Novel compound and organic light-emitting device containing the same

Abstract

The present invention provides novel compounds and organic light-emitting devices using the same.

Description

Technical Field

[0001] Cross-references to related applications

[0002] This application claims priority based on Korean Patent Application No. 10-2020-0120013 filed on September 17, 2020 and Korean Patent Application No. 10-2021-0121855 filed on September 13, 2021, and incorporates all disclosures of the Korean patent applications into this specification.

[0003] The present invention relates to novel compounds and organic light-emitting devices containing the same. Background Art

[0004] Organic light emitting diodes (OLEDs) are currently under extensive research due to their wide viewing angles, excellent contrast, and fast response times, as well as their superior brightness, drive voltage, and response speed.

[0005] An organic light-emitting device typically has a structure comprising an anode, a cathode, and an organic layer positioned between the anode and cathode. To improve the efficiency and stability of an organic light-emitting device, the organic layer is often formed from multiple layers composed of different materials. For example, it can be composed of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. In such an organic light-emitting device structure, when a voltage is applied between the two electrodes, holes are injected from the anode into the organic layer, and electrons are injected from the cathode into the organic layer. When the injected holes and electrons meet, excitons are formed. When these excitons transition back to the ground state, light is emitted.

[0006] As for organic substances used in the organic light-emitting devices described above, there is a continuous demand for the development of new materials.

[0007] Prior art literature

[0008] Patent Literature

[0009] (Patent Document 0001) Korean Patent Publication No. 10-2000-0051826 Summary of the Invention

[0010] Technical issues

[0011] The present invention relates to novel compounds and organic light-emitting devices containing the same.

[0012] Solution to the problem

[0013] The present invention provides a compound represented by the following Chemical Formula 1:

[0014] [Chemical Formula 1]

[0015]

[0016] In the above chemical formula 1,

[0017] Ar1 is substituted or unsubstituted C 6-60 Aryl; or substituted or unsubstituted C containing any one or more heteroatoms selected from N, O and S 2-60 heteroaryl,

[0018] Two of R1 to R5 are each independently N(Ar2)(Ar3), and the others are each independently hydrogen or deuterium,

[0019] However, this does not include the case where R2 and R4 are both N(Ar2)(Ar3).

[0020] Ar2 and Ar3 are each independently substituted or unsubstituted C 6-60 Aryl; or substituted or unsubstituted C containing any one or more heteroatoms selected from N, O and S 2-60 Heteroaryl.

[0021] Effects of the Invention

[0022] The compound represented by the above Chemical Formula 1 can be used as a material for an organic layer of an organic light-emitting device, and can achieve improved efficiency, lower driving voltage, and / or improved lifespan characteristics in the organic light-emitting device.

[0023] In particular, the compound represented by the above Chemical Formula 1 may be used as a hole injection, hole transport, hole injection and transport, light emitting, electron transport, or electron injection material. BRIEF DESCRIPTION OF THE DRAWINGS

[0024] Figure 1 The diagram shows an example of an organic light-emitting device composed of a substrate 1 , an anode 2 , a hole transport layer 3 , a light-emitting layer 4 , an electron transport layer 5 , an electron injection layer 6 , and a cathode 7 .

[0025] Figure 2 The diagram shows an example of an organic light-emitting device consisting of a substrate 1, an anode 2, a hole injection layer 8, a hole transport layer 3, an electron blocking layer 9, a light-emitting layer 4, a hole blocking layer 10, an electron transport layer 5, an electron injection layer 6 and a cathode 7. DETAILED DESCRIPTION

[0026] Hereinafter, the present invention will be described in more detail to facilitate understanding.

[0027] (Definition of terms)

[0028] In this manual, It represents a bond to other substituents.

[0029] In the present specification, the term "substituted or unsubstituted" refers to a group selected from deuterium; a halogen group; a cyano group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a phosphine oxide group; an alkoxy group; an aryloxy group; an alkylthio group; Arylthio Alkylsulfonyl Arylsulfonyl Silyl; boryl; alkyl; cycloalkyl; alkenyl; aryl; aralkyl; aralkenyl; alkylaryl; alkylamino; aralkylamino; heteroarylamino; arylamino; arylphosphino; or substituted or unsubstituted with one or more substituents selected from heteroaryl groups containing one or more N, O and S atoms, or substituted or unsubstituted with two or more substituents connected among the substituents exemplified above. For example, "a substituent formed by two or more substituents connected" can be a biphenyl group. That is, the biphenyl group can be an aryl group, and can also be interpreted as a substituent formed by two phenyl groups connected. As an example, the term "substituted or unsubstituted" can be understood as "unsubstituted; or selected from deuterium, a halogen group, C 1-10 Alkyl, C 1-10 Alkoxy and C 6-20 In the present specification, the term “substituted with one or more substituents” can be understood to mean, for example, “substituted with one to five substituents” or “substituted with one or two substituents”.

[0030] In the present specification, the number of carbon atoms in the carbonyl group is not particularly limited, but preferably the number of carbon atoms is 1 to 40. Specifically, the substituents may be of the following structures, but are not limited thereto.

[0031]

[0032] 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 substituents may be those of the following structural formulas, but are not limited thereto.

[0033]

[0034] In the present specification, the number of carbon atoms in the imide group is not particularly limited, but preferably the number of carbon atoms is 1 to 25. Specifically, the substituent may be a substituent of the following structure, but the substituent is not limited thereto.

[0035]

[0036] In the present specification, specific examples of the silyl group include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, and phenylsilyl, but are not limited thereto.

[0037] In the present specification, specific examples of the boryl group include trimethylboryl, triethylboryl, tert-butyldimethylboryl, triphenylboryl, and phenylboryl, but are not limited thereto.

[0038] In the present specification, examples of the halogen group include fluorine, chlorine, bromine, and iodine.

[0039] In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the number of carbon atoms in the alkyl group is 1 to 20. According to another embodiment, the number of carbon atoms in the alkyl group is 1 to 10. According to another embodiment, specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, 1-ethyl-propyl, 1,1-dimethylpropyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, isohexyl, 1-methylhexyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 5-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2,4,4-trimethyl-1-pentyl, 2,4,4-trimethyl-2-pentyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, etc., but are not limited thereto.

[0040] In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to 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 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-phenylethen-1-yl, 2-phenylethen-1-yl, 2,2-diphenylethen-1-yl, 2-phenyl-2-(naphthalen-1-yl)ethen-1-yl, 2,2-bis(diphenyl-1-yl)ethen-1-yl, stilbene, and styryl, but are not limited thereto.

[0041] In this specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 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. 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.

[0042] In this specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group having aromaticity. According to one embodiment, the carbon number of the aryl group is 6 to 30. According to one embodiment, the carbon number of the aryl group is 6 to 20. Regarding the aryl group, as a monocyclic aryl group, it may be phenyl, biphenyl, terphenyl, etc., but is not limited thereto. As the polycyclic aryl group, it may be naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, perylene, Base, etc., but not limited to this.

[0043] In the present specification, the heteroaryl group is a heteroaryl group containing one or more hetero elements selected from O, N, Si and S. The number of carbon atoms is not particularly limited, but preferably the number of carbon atoms is 2 to 60. Examples of the heteroaryl group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, Azolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzo[omicron] oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothiophenyl, dibenzothiophenyl, benzofuranyl, phenanthroline, isothiophene oxazolyl, thiadiazolyl, phenothiazinyl and dibenzofuranyl, etc., but are not limited thereto.

[0044] In this specification, the aryl group in aralkyl, aralkenyl, alkylaryl, arylamine, and arylsilyl groups is the same as the examples of aryl groups described above. In this specification, the alkyl group in aralkyl, alkylaryl, and alkylamine groups is the same as the examples of alkyl groups described above. In this specification, the heteroaryl group in heteroarylamine is the same as the examples of heteroaryl groups described above. In this specification, the alkenyl group in aralkenyl is the same as the examples of alkenyl groups described above. In this specification, the description of aryl groups described above is applicable except that an arylene group is a divalent group. In this specification, the description of heteroarylene groups described above is applicable except that a heteroarylene group is a divalent group. In this specification, the description of heteroaryl groups described above is applicable except that a hydrocarbon ring is not a monovalent group but is formed by bonding two substituents. In this specification, the description of aryl or cycloalkyl groups described above is applicable except that a heterocycle is not a monovalent group but is formed by bonding two substituents. In this specification, the description of heteroaryl groups described above is applicable except that a heterocycle is not a monovalent group but is formed by bonding two substituents.

[0045] (Compound)

[0046] The present invention provides a compound represented by the above Chemical Formula 1.

[0047] The compound represented by Chemical Formula 1 has a structure based on fluorene as a core, an aryl or heteroaryl group (Ar1), and a phenyl group having two amine substituents bonded thereto, respectively, at carbon number 9 of the core.

[0048] Here, the two amine substituents are each flanked by an aryl or heteroaryl group (N(Ar2)(Ar3)). However, this does not include a case where the two amine substituents are located at the meta position relative to carbon 9 of the nucleus (i.e., where R2 and R4 in the above chemical formula 1 are N(Ar2)(Ar3)).

[0049] In particular, the compound represented by the above chemical formula 1 can exhibit significantly superior capabilities in hole injection, hole transport and electron suppression due to the synergistic effect of the core structure and the position of the amine substituent, compared with the compound in which R2 and R4 are respectively N(Ar2)(Ar3), the compound in which only any one of R1 to R5 is N(Ar2)(Ar3), and the compound in which any one of R1 to R5 is N(Ar2)(Ar3) and N(Ar2)(Ar3) is also combined as a substituent of Ar1.

[0050] Therefore, an organic light-emitting device using the compound represented by the above Chemical Formula 1 as an organic layer of an organic light-emitting device, for example, as a material for a hole transport layer, can exhibit excellent characteristics in terms of driving voltage, luminous efficiency and lifespan compared to organic light-emitting devices using a compound in which R2 and R4 are respectively N(Ar2)(Ar3), a compound in which only any one of R1 to R5 is N(Ar2)(Ar3), and a compound in which any one of R1 to R5 is N(Ar2)(Ar3) and N(Ar2)(Ar3) is also combined as a substituent of Ar1.

[0051] Next, the above-mentioned Chemical Formula 1 and the compounds represented by the chemical formula will be described in detail as follows.

[0052] Preferably, two of R1 to R5 are each N(Ar2)(Ar3),

[0053] Here, the case where R2 and R4 are each N(Ar2)(Ar3) is not included.

[0054] R1 to R5 not represented by N(Ar2)(Ar3) are each independently hydrogen or deuterium.

[0055] Preferably, Ar1 can be substituted or unsubstituted C 6-30 Aryl; or substituted or unsubstituted C containing any one or more heteroatoms selected from N, O and S 2-30 Heteroaryl.

[0056] More preferably, Ar1 may be unsubstituted or selected from deuterium and C 1-10 One or more substituents in the alkyl group substituted C 6-20 Aryl; or unsubstituted or selected from deuterium and C 1-10 One or more substituents in the alkyl group substituted with one heteroatom of N, O and S 2-20 Heteroaryl.

[0057] For example, Ar1 may be a phenyl group, a biphenyl group, a naphthyl group, a phenanthrenyl group, a 9,9-dimethylfluorenyl group, or a dibenzofuranyl group.

[0058] More specifically, Ar can be any one selected from the following groups:

[0059]

[0060] Preferably, Ar2 and Ar3 are each independently substituted or unsubstituted C 6-30 Aryl; or substituted or unsubstituted C containing any one or more heteroatoms selected from N, O and S 2-30 Heteroaryl.

[0061] More preferably, Ar2 and Ar3 are each independently unsubstituted or selected from deuterium and C 1-10 One or more substituents in the alkyl group substituted C 6-20 Aryl; or unsubstituted or selected from deuterium and C 1-10 One or more substituents in the alkyl group substituted with one heteroatom of N, O and S 2-20 Heteroaryl.

[0062] For example, Ar2 and Ar3 may each independently be a phenyl group, a biphenyl group, a naphthyl group, a 9,9-dimethylfluorenyl group, or a dibenzofuranyl group.

[0063] Preferably, Ar2 and Ar3 are each independently unsubstituted or selected from deuterium and C 1-10 One or more substituents in the alkyl group substituted C 6-20 Aryl, or

[0064] At least one of Ar2 and Ar3 is unsubstituted or substituted with a substituted ... 1-10 One or more substituents in the alkyl group substituted with one heteroatom of N, O and S 2-20 Heteroaryl.

[0065] For example, Ar2 and Ar3 can each independently be phenyl, biphenyl, naphthyl, 9,9-dimethylfluorenyl or dibenzofuranyl; or

[0066] At least one of Ar2 and Ar3 may be a dibenzofuranyl group.

[0067] For example, the above Chemical Formula 1 can be represented by any one of the following Chemical Formulas 1-1 to 1-5:

[0068] [Chemical Formula 1-1]

[0069]

[0070] [Chemical formula 1-2]

[0071]

[0072] [Chemical formula 1-3]

[0073]

[0074] [Chemical formula 1-4]

[0075]

[0076] [Chemical Formula 1-5]

[0077]

[0078] In the above Chemical Formulas 1-1 to 1-5,

[0079] Ar 21 、Ar 22 、Ar 31 and Ar 32 are each independently unsubstituted or selected from deuterium and C 1-10 One or more substituents in the alkyl group substituted C 6-20 Aryl; or unsubstituted or selected from deuterium and C 1-10 One or more substituents in the alkyl group substituted with one heteroatom of N, O and S 2-20 heteroaryl,

[0080] R1 to R5 are each independently hydrogen or deuterium,

[0081] Ar1 is the same as defined in the above Chemical Formula 1.

[0082] Preferably, in the above chemical formulas 1-1 to 1-5, Ar 21 and Ar 31 Any one of Ar 22 Same, the other one is the same as Ar 32 same.

[0083] Preferably, in the above chemical formulas 1-1 to 1-5, Ar 21 、Ar 22 、Ar 31 and Ar 32 Each independently may be a phenyl group, a biphenyl group, a naphthyl group, a 9,9-dimethylfluorenyl group or a dibenzofuranyl group.

[0084] Representative examples of the compound represented by the above Chemical Formula 1 are shown below:

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097] Among the above compounds, as the compound represented by Chemical Formula 1-1, in Ar 21 with Ar 22 Same, Ar 31 with Ar 32 In the same case, as an example, the following reaction formula 1 can be used for production.

[0098] [Reaction formula 1]

[0099]

[0100] In the above reaction formula 1, X is independently a halogen, preferably chlorine or bromine, and the descriptions of other substituents are as described above.

[0101] Specifically, the compound represented by Chemical Formula 1-1 is produced by the amine substitution reaction of the starting materials SM1 and SM2. Here, the amine substitution reaction is preferably carried out in the presence of a palladium catalyst and a base, and the reactive group used for the amine substitution reaction can be modified according to techniques known in the art.

[0102] Furthermore, among the compounds represented by the above Chemical Formula 1, compounds having a structure different from that of the above Chemical Formula 1-1 can be produced by appropriately changing the structure of the starting materials in the above Reaction Formula 1. The above production method can be further embodied in the production examples described below.

[0103] (Organic Light-Emitting Devices)

[0104] In another aspect, the present invention provides an organic light-emitting device comprising the 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 disposed opposite 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 the compound represented by Chemical Formula 1.

[0105] The organic layer of the organic light-emitting device of the present invention may be a single-layer structure or a multilayer structure comprising two or more organic layers. For example, the organic light-emitting device of the present invention may include a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and the like as organic layers. However, the structure of the organic light-emitting device is not limited to this and may include a smaller number of organic layers.

[0106] Preferably, the organic layer containing the above compound may be a hole transport layer.

[0107] In one embodiment, the organic layer may include a hole transport layer, a light emitting layer, and an electron injection and transport layer. In this case, the organic layer containing the compound may be the hole transport layer.

[0108] In another embodiment, the organic layer may include a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, and an electron injection and transport layer. In this case, the organic layer containing the compound may be a hole transport layer.

[0109] In another embodiment, the organic layer may include a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, and an electron injection and transport layer. In this case, the organic layer containing the compound may be a hole transport layer.

[0110] In addition, the organic light-emitting device according to the present invention may be an organic light-emitting device having a structure (normal type) in which the first electrode is an anode and the second electrode is a cathode, and an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate. In addition, 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 the first electrode is a cathode and the second electrode is an anode, and 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 one embodiment of the present invention is shown in FIG. Figure 1 and 2 middle.

[0111] Figure 1 The diagram shows an example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole transport layer 3, a light-emitting layer 4, an electron transport layer 5, an electron injection layer 6, and a cathode 7. In the above structure, the compound represented by Chemical Formula 1 may be contained in the hole transport layer.

[0112] Figure 2The diagram shows an example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole injection layer 8, a hole transport layer 3, an electron blocking layer 9, a light-emitting layer 4, a hole blocking layer 10, an electron transport layer 5, an electron injection layer 6, and a cathode 7. In the above structure, the compound represented by Chemical Formula 1 can be contained in the hole injection layer, the hole transport layer, or the electron blocking layer.

[0113] The organic light-emitting device according to the present invention can be manufactured using materials and methods known in the art, except that at least one of the organic layers contains the compound represented by Chemical Formula 1. Furthermore, when the organic light-emitting device includes multiple organic layers, the organic layers can be formed of the same substance or different substances.

[0114] For example, an 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. In this case, the device can be manufactured as follows: a metal or a conductive metal oxide or an alloy thereof is deposited on a substrate using a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation to form an anode. An organic layer comprising a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer is then formed on the anode. A cathode material is then deposited on the organic layer. Alternatively, an organic light-emitting device can be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.

[0115] Furthermore, when manufacturing an organic light-emitting device, the compound represented by Chemical Formula 1 can be applied not only by vacuum evaporation but also by solution coating to form an organic layer. Solution coating methods include, but are not limited to, spin coating, dip coating, doctor blade coating, inkjet printing, screen printing, spraying, and roller coating.

[0116] In addition to these methods, an organic light-emitting device 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 this.

[0117] As an example, the first electrode is an anode and the second electrode is a cathode, or the first electrode is a cathode and the second electrode is an anode.

[0118] The anode material is preferably a material with a large work function to facilitate hole injection into the organic layer. Specific examples of the anode material include, but are not limited to, 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-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline.

[0119] The cathode material is preferably one with a low work function to facilitate electron injection into the organic layer. Specific examples of cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; and multilayer structures such as LiF / Al or LiO2 / Al.

[0120] The hole injection layer is a layer that injects holes from the electrode. As a hole injection material, it is preferably a compound that has the ability to transport holes, has the effect of injecting holes from the anode, has an excellent hole injection effect for the light-emitting layer or the light-emitting material, prevents the excitons generated in the light-emitting layer from migrating to the electron injection layer or the 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 anode material and the HOMO of the surrounding organic layer. Specific examples of hole injection materials include metal porphyrins, oligothiophenes, arylamine organics, hexanitrile hexaazatriphenylene organics, quinacridone organics, perylene organics, anthraquinones, polyaniline, and polythiophene conductive polymers, but are not limited thereto.

[0121] The hole transport layer is a layer that receives holes from the hole injection layer and transports them to the light-emitting layer. The hole transport material is a material that can receive holes from the anode or the hole injection layer and transfer them to the light-emitting layer. Materials with high hole mobility are suitable. The hole transport material can be a compound represented by Chemical Formula 1, or an arylamine-based organic compound, a conductive polymer, or a block copolymer containing both conjugated and non-conjugated portions, but is not limited thereto.

[0122] The electron-blocking layer is formed on the hole-transporting layer, preferably in contact with the light-emitting layer. It regulates hole mobility, prevents excessive electron migration, and increases the probability of hole-electron bonding, thereby improving the efficiency of the organic light-emitting device. The electron-blocking layer comprises an electron-blocking substance. Examples of such electron-blocking substances include, but are not limited to, the compound represented by Chemical Formula 1 or an arylamine-based organic compound.

[0123] The above-mentioned luminescent material is a material that can receive holes and electrons from the hole transport layer and the electron transport layer respectively and combine them to emit light in the visible light region, and preferably has a high quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxyquinoline aluminum complex (Alq3), carbazole compounds, dimerized styryl compounds, BAlq, 10-hydroxybenzoquinoline-metal compounds, benzo Examples of the present invention include, but are not limited to, oxazole, benzothiazole, and benzimidazole compounds, poly(p-phenylenevinylene) (PPV) polymers, spiro compounds, polyfluorene, and rubrene.

[0124] The above-mentioned light-emitting layer may include a host material and a dopant material as described above. The host material may also include an aromatic fused ring derivative or a heterocyclic compound. Specifically, as an aromatic fused ring derivative, there are anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., as heterocyclic compounds, there are carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, etc. Pyrimidine derivatives, etc., but are not limited thereto.

[0125] As dopant materials, there are aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, aromatic amine derivatives are aromatic fused ring derivatives having substituted or unsubstituted arylamino groups, such as pyrene, anthracene, , diindenopyrene, etc. Styrylamine compounds are compounds in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, and are substituted or unsubstituted with one or more substituents selected from aryl, silyl, alkyl, cycloalkyl, and arylamino groups. Specific examples include, but are not limited to, styrylamine, styryldiamine, styryltriamine, and styryltetramine. Furthermore, metal complexes include, but are not limited to, iridium complexes and platinum complexes.

[0126] The hole blocking layer is a layer formed on the light-emitting layer, preferably in contact with the light-emitting layer, and improves the efficiency of the organic light-emitting device by adjusting the electron mobility and preventing the excessive migration of holes to increase the probability of hole-electron bonding. The hole blocking layer contains a hole blocking substance. Examples of such hole blocking substances include azine derivatives including triazine, triazole derivatives, Compounds into which electron-withdrawing groups are introduced include, but are not limited to, oxadiazole derivatives, phenanthroline derivatives, phosphine oxide derivatives, and the like.

[0127] The electron transport layer is a layer that receives electrons from the electron injection layer and transfers the electrons to the light-emitting layer. The electron transport material is a material that can well receive electrons from the cathode and transfer them to the light-emitting layer. Materials with high electron mobility are suitable. As specific examples, there are Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free radical compounds, hydroxyflavone-metal complexes, etc., but are not limited to these. The electron transport layer can be used together with any desired cathode material as used in the prior art. In particular, examples of suitable cathode materials are common materials with low work function and accompanied by an aluminum layer or a silver layer. Specifically, cesium, barium, calcium, ytterbium and samarium, and in each case, they are accompanied by an aluminum layer or a silver layer.

[0128] The electron injection layer is a layer that injects electrons from the electrode. As the electron injection material contained in the electron injection layer, it is preferable to use the following compounds: compounds that have the ability to transport electrons, have the effect of injecting electrons from the cathode, have an excellent electron injection effect on the light-emitting layer or the light-emitting material, prevent the excitons generated in the light-emitting layer from migrating to the hole injection layer, and have excellent thin film forming ability. Specifically, as the electron injection material, there are LiF, NaCl, CsF, Li2O, BaO, fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, Azoles, Examples include, but are not limited to, diazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylene methane, anthrone, phenanthroline, and derivatives thereof, metal coordination compounds, and nitrogen-containing five-membered ring derivatives.

[0129] Examples of the metal coordination compounds 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)gallium chloride, bis(2-methyl-8-quinolinato)(o-cresol)gallium, bis(2-methyl-8-quinolinato)(1-naphthol)aluminum, and bis(2-methyl-8-quinolinato)(2-naphthol)gallium.

[0130] The organic light-emitting device according to the present invention may be a bottom emission device, a top emission device, or a bidirectional light-emitting device. In particular, it may be a bottom emission device requiring relatively high luminous efficiency.

[0131] In addition, the compound represented by the above Chemical Formula 1 may be included in an organic solar cell or an organic transistor in addition to being included in an organic light-emitting device.

[0132] The preparation of the compound represented by the above Chemical Formula 1 and the organic light-emitting device containing the same is specifically described in the following examples. However, the following examples are for illustrating the present invention, and the scope of the present invention is not limited thereto.

[0133] Preparation Example 1: Preparation of Compound 1

[0134]

[0135] Under a nitrogen atmosphere, compound A (7.5 g, 19.36 mmol) and compound a1 (6.59 g, 38.92 mmol) were completely dissolved in 290 mL of xylene in a 500 mL round-bottom flask. NaOtBu (5.58 g, 58.09 mmol) and bis(tri-tert-butylphosphine)palladium(0) (0.49 g, 0.97 mmol) were then added, followed by heating and stirring for 8 hours. The temperature was lowered to room temperature, the base was removed by filtration, and the xylene was concentrated under reduced pressure. The mixture was then recrystallized from 250 mL of ethyl acetate to produce compound 1 (10.05 g, yield: 79%).

[0136] MS[M+H] + =653

[0137] Preparation Example 2: Preparation of Compound 2

[0138]

[0139] Under a nitrogen atmosphere, compound B (8.20 g, 21.17 mmol) and compound a2 (10.44 g, 42.56 mmol) were completely dissolved in 310 mL of xylene in a 500 mL round-bottom flask. NaOtBu (6.10 g, 63.52 mmol) was then added, followed by bis(tri-tert-butylphosphine)palladium(0) (0.54 g, 1.06 mmol), and the mixture was heated and stirred for 8 hours. The temperature was lowered to room temperature, the base was removed by filtration, and the xylene was concentrated under reduced pressure. The mixture was recrystallized from 250 mL of ethyl acetate to produce compound 2 (11.02 g, yield: 65%).

[0140] MS[M+H] + =805

[0141] Preparation Example 3: Preparation of Compound 3

[0142]

[0143] Under a nitrogen atmosphere, compound C (7.35 g, 18.98 mmol) and compound a3 (12.26 g, 38.14 mmol) were completely dissolved in 285 mL of xylene in a 500 mL round-bottom flask. NaOtBu (5.47 g, 56.93 mmol) was then added, followed by bis(tri-tert-butylphosphine)palladium(0) (0.48 g, 0.95 mmol), and the mixture was heated and stirred for 8 hours. The temperature was lowered to room temperature, the base was removed by filtration, and the xylene was concentrated under reduced pressure. The mixture was recrystallized from 250 mL of ethyl acetate to produce compound 3 (13.45 g, yield: 74%).

[0144] MS[M+H] + =957

[0145] Preparation Example 4: Preparation of Compound 4

[0146]

[0147] Under a nitrogen atmosphere, compound D (8.05 g, 20.78 mmol) and compound a4 (11.25 g, 41.78 mmol) were completely dissolved in 312 mL of xylene in a 500 mL round-bottom flask. NaOtBu (5.99 g, 62.35 mmol) was then added, followed by bis(tri-tert-butylphosphine)palladium(0) (0.53 g, 1.04 mmol), and the mixture was heated and stirred for 8 hours. The temperature was lowered to room temperature, the base was removed by filtration, and the xylene was concentrated under reduced pressure. The mixture was recrystallized from 270 mL of ethyl acetate to produce compound 4 (12.55 g, yield: 71%).

[0148] MS[M+H] + =853

[0149] Preparation Example 5: Preparation of Compound 5

[0150]

[0151] Under a nitrogen atmosphere, compound E (7.40 g, 19.11 mmol) and compound a5 (8.42 g, 38.40 mmol) were completely dissolved in 287 mL of xylene in a 500 mL round-bottom flask. NaOtBu (5.51 g, 57.32 mmol) was added, followed by bis(tri-tert-butylphosphine)palladium(0) (0.49 g, 0.96 mmol), and the mixture was heated and stirred for 8 hours. The temperature was lowered to room temperature, the base was removed by filtration, and the xylene was concentrated under reduced pressure. The mixture was recrystallized from 280 mL of ethyl acetate to produce compound 5 (10.23 g, yield: 71%).

[0152] MS[M+H] + =753

[0153] Preparation Example 6: Preparation of Compound 6

[0154]

[0155] Under a nitrogen atmosphere, compound F (7.30 g, 18.85 mmol) and compound a6 (6.41 g, 37.89 mmol) were completely dissolved in 283 mL of xylene in a 500 mL round-bottom flask. NaOtBu (5.43 g, 56.55 mmol) was then added, followed by bis(tri-tert-butylphosphine)palladium(0) (0.48 g, 0.94 mmol), and the mixture was heated and stirred for 8 hours. The temperature was lowered to room temperature, the base was removed by filtration, and the xylene was concentrated under reduced pressure. The mixture was recrystallized from 280 mL of ethyl acetate to produce compound 6 (10.04 g, yield: 82%).

[0156] MS[M+H] + =653

[0157] Preparation Example 7: Preparation of Compound 7

[0158]

[0159] Under a nitrogen atmosphere, compound G (7.55 g, 16.29 mmol) and compound a7 (8.03 g, 32.75 mmol) were completely dissolved in 240 mL of xylene in a 500 mL round-bottom flask. NaOtBu (4.70 g, 48.88 mmol) was then added, followed by bis(tri-tert-butylphosphine)palladium(0) (0.42 g, 0.81 mmol), and the mixture was heated and stirred for 8 hours. The temperature was lowered to room temperature, the base was removed by filtration, and the xylene was concentrated under reduced pressure. The mixture was recrystallized from 230 mL of ethyl acetate to produce compound 7 (10.78 g, yield: 75%).

[0160] MS[M+H] + =881

[0161] Preparation Example 8: Preparation of Compound 8

[0162]

[0163] Under a nitrogen atmosphere, compound H (8.15 g, 18.63 mmol) and compound a8 (6.34 g, 37.46 mmol) were completely dissolved in 280 mL of xylene in a 500 mL round-bottom flask. NaOtBu (5.37 g, 55.90 mmol) was then added, followed by bis(tri-tert-butylphosphine)palladium(0) (0.48 g, 0.93 mmol), and the mixture was heated and stirred for 8 hours. The temperature was lowered to room temperature, the base was removed by filtration, and the xylene was concentrated under reduced pressure. The mixture was recrystallized from 240 mL of ethyl acetate to produce compound 8 (10.80 g, yield: 82%).

[0164] MS[M+H] + =703

[0165] Preparation Example 9: Preparation of Compound 9

[0166]

[0167] Under a nitrogen atmosphere, compound I (8.10 g, 16.97 mmol) and compound a9 (5.77 g, 34.10 mmol) were completely dissolved in 255 mL of xylene in a 500 mL round-bottom flask. NaOtBu (4.89 g, 50.90 mmol) was added, followed by bis(tri-tert-butylphosphine)palladium(0) (0.43 g, 0.85 mmol), and the mixture was heated and stirred for 8 hours. The temperature was lowered to room temperature, the base was removed by filtration, and the xylene was concentrated under reduced pressure. The mixture was recrystallized from 240 mL of ethyl acetate to produce compound 9 (7.70 g, yield: 61%).

[0168] MS[M+H] + =743

[0169] Preparation Example 10: Preparation of Compound 10

[0170]

[0171] Under a nitrogen atmosphere, compound J (7.80 g, 16.00 mmol) and compound a10 (5.44 g, 32.17 mmol) were completely dissolved in 240 mL of xylene in a 500 mL round-bottom flask. NaOtBu (4.61 g, 48.01 mmol) was added, followed by bis(tri-tert-butylphosphine)palladium(0) (0.41 g, 0.80 mmol), and the mixture was heated and stirred for 8 hours. The temperature was lowered to room temperature, the base was removed by filtration, and the xylene was concentrated under reduced pressure. The mixture was recrystallized from 240 mL of ethyl acetate to produce compound 10 (8.50 g, yield: 71%).

[0172] MS[M+H] + =753

[0173] Preparation Example 11: Preparation of Compound 11

[0174]

[0175] Under a nitrogen atmosphere, compound K (6.50 g, 16.78 mmol) and compound a11 (8.75 g, 33.73 mmol) were completely dissolved in 240 mL of xylene in a 500 mL round-bottom flask. NaOtBu (4.89 g, 50.35 mmol) was then added, followed by bis(tri-tert-butylphosphine)palladium(0) (0.43 g, 0.84 mmol), and the mixture was heated and stirred for 8 hours. The temperature was lowered to room temperature, the base was removed by filtration, and the xylene was concentrated under reduced pressure. The mixture was recrystallized from 240 mL of ethyl acetate to produce compound 11 (9.25 g, yield: 66%).

[0176] MS[M+H] + =833.0

[0177] Example 1

[0178] ITO (indium tin oxide) The thickness of the glass substrate coated with a film is placed in distilled water dissolved with a detergent and washed with ultrasonic waves. At this time, the detergent uses Fischer Co. products, and the distilled water uses distilled water filtered twice by a filter manufactured by Millipore Co. After the ITO was washed for 30 minutes, ultrasonic washing was performed twice with distilled water. After the distilled water washing is completed, ultrasonic washing is performed and dried with a solvent of isopropyl alcohol, acetone, and methanol, and then the substrate is transported to a plasma cleaning machine. In addition, after the above-mentioned substrate is cleaned for 5 minutes, the substrate is transported to a vacuum deposition machine.

[0179] On the thus prepared ITO transparent electrode, the following compound HI-1 and the following compound HI-2 were added in a ratio of 98:2 (molar ratio). On the hole injection layer, the compound 1-1 prepared in the above-mentioned preparation example 1 as a hole transporting substance was deposited. Then, a hole transport layer is formed by vacuum evaporation. The following compound EB-1 was vacuum-deposited to form an electron blocking layer.

[0180] Next, on the electron blocking layer, a film with a thickness of A compound represented by the following chemical formula BH and a compound represented by the following chemical formula BD were vacuum deposited at a weight ratio of 25:1 to form a light-emitting layer.

[0181] On the above-mentioned light-emitting layer, the film thickness is The following compound HB-1 was vacuum-deposited to form a hole blocking layer. Next, the following compound ET-1 and the following compound LiQ (lithium quinolate) were vacuum-deposited on the hole blocking layer at a weight ratio of 1:1, thereby forming a hole blocking layer. On the electron transport layer, lithium fluoride (LiF) is sequentially added with The thickness of the aluminum The electron injection layer and the cathode are formed by evaporation to a thickness of , respectively.

[0182] In the above process, the evaporation rate of organic matter is maintained at Lithium fluoride at the cathode maintains The evaporation speed of aluminum is maintained The evaporation speed is maintained at 2 x 10 -7 ~5ⅹ10 -6 The organic light-emitting device is thus produced.

[0183] The compounds used in the above Example 1 are as follows:

[0184]

[0185] Example 2 to Example 11

[0186] An organic light-emitting device was manufactured by the same method as in Example 1, except that the compounds described in Table 1 below were used instead of the compounds in Production Example 1.

[0187] Comparative Examples 1 to 5

[0188] An organic light-emitting device was manufactured by the same method as in Example 1, except that the compounds listed in Table 1 below were used instead of Compound 1 in Preparation Example 1. The compounds of the comparative examples used in Table 1 below are as follows:

[0189]

[0190] Experimental Example 1

[0191] The organic light emitting devices manufactured in the above examples and comparative examples were subjected to a current of 20 mA / cm 2 The driving voltage, luminous efficiency, and color coordinates were measured when the current was 1.5 volts. The time required for the luminance to decrease to 95% of the initial luminance (T95) was also measured. The results are shown in Table 1 below. T95 refers to the time required for the luminance to decrease from the initial luminance (1600 nits) to 95%.

[0192] [Table 1]

[0193]

[0194] As shown in Table 1 above, the organic light-emitting devices of the examples using the compound represented by Chemical Formula 1 as a hole transport layer material exhibit excellent characteristics in terms of driving voltage, luminous efficiency and lifespan compared to the organic light-emitting devices using the compound in which both R2 and R4 are N(Ar2)(Ar3) (Comparative Examples 1 and 2), the compound in which only any one of R1 to R5 is N(Ar2)(Ar3) (Comparative Examples 3 and 5), and the compound in which any one of R1 to R5 is N(Ar2)(Ar3) and N(Ar2)(Ar3) is also bonded as a substituent of Ar1 (Comparative Example 4).

[0195] Considering that the luminous efficiency and lifespan of an organic light-emitting device generally have a trade-off relationship, it can be seen that the organic light-emitting device using the compound of the present invention exhibits significantly improved device characteristics compared to the comparative example device.

[0196] [Explanation of symbols]

[0197] 1: Substrate 2: Anode

[0198] 3: Hole transport layer 4: Light-emitting layer

[0199] 5: Electron transport layer 6: Electron injection layer

[0200] 7: cathode 8: hole injection layer

[0201] 9: Electron blocking layer

[0202] 10: Hole blocking layer.

Claims

1. A compound represented by the following chemical formula 1: Chemical formula 1 In the chemical formula 1, Ar1 is unsubstituted or is selected from deuterium and C 1-10 One or more substituents in the alkyl group replace the C 6-20 Aryl; or unsubstituted or selected from deuterium and C 1-10 One or more substituents in the alkyl group substituted with one heteroatom of N, O and S 2-20 heteroaryl, Two of R1 to R5 are each independently N(Ar2)(Ar3), and the others are each independently hydrogen or deuterium, However, this does not include the case where R2 and R4 are both N(Ar2)(Ar3). Ar2 and Ar3 are each independently unsubstituted or selected from deuterium and C 1-10 One or more substituents in the alkyl group replace the C 6-20 Aryl; or unsubstituted or selected from deuterium and C 1-10 One or more substituents in the alkyl group substituted with one heteroatom of N, O and S 2-20 Heteroaryl.

2. The compound according to claim 1, wherein Ar1 is a phenyl group, a biphenyl group, a naphthyl group, a phenanthrenyl group, a 9,9-dimethylfluorenyl group, or a dibenzofuranyl group.

3. The compound according to claim 1, wherein Ar2 and Ar3 are each independently a phenyl group, a biphenyl group, a naphthyl group, a 9,9-dimethylfluorenyl group or a dibenzofuranyl group.

4. The compound according to claim 1, wherein The compound is represented by any one of the following chemical formulas 1-1 to 1-5: Chemical formula 1-1 Chemical formula 1-2 Chemical formula 1-3 Chemical formula 1-4 Chemical formula 1-5 In the chemical formulas 1-1 to 1-5, Ar 21 、Ar 22 、Ar 31 and Ar 32 are each independently unsubstituted or selected from deuterium and C 1-10 One or more substituents in the alkyl group replace the C 6-20 Aryl; or unsubstituted or selected from deuterium and C 1-10 One or more substituents in the alkyl group substituted with one heteroatom of N, O and S 2-20 heteroaryl, R1 to R5 are each independently hydrogen or deuterium, Ar1 is the same as defined in claim 1.

5. The compound according to claim 4, wherein Ar 21 and Ar 31 Any one of Ar 22 Same, the other one is the same as Ar 32 same.

6. The compound according to claim 4, wherein Ar 21 、Ar 22 、Ar 31 and Ar 32 Each is independently a phenyl group, a biphenyl group, a naphthyl group, a 9,9-dimethylfluorenyl group or a dibenzofuranyl group.

7. The compound according to claim 1, wherein The compound is any one selected from the following compounds:

8. An organic light-emitting device, wherein: include: 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 the compound according to any one of claims 1 to 7.

9. The organic light-emitting device according to claim 8, wherein The organic layer containing the compound is a hole transport layer.

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