Novel compounds and organic light-emitting devices comprising the same

Abstract

The present invention relates to novel compounds and organic light emitting devices comprising the same.

Description

Technical Field

[0001] Cross-reference with related applications

[0002] This application claims priority based on Korean Patent Application No. 10-2022-0005128 dated January 13, 2022 and Korean Patent Application No. 10-2022-0157379 dated November 22, 2022, the entire contents disclosed in those Korean patent applications being incorporated into this specification.

[0003] This invention relates to novel compounds and organic light-emitting devices containing the same. Background Technology

[0004] Organic light emission typically refers to the phenomenon of converting electrical energy into light energy using organic materials. Organic light-emitting devices (OLEDs) utilizing organic light emission exhibit wide viewing angles, excellent contrast ratios, fast response times, and superior brightness, driving voltage, and response speed characteristics, thus attracting extensive research.

[0005] Organic light-emitting devices (OLEDs) typically have a structure comprising an anode and a cathode, and an organic layer located between the anode and cathode. To improve the efficiency and stability of OLEDs, the organic layer is often formed by a multilayer structure composed of different materials, such as a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. In such an OLED structure, if a voltage is applied between the two electrodes, holes are injected into the organic layer from the anode, and electrons are injected into the organic layer from the cathode. When the injected holes and electrons meet, an exciton is formed. When this exciton re-enters the ground state, it emits light.

[0006] For organic materials used in organic light-emitting devices as described above, there is a continuous need to develop new materials.

[0007] Existing technical documents

[0008] Patent documents

[0009] (Patent Document 1) Korean Patent Publication No. 10-2000-0051826 Summary of the Invention

[0010] Technical issues

[0011] This invention relates to novel organic light-emitting materials and organic light-emitting devices containing the same.

[0012] Solution to the problem

[0013] This invention provides compounds represented by the following chemical formula 1:

[0014] [Chemical Formula 1]

[0015]

[0016] In the above chemical formula 1,

[0017] Ar1 and Ar3 are each independently substituted or unsubstituted C. 6-60 aryl; or substituted or unsubstituted C containing one or more of N, O, and S. 2-60 Heteroaryl, but two or more of Ar1 to Ar3 are substituted or unsubstituted C1s or C2s selected from N, O and S. 2-60 Mixed aromatics,

[0018] Ar2 can be a pyrimidinyl group substituted with two phenyl groups, a triazine group substituted with two phenyl groups, an imidazolyl group substituted with two phenyl groups and one methyl group, a phenylquinazolinyl group, a phenylpyridazinyl group, or a benzo[] group. Azolyl, benzothiazolyl, methylbenzimidazolyl, ethylbenzimidazolyl, or phenylbenzimidazolyl

[0019] The Ar2 atoms mentioned above were either not substituted or were substituted by more than one deuterium atom.

[0020] Ar4 can be hydrogen, phenyl, biphenyl, or naphthyl.

[0021] When Ar4 is phenyl, biphenyl, or naphthyl, Ar4 is either unsubstituted or substituted with one or more deuterium groups.

[0022] L1 is a single bond, or a substituted or unsubstituted C6-60 aryl group.

[0023] R1 to R3 are each independently either hydrogen or deuterium.

[0024] n1 is an integer from 0 to 2.

[0025] n2 and n3 are each independent integers from 0 to 4.

[0026] In addition, the present invention provides an organic light-emitting device, comprising: a first electrode, a second electrode disposed opposite to the first electrode, and an organic layer of one or more disposed between the first electrode and the second electrode, wherein one or more of the organic layers comprises a compound represented by the above chemical formula 1.

[0027] Invention Effects

[0028] The compounds represented by the above-described chemical formula 1 can be used as materials for the organic layer of organic light-emitting devices, thereby achieving improved efficiency, lower driving voltage, and / or improved lifetime characteristics in organic light-emitting devices. In particular, the compounds represented by the above-described chemical formula 1 can be used as materials for hole injection, hole transport, light emission, electron transport, and / or electron injection. Attached Figure Description

[0029] Figure 1 The illustration shows an example of an organic light-emitting device consisting of a substrate 1, an anode 2, a light-emitting layer 3, an electron injection and transport layer 4, and a cathode 5.

[0030] Figure 2 The illustration shows an example of an organic light-emitting device consisting of a substrate 1, an anode 2, a hole injection layer 6, a first hole transport layer 7, a second hole transport layer 8, a light-emitting layer 3, an electron injection and transport layer 4, and a cathode 5. Detailed Implementation

[0031] The invention will now be described in more detail to aid in understanding.

[0032] The present invention provides compounds represented by the above chemical formula 1.

[0033] In this instruction manual, This indicates a bond that is linked to other substituents.

[0034] In this specification, the term "substituted or unsubstituted" refers to a group selected from deuterium; halogen group; nitrile group; nitro group; hydroxyl group; carbonyl group; ester group; imide group; amino group; phosphine oxide group; alkoxy group; aryloxy group; alkyl thio group. aryl thiols alkylsulfonyl arylsulfonyl Silyl; boronyl; alkyl; cycloalkyl; alkenyl; aryl; aralkyl; arylene; alkylaryl; alkylamino; aralkylamino; heteroarylamino; arylamino; arylphosphinyl; or a substituent consisting of one or more heteroaryl groups containing N, O, and S atoms, substituted or unsubstituted, or substituted or unsubstituted by two or more substituents linked together as exemplified above. For example, "a substituent consisting of two or more substituents linked together" can be biphenyl. That is, biphenyl can be aryl, or it can be interpreted as a substituent consisting of two phenyl groups linked together.

[0035] In this specification, the number of carbon atoms in the carbonyl group is not particularly limited, but it is preferred to have 1 to 40 carbon atoms. Specifically, it can be a substituent with the following structures, but is not limited thereto.

[0036]

[0037] In this specification, the oxygen in the ester group can be replaced by a straight-chain, branched, or cyclic alkyl group having 1 to 25 carbon atoms, or an aryl group having 6 to 25 carbon atoms. Specifically, it can be a substituent of the following structural formula, but is not limited thereto.

[0038]

[0039] In this specification, the number of carbon atoms in the imide group is not particularly limited, but it is preferred to have 1 to 25 carbon atoms. Specifically, it can be a substituent with the following structure, but is not limited thereto.

[0040]

[0041] In this specification, silanes specifically include trimethylsilane, triethylsilane, tert-butyldimethylsilane, vinyldimethylsilane, propyldimethylsilane, triphenylsilane, diphenylsilane, phenylsilane, etc., but are not limited to these.

[0042] In this specification, boron groups specifically include trimethylboronyl, triethylboronyl, tert-butyldimethylboronyl, triphenylboronyl, phenylboronyl, etc., but are not limited to these.

[0043] Examples of halogen groups in this specification include fluorine, chlorine, bromine, or iodine.

[0044] In this specification, the alkyl group can be straight-chain 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 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 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, etc., but are not limited to these.

[0045] In this specification, the alkenyl group can be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to yet another embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, styryl, styryl, etc., but are not limited to these.

[0046] In this specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group with 3 to 60 carbon atoms. 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. Specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, etc., are used, but are not limited to these.

[0047] In this specification, the aryl group is not particularly limited, but is preferably an aryl group with 6 to 60 carbon atoms, and can be a monocyclic aryl or polycyclic aryl. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to another embodiment, the aryl group has 6 to 20 carbon atoms. Regarding the aforementioned aryl group, as a monocyclic aryl group, it can be phenyl, biphenyl, terphenyl, etc., but is not limited to these. As the aforementioned polycyclic aryl group, it can be naphthyl, anthraceneyl, phenanthryl, pyrene, perylene, etc. It includes bases, fluorenes, etc., but is not limited to these.

[0048] In this specification, the fluorene group can be substituted, and two substituents can combine with each other to form a spirostructure. When the fluorene group is substituted as described above, it can become... Etc. But it is not limited to this.

[0049] In this specification, a heteroaryl group is a heteroaryl group containing one or more of O, N, Si, and S as heteroelements. The number of carbon atoms is not particularly limited, but is preferably 2 to 60. According to one embodiment, the heteroaryl group has 6 to 30 carbon atoms. According to another embodiment, the heteroaryl group has 6 to 20 carbon atoms. Examples of heteroaryl groups include thiophene, furanyl, pyrrole, imidazolyl, and thiazolyl. azole group, Diazolyl, Triazolyl, Pyridyl, Bipyridyl, Pyrimidinyl, Triazinyl, Acridineyl, Pyridazinyl, Quinolinyl, Quinazolinyl, Quinoxalinyl, Phtharazineyl, Pyridopyrimidinyl, Pyridopyrazinyl, Pyrazenopyrazinyl, Isoquinolinyl, Indoleyl, Carbazoleyl, Benzo[] Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazole, benzothiophene, dibenzothiophene, benzofuranyl, phenanthroline, iso Azolyl, thiadiazolyl, phenthiazinyl, and dibenzofuranyl groups, but not limited to these.

[0050] In this specification, the aryl groups in aralkyl, aryl-alkenyl, alkylaryl, and arylamine are the same as those exemplified above. In this specification, the alkyl groups in aralkyl, alkylaryl, and alkylamine are the same as those exemplified above. In this specification, the heteroaryl groups in heteroarylamines are subject to the above description of heteroaryl groups. In this specification, the alkenyl groups in aryl-alkenyl are the same as those exemplified above. In this specification, arylene is a divalent group; otherwise, the above description of aryl groups applies. In this specification, heteroarylene is a divalent group; otherwise, the above description of heteroaryl groups applies. In this specification, the hydrocarbon ring is not a monovalent group but is formed by the combination of two substituents; otherwise, the above description of aryl or cycloalkyl groups applies. In this specification, heteroaryl is not a monovalent group but is formed by the combination of two substituents; otherwise, the above description of heteroaryl groups applies.

[0051] On the other hand, in this specification, the terms "first" and "second" should be understood as being arbitrarily ordered to distinguish between the two.

[0052] Preferably, the above chemical formula 1 can be represented by any one of the following chemical formulas 1-1 to 1-4:

[0053] [Chemical Formula 1-1]

[0054]

[0055] [Chemical Formula 1-2]

[0056]

[0057] [Chemical Formulas 1-3]

[0058]

[0059] [Chemical Formulas 1-4]

[0060]

[0061] In the above chemical formulas 1-1 to 1-4,

[0062] The descriptions of Ar1 to Ar4, L1, R1 to R3 and n1 to n3 are the same as those in the definitions in Formula 1 above.

[0063] Preferably, Ar1 can be substituted or unsubstituted C. 6-20 aryl; or substituted or unsubstituted C containing one or more of N, O, and S. 2-20 Mixed aromatics,

[0064] More preferably, Ar1 can be phenyl, biphenyl, naphthyl, pyrimidinyl substituted with two phenyl groups, triazine substituted with two phenyl groups, phenylquinazolinyl, phenylpyridazinyl, or benzo[] The Ar1 group can be azole, benzothiazolyl, ethylbenzimidazolyl, or phenylbenzimidazolyl, and may be unsubstituted or substituted with one or more deuterium groups.

[0065] Most preferably, Ar1 can be any one of the following groups:

[0066]

[0067] Preferably, Ar3 can be a substituted or unsubstituted C containing one or more of N, O, and S. 2-20 Mixed aromatics,

[0068] More preferably, Ar3 can be a pyrimidinyl group substituted with two phenyl groups, a triazine group substituted with two phenyl groups, an imidazolyl group substituted with two phenyl groups and one methyl group, a phenylquinazolinyl group, a phenylpyridazinyl group, or a benzo[] group. The Ar3 group can be azole, benzothiazolyl, methylbenzimidazolyl, ethylbenzimidazolyl, or phenylbenzimidazolyl, and may be unsubstituted or substituted with one or more deuterium groups.

[0069] Most preferably, Ar2 and Ar3 can each be independently selected from any of the following groups:

[0070]

[0071] Preferably, Ar2 and Ar3 can be the same as each other.

[0072] Preferably, Ar1 to Ar3 can be the same as each other.

[0073] Preferably, Ar4 can be hydrogen, an unsubstituted or 5-deuterium-substituted phenyl group, an unsubstituted or 9-deuterium-substituted biphenyl group, or an unsubstituted or 7-deuterium-substituted naphthyl group.

[0074] Preferably, when Ar4 is not hydrogen, L1-Ar1 and Ar4 can be the same as each other.

[0075] Representative examples of compounds represented by the above chemical formula 1 are shown below:

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085] As an example, the compound represented by the above chemical formula 1 can be manufactured by the manufacturing method shown in reaction formula 1 below, and other compounds can be manufactured in a similar manner.

[0086] [Reaction Formula 1]

[0087]

[0088] In the above reaction formula 1, L1 and Ar1 to Ar4 are defined as in the above chemical formula 1, and X is a halogen, preferably chlorine or bromine.

[0089] The above-described reaction formula 1 is a Suzuki coupling reaction, preferably carried out in the presence of a palladium catalyst and a base. The reactive group used in the Suzuki coupling reaction can be modified according to techniques known in the art. The above manufacturing method can be further specified in the manufacturing examples described later.

[0090] Furthermore, the present invention provides an organic light-emitting device comprising a compound represented by the above-described chemical formula 1. As an example, the present invention provides an organic light-emitting device comprising: a first electrode, a second electrode disposed opposite to the first electrode, and one or more organic layers disposed between the first electrode and the second electrode, wherein one or more of the organic layers comprises a compound represented by the above-described chemical formula 1.

[0091] The organic layer of the organic light-emitting device of the present invention can be formed as a single layer or as a multilayer structure with two or more organic layers stacked on top of each other. For example, the organic light-emitting device of the present invention can have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer as organic layers. However, the structure of the organic light-emitting device is not limited to this and may include fewer organic layers.

[0092] In addition, the organic layer may also include a light-emitting layer, which may contain a compound represented by the above chemical formula 1.

[0093] In addition, the aforementioned organic layer may include a hole transport layer, a hole injection layer, or a layer that performs both hole transport and hole injection simultaneously, and the aforementioned hole transport layer, hole injection layer, or layer that performs both hole transport and hole injection simultaneously may contain a compound represented by the aforementioned chemical formula 1.

[0094] In addition, the aforementioned organic layer may include an electron transport layer, an electron injection layer, or an electron injection and transport layer, wherein the aforementioned electron transport layer, electron injection layer, or electron injection and transport layer may contain a compound represented by the aforementioned chemical formula 1.

[0095] Furthermore, the organic light-emitting device according to the present invention can be a structure (normal type) in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate. Additionally, the organic light-emitting device according to the present invention can be a reverse structure (inverted type) in which a cathode, one or more organic layers, and an anode 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 below. Figure 1 and Figure 2 .

[0096] Figure 1 The illustration shows an example of an organic light-emitting device consisting of a substrate 1, an anode 2, a light-emitting layer 3, an electron injection and transport layer 4, and a cathode 5. Figure 2 The illustration shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a hole injection layer 6, a first hole transport layer 7, a second hole transport layer 8, a light-emitting layer 3, an electron injection and transport layer 4, and a cathode 5. In the structure described above, the compound represented by the above-described chemical formula 1 may be included in the electron injection and transport layer.

[0097] The organic light-emitting device according to the present invention, except that one or more of the organic layers contain a compound represented by the above-described chemical formula 1, can be manufactured using materials and methods known in the art. Furthermore, when the organic light-emitting device comprises a plurality of organic layers, the organic layers can be formed from the same substance or different substances.

[0098] For example, the organic light-emitting device according to the present invention can be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. This can be achieved by: depositing a metal or a conductive metal oxide or alloy thereof onto the substrate using a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation to form an anode; then forming an organic layer comprising a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer on the anode; and finally depositing a material suitable for use as a cathode onto the organic layer. Alternatively, the organic light-emitting device can also be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material onto the substrate.

[0099] Furthermore, the compound represented by the above chemical formula 1 can be used to form an organic layer in the manufacture of organic light-emitting devices not only by vacuum evaporation but also by solution coating. Here, solution coating refers to methods such as spin coating, dip coating, blade coating, inkjet printing, screen printing, spray coating, and roller coating, but is not limited to these.

[0100] In addition to these methods, organic light-emitting devices can also be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate (WO 2003 / 012890). However, the manufacturing method is not limited to these methods.

[0101] As an example, the first electrode is the anode and the second electrode is the cathode, or the first electrode is the cathode and the second electrode is the anode.

[0102] As the aforementioned anode material, a material with a high work function is preferred in order to facilitate the injection of holes into the organic layer. Specific examples of the aforementioned anode materials include metals such as vanadium, chromium, copper, zinc, and gold, or their alloys; 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; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylidene-1,2-dioxo)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited to these.

[0103] As the cathode material described above, a material with a low work function is generally preferred in order to facilitate the injection of electrons into the organic layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or their alloys; multilayer structures such as LiF / Al or LiO2 / Al, etc., but are not limited to these.

[0104] The aforementioned hole injection layer is a layer that injects holes from the electrode. Preferably, the hole injection material is a compound that possesses the ability to transport holes, the effect of injecting holes from the anode, excellent hole injection performance for the light-emitting layer or light-emitting material, prevents excitons generated in the light-emitting layer from migrating to the electron injection layer or electron injection material, and exhibits excellent thin film formation capability. Preferably, the HOMO (highest occupied molecular orbital) of the hole injection material is between that of the anode material and the HOMO of the surrounding organic layer. Specific examples of hole injection materials include, but are not limited to, metalloporphyrins, oligothiophenes, arylamine-based organic compounds, hexanitrile hexaazabenzophenanthrene-based organic compounds, quinacridone-based organic compounds, perylene-based organic compounds, anthraquinones, and conductive polymers based on polyaniline and polythiophene.

[0105] The aforementioned hole transport layer is a layer that receives holes from the hole injection layer and transports them to the light-emitting layer. The hole transport material is a material capable of receiving holes from the anode or hole injection layer and transferring them to the light-emitting layer; materials with high hole mobility are suitable. Specific examples include aryl amine-based organic compounds, conductive polymers, and block copolymers that simultaneously contain conjugated and non-conjugated portions, but are not limited to these.

[0106] The aforementioned luminescent material is capable of receiving holes and electrons from the hole transport layer and electron transport layer, respectively, and combining them to emit light in the visible light region. Preferably, it is a material with high quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxyquinoline aluminum complex (Alq3), carbazole compounds, and dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; and benzo[…]. Compounds of the azole, benzothiazole and benzimidazole series; poly(p-phenylenevinylene) (PPV) polymers; spirocyclic compounds; polyfluorene, fluorene, etc., but not limited to these.

[0107] The aforementioned luminescent layer may comprise a host material and a dopant material. The host material may be an aromatic fused-ring derivative or a heterocyclic compound. Specifically, aromatic fused-ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentane derivatives, phenanthrene compounds, and fluoranthene compounds; heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, and ladder-type furan compounds. Pyrimidine derivatives, etc., but not limited to these.

[0108] As dopant materials, there are aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, aromatic amine derivatives are aromatic fused-ring derivatives with substituted or unsubstituted aryl amino groups, such as pyrene, anthracene, etc. Diindrone pyrene, etc., styrylamine compounds are compounds in which at least one aryl vinyl group is substituted onto a substituted or unsubstituted arylamine, and is substituted or unsubstituted by one or more substituents selected from aryl, silyl, alkyl, cycloalkyl, and arylamino groups. Specifically, there are styrylamines, styryldiamines, styryltriamines, styryltetraamines, etc., but they are not limited to these. In addition, as metal complexes, there are iridium complexes, platinum complexes, etc., but they are not limited to these.

[0109] The aforementioned electron transport layer is the layer that receives electrons from the electron injection layer and transports them to the light-emitting layer. The electron transport material is a substance capable of effectively receiving electrons from the cathode and transferring them to the light-emitting layer; substances with high electron mobility are suitable. Specific examples include Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free radical compounds, hydroxyflavonoid-metal complexes, etc., but are not limited to these. The electron transport layer can be used with any desired cathode material as used in the prior art. In particular, suitable examples of cathode materials are common materials with low work functions and accompanied by an aluminum or silver layer. Specifically, cesium, barium, calcium, ytterbium, and samarium are all accompanied by an aluminum or silver layer. Preferably, compounds represented by the above-described chemical formula 1 can be used as the electron transport material.

[0110] The aforementioned electron injection layer is a layer that injects electrons from the electrode. Preferably, compounds are those that possess electron transport capabilities, effectively inject electrons from the cathode, exhibit excellent electron injection performance for the light-emitting layer or light-emitting material, prevent excitons generated in the light-emitting layer from migrating to the hole injection layer, and possess excellent thin-film forming ability. Specifically, these include fluorenone, anthraquinone dimethyl ether, biphenylquinone, thiamethoxam dioxide, etc. azole, Diazoles, triazoles, imidazoles, perylenetetracarboxylic acids, fluorenemethane, anthrones, and their derivatives, metal coordination compounds, and nitrogen-containing five-membered ring derivatives, etc., but not limited thereto. Preferably, compounds represented by the above chemical formula 1 can be used as electron-injecting substances.

[0111] Examples of the aforementioned metal coordination compounds include lithium 8-hydroxyquinoline, bis(8-hydroxyquinoline)zinc, bis(8-hydroxyquinoline)copper, bis(8-hydroxyquinoline)manganese, tris(8-hydroxyquinoline)aluminum, tris(2-methyl-8-hydroxyquinoline)aluminum, tris(8-hydroxyquinoline)gallium, bis(10-hydroxybenzo[h]quinoline)beryllium, bis(10-hydroxybenzo[h]quinoline)zinc, bis(2-methyl-8-quinoline)gallium chloride, bis(2-methyl-8-quinoline)(o-cresol)gallium, bis(2-methyl-8-quinoline)(1-naphthol)aluminum, and bis(2-methyl-8-quinoline)(2-naphthol)gallium, but are not limited to these.

[0112] On the other hand, in this invention, the “electron injection and transport layer” is a layer that fully utilizes the functions of the aforementioned electron injection layer and the aforementioned electron transport layer. It can be a substance that performs the functions of the aforementioned layers, either alone or in combination, but is not limited to this.

[0113] The organic light-emitting device according to the present invention can be a bottom-emission device, a top-emission device, or a bidirectional light-emitting device, and in particular, it can be a bottom-emission device that requires relatively high luminous efficiency.

[0114] In addition, the compound represented by the above chemical formula 1 can be included not only in organic light-emitting devices, but also in organic solar cells or organic transistors.

[0115] The present invention will now be described in more detail to aid in understanding. However, the embodiments described below are merely illustrative of the invention, and the scope of the invention is not limited to the embodiments described below.

[0116] [Manufacturing Example]

[0117] Manufacturing Example 1: Manufacturing of Compound E1

[0118]

[0119] Under a nitrogen atmosphere, compounds E1-A (20 g, 51.5 mmol) and E1-B (44.8 g, 103.0 mmol) were added to 400 mL of tetrahydrofuran, stirred, and refluxed. Then, potassium carbonate (21.4 g, 154.6 mmol) dissolved in 21 mL of water was added, and after thorough stirring, tetra(triphenylphosphine)palladium (1.8 g, 1.5 mmol) was added. After reacting for 2 hours, the mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was distilled off. It was then added back to 869 mL of chloroform and dissolved. After washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was stirred and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce a white solid compound E1 (29.1 g, 67%).

[0120] MS:[M+H] + =843

[0121] Manufacturing Example 2: Manufacturing of Compound E2

[0122]

[0123] The starting materials were used as described in the above reaction formula, except that the above compound E2 was manufactured by the same method as that used in manufacturing example 1.

[0124] MS:[M+H] + =819

[0125] Manufacturing Example 3: Manufacturing of Compound E3

[0126]

[0127] The starting materials were used as described in the above reaction formula, except that the above compound E3 was manufactured by the same method as that used in manufacturing example 1.

[0128] MS:[M+H] + =769

[0129] Manufacturing Example 4: Manufacturing of Compound E4

[0130]

[0131] The starting materials were used as described in the above reaction formula, except that the above compound E4 was manufactured by the same method as that used in manufacturing example 1.

[0132] MS:[M+H] + =595

[0133] Manufacturing Example 5: Manufacturing of Compound E5

[0134]

[0135] The starting materials were used as described in the above reaction formula, except that the above compound E5 was manufactured by the same method as that used in manufacturing example 1.

[0136] MS:[M+H] + =715

[0137] Manufacturing Example 6: Manufacturing of Compound E6

[0138]

[0139] The starting materials were used as described in the above reaction formula, except that the above compound E6 was manufactured by the same method as that used in manufacturing example 1.

[0140] MS:[M+H] + =845

[0141] Manufacturing Example 7: Manufacturing of Compound E7

[0142]

[0143] The starting materials were used as described in the above reaction formula, except that the above compound E7 was manufactured by the same method as that used in manufacturing example 1.

[0144] MS:[M+H] + =617

[0145] Manufacturing Example 8: Manufacturing of Compound E8

[0146]

[0147] The starting materials were used as described in the above reaction formula, except that the above compound E8 was manufactured by the same method as that used in manufacturing example 1.

[0148] MS:[M+H] + =691

[0149] Manufacturing Example 9: Manufacturing of Compound E9

[0150]

[0151] Under a nitrogen atmosphere, compounds E9-A (20 g, 35 mmol) and E9-B (15.2 g, 35 mmol) were added to 400 ml of a distillate. In a Dioxane solution, the mixture was stirred and refluxed. Potassium phosphate (22.3 g, 105.1 mmol) was dissolved in 22 mL of water and added to the solution. After thorough stirring, palladium dibenzylacetone (0.6 g, 1.1 mmol) and tricyclohexylphosphine (0.6 g, 2.1 mmol) were added. After reacting for 7 hours, the mixture was cooled to room temperature, and the resulting solid was filtered. The solid was dissolved in 887 mL of chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce a yellow solid compound E9 (4.4 g, 15%).

[0152] MS:[M+H] + =844

[0153] Manufacturing Example 10: Manufacturing of Compound E10

[0154]

[0155] The starting materials were used as described in the above reaction formula, except that the above compound E10 was manufactured by the same method as that used in manufacturing example 9.

[0156] MS:[M+H] + =817

[0157] Manufacturing Example 11: Manufacturing of Compound E11

[0158]

[0159] The starting materials were used as described in the above reaction formula, except that the above compound E11 was manufactured by the same method as that used in manufacturing example 9.

[0160] MS:[M+H] + =768

[0161] Manufacturing Example 12: Manufacturing of Compound E12

[0162]

[0163] Under a nitrogen atmosphere, compounds E12-A (20 g, 63.5 mmol) and E12-B (82.1 g, 190.5 mmol) were added to 400 mL of tetrahydrofuran, stirred, and refluxed. Then, potassium carbonate (26.3 g, 190.6 mmol) was dissolved in 26 mL of water and added to the solution. After thorough stirring, tetra(triphenylphosphine)palladium (2.2 g, 1.9 mmol) was added. After reacting for 1 hour, the mixture was cooled to room temperature, and the organic and aqueous layers were separated. The organic layer was distilled off. It was then dissolved in 1271 mL of chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce a white solid compound E12 (44.5 g, 70%).

[0164] MS:[M+H] + =1000

[0165] Manufacturing Example 13: Manufacturing of Compound E13

[0166]

[0167] The starting materials were used as described in the above reaction formula, except that the above compound E13 was manufactured by the same method as that used in manufacturing example 12.

[0168] MS:[M+H] + =706

[0169] Manufacturing Example 14: Manufacturing of Compound E14

[0170]

[0171] The starting materials were used as described in the above reaction formula, except that the above compound E14 was manufactured by the same method as that used in manufacturing example 12.

[0172] MS:[M+H] + =769

[0173] Manufacturing Example 15: Manufacturing of Compound E15

[0174]

[0175] The starting materials were used as described in the above reaction formula, except that the above compound E15 was manufactured by the same method as that used in manufacturing example 12.

[0176] MS:[M+H] + =782

[0177] Manufacturing Example 16: Manufacturing of Compound E16

[0178]

[0179] The starting materials were used as described in the above reaction formula, except that the above compound E16 was manufactured by the same method as that used in manufacturing example 1.

[0180] MS:[M+H] + =774

[0181] [Example]

[0182] Example 1

[0183] ITO (indium tin oxide) is used as A glass substrate coated with a thin film of ITO was immersed in distilled water containing detergent and washed using ultrasound. The detergent used was from Fischer Co., and the distilled water was filtered twice using a filter manufactured by Millipore Co. After washing the ITO for 30 minutes, the process was repeated twice with distilled water for 10 minutes of ultrasonic washing. Following the distilled water washing, the substrate was ultrasonically washed with a solvent of isopropanol, acetone, and methanol, dried, and then transferred to a plasma cleaner. Additionally, the substrate was cleaned with oxygen plasma for 5 minutes before being transferred to a vacuum evaporation machine.

[0184] On the ITO transparent electrode prepared in this way, the following compound HI-A is applied... A hole injection layer is formed by thermal vacuum evaporation to a thickness of [amount missing]. The following compounds are then sequentially applied to the hole injection layer. and the following compounds The first hole transport layer and the second hole transport layer are formed by vacuum evaporation.

[0185] Next, on the aforementioned second hole transport layer, with a film thickness... The following compounds, BH and BD, were vacuum-deposited in a weight ratio of 25:1 to form a light-emitting layer.

[0186] On the aforementioned light-emitting layer, the compound E1 manufactured above and the compound LiQ described below are vacuum-deposited in a 1:1 weight ratio, thereby achieving... The thickness forms an electron injection and transport layer. On this electron injection and transport layer, lithium fluoride (LiF) is sequentially applied... The thickness, using aluminum The cathode is formed by vapor deposition of a certain thickness.

[0187]

[0188] During the above process, the evaporation rate of organic matter is maintained. to Lithium fluoride maintenance of the cathode The evaporation rate of aluminum maintains The evaporation rate is such that the vacuum level is maintained at 1×10⁻⁶ during evaporation. -7 Up to 5×10 -5 This led to the creation of organic light-emitting devices.

[0189] Examples 2 to 16

[0190] Organic light-emitting devices were manufactured using the compounds listed in Table 1 below instead of compound E1, except that the method was the same as that used in Example 1 above.

[0191] Comparative Examples 1 to 4

[0192] Organic light-emitting devices were manufactured using the compounds listed in Table 1 below instead of compound E1, except that the method described in Example 1 above was not used. The compounds ET-1 to ET-4 used in Table 1 below are shown below.

[0193]

[0194] [Experimental Example]

[0195] For the organic light-emitting devices manufactured in Examples 1 to 16 and Comparative Examples 1 to 4 above, at 10 mA / cm 2 The driving voltage and luminous efficiency were measured at a current density of 20 mA / cm². 2 At a current density of [value missing], the time (T90) relative to the initial brightness was measured. The results are shown in Table 1 below.

[0196] [Table 1]

[0197]

[0198]

[0199] As shown in Table 1 above, the compounds represented by Chemical Formula 1 of the present invention can be used in organic layers of organic light-emitting devices that can simultaneously perform electron injection and electron transport, and exhibit excellent effects in terms of driving voltage, efficiency and lifetime.

[0200] [Symbol Explanation]

[0201] 1: Substrate 2: Anode

[0202] 3: Light-emitting layer; 4: Electron injection and transport layer

[0203] 5: Cathode; 6: Hole injection layer

[0204] 7: First hole transport layer; 8: Second hole transport layer.

Claims

1. A compound represented by the following chemical formula 1: [Chemical Formula 1] In the chemical formula 1, Ar1 represents phenyl, biphenyl, naphthyl, pyrimidinyl substituted with two phenyl groups, triazine substituted with two phenyl groups, phenylquinazolinyl, phenylpyridazinyl, or benzo[] The Ar1 group may be further substituted with one or more deuterium groups, including azole, benzothiazolyl, ethylbenzimidazolyl, or phenylbenzimidazolyl groups. Ar3 represents a pyrimidinyl group substituted with two phenyl groups, a triazine group substituted with two phenyl groups, an imidazolyl group substituted with two phenyl groups and one methyl group, a phenylquinazolinyl group, a phenylpyridazinyl group, or a benzo[] group. Azolyl, benzothiazolyl, methylbenzimidazolyl, ethylbenzimidazolyl, or phenylbenzimidazolyl The Ar3 is optionally further replaced by one or more deuterium atoms. Ar2 can be a pyrimidinyl group substituted with two phenyl groups, a triazine group substituted with two phenyl groups, an imidazolyl group substituted with two phenyl groups and one methyl group, a phenylquinazolinyl group, a phenylpyridazinyl group, or a benzo[] group. Azolyl, benzothiazolyl, methylbenzimidazolyl, ethylbenzimidazolyl, or phenylbenzimidazolyl Ar2 may optionally be further replaced by one or more deuterium atoms. Ar4 can be hydrogen, phenyl, biphenyl, or naphthyl. When Ar4 is phenyl, biphenyl, or naphthyl, Ar4 is either unsubstituted or substituted with one or more deuterium atoms. L1 is a single bond, or C 6-60 Alpha-aryl R1 to R3 are each independently either hydrogen or deuterium. n1 is an integer from 0 to 2. n2 and n3 are each independent integers from 0 to 4.

2. The compound according to claim 1, wherein, The chemical formula 1 is represented by any one of the following chemical formulas 1-1 to 1-4: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formulas 1-3] [Chemical Formulas 1-4] In the chemical formulas 1-1 to 1-4, The descriptions of Ar1 to Ar4, L1, R1 to R3 and n1 to n3 are the same as those in claim 1.

3. The compound according to claim 1, wherein, Ar1 is selected from any of the following: 。 4. The compound according to claim 1, wherein, Ar2 and Ar3 are each independently selected from any of the following: 。 5. The compound according to claim 1, wherein, Ar2 and Ar3 are identical to each other.

6. The compound according to claim 1, wherein, Ar4 is hydrogen, an unsubstituted or 5-deuterium-substituted phenyl group, an unsubstituted or 9-deuterium-substituted biphenyl group, or an unsubstituted or 7-deuterium-substituted naphthyl group.

7. The compound according to claim 1, wherein, When Ar4 is not hydrogen, L1-Ar1 and Ar4 are identical.

8. The compound according to claim 1, wherein, The compound represented by the chemical formula 1 is selected from any one of the following: 。 9. An organic light-emitting device, comprising: A first electrode, a second electrode disposed opposite to the first electrode, and an organic layer of one or more layers disposed between the first electrode and the second electrode, wherein one or more of the organic layers comprises the compound according to any one of claims 1 to 8.

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

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