WO2017073931A1

WO2017073931A1 - Spiro-type compound and organic light emitting element comprising same

Info

Publication number: WO2017073931A1
Application number: PCT/KR2016/011418
Authority: WO
Inventors: 차용범; 김진주; 서상덕; 김정범
Original assignee: 주식회사 엘지화학
Priority date: 2015-10-28
Filing date: 2016-10-12
Publication date: 2017-05-04

Abstract

The present specification provides a spiro-type compound and an organic light emitting element comprising the same.

Description

Spiro compound and organic light emitting device comprising the same

This application claims the benefit of the date of application of Korean Patent Application No. 10-2015-0150335 filed with the Korean Patent Office on October 28, 2015 and Korean Patent Application No. 10-2016-0130746 filed with the Korea Patent Office on October 10, 2016. Claim, all of which are hereby incorporated by reference.

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

In general, organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween. In this case, the organic material layer is often formed of a multi-layered structure composed of different materials to increase the efficiency and stability of the organic light emitting device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer. When the voltage is applied between the two electrodes in the structure of the organic light emitting device, holes are injected into the organic material layer at the anode and electrons are injected into the organic material layer, and excitons are formed when the injected holes and the electrons meet each other. When it falls back to the ground, it glows.

There is a continuing need for the development of new materials for such organic light emitting devices.

In this specification, a spiro 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:

[Formula 1]

In Chemical Formula 1,

L is a direct bond, a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

HAr is a substituted or unsubstituted heterocyclic group; Or a substituted or unsubstituted phosphine oxide group,

R1 to R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Substituted or unsubstituted amine group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted alkyl group; A 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 aryl sulfoxy group; Substituted or unsubstituted alkenyl group; A substituted or unsubstituted aralkyl group; Substituted or unsubstituted aralkenyl group; Substituted or unsubstituted alkylaryl group; Substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted heteroarylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted arylheteroarylamine group; Substituted or unsubstituted aryl phosphine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or may be combined with an adjacent group to form a substituted or unsubstituted ring,

a is an integer of 0 to 7, b is an integer of 0 to 7, c is an integer of 0 to 5, d is an integer of 0 to 4, n is an integer of 0 to 10, a, b, c, When d and n are each 2 or more, the structures in parentheses are the same or different from each other.

In addition, an exemplary embodiment of the present specification includes a first electrode; A second electrode provided to face the first electrode; And an organic light emitting device including at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound of Formula 1.

The compound described herein can be used as the material of the organic material layer of the organic light emitting device. The compound according to at least one exemplary embodiment may improve efficiency, low driving voltage, and / or lifetime characteristics in the organic light emitting diode. In particular, the compounds described herein can be used as hole injection, hole transport, hole injection and hole transport, luminescence, electron transport, or electron injection materials. In addition, the compounds described herein can be preferably used as the light emitting layer, electron transport or electron injection material. Further, more preferably, the compound described herein exhibits low voltage, high efficiency and / or long life when used as a material for hole injection, hole transport, and electron suppression layer.

FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4. As shown in FIG.

2 shows an example of an organic light emitting element consisting of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 3, an electron transport layer 7 and a cathode 4. It is.

1: substrate

2: anode

3: light emitting layer

4: cathode

5: hole injection layer

6: hole transport layer

7: electron transport layer

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

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

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

As used herein, the term "substituted or unsubstituted" is deuterium; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amine groups; Phosphine oxide groups; An alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy groups; Aryl sulfoxy group; A silyl group unsubstituted or substituted with an alkyl group; Boron group; Alkyl groups; Cycloalkyl group; Alkenyl groups; Aryl group; Aralkyl group; Ar alkenyl group; Alkylaryl group; Alkylamine group; Aralkyl amine groups; Heteroarylamine group; Arylamine group; Aryl phosphine group; And it is substituted or unsubstituted with one or more substituents selected from the group consisting of a heterocyclic group, or substituted or unsubstituted two or more substituents of the substituents exemplified above. For example, "a substituent to which two or more substituents are linked" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are linked.

In one embodiment of the present specification, the expression "substituted or unsubstituted" is preferably deuterium; Halogen group; Nitrile group; Alkyl groups; Trimethylsilyl group; Aryl group; And it may mean substituted or unsubstituted with one or more substituents selected from the group consisting of a heterocyclic group.

In the present specification, the term “adjacent” means a substituent substituted on an atom directly connected to the atom to which the corresponding substituent is substituted, a substituent positioned closest to the substituent, or another substituent substituted on the atom to which the substituent is substituted. Can be. For example, two substituents substituted at the ortho position in the benzene ring and two substituents substituted at the same carbon in the aliphatic ring may be interpreted as “adjacent” groups.

In this specification, although carbon number of a carbonyl group is not specifically limited, It is preferable that it is C1-C40. Specifically, it may be a compound having a structure as follows, but is not limited thereto.

In the present specification, the oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

In this specification, although carbon number of an imide group is not specifically limited, It is preferable that it is C1-C25. Specifically, it may be a compound having a structure as follows, but is not limited thereto.

In the present specification, the silyl group may be represented by the formula of -SiRR'R '', wherein R, R 'and R' 'are each hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group. Specific examples of the silyl group include trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, and phenylsilyl group. It doesn't happen.

In the present specification, the boron group may be represented by the formula of -BRR ', wherein R and R' are each hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group. The boron group is specifically trimethyl boron group, triethyl boron group, t-butyl dimethyl boron group, triphenyl boron group, phenyl boron group and the like, but is not limited thereto.

In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethylbutyl, pentyl, n- Pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2- Dimethylheptyl, 1-ethylpropyl, 1,1-dimethylpropyl, isohexyl, 4-methylhexyl, 5-methylhexyl, and the like, but is not limited thereto.

In the present specification, the alkenyl group may be linear or branched, and the carbon number is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary 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, and the like, but are not limited thereto.

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 exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3, 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but is not limited thereto.

In the present specification, the alkoxy group is not particularly limited, but is preferably 1 to 40 carbon atoms. According to an exemplary embodiment, the alkoxy group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkoxy group has 1 to 6 carbon atoms. Specific examples of the alkoxy group include methoxy group, ethoxy group, propoxy group, isobutyloxy group, sec-butyloxy group, pentyloxy group, iso-amyloxy group and hexyloxy group, but are not limited thereto. .

In the present specification, the amine group is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, 9-methylanthracenylamine group, Diphenylamine group, phenylnaphthylamine group, ditolylamine group, phenyltolylamine group, triphenylamine group and the like, but is not limited thereto.

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

Specific examples of the aryl amine group include phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, 3-methylphenylamine group, 4-methylnaphthylamine group, 2-methylbiphenylamine group, 9- Methyl anthracenylamine group, diphenylamine group, phenylnaphthylamine group, ditolylamine group, phenyltolylamine group, carbazole and triphenylamine group, etc., but are not limited thereto.

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

In the present specification, the arylheteroarylamine group means an amine group substituted with an aryl group and a heterocyclic group.

In the present specification, examples of the arylphosphine group include a substituted or unsubstituted monoarylphosphine group, a substituted or unsubstituted diarylphosphine group, or a substituted or unsubstituted triarylphosphine group. The aryl group in the arylphosphine group may be a monocyclic aryl group, may be a polycyclic aryl group. The arylphosphine group containing two or more aryl groups may simultaneously include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group.

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 an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms. The monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto. The polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, peryleneyl group, chrysenyl group, fluorenyl group, triphenylene group, etc., but is not limited thereto.

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

When the fluorenyl group is substituted,

,

,

,

,

,

And

And so on. However, the present invention is not limited thereto.

In the present specification, the heterocyclic group is a heterocyclic group containing one or more of N, O, S, Si, and Se as hetero atoms, and the carbon number is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of the heterocyclic group include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, triazole group, Acridyl group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group , Indole group, carbazole group, benzoxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, Benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group, thiazolyl group, isoxazolyl group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl group, phenoxazinyl group , Phenothiazinyl, dibenzofuranyl, 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 aryl group in the aryloxy group, arylthioxy group, aryl sulfoxy group, aryl phosphine group, aralkyl group, aralkylamine group, aralkenyl group, alkylaryl group, arylamine group, arylheteroarylamine group is described above. The description of one aryl group may apply.

In the present specification, the alkyl group among the alkyl thioxy group, the alkyl sulfoxy group, the aralkyl group, the aralkyl amine group, the alkyl aryl group, and the alkyl amine group may be described with respect to the alkyl group described above.

In the present specification, a heteroaryl group, a heteroarylamine group, and an arylheteroarylamine group among the heteroaryl groups may be applied to the description of the aforementioned heteroaryl group.

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

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 about the heteroaryl group described above may be applied except that the heteroarylene group is a divalent group.

In the present specification, the meaning of combining with adjacent groups to form a ring means combining with adjacent groups with each other for a substituted or unsubstituted aliphatic hydrocarbon ring; Substituted or unsubstituted aromatic hydrocarbon ring; Substituted or unsubstituted aliphatic heterocycle; Substituted or unsubstituted aromatic heterocycle; Or to form a condensed ring thereof.

In the present specification, the aliphatic hydrocarbon ring means a ring composed only of carbon and hydrogen atoms as a ring which is not aromatic.

In the present specification, examples of the aromatic hydrocarbon ring include, but are not limited to, benzene, naphthalene, anthracene, and the like.

In the present specification, the aliphatic heterocycle means an aliphatic ring containing one or more of the heteroatoms.

In the present specification, the aromatic heterocycle means an aromatic ring including at least one of heteroatoms.

In the present specification, the aliphatic hydrocarbon ring, aromatic hydrocarbon ring, aliphatic hetero ring and aromatic hetero ring may be monocyclic or polycyclic.

According to an exemplary embodiment of the present specification, Chemical Formula 1 may be represented by one of the following Chemical Formulas 2 to 5.

[Formula 2]

[Formula 3]

[Formula 4]

[Formula 5]

In Formulas 2 to 5, the definition of the substituent is the same as in Formula 1.

According to an exemplary embodiment of the present application, in the general formula 1 to 5, HAr is a substituted or unsubstituted pyridyl group; Substituted or unsubstituted pyrimidyl group; Substituted or unsubstituted triazinyl group; Substituted or unsubstituted furan group; Substituted or unsubstituted thiophene group; Substituted or unsubstituted oxadiazole group; Substituted or unsubstituted thiadiazole group; Substituted or unsubstituted phenanthrosine group; Substituted or unsubstituted quinolinyl group; Substituted or unsubstituted isoquinolinyl group; Substituted or unsubstituted quinazoline group; Substituted or unsubstituted benzoxazole group; Substituted or unsubstituted benzothiazole group; Substituted or unsubstituted benzimidazole group; Substituted or unsubstituted phenoxazine group; Substituted or unsubstituted phenothiazine group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted dibenzothiophene group; Substituted or unsubstituted carbazole group; Or a substituted or unsubstituted diaryl phosphine oxide group.

According to an exemplary embodiment of the present application, in the general formula 1 to 5, HAr is a substituted or unsubstituted aryl group; Substituted or unsubstituted heterocyclic group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted heteroarylamine group; Or a substituted or unsubstituted arylheteroarylamine group.

According to an exemplary embodiment of the present application, in Formulas 1 to 5, HAr may be substituted or unsubstituted with a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group.

According to an exemplary embodiment of the present application, in Chemical Formulas 1 to 5, HAr may be substituted or unsubstituted with a substituted or unsubstituted aryl group.

According to an exemplary embodiment of the present application, in Chemical Formulas 1 to 5, HAr may be substituted or unsubstituted with an aryl group.

According to an exemplary embodiment of the present application, in Formulas 1 to 5, HAr may be substituted or unsubstituted with a phenyl group, or a biphenylyl group.

According to an exemplary embodiment of the present application, in the formula 1 to 5,-(L) n-HAr may be represented by the following structural formula.

In the above structural formulas,

Ar1 to Ar3 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Substituted or unsubstituted heterocyclic group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted heteroarylamine group; Or a substituted or unsubstituted arylheteroarylamine group,

L 1 is a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

The structural formulas are deuterium; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Substituted or unsubstituted amine group; Phosphine oxide groups; An alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy groups; Aryl sulfoxy group; Silyl groups; Boron group; Alkyl groups; Cycloalkyl group; Alkenyl groups; Aryl group; Aralkyl group; Ar alkenyl group; Alkylaryl group; Alkylamine group; Aralkyl amine groups; Heteroarylamine group; Arylamine group; Aryl heteroaryl amine group; Aryl phosphine group; And it may be substituted or unsubstituted with one or more substituents selected from the group consisting of a heterocyclic group.

According to an example, the structural formulas exemplified as — (L) n-HAr may include a substituted or unsubstituted aryl group; Substituted or unsubstituted heterocyclic group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted heteroarylamine group; Or a substituted or unsubstituted arylheteroarylamine group.

According to an exemplary embodiment of the present invention, L and L1 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted 1 to 5 ring arylene group.

According to an exemplary embodiment of the present invention, L and L1 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted 1 to 4 ring arylene group.

According to an exemplary embodiment of the present invention, L and L1 are the same as or different from each other, and each independently a direct bond; Or an arylene group.

According to an exemplary embodiment of the present invention, L and L1 are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted phenylene group; A substituted or unsubstituted bivalent biphenyl group; A substituted or unsubstituted divalent terphenyl group; A substituted or unsubstituted divalent quarterphenyl group; A substituted or unsubstituted divalent naphthyl group; Substituted or unsubstituted divalent anthracenyl group; A substituted or unsubstituted divalent fluorenyl group; Substituted or unsubstituted divalent phenanthryl group; A substituted or unsubstituted divalent pyrenyl group; It is a substituted or unsubstituted divalent crysenyl group.

According to an exemplary embodiment of the present invention, L and L1 are the same as or different from each other, and each independently a direct bond; Phenylene group; Divalent biphenyl group; Divalent terphenyl group; Divalent quarterphenyl group; Divalent naphthyl group; Divalent anthracenyl group; Divalent fluorenyl group; Divalent phenanthryl group; Divalent pyrenyl group; It is a bivalent crysenyl group.

According to an exemplary embodiment of the present invention, L and L1 are the same as or different from each other, and each independently a substituted or unsubstituted heteroarylene group.

According to an exemplary embodiment of the present invention, L and L1 are the same as or different from each other, and each independently a substituted or unsubstituted heteroarylene group including O, N or S.

According to an exemplary embodiment of the present invention, L and L1 are the same as or different from each other, and each independently a heteroarylene group including O, N or S.

According to an exemplary embodiment of the present invention, L and L1 are the same as or different from each other, and each independently may be any one selected from a direct bond or the following structures.

In the above structural formula,

A1 and A2 are the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or may combine with each other to form a substituted or unsubstituted ring,

The structures are deuterium; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Substituted or unsubstituted amine group; Phosphine oxide groups; An alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy groups; Aryl sulfoxy group; Silyl groups; Boron group; Alkyl groups; Cycloalkyl group; Alkenyl groups; Aryl group; Aralkyl group; Ar alkenyl group; Alkylaryl group; Alkylamine group; Aralkyl amine groups; Heteroarylamine group; Arylamine group; Aryl phosphine group; And it may be substituted or unsubstituted with one or more substituents selected from the group consisting of a heterocyclic group.

In the above structural formula,

According to an exemplary embodiment of the present invention, L and L1 are the same as or different from each other, and each independently a direct bond; Or any one selected from the following structures.

In the above structural formula,

According to an exemplary embodiment of the present invention, L and L1 are the same as or different from each other, and each independently a direct bond; Phenylene group; Biphenylylene group; Or a fluorenylene group.

According to an exemplary embodiment of the present invention, L and L1 are the same as or different from each other, and each independently a direct bond; Or a phenylene group.

According to an exemplary embodiment of the present invention, in the above-described structural formula, Ar1 to Ar3 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.

According to an exemplary embodiment of the present invention, in the above-described structural formula, Ar1 to Ar3 are the same as or different from each other, each independently represent a substituted or unsubstituted aryl group.

According to an exemplary embodiment of the present invention, in the aforementioned structural formulas, Ar1 to Ar3 are the same as or different from each other, and each independently a phenyl group; Biphenylyl group; Or a naphthyl group.

According to an exemplary embodiment of the present invention, the compound of Formula 1 may be any one selected from the following compounds.

The compound represented by Chemical Formula 1 may be prepared based on the preparation examples described below. According to one embodiment, it may be prepared through the steps of Schemes 1-1 and 1-2.

Scheme 1-1 (Compound A, A-1, B, B-1, C, C-1, D, D-1)

Scheme 1-2

In the above schemes, the definitions of L1 and HAr are as described above.

Those skilled in the art can use the techniques known in the art to modify the reaction conditions, reagents, and starting materials described in the above-described schemes, and further introduce substituents as necessary.

In addition, the present specification provides an organic light emitting device including the compound represented by Formula 1.

In one embodiment of the present specification, the first electrode; A second electrode provided to face the first electrode; And an organic light emitting device including at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound of Formula 1.

The organic material layer of the organic light emitting device of the present specification may be formed of a single layer structure, but may be formed of a multilayer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer and the like as an organic material layer. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic material layers.

In an exemplary embodiment of the present specification, the organic material layer includes a hole injection layer, a hole transport layer, or a layer for simultaneously injecting and transporting holes, and the hole injection layer, a hole transport layer, or a layer for simultaneously injecting and transporting holes is It includes a compound of formula (1).

In another exemplary embodiment, the organic material layer includes a light emitting layer, and the light emitting layer includes the compound of Formula 1. According to one embodiment, the compound of Formula 1 serves as a host of the light emitting layer, in this case, the light emitting layer may further include a dopant. As the dopant, those known in the art may be used, for example, a phosphorescent dopant, specifically an iridium-based dopant, may be used together. As the iridium-based dopant, Ir (ppy) ₃ , [(piq) ₂ Ir (acac)], or the like may be used.

In one embodiment of the present specification, the organic material layer includes an electron suppression layer, and the electron suppression layer includes the compound of Formula 1.

In an exemplary embodiment of the present specification, the electron transport layer, the electron injection layer or the layer at the same time the electron transport and electron injection comprises a compound of the formula (1).

In another exemplary embodiment, the organic material layer includes a light emitting layer and an electron transport layer, and the electron transport layer includes the compound of Formula 1.

The electron transport layer may further include an n-type dopant, if necessary. The n-type dopant may use those known in the art, such as Li complex, specifically LiQrk.

According to an exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer may include a compound represented by the following Chemical Formula 1-A.

[Formula 1-A]

In Chemical Formula 1-A,

z1 is an integer of 1 or more, and if z1 is 2 or more, the structures in parentheses are the same as or different from each other,

Ar100 is a substituted or unsubstituted monovalent or higher benzofluorene group; Substituted or unsubstituted monovalent or higher fluoranthene group; A substituted or unsubstituted monovalent or higher pyrene group; Or a substituted or unsubstituted monovalent or higher chrysene group,

L100 is a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

R100 and R101 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted arylalkyl group; Or a substituted or unsubstituted heterocyclic group, or may be combined with each other to form a substituted or unsubstituted ring.

According to an exemplary embodiment of the present specification, the light emitting layer includes a compound represented by Formula 1-A as a dopant of the light emitting layer.

According to an exemplary embodiment of the present specification, the L100 is a direct bond.

According to an exemplary embodiment of the present specification, z1 is 2.

According to an exemplary embodiment of the present specification, Ar100 is a divalent pyrene group unsubstituted or substituted with deuterium, methyl, ethyl, iso-propyl, or tert-butyl groups; Or a divalent chrysene group unsubstituted or substituted with deuterium, methyl, ethyl, iso-propyl or tert-butyl groups.

According to an exemplary embodiment of the present specification, Ar100 is a divalent pyrene group unsubstituted or substituted with deuterium, methyl, ethyl, iso-propyl or tert-butyl groups.

According to an exemplary embodiment of the present specification, Ar100 is a divalent pyrene group.

According to an exemplary embodiment of the present specification, R100 and R101 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

According to an exemplary embodiment of the present specification, R100 and R101 are each independently a deuterium, an alkyl group, a nitrile group, an aryl group, an alkylsilyl group, or an alkyl group having 6 to 60 carbon atoms unsubstituted or substituted with an alkyl germanium group; Or a heterocyclic group having 2 to 60 carbon atoms unsubstituted or substituted with deuterium, an alkyl group, a nitrile group, an aryl group, an alkylsilyl group, or an alkylgermanium group.

According to an exemplary embodiment of the present specification, R100 and R101 are each independently substituted or unsubstituted with deuterium, methyl group, ethyl group, iso-propyl group, tert-butyl group, nitrile group, phenyl group, trimethylsilyl group or trimethylgermanium group Aryl groups having 6 to 60 carbon atoms; Or a heterocyclic group having 2 to 60 carbon atoms unsubstituted or substituted with deuterium, methyl group, ethyl group, iso-propyl group, tert-butyl group, nitrile group, phenyl group, trimethylsilyl group or trimethylgermanium group.

According to an exemplary embodiment of the present specification, R100 and R101 are each independently substituted or unsubstituted with deuterium, methyl group, ethyl group, iso-propyl group, tert-butyl group, nitrile group, phenyl group, trimethylsilyl group or trimethylgermanium group Phenyl group; Biphenyl group unsubstituted or substituted with deuterium, methyl group, ethyl group, iso-propyl group, tert-butyl group, nitrile group, phenyl group, trimethylsilyl group or trimethylgermanium group; Terphenyl groups unsubstituted or substituted with deuterium, methyl, ethyl, iso-propyl, tert-butyl, nitrile, phenyl, trimethylsilyl or trimethylgermanium groups; Or a dibenzofuran group unsubstituted or substituted with deuterium, methyl, ethyl, iso-propyl, tert-butyl, nitrile, phenyl, trimethylsilyl or trimethylgermanium groups.

According to an exemplary embodiment of the present specification, R100 and R101 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a trimethylgermanium group.

According to an exemplary embodiment of the present specification, the R100 is a phenyl group.

According to an exemplary embodiment of the present specification, R101 is a phenyl group substituted with a trimethylgermanium group.

According to an exemplary embodiment of the present specification, Formula 1-A may be selected from the following compounds.

According to an exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer may include a compound represented by the following Chemical Formula 1-B.

[Formula 1-B]

In Chemical Formula 1-B,

Ar101 and Ar102 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

L101 and L102 are the same as or different from each other, and are each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

R102 is hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Substituted or unsubstituted amine group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted alkyl group; A 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 aryl sulfoxy group; Substituted or unsubstituted alkenyl group; A substituted or unsubstituted aralkyl group; Substituted or unsubstituted aralkenyl group; Substituted or unsubstituted alkylaryl group; Substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted heteroarylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted arylheteroarylamine group; Substituted or unsubstituted aryl phosphine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

z2 and z3 are the same as or different from each other, and each independently an integer of 1 or 2, z4 is an integer of 0 to 8, when z2 to z4 is 2 or more, the substituents in parentheses are the same or different from each other,

m is an integer of 1 or more, and when m is an integer of 2 or more, the substituents in parentheses are the same as or different from each other.

According to an exemplary embodiment of the present specification, the light emitting layer includes a compound represented by Formula 1-B as a host of the light emitting layer.

According to an exemplary embodiment of the present specification, Ar101 and Ar102 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

According to an exemplary embodiment of the present specification, Ar101 and Ar102 are the same as or different from each other, and each independently an aryl group having 6 to 60 carbon atoms unsubstituted or substituted with an alkyl group, an aryl group or a heterocyclic group; Or a heterocyclic group having 2 to 60 carbon atoms unsubstituted or substituted with an alkyl group, an aryl group, or a heterocyclic group.

According to an exemplary embodiment of the present specification, Ar101 and Ar102 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with an aryl group or heterocyclic group; A biphenyl group unsubstituted or substituted with an aryl group or a heterocyclic group; Terphenyl groups unsubstituted or substituted with an aryl group or a heterocyclic group; A naphthyl group unsubstituted or substituted with an aryl group or a heterocyclic group; A fluorene group unsubstituted or substituted with an alkyl group, an aryl group or a heterocyclic group; Phenanthrene groups unsubstituted or substituted with an aryl group or a heterocyclic group; Or a triphenylene group unsubstituted or substituted with an aryl group or a heterocyclic group.

According to an exemplary embodiment of the present specification, Ar101 and Ar102 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; A fluorene group unsubstituted or substituted with a methyl group or a phenyl group; Phenanthrene group; Or a triphenylene group.

According to an exemplary embodiment of the present specification, Ar101 is a 2-naphthyl group.

According to an exemplary embodiment of the present specification, Ar102 is a phenyl group.

According to an exemplary embodiment of the present specification, the L101 and L102 are the same as or different from each other, and each independently a direct bond; Phenylene group; Or a naphthylene group.

According to an exemplary embodiment of the present specification, L101 is a phenylene group.

According to an exemplary embodiment of the present specification, L102 is a direct bond.

According to an exemplary embodiment of the present specification, z2 is 1.

According to an exemplary embodiment of the present specification, z3 is 1.

According to an exemplary embodiment of the present disclosure, wherein R102 is hydrogen.

According to an exemplary embodiment of the present specification, m is 1.

According to an exemplary embodiment of the present specification, m is 2.

According to an exemplary embodiment of the present specification, Formula 1-B may be selected from the following compounds.

According to the exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes the compound represented by Chemical Formula 1-A as a dopant of the light emitting layer, and the compound represented by Chemical Formula 1-B is a host of the light emitting layer. Include as.

In one embodiment of the present specification, the first electrode; A second electrode provided to face the first electrode; And a light emitting layer provided between the first electrode and the second electrode. An organic light emitting device including two or more organic material layers provided between the light emitting layer and the first electrode or between the light emitting layer and the second electrode, wherein at least one of the two or more organic material layers includes the spiro-type compound. In one exemplary embodiment, two or more organic material layers may be selected from the group consisting of an electron transport layer, an electron injection layer, a layer for simultaneously performing electron transport and electron injection, 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 spiro-type compound. Specifically, in one embodiment of the present specification, the spiro compound may be included in one layer of the two or more electron transport layers, and may be included in each of the two or more electron transport layers.

In addition, in one embodiment of the present specification, when the spiro-type compound is included in each of two or more electron transport layers, other materials except for the spiro-type compound may be the same or different from each other.

In another exemplary embodiment, the organic light emitting diode may be an organic light emitting diode having a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.

In another exemplary embodiment, the organic light emitting diode may be an organic light emitting diode having an inverted type in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.

For example, the structure of an organic light emitting diode according to one embodiment of the present specification is illustrated in FIGS. 1 and 2.

FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4. As shown in FIG. In such a structure, the compound may be included in the light emitting layer.

2 shows an example of an organic light emitting element consisting of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 3, an electron transport layer 7 and a cathode 4. It is. In such a structure, the compound may be included in one or more layers of the hole injection layer, hole transport layer, light emitting layer and electron transport layer.

The organic light emitting device of the present specification may be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound of the present specification, that is, the compound of Formula 1.

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

The organic light emitting device of the present specification may be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound represented by Chemical Formula 1, that is, the compound represented by Chemical Formula 1.

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

In addition, the compound of Formula 1 may be formed of an organic material layer by a solution coating method as well as a vacuum deposition method in the manufacture of the organic light emitting device. Here, the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, etc., but is not limited thereto.

In addition to such a method, an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material on a substrate (International Patent Application Publication No. 2003/012890). However, the manufacturing method is not limited thereto.

In one embodiment of the present specification, the first electrode is an anode, and the second electrode is a cathode.

In another exemplary embodiment, the first electrode is a cathode and the second electrode is an anode.

As the anode material, a material having a large work function is usually preferred to facilitate hole injection into the organic material layer. Specific examples of the positive electrode 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), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO ₂ : Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline, and the like, but are not limited thereto.

It is preferable that the cathode material is a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material that can be used in the present invention include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; Multilayer structure materials such as LiF / Al or LiO ₂ / Al, and the like, but are not limited thereto.

The hole injection layer is a layer for injecting holes from the electrode, and has a capability of transporting holes to the hole injection material, and has a hole injection effect at the anode, an excellent hole injection effect to the light emitting layer or the light emitting material, and is produced in the light emitting layer The compound which prevents the excitons from moving to the electron injection layer or the electron injection material, and is excellent in thin film formation ability is preferable. Preferably, the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene-based Organic materials, anthraquinone, and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.

The hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the light emitting layer. The hole transport material is a material capable of transporting holes from an anode or a hole injection layer and transferring them to the light emitting layer. The material is suitable. Specific examples thereof include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together, but are not limited thereto.

The light emitting material is a material capable of emitting light in the 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 with respect to fluorescence or phosphorescence is preferable. Specific examples thereof include 8-hydroxyquinoline aluminum complex (Alq ₃ ); Carbazole series compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzothiazole and benzimidazole series compounds; Poly (p-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene, rubrene and the like, but are not limited thereto.

The light emitting layer may include a host material and a dopant material. The host material is a condensed aromatic ring derivative or a heterocyclic containing compound. Specifically, the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and the heterocyclic containing compounds include carbazole derivatives, dibenzofuran derivatives and ladder types. Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

Dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like. Specifically, the aromatic amine derivatives include condensed aromatic ring derivatives having a substituted or unsubstituted arylamine group, and include pyrene, anthracene, chrysene, and periplanthene having an arylamine group, and a styrylamine compound may be substituted or unsubstituted. At least one arylvinyl group is substituted with the arylamine, and one or two or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamine group are substituted or unsubstituted. Specifically, styrylamine, styryldiamine, styryltriamine, styryltetraamine and the like, but is not limited thereto. In addition, the metal complex includes, but is not limited to, an iridium complex, a platinum complex, and the like.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer. The electron transporting material is a material that can inject electrons well from the cathode and transfer them to the light emitting layer. Suitable. Specific examples thereof include Al complexes of 8-hydroxyquinoline; Complexes including Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto. The electron transport layer can be used with any desired cathode material as used in accordance with the prior art. In particular, examples of suitable cathode materials are conventional materials having a low work function followed by an aluminum or silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, followed by an aluminum layer or silver layer in each case.

The electron injection layer is a layer that injects electrons from an electrode, has an ability to transport electrons, has an electron injection effect from a cathode, an electron injection effect with respect to a light emitting layer or a light emitting material, and hole injection of excitons generated in the light emitting layer The compound which prevents the movement to a layer and is excellent in thin film formation ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like and derivatives thereof, metal Complex compounds, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8-hydroxyquinolinato) manganese, Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis (10-hydroxybenzo [h] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtolato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtolato) gallium, 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 side emission type according to a material used.

Preparation of the compound represented by Chemical Formula 1 and an organic light emitting device including the same will be described in detail in the following Examples. However, the following examples are intended to illustrate the present specification, and the scope of the present specification is not limited thereto.

<< 제조예Production Example 1> 1>

Compound Synthesis of the Following Compound 1

230 ml of tetrahydrofuran with Compound B-1 (10 g, 16.50 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (5.31 g, 18.98 mmol) in a 500 ml round bottom flask in a nitrogen atmosphere After completely dissolved in 2M aqueous potassium carbonate solution (125ml) was added, tetrakis- (triphenylphosphine) palladium (0.19g, 0.17mmol) was added and stirred for 5 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 270 ml of ethyl acetate to obtain compound 1 (10.36 g, 88%).

MS [M + H] ⁺ = 712

<< 제조예Production Example 2> 2>

Compound Synthesis of the Following Compound 2

In a 500 ml round bottom flask in a nitrogen atmosphere, Compound B-1 (10 g, 16.50 mmol) and 2-chloro-4,6-diphenylpyrimidine (5.31 g, 18.98 mmol) were completely dissolved in 250 ml of tetrahydrofuran, followed by 2 M potassium carbonate. An aqueous solution (125ml) was added, tetrakis- (triphenylphosphine) palladium (0.19g, 0.17mmol) was added thereto, and the mixture was heated and stirred for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 230 ml of ethyl acetate to obtain compound 2 (9.78 g, 83%).

MS [M + H] ⁺ = 711

<< 제조예Production Example 3> 3>

Compound Synthesis of the Following Compound 3

In a 500 ml round bottom flask in a nitrogen atmosphere, Compound B-1 (10 g, 16.50 mmol) and 4-chloro-2,6-diphenylpyrimidine (5.31 g, 18.98 mmol) were completely dissolved in 260 ml of tetrahydrofuran, followed by 2 M potassium carbonate. An aqueous solution (125ml) was added, tetrakis- (triphenylphosphine) palladium (0.19g, 0.17mmol) was added thereto, and the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 240 ml of ethyl acetate to obtain compound 3 (8.65 g, 74%).

MS [M + H] ⁺ = 711

<< 제조예Production Example 4> 4>

Compound Synthesis of the Following Compound 4

In a 500 ml round-bottom flask in a nitrogen atmosphere, Compound B-1 (10 g, 16.50 mmol) and 2-chloro-4,6-diphenylpyridine (31 g, 18.98 mmol) were completely dissolved in 280 ml of tetrahydrofuran, followed by 2M aqueous potassium carbonate solution ( 125 ml) was added, tetrakis- (triphenylphosphine) palladium (0.19 g, 0.17 mmol) was added, and the mixture was heated and stirred for 2 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 280 ml of ethyl acetate to obtain compound 4 (7.74 g, 66%).

MS [M + H] ⁺ = 710

<< 제조예Production Example 5> 5>

Compound Synthesis of the Following Compound 5

Compound B-1 (10 g, 16.50 mmol), 2- (4-chlorophenyl) -4,6-diphenyl-1,3,5-triazine (6.51 g, 18.98 mmol) in a 500 ml round bottom flask in a nitrogen atmosphere After completely dissolved in 250ml of tetrahydrofuran, 2M aqueous potassium carbonate solution (125ml) was added, tetrakis- (triphenylphosphine) palladium (0.19g, 0.17mmol) was added thereto, and the mixture was heated and stirred for 5 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 300 ml of ethyl acetate to obtain compound 5 (10.36 g, 88%).

MS [M + H] ⁺ = 788

<< 제조예Production Example 6> 6>

Compound Synthesis of the Following Compound 6

In a 500 ml round bottom flask in a nitrogen atmosphere, Compound B-1 (10 g, 16.50 mmol) and 2-chloro-4-phenylquinazoline (4.57 g, 18.98 mmol) were completely dissolved in 250 ml of tetrahydrofuran, followed by 2M aqueous potassium carbonate solution (125 ml). ) Was added, tetrakis- (triphenylphosphine) palladium (0.19 g, 0.17 mmol) was added and the mixture was heated and stirred for 6 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 230 ml of ethyl acetate to obtain compound 6 (9.95 g, 74%).

MS [M + H] ⁺ = 685

<< 제조예Production Example 7> 7>

Compound Synthesis of the Following Compound 7

Compound B-1 (10 g, 16.50 mmol) and 3-bromo-9-phenyl-9H-carbazole (6.09 g, 18.98 mmol) were completely dissolved in 250 ml of tetrahydrofuran in a 500 ml round bottom flask in a nitrogen atmosphere, followed by 2M carbonate. Aqueous potassium solution (125 ml) was added, tetrakis- (triphenylphosphine) palladium (0.19 g, 0.17 mmol) was added, and the mixture was heated and stirred for 6 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 230 ml of ethyl acetate to obtain compound 7 (12.05 g, 85%).

MS [M + H] ⁺ = 722

<< 제조예Production Example 8> 8>

Compound Synthesis of the Following Compound 8

Dissolve Compound B-1 (10 g, 16.50 mmol) and (4-bromophenyl) diphenylphosphine oxide (7.71 g, 18.98 mmol) in 250 ml of tetrahydrofuran in a 500 ml round-bottom flask in a nitrogen atmosphere. An aqueous solution (125ml) was added, tetrakis- (triphenylphosphine) palladium (0.19g, 0.17mmol) was added thereto, and the mixture was heated and stirred for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 310 ml of ethyl acetate to obtain compound 8 (13.97 g, 94%).

MS [M + H] ⁺ = 757

<< 제조예Production Example 9> 9>

Compound Synthesis of the Following Compound 9

In a 500 ml round bottom flask in a nitrogen atmosphere, compound B-1 (10 g, 16.50 mmol), 2- (4-bromophenyl) -1-phenyl-1H-benzo [d] imidazole (7.71 g, 18.98 mmol) After completely dissolved in 250 ml of hydrofuran, 2M aqueous potassium carbonate solution (125 ml) was added thereto, and tetrakis- (triphenylphosphine) palladium (0.19 g, 0.17 mmol) was added thereto, followed by heating and stirring for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 310 ml of ethyl acetate to obtain compound 9 (12.24 g, 83%).

MS [M + H] ⁺ = 749

<< 제조예Production Example 10> 10>

Compound Synthesis of the Following Compound 10

In a 500 ml round-bottom flask in a nitrogen atmosphere, Compound B-1 (10 g, 16.50 mmol) and 2-bromodibenzo [b, d] furan (4.69 g, 18.98 mmol) were completely dissolved in 290 ml of tetrahydrofuran, followed by 2M aqueous potassium carbonate solution. (125 ml) was added, tetrakis- (triphenylphosphine) palladium (0.19 g, 0.17 mmol) was added, and the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 230 ml of ethyl acetate to obtain compound 10 (7.53 g, 59%).

MS [M + H] ⁺ = 647

<< 제조예Production Example 11> 11>

Compound Synthesis of the Following Compound 11

Compound B-1 (10 g, 16.50 mmol) and 2-bromodibenzo [b, d] thiophene (4.99 g, 18.98 mmol) were completely dissolved in 290 ml of tetrahydrofuran in a 500 ml round bottom flask in a nitrogen atmosphere. An aqueous solution (125ml) was added, tetrakis- (triphenylphosphine) palladium (0.19g, 0.17mmol) was added thereto, and the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 230 ml of ethyl acetate to obtain compound 11 (7.53 g, 59%).

MS [M + H] ⁺ = 663

<< 제조예Production Example 12> 내지 < 12> to < 제조예Production Example 22> 22>

Compound 12, 13, 14, 15, 16, 17, 18, in the same manner as in Preparation Examples 1 to 11 except that the starting material in Preparation Examples 1 to 11 was used as the compound C-1 instead of Compound B-1 19, 20, 21 and 22 were prepared.

화합물compound	MS[M+H]⁺ MS [M + H] ⁺	화합물compound	MS[M+H]⁺ MS [M + H] ⁺
1212	712712	1818	722722
1313	711711	1919	757757
1414	711711	2020	749749
1515	710710	2121	647647
1616	788788	2222	663663
1717	685685

<< 제조예Production Example 23> 내지 < 23> to < 제조예Production Example 33> 33>

Compounds 23, 24, 25, 26, 27, 28, 29, and 23, 24, 25, 26, 27, 28, 29 30, 31, 32 and 33 were prepared.

화합물compound	MS[M+H]⁺ MS [M + H] ⁺	화합물compound	MS[M+H]⁺ MS [M + H] ⁺
2323	712712	2929	722722
2424	711711	3030	757757
2525	711711	3131	749749
2626	710710	3232	647647
2727	788788	3333	663663
2828	685685

<< 제조예Production Example 34> 내지 < 34> to < 제조예Production Example 44> 44>

Compounds 34, 35, 36, 37, 38, 39, and 40 were prepared in the same manner as in Preparation Examples 1 to 11, except that starting materials were used in Preparation Examples 1 to 11 instead of Compound B-1. , 41, 42, 43 and 44 were prepared.

화합물compound	MS[M+H]⁺ MS [M + H] ⁺	화합물compound	MS[M+H]⁺ MS [M + H] ⁺
3434	712712	4040	722722
3535	711711	4141	757757
3636	711711	4242	749749
3737	710710	4343	647647
3838	788788	4444	663663
3939	685685

<< 실험예Experimental Example 1> 1>

After the compounds synthesized in the synthesis example was subjected to high purity sublimation purification by a commonly known method, a green organic light emitting device was manufactured by the following method.

A glass substrate coated with a thin film of ITO (indium tin oxide) at a thickness of 1,000 Å was placed in distilled water in which detergent was dissolved and ultrasonically cleaned. At this time, Fischer Co. product was used as a detergent, and distilled water filtered secondly as a filter of Millipore Co. product was used as distilled water. After ITO was washed for 30 minutes, ultrasonic washing was performed twice with distilled water for 10 minutes. After washing the distilled water, ultrasonic washing with a solvent of isopropyl alcohol, acetone, methanol, dried and transported to a plasma cleaner. In addition, the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.

Using CBP as a host on the prepared ITO transparent electrode, m-MTDATA (60 nm) / TCTA (80 nm) / CBP + 10% Ir (ppy) ₃ (300 nm) / BCP (10 nm) / Alq ₃ (30 nm) The organic light emitting device was manufactured by constructing the light emitting device in the order of) / LiF (1 nm) / Al (200nm).

The structures of m-MTDATA, TCTA, Ir (ppy) ₃ , CBP, and BCP are as follows.

<< 실험예Experimental Example 1-1> 1-1>

The organic light emitting device was manufactured by the same method as Experimental Example 1, except that compound 1 was used instead of CBP in Experimental Example 1.

<< 실험예Experimental Example 1-2> 1-2>

The organic light emitting device was manufactured by the same method as Experimental Example 1, except that compound 2 was used instead of CBP in Experimental Example 1.

<< 실험예Experimental Example 1-3> 1-3>

The organic light emitting device was manufactured by the same method as Experimental Example 1, except that compound 3 was used instead of CBP in Experimental Example 1.

<< 실험예Experimental Example 1-4> 1-4>

The organic light emitting device was manufactured by the same method as Experimental Example 1, except that compound 4 was used instead of CBP in Experimental Example 1.

<< 실험예Experimental Example 1-5> 1-5>

The organic light emitting device was manufactured by the same method as Experimental Example 1, except that compound 5 was used instead of CBP in Experimental Example 1.

<< 실험예Experimental Example 1-6> 1-6>

The organic light emitting device was manufactured by the same method as Experimental Example 1, except that compound 12 was used instead of CBP in Experimental Example 1.

<< 실험예Experimental Example 1-7> 1-7>

The organic light emitting device was manufactured by the same method as Experimental Example 1, except that compound 13 was used instead of CBP in Experimental Example 1.

<< 실험예Experimental Example 1-8> 1-8>

The organic light emitting device was manufactured by the same method as Experimental Example 1, except that compound 14 was used instead of CBP in Experimental Example 1.

<< 실험예Experimental Example 1-9> 1-9>

The organic light emitting device was manufactured by the same method as Experimental Example 1, except that compound 15 was used instead of CBP in Experimental Example 1.

<< 실험예Experimental Example 1-10> 1-10>

The organic light emitting device was manufactured by the same method as Experimental Example 1, except that compound 16 was used instead of CBP in Experimental Example 1.

<< 실험예Experimental Example 1-11> 1-11>

The organic light emitting device was manufactured by the same method as Experimental Example 1, except that compound 23 was used instead of CBP in Experimental Example 1.

<< 실험예Experimental Example 1-12> 1-12>

The organic light emitting device was manufactured by the same method as Experimental Example 1, except that compound 24 was used instead of CBP in Experimental Example 1.

<< 실험예Experimental Example 1-13> 1-13>

The organic light emitting device was manufactured by the same method as Experimental Example 1, except that compound 25 was used instead of CBP in Experimental Example 1.

<< 실험예Experimental Example 1-14> 1-14>

The organic light emitting device was manufactured by the same method as Experimental Example 1, except that compound 26 was used instead of CBP in Experimental Example 1.

<< 실험예Experimental Example 1-15> 1-15>

The organic light emitting device was manufactured by the same method as Experimental Example 1, except that compound 27 was used instead of CBP in Experimental Example 1.

<< 실험예Experimental Example 1-16> 1-16>

The organic light emitting device was manufactured by the same method as Experimental Example 1, except that compound 34 was used instead of CBP in Experimental Example 1.

<< 실험예Experimental Example 1-17> 1-17>

The organic light emitting device was manufactured by the same method as Experimental Example 1, except that compound 35 was used instead of CBP in Experimental Example 1.

<< 실험예Experimental Example 1-18> 1-18>

The organic light emitting device was manufactured by the same method as Experimental Example 1, except that compound 36 was used instead of CBP in Experimental Example 1.

<< 실험예Experimental Example 1-19> 1-19>

The organic light emitting device was manufactured by the same method as Experimental Example 1, except that compound 37 was used instead of CBP in Experimental Example 1.

<< 실험예Experimental Example 1-20> 1-20>

The organic light emitting device was manufactured by the same method as Experimental Example 1, except that compound 38 was used instead of CBP in Experimental Example 1.

When the electric current was applied to the organic light emitting element produced by Experimental Example 1 and Experimental Examples 1-1 to 1-20, the result of Table 4 was obtained.

	화합물(호스트)Compound (Host)	전압(V@10mA/cm²)Voltage (V @ 10mA / cm ² )	효율(cd/A@10mA/cm²)Efficiency (cd / A @ 10mA / cm ² )	EL 피크(nm)EL peak (nm)
실험예 1Experimental Example 1	CBPCBP	7.457.45	38.1238.12	516516
실험예 1-1Experimental Example 1-1	화합물 1 Compound 1	6.306.30	43.5343.53	517517
실험예 1-2Experimental Example 1-2	화합물 2 Compound 2	6.326.32	43.1443.14	517517
실험예 1-3Experimental Example 1-3	화합물 3 Compound 3	6.316.31	43.3243.32	517517
실험예 1-4Experimental Example 1-4	화합물 4 Compound 4	6.226.22	44.4544.45	518518
실험예 1-5Experimental Example 1-5	화합물 5 Compound 5	6.306.30	43.3143.31	517517
실험예 1-6Experimental Example 1-6	화합물 12Compound 12	6.236.23	44.6344.63	517517
실험예 1-7Experimental Example 1-7	화합물 13Compound 13	6.316.31	43.0243.02	516516
실험예 1-8Experimental Example 1-8	화합물 14Compound 14	6.326.32	43.2443.24	513513
실험예 1-9Experimental Example 1-9	화합물 15Compound 15	6.226.22	44.3844.38	516516
실험예 1-10Experimental Example 1-10	화합물 16Compound 16	6.316.31	43.8243.82	516516
실험예 1-11Experimental Example 1-11	화합물 23Compound 23	6.326.32	43.5043.50	517517
실험예 1-12Experimental Example 1-12	화합물 24Compound 24	6.316.31	43.1643.16	516516
실험예 1-13Experimental Example 1-13	화합물 25Compound 25	6.326.32	43.2343.23	516516
실험예 1-14Experimental Example 1-14	화합물 26Compound 26	6.266.26	44.4444.44	516516
실험예 1-15Experimental Example 1-15	화합물 27Compound 27	6.316.31	43.6243.62	516516
실험예 1-16Experimental Example 1-16	화합물 34Compound 34	6.296.29	44.7544.75	516516
실험예 1-17Experimental Example 1-17	화합물 35Compound 35	6.386.38	43.9143.91	516516
실험예 1-18Experimental Example 1-18	화합물 36Compound 36	6.236.23	44.8344.83	517517
실험예 1-19Experimental Example 1-19	화합물 37Compound 37	6.246.24	44.4244.42	516516
실험예 1-20Experimental Example 1-20	화합물 38Compound 38	6.276.27	44.5444.54	517517

As a result, the green organic light emitting device of Experimental Examples 1-1 to 1-20 using the compound according to the present invention as a host material of the light emitting layer has higher current efficiency and driving voltage than the green organic light emitting device of Experimental Example 1 using CBP. It was confirmed that the excellent performance in terms of. In particular, the compounds having triazine, pyrimidine or pyridine as substituents were found to be suitable as green organic light emitting devices.

<< 실험예Experimental Example 2> 2>

After the compounds synthesized in the synthesis example was subjected to high purity sublimation purification by a commonly known method, a red organic light emitting device was manufactured by the following method.

The light emitting area of the ITO glass was patterned to have a size of 2 mm × 2 mm and then washed. After mounting the substrate in a vacuum chamber, the base pressure was 1 × 10 ^-6 torr, and then organic materials were formed on the ITO to form a DNTPD layer (700 kPa) and an α-NPB layer (300 kPa). (90 wt%) was used, and the following (piq) ₂ Ir (acac) (10 wt%) was co-deposited (300 Pa) as a dopant to prepare a light emitting layer. Subsequently, an Alq ₃ layer (350 kV), a LiF layer (5 kPa) and an Al layer (1,000 kPa) were formed in this order, and the device characteristics were measured at 0.4 mA.

The structures of DNTPD, α-NPB, (piq) ₂ Ir (acac) and Alq ₃ are as follows.

<< 실험예Experimental Example 2-1> 내지 < 2-1> to < 실험예Experimental Example 2-4> 2-4>

The organic light emitting device was manufactured by the same method as Experimental Example 2, except for using the compounds 7, 18, 29, and 40 prepared in the aforementioned preparation examples instead of CBP in Experimental Example 2.

For organic light emitting devices manufactured according to Experimental Examples 2-1 to 2-4 and Experimental Example 2, voltage, current density, luminance, color coordinates, and lifetime were measured, and the results are shown in Table 5 below. T95 means the time taken for the luminance to be reduced to 95% from the initial luminance (5000 nits).

구분division	화합물(호스트)Compound (Host)	도펀트Dopant	전압Voltage	휘도(V)Luminance (V)	CIEx(cd/m²)CIEx (cd / m ² )	CIEy(cd/m²)CIEy (cd / m ² )	T95(hr)T95 (hr)
실험예 2-1Experimental Example 2-1	화합물 7Compound 7	[(piq)₂Ir(acac)][(piq) ₂ Ir (acac)]	4.34.3	17601760	0.6700.670	0.3290.329	465465
실험예 2-2Experimental Example 2-2	화합물 18Compound 18	[(piq)₂Ir(acac)][(piq) ₂ Ir (acac)]	4.24.2	18501850	0.6740.674	0.3250.325	415415
실험예 2-3Experimental Example 2-3	화합물 29Compound 29	[(piq)₂Ir(acac)][(piq) ₂ Ir (acac)]	4.14.1	19001900	0.6720.672	0.3270.327	390390
실험예 2-4Experimental Example 2-4	화합물 40Compound 40	[(piq)₂Ir(acac)][(piq) ₂ Ir (acac)]	4.34.3	17401740	0.6730.673	0.3350.335	475475
실험예 2Experimental Example 2	CBPCBP	[(piq)₂Ir(acac)][(piq) ₂ Ir (acac)]	7.57.5	12201220	0.6790.679	0.3390.339	285285

As a result, the red organic light emitting diodes of Experimental Examples 2-1 to 2-4 using the compounds represented by the compounds 7, 18, 29 and 40 prepared according to the present invention as host materials of the light emitting layer were tested using conventional CBP. It was confirmed that the red organic light emitting diode of Example 2 exhibited better performance in terms of current efficiency, driving voltage, and lifetime. In particular, the compounds having a carbazole as a substituent was found to be suitable as a red organic light emitting device.

<< 실험예Experimental Example 3-1> 3-1>

The hexanitrile hexaazatriphenylene (HAT) of the following formula was thermally vacuum deposited to a thickness of 500 kPa on the prepared ITO transparent electrode to form a hole injection layer.

[HAT]

Compound 4-4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (NPB) (400 kV), which is a substance for transporting holes on the hole injection layer, was vacuum deposited to form a hole transport layer. It was.

[NPB]

Subsequently, the light emitting layer was formed by vacuum depositing the following BH and BD in a weight ratio of 25: 1 on the hole transport layer with a film thickness of 300 GPa.

[BH]

[BD]

[LiQ]

Compound 1 prepared in Preparation Example 1 and the compound LiQ (Lithium Quinolate) were vacuum-deposited at a weight ratio of 1: 1 on the emission layer to form an electron injection and transport layer at a thickness of 300 Pa. On the electron injection and transport layer, lithium fluoride (LiF) and aluminum were deposited to have a thickness of 12 kW in order to form a cathode.

Was maintained at the deposition rate was 0.4 ~ 0.7Å / sec for organic material in the above process, the lithium fluoride of the cathode was 0.3Å / sec, aluminum is deposited at a rate of 2Å / sec, During the deposition, a vacuum 2 × 10 ^{- The} organic light emitting device was manufactured by maintaining ⁷ to 5 × 10 ⁻⁶ torr.

<< 실험예Experimental Example 3-2> 3-2>

Except for using the compound 5 instead of compound 1 as the electron transport layer in Experimental Example 3-1 was the same experiment.

<< 실험예Experimental Example 3-3> 3-3>

Except for using the compound 8 instead of compound 1 as the electron transport layer in Experimental Example 3-1 was the same experiment.

<< 실험예Experimental Example 3-4> 3-4>

Except for using the compound 9 instead of compound 1 as the electron transport layer in Experimental Example 3-1 was the same experiment.

<< 실험예Experimental Example 3-5> 3-5>

Except for using the compound 12 instead of compound 1 as the electron transport layer in Experimental Example 3-1 was the same experiment.

<< 실험예Experimental Example 3-6> 3-6>

Except for using compound 16 instead of compound 1 as the electron transport layer in Experimental Example 3-1 was the same experiment.

<< 실험예Experimental Example 3-7> 3-7>

Except for using the compound 19 instead of compound 1 as the electron transport layer in Experimental Example 3-1 was the same experiment.

<< 실험예Experimental Example 3-8> 3-8>

Except for using the compound 20 instead of compound 1 as the electron transport layer in Experimental Example 3-1 was the same experiment.

<< 실험예Experimental Example 3-9> 3-9>

Except for using the compound 23 instead of compound 1 as the electron transport layer in Experimental Example 3-1 was the same experiment.

<< 실험예Experimental Example 3-10> 3-10>

Except for using the compound 27 instead of compound 1 as the electron transport layer in Experimental Example 3-1 was the same experiment.

<< 실험예Experimental Example 3-11> 3-11>

Except for using the compound 30 instead of compound 1 as the electron transport layer in Experimental Example 3-1 was the same experiment.

<< 실험예Experimental Example 3-12> 3-12>

Except for using the compound 31 instead of compound 1 as the electron transport layer in Experimental Example 3-1 was the same experiment.

<< 실험예Experimental Example 3-13> 3-13>

Except for using the compound 34 instead of compound 1 as the electron transport layer in Experimental Example 3-1 was the same experiment.

<< 실험예Experimental Example 3-14> 3-14>

Except for using the compound 38 instead of compound 1 as the electron transport layer in Experimental Example 3-1 was the same experiment.

<< 실험예Experimental Example 3-15> 3-15>

Except for using the compound 41 instead of compound 1 as the electron transport layer in Experimental Example 3-1 was the same experiment.

<< 실험예Experimental Example 3-16> 3-16>

Except for using the compound 42 instead of compound 1 as the electron transport layer in Experimental Example 3-1 was the same experiment.

<< 실험예Experimental Example 3> 3>

Except that the following compound ET 1 was used instead of compound 1 as the electron transport layer in Experimental Example 3-1.

[ET 1]

When the electric current was applied to the organic light emitting element produced by Experimental Example 3-1 to 3-16 and Experimental Example 3, the result of Table 6 was obtained.

구분division	화합물(전자수송층)Compound (electron transport layer)	전압(V@10mA/cm²)Voltage (V @ 10mA / cm ² )	효율(cd/A@10mA/cm²)Efficiency (cd / A @ 10mA / cm ² )	EL 피크(nm)EL peak (nm)
실험예 3-1Experimental Example 3-1	화합물 1 Compound 1	6.286.28	46.9346.93	517517
실험예 3-2Experimental Example 3-2	화합물 5 Compound 5	6.366.36	45.2445.24	516516
실험예 3-3Experimental Example 3-3	화합물 8Compound 8	6.356.35	45.7945.79	518518
실험예 3-4Experimental Example 3-4	화합물 9Compound 9	6.296.29	46.1546.15	517517
실험예 3-5Experimental Example 3-5	화합물 12Compound 12	6.386.38	45.3145.31	515515
실험예 3-6Experimental Example 3-6	화합물 16Compound 16	6.336.33	45.6345.63	516516
실험예 3-7Experimental Example 3-7	화합물 19Compound 19	6.396.39	45.6245.62	516516
실험예 3-8Experimental Example 3-8	화합물 20Compound 20	6.376.37	45.6445.64	517517
실험예 3-9Experimental Example 3-9	화합물 23Compound 23	6.246.24	46.6846.68	518518
실험예 3-10Experimental Example 3-10	화합물 27Compound 27	6.386.38	45.8345.83	517517
실험예 3-11Experimental Example 3-11	화합물 30Compound 30	6.366.36	45.2445.24	516516
실험예 3-12Experimental Example 3-12	화합물 31Compound 31	6.446.44	44.9444.94	518518
실험예 3-13Experimental Example 3-13	화합물 34Compound 34	6.356.35	45.2245.22	517517
실험예 3-14Experimental Example 3-14	화합물 38Compound 38	6.336.33	45.7545.75	515515
실험예 3-15Experimental Example 3-15	화합물 41Compound 41	6.156.15	47.1647.16	516516
실험예 3-16Experimental Example 3-16	화합물 42Compound 42	6.246.24	46.3446.34	516516
실험예 3Experimental Example 3	ET 1 ET 1	7.457.45	35.5235.52	517517

As shown in Table 6, when comparing Experimental Examples 3-1 to 3-16, and Experimental Example 3, it was confirmed that the electron transport and injection ability is excellent. In particular, it was found that the compounds having triazine, benzimidazole or arylphosphine oxide as substituents are suitable as organic light emitting device materials.

Although preferred embodiments of the present invention (green light emitting layer, red light emitting layer, electron transport layer) have been described above, the present invention is not limited thereto, and various modifications are made within the scope of the claims and the detailed description of the invention. It is possible and this also belongs to the scope of the invention.

Claims

Compound represented by the following formula (1):

[Formula 1]

In Chemical Formula 1,

L is a direct bond, a substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

HAr is a substituted or unsubstituted heterocyclic group; Or a substituted or unsubstituted phosphine oxide group,

R1 to R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Substituted or unsubstituted amine group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted alkyl group; A 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 aryl sulfoxy group; Substituted or unsubstituted alkenyl group; A substituted or unsubstituted aralkyl group; Substituted or unsubstituted aralkenyl group; Substituted or unsubstituted alkylaryl group; Substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted heteroarylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted arylheteroarylamine group; Substituted or unsubstituted aryl phosphine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or may be combined with an adjacent group to form a substituted or unsubstituted ring,

a is an integer of 0 to 7, b is an integer of 0 to 7, c is an integer of 0 to 5, d is an integer of 0 to 4, n is an integer of 0 to 10, a, b, c, When d and n are each 2 or more, the structures in parentheses are the same or different from each other.
The compound of claim 1, wherein Formula 1 is represented by one of the following Formulas 2 to 5:

[Formula 2]

[Formula 3]

[Formula 4]

[Formula 5]

In Formulas 2 to 5, the definition of the substituent is the same as in Formula 1.
The method according to claim 1, wherein the HAr is substituted or unsubstituted pyridyl group; Substituted or unsubstituted pyrimidyl group; Substituted or unsubstituted triazinyl group; Substituted or unsubstituted furan group; Substituted or unsubstituted thiophene group; Substituted or unsubstituted oxadiazole group; Substituted or unsubstituted thiadiazole group; Substituted or unsubstituted phenanthrosine group; Substituted or unsubstituted quinolinyl group; Substituted or unsubstituted isoquinolinyl group; Substituted or unsubstituted quinazoline group; Substituted or unsubstituted benzoxazole group; Substituted or unsubstituted benzothiazole group; Substituted or unsubstituted benzimidazole group; Substituted or unsubstituted phenoxazine group; Substituted or unsubstituted phenothiazine group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted dibenzothiophene group; Substituted or unsubstituted carbazole group; Or a substituted or unsubstituted diaryl phosphine oxide group.
The compound of claim 1, wherein-(L) n-HAr is represented by the following structural formulas:

In the above structural formulas,

Ar1 to Ar3 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Substituted or unsubstituted heterocyclic group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted heteroarylamine group; Or a substituted or unsubstituted arylheteroarylamine group,

L 1 is a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

The structures are deuterium; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Substituted or unsubstituted amine group; Phosphine oxide groups; An alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy groups; Aryl sulfoxy group; Silyl groups; Boron group; Alkyl groups; Cycloalkyl group; Alkenyl groups; Aryl group; Aralkyl group; Ar alkenyl group; Alkylaryl group; Alkylamine group; Aralkyl amine groups; Heteroarylamine group; Arylamine group; Aryl phosphine group; And it may be substituted or unsubstituted with one or more substituents selected from the group consisting of a heterocyclic group.
The method according to claim 1, wherein L is a direct bond; Or a compound selected from the following structures:

In the above structural formula,

A1 and A2 are the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or may combine with each other to form a substituted or unsubstituted ring,

The structures are deuterium; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amine groups; Phosphine oxide groups; An alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy groups; Aryl sulfoxy group; Silyl groups; Boron group; Alkyl groups; Cycloalkyl group; Alkenyl groups; Aryl group; Aralkyl group; Ar alkenyl group; Alkylaryl group; Alkylamine group; Aralkyl amine groups; Heteroarylamine group; Arylamine group; Aryl phosphine group; And it may be substituted or unsubstituted with one or more substituents selected from the group consisting of a heterocyclic group.
The compound of claim 1, wherein the compound of Formula 1 is any one selected from the following structural formulas:
A first electrode; A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes a compound according to any one of claims 1 to 6. Organic light emitting device.
The organic light emitting device of claim 7, 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 8, wherein the light emitting layer further comprises a light emitting dopant.
The method according to claim 7, wherein the organic layer comprises an electron injection layer, an electron transport layer, or a layer for simultaneously transporting electrons and electron injection, the electron injection layer, the electron transport layer, or the layer for simultaneously transporting and electron injection is the compound Organic light emitting device comprising a.
The organic light emitting device of claim 10, wherein the electron transport layer further comprises an n-type dopant.
The method according to claim 7, wherein the organic layer comprises a hole injection layer, a hole transport layer, a layer for simultaneously injecting and transporting holes or an electron suppression layer, the hole injection layer, a hole transport layer, a layer for simultaneously injecting and transporting holes or an electron suppression And the layer comprises the compound.
The organic light emitting device of claim 7, wherein the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula 1-A:

[Formula 1-A]

In Chemical Formula 1-A,

z1 is an integer of 1 or more, and if z1 is 2 or more, the structures in parentheses are the same as or different from each other,

Ar100 is a substituted or unsubstituted monovalent or higher benzofluorene group; Substituted or unsubstituted monovalent or higher fluoranthene group; A substituted or unsubstituted monovalent or higher pyrene group; Or a substituted or unsubstituted monovalent or higher chrysene group,

L100 is a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

R100 and R101 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted arylalkyl group; Or a substituted or unsubstituted heterocyclic group, or may be combined with each other to form a substituted or unsubstituted ring.
The organic compound of claim 13, wherein z1 is 2, Ar100 is a divalent pyrene group, L100 is a direct bond, and R100 and R101 are the same or different from each other, and each independently an aryl group unsubstituted or substituted with an alkylgermanium group. Light emitting element.
The organic light emitting device of claim 7, wherein the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula 1-B:

[Formula 1-B]

In Chemical Formula 1-B,

Ar101 and Ar102 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

L101 and L102 are the same as or different from each other, and are each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

R102 is hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Substituted or unsubstituted amine group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted alkyl group; A 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 aryl sulfoxy group; Substituted or unsubstituted alkenyl group; A substituted or unsubstituted aralkyl group; Substituted or unsubstituted aralkenyl group; Substituted or unsubstituted alkylaryl group; Substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted heteroarylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted arylheteroarylamine group; Substituted or unsubstituted aryl phosphine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

z2 and z3 are the same as or different from each other, and each independently an integer of 1 or 2, z4 is an integer of 0 to 8, when z2 to z4 is 2 or more, the substituents in parentheses are the same or different from each other,

m is an integer of 1 or more, and when m is an integer of 2 or more, the substituents in parentheses are the same as or different from each other.
The organic light emitting device of claim 15, wherein Ar101 is a 2-naphthyl group, Ar102 is a phenyl group, L101 is a phenylene group, L102 is a direct bond, z2 is 1, R102 is hydrogen, and m is 1 .
The organic light emitting device of claim 13, wherein the light emitting layer comprises a compound represented by Chemical Formula 1-B:

[Formula 1-B]

In Chemical Formula 1-B,

Ar101 and Ar102 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

L101 and L102 are the same as or different from each other, and are each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

R102 is hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Substituted or unsubstituted amine group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted alkyl group; A 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 aryl sulfoxy group; Substituted or unsubstituted alkenyl group; A substituted or unsubstituted aralkyl group; Substituted or unsubstituted aralkenyl group; Substituted or unsubstituted alkylaryl group; Substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted heteroarylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted arylheteroarylamine group; Substituted or unsubstituted aryl phosphine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,

z2 and z3 are the same as or different from each other, and each independently an integer of 1 or 2, z4 is an integer of 0 to 8, when z2 to z4 is 2 or more, the substituents in parentheses are the same or different from each other,

m is an integer of 1 or more, and when m is an integer of 2 or more, the substituents in parentheses are the same as or different from each other.