WO2017047993A1

WO2017047993A1 - Compound and organic light emitting device containing same

Info

Publication number: WO2017047993A1
Application number: PCT/KR2016/010163
Authority: WO
Inventors: 차용범; 김진주; 김성소; 류제민
Original assignee: 주식회사 엘지화학
Priority date: 2015-09-16
Filing date: 2016-09-09
Publication date: 2017-03-23

Abstract

Provided are a compound represented by chemical formula 1 below, and an organic light emitting device containing the same, wherein in chemical formula 1, A is a substituted or unsubstituted four-membered aromatic ring, and at least one of R1 to R12 has a substituent other than hydrogen.

Description

Compound and organic light emitting device comprising same

This application is filed with the Korean Patent Application No. 10-2015-0131230 filed with the Korean Patent Office on September 16, 2015 and the Korean Patent Application No. 10-2016-0107194 filed with the Korean Patent Office on August 23, 2016. Claims the full benefit of which is incorporated herein by reference.

The present specification relates to a novel 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. 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 the electrons meet each other. When it falls back to the ground, it glows.

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

[Patent Documents]

International Patent Application Publication No. 2003-012890

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

According to an exemplary embodiment of the present specification, a compound represented by the following formula (1) is provided.

[Formula 1]

In Chemical Formula 1,

A is a substituted or unsubstituted tetracyclic aromatic ring,

R1 to R12 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amide 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 groups adjacent to each other may combine with each other to form a substituted or unsubstituted ring,

At least one of the above R1 to R12 has a substituent other than hydrogen.

Further, according to one embodiment of the present specification, the first electrode; A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes a compound represented by Chemical Formula 1. .

The organic light emitting device including the compound according to the exemplary embodiment of the present specification has excellent thermal stability, and may improve efficiency, low driving voltage, and / or lifespan characteristics.

1 illustrates an organic light emitting device 10 according to an exemplary embodiment of the present specification.

2 illustrates an organic light emitting device 11 according to another exemplary embodiment of the present specification.

Hereinafter, this specification is demonstrated in detail.

The present specification provides a 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.

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; 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; 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 a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are linked.

In 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-alkylarylamine 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-alkylarylamine 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 , wherein R ₁₀₀ and R ₁₀₁ 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.

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 naphthyl group, anthracenyl group, phenanthryl group, triphenyl group, pyrenyl group, perrylenyl group, chrysenyl group, fluorenyl group, etc., but is not limited thereto.

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

When the fluorenyl group is substituted,

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

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.

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, 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 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 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 a substituted or unsubstituted hetero ring.

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 an exemplary embodiment of the present specification, in the general formula 1, A is a substituted or unsubstituted fluoranthene ring; Or a substituted or unsubstituted triphenylene ring.

According to an exemplary embodiment of the present specification, in the general formula 1, A is represented by the formula A-1 or A-2.

[Formula A-1]

[Formula A-2]

In Chemical Formulas A-1 and A-2,

A1 and A2 of A1 to A22; A2 and A3; A4 and A5; A5 and A6; A7 and A8; A8 and A9; A9 and A10; A11 and A12; A12 and A13; A13 and A14; A15 and A16; A16 and A17; A17 and A18; A19 and A20; A20 and A21; Or A21 and A22 are moieties that are directly connected to Formula 1, and the others are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amide 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, Formula 1 is represented by the following formula 1-1 or 1-2.

[Formula 1-1]

[Formula 1-2]

In Chemical Formulas 1-1 and 1-2,

Definitions of R1 to R12 are the same as in the general formula (1),

A1, A4 to A11 and A14 to A22 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amide 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, Formula 1 is represented by the following formula 1-3 or 1-4.

[Formula 1-3]

[Formula 1-4]

In Chemical Formulas 1-3 and 1-4,

Definitions of R1 to R12 are the same as in the above formula (1).

According to an exemplary embodiment of the present specification, in the general formula 1, R1 to R12 are the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted substituted or unsubstituted diarylamine group; A substituted or unsubstituted diheteroarylamine group; Substituted or unsubstituted silyl group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

According to an exemplary embodiment of the present disclosure in the general formula 1, R1 to R12 are the same as or different from each other, each independently represent a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Substituted or unsubstituted phenanthrenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted terphenyl group; A substituted or unsubstituted fluorenyl group; Substituted or unsubstituted anthracenyl group; Substituted or unsubstituted chrysenyl group; A substituted or unsubstituted quarterphenyl group; Substituted or unsubstituted spirobifluorenyl group; Substituted or unsubstituted pyrenyl group; Substituted or unsubstituted triphenylenyl group; Substituted or unsubstituted perenyl group; Substituted or unsubstituted triazinyl group; Substituted or unsubstituted pyrimidyl group; Substituted or unsubstituted pyridyl group; Substituted or unsubstituted quinolinyl group; Substituted or unsubstituted quinazolinyl group; Substituted or unsubstituted benzoquinolinyl group; Substituted or unsubstituted phenanthrolinyl group; Substituted or unsubstituted quinoxalinyl group; Substituted or unsubstituted dibenzofuranyl group; Substituted or unsubstituted dibenzothiophene group; Substituted or unsubstituted benzonaphthofuranyl; Substituted or unsubstituted benzonaphthothiophene group; Substituted or unsubstituted dimethyl phosphine oxide group; Substituted or unsubstituted diphenylphosphine oxide; Substituted or unsubstituted dinaphthylphosphine oxide; Substituted or unsubstituted benzoxazolyl group; Substituted or unsubstituted benzothiazolyl group; Substituted or unsubstituted benzimidazolyl group; Substituted or unsubstituted triphenylsilyl group; Substituted or unsubstituted phenothiazinyl group; Substituted or unsubstituted phenoxazinyl group; Substituted or unsubstituted thiophene group; Substituted or unsubstituted diphenylamine group; A substituted or unsubstituted N-phenylnaphthylamine group; A substituted or unsubstituted N-phenylbiphenylamine group; A substituted or unsubstituted N-phenylphenanthrenylamine group; A substituted or unsubstituted N-biphenylnaphthylamine group; Substituted or unsubstituted dibiphenylamine group; A substituted or unsubstituted N-biphenylphenanthrenylamine group; A substituted or unsubstituted dinaphthylamine group; A substituted or unsubstituted N-quaterphenylfluorenylamine group; A substituted or unsubstituted N-terphenylfluorenylamine group; A substituted or unsubstituted N-biphenylterphenylamine group; A substituted or unsubstituted N-biphenylfluorenylamine group; A substituted or unsubstituted N-phenylfluorenylamine group; A substituted or unsubstituted N-naphthylfluorenylamine group; A substituted or unsubstituted N-phenanthrenylfluorenylamine group; A substituted or unsubstituted difluorenylamine group; A substituted or unsubstituted N-phenylterphenylamine group; A substituted or unsubstituted N-phenylcarbazolylamine group; A substituted or unsubstituted N-biphenylcarbazolylamine group; A substituted or unsubstituted N-phenylbenzocarbazolylamine group; A substituted or unsubstituted N-biphenylbenzocarbazolylamine group; A substituted or unsubstituted N-phenyldibenzofuranylamine group; A substituted or unsubstituted N-phenyldibenzothiophenamine group; Substituted or unsubstituted N-fluorenyl carbazolylamine group; Substituted or unsubstituted benzocarbazolyl group; A substituted or unsubstituted dibenzocarbazolyl group; Substituted or unsubstituted carbazolyl group; Substituted or unsubstituted

; Substituted or unsubstituted

; And it is selected from the group consisting of a structure represented by the formula a,

---- means a site bonded to the formula (1) through the L1.

[Formula a]

In Chemical Formula a,

Any one of X1 to X12 is a moiety bonded to Formula 1, and the others are the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or adjacent groups are connected to each other to form a substituted or unsubstituted ring.

According to an exemplary embodiment of the present specification, in the general formula a, any one of X1 to X12 is a site bonded to the formula (1), the rest is hydrogen.

According to an exemplary embodiment of the present specification, in the general formula a, X11 and X12 are connected to each other to form a substituted or unsubstituted monocyclic or polycyclic hydrocarbon ring having 6 to 20 carbon atoms.

According to an exemplary embodiment of the present specification, in the general formula a, X11 and X12 are connected to each other to form a substituted or unsubstituted monocyclic or polycyclic hydrocarbon ring having 6 to 10 carbon atoms.

According to an exemplary embodiment of the present specification, in the general formula a, X11 and X12 are connected to each other to form a substituted or unsubstituted benzene ring.

According to an exemplary embodiment of the present specification, in the general formula a, X11 and X12 are connected to each other to form a benzene ring.

According to an exemplary embodiment of the present specification, in the general formula 1, R1 to R12 are the same as or different from each other, and each independently hydrogen; Phenyl group; Biphenyl group; Phenanthrenyl group; Naphthyl group; Terphenyl group; Fluorenyl group; Anthracenyl group; Chrysenyl group; Quarter-phenyl group; Spirobifluorenyl group; Pyrenyl group; Triphenylenyl group; Perrylenyl group; Triazinyl group; Pyrimidyl groups; Pyridyl group; Quinolinyl group; Quinazolinyl group; Benzoquinolinyl group; Phenanthrolinyl group; Quinoxalinyl group; Dibenzofuranyl group; Dibenzothiophene group; Benzonaphthofuranyl; Benzonaphthothiophene group; Dimethyl phosphine oxide group; Diphenylphosphine oxide; Dinaphthylphosphine oxide; Benzoxazolyl group; Benzothiazolyl group; Benzimidazolyl group; Triphenylsilyl group; Phenothiazinyl group; Phenoxazinyl group; Thiophene group; Diphenylamine group; N-phenylnaphthylamine group; N-phenylbiphenylamine group; N-phenylphenanthrenylamine group; N-biphenyl naphthylamine group; Dibiphenylamine group; N-biphenylphenanthrenylamine group; Dinaphthylamine group; N-quaterphenyl fluorenyl amine group; N-terphenyl fluorenyl amine group; N-biphenyl terphenyl amine group; N-biphenyl fluorenyl amine group; A substituted or unsubstituted N-phenylfluorenylamine group; N-naphthylfluorenylamine group; N-phenanthrenyl fluorenyl amine group; Difluorenylamine group; N-phenylterphenylamine group; N-phenylcarbazolylamine group; N-biphenylcarbazolylamine group; N-phenylbenzocarbazolylamine group; N-biphenylbenzocarbazolylamine group; N-phenyldibenzofuranylamine group; N-phenyldibenzothiophenamine group; N-fluorenyl carbazolylamine group; Benzocarbazolyl group; Dibenzocarbazolyl group; Carbazolyl group;

Is selected from the group consisting of

At least one of the R1 to R12 has a substituent other than hydrogen,

R1 to R12 are deuterium; Fluorine group; Nitrile group; Methyl group; Ethyl group; n-propyl group; Isopropyl group; t-butyl group; Trimethylsilyl group; Trifluoromethyl group; Trifluoromethoxy group; Pentafluoroethyl group; Cyclohexyl group; Phenyl group; Biphenyl group; Naphthyl group; Fluorenyl group; Phenanthrenyl group; Carbazolyl group; Benzocarbazolyl group; Pyridyl group; Triazinyl group; Triphenylenyl group; Pyrimidyl groups; Quinolinyl group; Dibenzofuranyl group; Dibenzothiophene group; Benzimidazolyl group; Benzothiazolyl group; Benzoxazolyl group; Thiophene group; Dimethyl phosphine oxide group; Diphenylphosphine oxide group; Dinaphthyl phosphine oxide groups; Trimethylsilyl group; Triphenylsilyl group; Diphenylamine group; Dibiphenylamine group; N-phenylbiphenylamine group; N-phenylnaphthylamine group; N-biphenyl naphthylamine group; N-naphthylfluorenylamine group; N-phenylphenanthrenylamine group; N-biphenylphenanthrenylamine group; N-phenyl fluorenyl amine group; N-phenylterphenylamine group; N-phenanthrenyl fluorenyl amine group; N-biphenyl fluorenyl amine group; And

It may be substituted or unsubstituted with one or more selected from the group consisting of.

---- means a site bonded to the formula (1).

According to an exemplary embodiment of the present specification, in the general formula 1, R1 to R12 are the same as or different from each other, and each independently hydrogen; Or represented by any one of the following structural formulas [R-1] to [R-5], and at least one of R1 to R12 has a substituent other than hydrogen.

[R-1]

[R-2]

[R-3]

[R-4]

[R-5]

In the above structural formula --- means a moiety bonded to the formula (1).

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

According to an exemplary embodiment of the present specification, the compound represented by Formula 1 may be prepared by the following general formulas 1 to 4, but is not limited thereto.

The following general formulas (1) and (3) represent a general method for producing the core of Chemical Formula 1-1, and the following general formulas (2) and 4 represent a general method for producing the core of Formula 1-2.

[Formula 1]

[Formula 2]

[Formula 3]

[Formula 4]

According to an exemplary embodiment of the present specification, the 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 compound represented by Chemical Formula 1.

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

For example, the structure of the organic light emitting device of the present specification may have a structure as shown in FIGS. 1 and 2, but is not limited thereto.

1 illustrates a structure of an organic light emitting device 10 in which a first electrode 30, a light emitting layer 40, and a second electrode 50 are sequentially stacked on a substrate 20. 1 is an exemplary structure of an organic light emitting device according to an exemplary embodiment of the present specification, and may further include another organic material layer.

2 illustrates a first electrode 30, a hole injection layer 60, a hole transport layer 70, a light emitting layer 40, an electron transport layer 80, an electron injection layer 90, and a second electrode on a substrate 20. A structure of an organic light emitting device in which 50) is sequentially stacked is illustrated. 2 is an exemplary structure according to an exemplary embodiment of the present specification, and may further include another organic material layer.

According to an exemplary embodiment of the present specification, the organic material layer includes a hole injection layer or a hole transport layer, the hole injection layer or hole transport layer comprises a compound represented by the formula (1).

According to an exemplary embodiment of the present specification, the organic material layer includes an electron blocking layer, and the electron blocking layer includes a compound represented by Chemical Formula 1.

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

According to an exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula 1 as a host of the light emitting layer.

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 compound represented by Chemical Formula 1 as a phosphorescent host or a fluorescent host of the light emitting layer.

According to an exemplary embodiment of the present specification, the organic material layer includes the compound represented by Formula 1 as a host of the light emitting layer, and includes other organic compounds, metals or metal compounds as dopants.

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 compound represented by Chemical Formula 1 as a dopant of the light emitting layer.

According to an exemplary embodiment of the present specification, the organic material layer includes an electron transport layer, an electron injection layer, or a layer for simultaneously transporting and transporting electrons, and the electron transport layer, the electron injection layer, or the layer for simultaneously transporting and transporting electrons. It includes the compound.

According to the exemplary embodiment of the present specification, the organic material layer further includes a hole injection layer or a hole transport layer including a compound including an arylamino group, a carbazole group or a benzocarbazole group, in addition to the organic material layer including the compound represented by Chemical Formula 1 .

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

[Formula 1-A]

In Chemical Formula 1-A,

n1 is an integer of 1 or more,

Ar7 is a substituted or unsubstituted monovalent or higher benzofluorene group; Substituted or unsubstituted monovalent or higher fluoranthene group; A substituted or unsubstituted monovalent or higher pyrene group; Or a substituted or unsubstituted monovalent or higher chrysene group,

L4 is a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

Ar8 and Ar9 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted germanium group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted arylalkyl group; Or a substituted or unsubstituted heteroaryl group, or may combine with each other to form a substituted or unsubstituted ring,

When n1 is 2 or more, the structures in two or more parentheses are the same or different from each other.

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

According to an exemplary embodiment of the present specification, L4 is a direct bond.

According to an exemplary embodiment of the present specification, n1 is 2.

In one embodiment of the present specification, Ar7 is a divalent pyrene group unsubstituted or substituted with deuterium, a methyl group, an ethyl group, or a tert-butyl group.

According to an exemplary embodiment of the present specification, Ar8 and Ar9 are the same as or different from each other, and each independently represent a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to an exemplary embodiment of the present specification, Ar8 and Ar9 are the same as or different from each other, and each independently an aryl group unsubstituted or substituted with a germanium group substituted with an alkyl group.

According to an exemplary embodiment of the present specification, Ar8 and Ar9 are the same or different from each other, and each independently an aryl group unsubstituted or substituted with a trimethylgermanium group.

According to an exemplary embodiment of the present specification, Ar8 and Ar9 are the same as or different from each other, and each independently represent a substituted or unsubstituted phenyl group.

According to an exemplary embodiment of the present specification, Ar8 and Ar9 is a phenyl group unsubstituted or substituted with a trimethylgernium group.

According to an exemplary embodiment of the present specification, Chemical Formula 1-A is represented by the following 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 a compound represented by the following Chemical Formula 2-A.

[Formula 2-A]

In Chemical Formula 2-A,

G11 is 1-naphthyl group, 2-naphthyl group, 1-anthryl group, 2-anthryl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9- Phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group, 9-naphthacenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 3-methyl-2-naphthyl group, 4-methyl- 1-naphthyl group, or

ego,

G12 is a phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthryl group, 2-anthryl group, 9-anthryl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group, 9-naphthacenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 2-biphenylyl group , 3-biphenylyl group, 4-biphenylyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m -Terphenyl-3-yl group, m-terphenyl-2-yl group, o-tolyl group, m-tolyl group, p-tolyl group, pt-butylphenyl group, p- (2-phenylpropyl) phenyl group, 3-methyl 2-naphthyl group, 4-methyl-1-naphthyl group, 4-methyl-1-anthryl group, 4'-methylbiphenylyl group, 4 "-t-butyl-p-terphenyl-4-yl group, or 3-fluoranthenyl group,

G13 and G14 are the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

g12 is an integer of 1 to 5,

g13 and g14 are each an integer of 1 to 4,

When g12 to g14 are each two or more, the structures in two or more parentheses are the same as or different from each other.

According to an exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by Formula 2-A as a host of the light emitting layer.

According to an exemplary embodiment of the present specification, G11 is a 1-naphthyl group.

According to an exemplary embodiment of the present specification, the G12 is a 2-naphthyl group.

According to an exemplary embodiment of the present specification, the G13 and G14 is hydrogen.

According to an exemplary embodiment of the present specification, Formula 2-A is represented by the following compound.

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 represented by Chemical Formula 1.

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

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: physical vapor deposition) such as sputtering (e-beam evaporation), by depositing a metal or conductive metal oxide or an alloy thereof on the substrate It can be prepared by forming a first electrode, forming 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 second electrode 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 a first electrode material on a substrate. In addition, the compound represented by Chemical Formula 1 may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method in the manufacture of the organic light emitting device. Here, the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, etc., but is not limited thereto.

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

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

According to another exemplary embodiment of the present specification, 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, Mg / Ag, and the like, but are not limited thereto.

The hole injection layer is a layer for injecting holes from an electrode as a hole injection material, and has a capability of transporting holes with a hole injection material, and thus has an excellent hole injection effect at an anode and an excellent hole injection effect for the light emitting layer or the light emitting material The compound which prevents the movement of the excitons produced | generated in the light emitting layer 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 electron blocking layer is a layer that can prevent the holes injected from the hole injection layer to enter the electron injection layer through the light emitting layer to improve the life and efficiency of the device, if necessary, using a known material using a known material and the electron It may be formed in a suitable portion between the injection layers.

The light emitting material of the light emitting layer is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable. Specific examples thereof include 8-hydroxyquinoline aluminum complex (Alq ₃ ); Carbazole series compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzothiazole and benzimidazole series compounds; Poly (p-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene, rubrene and the like, but are not limited thereto.

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

Examples of the dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. 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 of the electron transporting layer is a layer for receiving electrons from the electron injection layer and transporting electrons to the light emitting layer. The electron transporting material is a material capable of injecting electrons well from the cathode and transferring them to the light emitting layer. This large material 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 hole blocking layer is a layer that blocks the reaching of the cathode of the hole, and may be generally formed under the same conditions as the hole injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, and the like, but are not limited thereto.

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.

According to an exemplary embodiment of the present specification, the compound represented by Formula 1 may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.

Hereinafter, the present invention will be described in detail with reference to Examples. However, embodiments according to the present disclosure may be modified in various other forms, and the scope of the present disclosure is not interpreted to be limited to the embodiments described below. The embodiments of the present specification are provided to more fully describe the present specification to those skilled in the art.

Preparation Example 1 Preparation of Compound 1-1

Compound A (15.0 g, 28.96 mmol), [1,1'-biphenyl] -4-ylboronic acid ([1,1'-biphenyl] -4-ylboronic acid) in a 500 ml round bottom flask in a nitrogen atmosphere ( 6.59g, 33.3mmol) was completely dissolved in 300ml of tetrahydrofuran, and then 2M aqueous potassium carbonate solution (150ml) was added, followed by addition of tetrakis- (triphenylphosphine) palladium (1.01g, 0.87mmol) and heating for 2 hours. Stirred. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 250 ml of ethyl acetate to obtain Compound 1-1 (14.98 g, yield: 87%).

MS [M + H] ⁺ = 593

Preparation Example 2 Preparation of Compound 1-2

Compound A (15.0g, 28.96mmol), (4- (diphenylamino) phenyl) boronic acid ((4- (diphenylamino) phenyl) boronic acid) (9.62g, 33.3mmol) in 500ml round bottom flask under nitrogen atmosphere After dissolving completely in 260ml of tetrahydrofuran, 2M aqueous potassium carbonate solution (130ml) was added thereto, and tetrakis- (triphenylphosphine) palladium (1.01g, 0.87mmol) was added thereto, followed by heating and stirring for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 200 ml of ethyl acetate to obtain Compound 1-2 (16.25 g, yield: 82%).

MS [M + H] ⁺ = 684

Preparation Example 3 Preparation of Compound 1-3

In a 500 ml round bottom flask in nitrogen atmosphere, Compound A (15.0 g, 28.96 mmol) and 9-phenyl-9H-carbazol-3-ylboronic acid (9.62 g, 33.3 mmol) were completely dissolved in 260 ml of tetrahydrofuran, followed by 2M aqueous potassium carbonate solution. (130 ml) was added, tetrakis- (triphenylphosphine) palladium (1.01 g, 0.87 mmol) was added thereto, and the mixture was heated and stirred for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 200 ml of ethyl acetate to obtain Compound 1-3 (14.63 g, yield: 74%).

MS [M + H] ⁺ = 682

Preparation Example 4 Preparation of Compound 1-4

In a 500 ml round-bottom flask in a nitrogen atmosphere, Compound A (15.0 g, 28.96 mmol) and diphenylamine (5.63 g, 33.3 mmol) were completely dissolved in 180 ml of Xylene, followed by addition of sodium tert-butoxide (3.62 g, 37.65 mol), and Bis ( tri- tert -butylphosphine) palladium (0) (0.15 g, 0.29 mmol) was added thereto, followed by heating and stirring for 2 hours. After the temperature was lowered to room temperature and the base was filtered to remove the base, Xylene was concentrated under reduced pressure, and tetrahydrofuran: hexane = 1:20 was used to prepare Compound 1-4 (14.25 g, yield: 81%).

MS [M + H] ⁺ = 608

Preparation Example 5 Preparation of Compound 1-5

Dissolve Compound A (15.0 g, 28.96 mmol) and N-phenyl- [1,1'-biphenyl] -4-amine (8.16 g, 33.3 mmol) in 280 ml of Xylene in a 500 ml round-bottom flask in a nitrogen atmosphere. -butoxide (3.62g, 37.65mol) was added, Bis (tri- tert -butylphosphine) palladium (0) (0.15g, 0.29mmol) was added thereto, and the mixture was heated and stirred for 3 hours. After lowering the temperature to room temperature and filtering to remove the base, Xylene was concentrated under reduced pressure and tetrahydrofuran: hexane = 1:15 to prepare the compound 1-5 (16.11 g, yield: 80%).

MS [M + H] ⁺ = 684

Preparation Example 6 Preparation of Compound 1-6

Dissolve Compound A (15.0 g, 28.96 mmol) and di ([1,1'-biphenyl] -4-yl) amine (10.69 g, 33.3 mmol) in 320 ml of Xylene in a 500 ml round-bottom flask in a nitrogen atmosphere. -butoxide (3.62g, 37.65mol) was added, Bis (tri- tert -butylphosphine) palladium (0) (0.15g, 0.29mmol) was added thereto, and the mixture was heated and stirred for 5 hours. After lowering the temperature to room temperature and filtering to remove the base, Xylene was concentrated under reduced pressure and tetrahydrofuran: hexane = 1: 9 to prepare the compound 1-6 (19.44g, yield: 93%).

MS [M + H] ⁺ = 760

Preparation Example 7 Preparation of Compound 1-7

Compound A (15.0 g, 28.96 mmol), N-([1,1'-biphenyl] -4-yl)-[1,1'-biphenyl] -2-amine (10.69 g) in a 500 ml round bottom flask under nitrogen atmosphere , 33.3mmol) was dissolved completely in 320ml of Xylene, then sodium tert-butoxide (3.62g, 37.65mol) was added, and Bis (tri- tert -butylphosphine) palladium (0) (0.15g, 0.29mmol) was added for 5 hours. Stirring while heating. After the temperature was lowered to room temperature and the base was filtered to remove the base, Xylene was concentrated under reduced pressure and tetrahydrofuran: hexane = 1:12 was used to prepare Compound 1-7 (15.89 g, yield: 75%).

MS [M + H] ⁺ = 760

Preparation Example 8 Preparation of Compound 1-8

Dissolve Compound A (15.0 g, 28.96 mmol) and 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine (9.52 g, 33.3 mmol) in 320 ml of Xylene in a 500 ml round-bottom flask in a nitrogen atmosphere. tert-butoxide (3.62g, 37.65mol) was added, Bis (tri- tert -butylphosphine) palladium (0) (0.15g, 0.29mmol) was added thereto, and the mixture was heated and stirred for 3 hours. After the temperature was lowered to room temperature and the base was filtered to remove the base, Xylene was concentrated under reduced pressure, and tetrahydrofuran: hexane = 1:18 was used to prepare Compound 1-8 (14.77 g, yield: 70%).

MS [M + H] ⁺ = 724

Preparation Example 9 Preparation of Compound 1-9

Compound A (15.0 g, 28.96 mmol), N-([1,1'-biphenyl] -4-yl) -9,9-dimethyl-9H-fluoren-2-amine (12.02) in a 500 ml round bottom flask in a nitrogen atmosphere. g, 33.3mmol) and then completely dissolved in Xylene 320ml was added to the sodium tert-butoxide (3.62g, 37.65mol ) , insert a Bis (tri- tert -butylphosphine) palladium ( 0) (0.15g, 0.29mmol) 3 Heat stirring for hours. After the temperature was lowered to room temperature and the base was filtered to remove the base, Xylene was concentrated under reduced pressure, and tetrahydrofuran: hexane = 1:18 was used to prepare Compound 1-9 (18.50 g, yield: 81%).

MS [M + H] ⁺ = 800

Preparation Example 10 Preparation of Compound 1-10

Compound A-1 (15.0g, 26.74mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (6.49g, 33.3mmol) in tetrahydrofuran 360ml in a 500ml round bottom flask in nitrogen atmosphere completely After dissolving, 2 M aqueous potassium carbonate solution (180 ml) was added, tetrakis- (triphenylphosphine) palladium (1.01 g, 0.87 mmol) was added thereto, and the mixture was heated and stirred for 6 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 300 ml of ethyl acetate to obtain Compound 1-10 (16.12 g, yield: 83%).

MS [M + H] ⁺ = 672

Preparation Example 11 Preparation of Compound 1-11

In a 500 ml round-bottom flask in a nitrogen atmosphere, completely dissolved in 360 ml of Compound A-1 (15.0 g, 26.74 mmol) and 2-chloro-4,6-diphenylpyrimidine (6.49 g, 33.3 mmol) tetrahydrofuran, followed by 2 M aqueous potassium carbonate solution (180 ml ) Was added, tetrakis- (triphenylphosphine) palladium (1.01 g, 0.87 mmol) was added thereto, and the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 280 ml of ethyl acetate to obtain the compound 1-11 (14.81 g, yield: 76%).

MS [M + H] ⁺ = 671

Preparation Example 12 Preparation of Compound 1-12

In a 500 ml round-bottom flask in nitrogen atmosphere, completely dissolved in 360 ml of Compound A-1 (15.0 g, 26.74 mmol) and 4-chloro-2,6-diphenylpyrimidine (6.49 g, 33.3 mmol) tetrahydrofuran, ) Was added, and tetrakis- (triphenylphosphine) palladium (1.01 g, 0.87 mmol) was added thereto, followed by heating and stirring for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 330 ml of ethyl acetate to obtain the compound 1-12 (13.52 g, yield: 71%).

MS [M + H] ⁺ = 671

Preparation Example 13 Preparation of Compound 1-13

In a 500 ml round-bottom flask in a nitrogen atmosphere, completely dissolved in 360 ml of Compound A-1 (15.0 g, 26.74 mmol) and 2-chloro-4,6-diphenylpyridine (6.49 g, 33.3 mmol) tetrahydrofuran, followed by 2 M aqueous potassium carbonate solution (180 ml ) Was added, tetrakis- (triphenylphosphine) palladium (1.01 g, 0.87 mmol) was added thereto, and the mixture was heated and stirred for 6 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 350 ml of ethyl acetate to obtain Compound 1-13 (11.19 g, yield: 62%).

MS [M + H] ⁺ = 670

Preparation Example 14 Preparation of Compound 1-14

In nitrogen atmosphere, 500 ml round bottom flask was completely dissolved in 360 ml of Compound A-1 (15.0 g, 26.74 mmol) and 2-chloro-4-phenylquinazoline (6.49 g, 33.3 mmol) tetrahydrofuran, followed by 2M aqueous potassium carbonate solution (180 ml). After addition, tetrakis- (triphenylphosphine) palladium (1.01 g, 0.87 mmol) was added thereto, and the mixture was heated and stirred for 7 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 350 ml of ethyl acetate to obtain Compound 1-14 (14.86 g, yield: 80%).

MS [M + H] ⁺ = 645

Preparation Example 15 Preparation of Compound 1-15

In a 500 ml round-bottom flask in a nitrogen atmosphere, completely dissolved in 360 ml of Compound A-1 (15.0 g, 26.74 mmol) and 2-bromodibenzo [b, d] furan (8.19 g, 33.3 mmol) tetrahydrofuran, followed by 2M aqueous potassium carbonate solution (180 ml ) Was added, tetrakis- (triphenylphosphine) palladium (1.01 g, 0.87 mmol) was added thereto, and the mixture was heated and stirred for 7 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 350 ml of ethyl acetate to obtain the compound 1-15 (14.67 g, yield: 84%).

MS [M + H] ⁺ = 607

Preparation Example 16 Preparation of Compound 1-16

In a 500 ml round-bottom flask in a nitrogen atmosphere, completely dissolved in 360 ml of Compound A-1 (15.0 g, 26.74 mmol) and 2-bromodibenzo [b, d] thiophene (8.19 g, 33.3 mmol) tetrahydrofuran, followed by 2M aqueous potassium carbonate solution (180 ml ) Was added, tetrakis- (triphenylphosphine) palladium (1.01 g, 0.87 mmol) was added thereto, and the mixture was heated and stirred for 5 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 350 ml of ethyl acetate to obtain Compound 1-16 (13.21 g, yield: 74%).

MS [M + H] ⁺ = 623

Preparation Example 17 Preparation of Compound 1-17

Compound A-1 (15.0g, 26.74mmol), 2-2- (4-bromophenyl) -1-phenyl-1H-benzo [d] imidazole (11.59g, 33.3mmol) tetrahydro into 500ml round bottom flask in nitrogen atmosphere After completely dissolved in 360 ml of furan, 2M aqueous potassium carbonate solution (180 ml) was added thereto, and tetrakis- (triphenylphosphine) palladium (1.01 g, 0.87 mmol) was added thereto, followed by heating and stirring for 5 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 350 ml of ethyl acetate to obtain Compound 1-17 (13.21 g, yield: 74%).

MS [M + H] ⁺ = 709

Preparation Examples 18 to 26 Preparation of Compounds 1-18 to 1-26

Except for using the compound of Formula 1 Formula B instead of Compound A in Preparation Examples 1 to 9 were prepared in the same manner as in Preparation Examples 1 to 9 to prepare the following compounds 1-18 to 1-26.

Preparation Examples 27 to 34 Preparation of Compounds 1-27 to 1-34

Except for using the compound B-1 of the general formula 1 in place of compound A-1 in Preparation Examples 10 to 17 in the same manner as in Preparation Examples 10 to 17, to the following compound 1-27 to 1-34 Prepared.

Preparation Examples 35 to 43 Preparation of Compounds 1-35 to 1-43

Except for using the compound of Formula 1 Formula C instead of Compound A in Preparation Examples 1 to 9 were prepared in the same manner as in Preparation Examples 1 to 9 to prepare the following compounds 1-35 to 1-43.

Preparation Examples 44 to 51 Preparation of Compounds 1-44 to 1-51

Preparation Example 10 to 17 except for using the compound C-1 of the general formula 1 in place of the compound A-1 in the same manner as in Preparation Examples 10 to 17, to the following compound 1-44 to 1-51 Prepared.

Preparation Examples 52 to 60 Preparation of Compounds 1-52 to 1-60

Except for using the compound D of the general formula 1 in place of Compound A in Preparation Examples 1 to 9 in the same manner as in Preparation Examples 1 to 9 to prepare the following compounds 1-52 to 1-60.

Preparation Examples 61 to 68 Preparation of Compounds 1-61 to 1-68

Except for using the compound D-1 of the general formula 1 in place of compound A-1 in Preparation Examples 10 to 17 in the same manner as in Preparation Examples 10 to 17, to the following compound 1-61 to 1-68 Prepared.

Preparation Examples 69 to 77 Preparation of Compounds 2-1 to 2-9

Except for using the compound E of the general formula 2 in place of the compound A in Preparation Examples 1 to 9 in the same manner as in Preparation Examples 1 to 9 to prepare the following compounds 2-1 to 2-10.

Preparation Examples 78 to 85 Preparation of Compounds 2-10 to 2-17

Except for using the compound E-1 of Formula 2 in place of the compound A-1 in Preparation Examples 10 to 17 in the same manner as in Preparation Examples 10 to 17, to the following compound 2-10 to 2-17 Prepared.

Preparation Examples 86 to 94 Preparation of Compounds 2-18 to 2-26

Except for using the compound F of the general formula (2) instead of compound A in Preparation Examples 1 to 9 in the same manner as in Preparation Examples 1 to 9 to prepare the following compounds 2-18 to 2-26.

Preparation Examples 95 to 102 Preparation of Compound 2-27 to 2-34

Except for using the compound of Formula 2 F-1 instead of Compound A-1 in Preparation Examples 10 to 17 in the same manner as in Preparation Examples 10 to 17, to the following compound 2-27 to 2-34 Prepared.

Preparation Examples 103 to 111 Preparation of Compound 2-35 to 2-43

Except for using the compound of Formula 2 in place of Compound A in Preparation Examples 1 to 9 in the same manner as in Preparation Examples 1 to 9 to prepare the compound 2-35 to 2-43.

Preparation Examples 112 to 119 Preparation of the Compound 2-44 to 2-51

Except for using the compound G-1 of the general formula 2 in place of compound A-1 in Preparation Examples 10 to 17 in the same manner as in Preparation Examples 10 to 17, to the following compound 2-44 to 2-51 Prepared.

Preparation Examples 120 to 128 Preparation of Compound 2-52 to 2-60

Except for using the compound H of the general formula 2 in place of the compound A in Preparation Examples 1 to 9 in the same manner as in Preparation Examples 1 to 9 to prepare the following compound 2-52 to 2-60.

Preparation Example 129 to 136 Preparation of Compound 2-61 to 2-68

Except for using the compound H-1 of Formula 2 in place of the compound A-1 in Preparation Examples 10 to 17 in the same manner as in Preparation Examples 10 to 17, to the following compound 2-61 to 2-68 Prepared.

Preparation Example 137 Preparation of Compound 1-69

Compound I (5.21g, 8.74mmol), 6- (tert-butyl) -N- (o-tolyl) dibenzo [b, d] furan-4-amine (6.04g, 18.36mmol) in 500ml round bottom flask in nitrogen atmosphere ) Completely dissolved in 160 ml of xylene, followed by adding sodium tert-butoxide (2.02 g, 20.98 mmol), adding Bis (tri- tert -butylphosphine) palladium (0) (0.04 g, 0.09 mmol) and stirring for 3 hours. It was. After the temperature was lowered to room temperature and the base was filtered to remove the base, Xylene was concentrated under reduced pressure, and tetrahydrofuran: hexane = 1:25 was used to prepare Compound 1-69 (4.59 g, purity: 99.99%, yield: 64%). It was.

MS [M + H] ⁺ = 1095

Preparation Example 138 Preparation of Compound 1-70

170 ml of Xylene with Compound I (4.35 g, 7.30 mmol), 6-cyclohexyl-N- (o-tolyl) dibenzo [b, d] furan-4-amine (5.44 g, 15.33 mmol) in a 500 ml round-bottom flask in a nitrogen atmosphere After completely dissolved in sodium tert-butoxide (1.68g, 17.52mmol) was added, Bis (tri- tert -butylphosphine) palladium (0) (0.04g, 0.07mmol) was added and stirred for 4 hours. After the temperature was lowered to room temperature and the base was filtered to remove the base, Xylene was concentrated under reduced pressure, and tetrahydrofuran: hexane = 1:20 was used to prepare Compound 1-70 (3.32 g, purity: 99.98%, yield: 42%). It was.

MS [M + H] ⁺ = 1147

Preparation Example 139 Preparation of Compound 1-71

Dissolve Compound I (5.36 g, 8.99 mmol) and 4- (tert-butyl) -N- (p-tolyl) aniline (4.51 g, 18.89 mmol) in 210 ml of Xylene in a 500 ml round-bottom flask in a nitrogen atmosphere. -butoxide (2.07g, 21.58mmol) was added, Bis (tri- tert -butylphosphine) palladium (0) (0.05g, 0.09mmol) was added thereto, and the mixture was heated and stirred for 3 hours. After the temperature was lowered to room temperature and the base was filtered to remove the base, Xylene was concentrated under reduced pressure, and tetrahydrofuran: hexane = 1:35 was used to prepare the compound 1-71 (2.67 g, purity: 99.99%, yield: 32%). It was.

MS [M + H] ⁺ = 915

Preparation Example 140 Preparation of Compound 1-72

Dissolve Compound I (4.81g, 8.07mmol) and bis (4- (tert-butyl) phenyl) amine (4.76g, 16.95mmol) in 180ml of Xylene in a 500ml round-bottom flask in nitrogen atmosphere, and then add sodium tert-butoxide (1.86). g, 19.37 mmol) was added, Bis (tri- tert- butylphosphine) palladium (0) (0.04 g, 0.08 mmol) was added thereto, and the mixture was heated and stirred for 5 hours. After the temperature was lowered to room temperature and the base was filtered to remove the base, Xylene was concentrated under reduced pressure, and tetrahydrofuran: hexane = 1:30 was used to prepare Compound 1-72 (3.47 g, purity: 99.99%, yield: 43%). It was.

MS [M + H] ⁺ = 999

Preparation Example 141 Preparation of Compound 2-69

Compound J (3.57g, 5.74mmol) and bis (4- (tert-butyl) phenyl) amine (3.39g, 12.05mmol) were completely dissolved in 200ml of Xylene in a 500ml round bottom flask in nitrogen atmosphere, followed by sodium tert-butoxide (1.32). was added to the g, 13.77mmol), insert a Bis (tri- tert -butylphosphine) palladium ( 0) (0.03g, 0.06mmol) was added and the mixture was heated and stirred for 4 hours. After the temperature was lowered to room temperature and the base was filtered to remove the base, Xylene was concentrated under reduced pressure, and tetrahydrofuran: hexane = 1:35 was used to prepare the compound 2-69 (3.47 g, purity: 99.99%, yield: 58%). It was.

MS [M + H] ⁺ = 1025

Preparation Example 142 Compound 2-70

Dissolve Compound J (3.64g, 5.85mmol), 4- (tert-butyl) -N- (4- (trimethylsilyl) phenyl) aniline (3.65g, 12.29mmol) in 230ml Xylene in a 500ml round bottom flask in a nitrogen atmosphere. After sodium tert-butoxide (1.35g, 14.05mmol) was added, Bis (tri- tert -butylphosphine) palladium (0) (0.03g, 0.06mmol) was added and stirred for 4 hours. After the temperature was lowered to room temperature and the base was filtered to remove the base, Xylene was concentrated under reduced pressure, and tetrahydrofuran: hexane = 1:25 was used to prepare the compound 2-70 (4.26 g, purity: 99.99%, yield: 69%). It was.

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

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

Compound 4-4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (NPB) (300 Pa), which is a substance for transporting holes on the hole injection layer, was vacuum deposited to form a hole transport layer. It was.

Subsequently, the following compound 1-2 was vacuum deposited to a film thickness of 100 kPa on the hole transport layer to form an electron blocking layer.

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

The compound ET1 and the compound LiQ (Lithium Quinolate) were vacuum-deposited on the emission layer in a weight ratio of 1: 1 to form an electron injection and transport layer having a thickness of 300 kPa. On the electron injection and transport layer, lithium fluoride (LiF) and aluminum were deposited to a thickness of 12 kPa in order to form a cathode.

In the above process, the deposition rate of the organic material was maintained at 0.4 ~ 0.7Å / sec, the lithium fluoride of the cathode was maintained at 0.3Å / sec, the deposition rate of aluminum was 2Å / sec, the vacuum degree during deposition is 2 10 ^-7 The organic light emitting device was manufactured by maintaining ˜5 10 ⁻⁶ torr.

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 1-3 was used instead of compound 1-2 in Experimental Example 1-1.

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 1-4 was used instead of compound 1-2 in Experimental Example 1-1.

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 1-5 was used instead of compound 1-2 in Experimental Example 1-1.

Experimental Example 1-5

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 1-6 was used instead of compound 1-2 in Experimental Example 1-1.

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 1-7 was used instead of compound 1-2 in Experimental Example 1-1.

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 1-8 was used instead of compound 1-2 in Experimental Example 1-1.

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 1-9 was used instead of compound 1-2 in Experimental Example 1-1.

Experimental Example 1-9

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 1-19 was used instead of compound 1-2 in Experimental Example 1-1.

Experimental Example 1-10

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 1-20 was used instead of compound 1-2 in Experimental Example 1-1.

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 1-21 was used instead of compound 1-2 in Experimental Example 1-1.

Experimental Example 1-12

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 1-22 was used instead of compound 1-2 in Experimental Example 1-1.

Experimental Example 1-13

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 1-23 was used instead of compound 1-2 in Experimental Example 1-1.

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 1-24 was used instead of compound 1-2 in Experimental Example 1-1.

Experimental Example 1-15

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 1-25 was used instead of compound 1-2 in Experimental Example 1-1.

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 1-26 was used instead of compound 1-2 in Experimental Example 1-1.

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 1-36 was used instead of compound 1-2 in Experimental Example 1-1.

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 1-37 was used instead of compound 1-2 in Experimental Example 1-1.

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 1-38 was used instead of compound 1-2 in Experimental Example 1-1.

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 1-39 was used instead of compound 1-2 in Experimental Example 1-1.

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 1-40 was used instead of compound 1-2 in Experimental Example 1-1.

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 1-41 was used instead of compound 1-2 in Experimental Example 1-1.

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 1-42 was used instead of compound 1-2 in Experimental Example 1-1.

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 1-43 was used instead of compound 1-2 in Experimental Example 1-1.

Experimental Example 1-25

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 1-53 was used instead of compound 1-2 in Experimental Example 1-1.

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 1-54 was used instead of compound 1-2 in Experimental Example 1-1.

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 1-55 was used instead of compound 1-2 in Experimental Example 1-1.

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 1-56 was used instead of compound 1-2 in Experimental Example 1-1.

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 1-57 was used instead of compound 1-2 in Experimental Example 1-1.

Experimental Example 1-30

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 1-58 was used instead of compound 1-2 in Experimental Example 1-1.

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 1-59 was used instead of compound 1-2 in Experimental Example 1-1.

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 1-60 was used instead of compound 1-2 in Experimental Example 1-1.

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

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 2-3 was used instead of compound 1-2 in Experimental Example 1-1.

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 2-4 was used instead of compound 1-2 in Experimental Example 1-1.

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 2-5 was used instead of compound 1-2 in Experimental Example 1-1.

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 2-6 was used instead of compound 1-2 in Experimental Example 1-1.

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 2-7 was used instead of compound 1-2 in Experimental Example 1-1.

Experimental Example 1-39

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 2-8 was used instead of compound 1-2 in Experimental Example 1-1.

Experimental Example 1-40

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 2-9 was used instead of compound 1-2 in Experimental Example 1-1.

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 2-19 was used instead of compound 1-2 in Experimental Example 1-1.

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 2-20 was used instead of compound 1-2 in Experimental Example 1-1.

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 2-21 was used instead of compound 1-2 in Experimental Example 1-1.

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 2-22 was used instead of compound 1-2 in Experimental Example 1-1.

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 2-23 was used instead of compound 1-2 in Experimental Example 1-1.

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 2-24 was used instead of compound 1-2 in Experimental Example 1-1.

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 2-25 was used instead of compound 1-2 in Experimental Example 1-1.

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 2-26 was used instead of compound 1-2 in Experimental Example 1-1.

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 2-36 was used instead of compound 1-2 in Experimental Example 1-1.

Experimental Example 1-50

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 2-37 was used instead of compound 1-2 in Experimental Example 1-1.

Experimental Example 1-51

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 2-38 was used instead of compound 1-2 in Experimental Example 1-1.

Experimental Example 1-52

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 2-39 was used instead of compound 1-2 in Experimental Example 1-1.

Experimental Example 1-53

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 2-40 was used instead of compound 1-2 in Experimental Example 1-1.

Experimental Example 1-54

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 2-41 was used instead of compound 1-2 in Experimental Example 1-1.

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 2-42 was used instead of compound 1-2 in Experimental Example 1-1.

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 2-43 was used instead of compound 1-2 in Experimental Example 1-1.

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 2-53 was used instead of compound 1-2 in Experimental Example 1-1.

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 2-54 was used instead of compound 1-2 in Experimental Example 1-1.

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 2-55 was used instead of compound 1-2 in Experimental Example 1-1.

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 2-56 was used instead of compound 1-2 in Experimental Example 1-1.

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 2-57 was used instead of compound 1-2 in Experimental Example 1-1.

Experimental Example 1-62

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 2-58 was used instead of compound 1-2 in Experimental Example 1-1.

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 2-59 was used instead of compound 1-2 in Experimental Example 1-1.

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 2-60 was used instead of compound 1-2 in Experimental Example 1-1.

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

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

Comparative Example 1-3

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that EB 3 was used instead of compound 1-2 in Experimental Example 1-1.

The organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that EB 4 was used instead of compound 1-2 in Experimental Example 1-1.

When the current was applied to the organic light emitting diodes manufactured according to Experimental Examples 1-1 to 1-64 and Comparative Examples 1-1 to 1-4, the results of Table 1 were obtained.

	화합물(전자차단층)Compound (electron blocking layer)	전압(V@10mA/cm²)Voltage (V @ 10mA / cm ² )	효율(cd/A@10mA/cm²)Efficiency (cd / A @ 10mA / cm ² )	색좌표(x,y)Color coordinates (x, y)
실험예 1-1Experimental Example 1-1	화합물 1-2Compound 1-2	3.953.95	5.255.25	(0.139, 0.122)(0.139, 0.122)
실험예 1-2Experimental Example 1-2	화합물 1-3Compound 1-3	3.823.82	5.385.38	(0.138, 0.126)(0.138, 0.126)
실험예 1-3Experimental Example 1-3	화합물 1-4Compound 1-4	3.673.67	5.715.71	(0.138, 0.127)(0.138, 0.127)
실험예 1-4Experimental Example 1-4	화합물 1-5Compound 1-5	3.683.68	5.625.62	(0.137, 0.125)(0.137, 0.125)
실험예 1-5Experimental Example 1-5	화합물 1-6Compound 1-6	3.693.69	5.735.73	(0.136, 0.125)(0.136, 0.125)
실험예 1-6Experimental Example 1-6	화합물 1-7Compound 1-7	3.643.64	5.675.67	(0.136, 0.127)(0.136, 0.127)
실험예 1-7Experimental Example 1-7	화합물 1-8Compound 1-8	3.633.63	5.785.78	(0.136, 0.125)(0.136, 0.125)
실험예 1-8Experimental Example 1-8	화합물 1-9Compound 1-9	3.643.64	5.615.61	(0.137, 0.125)(0.137, 0.125)
실험예 1-9Experimental Example 1-9	화합물 1-19Compound 1-19	3.733.73	5.585.58	(0.138, 0.125)(0.138, 0.125)
실험예 1-10Experimental Example 1-10	화합물 1-20Compound 1-20	3.783.78	5.425.42	(0.136, 0.125)(0.136, 0.125)
실험예 1-11Experimental Example 1-11	화합물 1-21Compound 1-21	3.733.73	5.575.57	(0.137, 0.125)(0.137, 0.125)
실험예 1-12Experimental Example 1-12	화합물 1-22Compound 1-22	3.753.75	5.455.45	(0.136, 0.125)(0.136, 0.125)
실험예 1-13Experimental Example 1-13	화합물 1-23Compound 1-23	3.823.82	5.585.58	(0.138, 0.126)(0.138, 0.126)
실험예 1-14Experimental Example 1-14	화합물 1-24Compound 1-24	3.873.87	5.515.51	(0.137, 0.125)(0.137, 0.125)
실험예 1-15Experimental Example 1-15	화합물 1-25Compound 1-25	3.803.80	5.425.42	(0.136, 0.127)(0.136, 0.127)
실험예 1-16Experimental Example 1-16	화합물 1-26Compound 1-26	3.813.81	5.535.53	(0.135, 0.127)(0.135, 0.127)
실험예 1-17Experimental Example 1-17	화합물 1-36Compound 1-36	3.643.64	5.675.67	(0.138, 0.127)(0.138, 0.127)
실험예 1-18Experimental Example 1-18	화합물 1-37Compound 1-37	3.733.73	5.585.58	(0.137, 0.125)(0.137, 0.125)
실험예 1-19Experimental Example 1-19	화합물 1-38Compound 1-38	3.643.64	5.615.61	(0.137, 0.125)(0.137, 0.125)
실험예 1-20Experimental Example 1-20	화합물 1-39Compound 1-39	3.733.73	5.585.58	(0.136, 0.127)(0.136, 0.127)
실험예 1-21Experimental Example 1-21	화합물 1-40Compound 1-40	3.643.64	5.625.62	(0.135, 0.127)(0.135, 0.127)
실험예 1-22Experimental Example 1-22	화합물 1-41Compound 1-41	3.733.73	5.575.57	(0.138, 0.127)(0.138, 0.127)
실험예 1-23Experimental Example 1-23	화합물 1-42Compound 1-42	3.693.69	5.655.65	(0.137, 0.125)(0.137, 0.125)
실험예 1-24Experimental Example 1-24	화합물 1-43Compound 1-43	3.783.78	5.685.68	(0.137, 0.125)(0.137, 0.125)
실험예 1-25Experimental Example 1-25	화합물 1-53Compound 1-53	3.573.57	5.815.81	(0.136, 0.125)(0.136, 0.125)
실험예 1-26Experimental Example 1-26	화합물 1-54Compound 1-54	3.613.61	5.855.85	(0.139, 0.122)(0.139, 0.122)
실험예 1-27Experimental Example 1-27	화합물 1-55Compound 1-55	3.633.63	5.985.98	(0.138, 0.126)(0.138, 0.126)
실험예 1-28Experimental Example 1-28	화합물 1-56Compound 1-56	3.623.62	5.815.81	(0.138, 0.127)(0.138, 0.127)
실험예 1-29Experimental Example 1-29	화합물 1-57Compound 1-57	3.643.64	5.825.82	(0.137, 0.125)(0.137, 0.125)
실험예 1-30Experimental Example 1-30	화합물 1-58Compound 1-58	3.603.60	5.835.83	(0.136, 0.125)(0.136, 0.125)
실험예 1-31Experimental Example 1-31	화합물 1-59Compound 1-59	3.613.61	5.975.97	(0.136, 0.127)(0.136, 0.127)
실험예 1-32Experimental Example 1-32	화합물 1-60Compound 1-60	3.603.60	5.885.88	(0.136, 0.125)(0.136, 0.125)
실험예 1-33Experimental Example 1-33	화합물 2-2Compound 2-2	4.054.05	5.155.15	(0.137, 0.125)(0.137, 0.125)
실험예 1-34Experimental Example 1-34	화합물 2-3Compound 2-3	3.923.92	5.285.28	(0.138, 0.125)(0.138, 0.125)
실험예 1-35Experimental Example 1-35	화합물 2-4Compound 2-4	3.773.77	5.615.61	(0.136, 0.125)(0.136, 0.125)
실험예 1-36Experimental Example 1-36	화합물 2-5Compound 2-5	3.783.78	5.525.52	(0.137, 0.125)(0.137, 0.125)
실험예 1-37Experimental Example 1-37	화합물 2-6Compound 2-6	3.793.79	5.635.63	(0.136, 0.125)(0.136, 0.125)
실험예 1-38Experimental Example 1-38	화합물 2-7Compound 2-7	3.743.74	5.575.57	(0.138, 0.126)(0.138, 0.126)
실험예 1-39Experimental Example 1-39	화합물 2-8Compound 2-8	3.733.73	5.685.68	(0.137, 0.125)(0.137, 0.125)
실험예 1-40Experimental Example 1-40	화합물 2-9Compound 2-9	3.743.74	5.515.51	(0.136, 0.127)(0.136, 0.127)
실험예 1-41Experimental Example 1-41	화합물 2-19Compound 2-19	3.833.83	5.485.48	(0.135, 0.127)(0.135, 0.127)
실험예 1-42Experimental Example 1-42	화합물 2-20Compound 2-20	3.883.88	5.325.32	(0.138, 0.127)(0.138, 0.127)
실험예 1-43Experimental Example 1-43	화합물 2-21Compound 2-21	3.833.83	5.475.47	(0.137, 0.125)(0.137, 0.125)
실험예 1-44Experimental Example 1-44	화합물 2-22Compound 2-22	3.853.85	5.355.35	(0.137, 0.125)(0.137, 0.125)
실험예 1-45Experimental Example 1-45	화합물 2-23Compound 2-23	3.923.92	5.485.48	(0.136, 0.127)(0.136, 0.127)
실험예 1-46Experimental Example 1-46	화합물 2-24Compound 2-24	3.973.97	5.415.41	(0.135, 0.127)(0.135, 0.127)
실험예 1-47Experimental Example 1-47	화합물 2-25Compound 2-25	3.903.90	5.325.32	(0.138, 0.127)(0.138, 0.127)
실험예 1-48Experimental Example 1-48	화합물 2-26Compound 2-26	3.913.91	5.435.43	(0.137, 0.125)(0.137, 0.125)
실험예 1-49Experimental Example 1-49	화합물 2-36Compound 2-36	3.743.74	5.575.57	(0.137, 0.125)(0.137, 0.125)
실험예 1-50Experimental Example 1-50	화합물 2-37Compound 2-37	3.833.83	5.485.48	(0.136, 0.125)(0.136, 0.125)
실험예 1-51Experimental Example 1-51	화합물 2-38Compound 2-38	3.743.74	5.515.51	(0.136, 0.125)(0.136, 0.125)
실험예 1-52Experimental Example 1-52	화합물 2-39Compound 2-39	3.833.83	5.485.48	(0.136, 0.125)(0.136, 0.125)
실험예 1-53Experimental Example 1-53	화합물 2-40Compound 2-40	3.743.74	5.525.52	(0.136, 0.125)(0.136, 0.125)
실험예 1-54Experimental Example 1-54	화합물 2-41Compound 2-41	3.833.83	5.475.47	(0.136, 0.125)(0.136, 0.125)
실험예 1-55Experimental Example 1-55	화합물 2-42Compound 2-42	3.793.79	5.555.55	(0.136, 0.125)(0.136, 0.125)
실험예 1-56Experimental Example 1-56	화합물 2-43Compound 2-43	3.883.88	5.585.58	(0.136, 0.125)(0.136, 0.125)
실험예 1-57Experimental Example 1-57	화합물 2-53Compound 2-53	3.673.67	5.715.71	(0.136, 0.125)(0.136, 0.125)
실험예 1-58Experimental Example 1-58	화합물 2-54Compound 2-54	3.713.71	5.755.75	(0.136, 0.125)(0.136, 0.125)
실험예 1-59Experimental Example 1-59	화합물 2-55Compound 2-55	3.733.73	5.885.88	(0.136, 0.125)(0.136, 0.125)
실험예 1-60Experimental Example 1-60	화합물 2-56Compound 2-56	3.723.72	5.715.71	(0.136, 0.125)(0.136, 0.125)
실험예 1-61Experimental Example 1-61	화합물 2-57Compound 2-57	3.743.74	5.725.72	(0.136, 0.125)(0.136, 0.125)
실험예 1-62Experimental Example 1-62	화합물 2-58Compound 2-58	3.703.70	5.735.73	(0.136, 0.125)(0.136, 0.125)
실험예 1-63Experimental Example 1-63	화합물 2-59Compound 2-59	3.713.71	5.875.87	(0.136, 0.125)(0.136, 0.125)
실험예 1-64Experimental Example 1-64	화합물 2-60Compound 2-60	3.703.70	5.785.78	(0.136, 0.125)(0.136, 0.125)
비교예 1-1Comparative Example 1-1	EB 1EB 1	4.364.36	4.634.63	(0.138, 0.127)(0.138, 0.127)
비교예 1-2Comparative Example 1-2	EB 2EB 2	4.314.31	4.584.58	(0.139, 0.125)(0.139, 0.125)
비교예 1-3Comparative Example 1-3	EB 3EB 3	4.494.49	4.424.42	(0.139, 0.126)(0.139, 0.126)
비교예 1-4Comparative Example 1-4	EB 4EB 4	4.564.56	4.324.32	(0.139, 0.127)(0.139, 0.127)

As shown in Table 1, the compounds of Experimental Examples 1-1 to 1-64 are not only EB 1 (TCTA) of Comparative Example 1-1 which is frequently used as an electron blocking layer in an organic light emitting device, but A of Formula 1 is phenyl It can be seen that the characteristics of lower voltage and higher efficiency are shown than Comparative Examples 1-2 to 1-4 made of, naphthalene or anthracene.

The compound of Chemical Formula 1 according to the present specification was excellent in electron blocking ability and showed low voltage and high efficiency and could be applied to an organic light emitting device.

EB 1 of Comparative Example 1-1 was used instead of Compound 1-2 as the electron blocking layer in Experimental Example 1-1, and the compounds of Experimental Examples 1-1 to 64 instead of NPB of Experimental Example 1-1 as the hole transporting layer. Except that used, the experiment was carried out in the same manner as in Experiment 1-1.

Except that EB 1 of Comparative Example 1-1 was used as the electron blocking layer in Experimental Example 1-1 and NPB (HT 1) of Experimental Example 1-1 was used as the hole transporting layer. Experiment was made.

Except for using the compound EB 1 of Comparative Example 1-1 as the electron blocking layer in Experimental Example 1-1, except that HT 2 was used as the hole transport layer was the same experiment.

Comparative Example 2-3

Except for using the compound EB 1 of Comparative Example 1-1 as the electron blocking layer in Experimental Example 1-1 and HT 3 as the hole transport layer was the same experiment.

Except for using the compound EB 1 of Comparative Example 1-1 as the electron blocking layer in Experimental Example 1-1, except that HT 4 was used as the hole transport layer was the same experiment.

Except for using the compound EB 1 of Comparative Example 1-1 as the electron blocking layer in Experimental Example 1-1 and HT 5 as the hole transport layer was the same experiment.

When the electric current was applied to the organic light emitting element produced by Experimental Example 2-1 to 2-64 and Comparative Examples 2-1 to 2-5, the result of Table 2 was obtained.

	화합물(정공수송층)Compound (hole transport layer)	전압(V@10mA/cm²)Voltage (V @ 10mA / cm ² )	효율(cd/A@10mA/cm²)Efficiency (cd / A @ 10mA / cm ² )	색좌표(x,y)Color coordinates (x, y)
실험예 2-1Experimental Example 2-1	화합물 1-2Compound 1-2	4.154.15	5.755.75	(0.139, 0.122)(0.139, 0.122)
실험예 2-2Experimental Example 2-2	화합물 1-3Compound 1-3	4.024.02	5.885.88	(0.138, 0.126)(0.138, 0.126)
실험예 2-3Experimental Example 2-3	화합물 1-4Compound 1-4	3.873.87	6.256.25	(0.138, 0.127)(0.138, 0.127)
실험예 2-4Experimental Example 2-4	화합물 1-5Compound 1-5	3.883.88	6.246.24	(0.137, 0.125)(0.137, 0.125)
실험예 2-5Experimental Example 2-5	화합물 1-6Compound 1-6	3.893.89	6.226.22	(0.136, 0.125)(0.136, 0.125)
실험예 2-6Experimental Example 2-6	화합물 1-7Compound 1-7	3.843.84	6.136.13	(0.136, 0.127)(0.136, 0.127)
실험예 2-7Experimental Example 2-7	화합물 1-8Compound 1-8	3.833.83	6.206.20	(0.136, 0.125)(0.136, 0.125)
실험예 2-8Experimental Example 2-8	화합물 1-9Compound 1-9	3.843.84	6.106.10	(0.137, 0.125)(0.137, 0.125)
실험예 2-9Experimental Example 2-9	화합물 1-19Compound 1-19	3.933.93	6.016.01	(0.138, 0.125)(0.138, 0.125)
실험예 2-10Experimental Example 2-10	화합물 1-20Compound 1-20	3.983.98	5.925.92	(0.136, 0.125)(0.136, 0.125)
실험예 2-11Experimental Example 2-11	화합물 1-21Compound 1-21	3.933.93	6.056.05	(0.137, 0.125)(0.137, 0.125)
실험예 2-12Experimental Example 2-12	화합물 1-22Compound 1-22	3.953.95	5.955.95	(0.136, 0.125)(0.136, 0.125)
실험예 2-13Experimental Example 2-13	화합물 1-23Compound 1-23	4.024.02	6.086.08	(0.138, 0.126)(0.138, 0.126)
실험예 2-14Experimental Example 2-14	화합물 1-24Compound 1-24	3.973.97	6.016.01	(0.137, 0.125)(0.137, 0.125)
실험예 2-15Experimental Example 2-15	화합물 1-25Compound 1-25	4.004.00	5.925.92	(0.136, 0.127)(0.136, 0.127)
실험예 2-16Experimental Example 2-16	화합물 1-26Compound 1-26	4.014.01	6.026.02	(0.135, 0.127)(0.135, 0.127)
실험예 2-17Experimental Example 2-17	화합물 1-36Compound 1-36	3.843.84	6.156.15	(0.138, 0.127)(0.138, 0.127)
실험예 2-18Experimental Example 2-18	화합물 1-37Compound 1-37	3.933.93	6.036.03	(0.137, 0.125)(0.137, 0.125)
실험예 2-19Experimental Example 2-19	화합물 1-38Compound 1-38	3.843.84	6.136.13	(0.137, 0.125)(0.137, 0.125)
실험예 2-20Experimental Example 2-20	화합물 1-39Compound 1-39	3.933.93	6.056.05	(0.136, 0.127)(0.136, 0.127)
실험예 2-21Experimental Example 2-21	화합물 1-40Compound 1-40	3.843.84	6.166.16	(0.135, 0.127)(0.135, 0.127)
실험예 2-22Experimental Example 2-22	화합물 1-41Compound 1-41	3.933.93	6.076.07	(0.138, 0.127)(0.138, 0.127)
실험예 2-23Experimental Example 2-23	화합물 1-42Compound 1-42	3.893.89	6.156.15	(0.137, 0.125)(0.137, 0.125)
실험예 2-24Experimental Example 2-24	화합물 1-43Compound 1-43	3.983.98	6.186.18	(0.137, 0.125)(0.137, 0.125)
실험예 2-25Experimental Example 2-25	화합물 1-53Compound 1-53	3.753.75	6.316.31	(0.136, 0.125)(0.136, 0.125)
실험예 2-26Experimental Example 2-26	화합물 1-54Compound 1-54	3.863.86	6.356.35	(0.139, 0.122)(0.139, 0.122)
실험예 2-27Experimental Example 2-27	화합물 1-55Compound 1-55	3.853.85	6.486.48	(0.138, 0.126)(0.138, 0.126)
실험예 2-28Experimental Example 2-28	화합물 1-56Compound 1-56	3.813.81	6.316.31	(0.138, 0.127)(0.138, 0.127)
실험예 2-29Experimental Example 2-29	화합물 1-57Compound 1-57	3.843.84	6.326.32	(0.137, 0.125)(0.137, 0.125)
실험예 2-30Experimental Example 2-30	화합물 1-58Compound 1-58	3.803.80	6.336.33	(0.136, 0.125)(0.136, 0.125)
실험예 2-31Experimental Example 2-31	화합물 1-59Compound 1-59	3.813.81	6.476.47	(0.136, 0.127)(0.136, 0.127)
실험예 2-32Experimental Example 2-32	화합물 1-60Compound 1-60	3.803.80	6.356.35	(0.136, 0.125)(0.136, 0.125)
실험예 2-33Experimental Example 2-33	화합물 2-2Compound 2-2	4.254.25	5.655.65	(0.137, 0.125)(0.137, 0.125)
실험예 2-34Experimental Example 2-34	화합물 2-3Compound 2-3	4.124.12	5.785.78	(0.138, 0.125)(0.138, 0.125)
실험예 2-35Experimental Example 2-35	화합물 2-4Compound 2-4	3.973.97	6.116.11	(0.136, 0.125)(0.136, 0.125)
실험예 2-36Experimental Example 2-36	화합물 2-5Compound 2-5	3.983.98	6.026.02	(0.137, 0.125)(0.137, 0.125)
실험예 2-37Experimental Example 2-37	화합물 2-6Compound 2-6	3.953.95	6.136.13	(0.136, 0.125)(0.136, 0.125)
실험예 2-38Experimental Example 2-38	화합물 2-7Compound 2-7	3.943.94	6.076.07	(0.138, 0.126)(0.138, 0.126)
실험예 2-39Experimental Example 2-39	화합물 2-8Compound 2-8	3.933.93	6.186.18	(0.137, 0.125)(0.137, 0.125)
실험예 2-40Experimental Example 2-40	화합물 2-9Compound 2-9	3.903.90	6.016.01	(0.136, 0.127)(0.136, 0.127)
실험예 2-41Experimental Example 2-41	화합물 2-19Compound 2-19	4.034.03	5.985.98	(0.135, 0.127)(0.135, 0.127)
실험예 2-42Experimental Example 2-42	화합물 2-20Compound 2-20	4.084.08	5.825.82	(0.138, 0.127)(0.138, 0.127)
실험예 2-43Experimental Example 2-43	화합물 2-21Compound 2-21	4.034.03	5.975.97	(0.137, 0.125)(0.137, 0.125)
실험예 2-44Experimental Example 2-44	화합물 2-22Compound 2-22	4.054.05	5.855.85	(0.137, 0.125)(0.137, 0.125)
실험예 2-45Experimental Example 2-45	화합물 2-23Compound 2-23	4.124.12	5.945.94	(0.136, 0.127)(0.136, 0.127)
실험예 2-46Experimental Example 2-46	화합물 2-24Compound 2-24	4.144.14	5.925.92	(0.135, 0.127)(0.135, 0.127)
실험예 2-47Experimental Example 2-47	화합물 2-25Compound 2-25	4.124.12	5.835.83	(0.138, 0.127)(0.138, 0.127)
실험예 2-48Experimental Example 2-48	화합물 2-26Compound 2-26	4.184.18	5.985.98	(0.137, 0.125)(0.137, 0.125)
실험예 2-49Experimental Example 2-49	화합물 2-36Compound 2-36	3.943.94	6.076.07	(0.137, 0.125)(0.137, 0.125)
실험예 2-50Experimental Example 2-50	화합물 2-37Compound 2-37	4.014.01	5.995.99	(0.136, 0.125)(0.136, 0.125)
실험예 2-51Experimental Example 2-51	화합물 2-38Compound 2-38	3.943.94	6.0156.015	(0.136, 0.125)(0.136, 0.125)
실험예 2-52Experimental Example 2-52	화합물 2-39Compound 2-39	4.034.03	5.965.96	(0.136, 0.125)(0.136, 0.125)
실험예 2-53Experimental Example 2-53	화합물 2-40Compound 2-40	3.943.94	6.026.02	(0.136, 0.125)(0.136, 0.125)
실험예 2-54Experimental Example 2-54	화합물 2-41Compound 2-41	4.034.03	5.925.92	(0.136, 0.125)(0.136, 0.125)
실험예 2-55Experimental Example 2-55	화합물 2-42Compound 2-42	3.983.98	6.056.05	(0.136, 0.125)(0.136, 0.125)
실험예 2-56Experimental Example 2-56	화합물 2-43Compound 2-43	4.054.05	6.016.01	(0.136, 0.125)(0.136, 0.125)
실험예 2-57Experimental Example 2-57	화합물 2-53Compound 2-53	3.843.84	6.216.21	(0.136, 0.125)(0.136, 0.125)
실험예 2-58Experimental Example 2-58	화합물 2-54Compound 2-54	3.933.93	6.256.25	(0.136, 0.125)(0.136, 0.125)
실험예 2-59Experimental Example 2-59	화합물 2-55Compound 2-55	3.923.92	6.386.38	(0.136, 0.125)(0.136, 0.125)
실험예 2-60Experimental Example 2-60	화합물 2-56Compound 2-56	3.973.97	6.216.21	(0.136, 0.125)(0.136, 0.125)
실험예 2-61Experimental Example 2-61	화합물 2-57Compound 2-57	3.993.99	6.226.22	(0.136, 0.125)(0.136, 0.125)
실험예 2-62Experimental Example 2-62	화합물 2-58Compound 2-58	3.983.98	6.236.23	(0.136, 0.125)(0.136, 0.125)
실험예 2-63Experimental Example 2-63	화합물 2-59Compound 2-59	3.913.91	6.376.37	(0.136, 0.125)(0.136, 0.125)
실험예 2-64Experimental Example 2-64	화합물 2-60Compound 2-60	3.903.90	6.286.28	(0.136, 0.125)(0.136, 0.125)
비교예 2-1Comparative Example 2-1	NPB(HT 1)NPB (HT 1)	4.564.56	5.135.13	(0.138, 0.127)(0.138, 0.127)
비교예 2-2Comparative Example 2-2	HT 2HT 2	4.514.51	5.085.08	(0.139, 0.125)(0.139, 0.125)
비교예 2-3Comparative Example 2-3	HT 3HT 3	4.694.69	4.924.92	(0.139, 0.126)(0.139, 0.126)
비교예 2-4Comparative Example 2-4	HT 4HT 4	4.764.76	4.824.82	(0.139, 0.127)(0.139, 0.127)
비교예 2-5Comparative Example 2-5	HT 5HT 5	4.824.82	4.954.95	(0.139, 0.127)(0.139, 0.127)

As shown in Table 2, the compounds of Experimental Examples 2-1 to 2-64 are not only NPBs (Comparative Example 2-1) which are frequently used as hole transporting layers in organic light emitting devices, but also A of Formula 1 is phenyl, naphthalene or anthracene. It can be seen that the characteristics of the lower voltage and higher efficiency than Comparative Examples 2-2 to 2-5 consisting of.

The compound of Chemical Formula 1 according to the present specification was excellent in hole transporting ability, showed low voltage and high efficiency, and could be applied to an organic light emitting device.

Experimental Example 3-1

After the compounds prepared in Preparation Example were subjected to high purity sublimation purification by a conventionally known method, a green organic light emitting device was manufactured by the following method.

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

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

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

Experimental Example 3-2

The organic light emitting device was manufactured by the same method as Experimental Example 3-1, except that compound 1-11 was used instead of compound 1-10 in Experimental Example 3-1.

Experimental Example 3-3

The organic light emitting device was manufactured by the same method as Experimental Example 3-1, except that compound 1-12 was used instead of compound 1-10 in Experimental Example 3-1.

Experimental Example 3-4

The organic light emitting device was manufactured by the same method as Experimental Example 3-1, except that compound 1-13 was used instead of compound 1-10 in Experimental Example 3-1.

The organic light emitting device was manufactured by the same method as Experimental Example 3-1, except that compound 1-14 was used instead of compound 1-10 in Experimental Example 3-1.

Experimental Example 3-6

The organic light emitting device was manufactured by the same method as Experimental Example 3-1, except that compound 1-27 was used instead of compound 1-10 in Experimental Example 3-1.

Experimental Example 3-7

The organic light emitting device was manufactured by the same method as Experimental Example 3-1, except that compound 1-28 was used instead of compound 1-10 in Experimental Example 3-1.

Experimental Example 3-8

The organic light emitting device was manufactured by the same method as Experimental Example 3-1, except that compound 1-29 was used instead of compound 1-10 in Experimental Example 3-1.

Experimental Example 3-9

The organic light emitting device was manufactured by the same method as Experimental Example 3-1, except that compound 1-30 was used instead of compound 1-10 in Experimental Example 3-1.

Experimental Example 3-10

The organic light emitting device was manufactured by the same method as Experimental Example 3-1, except that compound 1-31 was used instead of compound 1-10 in Experimental Example 3-1.

Experimental Example 3-11

The organic light emitting device was manufactured by the same method as Experimental Example 3-1, except that compound 1-44 was used instead of compound 1-10 in Experimental Example 3-1.

Experimental Example 3-12

The organic light emitting device was manufactured by the same method as Experimental Example 3-1, except that compound 1-45 was used instead of compound 1-10 in Experimental Example 3-1.

The organic light emitting device was manufactured by the same method as Experimental Example 3-1, except that compound 1-46 was used instead of compound 1-10 in Experimental Example 3-1.

The organic light emitting device was manufactured by the same method as Experimental Example 3-1, except that compound 1-47 was used instead of compound 1-10 in Experimental Example 3-1.

Experimental Example 3-15

The organic light emitting device was manufactured by the same method as Experimental Example 3-1, except that compound 1-48 was used instead of compound 1-10 in Experimental Example 3-1.

Experimental Example 3-16

The organic light emitting device was manufactured by the same method as Experimental Example 3-1, except that compound 1-61 was used instead of compound 1-10 in Experimental Example 3-1.

The organic light emitting device was manufactured by the same method as Experimental Example 3-1, except that compound 1-62 was used instead of compound 1-10 in Experimental Example 3-1.

Experimental Example 3-18

The organic light emitting device was manufactured by the same method as Experimental Example 3-1, except that compound 1-63 was used instead of compound 1-10 in Experimental Example 3-1.

The organic light emitting device was manufactured by the same method as Experimental Example 3-1, except that compound 1-64 was used instead of compound 1-10 in Experimental Example 3-1.

Experimental Example 3-20

The organic light emitting device was manufactured by the same method as Experimental Example 3-1, except that compound 1-65 was used instead of compound 1-10 in Experimental Example 3-1.

The organic light emitting device was manufactured by the same method as Experimental Example 3-1, except that compound 2-10 was used instead of compound 1-10 in Experimental Example 3-1.

The organic light emitting device was manufactured by the same method as Experimental Example 3-1, except that compound 2-11 was used instead of compound 1-10 in Experimental Example 3-1.

The organic light emitting device was manufactured by the same method as Experimental Example 3-1, except that compound 2-12 was used instead of compound 1-10 in Experimental Example 3-1.

The organic light emitting device was manufactured by the same method as Experimental Example 3-1, except that compound 2-13 was used instead of compound 1-10 in Experimental Example 3-1.

The organic light emitting device was manufactured by the same method as Experimental Example 3-1, except that compound 2-14 was used instead of compound 1-10 in Experimental Example 3-1.

The organic light emitting device was manufactured by the same method as Experimental Example 3-1, except that compound 2-27 was used instead of compound 1-10 in Experimental Example 3-1.

The organic light emitting device was manufactured by the same method as Experimental Example 3-1, except that compound 2-28 was used instead of compound 1-10 in Experimental Example 3-1.

The organic light emitting device was manufactured by the same method as Experimental Example 3-1, except that compound 2-29 was used instead of compound 1-10 in Experimental Example 3-1.

The organic light emitting device was manufactured by the same method as Experimental Example 3-1, except that compound 2-30 was used instead of compound 1-10 in Experimental Example 3-1.

Experimental Example 3-30

The organic light emitting device was manufactured by the same method as Experimental Example 3-1, except that compound 2-31 was used instead of compound 1-10 in Experimental Example 3-1.

The organic light emitting device was manufactured by the same method as Experimental Example 3-1, except that compound 2-44 was used instead of compound 1-10 in Experimental Example 3-1.

The organic light emitting device was manufactured by the same method as Experimental Example 3-1, except that compound 2-45 was used instead of compound 1-10 in Experimental Example 3-1.

The organic light emitting device was manufactured by the same method as Experimental Example 3-1, except that compound 2-46 was used instead of compound 1-10 in Experimental Example 3-1.

The organic light emitting device was manufactured by the same method as Experimental Example 3-1, except that compound 2-47 was used instead of compound 1-10 in Experimental Example 3-1.

The organic light emitting device was manufactured by the same method as Experimental Example 3-1, except that compound 2-48 was used instead of compound 1-10 in Experimental Example 3-1.

The organic light emitting device was manufactured by the same method as Experimental Example 3-1, except that compound 2-61 was used instead of compound 1-10 in Experimental Example 3-1.

The organic light emitting device was manufactured by the same method as Experimental Example 3-1, except that compound 2-62 was used instead of compound 1-10 in Experimental Example 3-1.

The organic light emitting device was manufactured by the same method as Experimental Example 3-1, except that compound 2-63 was used instead of compound 1-10 in Experimental Example 3-1.

The organic light emitting device was manufactured by the same method as Experimental Example 3-1, except that compound 2-64 was used instead of compound 1-10 in Experimental Example 3-1.

Experimental Example 3-40

The organic light emitting device was manufactured by the same method as Experimental Example 3-1, except that compound 2-65 was used instead of compound 1-10 in Experimental Example 3-1.

The organic light emitting device was manufactured by the same method as Experimental Example 3-1, except that GH 1 (CBP) was used instead of compound 1-10 in Experimental Example 3-1.

When the electric current was applied to the organic light emitting element produced by Experimental Example 3-1 to 3-40 and Comparative Example 3-1, the result of Table 3 was obtained.

	화합물(호스트)Compound (Host)	전압(V@10mA/cm²)Voltage (V @ 10mA / cm ² )	효율(cd/A@10mA/cm²)Efficiency (cd / A @ 10mA / cm ² )	EL 피크(nm)EL peak (nm)
실험예 3-1Experimental Example 3-1	화합물 1-10Compound 1-10	6.186.18	43.9343.93	517517
실험예 3-2Experimental Example 3-2	화합물 1-11Compound 1-11	6.266.26	45.2445.24	516516
실험예 3-3Experimental Example 3-3	화합물 1-12Compound 1-12	6.156.15	44.7944.79	518518
실험예 3-4Experimental Example 3-4	화합물 1-13Compound 1-13	6.296.29	46.1546.15	517517
실험예 3-5Experimental Example 3-5	화합물 1-14Compound 1-14	6.286.28	44.3144.31	515515
실험예 3-6Experimental Example 3-6	화합물 1-27Compound 1-27	6.136.13	45.6345.63	516516
실험예 3-7Experimental Example 3-7	화합물 1-28Compound 1-28	6.296.29	45.6245.62	516516
실험예 3-8Experimental Example 3-8	화합물 1-29Compound 1-29	6.276.27	46.6446.64	517517
실험예 3-9Experimental Example 3-9	화합물 1-30Compound 1-30	6.246.24	46.6846.68	518518
실험예 3-10Experimental Example 3-10	화합물 1-31Compound 1-31	6.186.18	43.8343.83	517517
실험예 3-11Experimental Example 3-11	화합물 1-44Compound 1-44	6.266.26	45.2445.24	516516
실험예 3-12Experimental Example 3-12	화합물 1-45Compound 1-45	6.156.15	44.5244.52	518518
실험예 3-13Experimental Example 3-13	화합물 1-46Compound 1-46	6.296.29	46.9546.95	517517
실험예 3-14Experimental Example 3-14	화합물 1-47Compound 1-47	6.286.28	44.3144.31	515515
실험예 3-15Experimental Example 3-15	화합물 1-48Compound 1-48	6.136.13	45.1345.13	516516
실험예 3-16Experimental Example 3-16	화합물 1-61Compound 1-61	6.296.29	45.4245.42	516516
실험예 3-17Experimental Example 3-17	화합물 1-62Compound 1-62	6.276.27	45.6445.64	517517
실험예 3-18Experimental Example 3-18	화합물 1-63Compound 1-63	6.246.24	46.0846.08	518518
실험예 3-19Experimental Example 3-19	화합물 1-64Compound 1-64	6.246.24	46.0846.08	518518
실험예 3-20Experimental Example 3-20	화합물 1-65Compound 1-65	6.246.24	46.0846.08	518518
실험예 3-21Experimental Example 3-21	화합물 2-10Compound 2-10	6.246.24	46.0846.08	518518
실험예 3-22Experimental Example 3-22	화합물 2-11Compound 2-11	6.246.24	46.0846.08	518518
실험예 3-23Experimental Example 3-23	화합물 2-12Compound 2-12	6.246.24	46.0846.08	518518
실험예 3-24Experimental Example 3-24	화합물 2-13Compound 2-13	6.246.24	46.0846.08	518518
실험예 3-25Experimental Example 3-25	화합물 2-14Compound 2-14	6.246.24	46.0846.08	518518
실험예 3-26Experimental Example 3-26	화합물 2-27Compound 2-27	6.246.24	46.0846.08	518518
실험예 3-27Experimental Example 3-27	화합물 2-28Compound 2-28	6.246.24	46.0846.08	518518
실험예 3-28Experimental Example 3-28	화합물 2-29Compound 2-29	6.246.24	46.0846.08	518518
실험예 3-29Experimental Example 3-29	화합물 2-30Compound 2-30	6.246.24	46.0846.08	518518
실험예 3-30Experimental Example 3-30	화합물 2-31Compound 2-31	6.246.24	46.0846.08	518518
실험예 3-31Experimental Example 3-31	화합물 2-44Compound 2-44	6.246.24	46.0846.08	518518
실험예 3-32Experimental Example 3-32	화합물 2-45Compound 2-45	6.246.24	46.0846.08	518518
실험예 3-33Experimental Example 3-33	화합물 2-46Compound 2-46	6.246.24	46.0846.08	518518
실험예 3-34Experimental Example 3-34	화합물 2-47Compound 2-47	6.246.24	46.0846.08	518518
실험예 3-35Experimental Example 3-35	화합물 2-48Compound 2-48	6.246.24	46.0846.08	518518
실험예 3-36Experimental Example 3-36	화합물 2-61Compound 2-61	6.246.24	46.0846.08	518518
실험예 3-37Experimental Example 3-37	화합물 2-62Compound 2-62	6.246.24	46.0846.08	518518
실험예 3-38Experimental Example 3-38	화합물 2-63Compound 2-63	6.246.24	46.0846.08	518518
실험예 3-39Experimental Example 3-39	화합물 2-64Compound 2-64	6.246.24	46.0846.08	518518
실험예 3-40Experimental Example 3-40	화합물 2-65Compound 2-65	6.246.24	46.0846.08	518518
비교예 3-1Comparative Example 3-1	GH 1(CBP)GH 1 (CBP)	7.017.01	38.7238.72	517517

As a result, the green organic light emitting device of Experimental Examples 3-1 to 3-40 using the compound represented by Chemical Formula 1 according to the present specification as a host material of the green light emitting layer was Comparative Example 3 using conventional CBP (GH 1). It was confirmed that the green organic light emitting device of -1 showed better performance in terms of current efficiency and driving voltage.

After the compounds prepared in Preparation Example were subjected to high purity sublimation purification by a conventionally known method, a red organic light emitting device was manufactured by the following method.

The light emitting area of the ITO glass was patterned to have a size of 2 mm × 2 mm and then washed. After mounting the substrate in a vacuum chamber, the base pressure was 1 × 10 ^-6 torr, and the organic material was placed on the ITO as DNTPD (700), α-NPB (300 kPa), and compound 1-14 as a host (90 wt%). (Piq) ₂ Ir (acac) (10 wt%) as a dopant, followed by Alq ₃ (350 kPa), LiF (5 kPa), Al (1,000 kPa) The film was formed at and measured at 0.4 mA.

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

The organic light emitting device was manufactured by the same method as Experimental Example 4-1, except that compound 1-10 was used instead of compound 1-14 in Experimental Example 4-1.

Experimental Example 4-3

The organic light emitting device was manufactured by the same method as Experimental Example 4-1, except that compound 1-27 was used instead of compound 1-14 in Experimental Example 4-1.

Experimental Example 4-4

The organic light emitting device was manufactured by the same method as Experimental Example 4-1, except that compound 1-31 was used instead of compound 1-14 in Experimental Example 4-1.

Experimental Example 4-5

The organic light emitting device was manufactured by the same method as Experimental Example 4-1, except that compound 1-44 was used instead of compound 1-14 in Experimental Example 4-1.

The organic light emitting device was manufactured by the same method as Experimental Example 4-1, except that compound 1-48 was used instead of compound 1-14 in Experimental Example 4-1. .

The organic light emitting device was manufactured by the same method as Experimental Example 4-1, except that compound 1-61 was used instead of compound 1-14 in Experimental Example 4-1.

The organic light emitting device was manufactured by the same method as Experimental Example 4-1, except that compound 1-65 was used instead of compound 1-14 in Experimental Example 4-1.

Comparative Example 1

An organic light emitting diode was manufactured according to the same method as Experimental Example 4-1 except for using the following compound RH 1 (CBP) instead of compound 1-14 in Experimental Example 4-1.

For organic light emitting diodes manufactured according to Experimental Examples 4-1 to 4-8 and Comparative Example 4-1, voltage, current density, luminance, color coordinate, and lifetime were measured, and the results are shown in Table 4 below. T95 means the time taken for the luminance to be reduced to 95% from the initial luminance (5000 nits).

구분division	호스트Host	도펀트Dopant	전압(V)Voltage (V)	휘도(cd/m²)Luminance (cd / m ² )	색좌표(x, y)Color coordinates (x, y)	T95(hr)T95 (hr)
실험예4-1Experimental Example 4-1	화합물 1-14Compound 1-14	(piq)₂Ir(acac)(piq) ₂ Ir (acac)	4.34.3	18601860	(0.670,0.329)(0.670,0.329)	465465
실험예4-2Experimental Example 4-2	화합물 1-10Compound 1-10	(piq)₂Ir(acac)(piq) ₂ Ir (acac)	4.24.2	18501850	(0.674,0.325)(0.674,0.325)	415415
실험예4-3Experimental Example 4-3	화합물 1-27Compound 1-27	(piq)₂Ir(acac)(piq) ₂ Ir (acac)	4.14.1	19001900	(0.672,0.327)(0.672,0.327)	440440
실험예4-4Experimental Example 4-4	화합물 1-31Compound 1-31	(piq)₂Ir(acac)(piq) ₂ Ir (acac)	4.34.3	18401840	(0.673,0.335)(0.673,0.335)	435435
실험예4-5Experimental Example 4-5	화합물 1-44Compound 1-44	(piq)₂Ir(acac)(piq) ₂ Ir (acac)	4.04.0	17901790	(0.675,0.333)(0.675,0.333)	405405
실험예4-6Experimental Example 4-6	화합물 1-48Compound 1-48	(piq)₂Ir(acac)(piq) ₂ Ir (acac)	4.24.2	18101810	(0.670,0.339)(0.670,0.339)	420420
실험예4-7Experimental Example 4-7	화합물 1-61Compound 1-61	(piq)₂Ir(acac)(piq) ₂ Ir (acac)	4.34.3	19701970	(0.671,0.338)(0.671,0.338)	445445
실험예4-8Experimental Example 4-8	화합물 1-65Compound 1-65	(piq)₂Ir(acac)(piq) ₂ Ir (acac)	4.34.3	18601860	(0.668,0.329)(0.668,0.329)	465465
비교예 4-1Comparative Example 4-1	RH 1RH 1	(piq)₂Ir(acac)(piq) ₂ Ir (acac)	6.16.1	12001200	(0.670,0.327)(0.670,0.327)	235235

As a result, red organic light emitting diodes of Experimental Examples 4-1 to 4-8 using the compound of Formula 1 as a host material of the light emitting layer according to the present specification were compared with those of Comparative Example 4-1 using conventional CBP (RH 1). It was confirmed that the red organic light emitting device showed better performance in terms of current efficiency, driving voltage, and lifetime.

Experimental Example 5-1

Compound N4, N4, N4 ', N4'-tetra ([1,1'-biphenyl] -4-yl)-[1,1'-biphenyl] -4, which is a material for transporting holes on the hole injection layer, 4'-diamine [HIL] (300 Pa) was vacuum deposited to form a hole transport layer.

Subsequently, the compound N, N-di ([1,1'-biphenyl] -4-yl) -4 '-(9H-carbazol-9-yl)-[1,1' has a thickness of 100 kPa on the hole transport layer. -biphenyl] -4-amine was vacuum deposited to form an electron blocking layer.

Subsequently, BH and the following Compound 1-69 were vacuum-deposited to BD at a weight ratio of 25: 1 on a film thickness of 300 kPa to form a light emitting layer on the electron blocking layer.

Experimental Example 5-2

The organic light emitting device was manufactured by the same method as Experimental Example 5-1, except that compound 1-70 was used instead of compound 1-69 in Experimental Example 5-1.

Experimental Example 5-3

The organic light emitting device was manufactured by the same method as Experimental Example 5-1, except that compound 1-71 was used instead of compound 1-69 in Experimental Example 5-1.

Experimental Example 5-4

The organic light emitting device was manufactured by the same method as Experimental Example 5-1, except that compound 1-72 was used instead of compound 1-69 in Experimental Example 5-1.

Experimental Example 5-5

The organic light emitting device was manufactured by the same method as Experimental Example 5-1, except that compound 2-69 was used instead of compound 1-69 in Experimental Example 5-1.

Experimental Example 5-6

The organic light emitting device was manufactured by the same method as Experimental Example 5-1, except that compound 2-70 was used instead of compound 1-69 in Experimental Example 5-1.

The organic light emitting device was manufactured by the same method as Experimental Example 5-1, except that Compound BD 1 was used instead of Compound 1-69 in Experimental Example 5-1.

The organic light emitting device was manufactured by the same method as Experimental Example 5-1, except that BD 2 was used instead of compound 1-69 in Experimental Example 5-1.

The organic light emitting device was manufactured by the same method as Experimental Example 5-1, except that BD 3 was used instead of compound 1-69 in Experimental Example 5-1.

When current was applied to the organic light emitting devices manufactured by Experimental Examples 5-1 to 5-6 and Comparative Examples 5-1 to 5-3, voltage, efficiency, color coordinate, and lifetime were measured, and the results are shown in Table 5 below. It was. T90 refers to the time it takes for the luminance to decrease to 90% from the initial luminance (5000 nits).

	화합물(발광층도펀트)Compound (Light Emitting Layer Dopant)	전압(V@10mA/cm²)Voltage (V @ 10mA / cm ² )	효율(cd/A@10mA/cm²)Efficiency (cd / A @ 10mA / cm ² )	색좌표(x,y)Color coordinates (x, y)	T90(hr)T90 (hr)
실험예 5-1Experimental Example 5-1	화합물 1-69Compound 1-69	4.364.36	6.726.72	(0.141, 0.044)(0.141, 0.044)	8686
실험예 5-2Experimental Example 5-2	화합물 1-70Compound 1-70	4.534.53	6.516.51	(0.142, 0.045)(0.142, 0.045)	7575
실험예 5-3Experimental Example 5-3	화합물 1-71Compound 1-71	4.454.45	6.486.48	(0.141, 0.046)(0.141, 0.046)	7979
실험예 5-4Experimental Example 5-4	화합물 1-72Compound 1-72	4.404.40	6.506.50	(0.141, 0.047)(0.141, 0.047)	8181
실험예 5-5Experimental Example 5-5	화합물 2-69Compound 2-69	4.394.39	6.586.58	(0.141, 0.047)(0.141, 0.047)	9595
실험예 5-6Experimental Example 5-6	화합물 2-70Compound 2-70	4.294.29	6.456.45	(0.141, 0.047)(0.141, 0.047)	102102
비교예 5-1Comparative Example 5-1	BD 1BD 1	4.954.95	5.615.61	(0.144, 0.046)(0.144, 0.046)	5151
비교예 5-2Comparative Example 5-2	BD 2BD 2	4.774.77	5.875.87	(0.145, 0.041)(0.145, 0.041)	5656
비교예 5-3Comparative Example 5-3	BD 3BD 3	4.704.70	5.985.98	(0.144, 0.040)(0.144, 0.040)	5454

As shown in Table 5, the compounds according to the exemplary embodiment of the present specification and the organic light emitting device using Examples 5-1 to 5-6 are silyl groups, fluorine groups, heteroaryl groups, aryl groups, etc. as dopants of the light emitting layer. Compounds containing substituted amine groups as substituents showed various color coordinates, showed low voltage and high efficiency in organic light emitting devices, and were applicable to organic light emitting devices. In particular, it can be seen that Compound 2-69 and Compound 2-70 having a core containing triphenylene greatly increase the lifespan.

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

[Description of the code]

10, 11: organic light emitting element

20: substrate

30: first electrode

40: light emitting layer

50: second electrode

60: hole injection layer

70: hole transport layer

80: electron transport layer

90: electron injection layer

Claims

Compound represented by the following formula (1):

[Formula 1]

In Chemical Formula 1,

A is a substituted or unsubstituted tetracyclic aromatic ring,

R1 to R12 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amide 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 groups adjacent to each other may combine with each other to form a substituted or unsubstituted ring,

At least one of the above R1 to R12 has a substituent other than hydrogen.
The method according to claim 1, wherein A is substituted or unsubstituted fluoranthene ring; Or a substituted or unsubstituted triphenylene ring.
The compound of claim 1, wherein A is represented by Formula A-1 or A-2:

[Formula A-1]

[Formula A-2]

In Chemical Formulas A-1 and A-2,

A1 and A2 of A1 to A22; A2 and A3; A4 and A5; A5 and A6; A7 and A8; A8 and A9; A9 and A10; A11 and A12; A12 and A13; A13 and A14; A15 and A16; A16 and A17; A17 and A18; A19 and A20; A20 and A21; Or A21 and A22 are moieties that are directly connected to Formula 1, and the others are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amide 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.
The compound of claim 1, wherein Formula 1 is represented by Formula 1-1 or 1-2:

[Formula 1-1]

[Formula 1-2]

In Chemical Formulas 1-1 and 1-2,

Definitions of R1 to R12 are the same as in the general formula (1),

A1, A4 to A11 and A14 to A22 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amide 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.
The compound of claim 1, wherein Formula 1 is represented by Formula 1-3 or 1-4:

[Formula 1-3]

[Formula 1-4]

In Chemical Formulas 1-3 and 1-4,

Definitions of R1 to R12 are the same as in the above formula (1).
The method according to claim 1, wherein R1 to R12 are the same as or different from each other, each independently hydrogen; Substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Substituted or unsubstituted phenanthrenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted terphenyl group; A substituted or unsubstituted fluorenyl group; Substituted or unsubstituted anthracenyl group; Substituted or unsubstituted chrysenyl group; A substituted or unsubstituted quarterphenyl group; Substituted or unsubstituted spirobifluorenyl group; Substituted or unsubstituted pyrenyl group; Substituted or unsubstituted triphenylenyl group; Substituted or unsubstituted perenyl group; Substituted or unsubstituted triazinyl group; Substituted or unsubstituted pyrimidyl group; Substituted or unsubstituted pyridyl group; Substituted or unsubstituted quinolinyl group; Substituted or unsubstituted quinazolinyl group; Substituted or unsubstituted benzoquinolinyl group; Substituted or unsubstituted phenanthrolinyl group; Substituted or unsubstituted quinoxalinyl group; Substituted or unsubstituted dibenzofuranyl group; Substituted or unsubstituted dibenzothiophene group; Substituted or unsubstituted benzonaphthofuranyl; Substituted or unsubstituted benzonaphthothiophene group; Substituted or unsubstituted dimethyl phosphine oxide group; Substituted or unsubstituted diphenylphosphine oxide; Substituted or unsubstituted dinaphthylphosphine oxide; Substituted or unsubstituted benzoxazolyl group; Substituted or unsubstituted benzothiazolyl group; Substituted or unsubstituted benzimidazolyl group; Substituted or unsubstituted triphenylsilyl group; Substituted or unsubstituted phenothiazinyl group; Substituted or unsubstituted phenoxazinyl group; Substituted or unsubstituted thiophene group; Substituted or unsubstituted diphenylamine group; A substituted or unsubstituted N-phenylnaphthylamine group; A substituted or unsubstituted N-phenylbiphenylamine group; A substituted or unsubstituted N-phenylphenanthrenylamine group; A substituted or unsubstituted N-biphenylnaphthylamine group; Substituted or unsubstituted dibiphenylamine group; A substituted or unsubstituted N-biphenylphenanthrenylamine group; A substituted or unsubstituted dinaphthylamine group; A substituted or unsubstituted N-quaterphenylfluorenylamine group; A substituted or unsubstituted N-terphenylfluorenylamine group; A substituted or unsubstituted N-biphenylterphenylamine group; A substituted or unsubstituted N-biphenylfluorenylamine group; A substituted or unsubstituted N-phenylfluorenylamine group; A substituted or unsubstituted N-naphthylfluorenylamine group; A substituted or unsubstituted N-phenanthrenylfluorenylamine group; A substituted or unsubstituted difluorenylamine group; A substituted or unsubstituted N-phenylterphenylamine group; A substituted or unsubstituted N-phenylcarbazolylamine group; A substituted or unsubstituted N-biphenylcarbazolylamine group; A substituted or unsubstituted N-phenylbenzocarbazolylamine group; A substituted or unsubstituted N-biphenylbenzocarbazolylamine group; A substituted or unsubstituted N-phenyldibenzofuranylamine group; A substituted or unsubstituted N-phenyldibenzothiophenamine group; Substituted or unsubstituted N-fluorenyl carbazolylamine group; Substituted or unsubstituted benzocarbazolyl group; A substituted or unsubstituted dibenzocarbazolyl group; Substituted or unsubstituted carbazolyl group; Substituted or unsubstituted
; Substituted or unsubstituted
; And it is selected from the group consisting of a structure represented by the formula a,

---- means a site bonded to the formula (1) through the L1.

[Formula a]

In Chemical Formula a,

Any one of X1 to X12 is a moiety bonded to Formula 1, and the others are the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or adjacent groups are linked to each other to form a substituted or unsubstituted ring.
The method according to claim 1, wherein R1 to R12 are the same as or different from each other, each independently hydrogen; Or a compound represented by any one of the following structural formulas [R-1] to [R-5], wherein at least one of R1 to R12 has a substituent other than hydrogen:

[R-1]

[R-2]

[R-3]

[R-4]

[R-5]

In the above structural formula --- means a moiety bonded to the formula (1).
The compound of claim 1, wherein Formula 1 is represented by any one of the following compounds:
A first electrode; A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound of any one of claims 1 to 8.
The organic light emitting device of claim 9, wherein the organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer includes the compound.
The organic light emitting device of claim 9, wherein the organic material layer comprises an electron blocking layer, and the electron blocking layer comprises the compound.
The organic light emitting device of claim 9, wherein the organic material layer comprises a light emitting layer, and the light emitting layer comprises the compound.
The method according to claim 9, wherein the organic layer comprises an electron transport layer, an electron injection layer or a layer for simultaneously transporting and electron injection, the electron transport layer, the electron injection layer or the layer for simultaneously transporting and electron injection and the compound includes the compound It is an organic light emitting device.
The organic light emitting device of claim 9, wherein the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula 1-A:

[Formula 1-A]

In Chemical Formula 1-A,

n1 is an integer of 1 or more,

Ar7 is a substituted or unsubstituted monovalent or higher benzofluorene group; Substituted or unsubstituted monovalent or higher fluoranthene group; A substituted or unsubstituted monovalent or higher pyrene group; Or a substituted or unsubstituted monovalent or higher chrysene group,

L4 is a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

Ar8 and Ar9 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted germanium group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted arylalkyl group; Or a substituted or unsubstituted heteroaryl group, or may combine with each other to form a substituted or unsubstituted ring,

When n1 is 2 or more, the structures in two or more parentheses are the same or different from each other.
The method according to claim 14, wherein L4 is a direct bond, Ar7 is a divalent pyrene group, Ar8 and Ar9 are the same or different from each other and each independently an aryl group unsubstituted or substituted with a germanium group substituted with an alkyl group, n1 is 2 It is an organic light emitting element.
The organic light emitting device of claim 9, wherein the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula 2-A:

[Formula 2-A]

In Chemical Formula 2-A,

G11 is 1-naphthyl group, 2-naphthyl group, 1-anthryl group, 2-anthryl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9- Phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group, 9-naphthacenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 3-methyl-2-naphthyl group, 4-methyl- 1-naphthyl group, or
ego,

G12 is a phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthryl group, 2-anthryl group, 9-anthryl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group, 9-naphthacenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 2-biphenylyl group , 3-biphenylyl group, 4-biphenylyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m -Terphenyl-3-yl group, m-terphenyl-2-yl group, o-tolyl group, m-tolyl group, p-tolyl group, pt-butylphenyl group, p- (2-phenylpropyl) phenyl group, 3-methyl 2-naphthyl group, 4-methyl-1-naphthyl group, 4-methyl-1-anthryl group, 4'-methylbiphenylyl group, 4 "-t-butyl-p-terphenyl-4-yl group, or 3-fluoranthenyl group,

G13 and G14 are the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

g12 is an integer of 1 to 5,

g13 and g14 are each an integer of 1 to 4,

When g12 to g14 are each two or more, the structures in two or more parentheses are the same as or different from each other.
The organic light emitting device of claim 16, wherein G11 is a 1-naphthyl group and G12 is a 2-naphthyl group.
The organic light emitting device of claim 14, wherein the light emitting layer comprises a compound represented by Chemical Formula 2-A:

[Formula 2-A]

In Chemical Formula 2-A,

G11 is 1-naphthyl group, 2-naphthyl group, 1-anthryl group, 2-anthryl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9- Phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group, 9-naphthacenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 3-methyl-2-naphthyl group, 4-methyl- 1-naphthyl group, or
ego,

G12 is a phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthryl group, 2-anthryl group, 9-anthryl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group, 9-naphthacenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 2-biphenylyl group , 3-biphenylyl group, 4-biphenylyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m -Terphenyl-3-yl group, m-terphenyl-2-yl group, o-tolyl group, m-tolyl group, p-tolyl group, pt-butylphenyl group, p- (2-phenylpropyl) phenyl group, 3-methyl 2-naphthyl group, 4-methyl-1-naphthyl group, 4-methyl-1-anthryl group, 4'-methylbiphenylyl group, 4 "-t-butyl-p-terphenyl-4-yl group, or 3-fluoranthenyl group,

G13 and G14 are the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

g12 is an integer of 1 to 5,

g13 and g14 are each an integer of 1 to 4,

When g12 to g14 are each two or more, the structures in two or more parentheses are the same as or different from each other.