KR102430077B1 - Novel compound and organic light emitting device comprising the same - Google Patents

Abstract

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

Description

Novel compound and organic light emitting device using 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, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. When a voltage is applied between the two electrodes in the structure of the organic light emitting device, holes are injected into the organic material layer from the anode and electrons from the cathode are injected into the organic material layer. When the injected holes and electrons meet, excitons are formed, and the excitons It lights up when it falls back to the ground state.

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

Korean Patent Publication No. 10-2013-073537

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 joined at the 1st or 2nd position to form a single bond,

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

Het is C _5-60 containing 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 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 of the present invention.

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

FIG. 1 shows an example of an organic light emitting device including 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 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 composed of 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 (D); halogen group; nitrile group; nitro group; hydroxyl group; carbonyl group; ester group; imid; amino group; phosphine oxide group; alkoxy group; aryloxy group; alkyl thiooxy group; arylthioxy group; an alkyl sulfoxy group; arylsulfoxy group; silyl group; boron group; an alkyl group; cycloalkyl group; alkenyl group; aryl group; aralkyl group; aralkenyl group; an alkylaryl group; an alkylamine group; an aralkylamine group; heteroarylamine group; arylamine group; an aryl phosphine group; Or N, O, and S atom means that it is substituted or unsubstituted with one or more substituents selected from the group consisting of a heterocyclic group containing one or more, or substituted or unsubstituted, two or more of the above-exemplified substituents are linked. . For example, "a substituent in which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected.

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

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

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

In the present specification, the silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like. However, the present invention is not limited thereto.

In the present specification, the boron group specifically includes a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, a phenylboron group, and the like, but is not limited thereto.

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

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

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

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

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

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

etc. can be However, the present invention is not limited thereto.

In the present specification, the heterocyclic group is a heterocyclic group including at least one of O, N, Si and S as a heterogeneous element, and the number of carbon atoms is not particularly limited, but it is preferably from 2 to 60 carbon atoms. Examples of the heterocyclic group include a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazine group, 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, the description of the heterocyclic group described above for heteroaryl among heteroarylamines may be applied. In the present specification, the alkenyl group among the aralkenyl groups is the same as the examples of the above-described alkenyl groups. In the present specification, the description of the above-described aryl group may be applied except that arylene is a divalent group. In the present specification, the description of the above-described 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)

The present invention provides a compound represented by the above formula (1). The compound represented by Formula 1 has an indolocarbazole core structure, two benzene rings are further condensed around one nitrogen atom of the core structure to form a heptagonal ring, and the other nitrogen atom is added to It is characterized in that it contains a heteroaryl group. Due to the condensed ring structure, stability with respect to electrons and holes is high, and energy transfer to a dopant is easy when applied as a host compound. Accordingly, when employed as a light emitting layer compound in an organic light emitting device, all characteristics of low driving voltage, high efficiency, and long life can be improved. The compound represented by Formula 1 is specifically as follows:

[Formula 1]

In Formula 1,

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

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

Het is C _5-60 containing 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 linked at the 1st or 2nd position to form a 7-membered ring, in this case, the compound represented by Formula 1 is represented by 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 defined above.

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

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

In the group,

R' is each independently, substituted or unsubstituted C _6-60 C _5-60 containing one or more heteroatoms selected from the group consisting of aryl, or substituted or unsubstituted N, O and S heteroaryl.

Preferably, each R' is 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 may be prepared according to Scheme 1:

[Scheme 1]

In the above scheme, each X is independently halogen, preferably bromo or chloro, and definitions for other substituents are as described above.

The compound represented by Formula 1 may be prepared through a reaction of introducing additional hetero substituents into the core structures of Core 1-1 and Core 1-2, and as a specific example, may be prepared through 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 element)

On the other hand, 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. .

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 blocking 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 simultaneously injects and transports holes, and the hole injection layer, the hole transport layer, or a layer that simultaneously injects and transports holes is represented by Formula 1 The indicated compounds are included.

In addition, the organic material layer may include a light emitting layer, and the light emitting layer includes the compound represented by Formula 1 above. Preferably, the compound represented by Formula 1 is used as the host compound of the light emitting 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 multi-layer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention further comprises a hole injection layer and a hole transport layer between the first electrode and the light emitting layer, and an electron transport layer and an electron injection layer between the light emitting layer and the second electrode in addition to the light emitting layer as an organic layer can have a structure that 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, 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 a cathode, one or more organic material layers and an 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 diode according to an embodiment of the present invention is illustrated in FIGS. 1 and 2 .

FIG. 1 shows an example of an organic light emitting device including a substrate 1 , an anode 2 , 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 light emitting layer.

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 composed of a cathode 6 are shown. In such a structure, the compound represented by Formula 1 may be included in the light emitting layer.

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

For example, the organic light emitting device according to the present invention may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. At this time, by using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, a metal or conductive metal oxide or an alloy thereof is deposited on a substrate to form an anode. and forming an organic material layer including a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking 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 the above method, an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material from a cathode material on a substrate (WO 2003/012890). However, the manufacturing method is not limited thereto.

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

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

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

The hole injection layer is a layer for injecting holes from the electrode, and as a hole injection material, it has the ability to transport holes, so it has a hole injection effect at the anode, an excellent hole injection effect on the light emitting layer or the light emitting material, and is produced in the light emitting layer A compound which prevents the movement of excitons to the electron injection layer or the electron injection material and is excellent in the ability to form a thin film is 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 them to the light emitting layer. The hole transport material is a material that can transport holes from the anode or the hole injection layer to the light emitting layer and transfer them to the light emitting layer. material is suitable. As the hole transport material, the compound represented by Formula 1, or an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together 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 an arylamine-based organic material may be used as an example of the electron blocking material, but is not limited thereto.

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

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

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

Preferably, the 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 electron mobility and prevent excessive movement of holes to increase the 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 examples of the hole-blocking material 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. Specific examples of the electron injecting and transporting material include an 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, fluorenylidene methane, anthrone, and 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 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, fluorenylidene methane, anthrone and the like, derivatives thereof, metal complex compounds, nitrogen-containing 5-membered ring derivatives, and the like can 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 intended to illustrate 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), refluxed, and stirred. When the reaction was completed after 3 hours, it was crystallized by pouring water and filtered. After that, it was completely dissolved in ethyl acetate, washed with water, and again under reduced pressure to remove about 70% of the solvent. Hexane was added again under reflux, 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

Compound 1-1-5 (342.7 g, 1.0 eq) with Pd(t-Bu ₃ P) ₂ (8.48 g, 0.01 eq), K ₂ CO ₃ (372.6 g, 2.00 eq) with dimethylacetamide (Dimethylacetamide, 2 L) and stirred under reflux. After 2 hours, the reaction product was poured into water to crystallize and 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 placed in THF (4 L), stirred, and potassium carbonate (560 g, 4051.6 mmol) was added. After dissolving in water, stirring sufficiently, and refluxing, 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, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to 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), refluxed and stirred. When the reaction was completed after 3 hours, it was crystallized by pouring water and filtered. After that, it was completely dissolved in ethyl acetate, washed with water, and again under reduced pressure to remove about 70% of the solvent. Hexane was added again under reflux, 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) and (2-nitrophenyl) boronic acid (53.32 g, 1.1 eq) were added to THF (1 L), stirred, and potassium carbonate (97.77 g, 3.0 eq) was added with water. It was dissolved in the mixture, stirred sufficiently, and when refluxed, Pd(t-Bu ₃ P) ₂ (1.48 g, 0.01 eq) was added. After the reaction for 2 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to 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), refluxed 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, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to 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), refluxed, and stirred. When the reaction was completed after 3 hours, it was crystallized by pouring water and filtered. After that, it was completely dissolved in ethyl acetate, washed with water, and again under reduced pressure to remove about 70% of the solvent. Hexane was added again under reflux, 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

Compound 1-2-3 (252.56 g, 1.0 eq) to Pd(t-Bu ₃ P) ₂ (2.98 g, 0.01 eq), K ₂ CO ₃ (130.97 g, 2.00 eq) Dimethylacetamide (Dimethylacetamide, 2 L) and stirred under reflux. After 2 hours, the reaction product 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) and stirred, and potassium carbonate (129.66 g, 3.0 eq) was added to water. It was dissolved in the mixture, stirred sufficiently, and then refluxed. Pd(t-Bu ₃ P) ₂ (1.96 g, 0.01 eq) was added. After the reaction for 2 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to 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), refluxed 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, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain compound 1-2 (50.46 g).

(Yield 57%, MS: [M+H] ⁺ = 407)

Synthesis Example 1: Preparation of compound 1

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) in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.7 mmol) was added thereto. After 4 hours, the reaction was completed, cooled to room temperature, and reduced pressure to remove the solvent. 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 1 (7.4 g).

(Yield 31%, MS: [M+H] ⁺ = 639)

Synthesis Example 2: Preparation of compound 2

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) in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added thereto. After 3 hours, the reaction was terminated, and the solvent was removed under reduced pressure after cooling to room temperature. 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 2 (11.3 g).

(Yield 60%, MS: [M+H] ⁺ = 790)

Synthesis Example 3: Synthesis of compound 3

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) in a nitrogen atmosphere, 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 terminated, and the solvent was removed under reduced pressure after cooling to room temperature. 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 3 (8 g).

(Yield 42%, MS: [M+H] ⁺ = 777)

Synthesis Example 4: Synthesis of compound 4

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) in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added thereto. After 2 hours, the reaction was terminated, and the solvent was removed under reduced pressure after cooling to room temperature. 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 4 (9.5 g).

(Yield 46%, MS: [M+H] ⁺ = 718)

Synthesis Example 5: Synthesis of compound 5

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) in a nitrogen atmosphere, 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 terminated, and the solvent was removed under reduced pressure after cooling to room temperature. 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 5 (8 g).

(Yield 41%, MS: [M+H] ⁺ = 762)

Synthesis Example 6: Synthesis of compound 6

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) in a nitrogen atmosphere, 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 terminated, and the solvent was removed under reduced pressure after cooling to room temperature. 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 6 (8.5 g).

(Yield 43%, MS: [M+H] ⁺ = 751)

Synthesis Example 7: Synthesis of compound 7

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) in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added thereto. After 4 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under 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 7 (5.9 g).

(Yield 30%, MS: [M+H] ⁺ = 752)

Synthesis Example 8: Synthesis of compound 8

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) in a nitrogen atmosphere, and the mixture was stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added thereto. After 2 hours, the reaction was terminated, and the solvent was removed under reduced pressure after cooling to room temperature. 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 8 (6.6 g).

(Yield 35%, MS: [M+H] ⁺ = 794)

Synthesis Example 9: Synthesis of compound 9

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) in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added thereto. After 2 hours, the reaction was completed and the solvent was removed by cooling to room temperature and reducing the 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 9 (10.4 g).

(Yield 52%, MS: [M+H] ⁺ = 744)

Synthesis Example 10: Synthesis of compound 10

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) in a nitrogen atmosphere, 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 terminated, and the solvent was removed under reduced pressure after cooling to room temperature. 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 10 (8.8 g).

(Yield 45%, MS: [M+H] ⁺ = 758)

Synthesis Example 11: Synthesis of compound 11

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) in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added thereto. After 4 hours, the reaction was completed, cooled to room temperature, and reduced pressure to remove the solvent. 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 (6.1 g).

(Yield 32%, MS: [M+H] ⁺ = 774)

Synthesis Example 12: Synthesis of compound 12

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) in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added thereto. After 3 hours, the reaction was terminated, and the solvent was removed under reduced pressure after cooling to room temperature. 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 12 (8.7 g).

(Yield 41%, MS: [M+H] ⁺ = 702)

Synthesis Example 13: Synthesis of compound 13

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) in a nitrogen atmosphere, and the mixture was 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 terminated, and the solvent was removed under reduced pressure after cooling to room temperature. 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 13 (8 g).

(Yield 40%, MS: [M+H] ⁺ = 742)

Synthesis Example 14: Synthesis of compound 14

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) in a nitrogen atmosphere, and the mixture was stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added thereto. After 3 hours, the reaction was terminated, and the solvent was removed under reduced pressure after cooling to room temperature. 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 (7.7 g).

(Yield 38%, MS: [M+H] ⁺ = 728)

Synthesis Example 15: Synthesis of compound 15

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) in a nitrogen atmosphere, and 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 terminated, and the solvent was removed under reduced pressure after cooling to room temperature. 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 15 (9.3 g).

(Yield 51%, MS: [M+H] ⁺ = 817)

Synthesis Example 16: Synthesis of compound 16

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) in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added thereto. After 4 hours, the reaction was completed, cooled to room temperature, and reduced pressure to remove the solvent. 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 16 (9.7 g).

(Yield 45%, MS: [M+H] ⁺ = 689)

Synthesis Example 17: Synthesis of compound 17

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) in a nitrogen atmosphere, 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 terminated, and the solvent was removed under reduced pressure after cooling to room temperature. 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 17 (9.7 g).

(Yield 50%, MS: [M+H] ⁺ = 765)

Synthesis Example 18: Synthesis of compound 18

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) in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added thereto. After 4 hours, the reaction was completed, cooled to room temperature, and reduced pressure to remove the solvent. 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 18 (9.6 g).

(Yield 47%, MS: [M+H] ⁺ = 729)

Synthesis Example 19: Synthesis of compound 19

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) in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.8 mmol) was added thereto. After 4 hours, the reaction was completed, cooled to room temperature, and reduced pressure to remove the solvent. 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 19 (8.4 g).

(Yield 33%, MS: [M+H] ⁺ = 612)

Synthesis Example 20: Synthesis of compound 20

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) in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added thereto. After 2 hours, the reaction was terminated, and the solvent was removed under reduced pressure after cooling to room temperature. 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 (8.8 g).

(Yield 42%, MS: [M+H] ⁺ = 712)

Synthesis Example 21: Synthesis of compound 21

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) in a nitrogen atmosphere, and the mixture was stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added thereto. After 2 hours, the reaction was terminated, and the solvent was removed under reduced pressure after cooling to room temperature. 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 21 (7.8 g).

(Yield 41%, MS: [M+H] ⁺ = 777)

Synthesis Example 22: Synthesis of compound 22

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) in a nitrogen atmosphere, 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 terminated, and the solvent was removed under reduced pressure after cooling to room temperature. 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 22 (5.8 g).

(Yield 30%, MS: [M+H] ⁺ = 762)

Synthesis Example 23: Synthesis of compound 23

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) in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.5 mmol) was added thereto. After 4 hours, the reaction was completed, cooled to room temperature, and reduced pressure to remove the solvent. 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 23 (11 g).

(Yield 60%, MS: [M+H] ⁺ = 814)

Synthesis Example 24: Synthesis of compound 24

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) in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.7 mmol) was added thereto. After 2 hours, the reaction was terminated, and the solvent was removed under reduced pressure after cooling to room temperature. 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 24 (12.6 g).

(Yield 56%, MS: [M+H] ⁺ = 668)

Synthesis Example 25: Synthesis of compound 25

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) in a nitrogen atmosphere, and the mixture was 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 terminated, and the solvent was removed under reduced pressure after cooling to room temperature. 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 25 (8.9 g).

(Yield 49%, MS: [M+H] ⁺ = 820)

Synthesis Example 26: Synthesis of compound 26

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) in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added thereto. After 2 hours, the reaction was terminated, and the solvent was removed under reduced pressure after cooling to room temperature. 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 26 (7.4 g).

(Yield 38%, MS: [M+H] ⁺ = 758)

Synthesis Example 27: Synthesis of compound 27

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) in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added thereto. After 2 hours, the reaction was terminated, and the solvent was removed under reduced pressure after cooling to room temperature. 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 27 (8.5 g).

(Yield 47%, MS: [M+H] ⁺ = 833)

Synthesis Example 28: Synthesis of compound 28

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) in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.7 mmol) was added thereto. After 3 hours, the reaction was terminated, and the solvent was removed under reduced pressure after cooling to room temperature. 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 28 (10.9 g).

(Yield 47%, MS: [M+H] ⁺ = 652)

Synthesis Example 29: Synthesis of compound 29

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) in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added thereto. After 4 hours, the reaction was completed, cooled to room temperature, and reduced pressure to remove the solvent. 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 29 (7.5 g).

(Yield 37%, MS: [M+H] ⁺ = 728)

Synthesis Example 30: Synthesis of compound 30

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) in a nitrogen atmosphere, and stirred and refluxed. Thereafter, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added thereto. After 4 hours, the reaction was completed, cooled to room temperature, and reduced pressure to remove the solvent. 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 30 (6.3 g).

(Yield 32%, MS: [M+H] ⁺ = 758)

(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. At this time, a product manufactured by Fischer Co. was used as the detergent, and distilled water that was secondarily filtered with a filter manufactured by Millipore Co. was used as the distilled water. After washing ITO for 30 minutes, ultrasonic cleaning was performed for 10 minutes by repeating twice with distilled water. After washing with distilled water, ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, and after drying, it was transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

On the thus prepared ITO transparent electrode, the following HI-1 compound was formed as a hole injection layer 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 at a weight ratio of 2:1 to form an electron injection and transport layer to a thickness of 300 Å. A cathode was formed by sequentially depositing lithium fluoride (LiF) to a thickness of 12 Å and aluminum to a thickness of 1,000 Å on the electron injection and transport layer.

In the above process, the deposition rate of organic material was maintained at 0.4~0.7 Å/sec, the deposition rate of lithium fluoride of the negative electrode was maintained at 0.3 Å/sec, and the deposition rate of aluminum was maintained at 2 Å/sec, and the vacuum degree during deposition was 2X10 ^-7 To maintain ~ 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 prepared above, voltage and efficiency were measured, and the results are shown in Table 1 below. The lifetime T95 means the time required for the luminance to decrease from the 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 conventionally widely used material, and had a structure using compound EB-1 as an electron blocking layer and compound RH-1/Dp-7 as a red light emitting layer. In Comparative Examples 2 to 9, organic light emitting devices were manufactured using C-1 to C-8 instead of RH-1.

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

Claims (8)

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

In Formula 1,
R is joined at the 1st or 2nd position to form a single bond,
L is a single bond, or substituted or unsubstituted C _6-60 arylene,
Het is C _5-60 containing 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.
According to claim 1,
Formula 1 is a compound 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 defined in claim 1.
According to claim 1,
L is a single bond, phenylene, or naphthylene.
According to claim 1,
Het is any one selected from the group consisting of:

In the group,
R' is each independently, substituted or unsubstituted C _6-60 C _5-60 containing one or more heteroatoms selected from the group consisting of aryl, or substituted or unsubstituted N, O and S heteroaryl.
5. The method of claim 4,
R' is each independently phenyl, biphenylyl, naphthyl, terphenylyl, phenylnaphthyl, naphthylphenyl, phenanthrenyl, triphenylenyl, dimethylfluorenyl, dibenzofuranyl, dibenzothiophenyl , which is carbazol-9-yl or 9-phenyl-9H-carbazolyl.
According to claim 1,
R ₁ , R ₂ , R ₃ , R ₄ and R ₅ are each independently hydrogen or deuterium.
According to claim 1,
The compound represented by Formula 1 is any one selected from the group consisting of:

.

.
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.

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