Novel compound and organic light-emitting device containing the same

Abstract

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

Description

Technical Field

[0001] Cross-references to related applications

[0002] This application claims priority based on Korean Patent Application No. 10-2021-0153380 filed on November 9, 2021 and Korean Patent Application No. 10-2022-0139164 filed on October 26, 2022, and incorporates all disclosures in the documents of the Korean patent applications as a part of 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 1) Korean Patent Publication No. 10-2000-0051826 Summary of the Invention

[0010] Technical issues

[0011] The present invention relates to a novel organic light-emitting material and an organic light-emitting device comprising 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] X is a single bond, O or S,

[0018] R1 and R2 are each independently hydrogen; deuterium; a halogen group; a nitrile group; a silyl group; a substituted or unsubstituted C 6-60 Aryl; or substituted or unsubstituted C containing any one or more selected from N, O, S 2-60 heteroaryl,

[0019] a is an integer from 0 to 3,

[0020] b is an integer from 0 to 4,

[0021] L1 to L3 are each independently a single bond; substituted or unsubstituted C 6-60 Arylene; or substituted or unsubstituted C containing any one or more selected from N, O, S 2-60 Heteroarylene,

[0022] Ar1 and Ar2 are each independently substituted or unsubstituted C 6-60 Aryl; or substituted or unsubstituted C containing any one or more selected from N, O, S 2-60 heteroaryl group, and at least one of Ar1 and Ar2 is a substituent represented by the following Chemical Formula 2,

[0023] [Chemical Formula 2]

[0024]

[0025] In the above chemical formula 2,

[0026] R3 is deuterium; a halogen group; a nitrile group; a silyl group; a substituted or unsubstituted C 6-60 Aryl; or substituted or unsubstituted C containing any one or more selected from N, O, S 2-60 heteroaryl,

[0027] R 11 to R 14 are each independently -CH3, -CH2D, -CHD2 or -CD3,

[0028] c is an integer from 0 to 7,

[0029] The above-mentioned silyl group refers to -Si(Z1)(Z2)(Z3), where Z1 to Z3 are each independently a substituted or unsubstituted C 1-60 Alkyl, or substituted or unsubstituted C6-60 Aryl.

[0030] In addition, the present invention provides an organic light-emitting device, which includes: a first electrode, a second electrode arranged opposite to the first electrode, and one or more organic layers arranged between the first electrode and the second electrode, wherein one or more of the organic layers contains the compound represented by the above Chemical Formula 1.

[0031] Effects of the Invention

[0032] The compound represented by Chemical Formula 1 can be used as a material for an organic layer of an organic light-emitting device, thereby achieving improved efficiency, lower driving voltage, and / or improved lifespan characteristics in the organic light-emitting device. In particular, the compound represented by Chemical Formula 1 can be used as a material for hole injection, hole transport, luminescence, electron transport, and / or electron injection. BRIEF DESCRIPTION OF THE DRAWINGS

[0033] Figure 1 An example of an organic light-emitting device composed of a substrate 1 , an anode 2 , a light-emitting layer 3 , and a cathode 4 is shown.

[0034] Figure 2 The figure shows an organic light emitting device composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron suppression layer 7, a light emitting layer 3, an electron injection and transport layer 8, and a cathode 4. DETAILED DESCRIPTION

[0035] Hereinafter, the present invention will be described in more detail to facilitate understanding.

[0036] The present invention provides a compound represented by the above Chemical Formula 1.

[0037] In this manual, or It represents a bond to other substituents.

[0038] In the present specification, the term "substituted or unsubstituted" refers to a group selected from deuterium; a halogen group; a nitrile 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 a heteroaryl group containing one or more N, O, and S atoms, which may be substituted or unsubstituted with one or more substituents, or with a substituent formed by linking two or more of the substituents listed above. For example, a "substituent formed by linking two or more substituents" may be a biphenyl group. That is, a biphenyl group may be an aryl group, or it may be interpreted as a substituent formed by linking two phenyl groups.

[0039] 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.

[0040]

[0041] 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.

[0042]

[0043] 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.

[0044]

[0045] 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.

[0046] In the present specification, specific examples of the boryl group include trimethylboryl, triethylboryl, tert-butyldimethylboryl, triphenylboryl, and phenylboryl, but are not limited thereto.

[0047] In the present specification, examples of the halogen group include fluorine, chlorine, bromine, and iodine.

[0048] In this specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the number of carbon atoms 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, the number of carbon atoms in the alkyl group is 1 to 6. Specific examples of the alkyl group include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, and 5-methylhexyl.

[0049] 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.

[0050] In the present 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.

[0051] 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. 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, pyrenyl, perylenyl, yl, fluorenyl, etc., but are not limited thereto.

[0052] In this specification, the fluorenyl group may be substituted, and two substituents may be combined with each other to form a spiro structure. etc. However, the present invention is not limited thereto.

[0053] In the present specification, the heteroaryl group is a heteroaryl group containing one or more of O, N, Si and S as hetero elements. The number of carbon atoms is not particularly limited, but preferably the number of carbon atoms is 2 to 60. According to one embodiment, the number of carbon atoms of the heteroaryl group is 6 to 30. According to one embodiment, the number of carbon atoms of the heteroaryl group is 6 to 20. 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.

[0054] In this specification, the aryl groups in aralkyl, aralkenyl, alkylaryl, and arylamine groups are the same as those exemplified above for aryl groups. In this specification, the alkyl groups in aralkyl, alkylaryl, and alkylamine groups are the same as those exemplified above for alkyl groups. In this specification, the heteroaryl groups in heteroarylamine groups are the same as those exemplified above for alkenyl groups. In this specification, the arylene groups are divalent groups, and the above description of aryl groups applies to them. In this specification, heteroarylene groups are divalent groups, and the above description of heteroaryl groups applies to them. In this specification, hydrocarbon rings are not monovalent groups but are formed by bonding two substituents, and the above description of aryl or cycloalkyl groups applies to them. In this specification, heteroaryl groups are not monovalent groups but are formed by bonding two substituents, and the above description of heteroaryl groups applies to them.

[0055] Preferably, R1 and R2 are each independently hydrogen; deuterium; substituted or unsubstituted C 6-20 Aryl; or substituted or unsubstituted C containing any one or more selected from N, O, S 2-20 Heteroaryl.

[0056] More preferably, R1 and R2 can each independently be hydrogen, deuterium, phenyl, phenyl substituted with 1 or 2 tert-butyl groups, biphenyl, naphthyl or The above R1 and R2 are each phenyl, phenyl substituted by 1 or 2 tert-butyl groups, biphenyl, naphthyl or When the above phenyl, phenyl substituted by 1 or 2 tert-butyl groups, biphenyl, naphthyl or It may be unsubstituted or substituted with one or more deuterium groups.

[0057] Preferably, L1 to L3 are each independently a single bond; substituted or unsubstituted C 6-20 Arylene; or substituted or unsubstituted C containing any one or more selected from N, O, S 2-20 Heteroarylene,

[0058] More preferably, L1 to L3 each independently may be a single bond, a phenylene group, or a phenylene group substituted with four deuterium groups.

[0059] Preferably, Ar1 and Ar2 are each independently substituted or unsubstituted C 6-20 Aryl; or substituted or unsubstituted C containing any one or more selected from N, O, S 2-20 heteroaryl group, and at least one of Ar1 and Ar2 may be a substituent represented by the following Chemical Formula 2,

[0060] [Chemical Formula 2]

[0061]

[0062] More preferably, among Ar1 and Ar2 above, R3 in Chemical Formula 2 is hydrogen or deuterium, and c may be an integer of 0 to 7.

[0063] More preferably, Ar1 and Ar2 are each independently phenyl, phenyl substituted by one tert-butyl group, phenyl substituted by one adamantyl group, biphenyl, terphenyl, naphthyl, phenylnaphthyl, naphthylphenyl, dimethylfluorenyl, phenylfluorenyl, diphenylfluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl or The above Ar1 and Ar2 may be unsubstituted or substituted with one or more deuteriums, and at least one of Ar1 and Ar2 may be unsubstituted or substituted with one or more deuteriums.

[0064] Most preferably, Ar1 and Ar2 are each independently any one selected from the group consisting of:

[0065]

[0066] Preferably, the substituent represented by the above Chemical Formula 2 may be any one selected from the group consisting of:

[0067]

[0068] Preferably, R 11 to R 14 Each may be -CH3.

[0069] Representative examples of the compound represented by the above Chemical Formula 1 are shown below:

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[0198] As an example, the compound represented by the above Chemical Formula 1 can be produced by the production method shown in the following Reaction Formula 1, and other compounds can be produced similarly.

[0199] [Reaction formula 1]

[0200]

[0201] In the above reaction formula 1, X, R1, R2, a, b, L1 to L3, Ar1 and Ar2 are the same as those defined in the above chemical formula 1, and Z is a halogen, preferably, chlorine or bromine.

[0202] The above reaction formula 1 is preferably carried out in the presence of a palladium catalyst and a base as an amine substitution reaction. The reactive groups used in the amine substitution reaction can be modified according to techniques known in the art. The above production method can be further embodied in the production examples described below.

[0203] The present invention also 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.

[0204] 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, an electron suppression 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 greater or lesser number of organic layers.

[0205] In addition, the above-mentioned organic layer may include a hole transport layer, a hole injection layer, a layer that simultaneously performs hole transport and hole injection, or an electron suppression layer, and the above-mentioned hole transport layer, hole injection layer, a layer that simultaneously performs hole transport and hole injection, or an electron suppression layer may contain the compound represented by the above-mentioned Chemical Formula 1.

[0206] 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 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 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 Figure 2 .

[0207] Figure 1 The figure shows an example of an organic light-emitting device composed of a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4. In the above structure, the compound represented by the above Chemical Formula 1 may be contained in the above light-emitting layer.

[0208] Figure 2The diagram shows an example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron suppression layer 7, a light-emitting layer 3, an electron injection and transport layer 8, and a cathode 4. In the above structure, the compound represented by Chemical Formula 1 can be contained in the hole transport layer or the electron suppression layer.

[0209] 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.

[0210] 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, an electron suppression 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.

[0211] 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.

[0212] 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.

[0213] 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.

[0214] 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 alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline.

[0215] 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.

[0216] 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.

[0217] The hole transport layer receives holes from the hole injection layer and transports them to the light-emitting layer. The hole transport material is a substance that can receive holes from the anode or hole injection layer and transfer them to the light-emitting layer. Suitable materials have high hole mobility. Specific examples include, but are not limited to, arylamine-based organic compounds, conductive polymers, and block copolymers containing both conjugated and non-conjugated portions. Preferably, the compound represented by Chemical Formula 1 can be used as the hole transport layer material.

[0218] On the other hand, in the present invention, the "hole injection and transport layer" is a layer that functions as both the hole injection layer and the hole transport layer. Substances that function as the above layers may be used alone or in combination, but are not limited thereto.

[0219] The electron suppression layer is placed between the hole transport layer and the light-emitting layer to prevent electrons injected from the cathode from recombining in the light-emitting layer and transferring to the hole transport layer. It is also called an electron blocking layer. The electron suppression layer is preferably composed of a material with a lower electron affinity than the electron transport layer. Preferably, the compound represented by Chemical Formula 1 can be used as the electron suppression layer material.

[0220] The 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. It is preferably a material with 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 Azoles, benzothiazoles and benzimidazole compounds; poly(p-phenylene vinylene) (PPV) polymers; spiro compounds; polyfluorenes, rubrene, etc., but are not limited thereto.

[0221] The above-mentioned light-emitting layer may include a host material and a dopant material. The host material includes 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.

[0222] 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, 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.

[0223] 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, in each case accompanied by an aluminum layer or a silver layer.

[0224] The electron injection layer is a layer that injects electrons from the electrode. Preferably, the following compounds 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, there are fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, Azoles, Examples include, but are not limited to, diazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylene methane, anthrone, and derivatives thereof, metal coordination compounds, and nitrogen-containing five-membered ring derivatives.

[0225] 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.

[0226] On the other hand, in the present invention, the "electron injection and transport layer" is a layer that functions as both the electron injection layer and the electron transport layer. Substances that function as the above layers may be used alone or in combination, but are not limited thereto.

[0227] 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.

[0228] 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.

[0229] 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.

[0230] <Synthesis example>

[0231] Synthesis Example 1. Synthesis of Compound 1

[0232]

[0233] Toluene (300 ml) was added to 2′-bromospiro[adamantane-2,9′-fluorene] (20.0 g, 54.75 mmol), N-([1,1′-biphenyl]-4-yl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-amine (19.85 g, 55.84 mmol), and sodium tert-butoxide (7.37 g, 76.65 mmol), followed by heating and stirring for 10 minutes. Bis(tri-tert-butylphosphine)palladium (0.14 g, 0.27 mmol) dissolved in toluene (30 ml) was added to the mixture, followed by heating and stirring for 1 hour. After the reaction was completed and filtered, the layers were separated using toluene and water. After removing the solvent, the product was recrystallized from ethyl acetate to obtain the above-mentioned compound 1 (27.5 g, yield 78.49%). (MS: [M+H] + =640)

[0234] Synthesis Example 2. Synthesis of Compound 2

[0235]

[0236] Compound 2 (29.5 g, 78.09% yield) was obtained by the same method as in Synthesis Example 1 using 2′-bromospiro[adamantane-2,9′-fluorene] (20.0 g, 54.75 mmol) and 5,5,8,8-tetramethyl-N-(4-(naphthalen-1-yl)phenyl)-5,6,7,8-tetrahydronaphthalen-2-amine (22.65 g, 55.84 mmol). (MS: [M+H] + =690)

[0237] Synthesis Example 3. Synthesis of Compound 3

[0238]

[0239] Using 2′-bromospiro[adamantane-2,9′-fluorene] (20.0 g, 54.75 mmol) and 9,9-dimethyl-N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-9H-fluoren-2-amine (22.09 g, 55.84 mmol), the above-mentioned compound 3 (28.5 g, yield 76.55%) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS: [M+H] + =680)

[0240] Synthesis Example 4. Synthesis of Compound 4

[0241]

[0242] Using 2′-bromospiro[adamantane-2,9′-fluorene] (20.0 g, 54.75 mmol) and N-(4-(tert-butyl)phenyl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-amine (19.85 g, 55.84 mmol), the above-mentioned compound 4 (26.5 g, yield 78.08%) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS: [M+H] + =620)

[0243] Synthesis Example 5. Synthesis of Compound 5

[0244]

[0245] Using 2′-bromospiro[adamantane-2,9′-fluorene] (20.0 g, 54.75 mmol) and N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)dibenzo[b,d]furan-3-amine (20.63 g, 55.84 mmol), the above-mentioned compound 5 (28.0 g, yield 78.21%) was obtained by the same method as in Synthesis Example 1. (MS: [M+H] + =654)

[0246] Synthesis Example 6. Synthesis of Compound 6

[0247]

[0248] Using 2′-bromospiro[adamantane-2,9′-fluorene] (20.0 g, 54.75 mmol) and bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine (21.76 g, 55.84 mmol), the above-mentioned compound 6 (29.0 g, yield 78.58%) was obtained by the same method as in Synthesis Example 1. (MS: [M+H] + =674)

[0249] Synthesis Example 7. Synthesis of Compound 7

[0250]

[0251] Compound 7 (30.5 g, 77.80% yield) was obtained by the same method as in Synthesis Example 1 using 2′-bromospiro[adamantane-2,9′-fluorene] (20.0 g, 54.75 mmol) and N-(4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)phenyl)-[1,1′-biphenyl]-4-amine (24.10 g, 55.84 mmol). (MS: [M+H] + =716)

[0252] Synthesis Example 8. Synthesis of Compound 8

[0253]

[0254] Using 2′-(4-chlorophenyl)spiro[adamantane-2,9′-fluorene] (20.0 g, 50.38 mmol) and N-([1,1′-biphenyl]-4-yl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-amine (18.27 g, 51.39 mmol), the above-mentioned compound 8 (28.5 g, yield 79.01%) was obtained by the same method as in Synthesis Example 1. (MS: [M+H] + =716)

[0255] Synthesis Example 9. Synthesis of Compound 9

[0256]

[0257] Using 2′-(4-chlorophenyl)spiro[adamantane-2,9′-fluorene] (20.0 g, 50.38 mmol) and bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine (20.02 g, 51.39 mmol), the above-mentioned compound 9 (30.0 g, yield 79.38%) was obtained by the same method as in Synthesis Example 1. (MS: [M+H] + =750)

[0258] Synthesis Example 10. Synthesis of Compound 10

[0259]

[0260] Using 2′-bromospiro[adamantane-2,9′-fluorene] (20.0 g, 54.75 mmol) and N-([1,1′-biphenyl]-4-yl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-1-amine (19.85 g, 55.84 mmol), the above-mentioned compound 10 (27.5 g, yield 78.49%) was obtained by the same method as in Synthesis Example 1. (MS: [M+H] + =640)

[0261] Synthesis Example 11. Synthesis of Compound 11

[0262]

[0263] Using 2′-bromospiro[adamantane-2,9′-fluorene] (20.0 g, 54.75 mmol) and bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-1-yl)amine (21.76 g, 55.84 mmol), the above-mentioned compound 11 (28.5 g, yield 77.23%) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS: [M+H] + =674)

[0264] Synthesis Example 12. Synthesis of Compound 12

[0265]

[0266] Using 4′-bromospiro[adamantane-2,9′-fluorene] (20.0 g, 54.75 mmol) and bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-1-yl)amine (21.76 g, 55.84 mmol), the above-mentioned compound 12 (28.5 g, yield 77.23%) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS: [M+H] + =674)

[0267] Synthesis Example 13. Synthesis of Compound 13

[0268]

[0269] Using 4′-bromospiro[adamantane-2,9′-fluorene] (20.0 g, 54.75 mmol) and N-([1,1′-biphenyl]-4-yl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-amine (19.85 g, 55.84 mmol), the above-mentioned compound 13 (27.5 g, yield 78.49%) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS: [M+H] + =640)

[0270] Synthesis Example 14. Synthesis of Compound 14

[0271]

[0272] Using 4′-bromospiro[adamantane-2,9′-fluorene] (20.0 g, 54.75 mmol) and bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine (21.76 g, 55.84 mmol), the above-mentioned compound 14 (29.0 g, yield 78.58%) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS: [M+H] + =674)

[0273] Synthesis Example 15. Synthesis of Compound 15

[0274]

[0275] Compound 15 (27.0 g, yield 77.06%) was obtained by the same method as in Synthesis Example 1 using 3′-bromospiro[adamantane-2,9′-fluorene] (20.0 g, 54.75 mmol) and N-([1,1′-biphenyl]-4-yl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-amine (19.85 g, 55.84 mmol). (MS: [M+H] + =640)

[0276] Synthesis Example 16. Synthesis of Compound 16

[0277]

[0278] Using 3′-bromospiro[adamantane-2,9′-fluorene] (20.0 g, 54.75 mmol) and bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine (21.76 g, 55.84 mmol), the above-mentioned compound 16 (28.5 g, yield 77.23%) was obtained by the same method as in Synthesis Example 1. (MS: [M+H] + =674)

[0279] Synthesis Example 17. Synthesis of Compound 17

[0280]

[0281] Compound 17 (27.0 g, 78.48% yield) was obtained by the same method as in Synthesis Example 1 using 2′-bromospiro[adamantane-2,9′-xanthene] (20.0 g, 52.45 mmol) and N-([1,1′-biphenyl]-4-yl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-amine (19.02 g, 53.50 mmol). (MS: [M+H] + =656)

[0282] Synthesis Example 18. Synthesis of Compound 18

[0283]

[0284] Compound 18 (28.5 g, 78.75% yield) was obtained by the same method as in Synthesis Example 1 using 2′-bromospiro[adamantane-2,9′-xanthene] (20.0 g, 52.45 mmol) and bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine (20.85 g, 53.50 mmol). (MS: [M+H] + =690)

[0285] Synthesis Example 19. Synthesis of Compound 19

[0286]

[0287] Compound 19 (27.0 g, 78.48% yield) was obtained by the same method as in Synthesis Example 1 using 3′-bromospiro[adamantane-2,9′-xanthene] (20.0 g, 52.45 mmol) and N-([1,1′-biphenyl]-4-yl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-amine (19.02 g, 53.50 mmol). (MS: [M+H] + =656)

[0288] Synthesis Example 20. Synthesis of Compound 20

[0289]

[0290] Using 3′-bromospiro[adamantane-2,9′-xanthene] (20.0 g, 52.45 mmol) and bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine (20.85 g, 53.50 mmol), the above-mentioned compound 20 (28.5 g, yield 78.75%) was obtained by the same method as in Synthesis Example 1. (MS: [M+H] + =690)

[0291] Synthesis Example 21. Synthesis of Compound 21

[0292]

[0293] Compound 21 (26.5 g, yield 77.03%) was obtained by the same method as in Synthesis Example 1 using 4′-bromospiro[adamantane-2,9′-xanthene] (20.0 g, 52.45 mmol) and N-([1,1′-biphenyl]-4-yl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-amine (19.02 g, 53.50 mmol). (MS: [M+H] + =656)

[0294] Synthesis Example 22. Synthesis of Compound 22

[0295]

[0296] Using 4′-bromospiro[adamantane-2,9′-xanthene] (20.0 g, 52.45 mmol) and bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine (20.85 g, 53.50 mmol), the above-mentioned compound 22 (28.0 g, yield 77.37%) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS: [M+H] + =690)

[0297] Synthesis Example 23. Synthesis of Compound 23

[0298]

[0299] Compound 23 (26.5 g, yield 78.35%) was obtained by the same method as in Synthesis Example 1 using 2′-bromospiro[adamantane-2,9′-thioxanthine] (20.0 g, 50.33 mmol) and N-([1,1′-biphenyl]-4-yl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-amine (18.25 g, 51.34 mmol). (MS: [M+H] + =672)

[0300] Synthesis Example 24. Synthesis of Compound 24

[0301]

[0302] Using 2′-bromospiro[adamantane-2,9′-thioxanthine] (20.0 g, 50.33 mmol) and bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine (20.00 g, 51.34 mmol), the above-mentioned compound 24 (28.0 g, yield 78.79%) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS: [M+H] + =706)

[0303] Synthesis Example 25. Synthesis of Compound 25

[0304]

[0305] Compound 25 (26.5 g, 78.35% yield) was obtained by the same method as in Synthesis Example 1 using 3′-bromospiro[adamantane-2,9′-thioxanthine] (20.0 g, 50.33 mmol) and N-([1,1′-biphenyl]-4-yl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-amine (18.25 g, 51.34 mmol). (MS: [M+H] + =672)

[0306] Synthesis Example 26. Synthesis of Compound 26

[0307]

[0308] Using 3′-bromospiro[adamantane-2,9′-thioxanthine] (20.0 g, 50.33 mmol) and bis(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amine (20.00 g, 51.34 mmol), the above-mentioned compound 26 (28.0 g, yield 78.79%) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS: [M+H] + =706)

[0309] Synthesis Example 27. Synthesis of Compound 27

[0310]

[0311] Compound 27 (28.5 g, 79.01% yield) was obtained by the same method as in Synthesis Example 1 using 5′-chloro-2′-phenylspiro[adamantane-2,9′-fluorene] (20.0 g, 50.38 mmol) and N-([1,1′-biphenyl]-4-yl)-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-amine (18.27 g, 51.39 mmol). (MS: [M+H] + =716)

[0312] Synthesis Example 28. Synthesis of Compound 28

[0313]

[0314] Compound 28 (30.0 g, yield 78.76%) was obtained by the same method as in Synthesis Example 1 using 2′-chloro-4′-phenylspiro[adamantane-2,9′-fluorene] (20.0 g, 50.38 mmol) and 9,9-dimethyl-N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-9H-fluoren-2-amine (20.33 g, 51.39 mmol). (MS: [M+H] + =756)

[0315] Synthesis Example 29. Synthesis of Compound 29

[0316]

[0317] Compound 29 (30.5 g, 80.01% yield) was obtained by the same method as in Synthesis Example 1 using 2′-chloro-7′-phenylspiro[adamantane-2,9′-fluorene] (20.0 g, 50.38 mmol) and 9,9-dimethyl-N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-9H-fluoren-2-amine (20.33 g, 51.39 mmol). (MS: [M+H] + =756)

[0318] Synthesis Example 30. Synthesis of Compound 30

[0319]

[0320] Compound 30 (28.5 g, 79.50% yield) was obtained by the same method as in Synthesis Example 1 using 2′-(4-(tert-butyl)phenyl)-7′-chlorospiro[adamantane-2,9′-fluorene] (20.0 g, 44.14 mmol) and 9,9-dimethyl-N-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-9H-fluoren-2-amine (17.81 g, 45.03 mmol). (MS: [M+H] + =812)

[0321] Synthesis Example 31. Synthesis of Compound 31

[0322]

[0323] Compound 31 (21.0 g, yield 77.67%) was obtained by the same method as in Synthesis Example 1 using N-([1,1′-biphenyl]-4-yl)-3′-phenylspiro[adamantane-2,9′-fluorene]-2′-amine (20.0 g, 37.76 mmol) and 6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (10.29 g, 38.51 mmol). (MS: [M+H] + =716)

[0324] Synthesis Example 32. Synthesis of Compound 32

[0325]

[0326] Compound 32 (20.0 g, yield 77.07%) was obtained by the same method as in Synthesis Example 1 using 3′-(4-(tert-butyl)phenyl)-N-(9,9-dimethyl-9H-fluoren-2-yl)spiro[adamantane-2,9′-fluoren]-2′-amine (20.0 g, 31.95 mmol) and 6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (8.71 g, 32.59 mmol). (MS: [M+H] + =812)

[0327] Synthesis Example 33. Synthesis of Compound 33

[0328]

[0329] Compound 33 (20.5 g, yield 75.82%) was obtained by the same method as in Synthesis Example 1 using N-([1,1′-biphenyl]-4-yl)-3′-phenylspiro[adamantane-2,9′-fluorene]-4′-amine (20.0 g, 37.76 mmol) and 6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (10.29 g, 38.51 mmol). (MS: [M+H] + =716)

[0330] Synthesis Example 34. Synthesis of Compound 34

[0331]

[0332] Toluene (300 ml) was added to 3'-phenylspiro[adamantane-2,9'-fluorene]-2'-amine (15.0 g, 39.73 mmol), 6-bromo-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene (21.76 g, 81.45 mmol), and sodium tert-butoxide (10.69 g, 111.24 mmol), and the mixture was heated and stirred for 10 minutes. Bis(tri-tert-butylphosphine)palladium (0.10 g, 0.20 mmol) dissolved in toluene (30 ml) was added to the above mixture, and the mixture was heated and stirred for 1 hour. After the reaction was completed and filtered, the layers were separated using toluene and water. After removing the solvent, the product was recrystallized from ethyl acetate to obtain the above compound 34 (23.5 g, yield 78.85%). (MS: [M+H] + =750)

[0333] <Example>

[0334] Example 1-1

[0335] 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.

[0336] On the ITO transparent electrode prepared in this way, the following compound HAT was applied to The hole injection layer was formed by thermal vacuum deposition of a thickness of 1000 nm. On the hole injection layer, the following compound HT1 was deposited as a hole transport layer. After vacuum deposition with a thickness of 1000 nm, the compound 1 prepared in the above-mentioned synthesis example 1 was coated on a substrate as an electron suppression layer. Then, as the light-emitting layer, the following compound BH and the following compound BD were mixed at a weight ratio of 25:1 and a thickness of 1000 nm. Then, as a hole suppression layer, the following compound HB1 was deposited in a vacuum evaporation process. Next, as a layer for simultaneously performing electron transport and electron injection, the following compound ET1 and the following compound Liq were mixed at a weight ratio of 1:1 and a thickness of On the electron transport and electron injection layers, lithium fluoride (LiF) is deposited in the form of The thickness of the aluminum A cathode is formed by evaporation with a thickness of , thereby manufacturing an organic light-emitting device.

[0337]

[0338] Examples 1-2 to 1-20 and Comparative Examples 1-1 to 1-4

[0339] Organic light-emitting devices of Examples 1-2 to 1-20 and Comparative Examples 1-1 to 1-4 were prepared by the same method as in Example 1-1, except that the compounds listed in Table 1 below were used instead of Compound 1. The structures of Compounds EB1 to EB4 used in Comparative Examples 1-1 to 1-4 are shown below.

[0340]

[0341] <Experimental Example 1>

[0342] The organic light emitting devices manufactured in Examples 1-1 to 1-20 and Comparative Examples 1-1 to 1-4 were subjected to a 10 mA / cm 2 The voltage, efficiency, color coordinates and lifespan were measured when the current was 1.5 %. The results are shown in Table 1. On the other hand, T95 refers to the time required for the luminance to decrease from the initial luminance (6000 nits) to 95%.

[0343] [Table 1]

[0344]

[0345] As shown in Table 1, it was confirmed that the compound of the present invention has excellent electron suppression ability, and an organic light-emitting device using the compound as an electron suppression layer exhibits significant effects in terms of driving voltage, efficiency, and life.

[0346] Examples 2-1 to 2-27 and Comparative Examples 2-1 to 2-5

[0347] Organic light-emitting devices of Examples 2-1 to 2-27 and Comparative Examples 2-1 to 2-5 were produced using the same method as Example 1-1, except that Compound EB1 was used instead of Compound 1 as the electron suppression layer, and the compounds listed in Table 2 below were used instead of Compound HT1 as the hole transport layer. The structures of Compounds HT2 to HT6 used in Comparative Examples 2-1 to 2-5 are shown below.

[0348]

[0349] <Experimental Example 2>

[0350] When a current of 10 mA / cm2 was applied to the organic light-emitting devices produced in Examples 2-1 to 2-27 and Comparative Examples 1-1 and 2-1 to 2-5, the voltage, efficiency, color coordinates, and lifetime were measured. The results are shown in Table 2. T95 refers to the time required for the luminance to decrease to 95% of the initial luminance (6000 nits).

[0351] [Table 2]

[0352]

[0353]

[0354] As shown in Table 2, it was confirmed that the compound of the present invention has excellent hole transporting ability, and an organic light-emitting device using the compound as a hole transporting layer exhibits remarkable effects in terms of driving voltage, efficiency, and lifespan.

[0355] [Explanation of symbols]

[0356] 1: Substrate 2: Anode

[0357] 3: Light-emitting layer 4: Cathode

[0358] 5: Hole injection layer 6: Hole transport layer

[0359] 7: Electron suppression layer 8: Electron injection and transport layer.

Claims

1. A compound represented by the following chemical formula 1: [Chemical Formula 1] In the chemical formula 1, X is a single bond, O or S, R1 and R2 are each independently hydrogen, deuterium, phenyl, phenyl substituted with 1 or 2 tert-butyl groups, biphenyl, naphthyl or Said R1 and R2 are each phenyl, phenyl substituted by 1 or 2 tert-butyl groups, biphenyl, naphthyl or When the phenyl group, the phenyl group substituted with 1 or 2 tert-butyl groups, the biphenyl group, the naphthyl group or unsubstituted or substituted with more than one deuterium, a is an integer from 0 to 3, b is an integer from 0 to 4, L1 to L3 are each independently a single bond, a phenylene group, or a phenylene group substituted with 4 deuterium atoms, Ar1 and Ar2 are each independently phenyl, phenyl substituted by one tert-butyl group, phenyl substituted by one adamantyl group, biphenyl, terphenyl, naphthyl, phenylnaphthyl, naphthylphenyl, dimethylfluorenyl, phenylfluorenyl, diphenylfluorenyl, carbazolyl, dibenzofuranyl, dibenzothiophenyl or Ar1 and Ar2 are unsubstituted or substituted with one or more deuteriums, At least one of Ar1 and Ar2 is unsubstituted or substituted with one or more deuteriums.

2. The compound according to claim 1, wherein Ar1 and Ar2 are unsubstituted or substituted with one or more deuterium Any one selected from the group consisting of:

3. The compound according to claim 1, wherein Ar1 and Ar2 are each independently any one selected from the group consisting of: as well as At least one of Ar1 and Ar2 is 4. The compound according to claim 1, wherein The compound represented by Chemical Formula 1 is any one selected from the group consisting of:

5. 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 4. The organic light-emitting device according to claim 5 , wherein: The organic layer is an electron suppression layer or a hole transport layer.

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