KR102240143B1 - Novel compound and organic light emitting device comprising the same - Google Patents

Abstract

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

Description

Novel compound and organic light emitting device comprising the same

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

In general, the organic light emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy by 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. When it falls back to the ground, it glows.

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 a novel compound and an organic light emitting device comprising the same.

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

[Formula 1]

In Formula 1,

A, B, and C are each independently benzene or pyridine,

One of R is -X-M, the other is hydrogen,

X is O, or S,

M is an alkali metal or an alkaline earth metal,

n1, n2, and n3 are each independently an integer of 0 to 3,

R ₁ and R ₂ are each independently hydrogen or deuterium; halogen; Cyano; Substituted or unsubstituted C _1-60 alkyl; Substituted or unsubstituted C _2-60 alkenyl; Substituted or unsubstituted C _2-60 alkynyl; Substituted or unsubstituted C _3-30 cycloalkyl; Substituted or unsubstituted C _6-60 aryl; _{Or a substituted or unsubstituted C 2-60} heteroaryl including any one or more heteroatoms selected from the group consisting of N, O and S; Or _one of R 1 and one of R ₂ are connected to each other to form -L-,

L is S, O, SO ₂ , P(=O)-Ar ₁ , or N-Ar ₁ ,

Ar ₁ is substituted or unsubstituted C _6-60 aryl; _{Or substituted or unsubstituted C 2-60} heteroaryl including any one or more selected from the group consisting of N, O and S,

R ₃ is hydrogen, pyridinyl, or -PO(Ar ₂ )(Ar ₃ ),

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

Provided that at least one of A, B, and C is pyridine; L is S, O, SO ₂ , or P(=O)-Ar ₁ ; Or R ₃ is pyridinyl.

In addition, the present invention is a first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes an electron injection layer, and the electron injection layer is represented by Formula 1 above. It provides an organic light-emitting device comprising a compound to be.

The compound represented by Chemical Formula 1 may be used as a material for an organic material layer of an organic light-emitting device, and may improve efficiency, low driving voltage, and/or lifetime characteristics in the organic light-emitting device. In particular, the compound represented by Formula 1 may be used as an electron injection material.

1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4.
2 is composed of a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), a light emitting layer (7), an electron transport layer (8), an electron injection layer (9) and a cathode (4). It shows an example of an organic light-emitting device.

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

The present invention provides a compound represented by Chemical Formula 1.

는 다른 치환기에 연결되는 결합을 의미한다. In this specification,

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 above-exemplified 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 a C1-C25 linear, branched or cyclic alkyl group or an aryl group having 6 to 25 carbon atoms in the oxygen of the ester 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, a phenyl boron group, and the like, 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 linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-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 preferably has 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 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,

Can be, 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 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, isoxazolyl group, thiiadia There are a zolyl group, a phenothiazinyl group, and a dibenzofuranyl group, 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 description of the aforementioned 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 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 two substituents are bonded to each other and formed.

Preferably, M is Li.

Preferably, R ₁ and R ₂ are both hydrogen; Alternatively _{, one of R 1} and one of R ₂ are connected to each other to form -L-, and all others are hydrogen.

Preferably, Ar ₁ is phenyl. At this time, one hydrogen of the phenyl _{may be combined with R 1} to form a single bond.

Preferably, Ar ₂ and Ar ₃ are phenyl.

Preferably, Formula 1 is represented by the following Formulas 1-1, 1-2, or 1-3:

[Formula 1-1]

In Formula 1-1,

R is -X-M

X is O, or S,

M is an alkali metal or an alkaline earth metal,

L is S, O, SO ₂ , or P(=O)-Ar ₁ ,

[Formula 1-2]

[Formula 1-3]

In Formulas 1-2 and 1-3,

R is -X-M

X is O, or S,

M is an alkali metal or an alkaline earth metal,

L is S, O, SO ₂ , P(=O)-Ar ₁ , or N-Ar ₁ .

Preferably, the formula 1 is represented by the following formula 1-4, or 1-5:

[Formula 1-4]

In Formula 1-4,

One of R is -X-M, the other is hydrogen,

X is O, or S,

M is an alkali metal or an alkaline earth metal,

One of Y ₂ and Y ₃ is CH, the other is N,

[Formula 1-5]

In Formula 1-5,

R is -X-M,

X is O, or S,

M is an alkali metal or an alkaline earth metal,

One of Y ₂ and Y ₃ is CH and the other is N.

Representative examples of the compound represented by Formula 1 are as follows:

In addition, the present invention provides a method for preparing a compound represented by Chemical Formula 1 as shown in Scheme 1 below.

[Scheme 1]

In Reaction Scheme 1, the rest except for R'are as defined above, and R'is -OH or -SH.

The reaction is a reaction of a compound represented by Formula 1'with an organolithium agent. The organolithium compound that can be used in the reaction may be appropriately selected according to the compound to be prepared, and n-butyl lithium may be used as an example. The manufacturing method may be more specific in the manufacturing examples to be described later.

In addition, the present invention provides an organic light-emitting device including the compound represented by Formula 1 above. For example, the present invention provides a first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes an electron injection layer, and the electron injection layer is represented by Formula 1 above. It provides an organic light-emitting device comprising the compound to be displayed.

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

In addition, the organic light-emitting device according to the present invention may be a normal type organic light-emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate. In addition, the organic light-emitting device according to the present invention may be an inverted type organic light-emitting device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate. For example, the structure of an organic light-emitting device according to an embodiment of the present invention is illustrated in FIGS. 1 and 2.

1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4.

2 is a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), a light emitting layer (7), an electron transport layer (8), an electron injection layer (9) and a cathode (4). It shows an example of an organic light-emitting device. In such a structure, the compound represented by Formula 1 may be included in the electron injection layer.

The organic light-emitting device according to the present invention may be manufactured by materials and methods known in the art, except for including the compound represented by Formula 1 in the electron injection layer. In addition, when the organic light-emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.

For example, the organic light emitting device according to the present invention may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. 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 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 this method, an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

In addition, the compound represented by Formula 1 may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device. Here, the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, and the like, but is not limited thereto.

In addition to 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.

For example, the first electrode is an anode, the second electrode is a cathode, or the first electrode is a cathode, and the second electrode is an anode.

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.

The hole injection layer is a layer that injects holes from the electrode, and has the ability to transport holes as a hole injection material, so that 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 is generated from the light emitting layer. A compound that prevents the movement of excitons to the electron injection layer or the electron injection material and has excellent ability to form a thin film is preferable. 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, but are not limited thereto.

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

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

The emission layer may include a host material and a dopant material. Host materials include condensed aromatic ring derivatives or heterocyclic-containing compounds. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

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, periflanthene and the like 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, and styryltetraamine, but are not limited thereto. In addition, examples of the metal complex include, but are not limited to, an iridium complex and a platinum complex.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the emission layer. As an electron transport material, a material capable of injecting electrons from the cathode and transferring them to the emission layer, and a material having high mobility for electrons is suitable. Do. Specific examples include Al complex of 8-hydroxyquinoline; Complexes containing Alq _3; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto. The electron transport layer can be used with any desired cathode material as used according to the prior art. In 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.

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.

In addition, the compound represented by Formula 1 may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.

The preparation of the compound represented by Formula 1 and the organic light-emitting device including the same 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.

[ Example ]

Example 1: Preparation of compound 1

Under a nitrogen stream, spiro[fluorene-9,9'-xanthene]-4'-ol (10 g, 28.7 mmol) was added to anhydrous THF solvent and cooled to -78°C. When the temperature of the solution reached -78°C, n-butyl lithium solution (in Hexane 2.5 M) (11.48 mL, 28.7 mmol) was slowly added dropwise. Then, it was slowly raised to room temperature and stirred for 2 hours. After completion of the reaction, the solvent was distilled to solidify and purified with ethanol to obtain compound 1 (6.5 g, yield 64%).

MS: [M+H] ⁺ = 355

Example 2: Preparation of compound 2

The same method as the preparation method of compound 1, except that spiro[fluorene-9,9'-xanthene]-4'-thiol was used instead of spiro[fluorene-9,9'-xanthene]-4'-ol To prepare compound 2.

MS: [M+H] ⁺ = 371

Example 3: Preparation of compound 3

Same as the preparation method of Compound 1, except that spiro[fluorene-9,9'-thioxanthene]-4'-ol was used instead of spiro[fluorene-9,9'-xanthene]-4'-ol Compound 3 was prepared by the method.

MS: [M+H] ⁺ = 371

Example 4: Preparation of compound 4

Same as the preparation method of Compound 1, except that spiro[fluorene-9,9'-thioxanthene]-4'-thiol was used instead of spiro[fluorene-9,9'-xanthene]-4'-ol Compound 4 was prepared by the method.

MS: [M+H] ⁺ = 387

Example 5: Preparation of compound 5

Except for using 4'-hydroxyspiro[fluorene-9,9'-thioxanthene]-10',10'-dioxide instead of spiro[fluorene-9,9'-xanthene]-4'-ol , Compound 5 was prepared in the same manner as in the preparation method of compound 1.

MS: [M+H] ⁺ = 403

Example 6: Preparation of compound 6

2-hydroxy-5'-phenylspiro[fluorene-9,10'-phosphinolino[3,2-c]pyridine]- instead of spiro[fluorene-9,9'-xanthene]-4'-ol Compound 6 was prepared in the same manner as in the preparation method of compound 1, except that 5′-oxide was used.

MS: [M+H] ⁺ = 464

Example 7: Preparation of compound 7

Compound 1, except that 3-(9-(pyridin-3-yl)-9H-fluoren-9-yl)phenol was used instead of spiro[fluorene-9,9'-xanthene]-4'-ol Compound 7 was prepared in the same manner as in the preparation method of.

MS: [M+H] ⁺ = 342

Example 8: Preparation of compound 8

Spiro[fluorene-9,5'-[1,6]naphthyridino[3,2,1-jk]carbazole]-2 instead of spiro[fluorene-9,9'-xanthene]-4'-ol -Compound 8 was prepared in the same manner as in the preparation method of compound 1, except that an ol was used.

MS: [M+H] ⁺ = 429

[ Experimental example ]

Experimental example One

A glass substrate coated with a thin film of 500Å of 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 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 washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

On the ITO transparent electrode prepared as described above, the following compound HAT was thermally vacuum deposited to a thickness of 50 Å to form a hole injection layer. The following compound NPB was vacuum deposited on the hole injection layer to a thickness of 1100 Å to form a hole transport layer. The following compound HT-A was vacuum-deposited to a thickness of 200 Å on the hole transport layer to form an electron blocking layer. A light emitting layer was formed by vacuum depositing the following compound BH and the following compound BD at a weight ratio of 25:1 on the electron blocking layer to a thickness of 350 Å. The following Compound ET-A and Compound 1 prepared in the above Example were vacuum-deposited at a 1:1 weight ratio on the emission layer to form a first electron transport layer with a thickness of 200Å. On the first electron transport layer, the following compounds ET-B and Li (lithium) were vacuum-deposited at a weight ratio of 100:1 to form a second electron transport layer having a thickness of 100 Å. A cathode was formed by depositing aluminum to a thickness of 1,000 Å on the second electron transport layer.

In the above process, the deposition rate of organic materials was maintained at 0.4 ~ 0.9 Å/sec, the deposition rate of lithium fluoride at the cathode was 0.3 Å/sec, and the deposition rate of aluminum was 2 Å/sec, and the vacuum degree during deposition was 1× An organic light emitting device was manufactured by maintaining ^{10 -7} to 5×10 ^{-8 torr.}

Experimental example 2 to 8

It was prepared in the same manner as in Experimental Example 1, but an organic light-emitting device was manufactured using the compound shown in Table 1 instead of Compound 1.

Comparative Experimental Example 1 to 3

It was prepared in the same manner as in Experimental Example 1, but an organic light-emitting device was manufactured using the compound shown in Table 1 instead of Compound 1. In Table 1 below, the compounds Liq, CGL A, and CGL B are the following compounds, respectively.

For the organic light emitting device prepared in the above Experimental Examples and Comparative Experimental Examples, the driving voltage, luminous efficiency and color coordinates were measured at a current density of ^{10 mA/cm 2} , and 90% of the initial luminance at a current density of ^{20 mA/cm 2} The time to become (T90) was measured. The results are shown in Table 1 below.

compound Voltage
(V) efficiency
(cd/A) Color coordinates
(x, y) Life (T90)
(hr) Experimental Example 1 Compound 1 4.13 6.19 (0.138, 0.112) 233 Experimental Example 2 Compound 2 4.15 6.01 (0.138, 0.110) 251 Experimental Example 3 Compound 3 4.11 6.12 (0.138, 0.111) 246 Experimental Example 4 Compound 4 4.16 6.05 (0.138, 0.112) 248 Experimental Example 5 Compound 5 4.12 6.22 (0.138, 0.112) 258 Experimental Example 6 Compound 6 4.02 6.27 (0.138, 0.111_ 242 Experimental Example 7 Compound 7 3.98 5.99 (0.138, 0.112) 244 Experimental Example 8 Compound 8 4.08 6.09 (0.138, 0.112) 250 Comparative Experimental Example 1 Liq 4.66 4.32 (0.138, 0.115) 213 Comparative Experiment 2 CGL A 4.72 4.48 (0.138, 0.113) 222 Comparative Experiment 3 CGL B 4.85 4.14 (0.138, 0.115) 198

As shown in Table 1, it was confirmed that the organic light-emitting device using the compound according to the present invention had a lower driving voltage, higher luminous efficiency, and improved life compared to the Comparative Experimental Example.

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

Claims (8)

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

In Formula 1,
A, B, and C are each independently benzene or pyridine,
One of R is -XM, the other is hydrogen,
X is O or S,
M is an alkali metal or an alkaline earth metal,
n1, n2, and n3 are each independently an integer of 0 to 3,
R ₁ and R ₂ are each independently hydrogen or deuterium; halogen; Cyano; Substituted or unsubstituted C _1-60 alkyl; Substituted or unsubstituted C _2-60 alkenyl; Substituted or unsubstituted C _2-60 alkynyl; Substituted or unsubstituted C _3-30 cycloalkyl; Substituted or unsubstituted C _6-60 aryl; _{Or a substituted or unsubstituted C 2-60} heteroaryl containing any one or more heteroatoms selected from the group consisting of N, O and S; Or _one of R 1 and one of R ₂ are connected to each other to form -L-,
Wherein L is S, O, SO ₂ , P(=O)-Ar ₁ , or N-Ar ₁ ,
Ar ₁ is substituted or unsubstituted C _6-60 aryl; _{Or substituted or unsubstituted C 2-60} heteroaryl including any one or more selected from the group consisting of N, O and S,
R ₃ is hydrogen, pyridinyl, or -PO(Ar ₂ )(Ar ₃ ),
Ar ₂ and Ar ₃ are each independently substituted or unsubstituted C _6-60 aryl; _{Or substituted or unsubstituted C 2-60} heteroaryl including any one or more selected from the group consisting of N, O and S,
Provided that at least one of A, B, and C is pyridine; L is S, O, SO ₂ , or P(=O)-Ar ₁ ; Or R ₃ is pyridinyl.
The method of claim 1,
M is Li,
compound.
The method of claim 1,
R ₁ and R ₂ are both hydrogen, or
_One of R 1 and one of R ₂ are connected to each other to form -L-, and the rest are all hydrogen,
compound.
The method of claim 1,
Ar ₂ and Ar ₃ are phenyl,
compound.
The method of claim 1,
Formula 1 is represented by the following Formulas 1-1, 1-2, or 1-3,
compound:
[Formula 1-1]

In Formula 1-1,
R is -XM
X is O, or S,
M is an alkali metal or an alkaline earth metal,
L is S, O, SO ₂ , or P(=O)-Ar ₁ ,
[Formula 1-2]

[Formula 1-3]

In Formulas 1-2 and 1-3,
R is -XM
X is O, or S,
M is an alkali metal or an alkaline earth metal,
L is S, O, SO ₂ , P(=O)-Ar ₁ , or N-Ar ₁ .
The method of claim 1,
Formula 1 is represented by the following Formula 1-4, or 1-5,
compound:
[Formula 1-4]

In Formula 1-4,
One of R is -XM, the other is hydrogen,
X is O, or S,
M is an alkali metal or an alkaline earth metal,
One of Y ₂ and Y ₃ is CH, the other is N,
[Formula 1-5]

In Formula 1-5,
R is -XM,
X is O, or S,
M is an alkali metal or alkaline earth metal,
One of Y ₂ and Y ₃ is CH and the other is N.
The method of claim 1,
The compound represented by Formula 1 is any one selected from the group consisting of the following,
compound:

A first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes an electron injection layer, and the electron injection layer includes the first to second electrodes. An organic light-emitting device comprising the compound according to any one of claims 7.

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