KR102020521B1 - Hrtrro-cyclic compound and organic light emitting device comprising the same - Google Patents

Abstract

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

Description

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

This application claims the benefit of the filing date of Korean Patent Application No. 10-2015-0169334 filed with the Korea Intellectual Property Office on November 30, 2015, 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 utilizing an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween. The organic material layer is often made 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 electrons meet. 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.

International Patent Application Publication No. 2003-012890

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

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

[Formula 1]

In Chemical Formula 1,

R ₀ to R ₉ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Imide group; Amide group; Carbonyl group; Ester group; Hydroxyl 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; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl phosphine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or two adjacent to each other of R ₀ to R ₉ combine with each other to form a substituted or unsubstituted 6 membered ring,

A ₁ and A ₂ are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or combine with each other to form a substituted or unsubstituted ring,

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

Z ₁ is a nitrile group; Substituted or unsubstituted aryl group; Substituted or unsubstituted two or more heteroaryl groups; Or a substituted or unsubstituted phosphine oxide group.

Another embodiment of the present specification is 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 including a light emitting layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises a heterocyclic compound represented by Chemical Formula 1. An organic light emitting device is provided.

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 the same, it is possible to improve efficiency, low driving voltage, and / or lifespan characteristics in the organic light emitting device.

1 to 5 are cross-sectional views illustrating a structure of an organic light emitting diode according to an exemplary embodiment of the present specification.
6 is a diagram showing an LC / MS graph of Chemical Formula 2-2-4 prepared from Preparation Example 7. FIG.
7 is a diagram showing an LC / MS graph of Chemical Formula 2-5-3 prepared from Preparation Example 15.
8 is a diagram showing an LC / MS graph of Chemical Formula 2-5-4 prepared from Preparation Example 16.

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, this means that it may further include other components, without excluding other components unless specifically stated otherwise.

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.

As used herein, the term "adjacent" means a substituent substituted on an atom directly connected to an atom to which the substituent is substituted, a substituent positioned closest to the substituent, or another substituent substituted on an 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.

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; Halogen group; Nitrile group; Nitro group; Imide group; Amide group; Carbonyl group; Ester group; Hydroxyl group; An alkyl group; Cycloalkyl group; An alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy groups; Aryl sulfoxy group; Alkenyl groups; Silyl groups; Boron group; Amine group; Aryl phosphine group; Phosphine oxide groups; Aryl group; And it means that it is substituted with one or two or more substituents selected from the group consisting of a heterocyclic group or substituted with a substituent to which two or more substituents in the above-described substituents are connected, or does not have any substituents. 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.

는 다른 치환기 또는 결합부에 결합되는 부위를 의미한다.In the present specification,

Means a site which is bonded to another substituent or binding moiety.

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

In this specification, although carbon number of an imide group is not specifically limited, It is preferable that it is C1-C30. Specifically, it may be a compound having a structure as follows, but is not limited thereto.

In the present specification, the amide group may be substituted with nitrogen of the amide group is hydrogen, a linear, branched or cyclic alkyl group having 1 to 30 carbon atoms or an aryl group having 6 to 30 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

Although carbon number of a carbonyl group in this specification is not specifically limited, It is preferable that it is C1-C30. Specifically, it may be a compound having a structure as follows, but is not limited thereto.

In the present specification, the ester group may be substituted with oxygen of the ester group having a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 30 carbon atoms. Specifically, it may be a compound of the following structural formula, but is 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, the cycloalkyl group is not particularly limited, but preferably has 3 to 30 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 are not limited thereto. It is not.

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, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, Isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy and the like It may be, but is not limited thereto.

In the present specification, the amine group is -NH ₂ ; Alkylamine group; N-arylalkylamine group; Arylamine group; N-aryl heteroaryl amine group; It may be selected from the group consisting of an N-alkylheteroarylamine group and a heteroarylamine group, carbon number 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, and 9-methyl-anthracenylamine group. , Diphenylamine group, N-phenylnaphthylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group and the like, but is not limited thereto.

In the present specification, the N-alkylarylamineamine group means an amine group in which an alkyl group and an aryl group are substituted for N of the amine group.

In the present specification, the N-arylheteroarylamine group means an amine group in which an aryl group and a heteroaryl group are substituted for N in the amine group.

In the present specification, the N-alkylheteroarylamine group means an amine group in which an alkyl group and a heteroarylamine group are substituted for N of the amine group.

In the present specification, the alkyl group in the alkylamine group, the N-arylalkylamine group, the alkylthioxy group, the alkyl sulfoxy group, and the N-alkylheteroarylamine group is the same as the example of the alkyl group described above. Specifically, the alkyl thioxy group includes a methyl thioxy group, an ethyl thioxy group, a tert-butyl thioxy group, a hexyl thioxy group, an octyl thioxy group, and the alkyl sulfoxy group includes mesyl, ethyl sulfoxy, propyl sulfoxy, and butyl sulfoxy groups. Etc., but is not limited thereto.

In the present specification, the alkenyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 2 to 30. 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, 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 boron group may be -BR ₁₀₀ R ₁₀₁ R ₁₀₂ , wherein R ₁₀₀ , R ₁₀₁ and R ₁₀₂ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; Nitrile group; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; Substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And it may be selected from the group consisting of a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

In the present specification, phosphine oxide groups include, but are not limited to, diphenylphosphine oxide group, dinaphthylphosphine oxide, and the like.

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, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.

In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.

,

,

및

등이 될 수 있다. 다만, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,

,

,

And

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

In the present specification, the aryl group in the aryloxy group, arylthioxy group, aryl sulfoxy group, N-arylalkylamine group, N-arylheteroarylamine group, and arylphosphine group is the same as the examples of the aryl group described above. Specifically, the aryloxy group may be a phenoxy group, p-tolyloxy group, m-tolyloxy group, 3,5-dimethyl-phenoxy group, 2,4,6-trimethylphenoxy group, p-tert-butylphenoxy group, 3- Biphenyloxy group, 4-biphenyloxy group, 1-naphthyloxy group, 2-naphthyloxy group, 4-methyl-1-naphthyloxy group, 5-methyl-2-naphthyloxy group, 1-anthryloxy group , 2-anthryloxy group, 9-anthryloxy group, 1-phenanthryloxy group, 3-phenanthryloxy group, 9-phenanthryloxy group, and the like. Examples of the arylthioxy group include a phenylthioxy group and 2- The methylphenyl thioxy group, 4-tert- butylphenyl thioxy group, etc. are mentioned, An aryl sulfoxy group includes a benzene sulfoxy group, p-toluene sulfoxy group, etc., but is not limited to this.

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. For example, the aryl group in the arylamine group may be selected from the examples of the aryl group described above.

In the present specification, in the present specification, the heteroaryl group includes one or more atoms other than carbon and hetero atoms, and specifically, the hetero atoms include one or more atoms selected from the group consisting of O, N, Se, and S, and the like. It may include. 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 Zolyl 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), thiazolyl group, isooxazolyl group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl group, phenothiazinyl group and dibenzofuranyl group and the like, but is 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 heteroarylamine group including two or more heteroaryl groups may simultaneously include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group. For example, the heteroaryl group in the heteroarylamine group may be selected from the examples of the heteroaryl group described above.

In the present specification, examples of the heteroaryl group in the N-arylheteroarylamine group and the N-alkylheteroarylamine group are the same as the examples of the heteroaryl group described above.

In the present specification, the heterocyclic group may be monocyclic or polycyclic, may be aromatic, aliphatic or a condensed ring of aromatic and aliphatic, and may be selected from examples of the heteroaryl group.

In the present specification, the arylene group refers to a divalent group having two bonding positions in the aryl group. The description of the aforementioned aryl group can be applied except that they are each divalent.

In the present specification, the heteroarylene group means a divalent group having two bonding positions in the heteroaryl group. The description of the aforementioned heteroaryl group can be applied except that they are each divalent.

In the present specification, in a substituted or unsubstituted ring in which adjacent groups are formed by bonding to each other, a “ring” means a substituted or unsubstituted hydrocarbon ring; Or substituted or unsubstituted heterocycle.

In the present specification, the hydrocarbon ring may be an aromatic, aliphatic or a condensed ring of aromatic and aliphatic, and may be selected from examples of the cycloalkyl group or aryl group except for the above-mentioned monovalent one.

In the present specification, the aromatic ring may be monocyclic or polycyclic, and may be selected from examples of the aryl group except that it is not monovalent.

In the present specification, the heterocycle 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. The heterocycle may be monocyclic or polycyclic, may be aromatic, aliphatic or a condensed ring of aromatic and aliphatic, and may be selected from examples of the heteroaryl group except that it is not monovalent.

According to another exemplary embodiment of the present specification, Chemical Formula 1 may be represented by any one of the following Chemical Formulas 1-1 to 1-3.

[Formula 1-1] [Formula 1-2] [Formula 1-3]

In Formulas 1-1 to 1-3, R ₀ to R ₉ , A ₁ , A ₂ , L, and Z ₁ are the same as defined in Formula 1,

R ₁₀ to R ₁₂ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Imide group; Amide group; Carbonyl group; Ester group; Hydroxyl 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; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl phosphine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or two adjacent to each other combine with each other to form a substituted or unsubstituted ring,

q is an integer of 1 to 4,

When q is two or more, the structures in two or more parentheses are the same or different from each other.

According to another exemplary embodiment of the present specification, Chemical Formula 1 may be represented by any one of the following Chemical Formulas 2-1 to 2-8.

[Formula 2-1] [Formula 2-2]

[Formula 2-3] [Formula 2-4]

[Formula 2-5] [Formula 2-6]

[Formula 2-7] [Formula 2-8]

In Chemical Formulas 2-1 and 2-8, R ₀ to R ₉ , L And Z ₁ is the same as defined in Formula 1,

R ₁₀ to R ₁₅ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Imide group; Amide group; Carbonyl group; Ester group; Hydroxyl 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; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl phosphine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or two adjacent to each other combine with each other to form a substituted or unsubstituted ring,

q is an integer of 1 to 4, t is an integer of 1 to 8, s is an integer of 1 to 5,

When q, t and s are each 2 or more, the structures in the two or more parentheses are the same as or different from each other.

According to an exemplary embodiment of the present specification, in the general formula 1, A ₁ and A ₂ is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification in the general formula 1, A ₁ And A ₂ Is a substituted or unsubstituted phenyl group; Or a fluorene group which is bonded to each other to form a substituted or unsubstituted ring.

According to an exemplary embodiment of the present specification in the general formula 1, A _One And A _{2 Are} phenyl; Or a fluorene group bonded to each other to form a ring.

According to an exemplary embodiment of the present specification, in the general formula 1, R _{0 To} R ₉ are each independently hydrogen.

According to an exemplary embodiment of the present disclosure in the general formula 1, L is a direct bond; a substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylylene group; Or a substituted or unsubstituted pyridylene group.

According to an exemplary embodiment of the present specification, in the general formula 1, L is a direct bond; Phenylene group; Biphenylylene group; Or a pyridylene group.

According to an exemplary embodiment of the present specification, in the general formula 1, Z ₁ Is a nitrile group; Phosphine oxide groups substituted with aryl groups; An aryl group unsubstituted or substituted with an aryl group; 2 or unsubstituted or substituted with a nitrile group, an aryl group, an aryl group substituted with a nitrile group, an aryl group substituted with an alkyl group, an aryl group substituted with a phosphine oxide group substituted with an aryl group, or a heteroaryl group substituted or unsubstituted with an aryl group Heteroaryl group more than a ring.

According to an exemplary embodiment of the present specification, in the general formula 1, Z ₁ Is a nitrile group; Phosphine oxide groups substituted with a phenyl group or a naphthyl group; A phenyl group unsubstituted or substituted with a phenyl group; Biphenyl group; Naphthyl group; Anthracenyl group unsubstituted or substituted with a phenyl group; Phenanthrenyl group; Fluoranthenyl group; Triphenylenyl group; Terphenyl group; Indazolyl group; Benzimidazole groups substituted with phenyl groups; Or represented by any one of the following Formulas A to D.

[Formula A]

In Chemical Formula A,

Y ₁ is N or R ₂₀₁ , Y ₂ is N or R ₂₀₂ , Y ₃ is N or R ₂₀₃ , Y ₄ is N or R ₂₀₄ , Y ₅ is N or R ₂₀₅ , Y ₆ is N or R ₂₀₆ , Y ₇ is N or R ₂₀₇ ,

Any one of R ₂₀₁ to R ₂₀₇ is a moiety bonded to Formula 1 through L of Formula 1, and the other are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Imide group; Amide group; Carbonyl group; Ester group; Hydroxyl 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; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl phosphine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or adjacent groups combine with each other to form a substituted or unsubstituted ring.

[Formula B]

In Chemical Formula B,

Y ₈ is N or R ₂₀₈ , Y ₉ is N or R ₂₀₉ , Y ₁₀ is N or R ₂₁₀ , Y ₁₁ is N or R ₂₁₁ , Y ₁₂ is N or R ₂₁₂ , Y ₁₃ is N or R ₂₁₃ , Y ₁₄ is N or R ₂₁₄ ,

Any one of R ₂₀₈ to R ₂₁₄ is a moiety bonded to Formula 1 through L in Formula 1, and the others are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Imide group; Amide group; Carbonyl group; Ester group; Hydroxyl 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; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl phosphine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or adjacent groups combine with each other to form a substituted or unsubstituted ring.

[Formula C]

In Chemical Formula C,

T ₁ is N or R ₃₀₉ , T ₂ is N or R ₃₁₀ ,

At least one of T ₁ and T ₂ is N,

Any one of R ₃₀₁ to R ₃₀₈ is a moiety bonded to Formula 1 through L of Formula 1, and the other and R ₃₀₉ and R ₃₁₀ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Imide group; Amide group; Carbonyl group; Ester group; Hydroxyl 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; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl phosphine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or R ₃₀₁ and R ₃₀₂ combine with each other to form a ring substituted with R _c ,

When R ₃₀₁ and R ₃₀₂ are bonded to each other to form a ring substituted with R _c , any one of R ₃₀₃ to R ₃₀₈ and R c may be a site bonded to Formula 1 through L of Formula 1, ,

R _c is hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Imide group; Amide group; Carbonyl group; Ester group; Hydroxyl 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; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl phosphine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

[Formula D]

In Chemical Formula D,

G ₁ is O, S, NR ₄₀₁ , or CR ₄₁₀ R ₄₁₁ ,

U ₁ is N or R ₄₀₂ , U ₂ is N or R ₄₀₃ , U ₃ is N or R ₄₀₄ , U ₄ is N or R ₄₀₅ , U ₅ is N or R ₄₀₆ , U ₆ is N or R ₄₀₇ , U ₇ is N or R ₄₀₈ , U ₈ is N or R ₄₀₉ ,

When G ₁ is CR ₄₁₀ R ₄₁₁ , at least one of U ₁ to U ₈ is N,

Any one of R ₄₀₁ to R ₄₁₁ is a moiety bonded to Formula 1 through L of Formula 1, and the other are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Imide group; Amide group; Carbonyl group; Ester group; Hydroxyl 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; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl phosphine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

According to an exemplary embodiment of the present specification, the formula A is represented by any one of the formulas A-1 to A-4.

[Formula A-1]

[Formula A-2]

[Formula A-3]

[Formula A-4]

In Formulas A-1 to A-4, the definitions of Y ₂ , Y ₃ , R ₂₀₁ and R ₂₀₄ to R ₂₀₇ are the same as those of Formula A.

According to an exemplary embodiment of the present specification, the formula A is represented by any one of the formulas A-5 to A-12.

[Formula A-5]

[Formula A-6]

[Formula A-7]

[Formula A-8]

[Formula A-9]

[Formula A-10]

[Formula A-11]

[Formula A-12]

In Formulas A-5 to A-12, the definitions of R ₂₀₁ to R ₂₀₇ are the same as those of Formula A.

According to an exemplary embodiment of the present specification, in the general formula A, any one of R ₂₀₁ to R ₂₀₇ is a site bonded to the general formula (1) through L of the general formula (1), the remainder are the same as or different from each other, and each independently Hydrogen; Nitrile group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

According to an exemplary embodiment of the present specification, in the general formula A, any one of R ₂₀₁ to R ₂₀₇ is a site bonded to the general formula (1) through L of the general formula (1), the remainder are the same as or different from each other, and each independently Hydrogen; Nitrile group; An alkyl group; An aryl group unsubstituted or substituted with a phosphine oxide group substituted with a nitrile group, an alkyl group, or an aryl group; Or a heteroaryl group unsubstituted or substituted with an aryl group.

According to an exemplary embodiment of the present specification, in the general formula A, any one of R ₂₀₁ to R ₂₀₇ is a site bonded to the general formula (1) through L of the general formula (1), the remainder are the same as or different from each other, and each independently Hydrogen; Nitrile group; Methyl group; A phenyl group substituted with a phosphine oxide group substituted with a nitrile group or an aryl group; Biphenyl group; Naphthyl group; A fluorenyl group unsubstituted or substituted with an alkyl group; Phenanthrenyl group; Pyridyl group; Carbazolyl group unsubstituted or substituted with an aryl group; Benzocarbazolyl group; Dibenzofuranyl group; Or a dibenzothiophene group.

According to an exemplary embodiment of the present specification, in the general formula A, any one of R ₂₀₁ to R ₂₀₇ is a site bonded to the general formula (1) through L of the general formula (1), the remainder are the same as or different from each other, and each independently Hydrogen; Nitrile group; Methyl group; A phenyl group substituted with a phosphine oxide group substituted with a nitrile group or a phenyl group; Biphenyl group; Naphthyl group; A fluorenyl group unsubstituted or substituted with a methyl group; Phenanthrenyl group; Pyridyl group; Carbazolyl group unsubstituted or substituted with a phenyl group; Benzocarbazolyl group; Dibenzofuranyl group; Or a dibenzothiophene group.

According to an exemplary embodiment of the present specification, the formula A is represented by any one of the following formula A-12 to A-14.

[Formula A-12]

[Formula A-13]

[Formula A-14]

In Formulas A-12 to A-14, the definitions of R ₂₀₁ to R ₂₀₇ are the same as those of Formula A,

Q ₁ is a direct bond; C (= 0); Or CR _a R _b ,

R ₂₂₀ to R ₂₂₂ , R _a and R _b are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Imide group; Amide group; Carbonyl group; Ester group; Hydroxyl 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; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl phosphine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

r220 and r221 are each an integer of 1 to 4,

r222 is an integer of 1 to 3,

When r220 to r222 are each 2 or more, the structures in the two or more parentheses are the same as or different from each other.

According to an exemplary embodiment of the present specification, the formula A-12 is represented by any one of the formulas A-15 to A-17.

[Formula A-15]

[Formula A-16]

[Formula A-17]

In Formulas A-15 to A-17, the definitions of R ₂₀₁ , R ₂₀₅ to R ₂₀₇ , R ₂₂₀ , r ₂₂₀ , R _a, and R _b are the same as those of Formula A-12.

R ₂₂₀ to R ₂₂₂ are hydrogen.

R _a and R _b are methyl groups.

According to an exemplary embodiment of the present specification, the formula B is represented by any one of the following formula B-1 to B-4.

[Formula B-1]

[Formula B-2]

[Formula B-3]

[Formula B-4]

In Formulas B-1 to B-4, the definitions of Y ₈ and R ₂₀₉ to R ₂₁₄ are the same as those of Formula B.

According to an exemplary embodiment of the present specification, the formula B is represented by any one of the following formula B-5 to B-7.

[Formula B-5]

[Formula B-6]

[Formula B-7]

In Formulas B-5 to B-7, the definitions of R ₂₀₉ to R ₂₁₄ are the same as those of Formula B.

According to an exemplary embodiment of the present specification, in the general formula B, any one of R ₂₀₈ to R ₂₁₄ is a moiety bonded to formula (1), through L of the formula (1), the rest are the same as or different from each other, and each independently Hydrogen; Nitrile group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

According to an exemplary embodiment of the present specification, in the general formula B, any one of R ₂₀₈ to R ₂₁₄ is a moiety bonded to formula (1), through L of the formula (1), the rest are the same as or different from each other, and each independently Hydrogen; Nitrile group; An alkyl group; An aryl group unsubstituted or substituted with a phosphine oxide group substituted with a nitrile group, an alkyl group, or an aryl group; Or a heteroaryl group unsubstituted or substituted with an aryl group.

According to an exemplary embodiment of the present specification, in the general formula B, any one of R ₂₀₈ to R ₂₁₄ is a moiety bonded to formula (1), through L of the formula (1), the rest are the same as or different from each other, and each independently Hydrogen; Nitrile group; Methyl group; A phenyl group substituted with a phosphine oxide group substituted with a nitrile group or an aryl group; Biphenyl group; Naphthyl group; A fluorenyl group unsubstituted or substituted with an alkyl group; Phenanthrenyl group; Pyridyl group; Carbazolyl group unsubstituted or substituted with an aryl group; Benzocarbazolyl group; Dibenzofuranyl group; Or a dibenzothiophene group.

According to an exemplary embodiment of the present specification, in the general formula B, any one of R ₂₀₈ to R ₂₁₄ is a moiety bonded to formula (1), through L of the formula (1), the rest are the same as or different from each other, and each independently Hydrogen; Nitrile group; Methyl group; A phenyl group substituted with a phosphine oxide group substituted with a nitrile group or a phenyl group; Biphenyl group; Naphthyl group; A fluorenyl group unsubstituted or substituted with a methyl group; Phenanthrenyl group; Pyridyl group; Carbazolyl group unsubstituted or substituted with a phenyl group; Benzocarbazolyl group; Dibenzofuranyl group; Or a dibenzothiophene group.

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

[Formula C-1]

In Chemical Formula C-1,

Any one of R ₃₀₁ to R ₃₀₈ is a moiety bonded to Formula 1 through L of Formula 1, and the others are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Imide group; Amide group; Carbonyl group; Ester group; Hydroxyl 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; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl phosphine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

According to an exemplary embodiment of the present specification, the formula C is represented by the following formula C-2.

[Formula C-2]

In Chemical Formula C-2,

Any one of R ₃₀₁ to R ₃₀₈ and R ₃₁₁ to R ₃₁₄ is a moiety bonded to Formula 1 through L of Formula 1, and the others are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Imide group; Amide group; Carbonyl group; Ester group; Hydroxyl 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; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl phosphine group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

According to an exemplary embodiment of the present specification, in the general formulas C-1 and C-2, any one of R ₃₀₁ to R ₃₁₄ is a portion bonded to the formula (1) through L of the formula (1), the rest is hydrogen to be.

According to an exemplary embodiment of the present specification, the formula D is represented by any one of the following formula D-1 to D-4.

[Formula D-1]

[Formula D-2]

[Formula D-3]

[Formula D-4]

In Chemical Formulas D-1 to D-4,

The definitions of U ₁ to U ₄ , R ₄₀₁ and R ₄₀₆ to R ₄₁₁ are the same as in the above formula (D).

According to an exemplary embodiment of the present specification, the formula D is represented by any one of the following formula D-5 to D-15.

[Formula D-5]

[Formula D-6]

[Formula D-7]

[Formula D-8]

[Formula D-9]

[Formula D-10]

[Formula D-11]

[Formula D-12]

[Formula D-13]

[Formula D-14]

[Formula D-15]

In Formulas D-5 to D-15, the definitions of R ₄₀₁ to R ₄₁₁ are the same as those of Formula D.

According to an exemplary embodiment of the present specification, any one of the R ₄₀₁ to R ₄₁₁ is a site bonded to the general formula (1) through L of the general formula (1), the rest are the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.

According to an exemplary embodiment of the present specification, any one of the R ₄₀₁ to R ₄₁₁ is a site bonded to the general formula (1) through L of the general formula (1), the rest are the same as or different from each other, and each independently hydrogen; An alkyl group; Or an aryl group.

According to an exemplary embodiment of the present specification, any one of the R ₄₀₁ to R ₄₁₁ is a site bonded to the general formula (1) through L of the general formula (1), the rest are the same as or different from each other, and each independently hydrogen; Methyl group; Phenyl group; Or a naphthyl group.

According to an exemplary embodiment of the present specification, Chemical Formula 2-1 may be selected from the following [R-1].

[R-1]

According to an exemplary embodiment of the present specification, Formula 2-2 may be selected from the following [R-2].

[R-2]

According to an exemplary embodiment of the present specification, Chemical Formula 2-3 may be selected from the following [R-3].

[R-3]

According to an exemplary embodiment of the present specification, Formula 2-4 may be selected from the following [R-4].

[R-4]

According to an exemplary embodiment of the present specification, Chemical Formula 2-5 may be selected from the following [R-5].

[R-5]

According to an exemplary embodiment of the present specification, Chemical Formula 2-6 may be selected from the following [R-6].

[R-6]

According to an exemplary embodiment of the present specification, Chemical Formula 2-7 may be selected from the following [R-7].

[R-7]

According to an exemplary embodiment of the present specification, Chemical Formula 2-8 may be selected from the following [R-8].

[R-8]

According to yet an embodiment of the present disclosure, the 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 at least one of the organic material layers includes a heterocyclic compound represented by Chemical Formula 1.

According to another exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes the heterocyclic compound.

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

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 transporting holes and holes, and the hole injection layer, the hole transport layer, or the layer for simultaneously transporting holes and holes. It includes the heterocyclic compound.

In one embodiment of the present specification, the organic material layer may further include a hole injection layer or a hole transport layer in addition to the organic material layer including the heterocyclic compound.

In one embodiment of the present specification, the organic material layer including the heterocyclic compound may include the heterocyclic compound as a host of the emission layer, and may include another organic compound, a metal, or a metal compound as a dopant.

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

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 the organic light emitting device according to the present invention is illustrated in FIGS.

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

2 illustrates a structure of an organic light emitting device in which an anode 2, a hole injection layer 3, a hole transport layer 4, a light emitting layer 5, and a cathode 7 are sequentially stacked on a substrate 1. In such a structure, the compound represented by Chemical Formula 1 or 2 may be included in the hole injection layer 3, the hole transport layer 4, or the light emitting layer 5.

3 illustrates a structure of an organic light emitting device in which an anode 2, a hole transport layer 4, a light emitting layer 5, an electron transport layer 6, and a cathode 7 are sequentially stacked on a substrate 1. In such a structure, the compound represented by Formula 1 or 2 may be included in the hole transport layer 4, the light emitting layer 5 or the electron transport layer (6).

4 illustrates a structure of an organic light emitting device in which an anode 2, a light emitting layer 5, an electron transport layer 6, and a cathode 7 are sequentially stacked on a substrate 1. In such a structure, the compound represented by Formula 1 or 2 may be included in the light emitting layer 5 or the electron transport layer (6).

5 illustrates a structure of an organic light emitting device in which an anode 2, a light emitting layer 5, and a cathode 7 are sequentially stacked on a substrate 1. In such a structure, the compound represented by Formula 1 or 2 may be included in the light emitting layer (5).

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 of the present specification, that is, the compound of Formula 1 or 2.

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 an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, and then 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 or 2 may be formed as an organic 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); ZnO: Al or SnO ₂ : Combination of metals and oxides such as 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 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 material is a layer for injecting holes from an electrode, and the hole injection material has a capability of transporting holes, and thus has a hole injection effect at an anode, an excellent hole injection effect for a light emitting layer or a light emitting material, and is generated in a light emitting layer. The compound which prevents the movement of the excited excitons 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. As a hole transport material, the hole transport material is a material capable of transporting holes from the anode or the hole injection layer 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, benzthiazole 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, pyrimidyl group 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 arylamino group, and include pyrene, anthracene, chrysene, and periplanthene having an arylamino group, and a styrylamine compound may be substituted or unsubstituted. At least one arylvinyl group is substituted with the substituted 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 arylamino 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 transporting material 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 move them to the light emitting layer. This is 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 aluminum layers or silver layers in each case.

The electron injection layer is a layer that injects electrons from an electrode, has an ability of transporting 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.

Hereinafter, the present invention will be described in more detail with reference to Examples. However, the following examples are only intended to illustrate the present invention and are not intended to limit the scope of the present invention.

Production Example

Preparation Example 1 Preparation of Core Structure of Chemical Formula 2-1

1) Preparation of Chemical Formula 2-1-a

3-bromo-9,9'-spirobi [fluorene] 300.0 g (758.9 mmol, 1.0 eq), 2-chloroaniline 106.5 g (834.8 mmol, 1.1 eq), K ₃ PO ₄ 209.7 g (1517.8 mmol, 2.0 eq) 1.9 g (3.8 mmol, 0.005 eq) of Pd (t-Bu ₃ P) ₂ was dissolved in 2 L of xylene and refluxed to stir. After 3 hours, when the reaction was completed, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in Ethyl acetate, washed with water, and then depressurized to remove the solvent, which was then subjected to column chromatography to obtain 261.6 g (591.9 mmol, yield 78%) of Chemical Formula 2-1-a.

2) Preparation of Chemical Formula 2-1-b

2-1-a 261.6 g (591.9 mmol, 1.0 eq) to Pd (dba) ₂ 3.4 g (5.9 mmol, 0.01 eq), PCy ₃ 4.9 g (17.7 mmol, 0.03 eq), K ₃ PO ₄ 251.2 g (1183.8 mmol, 2.0 eq) was added to 1.5 L of diethylacetamide and refluxed and stirred. After 3 hours the reaction was poured into water to drop crystals and filtered. The filtered solid was completely dissolved in Ethyl acetate and washed with water. The solution in which the product was dissolved was concentrated under reduced pressure, and the structural isomers and impurities were purified by column chromatography. 103.2 g (254.5 mmol, Yield 43%) of formula 2-1-b were obtained.

3) Preparation of Core Structure of Chemical Formula 2-1

By applying a variety of LZ ₁ to the formula 2-1-b to prepare a core structure of the formula 2-1 in the same manner as in the preparation of 1) Formula 2-1-a.

The definitions of L and Z ₁ are the same as in Chemical Formula 1.

Preparation Example 2 Preparation of Core Structure of Chemical Formula 2-2

Except for using 1-chloronaphthalen-2-amine instead of 2-chloroaniline in Preparation Example 1 was prepared in the same manner.

Preparation Example 3 Preparation of Core Structure of Chemical Formula 2-3

Except for using 2-chloronaphthalen-1-amine instead of 2-chloroaniline in Preparation Example 1 was prepared in the same manner.

Preparation Example 4 Preparation of Core Structure of Chemical Formula 2-4

Except for using 3-chloronaphthalen-2-amine instead of 2-chloroaniline in Preparation Example 1 was prepared in the same manner.

Preparation Example 5 Preparation of Core Structure of Chemical Formula 2-5

1) Preparation of Chemical Formula 2-5-a

300.0 g (758.9 mmol, 1.0 eq), 3-bromo-9,9-diphenyl-9H-fluorene, 106.5 g (834.8 mmol, 1.1 eq), 2-chloroaniline, 209.7 g (1517.8 mmol, 2.0 eq) K ₃ PO ₄ 1.9 g (3.8 mmol, 0.005 eq) of Pd (t-Bu ₃ P) ₂ was dissolved in 2 L of xylene and refluxed to stir. After the reaction was completed after 3 hours, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in Ethyl acetate, washed with water, and then depressurized to remove the solvent, which was then subjected to column chromatography to obtain 248.2 g (561.5 mmol, 74% yield) of Chemical Formula 2-5-a.

2) Preparation of Chemical Formula 2-5-b

2-5-a 248.2 g (561.5 mmol, 1.0 eq) to Pd (dba) ₂ 3.2 g (5.6 mmol, 0.01 eq), PCy ₃ 4.7 g (16.8 mmol, 0.03 eq), K ₃ PO ₄ 238.4 g (1123.2 mmol, 2.0 eq) was added to 1.5 L of diethylacetamide and refluxed and stirred. After 3 hours the reaction was poured into water to drop crystals and filtered. The filtered solid was completely dissolved in Ethyl acetate and washed with water. The solution in which the product was dissolved was concentrated under reduced pressure, and the structural isomers and impurities were purified by column chromatography. 91.1 g (224.6 mmol, 40% yield) of formula 2-5-b were obtained.

3) Preparation of Core Structure of Chemical Formula 2-5

By applying a variety of LZ ₁ to the formula 2-5-b to prepare a core structure of the formula 2-5 in the same manner as in the preparation of 1) Formula 2-5-a.

The definitions of L and Z ₁ are the same as in Chemical Formula 1.

Preparation Example 6 Preparation of Core Structure of Chemical Formula 2-6

Except for using 2-chloroaniline in Preparation Example 5 1-chloronaphthalen-2-amine was prepared in the same manner.

Preparation Example 7 Preparation of Core Structure of Chemical Formula 2-7

Except for using 2-chloroaniphthalen-1-amine instead of 2-chloroaniline in Preparation Example 5 was prepared in the same manner.

Preparation Example 8 Preparation of Core Structure of Chemical Formula 2-8

Except for using 3-chloronaphthalen-2-amine instead of 2-chloroaniline in Preparation Example 5 was prepared in the same manner.

Synthesis Example

Synthesis Example 1 Synthesis of Chemical Formula 2-1-1

10.0 g (24.6 mmol, 1.0 eq), 6.5 g (27.1 mmol, 1.1 eq) 2-chloro-3-phenylquinoxaline, 10.5 g (49.3 mmol, 2.0 eq) K ₃ PO ₄ , Pd (t 0.06 g (0.12 mmol, 0.005 eq) of -Bu ₃ P) ₂ was dissolved in 60 mL of xylene and refluxed to stir. After the reaction was completed after 3 hours, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and dried under reduced pressure to remove the solvent, which was then subjected to column chromatography to obtain 12.1 g (19.9 mmol, 81% yield) of Chemical Formula 2-1-1. [M + H] = 610

Synthesis Example 2 Synthesis of Chemical Formula 2-1-2

10.0 g (24.6 mmol, 1.0 eq), 3- (2-chloroquinazolin-4-yl) -9-phenyl-9H-carbazole 11.0 g (27.1 mmol, 1.1 eq), K ₃ PO ₄ 10.5 g (49.3 mmol, 2.0 eq) and 0.06 g (0.12 mmol, 0.005 eq) of Pd (t-Bu ₃ P) ₂ were dissolved in 60 mL of xylene and refluxed and stirred. After the reaction was completed after 2 hours, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and dried under reduced pressure to remove the solvent, which was then subjected to column chromatography to obtain 15.3 g (19.7 mmol, 80% yield) of Chemical Formula 2-1-2. [M + H] = 775

Synthesis Example 3 Synthesis of Chemical Formula 2-1-3

10.0 g (24.6 mmol, 1.0 eq), 2-chloro-4- (naphthalen-2-yl) quinazoline 7.8 g (27.1 mmol, 1.1 eq), K ₃ PO ₄ 10.5 g (49.3 mmol, 2.0 eq) and Pd (t-Bu ₃ P) ₂ 0.06 g (0.12 mmol, 0.005 eq) were dissolved in 60 mL of xylene and refluxed and stirred. After the reaction was completed after 2 hours, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and then depressurized to remove the solvent, which was then subjected to column chromatography to obtain 3.7 g (20.7 mmol, yield 84%) of Chemical Formula 2-1-3. [M + H] = 659

Synthesis Example 4 Synthesis of Chemical Formula 2-2-1

10.0 g (21.9 mmol, 1.0 eq), 2-chloro-4-phenylpyrido [2,3-d] pyrimidine 5.8 g (24.1 mmol, 1.1 eq), 9.3 g (43.9 mmol) K ₃ PO ₄ , 2.0 eq) and Pd (t-Bu ₃ P) ₂ 0.05 g (0.10 mmol, 0.005 eq) were dissolved in 60 mL of xylene and refluxed and stirred. After the reaction was completed after 2 hours, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and dried under reduced pressure to remove the solvent, which was then subjected to column chromatography to obtain 11.7 g (17.7 mmol, 81% yield) of Chemical Formula 2-2-1. [M + H] = 661

Synthesis Example 5 Synthesis of Chemical Formula 2-2-2

10.0 g (21.9 mmol, 1.0 eq), 4-([1,1'-biphenyl] -4-yl) -2-chloroquinazoline 7.6 g (24.1 mmol, 1.1 eq), K ₃ PO ₄ 9.3 g (43.9 mmol, 2.0 eq) and Pd (t-Bu ₃ P) ₂ 0.05 g (0.10 mmol, 0.005 eq) were dissolved in 60 mL of xylene and refluxed and stirred. After the reaction was completed after 2 hours, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and dried under reduced pressure to remove the solvent, which was then purified by column chromatography to obtain 12.9 g (17.5 mmol, 80% yield) of Chemical Formula 2-2-2. [M + H] = 736

Synthesis Example 6 Synthesis of Chemical Formula 2-2-3

10.0 g (21.9 mmol, 1.0 eq), 4 '-(2-chloroquinazolin-4-yl)-[1,1'-biphenyl] -4-carbonitrile 8.2 g (24.1 mmol, 1.1 eq) 9.3 g (43.9 mmol, 2.0eq), K ₃ PO ₄ , and 0.05 g (0.10 mmol, 0.005 eq) of Pd (t-Bu ₃ P) ₂ were dissolved in 60 mL of xylene and refluxed and stirred. After the reaction was completed after 2 hours, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and then depressurized to remove the solvent, which was then subjected to column chromatography to obtain 14.0 g (18.4 mmol, yield 84%) of Chemical Formula 2-2-3. [M + H] = 760

Synthesis Example 7 Synthesis of Chemical Formula 2-2-4

10.0 g (21.9 mmol, 1.0 eq), 2-chloro-4-phenylbenzofuro [3,2-d] pyrimidine, 9.3 g (24.1 mmol, 1.1 eq), 9.3 g (43.9 mmol) K ₃ PO ₄ , 2.0eq), and the mixture was stirred under reflux dissolving _{Pd (t-Bu 3 P)} 2 0.05 g (0.10 mmol, 0.005 eq) in 60 mL of xylene (xylene). After the reaction was completed after 3 hours, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and then depressurized to remove the solvent, which was then purified by column chromatography to obtain 12.4 g (17.7 mmol, 81% yield) of Chemical Formula 2-2-4. [M + H] = 700

6 is a diagram showing an LC / MS graph of Chemical Formula 2-2-4 prepared from Preparation Example 7. FIG.

Synthesis Example 8 Synthesis of Chemical Formula 2-2-5

10.0 g (21.9 mmol, 1.0 eq), 2-chloro-4-phenylbenzo [4,5] thieno [3,2-d] pyrimidine 7.1 g (24.1 mmol, 1.1 eq), K ₃ PO ₄ 9.3 g (43.9 mmol, 2.0 eq) and Pd (t-Bu ₃ P) ₂ 0.05 g (0.10 mmol, 0.005 eq) were dissolved in 60 mL of xylene and refluxed and stirred. After the reaction was completed after 3 hours, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and dried under reduced pressure to remove the solvent, which was then purified by column chromatography to obtain 12.0 g (16.9 mmol, 77% yield) of Chemical Formula 2-2-5. [M + H] = 716

Synthesis Example 9. Synthesis of Chemical Formula 2-3-1

Formula 2-3-b 10.0 g (21.9 mmol, 1.0 eq), 2- (4-bromophenyl) -3-phenylquinoxaline 8.7 g (24.1 mmol, 1.1 eq), K ₃ PO ₄ 9.3 g (43.9 mmol, 2.0 eq) 0.05 g (0.10 mmol, 0.005 eq) of Pd (t-Bu ₃ P) ₂ was dissolved in 60 mL of xylene and refluxed to stir. After the reaction was completed after 3 hours, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and then depressurized to remove the solvent, which was then purified by column chromatography to obtain 12.1 g (18.4 mmol, 84%) of Chemical Formula 2-3-1. [M + H] = 661

Synthesis Example 10 Synthesis of Chemical Formula 2-3-2

10.0 g (21.9 mmol, 1.0 eq), 2-3-b, 5.8 g (24.1 mmol, 1.1 eq), 2-chloro-4-phenylquinazoline, 9.3 g (43.9 mmol, 2.0 eq) K ₃ PO ₄ , Pd (t 0.05 g (0.10 mmol, 0.005 eq) of -Bu ₃ P) ₂ was dissolved in 60 mL of xylene and refluxed to stir. After the reaction was completed after 3 hours, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ and washed with water. Then, the solvent was removed under reduced pressure again, which was then purified by column chromatography to obtain 13.7 g (18.6 mmol, yield 85%). [M + H] = 736

Synthesis Example 11. Synthesis of Chemical Formula 2-4-1

10.0 g (21.9 mmol, 1.0 eq), 11-bromodibenzo [a, c] phenazine, 8.6 g (24.1 mmol, 1.1 eq), K ₃ PO ₄ 9.3 g (43.9 mmol, 2.0 eq), Pd 0.05 g (0.10 mmol, 0.005 eq) of (t-Bu ₃ P) ₂ was dissolved in 60 mL of xylene and refluxed to stir. After the reaction was completed after 1 hour, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and then depressurized to remove the solvent, which was then subjected to column chromatography to obtain 11.1 g (16.9 mmol, 77% yield) of the compound of formula 2-4-1. [M + H] = 661

Synthesis Example 12 Synthesis of Chemical Formula 2-4-2

Formula 2-4-b 10.0 g (21.9 mmol , 1.0 eq), 2-chloro-4- (naphthalen-1-yl) quinazoline 7.0 g (24.1 mmol, 1.1 eq), K 3 PO 4 9.3 g (43.9 mmol, 2.0 eq) and Pd (t-Bu ₃ P) ₂ 0.05 g (0.10 mmol, 0.005 eq) were dissolved in 60 mL of xylene and refluxed and stirred. After the reaction was completed after 2 hours, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl 3, washed with water, and dried under reduced pressure to remove the solvent, which was then subjected to column chromatography to obtain 13.2 g (18.0 mmol, 82% yield) of Chemical Formula 2-4-2. [M + H] = 736

Synthesis Example 13 Synthesis of Chemical Formula 2-5-1

2-5-b 10.0 g (24.5 mmol, 1.0 eq), 4-chloro-2-phenylquinazoline 6.5 g (26.9 mmol, 1.1 eq), K ₃ PO ₄ 10.4 g (49.0 mmol, 2.0 eq), Pd (t 0.06 g (0.12 mmol, 0.005 eq) of -Bu ₃ P) ₂ was dissolved in 60 mL of xylene and refluxed to stir. After the reaction was completed after 3 hours, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ and washed with water. Then, the solvent was removed under reduced pressure, and the residue was purified by column chromatography to obtain 12.1 g (19.9 mmol, 72% yield) of Chemical Formula 2-5-1. [M + H] = 611

Synthesis Example 14. Synthesis of Chemical Formula 2-5-2

Formula 2-5-b 10.0 g (24.6 mmol, 1.0 eq), 6-bromo-2,3-diphenylquinoxaline 9.7 g (26.9 mmol, 1.1 eq), K ₃ PO ₄ 10.4 g (49.0 mmol, 2.0 eq), Pd 0.06 g (0.12 mmol, 0.005 eq) of (t-Bu ₃ P) ₂ was dissolved in 60 mL of xylene and refluxed and stirred. After the reaction was completed after 1 hour, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and then depressurized to remove the solvent, which was then subjected to column chromatography to obtain 13.5 g (19.6 mmol, 77% yield) of Chemical Formula 2-5-2. [M + H] = 688

Synthesis Example 15 Synthesis of Chemical Formula 2-5-3

2-5-b 10.0 g (24.6 mmol, 1.0 eq), 2-chloro-4-phenylquinazoline 6.5 g (26.9 mmol, 1.1 eq), K ₃ PO ₄ 10.4 g (49.0 mmol, 2.0 eq), Pd (t 0.06 g (0.12 mmol, 0.005 eq) of -Bu ₃ P) ₂ was dissolved in 60 mL of xylene and refluxed to stir. After the reaction was completed after 2 hours, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and then depressurized to remove the solvent, which was then subjected to column chromatography to obtain 12.6 g (20.6 mmol, 85% yield) of Chemical Formula 2-5-3. [M + H] = 611

7 is a diagram showing an LC / MS graph of Chemical Formula 2-5-3 prepared from Preparation Example 15.

Synthesis Example 16 Synthesis of Chemical Formula 2-5-4

Formula 2-5-b 10.0 g (24.6 mmol, 1.0 eq), 2-chloro-4- (naphthalen-2-yl) quinazoline 7.8 g (26.9 mmol, 1.1 eq), K ₃ PO ₄ 10.4 g (49.0 mmol, 2.0 eq) and Pd (t-Bu ₃ P) ₂ 0.06 g (0.12 mmol, 0.005 eq) were dissolved in 60 mL of xylene and refluxed and stirred. After the reaction was completed after 2 hours, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and dried under reduced pressure to remove the solvent, which was then subjected to column chromatography to obtain 14.1 g (21.3 mmol, 87% yield) of Chemical Formula 2-5-4. [M + H] = 661

8 is a diagram showing an LC / MS graph of Chemical Formula 2-5-4 prepared from Preparation Example 16.

Synthesis Example 17 Synthesis of Chemical Formula 2-6-1

10.0 g (21.9 mmol, 1.0 eq), 2-chloro-4-phenylpyrido [2,3-d] pyrimidine 5.8 g (24.0 mmol, 1.1 eq), 9.3 g (43.7 mmol) K ₃ PO ₄ , 2.0 eq) and Pd (t-Bu ₃ P) ₂ 0.05 g (0.10 mmol, 0.005 eq) were dissolved in 60 mL of xylene and refluxed and stirred. After the reaction was completed after 2 hours, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and dried under reduced pressure to remove the solvent, which was then purified by column chromatography to obtain 11.8 g (17.9 mmol, 82% yield) of Chemical Formula 2-6-1. [M + H] = 663

Synthesis Example 18 Synthesis of Chemical Formula 2-6-2

2-6-b 10.0 g (21.9 mmol, 1.0 eq), 2-([1,1'-biphenyl] -4-yl) -4-chloroquinazoline 7.6 g (24.0 mmol, 1.1 eq), K ₃ PO ₄ 9.3 g (43.7 mmol, 2.0 eq) and Pd (t-Bu ₃ P) ₂ 0.05 g (0.10 mmol, 0.005 eq) were dissolved in 60 mL of xylene and refluxed and stirred. After the reaction was completed after 2 hours, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and dried under reduced pressure to remove the solvent, which was then purified by column chromatography to obtain 12.7 g (17.2 mmol, 79%) of Chemical Formula 2-6-2. [M + H] = 738

Synthesis Example 19 Synthesis of Chemical Formula 2-6-3

Formula 2-6-b 10.0 g (21.9 mmol, 1.0 eq), 6.8 g (24.0 mmol, 1.1 eq) 1-bromo-4-phenylphthalazine, 9.3 g (43.7 mmol, 2.0 eq) K ₃ PO ₄ , Pd (t 0.05 g (0.10 mmol, 0.005 eq) of -Bu ₃ P) ₂ was dissolved in 60 mL of xylene and refluxed to stir. After the reaction was completed after 1 hour, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and then depressurized to remove the solvent, which was then subjected to column chromatography to obtain 12.0 g (18.1 mmol, 83% yield) of Chemical Formula 2-6-3. [M + H] = 661

Synthesis Example 20 Synthesis of Chemical Formula 2-7-1

10.0 g (21.9 mmol, 1.0 eq), 3-bromoacenaphtho [1,2-b] quinoxaline 8.0 g (24.0 mmol, 1.1 eq), 9.3 g (43.7 mmol, 2.0 eq) K ₃ PO ₄ 0.05 g (0.10 mmol, 0.005 eq) of Pd (t-Bu ₃ P) ₂ was dissolved in 60 mL of xylene and refluxed to stir. After the reaction was completed after 3 hours, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and dried under reduced pressure to remove the solvent, which was then purified by column chromatography to obtain 11.6 g (16.3 mmol, 75% yield) of Chemical Formula 2-7-1. [M + H] = 710

Synthesis Example 21 Synthesis of Chemical Formula 2-7-2

Formula 2-7-b 10.0 g (21.9 mmol , 1.0 eq), 2-chloro-4- (naphthalen-2-yl) quinazoline 6.9 g (24.0 mmol, 1.1 eq), K 3 PO 4 9.3 g (43.7 mmol, 2.0 eq) and Pd (t-Bu ₃ P) ₂ 0.05 g (0.10 mmol, 0.005 eq) were dissolved in 60 mL of xylene and refluxed and stirred. After the reaction was completed after 3 hours, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and then depressurized to remove the solvent, which was then subjected to column chromatography to obtain 11.8 g (16.6 mmol, 76% yield) of Chemical Formula 2-7-2. [M + H] = 712

Synthesis Example 22 Synthesis of Chemical Formula 2-8-1

10.0 g (21.9 mmol, 1.0 eq), 4- (3- (4-bromophenyl) quinoxalin-2-yl) benzonitrile 9.2 g (24.0 mmol, 1.1 eq), 9.3 g (K ₃ PO ₄ ) 43.7 mmol, 2.0 eq) and 0.05 g (0.10 mmol, 0.005 eq) of Pd (t-Bu ₃ P) ₂ were dissolved in 60 mL of xylene and refluxed and stirred. After the reaction was completed after 1 hour, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and then depressurized to remove the solvent, which was then subjected to column chromatography to obtain 13.8 g (18.1 mmol, 83%) of Chemical Formula 2-8-1. [M + H] = 763

Synthesis Example 23 Synthesis of Chemical Formula 2-8-2

10.0 g (21.9 mmol, 1.0 eq), 9- (2-chloroquinazolin-4-yl) -9Hcarbazole 7.9 g (24.0 mmol, 1.1 eq), 9.3 g (43.7 mmol, 2.0) K ₃ PO ₄ eq) and Pd (t-Bu ₃ P) ₂ 0.05 g (0.10 mmol, 0.005 eq) were dissolved in 60 mL of xylene and refluxed and stirred. After the reaction was completed after 3 hours, the solvent was removed under reduced pressure. Thereafter, the mixture was completely dissolved in CHCl ₃ , washed with water, and dried under reduced pressure to remove the solvent, which was then subjected to column chromatography to obtain 13.1 g (17.4 mmol, 80% yield) of Chemical Formula 2-8-2. [M + H] = 751

<Example 1>

A glass substrate (corning 7059 glass) coated with ITO (Indium Tin Oxide) with a thickness of 1,000 Å was placed in distilled water in which a dispersant was dissolved, and ultrasonically washed. Fischer Co. products were used for the detergent, and Millipore Co. Secondly filtered distilled water was used as a filter of the product. After the ITO was washed for 30 minutes, the ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After washing the distilled water, the ultrasonic washing in the order of isopropyl alcohol, acetone, methanol solvent and dried. The hexanitrile hexaazatriphenylene (HAT-CN) was thermally vacuum deposited to a thickness of 50 kPa on the prepared ITO transparent electrode to form a hole injection layer. The following HT1 (700 Pa) was vacuum-deposited on the hole transport layer, and HT2 (200 Pa) was subsequently deposited. The light emitting layer was vacuum deposited to a thickness of 300 Å with the above formula 2-1-3 and the dopant Dp-7 compound as a host. Subsequently, E1 compound (300 kPa) was thermally vacuum deposited sequentially to the electron injection and transport layer. An organic light emitting device was manufactured by sequentially depositing 12 Å thick lithium fluoride (LiF) and 2,000 Å thick aluminum on the electron injection and transport layer to form a cathode. In the above process, the deposition rate of the organic material was maintained at 1 Å / sec, LiF was 0.2 Å / sec, and the aluminum was maintained at a deposition rate of 3 Å / sec to 7 Å / sec.

<Example 2>

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Chemical Formula 2-1-2 was used instead of Chemical Formula 2-1-3 in Example 1.

<Example 3>

An organic light emitting diode was manufactured according to the same method as Example 1 except for using Chemical Formula 2-2-4 instead of Chemical Formula 2-1-3 in Example 1.

<Example 4>

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Chemical Formula 2-2-5 was used instead of Chemical Formula 2-1-3 in Example 1.

Example 5

An organic light emitting diode was manufactured according to the same method as Example 1 except for using Chemical Formula 2-5-3 instead of Chemical Formula 2-1-3 in Example 1.

<Example 6>

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Chemical Formula 2-5-4 was used instead of Chemical Formula 2-1-3 in Example 1.

Comparative Example 1

An organic light emitting diode was manufactured according to the same method as Example 1 except for using A1 instead of Formula 2-1-3 in Example 1.

Comparative Example 2

An organic light emitting diode was manufactured according to the same method as Example 1 except for using A2 instead of Chemical Formula 2-1-3 in Example 1.

Comparative Example 3

An organic light emitting diode was manufactured according to the same method as Example 1 except for using the CBP instead of Chemical Formula 2-1-3 in Example 1.

When the current (10 mA reference) was applied to the organic light emitting diodes manufactured according to Examples 1 to 6 and Comparative Examples 1 to 3, the results of Table 1 were obtained.

division Chemical formula Driving voltage (V) Efficiency (cd / A) x-coordinate y coordinate Example 1 2-1-3 3.91 24.67 0.661 0.337 Example 2 2-1-2 3.84 25.83 0.662 0.337 Example 3 2-2-4 3.61 25.27 0.661 0.326 Example 4 2-2-5 3.52 25.32 0.662 0.337 Example 5 2-5-3 4.13 23.92 0.660 0.336 Example 6 2-5-4 4.01 24.16 0.661 0.336 Comparative Example 1 A1 3.95 18.35 0.660 0.333 Comparative Example 2 A2 3.91 19.73 0.660 0.331 Comparative Example 3 CBP 4.21 15.27 0.658 0.337

As can be seen from the results of Table 1, the organic light emitting device using the heterocyclic compound according to an exemplary embodiment of the present specification improved the luminous efficiency while lowering the driving voltage and all showed red light emission. In general, it showed a lower driving voltage and higher efficiency than the CBP used as a comparative host material, and A1 and A2, which are the materials of Comparative Examples 2 and 3, are also insufficient in improving the driving voltage and have a 30% or more efficiency drop. It is not superior to the heterocyclic compound according to one embodiment of. In addition, all of the compounds of Examples 1 to 6 showed similar lifetime results in the measurement of the lifespan of the fabricated organic light emitting device, whereas CBP, A1 and A2 of Comparative Examples 1 to 3 showed less than 10% based on T95. Therefore, the heterocyclic compound according to the exemplary embodiment of the present specification has the effect of high efficiency, low driving voltage and long life in the organic light emitting device.

1: substrate
2: anode
3: hole injection layer
4: hole transport layer
5: light emitting layer
6: electron transport layer
7: cathode

Claims (11)

Heterocyclic compounds represented by any one of the following formulas 2-1 to 2-4 and 2-6 to 2-8:
[Formula 2-1] [Formula 2-2]

[Formula 2-3] [Formula 2-4]

[Formula 2-6]

[Formula 2-7] [Formula 2-8]

In Chemical Formulas 2-1 to 2-4 and 2-6 to 2-8,
R ₀ to R ₁₄ are each hydrogen,
L is a direct bond; Phenylene group; Biphenylene group; Or naphthylene group,
Z ₁ is a 2- to 5 ring N unsubstituted or substituted with a nitrile group, a C6-C20 aryl group unsubstituted or substituted with a nitrile group, a C2-C20 heteroaryl group, or a C2-C20 arylheteroaryl group Containing heteroaryl group,
q is an integer of 1-4, t is an integer of 1-8, s is an integer of 1-5. delete The heterocyclic compound according to claim 1, wherein Z ₁ is represented by one of Formulas A to D:
[Formula A]

In Chemical Formula A,
Y ₁ is N or R ₂₀₁ , Y ₂ is N or R ₂₀₂ , Y ₃ is N or R ₂₀₃ , Y ₄ is N or R ₂₀₄ , Y ₅ is N or R ₂₀₅ , Y ₆ is N or R ₂₀₆ , Y ₇ is N or R ₂₀₇ ,
Any one of R ₂₀₁ to R ₂₀₇ is a moiety bonded to Formula 1 through L in Formula 1, and the other are the same as or different from each other, and each independently an aryl group having 6 to 20 carbon atoms; Or a heteroaryl group having 2 to 20 carbon atoms,
[Formula B]

In Chemical Formula B,
Y ₈ is N or R ₂₀₈ , Y ₉ is N or R ₂₀₉ , Y ₁₀ is N or R ₂₁₀ , Y ₁₁ is N or R ₂₁₁ , Y ₁₂ is N or R ₂₁₂ , Y ₁₃ is N or R ₂₁₃ , Y ₁₄ is N or R ₂₁₄ ,
Any one of R ₂₀₈ to R ₂₁₄ is a moiety bonded to Formula 1 through L in Formula 1, and the other are the same as or different from each other, and each independently an aryl group having 6 to 20 carbon atoms; Or a heteroaryl group having 2 to 20 carbon atoms,
[Formula C]

In Chemical Formula C,
T ₁ is N or R ₃₀₉ , T ₂ is N or R ₃₁₀ ,
At least one of T ₁ and T ₂ is N,
Any one of R ₃₀₁ to R ₃₀₈ is a moiety bonded to Formula 1 through L of Formula 1, and the other and R ₃₀₉ and R ₃₁₀ are the same as or different from each other, and each independently hydrogen; Nitrile group; Aryl groups having 6 to 20 carbon atoms; Or a heteroaryl group having 2 to 20 carbon atoms, or R ₃₀₁ and R ₃₀₂ combine with each other to form a ring substituted with R _c ,
When R ₃₀₁ and R ₃₀₂ are bonded to each other to form a ring substituted with R _c , any one of R ₃₀₃ to R ₃₀₈ and R c may be a site bonded to Formula 1 through L of Formula 1, ,
R _c is hydrogen; Nitrile group; Aryl groups having 6 to 20 carbon atoms; Or a heteroaryl group having 2 to 20 carbon atoms,
[Formula D]

In Chemical Formula D,
G ₁ is O, S, NR ₄₀₁ , or CR ₄₁₀ R ₄₁₁ ,
U ₁ is N or R ₄₀₂ , U ₂ is N or R ₄₀₃ , U ₃ is N or R ₄₀₄ , U ₄ is N or R ₄₀₅ , U ₅ is N or R ₄₀₆ , U ₆ is N or R ₄₀₇ , U ₇ is N or R ₄₀₈ , U ₈ is N or R ₄₀₉ ,
When G ₁ is CR ₄₁₀ R ₄₁₁ , at least one of U ₁ to U ₈ is N,
Any one of R ₄₀₁ to R ₄₁₁ is a moiety bonded to Formula 1 through L in Formula 1, and the other are the same as or different from each other, and each independently an aryl group having 6 to 20 carbon atoms; Or a heteroaryl group having 2 to 20 carbon atoms. delete delete delete The method according to claim 1, wherein any one of the formulas 2-1 to 2-4 and 2-6 to 2-8 are the following [R-1] to [R-4] and [R-6] to [R-8] Heterocyclic compounds selected from:
[R-1]

[R-2]

[R-3]

[R-4]

[R-6]

[R-7]

[R-8]

A first electrode; A second electrode provided to face the first electrode; And at least one organic material layer including a light emitting layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers is a heterocyclic ring according to any one of claims 1, 3, and 7. An organic light emitting device comprising a compound. The method according to claim 8, wherein the organic material layer includes an electron transport layer, an electron injection layer, a layer for simultaneously transporting electrons and electron injection, a light emitting layer, a hole transport layer, a hole injection layer or a layer for simultaneously hole transport and hole injection, the electron transport layer And an electron injection layer, a layer for simultaneously transporting electrons and electron injection, a light emitting layer, a hole transport layer, a hole injection layer, or a layer for both hole transport and hole injection simultaneously include the heterocyclic compound. The organic light emitting device of claim 8, wherein the organic material layer comprises a light emitting layer, and the light emitting layer comprises the heterocyclic compound. The organic light emitting device of claim 8, wherein the organic material layer includes a light emitting layer, and the light emitting layer includes the heterocyclic compound as a host of the light emitting layer.

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