KR102186088B1 - Polycyclic compound and organic light emitting device comprising the same - Google Patents

Abstract

The present invention relates to a compound represented by Chemical Formula 1 and an organic light-emitting device including the same.

Description

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

This application claims the benefit of the filing date of Korean Patent Application No. 10-2017-0153108 filed with the Korean Intellectual Property Office on November 16, 2017, the entire contents of which are incorporated herein.

The present invention relates to a polycyclic compound and an organic light emitting device comprising the same.

The organic light emission phenomenon is an example in which current is converted into visible light by an internal process of a specific organic molecule. The principle of the organic light emission phenomenon is as follows. When the organic material layer is placed between the anode and the cathode, when a voltage is applied between the two electrodes, electrons and holes are injected into the organic material layer from the cathode and the anode, respectively. The electrons and holes injected into the organic material layer recombine in the emission layer to form a molecular exiton, an electron-hole pair, and the excitons fall back to the low-energy ground state and light up. . An organic light-emitting device using this principle may generally be composed of an organic material layer including a cathode and an anode, and an organic material layer positioned therebetween, for example, a hole injection layer, a hole transport layer, an emission layer, and an electron transport layer.

Here, the light-emitting layer is composed of only a light-emitting material, or has a structure including a small amount of light-emitting material (dopant). When a light-emitting material is included, the material containing the light-emitting material is called a host material or a matrix material, and the light-emitting material is called a dopant or guest material. The light-emitting material generates more photons from excitons to improve the efficiency of the OLED, and each light-emitting material has a variety of colors, so it plays an advantageous role in controlling the color of the OLED.

Publication Patent Publication No. KR 10-2006-0134999

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

An exemplary embodiment of the present invention provides a compound represented by the following formula (1).

[Formula 1]

In Formula 1,

Cy1 to Cy4 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic or polycyclic ring,

a to d are each 0 or 1, provided that a+b+c+d is 1 or more,

Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or combine with each other to form a ring,

Ar3 and Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or combine with each other to form a ring,

R1 and R2 are the same as or different from each other, and each independently deuterium; Halogen group; Nitrile group; -SiR ₄₀ R ₄₁ R ₄₂ ; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

R ₄₀ to R ₄₂ 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,

Ra to Rd are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

a1, a2, m1 and m2 are each an integer greater than or equal to 0,

When a1 is 2 or more, R1 is the same as or different from each other,

When a2 is 2 or more, R2 is the same as or different from each other,

When m1 is 2 or more, NRaRb is the same as or different from each other,

When m2 is 2 or more, NRcRd is the same as or different from each other,

m1+m2 is 1 or more.

An exemplary embodiment of the present invention is an organic light emitting device comprising a first electrode, a second electrode, and one or more organic material layers disposed between the first electrode and the second electrode, wherein at least one of the organic material layers is described above. It provides an organic light-emitting device comprising a compound.

The compound of the present invention can be used as a dopant in the emission layer of an organic light-emitting device. When the compound is used in an organic light-emitting device, the luminous efficiency of the organic light-emitting device is improved, the driving voltage of the device is reduced, or the life of the device is reduced. Can be improved.

1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4.
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 I did it.
3 shows a substrate 1, an anode 2, a first hole injection layer 9, a second hole injection layer 10, a hole transport layer 6, an electron suppression layer 11, a light emitting layer 3, and electrons. An example of an organic light-emitting device comprising a transport layer 8, an electron injection layer 12, and a cathode 4 is shown.

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

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

In the present specification, the term "substituted or unsubstituted" refers to deuterium; Halogen group; Nitrile group; Silyl group; Alkyl group; Cycloalkyl group; Alkenyl group; Alkoxy group; Aryl group; Heteroaryl group; Alkylamine group; Arylamine group; Aralkylamine group; It means substituted or unsubstituted with one or more substituents selected from the group consisting of a heteroarylamine group and an arylheteroarylamine group, or substituted or unsubstituted with a group to which two or more substituents are connected among the above-exemplified substituents. For example, a group to which two substituents are connected is an aryl group substituted with an aryl group or a heteroaryl group; And a heteroaryl group substituted with an aryl group or a heteroaryl group. The biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are connected. In addition, examples of groups to which three substituents are connected include an aryl group substituted with a heteroaryl group substituted with an aryl group, an aryl group substituted with an aryl group substituted with a heteroaryl group, and a heteroaryl group substituted with an aryl group substituted with a heteroaryl group. .

In one embodiment, the term "substituted or unsubstituted" refers to an alkyl group; Silyl group; And it means that one group selected from the group consisting of an aryl group or two or more groups selected from the group is substituted or unsubstituted with a group linked to each other.

In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.

In the present specification, the silyl group may be represented by the formula of -SiRxRyRz, and Rx, Ry and Rz are each independently hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. In an exemplary embodiment, Rx, Ry, and Rz are each independently hydrogen; Alkyl group; Or it may be an aryl group. The silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, etc., but is not limited thereto. Does not.

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to an 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. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl , Isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, Cyclopentylmethyl, cycloheptylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1 ,1-dimethylpropyl, isohexyl, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.

In the present specification, the cycloalkyl group refers to a cyclic hydrocarbon group, and the number of carbon atoms is not particularly limited, but is preferably 3 to 60, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 20. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3, 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto.

In the present specification, the alkenyl group represents a linear or branched unsaturated hydrocarbon group, and may be a linear or branched chain. Although the number of carbon atoms is not particularly limited, it is preferably 2 to 30. According to an exemplary embodiment, the alkenyl group has 2 to 20 carbon atoms. Specific examples include ethenyl, vinyl, propenyl, allyl, isopropenyl, butenyl, isobutenyl, n-pentenyl, and n-hexenyl, but are not limited thereto.

In the present specification, the alkoxy group refers to a group in which an alkyl group is bonded to an oxygen atom, and carbon number is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the alkoxy group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkoxy group has 1 to 6 carbon atoms. Specific examples of the alkoxy group include, but are not limited to, methoxy group, ethoxy group, propoxy group, isobutyloxy group, sec-butyloxy group, pentyloxy group, iso-amyloxy group, hexyloxy group, and the like. .

In the present specification, an aryl group means a substituted or unsubstituted monocyclic or polycyclic that is wholly or partially unsaturated and has aromaticity. The number of carbon atoms 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 an exemplary embodiment, the aryl group has 6 to 40 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. The monocyclic aryl group may be a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, a triphenylenyl group, and the like, but is not limited thereto.

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

,

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

,

,

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,

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And

Etc. However, it is not limited thereto.

In the present specification, the heteroaryl group is a cyclic group including one or more of N, O, and S as a heteroatom, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. According to an exemplary embodiment, the heteroaryl group has 2 to 40 carbon atoms. According to another exemplary embodiment, the heteroaryl group has 2 to 30 carbon atoms. Examples of heteroaryl groups include thiophenyl group, furanyl group, pyrrolyl group, imidazolyl group, thiazolyl group, oxazolyl group, oxadiazolyl group, triazolyl group, pyridinyl group, bipyridinyl group, pyrimidinyl group, tria Genyl group, triazolyl group, acridinyl group, carbonyl group, acenaphthoquinoxalinyl group, indenoquinazolinyl group, indenoisoquinolinyl group, indenoquinolinyl group, pyridoindolyl group, pyridazinyl group, Pyrazinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazino pyrazinyl group, isoquinolinyl group, indolyl group, carbazolyl group , Benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, benzocarbazolyl group, benzothiophenyl group, dibenzothiophenyl group, benzofuranyl group, dibenzofuranyl group, phenanthroline group, thiazoli There are nil group, isoxazolyl group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl group, phenoxazinyl group, phenothiazinyl group, and the like, but are not limited thereto. The heteroaryl group includes an aliphatic heteroaryl group and an aromatic heteroaryl group.

In the present specification, the amine group refers to an organic compound and a functional group having an unshared electron pair on a nitrogen atom. Although the number of carbon atoms is not particularly limited, it is preferably 1 to 50.

In the present specification, an alkylamine group means a group in which the nitrogen atom of the amine is substituted with an alkyl group. Specific examples include, but are not limited to, a dimethylamine group, an ethylamine group, and a diethylamine group.

In the present specification, an arylamine group means a group in which the nitrogen atom of the amine is substituted with an aryl group. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group including two or more aryl groups may include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time. Specific examples of the arylamine group include phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, 3-methylphenylamine group, 4-methylnaphthylamine group, 2-methylbiphenylamine group, and 9- A methylanthracenylamine group, a diphenylamine group, a phenylnaphthylamine group, a ditolylamine group, a phenyltolylamine group, and the like, but are not limited thereto.

In the present specification, examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group or a substituted or unsubstituted diheteroarylamine group. The heteroaryl group in the heteroarylamine group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group. The heteroarylamine group including two or more heteroaryl groups may include a monocyclic heteroaryl group, a polycyclic hetearyl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group at the same time.

In the present specification, the aralkylamine group means an amine group substituted with an aryl group and an alkyl group.

In the present specification, an arylheteroarylamine group means an amine group substituted with an aryl group and a heteroaryl group.

In the present specification, the aryl group described above may be applied to the aryl group among the arylamine group, aralkylamine group, and arylheteroarylamine group.

In the present specification, the above description of the alkyl group may be applied to the alkyl group in the alkylamine group and the aralkylamine group.

In the present specification, the above description of the heteroaryl group may be applied to the heteroaryl group in the heteroarylamine group.

In the present specification, the "adjacent" group means a substituent substituted on an atom directly connected to the atom where the corresponding substituent is substituted, a substituent positioned three-dimensionally closest to the corresponding substituent, or another substituent substituted on the atom where the corresponding substituent is substituted. I can. For example, two substituents substituted at an ortho position in a benzene ring and two substituents substituted at the same carbon in an aliphatic ring may be interpreted as "adjacent" to each other.

According to an exemplary embodiment of the present invention, it provides a heterocyclic compound represented by the following formula (1).

[Formula 1]

In Formula 1,

Cy1 to Cy4 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic or polycyclic ring,

a to d are each 0 or 1, provided that a+b+c+d is 1 or more,

Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or combine with each other to form a ring,

Ar3 and Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or combine with each other to form a ring,

R1 and R2 are the same as or different from each other, and each independently deuterium; Halogen group; Nitrile group; -SiR ₄₀ R ₄₁ R ₄₂ ; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

R ₄₀ to R ₄₂ 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,

Ra to Rd are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

a1, a2, m1 and m2 are each an integer greater than or equal to 0,

When a1 is 2 or more, R1 is the same as or different from each other,

When a2 is 2 or more, R2 is the same as or different from each other,

When m1 is 2 or more, NRaRb is the same as or different from each other,

When m2 is 2 or more, NRcRd is the same as or different from each other,

m1+m2 is 1 or more.

When the ring represented by Cy1 to Cy4 is condensed in indenoindene, the resonance of the compound increases compared to indenoindene in which the ring is not condensed, so that the compound may have a light emission wavelength in a longer wavelength region. As the number of rings condensed to indenoindene among Cy1 to Cy4 increases, the emission wavelength may shift to a longer wavelength.

The compound represented by Formula 1 has at least one amine as a substituent. The amine group increases the band gap of the compound represented by Chemical Formula 1, and as a result, the compound represented by Chemical Formula 1 of the present invention can be used as a fluorescent dopant in blue and green hole trap versions.

As the number of amine groups substituted in the compound represented by Formula 1 increases, the band gap of the compound represented by Formula 1 may increase.

In the compound represented by Formula 1, the condensation of the ring of Cy1 or Cy4 is more advantageous in increasing the resonance compared to the case of condensation of the ring at the Cy2 or Cy3 position.

In Formula 1, Cy1 to Cy4 are the same or different from each other, and each independently a substituted or unsubstituted monocyclic or polycyclic ring means that a monocyclic or polycyclic ring (Cy1 to Cy4) is condensed to the central indenoindene ring Means you can be. For example, when Cy1 is a benzene ring and a is 1, Chemical Formula 1 may be expressed as a structure in which a benzene ring is condensed at the Cy1 position of indenoindene as shown in Chemical Formula 1-x.

[Formula 1-x]

Meanwhile, in Formula 1, three of a to d may be 0. The meaning that a to d is 0 means that a substituent of hydrogen, R1 or R2 is bonded to a position where Cy1 to Cy4 of indenoindene can be bonded. For example, when a is 0, the substituent of the benzene ring to which Cy1 of indenoindene can be condensed may be hydrogen or R2 in Formula 1, as shown in Formula 1-y below.

[Formula 1-y]

In Formula 1, Cy1 to Cy4 are the same as or different from each other, and each independently a substituted or unsubstituted hydrocarbon ring; A substituted or unsubstituted aliphatic hydrocarbon ring; A substituted or unsubstituted aromatic hydrocarbon ring; Or a substituted or unsubstituted heterocycle.

In the present specification, the hydrocarbon ring means a ring consisting only of carbon and hydrogen atoms, and the hydrocarbon ring may be an aliphatic hydrocarbon ring or an aromatic hydrocarbon ring.

In the present specification, the aliphatic hydrocarbon ring is a ring that is not aromatic and refers to a ring consisting only of carbon and hydrogen atoms. Examples of the aliphatic hydrocarbon ring include cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, cyclooctene, and the like, It is not limited to these only.

In the present specification, the aromatic hydrocarbon ring refers to an aromatic ring consisting only of carbon and hydrogen atoms. Examples of aromatic hydrocarbon rings include benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, phenalene, pyrene, tetracene, chrysene, pentacene, fluorene, indene, acetapthylene, Benzofluorene, spirofluorene, and the like, but are not limited thereto.

In the present specification, the heterocycle refers to a ring including one or more of heteroatoms, and the heterocycle may be an aliphatic heterocycle or an aromatic heterocycle.

In the present specification, the aliphatic heterocycle refers to an aliphatic ring containing at least one heteroatom. Examples of aliphatic heterocycles include oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxephan, azocaine , Thiocane, and the like, but are not limited thereto.

In the present specification, the aromatic heterocycle means an aromatic ring containing at least one heteroatom. Examples of aromatic heterocycles include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, parasol, oxazole, isoxazole, thiazole, isothiazole, triazole, oxadiazole, thia Diazole, dithiazole, tetrazole, pyran, thiopyran, diazine, oxazine, thiazine, dioxin, triazine, tetrazine, isoquinoline, quinoline, quinol, quinazoline, quinoxaline, naphthyridine, acridine , Phenanthridine, diazanaphthalene, dryazainden, indole, indolizine, benzothiazole, benzoxazole, benzimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzo Carbazole, dibenzocarbazole, phenazine, imidazopyridine, phenoxazine, phenanthridine, indolocarbazole, indenocarbazole, and the like, but are not limited thereto.

In the present specification, the aliphatic hydrocarbon ring, aromatic hydrocarbon ring, aliphatic hetero ring and aromatic hetero ring may be monocyclic or polycyclic.

In the exemplary embodiment of the present specification, Cy1 to Cy4 are the same as or different from each other, and each independently a substituted or unsubstituted aromatic hydrocarbon ring; Or a substituted or unsubstituted aromatic heterocycle.

In the exemplary embodiment of the present specification, Cy1 to Cy4 are the same as or different from each other, and each independently a substituted or unsubstituted C6-C18 aromatic hydrocarbon ring; Or a substituted or unsubstituted C2-C20 aromatic heterocycle.

In the exemplary embodiment of the present specification, Cy1 to Cy4 are the same as or different from each other, and each independently a substituted or unsubstituted C6-C10 aromatic hydrocarbon ring; Or a substituted or unsubstituted C2-C14 aromatic heterocycle.

In the exemplary embodiment of the present specification, Cy1 to Cy4 are the same as or different from each other, and each independently a substituted or unsubstituted 1 to 3 ring aromatic hydrocarbon ring; Or a substituted or unsubstituted 1 to 3 ring aromatic heterocycle.

In the exemplary embodiment of the present specification, Cy1 to Cy4 are the same as or different from each other, and each independently benzene; Benzofuran; Or benzothiophene.

According to an exemplary embodiment of the present invention, Formula 1 provides a compound represented by the following Formula 2 or Formula 3.

[Formula 2]

[Formula 3]

In Formulas 2 and 3,

Ar1, Ar2, Ar3, Ar4, R1, R2, Ra. Rb. Rc and Rd are as defined in Formula 1,

a3 is an integer of 0 to 4, and when a3 is 2 or more, R1 is the same as or different from each other,

a4 is an integer from 0 to 6, and when a4 is 2 or more, R2 is the same as or different from each other,

m3 is an integer from 0 to 4, and when m3 is 2 or more, NRaRb is the same as or different from each other,

m4 is an integer from 0 to 6, and when m4 is 2 or more, NRcRd is the same as or different from each other,

m3+m4 is an integer from 1 to 10,

a3+m3 is an integer from 0 to 4,

a4+m4 is an integer of 0-6.

According to an exemplary embodiment of the present invention, Formula 1 provides a compound represented by any one of the following Formulas 4 to 6.

[Formula 4]

[Formula 5]

[Formula 6]

In Formulas 4 to 6,

Ar1, Ar2, Ar3, Ar4, R1, R2, Ra, Rb, Rc and Rd are as defined in Formula 1,

a5 is an integer from 0 to 6, and when a5 is 2 or more, R2 is the same as or different from each other,

a6 is an integer from 0 to 6, and when a6 is 2 or more, R1 is the same as or different from each other, and

a7 is an integer from 0 to 8, and when a7 is 2 or more, R2 is the same as or different from each other,

m5 is an integer from 0 to 6, and when m5 is 2 or more, NRcRd is the same as or different from each other,

m6 is an integer from 0 to 6, and when m6 is 2 or more, NRaRb is the same as or different from each other,

m7 is an integer from 0 to 8, and when m7 is 2 or more, NRcRd is the same as or different from each other,

m5+m6 is an integer from 1 to 12,

m6+m7 is an integer from 1 to 14,

a5+m5 is an integer from 0 to 6,

a6+m6 is an integer from 0 to 6,

a7+m7 is an integer from 0 to 8.

According to an exemplary embodiment of the present invention, Cy1 to Cy4 are the same as or different from each other, and each independently a substituted or unsubstituted heterocycle.

According to an exemplary embodiment of the present invention, Cy1 to Cy4 are the same as or different from each other, and each independently benzofuran, benzothiophene or indole.

According to an exemplary embodiment of the present invention, Formula 1 provides a compound represented by the following Formula 7 or 8.

[Formula 7]

[Formula 8]

In Formulas 7 and 8,

Ar1, Ar2, Ar3, Ar4, R1, R2, Ra, Rb, Rc and Rd are as defined in Formula 1,

One of X1 and X2 is a direct bond, and the other is S, O or NR ₂₁ ,

R ₂₁ is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

a8 is an integer from 0 to 6, and when a8 is 2 or more, R2 is the same as or different from each other,

a9 is an integer from 0 to 4, and when a9 is 2 or more, R1 is the same as or different from each other,

m8 is an integer from 0 to 6, and when m8 is 2 or more, NRcRd is the same as or different from each other,

m9 is an integer of 0 to 4, and when m9 is 2 or more, NRaRb is the same as or different from each other,

m8+m9 is an integer from 1 to 10,

a8+m8 is an integer from 0 to 6,

a9+m9 is an integer of 0-4.

According to an exemplary embodiment of the present specification, Formula 1 provides a compound represented by Formula 9 below.

[Formula 9]

In Formula 9,

Ar1, Ar2, Ar3, Ar4, R1, R2, Ra, Rb, Rc and Rd are as defined in Formula 1,

One of X3 and X4 is a direct bond, and the other is S, O or NR ₂₂ ,

One of X5 and X6 is a direct bond, and the other is S, O or NR ₂₃ ,

R ₂₂ and R ₂₃ 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 alkenyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

a10 is an integer from 0 to 6, and when a10 is 2 or more, R1 is the same as or different from each other,

a11 is an integer from 0 to 6, and when a11 is 2 or more, R2 is the same as or different from each other,

m10 is an integer of 0 to 6, and when m10 is 2 or more, NRaRb is the same as or different from each other,

m11 is an integer from 0 to 6, and when m11 is 2 or more, NRcRd is the same as or different from each other,

m10+m11 is an integer from 1 to 12,

a10+m10 is an integer from 0 to 6,

a11+m11 is an integer of 0-6.

In an exemplary embodiment of the present specification, Chemical Formula 1 is represented by Chemical Formula 10 below.

[Formula 10]

In Formula 10,

Ar1, Ar2, Ar3, Ar4, R1, R2, Ra, Rb, Rc and Rd are as defined in Formula 1,

One of X7 and X8 is a direct bond, and the other is S, O or NR ₂₄ ,

R ₂₄ is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

a12 is an integer from 0 to 6, and when a12 is 2 or more, R1 is the same as or different from each other,

a13 is an integer from 0 to 6, and when a13 is 2 or more, R2 is the same as or different from each other,

m12 is an integer from 0 to 6, and when m12 is 2 or more, NRaRb is the same as or different from each other,

m13 is an integer from 0 to 6, and when m13 is 2 or more, NRcRd is the same as or different from each other,

m12+m13 is an integer from 1 to 12,

a12+m12 is an integer from 0 to 6,

a13+m13 is an integer of 0-6.

In the exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or combine with each other to form a ring.

In the exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group, or are bonded to each other to form a ring.

In the exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group, or are bonded to each other to form a hydrocarbon ring.

In the exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted C6-C25 aryl group, or combine with each other to form a C6-C30 hydrocarbon ring.

In the exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted C6-C18 aryl group, or combine with each other to form a C6-C25 hydrocarbon ring.

In the exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted C6-C13 aryl group, or combine with each other to form a C6-C20 hydrocarbon ring.

In the exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; Or a substituted or unsubstituted naphthyl group, or combine with each other to form a ring.

In the exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group; Or a naphthyl group, or combine with each other to form a ring.

In the exemplary embodiment of the present specification, the ring formed by bonding of Ar1 and Ar2 to each other is fluorene; Or benzofluorene. In this case, the bond between Ar1 and Ar2 is a single bond portion of the pentagonal ring of fluorene, and has a form in which fluorene is spiro bonded to indenoindene.

In the exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or combine with each other to form a ring.

In the exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group, or combine with each other to form a ring.

In the exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group, or are bonded to each other to form a hydrocarbon ring.

In the exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted C6-C25 aryl group, or combine with each other to form a C6-C30 hydrocarbon ring.

In the exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted C6-C18 aryl group, or combine with each other to form a C6-C25 hydrocarbon ring.

In the exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted C6-C13 aryl group, or combine with each other to form a C6-C20 hydrocarbon ring.

In the exemplary embodiment of the present specification, Ar3 and Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; Or a substituted or unsubstituted naphthyl group, or combine with each other to form a ring.

In the exemplary embodiment of the present specification, Ar3 and Ar4 are the same or different, and each independently a phenyl group; Or a naphthyl group, or combine with each other to form a ring.

In the exemplary embodiment of the present specification, the ring formed by bonding of Ar3 and Ar4 to each other is fluorene; Or benzofluorene. In this case, the bond between Ar3 and Ar4 is a single bond part of the pentagonal ring of fluorene, and has a form in which fluorene is spiro bonded to indenoindene.

In the exemplary embodiment of the present specification, Ar1 and Ar2 are the same.

In the exemplary embodiment of the present specification, Ar3 and Ar4 are the same.

In the exemplary embodiment of the present specification, Ar1 and Ar2 are the same as Ar3 and Ar4.

In the exemplary embodiment of the present specification, R1 is hydrogen.

In the exemplary embodiment of the present specification, R2 is hydrogen.

In the exemplary embodiment of the present specification, Ra to Rd are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In the exemplary embodiment of the present specification, Ra to Rd are the same as or different from each other, and each independently a substituted or unsubstituted C1-C20 alkyl group; A substituted or unsubstituted C6-C30 aryl group; Or a substituted or unsubstituted C2-C30 heteroaryl group.

In the exemplary embodiment of the present specification, Ra to Rd are the same as or different from each other, and each independently a substituted or unsubstituted aryl group.

In the exemplary embodiment of the present specification, Ra to Rd are the same as or different from each other, and each independently a substituted or unsubstituted C6-C25 aryl group.

In the exemplary embodiment of the present specification, Ra to Rd are the same as or different from each other, and each independently a substituted or unsubstituted C6-C20 aryl group.

In the exemplary embodiment of the present specification, Ra to Rd are the same as or different from each other, and each independently a substituted or unsubstituted C6-C16 aryl group.

In the exemplary embodiment of the present specification, Ra to Rd are the same as or different from each other, and each independently selected from the group consisting of a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and -SR ₅₀ R ₅₁ R ₅₂ An aryl group unsubstituted or substituted with one or more substituents, R ₅₀ , R ₅₁ and R ₅₂ are the same as or different from each other, and each independently hydrogen; Alkyl group; Or an aryl group.

In the exemplary embodiment of the present specification, Ra to Rd are the same as or different from each other, and each independently an alkyl group, an aryl group, or an aryl group unsubstituted or substituted with -SR ₅₀ R ₅₁ R ₅₂ , R ₅₀ , R ₅₁ And R ₅₂ are the same as or different from each other, and each independently hydrogen; Alkyl group; Or an aryl group.

In the exemplary embodiment of the present specification, Ra to Rd are the same as or different from each other, and each independently a C1-C10 alkyl group, a C6-C20 aryl group, or an aryl unsubstituted or substituted with -SR ₅₀ R ₅₁ R ₅₂ A group, R ₅₀ , R ₅₁ and R ₅₂ are the same as or different from each other, and each independently hydrogen; C1-C10 alkyl group; Or C6-C25 aryl group.

In the exemplary embodiment of the present specification, Ra to Rd are the same as or different from each other, and each independently a C1-C6 alkyl group, a C6-C12 aryl group, or an aryl unsubstituted or substituted with SR ₅₀ R ₅₁ R ₅₂ A group, R ₅₀ , R ₅₁ and R ₅₂ are the same as or different from each other, and each independently hydrogen; C1-C6 alkyl group; Or a C6-C12 aryl group.

In the exemplary embodiment of the present specification, Ra to Rd are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group or a substituted or unsubstituted naphthyl group, and a substituent of the substituted phenyl group or substituted naphthyl group Is an alkyl group, an aryl group, or -SR ₅₀ R ₅₁ R ₅₂ , R ₅₀ , R ₅₁ and R ₅₂ are the same as or different from each other, and each independently hydrogen, an alkyl group or an aryl group.

In the exemplary embodiment of the present specification, Ra to Rd are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group or a substituted or unsubstituted naphthyl group, and a substituent of the substituted phenyl group or substituted naphthyl group Is a methyl group, t-butyl group, trimethylsilyl group or phenyl group.

In the exemplary embodiment of the present specification, Ra is the same as Rc.

In the exemplary embodiment of the present specification, Rb is the same as Rd.

In the exemplary embodiment of the present specification, NRaRb is the same as NRcRd.

In the exemplary embodiment of the present specification, a to d are each 0 or 1, provided that a+b+c+d is 1 or more.

In the exemplary embodiment of the present specification, a is 1.

In the exemplary embodiment of the present specification, b is 1.

In the exemplary embodiment of the present specification, c is 1.

In the exemplary embodiment of the present specification, d is 1.

In the exemplary embodiment of the present specification, a+b+c+d is 2 or more.

In the exemplary embodiment of the present specification, a+b+c+d is 1.

In the exemplary embodiment of the present specification, a+b+c+d is 2.

In the exemplary embodiment of the present specification, m1 is 1.

In the exemplary embodiment of the present specification, m2 is 1.

In the exemplary embodiment of the present specification, m3 is 1.

In the exemplary embodiment of the present specification, m4 is 1.

In the exemplary embodiment of the present specification, m5 is 1.

In the exemplary embodiment of the present specification, m6 is 1.

In the exemplary embodiment of the present specification, m7 is 1.

In the exemplary embodiment of the present specification, m8 is 1.

In the exemplary embodiment of the present specification, m9 is 1.

In the exemplary embodiment of the present specification, m10 is 1.

In the exemplary embodiment of the present specification, m11 is 1.

In the exemplary embodiment of the present specification, a1 is 0.

In the exemplary embodiment of the present specification, a2 is 0.

In the exemplary embodiment of the present specification, a3 is 0.

In the exemplary embodiment of the present specification, a4 is 0.

In the exemplary embodiment of the present specification, a5 is 0.

In the exemplary embodiment of the present specification, a6 is 0.

In the exemplary embodiment of the present specification, a7 is 0.

In the exemplary embodiment of the present specification, a8 is 0.

In the exemplary embodiment of the present specification, a9 is 0.

In the exemplary embodiment of the present specification, a10 is 0.

In the exemplary embodiment of the present specification, a11 is 0.

In the exemplary embodiment of the present specification, X1 is O or S, and X2 is a direct bond.

In the exemplary embodiment of the present specification, X1 is a direct bond, and X2 is O or S.

In the exemplary embodiment of the present specification, X3 is O or S, and X4 is a direct bond.

In the exemplary embodiment of the present specification, X3 is a direct bond, and X4 is O or S.

In the exemplary embodiment of the present specification, X5 is O or S, and X6 is a direct bond.

In the exemplary embodiment of the present specification, X5 is a direct bond, and X6 is O or S.

In the exemplary embodiment of the present specification, X3 and X6 are the same.

In the exemplary embodiment of the present specification, X4 and X6 are the same.

In the exemplary embodiment of the present specification, X7 is O or S, and X8 is a direct bond.

In the exemplary embodiment of the present specification, X7 is a direct bond, and X8 is O or S.

In an exemplary embodiment of the present specification, Formula 1 is represented by the following Formula C.

[Formula C]

In Formula C,

Ar1, Ar2, Ar3, Ar4, R1, R2, Ra, Rb, Rc, Rd, a1, a2, m1, m2, a, b, c and d are as defined in Formula 1.

In an exemplary embodiment of the present specification, Chemical Formula 1 is represented by the following Chemical Formula D.

[Formula D]

In Formula D,

Ar1, Ar2, Ar3, Ar4, R1, R2, Ra, Rb, Rc, Rd, a1, a2, m1, m2, a, b, c and d are as defined in Formula 1,

One of Y1 and Y2 is a direct bond, and the other is S, O or NR ₃₁ ,

One of Y3 and Y4 is a direct bond, and the other is S, O or NR ₃₂ ,

One of Y5 and Y6 is a direct bond, and the other is S, O or NR ₃₃ ,

One of Y7 and Y8 is a direct bond, and the other is S, O or NR ₃₄ ,

R ₃₁ to R ₃₄ 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 alkenyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In an exemplary embodiment of the present specification, Formula 1 is represented by the following Formula E.

[Formula E]

In Formula E,

Ar1, Ar2, Ar3, Ar4, R1, R2, Ra, Rb, Rc, Rd, a1, a2, m1, m2, a, b, c, and d are as defined in Formula 1,

One of Y9 and Y10 is a direct bond, and the other is S, O or NR ₃₅ ,

One of Y11 and Y12 is a direct bond, and the other is S, O or NR ₃₆ ,

R ₃₅ and R ₃₆ 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 alkenyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In the exemplary embodiment of the present specification, R ₂₁ to R ₂₄ and R ₃₁ to R ₃₆ 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 alkenyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

In the exemplary embodiment of the present specification, R ₂₁ to R ₂₄ and R ₃₁ to R ₃₆ are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

According to an exemplary embodiment of the present invention, the compound of Formula 1 is selected from the following compounds.

The heterocyclic compound of Formula 1 according to an exemplary embodiment of the present specification may be prepared by the manufacturing method described in Preparation Examples to be described later. However, the synthesis method of the compound in the following Preparation Example is only one example of the synthesis method of the compound of Formula 1, and if some or all of the synthesis steps are capable of the same reaction, other known in the art It can be replaced by synthetic methods. In addition, in the synthesis method of the compound in the following Preparation Example, other compounds of Formula 1 not described in the Preparation Example may also be synthesized by varying the reactant or by adding a reaction to further introduce a substituent.

In addition, the present specification provides an organic light-emitting device including the compound represented by Formula 1 above.

In an exemplary embodiment of the present specification, an organic light-emitting device comprising a first electrode, a second electrode, and one or more organic material layers disposed between the first electrode and the second electrode, wherein at least one of the organic material layers is It provides an organic light-emitting device comprising a compound represented by Formula 1.

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

In the exemplary embodiment of the present specification, the organic material layer includes at least one of a hole injection layer, a hole transport, and a layer that simultaneously injects and transports holes, and includes the hole injection layer, the hole transport layer, and the hole injection and transport. At least one of the simultaneous layers includes the compound of Formula 1 above.

In another exemplary embodiment, the organic material layer includes an emission layer, and the emission layer includes the compound of Formula 1 above.

In another exemplary embodiment, the organic material layer includes an emission layer, and the emission layer includes the compound of Formula 1 as a dopant.

In the exemplary embodiment of the present specification, the organic material layer includes an emission layer, and the emission layer includes a host; And the compound of Formula 1 above.

In the exemplary embodiment of the present specification, the host may be represented by the following Formula H.

[Formula H]

In the formula H,

L1 and L2 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group,

Ar11 and Ar12 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group,

G1 is hydrogen; heavy hydrogen; Halogen group; Cyano group; Silyl group; Alkyl group; Alkenyl group; Alkynyl group; Alkoxy group; Aryloxy group; Amino group; Aryl group; Or a heteroaryl group,

b1 is an integer of 0 to 8, and when b1 is 2 or more, G1 is the same as or different from each other.

In the exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; Or an arylene group.

In the exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; Or it is a C6-C20 arylene group.

In the exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; Or a C6-C16 arylene group.

In the exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; Or a C6-C12 arylene group.

In the exemplary embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; Phenylene group; Biphenylene group; Anthracenylene group; Or it is a naphthalene group.

In the exemplary embodiment of the present specification, Ar11 and Ar12 are the same as or different from each other, and each independently a C6-C24 aryl group.

In the exemplary embodiment of the present specification, Ar11 and Ar12 are the same as or different from each other, and each independently a C6-C22 aryl group.

In the exemplary embodiment of the present specification, Ar11 and Ar12 are the same as or different from each other, and each independently a C6-C18 aryl group.

In the exemplary embodiment of the present specification, Ar11 and Ar12 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Terphenyl group; Or a naphthyl group.

In the exemplary embodiment of the present specification, G1 is hydrogen.

In the exemplary embodiment of the present specification, b1 is 0.

In the exemplary embodiment of the present specification, Formula H may be any one selected from the following compounds.

In the exemplary embodiment of the present specification, the host is included in an amount of 50% by weight or more to 100% by weight based on the total weight of the emission layer.

In the exemplary embodiment of the present specification, the compound represented by Formula 1 is 0.5% to 30% by weight based on the total weight of the emission layer; 1% to 20% by weight; Or 1% to 10% by weight.

In the exemplary embodiment of the present specification, the organic material layer includes an electron suppression layer, and the electron suppression layer includes the compound of Formula 1 above.

In one embodiment of the present specification, the organic material layer includes at least one of an electron transport layer, an electron injection layer, and a layer that simultaneously transports and injects electrons, and simultaneously performs the electron transport layer, the electron injection layer, and the electron transport and injection. At least one of the layers includes the compound of Formula 1.

In another exemplary embodiment, the organic material layer includes an emission layer and an electron transport layer, and the electron transport layer includes the compound of Formula 1 above.

In one embodiment, the organic light emitting device includes two or more hole injection layers. The two or more hole injection layers may be formed of the same or different materials.

In one embodiment, the organic light emitting device includes an electron suppression layer.

In one embodiment of the present specification, the first electrode; A second electrode; And a light emitting layer provided between the first electrode and the second electrode. An organic light-emitting device comprising two or more organic material layers provided between the light-emitting layer and the first electrode or between the light-emitting layer and the second electrode, wherein at least one of the two or more organic material layers contains the compound of Formula 1 .

In the exemplary embodiment of the present specification, the organic material layer includes two or more electron transport layers, and at least one of the two or more electron transport layers includes the compound of Formula 1 above. Specifically, in the exemplary embodiment of the present specification, the compound of Formula 1 may be included in one of the two or more electron transport layers, and may be included in each of two or more electron transport layers.

In another exemplary embodiment, the organic light emitting device may be an organic light emitting device having a structure (normal type) in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.

In another embodiment, the organic light-emitting device may be an inverted type organic light-emitting device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.

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

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

For example, the structure of an organic light-emitting device according to an exemplary embodiment of the present specification is illustrated in FIGS. 1 to 3.

1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4. In such a structure, the compound of Formula 1 may be included in the emission layer.

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 3, an electron transport layer 8, and a cathode 4 I did it. In such a structure, the compound may be included in one or more of the hole injection layer, the hole transport layer, the emission layer, and the electron transport layer. In an exemplary embodiment, the compound of Formula 1 is included as a dopant in the emission layer.

3 shows a substrate 1, an anode 2, a first hole injection layer 9, a second hole injection layer 10, a hole transport layer 6, an electron suppression layer 11, a light emitting layer 3, and electrons. An example of an organic light-emitting device comprising a transport layer 8, an electron injection layer 12, and a cathode 4 is shown. In such a structure, the compound of Formula 1 may be included in the emission layer 3.

The organic light-emitting device of the present specification may be manufactured by materials and methods known in the art, except that at least one of the organic material layers includes the compound of the present specification, that is, the compound of Formula 1.

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

For example, the organic light emitting device of the present specification may be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate. At this time, using a physical vapor deposition (PVD) such as sputtering or e-beam evaporation, deposit a metal or a conductive metal oxide or an alloy thereof on the substrate to the anode. After forming an organic material layer including a hole injection layer, a hole transport layer, an emission layer, and an electron transport layer thereon, a material that can be used as a cathode may be deposited thereon. In addition to this method, an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

In addition, the compound of Formula 1 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 coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, and the like, but is not limited thereto.

In addition to this method, an organic light-emitting device may be manufactured by sequentially depositing an organic material layer and an anode material from a cathode material on a substrate. However, the manufacturing method is not limited thereto.

As the anode material, a material having a large work function is preferable so that holes can be smoothly injected into the organic material layer. Specific examples of the cathode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO:Al or SnO ₂ :Sb; Poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), conductive polymers such as polypyrrole and polyaniline, and the like, but are not limited thereto.

It is preferable that the cathode material is a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material that can be used in the present invention include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; There are multi-layered materials such as LiF/Al or LiO ₂ /Al, but are not limited thereto.

The hole injection layer is a layer for injecting holes received from an electrode into an adjacent layer. The hole injection material has the ability to transport holes and thus has a hole injection effect at the anode, an excellent hole injection effect for the light emitting layer or the light emitting material, and prevents the movement of excitons generated in the light emitting layer to the electron injection layer or the electron injection material. It is preferable to use a compound that prevents and has excellent thin film formation ability. The HOMO (highest occupied molecular orbital) of the hole injection material is preferably between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, perylene There are a series of organic substances, anthraquinone, and polyaniline and a polythiophene series of conductive polymers, but are not limited thereto.

The hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the emission layer, and the hole transport material is a material capable of transporting holes from the anode or the hole injection layer to the emission layer, and has high mobility for holes. The material is suitable. Specific examples include an arylamine-based organic material, a conductive polymer, and a block copolymer including a conjugated portion and a non-conjugated portion, but are not limited thereto.

The electron suppression layer is a layer that prevents excess electrons passing through the emission layer from moving in the direction of the hole transport layer. The electron suppressing material is preferably a material having a lower LUMO (Lowest Unoccupied Molecular Orbital) level than the transport transport layer, and may be selected as an appropriate material in consideration of the energy level of the surrounding layer. In one embodiment, an arylamine-based organic material may be used as the electron blocking layer, but is not limited thereto. In an exemplary embodiment, the electron blocking layer includes the compound represented by Formula 1 above.

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

The emission layer may include a host material and a dopant material.

As a host material for the light emitting layer, a condensed aromatic ring derivative or a heterocyclic-containing compound may be used. The condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and the heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

Examples of the dopant material for the light emitting layer include an aromatic amine derivative, a styrylamine compound, a boron complex, a fluoranthene compound, and a metal complex. As the aromatic amine derivative, as a condensed aromatic ring derivative having a substituted or unsubstituted arylamine group, pyrene, anthracene, chrysene, periflanthene and the like having an arylamine group may be used. As the styrylamine compound, a compound in which at least one arylvinyl group is substituted with a substituted or unsubstituted arylamine may be used. Examples of the styrylamine compound include, but are not limited to, styrylamine, styryldiamine, styryltriamine, and styryltetraamine. The metal complex may be an iridium complex or a platinum complex, but is not limited thereto.

The hole suppression layer serves to prevent holes from entering the cathode through the emission layer in the driving process of the organic light emitting device. As the hole suppressing material, it is preferable to use a material having a very low level of Highest Occupied Molecular Orbital (HOMO). The hole blocking material specifically includes TPBi, BCP, CBP, PBD, PTCBI, BPhen, etc., but is not limited thereto. In one exemplary embodiment, the hole blocking layer is 2-(3'-(9,9-dimethyl-9H-fluoren-2-yl)-[1,1'-biphenyl]-3-yl)-4 ,6-diphenyl-1,3,5-triazine.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer. As the electron transport material, a material capable of receiving electrons well from the cathode and transferring them to the emission layer, and a material having high mobility for electrons is suitable. Examples of the electron transport material include Al complex of 8-hydroxyquinoline; Complexes containing Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto. The electron transport layer can be used with any desired cathode material as used according to the prior art. In an exemplary embodiment, the cathode material is a material having a low work function; And an aluminum layer or a silver layer. Examples of the material having the low work function include cesium, barium, calcium, ytterbium, and samarium, and an aluminum layer or a silver layer may be formed on the layer after forming a layer with the material.

The electron injection layer is a layer for injecting electrons received from an electrode into the light emitting layer. The electron injection material has an ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect on the light emitting layer or the light emitting material, and prevents the movement of excitons generated from the light emitting layer to the hole injection layer, In addition, it is preferable to use a compound excellent in thin film forming ability. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, and their derivatives, metals Complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.

Examples of the metal complex compound include lithium 8-hydroxyquinolinato, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)( o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, etc. It is not limited to this.

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

The embodiments according to the present invention are for a more detailed description of the invention, and may be modified in various forms other than those described below, and the scope of the present invention is limited to the embodiments described below. I'm not trying to.

<Preparation of compound 1>

Preparation of compound 1-1

Ethyl 2-(4-bromonaphthalen-1-yl)acetate (30 g, 10.23 mmol) was completely dissolved in dichloromethane (40 mL) in a 500 mL round-bottom flask, and then cooled to 0° C. and stirred. After stirring for 10 minutes, titanium chloride (IV) (28 mL, 25.58 mmol) was slowly added dropwise. After stirring for about 30 minutes, triethylamine (49.9 mL, 35.8 mmol) was slowly added dropwise. After the reaction was completed, an aqueous ammonium chloride solution was added and stirred for about 15 minutes. The temperature was raised to room temperature, the organic layer was extracted, moisture was removed with anhydrous magnesium sulfate, filtered, and then concentrated under reduced pressure. A small amount of absolute ethanol was added to the concentrate, stirred for 10 minutes, and filtered to prepare compound 1-1 (29g, yield: 90%).

MS:[M+H] ⁺ = 584

Preparation of compound 1-2

At room temperature in a 1L round bottom flask Compound 1-1 (29g, 4.963mmol) and potassium hydroxide (13.9g, 24.81mmol) were added to a solution (580mL) in which anhydrous ethanol and water were mixed in a weight ratio of 1:1, and stirred at 80°C for 4 hours. I did. After completion of the reaction, it was cooled to 0°C. Neutralized with hydrogen chloride (HCl) and filtered. The obtained solid was washed with an excess of water to prepare compound 1-2 (24.4 g, yield: 99%).

MS:[M+H] ⁺ = 528

Preparation of compound 1-3

Compound 1-2 (24g, 4.543mmol) was heated and stirred at 90° C. for 14 hours with triflic acid (99.68ml, 113.59mmol) in a 1L round bottom flask. After the reaction was completed, it was cooled to 0° C., and water (229 mL) was slowly added dropwise. The resulting solid was filtered, the obtained solid was diluted with chloroform, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. A solid was precipitated in the concentrate with absolute ethanol to prepare compound 1-3 (13.2 g, yield: 60%).

MS:[M+H] ⁺ = 492

Preparation of compound 1-4

In a 500 mL round bottom flask, compound 1-3 (10 g, 2.031 mmol), diphenylamine (7.2 g, 4.266 mmol), bis (tri-tert butyl phosphine) palladium (0) (0.031 g, 0.006093 mmol), sodium- Tert-butoxide (7.79g, 8.124mmol) and xylene (130mL) were added, followed by heating and stirring. After the reaction was completed, the temperature was lowered to room temperature and filtered. Then, the solid was collected, dissolved in chloroform, water was added, stirred for 10 minutes, and then the organic layer was collected and concentrated under reduced pressure. The concentrate was precipitated with absolute ethanol to prepare compound 1-4 (10g, yield: 65.35%).

MS:[M+H] ⁺ = 668

Preparation of compound 1-5

2-bromodiphenyl (5g, 2.144mmol) was dissolved in tetrahydrofuran in a 250mL round bottom flask, cooled to 0°C, and stirred for 10 minutes. Thereafter, normal butyl lithium (2ml, 2.144mmol) was added and stirred for 30 minutes. Thereafter, compound 1-4 (14.33g, 0.747mmol) was completely dissolved in tetrahydrofuran (150mL) and stirred. After the reaction was completed, ammonia water (50ml) was added and stirred. After removing the water layer, the organic layer was collected, moisture was removed with anhydrous magnesium sulfate, filtered, and then concentrated under reduced pressure. The concentrate was precipitated with methyl tert-butyl ester to prepare compound 1-5 (18 g, yield: 86%).

MS:[M+H] ⁺ = 977

Preparation of compound 1-6

Compound 1-5 (5g, 0.511mmol) was dissolved in tetrahydrofuran (200ml) in a 250mL round-bottom flask, followed by stirring at 60°C with sulfuric acid (5mL). After completion of the reaction, water was added to precipitate a solid, followed by filtration. The solid was again dissolved in chloroform and stirred with water. The organic layer was collected, moisture was removed with anhydrous magnesium sulfate, filtered, and then concentrated under reduced pressure. The concentrate was precipitated with methyl tert-butyl ester to prepare compound 1-6 (4 g, yield: 83.3%).

MS:[M+H] ⁺ = 941

Preparation of compound 1

Compound 1-6 (4g, 0.425mmol) was completely dissolved in chloroform (CHCl ₃ ) in a 250 mL round-bottom flask and stirred at room temperature. N-bromosuccinimide (1.89g, 1.064mmol) was added to the reaction solution, stirred for 10 minutes, and then pyridine (0.92ml, 1.147mmol) was added, followed by stirring for 1 hour. After completion of the reaction, the mixture was filtered, washed with water and methyl tert-butyl ester, to prepare compound 1 (3.5 g, yield: 87%).

MS:[M+H] ⁺ = 939

<Preparation of compound 4>

Preparation of compound 4-1

Ethyl 2-(1-bromodibenzo[b,d]furan-4-yl)acetate (30g, 9.004mmol) was completely dissolved in dichloromethane (400mL) in a 500mL round bottom flask, cooled to O℃ and stirred. I did. After stirring for 10 minutes, titanium chloride (IV) (24.68mL, 22.51mmol) was slowly added dropwise. After stirring for about 30 minutes, triethylamine (37.64mL, 27.01mmol) was slowly added dropwise. After the reaction was completed, an aqueous ammonium chloride solution was added and stirred for about 15 minutes. The temperature was raised to room temperature, the organic layer was extracted, moisture was removed with anhydrous magnesium sulfate, filtered, and then concentrated under reduced pressure. A small amount of absolute ethanol was added to the concentrate, stirred for 10 minutes, and filtered to prepare compound 4-1 (29g, yield: 90%).

MS:[M+H] ⁺ = 664

Preparation of compound 4-2

In a 1L round bottom flask, compound 4-1 (29g, 4.365mmol), potassium hydroxide (12.2g, 21.82mmol), and anhydrous ethanol and water were mixed in a weight ratio of 1:1 at room temperature (580 mL). And stirred at 80° C. for 4 hours. After completion of the reaction, it was cooled to 0°C. Neutralized with hydrogen chloride (HCl) and filtered. The obtained solid was washed with water to prepare compound 4-2 (25 g, yield: 94%).

MS:[M+H] ⁺ = 608

Preparation of compound 4-3

Compound 4-2 (25g, 4.111mmol) was heated and stirred at 90° C. for 14 hours with Triflic acid (108.23ml, 123.33mmol) in a 1L round bottom flask. After the reaction was completed, the mixture was cooled to 0° C., and water (250 mL) was slowly added dropwise. The resulting solid was filtered, the obtained solid was diluted with chloroform, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. A solid was precipitated from the concentrated solution with absolute ethanol to prepare compound 4-3 (15g, yield: 63.8%).

MS:[M+H] ⁺ = 572

Preparation of compound 4-4

In a 500 mL round bottom flask, compound 4-3 (10 g, 1.747 mmol), di-para-tolylamine (7.24 g, 3.669 mmol), bis (tri-tert butyl phosphine) palladium (0) (0.026 g, 0.005241 mmol) , Sodium-tert-butoxide (6.7g, 6.988mmol) and xylene (150mL) were added, followed by heating and stirring. After the reaction was completed, the temperature was lowered to room temperature and filtered. Then, the solid was collected, dissolved in chloroform, water was added, stirred for 10 minutes, and then the organic layer was collected and concentrated under reduced pressure. The concentrate was precipitated with absolute ethanol to prepare compound 4-4 (11 g, yield: 78.23%).

MS:[M+H] ⁺ = 804

Preparation of compound 4

Using compound 4-4 instead of compound 1-5, compound 4 (2g, yield: 65%) was prepared in the same manner as in the method of preparing compound 1-6 and compound 1 above.

MS:[M+H] ⁺ = 1075

<Preparation of compound 5>

Preparation of compound 5-4

In a 500 mL round bottom flask, compound 4-3 (1 g, 1.747 mmol), 4-methyl-N- (4-trimethylsilyl) phenyl) aniline (7.24 g, 3.669 mmol), bis (tri-tert butyl phosphine) palladium ( 0) (0.026g, 0.005241mmol), sodium-tert-butoxide (6.7g, 6.988mmol) and xylene (150 mL) were added, followed by heating and stirring. After the reaction was completed, the temperature was lowered to room temperature and filtered. Then, the solid was collected, dissolved in chloroform, water was added, stirred for 10 minutes, and then the organic layer was collected and concentrated under reduced pressure. The concentrate was precipitated with absolute ethanol to prepare compound 5-4 (11 g, yield: 78.23%).

MS:[M+H] ⁺ = 921

Preparation of compound 5

Using compound 5-4 instead of compound 1-5, compound 5 (2.2g, yield: 64%) was prepared in the same manner as the method of preparing compound 1-6 and compound 1 above.

MS:[M+H] ⁺ = 1191

<Preparation of compound 7>

Except for using ethyl 2-(1-bromodibenzo[b,d]thiophen-4-yl)acetate instead of ethyl 2-(1-bromodibenzo[b,d]furan-4-yl)acetate , Compound 7 was prepared in the same manner as in the preparation method of compound 4.

<Example 1>

A glass substrate coated with a thin film of ITO (Indium Tin Oxide) to a thickness of 1,400Å was put in distilled water dissolved in a detergent and washed with ultrasonic waves. In this case, Fischer Co. product was used as a detergent, and distilled water secondarily filtered with a filter made by Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, it was repeated twice with distilled water to perform ultrasonic cleaning for 10 minutes. After washing with distilled water, ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

On the prepared ITO transparent electrode, the following [HI-A] and hexanitrile hexaazatriphenylene (HAT) were sequentially thermally vacuum deposited to a thickness of 650Å and 50Å, respectively, to inject the first hole injection layer and the second hole injection. A layer was formed.

After vacuum deposition of [HT-A] as a hole transport layer to a thickness of 600 Å, [HT-B] as an electron suppression layer was thermally vacuum deposited to a thickness of 50 Å.

Subsequently, the following host [BH-A] and a 4 wt% dopant [Compound 1] were vacuum-deposited to a thickness of 200 Å as a light emitting layer.

Subsequently, the following [ET-A] and [Liq] as the electron transport layer and the electron injection layer were thermally vacuum deposited to a thickness of 360Å at a weight ratio of 1:1, and then [Liq] was vacuum deposited to a thickness of 5Å.

An organic light-emitting device was manufactured by sequentially depositing magnesium and silver on the electron injection layer to a thickness of 220 Å at a weight ratio of 10:1 and aluminum to a thickness of 1000 Å to form a cathode.

<Examples 2 to 7>

An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compound of Table 1 was used instead of compound 1 in Example 1.

<Comparative Examples 1 to 4>

An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compound of Table 1 was used instead of compound 1 in Example 1.

By applying a current to the organic light emitting device prepared from Examples 1 to 7 and Comparative Examples 1 to 4, voltage, efficiency and lifetime (T ₉₅ ) were measured, and the results are shown in Table 1 below. At this time, the voltage and efficiency were measured by applying a current density of 10 mA/cm ² , and T ₉₅ means the time until the initial luminance decreases to 95% at the current density of 20 mA/cm ² .

compound Voltage(V) Efficiency (cd/A) T ₉₅ (hr) Example 1 Compound 1 3.85 6.40 72 Example 2 Compound 2 3.82 6.50 72 Example 3 Compound 3 3.80 6.59 76 Example 4 Compound 4 3.80 6.49 78 Example 5 Compound 5 3.78 6.67 79 Example 6 Compound 6 3.81 6.38 75 Example 7 Compound 7 3.80 6.60 75 Comparative Example 1 BD-A 4.15 6.01 57 Comparative Example 2 BD-B 6.25 2.78 2 Comparative Example 3 BD-C 5.56 5.12 15 Comparative Example 4 BD-D 6.12 2.80 4

As can be seen in Table 1, when the amine substituent was introduced into the core, the driving voltage of the device was low, and the current efficiency related to the luminous efficiency was remarkably improved. In addition, it was confirmed that the efficiency was increased in the same core when a trimethylsilane group was introduced into the amine substituent as in Compound 3 and Compound 5. In conclusion, it was confirmed that when the compound of Formula 1 of the present invention was used as a dopant in the emission layer of an organic light-emitting device, it had a remarkable effect on reducing the driving voltage and increasing the efficiency at the same time.

1: substrate
2: anode
3: light emitting layer
4: cathode
5: hole injection layer
6: hole transport layer
8: electron transport layer
9: first hole injection layer
10: second hole injection layer
11: electron suppression layer
12: electron injection layer

Claims (13)

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

In Formula 1,
Cy1 to Cy4 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic or polycyclic ring,
a to d are each 0 or 1, provided that a+b+c+d is 1 or more,
Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or combine with each other to form a ring,
Ar3 and Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or combine with each other to form a ring,
The Ar1 and Ar2 are bonded to each other to form an aromatic ring, or the Ar3 and Ar4 are bonded to each other to form an aromatic ring,
R1 and R2 are the same as or different from each other, and each independently deuterium; Halogen group; Nitrile group; -SiR ₄₀ R ₄₁ R ₄₂ ; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
R ₄₀ to R ₄₂ 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,
Ra to Rd are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
a1, a2, m1 and m2 are each an integer greater than or equal to 0,
When a1 is 2 or more, R1 is the same as or different from each other,
When a2 is 2 or more, R2 is the same as or different from each other,
When m1 is 2 or more, NRaRb is the same as or different from each other,
When m2 is 2 or more, NRcRd is the same as or different from each other,
m1+m2 is 1 or more. The compound of claim 1, wherein Cy1 to Cy4 are the same as or different from each other, and each independently a substituted or unsubstituted hydrocarbon ring. The method according to claim 1, wherein the formula 1 is a compound represented by the following formula 2 or formula 3:
[Formula 2]

[Formula 3]

In Formulas 2 and 3,
Ar1, Ar2, Ar3, Ar4, R1, R2, Ra. Rb. Rc and Rd are as defined in Formula 1,
a3 is an integer of 0 to 4, and when a3 is 2 or more, R1 is the same as or different from each other,
a4 is an integer from 0 to 6, and when a4 is 2 or more, R2 is the same as or different from each other,
m3 is an integer from 0 to 4, and when m3 is 2 or more, NRaRb is the same as or different from each other,
m4 is an integer from 0 to 6, and when m4 is 2 or more, NRcRd is the same as or different from each other,
m3+m4 is an integer from 1 to 10,
a3+m3 is an integer from 0 to 4,
a4+m4 is an integer of 0-6. The compound of claim 1, wherein the formula 1 is represented by any one of the following formulas 4 to 6:
[Formula 4]

[Formula 5]

[Formula 6]

In Formulas 4 to 6,
Ar1, Ar2, Ar3, Ar4, R1, R2, Ra, Rb, Rc and Rd are as defined in Formula 1,
a5 is an integer from 0 to 6, and when a5 is 2 or more, R2 is the same as or different from each other,
a6 is an integer from 0 to 6, and when a6 is 2 or more, R1 is the same as or different from each other, and
a7 is an integer from 0 to 8, and when a7 is 2 or more, R2 is the same as or different from each other,
m5 is an integer from 0 to 6, and when m5 is 2 or more, NRcRd is the same as or different from each other,
m6 is an integer from 0 to 6, and when m6 is 2 or more, NRaRb is the same as or different from each other,
m7 is an integer from 0 to 8, and when m7 is 2 or more, NRcRd is the same as or different from each other,
m5+m6 is an integer from 1 to 12,
m6+m7 is an integer from 1 to 14,
a5+m5 is an integer from 0 to 6,
a6+m6 is an integer from 0 to 6,
a7+m7 is an integer from 0 to 8. The compound of claim 1, wherein Cy1 to Cy4 are the same as or different from each other, and each independently a substituted or unsubstituted heterocycle. The compound of claim 1, wherein Formula 1 is represented by Formula 7 or Formula 8 below:
[Formula 7]

[Formula 8]

In Formulas 7 and 8,
Ar1, Ar2, Ar3, Ar4, R1, R2, Ra, Rb, Rc and Rd are as defined in Formula 1,
One of X1 and X2 is a direct bond, and the other is S, O or NR ₂₁ ,
R ₂₁ is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
a8 is an integer from 0 to 6, and when a8 is 2 or more, R2 is the same as or different from each other,
a9 is an integer from 0 to 4, and when a9 is 2 or more, R1 is the same as or different from each other,
m8 is an integer from 0 to 6, and when m8 is 2 or more, NRcRd is the same as or different from each other,
m9 is an integer of 0 to 4, and when m9 is 2 or more, NRaRb is the same as or different from each other,
m8+m9 is an integer from 1 to 10,
a8+m8 is an integer from 0 to 6,
a9+m9 is an integer of 0-4. The compound of claim 1, wherein Formula 1 is represented by the following Formula 9:
[Formula 9]

In Formula 9,
Ar1, Ar2, Ar3, Ar4, R1, R2, Ra, Rb, Rc and Rd are as defined in Formula 1,
One of X3 and X4 is a direct bond, and the other is S, O or NR ₂₂ ,
One of X5 and X6 is a direct bond, and the other is S, O or NR ₂₃ ,
R ₂₂ and R ₂₃ 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 alkenyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
a10 is an integer from 0 to 6, and when a10 is 2 or more, R1 is the same as or different from each other,
a11 is an integer from 0 to 6, and when a11 is 2 or more, R2 is the same as or different from each other,
m10 is an integer of 0 to 6, and when m10 is 2 or more, NRaRb is the same as or different from each other,
m11 is an integer from 0 to 6, and when m11 is 2 or more, NRcRd is the same as or different from each other,
m10+m11 is an integer from 1 to 12,
a10+m10 is an integer from 0 to 6,
a11+m11 is an integer of 0-6. The compound of claim 1, wherein the formula 1 is represented by the following formula 10:
[Formula 10]

In Formula 10,
Ar1, Ar2, Ar3, Ar4, R1, R2, Ra, Rb, Rc and Rd are as defined in Formula 1,
One of X7 and X8 is a direct bond, and the other is S, O or NR ₂₄ ,
R ₂₄ is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
a12 is an integer from 0 to 6, and when a12 is 2 or more, R1 is the same as or different from each other,
a13 is an integer from 0 to 6, and when a13 is 2 or more, R2 is the same as or different from each other,
m12 is an integer from 0 to 6, and when m12 is 2 or more, NRaRb is the same as or different from each other,
m13 is an integer from 0 to 6, and when m13 is 2 or more, NRcRd is the same as or different from each other,
m12+m13 is an integer from 1 to 12,
a12+m12 is an integer from 0 to 6,
a13+m13 is an integer of 0-6. The compound of claim 1, wherein the compound is any one selected from the following compounds:

. An organic light emitting device comprising a first electrode, a second electrode, and at least one organic material layer disposed between the first electrode and the second electrode, wherein at least one of the organic material layers is defined in any one of claims 1 to 9 Organic light-emitting device comprising the compound according to. The method according to claim 10, wherein the organic material layer comprises at least one of an electron injection layer, an electron transport layer, and a layer that simultaneously injects and transports electrons, and at least one of the layers simultaneously injecting and transporting electrons and electrons An organic light-emitting device, wherein one layer contains the compound. The organic light-emitting device of claim 10, wherein the organic material layer includes an emission layer, and the emission layer includes the compound. The method according to claim 10, wherein the organic material layer comprises at least one of a hole injection layer, a hole transport layer, and a layer for simultaneously transporting and injecting holes, and among the layers for simultaneously transporting and injecting holes, the hole injection layer, the hole transport layer, and An organic light-emitting device, wherein at least one layer contains the compound.

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