KR20190135935A - Hetero compound and organic light emitting device comprising the same - Google Patents

Abstract

The present specification relates to a heterocyclic compound of chemical formula 1 and an organic light emitting device comprising the same. The heterocyclic compound according to an embodiment of the present specification can be used as a material of an organic material layer of the organic light emitting device, and by using the same, it is possible to improve efficiency, lower driving voltage, and/or improve lifespan characteristics in the organic light emitting device.

Description

Heterocyclic compound and organic light emitting device including the same {HETERO COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME}

The present invention claims the benefit of the filing date of Korean Patent Application No. 10-2018-0061013 filed with the Korea Intellectual Property Office on May 29, 2018, the entire contents of which are incorporated herein.

The present specification relates to a heterocyclic 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 meet the electrons. 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.

US Patent Application Publication No. 2004-0251816

The present specification provides a heterocyclic compound and an organic light emitting device including the same.

According to an exemplary embodiment of the present specification provides a heterocyclic compound represented by the formula (1).

[Formula 1]

In Chemical Formula 1,

X1 to X3 are the same as or different from each other, and each independently N or CH

At least one of X1 to X3 is N,

R1 is hydrogen, deuterium, halogen group, nitrile group, substituted or unsubstituted alkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted silyl group, substituted or unsubstituted carbonyl group, substituted or unsubstituted carboxy group , Substituted or unsubstituted alkenyl group, substituted or unsubstituted alkynyl group, substituted or unsubstituted phosphine oxide group, substituted or unsubstituted aryl group, substituted or unsubstituted aryloxy group, or substituted or unsubstituted Heteroaryl group,

Ar1 and Ar2 are the same as or different from each other, and each independently represent a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group,

L is a straight bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,

Y is a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, and Z is substituted or Unsubstituted aryl group,

When L is a direct bond and Y is a substituted or unsubstituted aryl group, Y and Z are different,

a is an integer from 0 to 5,

When a is a plurality, R1 is the same as or different from each other.

In addition, the present specification is a first electrode; A second electrode provided to face the first electrode; And an organic light emitting device including one or two or more organic material layers provided between the first electrode and the second electrode, wherein one or more layers of the organic material layers include the heterocyclic compound. .

The heterocyclic compound according to the exemplary embodiment of the present specification may be used as a material of the organic material layer of the organic light emitting device, and by using this, it is possible to improve efficiency, low driving voltage, and / or lifespan characteristics in the organic light emitting device.

1 illustrates an organic light emitting device according to an exemplary embodiment of the present specification.
2 illustrates an organic light emitting device according to an exemplary embodiment of the present specification.

Hereinafter, this specification is demonstrated in detail.

The present specification provides a heterocyclic compound represented by Chemical Formula 1.

In the present specification, when a part "includes" a certain component, it means that it may further include other components, without excluding the other components unless otherwise stated.

In this specification, when a member is located "on" another member, this includes not only when a member is in contact with another member but also when another member exists between the two members.

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

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

As used herein, the term "substituted or unsubstituted" is deuterium; Nitrile group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted aryl group; And it is substituted with one or two or more substituents selected from the group consisting of a substituted or unsubstituted heterocyclic group, or two or more of the substituents exemplified above are substituted with a substituent, or means that do not have any substituents. For example, "a substituent to which two or more substituents are linked" may be an aryl group substituted with an aryl group, an aryl group substituted with a heteroaryl group, a heterocyclic group substituted with an aryl group, an aryl group substituted with an alkyl group, or the like.

In the present specification, the halogen group may be fluorine, chlorine, bromine or iodine.

In the present specification, the alkoxy group may be linear, branched or cyclic. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C30. Specifically, it is preferable that it is C1-C20. More specifically, it is preferable that it is C1-C10. Specifically, methoxy group; Ethoxy group; n-propoxy group; Isopropoxy group; i-propyloxy group; n-butoxy group; Isobutoxy group; tert-butoxy group; sec-butoxy group; n-pentyloxy group; Neopentyloxy group; Isopentyloxy group; n-hexyloxy group; 3,3-dimethylbutyloxy group; 2-ethylbutyloxy group; n-octyloxy group; n-nonyloxy group; n-decyloxy group; Benzyloxy group; p-methylbenzyloxy group and the like, but is not limited thereto.

In the present specification, the alkenyl group may be linear or branched chain, the carbon number is not particularly limited, but is preferably 2 to 30. More specifically, it is preferable that it is C2-C20. Specific examples include vinyl groups; 1-propenyl group; Isopropenyl group; 1-butenyl group; 2-butenyl group; 3-butenyl group; 1-pentenyl group; 2-pentenyl group; 3-pentenyl group; 3-methyl-1-butenyl group; 1,3-butadienyl group; Allyl group; 1-phenylvinyl-1-yl group; 2-phenylvinyl-1-yl group; 2,2-diphenylvinyl-1-yl group; 2-phenyl-2- (naphthyl-1-yl) vinyl-1-yl group; 2, 2-bis (diphenyl- 1-yl) vinyl- 1-yl group; Stilbenyl group; Styrenyl group and the like, but is not limited thereto.

In the present specification, the alkynyl group may be linear or branched, and the carbon number is not particularly limited, but is preferably 2 to 30. More specifically, it is preferable that it is C2-C20.

In the present specification, the phosphine oxide group is specifically a diphenylphosphine oxide group; And dinaphthylphosphine oxide groups, but are not limited thereto.

In the present specification, the alkyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 1 to 30. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, 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-dimethyl Heptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but is not limited thereto.

In the present specification, specifically, the silyl group includes trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like. However, the present invention is not limited thereto.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.

When the aryl group is a monocyclic aryl group, carbon number is not particularly limited, but is preferably 6 to 30 carbon atoms. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto.

Carbon number is not particularly limited when the aryl group is a polycyclic aryl group. It is preferable that it is C10-30. Specifically, the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, triphenyl group, pyrenyl group, penalenyl group, perylenyl group, chrysenyl group, fluorenyl group, etc., but is not limited thereto. no.

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

In the present specification, the aryl group in the aryloxy group is the same as the example of the aryl group described above.

In the present specification, the heteroaryl group includes one or more atoms other than carbon and heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se, and S, and the like. Although carbon number is not particularly limited, it is preferably 2 to 30 carbon atoms, the heteroaryl group may be monocyclic or polycyclic. Examples of the heterocyclic group include thiophene group, furanyl group, pyrrole group, imidazolyl group, thiazolyl group, oxazolyl group, oxadiazolyl group, pyridyl group, bipyridyl group, pyrimidyl group, triazinyl group, tria Sleepyl group, acridil group, pyridazinyl group, pyrazinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group , Isoquinolinyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, benzocarbazolyl group, benzothiophene group, dibenzothiophene group, benzofuranyl group, pe Nanthrolinyl group (phenanthroline), isooxazolyl group, thiadiazolyl group, phenothiazinyl group and dibenzofuranyl group and the like, but is not limited thereto.

In the present specification, the arylene group is the same as the definition of an aryl group except that it is divalent.

In the present specification, the heteroarylene group is the same as the definition of the heteroaryl group, except that it is divalent.

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

[Formula 1-1]

In Chemical Formula 1-1, X1 to X3, L, Y, Ar1, Ar2, R, and a are the same as defined in Chemical Formula 1,

R2 and R 'are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted Substituted carbonyl group, substituted or unsubstituted carboxyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted alkynyl group, substituted or unsubstituted phosphine oxide group, substituted or unsubstituted aryl group, substituted or unsubstituted A substituted aryloxy group or a substituted or unsubstituted heteroaryl group,

b and m are integers from 0 to 5,

b + m ≦ 5,

n is an integer from 0 to 1,

When b is a plurality, R2 is the same as or different from each other,

When m is plural, the R's are the same as or different from each other.

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

[Formula 2]

[Formula 3]

[Formula 4]

In Chemical Formulas 2 to 4, X1 to X3, L, Y, Ar1, Ar2, R, and a are the same as defined in Chemical Formula 1,

R2 to R6 are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted Substituted carbonyl group, substituted or unsubstituted carboxyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted alkynyl group, substituted or unsubstituted phosphine oxide group, substituted or unsubstituted aryl group, substituted or unsubstituted Aryloxy group or substituted or unsubstituted heteroaryl group,

b, d and f are each an integer of 0 to 5,

c and e are each an integer of 0 to 4,

When b is a plurality, R2 is the same as or different from each other,

When c is a plurality, R3 is the same as or different from each other,

When d is a plurality, R4 is the same as or different from each other,

When e is plural, R5 is the same as or different from each other,

When f is plural, R6 is the same as or different from each other.

According to an exemplary embodiment of the present specification, Chemical Formula 1 is represented by any one of the following Chemical Formulas 5 to 7.

[Formula 5]

[Formula 6]

[Formula 7]

In Formulas 5 to 7, wherein X1 to X3, L, Y, Ar1, Ar2, R and a are as defined in the formula (1).

According to an exemplary embodiment of the present specification, X1 is N, and X2 and X3 are CH.

According to an exemplary embodiment of the present specification, X2 is N, and X1 and X3 are CH.

According to an exemplary embodiment of the present specification, X3 is N, and X1 and X2 are CH.

According to an exemplary embodiment of the present specification, X1 and X2 are N, and X3 is CH.

According to an exemplary embodiment of the present specification, X1 and X3 are N, and X2 is CH.

According to an exemplary embodiment of the present specification, X2 and X3 are N, and X2 is CH.

According to an exemplary embodiment of the present specification, X1 to X3 is N.

According to an exemplary embodiment of the present specification, the R1 to R6 is hydrogen.

According to an exemplary embodiment of the present specification, Z is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, Z is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.

According to an exemplary embodiment of the present specification, Y is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; A silyl group unsubstituted or substituted with an alkyl group or an aryl group; Phosphine oxide groups unsubstituted or substituted with aryl groups; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, Y is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; A silyl group unsubstituted or substituted with an alkyl group or an aryl group; Phosphine oxide groups unsubstituted and substituted with aryl groups; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group containing any one or more of N, O, and S having 3 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, Y is an alkyl group; Silyl groups; Phosphine oxide groups; Aryl group; Or a heteroaryl group,

The alkyl group; Silyl groups; Phosphine oxide groups; Aryl group; Or a heteroaryl group is unsubstituted or substituted with a deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group.

According to an exemplary embodiment of the present specification, Y is an alkyl group having 1 to 10 carbon atoms; Silyl groups; Phosphine oxide groups; Aryl groups having 6 to 30 carbon atoms; Or a heteroaryl group having 3 to 30 carbon atoms,

The alkyl group having 1 to 10 carbon atoms; Silyl groups; Phosphine oxide groups; Aryl groups having 6 to 30 carbon atoms; Or a heteroaryl group having 3 to 30 carbon atoms is unsubstituted or substituted with deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

According to an exemplary embodiment of the present specification, Y is a phenyl group; Biphenyl group; Naphthyl group; Terphenyl group; Triphenylene group; Phenanthrene group; Fluoranthene group; Benzoxazole group; Benzothiazole group; Benzofury pyrimidine group; Benzothienopyrimidine group; Phosphine oxide groups; Pyridine group; Pyrimidine groups; Triazine group; Methyl group; Or silyl,

The phenyl group; Biphenyl group; Naphthyl group; Terphenyl group; Triphenylene group; Phenanthrene group; Fluoranthene group; Benzoxazole group; Benzothiazole group; Benzofury pyrimidine group; Benzothienopyrimidine group; Phosphine oxide groups; Pyridine group; Pyrimidine groups; Triazine group; Methyl group; Or the silyl group is unsubstituted or substituted with deuterium, nitrile group, halogen group, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, substituted or unsubstituted heteroaryl group.

According to an exemplary embodiment of the present specification, Y is an alkyl group having 1 to 10 carbon atoms; Silyl groups; Phosphine oxide groups; Monocyclic aryl groups having 6 to 30 carbon atoms; Polycyclic aryl groups having 10 to 30 carbon atoms; Monocyclic heteroaryl group having 3 to 30 carbon atoms or polycyclic heteroaryl group having 3 to 30 carbon atoms,

The monocyclic aryl group having 6 to 30 carbon atoms; Polycyclic aryl groups having 10 to 30 carbon atoms; Monocyclic heteroaryl groups having 3 to 30 carbon atoms or polycyclic heteroaryl groups having 3 to 30 carbon atoms are deuterium, nitrile, halogen, aryl substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted carbon atoms 6 A silaryl group substituted with an aryl group of 30 to 30, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a heteroaryl group including any one or more of N, O or S having 3 to 30 carbon atoms substituted or unsubstituted, or Substituted or unsubstituted with an phosphine oxide group unsubstituted or substituted with an alkyl group or an aryl group.

According to an exemplary embodiment of the present specification, Y is a phenyl group unsubstituted or substituted with a nitrile group, triphenylmethyl group, naphthyl group, phenylnaphthyl group, triphenylsilyl group, or trimethylsilyl group; Naphthyl group; Biphenyl group; Phenanthrene group; Terphenyl group; Triphenylene group; Fluoranthene group; Benzoxazole group; Benzothiazole group; A benzopuropyrimidine group unsubstituted or substituted with a phenyl group; A benzothienopyrimidine group unsubstituted or substituted with a phenyl group; Phosphine oxide groups substituted with phenyl groups; A pyridine group unsubstituted or substituted with a phenyl group; A pyrimidine group unsubstituted or substituted with a phenyl group; Or a triazine group unsubstituted or substituted with a phenyl group.

According to an exemplary embodiment of the present specification, Y may be any one selected from the following substituents.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms to be.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as each other, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as each other, and a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as each other, and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are different from each other, each independently represent a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are different from each other, each independently represent a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are different from each other, each independently represent a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted polycyclic polycyclic group having 6 to 30 carbon atoms. An aryl group, a substituted or unsubstituted monocyclic heteroaryl group having 3 to 30 carbon atoms, or a substituted or unsubstituted polycyclic heteroaryl group having 3 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Naphthyl group; Terphenyl group; Fluorene group; Spirobifluorene group; Phenanthrene group; Triphenylene group; Carbazole groups; Dibenzofuran group; Dibenzothiophene group; Benzonaphthofuran group; Or a benzonaphthothiophene group,

The phenyl group; Biphenyl group; Naphthyl group; Terphenyl group; Fluorene group; Spirobifluorene group; Phenanthrene group; Triphenylene group; Carbazole groups; Dibenzofuran group; Dibenzothiophene group; Benzonaphthofuran group; Or the benzonaphthothiophene group is deuterium; Halogen group; An alkyl group having 1 to 10 carbon atoms; An aryl group having 6 to 20 carbon atoms unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 30 carbon atoms; And it is substituted or unsubstituted with one or more substituents selected from the group consisting of a heteroaryl group having 3 to 30 carbon atoms substituted or unsubstituted with an aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Naphthyl group; Terphenyl group; Fluorene group; Spirobifluorene group; Phenanthrene group; Triphenylene group; Carbazole groups; Dibenzofuran group; Dibenzothiophene group; Benzonaphthofuran group; Or a benzonaphthothiophene group,

The phenyl group; Biphenyl group; Naphthyl group; Terphenyl group; Fluorene group; Spirobifluorene group; Phenanthrene group; Triphenylene group; Carbazole groups; Dibenzofuran group; Dibenzothiophene group; Benzonaphthofuran group; Or the benzonaphthothiophene group is deuterium; Phenyl group; Naphthyl group; And one or more substituents selected from the group consisting of methyl groups.

According to an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Phenanthrene group; Carbazole groups unsubstituted or substituted with a phenyl group; Dibenzofuran group; Or a dibenzothiophene group.

According to an exemplary embodiment of the present specification, Ar1 is a phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Phenanthrene group; Carbazole groups unsubstituted or substituted with a phenyl group; Dibenzofuran group; Or a dibenzothiophene group.

According to an exemplary embodiment of the present specification, Ar2 is a phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Phenanthrene group; Carbazole groups unsubstituted or substituted with a phenyl group; Dibenzofuran group; Or a dibenzothiophene group.

According to an exemplary embodiment of the present specification, L is a direct bond, or a substituted or unsubstituted arylene group.

According to an exemplary embodiment of the present specification, L is a direct bond, or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, L is a direct bond or a monocyclic substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, L is a direct bond, or a polycyclic substituted or unsubstituted arylene group having 10 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, L is a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted bivalent biphenyl group, a substituted or unsubstituted divalent terphenyl group, substituted Or an unsubstituted divalent quarterphenyl group, a substituted or unsubstituted divalent fluorene group, a substituted or unsubstituted divalent anthracene group, a substituted or unsubstituted divalent pyrene group, a substituted or unsubstituted divalent triphenylene group Or a substituted or unsubstituted divalent phenanthrene group.

According to an exemplary embodiment of the present specification, L is a phenylene group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms, a naphthylene group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms A substituted or unsubstituted divalent biphenyl group, a divalent terphenyl group substituted or unsubstituted with a C1-10 alkyl group, a divalent quarterphenyl group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms A divalent fluorene group unsubstituted or substituted with a divalent anthracene group substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms, a divalent pyrene group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms, and having 1 to 10 carbon atoms. Or a divalent phenanthrene group unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms.

According to an exemplary embodiment of the present specification, L is a phenylene group, naphthylene group, divalent biphenyl group, divalent terphenyl group, divalent quarterphenyl group, divalent fluorene unsubstituted or substituted with an alkyl group having 1 to 10 carbon atoms Group, a bivalent anthracene group, a bivalent pyrene group, a bivalent triphenylene group, or a bivalent phenanthrene group.

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

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

According to an exemplary embodiment of the present specification, L is a divalent naphthyl group.

According to yet an embodiment of the present disclosure, the heterocyclic compound of Formula 1 may be represented by the following structural formula.

The organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention includes a first electrode; A second electrode provided to face the first electrode; And an organic light emitting device including one or two or more organic material layers provided between the first electrode and the second electrode, wherein one or more layers of the organic material layers may include the aforementioned heterocyclic compounds.

For example, the structure of the organic light emitting device of the present invention may have a structure as shown in FIG. 1, but is not limited thereto.

1 illustrates a structure of an organic light emitting device in which a first electrode 2, an organic material layer 3, and a second electrode 4 are sequentially stacked on a substrate 1.

2, the first electrode 2, the hole injection layer 5, the hole transport layer 6, the electron blocking layer 7, the light emitting layer 8, the electron transport layer 9, and the electron injection layer The structure of the organic light emitting device in which 10) and the second electrode 4 are sequentially stacked is illustrated. In particular, the compound of the present invention may be included in a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, and preferably may be included in a light emitting layer.

1 and 2 illustrate an organic light emitting device and are not limited thereto.

In an exemplary embodiment of the present invention, the organic material layer includes a light emitting layer, and the light emitting layer includes the heterocyclic compound.

The organic light emitting device of the present invention includes a light emitting layer, and the light emitting layer includes a host and a dopant in a mass ratio of 90:10 to 50:50.

The organic light emitting device of the present invention includes a light emitting layer, and the light emitting layer includes a host and a dopant in a mass ratio of 90:10 to 60:40.

The organic light emitting device of the present invention includes a light emitting layer, and the light emitting layer includes a host and a dopant in a mass ratio of 90:10 to 80:20.

In an exemplary embodiment of the present invention, the organic material layer includes a light emitting layer, and the light emitting layer includes the heterocyclic compound as a host.

In an exemplary embodiment of the present invention, the organic material layer may include a light emitting layer, and the light emitting layer may include an additional host.

In one embodiment of the present invention, the organic material layer may include a light emitting layer, and the light emitting layer may include an organic compound as an additional host.

In an exemplary embodiment of the present invention, the organic material layer includes a light emitting layer, and the light emitting layer may include a carbazole derivative as an additional host.

In an exemplary embodiment of the present invention, the organic material layer may include a light emitting layer, and the light emitting layer may include a bicarbazole compound as an additional host.

In an exemplary embodiment of the present invention, the organic material layer may include a light emitting layer, and the light emitting layer may include a compound of Formula X as an additional host.

[Formula X]

In Chemical Formula X,

Ax and Ay are the same as or different from each other, and each independently a substituted or unsubstituted aryl group,

Rx and Ry are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted Substituted carbonyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted alkynyl group, substituted or unsubstituted phosphine oxide group, substituted or unsubstituted aryl group, substituted or unsubstituted aryloxy group, or substituted or Unsubstituted heteroaryl group,

x and y are each an integer of 0 to 7,

When x and y are each plural, substituents in parentheses are the same or different from each other.

In one embodiment of the present invention, Ax and Ay are the same as or different from each other, and each independently an aryl group having 6 to 30 carbon atoms.

In one embodiment of the present invention, Ax and Ay are the same as or different from each other, and are each independently a phenyl group, a biphenyl group, a terphenyl group, an anthracene group, a phenanthrene group, a triphenylene group, a fluorene group, or a pyrene group.

In one embodiment of the present invention, Ax and Ay are the same as or different from each other, and are each independently a phenyl group or a biphenyl group.

In one embodiment of the present invention, Rx and Ry are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a nitrile group, or a substituted or unsubstituted alkyl group.

In one embodiment of the present invention, Rx and Ry are hydrogen.

In an exemplary embodiment of the present invention, the organic material layer may include a light emitting layer, and the light emitting layer may include an additional dopant.

In an exemplary embodiment of the present invention, the organic material layer may include a light emitting layer, and the light emitting layer may include a fluorescent dopant.

In an exemplary embodiment of the present invention, the organic material layer may include a light emitting layer, and the light emitting layer may include a phosphorescent dopant.

In an exemplary embodiment of the present invention, the organic material layer may include a light emitting layer, and the light emitting layer may include an iridium-based dopant.

In an exemplary embodiment of the present invention, the organic material layer may include a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, the hole transport layer, or the hole injection and transport layer may include the heterocyclic compound. have.

In an exemplary embodiment of the present invention, the organic material layer may include an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, an electron transport layer, or an electron injection and transport layer may include the heterocyclic compound. have.

In an exemplary embodiment of the present invention, the organic material layer may include an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer may include the heterocyclic compound.

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.

The preparation method of the heterocyclic compound of Formula 1 and the manufacture of an organic light emitting device using the same will be described in detail in the following Examples. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited thereto.

In the following preparation method, all compounds described in the present specification may be prepared by changing the type and the substitution position of the substituents.

 [Production example]

Preparation Example 1 Preparation of Compounds 1A to 1D

1) Preparation of Compound 1A

2-chloro-4,6-diphenyl-1,3,5-triazine (50.0 g, 187 mmol) and (2-chloro-3-fluorophenyl) boronic acid (48.9 g, 280 mmol) in a nitrogen atmosphere Was added to 400 ml of tetrahydrofuran and stirred and refluxed. Thereafter, potassium carbonate (77.6 g, 561 mmol) was dissolved in 210 ml of water, stirred sufficiently, and then tetrakistriphenyl-phosphinopalladium (6.5 g, 3 mol%) was added thereto. After the reaction for 12 hours, the temperature was lowered to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled under reduced pressure. The distillate was extracted with chloroform and water, and then the organic layer was dried over magnesium sulfate. After drying the organic layer was prepared compound 1A (52.1 g, 77%) through ethyl acetate recrystallization.

MS: [M + H] < + > = 362

* 2) Preparation of Compound 1B

Compound 1A (52.1 g, 144 mmol) and (3-chloro-2-hydroxyphenyl) boronic acid (37.6 g, 216 mmol) were added to 400 ml of tetrahydrofuran in a nitrogen atmosphere, and stirred and refluxed. Thereafter, potassium carbonate (77.6 g, 561 mmol) was dissolved in 210 ml of water, stirred sufficiently, and then tetrakistriphenyl-phosphinopalladium (6.5 g, 3 mol%) was added thereto. After the reaction for 12 hours, the temperature was lowered to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled under reduced pressure. The distillate was extracted with chloroform and water, and then the organic layer was dried over magnesium sulfate. After drying the organic layer was prepared compound 1B (32.0 g, 49%) through hexane and ethyl acetate column.

MS: [M + H] < + > = 454

3) Preparation of Compound 1C

Compound 1B (32.0 g, 144 mmol) was dissolved in 300 ml of chloroform in a nitrogen atmosphere, sufficiently stirred at 0 ° C., and N-bromosuccisidimide (11.8 g, 71 mmol) was added slowly dropwise thereto. After gradually raising the temperature to room temperature, the reaction was terminated by adding water after the reaction for 1 hour. After extracting twice each using water and sodium thiosulfate solution, the organic layer was distilled under reduced pressure. The distillate was extracted with chloroform and water, and then the organic layer was dried over magnesium sulfate. Thereafter, the organic layer was dried, and then compound 1C (31.9 g, 85%) was prepared through ethyl acetate recrystallization.

MS: [M + H] < + > = 532

4) Preparation of Compound 1D

Compound 1C (31.9 g, 60 mmol) was added to 200 ml of dimethyllotamide in a nitrogen atmosphere and stirred. Then potassium carbonate (16.6 g, 120 mmol) was added and refluxed. After 2 hours, the temperature was lowered to room temperature and filtered. The filtrate was extracted with chloroform and water, and the organic layer was dried over magnesium sulfate. Thereafter, the organic layer was distilled under reduced pressure and recrystallized with ethyl acetate. The resulting solid was filtered and dried to prepare compound 1D (21.8 g, 71%).

MS: [M + H] < + > = 512

Preparation Example 2 Preparation of Compounds 2A to 2B

1) Preparation of Compound 2A

Compound 1D (25.0 g, 49 mmol) and phenylboronic acid (7.2 g, 59 mmol) were added to 200 ml of tetrahydrofuran in a nitrogen atmosphere, and the mixture was stirred and refluxed. Thereafter, potassium carbonate (20.3 g, 147 mmol) was dissolved in 60 ml of water, stirred sufficiently, and then tetrakistriphenyl-phosphinopalladium (1.7 g, 3 mol%) was added thereto. After the reaction for 12 hours, the temperature was lowered to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled under reduced pressure. The distillate was extracted with chloroform and water, and then the organic layer was dried over magnesium sulfate. After drying the organic layer was prepared compound 2A (19.2 g, 77%) through ethyl acetate recrystallization.

MS: [M + H] < + > = 510

2) Preparation of Compound 2B

Intermediate 2A (19.2 g, 38 mmol), bis (pinacolato) diboron (10.2 g, 45 mmol) and potassium acetate (7.4 g, 75 mmol) are mixed in a nitrogen atmosphere, added to 200 ml of dioxane and heated with stirring It was. At reflux, bis (dibenzylideneacetone) palladium (0.7 g, 1.1 mmol) and tricyclohexylphosphine (0.7 g, 2.3 mmol) were added thereto, and the mixture was heated and stirred for 3 hours. After the reaction was completed, the temperature was lowered to room temperature, followed by filtration. Water was poured into the filtrate, and extracted with chloroform, and the organic layer was dried over anhydrous magnesium sulfate. After distillation under reduced pressure, compound 2B (18.1 g, 80%) was prepared by recrystallization with ethanol.

MS: [M + H] < + > = 602

Preparation Example 3 Preparation of Compounds 3A to 3B

1) Preparation of Compound 3A

Compound 1D (25.0 g, 49 mmol) and [1,1'-biphenyl] -4-ylboronic acid (11.6 g, 59 mmol) were added to 200 ml of tetrahydrofuran in a nitrogen atmosphere, and stirred and refluxed. Thereafter, potassium carbonate (20.3 g, 147 mmol) was dissolved in 60 ml of water, stirred sufficiently, and then tetrakistriphenyl-phosphinopalladium (1.7 g, 3 mol%) was added thereto. After the reaction for 12 hours, the temperature was lowered to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled under reduced pressure. The distillate was extracted with chloroform and water, and then the organic layer was dried over magnesium sulfate. After drying the organic layer was prepared compound 3A (23.8 g, 83%) through ethyl acetate recrystallization.

MS: [M + H] < + > = 586

1) Preparation of Compound 3B

Intermediate 3A (23.8 g, 41 mmol), bis (pinacolato) diboron (11.3 g, 45 mmol) and potassium acetate (7.4 g, 75 mmol) are mixed in a nitrogen atmosphere, added to 200 ml of dioxane and heated with stirring It was. Bis (dibenzylideneacetone) palladium (0.7 g, 1.2 mmol) and tricyclohexylphosphine (0.7 g, 2.4 mmol) were added under reflux, and the mixture was heated and stirred for 5 hours. After the reaction was completed, the temperature was lowered to room temperature, followed by filtration. Water was poured into the filtrate, and extracted with chloroform, and the organic layer was dried over anhydrous magnesium sulfate. Compound 3B (24.2 g, 88%) was prepared by recrystallization with ethanol after distillation under reduced pressure.

MS: [M + H] < + > = 678

Preparation Example 4 Preparation of Compounds 4A to 4B

1) Preparation of Compound 4A

Compound 1D (25.0 g, 49 mmol) and [1,1'-biphenyl] -3-ylboronic acid (11.6 g, 59 mmol) were added to 200 ml of tetrahydrofuran in a nitrogen atmosphere, and stirred and refluxed. Thereafter, potassium carbonate (20.3 g, 147 mmol) was dissolved in 60 ml of water, stirred sufficiently, and then tetrakistriphenyl-phosphinopalladium (1.7 g, 3 mol%) was added thereto. After the reaction for 12 hours, the temperature was lowered to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled under reduced pressure. The distillate was extracted with chloroform and water, and then the organic layer was dried over magnesium sulfate. After drying the organic layer was prepared compound 4A (18.9 g, 66%) through ethyl acetate recrystallization.

MS: [M + H] < + > = 586

2) Preparation of Compound 4B

Intermediate 4A (18.9 g, 32 mmol), bis (pinacolato) diboron (9.0 g, 35 mmol) and potassium acetate (6.3 g, 65 mmol) are mixed in a nitrogen atmosphere, added to 200 ml of dioxane and heated with stirring It was. At reflux, bis (dibenzylideneacetone) palladium (0.6 g, 1.0 mmol) and tricyclohexylphosphine (0.6 g, 1.9 mmol) were added thereto, and the mixture was heated and stirred for 5 hours. After the reaction was completed, the temperature was lowered to room temperature, followed by filtration. Water was poured into the filtrate, and extracted with chloroform, and the organic layer was dried over anhydrous magnesium sulfate. Compound 4B (10.9 g, 50%) was prepared by recrystallization with ethanol after distillation under reduced pressure.

MS: [M + H] < + > = 678

Preparation Example 5 Preparation of Compounds 1 to 15

1) Synthesis of Compound 1

In a nitrogen atmosphere, intermediate 2A (10 g, 20 mmol) and [1,1'-biphenyl] -4-ylboronic acid (8.0 g, 40 mmol) were added to 100 ml of dioxane and stirred and refluxed. After dissolving potassium phosphate (12.5g, 59mmol) in 40ml of water, the mixture was sufficiently stirred, and then stirred thoroughly. Input. After the reaction for 12 hours, the temperature was lowered to room temperature and filtered. The filtrate was extracted with chloroform and water, and the organic layer was dried over magnesium sulfate. Thereafter, the organic layer was distilled under reduced pressure and recrystallized with ethyl acetate. The resulting solid was filtered and dried to give compound 1 (9.5 g, 77%).

MS: [M + H] < + > = 628

2) Synthesis of Compound 2

Compound 2 (9.5 g, 54%) was synthesized in the same manner as in the synthesis of Compound 1, except that the compound was used instead of [1,1'-biphenyl] -4-ylboronic acid.

MS: [M + H] < + > = 704

3) Synthesis of Compound 3

Compound 3 (10.6 g, 83%) was synthesized in the same manner as in the synthesis of Compound 1, except that phenanthrene-2-ylboronic acid was used instead of [1,1'-biphenyl] -4-ylboronic acid.

MS: [M + H] < + > = 652

4) Synthesis of Compound 4

Compound 2B (10.0 g, 17 mmol) and 2-chlorobenzo [d] thiazole (3.1 g, 18 mmol) were added to 100 ml of tetrahydrofuran in a nitrogen atmosphere, and the mixture was stirred and refluxed. Thereafter, potassium carbonate (6.9 g, 49 mmol) was dissolved in 20 ml of water, and stirred sufficiently, and then tetrakistriphenyl-phosphinopalladium (0.6 g, 3 mol%) was added thereto. After the reaction for 12 hours, the temperature was lowered to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled under reduced pressure. The distillate was extracted with chloroform and water, and then the organic layer was dried over magnesium sulfate. After drying the organic layer was prepared compound 4 (4.5 g, 44%) through ethyl acetate recrystallization.

MS: [M + H] < + > = 609

5) Synthesis of Compound 5

Except for using 2-chloro-4,6-diphenyl-1,3,5-triazine in place of 2-chlorobenzo [d] thiazole, Compound 5 (8.7 g) was prepared in the same manner as in the synthesis of Compound 4. , 74%).

MS: [M + H] < + > = 707

6) Synthesis of Compound 6

In a nitrogen atmosphere, intermediate 3A (10 g, 17 mmol) and phenylboronic acid (2.2 g, 19 mmol) were added to 100 ml of dioxane and stirred and refluxed. After dissolving potassium phosphate (10.9g, 52mmol) in 30ml of water, the mixture was sufficiently stirred, and then stirred thoroughly. Input. After the reaction for 12 hours, the temperature was lowered to room temperature and filtered. The filtrate was extracted with chloroform and water, and the organic layer was dried over magnesium sulfate. Thereafter, the organic layer was distilled under reduced pressure and recrystallized with ethyl acetate. The resulting solid was filtered and dried to prepare compound 6 (6.8 g, 63%).

MS: [M + H] < + > = 628

7) Synthesis of Compound 7

Compound 7 (6.6 g, 55%) was synthesized in the same manner as in the synthesis of Compound 6, except that biphenyl-3-ylboronic acid was used instead of phenylboronic acid.

MS: [M + H] < + > = 704

8) Synthesis of Compound 8

Synthesis of Compound 6 was repeated except that naphthalen-2-ylboronic acid was used instead of phenylboronic acid. Compound 8 (9.0 g, 78%) was synthesized through the method.

MS: [M + H] < + > = 678

9) Synthesis of Compound 9

Compound 3B (10.0 g, 15 mmol) and 2-chlorobenzo [d] thiazole (2.7 g, 16 mmol) were added to 100 ml of tetrahydrofuran in a nitrogen atmosphere, and the mixture was stirred and refluxed. Thereafter, potassium carbonate (6.1 g, 44 mmol) was dissolved in 20 ml of water, stirred sufficiently, and then tetrakistriphenyl-phosphinopalladium (0.5 g, 3 mol%) was added thereto. After the reaction for 12 hours, the temperature was lowered to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled under reduced pressure. The distillate was extracted with chloroform and water, and then the organic layer was dried over magnesium sulfate. After drying the organic layer was prepared compound 9 (8.1 g, 80%) through ethyl acetate recrystallization.

MS: [M + H] < + > = 685

10) Synthesis of Compound 10

Compound 10 (9.1 g) was prepared in the same manner as in the synthesis of Compound 9, except that 2-chloro-4,6-diphenyl-1,3,5-triazine was used instead of 2-chlorobenzo [d] thiazole. , 79%) was synthesized.

MS: [M + H] < + > = 783

11) Synthesis of Compound 11

In a nitrogen atmosphere, intermediate 4A (10 g, 17 mmol) and phenylboronic acid (2.2 g, 19 mmol) were added to 100 ml of dioxane and stirred and refluxed. After dissolving potassium phosphate (10.9g, 52mmol) in 30ml of water, the mixture was sufficiently stirred, and then sufficiently stirred. Input. After the reaction for 12 hours, the temperature was lowered to room temperature and filtered. The filtrate was extracted with chloroform and water, and then the organic layer was dried over magnesium sulfate. The organic layer was then recrystallized using distillation under reduced pressure using ethyl acetate. The resulting solid was filtered and dried to give compound 11 (7.4 g, 64%).

MS: [M + H] < + > = 678

12) Synthesis of Compound 12

Compound 12 (6.8 g, 57%) was synthesized in the same manner as in the synthesis of Compound 11, except that [1,1'-biphenyl] -4-ylboronic acid was used instead of phenylboronic acid.

MS: [M + H] < + > = 704

13) Synthesis of Compound 13

Compound 13 (8.1 g, 70%) was synthesized in the same manner as in the synthesis of Compound 11, except that naphthalen-2-ylboronic acid was used instead of phenylboronic acid.

MS: [M + H] < + > = 678

14) Synthesis of Compound 14

Compound 4B (10.0 g, 15 mmol) and 2-chlorobenzo [d] thiazole (2.7 g, 16 mmol) were added to 100 ml of tetrahydrofuran in a nitrogen atmosphere, and the mixture was stirred and refluxed. Thereafter, potassium carbonate (6.1 g, 44 mmol) was dissolved in 20 ml of water, stirred sufficiently, and then tetrakistriphenyl-phosphinopalladium (0.5 g, 3 mol%) was added thereto. After the reaction for 12 hours, the temperature was lowered to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled under reduced pressure. The distillate was extracted with chloroform and water, and then the organic layer was dried over magnesium sulfate. After drying the organic layer was prepared compound 14 (4.2 g, 42%) through ethyl acetate recrystallization.

MS: [M + H] < + > = 685

15) Synthesis of Compound 15

Compound 15 (6.9 g) was prepared in the same manner as in the synthesis of Compound 14, except that 2-chloro-4,6-diphenyl-1,3,5-triazine was used instead of 2-chlorobenzo [d] thiazole. , 60%).

MS: [M + H] < + > = 783

Experimental Example

Experimental Example 1

The glass substrate coated with ITO (indium tin oxide) having a thickness of 1,300 kPa was put in distilled water in which detergent was dissolved and ultrasonically cleaned. In this case, Fischer Co. was used as a detergent, and distilled water was filtered secondly as a filter of Millipore Co. as a distilled water. After washing ITO for 30 minutes, the ultrasonic cleaning was repeated 10 times with distilled water twice. 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.

On the ITO transparent electrode prepared as above, the following HI-1 compound was thermally vacuum deposited to a thickness of 50 kPa to form a hole injection layer. A hole transport layer was formed by thermal vacuum deposition of the following HT-1 compound to a thickness of 250 GPa on the hole injection layer, and an electron blocking layer was formed by vacuum deposition of the following HT-2 compound to 50 GPa on the HT-1 deposition film. Compound 1, the following YGH-1 compound, and phosphorescent dopant YGD-1, prepared as a light emitting layer on the HT-2 deposited film by vacuum deposition at a weight ratio of 44:44:12, form a light emitting layer having a thickness of 400 kHz. The following ET-1 compound was vacuum deposited to a thickness of 250 kPa on the light emitting layer to form an electron transport layer, and the following ET-2 compound and Li were vacuum deposited on the electron transport layer at a weight ratio of 98: 2 to form an electron injection layer having a thickness of 100 kW. Formed. Aluminum was deposited to a thickness of 1000 Å on the electron injection layer to form a cathode.

In the above process, the deposition rate of the organic material was maintained at 0.4 ~ 0.7 Å / sec, the aluminum was maintained at the deposition rate of 2 Å / sec, the vacuum during deposition was maintained at 1 × 10 ^-7 ~ 5 × 10 ^-8 torr It was.

Experimental Examples 2 to 15

An organic light emitting diode was manufactured according to the same method as Experimental Example 1 except for using the compound described in Table 1 below instead of compound 1 in Experimental Example 1.

<Comparative Experimental Examples 1 to 3>

An organic light emitting diode was manufactured according to the same method as Experimental Example 1 except for using the compound described in Table 1 below instead of compound 1 in Experimental Example 1. The compounds of CE1 to CE3 in Table 1 are as follows.

Experimental Example and Comparative an organic light-emitting device of Experimental Example were measured and a voltage efficiency at a current density of 10mA / cm ^2, to measure the lifetime at a current density of 50mA / cm ² and the results are shown in Table 1. In this case, LT95 means a time of 95% of the initial luminance.

compound Voltage (V)
(@ 10mA / cm ² ) Efficiency (Cd / A)
(@ 10mA / cm ² ) Color coordinates
(x, y) Life (h)
(LT ₉₅ at 50mA / cm ² ) Experimental Example 1 Compound 1 3.8 80 0.45, 0.54 100 Experimental Example 2 Compound 2 3.9 82 0.46, 0.53 120 Experimental Example 3 Compound 3 4.0 78 0.45, 0.53 150 Experimental Example 4 Compound 4 3.9 81 0.45, 0.54 125 Experimental Example 5 Compound 5 3.7 82 0.45, 0.54 150 Experimental Example 6 Compound 6 3.8 80 0.45, 0.54 110 Experimental Example 7 Compound 7 3.9 81 0.46, 0.53 135 Experimental Example 8 Compound 8 4.0 84 0.45, 0.54 128 Experimental Example 9 Compound 9 4.3 81 0.45, 0.54 115 Experimental Example 10 Compound 10 3.9 82 0.45, 0.54 130 Experimental Example 11 Compound 11 3.7 84 0.46, 0.53 100 Experimental Example 12 Compound 12 3.8 83 0.45, 0.54 160 Experimental Example 13 Compound 13 4.1 80 0.46, 0.53 105 Experimental Example 14 Compound 14 4.0 80 0.45, 0.54 100 Experimental Example 15 Compound 15 3.8 80 0.45, 0.54 105 Comparative Experimental Example 1 CE1 4.5 70 0.46, 0.54 80 Comparative Experimental Example 2 CE2 4.0 75 0.47, 0.53 30 Comparative Experiment 3 CE3 6.0 45 0.43, 0.53 5

The compound of the present invention showed lower voltage, higher efficiency and longer life compared to CE1 which does not include a dibenzofuran core, and when N-containing monocyclic ring, such as CE2, binds to position 2 of dibenzofuran In comparison with Experimental Examples 1 to 15 using the compound of the present invention, it showed a low efficiency and a significantly short lifespan, and when the substituent at position 1 of the dibenzofuran is not N-containing monocyclic ring, such as CE3, the highest voltage and low Current efficiency and shortest lifetime were shown.

Therefore, when the compound of the present invention is used as a light emitting layer material, it was confirmed that exhibits excellent efficiency and lifespan as compared to the comparative experimental example. It is shown that the electron stability is increased by substituting the aryl group with the 6 and 8 substitution positions of the dibenzofuran substituent.

1: substrate
2: first electrode
3: organic layer
4: second electrode
5: hole injection layer
6: hole transport layer
7: electronic jersey
8: light emitting layer
9: electron transport layer
10: electron injection layer

Claims (8)

Heterocyclic compounds represented by the formula (1):
[Formula 1]

In Chemical Formula 1,
X1 to X3 are the same as or different from each other, and each independently N or CH
At least one of X1 to X3 is N,
R1 is hydrogen, deuterium, halogen group, nitrile group, substituted or unsubstituted alkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted silyl group, substituted or unsubstituted carbonyl group, substituted or unsubstituted carboxy group , Substituted or unsubstituted alkenyl group, substituted or unsubstituted alkynyl group, substituted or unsubstituted phosphine oxide group, substituted or unsubstituted aryl group, substituted or unsubstituted aryloxy group, or substituted or unsubstituted Heteroaryl group,
Ar1 and Ar2 are the same as or different from each other, and each independently represent a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group,
L is a straight bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,
Y is a substituted or unsubstituted alkyl group, a substituted or unsubstituted silyl group, a substituted or unsubstituted phosphine oxide group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group,
Z is a substituted or unsubstituted aryl group,
When L is a direct bond and Y is a substituted or unsubstituted aryl group, Y and Z are different,
a is an integer from 0 to 5,
When a is a plurality, R1 is the same as or different from each other. The heterocyclic compound according to claim 1, wherein Formula 1 is represented by any one of Formulas 2 to 4 below:
[Formula 2]

[Formula 3]

[Formula 4]

In Chemical Formulas 2 to 4, X1 to X3, L, Y, Ar1, Ar2, R, and a are the same as defined in Chemical Formula 1,
R2 to R6 are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted silyl group, a substituted or unsubstituted Substituted carbonyl group, substituted or unsubstituted carboxyl group, substituted or unsubstituted alkenyl group, substituted or unsubstituted alkynyl group, substituted or unsubstituted phosphine oxide group, substituted or unsubstituted aryl group, substituted or unsubstituted Aryloxy group or substituted or unsubstituted heteroaryl group,
b, d and f are each an integer of 0 to 5,
c and e are each an integer of 0 to 4,
When b is a plurality, R2 is the same as or different from each other,
When c is a plurality, R3 is the same as or different from each other,
When d is a plurality, R4 is the same as or different from each other,
When e is plural, R5 is the same as or different from each other,
When f is plural, R6 is the same as or different from each other. The method of claim 1, wherein Ar1 and Ar2 are the same as or different from each other, each independently substituted or unsubstituted monocyclic aryl group having 6 to 30 carbon atoms, substituted or unsubstituted polycyclic aryl group having 6 to 30 carbon atoms, substituted Or an unsubstituted monocyclic heteroaryl group having 3 to 30 carbon atoms or a substituted or unsubstituted polycyclic heteroaryl group having 3 to 30 carbon atoms. The heterocyclic compound according to claim 1, wherein L is a direct bond or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms. The method according to claim 1, wherein Y is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; A silyl group unsubstituted or substituted with an alkyl group or an aryl group; Phosphine oxide groups unsubstituted or substituted with aryl groups; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group including any one or more of N, O, and S having 3 to 30 carbon atoms. The heterocyclic compound according to claim 1, wherein Formula 1 is any one selected from the following compounds:

A first electrode; A second electrode provided to face the first electrode; And one or two or more organic material layers provided between the first electrode and the second electrode, wherein one or more layers of the organic material layers include the heterocyclic compound according to any one of claims 1 to 6. Phosphorescent 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 heterocyclic compound.

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