New compound and organic light-emitting device containing the same

Abstract

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

Description

Technical Field

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims the benefit of priority from Korean Patent Application No. 10-2022-0112123 filed on September 5, 2022, in the Korean Intellectual Property Office, the disclosure of which is incorporated herein by reference in its entirety.

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

[0004] Generally, the organic light emitting phenomenon refers to a phenomenon in which electrical energy is converted into light energy by using organic materials. Organic light emitting devices using the organic light emitting phenomenon have characteristics such as wide viewing angle, excellent contrast, fast response time, excellent brightness, driving voltage and response speed, and therefore many studies have been conducted.

[0005] An organic light-emitting device generally has a structure including an anode, a cathode, and an organic material layer between the anode and the cathode. The organic material layer generally has a multilayer structure including different materials to enhance the efficiency and stability of the organic light-emitting device. For example, the organic material layer may be formed of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. In the structure of the organic light-emitting device, if a voltage is applied between two electrodes, holes are injected from the anode into the organic material layer, and electrons are injected from the cathode into the organic material layer, and when the injected holes and electrons meet each other, excitons are formed, and light is emitted when the excitons fall back to the ground state.

[0006] There is a continuing need to develop new materials for organic materials used in organic light emitting devices as described above.

[0007] [Prior art literature]

[0008] [Patent Document]

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

[0010] Technical issues

[0011] An object of the present disclosure is to provide novel compounds and organic light-emitting devices comprising the same.

[0012] Technical Solution

[0013] Provided herein is a compound represented by the following Chemical Formula 1:

[0014] [Chemical formula 1]

[0015]

[0016] Wherein, in Chemical Formula 1,

[0017] each X is independently N, CH, or CD, provided that two or more of X are N,

[0018] L is a single bond, or a substituted or unsubstituted C 6-60 Arylene,

[0019] Ar1 and Ar2 are each independently substituted or unsubstituted C 6-60 Aryl,

[0020] Ar3 and Ar4 are each independently unsubstituted or substituted with at least one deuterium substituted phenyl group,

[0021] Any one of Ar1 to Ar4 is substituted by cyano,

[0022] HAr is unsubstituted or each independently selected from deuterium, substituted or unsubstituted C 1-60 Alkyl and substituted or unsubstituted C 6-60 pyrimidinyl substituted with 1 to 3 substituents of aryl; substituted with two substituted or unsubstituted C 6-60 Aryl substituted triazine group; or a substituted or unsubstituted C 6-60 Aryl substituted quinazolinyl,

[0023] a and b are each independently an integer from 0 to 4,

[0024] n and m are each independently 0 or 1,

[0025] The condition is that n+m is 1,

[0026] a+n is an integer from 0 to 4, and

[0027] b+m is an integer from 0 to 4.

[0028] Also provided herein is an organic light emitting device including: a first electrode; a second electrode disposed opposite to the first electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes the compound represented by Chemical Formula 1.

[0029] Beneficial Effects

[0030] The compound represented by Chemical Formula 1 as described above can be used as a material of an organic material layer in an organic light-emitting device, and can improve efficiency, achieve low driving voltage and / or improve life characteristics in the organic light-emitting device. In particular, the compound represented by Chemical Formula 1 can be used as a hole injection material, a hole transport material, a hole injection and transport material, a light-emitting material, an electron transport material, or an electron injection material. BRIEF DESCRIPTION OF THE DRAWINGS

[0031] Figure 1 An example of an organic light emitting device including a substrate 1 , an anode 2 , a light emitting layer 3 , and a cathode 4 is shown.

[0032] Figure 2 An example of an organic light emitting device including a substrate 1 , an anode 2 , a hole injection layer 5 , a hole transport layer 6 , a light emitting layer 3 , an electron transport and injection layer 7 , and a cathode 4 is shown. DETAILED DESCRIPTION

[0033] Hereinafter, embodiments of the present disclosure will be described to more completely understand the disclosed subject matter.

[0034] As used herein, the symbol "" means a bond to another substituent and "D" means deuterium.

[0035] As used herein, the term "substituted or unsubstituted" means unsubstituted or substituted with one or more substituents selected from the following: deuterium; halogen group; cyano group; nitro group; hydroxyl group; carbonyl group; ester group; imide group; amino group; phosphine oxide group; alkoxy group; aryloxy group; alkylthio group; arylthio group; alkylsulfonyl group; arylsulfonyl group; silyl group; boron group; alkyl group; cycloalkyl group; alkenyl group; aryl group; aralkyl group; aralkenyl group; alkylaryl group; alkylamino group; aralkylamino group; heteroarylamino group; arylamino group; arylphosphino group; or a heterocyclic group containing one or more of N, O and S atoms, or unsubstituted or substituted with a substituent in which two or more substituents are connected among the substituents exemplified above. For example, "a substituent in which two or more substituents are connected" can be a biphenyl group. That is, the biphenyl group can be an aryl group, or it can also be interpreted as a substituent in which two phenyl groups are connected. In one example, the term "substituted or unsubstituted" can be understood to mean "unsubstituted or selected from deuterium, halogen, cyano, C 1-10 Alkyl, C 1-10 Alkoxy and C 6-20The term "substituted with one or more substituents selected from the group consisting of deuterium, halogen, cyano, methyl, ethyl, phenyl and naphthyl" may be used herein to refer to "substituted with one or more substituents selected from the group consisting of aryl, deuterium, halogen, cyano, methyl, ethyl, phenyl and naphthyl". In addition, the term "substituted with one or more substituents" as used herein may be understood to mean "substituted with a single to the maximum number of replaceable hydrogen atoms". Alternatively, the term "substituted with one or more substituents" as used herein may be understood to mean "substituted with 1 to 5 substituents", or "substituted with one or two substituents".

[0036] In the present disclosure, the carbon number of the carbonyl group is not particularly limited, but is preferably 1 to 40. Specifically, it may be a substituent having the following structure, but is not limited thereto.

[0037]

[0038] In the present disclosure, the ester group may have a structure in which the oxygen of the ester group may be substituted by a linear, branched, or cyclic alkyl group having 1 to 25 carbon atoms, or an aryl group having 6 to 25 carbon atoms. Specifically, the ester group may be a substituent having the following structural formula, but is not limited thereto.

[0039]

[0040] In the present disclosure, the carbon number of the imide group is not particularly limited, but is preferably 1 to 25. Specifically, the imide group may be a substituent having the following structural formula, but is not limited thereto.

[0041]

[0042] In the present disclosure, a substituted or unsubstituted silyl group refers to -Si(Z1)(Z2)(Z3), wherein Z1, Z2 and Z3 may each independently represent hydrogen, deuterium, a substituted or unsubstituted C 1-60 Alkyl, substituted or unsubstituted C 1-60 Haloalkyl, substituted or unsubstituted C 2-60 Alkenyl, substituted or unsubstituted C 2-60 haloalkenyl, or substituted or unsubstituted C 6-60 According to one embodiment, Z1, Z2 and Z3 may each independently represent hydrogen, deuterium, substituted or unsubstituted C 1-10 Alkyl, substituted or unsubstituted C 1-10 haloalkyl, or substituted or unsubstituted C 6-20Specific examples of the silyl group include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl and the like, but are not limited thereto.

[0043] In the present disclosure, the boryl group specifically includes trimethylboryl, triethylboryl, tert-butyldimethylboryl, triphenylboryl, phenylboryl, and the like, but is not limited thereto.

[0044] In the present disclosure, examples of halogen groups include fluorine, chlorine, bromine or iodine.

[0045] In the present disclosure, the alkyl group may be linear or branched, and the carbon number thereof is not particularly limited, but is preferably 1 to 40. According to one embodiment, the carbon number of the alkyl group is 1 to 20. According to another embodiment, the carbon number of 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-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, 1-ethylpropyl, 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.

[0046] In the present disclosure, the alkenyl group may be linear or branched, and the carbon number thereof is not particularly limited, but is preferably 2 to 40. According to one embodiment, the carbon number of the alkenyl group is 2 to 20. According to another embodiment, the carbon number of the alkenyl group is 2 to 10. According to yet another embodiment, the carbon number of the alkenyl group is 2 to 6. Specific examples thereof include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbene, styryl, etc., but are not limited thereto.

[0047] In the present disclosure, alicyclic groups refer to monovalent substituents derived from saturated or unsaturated hydrocarbon ring compounds, which contain only carbon as ring atoms but do not have aromaticity, and are understood to include both monocyclic and condensed polycyclic compounds. According to one embodiment, the carbon number of the alicyclic group is 3 to 60. According to another embodiment, the carbon number of the cycloalkyl group is 3 to 30. According to yet another embodiment, the carbon number of the cycloalkyl group is 3 to 20. Examples of such alicyclic groups include monocyclic groups, such as cycloalkyl, bridged hydrocarbon groups, spirocyclic hydrocarbon groups, substituents derived from hydrogenated derivatives of aromatic hydrocarbon compounds, and the like.

[0048] Specific examples of cycloalkyl include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and the like, but are not limited thereto.

[0049] In addition, examples of the bridged hydrocarbon group include bicyclo[1.1.0]butyl, bicyclo[2.2.1]heptyl, bicyclo[4.2.0]octa-1,3,5-trienyl, adamantyl, decalinyl, and the like, but are not limited thereto.

[0050] Examples of the spirocyclic hydrocarbon group include spiro[3.4]octyl, spiro[5.5]undecyl, and the like, but are not limited thereto.

[0051] In addition, the substituent derived from the hydrogenated derivative of the aromatic hydrocarbon compound refers to a substituent derived from a compound in which hydrogen is added to a part of the unsaturated bond of the monocyclic or polycyclic aromatic hydrocarbon compound. Examples of such substituents include 1H-indenyl, 2H-indenyl, 4H-indenyl, 2,3-dihydro-1H-indenyl, 1,4-dihydronaphthyl, 1,2,3,4-tetrahydronaphthyl, 6,7,8,9-tetrahydro-5H-benzo[7]annulyl, 6,7-dihydro-5H-benzocycloheptenyl, etc., but are not limited thereto.

[0052] In the present disclosure, an aryl group is understood to mean a substituent derived from a monocyclic or condensed polycyclic compound having aromaticity while containing only carbon atoms as ring-constituting atoms, and its carbon number is not particularly limited, but is preferably 6 to 60. 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. As a monocyclic aryl group, the aryl group may be phenyl, biphenyl, terphenyl, etc., but is not limited thereto. Polycyclic aryl groups include naphthyl, anthracenyl, phenanthrenyl, pyrenyl, peryl, etc., but not limited thereto.

[0053] In the present disclosure, the fluorenyl group may be substituted, and two substituents may be connected to each other to form a spirocyclic structure. In the case where the fluorenyl group is substituted, etc. However, the structure is not limited thereto.

[0054] In the present disclosure, a heterocyclic group refers to a monovalent substituent derived from a monocyclic or condensed polycyclic compound containing at least one heteroatom selected from O, N, Si and S as a ring-constituting atom in addition to a carbon atom, and is understood to include both substituents having aromaticity and substituents not having aromaticity. According to one embodiment, the carbon number of the heterocyclic group is 2 to 60. According to another embodiment, the carbon number of the heterocyclic group is 2 to 30. According to yet another embodiment, the carbon number of the heterocyclic group is 2 to 20. Examples of heterocyclic groups include heteroaryl groups, substituents derived from hydrogenated derivatives of heteroaromatic compounds, and the like.

[0055] Specifically, the heteroaryl group refers to a substituent derived from a monocyclic or condensed polycyclic compound containing at least one heteroatom selected from N, O and S as a ring-constituting atom in addition to a carbon atom, and means a substituent having aromaticity. According to one embodiment, the carbon number of the heteroaryl group is 2 to 60. According to another embodiment, the carbon number of the heteroaryl group is 2 to 30. According to another embodiment, the carbon number of the heteroaryl group is 2 to 20. Examples of the heteroaryl group include thienyl, furanyl, pyrrolyl, imidazolyl, thiazolyl, Azolyl, oxadiazolyl, triazolyl, pyridinyl, bipyridinyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzo oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothiophenyl, dibenzothiophenyl, benzofuranyl, dibenzofuranyl, phenanthroline, isothiophene oxazolyl, thiadiazolyl, phenothiazinyl, etc., but not limited thereto.

[0056] In addition, the substituent derived from the hydrogenated derivative of the heteroaromatic compound refers to a substituent derived from a compound in which hydrogen is added to a portion of the unsaturated bond of the monocyclic or polycyclic heteroaromatic compound. Examples of such substituents include 1,3-dihydroisobenzofuranyl, 2,3-dihydrobenzofuranyl, 1,3-dihydrobenzo[c]thienyl, 2,3-dihydro[b]thienyl (2,3-dihydro[b]thienyl), etc., but are not limited thereto.

[0057] In the present disclosure, the aryl in aralkyl, aralkenyl, alkylaryl, arylamine and arylsilyl is the same as the example of aryl as defined above. In the present disclosure, the alkyl in aralkyl, alkylaryl and alkylamine is the same as the example of alkyl as defined above. In the present disclosure, the heteroaryl in heteroarylamine can apply the description of heteroaryl as defined above. In the present disclosure, the alkenyl in aralkenyl is the same as the example of alkenyl as defined above. In the present disclosure, the description of aryl as defined above can be applied, except that arylene is a divalent group. In the present disclosure, the description of heteroaryl as defined above can be applied, except that heteroarylene is a divalent group. In the present disclosure, the description of aryl or cycloalkyl as defined above can be applied, except that the hydrocarbon ring is not a monovalent group but is formed by combining two substituents. In the present disclosure, the description of the heteroaryl group as defined above may be applied except that the heterocyclic ring is not a monovalent group but is formed by combining two substituents.

[0058] In the present disclosure, the term "deuterated or substituted with deuterium" means that at least one of the replaceable hydrogens in a compound, a divalent linking group or a monovalent substituent is replaced with deuterium.

[0059] In addition, the term "unsubstituted or substituted with deuterium" or "substituted with deuterium or unsubstituted" means "unsubstituted or a single to maximum number of replaceable hydrogens are replaced with deuterium". In one example, considering that the maximum number of hydrogens that can be replaced with deuterium in the phenanthryl structure is 9, the term "unsubstituted or deuterium-substituted phenanthryl" can be understood to mean "phenanthryl that is unsubstituted or substituted with 1 to 9 deuterium atoms".

[0060] In addition, the term "deuterated structure" means a compound, a divalent linking group or a monovalent substituent including all structures in which at least one hydrogen is replaced by deuterium. In one example, the deuterated structure of phenyl can be understood to refer to the following monovalent substituents in which at least one replaceable hydrogen in phenyl is replaced by deuterium.

[0061]

[0062] In addition, the "deuterium substitution rate" or "deuteration degree" of a compound means the ratio of the number of substituted deuterium atoms to the total number of hydrogen atoms that can be present in the compound (the sum of the number of hydrogen atoms that can be replaced by deuterium in the compound and the number of substituted deuterium atoms) calculated as a percentage. Therefore, when the "deuterium substitution rate" or "deuteration degree" of a compound is "K%", this means that K% of the hydrogen atoms that can be replaced by deuterium in the compound are replaced by deuterium.

[0063] At this time, the "deuterium substitution rate" or "degree of deuteration" can be measured using MALDI-TOF MS (matrix-assisted laser desorption / ionization time-of-flight mass spectrometry), nuclear magnetic resonance spectroscopy ( 1 H NMR), TLC / MS (thin layer chromatography / mass spectrometry), GC / MS (gas chromatography / mass spectrometry), etc. are measured according to a well-known method. More specifically, when MALDI-TOF MS is used, the "deuterium substitution rate" or "deuteration degree" is obtained by determining the number of deuterium atoms substituted in the compound through MALDI-TOF MS analysis and then calculating the ratio of the number of deuterium atoms substituted to the total number of hydrogen atoms that can be present in the compound as a percentage.

[0064] (Compound)

[0065] According to the present disclosure, a compound represented by Chemical Formula 1 is provided.

[0066] Preferably, Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-3:

[0067] [Chemical formula 1-1]

[0068]

[0069] [Chemical formula 1-2]

[0070]

[0071] [Chemical formula 1-3]

[0072]

[0073] Among them, in Chemical Formulas 1-1 to 1-3,

[0074] X, L, Ar1, Ar2, Ar3, Ar4, a, b, n and m are as defined above,

[0075] Y is N or CR', provided that two or more of Y are N,

[0076] R' is hydrogen, deuterium, substituted or unsubstituted C 1-60 Alkyl, or substituted or unsubstituted C 6-60 Aryl,

[0077] R1 and R2 are each independently substituted or unsubstituted C 6-60 Aryl, and

[0078] c is an integer from 0 to 4.

[0079] Preferably, Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-4 to 1-9:

[0080] [Chemical formula 1-4]

[0081]

[0082] [Chemical formula 1-5]

[0083]

[0084] [Chemical formula 1-6]

[0085]

[0086] [Chemical formula 1-7]

[0087]

[0088] [Chemical formula 1-8]

[0089]

[0090] [Chemical formula 1-9]

[0091]

[0092] Wherein, in Chemical Formulae 1-4 to 1-9, X, L, Ar1, Ar2, Ar3, Ar4, HAr, a and b are as defined above.

[0093] Preferably, L is a single bond, a phenylene group or a biphenyl diyl group,

[0094] wherein the phenylene group and the biphenyldiyl group are unsubstituted or substituted with at least one deuterium group.

[0095] Preferably, Ar1 is phenyl which is unsubstituted or substituted with at least one deuterium.

[0096] Preferably, Ar2 is phenyl, biphenyl or naphthyl, wherein said Ar2 is unsubstituted or substituted with at least one deuterium.

[0097] Preferably, L is phenylene or biphenyldiyl, wherein said L is unsubstituted or substituted with at least one deuterium, and

[0098] Ar2 is phenyl substituted with cyano, or naphthyl substituted with cyano, wherein said Ar2 is deuterium substituted or unsubstituted.

[0099] More preferably, L is unsubstituted or substituted with at least one deuterium phenylene, or unsubstituted or substituted with at least one deuterium biphenyldiyl; and Ar2 is phenyl substituted with one cyano group and 0 to 4 deuteriums, or naphthyl substituted with one cyano group and 0 to 6 deuteriums.

[0100] Preferably, L is a single bond; Ar2 is phenyl or biphenyl, wherein said Ar2 is unsubstituted or substituted with at least one deuterium, and

[0101] Ar3 is phenyl substituted with cyano, wherein said Ar3 is deuterium substituted or unsubstituted.

[0102] More preferably, L is a single bond; Ar2 is phenyl which is unsubstituted or substituted with at least one deuterium, or biphenyl which is unsubstituted or substituted with at least one deuterium; and Ar3 is phenyl which is substituted with one cyano and 0 to 4 deuteriums.

[0103] Preferably, R' is hydrogen, deuterium, or methyl which is unsubstituted or substituted with at least one deuterium.

[0104] Preferably, R1 and R2 are each independently phenyl, biphenyl, or naphthyl, wherein said R1 and said R2 are unsubstituted or substituted with at least one deuterium.

[0105] Representative examples of the compound represented by Chemical Formula 1 are as follows:

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113] Furthermore, according to the present disclosure, a method for preparing a compound represented by Chemical Formula 1 as shown in the following Reaction Scheme 1 is provided.

[0114] [Reaction Scheme 1]

[0115]

[0116] In Reaction Scheme 1, X, L, Ar1, Ar2, Ar3, Ar4, HAr, a, b, n and m are the same as defined above, and Y is a halogen, preferably bromine or chlorine.

[0117] The compound represented by Chemical Formula 1 can be prepared by Suzuki coupling reaction. At this time, the Suzuki coupling reaction is preferably carried out in the presence of a palladium catalyst and a base, and the reactive group used for the reaction can be modified to any reactive group known in the art. Such a preparation method can be further presented in the preparation examples described later.

[0118] (Organic Light Emitting Devices)

[0119] In addition, according to the present disclosure, there is provided an organic light-emitting device including a compound represented by Chemical Formula 1. In one example, the present disclosure provides an organic light-emitting device including: a first electrode; a second electrode disposed opposite to the first electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes the compound represented by Chemical Formula 1.

[0120] The organic material layer of the organic light-emitting device of the present disclosure may have a single-layer structure, or it may have a multilayer structure in which two or more organic material layers are stacked. For example, the organic light-emitting device of the present disclosure may have a structure including a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. as an organic material layer. However, the structure of the organic light-emitting device is not limited thereto, and it may include a smaller number of organic layers.

[0121] In addition, the organic material layer may include a light emitting layer, wherein the light emitting layer may include the compound represented by Chemical Formula 1. In particular, the compound according to the present disclosure may be used as a dopant of the light emitting layer.

[0122] In addition, the organic material layer may include an electron transport layer, an electron injection layer, or a layer for simultaneous electron transport and electron injection, wherein the electron transport layer, the electron injection layer, or the layer for simultaneous electron transport and electron injection may contain the compound represented by Chemical Formula 1.

[0123] In addition, the organic material layer may include a hole injection layer, a hole transport layer, a light emitting layer, or an electron transport and injection layer, wherein the organic material layer including the above compound may be an electron transport and injection layer.

[0124] In addition, the organic light-emitting device according to the present disclosure may be a normal type organic light-emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate. In addition, the organic light-emitting device according to the present disclosure may be an inverted type organic light-emitting device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate. For example, Figure 1 and Figure 2 The structure of an organic light emitting device according to an embodiment of the present disclosure is shown.

[0125] Figure 1 An example of an organic light emitting device including a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4 is shown. In such a structure, the compound represented by Chemical Formula 1 may be contained in the light emitting layer.

[0126] Figure 2 An example of an organic light emitting device including a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 3, an electron transport and injection layer 7, and a cathode 4 is shown. In such a structure, the compound represented by Chemical Formula 1 may be contained in the electron transport and injection layer.

[0127] The organic light-emitting device according to the present disclosure can be manufactured by materials and methods known in the art, except that the light-emitting layer contains the compound according to the present disclosure and is manufactured as described above. In addition, when the organic light-emitting device includes a plurality of organic material layers, the organic material layers can be formed of the same material or different materials.

[0128] For example, an organic light-emitting device according to the present disclosure can be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. In this case, the organic light-emitting device can be manufactured by: depositing a metal, a conductive metal oxide, or an alloy thereof on a substrate using a PVD (physical vapor deposition) method such as a sputtering method or an electron beam evaporation method to form an anode; forming an organic material layer including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer on the anode, and then depositing a material that can be used as a cathode on the organic material layer. In addition to such a method, an organic light-emitting device can also be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

[0129] In addition, when manufacturing an organic light-emitting device, the compound represented by Chemical Formula 1 can be formed into an organic layer by a solution coating method and a vacuum deposition method. The solution coating method means spin coating, dip coating, blade coating, inkjet printing, screen printing, spraying, roller coating, etc., but is not limited thereto.

[0130] In addition to such a method, an organic light emitting device can also be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate (International Publication WO2003 / 012890). However, the manufacturing method is not limited thereto.

[0131] In one example, the first electrode is an anode and the second electrode is a cathode, or alternatively, the first electrode is a cathode and the second electrode is an anode.

[0132] As the anode material, it is generally preferred to use a material with a large work function so that holes can be smoothly injected into the organic material layer. Specific examples of anode materials include metals such as vanadium, chromium, copper, zinc and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole and polyaniline; etc., but are not limited thereto.

[0133] As the cathode material, it is generally preferred to use a material having a small work function so that electrons can be easily injected into the organic material layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; multilayer structure materials such as LiF / Al or LiO2 / Al; etc., but are not limited thereto.

[0134] The hole injection layer is a layer for injecting holes from the electrode, and the hole injection material is preferably such a compound: it has the ability to transport holes, so it has the effect of injecting holes in the anode and excellent hole injection effect on the light-emitting layer or the light-emitting material, preventing the excitons generated in the light-emitting layer from moving to the electron injection layer or the electron injection material, and the ability to form a thin film is further excellent. Preferably, the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of hole injection materials include metal porphyrins, oligothiophenes, organic materials based on arylamines, organic materials based on hexanitrile hexaazatriphenylene, organic materials based on quinacridone, organic materials based on perylene, anthraquinone, conductive polymers based on polyaniline and polythiophene, etc., but are not limited thereto.

[0135] The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer. The hole transport material is suitably a material having a large hole mobility that can receive holes from the anode or the hole injection layer and transport the holes to the light-emitting layer. Specific examples thereof include organic materials based on arylamine, conductive polymers, block copolymers in which conjugated parts and non-conjugated parts exist simultaneously, etc., but are not limited thereto.

[0136] The light-emitting material is preferably a material that can receive holes and electrons transmitted from the hole transport layer and the electron transport layer, respectively, combine the holes and the electrons to emit light in the visible light region, and has good quantum efficiency for fluorescence or phosphorescence. Specific examples of the light-emitting material include 8-hydroxy-quinoline aluminum complex (Alq3); carbazole-based compounds; diphenylethylene compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo-based azoles, benzothiazole-based and benzimidazole-based compounds; poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; polyfluorenes; rubrene; and the like, but are not limited thereto.

[0137] The light-emitting layer may include a host material and a dopant material. The host material includes fused aromatic ring derivatives, heterocyclic compounds, and the like. Specific examples of fused aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like. Examples of heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

[0138] Examples of dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, the aromatic amine derivative is a substituted or unsubstituted fused aromatic ring derivative having an arylamino group, and examples thereof include pyrene, anthracene, Diindenopyrene, etc. The styrylamine compound is a compound in which at least one arylvinyl group is substituted in a substituted or unsubstituted arylamine, wherein one or two or more substituents selected from aryl, silyl, alkyl, cycloalkyl and arylamino are substituted or unsubstituted. Specific examples thereof include styrylamine, styryldiamine, styryltriamine, styryltetramine, etc., but are not limited thereto. In addition, the metal complex includes iridium complex, platinum complex, etc., but are not limited thereto.

[0139] The electron injection and transport layer is a layer that injects electrons from the electrode and transports the received electrons to the light-emitting layer, and serves as both an electron transport layer and an electron injection layer, and is formed on the light-emitting layer or the hole blocking layer. The electron injection and transport material is suitably a material that can well receive electrons from the cathode and transfer the electrons to the light-emitting layer, and has a large electron mobility. The compound represented by Chemical Formula 1 can be used as an electron injection and transport layer material. Additional examples of electron injection and transport materials include: Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic free radical compounds; hydroxyflavone-metal complexes; triazine derivatives, etc., but are not limited thereto. Alternatively, it can be used together with: fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, Azoles, Oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenyl methane, anthrone, etc., and derivatives thereof; metal complex compounds; nitrogen-containing 5-membered ring derivatives; etc., but not limited thereto.

[0140] The electron injection and transport layer may also be formed as a separate layer, such as an electron injection layer and an electron transport layer. In such a case, the electron transport layer is formed on the light-emitting layer or the hole blocking layer, and the above-mentioned electron injection and transport material may be used as the electron transport material contained in the electron transport layer. In addition, the electron injection layer is formed on the electron transport layer, and examples of the electron injection material contained in the electron injection layer include LiF, NaCl, CsF, Li2O, BaO, fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, Azoles, Oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenyl methane, anthrone, etc., and their derivatives; metal complex compounds; nitrogen-containing 5-membered ring derivatives; and the like.

[0141] The metal complex compounds include 8-hydroxyquinoline lithium, bis(8-hydroxyquinoline) zinc, bis(8-hydroxyquinoline) copper, bis(8-hydroxyquinoline) manganese, tris(8-hydroxyquinoline) aluminum, tris(2-methyl-8-hydroxyquinoline) aluminum, tris(8-hydroxyquinoline) gallium, bis(10-hydroxybenzo[h]quinoline) beryllium, bis(10-hydroxybenzo[h]quinoline) zinc, bis(2-methyl-8-quinoline) chlorogallium, bis(2-methyl-8-quinoline)(o-cresol) gallium, bis(2-methyl-8-quinoline)(1-naphthol) aluminum, bis(2-methyl-8-quinoline)(2-naphthol) gallium, and the like, but are not limited thereto.

[0142] In one embodiment, the electron transport layer, the electron injection layer, or the electron injection and transport layer of the organic light-emitting device may include the compound represented by Chemical Formula 1 and the metal complex compound. In this case, the electron transport layer, the electron injection layer, or the electron injection and transport layer may include the compound represented by Chemical Formula 1 and the metal complex compound in a weight ratio of 10:90 to 90:10, a weight ratio of 30:70 to 70:30, or a weight ratio of 50:50.

[0143] The organic light emitting device according to the present disclosure may be a bottom emission type device, a top emission type device, or a double-sided emission type device, and in particular, it may be a bottom emission type light emitting device requiring relatively high light emission efficiency.

[0144] Furthermore, the compound represented by Chemical Formula 1 may be included in an organic solar cell or an organic transistor in addition to an organic light emitting device.

[0145] The preparation of the compound represented by Chemical Formula 1 and an organic light-emitting device including the same will be specifically described in the following examples. However, the following examples are provided only for illustrative purposes and are not intended to limit the scope of the present disclosure.

[0146] [Example]

[0147] Example 1: Preparation of Compound E1

[0148]

[0149] Under nitrogen atmosphere, E1-A (20 g, 38.4 mmol) and E1-B (16.7 g, 38.4 mmol) were added to 400 ml of 1,4-dihydroquinone. alkane, the mixture is stirred and refluxed. Then, tripotassium phosphate (24.4g, 115.2mmol) is dissolved in 24ml water, added thereto, the mixture is fully stirred, and then dibenzalacetone palladium (0.7g, 1.2mmol) and tricyclohexylphosphine (0.6g, 2.3mmol) are added thereto. After reacting for 7 hours, the reaction mixture is cooled to room temperature, and the solid produced is then filtered. The solid is added to 914mL chloroform, dissolved, washed with water twice, the organic layer is separated, anhydrous magnesium sulfate is added thereto, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is recrystallized from chloroform and ethyl acetate to obtain compound E1 (4.6g, yield: 15%) as a white solid.

[0150] MS:[M+H] + =794

[0151] Example 2: Preparation of Compound E2

[0152]

[0153] Compound E2 was prepared by the same process as the preparation method of Example 1, except that each starting material was used as in the above reaction scheme.

[0154] MS:[M+H] + =794

[0155] Example 3: Preparation of Compound E3

[0156]

[0157] Compound E3 was prepared by the same process as the preparation method of Example 1, except that each starting material was used as in the above reaction scheme.

[0158] MS:[M+H] + =794

[0159] Example 4: Preparation of Compound E4

[0160]

[0161] Compound E4 was prepared by the same process as the preparation method of Example 1, except that each starting material was used as in the above reaction scheme.

[0162] MS:[M+H] + =844

[0163] Example 5: Preparation of Compound E5

[0164]

[0165] Compound E5 was prepared by the same process as the preparation method of Example 1, except that each starting material was used as in the above reaction scheme.

[0166] MS:[M+H] + =718

[0167] Example 6: Preparation of Compound E6

[0168]

[0169] Compound E6 was prepared by the same process as the preparation method of Example 1, except that each starting material was used as in the above reaction scheme.

[0170] MS:[M+H] + =718

[0171] Example 7: Preparation of Compound E7

[0172]

[0173] Compound E7 was prepared by the same process as the preparation method of Example 1, except that each starting material was used as in the above reaction scheme.

[0174] MS:[M+H] + =794

[0175] Example 8: Preparation of Compound E8

[0176]

[0177] Compound E8 was prepared by the same process as the preparation method of Example 1, except that each starting material was used as in the above reaction scheme.

[0178] MS:[M+H] + =767

[0179] Example 9: Preparation of Compound E9

[0180]

[0181] Compound E9 was prepared by the same process as the preparation method of Example 1, except that each starting material was used as in the above reaction scheme.

[0182] MS:[M+H] + =767

[0183] Example 10: Preparation of Compound E10

[0184]

[0185] Compound E10 was prepared by the same process as the preparation method of Example 1, except that each starting material was used as in the above reaction scheme.

[0186] MS:[M+H] + =843

[0187] Example 11: Preparation of Compound E11

[0188]

[0189] Compound E11 was prepared by the same process as the preparation method of Example 1, except that each starting material was used as in the above reaction scheme.

[0190] MS:[M+H] + =793

[0191] Example 12: Preparation of Compound E12

[0192]

[0193] Compound E12 was prepared by the same process as the preparation method of Example 1, except that each starting material was used as in the above reaction scheme.

[0194] MS:[M+H] + =767

[0195] Example 13: Preparation of Compound E13

[0196]

[0197] Compound E13 was prepared by the same process as the preparation method of Example 1, except that each starting material was used as in the above reaction scheme.

[0198] MS:[M+H] + =799

[0199] [Experimental example]

[0200] Experimental Example 1

[0201] It is coated with a thickness of The glass substrate of ITO (indium tin oxide) film is put into the distilled water comprising the detergent dissolved therein, and carries out ultrasonic cleaning.At this moment, the detergent used is the product commercially available from Fisher Co., and the distilled water is the distilled water filtered twice by using the filter commercially available from Millipore Co..After ITO was washed for 30 minutes, distilled water was used to repeat ultrasonic cleaning twice for 10 minutes.After using distilled water to wash to complete, substrate isopropyl alcohol, acetone and methanol solvent ultrasonic cleaning and drying are used, and thereafter it is transferred to plasma cleaning machine.Then, substrate oxygen plasma is cleaned for 5 minutes, and then transferred to vacuum evaporation machine.

[0202] On the thus prepared ITO transparent electrode, the following compound HI-A was thermally vacuum deposited onto The hole injection layer is formed by coating a hexanitrile hexaazatriphenylene (HAT, ) and the following compound HT-A Vacuum deposition is sequentially performed to form a hole transport layer.

[0203] Then, the following compounds BH and BD were vacuum deposited on the hole transport layer at a weight ratio of 25:1. The compound E1 prepared in Example 1 and the following compound LiQ (lithium quinoline) were vacuum deposited on the light-emitting layer at a weight ratio of 1:1 to form a film with a thickness of The electron transport and injection layer is formed by sequentially depositing lithium fluoride (LiF) and aluminum on the electron transport and injection layer to have a thickness of 100 nm and a thickness of 100 nm, respectively. and thickness, thereby forming a cathode.

[0204]

[0205] During the above process, the vapor deposition rate of the organic material is maintained at to The deposition rates of lithium fluoride and aluminum at the cathode were kept at and The vacuum level during deposition was maintained at 1 × 10 -7 Up to 5×10 -8 Support, thereby manufacturing an organic light-emitting device.

[0206] Experimental Examples 2 to 13

[0207] An organic light-emitting device was manufactured in the same manner as in Experimental Example 1, except that the compounds shown in the following Table 1 were used instead of Compound E1 of Experimental Example 1.

[0208] Comparative Experimental Examples 1 to 13

[0209] An organic light-emitting device was manufactured in the same manner as in Experimental Example 1, except that the compounds shown in Table 1 below were used instead of Compound E1 of Experimental Example 1. Compounds ET-A to ET-M used in Table 1 below are as follows.

[0210]

[0211] At 10mA / cm 2 The driving voltage, luminous efficiency and color coordinates of the organic light-emitting devices manufactured in the experimental examples and the comparative experimental examples were measured at a current density of 20 mA / cm 2 The time (T90) required for the luminance to decrease to 90% of the initial luminance was measured at a current density of . The results are shown in Table 1 below.

[0212] [Table 1]

[0213]

[0214]

[0215] As shown in Table 1, it is determined that the organic light emitting device using the compound represented by Chemical Formula 1 of the present disclosure exhibits excellent characteristics in terms of voltage, efficiency, and / or lifespan (T90).

[0216] By comparing Experimental Examples 1 to 13 in Table 1 with Comparative Experimental Examples 1, 2, 4 to 6, 8, 12 and 13, it was determined that the organic light-emitting device including the compound of Chemical Formula 1 of the present disclosure exhibited significantly superior characteristics in terms of efficiency compared to the organic light-emitting device using compounds having different substituents between heterocyclic groups.

[0217] Comparing Experimental Examples 1 to 13 in Table 1 with Comparative Experimental Examples 3 and 10, it was determined that the organic light-emitting device including the compound of Chemical Formula 1 of the present disclosure exhibited significantly superior characteristics in terms of efficiency compared to the organic light-emitting device using the compound in which two cyano groups were substituted.

[0218] Comparing Experimental Examples 1 to 13 in Table 1 with Comparative Experimental Examples 7, 9, and 11, it was determined that the organic light-emitting device including the compound of Chemical Formula 1 of the present disclosure exhibited significantly superior characteristics in terms of lifespan compared to an organic light-emitting device using a compound in which a cyano group was not substituted.

[0219] [Explanation of Reference Numerals]

[0220] 1: Substrate 2: Anode

[0221] 3: Light-emitting layer 4: Cathode

[0222] 5: Hole injection layer 6: Hole transport layer

[0223] 7: Electron transport and injection layer

Claims

1. A compound represented by the following chemical formula 1: [Chemical formula 1] In Chemical Formula 1, X is N, or CH, provided that two or more of said X are N, L is a single bond, or a deuterium-substituted or unsubstituted C 6-30 Arylene, Ar1 and Ar2 are each independently deuterated or unsubstituted C 6-30 Aryl, Ar3 and Ar4 are phenyl groups, Any one of Ar1 to Ar4 is substituted by cyano, HAr is unsubstituted or substituted with 1 to 3 substituents of pyrimidinyl, wherein the substituents are deuterium, deuterium-substituted or unsubstituted C 1-20 Alkyl, or deuterium substituted or unsubstituted C 6-30 Aryl; through two C 6-30 Aryl-substituted triazine; or a C 6-30 Aryl substituted quinazolinyl, n and m are each independently 0 or 1, The condition is that n+m is 1.

2. The compound according to claim 1, wherein: Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-2 to 1-3: [Chemical formula 1-2] [Chemical formula 1-3] In Chemical Formulas 1-2 to 1-3, X, L, Ar1, Ar2, Ar3, Ar4, n and m are as defined in claim 1, R1 and R2 are each independently C 6-30 Aryl.

3. The compound according to claim 1, wherein: L is a single bond, a phenylene group, or a biphenyldiyl group.

4. The compound according to claim 1, wherein: Ar1 is phenyl.

5. The compound according to claim 1, wherein: Ar2 is phenyl or naphthyl.

6. The compound according to claim 1, wherein: L is phenylene or biphenyldiyl, and Ar2 is phenyl substituted by cyano, or naphthyl substituted by cyano.

7. The compound according to claim 1, wherein: L is a single bond, Ar2 is phenyl or biphenyl, and Ar3 is phenyl substituted by cyano.

8. The compound according to claim 2, wherein: R1 and R2 are each independently a phenyl group or a biphenyl group.

9. The compound according to claim 1, wherein: The compound represented by Chemical Formula 1 is any one selected from the following compounds:

10. An organic light-emitting device, comprising: a first electrode; a second electrode disposed opposite to the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein at least one layer of the organic material layers comprises the compound as defined in any one of claims 1 to 9, The organic material layer containing the compound is an electron transport layer, an electron injection layer, or an electron transport and injection layer.

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