KR20210020819A - 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 can be used as a material for an organic material layer of the organic light emitting device, thereby improving the efficiency, low driving voltage and/or lifespan characteristics of 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 emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy using organic materials. An organic light-emitting device using the organic light-emitting phenomenon has a wide viewing angle, excellent contrast, and fast response time, and has excellent luminance, driving voltage, and response speed characteristics, and thus many studies are being conducted.

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

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

Korean Patent Publication No. 10-2013-073537

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,

R is linked at position 1 or 2 to form a single bond,

L is a single bond, or substituted or unsubstituted C _6-60 Arylene,

_{Het is C 5-60} including any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S Heteroaryl,

R ₁ , R ₂ , R ₃ , R ₄ and R ₅ are each independently hydrogen, deuterium, or substituted or unsubstituted C _1-60 alkyl,

n1, n3, n4 and n5 are each independently an integer of 0 to 4,

n2 is an integer from 0 to 2.

In addition, the present invention is a first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises the compound of the present invention.

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

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

Hereinafter, it will be described in more detail to aid 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.

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

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

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

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

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

In the present specification, the boron group specifically includes a trimethyl boron group, a triethyl boron group, a t-butyldimethyl boron group, a triphenyl boron group, and a phenyl boron group, but is not limited thereto.

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

In the present specification, the alkyl group may be a linear or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n -Pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cycloheptylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2 -Dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, and the like, but are not limited thereto.

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

In the present specification, the cycloalkyl group is not particularly limited, but is preferably 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3, 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto.

In the present specification, the aryl group is not particularly limited, but is preferably 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a phenyl group, a biphenyl group, or a terphenyl group, but the monocyclic aryl group is not limited thereto. The polycyclic aryl group may be a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, and the like, but is not limited thereto.

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

Etc. However, it is not limited thereto.

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

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

(compound)

The present invention provides a compound represented by Chemical Formula 1. The compound represented by Formula 1 has an indolocarbazole core structure, forms a seven-membered ring in which two benzene rings are further condensed around one nitrogen atom of the core structure, and is added to the other nitrogen atom. Characterized in that it contains a heteroaryl group. The condensed ring structure has high stability against electrons and holes, and when applied as a host compound, energy transfer to the dopant is easy. Accordingly, when employed as an emission layer compound in an organic light emitting device, characteristics of a low driving voltage, high efficiency, and long life can all be improved. The compound represented by Formula 1 is specifically as follows:

[Formula 1]

In Formula 1,

R is connected at the 1st or 2nd position to form a single bond, thereby forming a 7-membered ring around the N atom,

L is a single bond or a substituted or unsubstituted C _6-60 Arylene,

_{Het is C 5-60} including any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S Heteroaryl,

R ₁ , R ₂ , R ₃ , R ₄ and R ₅ are each independently hydrogen, deuterium, or substituted or unsubstituted C _1-60 alkyl,

n1, n3, n4 and n5 are each independently an integer of 0 to 4,

n2 is an integer from 0 to 2.

In the compound represented by Formula 1, R is connected at the 1st or 2nd position to form a seven-membered ring, in which case the compound represented by Formula 1 is represented by the following Formula 1-1 or 1-2:

[Formula 1-1]

[Formula 1-2]

In Formulas 1-1 to 1-2,

n'2 is 0 or 1,

n'3 is an integer from 0 to 3,

L, Het, R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , n1, n2, n3, n4, and n5 are as previously defined.

Preferably, L is a single bond, phenylene, or naphthylene.

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

In the above group,

R'is each independently, substituted or unsubstituted C _{6-60 C 5-60} comprising at least one hetero atom selected from the group consisting of aryl, or substituted or unsubstituted N, O and S Is heteroaryl.

Preferably, R'is each independently, phenyl, biphenylyl, naphthyl, terphenylyl, phenylnaphthyl, naphthylphenyl, phenanthrenyl, triphenylenyl, dimethylfluorenyl, dibenzofuranyl, Dibenzothiophenyl, carbazol-9-yl or 9-phenyl-9H-carbazolyl.

Preferably, R ₁ , R ₂ , R ₃ , R ₄ and R ₅ are each independently hydrogen or deuterium, more preferably all of them are hydrogen.

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

.

.

The compound represented by Formula 1 can be prepared according to the following Scheme 1:

[Scheme 1]

In the above reaction formula, each of X is independently halogen, preferably bromo or chloro, and the definition of other substituents is as described above.

The compound represented by Formula 1 may be prepared through a reaction of introducing an additional hetero substituent to the core structures of Core 1-1 and Core 1-2, and a specific example may be prepared through Reaction Scheme 1-3. The reactor for the 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 device)

Meanwhile, the present invention provides an organic light-emitting device including the compound represented by Formula 1 above. For example, the present invention provides a first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes a compound represented by Formula 1 .

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

In addition, the organic material layer may include a hole injection layer, a hole transport layer, or a layer that simultaneously injects and transports holes, and the hole injection layer, a hole transport layer, or a layer that simultaneously injects and transports holes is represented by Formula 1 above. Including the indicated compound.

In addition, the organic material layer may include an emission layer, and the emission layer includes the compound represented by Chemical Formula 1. Preferably, the compound represented by Formula 1 is used as a host compound of the emission layer.

The organic material layer of the organic light emitting device of the present invention may have a single-layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention further includes a hole injection layer and a hole transport layer between the first electrode and the emission layer, and an electron transport layer and an electron injection layer between the emission layer and the second electrode in addition to the emission layer as an organic material layer. It can have a structure to However, the structure of the organic light emitting device is not limited thereto and may include a smaller number or a larger number of organic layers.

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

1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a hole transport layer 3, a light-emitting layer 4, an electron injection and transport layer 5, and a cathode 6. In such a structure, the compound represented by Formula 1 may be included in the emission layer.

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

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

For example, the organic light emitting device according to the present invention may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. At this time, using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, the anode is formed by depositing a metal or a conductive metal oxide or an alloy thereof on the substrate. And, an organic material layer including a hole injection layer, a hole transport layer, an electron suppression layer, an emission layer, a hole suppression layer and an electron transport layer is formed thereon, and then a material that can be used as a cathode may be deposited thereon. In addition to this method, an organic light-emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

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

In addition to such a method, an organic light-emitting device may be manufactured by sequentially depositing an organic material layer and an anode material from a cathode material on a substrate (WO 2003/012890). However, the manufacturing method is not limited thereto.

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

As the anode material, a material having a large work function is preferable so that holes can be smoothly injected into the organic material layer. Specific examples of the cathode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO:Al or SnO _{2 :Sb;} Poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), conductive polymers such as polypyrrole and polyaniline, and the like, but are not limited thereto.

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

The hole injection layer is a layer that injects holes from an electrode, and has the ability to transport holes as a hole injection material, so that it has a hole injection effect at the anode, an excellent hole injection effect for a light emitting layer or a light emitting material. A compound that prevents the movement of excitons to the electron injection layer or the electron injection material and has excellent ability to form a thin film is preferable. It is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of hole injection materials include metal porphyrin, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based organic substances. Organic substances, anthraquinone, polyaniline, and polythiophene-based conductive polymers, but are not limited thereto.

The hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the emission layer, and the hole transport material is a material capable of transporting holes from the anode or the hole injection layer to the emission layer, and has high mobility for holes. The 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 inhibiting layer (or electron blocking layer, electron blocking layer) is formed on the hole transport layer, and is preferably provided in contact with the light emitting layer to control hole mobility and prevent excessive movement of electrons, thereby preventing the hole-electron It refers to a layer that serves to improve the efficiency of an organic light emitting device by increasing the probability of coupling. The electron inhibiting layer includes an electron blocking material, and an arylamine-based organic material may be used as an example of the electron blocking material, but is not limited thereto.

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

The light emitting layer includes a host material and a dopant material, and a compound represented by Formula 1 herein is used as a host material.

In addition, as a host material, a condensed aromatic ring derivative or a heterocyclic compound may be further included. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

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

Preferably, the light emitting layer may include the following iridium complex compound as a dopant material, but is not limited thereto.

.

.

The hole inhibiting layer (or hole blocking layer, hole blocking layer) is formed on the light emitting layer, and is preferably provided in contact with the light emitting layer, to control electron mobility and prevent excessive movement of holes, thereby increasing the probability of hole-electron bonding. It refers to a layer that serves to improve the efficiency of an organic light-emitting device by increasing it. The hole-suppressing layer includes a hole-suppressing material, and examples of such a hole-blocking material include a subazine derivative including triazine; Triazole derivatives; Oxadiazole derivatives; Phenanthroline derivatives; A compound into which an electron withdrawing group such as a phosphine oxide derivative has been introduced may be used, but is not limited thereto.

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 an electrode and transporting received electrons to the emission layer, and is formed on the emission layer or the hole suppression layer. As such an 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 mobility for electrons 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 complex; Triazine derivatives and the like, but are not limited thereto. Or fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidene methane, anthrone, and their derivatives, metal complex compounds , Or a nitrogen-containing 5-membered cyclic derivative, but may be used, but is not limited thereto.

The electron injection and transport layer may be formed as separate layers 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 suppression 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 electron injection materials included in the electron injection layer include LiF, NaCl, CsF, Li ₂ O, BaO, fluorenone, anthraquinodimethane, diphenoquinone, Thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidene methane, anthrone, and the like, their derivatives, metal complex compounds, and nitrogen-containing 5-membered ring derivatives may be used.

Examples of the metal complex compound include lithium 8-hydroxyquinolinato, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)( o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, etc. It is not limited thereto.

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

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

Preparation of the compound represented by Formula 1 and an organic light emitting device including the same will be described in detail in the following examples. However, the following examples are for illustrating the present invention, and the scope of the present invention is not limited thereto.

(Production example)

Preparation Example 1: Synthesis of Compound 1-1 (Synthesis of Core Structure)

1) Preparation of compound 1-1-5

2-Bromo-5-chloroaniline (300.0 g, 1.0 eq), 2-fluoro-2'-iodo-1,1'-biphenyl (375.5 g, 1.0 eq), KOtBu (217.4 g, 1.3 eq ) Was dissolved in NMP (3 L) and stirred under reflux. When the reaction was completed after 3 hours, it was poured into water to crystallize and then filtered. Thereafter, it was completely dissolved in ethyl acetate, washed with water, and reduced pressure to remove about 70% of the solvent. Hexane was added under reflux again, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography to obtain compound 1-1-5 (342.7 g).

(Yield 73%, MS:[M+H] ⁺ =486)

2) Preparation of compound 1-1-4

To compound 1-1-5 (342.7 g, 1.0 eq), Pd(t-Bu ₃ P) ₂ (8.48 g, 0.01 eq), K ₂ CO ₃ (372.6 g, 2.00 eq) was added to dimethylacetamide. 2 L) and refluxed to stir. After 2 hours, the reactant was poured into water to crystallize and then filtered. The filtered solid was completely dissolved in toluene, washed with water, and the solution in which the product was dissolved was concentrated under reduced pressure to drop crystals, cooled, and filtered. This was purified by column chromatography to obtain compound 1-1-4 (361.25 g).

(Yield 61%, MS:[M+H] ⁺ =358)

3) Preparation of compound 1-1-3

Compound 1-1-4 (361.3 g, 1012.9 mmol) and (2-fluorophenyl) boronic acid (304.8 g, 1012.9 mmol) were added to THF (4 L), stirred, and potassium carbonate (560 g, 4051.6 mmol) was added. After dissolving in water and stirring sufficiently, when refluxed, tetrakistriphenyl-phosphinopalladium (5.2 g, 10.1 mmol) was added. After the reaction for 4 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, and the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 1-1-3 (233.5 g).

(Yield 62%, MS: [M+H] ⁺ = 373)

4) Preparation of compound 1-1-2

Compound 1-1-3 (233.5 g, 1.0 eq) and KOtBu (120.1 g, 1.3 eq) were dissolved in NMP (1.5 L) and stirred under reflux. When the reaction was completed after 3 hours, it was poured into water to crystallize and then filtered. Thereafter, it was completely dissolved in ethyl acetate, washed with water, and reduced pressure to remove about 70% of the solvent. Hexane was added under reflux again, the crystals were dropped, cooled, and filtered. This was purified by silica gel column chromatography to obtain compound 1-1-2 (102.2 g).

(Yield 54%, MS: [M+H] ⁺ =353)

5) Preparation of compound 1-1-1

Compound 1-1-2 (102.18 g, 1.0 eq), (2-nitrophenyl) boronic acid (53.32 g, 1.1 eq) was added to THF (1 L), stirred, and potassium carbonate (97.77 g, 3.0 eq) was added to water. After dissolving in and stirring sufficiently, Pd(t-Bu ₃ P) ₂ (1.48 g, 0.01 eq) was added when refluxed. After 2 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, and the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 1-1-1 (95.51 g).

(Yield 75%, MS: [M+H] ⁺ = 439)

6) Preparation of compound 1-1

Compound 1-1-1 (95.51 g, 1.0 eq) was added to P(OEt) ₃ (700 mL), followed by reflux and stirred. After the reaction for 2 hours, it was cooled to room temperature and the resulting crystals were filtered. This was again dissolved in ethyl acetate, washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 1-1 (54.89 g).

(Yield 62%, MS: [M+H] ⁺ = 407)

Preparation Example 2: Synthesis of Compound 1-2 (Synthesis of Core Structure)

1) Preparation of compound 1-2-3

9H-tribenzo[b,d,f]azepine (200.0 g, 1.0 eq), 1-bromo-4-chloro-2-fluorobenzene (223.8 g, 1.3 eq), KOtBu (184.47 g, 2.0 eq) ) Was dissolved in NMP (2 L) and stirred under reflux. When the reaction was completed after 3 hours, it was poured into water to crystallize and then filtered. Then, it was completely dissolved in ethyl acetate, washed with water, and reduced pressure to remove about 70% of the solvent. Hexane was added under reflux again, the crystals were dropped, cooled, and filtered. This was subjected to column chromatography to obtain compound 1-2-3 (252.5 g).

(Yield 71%, MS: [M+H] ⁺ =434)

2) Preparation of compound 1-2-2

To compound 1-2-3 (252.56 g, 1.0 eq), Pd(t-Bu ₃ P) ₂ (2.98 g, 0.01 eq), K ₂ CO ₃ (130.97 g, 2.00 eq) was added to dimethylacetamide. 2 L) and refluxed to stir. After 2 hours, the reactant was poured into water to crystallize and then filtered. The filtered solid was completely dissolved in toluene, washed with water, and the solution in which the product was dissolved was concentrated under reduced pressure to drop crystals, cooled, and filtered. This was purified by silica gel column chromatography to obtain compound 1-2-2 (135.52 g).

(Yield 66%, MS: [M+H] ⁺ =353)

3) Preparation of compound 1-2-1

Compound 1-2-2 (135.52 g, 1.0 eq), (2-nitrophenyl) boronic acid (70.73 g, 1.1 eq) was added to THF (1 L), stirred, and potassium carbonate (129.66 g, 3.0 eq) was added to water. After dissolving in and stirring sufficiently, Pd(t-Bu ₃ P) ₂ (1.96 g, 0.01 eq) was added when refluxed. After 2 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, and the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 1-2-1 (131.74 g).

(Yield 78%, MS: [M+H] ⁺ = 439)

4) Preparation of compound 1-2

Compound 1-2-1 (131.74 g, 1.0 eq) was added to P(OEt) ₃ (500 mL), followed by reflux and stirred. After the reaction for 2 hours, it was cooled to room temperature and the resulting crystals were filtered. This was again dissolved in ethyl acetate, washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 1-2 (50.46 g).

(Yield 57%, MS: [M+H] ⁺ = 407)

Synthesis Example 1: Preparation of Compound 1

In a nitrogen atmosphere, intermediate compound 1a (10 g, 37.4 mmol), compound 1-1 (15.2 g, 37.4 mmol), and NaOtBu (7.2 g, 74.7 mmol) were added to xylene (200 mL), followed by stirring and refluxing. After this, bis (tri-tert-butylphosphine) palladium (0) (0.4 g, 0.7 mmol) was added. After 4 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and 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 (7.4 g).

(Yield 31%, MS: [M+H] ⁺ = 639)

Synthesis Example 2: Preparation of Compound 2

In a nitrogen atmosphere, intermediate compound 2a (10 g, 23.8 mmol), compound 1-1 (9.7 g, 23.8 mmol), and NaOtBu (4.6 g, 47.6 mmol) were added to xylene (200 mL) and stirred and refluxed. After this, bis (tri-tert-butylphosphine) palladium (0) (0.2 g, 0.5 mmol) was added. After 3 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and 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 (11.3 g).

(Yield 60%, MS: [M+H] ⁺ = 790)

Synthesis Example 3: Synthesis of Compound 3

In a nitrogen atmosphere, intermediate compound 3a (10 g, 24.6 mmol), compound 1-1 (10 g, 24.6 mmol), and NaOtBu (4.7 g, 49.3 mmol) were added to xylene (200 mL) and stirred and refluxed. After this, bis (tri-tert-butylphosphine) palladium (0) (0.3 g, 0.5 mmol) was added. After 3 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and 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 g).

(Yield 42%, MS: [M+H] ⁺ = 777)

Synthesis Example 4: Synthesis of Compound 4

In a nitrogen atmosphere, intermediate compound 4a (10 g, 28.8 mmol), compound 1-1 (11.7 g, 28.8 mmol), and NaOtBu (5.5 g, 57.7 mmol) were added to xylene (200 mL), followed by stirring and refluxing. After this, bis (tri-tert-butylphosphine) palladium (0) (0.3 g, 0.6 mmol) was added. After 2 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and 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 (9.5 g).

(Yield 46%, MS: [M+H] ⁺ = 718)

Synthesis Example 5: Synthesis of Compound 5

In a nitrogen atmosphere, intermediate compound 5a (10 g, 25.6 mmol), compound 1-1 (10.4 g, 25.6 mmol), and NaOtBu (4.9 g, 51.2 mmol) were added to xylene (200 mL) and stirred and refluxed. After this, bis (tri-tert-butylphosphine) palladium (0) (0.3 g, 0.5 mmol) was added. After 3 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and 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 41%, MS: [M+H] ⁺ = 762)

Synthesis Example 6: Synthesis of Compound 6

In a nitrogen atmosphere, intermediate compound 6a (10 g, 26.3 mmol), compound 1-1 (10.7 g, 26.3 mmol), and NaOtBu (5.1 g, 52.7 mmol) were added to xylene (200 mL), followed by stirring and refluxing. After this, bis (tri-tert-butylphosphine) palladium (0) (0.3 g, 0.5 mmol) was added. After 3 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and 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 (8.5 g).

(Yield 43%, MS: [M+H] ⁺ = 751)

Synthesis Example 7: Synthesis of Compound 7

In a nitrogen atmosphere, intermediate compound 7a (10 g, 26.3 mmol), compound 1-1 (10.7 g, 26.3 mmol), and NaOtBu (5 g, 52.5 mmol) were added to xylene (200 mL) and stirred and refluxed. After this, bis (tri-tert-butylphosphine) palladium (0) (0.3 g, 0.5 mmol) was added. After 4 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and 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 (5.9 g).

(Yield 30%, MS: [M+H] ⁺ = 752)

Synthesis Example 8: Synthesis of Compound 8

In a nitrogen atmosphere, intermediate compound 8a (10 g, 23.6 mmol), compound 1-1 (9.6 g, 23.6 mmol), and NaOtBu (4.5 g, 47.3 mmol) were added to xylene (200 mL) and stirred and refluxed. After this, bis (tri-tert-butylphosphine) palladium (0) (0.2 g, 0.5 mmol) was added. After 2 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and 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 (6.6 g).

(Yield 35%, MS: [M+H] ⁺ = 794)

Synthesis Example 9: Synthesis of Compound 9

In a nitrogen atmosphere, intermediate compound 9a (10 g, 26.8 mmol), compound 1-1 (10.9 g, 26.8 mmol), and NaOtBu (5.2 g, 53.6 mmol) were added to xylene (200 mL), followed by stirring and refluxing. After this, bis (tri-tert-butylphosphine) palladium (0) (0.3 g, 0.5 mmol) was added. After 2 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and 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 (10.4 g).

(Yield 52%, MS: [M+H] ⁺ = 744)

Synthesis Example 10: Synthesis of Compound 10

In a nitrogen atmosphere, intermediate compound 10a (10 g, 25.8 mmol), compound 1-1 (10.5 g, 25.8 mmol), and NaOtBu (5 g, 51.7 mmol) were added to xylene (200 mL) and stirred and refluxed. After this, bis (tri-tert-butylphosphine) palladium (0) (0.3 g, 0.5 mmol) was added. After 3 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and 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 (8.8 g).

(Yield 45%, MS: [M+H] ⁺ = 758)

Synthesis Example 11: Synthesis of Compound 11

In a nitrogen atmosphere, intermediate compound 11a (10 g, 24.8 mmol), compound 1-1 (10.1 g, 24.8 mmol), and NaOtBu (4.8 g, 49.6 mmol) were added to xylene (200 mL) and stirred and refluxed. After this, bis (tri-tert-butylphosphine) palladium (0) (0.3 g, 0.5 mmol) was added. After 4 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and 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 (6.1 g).

(Yield 32%, MS: [M+H] ⁺ = 774)

Synthesis Example 12: Synthesis of Compound 12

In a nitrogen atmosphere, intermediate compound 12a (10 g, 30.2 mmol), compound 1-1 (12.3 g, 30.2 mmol), and NaOtBu (5.8 g, 60.5 mmol) were added to xylene (200 mL) and stirred and refluxed. After this, bis (tri-tert-butylphosphine) palladium (0) (0.3 g, 0.6 mmol) was added. After 3 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and 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 (8.7 g).

(Yield 41%, MS: [M+H] ⁺ = 702)

Synthesis Example 13: Synthesis of Compound 13

In a nitrogen atmosphere, intermediate compound 13a (10 g, 27 mmol), compound 1-1 (11 g, 27 mmol), and NaOtBu (5.2 g, 53.9 mmol) were added to xylene (200 mL) and stirred and refluxed. After this, bis (tri-tert-butylphosphine) palladium (0) (0.3 g, 0.5 mmol) was added. After 3 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and 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 g).

(Yield 40%, MS: [M+H] ⁺ = 742)

Synthesis Example 14: Synthesis of Compound 14

In a nitrogen atmosphere, intermediate compound 14a (10 g, 28 mmol), compound 1-1 (11.4 g, 28 mmol), and NaOtBu (5.4 g, 56.1 mmol) were added to xylene (200 mL) and stirred and refluxed. After this, bis (tri-tert-butylphosphine) palladium (0) (0.3 g, 0.6 mmol) was added. After 3 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and 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 (7.7 g).

(Yield 38%, MS: [M+H] ⁺ = 728)

Synthesis Example 15: Synthesis of Compound 15

In a nitrogen atmosphere, intermediate compound 15a (10 g, 22.4 mmol), compound 1-1 (9.1 g, 22.4 mmol), and NaOtBu (4.3 g, 44.9 mmol) were added to xylene (200 mL) and stirred and refluxed. After this, bis (tri-tert-butylphosphine) palladium (0) (0.2 g, 0.4 mmol) was added. After 3 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and 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 (9.3 g).

(Yield 51%, MS: [M+H] ⁺ = 817)

Synthesis Example 16: Synthesis of Compound 16

In a nitrogen atmosphere, intermediate compound 16a (10 g, 31.5 mmol), compound 1-2 (12.8 g, 31.5 mmol), and NaOtBu (6 g, 62.9 mmol) were added to xylene (200 mL) and stirred and refluxed. After this, bis (tri-tert-butylphosphine) palladium (0) (0.3 g, 0.6 mmol) was added. After 4 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and 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 (9.7 g).

(Yield 45%, MS: [M+H] ⁺ = 689)

Synthesis Example 17: Synthesis of Compound 17

In a nitrogen atmosphere, intermediate compound 17a (10 g, 25.4 mmol), compound 1-2 (10.3 g, 25.4 mmol), and NaOtBu (4.9 g, 50.8 mmol) were added to xylene (200 mL) and stirred and refluxed. After this, bis (tri-tert-butylphosphine) palladium (0) (0.3 g, 0.5 mmol) was added. After 3 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and 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 (9.7 g).

(Yield 50%, MS: [M+H] ⁺ = 765)

Synthesis Example 18: Synthesis of Compound 18

In a nitrogen atmosphere, intermediate compound 18a (10 g, 27.9 mmol), compound 1-2 (11.4 g, 27.9 mmol), and NaOtBu (5.4 g, 55.9 mmol) were added to xylene (200 mL) and stirred and refluxed. After this, bis (tri-tert-butylphosphine) palladium (0) (0.3 g, 0.6 mmol) was added. After 4 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and 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 (9.6 g).

(Yield 47%, MS: [M+H] ⁺ = 729)

Synthesis Example 19: Synthesis of Compound 19

In a nitrogen atmosphere, intermediate compound 19a (10 g, 41.5 mmol), compound 1-2 (16.9 g, 41.5 mmol), and NaOtBu (8 g, 83.1 mmol) were added to xylene (200 mL) and stirred and refluxed. After this, bis (tri-tert-butylphosphine) palladium (0) (0.4 g, 0.8 mmol) was added. After 4 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and 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 (8.4 g).

(Yield 33%, MS: [M+H] ⁺ = 612)

Synthesis Example 20: Synthesis of Compound 20

In a nitrogen atmosphere, intermediate compound 20a (10 g, 29.3 mmol), compound 1-2 (11.9 g, 29.3 mmol), and NaOtBu (5.6 g, 58.7 mmol) were added to xylene (200 mL) and stirred and refluxed. After this, bis (tri-tert-butylphosphine) palladium (0) (0.3 g, 0.6 mmol) was added. After 2 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and 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 (8.8 g).

(Yield 42%, MS: [M+H] ⁺ = 712)

Synthesis Example 21: Synthesis of Compound 21

In a nitrogen atmosphere, intermediate compound 21a (10 g, 24.6 mmol), compound 1-2 (10 g, 24.6 mmol), and NaOtBu (4.7 g, 49.3 mmol) were added to xylene (200 mL) and stirred and refluxed. After this, bis (tri-tert-butylphosphine) palladium (0) (0.3 g, 0.5 mmol) was added. After 2 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and 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 (7.8 g).

(Yield 41%, MS: [M+H] ⁺ = 777)

Synthesis Example 22: Synthesis of Compound 22

In a nitrogen atmosphere, intermediate compound 22a (10 g, 25.6 mmol), compound 1-2 (10.4 g, 25.6 mmol), and NaOtBu (4.9 g, 51.2 mmol) were added to xylene (200 mL) and stirred and refluxed. After this, bis (tri-tert-butylphosphine) palladium (0) (0.3 g, 0.5 mmol) was added. After 3 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and 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 (5.8 g).

(Yield 30%, MS: [M+H] ⁺ = 762)

Synthesis Example 23: Synthesis of Compound 23

In a nitrogen atmosphere, intermediate compound 23a (10 g, 22.6 mmol), compound 1-2 (9.2 g, 22.6 mmol), and NaOtBu (4.3 g, 45.2 mmol) were added to xylene (200 mL) and stirred and refluxed. After this, bis (tri-tert-butylphosphine) palladium (0) (0.2 g, 0.5 mmol) was added. After 4 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and 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 (11 g).

(Yield 60%, MS: [M+H] ⁺ = 814)

Synthesis Example 24: Synthesis of Compound 24

In a nitrogen atmosphere, intermediate compound 24a (10 g, 33.7 mmol), compound 1-2 (13.7 g, 33.7 mmol), and NaOtBu (6.5 g, 67.4 mmol) were added to xylene (200 mL) and stirred and refluxed. After this, bis (tri-tert-butylphosphine) palladium (0) (0.3 g, 0.7 mmol) was added. After 2 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and 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 (12.6 g).

(Yield 56%, MS: [M+H] ⁺ = 668)

Synthesis Example 25: Synthesis of Compound 25

In a nitrogen atmosphere, intermediate compound 25a (10 g, 22.3 mmol), compound 1-2 (9.1 g, 22.3 mmol), and NaOtBu (4.3 g, 44.5 mmol) were added to xylene (200 mL) and stirred and refluxed. After this, bis (tri-tert-butylphosphine) palladium (0) (0.2 g, 0.4 mmol) was added. After 3 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and 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 (8.9 g).

(Yield 49%, MS: [M+H] ⁺ = 820)

Synthesis Example 26: Synthesis of Compound 26

In a nitrogen atmosphere, intermediate compound 26a (10 g, 25.8 mmol), compound 1-2 (10.5 g, 25.8 mmol), and NaOtBu (5 g, 51.7 mmol) were added to xylene (200 mL) and stirred and refluxed. After this, bis (tri-tert-butylphosphine) palladium (0) (0.3 g, 0.5 mmol) was added. After 2 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and 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 (7.4 g).

(Yield 38%, MS: [M+H] ⁺ = 758)

Synthesis Example 27: Synthesis of Compound 27

In a nitrogen atmosphere, intermediate compound 27a (10 g, 21.6 mmol), compound 1-2 (8.8 g, 21.6 mmol), and NaOtBu (4.2 g, 43.3 mmol) were added to xylene (200 mL) and stirred and refluxed. After this, bis (tri-tert-butylphosphine) palladium (0) (0.2 g, 0.4 mmol) was added. After 2 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and 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 27 (8.5 g).

(Yield 47%, MS: [M+H] ⁺ = 833)

Synthesis Example 28: Synthesis of Compound 28

In a nitrogen atmosphere, intermediate compound 28a (10 g, 35.6 mmol), compound 1-2 (14.5 g, 35.6 mmol), and NaOtBu (6.8 g, 71.2 mmol) were added to xylene (200 mL) and stirred and refluxed. After this, bis (tri-tert-butylphosphine) palladium (0) (0.4 g, 0.7 mmol) was added. After 3 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and 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 28 (10.9 g).

(Yield 47%, MS: [M+H] ⁺ = 652)

Synthesis Example 29: Synthesis of Compound 29

In a nitrogen atmosphere, intermediate compound 29a (10 g, 28 mmol), compound 1-2 (11.4 g, 28 mmol), and NaOtBu (5.4 g, 56.1 mmol) were added to xylene (200 mL), followed by stirring and refluxing. After this, bis (tri-tert-butylphosphine) palladium (0) (0.3 g, 0.6 mmol) was added. After 4 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and 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 29 (7.5 g).

(Yield 37%, MS: [M+H] ⁺ = 728)

Synthesis Example 30: Synthesis of Compound 30

In a nitrogen atmosphere, intermediate compound 30a (10 g, 25.8 mmol), compound 1-2 (10.5 g, 25.8 mmol), and NaOtBu (5 g, 51.7 mmol) were added to xylene (200 mL) and stirred and refluxed. After this, bis (tri-tert-butylphosphine) palladium (0) (0.3 g, 0.5 mmol) was added. After 4 hours, the reaction was terminated, cooled to room temperature, and reduced pressure to remove the solvent. Thereafter, the compound was completely dissolved in chloroform again, washed twice with water, and 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 30 (6.3 g).

(Yield 32%, MS: [M+H] ⁺ = 758)

(Examples and Comparative Examples)

Comparative Example 1

A glass substrate coated with a thin film of ITO (indium tin oxide) to a thickness of 1,000 Å was put in distilled water dissolved in a detergent and washed with ultrasonic waves. At this time, a product made by Fischer Co. was used as a detergent, and distilled water secondarily filtered with a filter manufactured by Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, it was repeated twice with distilled water to perform ultrasonic cleaning for 10 minutes. After washing with distilled water, ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. Further, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

The 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 compound A-1 was p-doping 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. Subsequently, the following EB-1 compound was vacuum deposited on the hole transport layer with a film thickness of 150 Å to form an electron suppressing layer. Subsequently, the following RH-1 compound and the following Dp-7 compound were vacuum-deposited at a weight ratio of 98:2 on the EB-1 deposition film 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 with a thickness of 30 Å on the emission layer. Subsequently, the following ET-1 compound and the following LiQ compound were vacuum-deposited at a weight ratio of 2:1 on the hole blocking layer to form an electron injection and transport layer with a thickness of 300 Å. Lithium fluoride (LiF) at a thickness of 12 Å and aluminum at a thickness of 1,000 Å were sequentially deposited on the electron injection and transport layer to form a negative electrode.

In the above process, the deposition rate of organic material was maintained at 0.4 to 0.7 Å/sec, the deposition rate of lithium fluoride at the cathode was 0.3 Å/sec, and the deposition rate of aluminum was 2 Å/sec, and the vacuum degree during deposition was 2X10 ^-7 By maintaining ~ 5X10 ^-6 torr, an organic light emitting device was manufactured.

Preparation of Examples 1 to 30

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that the compounds of Compounds 1 to 30 synthesized above were used instead of RH-1 in the organic light-emitting device of Comparative Example 1.

Preparation of Comparative Examples 2 to 9

An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that the following compounds C-1 to C-8 were used instead of RH-1 in the organic light-emitting device of Comparative Example 1.

(Experimental example)

^{When a current (10 mA/cm 2} ) was applied to the organic light emitting devices of Examples 1 to 30 and Comparative Examples 1 to 9, voltage and efficiency were measured, and the results are shown in Table 1 below. The lifetime T95 refers to the time it takes for the luminance to decrease from initial luminance (6000 nit) to 95%.

division matter Driving voltage (V) Efficiency (cd/A) Life T95(hr) Luminous color Example 1 Compound 1 3.63 28.5 154 Red Example 2 Compound 2 3.51 28.3 217 Red Example 3 Compound 3 3.52 24.5 193 Red Example 4 Compound 4 3.88 25.7 160 Red Example 5 Compound 5 3.63 26.2 175 Red Example 6 Compound 6 3.65 26.8 170 Red Example 7 Compound 7 3.63 26.3 178 Red Example 8 Compound 8 3.61 26.4 191 Red Example 9 Compound 9 3.64 26.5 164 Red Example 10 Compound 10 3.58 26.6 168 Red Example 11 Compound 11 3.63 25.1 170 Red Example 12 Compound 12 3.61 26.8 173 Red Example 13 Compound 13 3.73 27.0 195 Red Example 14 Compound 14 3.61 26.9 169 Red Example 15 Compound 15 3.65 26.7 181 Red Example 16 Compound 16 3.50 28.1 192 Red Example 17 Compound 17 3.51 28.0 221 Red Example 18 Compound 18 3.48 28.7 210 Red Example 19 Compound 19 3.81 27.0 224 Red Example 20 Compound 20 3.73 27.5 163 Red Example 21 Compound 21 3.80 26.1 160 Red Example 22 Compound 22 3.74 26.8 163 Red Example 23 Compound 23 3.75 26.0 165 Red Example 24 Compound 24 3.69 25.9 205 Red Example 25 Compound 25 3.65 26.7 197 Red Example 26 Compound 26 3.63 26.2 192 Red Example 27 Compound 27 3.70 27.4 164 Red Example 28 Compound 28 3.65 26.3 201 Red Example 29 Compound 29 3.61 27.0 184 Red Example 30 Compound 30 3.67 27.5 177 Red Comparative Example 1 RH-1 4.04 21.3 120 Red Comparative Example 2 C-1 3.95 13.3 37 Red Comparative Example 3 C-2 3.98 15.9 77 Red Comparative Example 4 C-3 3.93 20.7 103 Red Comparative Example 5 C-4 4.25 20.2 127 Red Comparative Example 6 C-5 4.03 18.5 85 Red Comparative Example 7 C-6 4.02 19.3 91 Red Comparative Example 8 C-7 4.09 20.5 105 Red Comparative Example 9 C-8 4.11 20.3 98 Red

The red organic light-emitting device of Comparative Example 1 used a material that has been widely used in the past, and has a structure using compound EB-1 as an electron blocking layer and compounds RH-1/Dp-7 as a red light emitting layer. In Comparative Examples 2 to 9, an organic light-emitting device was manufactured using C-1 to C-8 instead of RH-1.

As can be seen from the above experimental data, when the compound of the present invention was used as a host of the red light emitting layer, energy transfer from the host to the red dopant was well performed compared to the material of the comparative example, so that the driving voltage was significantly lowered and the efficiency was greatly increased. . In addition, it was confirmed that the organic light-emitting device employing the present compound significantly improved lifespan characteristics by more than two times while maintaining high efficiency.

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 suppression layer

Claims (8)

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

In Formula 1,
R is connected at position 1 or 2 to form a single bond,
L is a single bond, or substituted or unsubstituted C _6-60 Arylene,
_{Het is C 5-60} including any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S Heteroaryl,
R ₁ , R ₂ , R ₃ , R ₄ and R ₅ are each independently hydrogen, deuterium, or substituted or unsubstituted C _1-60 alkyl,
n1, n3, n4 and n5 are each independently an integer of 0 to 4,
n2 is an integer from 0 to 2.
The method of claim 1,
Formula 1 is represented by the following Formula 1-1 or 1-2,
compound:
[Formula 1-1]

[Formula 1-2]

In Formulas 1-1 to 1-2,
n'2 is 0 or 1,
n'3 is an integer from 0 to 3,
L, Het, R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , n1, n2, n3, n4 and n5 are as defined in claim 1.
The method of claim 1,
L is a single bond, phenylene, or naphthylene,
compound.
The method of claim 1,
Het is any one selected from the group consisting of,
compound:

In the above group,
R'is each independently, substituted or unsubstituted C _{6-60 C 5-60} comprising at least one hetero atom selected from the group consisting of aryl, or substituted or unsubstituted N, O and S Is heteroaryl.
The method of claim 4,
R'is each independently phenyl, biphenylyl, naphthyl, terphenylyl, phenylnaphthyl, naphthylphenyl, phenanthrenyl, triphenylenyl, dimethylfluorenyl, dibenzofuranyl, dibenzothiophenyl , Carbazol-9-yl or 9-phenyl-9H-carbazolyl,
compound.
The method of claim 1,
R ₁ , R ₂ , R ₃ , R ₄ and R ₅ are each independently hydrogen or deuterium,
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 one or more organic material layers 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 That is, an organic light-emitting device.

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