KR20210097649A - 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. The present invention provides a compound represented by chemical formula 1. The compound represented by chemical formula 1 described above can be used as a material for an organic layer of the organic light emitting device, and can improve efficiency, lower driving voltage, and/or improve lifespan characteristics in the organic light emitting device.

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 using 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, and may include, 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. In the structure of the organic light emitting device, when a voltage is applied between the two electrodes, 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 When it falls back to the ground state, it lights up.

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

Korean Patent Publication No. 10-2013-073537

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 is a naphthalene ring, B is a benzene ring; or B is a naphthalene ring, A is a benzene ring,

L ₁ is a direct bond; substituted or unsubstituted C _6-60 arylene; _{Or a substituted or unsubstituted C 2-60} heteroarylene containing one or more hetero atoms selected from the group consisting of N, O and S,

L ₂ and L ₃ are each independently, a direct bond; or substituted or unsubstituted C _6-60 arylene,

Ar ₁ and Ar ₂ are each independently, substituted or unsubstituted C _6-60 aryl; _{Or C 2-60} substituted or unsubstituted aromatic heteroaryl containing one or more heteroatoms selected from the group consisting of N, O and S;

R ₁ , R ₂ and R ₃ are each independently hydrogen; heavy hydrogen; or substituted or unsubstituted C _1-60 alkyl;

a1, a2, and a3 are each independently an integer of 0-4.

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 organic material layer includes the compound of the present invention.

The compound represented by Formula 1 described above may be used as a material for an organic layer of an 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 Chemical Formula 1 described above may be used as a material for an electron suppression layer of an organic light emitting device.

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

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

(Explanation of terms)

및

는 다른 치환기에 연결되는 결합을 의미한다. In this specification,

and

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 arylphosphine 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 heterocyclic group containing one or more atoms, or substituted or unsubstituted with two or more substituents connected among the above-exemplified substituents . 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 in the carbonyl group is not particularly limited, but 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, 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, but is not limited to, a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, a phenylboron group, and the like.

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 includes at least one of O, N, Si and S as a heterogeneous element, and as a heterocyclic group having aromaticity, the number of carbon atoms is not particularly limited, but those having 2 to 60 carbon atoms are desirable. 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, thiazolyl group, isoxazolyl group group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl group, phenothiazinyl group, dibenzofuranyl group, and the like, 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, as for heteroaryl among heteroarylamines, the description of the above-described heterocyclic group may be applied. In the present specification, the alkenyl group among the aralkenyl groups is the same as the above-described examples of the alkenyl group. 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 heterocyclic 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, the heterocyclic group is not a monovalent group, and the description of the above-described heterocyclic group may be applied, except that it is formed by combining two substituents.

(compound)

,

,

) 등의 치환기를 가지는 화합물과 대비하여 우수한 효율, 저 구동 전압, 고휘도 및 장수명을 구현할 수 있다. 화학식 1의 구조를 살펴보면 다음과 같다.The present invention provides a compound represented by the above formula (1). The compound represented by Formula 1 is a compound including a benzene ring or a naphthalene ring condensed on a heptagonal azepine core, respectively, and includes an additional amine substituent at N of azepine, and thus, the electron suppression layer of an organic light emitting device When applied to , it can facilitate energy transfer from the host to the red dopant. In particular, the additional amine substituent is a semi-aromatic hetero ring (

,

,

) can implement excellent efficiency, low driving voltage, high luminance and long life compared to compounds having a substituent such as . The structure of Chemical Formula 1 is as follows.

[Formula 1]

In Formula 1,

A is a naphthalene ring, B is a benzene ring; or B is a naphthalene ring, A is a benzene ring,

L ₁ is a direct bond; substituted or unsubstituted C _6-60 arylene; _{Or a substituted or unsubstituted C 2-60} heteroarylene containing one or more hetero atoms selected from the group consisting of N, O and S,

L ₂ and L ₃ are each independently, a direct bond; or substituted or unsubstituted C _6-60 arylene,

Ar ₁ and Ar ₂ are each independently, substituted or unsubstituted C _6-60 aryl; _{Or C 2-60} substituted or unsubstituted aromatic heteroaryl containing one or more heteroatoms selected from the group consisting of N, O and S;

R ₁ , R ₂ and R ₃ are each independently hydrogen; heavy hydrogen; or substituted or unsubstituted C _1-60 alkyl;

a1, a2, and a3 are each independently an integer of 0-4.

Preferably, the compound represented by Formula 1 is a compound represented by Formula 1-1 or 1-5 below:

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

In Formulas 1-1 to 1-5,

L ₁ , L ₂ , L ₃ , Ar ₁ , Ar ₂ , R ₁ , R ₂ , R ₃ , a1 , a2 and a3 are the same as defined above.

Preferably, L ₁ is a direct bond, phenylene, biphenylrylene, terphenylrylene, naphthylene, phenanthrenylene, anthracenylene, triphenylenylene, fluorenylene, dibenzofuranylene or dibenzothiophenyl it's ren

More preferably, L ₁ is a direct bond, phenylene, biphenylrylene, terphenylrylene, naphthylene or dibenzofuranylene.

Preferably, L ₂ and L ₃ are each independently a direct bond, phenylene, biphenylrylene, terphenylrylene, naphthylene, phenanthrenylene, anthracenylene, triphenylenylene or fluorenylene.

More preferably, L ₂ and L ₃ are each independently a direct bond, phenylene, biphenylylene, or naphthylene.

,

및

의 치환기는 제외되는 것을 의미한다.wherein Ar ₁ and Ar ₂ are each independently, substituted or unsubstituted C _6-60 aryl; _{Or C 2-60} substituted or unsubstituted aromatic heteroaryl containing one or more heteroatoms selected from the group consisting of N, O and S, wherein heteroaryl refers to a compound having aromaticity, for example , semi-aromatic

,

and

Substituents of means to be excluded.

Preferably, Ar ₁ and Ar ₂ are each independently phenyl, biphenyl, terphenylyl, naphthyl, phenanthrenyl, anthracenyl, triphenylenyl, dimethylfluorenyl, diphenylfluorenyl, dibenzo furanyl, dibenzothiophenyl, carbazol-9-yl, or 9-phenyl-9H-carbazolyl.

Preferably, R ₁ , R ₂ and R ₃ are each independently hydrogen, deuterium, or C _1-10 alkyl.

More preferably R ₁ , R ₂ and R ₃ are each independently hydrogen.

Preferably, a1 representing the number of repeating units of _{R 1} is 0, 1 or 2, a2 representing the number of repeating units of _{R 2} is 0, 1 or 2, a3 representing the number of repeating units of _{R 3 is 0,} 1 or 2. More preferably, a1, a2 and a3 are each independently 0 or 1. Here, when a1, a2, and a3 are 0, it means that when there are no substituents R ₁ , R ₂ and R ₃ , R ₁ , R _{2 ,} and R ₃ are all hydrogen.

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

.

.

The compound represented by Formula 1 may be prepared through the following Reaction Scheme 1:

[Scheme 1]

In Scheme 1, definitions of substituents other than X are the same as described above, and X is halogen, preferably bromo or chloro.

Specifically, the compound represented by Formula 1 is prepared by combining starting materials SM1 and SM2 through an amine substitution reaction. These amine substitution reactions are preferably performed in the presence of a palladium catalyst and a base, respectively. In addition, the reactive group for the amine substitution reaction may be appropriately changed, and the method for preparing the compound represented by Formula 1 may be more specific in Preparation Examples to be described later.

(organic light emitting element)

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, an electron suppression layer, a light emitting layer, a hole blocking 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 layers.

In addition, the organic layer may include a hole injection layer, a hole transport layer, or a layer that injects and transports holes at the same time, and the hole injection layer, the hole transport layer, or a layer that simultaneously injects and transports holes is represented by Formula 1 The compounds shown are included.

In addition, the organic layer may include an electron blocking layer, and the electron blocking layer includes the compound represented by Formula 1 above.

In addition, the organic layer may include an emission layer, and the emission layer includes the compound represented by Formula 1 above.

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

In addition, the organic layer may include a hole blocking layer, the light emitting layer includes the compound represented by the formula (1).

In addition, in the organic light emitting diode according to the present invention, an anode, one or more organic material layers and a cathode are sequentially stacked on a substrate, wherein the first electrode is an anode and the second electrode is a cathode. may be small. In addition, in the organic light emitting device according to the present invention, the first electrode is a cathode and the second electrode is an anode, and the cathode, one or more organic material layers and the anode are sequentially stacked on a substrate of an inverted type organic structure. It may be a light emitting device. For example, the structure of the organic light emitting device 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 8 , a light emitting layer 4 , and a cathode 6 . In such a structure, the compound represented by Formula 1 may be included in the electron blocking layer 8 .

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

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 forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer thereon, and then 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 into 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 this 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 multilayer structure 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 with respect to 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 preferable. 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 the holes to the light emitting layer. material is suitable. As the hole transport material, the compound represented by Formula 1 may be used, or an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion may be used, but the present invention is not limited thereto. .

The electron blocking layer (or electron blocking layer, electron blocking layer) is formed on the hole transport layer, preferably provided in contact with the light emitting layer, to control hole mobility and prevent excessive movement of electrons between holes and electrons It refers to a layer that serves to improve the efficiency of the organic light emitting device by increasing the bonding probability. The electron blocking layer includes an electron blocking material, and as an example of the electron blocking material, a compound represented by Formula 1 may be used, and an arylamine-based organic material may be additionally used, but is not limited thereto.

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 light emitting layer may include a host material and a dopant material as described above. The host material may further include 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, and the like, and heterocyclic-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

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, and the styrylamine compound is a substituted or unsubstituted derivative. 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 light emitting layer may include the following iridium complex compound as a dopant material, but is not limited thereto:

.

.

The hole blocking layer (or hole blocking layer, hole blocking layer) is formed on the light emitting layer, preferably provided in contact with the light emitting layer, to control the electron mobility and prevent excessive movement of holes hole-electron coupling probability It refers to a layer that serves to improve the efficiency of the organic light emitting device by increasing it. The hole blocking layer includes a hole blocking material, and the compound represented by Formula 1 of the present invention may be used. Examples of additionally usable hole blocking materials include azine derivatives including triazine; triazole derivatives; oxadiazole derivatives; phenanthroline derivatives; A compound into which an electron withdrawing group is introduced, such as a phosphine oxide derivative, may be used, but the present invention is not limited thereto.

The electron injection and transport layer is a layer that simultaneously serves as an electron transport layer and an electron injection layer for injecting electrons from the electrode and transporting the received electrons to the emission layer, and is formed on the emission layer or the hole blocking layer. As the electron injection and transport material, a material capable of receiving electrons from the cathode and transferring them to the light emitting layer is suitable, and a material having high electron mobility is suitable. Examples of specific electron injection and transport materials include Al complex of 8-hydroxyquinoline; complexes containing Alq _{3 ;} organic radical compounds; hydroxyflavone-metal complexes; and triazine derivatives, but is not limited thereto. or fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc., derivatives thereof, metal complex compounds , or may be used together with a nitrogen-containing 5-membered ring derivative, and the like, but is not limited thereto.

The electron injection and transport layer may also be formed as a separate layer such as an electron injection layer and an electron transport layer. In this case, the electron transport layer is formed on the emission layer or the hole blocking layer, and the electron injection and transport material described above may be used as the electron transport material included in the electron transport layer. In addition, the electron injection layer is formed on the electron transport layer, and the electron injection material included in the electron injection layer is LiF, NaCl, CsF, Li ₂ O, BaO, fluorenone, anthraquinodimethane, diphenoquinone, Thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like may be used.

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. The present invention is not limited thereto.

The organic light emitting device according to the present invention may be a top emission type, a back emission type, or a double side 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 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 for illustrating the present invention, and the scope of the present invention is not limited thereto.

[Synthesis Example]

Synthesis Example 1: Synthesis of Compound 1

In a nitrogen atmosphere, sub1 (10 g, 52.2 mmol), sub2 (16.8 g, 52.2 mmol), and sodium tert-butoxide (7.5 g, 78.3 mmol) were added to 200 ml of Toluene, stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added thereto. After 3 hours, the reaction was completed, and the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain subA-1. (14.6 g, yield 65%, MS: [M+H] ⁺ = 432)

In a nitrogen atmosphere, subA-1 (10 g, 23.2 mmol), Formula A (6.8 g, 23.2 mmol), and sodium tert-butoxide (4.4 g, 46.3 mmol) were added to 200 ml of Xylene, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 3 hours, the reaction was completed, and the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 1. (8.4 g, yield 53%, MS: [M+H] ⁺ = 689)

Synthesis Example 2: Synthesis of compound 2

In a nitrogen atmosphere, sub1 (10 g, 52.2 mmol), sub3 (15.4 g, 52.2 mmol), and sodium tert-butoxide (7.5 g, 78.3 mmol) were added to 200 ml of Toluene, stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added thereto. After 3 hours, the reaction was completed, and the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain subA-2. (11.2 g, yield 53%, MS: [M+H] ⁺ = 406)

In a nitrogen atmosphere, subA-2 (10 g, 24.6 mmol), Formula A (7.2 g, 24.6 mmol), and sodium tert-butoxide (4.7 g, 49.3 mmol) were added to 200 ml of Xylene, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 3 hours, the reaction was completed, and the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 2. (10 g, yield 61%, MS: [M+H] ⁺ = 663)

Synthesis Example 3: Synthesis of compound 3

In a nitrogen atmosphere, sub4 (10 g, 52.2 mmol), sub2 (16.8 g, 52.2 mmol), and sodium tert-butoxide (7.5 g, 78.3 mmol) were added to 200 ml of Toluene, stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added thereto. After 3 hours, the reaction was completed, and the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain subA-3. (15.1 g, yield 67%, MS: [M+H] ⁺ = 432)

In a nitrogen atmosphere, subA-3 (10 g, 23.2 mmol), Formula A (6.8 g, 23.2 mmol), and sodium tert-butoxide (4.4 g, 46.3 mmol) were added to 200 ml of Xylene, followed by stirring and reflux. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 3 hours, the reaction was completed, and the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 3. (8.4 g, yield 53%, MS: [M+H] ⁺ = 689)

Synthesis Example 4: Synthesis of compound 4

In a nitrogen atmosphere, sub1 (10 g, 52.2 mmol), sub5 (18 g, 52.2 mmol), and sodium tert-butoxide (7.5 g, 78.3 mmol) were added to 200 ml of Toluene, stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added thereto. After 3 hours, the reaction was completed, and the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain subA-4. (13.3 g, yield 56%, MS: [M+H] ⁺ = 456)

In a nitrogen atmosphere, subA-4 (10 g, 21.9 mmol), Formula A (6.4 g, 21.9 mmol), and sodium tert-butoxide (4.2 g, 43.9 mmol) were added to 200 ml of Xylene, stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 3 hours, the reaction was completed, and the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 4. (10.6 g, yield 68%, MS: [M+H] ⁺ = 713)

Synthesis Example 5: Synthesis of compound 5

In a nitrogen atmosphere, sub1 (10 g, 52.2 mmol), sub (18.2 g, 52.2 mmol), and sodium tert-butoxide (7.5 g, 78.3 mmol) were added to 200 ml of Toluene, stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added thereto. After 3 hours, the reaction was completed, and the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain subA-5. (16.1 g, yield 67%, MS: [M+H] ⁺ = 460)

In a nitrogen atmosphere, subA-5 (10 g, 21.9 mmol), Formula A (6.4 g, 21.9 mmol), and sodium tert-butoxide (4.2 g, 43.9 mmol) were added to 200 ml of Xylene, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 3 hours, the reaction was completed, and the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 5. (8 g, yield 51%, MS: [M+H] ⁺ = 717)

Synthesis Example 6: Synthesis of compound 6

In a nitrogen atmosphere, sub7 (10 g, 37.4 mmol), sub8 (14.9 g, 37.4 mmol), and sodium tert-butoxide (5.4 g, 56.1 mmol) were added to 200 ml of Toluene, stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added thereto. After 3 hours, the reaction was completed, and the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain subA-6. (14 g, yield 64%, MS: [M+H] ⁺ = 584)

In a nitrogen atmosphere, subA-6 (10 g, 17.1 mmol), Formula A (5 g, 17.1 mmol), and sodium tert-butoxide (3.3 g, 34.2 mmol) were added to 200 ml of Xylene, followed by stirring and reflux. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 3 hours, the reaction was completed, and the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 6. (9.5 g, yield 66%, MS: [M+H] ⁺ = 841)

Synthesis Example 7: Synthesis of compound 7

In a nitrogen atmosphere, sub4 (10 g, 52.2 mmol), sub9 (18 g, 52.2 mmol), and sodium tert-butoxide (7.5 g, 78.3 mmol) were added to 200 ml of Toluene, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added thereto. After 3 hours, the reaction was completed, and the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain subA-7. (15.9 g, yield 67%, MS: [M+H] ⁺ = 456)

In a nitrogen atmosphere, subA-7 (10 g, 21.9 mmol), Formula A (6.4 g, 21.9 mmol), and sodium tert-butoxide (4.2 g, 43.9 mmol) were added to 200 ml of Xylene, followed by stirring and reflux. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 3 hours, the reaction was completed, and the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 7. (8.6 g, yield 55%, MS: [M+H] ⁺ = 713)

Synthesis Example 8: Synthesis of compound 8

In a nitrogen atmosphere, sub10 (10 g, 37.4 mmol), sub11 (13.5 g, 37.4 mmol), and sodium tert-butoxide (5.4 g, 56.1 mmol) were added to 200 ml of Toluene, stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added thereto. After 3 hours, the reaction was completed, and the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain subA-8. (13.5 g, yield 66%, MS: [M+H] ⁺ = 548)

In a nitrogen atmosphere, subA-8 (10 g, 18.2 mmol), Formula A (5.4 g, 18.2 mmol), and sodium tert-butoxide (3.5 g, 36.5 mmol) were added to 200 ml of Xylene, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 3 hours, the reaction was completed, and the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 8. (9.2 g, yield 63%, MS: [M+H] ⁺ = 805)

Synthesis Example 9: Synthesis of compound 9

In a nitrogen atmosphere, sub12 (10 g, 37.4 mmol), sub13 (15.3 g, 37.4 mmol), and sodium tert-butoxide (5.4 g, 56.1 mmol) were added to 200 ml of Toluene, stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added thereto. After 3 hours, the reaction was completed, and the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain subA-9. (11.1 g, yield 50%, MS: [M+H] ⁺ = 597)

In a nitrogen atmosphere, subA-9 (10 g, 16.7 mmol), Formula A (4.9 g, 16.7 mmol), and sodium tert-butoxide (3.2 g, 33.5 mmol) were added to 200 ml of Xylene, followed by stirring and reflux. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 3 hours, the reaction was completed, and the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 9. (9.9 g, yield 69%, MS: [M+H] ⁺ = 854)

Synthesis Example 10: Synthesis of compound 10

In a nitrogen atmosphere, sub10 (10 g, 37.4 mmol), sub14 (9.2 g, 37.4 mmol), and sodium tert-butoxide (5.4 g, 56.1 mmol) were added to 200 ml of Toluene, followed by stirring and reflux. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added thereto. After 3 hours, the reaction was completed, and the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain subB-1. (10.8 g, yield 67%, MS: [M+H] ⁺ = 432)

In a nitrogen atmosphere, subB-1 (10 g, 23.2 mmol), Formula B (6.8 g, 23.2 mmol), and sodium tert-butoxide (4.4 g, 46.3 mmol) were added to Xylene 200 ml, stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 3 hours, the reaction was completed, and the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 10. (10.4 g, yield 65%, MS: [M+H] ⁺ = 689)

Synthesis Example 11: Synthesis of compound 11

In a nitrogen atmosphere, sub1 (10 g, 52.2 mmol), sub15 (15.4 g, 52.2 mmol), and sodium tert-butoxide (7.5 g, 78.3 mmol) were added to 200 ml of Toluene, stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added thereto. After 3 hours, the reaction was completed, and the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain subB-2. (12.3 g, yield 58%, MS: [M+H] ⁺ = 406)

In a nitrogen atmosphere, subB-2 (10 g, 24.6 mmol), Formula B (7.2 g, 24.6 mmol), and sodium tert-butoxide (4.7 g, 49.3 mmol) were added to 200 ml of Xylene, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 3 hours, the reaction was completed, and the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 11. (8.5 g, yield 52%, MS: [M+H] ⁺ = 663)

Synthesis Example 12: Synthesis of compound 12

In a nitrogen atmosphere, sub16 (10 g, 35.5 mmol), sub17 (9.8 g, 35.5 mmol), and sodium tert-butoxide (5.1 g, 53.3 mmol) were added to 200 ml of Toluene, stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added thereto. After 3 hours, the reaction was completed, and the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain subB-3. (11.3 g, yield 67%, MS: [M+H] ⁺ = 476)

In a nitrogen atmosphere, subB-3 (10 g, 21 mmol), Formula B (6.2 g, 21 mmol), and sodium tert-butoxide (4 g, 42 mmol) were added to 200 ml of Xylene, followed by stirring and reflux. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 3 hours, the reaction was completed, and the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 12. (7.7 g, yield 50%, MS: [M+H] ⁺ = 733)

Synthesis Example 13: Synthesis of compound 13

In a nitrogen atmosphere, sub1 (10 g, 52.2 mmol), sub18 (20.8 g, 52.2 mmol), and sodium tert-butoxide (7.5 g, 78.3 mmol) were added to 200 ml of Toluene, stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added thereto. After 3 hours, the reaction was completed, and the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain subB-4. (14.8 g, yield 56%, MS: [M+H] ⁺ = 508)

In a nitrogen atmosphere, subB-4 (10 g, 19.7 mmol), Formula B (5.8 g, 19.7 mmol), and sodium tert-butoxide (3.8 g, 39.4 mmol) were added to 200 ml of Xylene, followed by stirring and reflux. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 3 hours, the reaction was completed, and the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 13. (8.7 g, yield 58%, MS: [M+H] + = 765)

Synthesis Example 14: Synthesis of compound 14

In a nitrogen atmosphere, sub19 (10 g, 52.2 mmol), sub20 (16.8 g, 52.2 mmol), and sodium tert-butoxide (7.5 g, 78.3 mmol) were added to 200 ml of Toluene, stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added thereto. After 3 hours, the reaction was completed, and the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain subC-1. (13.3 g, yield 59%, MS: [M+H] ⁺ = 432)

In a nitrogen atmosphere, subC-1 (10 g, 23.2 mmol), formula C (6.8 g, 23.2 mmol), and sodium tert-butoxide (4.4 g, 46.3 mmol) were added to 200 ml of Xylene, stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 3 hours, the reaction was completed, and the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 14. (10 g, yield 63%, MS: [M+H] ⁺ = 689)

Synthesis Example 15: Synthesis of compound 15

In a nitrogen atmosphere, sub10 (10 g, 37.4 mmol), sub21 (12.9 g, 37.4 mmol), and sodium tert-butoxide (5.4 g, 56.1 mmol) were added to 200 ml of Toluene, stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added thereto. After 3 hours, the reaction was completed, and the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain subC-2. (9.9 g, yield 50%, MS: [M+H] ⁺ = 532)

In a nitrogen atmosphere, subC-2 (10 g, 18.8 mmol), Formula C (5.5 g, 18.8 mmol), and sodium tert-butoxide (3.6 g, 37.6 mmol) were added to 200 ml of Xylene, followed by stirring and reflux. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 3 hours, the reaction was completed, and the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 15. (9.8 g, yield 66%, MS: [M+H] ⁺ = 789)

Synthesis Example 16: Synthesis of compound 16

In a nitrogen atmosphere, sub22 (10 g, 35.5 mmol), sub14 (8.7 g, 35.5 mmol), and sodium tert-butoxide (5.1 g, 53.3 mmol) were added to 200 ml of Toluene, stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added thereto. After 3 hours, the reaction was completed, and the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain subC-3. (10.6 g, yield 67%, MS: [M+H] ⁺ = 446)

In a nitrogen atmosphere, subC-3 (10 g, 22.4 mmol), formula C (6.6 g, 22.4 mmol), and sodium tert-butoxide (4.3 g, 44.8 mmol) were added to 200 ml of Xylene, followed by stirring and reflux. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 3 hours, the reaction was completed, and the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 16. (10.7 g, yield 68%, MS: [M+H] ⁺ = 703)

Synthesis Example 17: Synthesis of compound 17

In a nitrogen atmosphere, sub1 (10 g, 52.2 mmol), sub23 (20.8 g, 52.2 mmol), and sodium tert-butoxide (7.5 g, 78.3 mmol) were added to 200 ml of Toluene, stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added thereto. After 3 hours, the reaction was completed, and the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain subC-4. (16.2 g, yield 61%, MS: [M+H] ⁺ = 508)

In a nitrogen atmosphere, subC-4 (10 g, 19.7 mmol), formula C (5.8 g, 19.7 mmol), and sodium tert-butoxide (3.8 g, 39.4 mmol) were added to 200 ml of Xylene, stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 3 hours, the reaction was completed, and the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 17. (10.2 g, yield 68%, MS: [M+H] ⁺ = 765)

Synthesis Example 18: Synthesis of compound 18

In a nitrogen atmosphere, sub24 (10 g, 41.4 mmol), sub25 (14.6 g, 41.4 mmol), and sodium tert-butoxide (6 g, 62.1 mmol) were added to 200 ml of Toluene, stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added thereto. After 3 hours, the reaction was completed, and the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain subC-5. (11.4 g, yield 54%, MS: [M+H] ⁺ = 512)

In a nitrogen atmosphere, subC-5 (10 g, 19.5 mmol), Formula C (5.7 g, 19.5 mmol), and sodium tert-butoxide (3.8 g, 39.1 mmol) were added to 200 ml of Xylene, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 3 hours, the reaction was completed, and the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 18. (8.9 g, yield 59%, MS: [M+H] ⁺ = 769)

Synthesis Example 19: Synthesis of compound 19

In a nitrogen atmosphere, sub19 (10 g, 52.2 mmol), sub26 (21.4 g, 52.2 mmol), and sodium tert-butoxide (7.5 g, 78.3 mmol) were added to 200 ml of Toluene, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added thereto. After 3 hours, the reaction was completed, and the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain subC-6. (Yield 68%, MS: [M+H] ⁺ = 521)

In a nitrogen atmosphere, subC-6 (10 g, 19.2 mmol), Formula C (5.6 g, 19.2 mmol), and sodium tert-butoxide (3.7 g, 38.4 mmol) were added to 200 ml of Xylene, followed by stirring and reflux. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 3 hours, the reaction was completed, and the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 19. (8.7 g, yield 58%, MS: [M+H] ⁺ = 778)

Synthesis Example 20: Synthesis of compound 20

In a nitrogen atmosphere, sub27 (10 g, 37.4 mmol), sub28 (15.8 g, 37.4 mmol), and sodium tert-butoxide (5.4 g, 56.1 mmol) were added to 200 ml of Toluene, stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added thereto. After 3 hours, the reaction was completed, and the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain subC-7. (Yield 60%, MS: [M+H] ⁺ = 608)

In a nitrogen atmosphere, subC-7 (10 g, 16.4 mmol), Formula C (4.8 g, 16.4 mmol), and sodium tert-butoxide (3.2 g, 32.9 mmol) were added to 200 ml of Xylene, followed by stirring and reflux. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 3 hours, the reaction was completed, and the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved in chloroform again, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 20. (9.8 g, yield 69%, MS: [M+H] ⁺ = 865)

Synthesis Example 21: Synthesis of compound 21

In a nitrogen atmosphere, subB-2 (10 g, 24.6 mmol), Formula D (7.2 g, 24.6 mmol), and sodium tert-butoxide (4.7 g, 49.3 mmol) were added to 200 ml of Xylene, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 3 hours, the reaction was completed, and the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 21. (9.5 g, yield 58%, MS: [M+H] ⁺ = 663)

Synthesis Example 22: Synthesis of compound 22

In a nitrogen atmosphere, sub7 (10 g, 37.4 mmol), sub28 (15.8 g, 37.4 mmol), and sodium tert-butoxide (5.4 g, 56.1 mmol) were added to 200 ml of Toluene, stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added thereto. After 3 hours, the reaction was completed, and the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain subD-1. (12.5 g, yield 55%, MS: [M+H] ⁺ = 608)

In a nitrogen atmosphere, subD-1 (10 g, 16.4 mmol), Formula D (4.8 g, 16.4 mmol), and sodium tert-butoxide (3.2 g, 32.9 mmol) were added to 200 ml of Xylene, stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 3 hours, the reaction was completed, and the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 22. (7.7 g, yield 54%, MS: [M+H] ⁺ = 865)

Synthesis Example 23: Synthesis of compound 23

In a nitrogen atmosphere, sub4 (10 g, 52.2 mmol), sub29 (14.9 g, 52.2 mmol), and sodium tert-butoxide (7.5 g, 78.3 mmol) were added to 200 ml of Toluene, stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added thereto. After 3 hours, the reaction was completed, and the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain subD-2. (13.2 g, yield 64%, MS: [M+H] ⁺ = 396)

In a nitrogen atmosphere, subD-2 (10 g, 25.3 mmol), formula D (7.4 g, 25.3 mmol), and sodium tert-butoxide (4.9 g, 50.5 mmol) were added to 200 ml of Xylene, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added thereto. After 3 hours, the reaction was completed, and the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 23. (10 g, yield 61%, MS: [M+H] ⁺ = 653)

Synthesis Example 24: Synthesis of compound 24

In a nitrogen atmosphere, subB-3 (10 g, 21 mmol), Formula D (6.2 g, 21 mmol), and sodium tert-butoxide (4 g, 42 mmol) were added to 200 ml of Xylene, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 3 hours, the reaction was completed, and the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 24. (9.5 g, yield 62%, MS: [M+H] ⁺ = 733)

Synthesis Example 25: Synthesis of compound 25

In a nitrogen atmosphere, sub1 (10 g, 52.2 mmol), sub30 (22 g, 52.2 mmol), and sodium tert-butoxide (7.5 g, 78.3 mmol) were added to 200 ml of Toluene, stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added thereto. After 3 hours, the reaction was completed, and the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain subD-3. (18.3 g, yield 66%, MS: [M+H] ⁺ = 532)

In a nitrogen atmosphere, subD-3 (10 g, 18.8 mmol), Formula D (5.5 g, 18.8 mmol), and sodium tert-butoxide (3.6 g, 37.6 mmol) were added to 200 ml of Xylene, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 3 hours, the reaction was completed, and the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 25. (7.7 g, yield 52%, MS: [M+H] ⁺ = 789)

Synthesis Example 26: Synthesis of compound 26

In a nitrogen atmosphere, sub4 (10 g, 52.2 mmol), sub31 (18.4 g, 52.2 mmol), and sodium tert-butoxide (7.5 g, 78.3 mmol) were added to 200 ml of Toluene, stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added thereto. After 3 hours, the reaction was completed, and the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain subD-4. (16.9 g, yield 70%, MS: [M+H] ⁺ = 462)

In a nitrogen atmosphere, subD-4 (10 g, 21.6 mmol), formula D (6.3 g, 21.6 mmol), and sodium tert-butoxide (4.2 g, 43.3 mmol) were added to 200 ml of Xylene, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.2 mmol) was added. After 3 hours, the reaction was completed, and the solvent was removed by cooling to room temperature and reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 26. (9.8 g, yield 63%, MS: [M+H] ⁺ = 719)

[Examples and Comparative Examples]

Comparative Example 1

A glass substrate coated with indium tin oxide (ITO) to a thickness of 1,000 Å was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves. In this case, 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, 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.

The following HI-1 compound was formed as a hole injection layer on the prepared ITO transparent electrode to a thickness of 1150 Å, but the following A-1 compound was p-doped at a concentration of 1.5%. The following HT-1 compound was vacuum-deposited on the hole injection layer to form a hole transport layer having a thickness of 800 Å. Then, the following EB-1 compound was vacuum-deposited to a thickness of 150 Å on the hole transport layer to form an electron blocking layer. Then, the following RH-1 compound and the following Dp-7 compound were vacuum-deposited on the EB-1 deposited film 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 HB-1 compound to a thickness of 30 Å on the light emitting layer. Then, on the hole blocking layer, the following ET-1 compound and the following LiQ compound were vacuum-deposited in 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 1,000 Å on the electron injection and transport layer.

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

Examples 1-26

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 EB-1 in the organic light emitting device of Comparative Example 1.

Comparative Examples 2 to 8

An organic light emitting device was manufactured in the same manner as in Comparative Example 1, except that compounds C-1 to C-7 shown in Table 1 were used instead of EB-1 in the organic light emitting device of Comparative Example 1.

[Experimental example]

When a current was applied to the organic light emitting diodes prepared in Examples 1 to 26 and Comparative Examples 1 to 8, voltage and efficiency were measured (10 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 from the initial luminance (6000 nit) to 95%.

division matter
(electron suppression layer) Driving voltage (V) Efficiency (cd/A) Life T95 (hr) luminous color Comparative Example 1 EB-1 4.15 21.5 131 Red Example 1 compound 1 3.73 23.5 163 Red Example 2 compound 2 3.75 22.8 161 Red Example 3 compound 3 3.71 23.1 167 Red Example 4 compound 4 3.79 23.0 158 Red Example 5 compound 5 3.74 23.3 171 Red Example 6 compound 6 3.75 23.3 179 Red Example 7 compound 7 3.72 23.2 171 Red Example 8 compound 8 3.78 23.4 192 Red Example 9 compound 9 3.74 23.3 178 Red Example 10 compound 10 3.67 24.5 192 Red Example 11 compound 11 3.65 24.8 174 Red Example 12 compound 12 3.68 25.0 186 Red Example 13 compound 13 3.67 24.9 189 Red Example 14 compound 14 3.61 24.4 193 Red Example 15 compound 15 3.63 24.7 184 Red Example 16 compound 16 3.60 24.2 162 Red Example 17 compound 17 3.62 25.1 151 Red Example 18 compound 18 3.77 23.7 158 Red Example 19 compound 19 3.74 23.0 182 Red Example 20 compound 20 3.80 23.5 171 Red Example 21 compound 21 3.65 24.7 188 Red Example 22 compound 22 3.63 23.8 171 Red Example 23 compound 23 3.75 24.9 193 Red Example 24 compound 24 3.78 24.0 173 Red Example 25 compound 25 3.65 25.1 164 Red Example 26 compound 26 3.60 24.7 167 Red Comparative Example 2 C-1 4.12 19.3 84 Red Comparative Example 3 C-2 4.04 18.3 77 Red Comparative Example 4 C-3 3.99 18.6 81 Red Comparative Example 5 C-4 3.94 18.1 63 Red Comparative Example 6 C-5 3.88 19.5 101 Red Comparative Example 7 C-6 4.18 18.7 80 Red Comparative Example 8 C-7 4.15 18.0 51 Red

The red organic light emitting device of Comparative Example 1 uses a material commonly used for the electron suppressing layer, and has a structure using the compound [EB-1] as the electron suppressing layer and [RH-1/Dp-7] as the red light emitting layer am.

Referring to 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 it was found that the efficiency was greatly increased from the host to the red dopant. It was found that the energy transfer was well done. In addition, it was confirmed that the service life characteristics were greatly improved while maintaining high efficiency. This is because the compound of the present invention has higher electron and hole stability than the comparative example compound, and it can be confirmed that the driving voltage, luminous efficiency and lifespan characteristics of the organic light emitting device can be improved when the compound of the present invention is used.

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

Claims (9)

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

In Formula 1,
A is a naphthalene ring, B is a benzene ring; or B is a naphthalene ring, A is a benzene ring,
L ₁ is a direct bond; substituted or unsubstituted C _6-60 arylene; _{Or a substituted or unsubstituted C 2-60} heteroarylene containing one or more hetero atoms selected from the group consisting of N, O and S,
L ₂ and L ₃ are each independently, a direct bond; or substituted or unsubstituted C _6-60 arylene,
Ar ₁ and Ar ₂ are each independently, substituted or unsubstituted C _6-60 aryl; _{Or C 2-60} substituted or unsubstituted aromatic heteroaryl containing one or more heteroatoms selected from the group consisting of N, O and S;
R ₁ , R ₂ and R ₃ are each independently hydrogen; heavy hydrogen; or substituted or unsubstituted C _1-60 alkyl;
a1, a2, and a3 are each independently an integer of 0-4.
The method of claim 1,
The compound represented by Formula 1 is represented by the following Formulas 1-1 to 1-5,
compound:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

[Formula 1-5]

In Formulas 1-1 to 1-5,
L ₁ , L ₂ , L ₃ , Ar ₁ , Ar ₂ , R ₁ , R ₂ , R ₃ , a1 , a2 and a3 are as defined in claim 1.
The method of claim 1,
L ₁ is a direct bond, phenylene, biphenylrylene, terphenylrylene, naphthylene, phenanthrenylene, anthracenylene, triphenylenylene, fluorenylene, dibenzofuranylene or dibenzothiophenylene;
compound.
The method of claim 1,
L ₂ and L ₃ are each independently a direct bond, phenylene, biphenylrylene, terphenylrylene, naphthylene, phenanthrenylene, anthracenylene, triphenylenylene or fluorenylene;
compound.
The method of claim 1,
Ar ₁ and Ar ₂ are each independently, phenyl, biphenyl, terphenylyl, naphthyl, phenanthrenyl, anthracenyl, triphenylenyl, dimethylfluorenyl, diphenylfluorenyl, dibenzofuranyl, di which is benzothiophenyl, carbazol-9-yl, or 9-phenyl-9H-carbazolyl;
compound.
The method of claim 1,
R ₁ , R ₂ and R ₃ are each independently hydrogen, deuterium, or C _1-10 alkyl;
compound.
The method of 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 7 which is an organic light emitting device.
9. The method of claim 8,
The organic layer containing the compound is an electron suppression layer,
organic light emitting device.

Images