WO2019088751A1 - Compound and organic light emitting device comprising same - Google Patents

Abstract

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

Description

Compounds and organic light emitting devices containing them

This application claims priority to Korean Patent Application No. 10-2017-0145960, filed on November 3, 2017, and Korean Patent Application No. 10-2018-0132914 filed on November 1, 2018, The contents of which are incorporated herein by reference.

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a compound and an organic light emitting device including the same.

In order to commercialize an organic light emitting device, it is necessary to improve the efficiency of a light emitting material. For this purpose, studies on phosphorescent and retarding fluorescent materials have been actively conducted. However, in the case of the above-mentioned phosphorescent material, there is a problem that the cost of the metal complex required to realize phosphorescence is high and the lifetime is short, although high efficiency can be achieved.

Recently, the introduction of the concept of thermally activated delayed fluorescence (TADF) in the case of the retarded fluorescent material has revealed a highly efficient green fluorescent material having a high external quantum efficiency as well as a fluorescent material. The concept of thermally activated delayed fluorescence (TADF) is a phenomenon in which the inverse energy transfer from the excited triplet state to the excited singlet state is caused by thermal activation, leading to fluorescence emission. Generally, the lifetime It is called delayed fluorescence in that long luminescence occurs. Since the retardation fluorescent material can use both fluorescence emission and phosphorescence emission, the problem of the cost of the phosphorescent material can be solved in that the problem of the external quantum efficiency of the conventional fluorescent material can be solved and the metal complex is not required.

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

The present invention provides a compound represented by the following formula (1).

[Chemical Formula 1]

In Formula 1,

X1 is O or S,

Ar1 and Ar2 are the same or different and each independently represents a substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

R1 to R4 are the same or different from each other and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; Carbonyl group; An ester group; Imide; Amide group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

r1 is an integer of 1 to 6,

r2 and r3 are each an integer of 1 to 7,

r4 is an integer of 1 to 5,

When each of r1 to r4 is 2 or more, the structures in parentheses of 2 or more are equal to or different from each other.

Also, the present specification discloses a plasma display panel comprising a first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes the compound described above.

The organic light emitting device including the compound represented by Chemical Formula 1 according to one embodiment of the present invention can improve the efficiency, improve the driving voltage and / or the lifetime characteristics.

1 shows an organic light emitting device according to an embodiment of the present invention.

<Description of Symbols>

10: Organic light emitting device

20: substrate

30: first electrode

40: light emitting layer

50: second electrode

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

The present invention provides a compound represented by the above formula (1).

The compound represented by Chemical Formula 1 according to one embodiment of the present invention includes a triazine group serving as an electron acceptor to facilitate electron injection, and the organic light emitting device including the compound has high efficiency and long life.

In addition, since the compound represented by Formula 1 is separated with a triazine group acting as an electron acceptor and a biscarvazole acting as an electron pair between the linker, the retarded fluorescent property is enhanced and the organic light- Can be improved.

According to one embodiment of the present invention, the compound represented by Formula 1 is a retardation fluorescent compound.

In the general organic light emitting device, the number of excitons generated in the singlet and triplet is generated at a ratio of 25:75 (monomodal: triplet), and depending on the type of emission due to exciton migration, fluorescence emission, It can be divided into luminescence. In the case of the phosphorescent light emission, it means that the exciton of the excited state moves to the ground state and emits light. In the case of the fluorescent emission, the exciton of the excited state is in the ground state ground state, and the light is emitted. The thermal activation delay fluorescent light emission is induced in the excited state from the excited state to the excited state, and the singlet excited state Means that the exciton moves to the ground state to cause fluorescent light emission.

The thermal activation delayed fluorescence emission is distinguished from fluorescence emission in that the peak position of the emission spectrum is the same as that of fluorescence but the decay time is long. The decay time is long, but the peak position of the emission spectrum differs from the phosphorescence spectrum and S ₁ -T ₁ &lt; / RTI &gt; energy difference. Here, S ₁ is a singlet energy level, and T ₁ is a triplet energy level.

In this specification, when a part is referred to as " including " an element, it is to be understood that it may include other elements as well, without departing from the other elements unless specifically stated otherwise.

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

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

As used herein, the term " substituted or unsubstituted " A halogen group; A nitrile group; A nitro group; Imide; Amide group; Carbonyl group; An ester group; A hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group, or that at least two of the substituents exemplified above are substituted with a substituent to which they are linked, or have no substituent. For example, " a substituent to which at least two substituents are connected " may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected.

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

In the present specification, the number of carbon atoms in the imide group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

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

In the present specification, the carbon number of the carbonyl group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

 In the present specification, the ester group may be substituted with an ester group oxygen in a straight chain, branched chain or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 30 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec- N-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-hexyl, Cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethyl Heptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like.

In the present specification, the cycloalkyl group is not particularly limited, but is preferably a group having 3 to 30 carbon atoms. Specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, But are not limited to, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, isobutyl, sec-butyl, It is not.

In the present specification, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specific examples include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n Butyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy and the like. But is not limited thereto.

In this specification, the amine group is -NH ₂ ; An alkylamine group; N-alkylarylamine groups; An arylamine group; An N-arylheteroarylamine group; An N-alkylheteroarylamine group, and a heteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include methylamine, dimethylamine, ethylamine, diethylamine, phenylamine, naphthylamine, biphenylamine, anthracenylamine, 9-methyl- , Diphenylamine group, N-phenylnaphthylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-phenylbiphenylamine group, N-phenylnaphthylamine group, Phenylnaphthylenediamine group, N-phenylphenylenediamine group, N-phenyltriphenylamine group, N-phenylphenanthrenylamine group, N-phenylphenanthrenylamine group, Group, an N-phenanthrenylfluorenylamine group, and an N-biphenylfluorenylamine group, but the present invention is not limited thereto.

In the present specification, the N-alkylarylamine group means an amine group in which N of the amine group is substituted with an alkyl group and an aryl group.

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

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

In the present specification, the alkyl group in the alkylamine group, the N-arylalkylamine group, the alkylthio group, the alkylsulfoxy group and the N-alkylheteroarylamine group is the same as the alkyl group described above. Specific examples of the alkyloxy group include a methylthio group, an ethylthio group, a tert-butylthio group, a hexylthio group and an octylthio group. Examples of the alkylsulfoxy group include a mesyl group, an ethylsulfoxy group, a propylsulfoxy group, And the like, but the present invention is not limited thereto.

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, Butenyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, (Diphenyl-1-yl) vinyl-1-yl, stilbenyl, stilenyl, and the like.

In the present specification, the alkynyl group may be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably from 2 to 30. Specific examples include but are not limited to ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl, octynyl, nonynyl, And the like, but the present invention is not limited thereto.

In the present specification, 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, However, the present invention is not limited thereto.

In the present specification, the boron group may be -BR ₁₀₀ R ₁₀₁ , wherein R ₁₀₀ and R ₁₀₁ are the same or different and each independently hydrogen; heavy hydrogen; halogen; A nitrile group; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted, straight or branched chain alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.

In the present specification, the phosphine oxide group specifically includes a diphenylphosphine oxide group, a dinaphthylphosphine oxide group, and the like, but is not limited thereto.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.

When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 30 carbon atoms. Specific examples of the monocyclic aryl group include a phenyl group, a biphenyl group, a terphenyl group, and the like, but are not limited thereto.

When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. And preferably 10 to 30 carbon atoms. Specific examples of the polycyclic aryl group include naphthyl, anthracenyl, phenanthryl, triphenyl, pyrenyl, phenalenyl, perylenyl, , But is not limited thereto.

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

When the fluorenyl group is substituted,

And

And the like. However, the present invention is not limited thereto.

As used herein, the term " adjacent " means that the substituent is a substituent substituted on an atom directly connected to the substituted atom, a substituent stereostructically closest to the substituent, or another substituent substituted on the substituted atom . For example, two substituents substituted in the benzene ring to the ortho position and two substituents substituted on the same carbon in the aliphatic ring may be interpreted as " adjacent " groups to each other.

In the present specification, the aryl group in the aryloxy group, the arylthioxy group, the arylsulfoxy group, the N-arylalkylamine group, the N-arylheteroarylamine group and the arylphosphine group is the same as the aforementioned aryl group. Specific examples of the aryloxy group include a phenoxy group, a p-tolyloxy group, a m-tolyloxy group, a 3,5-dimethyl-phenoxy group, a 2,4,6- trimethylphenoxy group, a p- Naphthyloxy group, 4-methyl-1-naphthyloxy group, 5-methyl-2-naphthyloxy group, 1-anthryloxy group , 2-anthryloxy group, 9-anthryloxy group, 1-phenanthryloxy group, 3-phenanthryloxy group and 9-phenanthryloxy group and the arylthioxy group includes phenylthio group, 2- Methylphenylthio group, 4-tert-butylphenylthio group and the like, and examples of the arylsulfoxy group include a benzene sulfoxide group and a p-toluenesulfoxy group. However, the present invention is not limited thereto.

In the present specification, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, or a substituted or unsubstituted diarylamine group. The aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group. The arylamine group having at least two aryl groups may contain a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time. For example, the aryl group in the arylamine group may be selected from the examples of the aryl group described above.

In the present specification, the heteroaryl group includes at least one non-carbon atom and at least one hetero atom. Specifically, the hetero atom may include one or more atoms selected from the group consisting of O, N, Se and S, and the like. The number of carbon atoms is not particularly limited, but is preferably 2 to 30 carbon atoms, and the heteroaryl group may be monocyclic or polycyclic. Examples of the heterocyclic group include a thiophene group, a furanyl group, a pyrrolyl group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a pyridyl group, a bipyridyl group, a pyrimidyl group, A substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, , An isoquinolyl group, an indolyl group, a carbazolyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzocarbazolyl group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, Phenanthroline, isoxazolyl group, thiadiazolyl group, phenothiazinyl group, and dibenzofuranyl group, but the present invention is 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 heteroarylamine group having two or more heteroaryl groups may include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group at the same time. For example, the heteroaryl group in the heteroarylamine group may be selected from the examples of the above-mentioned heteroaryl group.

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

According to one embodiment of the present invention, in the general formula (1), R 1 to R 4 are hydrogen.

According to one embodiment of the present invention, the formula (1) is represented by the following formula (1-1).

[Formula 1-1]

In Formula 1-1,

X1, Ar1 and Ar2 are as defined in the above formula (1).

According to one embodiment of the present invention, the formula (1) is represented by the following formula (1-2) or (1-3).

[Formula 1-2]

[Formula 1-3]

In Formulas 1-2 and 1-3,

X1, Ar1 and Ar2 are as defined in the above formula (1).

According to one embodiment of the present invention, Ar 1 and Ar 2 are the same or different and each independently represents a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.

According to one embodiment of the present invention, Ar 1 and Ar 2 are the same or different and each independently represents an aryl group substituted or unsubstituted with an alkyl group; Or a heteroaryl group substituted or unsubstituted with an aryl group.

According to one embodiment of the present invention, in the general formula (1), Ar1 and Ar2 are the same or different and are each independently a phenyl group; A biphenyl group; A fluorenyl group substituted or unsubstituted with an alkyl group; A dibenzofurane group; A dibenzothiophene group; Or a carbazolyl group substituted or unsubstituted with an aryl group.

According to one embodiment of the present invention, in the general formula (1), Ar1 and Ar2 are the same or different and are each independently a phenyl group; A biphenyl group; A fluorenyl group substituted or unsubstituted with a methyl group; A dibenzofurane group; A dibenzothiophene group; Or a carbazolyl group substituted or unsubstituted with a phenyl group.

According to one embodiment of the present disclosure, Formula 1 is selected from the following compounds.

According to one embodiment of the present invention, the triplet energy level of the compound represented by Formula 1 is 2.1 eV or more, preferably 2.1 eV or more and 3.0 eV or less, 2.2 eV or more and 3.0 eV or less, 2.4 eV or more It can be less than 2.9 eV. When the triplet energy level of the compound represented by the formula (1) satisfies the above-mentioned range, the electron injection becomes easy and the formation ratio of the exciton increases, so that the luminous efficiency is increased.

According to one embodiment of the present invention, ΔE _st of the compound represented by Formula 1 is 0 eV to 0.3 eV, preferably 0 eV to 0.2 eV. When the difference between the singlet energy level and the triplet energy level of the compound represented by the above formula (1) satisfies the above range, the exciton generated in the triplet is converted to a singlet state by RISC The migration rate and speed are increased, and the time for the excitons to stay in the triplet is reduced, so that the efficiency and lifetime of the organic light emitting device are advantageously increased.

According to one embodiment of the present invention, the ΔE _st of the compound represented by Formula 1 is less than 0.2 eV. Here,? E _st means the difference between the singlet energy level (S ₁ ) and the triplet energy level (T ₁ ) of the compound represented by the formula ( ₁ ).

When the? E _st of the compound represented by the formula (1) is less than 0.2 eV, the transition from triplet to singlet effectively occurs and the external luminous efficiency and lifetime of the device are increased. When ΔE _st is 0.2 eV or more, The transition from the term to the singular is difficult to occur and the efficiency and lifetime are lowered.

According to one embodiment of the present disclosure, there is provided a liquid crystal display comprising: a first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes a compound represented by the general formula (1) .

According to one embodiment of the present disclosure, the organic material layer of the organic light emitting device 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 injecting layer, a hole transporting layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transporting layer, and an electron injecting layer 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 layers.

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

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

According to one embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer includes a compound represented by the general formula (1).

According to one embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer includes the compound represented by the general formula (1) as a dopant of the light emitting layer.

According to one embodiment of the present invention, the light emitting material of the light emitting layer is a material capable of emitting light in the visible light region by transporting and combining holes and electrons from the hole transporting layer and the electron transporting layer, At least one of the singlet energy and the triplet energies has a higher value than the light emitting material of the compound and has a hole transporting ability and an electron transporting ability and also has a long wavelength of light emission Can be prevented, and an organic compound having a high glass transition temperature can be included as a host.

According to one embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer includes a host.

According to one embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer includes at least one selected from a condensed aromatic ring derivative and a heterocyclic compound as a host of the light emitting layer.

According to one embodiment of the present invention, the condensed aromatic ring derivative includes an anthracene derivative, a pyrene derivative, a naphthalene derivative, a pentacene derivative, a phenanthrene compound, a fluoranthene compound and the like. Examples of the heterocyclic compound include carbazole derivatives , Dibenzofuran derivatives, ladder furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

According to one embodiment of the present invention, the host may include any one or more selected from the following compounds, but is not limited thereto.

According to one embodiment of the present invention, the organic material layer includes a light emitting layer, and the light emitting layer contains the compound represented by the general formula (1) as a dopant of the light emitting layer, and at least one selected from a condensed aromatic ring derivative and a heterocyclic compound As a host of the light emitting layer.

According to one embodiment of the present disclosure, the light emitting layer contains the dopant and the host in a weight ratio of 1:99 to 50:50.

According to one embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer includes at least one selected from the group consisting of a dopant including the compound represented by the formula (1) and the condensed aromatic ring derivative and a heterocyclic compound Lt; / RTI &gt; in a weight ratio of 1:99 to 50:50.

According to one embodiment of the present invention, the organic layer includes a light emitting layer, and the light emitting layer may further include a fluorescent emitter.

When the fluorescent layer includes the fluorescent emitter, the fluorescent emitter and the host are contained in a weight ratio of 0.5: 99.5 to 10: 90.

In the present specification, the fluorescent emitter can be an anthracene compound, a pyrene compound, a boron compound or the like, but is not limited thereto.

The organic luminescent device of the present invention includes the compound of the present specification as the dopant of the luminescent layer, that is, the compound represented by the above-mentioned formula (1), and is selected from the above-mentioned condensed aromatic ring derivative and the heterocyclic compound But may be made of materials and methods known in the art, except for including one or more of the foregoing.

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

For example, the organic light emitting device of the present invention can be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate. At this time, a metal or a metal oxide having conductivity or an alloy thereof is deposited on the substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation Forming a first electrode, forming an organic material layer including a hole injecting layer, a hole transporting layer, a light emitting layer, and an electron transporting layer on the first electrode, and depositing a material usable as a second electrode thereon. In addition to such a method, an organic light emitting device can be formed by sequentially depositing a second electrode material, an organic material layer, and a first electrode material on a substrate. The heterocyclic compound represented by Formula 1 may be formed into an organic layer by a solution coating method as well as a vacuum deposition method in the production of an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating and the like, but is not limited thereto.

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

According to another embodiment of the present invention, the first electrode is a cathode and the second electrode is a cathode.

As the anode material, a material having a large work function is preferably used so that hole injection can be smoothly conducted 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); ZnO: Al or SnO _2: a combination of a metal and an oxide such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline.

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

The hole injecting layer is a layer for injecting holes from an electrode. The hole injecting material has a hole injecting effect, and has a hole injecting effect on the light emitting layer or a light emitting material. A compound which prevents the migration of excitons to the electron injecting layer or the electron injecting material and is also excellent in the thin film forming ability is preferable. It is preferable that the highest occupied molecular orbital (HOMO) of the hole injecting material be between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injecting material include metal porphyrin, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, and perylene- , Anthraquinone, polyaniline and polythiophene-based conductive polymers, but the present invention is not limited thereto.

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

The electron transporting layer is a layer that receives electrons from the electron injecting layer and transports electrons to the light emitting layer. The electron transporting material is a material capable of transferring electrons from the cathode well to the light emitting layer. Do. Specific examples include an 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 transporting layer can be used with any desired cathode material as used according to the prior art. In particular, examples of suitable cathode materials are conventional materials with a low work function followed by an aluminum or silver layer, specifically cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum or silver layer.

The electron injection layer is a layer for injecting electrons from the electrode. The electron injection layer has an ability to transport electrons, has an electron injection effect from the cathode, and has an excellent electron injection effect with respect to the light emitting layer or the light emitting material. A compound which prevents migration to a layer and is excellent in a thin film forming ability is preferable. Specific examples thereof include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, A complex compound and a nitrogen-containing five-membered ring derivative, 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- Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8- hydroxyquinolinato) gallium, bis (10- Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8- quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, and the like, But is not limited thereto.

The organic light emitting device according to the present invention may be of a top emission type, a back emission type, or a both-side emission type, depending on the material used.

Hereinafter, the present invention will be described in detail by way of examples with reference to the drawings. However, the embodiments according to the present disclosure can be modified in various other forms, and the scope of the present specification is not construed as being limited to the embodiments described below. Embodiments of the present disclosure are provided to more fully describe the present disclosure to those of ordinary skill in the art.

<Production Example>

The process for preparing the material of the present invention begins with the reaction of synthesizing bromine and chlorine substituted dibenzofurane or dibenzothiophene as follows. Dibenzofuran in which bromine and chlorine are substituted, or fluorine and chlorine are substituted. The compounds of the specific examples were synthesized by introducing an epenergent triazine and a biscarbazole.

Production Example 1-1 Synthesis of Compound 1-A

[Reaction Scheme 1-1]

(89.5 mmol) of 2-bromo-1-chloro-4-fluoro-3-iodobenzene, 90 mmol of a (2-hydroxyphenyl) boronic acid seed, 200 mL of tetrahydrofuran and 100 mL of water were mixed . 268.5 mmol of potassium carbonate and 1 mmol% of tetrakis triphenylphosphine palladium were added thereto and stirred for 3 hours under reflux. After the reaction, the organic layer was extracted from the reaction solution returned to room temperature and then distilled. The residue was purified by column chromatography with chloroform / hexane to obtain 21.6 g (yield 80%) of the compound 1-A.

MS [M + H] &lt; + &gt; = 301

PREPARATION EXAMPLE 1-2 Synthesis of Compound 1-B

[Reaction Scheme 1-2]

30 g (89.5 mmol) of 1-bromo-4-chloro-3-fluoro-2-iodobenzene, 90 mmol of benzene thiol, 200 mL of tetrahydrofuran and 100 mL of water are mixed and heated to 60 ° C. 268.5 mmol of potassium carbonate and 1 mmol% of tetrakis triphenylphosphine palladium were added thereto and stirred for 3 hours under reflux. After the reaction, the organic layer was extracted from the reaction solution returned to room temperature and then distilled. The residue was purified by column chromatography with chloroform / hexane to obtain 22.8 g (yield 70%) of the compound 1-B.

MS [M + H] &lt; + &gt; = 364

PREPARATION EXAMPLE 2-1 Synthesis of Compound 2-A

[Reaction Scheme 2-1]

20 g (66.3 mmol) of the compound 1-A, 200 mL of dimethylformamide and 133 mmol of potassium carbonate were mixed and heated to 100 DEG C for 5 hours. After the reaction, the reaction solution returned to room temperature was reprecipitated in water to obtain a solid. The resulting solid was purified by column chromatography with chloroform / hexane to obtain 17.7 g (yield 95%) of the compound 2-A.

MS [M + H] &lt; + &gt; = 281

PREPARATION EXAMPLE 2-2 Synthesis of Compound 2-B

[Reaction Scheme 2-2]

20 g (54.8 mmol) of the compound 1-B, 200 mL of dimethylformamide, 110 mmol of potassium acetate and 2 mmol% of palladium acetate were mixed and stirred for 6 hours under reflux. After the reaction, the reaction solution returned to room temperature was reprecipitated in water to obtain a solid. The resulting solid was purified by column chromatography with chloroform / hexane to obtain 9.7 g (yield 75%) of the compound 2-B.

MS [M + H] &lt; + &gt; = 236

PREPARATION EXAMPLE 3-1 Synthesis of Compound 3-A

[Reaction Scheme 3-1]

10.5 g (35.5 mmol) of the compound 2-A, 35.5 mmol of 9-phenyl-9H, 9'H-3,3'-biscarbazole, 100 ml of toluene and 53.3 mmol of sodium tertbutoxide were mixed and heated to 100 ° C. 1 mmol% of tetrakis triphenylphosphine palladium was added thereto, and the mixture was stirred in reflux for 3 hours. After the reaction, the reaction solution returned to room temperature was extracted with water, and the organic layer was distilled to obtain a solid. The resulting solid was purified by column chromatography with chloroform / hexane to obtain 19.8 g (yield: 92%) of the compound 3-A.

MS [M + H] &lt; + &gt; = 609

<Production example 3-2> Synthesis of compound 3-B

[Reaction Scheme 3-2]

35.5 mmol of 9-phenyl-9H, 9'H-2,3'-bicycarbazole, 100 mL of toluene and 53.3 mmol of sodium tertbutoxide was mixed with 10 g (35.5 mmol) of the compound 2-A and heated to 100 ° C. 1 mmol% of tetrakis triphenylphosphine palladium was added thereto, and the mixture was stirred in reflux for 3 hours. After the reaction, the reaction solution returned to room temperature was extracted with water, and the organic layer was distilled to obtain a solid. The resulting solid was purified by column chromatography with chloroform / hexane to obtain 20.1 g (yield: 93%) of the compound 3-B.

MS [M + H] &lt; + &gt; = 609

PREPARATION EXAMPLE 3-3 Synthesis of Compound 3-C

[Reaction Scheme 3-3]

10 g (42.2 mmol) of the compound 2-B, 9.2-phenyl-9H, 42.2 mmol of 9'H-3,3'-biscarbazole, 100 ml of toluene and 63.3 mmol of sodium tertbutoxide were mixed and heated to 100 ° C. 1 mmol% of tetrakis triphenylphosphine palladium was added thereto, and the mixture was stirred in reflux for 3 hours. After the reaction, the reaction solution returned to room temperature was extracted with water, and the organic layer was distilled to obtain a solid. The resulting solid was purified by column chromatography with chloroform / hexane to obtain 23.7 g (yield: 90%) of the compound 3-C.

MS [M + H] &lt; + &gt; = 625

<Production example 4-1> Synthesis of compound 4-A

[Reaction Scheme 4-1]

10 g (16.4 mmol) of the compound 3-A, 16.4 mmol of bis (pinacolato) diboron, 49.2 mmol of potassium acetate and 100 mL of 1,4-dioxane were mixed and heated to 100 ° C. 1 mmol% of palladium acetate was added thereto, and the mixture was stirred in a reflux condition for 12 hours. After the reaction, the reaction solution returned to room temperature was extracted with water, and the organic layer was distilled to obtain a solid. The resulting solid was purified by column chromatography with chloroform / hexane to obtain 10 g (yield: 87%) of the compound 4-A.

MS [M + H] &lt; + &gt; = 701

<Production example 4-2> Synthesis of compound 4-B

[Reaction Scheme 4-2]

10 g (16.4 mmol) of the compound 3-B, 16.4 mmol of bis (pinacolacto) diboron, 49.2 mmol of potassium acetate and 100 ml of 1,4-dioxane were mixed and heated to 100 占 폚. 1 mmol% of palladium acetate was added thereto, and the mixture was stirred in a reflux condition for 12 hours. After the reaction, the reaction solution returned to room temperature was extracted with water, and the organic layer was distilled to obtain a solid. The obtained solid was purified by column chromatography with chloroform / hexane to obtain 9.8 g (yield: 85%) of the compound 4-B.

MS [M + H] &lt; + &gt; = 701

<Production example 4-3> Synthesis of compound 4-C

[Reaction Scheme 4-3]

10 mmol (16 mmol) of the compound 3-C, 16 mmol of bis (pinacolacto) diboron, 48 mmol of potassium acetate and 100 mL of 1,4-dioxane were mixed and heated to 100 占 폚. 1 mmol% of palladium acetate was added thereto, and the mixture was stirred in a reflux condition for 12 hours. After the reaction, the reaction solution returned to room temperature was extracted with water, and the organic layer was distilled to obtain a solid. The resulting solid was purified by column chromatography with chloroform / hexane to obtain 9.7 g (yield: 85%) of the compound 4-C.

MS [M + H] &lt; + &gt; = 717

Production Example 5-1 Synthesis of Compound 1

[Reaction Scheme 5-1]

5 g (7.1 mmol) of the compound 4-A, 7.1 mmol of 2-chloro-4,6-diphenyl-1,3,5-triazine, 50 mL of tetrahydrofuran and 25 mL of water were mixed and heated to 60 ° C. 21.3 mmol of potassium carbonate and 1 mmol% of tetrakis triphenylphosphine palladium were added thereto and stirred for 3 hours in a reflux state. After the reaction, the organic layer was extracted from the reaction solution returned to room temperature and then distilled. The residue was purified by column chromatography with chloroform / hexane to obtain 5.1 g (yield: 90%) of Compound 1 .

MS [M + H] &lt; + &gt; = 806

&Lt; Preparation Example 5-2 > Synthesis of Compound 2

[Reaction Scheme 5-2]

7.1 mmol of the compound 4-A, 7.1 mmol of 2 - ([1,1'-diphenyl] -3-yl) -4-chloro-6-phenyl-1,3,5-triazine, 50 mL and 25 mL of water were mixed and heated to 60 &lt; 0 &gt; C. 21.3 mmol of potassium carbonate and 1 mmol% of tetrakis triphenylphosphine palladium were added thereto and stirred for 3 hours in a reflux state. After the reaction, the organic layer was extracted from the reaction solution returned to room temperature and then distilled. The residue was purified by column chromatography with chloroform / hexane to obtain 5.5 g (yield: 88%) of Compound 2 .

MS [M + H] &lt; + &gt; = 882

<Production example 5-3> Synthesis of compound 3

[Reaction Scheme 5-3]

5 g (7.1 mmol) of the compound 4-B, 7.1 mmol of 2-chloro-4,6-diphenyl-1,3,5-triazine, 50 mL of tetrahydrofuran and 25 mL of water were mixed and heated to 60 ° C. 21.3 mmol of potassium carbonate and 1 mmol% of tetrakis triphenylphosphine palladium were added thereto and stirred for 3 hours in a reflux state. After the reaction, the organic layer was extracted from the reaction solution returned to room temperature and then distilled. The residue was purified by column chromatography with chloroform / hexane to obtain 5.2 g (yield: 91%) of Compound 3 .

MS [M + H] &lt; + &gt; = 806

<Production example 5-4> Synthesis of compound 4

[Reaction 5-4]

5.1 mmol (7.1 mmol) of the compound 4-C, 7.1 mmol of 2-chloro-4,6-diphenyl-1,3,5-triazine, 50 mL of tetrahydrofuran and 25 mL of water were mixed and heated to 60 ° C. 21.3 mmol of potassium carbonate and 1 mmol% of tetrakis triphenylphosphine palladium were added thereto and stirred for 3 hours in a reflux state. After the reaction, the organic layer was extracted from the reaction solution returned to room temperature and then distilled. The residue was purified by column chromatography with chloroform / hexane to obtain 5.2 g (yield 90%) of Compound 4. [

MS [M + H] &lt; + &gt; = 822

<Production example 5-5> Synthesis of compound 5

[Reaction Scheme 5-5]

In the same manner as in Production Example 5-4, except that 7.1 mmol of 2-chloro-4,6-diphenyl-1,3,5-triazine was used instead of 2 - ([1,1'-biphenyl] Chloro-6-phenyl-1,3,5-triazine (7.1 mmol) was used to obtain 5.6 g of Compound 5 (yield: 88%).

MS [M + H] &lt; + &gt; = 898

<Production example 5-6> Synthesis of compound 6

[Reaction Scheme 5-6]

In the same manner as in Production Example 5-2, except that 7.1 mmol of 2 - ([1,1'-diphenyl] -3-yl) -4-chloro-6-phenyl- - (dibenzo [b, d] furan-4-yl) -6-phenyl-1,3,5-triazine, except for using 7.1 mmol equally produced to give the compound 6 5.4g (85% yield) .

MS [M + H] &lt; + &gt; = 896

<Production example 5-7> Synthesis of compound 7

[Reaction 5-7]

7.1 mmol of the compound 4-C, 7.1 mmol of 2-chloro-4- (dibenzo [b, d] thiophen-2-yl) -6-phenyl-1,3,5-triazine, 50 mL of furan and 25 mL of water were mixed and heated to 60 ° C. 21.3 mmol of potassium carbonate and 1 mmol% of tetrakis triphenylphosphine palladium were added thereto and stirred for 3 hours in a reflux state. After the reaction, the organic layer was extracted from the reaction solution returned to room temperature and then distilled. The residue was purified by column chromatography with chloroform / hexane to obtain 5.7 g (yield: 87%) of Compound 7 .

MS [M + H] &lt; + &gt; = 928

<Production example 5-8> Synthesis of compound 8

[Reaction Scheme 5-8]

In the same manner as in Production Example 5-2, except that 7.1 mmol of 3- (4-chloro-phenyl) -1,3,5-triazine was used in place of 7.1 mmol of 2 - ([1,1'- chloro-6-phenyl-1,3,5-triazin-2-yl) -9-phenyl -9H- carbazole except for using 7.1 mmol sol and the same manufacturing compound 8 5.7 g (yield 83%) of the .

MS [M + H] &lt; + &gt; = 971

<Production example 5-9> Synthesis of compound 9

[Reaction Scheme 5-9]

In the same manner as in Production Example 5-2, except that 7.1 mmol of 2 - ([1,1'-diphenyl] -3-yl) -4-chloro-6-phenyl- - (9,9-dimethyl--9H- fluorene -2-yl) except for using the same to manufacture 6-phenyl-1,3,5-triazine 7.1 mmol 5.4g compound 9 (yield: 82% ).

MS [M + H] &lt; + &gt; = 922

By using the same reaction as the above reaction formula, bicabaazole and triazine were variously introduced to synthesize the substances in the specific examples.

<Examples>

[Example 1]

In the present embodiment, the compound represented by Formula 1 according to one embodiment of the present invention is incorporated into a light emitting layer together with a host material (m-CBP) having a triplet value of 2.5 eV or more to prepare an organic light emitting device, Respectively.

The glass substrate coated with ITO (indium tin oxide) thin film with a thickness of 1,000 Å was immersed in distilled water containing detergent and washed with ultrasonic waves. In this case, Fischer Co. was used as a detergent, and distilled water filtered by a filter of Millipore Co. was used as distilled water. The ITO was washed for 30 minutes and then washed twice with distilled water and ultrasonically cleaned for 10 minutes. After the distilled water was washed, it was ultrasonically washed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. Further, the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transported by a vacuum evaporator. Each thin film was laminated on the prepared ITO transparent electrode with a vacuum degree of 5.0 x 10 &lt; ^-4 &gt; Pa. First, hexanitrile hexaazatriphenylene (HAT) was thermally vacuum deposited on ITO to a thickness of 500 Å to form a hole injection layer.

N-phenylamino] biphenyl (NPB) (300 Å) was vacuum-deposited on the hole injection layer to form a hole transport layer, which is a material for transporting holes, and the following compound 4-4'-bis [N- (1-naphthyl) Respectively.

([1,1'-biphenyl] -4-yl) -N- (4- (11 - ([1,1'-biphenyl] -4-yl ) -11H-benzo [a] carbazole-5-yl) phenyl) - [1,1'-biphenyl] -4-amine (EB1) (100 Å) was vacuum deposited thereon to form an electron blocking layer.

Subsequently, the following m-CBP and Compound 1 were vacuum deposited on the electron blocking layer to a thickness of 300 ANGSTROM at a weight ratio of 70:30 to form a light emitting layer.

Compound HB1 was vacuum deposited on the light emitting layer to a thickness of 100 Å to form a hole blocking layer.

Compound ET1 and compound LiQ (Lithium Quinolate) were vacuum deposited on the hole blocking layer at a weight ratio of 1: 1 to form an electron injection and transport layer having a thickness of 300 Å. Lithium fluoride (LiF) and aluminum having a thickness of 2000 Å were sequentially deposited on the electron injecting and transporting layer to form a cathode.

Was maintained at the deposition rate was 0.4 ~ 0.7Å / sec for organic material in the above process, the lithium fluoride of the cathode was 0.3Å / sec, aluminum is deposited at a rate of 2Å / sec, During the deposition, a vacuum 2 × 10 ^{- 7} to 5 x 10 &lt; ^-6 &gt; torr to manufacture an organic light emitting device.

[Examples 2 to 9]

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

[Comparative Examples 1 to 5]

An organic light emitting device was fabricated in the same manner as in Example 1, except that the compound of the following T1 to T4 and 4CzIPN was used instead of the compound 1 in Example 1.

When current was applied to the organic light-emitting devices manufactured in Examples 1 to 9 and Comparative Examples 1 to 5, the results shown in Table 1 below were obtained.

division	Compound (light emitting layer)	Voltage (V @ 10 mA / cm 2 )	Efficiency (cd / A @ 10 mA / cm 2 )	The color coordinates (x, y)
Example 1	Compound 1	3.9	25	(0.33, 0.63)
Example 2	Compound 2	4.0	24	(0.34, 0.62)
Example 3	Compound 3	4.1	24	(0.33, 0.63)
Example 4	Compound 4	4.1	23	(0.33, 0.64)
Example 5	Compound 5	4.0	24	(0.33, 0.62)
Example 6	Compound 6	3.9	25	(0.32, 0.63)
Example 7	Compound 7	3.9	24	(0.33, 0.64)
Example 8	Compound 8	3.9	25	(0.34, 0.62)
Example 9	Compound 9	3.9	24	(0.33, 0.64)
Comparative Example 1	T1	5.1	2	(0.25, 0.25)
Comparative Example 2	T2	5.1	3	(0.29, 0.28)
Comparative Example 3	T3	4.9	13	(0.34, 0.57)
Comparative Example 4	T4	4.8	14	(0.33, 0.58)
Comparative Example 5	4CzIPN	4.7	17	(0.34, 0.62)

As shown in Table 1, all of the devices of Examples 1 to 9 using the compound having the structure of the formula (1) as a core had lower voltage and higher efficiency than those of the device using the compound 4CzIPN in Comparative Example 5 . Comparing the devices of Comparative Examples 1 to 4 with those of the present example, the compounds (T3 and T4) in which the benzene ring of the dibenzofuran is bonded at the meta position with the triazine group and the carbazole group and the dibenzofuran or dibenzo It was found that the structures of the embodiments of the present invention are more improved in terms of voltage and efficiency than the compounds (T1 and T2) in which the thiophene triazine group is not bonded. As shown in Table 1, it was confirmed that the compound of the present invention is applicable to a delayed fluorescent organic light emitting device because of its excellent light emitting ability and high color purity.

[Experimental Example]

In the case of HOMO and LUMO (Lowest Unoccupied Molecular Orbital), the measurement compound was dissolved in dimethylformamide (DMF) at a concentration of 5 mM and the electrolyte was measured at a concentration of 0.1 M, and oxidation and reduction potentials were determined by CV measurement. Respectively.

In the case of fluorescence measurement for measuring S ₁ and T ₁ , the measurement compound was dissolved in toluene at a concentration of 10 ^-5 M, and S ₁ was confirmed as the peak maximum value through fluorescence measurement at room temperature. In the cryogenic temperature state, T ₁ was confirmed from the maximum value. The fluorescence was measured at room temperature and low temperature by excitation using a 300 nm light source.

	S 1 (eV)	T 1 (eV)	HOMO (eV)	LUMO (eV)	? E st (eV)
Compound 1	2.41	2.40	5.61	3.01	0.01
Compound 2	2.42	2.39	5.58	3.10	0.03
Compound 3	2.41	2.39	5.59	3.05	0.02
Compound 4	2.43	2.40	5.60	3.12	0.03
Compound 5	2.40	2.38	5.58	3.07	0.02
Compound 6	2.41	2.38	5.61	3.02	0.03
Compound 7	2.42	2.41	5.60	3.08	0.01
Compound 8	2.40	2.39	5.57	3.07	0.01
Compound 9	2.43	2.41	5.55	3.09	0.02
T1	2.83	2.38	6.01	2.55	0.45
T2	2.82	2.38	5.98	2.53	0.44
T3	2.50	2.45	5.71	2.89	0.05
T4	2.50	2.46	5.70	2.87	0.04
4CzIPN	2.44	2.39	5.55	3.15	0.05

It can be seen that all of the compounds 1 to 9 used in the examples herein are suitable as retarded fluorescent compounds with ΔE _st of less than 0.2 eV. However, in T1 and T2, ΔE _st is 0.2 eV or more, and the efficiency is low because the delayed fluorescence characteristic is not exhibited.

T3, T4 and 4CzIPN correspond to retarded fluorescent compounds with ΔE _st of less than 0.2 eV, but as shown in Table 1, compounds 1 to 9 exhibit better voltage and efficiency characteristics than T3, T4 and 4CzIPN there was.

While the present invention has been particularly shown and described with reference to exemplary embodiments thereof, it is to be understood that the invention is not limited to the disclosed exemplary embodiments, but, on the contrary, is intended to cover various modifications and equivalent arrangements included within the spirit and scope of the appended claims. .

Claims (15)

1. A compound represented by the following formula (1):

   [Chemical Formula 1]

   

   In Formula 1,

   X1 is O or S,

   Ar1 and Ar2 are the same or different and each independently represents a substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

   R1 to R4 are the same or different from each other and each independently hydrogen; heavy hydrogen; A halogen group; A nitrile group; A nitro group; A hydroxy group; Carbonyl group; An ester group; Imide; Amide group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A substituted or unsubstituted arylphosphine group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,

   r1 is an integer of 1 to 6,

   r2 and r3 are each an integer of 1 to 7,

   r4 is an integer of 1 to 5,

   When each of r1 to r4 is 2 or more, the structures in parentheses of 2 or more are equal to or different from each other.
2. The compound according to claim 1, wherein the compound represented by Formula 1 is represented by Formula 1-1:

   [Formula 1-1]

   

   In Formula 1-1,

   X1, Ar1 and Ar2 are as defined in the above formula (1).
3. The compound according to claim 1, wherein the compound represented by Formula 1 is represented by Formula 1-2 or 1-3:

   [Formula 1-2]

   

   [Formula 1-3]

   

   In Formulas 1-2 and 1-3,

   X1, Ar1 and Ar2 are as defined in the above formula (1).
4. [2] The compound according to claim 1, wherein Ar1 and Ar2 are the same or different and each independently represents an aryl group substituted or unsubstituted with an alkyl group; Or a heteroaryl group substituted or unsubstituted with an aryl group.
5. The compound according to claim 1, wherein the compound of formula (1) is selected from the following compounds:

   

   

   

   

   

   
6. The compound according to claim 1, wherein ΔE _st of the compound represented by Formula (1) is less than 0.2 eV.
7. The compound according to claim 1, wherein the compound represented by Formula 1 is a retardation fluorescent compound.
8. A first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers comprises a compound according to any one of claims 1 to 7.
9. 9. The organic light emitting device according to claim 8, wherein the organic layer includes a light emitting layer, and the light emitting layer comprises the compound.
10. 9. The organic light emitting device according to claim 8, wherein the organic layer includes a light emitting layer, and the light emitting layer includes the compound as a dopant of the light emitting layer.
11. 9. The organic light emitting device according to claim 8, wherein the organic layer includes a light emitting layer, and the light emitting layer includes at least one selected from a condensed aromatic ring derivative and a heterocyclic compound as a host of the light emitting layer.
12. 12. The organic electroluminescent device according to claim 11, wherein the host comprises at least one selected from the following compounds:

    

    

    

    

    
13. 9. The organic electroluminescent device according to claim 8, wherein the organic material layer includes a light emitting layer, the light emitting layer contains the compound as a dopant of the light emitting layer, and includes at least one selected from a condensed aromatic ring derivative and a heterocyclic compound as a host of the light emitting layer Organic light emitting device.
14. 14. The organic light emitting device according to claim 13, wherein the light emitting layer includes the dopant and the host in a weight ratio of 1:99 to 50:50.
15. The organic light emitting device according to claim 8, wherein the organic layer includes a light emitting layer, and the light emitting layer further comprises a fluorescent emitter.

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