KR102413614B1 - Novel compound and organic light emitting device comprising the same - Google Patents

Abstract

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

Description

Novel compound and organic light emitting device comprising the same

The present invention relates to a novel compound and an organic light emitting device 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. In the structure of the organic light emitting device, when a voltage is applied between the two electrodes, holes are injected into the organic material layer from the anode and electrons from the cathode are injected into the organic material layer. When the injected holes and electrons meet, excitons are formed, and the excitons When it falls back to the ground state, it lights up.

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

Korean Patent Publication No. 10-2013-073537

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

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

[Formula 1]

In Formula 1,

R ₁ to R ₄ are each independently hydrogen, deuterium, or substituted or unsubstituted C _6-60 aryl; or two adjacent of them may combine with each other to form a benzene ring,

R ₅ and R ₆ are each independently substituted or unsubstituted C _6-60 aryl, or substituted or unsubstituted C _5-60 containing one or more heteroatoms selected from the group consisting of N, O and S heteroaryl;

A is a substituent represented by the following formula 1A,

[Formula 1A]

In Formula 1A,

X is O or S;

Any one of R ₁₁ to R ₁₈ is connected to Formula 1,

of R ₁₁ to R ₁₈ , the remainder not connected to Formula 1 are each independently hydrogen, deuterium, or substituted or unsubstituted C _6-60 aryl; Or two adjacent of them may combine with each other to form a benzene ring.

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 as described above.

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

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

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

(Explanation of terms)

및

은 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; a phosphine oxide group; alkoxy group; aryloxy group; alkyl thiooxy group; arylthioxy group; an alkyl sulfoxy group; arylsulfoxy group; silyl group; boron group; an alkyl group; cycloalkyl group; alkenyl group; aryl group; aralkyl group; aralkenyl group; an alkylaryl group; an alkylamine group; an aralkylamine group; heteroarylamine group; arylamine group; an arylphosphine group; Or N, O, and S atom means that it is substituted or unsubstituted with one or more substituents selected from the group consisting of a heterocyclic group containing one or more, 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 in the carbonyl group is not particularly limited, but preferably 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.

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

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

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

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

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

In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the number of carbon atoms in the alkyl group is 1 to 20. According to another exemplary embodiment, the number of carbon atoms in the alkyl group is 1 to 10. 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 above-described examples of the alkenyl group. In the present specification, the description of the above-described aryl group may be applied, except that arylene is a divalent group. In the present specification, the description of the above-described heterocyclic group may be applied, except that heteroarylene is a divalent group. In the present specification, the hydrocarbon ring is not a monovalent group, and the description of the above-described aryl group or cycloalkyl group may be applied, except that it is formed by combining two substituents. In the present specification, the heterocyclic group is not a monovalent group, and the description of the above-described heterocyclic group may be applied, except that it is formed by combining two substituents.

(compound)

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

The compound represented by Formula 1 has a structure in which a benzocarbazolyl-based substituent and a triazine-based substituent are connected to the para position of the phenylene linker, and an additional A substituent (di It has a structure containing benzofuranyl, dibenzothiophenyl). Here, the phenylene linker does not include additional substituents other than the benzocarbazolyl-based substituent, the triazine-based substituent, and the A substituent, that is, the remaining carbon of the phenylene linker refers to a structure in which hydrogen is substituted. Due to this structure, the compound represented by Formula 1 has high stability to electrons and holes, and can stably maintain the balance of electrons and holes. When the compound of the present invention is employed as a light emitting layer in an organic light emitting device, it is preferable because it can exhibit characteristics of low driving voltage, high efficiency and long life.

Meanwhile, in Formula 1, A is a substituent represented by Formula 1A, and in Formula 1A, any one of R ₁₁ to R ₁₈ is connected to Formula 1 (connected to a phenylene linker), and in this case, Formula 1 is represented by Formula 1- It is represented by any one of 1 to 1-4:

[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

In Formulas 1-1 to 1-4,

X, R ₁ to R ₆ and R ₁₁ to R ₁₈ are as defined above.

Preferably, among R ₁₁ to R ₁₈ in Formula 1A, the remainder not connected to Formula 1 are each independently hydrogen, deuterium or phenyl; or adjacent two of them combine with each other to form a benzene ring.

Meanwhile, in Formula 1A, the fact that two adjacent ones of R ₁₁ to R ₁₈ that are not connected with Formula 1 combine with each other to form a benzene ring means that, for example, when R ₁₁ is connected with Formula 1, R ₁₂ and R ₁₃ are or R ₁₃ and R ₁₄ are bonded, R ₁₅ and R ₁₆ are bonded, R ₁₆ and R ₁₇ are bonded, or R ₁₇ and R ₁₈ are bonded to form a benzene ring. Even when other substituents are connected to Chemical Formula 1, two adjacent ones of the remaining groups may form a benzene ring in a similar manner. Preferably, the remainder without the formation of a benzene ring is all hydrogen.

Preferably, formula 1A is any one selected from the group consisting of:

은 화학식 1에 연결되는 결합을 의미하고,In the formula,

means a bond connected to Formula 1,

R" is each independently hydrogen, deuterium or substituted or unsubstituted C _6-60 aryl,

m is an integer from 1 to 7.

Preferably, each R″ is independently hydrogen or phenyl.

Preferably, m is 1 or 2.

Meanwhile, in Formula 1, when adjacent two of R ₁ to R ₄ are bonded to each other to form a benzene ring, specifically, R ₁ and R ₂ are bonded, R ₂ and R ₃ are bonded, or R ₃ and R ₄ combine to form a benzene ring. Preferably, the remainder without the formation of a benzene ring is all hydrogen.

For example, when two adjacent ones of R ₁ to R ₄ combine with each other to form a benzene ring, Formula 1 is represented by any one of compounds represented by Formulas 2-1 to 2-4:

[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Formula 2-4]

In Formulas 2-1 to 2-4,

R' is each independently hydrogen, deuterium, or substituted or unsubstituted C _6-60 aryl,

n is an integer from 0 to 4,

A, R ₅ and R ₆ are as defined above.

Preferably, R' is hydrogen or phenyl.

Preferably, R ₅ and R ₆ are each independently, phenyl, biphenylyl, terphenylyl, naphthyl, phenanthrenyl, anthracenyl, triphenylenyl, dibenzofuranyl, dibenzothiophenyl, carba zol-9-yl, or 9-phenyl-9H-carbazolyl.

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

.

.

The compound represented by Chemical Formula 1 may be prepared by a preparation method as shown in Scheme 1:

[Scheme 1]

In Scheme 1, R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ and A are as defined in Formula 1, and X is halogen, preferably chloro or bromo.

The reaction scheme is a Suzuki coupling reaction, and reaction conditions such as reactants, catalysts, and solvents used in the reaction may be appropriately changed depending on the type and position of the substituent of Formula 1 of the present invention.

(organic light emitting element)

In addition, the present invention provides an organic light emitting device comprising the compound represented by Formula 1 above. 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 layer of the organic material layer includes the compound represented by Formula 1 above. do. In this case, when the first electrode is an anode, the second electrode is a cathode, and when the first electrode is a cathode, the second electrode is an anode.

Specifically, the organic light emitting device may be a normal type organic light emitting device in which an anode, a light emitting layer, and a cathode are sequentially stacked on a substrate. Alternatively, the organic light emitting device may be an inverted organic light emitting device in which a cathode, a light emitting layer, and an anode are sequentially stacked on a substrate.

The organic material layer of the organic light emitting device of the present invention may have a single-layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, an electron suppression layer, a light emitting layer, a hole blocking layer, an electron injection and transport layer 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.

The structure of an organic light emitting diode 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 including a substrate 1 , an anode 2 , a light emitting layer 3 , and a cathode 4 . In such a structure, the compound represented by Formula 1 may be included in the light emitting layer.

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

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

In addition, the compound represented by Formula 1 may be formed 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, spray method, roll coating, and the like, but is not limited thereto.

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

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

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

The cathode material is preferably a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the anode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; and a 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, and conductive polymers of polyaniline and polythiophene series, 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. As a hole transport material, a material capable of transporting holes from the anode or hole injection layer to the light emitting layer and transferring them to the light emitting layer. This is suitable. Specific examples include, but are not limited to, an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together.

The light emitting layer is a layer in which the holes and electrons transported from the hole transport layer and the electron transport layer are combined to emit light in the visible ray region. The compound represented by Formula 1 is used as a host material in the emission layer.

The light emitting material is a material capable of emitting light in the visible ray region by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq ₃ ); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compounds; compounds of the benzoxazole, benzthiazole and benzimidazole series; Poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; polyfluorene, rubrene, and the like, but is not limited thereto.

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

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

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

The electron suppression layer is formed on the hole transport layer, preferably provided in contact with the light emitting layer, adjusts hole mobility, prevents excessive movement of electrons, and increases the hole-electron coupling probability, thereby increasing the efficiency of the organic light emitting device It means a layer that plays a role in improving The electron blocking layer includes an electron blocking material, and as an example of the electron blocking material, a compound represented by Formula 1 or an arylamine-based organic material may be used, but is not limited thereto.

The 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, thereby improving the efficiency of the organic light emitting device layer that plays a role. 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 transport layer is a layer that receives electrons from the electron injection layer and transports them to the light emitting layer. do. Specific examples include Al complex of 8-hydroxyquinoline; complexes containing Alq ₃ ; organic radical compounds; hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transport layer may be used with any desired cathode material as used in accordance with the prior art. In particular, examples of suitable cathode materials are conventional materials having a low work function and followed by a layer of aluminum or silver. Specifically cesium, barium, calcium, ytterbium and samarium, followed in each case by an aluminum layer or a silver layer.

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

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

On the other hand, the electron transport layer and the electron injection layer can be provided in the form of an electron injection and transport layer that simultaneously performs the roles of the electron transport layer and the electron injection layer for transporting the received electrons to the light emitting layer.

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.

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.

Preparation Example 1: Synthesis of the core structure

Preparation Example 1-1: Synthesis of compound a

1) Preparation of compound a-1

naphthalen-2-amine 300.0 g (1.0 eq), 1-bromo-2-iodobenzene 592.7 g (1.0 eq), NaOtBu 302.0 g (1.5 eq), Pd(OAc) ₂ 4.70 g (0.01 eq), Xantphos 12.12 g ( 0.01 eq), dissolved in 1,4-dioxane 5L, refluxed, and stirred. When the reaction was completed after 3 hours, the solvent was removed under reduced pressure. After that, it was completely dissolved in ethylacetate, washed with water, and again under reduced pressure to remove about 70% of the solvent. Hexane was added under reflux again, crystals were dropped, cooled, and filtered. This was subjected to column chromatography to obtain 443.5 g of compound a-1. (Yield 71%, MS: [M+H] ⁺ = 299)

2) Preparation of compound a (5H-benzo[b]carbazole)

Compound a-1 443.5 g (1.0 eq) of Pd(t-Bu ₃ P) ₂ 8.56 g (0.01 eq), K ₂ CO ₃ 463.2 g (2.00 eq) was put in 4L of diethylacetamide (Dimethylacetamide) and refluxed. stirred. After 3 hours, the reaction product was poured into water to drop crystals and filtered. The filtered solid was completely dissolved in 1,2-dichlorobenzene, 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 174.8 g of compound a (5H-benzo[b]carbazole). (Yield 48%, MS: [M+H] ⁺ = 218)

Preparation 1-2: Synthesis of compound b

The following compound b (7H-dibenzo[b,g]carbazole) was synthesized in the same manner as in the preparation of compound a using 1-bromo-2-iodonaphthalene instead of 1-bromo-2-iodobenzene. (MS: [M+H] ⁺ = 268)

Preparation Example 1-3: Synthesis of compound c

Compound c (6H-dibenzo[b,h]carbazole) was synthesized in the same manner as in the preparation of the compound using 2,3-dibromonaphthalene instead of 1-bromo-2-iodobenzene. (MS: [M+H] ⁺ = 268)

Preparation Example 1-4: Synthesis of compound d

Compound d (13H-dibenzo[a,h]carbazole) was synthesized in the same manner as in the preparation of compound a, using 2-bromo-1-iodonaphthalene instead of 1-bromo-2-iodobenzene.

MS: [M+H] ⁺ = 268

Preparation Example 2: Synthesis of intermediate compound

Preparation 2-1: Synthesis of intermediate compound A

1) Synthesis of intermediate compound 1-a

2-chloro-4-(naphthalen-2-yl)-6-phenyl-1,3,5-triazine (30 g, 94.4 mmol) and (2-bromo-4-chlorophenyl) boronic acid (24.4 g, 103.8 mmol) was put in 600ml of THF and stirred, and potassium carbonate (52.2g, 377.6mmol) was dissolved in water and added. After the mixture was sufficiently stirred and refluxed, bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.9 mmol) was added thereto. 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, and the intermediate compound 1-a (2-(2-bromo-4-chlorophenyl)-4-(naphthalen-2-yl)-6-phenyl-1,3,5- triazine) was prepared in 31.2 g. (yield 70%)

MS: [M+H] ⁺ = 474

2) Synthesis of intermediate compound A

Intermediate compound 1-a (31.2 g, 66 mmol) and 2-(dibenzo[b,d]furan-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (19.4 g, 66 mmol) ) was added to 624ml of THF, stirred, and potassium carbonate (36.5g, 264mmol) was dissolved in water, stirred sufficiently, refluxed, and then bis(tri-tert-butylphosphine)palladium(0) (0.3g, 0.7mmol) was added. did After the reaction for 3 hours, it was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled. This was again dissolved in chloroform, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to prepare 23.3 g of intermediate compound A. (Yield 63%)

MS: [M+H] ⁺ = 561

Preparation Example 2-2: Synthesis of intermediate compounds B to Y

The following intermediate compounds B to Y were synthesized in the same manner as in Preparation Example 2-1, except that reactants having different types of substituents were used in Preparation Example 2-1.

Preparation Example 3: Synthesis of a compound represented by Formula 1 herein

Preparation 3-1: Synthesis of Compound 1

Intermediate compound A (20 g, 35.7 mmol), compound a (7.8 g, 35.7 mmol), and sodium tert-butoxide (6.9 g, 71.4 mmol) were added to 400 ml of Xylene in a nitrogen atmosphere, and stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.7 mmol) was added. After the reaction was completed after 3 hours, it was cooled to room temperature and the solvent was removed under reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 16.1 g of Compound 1. (Yield 61%, MS: [M+H] ⁺ = 742)

Preparation 3-2: Synthesis of compound 2

Intermediate compound B (20 g, 33.3 mmol), compound a (7.2 g, 33.3 mmol), and sodium tert-butoxide (6.4 g, 66.7 mmol) were added to 400 ml of Xylene in a nitrogen atmosphere, and stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.7 mmol) was added. After the reaction was completed after 3 hours, it was cooled to room temperature and the solvent was removed under reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 14.1 g of Compound 2. (Yield 54%, MS: [M+H] ⁺ = 782)

Preparation 3-3: Synthesis of compound 3

In a nitrogen atmosphere, the intermediate compound C (20 g, 28.9 mmol), compound a (6.3 g, 28.9 mmol), and sodium tert-butoxide (5.6 g, 57.9 mmol) were added to 400 ml of Xylene, followed by stirring and reflux. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After the reaction was completed after 3 hours, it was cooled to room temperature and the solvent was removed under reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 16.4 g of Compound 3. (Yield 65%, MS: [M+H] ⁺ = 873)

Preparation 3-4: Synthesis of compound 4

In a nitrogen atmosphere, the intermediate compound D (20 g, 30.8 mmol), compound a (6.7 g, 30.8 mmol), and sodium tert-butoxide (5.9 g, 61.5 mmol) were added to 400 ml of Xylene, followed by stirring and reflux. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After the reaction was completed after 3 hours, it was cooled to room temperature and the solvent was removed under reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 15.1 g of Compound 4. (yield 59%, MS: [M+H] ⁺ = 832)

Preparation 3-5: Synthesis of compound 5

In a nitrogen atmosphere, the intermediate compound E (20 g, 27.5 mmol), compound a (6 g, 27.5 mmol), and sodium tert-butoxide (5.3 g, 54.9 mmol) were added to 400 ml of Xylene, followed by stirring and reflux. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After the reaction was completed after 3 hours, it was cooled to room temperature and the solvent was removed under reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 16.2 g of compound 5. (Yield 65%, MS: [M+H] ⁺ = 910)

Preparation 3-6: Synthesis of compound 6

Intermediate compound F (20 g, 30 mmol), compound a (6.5 g, 30 mmol), and sodium tert-butoxide (5.8 g, 60 mmol) were added to 400 ml of Xylene in a nitrogen atmosphere, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After the reaction was completed after 3 hours, it was cooled to room temperature and the solvent was removed under reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 17.3 g of compound 6. (Yield 68%, MS: [M+H] ⁺ = 848)

Preparation 3-7: Synthesis of compound 7

In a nitrogen atmosphere, the intermediate compound G (20 g, 30.7 mmol), compound a (6.7 g, 30.7 mmol), and sodium tert-butoxide (5.9 g, 61.3 mmol) were added to 400 ml of Xylene, followed by stirring and reflux. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After the reaction was completed after 3 hours, it was cooled to room temperature and the solvent was removed under reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 12.3 g of Compound 7. (Yield 48%, MS: [M+H] ⁺ = 834)

Preparation 3-8: Synthesis of compound 8

In a nitrogen atmosphere, the intermediate compound H (20 g, 30.8 mmol), compound a (6.7 g, 30.8 mmol), and sodium tert-butoxide (5.9 g, 61.5 mmol) were added to 400 ml of Xylene, followed by stirring and reflux. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After the reaction was completed after 3 hours, it was cooled to room temperature and the solvent was removed under reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 12.3 g of compound 8. (Yield 48%, MS: [M+H] ⁺ = 832)

Preparation 3-9: Synthesis of compound 9

In a nitrogen atmosphere, the intermediate compound I (20 g, 32.8 mmol), compound a (7.1 g, 32.8 mmol), and sodium tert-butoxide (6.3 g, 65.6 mmol) were added to 400 ml of Xylene, followed by stirring and reflux. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.7 mmol) was added. After the reaction was completed after 3 hours, it was cooled to room temperature and the solvent was removed under reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 15.6 g of compound 9. (yield 60%, MS: [M+H] ⁺ = 792)

Preparation 3-10: Synthesis of compound 10

In a nitrogen atmosphere, the intermediate compound J (20 g, 29.3 mmol), compound a (6.4 g, 29.3 mmol), and sodium tert-butoxide (5.6 g, 58.6 mmol) were added to 400 ml of Xylene, followed by stirring and reflux. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After the reaction was completed after 3 hours, it was cooled to room temperature and the solvent was removed under reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 16.2 g of compound 10. (Yield 64%, MS: [M+H] ⁺ = 864)

Preparation 3-11: Synthesis of compound 11

In a nitrogen atmosphere, the intermediate compound K (20 g, 27.1 mmol), compound a (5.9 g, 27.1 mmol), and sodium tert-butoxide (5.2 g, 54.2 mmol) were added to 400 ml of Xylene, followed by stirring and reflux. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.5 mmol) was added. After the reaction was completed after 3 hours, it was cooled to room temperature and the solvent was removed under reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 10 g of compound 11. (Yield 40%, MS: [M+H] ⁺ = 920)

Preparation 3-12: Synthesis of compound 12

In a nitrogen atmosphere, the intermediate compound L (20 g, 27.5 mmol), compound a (6 g, 27.5 mmol), and sodium tert-butoxide (5.3 g, 55.1 mmol) were added to 400 ml of Xylene, followed by stirring and reflux. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After the reaction was completed after 3 hours, it was cooled to room temperature and the solvent was removed under reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 17.5 g of Compound 12. (Yield 70%, MS: [M+H] ⁺ = 908)

Preparation 3-13: Synthesis of compound 13

In a nitrogen atmosphere, the intermediate compound M (20 g, 29 mmol), compound a (6.3 g, 29 mmol), and sodium tert-butoxide (5.6 g, 58 mmol) were added to 400 ml of Xylene, followed by stirring and reflux. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After the reaction was completed after 3 hours, it was cooled to room temperature and the solvent was removed under reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 15.4 g of compound 13. (Yield 61%, MS: [M+H] ⁺ = 872)

Preparation 3-14: Synthesis of compound 14

In a nitrogen atmosphere, the intermediate compound N (20 g, 28.3 mmol), compound c (7.6 g, 28.3 mmol), and sodium tert-butoxide (5.4 g, 56.6 mmol) were added to 400 ml of Xylene, followed by stirring and reflux. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After the reaction was completed after 3 hours, it was cooled to room temperature and the solvent was removed under reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 11.7 g of compound 14. (Yield 44%, MS: [M+H] ⁺ = 938)

Preparation 3-15: Synthesis of compound 15

In a nitrogen atmosphere, the intermediate compound O (20 g, 38 mmol), compound c (10.2 g, 38 mmol), and sodium tert-butoxide (7.3 g, 76 mmol) were added to 400 ml of Xylene, followed by stirring and reflux. After that, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.8 mmol) was added. After the reaction was completed after 3 hours, it was cooled to room temperature and the solvent was removed under reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 15 g of compound 15. (Yield 52%, MS: [M+H] ⁺ = 758)

Preparation 3-16: Synthesis of compound 16

Intermediate compound P (20 g, 29 mmol), 1-phenyl-5H-benzo[b]carbazole (8.5 g, 29 mmol), sodium tert-butoxide (5.6 g, 58 mmol) in 400 ml of Xylene under nitrogen atmosphere, stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After the reaction was completed after 3 hours, it was cooled to room temperature and the solvent was removed under reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 14.5 g of compound 16. (Yield 53%, MS: [M+H] ⁺ = 948)

Preparation 3-17: Synthesis of compound 17

Intermediate compound Q (20 g, 31.9 mmol), 1-phenyl-5H-benzo[b]carbazole (9.4 g, 31.9 mmol), and sodium tert-butoxide (6.1 g, 63.9 mmol) were added to 400 ml of Xylene and stirred in a nitrogen atmosphere. and reflux. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After the reaction was completed after 3 hours, it was cooled to room temperature and the solvent was removed under reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 17.5 g of compound 17. (Yield 62%, MS: [M+H]+= 884)

Preparation 3-18: Synthesis of compound 18

In a nitrogen atmosphere, the intermediate compound R (20 g, 30.2 mmol), compound d (8.1 g, 30.2 mmol), and sodium tert-butoxide (5.8 g, 60.4 mmol) were added to 400 ml of Xylene, followed by stirring and reflux. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After the reaction was completed after 3 hours, it was cooled to room temperature and the solvent was removed under reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 15.6 g of compound 18. (Yield 58%, MS: [M+H] ⁺ = 894)

Preparation 3-19: Synthesis of compound 19

In a nitrogen atmosphere, the intermediate compound S (20 g, 31.9 mmol), compound d (8.5 g, 31.9 mmol), and sodium tert-butoxide (6.1 g, 63.9 mmol) were added to 400 ml of Xylene, followed by stirring and reflux. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After the reaction was completed after 3 hours, it was cooled to room temperature and the solvent was removed under reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 18.1 g of compound 19. (Yield 66%, MS: [M+H] ⁺ = 858)

Preparation 3-20: Synthesis of compound 20

In a nitrogen atmosphere, the intermediate compound T (20 g, 38 mmol), compound b (10.2 g, 38 mmol), and sodium tert-butoxide (7.3 g, 76 mmol) were added to 400 ml of Xylene, followed by stirring and reflux. After that, bis(tri-tert-butylphosphine)palladium(0) (0.4 g, 0.8 mmol) was added. After the reaction was completed after 3 hours, it was 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 17.6 g of compound 20. (Yield 61%, MS: [M+H] ⁺ = 758)

Preparation 3-21: Synthesis of compound 21

In a nitrogen atmosphere, the intermediate compound U (20 g, 32.8 mmol), compound b (8.8 g, 32.8 mmol), and sodium tert-butoxide (6.3 g, 65.6 mmol) were added to 400 ml of Xylene, followed by stirring and reflux. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.7 mmol) was added. After the reaction was completed after 3 hours, it was cooled to room temperature and the solvent was removed under reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 13.2 g of compound 21. (Yield 48%, MS: [M+H] ⁺ = 842)

Preparation 3-22: Synthesis of compound 22

In a nitrogen atmosphere, the intermediate compound V (20 g, 29.6 mmol), compound a (6.4 g, 29.6 mmol), and sodium tert-butoxide (5.7 g, 59.2 mmol) were added to 400 ml of Xylene, followed by stirring and reflux. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After the reaction was completed after 3 hours, it was 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 15.7 g of compound 22. (Yield 62%, MS: [M+H] ⁺ = 857)

Preparation 3-23: Synthesis of compound 23

In a nitrogen atmosphere, the intermediate compound W (20 g, 29.6 mmol), compound a (6.4 g, 29.6 mmol), and sodium tert-butoxide (5.7 g, 59.2 mmol) were added to 400 ml of Xylene, followed by stirring and reflux. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After the reaction was completed after 3 hours, it was cooled to room temperature and the solvent was removed under reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 11.4 g of compound 23. (Yield 45%, MS: [M+H] ⁺ = 858)

Preparation 3-24: Synthesis of compound 24

Intermediate compound X (20 g, 28.9 mmol), compound a (6.3 g, 28.9 mmol), and sodium tert-butoxide (5.6 g, 57.9 mmol) were added to 400 ml of Xylene in a nitrogen atmosphere, and stirred and refluxed. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After the reaction was completed after 3 hours, it was 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 11.4 g of Compound 24. (Yield 45%, MS: [M+H] ⁺ = 873)

Preparation 3-25: Synthesis of compound 25

In a nitrogen atmosphere, the intermediate compound Y (20 g, 32.8 mmol), compound a (7.1 g, 32.8 mmol), and sodium tert-butoxide (6.3 g, 65.6 mmol) were added to 400 ml of Xylene, followed by stirring and reflux. After that, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.7 mmol) was added. After the reaction was completed after 3 hours, it was cooled to room temperature and the solvent was removed under reduced pressure. After that, the compound was completely dissolved again in chloroform, washed twice with water, the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 10.9 g of compound 25. (Yield 42%, MS: [M+H] ⁺ = 792)

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 in a weight ratio of 98:2 on the EB-1 deposited layer 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, the following ET-1 compound and the following LiQ compound were vacuum deposited on the hole blocking layer 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 0.4~0.7Å/sec, the deposition rate of lithium fluoride of the negative electrode was maintained at 0.3Å/sec, and the deposition rate of aluminum was maintained at 2Å/sec, and the vacuum degree during deposition was 2×10 ^-7 ~ By maintaining 5×10 ^-6 torr, an organic light emitting diode was manufactured.

Examples 1 to 25 and Comparative Examples 2 to 13

An organic light emitting device was manufactured in the same manner as in Comparative Example 1, except that the compound shown in Table 1 below was used instead of RH-1 for the light emitting layer in the organic light emitting device of Comparative Example 1. The following compounds of C-1 to C-12 are compounds used in Comparative Examples 2 to 13.

Experimental example

By applying a current to the organic light emitting devices of Examples 1 to 25 and Comparative Examples 1 to 13, voltage and efficiency were measured (10 mA/cm ² ), 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 light emitting layer
matter Driving voltage (V) Efficiency (cd/A) Life T95 (hr) luminous color Comparative Example 1 RH-1 4.12 21.1 133 Red Example 1 compound 1 3.60 25.5 181 Red Example 2 compound 2 3.61 24.7 170 Red Example 3 compound 3 3.64 25.8 167 Red Example 4 compound 4 3.62 26.1 168 Red Example 5 compound 5 3.73 26.5 176 Red Example 6 compound 6 3.70 25.3 161 Red Example 7 compound 7 3.71 24.9 188 Red Example 8 compound 8 3.61 25.5 177 Red Example 9 compound 9 3.60 26.3 163 Red Example 10 compound 10 3.65 25.1 162 Red Example 11 compound 11 3.63 25.8 177 Red Example 12 compound 12 3.68 24.3 189 Red Example 13 compound 13 3.64 26.9 175 Red Example 14 compound 14 3.51 28.1 227 Red Example 15 compound 15 3.50 29.0 234 Red Example 16 compound 16 3.49 28.2 217 Red Example 17 compound 17 3.52 29.6 210 Red Example 18 compound 18 3.47 27.9 223 Red Example 19 compound 19 3.50 28.1 230 Red Example 20 compound 20 3.48 28.5 214 Red Example 21 compound 21 3.53 29.6 208 Red Example 22 compound 22 3.71 26.3 175 Red Example 23 compound 23 3.67 25.7 151 Red Example 24 compound 24 3.69 26.5 187 Red Example 25 compound 25 3.65 25.3 174 Red Comparative Example 2 C-1 3.85 20.1 105 Red Comparative Example 3 C-2 3.80 20.9 118 Red Comparative Example 4 C-3 4.01 20.1 109 Red Comparative Example 5 C-4 3.95 19.3 84 Red Comparative Example 6 C-5 4.51 15.2 15 Red Comparative Example 7 C-6 4.57 15.8 24 Red Comparative Example 8 C-7 4.69 14.2 18 Red Comparative Example 9 C-8 4.39 13.4 57 Red Comparative Example 10 C-9 4.11 21.6 84 Red Comparative Example 11 C-10 4.15 22.5 79 Red Comparative Example 12 C-11 4.39 15.7 21 Red Comparative Example 13 C-12 4.31 18.6 46 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 suppressing layer and RH-1/Dp-7 as a red light emitting layer. In Comparative Examples 2 to 13, organic light emitting devices were manufactured using C-1 to C-12 instead of RH-1.

Looking at the results of Table 1, the compound of the present invention has high stability to electrons and holes, so that when applied as a host of a red light emitting layer, the driving voltage is significantly lower than that of the material used in the comparative example, and it was confirmed that it was excellent in terms of efficiency. . Accordingly, it was confirmed that the energy transfer from the host to the red dopant was excellent when the compound of the present application was used. In addition, it was confirmed that, when the compound of the present application was used, the lifespan characteristics could be improved by up to 2 times or more while maintaining high efficiency.

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

Claims (7)

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

In Formula 1,
R ₁ to R ₄ are each independently hydrogen, deuterium, or substituted or unsubstituted C _6-60 aryl; or two adjacent of them may combine with each other to form a benzene ring,
R ₅ and R ₆ are each independently substituted or unsubstituted C _6-60 aryl, or substituted or unsubstituted C _5-60 containing one or more heteroatoms selected from the group consisting of N, O and S heteroaryl;
A is a substituent represented by the following formula 1A,
[Formula 1A]

In Formula 1A,
X is O or S;
Any one of R ₁₁ to R ₁₈ is connected to Formula 1,
of R ₁₁ to R ₁₈ , the remainder not connected to Formula 1 are each independently hydrogen, deuterium, or substituted or unsubstituted C _6-60 aryl; Or two adjacent of them may combine with each other to form a benzene ring.
The method of claim 1,
The compound represented by Formula 1 is a compound represented by any one of the following Formulas 1-1 to 1-4:
[Formula 1-1]

[Formula 1-2]

[Formula 1-3]

[Formula 1-4]

In Formulas 1-1 to 1-4,
X, R ₁ to R ₆ and R ₁₁ to R ₁₈ are as defined in claim 1.
The method of claim 1,
The compound represented by Formula 1 is a compound represented by any one of the following Formulas 2-1 to 2-4:
[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Formula 2-4]

In Formulas 2-1 to 2-4,
R' is each independently hydrogen, deuterium, or substituted or unsubstituted C _6-60 aryl,
n is an integer from 1 to 4,
A, R ₅ and R ₆ are as defined in claim 1.
The method of claim 1,
R ₅ and R ₆ are each independently phenyl, biphenylyl, terphenylyl, naphthyl, phenanthrenyl, anthracenyl, triphenylenyl, dibenzofuranyl, dibenzothiophenyl, carbazol-9-yl or 9-phenyl-9H-carbazolyl.
The method of claim 1,
Formula 1A is any one selected from the group consisting of, the compound:

In the formula,
R" is each independently hydrogen, deuterium or substituted or unsubstituted C _6-60 aryl,
m is an integer from 1 to 7.
The method of 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 organic material layer includes the compound according to any one of claims 1 to 6 which is an organic light emitting device.

Images