KR102145024B1 - Organic light emitting device - Google Patents

Abstract

The present invention relates to an organic light emitting device without distortion of the emission spectrum.

Description

Organic light emitting device

The present invention relates to an organic light emitting device without distortion of the emission spectrum.

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.

An 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.

On the other hand, the light emitting layer of the organic light emitting device is made of one or more host materials and a light emitting dopant material that actually emits light. Accordingly, although each material of the light-emitting dopant exhibits a unique emission spectrum, a spectrum shift occurs depending on the type or combination of the host material to be used, so that a desired color is often not obtained. Accordingly, in an organic light-emitting device using a color filter, the light transmission range of the color filter does not fit, resulting in a problem of reducing efficiency. In addition, even in an organic light-emitting device that does not use a color filter, a color different from the color of the actually intended light-emitting dopant is generated, causing a problem in realizing color or luminance.

Accordingly, the present inventors confirmed the present invention by identifying an organic light-emitting device capable of solving the above problems, as will be described later.

Korean Patent Publication No. 10-2000-0051826

The present invention is to provide an organic light emitting device without distortion of the emission spectrum.

In order to solve the above problems, the present invention is a positive electrode; cathode; And an emission layer between the anode and the cathode, wherein the emission layer includes a compound having a dipole moment of 4.5 or less as a first host.

The organic light-emitting device according to the present invention can provide an organic light-emitting device without distortion of an emission spectrum by using a material of a host and a dopant that satisfies a specific dipole moment value.

FIG. 1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4.
FIG. 2 shows an example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole transport layer 5, a light-emitting layer 3, an electron transport layer 6, and a cathode 4.
3 shows a substrate 1, an anode 2, a hole injection layer 7, a hole transport layer 5, a light emitting layer 3, an electron transport layer 6, an electron injection layer 8 and a cathode 4 It shows an example of the formed organic light emitting device.
4 shows emission spectra of Examples and Comparative Examples of the present invention.

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

Definition of Terms

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; Nitrile 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 heterocyclic 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 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 C 1 to C 25 linear, branched or cyclic chain alkyl group or a C 6 to C 25 aryl group. 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 trimethyl boron group, a triethyl boron group, a t-butyldimethyl boron group, a triphenyl boron group, and a phenyl boron 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, cycloheptylmethyl, 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 number of carbon atoms in the aryl group is 6 to 30. 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 phenanthryl 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, the heterocyclic group is a heterocyclic group containing at least one of O, N, Si and S as a heterogeneous element, and the number of carbon atoms is not particularly limited, but it is preferably 2 to 60 carbon atoms. Examples of the heterocyclic group include a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazine group, a triazole 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, thiazolyl group, Isoxazolyl group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl 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 description of the heterocyclic group 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 aforementioned heterocyclic group 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 heterocycle is not a monovalent group, and the description of the aforementioned heterocyclic group may be applied except that the heterocycle is formed by bonding of two substituents.

Emitting layer

The present invention, the anode; cathode; And an emission layer between the anode and the cathode, wherein the emission layer includes a compound having a dipole moment of 4.5 or less as a host.

The emission spectrum of the dopant may shift according to the type or combination of hosts included in the emission layer of the organic light emitting device. This is due to a solid state solvation effect generated by the dipole moment of the host, and causes problems such as defects and reduced efficiency because the intended emission spectrum cannot be obtained.

Accordingly, in the present invention, a compound having a dipole moment value of 4.5 or less is used as a host of the emission layer so that the emission spectrum shift of the emission layer of the organic light emitting device can be minimized.

The term "dipole moment" used herein refers to a physical quantity representing the degree of polarity, and may be calculated as in Equation 3 below.

[Equation 3]

In Equation 3, the molecular density is calculated and the value of the dipole moment can be obtained. For example, the molecular density can be obtained by calculating the charge and dipole for each atom using the Hirshfeld Charge Analysis method, and calculating it according to the following equation, and the calculation result is put in Equation 3 above to obtain the dipole moment ( Dipole Moment) can be obtained.

As described above, when a compound having a dipole moment value of 4.5 or less is used as the host of the emission layer, a solid state solvation effect hardly occurs, thus minimizing spectrum shift. Can be.

Preferably, the light-emitting layer includes a light-emitting dopant, and the host and the light-emitting dopant satisfy Equation 1 below:

[Equation 1]

[fh×DM(host) + fd×DM(luminescent dopant)] ≤ 4.5

In Equation 1,

DM (host) and DM (light emitting dopant) are dipole moment values of the host and the light emitting dopant, respectively,

fh means a value obtained by dividing the weight of the host by the total weight of the host and the light emitting dopant,

fd denotes a value obtained by dividing the weight of the light emitting dopant by the total weight of the host and the light emitting dopant.

In addition, preferably, the emission layer includes n materials different from each other, where n is an integer of 2 or more, at least one of the n materials is a light-emitting dopant, and the n materials satisfy Equation 2 below. do:

[Equation 2]

In Equation 2,

DM _i means the dipole moment value of each material,

A _i means the weight of each substance divided by the total weight of the n substances.

Preferably, n is 2, 3, or 4.

That is, the emission layer of the organic light emitting device according to the present invention may include a compound having a dipole moment value of greater than 4.5 in addition to a compound having a dipole moment value of 4.5 or less, but the total dipole moment value must be 4.5 or less depending on their concentration. .

As the host, a compound having a dipole moment value of 4.5 or less may be used, and as an example, a compound represented by the following Formula 1 or a compound represented by the following Formula 2 may be used:

[Formula 1]

In Formula 1,

Ar ₁₁ and Ar ₁₂ are each independently substituted or unsubstituted C _6-60 aryl, or substituted or unsubstituted N, O, and C _2- including any one or more hetero atoms selected from the group consisting of S ₆₀ heteroaryl,

L ₁₁ and L ₁₂ are each independently a single bond, or a substituted or unsubstituted C _6-60 arylene,

Each R ₁ is independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted C _1-60 alkyl; C _1-60 haloalkyl; Substituted or unsubstituted C _1-60 alkoxy; Substituted or unsubstituted C _1-60 haloalkoxy; Substituted or unsubstituted C _3-60 cycloalkyl; A substituted or unsubstituted C _2-60 alkenyl group; Substituted or unsubstituted C _6-60 aryloxy; Substituted or unsubstituted C _6-60 aryl; Substituted or unsubstituted amine; Substituted or unsubstituted silyl; Or a substituted or unsubstituted C _2-60 heterocyclic group including at least one of O, N, Si and S,

h and i are each independently 1 or 2,

x is an integer from 0 to 8,

[Formula 2]

In Formula 2,

Ar ₂₁ , Ar ₂₂ and Ar ₂₃ are each independently, substituted or unsubstituted C _6-60 aryl, or substituted or unsubstituted N, O and S containing any one or more hetero atoms selected from the group consisting of C _2-60 heteroaryl,

L ₂₁ , L ₂₂ and L ₂₃ are each independently a single bond, or a substituted or unsubstituted C _6-60 arylene,

Each R ₂ is independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted C _1-60 alkyl; Substituted or unsubstituted C _1-60 haloalkyl; Substituted or unsubstituted C _1-60 alkoxy; Substituted or unsubstituted C _1-60 haloalkoxy; Substituted or unsubstituted C _3-60 cycloalkyl; A substituted or unsubstituted C _2-60 alkenyl group; Substituted or unsubstituted C _6-60 aryloxy; Substituted or unsubstituted C _6-60 aryl; Substituted or unsubstituted amine; Substituted or unsubstituted silyl; Or a substituted or unsubstituted C _2-60 heterocyclic group including at least one of O, N, Si and S,

m, n and o are each independently 1 or 2,

y is an integer from 0 to 8.

Preferably, the emission layer includes both the compound represented by Formula 1 and the compound represented by Formula 2 as hosts.

The compound represented by Formula 1 has an anthracene structure, and an aromatic ring or a heteroaromatic ring is substituted at positions 9 and 10 of the anthracene to have a small dipole moment value.

Preferably, Ar ₁₁ and Ar ₁₂ are each independently selected from phenyl, naphthyl, biphenylyl, or the group consisting of, and Ar ₁₁ and Ar ₁₂ are unsubstituted or methyl or trimethylsilyl. Is replaced:

In the above, X ₁ is S or O.

Preferably, L ₁₁ and L ₁₂ are each independently a single bond, phenylene, naphthylene, anthracenylene, or thiophenylene.

Preferably, the compound represented by Formula 1 is any one compound selected from the group consisting of:

The compound represented by Chemical Formula 1 can be prepared by a manufacturing method as shown in Scheme 1.

[Scheme 1]

In Reaction Scheme 1, the definitions other than X are as defined above, and X is halogen, more preferably bromo. The manufacturing method is a Suzuki coupling reaction, a reaction in which a substituent is introduced at No. 9 or No. 10 of anthracene, and may be more specific in Preparation Examples to be described later.

The compound represented by Formula 2 has an anthracene structure, an aromatic ring or a heteroaromatic ring is substituted at positions 1 and 8 of an anthracene, and an aromatic ring or heteroaromatic ring is substituted at position 10, so that a small dipole moment value It is characterized by having.

Preferably, Ar ₂₁ , Ar ₂₂ and Ar ₂₃ are each independently, phenyl, dimethylphenyl, naphthyl, biphenylline, terphenyl, or any one selected from the group consisting of:

Above,

X ₂ is S, O, N(R ₃ ), or C(R ₄ )(R ₅ ),

R ₃ to R ₅ are each independently substituted or unsubstituted C _1-60 alkyl, substituted or unsubstituted C _6-60 aryl, or R ₄ and R ₅ are substituted or unsubstituted C _{6-60 together} Form aryl.

Preferably, Ar ₂₁ and Ar ₂₂ are identical to each other.

Preferably, L ₂₁ , L ₂₂ and L ₂₃ are each independently a single bond, phenylene, or naphthylenyl.

Preferably, the compound represented by Formula 2 is any one compound selected from the group consisting of:

The compound represented by Chemical Formula 2 can be prepared by the same method as in Scheme 2 below. The manufacturing method may be more specific in the manufacturing examples to be described later.

[Scheme 2]

In Reaction Scheme 2, the definitions other than X are as defined above, and X is halogen, more preferably bromo. The manufacturing method is a Suzuki coupling reaction, a reaction of introducing a substituent to anthracene Nos. 1, 8, and 10, and may be more specific in Preparation Examples to be described later.

Meanwhile, the organic light-emitting devices other than the above-described host are not particularly limited as long as they can be used for the organic light-emitting device, and each configuration will be described below.

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); Combinations of metals and oxides such as ZnO:Al or SNO ₂ :Sb; Poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), conductive polymers such as polypyrrole and polyaniline, and the like, but are not limited thereto.

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

Hole injection layer

The organic light-emitting device according to the present invention may include a hole injection layer for injecting holes from an electrode.

The hole injection material has the ability to transport holes, so it 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 excellent in thin film formation ability is preferred. It is preferable 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 hole injection materials include metal porphyrin, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based organic substances. Organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers, etc., but are not limited thereto.

Hole transport layer

The organic light-emitting device according to the present invention may include a hole transport layer that receives holes from an anode or a hole injection layer and transports holes to the emission layer.

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

Emitting layer

The emission layer of the organic light-emitting device according to the present invention may include a dopant in addition to the above-described host.

Dopant materials 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 aryl group, silyl group, alkyl group, cycloalkyl group and arylamino group are substituted or unsubstituted. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetraamine, etc., 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, a compound represented by the following Formula 3 may be used as the dopant:

[Chemical Formula 3]

In Chemical Formula 3,

R ₁ to R ₈ are each independently hydrogen, halogen, substituted or unsubstituted C _1-20 alkyl, substituted or unsubstituted C _3-10 cycloalkyl, substituted or unsubstituted silyl, cyano, or substituted or _{Unsubstituted} C _6-30 aryl,

Ar ₁ to Ar ₄ are each independently a substituted or unsubstituted C _6-30 aryl, or a C _2-60 heterocyclic group containing at least one of substituted or unsubstituted O, N, Si and S, provided that, At least one of Ar ₁ to Ar ₄ is represented by Formula 4:

[Formula 4]

In Chemical Formula 4,

X is O, or S,

R ₉ and R ₁₀ are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted C _1-60 alkyl; Substituted or unsubstituted C _1-60 haloalkyl; Substituted or unsubstituted C _1-60 alkoxy; Substituted or unsubstituted C _1-60 haloalkoxy; Substituted or unsubstituted C _3-60 cycloalkyl; Substituted or unsubstituted C _2-60 alkenyl; Substituted or unsubstituted C _6-60 aryloxy; Substituted or unsubstituted C _6-60 aryl; Substituted or unsubstituted amine; Substituted or unsubstituted silyl; Or a substituted or unsubstituted C _2-60 heterocyclic group including at least one of O, N, Si and S.

Preferably, R ₁ to R ₈ are hydrogen.

Preferably, Ar ₁ and Ar ₃ are phenyl and Ar ₂ and Ar ₄ are dibenzofuranyl.

Examples of the compound represented by Formula 3 are as follows:

Electron transport layer

The organic light-emitting device according to the present invention may include an electron transport layer that receives electrons from a cathode or an electron injection layer and transports electrons to the emission layer.

As the electron transport material, a material capable of receiving electrons from the cathode and transferring them to the emission layer is suitable, and a material having high mobility for electrons is suitable. Specific examples include the Al complex of 8-hydroxyquinoline; Complexes containing Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto. The electron transport layer can be used with any desired cathode material as used according to the prior art. In particular, examples of suitable cathode materials are conventional materials that have a low work function and are followed by an aluminum layer or a silver layer. Specifically, they are cesium, barium, calcium, ytterbium and samarium, and in each case an aluminum layer or a silver layer follows.

Electron injection layer

The organic light emitting device according to the present invention may include an electron injection layer for injecting electrons from an electrode.

As an electron injection material, it has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect for the light emitting layer or the light emitting material, prevents the movement of excitons generated from the light emitting layer to the hole injection layer, and , A compound having excellent thin film forming ability is preferable.

Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, and their derivatives, metals Complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto. Examples of the metal complex compound include lithium 8-hydroxyquinolinato, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)( o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, etc. It is not limited to this.

Organic light emitting element

The structure of the organic light emitting device according to the present invention is illustrated in FIGS. 1 to 3. FIG. 1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4.

FIG. 2 shows an example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole transport layer 5, a light-emitting layer 3, an electron transport layer 6, and a cathode 4.

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

The organic light emitting device according to the present invention can be manufactured by sequentially stacking the above-described configurations. At this time, by using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, a metal or conductive metal oxide or alloy thereof is deposited on the substrate to form an anode. And, after forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer thereon, it can be prepared by depositing a material that can be used as a cathode thereon. In addition to such a 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 for 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.

Hereinafter, preferred embodiments are presented to aid in understanding the present invention. However, the following examples are provided for easier understanding of the present invention, and the contents of the present invention are not limited thereby.

Manufacturing example 1: Preparation of the compound represented by Formula 1

Manufacturing example 1-8

9-bromo-10-phenylanthracene (A, 10 g, 30.1 mmol) and (4-phenylnaphthalene-1-yl) boronic acid (B, 9 g, 36.1 mmol), Pd(t-Bu ₃ P) ₂ (0.8 g , 0.15 mmol) was added to 2M K ₂ CO ₃ aqueous solution (30 mL) and THF (100 mL), and stirred under reflux for about 12 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, the organic layer was separated from the reaction mixture, the organic layer was dried over magnesium sulfate, distilled under reduced pressure, and recrystallized from Tol (toluene)/EA (ethyl acetate) to prepare a compound (12.8 g, 93). %) was prepared.

MS [M ⁺ ] = found 456.32, calc. 456.19

Manufacturing example 1-18

Prepared in the same manner as in Preparation Example 1-8, but using 9-bromo-10-(naphthalene-1-yl)anthracene instead of Compound A and (4-phenylnaphthalene-2-yl)boronic acid instead of Compound B, prepared Examples 1-18 compounds were prepared.

MS [M ⁺ ] = found 506.98, calc. 506.20

Manufacturing example 1-20

Prepared in the same manner as in Preparation Example 1-8, but using 9-bromo-10-(naphthalene-1-yl)anthracene instead of Compound A and (4-phenylnaphthalene-1-yl)boronic acid instead of Compound B, prepared Examples 1-20 compounds were prepared.

MS [M ⁺ ] = found 506.22, calc. 506.20

Manufacturing example 1-26

Prepared in the same manner as in Preparation Example 1-8, but using 9-bromo-10-(naphthalene-1-yl)anthracene instead of compound A and (1,1′-binaphthalen)-4-ylboronic acid instead of compound B , Preparation Example 1-26 compound was prepared.

MS [M ⁺ ] = found 556.09, calc. 556.22

Manufacturing example 1-33

Prepared in the same manner as in Preparation Example 1-8, but using 9-bromo-10-(naphthalene-2-yl)anthracene instead of Compound A and (4-phenylnaphthalene-2-yl)boronic acid instead of Compound B, prepared Examples 1-33 compounds were prepared.

MS [M ⁺ ] = found 506.94, calc. 506.20

Manufacturing example 1-34

Prepared in the same manner as in Preparation Example 1-8, but using 9-bromo-10-(naphthalene-2-yl)anthracene instead of Compound A and (1,1'-binaphthalen)-4-ylboronic acid instead of Compound B , Preparation Example 1-34 compound was prepared.

MS [M ⁺ ] = found 456.32, calc. 456.19

Manufacturing example 1-35

Prepared in the same manner as in Preparation Example 1-8, but using 9-bromo-10-(naphthalene-2-yl)anthracene instead of Compound A and (4-(naphthalene-1-yl)phenyl)boronic acid instead of Compound B Thus, a compound of Preparation Example 1-35 was prepared.

MS [M ⁺ ] = found 506.75, calc. 506.20

Manufacturing example 1-36

Prepared in the same manner as in Preparation Example 1-8, but using 9-bromo-10-(naphthalene-2-yl)anthracene instead of compound A and (6-phenylnaphthalene-2-yl) boronic acid instead of compound B, prepared Examples 1-36 compounds were prepared.

MS [M ⁺ ] = found 506.98, calc. 506.20

Manufacturing example 1-38

Prepared in the same manner as in Preparation Example 1-8, but using 9-bromo-10-(naphthalene-2-yl)anthracene instead of compound A and (8-phenylnaphthalene-2-yl)boronic acid instead of compound B, prepared Examples 1-38 compounds were prepared.

MS [M ⁺ ] = found 506.88, calc. 506.20

Manufacturing example 1-43

Prepared in the same manner as in Preparation Example 1-8, but using 9-bromo-10-(naphthalene-2-yl)anthracene instead of compound A and (5-phenylnaphthalene-2-yl) boronic acid instead of compound B, prepared Example 1-43 The compound was prepared.

MS [M ⁺ ] = found 506.91, calc. 506.20

Manufacturing example 1-73

Prepared in the same manner as in Preparation Example 1-8, except for 9-bromo-10-(naphthalene-1-yl)anthracene instead of Compound A, and indolo[3,2,1-jk]carbazol-6-ylboronic acid instead of Compound B Using, Preparation Example 1-72 compound was prepared.

MS [M ⁺ ] = found 543.69, calc. 543.20

Manufacturing example 1-79

Prepared in the same manner as in Preparation Example 1-8, but instead of Compound A, 9-bromo-10-(naphthalene-1-yl)anthracene, instead of Compound B (3-(5-phenylthiophen-2-yl)phenyl)boronic acid Using, Preparation Example 1-79 compound was prepared.

MS [M ⁺ ] = found 538.88, calc. 538.18

Manufacturing example 1-81

Prepared in the same manner as in Preparation Example 1-8, but instead of Compound A, 9-bromo-10-(naphthalene-2-yl)anthracene, instead of Compound B (3-(5-phenylthiophen-2-yl)phenyl)boronic acid Using, Preparation Example 1-81 compound was prepared.

MS [M ⁺ ] = found 538.85, calc. 538.18

Manufacturing example 1-86

It was prepared in the same manner as in Preparation Example 1-8, but using 9-([1,1'-biphenyl]-4-yl)-10-bromoanthracene) instead of Compound A, Preparation Example 1-86 was prepared.

MS [M ⁺ ] = found 532.18, calc. 532.22

Manufacturing example 1-87

It was prepared in the same manner as in Preparation Example 1-8, but using 9-bromo-10-(4-(naphthalene-1-yl)phenyl)anthracene instead of Compound A, Preparation Example 1-87 compound was prepared.

MS [M ⁺ ] = found 582.65, calc. 582.23

Manufacturing example 2: Preparation of the compound represented by Formula 2

Manufacturing example 2-1

(Step 1)

Dissolved in 1,8-dichloroanthraquinone (A', 100 g, 360 mmol) and aqueous ammonia (4000 L), Zn dust (3000 g) was added and stirred under reflux. After the reaction was completed, cooled to room temperature, filtered, the organic layer was separated from the reaction filtrate, the organic layer was dried over magnesium sulfate, distilled under reduced pressure, and the solid obtained by recrystallization with Hexane was dissolved in isopropyl alcohol, and concentrated hydrochloric acid was added to reflux for 5 hours Stirred. After the reaction was completed, the mixture was cooled to room temperature, and the resulting solid was filtered, washed with water, and dried to obtain 1,8-dichloroanthracene (B', 55.6 g, 63%).

MS [M ⁺ ] = found 246.33, calc. 246.00

(Step 2)

1,8-dichloroanthracene (B', 10 g, 40.5 mmol), dibenzo[b,d]furan-4-ylboronic acid (15.3 g, 89 mmol), Pd(dba) ₂ (0.7 g, 1.22 mmol), PCy ₃ (tricyclohexylphosphine, 0.67 g, 2.43 mmol) was added to 2M K ₃ PO ₄ aqueous solution (50 mL) and THF (250 mL), and stirred under reflux for about 12 hours. After the reaction is finished, the reaction mixture is cooled to room temperature, the organic layer is separated from the reaction mixture, the organic layer is dried over magnesium sulfate, distilled under reduced pressure, and recrystallized with THF/EtOH to obtain 1,8-bis(dibenzo[b,d]furan-4-yl ) ananthracene (C', 14 g, 68%) was obtained.

MS [M ⁺ ] = found 510.09, calc. 510.16

(Step 3)

1,8-bis(dibenzo[b,d]furan-4-yl)anthracene (C', 14 g, 27.5 mmol) was dissolved in chloroform (250 mL) and then NBS (5.4 g, 30.3 mmol) was added at 0°C. And stirred at room temperature for 12 hours. After completion of the reaction, the solid generated during the reaction was filtered, washed with distilled water, and dried, 4,4'-(10-bromoanthracene-1,8-diyl)didibenzo[b,d]furan (D', 13.0 g, 85%).

MS [M ⁺ ] = found 588.21, calc. 588.07

(Step 4)

4,4'-(10-bromoanthracene-1,8-diyl)didibenzo[b,d]furan (D', 10.0 g, 17.0 mmol), naphthalene-1-ylboronic acid (3.22 g, 18.7 mmol), Pd( t-Bu3)P2 (0.43 g, 0.09 mmol) was added to 2M K ₂ CO ₃ aqueous solution (50 mL) and THF (150 mL), followed by reflux stirring for about 12 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, the organic layer was separated from the reaction mixture, the organic layer was dried over magnesium sulfate, distilled under reduced pressure, and recrystallized from Tol/EA to obtain Preparation Example compound 2-1 (10.1 g, 93%).

MS [M ⁺ ] = found 635.52, calc. 636.21

Manufacturing example 2-2

In step 2 of Preparation Example 2-1, naphthalene-1-ylboronic acid was used instead of dibenzo[b,d]furan-4-ylboronic acid, and dibenzo[b,d]furan- instead of naphthalene-1-ylboronic acid in step 4 Using 4-ylboronic acid, a compound of Preparation Example 2-2 was prepared.

MS [M ⁺ ] = found 596.25, calc. 596.21

Manufacturing example 2-3

In step 4 of Preparation Example 2-1, using dibenzo[b,d]furan-4-ylboronic acid instead of naphthalene-1-ylboronic acid, Preparation Example 2-3 was prepared.

MS [M ⁺ ] = found 676.51, calc. 676.20

Manufacturing example 2-10

In step 4 of Preparation Example 2-1, using phenylboronic acid instead of naphthalene-1-ylboronic acid, a compound of Preparation Example 2-10 was prepared.

MS [M ⁺ ] = found 586.33, calc. 586.19

Manufacturing example 2-45

In Step 2 of Preparation Example 2-1, naphthalene-1-ylboronic acid was used instead of dibenzo[b,d]furan-4-ylboronic acid, and phenylboronic acid was used instead of naphthalene-1-ylboronic acid in Step 4, Preparation Example Compound 2-45 was prepared.

MS [M ⁺ ] = found 506.88, calc. 506.20

Manufacturing example 2-46

In step 2 of Preparation Example 2-1, naphthalene-1-ylboronic acid was used instead of dibenzo[b,d]furan-4-ylboronic acid, and (1,1'-biphenyl) instead of naphthalene-1-ylboronic acid in step 4 Using 2-ylboronic acid, the compound of Preparation Example 2-46 was prepared.

MS [M ⁺ ] = found 582.51, calc. 582.23

Manufacturing example 2-47

In step 2 of Preparation Example 2-1, (3,5-dimethylphenyl)boronic acid was used instead of dibenzo[b,d]furan-4-ylboronic acid, and phenylboronic acid was used instead of naphthalene-1-ylboronic acid in step 4 , Preparation Example 2-47 compound was prepared.

MS [M ⁺ ] = found 462.38, calc. 462.23

Manufacturing example 2-48

In step 2 of Preparation Example 2-1, (3,5-dimethylphenyl)boronic acid was used instead of dibenzo[b,d]furan-4-ylboronic acid, and (1,1′) instead of naphthalene-1-ylboronic acid in step 4 Using -biphenyl)2-ylboronic acid, Preparation Example 2-48 compound was prepared.

MS [M ⁺ ] = found 538.30, calc. 538.27

Manufacturing example 2-49

In step 4 of Preparation Example 2-1, using (1,1'-biphenyl)2-ylboronic acid instead of naphthalene-1-ylboronic acid, Preparation Example 2-49 compound was prepared.

MS [M ⁺ ] = found 662.42, calc. 662.22

Manufacturing example 2-50

In step 2 of Preparation Example 2-1, using naphthalene-1-ylboronic acid instead of dibenzo[b,d]furan-4-ylboronic acid, Preparation Example 2-50 compound was prepared.

MS [M ⁺ ] = found 556.63, calc. 556.22

Manufacturing example 2-51

In step 2 of Preparation Example 2-1, (9,9-diphenyl-9H-fluoren-4-yl)boronic acid was used instead of dibenzo[b,d]furan-4-ylboronic acid, and naphthalene-1-in step 4 Using phenylboronic acid instead of ylboronic acid, Preparation Example 2-51 compound was prepared.

MS [M ⁺ ] = found 886.11, calc. 886.36

Manufacturing example 2-52

In step 2 of Preparation Example 2-1, (9,9-diphenyl-9H-fluoren-4-yl)boronic acid was used instead of dibenzo[b,d]furan-4-ylboronic acid, and naphthalene-1-in step 4 Using dibenzo[b,d]furan-4-ylboronic acid instead of ylboronic acid, the compound of Preparation Example 2-52 was prepared.

MS [M ⁺ ] = found 976.22, calc. 976.37

Manufacturing example 2-53

In step 2 of Preparation Example 2-1, dibenzo[b,d]furan-1-ylboronic acid was used instead of dibenzo[b,d]furan-4-ylboronic acid to prepare a compound of Preparation Example 2-53.

MS [M ⁺ ] = found 636.31, calc. 636.21

Manufacturing example 2-54

Using (3-(dibenzo[b,d]furan-4-yl)phenyl)boronic acid instead of dibenzo[b,d]furan-4-ylboronic acid in Step 2 of Preparation Example 2-1, Preparation Example 2- 54 compound was prepared.

MS [M ⁺ ] = found 780.30, calc. 788.27

On the other hand, in addition to the compounds prepared in the above Preparation Example, the structures of the compounds used in the following Examples were as follows, respectively.

Example One

A glass substrate coated with a thin film of 150 nm indium tin oxide (ITO) was placed 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 by a filter made by Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, it was repeated twice with distilled water to perform ultrasonic cleaning for 10 minutes. After washing with distilled water, ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using nitrogen plasma, the substrate was transported to a vacuum evaporator. The following HAT-CN compound was thermally vacuum deposited to a thickness of 5 nm on the prepared ITO transparent electrode to form a hole injection layer. Subsequently, HTL1 was thermally vacuum evaporated to a thickness of 100 nm, and HTL2 was thermally vacuum evaporated to a thickness of 10 nm to form a hole transport layer. Subsequently, BH1 as a host and BD (weight ratio 95:5) as a dopant were simultaneously vacuum-deposited to form a light emitting layer having a thickness of 20 nm. Subsequently, ETL was vacuum deposited to a thickness of 20 nm to form an electron transport layer. Subsequently, LiF was vacuum deposited to a thickness of 0.5 nm to form an electron injection layer. Then, aluminum was deposited to a thickness of 100 nm to form a cathode, thereby manufacturing an organic light emitting device.

Example 2-63 and Comparative example 1~7

An organic light-emitting device was manufactured in the same manner as in Example 1, but using the materials and contents of Tables 1 and 2 as a host and a dopant. 1-13, 2-1, etc., corresponding to the substances in Tables 1 and 2 below, mean that the compounds prepared in each preparation example were used, and the total EML DM is the value obtained by multiplying the dipole moment value of each host and dopant by the content. It was calculated by summation.

Experimental example

The characteristics of the organic light-emitting devices prepared in Examples and Comparative Examples were evaluated, and the results are shown in Tables 3 and 4.

In addition, emission spectra of the organic light emitting diodes of Examples 1, 2, and 1 are shown in FIG. 3.

As shown in FIG. 4, the total DM of the emission layer of Example 1 and Example 2 was 0.09 and 4.47, respectively, and the total DM of the emission layer of Comparative Example 1 was 4.93. The peak max positions of each spectrum are 458 nm, 464 nm, and 476 nm in the order of Example 1, Example 2, and Comparative Example 1, respectively, and as the total DM of the emission layer increases, the spectrum moves toward a longer wavelength, and the dipole moment value of the host If this exceeds 4.5, the FWHM also increases rapidly. When this spectrum is represented by (CIE_x, CIE_y) as the CIE 1931 color space, Example 1, Example 2, and Comparative Example 1 are respectively (0.137, 0.092), (0.131, 0.152) and (0.156, 0.22). , When the value of the dipole moment of the host exceeded 4.5, the spectrum shifted to a long wavelength and the color purity rapidly deteriorated due to an increase in FWHM.

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

Claims (13)

anode; cathode; And a light emitting layer between the anode and the cathode,
The emission layer includes n materials different from each other,
Here, n is 3 or 4, at least one of the n materials is a light emitting dopant,
The n substances satisfy Equation 2 below,
The emission layer comprises a compound represented by the following Formula 1, and a compound represented by the following Formula 2 as a host,
Organic light emitting element:
[Equation 2]

In Equation 2,
DM _i means the dipole moment value of each material,
A _i means the weight of each substance divided by the total weight of the n substances,
[Formula 1]

In Formula 1,
Ar ₁₁ and Ar ₁₂ are each independently substituted or unsubstituted C _6-60 aryl, or substituted or unsubstituted N, O, and C _2- including any one or more hetero atoms selected from the group consisting of S ₆₀ heteroaryl,
L ₁₁ and L ₁₂ are each independently a single bond, or a substituted or unsubstituted C _6-60 arylene,
Each R ₁ is independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted C _1-60 alkyl; Substituted or unsubstituted C _1-60 haloalkyl; Substituted or unsubstituted C _1-60 alkoxy; Substituted or unsubstituted C _1-60 haloalkoxy; Substituted or unsubstituted C _3-60 cycloalkyl; A substituted or unsubstituted C _2-60 alkenyl group; Substituted or unsubstituted C _6-60 aryloxy; Substituted or unsubstituted C _6-60 aryl; Substituted or unsubstituted amine; Substituted or unsubstituted silyl; Or a substituted or unsubstituted C _2-60 heterocyclic group including at least one of O, N, Si and S,
h and i are each independently 1 or 2,
x is an integer from 0 to 8,
[Formula 2]

In Formula 2,
Ar ₂₁ , Ar ₂₂ and Ar ₂₃ are each independently a substituted or unsubstituted C _6-60 aryl, or a substituted or unsubstituted N, O and S containing any one or more hetero atoms selected from the group consisting of C _2-60 heteroaryl,
L ₂₁ , L ₂₂ and L ₂₃ are each independently a single bond, or a substituted or unsubstituted C _6-60 arylene,
Each R ₂ is independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted C _1-60 alkyl; Substituted or unsubstituted C _1-60 haloalkyl; Substituted or unsubstituted C _1-60 alkoxy; Substituted or unsubstituted C _1-60 haloalkoxy; Substituted or unsubstituted C _3-60 cycloalkyl; A substituted or unsubstituted C _2-60 alkenyl group; Substituted or unsubstituted C _6-60 aryloxy; Substituted or unsubstituted C _6-60 aryl; Substituted or unsubstituted amine; Substituted or unsubstituted silyl; Or a substituted or unsubstituted C _2-60 heterocyclic group including at least one of O, N, Si and S,
m, n and o are each independently 1 or 2,
y is an integer from 0 to 8.
delete delete delete delete The method of claim 1,
Ar ₁₁ and Ar ₁₂ are each independently selected from the group consisting of phenyl, naphthyl, biphenylyl, or the following, and Ar ₁₁ and Ar ₁₂ are unsubstituted or substituted with methyl or trimethylsilyl,
Organic light emitting element:

In the above, X ₁ is S or O.
The method of claim 1,
L ₁₁ and L ₁₂ are each independently a single bond, phenylene, naphthylene, anthracenylene, or thiophenylene,
Organic light emitting device.
The method of claim 1,
The compound represented by Formula 1 is any one compound selected from the group consisting of:
Organic light emitting element:

The method of claim 1,
Ar ₂₁ , Ar ₂₂ and Ar ₂₃ are each independently, phenyl, dimethylphenyl, naphthyl, biphenylline, terphenyl, or any one selected from the group consisting of,
Organic light emitting element:

Above,
X ₂ is S, O, N(R ₃ ), or C(R ₄ )(R ₅ ),
R ₃ to R ₅ are each independently substituted or unsubstituted C _1-60 alkyl, substituted or unsubstituted C _6-60 aryl, or R ₄ and R ₅ are substituted or unsubstituted C _{6-60 together} Forming aryl,
Organic light emitting device.
The method of claim 1,
Ar ₂₁ and Ar ₂₂ are the same as each other,
Organic light emitting device.
The method of claim 1,
L ₂₁ , L ₂₂ and L ₂₃ are each independently a single bond, phenylene, or naphthylenyl,
Organic light emitting device.
The method of claim 1,
The compound represented by Formula 2 is any one compound selected from the group consisting of,
Organic light emitting element:

The organic light-emitting device of claim 1, wherein the emission layer comprises a compound represented by Formula 3 below as a dopant.
[Chemical Formula 3]

In Chemical Formula 3,
R ₁ to R ₈ are each independently hydrogen, halogen, substituted or unsubstituted C _1-20 alkyl, substituted or unsubstituted C _3-10 cycloalkyl, substituted or unsubstituted silyl, cyano, or substituted or _{Unsubstituted} C _6-30 aryl,
Ar ₁ to Ar ₄ are each independently a substituted or unsubstituted C _6-30 aryl, or a C _2-60 heterocyclic group containing at least one of substituted or unsubstituted O, N, Si and S, provided that, At least one of Ar ₁ to Ar ₄ is represented by Formula 4:
[Formula 4]

In Chemical Formula 4,
X is O, or S,
R ₉ and R ₁₀ are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted C _1-60 alkyl; Substituted or unsubstituted C _1-60 haloalkyl; Substituted or unsubstituted C _1-60 alkoxy; Substituted or unsubstituted C _1-60 haloalkoxy; Substituted or unsubstituted C _3-60 cycloalkyl; Substituted or unsubstituted C _2-60 alkenyl; Substituted or unsubstituted C _6-60 aryloxy; Substituted or unsubstituted C _6-60 aryl; Substituted or unsubstituted amine; Substituted or unsubstituted silyl; Or a substituted or unsubstituted C _2-60 heterocyclic group including at least one of O, N, Si and S.

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