KR20200129990A - Organic light emitting device - Google Patents

Abstract

The present invention provides an organic light emitting element capable of exhibiting high light emitting efficiency and long life characteristics. The organic light emitting element comprises: an anode; a cathode provided to be opposite to the anode; a light emitting layer provided between the anode and the cathode; a hole transport region provided between the anode and the light emitting layer; and an electron transport region provided between the light emitting layer and the cathode.

Description

Organic light emitting device TECHNICAL FIELD

The present invention relates to an organic light-emitting device having a low driving voltage, high luminous efficiency, and excellent lifespan.

In general, the organic light emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material. An organic light-emitting device using the organic light-emitting phenomenon has a wide viewing angle, excellent contrast, and fast response time, and has excellent luminance, driving voltage, and response speed characteristics, and thus many studies are being conducted.

The organic light emitting device generally has a structure including an anode and a cathode, and an organic material layer between the anode and the cathode. The organic material layer is often made of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device.For example, it may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. In the structure of such an organic light-emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode are injected into the organic material layer, and excitons are formed when the injected holes and electrons meet. It glows when it falls back to the ground.

Development of new materials for organic materials used in organic light emitting devices as described above is continuously required.

Korean Patent Publication No. 10-2000-0051826

The present invention relates to an organic light-emitting device having a low driving voltage, high luminous efficiency, and excellent lifespan.

In order to solve the above problems, the present invention provides the following organic light emitting device.

anode;

A negative electrode provided opposite to the positive electrode;

A light emitting layer provided between the anode and the cathode;

A hole transport region provided between the anode and the emission layer; And

Including an electron transport region provided between the light emitting layer and the cathode,

The hole transport region includes a first compound represented by the following formula (1),

The emission layer includes a second compound represented by Formula 2 below,

The electron transport region includes a third compound represented by Formula 3 below,

[Formula 1]

In Formula 1,

L ₁ and L ₂ are each independently a single bond; Substituted or unsubstituted C _6-60 arylene; Or substituted or unsubstituted C _2-60 heteroarylene including any one or more heteroatoms selected from the group consisting of N, O and S,

Ar ₁ is substituted or unsubstituted C _6-60 aryl,

R ₁ to R ₄ are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Substituted or unsubstituted C _1-20 alkyl; Substituted or unsubstituted C _6-60 aryl; Or substituted or unsubstituted C _2-60 heteroaryl including any one or more heteroatoms selected from the group consisting of N, O and S,

a is an integer from 0 to 4,

b is an integer from 0 to 3,

[Formula 2]

In Chemical Formula 2,

L ₃ and L ₄ are each independently a single bond; Substituted or unsubstituted C _6-60 arylene; Or substituted or unsubstituted C _2-60 heteroarylene including any one or more heteroatoms selected from the group consisting of N, O and S,

Ar ₂ and Ar ₃ are each independently a substituted or unsubstituted C _6-60 aryl; Or substituted or unsubstituted C _2-60 heteroaryl including any one or more heteroatoms selected from the group consisting of N, O and S,

R ₅ is substituted or unsubstituted C _6-18 aryl; Substituted or unsubstituted carbazolyl; Substituted or unsubstituted dibenzofuranyl; Or a substituted or unsubstituted dibenzothiophenyl,

[Formula 3]

In Chemical Formula 3,

X ₁ to X ₃ are each independently N or CH, but at least one of X ₁ to X ₃ is N,

L ₅ is a single bond; Substituted or unsubstituted C _6-60 arylene; Or substituted or unsubstituted C _2-60 heteroarylene including any one or more heteroatoms selected from the group consisting of N, O and S,

Ar ₄ and Ar ₅ are each independently a substituted or unsubstituted C _6-60 aryl; Or substituted or unsubstituted C _2-60 heteroaryl including any one or more heteroatoms selected from the group consisting of N, O and S.

The above-described organic light-emitting device includes a compound having a specific structure in each of the hole transport region, the light emitting layer, and the electron transport region, and may exhibit low driving voltage, high luminous efficiency, and long lifespan characteristics.

FIG. 1 shows an example of an organic light-emitting device comprising a substrate 10, an anode 20, a hole transport region 30, an emission layer 40, an electron transport region 50, and a cathode 60.
2 is composed of a substrate 10, an anode 20, a hole transport region 30, a light emitting layer 40, an electron transport region 50 and a cathode 60, the hole transport region 30 is an anode ( A hole injection layer 31, a hole transport layer 33, and an electron blocking layer 35 are sequentially stacked from 20), and the electron transport region 50 is a hole blocking layer 51 sequentially stacked from the light emitting layer 40. ), an example of an organic light-emitting device including an electron transport layer 53 and an electron injection layer 55 is shown.

Hereinafter, it will be described in more detail to aid in understanding the present invention.

,

및

는 다른 치환기에 연결되는 결합을 의미한다.In this specification,

,

And

Means a bond connected to another substituent.

In the present specification, the term "substituted or unsubstituted" refers to deuterium; Halogen group; Cyano group; Nitro group; Hydroxy group; Carbonyl group; Ester group; Imide group; Amino group; Phosphine oxide group; Alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy group; Arylsulfoxy group; Silyl group; Boron group; Alkyl group; Cycloalkyl group; Alkenyl group; Aryl group; Aralkyl group; Aralkenyl group; Alkylaryl group; Alkylamine group; Aralkylamine group; Heteroarylamine group; Arylamine group; Arylphosphine group; Or it means substituted or unsubstituted with one or more substituents selected from the group consisting of a heteroaryl group containing one or more of N, O, and S atoms, or substituted or unsubstituted with two or more substituents connected among the aforementioned substituents. . For example, "a substituent to which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are connected.

In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but it is preferably 1 to 40 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 oxygen of the ester group with a straight chain, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.

In the present specification, the number of carbon atoms of the imide group is not particularly limited, but it is preferably 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, the silyl group is specifically trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc. However, it is not limited thereto.

In the present specification, the boron group specifically includes a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, and a phenylboron group, but is not limited thereto.

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

In the present specification, the alkyl group may be a linear or branched chain, 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-methyl-butyl, 1-ethyl-butyl, pentyl, n -Pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2 -Dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.

In the present specification, the alkenyl group may be a linear or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( Naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl group, styrenyl group, and the like, but are not limited thereto.

In the present specification, the cycloalkyl group is not particularly limited, but is preferably 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. 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 aryl group is not particularly limited, but is preferably 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a phenyl group, a biphenyl group, or a terphenyl group, but the monocyclic aryl group 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, and the like, but is not limited thereto.

등이 될 수 있다. 다만, 이에 한정되는 것은 아니다.In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. When the fluorenyl group is substituted,

Etc. However, it is not limited thereto.

In the present specification, heteroaryl is a heteroaryl containing at least one of O, N, Si, and S as a heterogeneous element, and the number of carbons is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of heteroaryl include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, acridyl group, Pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group, Carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group (phenanthroline), isoxazolyl group, thiadiazolyl Group, phenothiazinyl group, dibenzofuranyl group, and the like, but are not limited thereto.

In the present specification, the aryl group among the aralkyl group, aralkenyl group, alkylaryl group, and arylamine group is the same as the example of the aryl group described above. In the present specification, the alkyl group among the aralkyl group, the alkylaryl group and the alkylamine group is the same as the example of the aforementioned alkyl group. In the present specification, for heteroaryl among heteroarylamines, the above-described description of heteroaryl may be applied. In the present specification, the alkenyl group of the aralkenyl group is the same as the example of the alkenyl group described above. In the present specification, the description of the aryl group described above may be applied except that the arylene is a divalent group. In the present specification, the description of the above-described heteroaryl may be applied except that the heteroarylene is a divalent group. In the present specification, the hydrocarbon ring is not a monovalent group, and the description of the aryl group or the cycloalkyl group described above may be applied except that the hydrocarbon ring is formed by bonding of two substituents. In the present specification, the heteroaryl is not a monovalent group, and the description of the above-described heteroaryl may be applied except that the heterocycle is formed by bonding of two substituents.

The present invention provides an organic light emitting device having the following structure:

anode;

A negative electrode provided opposite to the positive electrode;

A light emitting layer provided between the anode and the cathode and including the second compound;

A hole transport region provided between the anode and the emission layer and including the first compound; And

An electron transport region provided between the light emitting layer and the cathode and including the third compound.

Hereinafter, the present invention will be described in detail for each configuration.

Anode and cathode

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 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); A combination of a metal and an oxide 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 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.

Hole transport area

The organic light emitting device according to the present invention includes a hole transport region for receiving holes from an anode provided between the anode and the emission layer and transporting holes to the emission layer, and the hole transport region includes the first compound represented by Formula 1 do.

The first compound has a tertiary amine structure in which fluorene and spirobifluorene are substituted, and has excellent hole injection characteristics and characteristics of moving holes to the emission layer, and accordingly, the organic light-emitting device employing the first compound May represent a low driving voltage and high efficiency.

Preferably, in Formula 1, L ₁ and L ₂ may each independently be a single bond, or any one selected from the group consisting of:

Above,

A ₁ is O, S, N(C _6-20 aryl), C(C _1-4 alkyl) ₂ , or C(C _6-20 aryl) ₂ .

For example, A ₁ is O, S, N (phenyl), C (methyl) ₂ , or C (phenyl) ₂ .

More preferably, L ₁ and L ₂ are each independently a single bond; Phenylene; Or naphthalenediyl.

Preferably, Ar ₁ is any one selected from the group consisting of:

Preferably, a and b are each 0, 1 or 2. In this case, when a and b are each 2 or more, the structures in parentheses are the same or different, respectively. More preferably, a and b are each 0 or 1.

Preferably, R ₁ and R ₂ are each independently C _1-10 alkyl; Or C _6-20 aryl, and R ₃ and R ₄ are hydrogen.

Preferably, R ₁ and R ₂ are the same as each other, more preferably R ₁ and R ₂ are methyl or phenyl.

Specifically, the first compound is represented by the following Formula 1-1 or 1-2:

[Formula 1-1]

[Formula 1-2]

In Formula 1-1 or 1-2,

Description of L ₁ , L ₂ and Ar ₁ are as defined in Formula 1.

Representative examples of the first compound are as follows:

In this case, the first compound may be prepared by a manufacturing method as shown in Scheme 1 below, for example.

[Scheme 1]

In Scheme 1, T is halogen, preferably bromo, or chloro, and the definition of other substituents is as described above.

Specifically, the compound represented by Formula 1 is prepared by combining starting materials through a Suzuki coupling reaction. Such a Suzuki coupling reaction is preferably carried out in the presence of a palladium catalyst and a base, and the reactor for the Suzuki coupling reaction can be changed as known in the art. The manufacturing method may be more specific in the manufacturing examples to be described later.

Meanwhile, the hole transport region may include a hole injection layer, a hole transport layer, and an electron blocking layer sequentially stacked from the anode. Preferably, the electron blocking layer is located in contact with the light emitting layer, and the first compound is included in the hole transport layer or the electron blocking layer. More preferably, the first compound is included in the electron blocking layer.

Hereinafter, each organic layer will be described in detail.

(Hole injection floor)

The hole injection layer is disposed on the anode and injects holes from the anode, and includes a hole injection material. Such a hole injection material has the ability to transport holes, 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. In addition, a compound having excellent thin film formation ability is preferable. In particular, it is suitable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer.

Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, perylene Organic materials, anthraquinone, polyaniline, and polythiophene-based conductive polymers, but are not limited thereto.

(Hole transport layer)

The hole transport layer is formed on the hole injection layer to receive holes from the hole injection layer and transport holes to the light emitting layer. The hole transport layer includes a hole transport material, and a material having high mobility for holes capable of transporting holes from the anode or the hole injection layer and transferring them to the light emitting layer is suitable as the hole transport material.

Preferably, the first compound represented by Formula 1 is used as the hole transport material. Alternatively, an arylamine-based organic material, a conductive polymer, and a block copolymer including a conjugated portion and a non-conjugated portion may be used as the hole transport material, but the present invention is not limited thereto.

(Electron blocking layer)

The electron blocking layer is formed on the hole transport layer and is preferably provided in contact with the light emitting layer to control hole mobility and prevent excessive movement of electrons, thereby increasing the probability of hole-electron coupling, thereby increasing the efficiency of the organic light-emitting device. Serves to improve The electron blocking layer includes an electron blocking material, and a material having a stable structure in which electrons do not flow out of the emission layer is suitable as the electron blocking material.

Preferably, the first compound represented by Formula 1 is used as the electron blocking material. Alternatively, an arylamine-based organic material may be used as the electron blocking material, but is not limited thereto.

Emitting layer

The organic light-emitting device according to the present invention includes an anthracene compound in which positions 2, 9, and 10, which are the second compound represented by Chemical Formula 2, are substituted as a host material. In particular, the second compound has a structure in which the same or different substituents are introduced at positions 9 and 10 and a substituent is introduced at the second position, so that the material stability is higher than that of the compound in which the substituent is not introduced at the 2nd position. It is excellent and can contribute to the improvement of lifespan characteristics when used in organic light emitting devices.

Preferably, in Formula 2, L ₃ and L ₄ may each independently be a single bond, or any one selected from the group consisting of:

Above,

A ₂ is O, S, N(C _6-20 aryl), C(C _1-4 alkyl) ₂ , or C(C _6-20 aryl) ₂ .

For example, A ₂ is O, S, N(phenyl), C(methyl) ₂ , or C(phenyl) ₂ .

More preferably, L ₃ and L ₄ are each independently a single bond or phenylene.

Preferably, Ar ₂ and Ar ₃ are each independently C _6-20 aryl; Or C _2-60 heteroaryl including O or S.

More preferably, Ar ₂ and Ar ₃ are each independently phenyl, biphenylyl, terphenylyl, naphthyl, phenanthrenyl, dibenzofuranyl, or dibenzothiophenyl.

Preferably, R ₅ is phenyl, biphenylyl, terphenylyl, naphthyl, phenanthrenyl, triphenylenyl, fluorenyl, carbazolyl, dibenzofuranyl, or dibenzothiophenyl,

Here, R ₅ is unsubstituted or with 1 to 5 substituents each independently selected from the group consisting of deuterium, C _1-10 alkyl, tri(C _1-4 alkyl) silyl and C _6-20 aryl Can be substituted.

More preferably, R ₅ is any one selected from the group consisting of:

Above,

Q is hydrogen, C _1-10 alkyl, Si(C _1-4 alkyl) ₃ , or C _6-20 aryl,

Y ₁ is O, S, N(C _6-20 aryl), C(C _1-4 alkyl) ₂ , or C(C _6-20 aryl) ₂ .

For example, Q is hydrogen, tert-butyl, Si(methyl) ₃ , phenyl, or naphthyl,

Y ₁ is O, S, N (phenyl), C (methyl) ₂ , or C (phenyl) ₂ .

Preferably, the second compound is represented by the following formula 2-1 or 2-2:

[Formula 2-1]

[Formula 2-2]

In Formulas 2-1 and 2-2,

Description of L ₄ , Ar ₃ and R ₅ is as defined in Chemical Formula 2.

Representative examples of the second compound are as follows:

At this time, the second compound may be prepared by a manufacturing method as shown in Scheme 2 below, for example.

[Scheme 2]

In Scheme 2, T is halogen, preferably bromo, or chloro, and the definition of other substituents is as described above.

Specifically, the compound represented by Formula 2 is prepared by introducing a R ₅ substituent to a starting material through a Suzuki coupling reaction. Such a Suzuki coupling reaction is preferably carried out in the presence of a palladium catalyst and a base, and the reactor for the Suzuki coupling reaction can be changed as known in the art. The manufacturing method may be more specific in the manufacturing examples to be described later.

Meanwhile, the emission layer may further include a dopant material. Examples of the dopant material include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, and periflanthene having an arylamino group, and the styrylamine compound is substituted or unsubstituted As a compound in which at least one arylvinyl group is substituted on the arylamine, one or two or more substituents selected from the group consisting of an aryl group, silyl group, alkyl group, cycloalkyl group, and arylamino group are substituted or unsubstituted. Specifically, there are styrylamine, styryldiamine, styryltriamine, and styryltetraamine, but are not limited thereto. In addition, the metal complex includes an iridium complex, a platinum complex, and the like, but is not limited thereto. Preferably, the emission layer may include an iridium complex as a dopant material.

The organic light-emitting device including the emission layer including the host material and the dopant material described above may exhibit a maximum wavelength λ _max in the emission spectrum at about 400 nm to about 500 nm. Accordingly, the organic light-emitting device is a blue light-emitting organic light-emitting device.

Electronic transport area

The organic light-emitting device according to the present invention includes an electron transport region provided between the emission layer and the cathode, and transports electrons from the cathode to the emission layer, and the electron transport region includes a third compound represented by Chemical Formula 3.

The third compound has a structure in which an N-containing 6 membered heterocyclic group, which is an electron deficient substituent, is bonded to an electron-rich spiro (fluorene-9,9'-xanthene) core, and has a low dipole moment (dipole moment) values and amorphous properties. Accordingly, when such a third compound is employed in an organic light emitting device, destruction of the device due to crystallization, which may be caused by heat generated during operation of the device, can be prevented. Accordingly, the organic light emitting device employing the third compound has a driving voltage This can indicate low and high efficiency.

The third compound is represented by any one of the following formulas 3-1 to 3-4, depending on the substitution position of the N-containing 6 membered heterocyclic group:

[Formula 3-1]

[Chemical Formula 3-2]

[Chemical Formula 3-3]

[Formula 3-4]

In Formulas 3-1 to 3-4,

L ₅ , X ₁ to X ₃ , Ar ₄ and Ar ₅ are as defined in Chemical Formula 1.

Preferably, the third compound is represented by any one of Formulas 3-1 to 3-3.

Preferably, X ₁ to X ₃ are all N;

X ₁ and X ₂ are N and X ₃ is CH;

X ₁ and X ₃ are N and X ₂ is CH;

X ₁ is N and X ₂ and X ₃ are CH; or

X ₃ is N, and X ₁ and X ₂ are CH.

Preferably, L ₅ is a single bond, or any one selected from the group consisting of:

Above,

X is O, S, N(C _6-20 aryl), C(C _1-4 alkyl) ₂ , or C(C _6-20 aryl) ₂ .

For example, X is O, S, N(phenyl), C(methyl) ₂ , or C(phenyl) ₂ .

More preferably, L ₅ is a single bond, phenylene, or biphenyldiyl.

Most preferably, L ₅ is a single bond, or any one selected from the group consisting of:

Preferably, Ar ₄ and Ar ₅ are each independently, phenyl, biphenylyl, terphenylyl, naphthyl, phenanthrenyl, triphenylenyl, fluorenyl, spirobifluorenyl, carbazolyl, dibenzo. Furanyl or dibenzothiophenyl,

Here, Ar ₄ and Ar ₅ are unsubstituted or independently selected from the group consisting of deuterium, cyano, halogen, Si(C _1-4 alkyl) _3, C _1-10 alkyl and C _6-20 aryl It may be substituted with 1 to 5 substituents.

More preferably, Ar ₄ and Ar ₅ are each independently any one selected from the group consisting of:

Above,

Z is hydrogen, cyano, halogen, Si(C _1-4 alkyl) ₃ , C _1-10 alkyl, or C _6-20 aryl,

X'is O, S, N(C _6-20 aryl), C(C _1-4 alkyl) ₂ , or C(C _6-20 aryl) ₂ .

For example, Z is hydrogen, cyano, fluoro, Si(CH ₃ ) _3, methyl, phenyl, naphthyl, or phenanthrenyl, and X'is O, S, N(phenyl), N(naphthyl ), C(methyl) ₂ , or C(phenyl) ₂ .

Representative examples of the third compound are as follows:

In this case, the third compound may be prepared by a manufacturing method as shown in Scheme 3 below, as an example. The manufacturing method may be more specific in the manufacturing examples to be described later.

[Scheme 3]

In Reaction Scheme 3, T is each independently halogen, preferably bromo or chloro, and the definition of other substituents is as described above.

Specifically, steps 3-1 and 3-2 are steps of preparing a spiro [fluorene-9,9'-xanthene) core through a cyclic reaction after reducing the starting material in the presence of a strong base, and the step 3 -3 is a step of introducing a reactor for performing a Suzuki coupling reaction to the prepared core, and step 3-4 is a step of introducing an N-containing-6 membered heterocyclic group to the core through a Suzuki coupling reaction, This is the step of preparing the displayed compound. Such a Suzuki coupling reaction is preferably carried out in the presence of a palladium catalyst and a base, and the reactor for the Suzuki coupling reaction can be changed as known in the art. The manufacturing method may be more specific in the manufacturing examples to be described later.

Meanwhile, the electron transport region may include a hole blocking layer and an electron transport layer sequentially stacked from the light emitting layer; Hole blocking layer and electron injection and transport layer; Alternatively, it may be composed of a hole blocking layer, an electron transport layer, and an electron injection layer. Preferably, the hole blocking layer is located in contact with the emission layer, and the first compound is included in the hole blocking layer or the electron transport layer. More preferably, the first compound is included in the electron transport layer.

Hereinafter, each organic layer will be described in detail.

(Hole blocking layer)

The hole blocking layer is formed on the emission layer, and specifically, the hole blocking layer is provided in contact with the emission layer to prevent excessive movement of holes, thereby increasing the probability of hole-electron bonding, thereby improving the efficiency of the organic light-emitting device. Do it. The hole blocking layer includes a hole blocking material, and as such a hole blocking material, a material having a stable structure in which holes do not flow out of the emission layer is suitable.

Preferably, the third compound represented by Chemical Formula 3 is used as the hole blocking material. Or, a azine derivative including triazine as the hole blocking material; Triazole derivatives; Oxadiazole derivatives; Phenanthroline derivatives; A compound into which an electron withdrawing group such as a phosphine oxide derivative has been introduced may be used, but is not limited thereto.

(Electron transport layer)

The electron transport layer is formed between the light emitting layer and the cathode, preferably between the hole blocking layer and an electron injection layer to be described later to receive electrons from the electron injection layer to transport electrons to the light emitting layer. The electron transport layer includes an electron transport material, and the electron transport material is a material capable of receiving electrons from the cathode and transferring them to the light emitting layer, and a material having high mobility for electrons is suitable.

Preferably, a third compound represented by Formula 3 is used as the electron transport material. Alternatively, a pyridine derivative as the electron transport material; Pyrimidine derivatives; Triazole derivatives; Triazine derivatives; Al complex of 8-hydroxyquinoline; Complexes containing Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes and the like may be used, but are not limited thereto.

In addition, the electron transport layer may include a metal complex compound together with the electron transport material. 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. , This, is not limited.

(Electron injection layer)

The electron injection layer is located between the electron transport layer and the cathode, and serves to inject electrons from the cathode. The electron injection layer includes an electron injection material, and a material having excellent electron injection effect with respect to the light-emitting layer or the light-emitting material while having the ability to transport electrons and having excellent thin film formation ability is suitable as the electron injection material.

Specific examples of the electron injection material include LiF, NaCl, CsF, Li ₂ O, BaO, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, Derivatives thereof, such as perylene tetracarboxylic acid, preorenylidene methane, and anthrone, metal complex compounds, and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.

Organic light emitting element

The structure of the organic light emitting device according to the present invention is illustrated in FIGS. 1 and 2.

FIG. 1 shows an example of an organic light-emitting device comprising a substrate 10, an anode 20, a hole transport region 30, an emission layer 40, an electron transport region 50, and a cathode 60. In this structure, the first compound may be included in the hole transport region 30, the second compound may be included in the emission layer 40, and the third compound may be included in the electron transport region 50. .

2 is composed of a substrate 10, an anode 20, a hole transport region 30, a light emitting layer 40, an electron transport region 50 and a cathode 60, the hole transport region 30 is an anode ( A hole injection layer 31, a hole transport layer 33, and an electron blocking layer 35 are sequentially stacked from 20), and the electron transport region 50 is a hole blocking layer 51 sequentially stacked from the light emitting layer 40. ), an example of an organic light-emitting device including an electron transport layer 53 and an electron injection layer 55 is shown. In this structure, the first compound is the hole transport layer 33 or the electron blocking layer 35, the second compound is the light emitting layer 40, the third compound is the hole blocking layer 51 Alternatively, each may be included in the electron transport layer 53.

The organic light emitting device according to the present invention can be manufactured by sequentially stacking the above-described configurations. At this time, using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, the anode is formed by depositing a metal or a conductive metal oxide or an alloy thereof on the substrate. And, after forming each of the above-described layers thereon, it can be prepared by depositing a material that can be used as a cathode 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 light emitting layer may be formed by a solution coating method as well as a vacuum deposition method of a host and a dopant. 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 such a 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 (WO 2003/012890). However, the manufacturing method is not limited thereto.

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

The fabrication of the organic light emitting device will be described in detail in the following examples. However, the following examples are for illustrating the present invention, and the scope of the present invention is not limited thereto.

Preparation Example 1: Preparation of compound 1-1

Compound 4-bromo-9,9'-spirobi[fluorene] (6.50 g, 16.50 mmol), and compound N-([1,1':4',1') in a 500 mL round bottom flask in a nitrogen atmosphere. '-Terphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine (7.21 g, 16.50 mmol) was completely dissolved in 270 mL of Xylene, and NaOtBu (2.38 g, 24.75 mmol) was added. Then, bis(tri-ter-butylphosphine)palladium (0) (0.17 g, 0.34 mmol) was added, followed by heating and stirring for 4 hours. After lowering the temperature to room temperature and removing the base by filtering, Xylene was concentrated under reduced pressure and recrystallized with 210 mL of tetrahydrofuran to prepare compound 1-1 (6.65 g, yield: 54%).

MS[M+H]+= 752

Preparation Example 2: Preparation of compound 1-2

Compound 4-bromo-9,9'-spirobi[fluorene](6.50g, 16.50mmol), (4-([1,1'-biphenyl]-4-yl) in a 500ml round bottom flask in a nitrogen atmosphere (9,9-dimethyl-9H-fluoren-2-yl) amino) phenyl) boronic acid (7.94 g, 16.50 mmol) was completely dissolved in 220 ml of tetrahydrofuran, and then 2M aqueous potassium carbonate solution (110 ml) was added, and tetrahydrofuran was added. After adding kiss-(triphenylphosphine)palladium (0.57g, 0.49mmol), the mixture was heated and stirred for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 310 ml of ethyl acetate to prepare compound 1-2 (7.49g, 60%).

MS[M+H] ⁺ = 752

Preparation Example 3: Preparation of compound 1-3

Compound 4-bromo-9,9'-spirobi[fluorene](6.50g, 16.50mmol), (3-([1,1'-biphenyl]-4-yl) in a 500ml round bottom flask in a nitrogen atmosphere (9,9-dimethyl-9H-fluoren-2-yl) amino) phenyl) boronic acid (7.94 g, 16.50 mmol) was completely dissolved in 220 ml of tetrahydrofuran, and then 2M aqueous potassium carbonate solution (110 ml) was added, and tetrahydrofuran was added. After adding kiss-(triphenylphosphine)palladium (0.57g, 0.49mmol), the mixture was heated and stirred for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 310 ml of ethyl acetate to prepare compound 1-3 (6.75 g, 54%).

MS[M+H] ⁺ = 752

Preparation Example 4: Preparation of compound 2-1

Compound 10-([1,1':2',1''-terphenyl]-4-yl)-2-bromo-9-phenylanthracene (11.50 g, 20.54 mmol) in a 500 ml round bottom flask in a nitrogen atmosphere , Phenylboronic acid (2.51g, 20.54mmol) was completely dissolved in 220ml of tetrahydrofuran, 2M aqueous potassium carbonate solution (110ml) was added, and tetrakis-(triphenylphosphine)palladium (0.71g, 0.62mmol) was added. Then, it was heated and stirred for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 270 ml of ethyl acetate to prepare compound 2-1 (5.44 g, 66%).

MS[M+H] ⁺ = 559

Preparation Example 5: Preparation of compound 2-2

Compound 2-bromo-10-(naphthalen-1-yl)-9-phenylanthracene (8.50g, 18.56mmol), dibenzo[b,d]furan-2-ylboronic acid ( 3.93g, 18.56mmol) was completely dissolved in 240ml of tetrahydrofuran, 2M aqueous potassium carbonate solution (120ml) was added, tetrakis-(triphenylphosphine)palladium (0.64g, 0.56mmol) was added, and then heated for 3 hours. Stirred. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 270 ml of ethyl acetate to prepare compound 2-2 (6.22 g, 61%).

MS[M+H] ⁺ = 547

Preparation Example 6: Preparation of compound 2-3

Compound 3-(3-bromo-10-phenylanthracene-9-yl)dibenzo[b,d]thiophene (7.50g, 14.59mmol), [1,1'- ratio) in a 500ml round bottom flask in a nitrogen atmosphere. Phenyl]-3-ylboronic acid (3.18g, 16.05mmol) was completely dissolved in 180ml of tetrahydrofuran, 2M aqueous potassium carbonate solution (90ml) was added, and tetrakis-(triphenylphosphine)palladium (0.51g, 0.44mmol) ) And then heated and stirred for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 270 ml of ethyl acetate to prepare compound 2-3 (5.11 g, 60%).

MS[M+H] ⁺ = 589

Preparation Example 7: Preparation of compound 3-1

Compound A (12.13 g, 26.49 mmol), (3-(4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) boronic acid (8.50 g, in a 500 ml round bottom flask in a nitrogen atmosphere) 24.08mmol) was completely dissolved in 200ml of tetrahydrofuran, 2M aqueous potassium carbonate solution (100ml) was added, tetrakis-(triphenylphosphine)palladium (0.83g, 0.72mmol) was added, followed by heating and stirring for 5 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 230 ml of ethyl acetate to prepare compound 3-1 (10.05 g, 64%).

MS[M+H] ⁺ = 640

Preparation Example 8: Preparation of compound 3-2

Compound B (10.70g, 23.37mmol), 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5- in a 500 ml round bottom flask in a nitrogen atmosphere. Triazine (7.5g, 21.25mmol) was completely dissolved in 220ml of tetrahydrofuran, 2M potassium carbonate aqueous solution (110ml) was added, tetrakis-(triphenylphosphine)palladium (0.74g, 0.64mmol) was added, and then 4 Heated and stirred for hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 240 ml of ethyl acetate to prepare compound 3-2 (7.62g, 55%).

MS[M+H] ⁺ = 640

Preparation Example 9: Preparation of compound 3-3

Compound C (7.49g, 16.36mmol), 2-(4-bromophenyl)-4-(naphthalen-1-yl)-6-phenyl-1,3,5-triazine in a 500ml round bottom flask in nitrogen atmosphere (6.50g, 14.87mmol) was completely dissolved in 200ml of tetrahydrofuran, 2M aqueous potassium carbonate solution (100ml) was added, tetrakis-(triphenylphosphine)palladium (0.52g, 0.45mmol) was added, and then for 3 hours. Heated and stirred. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 180 ml of tetrahydrofuran to prepare compound 3-3 (5.89g, 62%).

MS[M+H] ⁺ = 690

Example 1

A glass substrate coated with a thin film of ITO (indium tin oxide) having a thickness of 1,000Å was put in distilled water dissolved in a detergent and washed with ultrasonic waves. At this time, a product made by Fischer Co. was used as a detergent, and distilled water secondarily filtered with a filter manufactured 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 cleaning 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 thus prepared ITO transparent electrode, the compounds of the following formula HI-1 and the following formula HI-2 were thermally vacuum deposited to a thickness of 100 Å in a ratio of 98:2 (molar ratio) to form a hole injection layer.

The following compound HT-1 (1150Å), which is a material for transporting holes, was vacuum deposited on the hole injection layer to form a hole transport layer.

Subsequently, compound 1-1 prepared in Preparation Example 1 with a film thickness of 50 Å was vacuum deposited on the hole transport layer to form an electron blocking layer.

Subsequently, a light emitting layer was formed by vacuum depositing the compound 2-1 (host) prepared in Preparation Example 4 and the compound BD-1 (dopant) below at a weight ratio of 40:1 on the electron blocking layer with a film thickness of 200 Å.

Compound HB-1 was vacuum-deposited on the emission layer with a thickness of 50 Å to form a hole blocking layer.

Subsequently, on the hole blocking layer, Compound 3-1 prepared in Preparation Example 7 and LiQ (Lithium Quinolate) were vacuum-deposited at a weight ratio of 1:1 to form an electron transport layer having a thickness of 300Å.

Lithium fluoride (LiF) in a thickness of 12 Å and aluminum in a thickness of 2,000 Å were sequentially deposited on the electron transport layer to form an electron injection layer and a negative electrode, respectively.

In the above process, the deposition rate of the organic material was maintained at 0.4 ~ 0.7 Å/sec, the deposition rate of lithium fluoride at the negative electrode was 0.3 Å/sec, and the deposition rate of aluminum was 2 Å/sec, and the vacuum degree during deposition was 2×10-7. An organic light-emitting device was manufactured by maintaining ~5 x 10-6 torr.

The compound used in Example 1 is as follows.

Examples 2 to 9 and Comparative Examples 1 to 13

In Example 1, in the same manner as in Example 1, except that the compounds shown in Table 1 were used instead of the electron blocking layer compound 1-1, the host compound 2-1, and the electron transport layer compound 3-1, respectively. An organic light emitting device was manufactured. The compounds used in Examples and Comparative Examples are as follows.

Experimental example

When a current of 20 mA/cm ² was applied to the organic light-emitting device prepared in the above Examples and Comparative Examples, the prepared organic light-emitting device was measured for driving voltage, luminous efficiency, and color coordinates at a current density of 20 mA/cm ² . It was measured, and the time (T95) was measured at a current density of 20 mA/cm ² compared to the initial luminance at 95%. The results are shown in Table 1 below. At this time, T95 refers to the time required for the luminance to decrease from the initial luminance (1600 nit) to 95%.

compound
(Electronic
Transport layer) compound
(Electronic
Barrier layer) compound
(Emitting layer host) Voltage
(V
@20mA
/cm ² ) efficiency
(cd/A
@20mA
/cm ² 8 Color coordinates
(x,y) T95
(hr) Example 1 3-1 1-1 2-1 3.51 6.69 (0.144, 0.046) 360 Example 2 3-2 1-1 2-2 3.53 6.64 (0.145, 0.047) 345 Example 3 3-3 1-1 2-3 3.54 6.71 (0.144, 0.048) 355 Example 4 3-1 1-2 2-1 3.63 6.70 (0.145, 0.044) 365 Example 5 3-2 1-2 2-2 3.64 6.63 (0.144, 0.046) 340 Example 6 3-3 1-2 2-3 3.65 6.65 (0.146, 0.044) 335 Example 7 3-1 1-3 2-1 3.78 6.76 (0.145, 0.046) 360 Example 8 3-2 1-3 2-2 3.73 6.69 (0.144, 0.044) 345 Example 9 3-3 1-3 2-3 3.72 6.64 (0.143, 0.046) 330 Comparative Example 1 3-1 EB-1 BH-1 4.00 6.06 (0.144, 0.045) 260 Comparative Example 2 3-2 EB-1 BH-1 4.01 6.05 (0.145, 0.048) 275 Comparative Example 3 3-3 EB-1 BH-1 4.02 6.03 (0.144, 0.046) 240 Comparative Example 4 ET-1 EB-1 2-1 4.18 5.80 (0.144, 0.045) 330 Comparative Example 5 ET-1 EB-1 2-2 4.17 5.86 (0.146, 0.042) 315 Comparative Example 6 ET-1 EB-1 2-3 4.15 5.84 (0.145, 0.046) 305 Comparative Example 7 ET-1 1-1 BH-1 3.92 5.83 (0.144, 0.047) 250 Comparative Example 8 ET-1 1-2 BH-1 3.96 5.91 (0.144, 0.047) 160 Comparative Example 9 ET-1 1-3 BH-1 3.95 5.97 (0.145, 0.048) 175 Comparative Example 10 ET-2 1-1 2-1 3.76 6.31 (0.144, 0.047) 280 Comparative Example 11 3-1 1-1 BH-2 3.72 6.45 (0.144, 0.047) 220 Comparative Example 12 3-1 EB-1 2-1 3.85 6.43 (0.145, 0.048) 245 Comparative Example 13 ET-1 EB-1 BH-1 4.25 5.86 (0.144, 0.047) 250

As shown in Table 1, the compound represented by Formula 1 was used as the electron blocking layer material, and the compound represented by Formula 2 was used as the host material of the emission layer and the compound represented by Formula 3 was simultaneously used as the electron transport layer material. The organic light-emitting device of the embodiment exhibits superior characteristics in terms of driving voltage, luminous efficiency, and lifespan compared to the organic light-emitting device of Comparative Example in which only one or two of the compounds represented by Formulas 1 to 3 are employed, or neither is employed. Done.

Specifically, looking at Comparative Examples 7 to 9 and Comparative Example 13, the compound represented by Formula 1 has a hole injection property and a property of moving holes to the light emitting layer compared to the compound EB-1 in which a tertiary amine group is substituted with triphenylene. It can be seen that this is excellent and contributes to the improvement of the efficiency of the device. In addition, looking at Comparative Examples 1 to 3 and Comparative Example 13, the compound represented by Formula 3 has electron injection characteristics and light emitting layer compared to ET-1 in which a triazinyl group is connected to 9,9-diphenyl-9H-fluorene. It can be seen that the electron transfer property is excellent, which contributes to the improvement of the device efficiency. And, looking at Comparative Examples 4 to 6 and Comparative Example 13, the compound represented by Chemical Formula 2 has excellent material stability compared to Comparative Example Compound BH-1 which does not have a substituent at the anthracene 2 position, and thus has excellent longevity characteristics of the device. It can be seen that it contributes.

In addition, unlike the organic light-emitting device of Comparative Example 13, in which efficiency and lifespan characteristics are not simultaneously improved even when EB-1, BH-1, and ET-1 are combined with each other, the compound represented by Formula 1 is represented by Formula 2 It is confirmed that the organic light emitting device of the embodiment according to the present invention employing both the compound represented by the compound and the compound represented by Chemical Formula 3 improves efficiency and lifespan characteristics at the same time. In general, when considering that the luminous efficiency and lifetime characteristics of the organic light-emitting device have a trade-off relationship with each other, the organic light-emitting device employing a combination of the compounds of the present invention has significantly improved device characteristics compared to the comparative example device. It can be seen that it represents.

10: substrate 20: anode
30: hole transport area 31: hole injection layer
33: hole transport layer 35: electron blocking layer
40: light emitting layer 50: electron transport region
51: hole blocking layer 53: electron transport layer
55: electron injection layer 60: cathode

Claims (17)

anode;
A negative electrode provided opposite to the positive electrode;
A light emitting layer provided between the anode and the cathode;
A hole transport region provided between the anode and the emission layer; And
Including an electron transport region provided between the light emitting layer and the cathode,
The hole transport region includes a first compound represented by the following formula (1),
The light emitting layer includes a second compound represented by the following formula (2),
The electron transport region contains a third compound represented by the following formula (3),
Organic light emitting element:
[Formula 1]

In Formula 1,
L ₁ and L ₂ are each independently a single bond; Substituted or unsubstituted C _6-60 arylene; Or substituted or unsubstituted C _2-60 heteroarylene including any one or more heteroatoms selected from the group consisting of N, O and S,
Ar ₁ is substituted or unsubstituted C _6-60 aryl,
R ₁ to R ₄ are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Substituted or unsubstituted C _1-20 alkyl; Substituted or unsubstituted C _6-60 aryl; Or substituted or unsubstituted C _2-60 heteroaryl including any one or more heteroatoms selected from the group consisting of N, O and S,
a is an integer from 0 to 4,
b is an integer from 0 to 3,
[Formula 2]

In Chemical Formula 2,
L ₃ and L ₄ are each independently a single bond; Substituted or unsubstituted C _6-60 arylene; Or substituted or unsubstituted C _2-60 heteroarylene including any one or more heteroatoms selected from the group consisting of N, O and S,
Ar ₂ and Ar ₃ are each independently a substituted or unsubstituted C _6-60 aryl; Or substituted or unsubstituted C _2-60 heteroaryl including any one or more heteroatoms selected from the group consisting of N, O and S,
R ₅ is substituted or unsubstituted C _6-18 aryl; Substituted or unsubstituted carbazolyl; Substituted or unsubstituted dibenzofuranyl; Or a substituted or unsubstituted dibenzothiophenyl,
[Formula 3]

In Chemical Formula 3,
X ₁ to X ₃ are each independently N or CH, but at least one of X ₁ to X ₃ is N,
L ₅ is a single bond; Substituted or unsubstituted C _6-60 arylene; Or substituted or unsubstituted C _2-60 heteroarylene including any one or more heteroatoms selected from the group consisting of N, O and S,
Ar ₄ and Ar ₅ are each independently a substituted or unsubstituted C _6-60 aryl; Or substituted or unsubstituted C _2-60 heteroaryl including any one or more heteroatoms selected from the group consisting of N, O and S.
The method of claim 1,
L ₁ and L ₂ are each independently a single bond; Phenylene; Or naphthalenediyl, an organic light-emitting device.
The method of claim 1,
Ar ₁ is any one selected from the group consisting of,
Organic light emitting element:

.
The method of claim 1,
R ₁ and R ₂ are each independently C _1-10 alkyl; Or C _6-20 aryl,
R ₃ and R ₄ are hydrogen,
Organic light emitting element:
The method of claim 1,
The first compound is represented by the following Formula 1-1 or 1-2,
Organic light emitting element:
[Formula 1-1]

[Formula 1-2]

In Formula 1-1 or 1-2,
Description of L ₁ , L ₂ and Ar ₁ is as defined in paragraph 1.
The method of claim 1,
The first compound is any one selected from the group consisting of,
Organic light emitting element:

The method of claim 1,
L ₃ and L ₄ are each independently a single bond or phenylene,
Organic light emitting device.
The method of claim 1,
Ar ₂ and Ar ₃ are each independently phenyl, biphenylyl, terphenylyl, naphthyl, phenanthrenyl, dibenzofuranyl, or dibenzothiophenyl,
Organic light emitting device.
The method of claim 1,
R ₅ is any one selected from the group consisting of,
Organic light emitting element:

Above,
Q is hydrogen, C _1-10 alkyl, Si(C _1-4 alkyl) ₃ , or C _6-20 aryl,
Y ₁ is O, S, N(C _6-20 aryl), C(C _1-4 alkyl) ₂ , or C(C _6-20 aryl) ₂ .
The method of claim 1,
The second compound is represented by the following formula 2-1 or 2-2,
Organic light emitting element:
[Formula 2-1]

[Formula 2-2]

In Formulas 2-1 and 2-2,
Description of L ₄ , Ar ₃ and R ₅ is as defined in claim 1.
The method of claim 1,
The second compound is any one selected from the group consisting of,
Organic light emitting element:

The method of claim 1,
The third compound is represented by any one of the following Formulas 3-1 to 3-3,
Organic light emitting element:
[Formula 3-1]

[Chemical Formula 3-2]

[Chemical Formula 3-3]

In Formulas 3-1 to 3-3,
L ₅ , X ₁ to X ₃ , Ar ₄ and Ar ₅ are as defined in claim 1.
The method of claim 1,
All of X ₁ to X ₃ are N;
X ₁ and X ₂ are N and X ₃ is CH;
X ₁ and X ₃ are N and X ₂ is CH;
X ₁ is N and X ₂ and X ₃ are CH; or
X ₃ is N, and X ₁ and X ₂ are CH,
Organic light emitting device.
The method of claim 1,
L ₅ is a single bond, or any one selected from the group consisting of,
Organic light emitting element:

The method of claim 1,
Ar ₄ and Ar ₅ are each independently, any one selected from the group consisting of,
Organic light emitting element:

Above,
Z is hydrogen, cyano, halogen, Si(C _1-4 alkyl) ₃ , C _1-10 alkyl, or C _6-20 aryl,
X'is O, S, N(C _6-20 aryl), C(C _1-4 alkyl) ₂ , or C(C _6-20 aryl) ₂ .
The method of claim 1,
The third compound is any one selected from the group consisting of,
Organic light emitting element:

The method of claim 1,
The hole transport region includes a hole injection layer, a hole transport layer, and an electron blocking layer,
The electron blocking layer is located in contact with the emission layer,
The first compound is contained in the hole transport layer or the electron blocking layer,
Organic light emitting device.

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