WO2020080849A1 - Compound and organic light-emitting device comprising same - Google Patents

Abstract

The present specification relates to a compound of chemical formula 1 and an organic light-emitting device comprising same.

Description

Compound and organic light emitting device comprising same

This specification claims the benefit of Korean Patent Application No. 10-2018-0123745 filed with the Korean Intellectual Property Office on October 17, 2018, the entire contents of which are incorporated herein.

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

In general, the organic light emitting phenomenon refers to a phenomenon that converts 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 and a cathode and an organic material layer therebetween. Here, in order to increase the efficiency and stability of the organic light emitting device, the organic material layer is often composed of a multi-layered structure composed of different materials, for example, may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. When a voltage is applied between the two electrodes in the structure of the organic light emitting device, holes are injected at the anode, and electrons are injected at the cathode, and an exciton is formed when the injected holes meet the electrons. When it falls to the ground again, it will shine.

The development of new materials for such organic light-emitting devices continues to be required.

(Patent Document) US Patent Application Publication No. 2004-0251816

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

The present invention provides a compound represented by Formula 1 below.

[Formula 1]

In Chemical Formula 1,

A is a substituted or unsubstituted divalent aromatic ring; Or a substituted or unsubstituted divalent heterocycle,

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

R ₁ to R ₄ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitrile group; Halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted silyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

a1 and a2 are integers from 0 to 4,

a3 and a4 are integers from 0 to 3,

When a1 is plural, R ₁ is the same as or different from each other,

When a2 is plural, R ₂ is the same as or different from each other,

When a3 is plural, R ₃ is the same as or different from each other,

When a4 is plural, R ₄ is the same as or different from each other.

In addition, the present specification is a first electrode; A second electrode provided opposite to the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer provides an organic light emitting device including the compound.

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

In addition, the compound according to an exemplary embodiment of the present specification can improve the efficiency and life of the OLED device by simultaneously controlling the electrical and luminescence properties, so that the compound of the existing simple spiro structure (for example, dimethylfluorene) Compared to the organic light emitting device employing, it may have high efficiency, low driving voltage, high brightness, and long life.

1 shows an organic light emitting diode according to an exemplary embodiment of the present specification.

2 shows an organic light emitting diode according to an exemplary embodiment of the present specification.

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

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

The present specification provides a compound represented by Chemical Formula 1:

[Formula 1]

In Chemical Formula 1,

A is a substituted or unsubstituted divalent aromatic ring; Or a substituted or unsubstituted divalent heterocycle,

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

R ₁ to R ₄ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitrile group; Halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted silyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

a1 and a2 are integers from 0 to 4,

a3 and a4 are integers from 0 to 3,

When a1 is plural, R ₁ is the same as or different from each other,

When a2 is plural, R ₂ is the same as or different from each other,

When a3 is plural, R ₃ is the same as or different from each other,

When a4 is plural, R ₄ is the same as or different from each other.

The compound according to the exemplary embodiment of the present specification includes fluorene in which two adamantines are substituted in the core (A), so that the core structure has large bulkiness and rigidity, and is excellent. The luminous efficiency increases and the thermal stability is excellent due to the sublimation and stability of the chemical structure. In particular, it is possible to improve the efficiency and lifespan of an OLED device by simultaneously controlling the electrical and luminescence properties, so it is more efficient than an organic light emitting device that employs a compound of a conventional simple spiro structure (for example, dimethylfluorene). , It can have low driving voltage, high brightness and long life.

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

The term "substitution" means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited to a position where the hydrogen atom is substituted, that is, a position where the substituent is substitutable, and when two or more are substituted , 2 or more substituents may be the same or different from each other.

In addition, the term “substitution” includes two hydrogen atoms bonded to a carbon atom of a compound, each of which is replaced with a different substituent to combine with each other to form a ring.

The term "substituted or unsubstituted" as used herein refers to deuterium; Halogen group; Nitrile group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group, substituted with 1 or 2 or more substituents selected from the group, or substituted with 2 or more substituents among the exemplified substituents, or having no substituents. For example, the "substituent in which two or more substituents are connected" may be an aryl group substituted with an aryl group, an aryl group substituted with a heteroaryl group, a heterocyclic group substituted with an aryl group, an aryl group substituted with an alkyl group, or the like.

In the present specification, the alkyl group may be straight chain or branched chain, and carbon number is not particularly limited, but is preferably 1 to 30. Specifically, it is preferable to have 1 to 20 carbon atoms. More specifically, it is preferable to have 1 to 10 carbon atoms. Specific examples include methyl groups; Ethyl group; Propyl group; n-propyl group; Isopropyl group; Butyl group; n-butyl group; Isobutyl group; tert-butyl group; sec-butyl group; 1-methylbutyl group; 1-ethyl butyl group; Pentyl group; n-pentyl group; Isopentyl group; Neopentyl group; tert-pentyl group; Hexyl group; n-hexyl group; 1-methylpentyl group; 2-methylpentyl group; 4-methyl-2-pentyl group; 3,3-dimethylbutyl group; 2-ethylbutyl group; Heptyl group; n-heptyl group; 1-methylhexyl group; Cyclopentyl methyl group; Cyclohexylmethyl group; Octyl group; n-octyl group; tert-octyl group; 1-methylheptyl group; 2-ethylhexyl group; 2-propylpentyl group; n-nonyl group; 2,2-dimethylheptyl group; 1-ethylpropyl group; 1,1-dimethylpropyl group; Isohexyl group; 2-methylpentyl group; 4-methylhexyl group; 5-methylhexyl group, and the like, but is not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but is preferably 3 to 30 carbon atoms, and more preferably 3 to 20 carbon atoms. Specifically, a cyclopropyl group; Cyclobutyl group; Cyclopentyl group; 3-methylcyclopentyl group; 2,3-dimethylcyclopentyl group; Cyclohexyl group; 3-methylcyclohexyl group; 4-methylcyclohexyl group; 2,3-dimethylcyclohexyl group; 3,4,5-trimethylcyclohexyl group; 4-tert-butylcyclohexyl group; Cycloheptyl group; Cyclooctyl group, and the like, but is not limited thereto.

In the present specification, the alkoxy group may be a straight chain, branched chain or cyclic chain. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specifically, it is preferable to have 1 to 20 carbon atoms. More specifically, it is preferable to have 1 to 10 carbon atoms. Specifically, a methoxy group; Ethoxy group; n-propoxy group; Isopropoxy group; i-propyloxy group; n-butoxy group; Isobutoxy group; tert-butoxy group; sec-butoxy group; n-pentyloxy group; Neopentyloxy group; Isopentyloxy group; n-hexyloxy group; 3,3-dimethylbutyloxy group; 2-ethylbutyloxy group; n-octyloxy group; n-nonyloxy group; n-decyloxy group; Benzyloxy group; p-methylbenzyloxy group, and the like, but is not limited thereto.

In the present specification, the amine group is -NH ₂ ; Alkylamine groups; N-alkylarylamine group; Arylamine group; N-aryl heteroarylamine group; It may be selected from the group consisting of N-alkylheteroarylamine groups and heteroarylamine groups, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of amine groups include methylamine groups; Dimethylamine group; Ethylamine group; Diethylamine group; Phenylamine group; Naphthylamine group; Biphenylamine group; Anthracenylamine group; 9-methyl anthracenylamine group; Diphenylamine group; N-phenyl naphthylamine group; Ditolylamine group; N-phenyltolylamine group; Triphenylamine group; N-phenylbiphenylamine group; N-phenyl naphthylamine group; N-biphenyl naphthylamine group; N-naphthylfluorenylamine group; N-phenylphenanthrenylamine group; N-biphenylphenanthrenylamine group; N-phenylfluorenylamine group; N-phenyl terphenylamine group; N-phenanthrenylfluorenylamine group; N-biphenyl fluorenylamine group and the like, but is not limited thereto.

In the present specification, the silyl group may be represented by the formula of -SiRaRbRc, wherein Ra, Rb and Rc are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. The silyl group is specifically a trimethylsilyl group; Triethylsilyl group; tert-butyldimethylsilyl group; Vinyl dimethyl silyl group; Propyl dimethyl silyl group; Triphenylsilyl group; Diphenylsilyl group; Phenylsilyl group, and the like, but is not limited thereto.

In the present specification, the aryl group is not particularly limited, but is preferably 6 to 30 carbon atoms, and more preferably 6 to 20 carbon atoms. The aryl group may be monocyclic or polycyclic. When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 30 carbon atoms. More specifically, it is preferable that it has 6 to 20 carbon atoms. Specifically, as the monocyclic aryl group, a phenyl group; Biphenyl group; It may be a terphenyl group, but is not limited thereto. When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. It is preferably 10 to 30 carbon atoms, and more preferably 10 to 20 carbon atoms. Specifically, a polycyclic aryl group is a naphthyl group; Anthracenyl group; Phenanthryl group; Triphenyl group; Pyrenyl group; Phenenyl group; Perylenyl group; Chrysenyl group; It may be a fluorenyl group, and the like, but is not limited thereto.

When the fluorenyl group is substituted, two substituents of carbon number 9 of the fluorenyl group may be bonded to each other to form a spiro structure such as 9,9-dimethylfluorenyl group or 9,9-diphenylfluorenyl group. However, it is not limited thereto.

In the present specification, the “adjacent” group refers to a substituent substituted on an atom directly connected to an atom in which the substituent is substituted, a substituent positioned closest to the substituent and the other substituent substituted on the atom in which the substituent is substituted. You can. For example, two substituents substituted in the ortho position on the benzene ring and two substituents substituted on the same carbon in the aliphatic ring may be interpreted as "adjacent" groups to each other.

In the present specification, in the substituted or unsubstituted ring formed by bonding to each other, "ring" is a hydrocarbon ring; Or a hetero ring.

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

In this specification, the description of the aryl group can be applied, except that the aromatic hydrocarbon ring is divalent.

The description of the following heterocyclic groups can be applied to the heterocycle except that it is divalent.

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 or a polycyclic aryl group. The arylamine group containing two or more aryl groups may include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time. For example, the aryl group in the arylamine group can be selected from the examples of the aryl group described above.

In the present specification, the heterocyclic group includes one or more non-carbon atoms, that is, heteroatoms, and specifically, the heteroatoms include one or more atoms selected from the group consisting of O, N, Se, SO, SO ₂ and S, etc. It can contain. The number of carbon atoms is not particularly limited, preferably 2 to 60 carbon atoms, more preferably 2 to 30 carbon atoms, and the heterocyclic group may be monocyclic or polycyclic. Examples of the heteroaryl group include a thiophene group; Furanyl group; Pyrrol group; Imidazolyl group; Thiazolyl group; Oxazolyl group; Oxadiazolyl group; Pyridyl group; Bipyridyl group; Pyrimidyl group; Triazinyl group; Triazolyl group; Acridil group; Pyridazinyl group; Pyrazinyl group; Quinolinyl group; Quinazolinyl group; Quinoxalinyl group; Phthalazinyl group; Pyridopyrimidyl group; Pyrido pyrazinyl group; Pyrazino pyrazinyl group; Isoquinolinyl group; Indole group; Carbazolyl group; Benzoxazolyl group; Benzimidazole group; Benzothiazolyl group; Benzocarbazolyl group; Benzothiophene group; Dibenzothiophene group; Benzofuranyl group; Phenanthroline group (phenanthroline); Isooxazolyl group; Thiadiazolyl group; Phenothiazinyl group and dibenzofuranyl group, and the like, but is not limited thereto.

According to an exemplary embodiment of the present specification, A is a substituted or unsubstituted divalent aromatic ring; Or a substituted or unsubstituted divalent heterocyclic ring. The aromatic ring may be applied to the description of the aromatic hydrocarbon ring described above.

According to another exemplary embodiment, A is a substituted or unsubstituted divalent aromatic ring having 6 to 60 carbon atoms; Or a substituted or unsubstituted hetero element is a divalent heterocycle having 2 to 60 carbon atoms containing at least one of N, O, S, SO and SO ₂ .

In another exemplary embodiment, the amine group bound to A may be bonded to the core structure of A or a substituent.

According to another exemplary embodiment, A may be represented by [A1] a-[A2] b-[A3] c, wherein A1 to A3 are the same as or different from each other, and each independently substituted or unsubstituted Aromatic ring, a, b and c are 0 or 1, respectively, and a + b + c is an integer from 1 to 3. When A has a structure of [A1] a-[A2] b-[A3] c, it may be combined in the order of [phenylene]-[fluorenylene]-[phenylene], and number 9 of fluorenylene It may have a structure in which a divalent phenylene is bonded to a carbon atom.

According to an exemplary embodiment of the present specification, A is a substituted or unsubstituted divalent 1 to 8 ring aromatic ring; Or a substituted or unsubstituted divalent 1 to 8 ring heterocycle.

According to an exemplary embodiment of the present specification, A is a substituted or unsubstituted divalent 1 to 8 ring condensed aromatic ring; Or a substituted or unsubstituted divalent 1 to 8 ring condensed heterocycle.

In one embodiment of the present specification, A is represented by any one of the following [Chemical Formula 1-1] to [Chemical Formula 1-10].

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

[Formula 1-6]

[Formula 1-7]

[Formula 1-8]

[Formula 1-9]

[Formula 1-10]

In Chemical Formulas 1-1 to 1-10,

X ₁ to X ₁₆ are the same as or different from each other, and each independently O; S; SO; SO ₂ ; Or CR'R ",

R 'and R "are the same as or different from each other, and each independently hydrogen; deuterium; nitrile group; halogen group; substituted or unsubstituted alkyl group; substituted or unsubstituted alkoxy group; substituted or unsubstituted silyl group; substituted or An unsubstituted amine group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, or combine with each other to form a substituted or unsubstituted ring,

n1 to n9, and m1 to m9 are integers from 0 to 2,

When n1 to n9, and m1 to m9 are 2, rings in parentheses may overlap.

In one embodiment of the present specification, A is represented by one of the following structural formulas.

In the above structural formula, X is O; S; SO; SO ₂ ; Or CR'R ".

In one embodiment of the present specification, X ₁ to X ₁₄ are the same as or different from each other, and each independently O; S; SO; SO ₂ ; Or CR'R ".

According to an exemplary embodiment of the present specification, the R 'and R "are the same as or different from each other, and each independently substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; or substituted or unsubstituted aryl group having 6 to 60 carbon atoms. Or, they combine with each other to form a substituted or unsubstituted C 2 to C 60 ring.

In another exemplary embodiment, R 'and R "are the same as or different from each other, and each independently an alkyl group having 1 to 20 carbon atoms; or an aryl group having 6 to 60 carbon atoms, or in combination with each other, having 2 to 60 carbon atoms. Form a ring.

In one embodiment of the present specification, Ar ₁ and Ar ₂ are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; A heteroaryl group containing 1 to 3 heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S; Or a substituted or unsubstituted alkyl group.

According to another exemplary embodiment, Ar ₁ and Ar ₂ are the same as or different from each other, and each independently substituted or unsubstituted aryl group having 6 to 60 carbon atoms; A heteroaryl group having 2 to 60 carbon atoms containing 1 to 3 heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S; Or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

In another exemplary embodiment, Ar ₁ and Ar ₂ are the same as or different from each other, and each independently substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A heteroaryl group having 2 to 30 carbon atoms containing 1 to 3 heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S; Or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

According to another exemplary embodiment, Ar ₁ and Ar ₂ are the same as or different from each other, and each independently substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A heteroaryl group having 2 to 30 carbon atoms containing 1 to 3 heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S; Or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms. The 'substituted or unsubstituted' is deuterium; Halogen group; Nitrile group; An alkyl group having 1 to 10 carbon atoms; An aryl group having 6 to 30 carbon atoms; A silyl group having 1 to 30 carbon atoms; And it means that one or more selected from the group consisting of a heteroaryl group having 2 to 30 carbon atoms is substituted or unsubstituted with a linked substituent.

According to another exemplary embodiment, Ar ₁ and Ar ₂ are the same as or different from each other, and each independently substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted dibenzofuranyl group; A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; Or a substituted or unsubstituted butyl group. The 'substituted or unsubstituted' is deuterium; Halogen group; Nitrile group; Methyl group; Ethyl group; Butyl group; Phenyl group; Biphenyl group; Toughness group; Naphthyl group; Trimethylsilyl group; Triphenylsilyl group; Dimethylfluorenyl group; Dibenzofuranyl group; Dibenzothiophene group; And one or more substituents selected from the group consisting of carbazole, substituted or unsubstituted.

According to the exemplary embodiment of the present specification, R ₁ and R ₄ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitrile group; Halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted silyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In another exemplary embodiment, R ₁ and R ₄ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitrile group; Halogen group; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms; A substituted or unsubstituted silyl group having 1 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

According to another exemplary embodiment, R ₁ and R ₄ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; An alkyl group having 1 to 10 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to another exemplary embodiment, R ₁ and R ₄ are the same as or different from each other, and each independently hydrogen; Methyl group; Ethyl group; Butyl group; Cyclopentyl group; Cyclohexyl group; Or a phenyl group.

According to the exemplary embodiment of the present specification, a1 and a2 are 0 or 1, respectively.

According to the exemplary embodiment of the present specification, a3 and a4 are 0 or 1, respectively.

In one embodiment of the present specification, Chemical Formula 1 is any one selected from the following compounds.

In the present specification, when a part “includes” a certain component, it means that the component may further include other components, not to exclude other components, unless otherwise stated.

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

The organic light emitting device of the present invention comprises a first electrode; A second electrode provided opposite to the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer may include the above-described compound.

For example, the structure of the organic light emitting device of the present invention may have a structure as shown in FIGS. 1 to 3, but is not limited thereto.

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

1 illustrates an organic light emitting device and is not limited thereto.

2 illustrates a structure of an organic light emitting device in which a first electrode 2, a light emitting layer 5, and a second electrode 4 are sequentially stacked on a substrate 1.

2 illustrates an organic light emitting device, and is not limited thereto, and may further include an additional organic material layer between the first electrode 2 and the light emitting layer 5 and the light emitting layer 5 and the second electrode 4. have.

3, a first electrode 2, a hole injection layer 6, a hole transport layer-1 (7), a hole transport layer-2 (8), a light emitting layer 5, an electron transport layer 9 and a first electrode on the substrate 1 are shown in FIG. The structure of the organic light emitting device in which the two electrodes 4 are sequentially stacked is illustrated.

In an exemplary embodiment of the present invention, the organic material layer includes a light emitting layer, and the light emitting layer includes a compound of Formula 1 above.

The organic light emitting device of the present invention includes a light emitting layer, and the light emitting layer may include a host and a dopant (host: dopant) in a mass ratio of 99.9: 0.1 to 80:20.

The organic light emitting device of the present invention includes a light emitting layer, and the light emitting layer may include a host and a dopant (host: dopant) in a mass ratio of 99.9: 0.1 to 90:10.

In one embodiment of the present invention, the organic material layer includes a light emitting layer, and the light emitting layer includes the compound of Formula 1 as a dopant.

In an exemplary embodiment of the present invention, the organic material layer includes at least one layer of a hole injection layer, a hole transport layer, and a hole injection and transport layer, and at least one layer of the hole injection layer, a hole transport layer, and a hole injection and transport layer is The compound of Formula 1 may be included.

In an exemplary embodiment of the present invention, the organic material layer includes at least one layer of an electron injection layer, an electron transport layer, and an electron injection and transport layer, and at least one layer of the electron injection layer, the electron transport layer, and the electron injection and transport layer is The compound of Formula 1 may be included.

In one embodiment of the present invention, the organic material layer includes one or more of the electron blocking layer and the hole blocking layer, and the electron blocking layer and / or the hole blocking layer may include the compound of Formula 1.

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

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

The present specification also provides a method of manufacturing an organic light emitting device formed using the compound.

For example, the organic light emitting device according to the present invention uses a metal vapor deposition (PVD) method, such as sputtering or e-beam evaporation, to have a metal or conductive metal oxide on the substrate or alloys thereof To form an anode, and then form an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an organic material layer containing the compound of Formula 1, and then use a material that can be used as a cathode thereon. It can be produced by vapor deposition. In addition to this method, an organic light emitting device may be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.

The positive electrode material is usually a material having a large work function 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), and indium zinc oxide (IZO); ZnO: Al or SnO ₂ : Combination of metal and oxide such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

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

As the hole injection material, a hole injection material can be well injected from the anode at a low voltage, and it is preferable that the hole injection material has a high occupied molecular orbital (HOMO) between the work function of the cathode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrine, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based substances. Organic compounds, anthraquinones, and polyaniline-based conductive polymers of a poly compound, and the like, but are not limited thereto.

As the hole transport material, a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer is suitable as a material having high mobility for holes. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion, but are not limited thereto.

As the light-emitting material, a material capable of emitting light in the visible light region by receiving and bonding holes and electrons from the hole transport layer and the electron transport layer, respectively, is preferably a material having good quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole compounds; Poly (p-phenylenevinylene) (PPV) polymers; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited to these.

Examples of the dopant material include an aromatic compound, a strylamine compound, a boron complex, a fluoranthene compound, and a metal complex. Specifically, the aromatic compound is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, periplanene, etc. having an arylamino group, and substituted or unsubstituted as a styrylamine compound. A compound in which at least one arylvinyl group is substituted with an arylamine, a substituent selected from 1 or 2 or more from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamino group is substituted or unsubstituted. Specifically, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like, but are not limited thereto. In addition, examples of the metal complex include an iridium complex and a platinum complex, but are not limited thereto.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer. As the electron transport material, a material capable of receiving electrons from the cathode and transferring them to the light emitting layer is suitable. Do. Specific examples include Al complexes of 8-hydroxyquinoline; Complexes including Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited to these. The electron transport layer can be used with any desired cathode material as used according to the prior art. In particular, examples of suitable cathode materials are those that have a low work function and are followed by an aluminum or silver layer. Specifically, cesium, barium, calcium, ytterbium and samarium, each case followed by an aluminum layer or a silver layer.

The electron injection layer is a layer that injects electrons from an electrode, has the ability to transport electrons, has an electron injection effect from a cathode, has an excellent electron injection effect on a light emitting layer or a light emitting material, and hole injection of excitons generated in the light emitting layer A compound that prevents migration to the layer and has excellent thin film forming ability is preferred. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like and their derivatives, metal Complex compounds, nitrogen-containing 5-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) ( There are o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtholato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, It is not limited to this.

The hole blocking layer is a layer that prevents the cathode from reaching the cathode, 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 complex, and the like, but are not limited thereto.

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

Hereinafter, examples will be described in detail to specifically describe the present specification. However, the embodiments according to the present specification may be modified in various other forms, and the scope of the present specification 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.

< Manufacturing example >

The compound represented by Formula 1 may be prepared by a manufacturing method according to the multi-step reaction of Scheme 1 below. Scheme 1 below may be more specific in the production examples to be described later.

[Scheme 1]

Manufacturing example  1: Synthesis of Compound 1

(1) Preparation Example 1-1: Synthesis of Intermediate Compound C

Compound A (24 g, 90.0 mmol) was added to tetrahydrofuran (900 mL). After adding 2.5M nBuLi (36 mL) at 0 ° C, the mixture was stirred for 5 hours under nitrogen conditions. After raising the temperature to room temperature, the compound B (13.5 g, 90.0 mmol) was added, followed by stirring for 12 hours. After the reaction, 3M NH ₄ Cl (300 mL) was added, and the organic layer was extracted and recrystallized with ethanol to prepare Compound C (26.8 g, yield 88%, MS: [M + H] + = 405).

(2) Preparation Example 1-2: Synthesis of Intermediate Compound D

The compound C (26.8 g, 79.10 mmol) and CH ₃ SO ₂ OH (64 mL) were added, followed by stirring for 5 hours. After cooling to room temperature, the reactant was poured into water, and the resulting solid was filtered to recrystallize the resulting solid with chloroform and ethanol to prepare Compound D (19.3 g, yield 76%, MS: [M + H] + = 387). .

(3) Preparation Example 1-3: Synthesis of Intermediate Compound 1-1

The compound D (30.78 g, 96.0 mmol) and the compound E (13.74 g, 96.0 mmol) were added to xylene (400 mL). After adding NatBuO (55.5 g) and Bis (tri-tert-butylphosphine) palladium (BTP, 0.3 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the resulting solid was recrystallized with ethyl acetate three times to prepare the compound 1-1 (33.24 g, yield 81%, MS: [M + H] + = 428).

(4) Preparation Example 1-4: Synthesis of Compound 1

The compound X-1 (14.92 g, 32.0 mmol) and the compound 1-1 (27.37 g, 64.0 mmol) were added to xylene (400 mL). After adding NatBuO (18.5 g) and BTP (0.2 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the produced solid was recrystallized from ethyl acetate three times to prepare Compound 1 (26.71 g, yield 72%, MS: [M + H] + = 1160).

Manufacturing example  2: Synthesis of Compound 2

The compound X-2 (14.92 g, 32.0 mmol) and the compound 1-2 (20.19 g, 64.0 mmol) were added to xylene (400 mL). After adding NatBuO (18.5 g) and BTP (0.2 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the solid produced by filtration was recrystallized from ethyl acetate three times to prepare Compound 2 (16.16 g, yield 54%, MS: [M + H] + = 936).

Manufacturing example  3: Synthesis of Compound 3

The compound X-3 (15.43 g, 32.0 mmol) and the compound 1-3 (22.88 g, 64.0 mmol) were added to xylene (400 mL). After adding NatBuO (18.5 g) and BTP (0.2 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the produced solid was recrystallized from ethyl acetate three times to prepare the compound 3 (14.58 g, yield 44%, MS: [M + H] + = 1036).

Manufacturing example  4: Synthesis of Compound 4

The compound X-4 (13.83 g, 32.0 mmol) and the compound 1-4 (21.09 g, 64.0 mmol) were added to xylene (400 mL). After adding NatBuO (18.5 g) and BTP (0.2 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the resulting solid was recrystallized from ethyl acetate three times to prepare compound 4 (16.65 g, yield 56%, MS: [M + H] + = 930).

Manufacturing example  5: Synthesis of Compound 5

The compound X-5 (14.92 g, 32.0 mmol) and the compound 1-5 (40.57 g, 64.0 mmol) were added to xylene (400 mL). After adding NatBuO (18.5 g) and BTP (0.2 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the solid produced by filtration was recrystallized from ethyl acetate three times to prepare the compound 5 (27.67 g, yield 55%, MS: [M + H] + = 1572).

Manufacturing example  6: Synthesis of Compound 6

The compound X-6 (15.43 g, 32.0 mmol) and the compound 1-6 (31.73 g, 64.0 mmol) were added to xylene (400 mL). After adding NatBuO (18.5 g) and BTP (0.2 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the solid produced by filtration was recrystallized from ethyl acetate three times to prepare Compound 6 (27.27 g, yield 65%, MS: [M + H] + = 1312).

Manufacturing example  7: Synthesis of Compound 7

The compound X-7 (15.43 g, 32.0 mmol) and the compound 1-7 (33.90 g, 64.0 mmol) were added to xylene (400 mL). After adding NatBuO (18.5 g) and BTP (0.2 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the resulting solid was recrystallized from ethyl acetate three times to prepare the compound 7 (28.70 g, yield 65%, MS: [M + H] + = 1380).

Manufacturing example  8: Synthesis of Compound 8

The compound X-8 (15.69 g, 32.0 mmol) and the compound 1-8 (24.16 g, 64.0 mmol) were added to xylene (400 mL). After adding NatBuO (18.5 g) and BTP (0.2 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized three times with ethyl acetate to prepare the compound 8 (22.88 g, yield 66%, MS: [M + H] + = 1084).

Manufacturing example  9: Synthesis of Compound 9

The compound X-9 (15.24 g, 32.0 mmol) and the compound 1-9 (54.57 g, 64.0 mmol) were added to xylene (400 mL). After adding NatBuO (18.5 g) and BTP (0.2 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the solid produced by filtration was recrystallized from ethyl acetate three times to prepare the compound 9 (35.05 g, yield 63%, MS: [M + H] + = 1739).

Manufacturing example  10: Synthesis of Compound 10

The compound X-10 (15.75 g, 32.0 mmol) and the compound 1-10 (35.83 g, 64.0 mmol) were added to xylene (400 mL). After adding NatBuO (18.5 g) and BTP (0.2 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the produced solid was recrystallized from ethyl acetate three times to prepare the compound 10 (25.05 g, yield 54%, MS: [M + H] + = 1450).

Manufacturing example  11: Synthesis of Compound 11

The compound X-11 (18.03 g, 32.0 mmol) and the compound 1-11 (40.70 g, 64.0 mmol) were added to xylene (400 mL). After adding NatBuO (18.5 g) and BTP (0.2 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the resulting solid was recrystallized with ethyl acetate three times to prepare the compound 11 (31.59 g, yield 59%, MS: [M + H] + = 1674).

Manufacturing example  12: Synthesis of Compound 12

The compound X-12 (13.83 g, 32.0 mmol) and the compound 1-12 (27.37 g, 64.0 mmol) were added to xylene (400 mL). After adding NatBuO (18.5 g) and BTP (0.2 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the resulting solid was recrystallized with ethyl acetate three times to prepare the compound 12 (22.69 g, yield 63%, MS: [M + H] + = 1126).

Manufacturing example  13: Synthesis of Compound 13

The compound X-13 (15.75 g, 32.0 mmol) and the compound 1-13 (40.70 g, 64.0 mmol) were added to xylene (400 mL). After adding NatBuO (18.5 g) and BTP (0.2 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the resulting solid was recrystallized from ethyl acetate three times to prepare the compound 13 (38.45 g, yield 75%, MS: [M + H] + = 1603).

Manufacturing example  14: Synthesis of Compound 14

The compound X-14 (14.85 g, 32.0 mmol) and the compound 1-14 (40.70 g, 64.0 mmol) were added to xylene (400 mL). After adding NatBuO (18.5 g) and BTP (0.2 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized three times with ethyl acetate to prepare the compound 14 (25.18 g, yield 50%, MS: [M + H] + = 1575).

Manufacturing example  15: Synthesis of Compound 15

The compound X-15 (13.83 g, 32.0 mmol) and the compound 1-15 (31.60 g, 64.0 mmol) were added to xylene (400 mL). After adding NatBuO (18.5 g) and BTP (0.2 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized three times with ethyl acetate to prepare the compound 15 (16.90 g, yield 42%, MS: [M + H] + = 1258).

Manufacturing example  16: Synthesis of Compound 16

The compound X-16 (14.15 g, 32.0 mmol) and the compound 1-16 (35.83 g, 64.0 mmol) were added to xylene (400 mL). After adding NatBuO (18.5 g) and BTP (0.2 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the produced solid was recrystallized from ethyl acetate three times to prepare the compound 16 (23.29 g, yield 52%, MS: [M + H] + = 1400).

Manufacturing example  17: Synthesis of Compound 17

The compound X-17 (14.85 g, 32.0 mmol) and the compound 1-17 (39.67 g, 64.0 mmol) were added to xylene (400 mL). After adding NatBuO (18.5 g) and BTP (0.2 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the produced solid was recrystallized from ethyl acetate three times to prepare the compound 17 (26.15 g, yield 53%, MS: [M + H] + = 1542).

Manufacturing example  18: Synthesis of Compound 18

The compound X-18 (10.95 g, 32.0 mmol) and the compound 1-18 (35.83 g, 64.0 mmol) were added to xylene (400 mL). After adding NatBuO (18.5 g) and BTP (0.2 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized three times with ethyl acetate to prepare the compound 18 (32.86 g, yield 79%, MS: [M + H] + = 1300).

Manufacturing example  19: Synthesis of Compound 19

The compound X-19 (14.15 g, 32.0 mmol) and the compound 1-19 (39.61 g, 64.0 mmol) were added to xylene (400 mL). After adding NatBuO (18.5 g) and BTP (0.2 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized three times with ethyl acetate to prepare the compound 19 (34.00 g, yield 70%, MS: [M + H] + = 1519).

Manufacturing example  20: Synthesis of Compound 20

The compound X-20 (14.15 g, 32.0 mmol) and the compound 1-20 (29.03 g, 64.0 mmol) were added to xylene (400 mL). After adding NatBuO (18.5 g) and BTP (0.2 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the produced solid was recrystallized from ethyl acetate three times to prepare the compound 20 (22.80 g, yield 60%, MS: [M + H] + = 1188).

Manufacturing example  21: Synthesis of Compound 21

The compound X-21 (12.35 g, 32.0 mmol) and the compound 21 (35.83 g, 64.0 mmol) were added to xylene (400 mL). After adding NatBuO (18.5 g) and BTP (0.2 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the produced solid was recrystallized from ethyl acetate three times to prepare the compound 21 (27.09 g, yield 63%, MS: [M + H] + = 1344).

Manufacturing example  22: Synthesis of Compound 22

The compound X-22 (12.03 g, 32.0 mmol) and the compound 1-22 (40.70 g, 64.0 mmol) were added to xylene (400 mL). After adding NatBuO (18.5 g) and BTP (0.2 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the produced solid was recrystallized from ethyl acetate three times to prepare the compound 22 (23.78 g, yield 50%, MS: [M + H] + = 1487).

Manufacturing example  23: Synthesis of Compound 23

The compound X-23 (13.64 g, 32.0 mmol) and the compound 1-23 (29.03 g, 64.0 mmol) were added to xylene (400 mL). After adding NatBuO (18.5 g) and BTP (0.2 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the solid produced by filtration was recrystallized from ethyl acetate three times to prepare the compound 23 (20.62 g, yield 55%, MS: [M + H] + = 1172).

Manufacturing example  24: Synthesis of Compound 24

The compound X-24 (12.35 g, 32.0 mmol) and the compound 1-24 (34.80 g, 64.0 mmol) were added to xylene (400 mL). After adding NatBuO (18.5 g) and BTP (0.2 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the produced solid was recrystallized from ethyl acetate three times to prepare the compound 24 (22.67 g, yield 54%, MS: [M + H] + = 1312).

Manufacturing example  25: Synthesis of Compound 25

The compound X-25 (11.52 g, 32.0 mmol) and the compound 1-25 (31.60 g, 64.0 mmol) were added to xylene (400 mL). After adding NatBuO (18.5 g) and BTP (0.2 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the solid produced by filtration was recrystallized from ethyl acetate three times to prepare the compound 25 (20.49 g, yield 54%, MS: [M + H] + = 1186).

Manufacturing example  26: Synthesis of Compound 26

The compound X-26 (13.64 g, 32.0 mmol) and the compound 1-26 (35.83 g, 64.0 mmol) were added to xylene (400 mL). After adding NatBuO (18.5 g) and BTP (0.2 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the produced solid was recrystallized from ethyl acetate three times to prepare the compound 26 (24.36 g, yield 55%, MS: [M + H] + = 1384).

Manufacturing example  27: Synthesis of Compound 27

The compound X-27 (14.15 g, 32.0 mmol) and the compound 1-27 (34.80 g, 64.0 mmol) were added to xylene (400 mL). After adding NatBuO (18.5 g) and BTP (0.2 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the solid produced by filtration was recrystallized with ethyl acetate three times to prepare the compound 27 (24.51 g, yield 56%, MS: [M + H] + = 1368).

Manufacturing example  28: Synthesis of Compound 28

The compound X-28 (14.15 g, 32.0 mmol) and the compound 1-28 (34.80 g, 64.0 mmol) were added to xylene (400 mL). After adding NatBuO (18.5 g) and BTP (0.2 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the produced solid was recrystallized from ethyl acetate three times to prepare the compound 28 (34.14 g, yield 78%, MS: [M + H] + = 1368).

Manufacturing example  29: Synthesis of Compound 29

The compound X-29 (14.15 g, 32.0 mmol) and the compound 1-29 (35.83 g, 64.0 mmol) were added to xylene (400 mL). After adding NatBuO (18.5 g) and BTP (0.2 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the solid produced by filtration was recrystallized from ethyl acetate three times to prepare the compound 29 (30.46 g, yield 68%, MS: [M + H] + = 1400).

Manufacturing example  30: Synthesis of Compound 30

The compound X-30 (10.95 g, 32.0 mmol) and the compound 1-30 (27.37 g, 64.0 mmol) were added to xylene (400 mL). After adding NatBuO (18.5 g) and BTP (0.2 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized three times with ethyl acetate to prepare the compound 30 (18.89 g, yield 57%, MS: [M + H] + = 1036).

Manufacturing example  31: Synthesis of Compound 31

The compound X-31 (14.15 g, 32.0 mmol) and the compound 1-31 (31.60 g, 64.0 mmol) were added to xylene (400 mL). After adding NatBuO (18.5 g) and BTP (0.2 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the produced solid was recrystallized from ethyl acetate three times to prepare the compound 31 (27.59 g, yield 68%, MS: [M + H] + = 1268).

Manufacturing example  32: Synthesis of Compound 32

The compound X-32 (12.55 g, 32.0 mmol) and the compound 1-32 (34.73 g, 64.0 mmol) were added to xylene (400 mL). After adding NatBuO (18.5 g) and BTP (0.2 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the produced solid was recrystallized from ethyl acetate three times to prepare the compound 32 (24.00 g, yield 57%, MS: [M + H] + = 1316).

Manufacturing example  33: Synthesis of Compound 33

The compound X-33 (14.15 g, 32.0 mmol) and the compound 1-33 (29.03 g, 64.0 mmol) were added to xylene (400 mL). After adding NatBuO (18.5 g) and BTP (0.2 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the solid produced by filtration was recrystallized with ethyl acetate three times to prepare the compound 33 (24.32 g, yield 64%, MS: [M + H] + = 1188).

Manufacturing example  34: Synthesis of Compound 34

The compound X-34 (14.15 g, 32.0 mmol) and the compound 1-34 (35.83 g, 64.0 mmol) were added to xylene (400 mL). After adding NatBuO (18.5 g) and BTP (0.2 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the produced solid was recrystallized from ethyl acetate three times to prepare the compound 34 (27.33 g, yield 61%, MS: [M + H] + = 1400).

Manufacturing example  35: Synthesis of Compound 35

The compound X-35 (12.55 g, 32.0 mmol) and the compound 1-35 (27.37 g, 64.0 mmol) were added to xylene (400 mL). After adding NatBuO (18.5 g) and BTP (0.2 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the resulting solid was recrystallized with ethyl acetate three times to prepare the compound 35 (18.06 g, yield 52%, MS: [M + H] + = 1086).

Manufacturing example  36: Synthesis of Compound 36

The compound X-36 (17.29 g, 32.0 mmol) and the compound 1-36 (40.70 g, 64.0 mmol) were added to xylene (400 mL). After adding NatBuO (18.5 g) and BTP (0.2 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the produced solid was recrystallized with ethyl acetate three times to prepare the compound 36 (28.52 g, yield 54%, MS: [M + H] + = 1651).

Manufacturing example  37: Synthesis of Compound 37

The compound X-37 (15.94 g, 32.0 mmol) and the compound 1-37 (29.03 g, 64.0 mmol) were added to xylene (400 mL). After adding NatBuO (18.5 g) and BTP (0.2 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the resulting solid was recrystallized with ethyl acetate three times to prepare the compound 37 (23.08 g, yield 58%, MS: [M + H] + = 1244).

Manufacturing example  38: Synthesis of Compound 38

The compound X-38 (17.87 g, 32.0 mmol) and the compound 1-38 (34.73 g, 64.0 mmol) were added to xylene (400 mL). After adding NatBuO (18.5 g) and BTP (0.2 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the produced solid was recrystallized with ethyl acetate three times to prepare the compound 38 (32.72 g, yield 69%, MS: [M + H] + = 1483).

Preparation 39: Synthesis of Compound 39

The compound X-39 (16.52 g, 32.0 mmol) and the compound 1-39 (27.76 g, 64.0 mmol) were added to xylene (400 mL). After adding NatBuO (18.5 g) and BTP (0.2 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the solid produced by filtration was recrystallized from ethyl acetate three times to prepare the compound 39 (30.48 g, yield 71%, MS: [M + H] + = 1342).

Preparation 40: Synthesis of Compound 40

The compound X-40 (16.52 g, 32.0 mmol) and the compound 1-40 (29.03 g, 64.0 mmol) were added to xylene (400 mL). After adding NatBuO (18.5 g) and BTP (0.2 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized three times with ethyl acetate to prepare the compound 40 (25.43 g, yield 63%, MS: [M + H] + = 1262).

Preparation Example 41: Synthesis of Compound 41

The compound X-41 (12.03 g, 32.0 mmol) and the compound 1-41 (34.73 g, 64.0 mmol) were added to xylene (400 mL). After adding NatBuO (18.5 g) and BTP (0.2 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the produced solid was recrystallized from ethyl acetate three times to prepare the compound 41 (22.04 g, yield 53%, MS: [M + H] + = 1300).

Preparation 42: Synthesis of Compound 42

The compound X-42 (13.64 g, 32.0 mmol) and the compound 1-42 (39.67 g, 64.0 mmol) were added to xylene (400 mL). After adding NatBuO (18.5 g) and BTP (0.2 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the produced solid was recrystallized from ethyl acetate three times to prepare the compound 42 (26.47 g, yield 55%, MS: [M + H] + = 1504).

Preparation 43: Synthesis of Compound 43

The compound X-43 (16.97 g, 32.0 mmol) and the compound 1-43 (35.83 g, 64.0 mmol) were added to xylene (400 mL). After adding NatBuO (18.5 g) and BTP (0.2 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the solid produced by filtration was recrystallized from ethyl acetate three times to prepare the compound 43 (30.47 g, yield 64%, MS: [M + H] + = 1489).

Preparation 44: Synthesis of Compound 44

The compound X-44 (17.87 g, 32.0 mmol) and the compound 1-44 (34.80 g, 64.0 mmol) were added to xylene (400 mL). After adding NatBuO (18.5 g) and BTP (0.2 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the produced solid was recrystallized from ethyl acetate three times to prepare the compound 44 (32.29 g, yield 68%, MS: [M + H] + = 1485).

Preparation Example 45 Synthesis of Compound 45

The compound X-45 (16.52 g, 32.0 mmol) and the compound 1-45 (29.03 g, 64.0 mmol) were added to xylene (400 mL). After adding NatBuO (18.5 g) and BTP (0.2 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the resulting solid was recrystallized with ethyl acetate three times to prepare the compound 45 (29.88 g, yield 74%, MS: [M + H] + = 1262).

Preparation 46: Synthesis of Compound 46

The compound X-46 (14.92 g, 32.0 mmol) and the compound 1-46 (35.83 g, 64.0 mmol) were added to xylene (400 mL). After adding NatBuO (18.5 g) and BTP (0.2 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the produced solid was recrystallized from ethyl acetate three times to prepare the compound 46 (28.70 g, yield 63%, MS: [M + H] + = 1424).

Preparation 47: Synthesis of Compound 47

The compound X-47 (14.92 g, 32.0 mmol) and the compound 1-47 (39.67 g, 64.0 mmol) were added to xylene (400 mL). After adding NatBuO (18.5 g) and BTP (0.2 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the produced solid was recrystallized from ethyl acetate three times to prepare the compound 47 (26.68 g, yield 54%, MS: [M + H] + = 1544).

Preparation 48: Synthesis of Compound 48

The compound X-48 (15.75 g, 32.0 mmol) and the compound 1-48 (34.73 g, 64.0 mmol) were added to xylene (400 mL). After adding NatBuO (18.5 g) and BTP (0.2 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized three times with ethyl acetate to prepare the compound 48 (20.39 g, yield 45%, MS: [M + H] + = 1416).

Preparation 49: Synthesis of Compound 49

The compound X-49 (15.37 g, 32.0 mmol) and the compound 1-49 (27.37 g, 64.0 mmol) were added to xylene (400 mL). After adding NatBuO (18.5 g) and BTP (0.2 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the produced solid was recrystallized from ethyl acetate three times to prepare the compound 49 (18.03 g, yield 48%, MS: [M + H] + = 1174).

Preparation Example 50: Synthesis of Compound 50

The compound X-50 (15.94 g, 32.0 mmol) and the compound 1-50 (29.03 g, 64.0 mmol) were added to xylene (400 mL). After adding NatBuO (18.5 g) and BTP (0.2 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the produced solid was recrystallized from ethyl acetate three times to prepare the compound 50 (23.08 g, yield 58%, MS: [M + H] + = 1244).

Preparation 51: Synthesis of Compound 51

The compound X-51 (14.92 g, 32.0 mmol) and the compound 1-51 (20.19 g, 64.0 mmol) were added to xylene (400 mL). After adding NatBuO (18.5 g) and BTP (0.2 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the solid produced by filtration was recrystallized with ethyl acetate three times to prepare the compound 51 (16.46 g, yield 55%, MS: [M + H] + = 936).

Preparation 52: Synthesis of Compound 52

The compound X-52 (14.92 g, 32.0 mmol) and the compound 1-52 (32.24 g, 64.0 mmol) were added to xylene (400 mL). After adding NatBuO (18.5 g) and BTP (0.2 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the solid produced by filtration was recrystallized from ethyl acetate three times to prepare the compound 52 (28.96 g, yield 69%, MS: [M + H] + = 1312).

Preparation 53: Synthesis of Compound 53

The compound X-53 (14.92 g, 32.0 mmol) and the compound 1-53 (34.29 g, 64.0 mmol) were added to xylene (400 mL). After adding NatBuO (18.5 g) and BTP (0.2 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the produced solid was recrystallized from ethyl acetate three times to prepare the compound 53 (18.49 g, yield 42%, MS: [M + H] + = 1376).

Preparation 54: Synthesis of Compound 54

The compound X-54 (14.92 g, 32.0 mmol) and the compound 1-54 (20.19 g, 64.0 mmol) were added to xylene (400 mL). After adding NatBuO (18.5 g) and BTP (0.2 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the produced solid was recrystallized from ethyl acetate three times to prepare the compound 54 (20.35 g, yield 68%, MS: [M + H] + = 936).

Preparation Example 55: Synthesis of Compound 55

The compound X-55 (15.43 g, 32.0 mmol) and the compound 1-55 (33.39 g, 64.0 mmol) were added to xylene (400 mL). After adding NatBuO (18.5 g) and BTP (0.2 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized three times with ethyl acetate to prepare the compound 55 (24.00 g, yield 55%, MS: [M + H] + = 1364).

Preparation 56: Synthesis of Compound 56

The compound X-56 (15.43 g, 32.0 mmol) and the compound 1-56 (33.90 g, 64.0 mmol) were added to xylene (400 mL). After adding NatBuO (18.5 g) and BTP (0.2 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the solid produced by filtration was recrystallized from ethyl acetate three times to prepare the compound 56 (24.28 g, yield 55%, MS: [M + H] + = 1380).

Preparation Example 57: Synthesis of Compound 57

The compound X-57 (15.43 g, 32.0 mmol) and the compound 1-57 (33.90 g, 64.0 mmol) were added to xylene (400 mL). After adding NatBuO (18.5 g) and BTP (0.2 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the resulting solid was recrystallized from ethyl acetate three times to prepare compound 57 (23.40 g, yield 53%, MS: [M + H] + = 1380).

Preparation 58: Synthesis of Compound 58

The compound X-58 (15.43 g, 32.0 mmol) and the compound 1-58 (21.09 g, 64.0 mmol) were added to xylene (400 mL). After adding NatBuO (18.5 g) and BTP (0.2 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the produced solid was recrystallized from ethyl acetate three times to prepare the compound 58 (19.43 g, yield 62%, MS: [M + H] + = 980).

Preparation 59: Synthesis of Compound 59

The compound X-59 (13.83 g, 32.0 mmol) and the compound 1-59 (21.09 g, 64.0 mmol) were added to xylene (400 mL). After adding NatBuO (18.5 g) and BTP (0.2 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the solid produced by filtration was recrystallized from ethyl acetate three times to prepare the compound 59 (17.84 g, yield 60%, MS: [M + H] + = 930).

Preparation Example 60: Synthesis of Compound 60

The compound X-60 (13.83 g, 32.0 mmol) and the compound 1-60 (21.09 g, 64.0 mmol) were added to xylene (400 mL). After adding NatBuO (18.5 g) and BTP (0.2 g), the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the resulting solid was recrystallized from ethyl acetate three times to prepare the compound 60 (18.14 g, yield 61%, MS: [M + H] + = 930).

<Experimental Example>

Example  1: Preparation of organic light emitting device

A glass substrate (corning 7059 glass) coated with a thin film of ITO (indium tin oxide) at a thickness of 1,000 Å was put in distilled water in which a dispersing agent was dissolved and washed with ultrasonic waves. As a detergent, a product of Fischer Co. was used, and distilled water was used by Millipore Co. Distilled water filtered secondarily was used as a filter of the product. After washing the ITO for 30 minutes, ultrasonic washing was repeated for 10 minutes by repeating it twice with distilled water. After washing with distilled water, ultrasonic cleaning was performed in the order of isopropyl alcohol, acetone, and methanol, followed by drying.

On the prepared ITO transparent electrode, the following HAT was thermally vacuum-deposited to a thickness of 50 Pa to form a hole injection layer. The following HT-A 1000 Pa was vacuum-deposited as a hole transport layer, and the following HT-B 100 Pa was deposited. The compound 1 of Preparation Example 1 was doped with 4 wt% as a dopant in the following H-A as a host as a light emitting layer, and then vacuum-deposited to a thickness of 200 Pa. Subsequently, the following ET-A and the following Liq were deposited at 300Å in a 1: 1 ratio to form an electron transport layer, and on this, 150Å thick silver (Ag) was sequentially doped with 10wt% magnesium (Mg), and 1,000Å An anode was formed by depositing aluminum having a thickness, thereby manufacturing an organic light emitting device.

In the above process, the deposition rate of the organic material was maintained at 1 Å / sec, LiF was 0.2 Å / sec, and aluminum was maintained at a deposition rate of 3 Å / sec to 7 Å / sec.

Example  2 to 120 and Comparative example  1 to 8: Preparation of organic light emitting device

When manufacturing the organic light emitting device of Example 1, using the compounds of Table 1 and Table 2 below instead of HA as a light emitting layer host, using the compounds of Table 1 and Table 2 instead of Compound 1 of Preparation Example 1 as a light emitting layer dopant An organic light emitting device was manufactured in the same manner as in Example 1 except for the above.

The driving voltage and luminous efficiency of the organic light emitting devices of Examples 1 to 120 and Comparative Examples 1 to 8 were measured at a current density of 10 mA / cm ² , and 95% of the initial luminance at a current density of 20 mA / cm ² was Time (LT95) was measured. The results are shown in Table 1 and Table 2 below.

	Host	Dopant	@ 10 mA / cm 2			LT95
			Voltage (V)	Efficiency (cd / A)	color	Life (hr)
Example 1	H-A	Compound 1	4.21	6.30	blue	100
Example 2	H-A	Compound 2	4.22	6.20	blue	110
Example 3	H-A	Compound 3	4.25	6.00	blue	120
Example 4	H-A	Compound 4	4.26	5.95	blue	125
Example 5	H-A	Compound 5	4.31	5.80	blue	105
Example 6	H-A	Compound 6	4.19	6.03	blue	105
Example 7	H-A	Compound 7	4.21	6.06	blue	110
Example 8	H-A	Compound 8	4.18	6.08	blue	115
Example 9	H-A	Compound 9	4.23	6.12	blue	110
Example 10	H-A	Compound 10	4.10	6.04	blue	110
Example 11	H-A	Compound 11	4.00	6.11	blue	110
Example 12	H-A	Compound 12	4.10	6.20	blue	115
Example 13	H-A	Compound 13	4.20	6.22	blue	100
Example 14	H-A	Compound 14	4.10	6.20	blue	95
Example 15	H-A	Compound 15	4.15	6.20	blue	100
Example 16	H-A	Compound 16	4.10	6.98	blue	105
Example 17	H-A	Compound 17	4.00	6.28	blue	100
Example 18	H-A	Compound 18	4.00	6.29	blue	100
Example 19	H-A	Compound 19	4.10	6.27	blue	105
Example 20	H-A	Compound 20	4.15	6.25	blue	130
Example 21	H-A	Compound 21	4.20	6.10	blue	140
Example 22	H-A	Compound 22	4.20	6.55	blue	135
Example 23	H-A	Compound 23	4.20	6.10	blue	100
Example 24	H-A	Compound 24	4.15	6.05	blue	110
Example 25	H-A	Compound 25	4.22	6.00	blue	120
Example 26	H-A	Compound 26	4.31	6.03	blue	120
Example 27	H-A	Compound 27	4.20	6.08	blue	115
Example 28	H-A	Compound 28	4.19	6.30	blue	120
Example 29	H-A	Compound 29	4.17	6.04	blue	130
Example 30	H-A	Compound 30	4.16	6.11	blue	125
Example 31	H-A	Compound 31	4.11	6.28	blue	110
Example 32	H-A	Compound 32	3.99	6.05	blue	115
Example 33	H-A	Compound 33	4.00	6.36	blue	110
Example 34	H-A	Compound 34	4.15	6.50	blue	120
Example 35	H-A	Compound 35	4.11	6.60	blue	140
Example 36	H-A	Compound 36	4.12	6.45	blue	135
Example 37	H-A	Compound 37	4.30	5.90	blue	130
Example 38	H-A	Compound 38	4.30	5.80	blue	130
Example 39	H-A	Compound 39	4.15	6.10	blue	110
Example 40	H-A	Compound 40	4.18	6.15	blue	95
Example 41	H-A	Compound 41	4.19	6.15	blue	100
Example 42	H-A	Compound 42	4.30	6.13	blue	115
Example 43	H-A	Compound 43	4.22	6.18	blue	110
Example 44	H-A	Compound 44	4.20	6.28	blue	100
Example 45	H-A	Compound 45	4.07	5.84	blue	110
Example 46	H-A	Compound 46	4.10	6.81	blue	110
Example 47	H-A	Compound 47	4.06	6.50	blue	105
Example 48	H-A	Compound 48	4.05	6.70	blue	115
Example 49	H-A	Compound 49	4.05	6.68	blue	105
Example 50	H-A	Compound 50	4.00	6.98	blue	120
Example 51	H-A	Compound 51	4.00	6.28	blue	125
Example 52	H-A	Compound 52	4.05	6.29	blue	110
Example 53	H-A	Compound 53	4.06	6.27	blue	100
Example 54	H-A	Compound 54	4.09	6.78	blue	105
Example 55	H-A	Compound 55	4.14	6.28	blue	95
Example 56	H-A	Compound 56	4.11	6.10	blue	90
Example 57	H-A	Compound 57	4.15	6.22	blue	125
Example 58	H-A	Compound 58	4.09	6.13	blue	130
Example 59	H-A	Compound 59	4.05	6.00	blue	115
Example 60	H-A	Compound 60	4.00	6.05	blue	110
Comparative Example 1	H-A	D-1	4.39	5.31	blue	75
Comparative Example 2	H-A	D-2	4.42	3.50	blue	50
Comparative Example 3	H-A	D-3	4.40	4.88	blue	85
Comparative Example 4	H-A	D-4	4.50	2.05	blue	10

	Host	Dopant	@ 10 mA / cm 2			LT95
			Voltage (V)	Efficiency (cd / A)	color	Life (hr)
Example 61	H-B	Compound 1	4.25	6.15	blue	105
Example 62	H-B	Compound 2	4.27	6.13	blue	120
Example 63	H-B	Compound 3	4.30	6.98	blue	125
Example 64	H-B	Compound 4	4.26	6.29	blue	110
Example 65	H-B	Compound 5	4.30	6.27	blue	130
Example 66	H-B	Compound 6	4.20	6.78	blue	125
Example 67	H-B	Compound 7	4.20	6.28	blue	110
Example 68	H-B	Compound 8	4.30	6.10	blue	115
Example 69	H-B	Compound 9	4.33	6.22	blue	110
Example 70	H-B	Compound 10	4.31	6.04	blue	120
Example 71	H-B	Compound 11	4.28	6.11	blue	115
Example 72	H-B	Compound 12	4.22	6.28	blue	110
Example 73	H-B	Compound 13	4.32	6.05	blue	100
Example 74	H-B	Compound 14	4.32	6.36	blue	110
Example 75	H-B	Compound 15	4.20	6.28	blue	120
Example 76	H-B	Compound 16	4.20	6.29	blue	120
Example 77	H-B	Compound 17	4.19	6.11	blue	130
Example 78	H-B	Compound 18	4.20	6.28	blue	125
Example 79	H-B	Compound 19	4.32	6.03	blue	115
Example 80	H-B	Compound 20	4.30	6.08	blue	125
Example 81	H-B	Compound 21	4.20	6.30	blue	110
Example 82	H-B	Compound 22	4.30	6.04	blue	115
Example 83	H-B	Compound 23	4.33	6.11	blue	110
Example 84	H-B	Compound 24	4.31	6.28	blue	120
Example 85	H-B	Compound 25	4.28	6.03	blue	140
Example 86	H-B	Compound 26	4.28	6.08	blue	135
Example 87	H-B	Compound 27	4.22	6.30	blue	130
Example 88	H-B	Compound 28	4.32	6.04	blue	125
Example 89	H-B	Compound 29	4.41	6.11	blue	110
Example 90	H-B	Compound 30	4.29	6.28	blue	115
Example 91	H-B	Compound 31	4.30	6.05	blue	110
Example 92	H-B	Compound 32	4.29	6.77	blue	120
Example 93	H-B	Compound 33	4.28	6.98	blue	140
Example 94	H-B	Compound 34	4.25	6.45	blue	115
Example 95	H-B	Compound 35	4.32	6.44	blue	110
Example 96	H-B	Compound 36	4.31	6.37	blue	100
Example 97	H-B	Compound 37	4.40	6.28	blue	110
Example 98	H-B	Compound 38	4.29	6.77	blue	110
Example 99	H-B	Compound 39	4.32	6.98	blue	105
Example 100	H-B	Compound 40	4.31	6.45	blue	115
Example 101	H-B	Compound 41	4.40	6.44	blue	105
Example 102	H-B	Compound 42	4.32	6.37	blue	120
Example 103	H-B	Compound 43	4.31	6.28	blue	120
Example 104	H-B	Compound 44	4.40	6.98	blue	130
Example 105	H-B	Compound 45	4.46	6.45	blue	125
Example 106	H-B	Compound 46	4.41	6.44	blue	115
Example 107	H-B	Compound 47	4.29	6.37	blue	120
Example 108	H-B	Compound 48	4.30	6.28	blue	130
Example 109	H-B	Compound 49	4.30	6.57	blue	125
Example 110	H-B	Compound 50	4.25	6.48	blue	115
Example 111	H-B	Compound 51	4.25	6.53	blue	115
Example 112	H-B	Compound 52	4.27	6.38	blue	110
Example 113	H-B	Compound 53	4.29	6.28	blue	100
Example 114	H-B	Compound 54	4.28	6.29	blue	110
Example 115	H-B	Compound 55	4.25	6.27	blue	110
Example 116	H-B	Compound 56	4.26	6.78	blue	105
Example 117	H-B	Compound 57	4.25	6.28	blue	115
Example 118	H-B	Compound 58	4.25	6.10	blue	105
Example 119	H-B	Compound 59	4.29	6.53	blue	105
Example 120	H-B	Compound 60	4.30	6.38	blue	115
Comparative Example 5	H-B	D-1	4.56	5.12	blue	80
Comparative Example 6	H-B	D-2	4.54	4.50	blue	60
Comparative Example 7	H-B	D-3	4.55	5.32	blue	95
Comparative Example 8	H-B	D-4	4.80	2.00	blue	10

From Tables 1 and 2, it can be seen that Examples 1 to 120 of the present application have lower driving voltages of devices than Comparative Examples 1 to 8, and are very excellent in efficiency and lifespan characteristics.

Claims (8)

1. Compound represented by the formula (1):

   [Formula 1]

   

   In Chemical Formula 1,

   A is a substituted or unsubstituted divalent aromatic ring; Or a substituted or unsubstituted divalent heterocycle,

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

   R ₁ to R ₄ are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Nitrile group; Halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted silyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

   a1 and a2 are integers from 0 to 4,

   a3 and a4 are integers from 0 to 3,

   When a1 is plural, R ₁ is the same as or different from each other,

   When a2 is plural, R ₂ is the same as or different from each other,

   When a3 is plural, R ₃ is the same as or different from each other,

   When a4 is plural, R ₄ is the same as or different from each other.
2. The method according to claim 1, wherein A is any one of the following Formula 1-1 to Formula 1-10:

   [Formula 1-1]

   

   [Formula 1-2]

   

   [Formula 1-3]

   

   [Formula 1-4]

   

   [Formula 1-5]

   

   [Formula 1-6]

   

   [Formula 1-7]

   

   [Formula 1-8]

   

   [Formula 1-9]

   

   [Formula 1-10]

   

   In Chemical Formulas 1-1 to 1-10,

   X ₁ to X ₁₆ are the same as or different from each other, and each independently O; S; SO; SO ₂ ; Or CR'R ",

   R 'and R "are the same as or different from each other, and each independently hydrogen; deuterium; nitrile group; halogen group; substituted or unsubstituted alkyl group; substituted or unsubstituted alkoxy group; substituted or unsubstituted silyl group; substituted or An unsubstituted amine group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, or combine with each other to form a substituted or unsubstituted ring,

   n1 to n9, and m1 to m9 are integers from 0 to 2,

   When n1 to n9, and m1 to m9 are 2, rings in parentheses may overlap.
3. The method according to claim 1, wherein A is a substituted or unsubstituted divalent 1 to 8 ring aromatic ring; Or a substituted or unsubstituted divalent 1 to 8 ring heterocycle.
4. The method according to claim 1, wherein Ar ₁ and Ar ₂ are the same as or different from each other, and each independently substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms containing 1 to 3 heteroatoms selected from the group consisting of N, O and S.
5. The method according to claim 1, wherein Formula 1 is any one compound selected from the following compounds:

   

   

   

   

   

   

   

   

   

   .
6. A first electrode; A second electrode provided opposite to 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 of the organic material layers comprises the compound of claim 1. Light emitting element.
7. The method according to claim 6, The organic layer comprises a light emitting layer, the light emitting layer is an organic light emitting device comprising a host and a dopant in a mass ratio of 99.9: 0.1 to 80:20.
8. The method according to claim 6, The organic layer comprises a light emitting layer, the light emitting layer is an organic light emitting device comprising the compound as a dopant.

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