KR20220117848A - 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 containing the same, wherein the provided compound is represented by a chemical formula 1 below.

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 emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy using an organic material. The organic light emitting device using the organic light emitting phenomenon has a wide viewing angle, excellent contrast, fast response time, and 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 layer is often formed 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, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. When a voltage is applied between the two electrodes in the structure of the organic light emitting device, holes are injected into the organic material layer from the anode and electrons from the cathode are injected into the organic material layer. When the injected holes and electrons meet, excitons are formed, and the excitons It lights up when it falls back to the ground state.

The 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 organic light emitting material 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,

Any one of R ₁ to R ₁₂ is a substituent represented by the following formula (2), the rest are each independently hydrogen or deuterium;

[Formula 2]

In Formula 2,

이고,L ₁ is substituted or unsubstituted phenylene, substituted or unsubstituted biphenyldiyl, substituted or unsubstituted naphthalenediyl, or

ego,

L ₂ and L ₃ are each independently, a single bond; substituted or unsubstituted C _6-60 arylene; Or substituted or unsubstituted C _2-60 heteroarylene comprising any one or more selected from the group consisting of N, O and S,

Ar ₁ is substituted or unsubstituted C _6-60 aryl; Or substituted or unsubstituted C _2-60 heteroaryl comprising any one or more selected from the group consisting of N, O and S,

Ar ₂ is biphenylyl, terphenylyl, naphthyl, phenanthrenyl, phenyl naphthyl, dibenzofuranyl, dibenzothiophenyl, phenyl carbazole, dimethyl fluorenyl, benzonaphthofuranyl, or benzonaphtho thiophenyl.

In addition, the present invention is a first electrode; a second electrode provided to face the first electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound represented by Formula 1 above. .

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

FIG. 1 shows an example of an organic light emitting device including a substrate 1 , an anode 2 , an electron suppression layer 3 , a light emitting layer 4 , and a cathode 5 .
2 shows a substrate 1, an anode 2, a hole injection layer 6, a hole transport layer 7, an electron blocking layer 3, a light emitting layer 4, a hole blocking layer 8, an electron transport and injection layer An example of an organic light emitting device composed of (9) and a cathode (5) is shown.

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

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

또는

는 다른 치환기에 연결되는 결합을 의미한다. In this specification,

or

means a bond connected to another substituent.

As used herein, the term "substituted or unsubstituted" refers to deuterium; halogen group; nitrile group; nitro group; hydroxyl group; carbonyl group; ester group; imid; amino group; phosphine oxide group; alkoxy group; aryloxy group; alkyl thiooxy group; arylthioxy group; an alkyl sulfoxy group; arylsulfoxy group; silyl group; boron group; an alkyl group; cycloalkyl group; alkenyl group; aryl group; aralkyl group; aralkenyl group; an alkylaryl group; an alkylamine group; an aralkylamine group; heteroarylamine group; arylamine group; an aryl phosphine group; or N, O, and S atom means that it is substituted or unsubstituted with one or more substituents selected from the group consisting of a heteroaryl group containing one or more of the atoms, or substituted or unsubstituted with two or more substituents of the above-exemplified substituents connected . For example, "a substituent in which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected.

In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but it is preferably from 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

In the present specification, in the ester group, the oxygen of the ester group may be substituted with a linear, 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 from 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 specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like. However, the present invention 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, a phenylboron 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 number of carbon atoms in the alkyl group is 1 to 20. 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 linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the carbon number of the alkenyl group is 2 to 20. According to another exemplary embodiment, the carbon number of the alkenyl group is 2 to 10. 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 carbon number of the cycloalkyl group is 3 to 20. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3, 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but is not limited thereto.

In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the carbon number of the aryl group is 6 to 30. According to an exemplary embodiment, the carbon number of the aryl group is 6 to 20. The aryl group may be a monocyclic aryl group, such as a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, an anthracenyl group, a 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. can be However, the present invention is not limited thereto.

In the present specification, the heteroaryl group is a heteroaryl group including 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 from 2 to 60 carbon atoms. According to an exemplary embodiment, the heteroaryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the heteroaryl group has 6 to 20 carbon atoms. Examples of the heteroaryl 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, an 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, thiadia and a jolyl group, a phenothiazinyl group, and a dibenzofuranyl group, but is not limited thereto.

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

Preferably, any one of R ₁ to R ₃ , R ₅ to R ₉ , R ₁₁ and R ₁₂ is a substituent represented by the following Chemical Formula 2, the rest are each independently hydrogen or deuterium, R ₄ and R ₁₀ are Each independently may be hydrogen or deuterium. More preferably, any one of R ₁ to R ₃ , R ₅ to R ₉ , R ₁₁ and R ₁₂ is a substituent represented by the following formula (2), the rest are each hydrogen, and R ₄ and R ₁₀ are each hydrogen. can

일 수 있다.Preferably, L ₁ is phenylene unsubstituted or substituted with 1 phenyl, biphenyldiyl unsubstituted or substituted with 1 phenyl, naphthalenediyl unsubstituted or substituted with 1 phenyl, or

can be

More preferably, L ₁ may be any one selected from the group consisting of:

.

.

More preferably, L ₁ may be phenylene unsubstituted or substituted with one phenyl, biphenyldiyl unsubstituted or substituted with one phenyl, or naphthalenediyl.

More preferably, L ₁ may be any one selected from the group consisting of:

.

.

More preferably, when R ₅ or R ₁₁ is a substituent represented by Formula 2, L ₁ may be any one selected from the group consisting of:

.

.

Preferably, L ₂ and L ₃ are each independently a single bond; substituted or unsubstituted C _6-20 arylene; Or it may be C _2-20 heteroarylene including any one or more selected from the group consisting of substituted or unsubstituted N, O and S.

More preferably, L ₂ and L ₃ may each independently represent a single bond, phenylene, phenylene substituted with one phenyl, biphenyldiyl, biphenyldiyl substituted with one phenyl, or naphthalenediyl .

Most preferably, L ₂ and L ₃ may each independently be a single bond or any one selected from the group consisting of:

.

Preferably, Ar ₁ is substituted or unsubstituted C _6-20 aryl; Or it may be C _2-20 heteroaryl including any one or more selected from the group consisting of substituted or unsubstituted N, O and S.

More preferably, Ar ₁ is phenyl, biphenylyl, terphenylyl, naphthyl, phenanthrenyl, phenyl naphthyl, dibenzofuranyl, dibenzothiophenyl, phenyl carbazole, dimethyl fluorenyl, benzonaph tofuranyl, or benzonaphthothiophenyl.

More preferably, Ar ₁ may be any one selected from the group consisting of:

.

More preferably, Ar ₁ may be any one selected from the group consisting of:

.

Preferably, Ar ₂ may be any one selected from the group consisting of:

.

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

.

Among the compounds represented by Formula 1, any one of R ₁ to R ₁₂ is a substituent represented by Formula 2 below, and the remainder is hydrogen, for example, it may be prepared by a manufacturing method as shown in Scheme 1 below, and the rest The compounds can be prepared analogously.

[Scheme 1]

In Scheme 1, L ₁ to L ₃ , Ar ₁ and Ar ₂ are as defined in Formula 1 above, and X is halogen, preferably X is chloro or bromo.

Reaction Scheme 1 is a Suzuki coupling reaction, which is preferably performed 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 Preparation Examples to be described later.

In addition, the present invention provides an organic light emitting device including the compound represented by the formula (1). In one example, the present invention provides a first electrode; a second electrode provided to face the first electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound represented by Formula 1 above. do.

The organic material layer of the organic light emitting device of the present invention may have a single-layer structure, but may have a multi-layer 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, etc. 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 material layers.

Also, the organic layer may include a light emitting layer, and the light emitting layer may include a compound represented by Formula 1 above.

In addition, the organic layer may include a hole transport layer, a hole injection layer, or a layer that transports and injects holes at the same time. It may include a compound represented by 1.

In addition, the organic layer may include an electron transport layer, an electron injection layer, or an electron injection and transport layer, and the electron transport layer, the electron injection layer, or the electron injection and transport layer may include a compound represented by Formula 1 .

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. Also, 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 the organic light emitting diode according to an embodiment of the present invention is illustrated in FIGS. 1 and 2 .

FIG. 1 shows an example of an organic light emitting device including a substrate 1 , an anode 2 , an electron suppression layer 3 , a light emitting layer 4 , and a cathode 5 . 2 shows a substrate 1, an anode 2, a hole injection layer 6, a hole transport layer 7, an electron blocking layer 3, a light emitting layer 4, a hole blocking layer 8, an electron transport and injection layer An example of an organic light emitting device composed of (9) and a cathode (5) is shown. In such a structure, the compound represented by Formula 1 may be included in the hole transport layer, the electron suppression layer, or the light emitting layer.

The organic light emitting device according to the present invention may be manufactured using materials and methods known in the art, except that at least one layer of the organic material layer includes the compound represented by Formula 1 above. Also, 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, by using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, a metal or conductive metal oxide or an alloy thereof is deposited on a substrate to form an anode. And, after forming an organic 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, spraying, roll coating, and the like, but is not limited thereto.

In addition to the above 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.

In one 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 generally preferred so that holes can be smoothly injected into the organic material layer. Specific examples of the anode material include metals such as vanadium, chromium, copper, zinc, 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; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

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

The hole injection layer is a layer for injecting holes from the electrode, and as a hole injection material, it has the ability to transport holes, so it has a hole injection effect at the anode, an excellent hole injection effect on the light emitting layer or the light emitting material, and is produced in the light emitting layer A compound which prevents the movement of excitons to the electron injection layer or the electron injection material and is excellent in the ability to form a thin film is preferred. It is preferable that the highest occupied molecular orbital (HOMO) 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, and perylene-based organic material. of organic substances, anthraquinones, polyaniline and polythiophene-based conductive polymers, and the like, but are not limited thereto.

The hole transport layer is a layer that receives holes from the hole injection layer and transports them to the light emitting layer. A material capable of transporting holes from the anode or hole injection layer to the light emitting layer as a hole transport material. This is suitable. Specific examples include, but are not limited to, an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together. Preferably, the compound represented by Formula 1 may be used as the hole transport layer material.

The electron blocking layer is a layer placed between the hole transport layer and the emission layer in order to prevent electrons injected from the cathode from passing to the hole transport layer without recombination in the emission layer, and is also called an electron blocking layer. A material having a lower electron affinity than the electron transport layer is preferable for the electron suppressing layer. Preferably, the compound represented by Formula 1 may be used as the electron blocking layer material.

The light emitting material is a material capable of emitting light in the visible ray region by receiving 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 include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compounds; compounds of the benzoxazole, benzthiazole and benzimidazole series; Poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; polyfluorene, rubrene, and the like, but is not limited thereto.

The emission layer may include a host material and a dopant material. The host material includes a condensed aromatic ring derivative or a heterocyclic compound containing compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto. Preferably, the compound represented by Formula 1 may be used as the host material.

Examples of the dopant material include an aromatic amine derivative, a strylamine compound, a boron complex, a fluoranthene compound, and a metal complex. 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. As the styrylamine compound, a substituted or unsubstituted It is a compound in which at least one arylvinyl group is substituted in the arylamine, and one or two or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group are substituted or unsubstituted. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like, but is 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 dopant material may be at least one selected from the group consisting of:

.

.

The hole blocking layer is a layer interposed between the electron transport layer and the emission layer to prevent the holes injected from the anode from passing to the electron transport layer without recombination in the emission layer, and is also called a hole blocking layer. A material having high ionization energy is preferable for the hole blocking layer.

The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer. 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 may be used with any desired cathode material as used in accordance with the prior art. In particular, examples of suitable cathode materials are conventional materials having a low work function and followed by a layer of aluminum or silver. Specifically cesium, barium, calcium, ytterbium and samarium, followed in each case by an aluminum layer or a silver layer.

The electron injection layer is a layer that injects electrons from the electrode, has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect on the light emitting layer or the light emitting material, and hole injection of excitons generated in the light emitting layer. A compound which prevents movement to a layer and is excellent in the ability to form a thin film is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc., derivatives thereof, metals complex compounds and nitrogen-containing 5-membered ring derivatives, but are not limited thereto.

Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-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-crezolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, etc. However, the present invention is not limited thereto.

On the other hand, in the present invention, the "electron injection and transport layer" is a layer that performs both the role of the electron injection layer and the electron transport layer, and the materials serving the respective layers may be used alone or in combination, but limited thereto. doesn't happen

The organic light emitting device according to the present invention may be a bottom emission device, a top emission device, or a double-sided light emitting device, and in particular, may be a bottom emission device requiring relatively high luminous efficiency.

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 compound represented by Formula 1 and the preparation of an organic light emitting device including the same will be described in detail in Examples below. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited thereto.

[Production Example]

Preparation Example 1

In a nitrogen atmosphere, compound A (15 g, 57.1 mmol) and compound amine1 (34 g, 59.9 mmol) were added to 300 ml of THF, stirred and refluxed. After that, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After the reaction for 12 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 29.1 g of Compound 1. (Yield 68%, MS: [M+H] ⁺ = 750)

Preparation 2

In a nitrogen atmosphere, compound A (15 g, 57.1 mmol) and compound amine2 (32.5 g, 59.9 mmol) were added to 300 ml of THF, followed by stirring and reflux. After that, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After the reaction for 11 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 31 g of compound 2. (yield 75%, MS: [M+H] ⁺ = 724)

Preparation 3

Compound A (15 g, 57.1 mmol) and compound amine3 (24.9 g, 59.9 mmol) were added to 300 ml of THF in a nitrogen atmosphere, and the mixture was stirred and refluxed. After that, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After the reaction for 9 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 25.2 g of compound 3. (yield 74%, MS: [M+H] ⁺ = 598)

Preparation 4

In a nitrogen atmosphere, compound A (15 g, 57.1 mmol) and compound amine4 (32.5 g, 59.9 mmol) were added to 300 ml of THF, followed by stirring and reflux. After that, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After the reaction for 9 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 26.8 g of compound 4. (Yield 65%, MS: [M+H] ⁺ = 724)

Preparation 5

Compound A (15 g, 57.1 mmol) and compound amine5 (31.9 g, 59.9 mmol) were added to 300 ml of THF in a nitrogen atmosphere, and stirred and refluxed. After that, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After the reaction for 12 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 26.5 g of compound 5. (Yield 65%, MS: [M+H] ⁺ = 714)

Preparation 6

In a nitrogen atmosphere, compound A (15 g, 57.1 mmol) and compound amine6 (28.3 g, 59.9 mmol) were added to 300 ml of THF, stirred and refluxed. After that, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 27.2 g of compound 6. (Yield 73%, MS: [M+H] ⁺ = 654)

Preparation 7

In a nitrogen atmosphere, compound A (15 g, 57.1 mmol) and compound amine7 (27.2 g, 59.9 mmol) were added to 300 ml of THF, stirred and refluxed. After that, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After the reaction for 9 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 28.3 g of compound 7. (yield 78%, MS: [M+H] ⁺ = 637)

Preparation 8

In a nitrogen atmosphere, compound A (15 g, 57.1 mmol) and compound amine8 (24.3 g, 59.9 mmol) were added to 300 ml of THF, followed by stirring and reflux. After that, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After the reaction for 8 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 21.1 g of compound 8. (Yield 63%, MS: [M+H] ⁺ = 588)

Preparation 9

In a nitrogen atmosphere, compound A (15 g, 57.1 mmol) and compound amine9 (29.5 g, 59.9 mmol) were added to 300 ml of THF, followed by stirring and reflux. After that, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After the reaction for 9 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 24.2 g of compound 9. (Yield 63%, MS: [M+H] ⁺ = 674)

Preparation 10

Compound A (15 g, 57.1 mmol) and compound amine10 (29.5 g, 59.9 mmol) were added to 300 ml of THF in a nitrogen atmosphere, and the mixture was stirred and refluxed. After that, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After the reaction for 11 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 27.3 g of compound 10. (Yield 71%, MS: [M+H] ⁺ = 674)

Preparation 11

Compound A (15 g, 57.1 mmol) and compound amine 11 (29.5 g, 59.9 mmol) were added to 300 ml of THF in a nitrogen atmosphere, and the mixture was stirred and refluxed. After that, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 26.5 g of compound 11. (yield 69%, MS: [M+H] ⁺ = 674)

Preparation 12

In a nitrogen atmosphere, compound A (15 g, 57.1 mmol) and compound amine12 (32.5 g, 59.9 mmol) were added to 300 ml of THF, stirred and refluxed. After that, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After the reaction for 12 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 24.8 g of compound 12. (Yield 60%, MS: [M+H] ⁺ = 724)

Preparation 13

In a nitrogen atmosphere, compound A (15 g, 57.1 mmol) and compound amine13 (34 g, 59.9 mmol) were added to 300 ml of THF, stirred and refluxed. After that, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After the reaction for 8 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 33.8 g of compound 13. (Yield 79%, MS: [M+H] ⁺ = 750)

Preparation 14

Compound A (15 g, 57.1 mmol) and compound amine 14 (31 g, 59.9 mmol) were added to 300 ml of THF in a nitrogen atmosphere, and the mixture was stirred and refluxed. After that, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After the reaction for 9 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 30.3 g of compound 14. (Yield 76%, MS: [M+H] ⁺ = 700)

Preparation 15

In a nitrogen atmosphere, compound B (15 g, 57.1 mmol) and compound amine15 (24.9 g, 59.9 mmol) were added to 300 ml of THF, followed by stirring and reflux. After that, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 21.8 g of compound 15. (Yield 64%, MS: [M+H] ⁺ = 598)

Preparation 16

In a nitrogen atmosphere, compound B (15 g, 57.1 mmol) and compound amine 16 (31 g, 59.9 mmol) were added to 300 ml of THF, stirred and refluxed. After that, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After the reaction for 9 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 26.3 g of compound 16. (Yield 66%, MS: [M+H] ⁺ = 700)

Preparation 17

In a nitrogen atmosphere, compound B (15 g, 57.1 mmol) and compound amine17 (29.5 g, 59.9 mmol) were added to 300 ml of THF, stirred and refluxed. After that, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After the reaction for 12 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 27.7 g of compound 17. (Yield 72%, MS: [M+H] ⁺ = 674)

Preparation 18

In a nitrogen atmosphere, compound B (15 g, 57.1 mmol) and compound amine18 (27.9 g, 59.9 mmol) were added to 300 ml of THF, followed by stirring and reflux. After that, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After the reaction for 12 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 24.4 g of compound 18. (Yield 66%, MS: [M+H] ⁺ = 648)

Preparation 19

In a nitrogen atmosphere, compound B (15 g, 57.1 mmol) and compound amine19 (28.1 g, 59.9 mmol) were added to 300 ml of THF, stirred and refluxed. After that, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After the reaction for 9 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 27.5 g of compound 19. (Yield 74%, MS: [M+H] ⁺ = 652)

Preparation 20

In a nitrogen atmosphere, compound B (15 g, 57.1 mmol) and compound amine 20 (30.3 g, 59.9 mmol) were added to 300 ml of THF, followed by stirring and reflux. After that, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 28.3 g of compound 20. (Yield 72%, MS: [M+H] ⁺ = 688)

Preparation 21

In a nitrogen atmosphere, compound B (15 g, 57.1 mmol) and compound amine21 (28.9 g, 59.9 mmol) were added to 300 ml of THF, followed by stirring and reflux. After that, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After the reaction for 11 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 25.8 g of compound 21. (Yield 68%, MS: [M+H] ⁺ = 664)

Preparation 22

In a nitrogen atmosphere, compound B (15 g, 57.1 mmol) and compound amine22 (30.3 g, 59.9 mmol) were added to 300 ml of THF, followed by stirring and reflux. After that, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After the reaction for 8 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 30.6 g of compound 22. (Yield 78%, MS: [M+H] ⁺ = 688)

Preparation 23

In a nitrogen atmosphere, compound C (15 g, 57.1 mmol) and compound amine23 (26.5 g, 59.9 mmol) were added to 300 ml of THF, followed by stirring and reflux. After that, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After the reaction for 9 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 24.6 g of compound 23. (yield 69%, MS: [M+H] ⁺ = 624)

Preparation 24

In a nitrogen atmosphere, compound C (15 g, 57.1 mmol) and compound amine24 (27.9 g, 59.9 mmol) were added to 300 ml of THF, followed by stirring and reflux. After that, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After the reaction for 11 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 27.3 g of Compound 24. (Yield 74%, MS: [M+H] ⁺ = 648)

Preparation 25

In a nitrogen atmosphere, compound C (15 g, 57.1 mmol) and compound amine25 (26.5 g, 59.9 mmol) were added to 300 ml of THF, followed by stirring and reflux. After that, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After the reaction for 11 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 23.5 g of compound 25. (Yield 66%, MS: [M+H] ⁺ = 624)

Preparation 26

Compound C (15 g, 57.1 mmol) and compound amine 26 (30.1 g, 59.9 mmol) were added to 300 ml of THF in a nitrogen atmosphere, and the mixture was stirred and refluxed. After that, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After the reaction for 8 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 24.2 g of compound 26. (Yield 62%, MS: [M+H] ⁺ = 684)

Preparation 27

In a nitrogen atmosphere, compound C (15 g, 57.1 mmol) and compound amine27 (26.7 g, 59.9 mmol) were added to 300 ml of THF, followed by stirring and reflux. After that, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After the reaction for 11 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 24.7 g of compound 27. (yield 69%, MS: [M+H] ⁺ = 628)

Preparation 28

In a nitrogen atmosphere, compound D (15 g, 57.1 mmol) and compound amine28 (26.5 g, 59.9 mmol) were added to 300 ml of THF, stirred and refluxed. After that, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After the reaction for 12 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 24.2 g of compound 28. (Yield 68%, MS: [M+H] ⁺ = 624)

Preparation 29

In a nitrogen atmosphere, compound D (15 g, 57.1 mmol) and compound amine29 (32.5 g, 59.9 mmol) were added to 300 ml of THF, stirred and refluxed. After that, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After the reaction for 12 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 24.8 g of compound 29. (Yield 60%, MS: [M+H] ⁺ = 724)

Preparation 30

In a nitrogen atmosphere, compound D (15 g, 57.1 mmol) and compound amine30 (31 g, 59.9 mmol) were added to 300 ml of THF, followed by stirring and reflux. After that, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 31.9 g of compound 30. (Yield 80%, MS: [M+H] ⁺ = 700)

Preparation 31

In a nitrogen atmosphere, compound D (15 g, 57.1 mmol) and compound amine31 (29.5 g, 59.9 mmol) were added to 300 ml of THF, stirred and refluxed. After that, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After the reaction for 8 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 30.8 g of compound 31. (yield 80%, MS: [M+H] ⁺ = 674)

Preparation 32

In a nitrogen atmosphere, compound D (15 g, 57.1 mmol) and compound amine32 (29.5 g, 59.9 mmol) were added to 300 ml of THF, stirred and refluxed. After that, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After the reaction for 11 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 28.1 g of compound 32. (Yield 73%, MS: [M+H] ⁺ = 674)

Preparation 33

Compound D (15 g, 57.1 mmol) and compound amine 33 (28.9 g, 59.9 mmol) were added to 300 ml of THF in a nitrogen atmosphere, and the mixture was stirred and refluxed. After that, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After the reaction for 9 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 29.9 g of compound 33. (yield 79%, MS: [M+H] ⁺ = 664)

Preparation 34

In a nitrogen atmosphere, compound D (15 g, 57.1 mmol) and compound amine34 (29.1 g, 59.9 mmol) were added to 300 ml of THF, stirred and refluxed. After that, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After the reaction for 9 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 27.4 g of compound 34. (Yield 72%, MS: [M+H] ⁺ = 668)

Preparation 35

In a nitrogen atmosphere, compound D (15 g, 57.1 mmol) and compound amine35 (30.3 g, 59.9 mmol) were added to 300 ml of THF, stirred and refluxed. After that, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After the reaction for 8 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 23.5 g of compound 35. (Yield 60%, MS: [M+H] ⁺ = 688)

Preparation 36

In a nitrogen atmosphere, compound D (15 g, 57.1 mmol) and compound amine36 (26.7 g, 59.9 mmol) were added to 300 ml of THF, followed by stirring and reflux. After that, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 25.4 g of compound 36. (Yield 71%, MS: [M+H] ⁺ = 628)

Preparation 37

In a nitrogen atmosphere, compound D (15 g, 57.1 mmol) and compound amine37 (31 g, 59.9 mmol) were added to 300 ml of THF, stirred and refluxed. After that, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 31.9 g of compound 37. (Yield 80%, MS: [M+H] ⁺ = 700)

Preparation 38

In a nitrogen atmosphere, compound D (15 g, 57.1 mmol) and compound amine38 (24.9 g, 59.9 mmol) were added to 300 ml of THF, stirred and refluxed. After that, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After the reaction for 9 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 23.5 g of compound 38. (yield 69%, MS: [M+H] ⁺ = 598)

Preparation 39

In a nitrogen atmosphere, compound D (15 g, 57.1 mmol) and compound amine39 (32.5 g, 59.9 mmol) were added to 300 ml of THF, followed by stirring and reflux. After that, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After the reaction for 11 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 30.6 g of compound 39. (Yield 74%, MS: [M+H] ⁺ = 724)

Preparation 40

In a nitrogen atmosphere, compound D (15 g, 57.1 mmol) and compound amine 40 (34 g, 59.9 mmol) were added to 300 ml of THF, stirred and refluxed. After that, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After the reaction for 9 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 30.8 g of compound 40. (Yield 72%, MS: [M+H] ⁺ = 750)

Preparation 41

In a nitrogen atmosphere, compound D (15 g, 57.1 mmol) and compound amine41 (32.5 g, 59.9 mmol) were added to 300 ml of THF, followed by stirring and reflux. After that, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After the reaction for 8 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 26 g of compound 41. (Yield 63%, MS: [M+H] ⁺ = 724)

Preparation 42

In a nitrogen atmosphere, compound E (15 g, 57.1 mmol) and compound amine42 (26.5 g, 59.9 mmol) were added to 300 ml of THF, stirred and refluxed. After that, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After the reaction for 9 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 25.6 g of compound 42. (Yield 72%, MS: [M+H] ⁺ = 624)

Preparation 43

In a nitrogen atmosphere, compound E (15 g, 57.1 mmol) and compound amine 43 (29.5 g, 59.9 mmol) were added to 300 ml of THF, stirred and refluxed. After that, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After the reaction for 11 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 29.2 g of compound 43. (Yield 76%, MS: [M+H] ⁺ = 674)

Preparation 44

In a nitrogen atmosphere, compound E (15 g, 57.1 mmol) and compound amine 44 (32.5 g, 59.9 mmol) were added to 300 ml of THF, followed by stirring and reflux. After that, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After the reaction for 9 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 26.4 g of compound 44. (Yield 64%, MS: [M+H] ⁺ = 724)

Preparation 45

In a nitrogen atmosphere, compound E (15 g, 57.1 mmol) and compound amine45 (22.7 g, 59.9 mmol) were added to 300 ml of THF, followed by stirring and reflux. After that, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After the reaction for 8 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 22.4 g of compound 45. (Yield 70%, MS: [M+H] ⁺ = 562)

Preparation 46

In a nitrogen atmosphere, compound E (15 g, 57.1 mmol) and compound amine46 (31.8 g, 59.9 mmol) were added to 300 ml of THF, followed by stirring and reflux. After that, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After the reaction for 8 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 25.6 g of compound 46. (Yield 63%, MS: [M+H] ⁺ = 713)

Preparation 47

In a nitrogen atmosphere, compound E (15 g, 57.1 mmol) and compound amine 47 (25.7 g, 59.9 mmol) were added to 300 ml of THF, followed by stirring and reflux. After that, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 24.4 g of compound 47. (Yield 70%, MS: [M+H] ⁺ = 612)

Preparation 48

Compound E (15 g, 57.1 mmol) and compound amine48 (31 g, 59.9 mmol) were added to 300 ml of THF in a nitrogen atmosphere, and the mixture was stirred and refluxed. After that, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After the reaction for 9 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 31.5 g of compound 48. (yield 79%, MS: [M+H] ⁺ = 700)

Preparation 49

In a nitrogen atmosphere, compound E (15 g, 57.1 mmol) and compound amine49 (32.5 g, 59.9 mmol) were added to 300 ml of THF, stirred and refluxed. After that, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After the reaction for 8 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 25.2 g of compound 49. (Yield 61%, MS: [M+H] ⁺ = 724)

Preparation 50

Compound F (15 g, 57.1 mmol) and compound amine 50 (26.5 g, 59.9 mmol) were added to 300 ml of THF in a nitrogen atmosphere, stirred and refluxed. After that, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After the reaction for 9 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 25.3 g of compound 50. (Yield 71%, MS: [M+H] ⁺ = 624)

Preparation 51

In a nitrogen atmosphere, compound F (15 g, 57.1 mmol) and compound amine51 (31 g, 59.9 mmol) were added to 300 ml of THF, stirred and refluxed. After that, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After the reaction for 12 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 25.2 g of compound 51. (Yield 63%, MS: [M+H] ⁺ = 700)

Preparation 52

In a nitrogen atmosphere, compound F (15 g, 57.1 mmol) and compound amine52 (29.5 g, 59.9 mmol) were added to 300 ml of THF, followed by stirring and reflux. After that, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 10 hours of reaction, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 28.1 g of compound 52. (Yield 73%, MS: [M+H] ⁺ = 674)

Preparation 53

In a nitrogen atmosphere, compound F (15 g, 57.1 mmol) and compound amine53 (31 g, 59.9 mmol) were added to 300 ml of THF, followed by stirring and reflux. After that, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After the reaction for 12 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 25.9 g of compound 53. (Yield 65%, MS: [M+H] ⁺ = 700)

Preparation 54

Compound F (15 g, 57.1 mmol) and compound amine54 (34 g, 59.9 mmol) were added to 300 ml of THF in a nitrogen atmosphere, and the mixture was stirred and refluxed. After that, potassium carbonate (23.7 g, 171.3 mmol) was dissolved in 71 ml of water and thoroughly stirred, and then bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After the reaction for 8 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 30.4 g of compound 54. (Yield 71%, MS: [M+H] ⁺ = 750)

[Example]

Example 1

A glass substrate coated with indium tin oxide (ITO) to a thickness of 1000 Å was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, a product manufactured by Fischer Co. was used as the detergent, and distilled water that was secondarily filtered with a filter manufactured by Millipore Co. was used as the distilled water. After washing ITO for 30 minutes, ultrasonic cleaning was performed for 10 minutes by repeating twice with distilled water. After washing with distilled water, ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, and after drying, it was 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.

The following compound HI-1 was formed to a thickness of 1150 Å as a hole injection layer on the prepared ITO transparent electrode, but the following compound A-1 was p-doped at 1.5 wt%. The following compound HT-1 was vacuum-deposited on the hole injection layer to form a hole transport layer having a thickness of 800 Å. Subsequently, the compound 1 prepared in Preparation Example 1 was vacuum-deposited to a film thickness of 150 Å on the hole transport layer to form an electron suppression layer. Then, the following compound RH-1 as a host and the following compound Dp-7 as a dopant were vacuum-deposited on the electron suppression layer in a weight ratio of 98:2 to form a red light-emitting layer having a thickness of 400 Å. A hole blocking layer was formed by vacuum-depositing the following compound HB-1 to a thickness of 30 Å on the light emitting layer. Then, on the hole blocking layer, the following compound ET-1 and the following compound LiQ were vacuum-deposited at a weight ratio of 2:1 to form an electron injection and transport layer to a thickness of 300 Å. A cathode was formed by sequentially depositing lithium fluoride (LiF) to a thickness of 12 Å and aluminum to a thickness of 1000 Å on the electron injection and transport layer.

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

Examples 2 to 54

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

Comparative Examples 1 to 16

An organic light emitting device was manufactured in the same manner as in Comparative Example 1, except that the compound shown in Table 1 was used instead of Compound 1 in the organic light emitting device of Example 1. The structures of compounds C-1 to C-16 of Table 1 are as follows.

[Experimental example]

When a current was applied to the organic light emitting diodes prepared in Examples 1 to 54 and Comparative Examples 1 to 16, voltage and efficiency were measured (15 mA/cm ² ), and the results are shown in Table 1 below. The lifetime T95 means the time it takes for the luminance to decrease to 95% from the initial luminance (6000 nit).

division matter Driving voltage (V) Efficiency (cd/A) Life T95 (hr) luminous color Example 1 compound 1 3.62 19.50 213 Red Example 2 compound 2 3.58 19.27 222 Red Example 3 compound 3 3.57 19.95 206 Red Example 4 compound 4 3.59 20.27 219 Red Example 5 compound 5 3.61 20.17 213 Red Example 6 compound 6 3.57 20.25 208 Red Example 7 compound 7 3.61 18.96 222 Red Example 8 compound 8 3.58 19.76 217 Red Example 9 compound 9 3.62 19.76 222 Red Example 10 compound 10 3.61 19.56 208 Red Example 11 compound 11 3.57 20.57 205 Red Example 12 compound 12 3.53 19.12 210 Red Example 13 compound 13 3.53 20.34 207 Red Example 14 compound 14 3.68 18.31 177 Red Example 15 compound 15 3.73 18.25 172 Red Example 16 compound 16 3.71 18.17 179 Red Example 17 compound 17 3.76 18.22 185 Red Example 18 compound 18 3.79 18.28 184 Red Example 19 compound 19 3.77 17.67 178 Red Example 20 compound 20 3.74 18.33 180 Red Example 21 compound 21 3.68 18.07 175 Red Example 22 compound 22 3.79 17.37 169 Red Example 23 compound 23 3.86 17.22 163 Red Example 24 compound 24 3.85 17.58 169 Red Example 25 compound 25 3.86 16.96 165 Red Example 26 compound 26 3.83 17.62 159 Red Example 27 compound 27 3.59 19.03 226 Red Example 28 compound 28 3.55 19.07 225 Red Example 29 compound 29 3.59 20.38 210 Red Example 30 compound 30 3.57 19.94 225 Red Example 31 compound 31 3.61 20.74 226 Red Example 32 compound 32 3.59 20.33 208 Red Example 33 compound 33 3.53 19.72 213 Red Example 34 compound 34 3.55 19.29 217 Red Example 35 compound 35 3.59 20.11 210 Red Example 36 compound 36 3.61 19.99 223 Red Example 37 compound 37 3.61 20.62 220 Red Example 38 compound 38 3.56 18.97 220 Red Example 39 compound 39 3.55 20.84 223 Red Example 40 compound 40 3.58 20.88 222 Red Example 41 compound 41 3.70 19.06 226 Red Example 42 compound 42 3.61 19.39 211 Red Example 43 compound 43 3.70 19.04 208 Red Example 44 compound 44 3.68 19.37 213 Red Example 45 compound 45 3.69 20.68 212 Red Example 46 compound 46 3.65 19.30 206 Red Example 47 compound 47 3.61 20.00 206 Red Example 48 compound 48 3.69 21.06 208 Red Example 49 compound 49 3.76 18.24 187 Red Example 50 compound 50 3.73 17.56 174 Red Example 51 compound 51 3.78 18.26 172 Red Example 52 compound 52 3.68 18.25 170 Red Example 53 compound 53 3.76 17.51 170 Red Example 54 compound 54 3.79 18.17 177 Red Comparative Example 1 compound C-1 4.11 14.97 125 Red Comparative Example 2 compound C-2 4.06 14.88 112 Red Comparative Example 3 compound C-3 4.28 13.48 91 Red Comparative Example 4 compound C-4 4.26 14.58 96 Red Comparative Example 5 compound C-5 4.23 14.30 92 Red Comparative Example 6 compound C-6 4.19 14.60 93 Red Comparative Example 7 compound C-7 4.46 13.41 81 Red Comparative Example 8 compound C-8 4.39 12.48 63 Red Comparative Example 9 compound C-9 4.15 14.88 121 Red Comparative Example 10 compound C-10 4.42 12.18 64 Red Comparative Example 11 compound C-11 4.41 12.32 57 Red Comparative Example 12 compound C-12 4.22 15.28 103 Red Comparative Example 13 compound C-13 4.18 15.11 101 Red Comparative Example 14 compound C-14 4.09 15.36 126 Red Comparative Example 15 compound C-15 4.17 15.06 94 Red Comparative Example 16 compound C-16 4.38 13.33 77 Red

When a current was applied to the organic light emitting diodes fabricated in Examples 1 to 54 and Comparative Examples 1 to 16, the results shown in Table 1 were obtained. In the above Examples and Comparative Examples, a material that has been widely used in the prior art was used as a material other than the electron suppression layer, and Dp-7 is used as the dopant of the red light emitting layer.

Looking at the results in Table 1, when the compound of the present invention was used as the electron suppression layer, the driving voltage was significantly lowered compared to the comparative example material, and the efficiency was also increased, indicating that energy transfer from the host to the red dopant was well performed. could In addition, it was found that the lifetime characteristics can be greatly improved while maintaining high efficiency.

In conclusion, it was confirmed that the driving voltage, luminous efficiency, and lifespan characteristics of the organic light emitting device could be improved when the compound of the present invention was used as the electron suppression layer of the red light emitting layer.

1: Substrate 2: Anode
3: electron suppression layer 4: light emitting layer
5: Cathode 6: Hole injection layer
7: hole transport layer 8: hole blocking layer
9: Electron transport and injection layer

Claims (10)

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

In Formula 1,
Any one of R ₁ to R ₁₂ is a substituent represented by the following formula (2), and the rest are each independently hydrogen or deuterium;
[Formula 2]

In Formula 2,
L ₁ is substituted or unsubstituted phenylene, substituted or unsubstituted biphenyldiyl, substituted or unsubstituted naphthalenediyl, or

ego,
L ₂ and L ₃ are each independently, a single bond; substituted or unsubstituted C _6-60 arylene; Or a C _2-60 heteroarylene comprising at least one selected from the group consisting of substituted or unsubstituted N, O and S,
Ar ₁ is substituted or unsubstituted C _6-60 aryl; Or substituted or unsubstituted C _2-60 heteroaryl comprising any one or more selected from the group consisting of N, O and S,
Ar ₂ is biphenylyl, terphenylyl, naphthyl, phenanthrenyl, phenyl naphthyl, dibenzofuranyl, dibenzothiophenyl, phenyl carbazole, dimethyl fluorenyl, benzonaphthofuranyl, or benzonaphtho thiophenyl.
According to claim 1,
L ₁ is any one selected from the group consisting of
compound:

.
According to claim 1,
L ₂ and L ₃ are each independently a single bond, phenylene, phenylene substituted with one phenyl, biphenyldiyl, biphenyldiyl substituted with one phenyl, or naphthalenediyl;
compound.
According to claim 1,
L ₂ and L ₃ are each independently any one selected from the group consisting of a single bond or the following,
compound:

.
According to claim 1,
Ar ₁ is phenyl, biphenylyl, terphenylyl, naphthyl, phenanthrenyl, phenyl naphthyl, dibenzofuranyl, dibenzothiophenyl, phenyl carbazole, dimethyl fluorenyl, benzonaphthofuranyl, or benzo naphthothiophenyl,
compound.
According to claim 1,
Ar ₁ is any one selected from the group consisting of
compound:

.
According to claim 1,
Ar ₂ is any one selected from the group consisting of
compound:

.
According to claim 1,
The compound represented by Formula 1 is any one selected from the group consisting of
compound:

.
a first electrode; a second electrode provided to face the first electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers contains the compound according to any one of claims 1 to 8 doing,
organic light emitting device.
10. The method of claim 9,
The organic layer is a light emitting layer,
organic light emitting device.

Images