NOVEL COMPOUND AND ORGANIC LIGHT-EMITTING DEVICE COMPRISING 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 based on Korean Patent Application No. 10-2023-0035467 dated March 17, 2023 and Korean Patent Application No. 10-2024-0032010 dated March 6, 2024, and all contents disclosed in the documents of the Korean patent application are incorporated by reference herein. The present invention relates to a novel compound and an organic light-emitting device including the same. [Background technology]

[0002] Generally, organic light emitting phenomenon refers to the phenomenon of converting electrical energy into light energy using organic materials. Organic light emitting devices that utilize 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, so much research is being conducted.

[0003] An organic light emitting device generally has a structure including a positive electrode, a negative electrode, and an organic material layer between the positive electrode and the negative electrode. The organic material layer is often a multi-layer structure composed of different materials to improve the efficiency and safety of the organic light emitting device, and may be, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, etc. In such an organic light emitting device structure, when a voltage is applied between two electrodes, holes are injected into the organic material layer at the positive electrode and electrons are injected into the organic material layer at the negative electrode. When the injected holes and electrons meet, excitons are formed, and when the excitons fall back to the ground state, light is emitted.

[0004] There is a continuous demand for the development of new organic materials for use in such organic light emitting devices. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] Korean Patent No. 10-2000-0051826 Summary of the Invention [Problem to be solved by the invention]

[0006] The present invention relates to a novel organic light-emitting material and an organic light-emitting device containing the same. [Means for solving the problem]

[0007] The present invention provides a compound represented by the following formula 1: [ka] In the above Chemical Formula 1, Ar 1 and Ar 2 each independently represents a substituted or unsubstituted C 6-60 aryl; or C containing one or more selected from the group consisting of substituted or unsubstituted O and S 2-60 is heteroaryl, R 1 ~R 8 are each independently hydrogen; deuterium; or substituted or unsubstituted C 6-60 Although it is aryl, R 1 ~R 8 At least one of the is deuterium, Ra to Rd are each independently hydrogen; deuterium; or unsubstituted or deuterium-substituted C 6-60 It is aryl.

[0008] 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 a compound represented by Chemical Formula 1. Effect of the Invention

[0009] The compound represented by the above-mentioned Chemical Formula 1 can be 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-mentioned Chemical Formula 1 can be used as a hole injection, hole transport, light-emitting, electron transport, and / or electron injection material. [Brief description of the drawings]

[0010] [Figure 1] 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 is shown. [Diagram 2] 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 blocking layer 7, a light-emitting layer 3, a hole blocking layer 8, an electron transport layer 9, an electron injection layer 10, and a negative electrode 4 is shown. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0011] The present invention will now be described in more detail for easier understanding.

[0012] The present invention provides a compound represented by the above formula 1.

[0013] In this specification, [ka] denotes a bond that is connected to another substituent.

[0014] In the present specification, the term "substituted or unsubstituted" means that two or more of the above-listed substituents are linked and 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 heteroaryl group containing one or more of N, O and S atoms. For example, the "substituent to which two or more substituents are linked" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent to which two phenyl groups are linked. As an example, the term "substituted or unsubstituted" means "unsubstituted or substituted with deuterium, halogen, C 1-10 Alkyl, C 1-10 Alkoxy, C 6-20 Aryl and C containing one or more heteroatoms of N, O and S 2-20 In the present specification, the term "substituted with one or more substituents" can be understood to mean, for example, "substituted with 1 to 5 substituents" or "substituted with 1 or 2 substituents".

[0015] In this specification, the number of carbon atoms in the carbonyl group is not particularly limited, but the carbon number is preferably 1 to 40. Specifically, a substituent having the following structure can be formed, 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 substituent has 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 has a substituent having the following structure, but is not limited thereto. [ka]

[0018] In this specification, specific examples of the silyl group include, but are not limited to, 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.

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

[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 alkyl group has 1 to 20 carbon atoms. According to yet another embodiment, the alkyl group has 1 to 10 carbon atoms. According to yet another embodiment, the alkyl group has 1 to 6 carbon atoms. 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 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, but are not limited to these.

[0023] In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to 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, but is not limited to, a phenyl group, a biphenyl group, a terphenyl group, etc. The polycyclic aryl group may be, but is not limited to, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, etc.

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

[0026] In the present specification, the heteroaryl group is a heteroaryl group containing one or more hetero elements selected from the group consisting of O, N, Si, and S, and is not particularly limited in number of carbon atoms, but preferably has 2 to 60 carbon atoms. According to one embodiment, the heteroaryl group has 6 to 30 carbon atoms. According to one embodiment, the heteroaryl group has 6 to 20 carbon atoms. Examples of heteroaryl groups include, but are not limited to, thiophene, furan, pyrrole, imidazole, thiazole, oxazole, oxadiazole, triazole, pyridyl, bipyridyl, pyrimidine, triazine, acridyl, pyridazine, pyrazinyl, quinolinyl, quinazoline, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinoline, indole, carbazole, benzoxazole, benzimidazole, benzothiazole, benzocarbazole, benzothiophene, dibenzothiophene, benzofuranyl, phenanthroline, isoxazolyl, thiadiazolyl, phenothiazinyl, and dibenzofuranyl groups.

[0027] In this specification, the aryl group in the aralkyl group, the aralkenyl group, the alkylaryl group, and the arylamine group is the same as the above-mentioned aryl group examples. In this specification, the alkyl group in the aralkyl group, the alkylaryl group, and the alkylamine group is the same as the above-mentioned alkyl group examples. In this specification, the heteroaryl in the heteroarylamine can be applied to the above-mentioned heteroaryl group explanation. In this specification, the alkenyl group in the aralkenyl group is the same as the above-mentioned alkenyl group examples. In this specification, the aryl group explanation can be applied to the above-mentioned aryl group except that the arylene is a divalent group. In this specification, the heteroaryl group explanation can be applied to the above-mentioned heteroarylene except that the heteroaryl group is a divalent group. In this specification, the hydrocarbon ring is not a monovalent group, but is formed by bonding two substituents, but is the above-mentioned aryl group or cycloalkyl group explanation can be applied. In this specification, the heteroaryl is not a monovalent group, but is formed by bonding two substituents, but is the above-mentioned heteroaryl group explanation can be applied.

[0028] Preferably, Ar 1 and Ar 2 each independently represents a substituted or unsubstituted C 6-20 aryl; or C containing one or more selected from the group consisting of substituted or unsubstituted O and S 2-20 It may be a heteroaryl.

[0029] More preferably, Ar 1 and Ar 2 may each independently be phenyl, biphenylyl, dibenzofuranyl, or dibenzothiophenyl; 1 and Ar 2 can each independently be unsubstituted or substituted with one or more deuterium atoms.

[0030] Preferably, Ar 1 and Ar 2At least one of the groups may be unsubstituted or substituted with one or more deuterium atoms.

[0031] R 1 ~R 8 are each independently hydrogen; deuterium; or substituted or unsubstituted C 6-20 Although it is aryl, R 1 ~R 8 At least one of the groups may be deuterium.

[0032] More preferably, R 1 ~R 8 are each independently hydrogen, deuterium, or phenyl substituted with five deuteriums, while R 1 ~R 8 At least one of the groups may be deuterium.

[0033] More preferably, R 1 ~R 8 are each independently deuterium or phenyl substituted with five deuteriums, while R 1 ~R 8 At least one of the groups may be deuterium.

[0034] Preferably, R 1 ~R 8 More preferably, four or more of R 1 ~R 8 Six or more of R may be deuterium. Most preferably, R 1 ~R 8 Seven or more of the may be deuterium.

[0035] Preferably, Ra to Rd are each independently hydrogen; deuterium; or unsubstituted or deuterium-substituted C 6-20 It may be aryl.

[0036] More preferably, Ra to Rd may each independently be hydrogen, deuterium, phenyl, biphenylyl, terphenylyl, naphthyl, anthracenyl, phenanthrenyl, or triphenylenyl, and the phenyl, biphenylyl, terphenylyl, naphthyl, anthracenyl, phenanthrenyl, or triphenylenyl may each independently be unsubstituted or substituted with one or more deuterium atoms.

[0037] More preferably, Ra to Rd may each independently be hydrogen, phenyl, biphenylyl, terphenylyl, naphthyl, anthracenyl, phenanthrenyl, or triphenylenyl, and the phenyl, biphenylyl, terphenylyl, naphthyl, anthracenyl, phenanthrenyl, or triphenylenyl may each independently be unsubstituted or substituted with one or more deuterium atoms.

[0038] More preferably, any one of Ra to Rd is phenyl, biphenylyl, terphenylyl, naphthyl, anthracenyl, phenanthrenyl, or triphenylenyl, and the phenyl, biphenylyl, terphenylyl, naphthyl, anthracenyl, phenanthrenyl, and triphenylenyl may each independently be unsubstituted or substituted with one or more deuterium atoms, and the remainder may be hydrogen.

[0039] Most preferably, any one of Ra to Rd is any one selected from the group consisting of the following, and the rest may be hydrogen: [ka]

[0040] Representative examples of the compound represented by Formula 1 are as follows: [ka]

[0041] [ka]

[0042]

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[0063] [ka]

[0064] [ka]

[0065] [ka]

[0066] [ka]

[0067] [ka]

[0068] [ka]

[0069] The compound represented by Chemical Formula 1 can be prepared, for example, by the method shown in Reaction Scheme 1 below, and the remaining compounds can be prepared in a similar manner.

[0070] [ka]

[0071] In the above reaction scheme 1, R 1 ~R 8 , Ra~Rd, Ar 1 and Ar 2 is as defined in Formula 1 above, and X is a halogen, preferably X is chloro or bromo.

[0072] The reaction scheme 1 is an amine substitution reaction, which is preferably carried out in the presence of a palladium catalyst and a base, and the reactive group for the amine substitution reaction can be changed according to the known methods in the art. The preparation method can be more specifically described in the preparation examples described below.

[0073] The present invention also provides an organic light-emitting device comprising a compound represented by Chemical Formula 1. 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 one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises a compound represented by Chemical Formula 1.

[0074] 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 blocking layer, a light-emitting layer, a hole blocking 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.

[0075] In addition, the organic layer may include a light-emitting layer, and the light-emitting layer may include the compound represented by Chemical Formula 1.

[0076] In addition, the organic layer may include a hole transport layer, a hole injection layer, or a layer that simultaneously transports and injects holes, and the hole transport layer, the hole injection layer, or the layer that simultaneously transports and injects holes may include a compound represented by Chemical Formula 1.

[0077] In addition, the organic layer may include an electron transport layer, an electron injection layer, or an electron injection and transport layer, and the electron transport layer, the electron injection layer, or the electron injection and transport layer may include the compound represented by Chemical Formula 1.

[0078] 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. 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 illustrated in FIG. 1 and FIG. 2.

[0079] Fig. 1 illustrates 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. Fig. 2 illustrates 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 blocking layer 7, a light-emitting layer 3, a hole blocking layer 8, an electron transport layer 9, an electron injection layer 10, and a negative electrode 4.

[0080] In this structure, the compound represented by Formula 1 may be included in the light emitting layer.

[0081] 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 the compound represented by Formula 1. 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.

[0082] 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 on the cathode, and a material that can be used as an anode may be deposited on the anode. 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.

[0083] In addition, the compound represented by Formula 1 can be formed in 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 blade, inkjet printing, screen printing, spraying, roll coating, etc.

[0084] In addition to the above 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.

[0085] 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.

[0086] The cathode 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 cathode material include metals such as vanadium, chromium, copper, zinc, and gold, and alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO:Al, or SnO. 2These include, but are not limited to: combinations of metals and oxides such as Sb; and conducting polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline.

[0087] 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 metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; LiF / Al or LiO 2 Examples of suitable materials include, but are not limited to, multi-layered materials such as SiO2 / Al.

[0088] 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 at the positive electrode, has an excellent hole injection effect for 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.

[0089] The hole transport layer is a layer that receives holes from the hole injection layer and transports them to the light emitting layer, and a material that can receive holes from the anode or the hole injection layer and move them to the light emitting layer and has high mobility for holes is suitable as a hole transport material.Specific examples include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers having both conjugated and non-conjugated portions.

[0090] The electron blocking layer is a layer placed between the hole transport layer and the light emitting layer to prevent electrons injected from the anode from being recombined in the light emitting layer and passing to the hole transport layer, and is also called an electron inhibiting layer or an electron blocking layer. The electron blocking layer is preferably made of a material having a smaller electron affinity than the electron transport layer.

[0091] The light-emitting material is preferably a material that can emit light in the visible light range by receiving and combining holes and electrons transported from the hole transport layer and electron transport layer, respectively, and has good quantum efficiency for fluorescence or phosphorescence. 3 ); carbazole compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzoxazole, benzothiazole and benzimidazole compounds; poly(p-phenylenevinylene) (PPV) polymers; spiro compounds; polyfluorene, rubrene, etc., but are not limited to these.

[0092] The light-emitting layer may include a host material and a dopant material. The host material may be a condensed aromatic ring derivative or a heterocyclic ring-containing compound. Specifically, the condensed aromatic ring derivative may be an anthracene derivative, a pyrene derivative, a naphthalene derivative, a pentacene derivative, a phenanthrene compound, a fluoranthene compound, etc., 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, etc.

[0093] The dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, the aromatic amine derivatives include fused aromatic ring derivatives having substituted or unsubstituted arylamino groups, such as pyrene, anthracene, chrysene, and periflanthene, which have arylamino groups, and the styrylamine compounds include substituted or unsubstituted arylamines substituted with at least one arylvinyl group, in which one or more substituents selected from the group consisting of aryl groups, silyl groups, alkyl groups, cycloalkyl groups, and arylamino groups are substituted or unsubstituted. Specifically, the dopant materials include, but are not limited to, styrylamines, styryldiamines, styryltriamines, and styryltetraamines. In addition, the metal complexes include, but are not limited to, iridium complexes and platinum complexes.

[0094] The hole blocking layer is a layer placed between the electron transport layer and the light emitting layer to prevent holes injected from the positive electrode from being recombined in the light emitting layer and passing to the electron transport layer, and is also called a hole suppression layer or hole blocking layer. For the hole blocking layer, a material with a large ionization energy is preferable.

[0095] The electron transport layer is a layer that receives electrons from the electron injection layer and transports them to the light emitting layer. As the electron transport material, a material that can efficiently receive electrons injected from the negative electrode and transfer them to the light emitting layer and has high mobility for electrons is suitable. Specific examples include Al complex of 8-hydroxyquinoline; Alq 3 These include, but are not limited to, complexes containing; organic radical compounds; hydroxyflavone-metal complexes. The electron transport layer can be used with any desired cathode material as used by conventional techniques. In particular, examples of suitable cathode materials are conventional materials having low work functions followed by an aluminum or silver layer. Specifically, cesium, barium, calcium, ytterbium and samarium, each followed by an aluminum or silver layer.

[0096] The electron injection layer is a layer that injects electrons from an electrode, and is preferably a compound that has the ability to transport 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 has excellent thin-film forming ability.Specific examples of the compound include, but are not limited to, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, preolenylidene methane, anthrone, and their derivatives, metal complex compounds, and nitrogen-containing 5-membered ring derivatives.

[0097] 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.

[0098] Meanwhile, in the present invention, the "electron injection and transport layer" is a layer that serves both the functions of the electron injection layer and the electron transport layer, and a material that serves the functions of each layer may be used alone or in combination or by lamination, but is not limited thereto.

[0099] The organic light emitting device according to the present invention may be a bottom light emitting device, a top light emitting device, or a double sided light emitting device, and may be a bottom light emitting device which requires relatively high light emitting efficiency.

[0100] In addition, the compound represented by Chemical Formula 1 may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device. EXAMPLES

[0101] The present invention will be described in more detail below to help understanding of the present invention. However, the following examples are merely illustrative of the present invention, and the content of the present invention is not limited to the following examples.

[0102] [Production Example] Preparation Example A: Preparation of Compound A1 [ka]

[0103] 1) Preparation of Compound A1-1 Under a nitrogen atmosphere, 5-chloro-2-fluorophenyl)boronic acid (40g, 229.4mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (61.4g, 229.4mmol) were added to 400ml of tetrahydrofuran and stirred and refluxed. Then, potassium carbonate (95.1g, 688.2mmol) was dissolved in 95ml of water and added, and after thorough stirring, [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (3.4g, 4.6mmol) was added. After 11 hours of reaction, the mixture 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 830mL of toluene and dissolved, washed twice with water, and 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 through a silica column using toluene and ethyl acetate to produce a grey solid compound A1-1 (58.9 g, 71%, MS: [M+H]+=362.8).

[0104] 2) Preparation of Compound A1 Under a nitrogen atmosphere, A1-1 (50g, 138.2mmol) and bis(pinacolato)diboron (38.7g, 165.8mmol) were added to 750ml of Diox and stirred and refluxed. Then, potassium acetate (39.9g, 414.6mmol) was added and thoroughly stirred, and then palladium dibenzylideneacetone palladium (2.4g, 4.1mmol) and tricyclohexylphosphine (2.3g, 8.3mmol) were added. After reacting for 5 hours, the mixture was cooled to room temperature, and the organic layer was filtered to remove salts, and the filtered organic layer was distilled. This was again dissolved in 626mL of chloroform, washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added and stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified through a silica column using chloroform and ethyl acetate to produce a yellow solid compound A1 (53.3 g, 85%, MS: [M+H]+=454.3).

[0105] Preparation Example B: Preparation of Compound B1 [ka]

[0106] Compound B1 (35.3 g, 73%, MS: [M+H]+=530.4) was prepared in the same manner as in Preparation A1, except that 2-chloro-4,6-diphenyl-1,3,5-triazine was replaced with 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine in Preparation A.

[0107] Preparation Example C: Preparation of Compound C1 [ka]

[0108] 1) Preparation of Compound C1-1 Under a nitrogen atmosphere, (4-chloro-2-fluorophenyl)boronic acid (40g, 229.4mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (61.4g, 229.4mmol) were added to 400ml of tetrahydrofuran and stirred and refluxed. Then, potassium carbonate (95.1g, 688.2mmol) was dissolved in 95ml of water and added, and after thorough stirring, [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (3.4g, 4.6mmol) was added. After 6 hours of reaction, the mixture 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 830mL of toluene and dissolved, washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added and stirred, then filtered and the filtrate was distilled under reduced pressure. The concentrated compound was purified through a silica column using toluene and ethyl acetate to produce a grey solid compound C1-1 (66.4 g, 80%, MS: [M+H]+=362.8).

[0109] 2) Preparation of Compound C1 Under a nitrogen atmosphere, C1-1 (40g, 110.6mmol) and bis(pinacolato)diboron (30.9g, 132.7mmol) were added to 600ml of Diox and stirred and refluxed. Then, potassium acetate (31.9g, 331.7mmol) was added and thoroughly stirred, and then palladium dibenzylideneacetone palladium (1.9g, 3.3mmol) and tricyclohexylphosphine (1.9g, 6.6mmol) were added. After reacting for 6 hours, the mixture was cooled to room temperature, and the organic layer was filtered to remove salts, and the filtered organic layer was distilled. This was again dissolved in 501mL of chloroform, washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added and stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified through a silica column using chloroform and ethyl acetate to produce a grey solid compound C1 (31.6 g, 63%, MS: [M+H]+=454.3).

[0110] Preparation Example D: Preparation of Compound D1 [ka]

[0111] Compound D1 (30.5 g, 70%, MS: [M+H]+=461.2) was prepared in the same manner as in Preparation Example A1, except that 2-chloro-4,6-diphenyl-1,3,5-triazine was replaced with 2-chloro-4,6-bis(phenyl-2,3,4,5-d4)-1,3,5-triazine.

[0112] Preparation Example E: Preparation of Compound E1 [ka]

[0113] Compound E1 (35.8 g, 77%, MS: [M+H]+=529) was prepared in the same manner as in Preparation A1, except that 2-chloro-4,6-diphenyl-1,3,5-triazine was replaced with 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine in Preparation A.

[0114] Production Example 1: Production of Compound 1 [ka]

[0115] Step 1) Preparation of compound Sub1 Under a nitrogen atmosphere, compound A1 (36 g, 79.4 mmol) and 3-bromo-1,1'-biphenyl (18.5 g, 79.4 mmol) were added to 720 ml of tetrahydrofuran and stirred and refluxed. Then, potassium carbonate (32.9 g, 238.2 mmol) was dissolved in 33 ml of water and added, and after thorough stirring, bis(tri-tertiarybutylphosphine)palladium (0.8 g, 1.6 mmol) was added. After 3 hours of reaction, the mixture was cooled to room temperature and the resulting solid was filtered. The solid was dissolved in 1904 mL of chloroform and washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added and stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified through a silica column using chloroform and ethyl acetate to produce a gray solid compound Sub1 (28.9 g, 76%, MS: [M+H]+=480.6).

[0116] Step 2) Preparation of Compound 1 Compound Sub1 (40g, 83.4mmol) and 9H-carbazole-1,3,4,5,6,8-d6 (14.5g, 83.4mmol) were added to 320ml of dimethylacetamide under nitrogen atmosphere and stirred and refluxed. Then, tripotassium phosphate (53.1g, 250.2mmol) was added and thoroughly stirred, and after reacting for 1 hour, it was cooled to room temperature, and the organic layer was filtered to remove salts, and the filtered organic layer was distilled. This was again added to 1583mL of chloroform and dissolved, washed twice with water, and 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 through a silica column using chloroform and ethyl acetate to produce a yellow solid compound 1 (30.1g, 57%, MS: [M+H]+=633.8).

[0117] Production Example 2: Production of Compound 2 [ka]

[0118] Step 1) Preparation of compound Sub2 Under a nitrogen atmosphere, compound A1 (36 g, 79.4 mmol) and 4-iodo-1,1'-biphenyl (22.2 g, 79.4 mmol) were added to 720 ml of tetrahydrofuran and stirred and refluxed. Then, potassium carbonate (32.9 g, 238.2 mmol) was dissolved in 33 ml of water and added, and the mixture was thoroughly stirred, and then bis(tri-tertiarybutylphosphine)palladium (0.8 g, 1.6 mmol) was added. After 4 hours of reaction, the mixture was cooled to room temperature and the resulting solid was filtered. The solid was dissolved in 1904 mL of chloroform and washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate to produce red solid compound Sub2 (34.7 g, 91%, MS: [M+H]+=480.6).

[0119] Step 2) Preparation of Compound 2 Compound Sub (240g, 83.4mmol) and 9H-carbazole-1,3,4,5,6,8-d6 (14.5g, 83.4mmol) were added to 320ml of dimethylacetamide under nitrogen atmosphere and stirred and refluxed. Then, tripotassium phosphate (53.1g, 250.2mmol) was added and thoroughly stirred, and after reacting for 1 hour, it was cooled to room temperature, and the organic layer was filtered to remove salts, and the filtered organic layer was distilled. This was again added to 1583mL of chloroform and dissolved, washed twice with water, and 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 through a silica column using chloroform and ethyl acetate to produce a yellow solid compound (241.7g, 79%, MS: [M+H]+=633.8).

[0120] Production Example 3: Production of Compound 3 [ka]

[0121] Step 1) Preparation of compound Sub3 Under a nitrogen atmosphere, compound A1 (36 g, 79.4 mmol) and 5'-bromo-1,1':3',1''-terphenyl (24.6 g, 79.4 mmol) were added to 720 ml of tetrahydrofuran and stirred and refluxed. Then, potassium carbonate (32.9 g, 238.2 mmol) was dissolved in 33 ml of water and added, and the mixture was thoroughly stirred, and then bis(tri-tertiarybutylphosphine)palladium (0.8 g, 1.6 mmol) was added. After 3 hours of reaction, the mixture was cooled to room temperature and the resulting solid was filtered. The solid was dissolved in 2206 mL of chloroform and washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate to produce gray solid compound Sub3 (27.4 g, 62%, MS: [M+H]+=556.7).

[0122] Step 2) Preparation of Compound 3 Compound Sub (340g, 72mmol) and 9H-carbazole-1,3,4,5,6,8-d6 (12.5g, 72mmol) were added to 320ml of dimethylacetamide under nitrogen atmosphere and stirred and refluxed. Then, tripotassium phosphate (45.8g, 216mmol) was added and thoroughly stirred, and after reacting for 2 hours, it was cooled to room temperature, and the organic layer was filtered to remove salts, and the filtered organic layer was distilled. This was again added to 1531mL of chloroform and dissolved, washed twice with water, and 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 through a silica column using chloroform and ethyl acetate to produce a yellow solid compound 3 (40.8g, 80%, MS: [M+H]+=709.9).

[0123] Production Example 4: Production of Compound 4 [ka]

[0124] Step 1) Preparation of compound Sub4 Compound A1 (30g, 66.2mmol) and bromobenzene 10.4g, 66.2mmol) were added to 300ml of tetrahydrofuran under nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (27.4g, 198.5mmol) was dissolved in 27ml of water and added, stirred thoroughly, and then bis(tri-tertiarybutylphosphine)palladium (0.7g, 1.3mmol) was added. After 3 hours of reaction, the mixture was cooled to room temperature and the resulting solid was filtered. The solid was dissolved in 1335mL of chloroform and washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added and stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized with chloroform and ethyl acetate to produce gray solid compound Sub4 (19.5g, 73%, MS: [M+H]+=404.5).

[0125] Step 2) Preparation of compound 4 Compound Sub4 (30g, 74.4mmol) and 3-(phenyl-2,4,6-d3)-9H-carbazole-1,2,4,5,6,8-d6 (18.8g, 74.4mmol) were added to 240ml of dimethylacetamide under nitrogen atmosphere and stirred and refluxed. Then, tripotassium phosphate (47.4g, 223.1mmol) was added and thoroughly stirred, and after reacting for 1 hour, it was cooled to room temperature, and the organic layer was filtered to remove salts, and the filtered organic layer was distilled. This was again added to 1418mL of chloroform and dissolved, washed twice with water, and 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 through a silica column using chloroform and ethyl acetate to produce a yellow solid compound 4 (32.1g, 68%, MS: [M+H]+=636.8).

[0126] Production Example 5: Production of Compound 5 [ka]

[0127] Step 1) Preparation of compound Sub5 Compound B1 (30g, 56.7mmol) and bromobenzene (8.9g, 56.7mmol) were added to 450ml of tetrahydrofuran under nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (23.5g, 170mmol) was dissolved in 23ml of water and added, and after thorough stirring, [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.8g, 1.1mmol) was added. After 12 hours of reaction, the mixture 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 272mL of toluene and dissolved, washed twice with water, and the organic layer was separated, stirred with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified through a silica column using toluene and ethyl acetate to produce a gray solid compound Sub5 (16.6g, 61%, MS: [M+H]+=480.6).

[0128] Step 2) Preparation of Compound 5 Compound Sub5 (30g, 62.6mmol) and 9H-carbazole-d8 (11g, 62.6mmol) were added to 240ml of dimethylacetamide under nitrogen atmosphere and stirred and refluxed. Then, tripotassium phosphate (39.8g, 187.7mmol) was added and thoroughly stirred, and after reacting for 1 hour, it was cooled to room temperature, and the organic layer was filtered to remove salts, and the filtered organic layer was distilled. This was again added to 1191mL of chloroform and dissolved, washed twice with water, and 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 through a silica column using chloroform and ethyl acetate to produce a yellow solid compound 5 (20.7g, 52%, MS: [M+H]+=635.8).

[0129] Production Example 6: Production of Compound 6 [ka]

[0130] Step 1) Preparation of compound Sub6 Under a nitrogen atmosphere, compound C1 (35 g, 77.2 mmol) and 4-iodo-1,1'-biphenyl (21.6 g, 77.2 mmol) were added to 350 ml of tetrahydrofuran and stirred and refluxed. Then, potassium carbonate (32 g, 231.6 mmol) was dissolved in 32 ml of water and added, and after thorough stirring, bis(tri-tertiarybutylphosphine)palladium (0.8 g, 1.5 mmol) was added. After 4 hours of reaction, the mixture was cooled to room temperature and the resulting solid was filtered. The solid was dissolved in 1851 mL of chloroform and washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified through a silica column using chloroform and ethyl acetate to produce a gray solid compound Sub6 (29.3 g, 79%, MS: [M+H]+=480.6).

[0131] Step 2) Preparation of compound 6 Compound Sub6 (25g, 52.1mmol) and 9H-carbazole-d8 (9.1g, 52.1mmol) were added to 200ml of dimethylacetamide under nitrogen atmosphere and stirred and refluxed. Then, tripotassium phosphate (33.2g, 156.4mmol) was added and thoroughly stirred, and after reacting for 2 hours, it was cooled to room temperature, and the organic layer was filtered to remove salts, and the filtered organic layer was distilled. This was again added to 993mL of chloroform and dissolved, washed twice with water, and 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 through a silica column using chloroform and ethyl acetate to produce a yellow solid compound 6 (17.5g, 53%, MS: [M+H]+=635.8).

[0132] Preparation Example 7: Preparation of Compound 7 [ka]

[0133] Compound 7 (29.5 g, 66%, MS: [M+H]+=715.9) was prepared in the same manner as in Preparation Example 6, except that 9H-carbazole-d8 was replaced with 3-(phenyl-d5-9H-carbazole-1,2,4,5,6,7,8-d7.

[0134] Production Example 8: Production of Compound 8 [ka]

[0135] Step 1) Preparation of compound F1 Compound F1 (39.4 g, 75%, MS: [M+H]+=544.4) was prepared in the same manner as in Preparation Example 1 for Compound A1, except that 2-chloro-4,6-diphenyl-1,3,5-triazine was replaced with 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine.

[0136] Step 2) Preparation of compound Sub7 Under a nitrogen atmosphere, compound F1 (35g, 64.4mmol) and 3-bromo-1,1'-biphenyl1 (5g, 64.4mmol) were added to 350ml of tetrahydrofuran and stirred and refluxed. Then, potassium carbonate (26.7g, 193.2mmol) was dissolved in 27ml of water and added, and after thorough stirring, bis(tri-tertiarybutylphosphine)palladium (0.7g, 1.3mmol) was added. After 3 hours of reaction, the mixture was cooled to room temperature and the resulting solid was filtered. The solid was dissolved in 1834mL of chloroform and washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added and stirred, then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified through a silica column using chloroform and ethyl acetate to produce a gray solid compound sub7 (22.4g, 61%, MS: [M+H]+=570.6).

[0137] Step 3) Preparation of compound 8 Compound Sub7 (30g, 52.7mmol) and 9H-carbazole-d8 (9.2g, 52.7mmol) were added to 240ml of dimethylacetamide under nitrogen atmosphere and stirred and refluxed. Then, tripotassium phosphate (33.5g, 158mmol) was added and thoroughly stirred, and after 3 hours of reaction, the mixture was cooled to room temperature, and the organic layer was filtered to remove salts, and the filtered organic layer was distilled. This was again added to 1142mL of chloroform and dissolved, washed twice with water, and 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 through a silica column using chloroform and ethyl acetate to produce a yellow solid compound 8 (25.5g, 67%, MS: [M+H]+=723.9).

[0138] Preparation Example 9: Preparation of Compound 9 [ka]

[0139] Compound 9 (34.1 g, 69%, MS: [M+H]+=806) was prepared in the same manner as in Preparation Example 8, except that 9H-carbazole-d8 was replaced with 3-(phenyl-d5-9H-carbazole-1,2,4,5,6,7,8-d7.

[0140] Preparation Example 10: Preparation of Compound 10 [ka]

[0141] Step 1) Preparation of compound G1 Compound G1 (26.6 g, 52%, MS: [M+H]+=560.5) was prepared in the same manner as in Preparation Example 1 for Compound A1, except that 2-chloro-4,6-diphenyl-1,3,5-triazine was replaced with 2-chloro-4-(dibenzo[b,d]thiophen-3-yl)-6-phenyl-1,3,5-triazine.

[0142] Step 2) Preparation of compound Sub8 Compound Sub8 (26.4 g, 72%, MS: [M+H]+=586.7) was prepared in the same manner as for preparing compound Sub7, except that compound F1 in Preparation Example 8 was replaced with compound G1.

[0143] Step 3) Preparation of Compound 10 Compound Sub8 (25g, 42.7mmol) and 9H-carbazole-d8 (7.5g, 42.7mmol) were added to 200ml of dimethylacetamide under nitrogen atmosphere and stirred and refluxed. Then, tripotassium phosphate (27.2g, 128.1mmol) was added and thoroughly stirred, and after reacting for 2 hours, it was cooled to room temperature, and the organic layer was filtered to remove salts, and the filtered organic layer was distilled. This was again added to 949mL of chloroform and dissolved, washed twice with water, and 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 through a silica column using chloroform and ethyl acetate to produce a yellow solid compound 10 (25.3g, 80%, MS: [M+H]+=742).

[0144] Preparation Example 11: Preparation of Compound 11 [ka]

[0145] Compound 11 (21.5 g, 70%, MS: [M+H]+=634) was prepared in the same manner as in Preparation Example 2, except that 9H-carbazole-d8 was used instead of 9H-carbazole-d6.

[0146] Preparation Example 12: Preparation of Compound 12 [ka]

[0147] Step 1) Preparation of compound Sub9 Compound D1 (35g, 75.9mmol) and 4-iodo-1,1'-biphenyl (21.2g, 75.9mmol) were added to 350ml of tetrahydrofuran under nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (31.5g, 227.6mmol) was dissolved in 31ml of water and added, stirred thoroughly, and then bis(tri-tertiarybutylphosphine)palladium (0.8g, 1.5mmol) was added. After 5 hours of reaction, the mixture was cooled to room temperature and the resulting solid was filtered. The solid was dissolved in 1850mL of chloroform and washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added and stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified through a silica column using chloroform and ethyl acetate to produce a gray solid compound Sub9 (27g, 73%, MS: [M+H]+=488).

[0148] Step 2) Preparation of compound 12 Compound Sub9 (25g, 51.3mmol) and 9H-carbazole-1,2,3,4,5,6,8-d7 (8.9g, 51.3mmol) were added to 200ml of dimethylacetamide under nitrogen atmosphere and stirred and refluxed. Then, tripotassium phosphate (32.6g, 153.8mmol) was added and thoroughly stirred, and after reacting for 1 hour, it was cooled to room temperature, and the organic layer was filtered to remove salts, and the filtered organic layer was distilled. This was again added to 987mL of chloroform and dissolved, washed twice with water, and 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 through a silica column using chloroform and ethyl acetate to produce a yellow solid compound compound 12 (17.4g, 53%, MS: [M+H]+=642).

[0149] Preparation Example 13: Preparation of Compound 13 [ka]

[0150] Step 1) Preparation of compound Sub10 Under a nitrogen atmosphere, compound D1 (35 g, 75.9 mmol) and 3-bromo-1,1'-biphenyl (17.7 g, 75.9 mmol) were added to 350 ml of tetrahydrofuran and stirred and refluxed. Then, potassium carbonate (31.5 g, 227.6 mmol) was dissolved in 31 ml of water and added, and the mixture was thoroughly stirred, and then bis(tri-tertiarybutylphosphine)palladium (0.8 g, 1.5 mmol) was added. After 4 hours of reaction, the mixture was cooled to room temperature and the resulting solid was filtered. The solid was dissolved in 1850 mL of chloroform and washed twice with water, and the organic layer was separated, anhydrous magnesium sulfate was added and stirred, and then filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified through a silica column using chloroform and ethyl acetate to produce a gray solid compound Sub10 (29.2 g, 79%, MS: [M+H]+=488.6).

[0151] Step 2) Preparation of compound 13 In a nitrogen atmosphere, compound Sub10 (25g, 51.3mmol) and 4-(phenyl-d5-9H-carbazole-1,5,6,8-d4 (12.9g, 51.3mmol) were added to 200ml of dimethylacetamide and stirred and refluxed. Then, tripotassium phosphate (32.6g, 153.8mmol) was added and thoroughly stirred, and after reacting for 2 hours, the mixture was cooled to room temperature, and the organic layer was filtered to remove salts, and the filtered organic layer was distilled. This was again added to 1093mL of chloroform and dissolved, washed twice with water, and 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 through a silica column using chloroform and ethyl acetate to produce a yellow solid compound 13 (23.7g, 65%, MS: [M+H]+ = 720).

[0152] Preparation Example 14: Preparation of Compound 14 [ka]

[0153] Step 1) Preparation of compound Sub11 Compound E1 (35g, 66.1mmol) and bromobenzene (10.4g, 66.1mmol) were added to 350ml of tetrahydrofuran under nitrogen atmosphere and stirred and refluxed. Then, potassium carbonate (27.4g, 198.3mmol) was dissolved in 27ml of water and added, stirred thoroughly, and then bis(tri-tertiarybutylphosphine)palladium (0.7g, 1.3mmol) was added. After 3 hours of reaction, the mixture was cooled to room temperature and the resulting solid was filtered. The solid was dissolved in 1585mL of chloroform and washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added and stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified through a silica column using chloroform and ethyl acetate to produce a gray solid compound Sub11 (25.4g, 80%, MS: [M+H]+=480.6).

[0154] Step 2) Preparation of compound 14 Compound Sub11 (25g, 52.1mmol) and 4-(phenyl-d5)-9H-carbazole-2,5,6,8-d4 (13.2g, 52.1mmol) were added to 200ml of dimethylacetamide under nitrogen atmosphere and stirred and refluxed. Then, tripotassium phosphate (33.2g, 156.4mmol) was added and thoroughly stirred, and after 3 hours of reaction, the mixture was cooled to room temperature, and the organic layer was filtered to remove salts, and the filtered organic layer was distilled. This was again added to 1099mL of chloroform and dissolved, washed twice with water, and 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 through a silica column using chloroform and ethyl acetate to produce a yellow solid compound 14 (23.1g, 63%, MS: [M+H]+=712).

[0155] [Example] Example 1: Fabrication of an organic light-emitting device A glass substrate coated with a 1400 Å-thick thin film of ITO (Indium Tin Oxide) was placed in distilled water containing detergent 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 washed for 30 minutes, and then ultrasonically cleaned twice with distilled water for 10 minutes. After the distilled water cleaning was completed, the substrate was ultrasonically cleaned with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transferred to a plasma cleaner. The substrate was then cleaned for 5 minutes using oxygen plasma, and then transferred to a vacuum deposition device.

[0156] On the ITO transparent electrode thus prepared, the following compound HT-A and the following compound PD were thermally vacuum deposited in a thickness of 100 Å in a weight ratio of 95:5, and then the following compound HT-A alone was deposited in a thickness of 1150 Å to form a hole transport layer. On the hole transport layer, the following compound HT-B was thermally vacuum deposited in a thickness of 450 Å to form an electron blocking layer. On the electron blocking layer, the previously prepared compound 1 and the following compound GD were vacuum deposited in a weight ratio of 85:15 in a thickness of 400 Å to form a light emitting layer. On the light emitting layer, the following compound ET-A was vacuum deposited in a thickness of 50 Å to form a hole blocking layer. On the hole blocking layer, the following compound ET-B and the following compound Liq were thermally vacuum deposited in a thickness of 250 Å in a weight ratio of 2:1, and then Lif and magnesium were vacuum deposited in a weight ratio of 1:1 in a thickness of 30 Å to form an electron transport and injection layer. On the electron injection layer, magnesium and silver were deposited in a weight ratio of 1:4 to a thickness of 160 Å to form a negative electrode, thereby completing an organic light emitting device.

[0157] [ka]

[0158] During the above process, the deposition rate of the organic material was maintained at 0.4-0.7 Å / sec, the deposition rate of magnesium and silver was maintained at 2 Å / sec, and the vacuum degree during deposition was 2×10 -7 ~5×10 -6Torr was maintained to fabricate an organic light-emitting device.

[0159] Examples 2 to 12 and Comparative Examples 1 to 9 Organic light emitting devices of Examples 2 to 12 and Comparative Examples 1 to 9 were fabricated using the same method as in Example 1, except that the host material was changed as shown in Table 1 below. Compounds GH-A, GH-B, GH-C, GH-D, GH-E, GH-F, GH-G, GH-H and GH-I in Table 1 below are respectively as follows. 14 means that 14 hydrogens in the compound inside the brackets have been replaced with deuterium.

[0160] [ka]

[0161] [Experimental Example] A current was applied to the organic light-emitting devices prepared in the examples and comparative examples to measure the voltage, efficiency, and lifespan (T95), and the results are shown in Table 1 below. 2 The measurements were performed by applying a current density of 20 mA / cm. 2 means the time measured until the initial brightness decreases to 95%.

[0162] [Table 1]

[0163] In the compound represented by Chemical Formula 1, a polycyclic nitrogen-containing heterocyclic substituent that acts as an intramolecular electron donor and a monocyclic nitrogen-containing heterocyclic ring that acts as an electron acceptor are bonded to each other at the ortho position, facilitating intracharge transfer.

[0164] Furthermore, a compound in which a benzene ring and a polycyclic nitrogen-containing heterocycle, which act as electron donors, are bonded to each other at para positions in the molecule has high molecular stability and is advantageous for transporting holes and electrons.

[0165] Therefore, as shown in Table 1, when the compound of Formula 1 is used as a host for an organic light emitting device, it is possible to obtain characteristics of low voltage, high efficiency, and long life. [Explanation of symbols]

[0166] 1: Substrate 2: Positive electrode 3: Light-emitting layer 4: Negative electrode 5: Hole injection layer 6: Hole transport layer 7: Electron blocking layer 8: Hole blocking layer 9: Electron transport layer 10: Electron injection layer

Claims

1. A compound represented by the following chemical formula 1. 【Chemistry 1】 In the above Chemical Formula 1, Ar １ and Ar ２ each independently represents a substituted or unsubstituted C ６－６０ aryl; or C containing one or more selected from the group consisting of substituted or unsubstituted O and S ２－６０ is heteroaryl, R １ ~R ８ are each independently hydrogen; deuterium; or substituted or unsubstituted C ６－６０ aryl, R １ ~R ８ At least one of the is deuterium, Ra-Rd are each independently hydrogen; deuterium; or unsubstituted or deuterium-substituted C ６－６０ It is aryl.

2. Ar １ and Ar ２ are each independently phenyl, biphenylyl, dibenzofuranyl, or dibenzothiophenyl; The Ar １ and Ar ２ are each independently unsubstituted or substituted with one or more deuterium atoms; The compound of claim 1.

3. Ar １ and Ar ２ at least one of the groups is unsubstituted or substituted with one or more deuterium atoms; The compound of claim 1.

4. R １ ~R ８ are each independently hydrogen, deuterium, or phenyl substituted with five deuteriums; R １ ~R ８ At least one of the is deuterium, The compound of claim 1.

5. R １ ~R ８ At least four of the atoms are deuterium. The compound of claim 1.

6. Ra to Rd each independently represent hydrogen, deuterium, phenyl, biphenylyl, terphenylyl, naphthyl, anthracenyl, phenanthrenyl, or triphenylenyl; The phenyl, biphenylyl, terphenylyl, naphthyl, anthracenyl, phenanthrenyl, or triphenylenyl are each independently unsubstituted or substituted with one or more deuterium atoms. The compound of claim 1.

7. Ra to Rd each independently represent hydrogen, phenyl, biphenylyl, terphenylyl, naphthyl, anthracenyl, phenanthrenyl, or triphenylenyl; The phenyl, biphenylyl, terphenylyl, naphthyl, anthracenyl, phenanthrenyl, or triphenylenyl are each independently unsubstituted or substituted with one or more deuterium atoms. The compound of claim 1.

8. Any one of Ra to Rd is phenyl, biphenylyl, terphenylyl, naphthyl, anthracenyl, phenanthrenyl, or triphenylenyl; the phenyl, biphenylyl, terphenylyl, naphthyl, anthracenyl, phenanthrenyl and triphenylenyl are each independently unsubstituted or substituted with one or more deuterium atoms; The remainder is hydrogen. The compound of claim 1.

9. The compound represented by the formula 1 is any one selected from the group consisting of: The compound of claim 1. 【Chemistry 2】 【Chemistry 3】 【Chemistry 4】 【Chemistry 5】 【Chemistry 6】 【Chemistry 7】 【Chemistry 8】 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】 【Chemistry 16】 【Chemistry 17】 【Chemistry 18】 【Chemistry 19】 【Chemistry 20】 【Chemistry 21】 【Chemical 22】 【Chemistry 23】 【Chemistry 24】 【Chemistry 25】 【Chemistry 26】 【Chemical 27】 【Chemistry 28】 【Chemical Formula 29】 【Chemistry 30】

10. 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, At least one of the organic layers contains a compound according to any one of claims 1 to 9. Organic light-emitting devices.

11. The organic layer is a light-emitting layer. The organic light-emitting device according to claim 10.

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