitting light in a visible region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency against fluorescence or phosphorescence is preferable. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compound; Benzoxazole, benzthiazole, and benzimidazole-based compounds; Poly(p-phenylenevinylene) (PPV)-based polymer; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.

Examples of the host material for the light emitting layer include condensed aromatic ring derivatives or heterocyclic 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, ladder type Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

When the emission layer emits red light, the emission dopants include PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline)iridium). ), a phosphorescent material such as octaethylporphyrin platinum (PtOEP), or a fluorescent material such as Alq ₃ (tris(8-hydroxyquinolino)aluminum), but is not limited thereto. When the emission layer emits green light, a phosphor such as Ir(ppy) ₃ (fac tris(2-phenylpyridine)iridium) or a fluorescent material such as Alq ₃ (tris(8-hydroxyquinolino)aluminum) may be used as the emission dopant. However, it is not limited thereto. When the light emitting layer emits blue light, the light emitting dopant is a phosphorescent material such as (4,6-F ₂ ppy) ₂ Irpic, but spiro-DPVBi, spiro-6P, distillbenzene (DSB), distrylarylene (DSA ), a fluorescent material such as a PFO-based polymer or a PPV-based polymer may be used, but is not limited thereto.

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

The electron transport layer serves to facilitate the transport of electrons. As the electron transport material, a material capable of receiving electrons from the cathode and transferring them to the light emitting layer is suitable, and a material having high mobility for electrons is suitable. Specific examples include Al complex of 8-hydroxyquinoline; Complexes containing Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto.

The electron injection layer serves to facilitate injection of electrons. As the electron injection material, a compound having an ability to transport electrons, an electron injection effect from the cathode, an excellent electron injection effect to a light emitting layer or a light emitting material, and excellent in thin film formation ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, preorenylidene methane, anthrone, etc. Complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.

Examples of the metal complex compound include lithium 8-hydroxyquinolinato, 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-naphtholato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, etc. It is not limited to this.

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

The organic light-emitting device of the present invention may be manufactured by a conventional method and material of an organic light-emitting device, except that one or more organic material layers are formed by using the above-described compound.

The manufacturing method of the compound of Formula 1 and the manufacturing of an organic light emitting device using the same will be described in detail in the following examples. However, the following examples are for illustrating the present invention, and the scope of the present invention is not limited thereto.

Preparation Example 1: Preparation of Compound 1

In a nitrogen atmosphere, sub1 (10 g, 28.3 mmol), formula A (17.3 g, 31.2 mmol), sodium tert-butoxide (5.4 g, 56.7 mmol) was added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 3 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 1 and 13.1 g. (Yield 53%, MS: [M+H] ⁺ = 870)

Preparation Example 2: Preparation of Compound 2

In a nitrogen atmosphere, sub2 (10 g, 24.4 mmol), formula B (18 g, 26.8 mmol), sodium tert-butoxide (4.7 g, 48.8 mmol) were added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After 2 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 2 and 14.2 g. (Yield 56%, MS: [M+H] ⁺ = 1043)

Preparation Example 3: Preparation of compound 3

In a nitrogen atmosphere, sub3 (10 g, 23.8 mmol), formula C (19.2 g, 26.1 mmol), sodium tert-butoxide (4.6 g, 47.5 mmol) was added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After 2 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 3 and 15.7 g. (Yield 59%, MS: [M+H] ⁺ = 1121)

Preparation Example 4: Preparation of compound 4

In a nitrogen atmosphere, sub4 (10 g, 24.3 mmol), formula D (10.1 g, 26.8 mmol), sodium tert-butoxide (4.7 g, 48.7 mmol) was added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added. After 3 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain Compound 4 and 9.1 g. (Yield 50%, MS: [M+H] ⁺ = 752)

Preparation Example 5: Preparation of compound 5

In a nitrogen atmosphere, sub5 (10 g, 21 mmol), formula E (14.8 g, 23.1 mmol), sodium tert-butoxide (4 g, 41.9 mmol) was added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 5 and 13.6 g. (Yield 60%, MS: [M+H] ⁺ = 1084)

Preparation Example 6: Preparation of compound 6

In a nitrogen atmosphere, sub6 (10 g, 21.7 mmol), formula F (13 g, 23.9 mmol), sodium tert-butoxide (4.2 g, 43.4 mmol) was added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 3 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 6 and 13.6 g. (Yield 65%, MS: [M+H] ⁺ = 968)

Preparation Example 7: Preparation of compound 7

In a nitrogen atmosphere, sub7 (10 g, 21 mmol), formula G (15.1 g, 23.1 mmol), sodium tert-butoxide (4 g, 41.9 mmol) was added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 7, 15.8 g. (Yield 69%, MS: [M+H] ⁺ = 1094)

Preparation Example 8: Preparation of compound 8

In a nitrogen atmosphere, sub8 (10 g, 21 mmol), formula H (15.2 g, 23.1 mmol), sodium tert-butoxide (4 g, 41.9 mmol) was added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 8 and 13.8 g. (Yield 60%, MS: [M+H] ⁺ = 1100)

Preparation Example 9: Preparation of compound 9

In a nitrogen atmosphere, sub9 (10 g, 21 mmol), formula I (15.8 g, 23.1 mmol), sodium tert-butoxide (4 g, 41.9 mmol) was added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 3 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 9 (14.6 g). (Yield 62%, MS: [M+H] ⁺ = 1126)

Preparation Example 10: Preparation of Compound 10

In a nitrogen atmosphere, sub10 (10 g, 21 mmol), formula J (13.9 g, 23.1 mmol), sodium tert-butoxide (4 g, 41.9 mmol) was added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 10 and 13.6 g. (Yield 62%, MS: [M+H] ⁺ = 1044)

Preparation Example 11: Preparation of compound 11

In a nitrogen atmosphere, sub11 (10 g, 21.7 mmol), formula K (15.4 g, 23.9 mmol), sodium tert-butoxide (4.2 g, 43.4 mmol) was added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 11 and 13.4 g. (Yield 58%, MS: [M+H] ⁺ = 1068)

Preparation Example 12: Preparation of compound 12

In a nitrogen atmosphere, sub12 (10 g, 21 mmol), formula L (12.2 g, 23.1 mmol), sodium tert-butoxide (4 g, 41.9 mmol) was added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 3 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compounds 12 and 14 g. (Yield 69%, MS: [M+H] ⁺ = 968)

Preparation Example 13: Preparation of compound 13

In a nitrogen atmosphere, sub13 (10 g, 21 mmol), formula M (14.4 g, 23.1 mmol), sodium tert-butoxide (4 g, 41.9 mmol) was added to 200 ml of Xylene, and stirred and refluxed. After this, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 13 and 15.6 g. (Yield 70%, MS: [M+H] ⁺ = 1064)

<Experimental Example 1>

A glass substrate coated with a thin film of ITO (indium tin oxide) to a thickness of 1,000Å was put in distilled water dissolved in a detergent and washed with ultrasonic waves. In this case, Fischer Co. product was used as a detergent, and distilled water secondarily filtered with a filter made by Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, it was repeated twice with distilled water to perform ultrasonic cleaning for 10 minutes. After washing with distilled water, ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

On the thus prepared ITO transparent electrode, the following compound [HI-A] was thermally vacuum deposited to a thickness of 600Å to form a hole injection layer. Compound 1 prepared in Preparation Example 1 was vacuum deposited on the hole injection layer to form a hole transport layer.

Subsequently, the following compounds [BH] and [BD] were vacuum deposited on the hole transport layer at a weight ratio of 25:1 to a film thickness of 200Å to form a light emitting layer.

On the emission layer, [ET] and the following compound [LiQ] (Lithiumquinolate) were vacuum-deposited in a 1:1 weight ratio to form an electron injection and transport layer with a thickness of 150Å. Lithium fluoride (LiF) at a thickness of 10Å and aluminum at a thickness of 1,000Å were sequentially deposited on the electron injection and transport layer to form a negative electrode.

In the above process, the deposition rate of organic matter was maintained at 0.4 to 0.9 Å/sec, lithium fluoride at the cathode was maintained at a deposition rate of 0.3 Å/sec, and for aluminum 2 Å/sec, the vacuum degree during deposition was 1 × 10. Maintaining ^-7 to 5 × 10 ^-8 torr, an organic light emitting device was manufactured.

<Experimental Examples 2 to 13>

An organic light-emitting device was manufactured in the same manner as in Experimental Example 1, except that the compound shown in Table 1 was used instead of Compound 1 in Experimental Example 1.

<Comparative Examples 1 to 6>

An organic light-emitting device was manufactured in the same manner as in Experimental Example 1, except that the compound shown in Table 1 was used instead of Compound 1 in Experimental Example 1.

HT-01 to HT-06 in Table 1 are as follows.

In Experimental Examples 1 to 13 and Comparative Examples 1 to 6, the driving voltage and luminous efficiency were measured at a current density of 10 mA/cm ² for the organic light emitting device manufactured using each compound as the hole transport layer, and 20 mA/cm ² The time (LT98) to be 98% of the initial luminance at the current density of was measured.

The results are shown in Table 1 below.

division Hole transport layer Voltage
(V) Current efficiency
(cd/A) Life Time(hr) 98% at 20mA/cm ² Experimental Example 1 Compound 1 3.71 5.64 70 Experimental Example 2 Compound 2 3.89 5.68 72 Experimental Example 3 Compound 3 3.82 5.76 81 Experimental Example 4 Compound 4 3.66 5.71 89 Experimental Example 5 Compound 5 3.59 5.81 76 Experimental Example 6 Compound 6 3.72 5.69 69 Experimental Example 7 Compound 7 3.81 5.61 91 Experimental Example 8 Compound 8 3.72 5.78 86 Experimental Example 9 Compound 9 3.75 5.81 79 Experimental Example 10 Compound 10 3.92 5.92 75 Experimental Example 11 Compound 11 3.64 5.88 81 Experimental Example 12 Compound 12 3.59 5.63 90 Experimental Example 13 Compound 13 3.69 5.93 77 Comparative Example 1 HT-01 4.70 4.40 28 Comparative Example 2 HT-02 4.77 4.42 32 Comparative Example 3 HT-03 4.85 4.45 30 Comparative Example 4 HT-04 4.87 4.40 32 Comparative Example 5 HT-05 4.93 4.47 29 Comparative Example 6 HT-06 4.89 4.42 23

According to Table 1, Experimental Examples 1 to 13, which are organic light emitting devices including Formula 1 in the hole transport layer according to an exemplary embodiment of the present specification, have lower driving voltages than the organic light emitting devices of Comparative Examples 1 to 6, and have efficiency and It was found that the life effect was excellent. Although preferred embodiments of the present invention have been described above, the present invention is not limited thereto, and various modifications can be made within the scope of the claims and detailed description of the invention, and this also belongs to the scope of the invention. .

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

Claims (14)

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

In Formula 1,
A and B are the same as or different from each other, and each independently a substituted or unsubstituted aromatic hydrocarbon ring; Or a substituted or unsubstituted aromatic heterocycle,
X is a single bond; C(R1)(R2); Si(R3)(R4); N(R5); O; S; Or SO ₂ ,
R1 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitrile group; Nitro group; Hydroxy group; Carbonyl group; Ester group; Imide group; Amide group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkyl thioxy group; A substituted or unsubstituted arylthioxy group; A substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, and may be combined with an adjacent group, A or B to form a substituted or unsubstituted ring,
L, L1 and L2 are the same as or different from each other, and each independently a single bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
Ar is hydrogen; heavy hydrogen; Nitrile group; Nitro group; Hydroxy group; Carbonyl group; Ester group; Imide group; Amide group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkyl thioxy group; A substituted or unsubstituted arylthioxy group; A substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, provided that diphenylfluorene is excluded,
m1 is 1 or 2, m3 is an integer from 0 to 2,
When m1 is 1, m2 is 2 or 3, when m1 is 2, m2 is 1, and m2+m3 is 3,
When m1 to m3 are each 2 or more, the substituents in parentheses are the same or different from each other,
* Combines with any one of A, B and R1 to R5. The method according to claim 1,
A and B are the same as or different from each other, and each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms; Or a substituted or unsubstituted C 2 to C 60 aromatic heterocyclic compound containing at least one hetero element selected from the group consisting of O, S and N. The method according to claim 1,
Formula 1 is a compound represented by any one of the following Formulas 2 to 4:
[Formula 2]

[Formula 3]

[Formula 4]

In Formulas 2 to 4,
*, A, B and X are defined as in Formula 1,
X1 is a single bond; C(R6)(R7); Si(R8)(R9); N(R10); O; S; Or SO ₂ ,
R6 to R10 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or may be combined with an adjacent group, A or B to form a substituted or unsubstituted ring,
L11 to L15 are the same as or different from each other, and each independently a single bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
Ar1 to Ar3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitrile group; Nitro group; Hydroxy group; Carbonyl group; Ester group; Imide group; Amide group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkyl thioxy group; A substituted or unsubstituted arylthioxy group; A substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, provided that diphenylfluorene is excluded,
The structures within the two [] are the same or different. The method according to claim 1,
Wherein A and B are substituted or unsubstituted benzene; Substituted or unsubstituted naphthalene; Substituted or unsubstituted dibenzofuran; Or a substituted or unsubstituted dibenzothiophene compound. The method according to claim 1,
remind '

'Is a compound represented by any one of the following structures:

In the above structures,
W1 is O or S,
W2 is Si or C,
Y is O, S or NR,
R is a substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
The structures are alkyl groups; Aryl group; Or it may be further substituted with a heterocyclic group. The method according to claim 1,
Formula 1 is a compound represented by any one of the following Formulas 1-1 to 1-7:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

[Formula 1-6]

[Formula 1-7]

In Formulas 1-1 to 1-7,
Y is O, S or NR,
R is a substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
L12, L13, L15, and L101 to L110 are the same as or different from each other, and each independently a single bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
Ar1 to Ar3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitrile group; Nitro group; Hydroxy group; Carbonyl group; Ester group; Imide group; Amide group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkyl thioxy group; A substituted or unsubstituted arylthioxy group; A substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, provided that diphenylfluorene is excluded,
The structures within 2 or 3 [] are the same or different from each other,
The structures are alkyl groups; Aryl group; Or it may be further substituted with a heterocyclic group. The method according to claim 1,
Formula 1 is a compound of any one of the following compounds:

. anode; cathode; And at least one organic material layer provided between the anode and the cathode, and at least one of the organic material layers comprises the compound according to any one of claims 1 to 7. The method of claim 8,
The organic material layer includes an emission layer, and an organic light-emitting device comprising at least one organic material layer including the compound between the anode and the emission layer. The method of claim 9,
At least one organic material layer containing the compound is an organic light emitting device selected from the group consisting of a hole transport layer, a hole injection layer, a layer for simultaneously transporting and injecting holes, and an electron blocking layer. The method of claim 8,
The organic material layer includes an emission layer, and an organic light-emitting device comprising at least one organic material layer including the compound between the cathode and the emission layer. The method of claim 11,
At least one organic material layer comprising the compound is an organic light emitting device selected from the group consisting of an electron transport layer, an electron injection layer, a layer that simultaneously transports electrons and injects electrons, and a hole blocking layer. The method of claim 8,
One or more organic material layers including the compound are an emission layer. The method of claim 8,
The organic material layer is one of a hole transport layer, a hole injection layer, an electron blocking layer, a layer that simultaneously transports and injects holes, a light emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, and a layer that simultaneously transports and injects electrons. An organic light-emitting device comprising the above.

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