Novel compound and organic light-emitting device containing the same

Abstract

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

Description

[Technical field]

[0001] [CROSS REFERENCE TO RELATED APPLICATIONS] This application claims the benefit of priority to Korean Patent Application No. 10-2021-0030417 dated March 8, 2021, and all contents disclosed in the documents of that Korean patent application are incorporated herein by reference.

[0002] The present invention relates to a novel compound and an organic light-emitting device containing the same. [Background technology]

[0003] Generally, organic light emitting phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material. Organic light emitting devices using the organic light emitting phenomenon have a wide viewing angle, excellent contrast, and fast response time, and are excellent in brightness, driving voltage, and response speed characteristics, and therefore many researches are being conducted on them.

[0004] An organic light-emitting device generally has a structure including a positive electrode, a negative electrode, and an organic layer between the positive electrode and the negative electrode. The organic layer is often a multi-layer structure composed of different materials to improve the efficiency and safety 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, etc. When a voltage is applied between the two electrodes in such an organic light-emitting device structure, holes are injected from the positive electrode and electrons are injected from the negative electrode into the organic layer. When the injected holes and electrons come into contact with each other, excitons are formed, and when the excitons fall back to the ground state, light is emitted.

[0005] There is a continuing demand for the development of new organic materials for use in such organic light-emitting devices. [Prior art documents] [Patent documents]

[0006] [Patent Document 1] Korean Patent Publication No. 10-2000-0051826 [Patent Document 2] U.S. Patent Publication No. 2007-0196692 [Patent Document 3] Korean Patent Publication No. 10-2017-0048159 [Patent Document 4] U.S. Patent Registration No. 6821643 Summary of the Invention [Problem to be solved by the invention]

[0007] The present invention relates to a novel compound and an organic light-emitting device containing the same. [Means for solving the problem]

[0008] The present invention provides a compound represented by the following formula 1 or formula 2: [Chemical formula 1] [ka] [Chemical formula 2] [ka] In the above Chemical Formula 1 or Chemical Formula 2, R1 to R4 are each independently hydrogen or deuterium; n1 to n4 are integers from 1 to 4, L1 and L2 each independently represent a direct bond; or a substituted or unsubstituted arylene having 6 to 60 carbon atoms; Ar1 and Ar2 are each independently a substituent represented by the following chemical formula 3. [Chemical formula 3] [ka] In the above Chemical Formula 3, X1 to X5 each independently represent N or C(R5), and at least two of X1 to X5 represent N; Each R5 is independently hydrogen, deuterium, a substituted or unsubstituted alkyl having 1 to 20 carbon atoms, a substituted or unsubstituted aryl having 6 to 60 carbon atoms, or a heteroaryl having 2 to 60 carbon atoms containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O, and S, or two adjacent R5s among these are bonded to form a benzene ring.

[0009] The present invention also provides an organic light-emitting device comprising: a first electrode; a second electrode provided opposite to the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein at least one of the organic layers comprises at least one of the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2. Effect of the Invention

[0010] The compound represented by the above Chemical Formula 1 or Chemical Formula 2 is used as a material for an organic layer of an organic light-emitting device, and can improve the efficiency, low driving voltage, and / or life characteristics of the organic light-emitting device. In particular, the compound represented by the above Chemical Formula 1 is used as a hole injection, hole transport, hole injection and transport, light-emitting, electron transport, or electron injection material. [Brief description of the drawings]

[0011] [Figure 1] FIG. 1 is a diagram showing an example of an organic light-emitting element composed of a substrate 1, a positive electrode 2, a light-emitting layer 3, and a negative electrode 4. [Diagram 2] FIG. 1 shows an example of an organic light-emitting device consisting of a substrate 1, a positive electrode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 7, an electron transport and injection layer 8, and a negative electrode 4. [Diagram 3] FIG. 1 shows an example of an organic light-emitting device consisting of a substrate 1, a positive electrode 2, a hole injection layer 5, a hole transport layer 6, an electron inhibiting layer 9, a light-emitting layer 7, a hole blocking layer 10, an electron transport and injection layer 8, and a negative electrode 4. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0012] The present invention will now be described in more detail to aid in understanding the invention.

[0013] In the present invention, [ka] denotes a bond that is connected to another substituent.

[0014] In the present invention, the term "substituted or unsubstituted" means that the group is substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium; halogen group; nitrile group; nitro group; hydroxy group; carbonyl group; ester group; imide group; amino group; phosphine oxide group; alkoxy group; aryloxy group; alkylthiooxy group; arylthiooxy group; alkylsulfoxy group; arylsulfoxy group; silyl group; boron group; alkyl group; cycloalkyl group; alkenyl group; aryl group; aralkyl group; aralkenyl group; alkylaryl group; alkylamine group; aralkylamine group; heteroarylamine group; arylamine group; arylphosphine group; or heterocyclic group containing one or more of N, O and S atoms, or that the group is substituted or unsubstituted with two or more of the above-mentioned exemplified substituents connected to each other. For example, the "substituent having two or more substituents connected to each other" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent having two phenyl groups connected to each other.

[0015] In the present invention, the number of carbon atoms in the carbonyl group is not particularly limited, but is preferably 1 to 40. Specifically, the carbonyl group may have a structure as shown below, but is not limited thereto. [ka]

[0016] In the present specification, 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, the ester group may be a compound having the following structural formula, but is not limited thereto. [ka]

[0017] In this specification, the number of carbon atoms of the imido group is not particularly limited, but is preferably 1 to 25. Specifically, the imido group may have a structure as shown below, but is not limited thereto. [ka]

[0018] In this specification, specific examples of the silyl group include a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, and a phenylsilyl group, but are not limited to these.

[0019] In this specification, specific examples of the boron group include a trimethyl boron group, a triethyl boron group, a t-butyl dimethyl boron group, a triphenyl boron group, and a phenyl boron group, but are not limited to these.

[0020] In this specification, examples of halogen groups include fluorine, chlorine, bromine or iodine.

[0021] In this 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 one embodiment, the number of carbon atoms of the alkyl group is 1 to 20. According to yet another embodiment, the number of carbon atoms of the alkyl group is 1 to 10. According to yet another embodiment, the number of carbon atoms of the alkyl group is 1 to 6. Specific examples of alkyl groups include, but are not limited to, 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.

[0022] In this 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 one embodiment, the number of carbon atoms of the alkenyl group is 2 to 20. According to yet another embodiment, the number of carbon atoms of the alkenyl group is 2 to 10. According to yet another embodiment, the number of carbon atoms of the alkenyl group is 2 to 6. Specific examples include, but are not limited to, 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, a stilbenyl group, and a styrenyl group.

[0023] In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and in one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. In another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. In another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specific examples include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, and cyclooctyl.

[0024] 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 one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., 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, etc., but is not limited thereto.

[0025] In this specification, the fluorenyl group may be substituted, and two of the substituents may be bonded together to form a spiro structure. When the fluorenyl group is substituted, [ka] However, the present invention is not limited to these.

[0026] In this specification, the heterocyclic group is a heterocyclic group containing one or more of O, N, Si and S as a hetero element, and the number of carbon atoms is not particularly limited, but preferably has 2 to 60 carbon atoms. Examples of heterocyclic groups include, but are not limited to, thiophene, furan, pyrrole, imidazole, thiazole, oxazole, oxadiazole, triazole, pyridyl, bipyridyl, pyrimidyl, triazine, acridyl, pyridacin, pyrazinyl, quinolinyl, quinazoline, quinoxalinyl, furalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinoline, indole, carbazole, benzoxazole, benzimidazole, benzothiazole, benzocarbazole, benzothiophene, dibenzothiophene, benzofuranyl, phenanthroline, isoxazolyl, thiadiazolyl, phenothiazinyl, and dibenzofuranyl.

[0027] In this specification, the above-mentioned explanation regarding the aryl group is applicable to the aralkyl group, the aralkenyl group, the alkylaryl group, and the aryl group in the arylamine group. In this specification, the above-mentioned explanation regarding the alkyl group is applicable to the aralkyl group and the alkyl group in the alkylaryl group. In this specification, the above-mentioned explanation regarding the heterocyclic group is applicable to the heteroaryl in the heteroarylamine. In this specification, the above-mentioned explanation regarding the alkenyl group is applicable to the alkenyl group in the aralkenyl group. In this specification, the above-mentioned explanation regarding the aryl group is applicable to the arylene, except that it is a divalent group. In this specification, the above-mentioned explanation regarding the heterocyclic group is applicable to the heteroarylene, except that it is a divalent group. In this specification, the above-mentioned explanation regarding the aryl group or the cycloalkyl group is applicable to the hydrocarbon ring, except that it is not a monovalent group but is formed by bonding two substituents. In this specification, the above-mentioned explanation regarding the heterocyclic group is applicable to the heterocycle, except that it is not a monovalent group but is formed by bonding two substituents.

[0028] (compound)

[0029] The present invention provides a compound represented by Chemical Formula 1 or Chemical Formula 2.

[0030] Preferably, the formula 1 is represented by the following formula 1-1, and the formula 2 is represented by the following formula 2-1. [Chemical formula 1-1] [ka] [Chemical formula 2-1] [ka] In the above Chemical Formula 1-1 or Chemical Formula 2-1, L1, L2, Ar1, and Ar2 are as defined above. Preferably, L1 and L2 are each independently a direct bond, phenylene, or biphenyldiyl.

[0031] Preferably, Ar1 and Ar2 are each independently any one selected from the group consisting of: [ka] In the above group, R5 is as defined above.

[0032] Preferably, each R5 is independently hydrogen, deuterium, methyl, tert-butyl, phenyl, biphenylyl, terphenylyl, naphthyl, pyridinyl, furanyl, or thiophenyl, or adjacent two R5 are bonded to form a benzene ring; each of the phenyl, biphenylyl, terphenylyl, naphthyl, pyridinyl, furanyl, or thiophenyl is independently unsubstituted or substituted with deuterium, methyl, or tert-butyl.

[0033] Preferably, Ar1 and Ar2 are each independently any one selected from the group consisting of: [ka] [ka]

[0034] Representative examples of the compounds represented by Chemical Formula 1 or Chemical Formula 2 are as follows: [ka] [ka] [ka] [ka] [ka]

[0035] The present invention also provides a method for producing the compound represented by Chemical Formula 1 or 2, as shown in the following Reaction Schemes 1 to 4. [Reaction Scheme 1] [ka] [Reaction Scheme 2] [ka] [Reaction Scheme 3] [ka] [Reaction Scheme 4] [ka] In the reaction formulas 1 to 4, L is independently L1 or L2, Ar is independently Ar1 or Ar2, R is independently any one of R1 to R4, and n is independently any one of n1 to n4. L1, L2, Ar1, Ar2, R1 to R4, and n1 to n4 are as defined above, and X is a halogen, preferably bromo or chloro.

[0036] (Organic light-emitting device)

[0037] The present invention also provides an organic light-emitting device comprising at least one of the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2. As an example, the present invention provides an organic light-emitting device comprising a first electrode, a second electrode provided opposite to 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 comprises at least one of the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2.

[0038] The organic layer of the organic light-emitting device of the present invention may have a single-layer structure, or may have a multi-layer structure in which two or more organic layers are laminated. 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 inhibiting layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. as the organic layer. However, the structure of the organic light-emitting device is not limited thereto, and may include a smaller number of organic layers.

[0039] 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 the layer that simultaneously injects and transports holes may include one or more of the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2.

[0040] In addition, the organic layer may include a light-emitting layer, and the light-emitting layer may include at least one of the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2.

[0041] In addition, the organic layer may include an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer may include any one or more of the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2.

[0042] The electron transport layer, the electron injection layer, or the layer that simultaneously injects and transports electrons may contain at least one of the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2.

[0043] The organic layer may include an electron inhibiting layer between the positive electrode and the light emitting layer. The electron inhibiting layer may include at least one of the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2.

[0044] The organic layer may include a light-emitting layer and an electron transport layer, and the electron transport layer may include at least one of the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2.

[0045] The organic layer may include a hole blocking layer between the anode and the light emitting layer. The hole blocking layer prevents holes injected from the anode from being recombined in the light emitting layer and being transferred to the anode, thereby improving the efficiency of the organic light emitting device. The hole blocking layer may include at least one of the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2.

[0046] Preferably, the organic layer is an electron transport layer, an electron injection layer, or an electron transport and injection layer.

[0047] Preferably, the electron transport layer, the electron injection layer, or the electron transport and injection layer may further comprise a compound represented by the following Chemical Formula 4: [Chemical formula 4] [ka]

[0048] In addition, the organic light emitting device according to the present invention may be an organic light emitting device having a structure (normal type) in which a positive electrode, one or more organic layers, and a negative electrode are sequentially stacked on a substrate. Furthermore, the organic light emitting device according to the present invention may be an organic light emitting device having an inverted structure (inverted type) in which a negative electrode, one or more organic layers, and a positive electrode are sequentially stacked on a substrate. For example, the structure of an organic light emitting device according to an embodiment of the present invention is shown in Figures 1 to 3.

[0049] 1 is a diagram showing an example of an organic light-emitting device consisting of a substrate 1, a positive electrode 2, a light-emitting layer 3, and a negative electrode 4. In this structure, any one or more of the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 may be contained in the light-emitting layer.

[0050] 2 is a diagram showing an example of an organic light-emitting device consisting of a substrate 1, a positive electrode 2, a hole injection layer 5, a hole transport layer 6, an emitting layer 7, an electron transport and injection layer 8, and a negative electrode 4. In this structure, any one or more of the compounds represented by Chemical Formula 1 and Chemical Formula 2 may be contained in one or more of the hole injection layer, the hole transport layer, the emitting layer, and the electron transport layer.

[0051] 3 is a diagram showing an example of an organic light-emitting device consisting of a substrate 1, a positive electrode 2, a hole injection layer 5, a hole transport layer 6, an electron inhibiting layer 9, an emitting layer 7, a hole blocking layer 10, an electron transport and injection layer 8, and a negative electrode 4. In this structure, any one or more of the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2 may be contained in one or more of the hole injection layer, the hole transport layer, the electron inhibiting layer, the emitting layer, the hole blocking layer, and the electron transport and injection layer.

[0052] 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 of the organic layers contains at least one of the compounds represented by Chemical Formula 1 and Chemical Formula 2. In addition, when the organic light emitting device includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.

[0053] For example, the organic light emitting device according to the present invention may be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. In this case, a metal or a conductive metal oxide or an alloy thereof may be deposited on a substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation to form a cathode, and an organic layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer may be formed thereon, and a material to be used as an anode may be deposited thereon. In addition to this method, an organic light emitting device may be manufactured by sequentially depositing an anode material, an organic layer, and an anode material on a substrate.

[0054] In addition, at least one of the compounds represented by Formula 1 and Formula 2 may be formed as an organic layer by a solution coating method as well as a vacuum deposition method during the manufacture of an organic light emitting device, where the solution coating method refers to, but is not limited to, spin coating, dip coating, doctor blading, ink jet printing, screen printing, spraying, roll coating, etc.

[0055] In addition to this method, an organic light-emitting device can be manufactured by sequentially depositing a negative electrode material, an organic layer, and a positive electrode material on a substrate (WO2003 / 012890). However, the manufacturing method is not limited to this.

[0056] As an example, the first electrode is a positive electrode and the second electrode is a negative electrode, or the first electrode is a negative electrode and the second electrode is a positive electrode.

[0057] The positive electrode material is preferably a material having a large work function so that holes can be easily injected into the organic layer.Specific examples of the positive electrode material include, but are not limited to, metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SNO2:Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline.

[0058] The negative electrode material is preferably a material having a small work function so that electrons can be easily injected into the organic layer. Specific examples of the negative electrode material include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; and multilayer structures such as LiF / Al or LiO2 / Al.

[0059] The hole injection layer is a layer that injects holes from the electrode, and the hole injection material is preferably a compound that has the ability to transport holes, has a hole injection effect from the positive electrode, has an excellent hole injection effect on the light emitting layer or light emitting material, prevents the movement of excitons generated in the light emitting layer to the electron injection layer or electron injection material, and has excellent thin film forming ability. The HOMO (highest occupied molecular orbital) of the hole injection material is preferably between the work function of the positive electrode material and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, perylene-based organic materials, anthraquinone, and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.

[0060] The hole transport layer is a layer that receives holes from the hole injection layer and transports them to the light emitting layer, and the hole transport material is a material that can receive holes from the positive electrode or the hole injection layer and move them to the light emitting layer, and is preferably a material that has high mobility for holes.Specific examples include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers that exist in conjugated and non-conjugated conjugates.

[0061] The light-emitting material is preferably a material that can emit light in the visible light region by receiving and combining holes and electrons transported from the hole transport layer and electron transport layer, and has good quantum efficiency for fluorescence and phosphorescence.Specific examples include, but are not limited to, 8-hydroxy-quinoline aluminum complex (Alq3), carbazole-based compounds, dimerized styryl compounds, BAlq, 10-hydroxybenzoquinoline-metal compounds, benzoxazole, benzothiazole and benzimidazole-based compounds, poly(p-phenylenevinylene) (PPV)-based polymers, spiro compounds, polyfluorene, rubrene, etc.

[0062] The light-emitting layer may include a host material and a dopant material. The host material may be a fused aromatic ring derivative or a heterocyclic ring-containing compound. Specifically, the fused aromatic ring derivative may be an anthracene derivative, a pyrene derivative, a naphthalene derivative, a pentacene derivative, a phenanthrene compound, a fluoranthene compound, and the heterocyclic ring-containing compound may be, but is not limited to, a carbazole derivative, a dibenzofuran derivative, a ladder-type furan compound, a pyrimidine derivative, and the like.

[0063] The dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, the aromatic amine derivatives are condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, such as pyrene, anthracene, chrysene, and periflanthene, which have an arylamino group, and the styrylamine compounds are compounds in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, and one 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, the dopant materials include, but are not limited to, styrylamine, styryldiamine, styryltriamine, and styryltetraamine. In addition, the metal complexes include, but are not limited to, iridium complexes and platinum complexes.

[0064] The electron transport layer is a layer that receives electrons from the electron injection layer and transports them to the light-emitting layer. The electron transport material is a material that can easily receive electrons injected from the negative electrode and transfer them to the light-emitting layer, and is preferably a material with high mobility for electrons. Specific examples include, but are not limited to, Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic radical compounds; and hydroxyflavone-metal complexes. The electron transport layer may be used with any desired cathode material as used in the prior art. In particular, examples of suitable cathode materials are conventional materials that have a low work function and have an aluminum or silver layer attached thereto. Specific examples include cesium, barium, calcium, ytterbium, and samarium, each of which is followed by an aluminum or silver layer.

[0065] The electron injection layer is a layer that injects electrons from an electrode, and is capable of transporting electrons, has an excellent electron injection effect from a negative electrode, an excellent electron injection effect for the light-emitting layer or light-emitting material, prevents the excitons generated in the light-emitting layer from moving to the hole injection layer, and is preferably a compound that has excellent thin-film forming ability.Specific examples of the electron injection layer include, but are not limited to, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone, and derivatives thereof, metal complex compounds, and nitrogen-containing five-membered ring derivatives.

[0066] Examples of the metal complex compound include, but are not limited to, 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-cresolato) gallium, bis(2-methyl-8-quinolinato) (1-naphtholato) aluminum, and bis(2-methyl-8-quinolinato) (2-naphtholato) gallium.

[0067] The organic light emitting devices according to the present invention can be front-emitting, back-emitting or double-sided emitting, depending on the materials used.

[0068] Furthermore, the compound according to the present invention can be included in an organic solar cell or an organic transistor other than the organic light-emitting device.

[0069] The compound represented by Formula 1 or Formula 2 and the preparation of an organic light-emitting device including the same will be described in detail in the following examples. However, the following examples are merely for illustrating the present invention, and the scope of the present invention is not limited thereto.

[0070] [Example]

[0071] Example 1: Preparation of Compound E1 [ka] E1-A (20g, 64.1mmol) and E1-B (55.8g, 128.2mmol) were added to tetrahydrofuran (400ml) under nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (26.6g, 192.3mmol) was dissolved in water (27ml) and added, stirred thoroughly, and then tetrakistriphenyl-phosphinopalladium (2.2g, 1.9mmol) was added. After reacting for 1 hour, it was cooled to room temperature, and the organic layer and aqueous layer were separated and the organic layer was distilled. This was again added to chloroform (20 times, 986mL) and dissolved, washed twice with water, separated the organic layer, added anhydrous magnesium sulfate, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate to produce white solid compound E1 (32.5g, 66%).

[0072] MS: [M+H] + =769

[0073] Example 2: Preparation of Compound E2 [ka] The compound E2 was prepared in the same manner as in Example 1, except that the starting materials were as shown in the above reaction scheme.

[0074] MS: [M+H] + =767

[0075] Example 3: Preparation of Compound E3 [ka] The compound E3 was prepared in the same manner as in Example 1, except that the starting materials were as shown in the above reaction scheme.

[0076] MS: [M+H] + =715

[0077] Example 4: Preparation of Compound E4 [ka] Compound E4 was prepared in the same manner as in Example 1, except that the starting materials were as shown in the above reaction scheme.

[0078] MS: [M+H] + =615

[0079] Example 5: Preparation of Compound E5 [ka] The compound E5 was prepared in the same manner as in Example 1, except that the starting materials were as shown in the above reaction scheme.

[0080] MS: [M+H] + =619

[0081] Example 6: Preparation of Compound E6 [ka] The compound E6 was prepared in the same manner as in Example 1, except that the starting materials were as shown in the above reaction scheme.

[0082] MS: [M+H] + =715

[0083] Example 7: Preparation of Compound E7 [ka] The compound E7 was prepared in the same manner as in Example 1, except that the starting materials were as shown in the above reaction scheme.

[0084] MS: [M+H] +=919

[0085] Example 8: Preparation of Compound E8

[0086] [ka] E8-A (20g, 47.6mmol) and E8-B (28g, 47.6mmol) were added to 1,4-dioxane (400ml) under nitrogen atmosphere and stirred and refluxed. Then, tripotassium phosphate (30.3g, 142.9mmol) was dissolved in water (30ml) and added, stirred thoroughly, and dibenzylideneacetonepalladium (0.8g, 1.4mmol) and tricyclohexylphosphine (0.8g, 2.9mmol) were added. After 5 hours of reaction, the mixture was cooled to room temperature and the resulting solid was filtered. The solid was dissolved in chloroform (30 times, 1207mL) and 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 recrystallized with chloroform and ethyl acetate to produce white solid compound E8 (6g, 15%).

[0087] MS: [M+H] + =845

[0088] Example 9: Preparation of Compound E9 [ka] The compound E9 was prepared in the same manner as in Example 8, except that the starting materials were as shown in the above reaction scheme.

[0089] MS: [M+H] + =769

[0090] Example 10: Preparation of Compound E10 [ka] The compound E10 was prepared in the same manner as in Example 8, except that the starting materials were as shown in the above reaction scheme.

[0091] MS: [M+H] + =843

[0092] Example 11: Preparation of Compound E11 [ka] The compound E11 was prepared in the same manner as in Example 1, except that the starting materials were as shown in the above reaction scheme.

[0093] MS: [M+H] + =769

[0094] Example 12: Preparation of Compound E12 [ka] The compound E12 was prepared in the same manner as in Example 1, except that the starting materials were as shown in the above reaction scheme.

[0095] MS: [M+H] + =715

[0096] Example 13: Preparation of compound E13 [ka] The compound E13 was prepared in the same manner as in Example 1, except that the starting materials were as shown in the above reaction scheme.

[0097] MS: [M+H] + =795

[0098] Example 14: Preparation of compound E14 [ka] The compound E14 was prepared in the same manner as in Example 1, except that the starting materials were as shown in the above reaction scheme.

[0099] MS: [M+H] + =869

[0100] Example 15: Preparation of Compound E15 [ka] The compound E15 was prepared in the same manner as in Example 1, except that the starting materials were as shown in the above reaction scheme.

[0101] MS: [M+H] + =919

[0102] Example 16: Preparation of Compound E16 [ka] The compound E16 was prepared in the same manner as in Example 8, except that the starting materials were as shown in the above reaction scheme.

[0103] MS: [M+H] + =768

[0104] Example 17: Preparation of Compound E17 [ka] The compound E17 was prepared in the same manner as in Example 8, except that the starting materials were as shown in the above reaction scheme.

[0105] MS: [M+H] + =845

[0106] Example 18: Preparation of Compound E18 [ka] The compound E18 was prepared in the same manner as in Example 8, except that the starting materials were as shown in the above reaction scheme.

[0107] MS: [M+H] +=775

[0108] Example 19: Preparation of Compound E19 [ka] The compound E19 was prepared in the same manner as in Example 1, except that the starting materials were as shown in the above reaction scheme.

[0109] MS: [M+H] + =921

[0110] Example 20: Preparation of compound E20 [ka] The compound E20 was prepared in the same manner as in Example 1, except that the starting materials were as shown in the above reaction scheme.

[0111] MS: [M+H] + =919

[0112] [Experimental Example]

[0113] Experimental Example 1 A glass substrate coated with a 1,000Å-thick thin film of ITO (indium tin oxide) was placed in distilled water with detergent dissolved therein and ultrasonically cleaned. The detergent used was a product of Fischer Co., and the distilled water used was distilled water that had been filtered a second time with a filter made by Millipore Co. The ITO was cleaned for 30 minutes, then ultrasonically cleaned twice with distilled water for 10 minutes. After the distilled water cleaning was complete, the substrate was ultrasonically cleaned with solvents of isopropyl alcohol, acetone, and methanol, dried, and then transferred to a plasma cleaning device. The substrate was then cleaned for 5 minutes using oxygen plasma, and then transferred to a vacuum deposition device.

[0114] On the ITO transparent electrode thus prepared, the following compound HI-A was thermally vacuum deposited to a thickness of 600 Å to form a hole injection layer. On the hole injection layer, hexaaazatriphenylene (HAT, 50 Å) of the following formula and the following compound HT-A (600 Å) were sequentially vacuum deposited to form a hole transport layer.

[0115] Subsequently, the following compounds BH and BD were vacuum-deposited on the hole transport layer in a weight ratio of 25:1 to form a light-emitting layer having a thickness of 200 Å.

[0116] On the light-emitting layer, the compound (E1) of Example 1 and the compound [LiQ] (lithium quinolate) were vacuum-deposited in a weight ratio of 1:1 to form an electron transport and injection layer with a thickness of 350 Å. On the electron transport and injection layer, lithium fluoride (LiF) was sequentially deposited with a thickness of 10 Å and aluminum with a thickness of 1,000 Å to form a negative electrode. [ka]

[0117] During the above process, the deposition rate of the organic material was maintained at 0.4 to 0.9 Å / sec, the deposition rate of the lithium fluoride of the negative electrode was maintained at 0.3 Å / sec, and the deposition rate of the aluminum was maintained at 2 Å / sec. The degree of vacuum during deposition was 1×10 -7 ~5×10 -8 Torr was maintained to fabricate an organic light-emitting device.

[0118] Experimental Examples 2-20 An organic light emitting device was manufactured in the same manner as in Experimental Example 1, except that the compound in Table 1 was used instead of the compound in Example 1.

[0119] Comparative Experimental Examples 1-19 An organic light emitting device was manufactured in the same manner as in Experimental Example 1, except that the compounds in Table 1 were used instead of the compounds in Example 1. Compounds ET-1 to ET-19 used in Table 1 are as follows. [ka]

[0120] For the organic light-emitting devices manufactured in the above experimental examples and comparative experimental examples, 2 The driving voltage, luminous efficiency and color coordinates were measured at a current density of 20 mA / cm 2 Time to reach 90% of initial brightness at current density (T 90 The results are shown in Table 1 below.

[0121] [Table 1] [Table 1] [Table 2]

[0122] As shown in Table 1, the compound represented by Formula 1 or Formula 2 of the present invention is used in an organic layer capable of simultaneously transporting and injecting electrons in an organic light emitting device.

[0123] Comparing Experimental Examples 1 to 20 and Comparative Experimental Examples 1 to 11 in Table 1, it was found that an organic light-emitting device including a heterocyclic compound of Chemical Formula 1 or Chemical Formula 2 of the present invention exhibits significantly superior properties in terms of efficiency and lifetime compared to an organic light-emitting device including a compound in which a phenyl group less than quaterphenyl is substituted between Ar1 and Ar2.

[0124] Comparing Experimental Examples 1 to 20 and Comparative Experimental Examples 12 to 17 in Table 1, it was found that an organic light-emitting device including a heterocyclic compound of Chemical Formula 1 or Chemical Formula 2 of the present invention exhibits significantly superior properties in terms of efficiency and lifetime compared to an organic light-emitting device including a compound in which a quaterphenyl is substituted at a substitution position different from that of the present application.

[0125] Comparing Experimental Examples 1 to 20 and Comparative Experimental Example 18 in Table 1, it was found that an organic light-emitting device including a heterocyclic compound of Chemical Formula 1 or Chemical Formula 2 of the present invention exhibits significantly superior properties in terms of efficiency and lifetime compared to an organic light-emitting device including a compound in which naphthalene is substituted between Ar1 and Ar2.

[0126] Comparing Experimental Examples 1 to 20 and Comparative Experimental Example 19 in Table 1, it was found that an organic light-emitting device including a heterocyclic compound of Chemical Formula 1 or Chemical Formula 2 of the present invention exhibits significantly superior properties in terms of efficiency and lifetime compared to an organic light-emitting device including a compound in which a heteroaryl is additionally substituted on a quaternary phenylene. [Explanation of symbols]

[0127] 1 Board 2 Positive electrode 3. Light-emitting layer 4 Negative electrode 5. Hole injection layer 6. Hole transport layer 7. Light-emitting layer 8 Electron transport and injection layers 9 Electron suppression layer 10 Hole blocking layer

Claims

1. A compound represented by the following chemical formula 1 or 2: [Chemical formula 1] 【Chemistry 1】 [Chemical formula 2] 【Chemistry 2】 In the above Chemical Formula 1 or Chemical Formula 2, R １ ~R ４ are each independently hydrogen or deuterium; n1 to n4 are integers from 1 to 4, L １ and L ２ each independently represents a direct bond; or a substituted or unsubstituted arylene having 6 to 60 carbon atoms; Ar １ and Ar ２ are each independently a substituent represented by the following chemical formula 3: [Chemical formula 3] 【Chemistry 3】 In the above Chemical Formula 3, X １ ~X ５ are each independently N or C(R ５ ) and X １ ~X ５ At least two of are N; R ５ are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms and containing one or more heteroatoms selected from the group consisting of N, O, and S; or two adjacent R ５ are bonded to form a benzene ring.

2. Chemical formula 1 is represented by the following chemical formula 1-1: The compound according to claim 1, represented by the following chemical formula 2-1: [Chemical formula 1-1] 【Chemistry 4】 [Chemical formula 2-1] 【Chemistry 5】 In the above Chemical Formula 1-1 or Chemical Formula 2-1, L １ , L ２ , Ar １ and Ar ２ is as defined in claim 1.

3. L １ and L ２ The compound of claim 1 or 2, wherein each is independently a direct bond, phenylene, or biphenyldiyl.

4. Ar １ and Ar ２ is independently any one selected from the group consisting of: 【Chemistry 6】 In the above group, R ５ is as defined in claim 1.

5. R ５ are each independently hydrogen, deuterium, methyl, tert-butyl, phenyl, biphenylyl, terphenylyl, naphthyl, pyridinyl, furanyl, or thiophenyl, or two adjacent R ５ are bonded to form a benzene ring, 5. The compound of any one of claims 1 to 4, wherein said phenyl, biphenylyl, terphenylyl, naphthyl, pyridinyl, furanyl, or thiophenyl is each independently unsubstituted or substituted with deuterium, methyl, or tert-butyl.

6. Ar １ and Ar ２ is independently any one selected from the group consisting of: 【Chemistry 7】 【Chemistry 8】 。

7. The compound according to claim 1, wherein the compound represented by Chemical Formula 1 or Chemical Formula 2 is any one selected from the group consisting of the following compounds: 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】 。

8. An organic light-emitting device comprising: a first electrode; a second electrode provided opposite to the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein one or more of the organic material layers comprises the compound according to any one of claims 1 to 7.

9. The organic light-emitting device according to claim 8 , wherein the organic layer is an electron transport layer, an electron injection layer, or an electron transport and injection layer.

10. The organic light-emitting device according to claim 9 , wherein the electron transport layer, the electron injection layer, or the electron transport and injection layer further comprises a compound represented by the following Chemical Formula 4: [Chemical formula 4] 【Chemistry 14】 。

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