KR102141284B1 - Multicyclic compound and organic light emitting device comprising the same - Google Patents

Abstract

The present specification provides a compound represented by Chemical Formula 1 and an organic light emitting device including the same.

Description

Polycyclic compound and an organic light emitting device comprising the same{MULTICYCLIC COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME}

This application claims the benefit of the filing date of Korean Patent Application No. 10-2017-0146798 filed with the Korean Intellectual Property Office on November 6, 2017, 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 the present specification, the organic light emitting device is a light emitting device using an organic semiconductor material, and requires the exchange of holes and/or electrons between the electrode and the organic semiconductor material. The organic light emitting device can be roughly divided into two types according to the operation principle. First, excitons are formed in the organic layer by photons introduced into the device from an external light source, and the excitons are separated into electrons and holes, and the electrons and holes are transferred to different electrodes to be used as current sources (voltage sources). It is a light emitting device of the form. The second is a light emitting device in which holes and/or electrons are injected into a layer of an organic semiconductor material that interfaces with an electrode by applying voltage or current to two or more electrodes, and operated by the injected electrons and holes.

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 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 excitons are formed when the injected holes meet the electrons. When it falls to the ground again, it will shine. It is known that such an organic light emitting device has characteristics such as self-luminescence, high luminance, high efficiency, low driving voltage, wide viewing angle, and high contrast.

Materials used as the organic material layer in the organic light emitting device may be classified into light emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials, depending on their function. The light emitting materials include blue, green, and red light emitting materials, and yellow and orange light emitting materials necessary for realizing a better natural color depending on the light emitting color.

In addition, a host/dopant system may be used as a light emitting material in order to increase color purity and increase light emission efficiency through energy transfer. The principle is that when a small amount of a dopant having a smaller energy band gap and a higher luminous efficiency is mixed with a light emitting layer than a host mainly constituting the light emitting layer, excitons generated from the host are transported as a dopant to produce high efficiency light. At this time, since the wavelength of the host moves to the wavelength of the dopant, light of a desired wavelength can be obtained according to the type of the dopant used.

In order to sufficiently exhibit the excellent characteristics of the above-described organic light-emitting device, a material forming an organic material layer in the device, such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc., are supported by stable and efficient materials. Development of new materials continues to be required.

Chinese Patent Publication No. 106467553

In this specification, a compound and an organic light emitting device including the same are described.

One embodiment of the present specification provides a compound represented by the following Chemical Formula 1.

[Formula 1]

In Chemical Formula 1,

A1 is a substituted or unsubstituted aromatic hydrocarbon ring; Or a substituted or unsubstituted aromatic heterocycle,

W is O, S, Se, NRa, PRb, C=O, CRcRd, SiReRf or P(=O)Rg,

X1 is N or CR11, X2 is N or CR12, X3 is N or CR13,

However, when X2 is N, X3 is CR13, and when X3 is N, X2 is CR12,

Ra to Rg, R11 to R13, Ar1 and Ar2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Alkyl silyl groups; Arylsilyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted alkoxyaryl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or combine with adjacent groups to form a substituted or unsubstituted ring,

R1 and R2 are connected to the dotted line of Formula 2 to form a ring,

R3 and R12; Or R3 and R13 are connected to the dotted portion of the formula (2) to form a ring,

[Formula 2]

In Chemical Formula 2,

Y is O, S, Se, NR21, PR22, C=O, CR23R24, SiR25R26 or P(=O)R27,

R21 to R27 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or combine with adjacent groups to form a substituted or unsubstituted ring,

A2 is a substituted or unsubstituted aromatic hydrocarbon ring; Or a substituted or unsubstituted aromatic heterocycle.

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

The compound described herein can be used as a material for an organic material layer of an organic light emitting device as a polycyclic condensed ring compound containing boron (B). The compound according to at least one embodiment can improve the characteristics of the device, such as light emission efficiency, color purity, and lifespan characteristics, in an organic light emitting device, and obtain a device having a low driving voltage.

1 shows an example of an organic light emitting device including a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
FIG. 2 shows an example of an organic light emitting device comprising a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4 It is done.

Hereinafter, this specification will be described in more detail.

The present specification provides a compound represented by Formula 1 below. By including B in the compound represented by Formula 1, and connected to the dotted portion of Formula 2 to form a ring, The aryl group directly bonded to the triaryl borane was bonded using nitrogen or other form of atom (W) that does not extend the conjugation, thereby improving the warping characteristics due to steric hindrance of the aryl group. These molecules can significantly improve the lifespan in driving an organic light emitting device by increasing the stability of the molecule as compared to the light emitting material previously invented. In addition, increasing the stability of the molecule can improve the processability by increasing the deposition process speed.

In addition, the compound of the present invention can improve the life, color reproducibility, and charge balance characteristics of an existing organic light-emitting device and improve characteristics such as processability and material modification during panel production.

[Formula 1]

In Chemical Formula 1,

A1 is a substituted or unsubstituted aromatic hydrocarbon ring; Or a substituted or unsubstituted aromatic heterocycle,

W is O, S, Se, NRa, PRb, C=O, CRcRd, SiReRf or P(=O)Rg,

X1 is N or CR11, X2 is N or CR12, X3 is N or CR13,

However, when X2 is N, X3 is CR13, and when X3 is N, X2 is CR12,

Ra to Rg, R11 to R13, Ar1 and Ar2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Alkyl silyl groups; Arylsilyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted alkoxyaryl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or combine with adjacent groups to form a substituted or unsubstituted ring,

R1 and R2 are connected to the dotted line of Formula 2 to form a ring,

R3 and R12; Or R3 and R13 are connected to the dotted portion of the formula (2) to form a ring,

[Formula 2]

In Chemical Formula 2,

Y is O, S, Se, NR21, PR22, C=O, CR23R24, SiR25R26 or P(=O)R27,

R21 to R27 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or combine with adjacent groups to form a substituted or unsubstituted ring,

A2 is a substituted or unsubstituted aromatic hydrocarbon ring; Or a substituted or unsubstituted aromatic heterocycle.

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.

Examples of the substituent in this 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.

The term "substituted or unsubstituted" in this specification is deuterium; Halogen group; Hydroxy group; Cyano group (-CN); Nitro group; Silyl group; Boron group; Alkyl groups; Cycloalkyl group; Alkoxy groups; Alkenyl group; Alkynyl group; Aryloxy group; Aryl group; Amine group; And one or two or more substituents selected from the group consisting of heterocyclic groups, or substituted with two or more substituents of the above-exemplified substituents, or having no substituents. For example, "a substituent having two or more substituents" 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 connected.

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

In the present specification, examples of the halogen group include fluorine (F), chlorine (Cl), bromine (Br), or iodine (I).

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 60. According to an exemplary embodiment, the alkyl group has 1 to 30 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. Specific examples of the alkyl group are methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-ox Tilgi, and the like, but are not limited to these.

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. It is not.

In the present specification, the alkoxy group may be straight chain or branched chain. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 30 carbon atoms. 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, 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 the amine group are methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, and 9-methyl-anthracenylamine group , Diphenylamine 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-biphenylfluorenylamine 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-aryl heteroarylamine group means an amine group in which an aryl group and a heteroaryl group are substituted with N of the amine group.

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

In the present specification, examples of the alkylamine group include a substituted or unsubstituted monoalkylamine group, or a substituted or unsubstituted dialkylamine group. The alkyl group in the alkylamine group may be a linear or branched alkyl group. The alkylamine group including two or more alkyl groups may include a straight chain alkyl group, a branched chain alkyl group, or a straight chain alkyl group and a branched chain alkyl group at the same time. For example, the alkyl group in the alkylamine group can be selected from the examples of the alkyl groups described above.

In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms 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, and the like, but is not limited thereto.

In the present specification, the silyl group may be -SiR ₁₀₁ R ₁₀₂ R ₁₀₃ , wherein R ₁₀₁ to R ₁₀₃ are the same or different, and each independently hydrogen; heavy hydrogen; halogen; Cyano 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; A 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, the alkylsilyl group means a silyl group substituted with an alkyl group.

In the present specification, the arylsilyl group means a silyl group substituted with an aryl group.

Specifically, there are trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like, but is not limited thereto. .

In the present specification, the boron group may be -BR ₁₀₄ R ₁₀₅ , wherein R ₁₀₄ and R ₁₀₅ are the same or different, and each independently hydrogen; heavy hydrogen; halogen; Cyano 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; A 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, the aryl group is not particularly limited, but is preferably 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the carbon number of the aryl group is 6 to 30. According to one embodiment, the carbon number of the aryl group is 6 to 20. The aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., as a monocyclic aryl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, anthracenyl group, indenyl group, phenanthrenyl group, pyrenyl group, perylene group, triphenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.

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

,

등의 스피로플루오레닐기,

(9,9-디메틸플루오레닐기), 및

(9,9-디페닐플루오레닐기) 등의 치환된 플루오레닐기가 될 수 있다. 다만, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,

,

Spirofluorenyl groups, such as

(9,9-dimethylfluorenyl group), and

It may be a substituted fluorenyl group, such as (9,9-diphenylfluorenyl group). However, it is not limited thereto.

In the present specification, the heterocyclic group is a hetero atom and is a ring group containing one or more of N, O, P, S, Si, and Se, and carbon number is not particularly limited, but is preferably 2 to 60 carbon atoms. According to an exemplary embodiment, the heterocyclic group has 2 to 30 carbon atoms. Examples of the heterocyclic group include pyridyl group, pyrrol group, pyrimidyl group, pyridazinyl group, furanyl group, thiophenyl group, carbazole group, imidazole group, pyrazole group, dibenzofuranyl group, dibenzothiophenyl group, etc. However, it is not limited to these.

In the present specification, a description of the aforementioned heterocyclic group may be applied, except that the heteroaryl group is aromatic.

In this specification, "adjacent" A group may mean a substituent substituted on an atom directly connected to an atom in which the substituent is substituted, a substituent positioned closest in conformation to the substituent, or another substituent substituted on the atom in which the substituent is substituted. 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" to each other.

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

In the present specification, 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 non-monovalent.

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

In the present specification, the heterocycle is a non-carbon atom, and contains at least one heteroatom, specifically, the heteroatom contains at least one atom selected from the group consisting of N, O, P, S, Si and Se, etc. can do. The heterocycle may be monocyclic or polycyclic, and may be aromatic, aliphatic, or a condensed ring of aromatic and aliphatic, and the aromatic heterocycle may be selected from examples of the heteroaryl group except that it is not monovalent.

According to an exemplary embodiment of the present specification, X1 is N or CR11.

In one embodiment of the present specification, R11 is hydrogen; heavy hydrogen; Halogen group; An alkylsilyl group having 1 to 20 carbon atoms; 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 arylamine group having 12 to 60 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, or combine with adjacent groups to form a substituted or unsubstituted ring.

According to another exemplary embodiment, R11 is hydrogen; heavy hydrogen; Halogen group; Trialkylsilyl groups having 3 to 20 carbon atoms; A substituted or unsubstituted methyl group; A substituted or unsubstituted butyl group; A substituted or unsubstituted cyclohexyl group; A substituted or unsubstituted diphenylamine group; A substituted or unsubstituted phenyl group; Or a substituted or unsubstituted carbazole group, or combines with adjacent groups to form a substituted or unsubstituted ring.

In another exemplary embodiment, R11 is hydrogen; heavy hydrogen; Fluorine (-F); Trimethylsilyl group; Methyl group; tert-butyl group; Cyclohexyl group; Diphenylamine group; Phenyl group; Or a carbazole group, or combines with R21 to form a substituted or unsubstituted ring.

According to an exemplary embodiment of the present specification, X2 is N or CR12, X3 is N or CR13, X3 is CR13 when X2 is N, and X2 is CR12 when X3 is N.

According to an exemplary embodiment of the present specification, X2 is N or CR12, X3 is CR13.

According to another exemplary embodiment, X2 is CR12 and X3 is N or CR13.

According to an exemplary embodiment of the present specification, the R3 And R12; Or R3 and R13 are connected to the dotted portion of the formula (2) to form a ring.

In one embodiment of the present specification, when R12 is connected to the dotted portion of Formula 2 and does not form a ring, R12 is hydrogen; heavy hydrogen; Halogen group; An alkylsilyl group having 1 to 20 carbon atoms; 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 arylamine group having 12 to 60 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, or combine with adjacent groups to form a substituted or unsubstituted ring.

According to another exemplary embodiment, when R12 is connected to the dotted portion of Formula 2 and does not form a ring, R12 is hydrogen; heavy hydrogen; Halogen group; Trialkylsilyl groups having 3 to 20 carbon atoms; A substituted or unsubstituted methyl group; A substituted or unsubstituted butyl group; A substituted or unsubstituted cyclohexyl group; A substituted or unsubstituted diphenylamine group; A substituted or unsubstituted phenyl group; Or a substituted or unsubstituted carbazole group, or combines with adjacent groups to form a substituted or unsubstituted ring.

In another exemplary embodiment, when R12 is connected to the dotted portion of Formula 2 and does not form a ring, R12 is hydrogen; heavy hydrogen; Fluorine (-F); Trimethylsilyl group; Methyl group; tert-butyl group; Cyclohexyl group; Diphenylamine group; Phenyl group; Or a carbazole group, or combine with adjacent groups to form a substituted or unsubstituted ring.

In one embodiment of the present specification, when R13 is connected to the dotted portion of Formula 2 and does not form a ring, R13 is hydrogen; heavy hydrogen; Halogen group; An alkylsilyl group having 1 to 20 carbon atoms; 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 arylamine group having 12 to 60 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, or combine with adjacent groups to form a substituted or unsubstituted ring.

According to another exemplary embodiment, when R13 is connected to the dotted portion of Formula 2 and does not form a ring, R13 is hydrogen; heavy hydrogen; Halogen group; Trialkylsilyl groups having 3 to 20 carbon atoms; A substituted or unsubstituted methyl group; A substituted or unsubstituted butyl group; A substituted or unsubstituted cyclohexyl group; A substituted or unsubstituted diphenylamine group; A substituted or unsubstituted phenyl group; Or a substituted or unsubstituted carbazole group, or combines with adjacent groups to form a substituted or unsubstituted ring.

In another exemplary embodiment, when R13 is connected to the dotted portion of Formula 2 and does not form a ring, R13 is hydrogen; heavy hydrogen; Fluorine (-F); Trimethylsilyl group; Methyl group; tert-butyl group; Cyclohexyl group; Diphenylamine group; Phenyl group; Or a carbazole group, or combine with adjacent groups to form a substituted or unsubstituted ring.

According to another exemplary embodiment, when R13 is connected to the dotted portion of Formula 2 and does not form a ring, R13 is hydrogen.

According to an exemplary embodiment of the present specification, the R3 And R12; Or R3 and R13 are connected to the dotted portion of the formula (2) to form a ring.

In one embodiment of the present specification, Chemical Formula 1 may be represented by the following Chemical Formula 1-1 or Chemical Formula 1-2.

[Formula 1-1]

[Formula 1-2]

In Formula 1-1 and Formula 1-2,

W, X1, R1, R2, A1, Ar1 and Ar2 are the same as defined in Chemical Formula 1,

X21 and X31 are the same as or different from each other, and each independently N or CR41,

R41 is hydrogen; heavy hydrogen; Halogen group; Cyano group; Alkyl silyl groups; Arylsilyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted alkoxyaryl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or combine with adjacent groups to form a substituted or unsubstituted ring,

R3 and R4; And R3 and R5 are connected to the dotted portion of Formula 2 to form a ring.

In one embodiment of the present specification, R41 is hydrogen; heavy hydrogen; Halogen group; An alkylsilyl group having 1 to 20 carbon atoms; 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 arylamine group having 12 to 60 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, or combine with adjacent groups to form a substituted or unsubstituted ring.

According to another exemplary embodiment, R41 is hydrogen; heavy hydrogen; Halogen group; Trialkylsilyl groups having 3 to 20 carbon atoms; A substituted or unsubstituted methyl group; A substituted or unsubstituted butyl group; A substituted or unsubstituted cyclohexyl group; A substituted or unsubstituted diphenylamine group; A substituted or unsubstituted phenyl group; Or a substituted or unsubstituted carbazole group, or combines with adjacent groups to form a substituted or unsubstituted ring.

In another exemplary embodiment, R41 is hydrogen; heavy hydrogen; Fluorine (-F); Trimethylsilyl group; Methyl group; tert-butyl group; Cyclohexyl group; Diphenylamine group; Phenyl group; Or a carbazole group, or combine with adjacent groups to form a substituted or unsubstituted ring.

According to the exemplary embodiment of the present specification, Y is O, S, Se, NR21, PR22, C=O, CR23R24, SiR25R26, or P(=O)R27.

In one embodiment of the present specification, R21 is a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or combine with adjacent groups to form a substituted or unsubstituted ring,

According to another exemplary embodiment, R21 is a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or combine with adjacent groups to form a substituted or unsubstituted ring.

In another exemplary embodiment, R21 is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or combines with adjacent groups to form a substituted or unsubstituted ring.

According to another exemplary embodiment, R21 is a substituted or unsubstituted methyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted naphthyl group, or combines with adjacent groups to form a substituted or unsubstituted ring.

In another exemplary embodiment, R21 is a methyl group; Phenyl group; Biphenyl group; Or a naphthyl group, or combine with adjacent groups to form a substituted or unsubstituted ring.

In one embodiment of the present specification, R22 is a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.

According to another exemplary embodiment, R22 is a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

In another exemplary embodiment, R22 is a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

According to another exemplary embodiment, R22 is a substituted or unsubstituted methyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted naphthyl group.

In another exemplary embodiment, R22 is a methyl group; Phenyl group; Biphenyl group; Or a naphthyl group.

According to an exemplary embodiment of the present specification, R23 and R24 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or combine with each other to form a substituted or unsubstituted ring.

In another exemplary embodiment, R23 and R24 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or combine with each other to form a substituted or unsubstituted ring.

According to another exemplary embodiment, R23 and R24 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or combine with each other to form a substituted or unsubstituted hydrocarbon ring having 6 to 60 carbon atoms.

In another exemplary embodiment, R23 and R24 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted propyl group; A substituted or unsubstituted butyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted naphthyl group, or combine with each other to form a substituted or unsubstituted hydrocarbon ring having 6 to 30 carbon atoms.

According to another exemplary embodiment, R23 and R24 are the same as or different from each other, and each independently hydrogen; Methyl group; Ethyl group; Isopropyl group; tert-butyl group; Phenyl group; Biphenyl group; Or a naphthyl group, or combine with each other to form a fluorene ring.

According to one embodiment of the present specification, R25 to R27 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.

In another exemplary embodiment, R25 to R27 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

According to another exemplary embodiment, R25 to R27 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

In one embodiment of the present specification, A1 is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms; Or a substituted or unsubstituted aromatic heterocycle having 2 to 60 carbon atoms.

According to another exemplary embodiment, A1 is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms; Or a substituted or unsubstituted aromatic heterocycle having 2 to 30 carbon atoms.

In another exemplary embodiment, A1 is a substituted or unsubstituted benzene ring.

According to an exemplary embodiment of the present specification, A1 is 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 aryl group having 6 to 30 carbon atoms, It is an aromatic hydrocarbon ring having 6 to 30 carbon atoms substituted or unsubstituted with one or more substituents selected from the group consisting of substituted or unsubstituted amine groups and substituted or unsubstituted heterocyclic groups having 2 to 30 carbon atoms.

In another exemplary embodiment, A1 is a substituted or unsubstituted C 1 to C 20 alkyl group, a C 3 to C 30 cycloalkyl group, a C 1 to C 20 alkyl group substituted or unsubstituted C 6 to 30 carbon group. At least one selected from the group consisting of an aryl group of 1 to 20 carbon atoms or an arylamine group of 12 to 30 carbon atoms unsubstituted or substituted, and a heterocyclic group of 2 to 30 carbon atoms containing S, O or N as heterogeneous element It is an aromatic hydrocarbon ring having 6 to 30 carbon atoms unsubstituted or substituted with a substituent.

According to another exemplary embodiment, A1 is a diphenyl substituted or unsubstituted with a methyl group unsubstituted or substituted with deuterium, a tert-butyl group, a cyclohexyl group, a phenyl group unsubstituted or substituted with a methyl group, or a tert-butyl group. It is an aromatic hydrocarbon ring having 6 to 30 carbon atoms unsubstituted or substituted with one or more substituents selected from the group consisting of amine groups and carbazole groups.

According to another exemplary embodiment, A1 is a substituted or unsubstituted C 1 to C 20 alkyl group, a C 3 to C 30 cycloalkyl group, a C 1 to C 20 alkyl group substituted or unsubstituted C 6 to 30 carbon group. At least one selected from the group consisting of an aryl group of 1 to 20 carbon atoms or an arylamine group of 12 to 30 carbon atoms unsubstituted or substituted, and a heterocyclic group of 2 to 30 carbon atoms containing S, O or N as heterogeneous element It is a benzene ring unsubstituted or substituted with a substituent.

According to another exemplary embodiment, A1 is a diphenyl substituted or unsubstituted with a methyl group unsubstituted or substituted with deuterium, a tert-butyl group, a cyclohexyl group, a phenyl group unsubstituted or substituted with a methyl group, or a tert-butyl group. It is a benzene ring substituted or unsubstituted with one or more substituents selected from the group consisting of amine groups and carbazole groups.

In one embodiment of the present specification, A2 is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms; Or a substituted or unsubstituted aromatic heterocycle having 2 to 60 carbon atoms.

According to another exemplary embodiment, A2 is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms; Or a substituted or unsubstituted aromatic heterocycle having 2 to 30 carbon atoms.

In another exemplary embodiment, A2 is a substituted or unsubstituted alkylsilyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl An aromatic hydrocarbon ring having 6 to 30 carbon atoms unsubstituted or substituted with one or more substituents selected from the group consisting of groups and substituted or unsubstituted heterocyclic groups; Or a substituted or unsubstituted alkylsilyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group It is an aromatic heterocycle having 2 to 30 carbon atoms unsubstituted or substituted with one or more substituents selected from the group consisting of.

According to another exemplary embodiment, A2 is a trialkylsilyl group having 3 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms unsubstituted or substituted with deuterium, a cycloalkyl group having 3 to 30 carbon atoms, aryl having 12 to 30 carbon atoms Aromatic hydrocarbon having 6 to 30 carbon atoms unsubstituted or substituted with one or more substituents selected from the group consisting of an amine group, a halogen group or an aryl group having 6 to 30 carbon atoms unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms and a heterocyclic group ring; Or a trialkylsilyl group having 3 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms unsubstituted or substituted with deuterium, a cycloalkyl group having 3 to 30 carbon atoms, an arylamine group having 12 to 30 carbon atoms, a halogen group, or 1 to 20 carbon atoms. It is an aromatic heterocycle having 2 to 30 carbon atoms unsubstituted or substituted with one or more substituents selected from the group consisting of an aryl group having 6 to 30 carbon atoms unsubstituted or substituted with an alkyl group, and a heterocyclic group.

In another exemplary embodiment, A2 is a trialkylsilyl group having 3 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms unsubstituted or substituted with deuterium, a cycloalkyl group having 3 to 30 carbon atoms, aryl having 12 to 30 carbon atoms. A benzene ring substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl group having 6 to 30 carbon atoms unsubstituted or substituted with an amine group, a halogen group or an alkyl group having 1 to 20 carbon atoms, and a heterocyclic group; Trialkylsilyl group having 3 to 20 carbon atoms, alkyl group having 1 to 20 carbon atoms unsubstituted or substituted with deuterium, cycloalkyl group having 3 to 30 carbon atoms, arylamine group having 12 to 30 carbon atoms, halogen group or alkyl group having 1 to 20 carbon atoms A naphthalene ring unsubstituted or substituted with one or more substituents selected from the group consisting of an aryl group having 6 to 30 carbon atoms unsubstituted or substituted with a heterocyclic group; Or a trialkylsilyl group having 3 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms unsubstituted or substituted with deuterium, a cycloalkyl group having 3 to 30 carbon atoms, an arylamine group having 12 to 30 carbon atoms, a halogen group or 1 to 20 carbon atoms It is a dibenzofuran ring unsubstituted or substituted with one or more substituents selected from the group consisting of an aryl group having 6 to 30 carbon atoms unsubstituted or substituted with an alkyl group, and a heterocyclic group.

According to another exemplary embodiment, A2 is a trimethylsilyl group, a methyl group substituted with deuterium, a propyl group, a butyl group, a cyclohexyl group, a diphenylamine group, a phenyl group unsubstituted or substituted with a fluorine or butyl group, and a carba A benzene ring unsubstituted or substituted with one or more substituents selected from the group consisting of sol groups; Naphthalene ring; Or dibenzofuran ring.

According to one embodiment of the present specification, Chemical Formula 1 may be represented by any one of the following Chemical Formulas 2-1 to 2-7.

[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Formula 2-4]

[Formula 2-5]

[Formula 2-6]

[Formula 2-7]

In Chemical Formulas 2-1 to 2-7,

W, X1, X2, X3, A1, Ar1 and Ar2 are the same as defined in Chemical Formula 1,

Y1 to Y14 are the same as or different from each other, and each independently the same as the definition of Y in Formula 2,

A21 to A34 are the same as or different from each other, and each independently is the same as the definition of A2 in Formula 2 above.

According to the exemplary embodiment of the present specification, Y1 to Y14 are the same as or different from each other, and are each independently defined as for Y in Chemical Formula 2.

According to one embodiment of the present specification, Y1 to Y14 are the same as or different from each other, and each independently O, S, Se, NR21, PR22, C=O, CR23R24, SiR25R26, or P(=O)R27, and R21 To R27 are as defined above.

In one embodiment of the present specification, A21 to A34 are the same as or different from each other, and each independently substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms; Or a substituted or unsubstituted aromatic heterocycle having 2 to 60 carbon atoms.

According to another exemplary embodiment, A21 to A34 are the same as or different from each other, and each independently substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms; Or a substituted or unsubstituted aromatic heterocycle having 2 to 30 carbon atoms.

In another exemplary embodiment, A21 to A34 are the same as or different from each other, and each independently a substituted or unsubstituted alkylsilyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted An aromatic hydrocarbon ring having 6 to 30 carbon atoms unsubstituted or substituted with one or more substituents selected from the group consisting of a substituted amine group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group; Or a substituted or unsubstituted alkylsilyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted amine group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted heterocyclic group It is an aromatic heterocycle having 2 to 30 carbon atoms unsubstituted or substituted with one or more substituents selected from the group consisting of.

According to another exemplary embodiment, A21 to A34 are the same as or different from each other, and each independently a trialkylsilyl group having 3 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms unsubstituted or substituted with deuterium, 3 to carbon atoms Substituted with one or more substituents selected from the group consisting of a cycloalkyl group of 30, an arylamine group of 12 to 30 carbon atoms, a halogen group or an aryl group of 6 to 30 carbon atoms unsubstituted or substituted with an alkyl group of 1 to 20 carbon atoms, and a heterocyclic group Or an unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms; Or a trialkylsilyl group having 3 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms unsubstituted or substituted with deuterium, a cycloalkyl group having 3 to 30 carbon atoms, an arylamine group having 12 to 30 carbon atoms, a halogen group, or 1 to 20 carbon atoms. It is an aromatic heterocycle having 2 to 30 carbon atoms unsubstituted or substituted with one or more substituents selected from the group consisting of an aryl group having 6 to 30 carbon atoms unsubstituted or substituted with an alkyl group, and a heterocyclic group.

In another exemplary embodiment, A21 to A34 are the same as or different from each other, and each independently has a trialkylsilyl group having 3 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms unsubstituted or substituted with deuterium, and a carbon number of 3 to 20. Substituted with one or more substituents selected from the group consisting of a cycloalkyl group of 30, an arylamine group of 12 to 30 carbon atoms, a halogen group or an aryl group of 6 to 30 carbon atoms unsubstituted or substituted with an alkyl group of 1 to 20 carbon atoms, and a heterocyclic group Or an unsubstituted benzene ring; Trialkylsilyl group having 3 to 20 carbon atoms, alkyl group having 1 to 20 carbon atoms unsubstituted or substituted with deuterium, cycloalkyl group having 3 to 30 carbon atoms, arylamine group having 12 to 30 carbon atoms, halogen group or alkyl group having 1 to 20 carbon atoms A naphthalene ring unsubstituted or substituted with one or more substituents selected from the group consisting of an aryl group having 6 to 30 carbon atoms unsubstituted or substituted with a heterocyclic group; Or a trialkylsilyl group having 3 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms unsubstituted or substituted with deuterium, a cycloalkyl group having 3 to 30 carbon atoms, an arylamine group having 12 to 30 carbon atoms, a halogen group or 1 to 20 carbon atoms It is a dibenzofuran ring unsubstituted or substituted with one or more substituents selected from the group consisting of an aryl group having 6 to 30 carbon atoms unsubstituted or substituted with an alkyl group, and a heterocyclic group.

According to another exemplary embodiment, A21 to A34 are the same as or different from each other, and each independently a trimethylsilyl group, a methyl group substituted with deuterium, a propyl group, a butyl group, a cyclohexyl group, a diphenylamine group, fluorine, or A benzene ring substituted or unsubstituted with one or more substituents selected from the group consisting of a phenyl group unsubstituted or substituted with a butyl group, and a carbazole group; Naphthalene ring; Or dibenzofuran ring.

In one embodiment of the present specification, W is O, S, Se, NRa, PRb, C=O, CRcRd, SiReRf, or P(=O)Rg.

According to an exemplary embodiment of the present specification, the Ra to Rg are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or combine with adjacent groups to form a substituted or unsubstituted ring.

In one embodiment of the present specification, Ra is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

According to another exemplary embodiment, Ra is a C 6 to C 60 aryl group substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, a halogen group, and an alkyl group having 1 to 20 carbon atoms.

According to another exemplary embodiment, Ra is a phenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, halogen groups, and alkyl groups having 1 to 20 carbon atoms; A naphthyl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, halogen groups, and alkyl groups having 1 to 20 carbon atoms; Or a biphenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, halogen groups, and alkyl groups having 1 to 20 carbon atoms.

In another exemplary embodiment, Ra is an aryl group having 6 to 60 carbon atoms unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, fluorine (-F), and butyl groups.

According to another exemplary embodiment, Ra is a phenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, fluorine (-F), and butyl groups; A naphthyl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, fluorine (-F) and butyl groups; Or a biphenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, fluorine (-F) and butyl groups.

According to an exemplary embodiment of the present specification, Rb is an aryl group having 6 to 30 carbon atoms.

According to another exemplary embodiment, Rb is a substituted or unsubstituted phenyl group.

According to another exemplary embodiment, Rb is a phenyl group.

According to an exemplary embodiment of the present specification, the Rc and Rd are the same as or different from each other, and each independently substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or combine with each other to form a substituted or unsubstituted hydrocarbon ring having 6 to 30 carbon atoms.

In another exemplary embodiment, Rc and Rd 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 30 carbon atoms unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms, or bonded to each other to form a substituted or unsubstituted hydrocarbon ring having 6 to 30 carbon atoms.

According to another exemplary embodiment, Rc and Rd are the same as or different from each other, and each independently a substituted or unsubstituted methyl group; Or a substituted or unsubstituted phenyl group, or combine with each other to form a substituted or unsubstituted hydrocarbon ring having 6 to 30 carbon atoms.

In another exemplary embodiment, Rc and Rd are the same as or different from each other, and each independently a methyl group; Or a phenyl group unsubstituted or substituted with a methyl group, or combine with each other to form a fluorene ring.

According to an exemplary embodiment of the present specification, Re to Rg are the same as or different from each other, and each independently substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or combine with each other to form a substituted or unsubstituted hydrocarbon ring having 6 to 30 carbon atoms.

In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, or combine with adjacent groups to form a substituted or unsubstituted ring.

In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently an aryl group having 6 to 60 carbon atoms unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms.

According to another exemplary embodiment, Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms; A biphenyl group unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms; Or a naphthyl group unsubstituted or substituted with an alkyl group having 1 to 20 carbon atoms.

According to another exemplary embodiment, Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a methyl group or a butyl group; Biphenyl group; Or a naphthyl group.

In one embodiment of the present specification, Chemical Formula 1 may be represented by any one of the following structures.

The compound of Formula 1 according to an exemplary embodiment of the present specification may be prepared by a manufacturing method described later.

For example, the compound of Formula 1 may have a core structure as in a manufacturing method described later. Substituents can be combined by methods known in the art, and the type, location, or number of substituents can be varied according to techniques known in the art.

In addition, by introducing various substituents to the core structure of the structure as described above, it is possible to synthesize a compound having intrinsic properties of the introduced substituents. For example, by introducing a substituent mainly used for a hole injection layer material, a hole transport material, a light emitting layer material, and an electron transport layer material used in manufacturing an organic light emitting device into the core structure, a material satisfying the conditions required for each organic material layer can be synthesized. Can.

In addition, the organic light emitting device according to the present invention includes a first electrode; A second electrode provided to face 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 comprises the compound of Formula 1.

According to an exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, at least one layer of the organic material layer includes the above-described compound, the light emitting layer may include a compound represented by the following formula 1A.

[Formula 1A]

In Formula 1A,

L103 to L106 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

Ar5 to Ar8 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

R101 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

p is an integer from 0 to 6,

When p is 2 or more, the substituents in parentheses are the same as or different from each other.

In one embodiment of the present specification, L103 to L106 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms.

In one embodiment of the present specification, L103 to L106 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 40 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 40 carbon atoms.

According to another exemplary embodiment, the L103 to L106 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylylene group; A substituted or unsubstituted terphenylene group; A substituted or unsubstituted naphthylene group; A substituted or unsubstituted anthracenyl group; A substituted or unsubstituted phenanthrenylene group; A substituted or unsubstituted triphenylene group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted thiophenylene group; A substituted or unsubstituted furanylene group; A substituted or unsubstituted dibenzothiophenylene group; A substituted or unsubstituted dibenzofuranylene group; Or a substituted or unsubstituted carbazolylene group.

In another exemplary embodiment, the L103 to L106 are the same as or different from each other, and each independently a direct bond; Phenylene group; Biphenylylene group; Terphenylene group; Naphthylene group; Anthracenyl group; Phenanthrenylene group; Triphenylene group; A fluorenyl group unsubstituted or substituted with a methyl group or a phenyl group; Thiophenylene group; Furanylene group; Dibenzothiophenylene group; Dibenzofuranylene group; Or a carbazolylene group unsubstituted or substituted with an ethyl group or a phenyl group.

According to another exemplary embodiment, the L103 to L106 are the same as or different from each other, and each independently a direct bond; Or it may be selected from the following structures.

According to an exemplary embodiment of the present specification, L103 is a direct bond.

According to an exemplary embodiment of the present specification, L104 is a phenylene group.

According to an exemplary embodiment of the present specification, L105 and L106 are a direct bond.

In one embodiment of the present specification, R101 is hydrogen; heavy hydrogen; Halogen group; Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted aryl heteroarylamine group; Or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, R101 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, R101 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 40 carbon atoms.

In one embodiment of the present specification, R101 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 25 carbon atoms.

In another exemplary embodiment, R101 is hydrogen.

According to an exemplary embodiment of the present specification, the p is 0 or 1.

In one embodiment of the present specification, Ar5 to Ar8 are the same as or different from each other, and each independently substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

According to another exemplary embodiment, Ar5 to Ar8 are the same as or different from each other, and each independently hydrogen; An aryl group having 6 to 60 carbon atoms unsubstituted or substituted with an aryl group having 6 to 60 carbon atoms or a heteroaryl group having 2 to 60 carbon atoms; Or a C2-C60 heteroaryl group substituted or unsubstituted with a C2-C60 aryl group or a C2-C60 heteroaryl group.

In another exemplary embodiment, Ar5 to Ar8 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted phenanthrene group; A substituted or unsubstituted anthracene group; A substituted or unsubstituted triphenylene group; A substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted naphthobenzofuran group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted fluorene group; A substituted or unsubstituted thiophene group; A substituted or unsubstituted furan group; A substituted or unsubstituted benzothiophene group; A substituted or unsubstituted benzofuran group; A substituted or unsubstituted benzocarbazole group; A substituted or unsubstituted benzofluorene group; A substituted or unsubstituted indolcarbazole group; A substituted or unsubstituted pyridyl group; A substituted or unsubstituted isoquinolyl group; A substituted or unsubstituted quinolyl group; A substituted or unsubstituted quinazolyl group; A substituted or unsubstituted triazine group; A substituted or unsubstituted benzimidazole group; A substituted or unsubstituted benzoxazole group; A substituted or unsubstituted benzothiazole group; A substituted or unsubstituted dihydroacridine group; A substituted or unsubstituted xanthene group; Or a substituted or unsubstituted dibenzosilol group.

According to another exemplary embodiment, Ar5 to Ar8 are the same as or different from each other, and each independently hydrogen; Phenyl group; Biphenyl group; A naphthyl group unsubstituted or substituted with an aryl group; Phenanthrene group; Anthracene group; Triphenylene group; A dibenzofuran group unsubstituted or substituted with an aryl group; Naphthobenzofuran group; A dibenzothiophene group unsubstituted or substituted with an aryl group; A carbazole group unsubstituted or substituted with an alkyl group or an aryl group; A fluorene group unsubstituted or substituted with an alkyl group or an aryl group; Thiophene group unsubstituted or substituted with an aryl group; A furan group unsubstituted or substituted with an aryl group; Benzothiophene group; Benzofuran group; A benzocarbazole group unsubstituted or substituted with an alkyl group or an aryl group; A benzofluorene group unsubstituted or substituted with an alkyl group or an aryl group; Indole carbazole; Pyridyl group; An isoquinolyl group unsubstituted or substituted with an aryl group; Quinolyl group; A quinazolyl group unsubstituted or substituted with an aryl group; A triazine group unsubstituted or substituted with an aryl group; A benzimidazole group unsubstituted or substituted with an aryl group; A benzoxazole group unsubstituted or substituted with an aryl group; A benzothiazole group unsubstituted or substituted with an aryl group; A dihydroacridine group unsubstituted or substituted with an alkyl group or an aryl group; Xanthene group unsubstituted or substituted with an alkyl group or an aryl group; Or a dibenzosilol group unsubstituted or substituted with an alkyl group or an aryl group.

In another exemplary embodiment, Ar5 to Ar8 are the same as or different from each other, and each independently hydrogen; Phenyl group; Biphenyl group; A naphthyl group unsubstituted or substituted with a phenyl group; Phenanthrene group; Anthracene group; Triphenylene group; A dibenzofuran group unsubstituted or substituted with a phenyl group; Naphthobenzofuran group; A dibenzothiophene group unsubstituted or substituted with a phenyl group; A carbazole group unsubstituted or substituted with a methyl group, an ethyl group, or a phenyl group; A fluorene group unsubstituted or substituted with a methyl group or a phenyl group; Thiophene group unsubstituted or substituted with a phenyl group; A furan group unsubstituted or substituted with a phenyl group; Benzothiophene group; Benzofuran group; A benzocarbazole group unsubstituted or substituted with a methyl group or a phenyl group; A benzofluorene group unsubstituted or substituted with a methyl group or a phenyl group; Indole carbazole; A pyridyl group unsubstituted or substituted with a phenyl group or a naphthyl group; An isoquinolyl group unsubstituted or substituted with a phenyl group; Quinolyl group; A quinazolyl group unsubstituted or substituted with a phenyl group; A triazine group unsubstituted or substituted with a phenyl group; A benzimidazole group unsubstituted or substituted with a phenyl group; A benzoxazole group unsubstituted or substituted with a phenyl group; A benzothiazole group unsubstituted or substituted with a phenyl group; A dihydroacridine group unsubstituted or substituted with a methyl group or a phenyl group; A xanthene group unsubstituted or substituted with a methyl group or a phenyl group; Or a dibenzosilol group unsubstituted or substituted with a methyl group or a phenyl group.

In one embodiment of the present specification, Ar5 to Ar8 are the same as or different from each other, and each independently hydrogen; Or it may be selected from the following structures.

According to an exemplary embodiment of the present specification, the organic material layer includes a light emitting layer, at least one layer of the organic material layer includes the above-described compound, the light emitting layer may include a compound represented by the formula (1B).

Among the organic material layers of the organic light emitting device of the present specification, a structure of Formula 1B may be included as a material for a host of the light emitting layer.

[Formula 1B]

In Formula 1B,

L107 to L109 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,

Ar9 to Ar11 are the same as or different from each other, and each independently hydrogen; Or a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

R102 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

q is an integer from 0 to 7,

When q is 2 or more, the substituents in parentheses are the same or different from each other.

In one embodiment of the present specification, R102 is hydrogen; heavy hydrogen; Halogen group; Silyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted aryl heteroarylamine group; Or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, R102 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.

In one embodiment of the present specification, R102 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 40 carbon atoms.

In one embodiment of the present specification, R102 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 25 carbon atoms.

In another exemplary embodiment, R102 is hydrogen.

According to an exemplary embodiment of the present specification, q is 0 or 1.

In one embodiment of the present specification, L107 to L109 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms.

In one embodiment of the present specification, L107 to L109 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 40 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 40 carbon atoms.

According to another exemplary embodiment, L107 to L109 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylylene group; A substituted or unsubstituted terphenylene group; A substituted or unsubstituted naphthylene group; A substituted or unsubstituted anthracenyl group; A substituted or unsubstituted phenanthrenylene group; A substituted or unsubstituted triphenylene group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted thiophenylene group; A substituted or unsubstituted furanylene group; A substituted or unsubstituted dibenzothiophenylene group; A substituted or unsubstituted dibenzofuranylene group; Or a substituted or unsubstituted carbazolylene group.

In another exemplary embodiment, L107 to L109 are the same as or different from each other, and each independently a direct bond; Phenylene group; Biphenylylene group; Terphenylene group; Naphthylene group; Anthracenyl group; Phenanthrenylene group; Triphenylene group; A fluorenyl group unsubstituted or substituted with a methyl group or a phenyl group; Thiophenylene group; Furanylene group; Dibenzothiophenylene group; Dibenzofuranylene group; Or a carbazolylene group unsubstituted or substituted with an ethyl group or a phenyl group.

According to another exemplary embodiment, L107 to L109 are the same as or different from each other, and each independently a direct bond; Or it may be selected from the following structures.

In one embodiment of the present specification, L107 to L109 are a direct bond.

In one embodiment of the present specification, Ar9 to Ar11 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

According to another exemplary embodiment, Ar9 to Ar11 are the same as or different from each other, and each independently hydrogen; An aryl group having 6 to 60 carbon atoms unsubstituted or substituted with an aryl group having 6 to 60 carbon atoms or a heteroaryl group having 2 to 60 carbon atoms; Or a C2-C60 heteroaryl group substituted or unsubstituted with a C2-C60 aryl group or a C2-C60 heteroaryl group.

In another exemplary embodiment, Ar9 to Ar11 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted phenanthrene group; A substituted or unsubstituted anthracene group; A substituted or unsubstituted triphenylene group; A substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted naphthobenzofuran group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted fluorene group; A substituted or unsubstituted thiophene group; A substituted or unsubstituted furan group; A substituted or unsubstituted benzothiophene group; A substituted or unsubstituted benzofuran group; A substituted or unsubstituted benzocarbazole group; A substituted or unsubstituted benzofluorene group; A substituted or unsubstituted indolcarbazole group; A substituted or unsubstituted pyridyl group; A substituted or unsubstituted isoquinolyl group; A substituted or unsubstituted quinolyl group; A substituted or unsubstituted quinazolyl group; A substituted or unsubstituted triazine group; A substituted or unsubstituted benzimidazole group; A substituted or unsubstituted benzoxazole group; A substituted or unsubstituted benzothiazole group; A substituted or unsubstituted dihydroacridine group; A substituted or unsubstituted xanthene group; Or a substituted or unsubstituted dibenzosilol group.

According to another exemplary embodiment, Ar9 to Ar11 are the same as or different from each other, and each independently hydrogen; Phenyl group; Biphenyl group; A naphthyl group unsubstituted or substituted with an aryl group; Phenanthrene group; Anthracene group; Triphenylene group; A dibenzofuran group unsubstituted or substituted with an aryl group; Naphthobenzofuran group; A dibenzothiophene group unsubstituted or substituted with an aryl group; A carbazole group unsubstituted or substituted with an alkyl group or an aryl group; A fluorene group unsubstituted or substituted with an alkyl group or an aryl group; Thiophene group unsubstituted or substituted with an aryl group; A furan group unsubstituted or substituted with an aryl group; Benzothiophene group; Benzofuran group; A benzocarbazole group unsubstituted or substituted with an alkyl group or an aryl group; A benzofluorene group unsubstituted or substituted with an alkyl group or an aryl group; Indole carbazole; Pyridyl group; An isoquinolyl group unsubstituted or substituted with an aryl group; Quinolyl group; A quinazolyl group unsubstituted or substituted with an aryl group; A triazine group unsubstituted or substituted with an aryl group; A benzimidazole group unsubstituted or substituted with an aryl group; A benzoxazole group unsubstituted or substituted with an aryl group; A benzothiazole group unsubstituted or substituted with an aryl group; A dihydroacridine group unsubstituted or substituted with an alkyl group or an aryl group; Xanthene group unsubstituted or substituted with an alkyl group or an aryl group; Or a dibenzosilol group unsubstituted or substituted with an alkyl group or an aryl group.

In another exemplary embodiment, Ar9 to Ar11 are the same as or different from each other, and each independently hydrogen; Phenyl group; Biphenyl group; A naphthyl group unsubstituted or substituted with a phenyl group; Phenanthrene group; Anthracene group; Triphenylene group; A dibenzofuran group unsubstituted or substituted with a phenyl group; Naphthobenzofuran group; A dibenzothiophene group unsubstituted or substituted with a phenyl group; A carbazole group unsubstituted or substituted with a methyl group, an ethyl group, or a phenyl group; A fluorene group unsubstituted or substituted with a methyl group or a phenyl group; Thiophene group unsubstituted or substituted with a phenyl group; A furan group unsubstituted or substituted with a phenyl group; Benzothiophene group; Benzofuran group; A benzocarbazole group unsubstituted or substituted with a methyl group or a phenyl group; A benzofluorene group unsubstituted or substituted with a methyl group or a phenyl group; Indole carbazole; A pyridyl group unsubstituted or substituted with a phenyl group or a naphthyl group; An isoquinolyl group unsubstituted or substituted with a phenyl group; Quinolyl group; A quinazolyl group unsubstituted or substituted with a phenyl group; A triazine group unsubstituted or substituted with a phenyl group; A benzimidazole group unsubstituted or substituted with a phenyl group; A benzoxazole group unsubstituted or substituted with a phenyl group; A benzothiazole group unsubstituted or substituted with a phenyl group; A dihydroacridine group unsubstituted or substituted with a methyl group or a phenyl group; A xanthene group unsubstituted or substituted with a methyl group or a phenyl group; Or a dibenzosilol group unsubstituted or substituted with a methyl group or a phenyl group.

In one embodiment of the present specification, Ar9 to Ar11 are the same as or different from each other, and each independently hydrogen; Or it may be selected from the following structures.

The organic light-emitting device of the present invention can be manufactured by a conventional method and material for manufacturing an organic light-emitting device, except that one or more organic material layers are formed using the compound represented by Chemical Formula 1 above.

The compound may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device. Here, the solution application method means spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited to these.

The organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, etc. as an organic material layer. However, the structure of the organic light emitting device is not limited to this, and may include fewer organic material layers.

In the organic light emitting device of the present invention, the organic material layer may include an electron transport layer or an electron injection layer, and the electron transport layer or electron injection layer may include a compound represented by Chemical Formula 1.

In the organic light emitting device of the present invention, the organic material layer may include a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer may include a compound represented by Chemical Formula 1.

In another exemplary embodiment, the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula 1.

According to another exemplary embodiment, the organic material layer includes a light emitting layer, and the light emitting layer may include a compound represented by Chemical Formula 1 as a dopant in the light emitting layer.

In another exemplary embodiment, the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by Formula 1 as a dopant in the light emitting layer, and includes a fluorescent host or a phosphorescent host, and other organic compounds, metals or metal compounds It may include as a dopant.

As another example, the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by Formula 1 as a dopant in the light emitting layer, a fluorescent host or a phosphorescent host, and can be used with an iridium-based (Ir) dopant. have.

In one embodiment of the present specification, the organic light emitting device is a green organic light emitting device in which the light emitting layer includes a compound represented by Formula 1 as a dopant.

According to the exemplary embodiment of the present specification, the organic light emitting device is a red organic light emitting device in which the light emitting layer includes the compound represented by Chemical Formula 1 as a dopant.

In another exemplary embodiment, the organic light emitting device is a blue organic light emitting device in which the light emitting layer includes a compound represented by Chemical Formula 1 as a dopant.

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

As another example, the organic material layer may include a light emitting layer, and the light emitting layer may include a compound represented by Chemical Formula 1 as a host of the light emitting layer, and a dopant.

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

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

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

1 illustrates the structure of an organic light emitting device in which an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked on a substrate 1. In such a structure, the compound may be included in the light emitting layer 3.

2 shows an organic light emitting device in which an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8, and a cathode 4 are sequentially stacked on a substrate 1 The structure is illustrated. In such a structure, the compound may be included in the hole injection layer 5, the hole transport layer 6, the light emitting layer 7 or the electron transport layer 8.

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 It can be prepared by depositing an anode to form an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon. In addition to this method, an organic light emitting device may be made by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.

The organic material layer may have a multi-layer structure including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer, but is not limited thereto, and may have a single layer structure. In addition, the organic material layer has a smaller number of solvent processes, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer, using a variety of polymer materials. Can be prepared in layers.

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, gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); A combination of metal and oxide such as ZnO: Al or SnO ₂ : Sb; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole and polyaniline, but are not limited thereto.

The cathode material is preferably a material having a small work function to facilitate electron injection into an 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.

The hole-injecting material is a material that can be easily injected holes from the anode at a low voltage, and it is preferable that the high-occupied molecular orbital (HOMO) of the hole-injecting material is between the work function of the anode 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 materials, anthraquinones, and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.

As the hole transport material, a material capable of receiving holes from the anode or the hole injection layer and transporting them to the light emitting layer is suitable for 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.

The light emitting layer may emit red, green, or blue light, and may be made of a phosphorescent material or a fluorescent material. As the light-emitting material, a material capable of emitting light in the visible 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)-based polymers; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited to these.

The host material of the light emitting layer includes a condensed aromatic ring derivative or a heterocyclic compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic 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, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, the aromatic amine derivative 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 the 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, metal complexes include, but are not limited to, iridium complexes, platinum complexes, and the like.

As the electron transport material, a material capable of receiving electrons from the cathode well and transferring them to the light emitting layer, a material having high mobility for electrons is suitable. Specific examples include the Al complex of 8-hydroxyquinoline; Complexes including Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto.

The electron injection material has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect for the light emitting layer or the light emitting material, prevents movement of excitons generated in the light emitting layer to the hole injection layer, Also, a compound having 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 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 complex, and the like, but are not limited thereto.

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

< Synthetic example >

Synthetic example One.

Synthetic example 1. <Intermediate 1- 1> of synthesis

Intermediate 1-1 was synthesized according to Scheme 1 below.

[Scheme 1]

1-chloro-3-fluorodibenzo[b,d]furan[1-chloro-3-fluorodibenzo[b,d]furan] (25.0g, 0.113mol) and aniline (11.6g, 0.125mol) under nitrogen atmosphere, Bis(tri-tert-butylphosphine)palladium(0) [Bis(tri-tert-butylphosphine)palladium(0)] (1.2g, 2.27mmol ), NaOtBu (27.g, 0.283mol) and xylene 200mL The flask was heated and stirred for 12 hours. After the reaction solution was cooled to room temperature, water and dichloromethane were added, followed by extraction and washing. The organic layer was recovered and the extraction solvent was removed, followed by silica gel column chromatography (developer: dichloromethane / normal hexane = 1/1 (volume ratio)) to purify the white intermediate 1-1 in 18.0 g, 55% yield ( HPLC (High-performance liquid chromatography) 99% purity). MS:[M+H] ⁺ = 278

Synthetic example 2. <Intermediate 1- 2> of synthesis

Intermediate 1-2 was synthesized according to Scheme 2 below.

[Scheme 2]

In Synthesis Example 1, 1-chloro-3-fluorodibenzo[b,d]furan [1-chloro-3-fluorodibenzo[b,d]furan] is replaced with 1-chloro-3-methoxydibenzo[b,d]. Synthesis was carried out in almost the same way except for the change to furan [1-chloro-3-methoxydibenzo[b,d]furan] to obtain white powdery intermediate 1-2 in 22.5 g, 67% yield. MS:[M+H] ⁺ =290

Synthetic example 3. <Intermediate 2> of synthesis

Intermediate 2 was synthesized according to Scheme 3 below.

[Scheme 3]

Intermediate 1-1 (18.0g, 0.065mol), sodium tert-butoxide (15.0g, 0.162mol), dichlorobis[di-tert-butyl(p-dimethylaminophenyl)phosphine under nitrogen atmosphere Pino]palladium(II) {dichlorobis[di-tert-butyl(p-dimethylaminophenyl)phosphino]palladium(II)} (1.38g, 1.95mmol) and 1-bromo-2,3-dichlorobenzene [1-bromo- 2,3-dichlorobenzene] (14.7 g, 0.065 mol) was dissolved in 150 ml of o-xylene and refluxed for 6 hours. After the reaction mixture was cooled, ethyl acetate and distilled water were added to separate the layers, and then the organic layer was recovered. Thereafter, the organic layer was washed twice with distilled water, and then the solvent was removed to obtain a brown solid. Using column chromatography (developer: ethyl acetate/normal hexane = 1/5 (volume ratio)), intermediate 2 in the form of pure powder was obtained in a yield of 14 g, 51%. MS:[M+H] ⁺ = 422

Synthetic example 4. <Intermediate 3> of synthesis

Intermediate 3 was synthesized according to Scheme 4 below.

[Scheme 4]

Under nitrogen atmosphere, intermediate 2 (21.0 g, 0.050 mol), intermediate 1-2 (15.8 g, 0.055 mol), sodium tert-butoxide (12.0 g, 0.124 mol), and dichlorobis [di- tert-butyl(p-dimethylaminophenyl)phosphino]palladium(II) {dichlorobis[di-tert-butyl(p-dimethylaminophenyl)phosphino]palladium(II)} (1.06g, 1.49mmol) in o-xylene 100mL After melting, the mixture was refluxed and stirred for 12 hours. After cooling the reaction mixture, ethyl acetate and distilled water were added to separate the layers, and then the organic layer was recovered. Thereafter, the organic layer was washed twice with distilled water, and then the solvent was removed to obtain a brown solid. Using column chromatography (developer: ethyl acetate/normal hexane = 1/3 (volume ratio)), intermediate 3 in the form of pure powder was obtained with a yield of 61%. MS:[M+H] ⁺ = 675

Synthetic example 5. <Intermediate 4> of synthesis

Intermediate 4 was synthesized according to Scheme 5 below.

[Scheme 5]

Under an argon atmosphere, tert-butyl lithium pentane solution (2.0 eq) was slowly injected into a solution in which intermediate 3 (1.0 eq) was dissolved in tert-butylbenzene. At this time, the temperature was maintained at -10°C. Thereafter, the temperature was raised to 60°C, stirred for 2 hours, cooled to -50°C, and boron tribromide (2.0 eq.) was slowly added. After the addition was completed, the temperature was gradually increased to room temperature, and then again to 0°C. Cool down and add N,N-diisopropylethylamine (2.0 eq). Thereafter, a distillation tube and a cooling tube were installed to raise the temperature while removing the low-boiling point solvent while raising the temperature, raised to 120°C, and stirred for 3 hours. After completion of the reaction, the reaction solution was cooled to room temperature, and stirred by adding a cold aqueous sodium acetate solution. After adding ethyl acetate to the reaction mixture, the organic layer was separated to remove the solvent, and purified by recrystallization using toluene/normal hexane. After drying, Intermediate 4 was obtained in 27% yield. MS:[M+H] ⁺ = 635

Synthetic example 6. <Compound 1> of synthesis

Compound 1 was synthesized according to Scheme 6 below.

[Scheme 6]

Intermediate 4 (1.0 eq.) was dissolved in dimethylformamide [DMF] and 2,6-di-tert-butylpyridine [2,6-Di-tert-butylpyridine] (1.3 eq.) was added and stirred with heating at 100°C for 12 hours. Did. The reaction was added to an aqueous hydrochloric acid solution at a concentration of 1 mol, and then the precipitate was filtered. The filtrate was again purified by recrystallization (toluene) to obtain pure compound 1 in a yield of 89%. MS:[M+H] ⁺ = 615

Synthetic example 7. <Intermediate 6> of synthesis

Under nitrogen atmosphere, intermediate 5 (13.2 g, 0.055 mol), intermediate 1-2 (15.8 g, 0.055 mol), sodium tert-butoxide (10.6 g, 0.11 mol) and bis(tri-tert-) Butylphosphine)palladium(0) [Bis(tri-tert-butylphosphine)palladium(0)] (0.28 g, 0.55 mmol) was dissolved in 200 mL of toluene and refluxed and stirred for 12 hours. After the reaction mixture was cooled, ethyl acetate and distilled water were added to separate the layers, and then the organic layer was recovered. After washing the organic layer twice with distilled water, the solvent was removed and recrystallization was performed using chloroform and hexane. Intermediate 6, in pure powder form, was obtained with a yield of 76%. MS:[M+H] ⁺ = 448

Synthetic example 8. <Intermediate 7> of synthesis

Under nitrogen atmosphere, intermediate 6 (23.8 g, 0.053 mol), intermediate 1-1 (17.5 g, 0.063 mol), sodium tert-butoxide (10.6 g, 0.11 mol) and bis(tri-tert-) After dissolving butylphosphine)palladium(0) [Bis(tri-tert-butylphosphine)palladium(0)] (0.27g, 0.53mmol) in 200mL of o-xylene [o-xylene], the mixture was refluxed and stirred for 12 hours. After cooling the reaction mixture, ethyl acetate and distilled water were added to separate the layers, and then the organic layer was recovered. After washing the organic layer twice with distilled water, the solvent was removed and recrystallization was performed using chloroform and hexane. Intermediate 7 in pure powder form was obtained with a yield of 68%. MS:[M+H] ⁺ = 689

Synthetic example 9. <Intermediate 8> of synthesis

Intermediate 8 was obtained in the same manner as in Synthesis Example 5 in 21% yield. MS:[M+H] ⁺ = 649

Synthetic example 10. <Compound 2> of synthesis

Compound 2 was obtained in the same manner as in Synthesis Example 6 in 63% yield. MS: [M+H] ⁺ = 629

Synthetic example 11. <Intermediate 9> of synthesis

Compound 2 (5 g, 8 mmol) was dissolved in tetrahydrofuran (THF) 140 mL under a nitrogen atmosphere, and then cooled to 0°C. After dissolving N-bromosuccinimide [N-bromosuccinimide] (2.8 g, 16 mmol) in 20 mL of N,N-dimethylformamide [N,N-dimethylformamide], it was dissolved in a reaction solution containing compound 2 for 30 minutes at 0°C. Dropwise slowly. Thereafter, the mixture was stirred at room temperature for 1 hour, and a saturated solution of sodium thiosulfate was added, followed by layer separation to recover the organic layer. Thereafter, the organic layer was washed twice with a brine solution, and then the solvent was removed, followed by recrystallization using hexane. Intermediate 9, in pure powder form, was obtained with a yield of 81%. MS:[M+H] ⁺ = 785

Synthetic example 12. <Compound 3> of synthesis

Intermediate 9 (4.8g, 6.1mmol), phenylboronic acid (1.6g, 13.4mmol), potassium phosphate tribasic (3.9g, 18.3mmol) and bis(tri-tert-) under nitrogen atmosphere 6 hours after dissolving butylphosphine)palladium(0) [Bis(tri-tert-butylphosphine)palladium(0)] (30mg, 0.06mmol) in 30mL of 1,4-dioxane [1,4-dioxane]/distilled water 10mL It was refluxed and stirred. After cooling the reaction mixture, ammonium chloride and distilled water were added to separate the layers, and then the organic layer was recovered. After washing the organic layer twice with distilled water, the solvent was removed, and then recrystallized using toluene and hexane. Compound 3, in pure powder form, was obtained with a yield of 74%. MS:[M+H] ⁺ = 781

Synthetic example 13. <Intermediate 12> synthesis

Under nitrogen atmosphere, intermediate 11 (18 g, 0.052 mol), intermediate 10 (34.6 g, 0.109 mol), sodium tert-butoxide (22.5 g, 0.234 mol) and bis(tri-tert-butylphosphine) ) Palladium(0) [Bis(tri-tert-butylphosphine)palladium(0)](0.27g, 0.52mmol) was dissolved in 200mL of o-xylene [o-xylene] and refluxed and stirred for 12 hours. After the reaction mixture was cooled, ethyl acetate and a saturated aqueous solution of ammonium chloride were added to separate the layers, and then the organic layer was recovered. After washing the organic layer twice with distilled water, the solvent was removed and recrystallization was performed using chloroform and hexane. Intermediate 12 in pure powder form was obtained with a yield of 64%. MS:[M+H] ⁺ = 819

Synthetic example 14. <Intermediate 13> synthesis

In the same manner as in Synthesis Example 5, Intermediate 13 was obtained in 23% yield. MS:[M+H] ⁺ = 765

Synthetic example 15. <Compound 4> of synthesis

Dissolve intermediate 13 (5.5g, 7.2mmol) and p-toluenesulfonic acid monohydrate (2.74g, 14.4mmol) in 50mL o-xylene [o-xylene] under nitrogen atmosphere, then Dean-Stark (Dean-Stark) The mixture was refluxed and stirred for 24 hours using choja. After cooling to room temperature, a large amount of toluene and a saturated aqueous solution of sodium hydrogen carbonate were added to separate the layers, and then the organic layer was recovered. After washing the organic layer twice with distilled water, the solvent was removed, and then recrystallized using toluene and hexane. Compound 4, in pure powder form, was obtained in 80% yield. MS:[M+H] ⁺ = 747

< Example >

Example One.

A glass substrate coated with a thin film of indium tin oxide (ITO) at a thickness of 1300 에 was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, Fischer (Fischer Co.) was used as a detergent, and distilled water filtered secondarily by a filter of Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, ultrasonic washing was repeated 10 times with distilled water for 10 minutes. After washing with distilled water, ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, followed by drying and then transported to a plasma cleaner. In addition, the substrate was washed for 5 minutes using oxygen plasma, and then transferred to a vacuum evaporator.

The following compound [HI-A] was vacuum-deposited to a thickness of 600 Pa on an ITO transparent electrode prepared as described above to form a hole injection layer. The following compound [HAT-CN] (50 kPa) and the following compound [HT-A] (600 kPa) were sequentially vacuum deposited on the hole injection layer to form a hole transport layer.

delete

After this preparation, [BH-A] and Compound 1 were vacuum-deposited to a thickness of 200 Pa in a weight ratio of 25:1 as a host to form a light emitting layer. Subsequently, 300-of [ET-A] and Liq were deposited at a 1:1 ratio, and lithium fluoride (LiF) and aluminum at a thickness of 1,000 순차적 were sequentially deposited on top of this to form a cathode to form organic cathodes. The device was prepared.

In the above process, the deposition rate of the organic material was maintained at 0.4 to 0.9 Å/sec, the lithium fluoride of the negative electrode was maintained at a deposition rate of 0.3 Å/sec, and the aluminum was maintained at a deposition rate of 2 Å/sec. ^-7 to 5 x 10 ^-8 torr was maintained to produce an organic light emitting device.

Example 2.

In Example 1, an organic light emitting device was manufactured in the same manner as in Example 1, except that Compound 3 was used instead of Compound 1 and [BH-B] was used instead of the host [BH-A].

Example 3.

In Example 1, an organic light emitting diode was manufactured according to the same method as Example 1 except for using Compound 3 instead of Compound 1 and [BH-C] instead of the host [BH-A].

Example 4.

In Example 1, using Compound 3 instead of Compound 1, the host [BH-A] further includes the host [BH-B] ([BH-A] and [BH-B]) in a weight ratio of 1:1 An organic light emitting device was manufactured in the same manner as in Example 1, except that).

Example 5.

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

Example 6.

An organic light emitting diode was manufactured according to the same method as Example 1 except for using Compound 4 instead of Compound 1 in Example 1.

< Comparative example >

Comparative example One.

An organic light emitting device was manufactured in the same manner as in Example 1, except that [BD-A] was used instead of Compound 1 in Example 1.

Comparative example 2.

[BD-B] was used instead of Compound 1 in Example 1, and an organic light emitting device was manufactured in the same manner as in Example 1.

Comparative example 3.

[BD-C] was used instead of Compound 1 in Example 1, and an organic light emitting device was manufactured in the same manner as in Example 1.

The driving voltage and luminous efficiency of the organic light emitting device manufactured by the above-described method were measured at a current density of 10 mA/cm ² , and a time (T ₉₀ ) of 90% of the initial luminance at a current density of 20 mA/cm ² was measured. It was measured. The results are shown in Table 1 below.

number Host Dopant Voltage (V) Efficiency (Cd/A) Color coordinate (x,y) Life (hr) at 10mA/cm ² at 10mA/cm ² T ₉₀ at 20mA/cm ² Example 1 BH-A Compound 1 3.55 4.9 (0.13, 0.05) 160 Example 2 BH-B Compound 3 3.40 5.40 (0.13, 0.05) 230 Example 3 BH-C Compound 3 3.72 5.30 (0.13, 0.06) 210 Example 4 BH-A + BH-B Compound 3 3.40 5.40 (0.13, 0.06) 230 Example 5 BH-A Compound 3 3.47 5.45 (0.13, 0.06) 215 Example 6 BH-A Compound 4 3.50 5.47 (0.13, 0.06) 240 Comparative Example 1 BH-A BD-A 3.65 4.9 (0.13, 0.12) 200 Comparative Example 2 BH-A BD-B 3.60 5.33 (0.13, 0.05) 115 Comparative Example 3 BH-A BD-C 3.43 3.78 (0.12, 0.04) 110

From the results of Table 1, it can be seen that the compounds represented by Chemical Formula 1 according to the present invention have characteristics of high luminous efficiency and long life, respectively, in the blue organic light emitting device. Specifically, it can be confirmed that Examples 1 to 6 of the present application have superior life characteristics of Comparative Examples 2 and 3 using boron-based compounds or compounds having a structure different from Formula 1 of the present application.

In addition, since Comparative Example 1 using a pyrene-based compound instead of the compound represented by Formula 1 herein represents a value of y in the color coordinates as 0.12, it can be confirmed that the color purity is very low.

1: Substrate
2: anode
3: light emitting layer
4: Cathode
5: hole injection layer
6: hole transport layer
7: emitting layer
8: electron transport layer

Claims (16)

Compound represented by the formula (1):
[Formula 1]

In Chemical Formula 1,
A1 is a substituted or unsubstituted aromatic hydrocarbon ring; Or a substituted or unsubstituted aromatic heterocycle,
W is O, S, Se, PRb, C=O, CRcRd, SiReRf or P(=O)Rg,
X1 is N or CR11, X2 is N or CR12, X3 is N or CR13,
However, when X2 is N, X3 is CR13, and when X3 is N, X2 is CR12,
Rb to Rg, R11 to R13, Ar1 and Ar2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Alkyl silyl groups; Arylsilyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted alkoxyaryl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or combine with adjacent groups to form a substituted or unsubstituted ring,
R1 and R2 are connected to the dotted line of Formula 2 to form a ring,
R3 and R12; Or R3 and R13 are connected to the dotted portion of the formula (2) to form a ring,
[Formula 2]

In Chemical Formula 2,
Y is O, S, Se, NR21, PR22, C=O, CR23R24, SiR25R26 or P(=O)R27,
R21 to R27 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or combine with adjacent groups to form a substituted or unsubstituted ring,
A2 is a substituted or unsubstituted aromatic hydrocarbon ring; Or a substituted or unsubstituted aromatic heterocycle. The method according to claim 1,
Formula 1 is a compound represented by the following Formula 1-1 or Formula 1-2:
[Formula 1-1]

[Formula 1-2]

In Formula 1-1 and Formula 1-2,
W, X1, R1, R2, A1, Ar1 and Ar2 are the same as defined in Chemical Formula 1,
X21 and X31 are the same as or different from each other, and each independently N or CR41,
R41 is hydrogen; heavy hydrogen; Halogen group; Cyano group; Alkyl silyl groups; Arylsilyl group; Boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkylamine group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted heteroarylamine group; A substituted or unsubstituted alkoxyaryl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or combine with adjacent groups to form a substituted or unsubstituted ring,
R3 and R4; And R3 and R5 are connected to the dotted portion of Formula 2 to form a ring. The method according to claim 1,
Chemical Formula 1 is a compound represented by any one of the following Chemical Formulas 2-1 to 2-7:
[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Formula 2-4]

[Formula 2-5]

[Formula 2-6]

[Formula 2-7]

In Chemical Formulas 2-1 to 2-7,
W, X1, X2, X3, A1, Ar1 and Ar2 are the same as defined in Chemical Formula 1,
Y1 to Y14 are the same as or different from each other, and each independently the same as the definition of Y in Formula 2,
A21 to A34 are the same as or different from each other, and each independently is the same as the definition of A2 in Formula 2 above. The method according to claim 1,
Ar1 and Ar2 are the same as or different from each other, and each independently substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms. The method according to claim 1,
The compound represented by Formula 1 is a compound represented by any one of the following structures:

. A first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein one or more of the organic material layers comprises a compound according to any one of claims 1 to 5 Light emitting element. The method according to claim 6,
The organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer comprises the compound. The method according to claim 6,
The organic material layer includes an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes the compound. The method according to claim 6,
The organic material layer includes an emission layer, and the emission layer includes the compound. The method according to claim 6, The organic material layer comprises an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer comprises the compound. The method according to claim 6,
The organic material layer includes a light emitting layer, the light emitting layer is an organic light emitting device comprising a compound represented by the formula (1A):
[Formula 1A]

In Formula 1A,
L103 to L106 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
Ar5 to Ar8 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
R101 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
p is an integer from 0 to 6,
When p is 2 or more, the substituents in parentheses are the same as or different from each other. The method according to claim 11,
L103 to L106 are the same as or different from each other, and each independently a direct bond; Or an organic light emitting device that is selected from the following structures:

. The method according to claim 11,
Ar5 to Ar8 are the same as or different from each other, and each independently hydrogen; Or an organic light emitting device that is selected from the following structures:

. 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 compound represented by the formula (1B):
[Formula 1B]

In Formula 1B,
L107 to L109 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
Ar9 to Ar11 are the same as or different from each other, and each independently hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
R102 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
q is an integer from 0 to 7,
When q is 2 or more, the substituents in parentheses are the same or different from each other. The method according to claim 14,
L107 to L109 are the same as or different from each other, and each independently a direct bond; Or an organic light emitting device that is selected from the following structures:

. The method according to claim 14,
Ar9 to Ar11 are the same as or different from each other, and each independently hydrogen; Or an organic light emitting device that is selected from the following structures:

.

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