Novel compound and organic light-emitting device comprising same

Abstract

The present invention provides a novel compound 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. 10-2023-0139310 filed on October 18, 2023, and incorporates all the contents disclosed in the document of the Korean Patent Application as a part of this specification.

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

[0004] Generally speaking, the organic light-emitting phenomenon refers to the phenomenon of converting electrical energy into light energy using organic substances. Organic light-emitting devices using the organic light-emitting phenomenon have wide viewing angles, excellent contrast, fast response time, and excellent brightness, driving voltage, and response speed characteristics, so a lot of research is being carried out.

[0005] An organic light-emitting device generally has a structure including an anode and a cathode and an organic layer located between the anode and the cathode. In order to improve the efficiency and stability of the organic light-emitting device, the organic layer is usually formed by a multilayer structure composed of different substances, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. For such an organic light-emitting device structure, if 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, and when the excitons transition back to the ground state, light is emitted.

[0006] As for organic substances used for organic light-emitting devices as described above, development of new materials continues to be required.

[0007] Prior art literature

[0008] Patent Literature

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

[0010] Technical issues

[0011] The present invention relates to novel compounds and organic light-emitting devices 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 independently N, CH or CD, and two or more of X are N, L is a single bond, or a substituted or unsubstituted C 6-60 Arylene, Ar1 and Ar2 are each independently substituted or unsubstituted C 6-60 Aryl, Ar3 and Ar4 are each independently a substituent represented by the following Chemical Formula 2:

[0018]

[0019] In the above chemical formula 2,

[0020] o and p are each independently 0 or 1,

[0021] q is an integer from 0 to 4,

[0022] r is an integer from 0 to 7,

[0023] s is an integer from 0 to 5,

[0024] However, o+p+r is an integer from 0 to 7.

[0025] Any one of Ar1 to Ar4 is substituted by a cyano group,

[0026] HAr is each independently selected from deuterium, substituted or unsubstituted C 1-60 Alkyl, and substituted or unsubstituted C 6-60 1 to 3 substituents in aryl substituted with pyrimidinyl; 2 substituted or unsubstituted C 6-60 triazine substituted with aryl; or substituted or unsubstituted with 1 C 6-60 Aryl substituted quinazolinyl,

[0027] a and b are each independently an integer from 0 to 4,

[0028] n and m are each independently 0 or 1,

[0029] However, n+m is 1,

[0030] a+n is an integer from 0 to 4,

[0031] b+m is an integer from 0 to 4.

[0032] In addition, the present invention provides an organic light-emitting device, comprising: 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 a compound represented by the above chemical formula 1.

[0033] Effects of the Invention

[0034] The compound represented by the above chemical formula 1 can be used as a material for an organic layer of an organic light-emitting device, in which improved efficiency, lower driving voltage and / or improved life characteristics can be achieved. In particular, the compound represented by the above chemical formula 1 can be used as a material for hole injection, hole transport, hole injection and transport, light emission, electron transport, or electron injection. BRIEF DESCRIPTION OF THE DRAWINGS

[0035] 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 .

[0036] Figure 2 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 , a light-emitting layer 3 , an electron transport and injection layer 7 , and a cathode 4 is shown.

[0037] Explanation of symbols

[0038] 1: Substrate 2: Anode

[0039] 3: Light-emitting layer 4: Cathode

[0040] 5: Hole injection layer 6: Hole transport layer

[0041] 7: Electron transport and injection layer DETAILED DESCRIPTION

[0042] In the following, the present invention will be described in more detail to help understanding the present invention.

[0043] In this manual, and "D" represents a bond to other substituents, and "D" represents deuterium.

[0044] In the present specification, the term "substituted or unsubstituted" refers to a group selected from deuterium; a halogen group; a cyano group; a nitro group; a hydroxyl group; a carbonyl group; an ester group; an imide group; an amino group; a phosphine oxide group; an alkoxy group; an aryloxy group; an alkylthio group Arylthio Alkylsulfonyl Arylsulfonyl Silyl; boryl; alkyl; cycloalkyl; alkenyl; aryl; aralkyl; aralkenyl; alkylaryl; alkylamino; aralkylamino; heteroarylamino; arylamino; arylphosphino; or substituted or unsubstituted with one or more substituents in a heterocyclic group containing one or more N, O and S atoms, or substituted or unsubstituted with a substituent formed by connecting two or more substituents among the substituents exemplified above. For example, "a substituent formed by connecting two or more substituents" can be a biphenyl group. That is, the biphenyl group can be an aryl group, and can also be interpreted as a substituent formed by connecting two phenyl groups. As an example, the term "substituted or unsubstituted" can be understood as "unsubstituted or substituted with a substituent selected from deuterium, halogen, cyano, C 1-10 Alkyl, C 1-10 Alkoxy and C 6-20 In the present specification, the term “substituted with one or more substituents in the aryl group” or “unsubstituted or substituted with one or more substituents selected from deuterium, halogen, cyano, methyl, ethyl, phenyl and naphthyl” may be understood as “substituted with 1 to the maximum number of replaceable hydrogen atoms”. Alternatively, in the present specification, the term “substituted with one or more substituents” may be understood as “substituted with 1 to 5 substituents” or “substituted with 1 or 2 substituents”.

[0045] In the present specification, the number of carbon atoms in the carbonyl group is not particularly limited, but the number of carbon atoms is preferably 1 to 40. Specifically, the substituent may be a substituent of the following structure, but the substituent is not limited thereto.

[0046]

[0047] In the present specification, in the ester group, 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 substituents may be of the following structural formulas, but are not limited thereto.

[0048]

[0049] In the present specification, the number of carbon atoms in the imide group is not particularly limited, but the number of carbon atoms is preferably 1 to 25. Specifically, the substituent may be a substituent of the following structure, but the substituent is not limited thereto.

[0050]

[0051] In the present specification, a substituted or unsubstituted silyl group refers to -Si(Z1)(Z2)(Z3), where Z1, Z2 and Z3 are each independently hydrogen, deuterium, substituted or unsubstituted C 1-60 Alkyl, substituted or unsubstituted C1-60 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 can each independently be hydrogen, deuterium, substituted or unsubstituted C 1-10 Alkyl, substituted or unsubstituted C 1-10 Haloalkyl, substituted or unsubstituted C 1-10 haloalkyl, or substituted or unsubstituted C 6-20 Specific examples of the silyl group include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, and phenylsilyl, but are not limited thereto.

[0052] In the present specification, specific examples of the boryl group include trimethylboryl, triethylboryl, tert-butyldimethylboryl, triphenylboryl, and phenylboryl, but are not limited thereto.

[0053] In the present specification, as examples of the halogen group, there are fluorine, chlorine, bromine or iodine.

[0054] In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the number of carbon atoms in the alkyl group is 1 to 20. According to another embodiment, the number of carbon atoms in the alkyl group is 1 to 10. According to another embodiment, specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, 1-ethyl-propyl, 1,1-dimethylpropyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, isohexyl, 1-methylhexyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 5-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2,4,4-trimethyl-1-pentyl, 2,4,4-trimethyl-2-pentyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl and the like, but are not limited thereto.

[0055] 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 number of carbon atoms of the alkenyl group is 2 to 20. According to another embodiment, the number of carbon atoms of the alkenyl group is 2 to 10. According to another embodiment, the number of carbon atoms of the alkenyl group is 2 to 6. As specific examples, there are 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-(naphthalene-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbene, styryl, etc., but are not limited thereto.

[0056] In this specification, the alicyclic group refers to a monovalent substituent derived from a saturated or unsaturated hydrocarbon ring compound containing only carbon as a ring atom and not having aromaticity, and is understood to include all monocyclic or condensed polycyclic compounds. According to one embodiment, the alicyclic group has 3 to 60 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. Examples of such alicyclic groups include monocyclic groups such as cycloalkyl, bridged hydrocarbon groups, spirohydrocarbon groups, substituents derived from hydrogenated derivatives of aromatic hydrocarbon compounds, and the like.

[0057] Specifically, examples of the cycloalkyl group 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, and cyclooctyl, but are not limited thereto.

[0058] Examples of the bridged cyclic hydrocarbon group include, but are not limited to, bicyclo[1.1.0]butyl, bicyclo[2.2.1]heptyl, bicyclo[4.2.0]octa-1,3,5-trienyl, adamantyl, and decalinyl.

[0059] In addition, examples of the spirocyclic hydrocarbon group include spiro[3.4]octyl and spiro[5.5]undecyl, but are not limited to these.

[0060] The substituents derived from hydrogenated derivatives of aromatic hydrocarbon compounds are substituents derived from compounds obtained by hydrogenating some unsaturated bonds of monocyclic or polycyclic aromatic hydrocarbon compounds. Examples of such substituents include, but are not limited to, 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]annulenyl and 6,7-dihydro-5H-benzocycloheptenyl.

[0061] In the present specification, an aryl group is understood to mean a substituent derived from a monocyclic or condensed polycyclic compound containing only carbon as a ring atom and having aromaticity. The number of carbon atoms is not particularly limited, but preferably the number of carbon atoms is 6 to 60. According to one embodiment, the number of carbon atoms of the above aryl group is 6 to 30. According to one embodiment, the number of carbon atoms of the above aryl group is 6 to 20. Regarding the above aryl group, as a monocyclic aryl group, it can be phenyl, biphenyl, terphenyl, etc., but it is not limited thereto. As the above polycyclic aryl group, it can be naphthyl, anthracenyl, phenanthrenyl, pyrenyl, peryl, yl, fluorenyl, etc., but are not limited to these.

[0062] In the present 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.

[0063] In this specification, a heterocyclic group refers to a monovalent substituent derived from a monocyclic or condensed polycyclic compound containing one or more heteroatoms selected from O, N, Si and S as ring atoms in addition to carbon, and is understood to include all substituents having aromaticity or substituents not having aromaticity. According to one embodiment, the number of carbon atoms in the heterocyclic group is 2 to 60. According to another embodiment, the number of carbon atoms in the heterocyclic group is 2 to 30. According to another embodiment, the number of carbon atoms in the heterocyclic group is 2 to 20. Examples of such heterocyclic groups include heteroaryl groups, substituents derived from hydrogenated derivatives of heteroaromatic compounds, and the like.

[0064] Specifically, the heteroaryl group refers to a substituent derived from a monocyclic or condensed polycyclic compound containing one or more heteroatoms selected from N, O and S as ring atoms in addition to carbon, and refers to a substituent having aromaticity. According to one embodiment, the number of carbon atoms in the heteroaryl group is 2 to 60. According to another embodiment, the number of carbon atoms in the heteroaryl group is 2 to 30. According to another embodiment, the number of carbon atoms in 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 Examples of the present invention include, but are not limited to, oxazolyl, thiadiazolyl, and phenothiazinyl.

[0065] The substituent derived from a hydrogenated derivative of a heteroaromatic compound refers to a substituent derived from a compound obtained by hydrogenating a portion of unsaturated bonds of a monocyclic or polycyclic heteroaromatic compound. Examples of such a substituent include, but are not limited to, 1,3-dihydroisobenzofuranyl, 2,3-dihydrobenzofuranyl, 1,3-dihydrobenzo[c]thiophenyl, and 2,3-dihydro[b]thiophenyl.

[0066] In the present specification, the aryl group in aralkyl, aralkenyl, alkylaryl, arylamine, and arylsilyl is the same as the aryl group exemplified above. In the present specification, the alkyl group in aralkyl, alkylaryl, and alkylamine is the same as the alkyl group exemplified above. In the present specification, the heteroaryl group in heteroarylamine can be applied to the above description of heteroaryl. In the present specification, the alkenyl group in aralkenyl is the same as the alkenyl group exemplified above. In the present specification, the arylene group is a divalent group, and the above description of aryl can be applied otherwise. In the present specification, the heteroarylene group is a divalent group, and the above description of heteroaryl can be applied otherwise. In the present specification, the hydrocarbon ring is not a monovalent group, but is formed by combining two substituents, and the above description of aryl or cycloalkyl can be applied otherwise. In the present specification, the heterocycle is not a monovalent group, but is formed by combining two substituents, and the above description of heteroaryl can be applied otherwise.

[0067] In the present specification, the term "deuterated or substituted with deuterium" means that at least one of the replaceable hydrogen atoms in a compound, a divalent linking group or a monovalent substituent is substituted with deuterium.

[0068] In addition, the meaning of "unsubstituted or substituted with deuterium" or "substituted with deuterium or unsubstituted" means "unsubstituted or substituted with 1 to 9 deuteriums in the replaceable hydrogens". As an example, the term "unsubstituted or substituted with deuterium phenanthrenyl" can be understood to mean "unsubstituted or substituted with 1 to 9 deuteriums in the phenanthrenyl structure" when considering that the maximum number of hydrogens that can be replaced with deuterium in the phenanthrenyl structure is 9.

[0069] In addition, the meaning of "deuterated structure" refers to compounds, divalent linking groups or monovalent substituents including all structures in which at least one hydrogen is replaced by deuterium. As an example, the deuterated structure of phenyl shown below can be understood as a monovalent substituent in which at least one substitutable hydrogen in phenyl is replaced by deuterium.

[0070]

[0071] In addition, the "deuterium substitution rate" or "deuteration degree" of a compound refers to the value calculated as a percentage of the ratio of the number of deuterium substituted in the compound to the total number of hydrogens that can exist (the sum of the number of hydrogens that can be replaced by deuterium in the compound and the number of deuteriums replaced). Therefore, the "deuterium substitution rate" or "deuteration degree" of a compound as "K%" means that K% of the hydrogens that can be replaced by deuterium in the compound are replaced by deuterium.

[0072] In this case, the above-mentioned "deuterium substitution rate" or "deuteration degree" can be measured by MALDI-TOF MS (Matrix-Assisted Laser Desorption / Ionization Time-of-Flight Mass Spectrometer), nuclear magnetic resonance spectroscopy ( 1 H NMR), TLC / MS (Thin-Layer Chromatography / Mass Spectrometry), or GC / MS (Gas Chromatography / Mass Spectrometry), etc., and are measured according to generally known methods. More specifically, when MALDI-TOF MS is used, the above-mentioned "deuterium substitution rate" or "deuteration degree" can be determined by analyzing the number of deuterium substituted in the compound through MALDI-TOF MS, and then calculating the ratio of the number of deuterium substituted in the compound to the total number of hydrogen that can exist as a percentage.

[0073] (Compound)

[0074] The present invention provides a compound represented by the above Chemical Formula 1.

[0075] Preferably, the above Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-3:

[0076] [Chemical formula 1-1]

[0077]

[0078] [Chemical formula 1-2]

[0079]

[0080] [Chemical formula 1-3]

[0081]

[0082] In the above chemical formulas 1-1 to 1-3,

[0083] X, L, Ar1, Ar2, Ar3, Ar4, a, b, n and m are the same as defined above,

[0084] Y is N or CR', and two or more of Y are N,

[0085] R' is hydrogen, deuterium, substituted or unsubstituted C 1-60 Alkyl, or substituted or unsubstituted C 6-60 Aryl,

[0086] R1 and R2 are each independently substituted or unsubstituted C 6-60 Aryl,

[0087] c is an integer from 0 to 4.

[0088] Preferably, the above Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-4 to 1-9:

[0089] [Chemical formula 1-4]

[0090]

[0091] [Chemical formula 1-5]

[0092]

[0093] [Chemical formula 1-6]

[0094]

[0095] [Chemical formula 1-7]

[0096]

[0097] [Chemical formula 1-8]

[0098]

[0099] [Chemical formula 1-9]

[0100]

[0101] In the above chemical formulas 1-4 to 1-9,

[0102] X, L, Ar1, Ar2, Ar3, Ar4, a and b are the same as defined above.

[0103] Preferably, L is a single bond, a phenylene group or a biphenyl diyl group,

[0104] The above-mentioned phenylene group and biphenyldiyl group are unsubstituted or substituted with one or more deuterium groups.

[0105] Preferably, Ar1 is a phenyl group which is unsubstituted or substituted with any one or more of deuterium and methyl.

[0106] Preferably, Ar2 is phenyl, biphenyl or naphthyl, and the above Ar2 is unsubstituted or substituted with one or more deuterium.

[0107] Preferably, L is phenylene or biphenylene, wherein the above L is unsubstituted or substituted with one or more deuteriums,

[0108] Ar2 is a phenyl group substituted by a cyano group, or a naphthyl group substituted by a cyano group, wherein the above Ar2 is substituted by deuterium or is unsubstituted.

[0109] More preferably, L is a phenylene group which is unsubstituted or substituted with one or more deuteriums, or a biphenyldiyl group which is unsubstituted or substituted with one or more deuteriums, and Ar2 is a phenyl group which is substituted with one cyano group and 0 to 4 deuteriums, or a naphthyl group which is substituted with one cyano group and 0 to 6 deuteriums.

[0110] Preferably, L is a single bond,

[0111] Ar2 is phenyl, biphenyl or naphthyl, wherein the above Ar2 is unsubstituted or substituted by any one or more of deuterium and methyl,

[0112] Any one of Ar3 and Ar4 is any one selected from the following groups and their deuterated structures:

[0113]

[0114] Preferably, R' is hydrogen, deuterium, methyl or phenyl, and the methyl and phenyl groups are unsubstituted or substituted with one or more deuterium.

[0115] Preferably, R1 and R2 are each independently a phenyl group or a biphenyl group, and the above R1 and R2 are unsubstituted or substituted with one or more deuteriums.

[0116] Representative examples of the compound represented by the above Chemical Formula 1 are shown below:

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124] In addition, the present invention provides a method for producing the compound represented by the above Chemical Formula 1 as shown in the following Reaction Formula 1.

[0125] [Reaction formula 1]

[0126]

[0127] In the above reaction formula 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.

[0128] The compound represented by the above chemical formula 1 can be manufactured 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 changed to a reactive group known in the art. Such a manufacturing method can be more specifically described in the manufacturing example described later.

[0129] (Organic Light Emitting Devices)

[0130] In addition, the present invention provides an organic light-emitting device including the compound represented by the above Chemical Formula 1. As an example, the present invention provides an organic light-emitting device including: a first electrode, a second electrode disposed opposite to the above first electrode, and one or more organic layers disposed between the above first electrode and the above second electrode, wherein one or more of the organic layers includes the compound represented by the above Chemical Formula 1.

[0131] The organic layer of the organic light-emitting device of the present invention may be formed of a single-layer structure or a multi-layer structure in which two or more organic layers are stacked. For example, the organic light-emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, an electron suppression layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. as organic layers. However, the structure of the organic light-emitting device is not limited thereto and may include a smaller number of organic layers.

[0132] In addition, the organic layer may include a light emitting layer, and the light emitting layer may include the compound represented by the chemical formula 1. In particular, the compound according to the present invention may be used as a dopant of the light emitting layer.

[0133] In addition, the organic layer may include an electron transport layer, an electron injection layer, or a layer that simultaneously transports and injects electrons, and the electron transport layer, the electron injection layer, or the layer that simultaneously transports and injects electrons may include the compound represented by Chemical Formula 1.

[0134] In addition, the organic layer may include a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport and injection layer. In this case, the organic layer containing the compound may be an electron transport and injection layer.

[0135] 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 inverse 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 2 .

[0136] 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.

[0137] Figure 2 The 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, a light-emitting layer 3, an electron transport and injection layer 7, and a cathode 4. In the structure described above, the compound represented by the above Chemical Formula 1 may be contained in the above electron transport and injection layer.

[0138] 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 the above Chemical Formula 1. In addition, when the organic light-emitting device includes a plurality of organic layers, the organic layers can be formed of the same substance or different substances.

[0139] For example, the organic light-emitting device according to the present invention can be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. In this case, it can be manufactured as follows: a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation is used to vapor-deposit a metal or a conductive metal oxide or an alloy thereof on a substrate to form an anode, and then an organic layer including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer is formed on the anode, and then a substance that can be used as a cathode is vapor-deposited on the organic layer. In addition to this method, an organic light-emitting device can also be manufactured by sequentially vapor-depositing a cathode substance, an organic layer, and an anode substance on a substrate.

[0140] In addition, the compound represented by the above chemical formula 1 can be used not only by vacuum evaporation method but also by solution coating method to form an organic layer when manufacturing an organic light-emitting device. Here, the so-called solution coating method refers to spin coating method, dip coating method, blade coating method, inkjet printing method, screen printing method, spray method, roller coating method, etc., but is not limited to these.

[0141] 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.

[0142] 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.

[0143] As the above-mentioned anode material, in order to enable holes to be smoothly injected into the organic layer, a material with a large work function is preferably used. Specific examples of the above-mentioned anode material include metals such as vanadium, chromium, copper, zinc, gold, or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), 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, but are not limited thereto.

[0144] In order to facilitate the injection of electrons into the organic layer, the cathode material is preferably a material with a small work function. 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.

[0145] The hole injection layer is a layer for injecting holes from the electrode. As a hole injection material, it is preferably a compound having the ability to transport holes, the effect of injecting holes from the anode, an excellent hole injection effect for the light-emitting layer or the light-emitting material, and a compound having excellent thin film forming ability to prevent the excitons generated in the light-emitting layer from migrating to the electron injection layer or the electron injection material. 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. As specific examples of hole injection materials, there are metal porphyrins, oligothiophenes, arylamine organics, hexanitrile hexaazatriphenylene organics, quinacridone organics, perylene organics, anthraquinones, polyaniline and polythiophene conductive polymers, but are not limited thereto.

[0146] The hole transport layer is a layer that receives holes from the hole injection layer and transfers the holes to the light-emitting layer. The hole transport material is a material that can receive holes from the anode or the hole injection layer and transfer them to the light-emitting layer. Materials with high hole mobility are suitable. Specific examples include arylamine organic substances, conductive polymers, and block copolymers having both conjugated and non-conjugated parts, but are not limited thereto.

[0147] 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, and is preferably a material with high quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq3); carbazole compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo Compounds of the oxazole, benzothiazole and benzimidazole series; polymers of the poly(p-phenylene vinylene) (PPV) series; spiro compounds; polyfluorene, rubrene, etc., but are not limited thereto.

[0148] 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 to these.

[0149] 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, and there are pyrene, anthracene, The styrylamine compound is a compound in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, and is substituted or unsubstituted with one or more substituents selected from aryl, silyl, alkyl, cycloalkyl and arylamino. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetramine, etc., but not limited thereto. In addition, as metal complexes, there are iridium complexes, platinum complexes, etc., but not limited thereto.

[0150] The electron transport and injection layer is a layer that injects electrons from the electrode and transfers the received electrons to the light-emitting layer, and plays the role of both the electron transport layer and the electron injection layer, and is formed on the light-emitting layer or the hole blocking layer. Such an electron injection and transport substance is a substance that can well receive electrons from the cathode and transfer them to the light-emitting layer, and a substance with a large electron mobility is suitable. As such an electron injection and transport layer substance, a compound represented by the above chemical formula 1 can be used. As examples of other electron injection and transport substances, there are Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free radical compounds, hydroxyflavone-metal complexes, triazine derivatives, etc., but are not limited to these. Alternatively, it can also be combined with fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, Azoles, Oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylene methane, anthrone and the like, and derivatives thereof, metal coordination compounds, or nitrogen-containing five-membered ring derivatives and the like can be used together, but are not limited thereto.

[0151] The electron transport and injection layer may also be formed as a separate layer such as an electron injection layer and an electron transport layer. In this case, the electron transport layer is formed on the light-emitting layer or the hole blocking layer, and as the electron transport material contained in the electron transport layer, the electron injection and transport material mentioned above can be used. In addition, the electron injection layer is formed on the electron transport layer, and as the electron injection material contained in the electron injection layer, 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 coordination compounds and nitrogen-containing five-membered ring derivatives, etc.

[0152] Examples of the metal coordination compounds include, but are not limited to, 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-hydroxyquinoline) gallium chloride, bis(2-methyl-8-hydroxyquinoline)(o-cresol) gallium, bis(2-methyl-8-hydroxyquinoline)(1-naphthol) aluminum, and bis(2-methyl-8-hydroxyquinoline)(2-naphthol) gallium.

[0153] In one embodiment, the electron transport layer, the electron injection layer, or the electron transport and injection layer of the organic light-emitting device may include the compound represented by the above chemical formula 1 and the above metal coordination compound. In this case, the electron transport layer, the electron injection layer, or the electron transport and injection layer may include the compound represented by the above chemical formula 1 and the above metal coordination 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.

[0154] 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, and in particular, may be a bottom emission device requiring relatively high light-emitting efficiency.

[0155] In addition, the compound according to the present invention may be contained in an organic solar cell or an organic transistor in addition to being contained in an organic light-emitting device.

[0156] The preparation of the compound represented by the above Chemical Formula 1 and the organic light-emitting device including the same is specifically described in the following examples. However, the following examples are used to illustrate the present invention, and the scope of the present invention is not limited thereto.

[0157] [Manufacturing example]

[0158] Preparation Example 1: Preparation of Compound E1

[0159]

[0160] Under nitrogen atmosphere, E1-A (20 g, 35 mmol) and E1-B (15.2 g, 35 mmol) were added to 400 ml of 1,4-dihydroquinone. alkane (1,4-Dioxane), stirring and reflux. Then, potassium phosphate (22.3g, 105.1mmol) was dissolved in 22ml of water and added. After sufficient stirring, dibenzylideneacetone palladium (0.6g, 1.1mmol) and tricyclohexylphosphine (0.6g, 2.1mmol) were added. After reacting for 7 hours, the solid was cooled to room temperature and filtered. The solid was dissolved in 887mL of chloroform, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce a yellow solid compound E1 (4.4g, 15%).

[0161] MS:[M+H] + =844

[0162] Preparation Example 2: Preparation of Compound E2

[0163]

[0164] The compound E2 was produced by the same method as in Production Example 1 except that the starting materials were used as in the above reaction formula.

[0165] MS:[M+H] + =894

[0166] Preparation Example 3: Preparation of Compound E3

[0167]

[0168] The compound E3 was produced by the same method as in Production Example 1 except that the starting materials were used as in the above reaction formula.

[0169] MS:[M+H] + =844

[0170] Preparation Example 4: Preparation of Compound E4

[0171]

[0172] The compound E4 was produced by the same method as in Production Example 1 except that the starting materials were used as in the above reaction formula.

[0173] MS:[M+H] + =768

[0174] Preparation Example 5: Preparation of Compound E5

[0175]

[0176] The compound E5 was produced by the same method as in Production Example 1 except that the starting materials were used as in the above reaction formula.

[0177] MS:[M+H] + =844

[0178] Preparation Example 6: Preparation of Compound E6

[0179]

[0180] The compound E6 was produced by the same method as in Production Example 1 except that the starting materials were used as in the above reaction formula.

[0181] MS:[M+H] + =818

[0182] Preparation Example 7: Preparation of Compound E7

[0183]

[0184] The compound E7 was produced by the same method as in Production Example 1 except that the starting materials were used as in the above reaction formula.

[0185] MS:[M+H] + =791

[0186] Preparation Example 8: Preparation of Compound E8

[0187]

[0188] The compound E8 was produced by the same method as in Production Example 1 except that the starting materials were used as in the above reaction formula.

[0189] MS:[M+H] + =767

[0190] Preparation Example 9: Preparation of Compound E9

[0191]

[0192] The compound E9 was produced by the same method as in Production Example 1 except that the starting materials were used as in the above reaction formula.

[0193] MS:[M+H] + =919

[0194] Preparation Example 10: Preparation of Compound E10

[0195]

[0196] The compound E10 was produced by the same method as in Production Example 1 except that the starting materials were used as in the above reaction formula.

[0197] MS:[M+H] + =776

[0198] Preparation Example 11: Preparation of Compound E11

[0199]

[0200] The compound E11 was produced by the same method as in Production Example 1 except that the starting materials were used as in the above reaction formula.

[0201] MS:[M+H] + =768

[0202] [Example]

[0203] Example 1

[0204] ITO (indium tin oxide) is used The glass substrate coated with a film of a thickness of 10000 mm was placed in distilled water dissolved with a detergent and washed with ultrasonic waves. At this time, the detergent used a product of Fischer Co., and the distilled water used distilled water filtered twice by a filter manufactured by Millipore Co. After ITO was washed for 30 minutes, ultrasonic washing was repeated twice with distilled water for 10 minutes. After the distilled water washing was completed, ultrasonic washing was carried out with a solvent of isopropanol, acetone, and methanol and dried, and then transported to a plasma cleaning machine. In addition, after the above-mentioned substrate was cleaned for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

[0205] On the ITO transparent electrode prepared in this way, the following compound HI-A was applied as The hole injection layer was formed by thermal vacuum deposition of a thickness of 1000 nm. On the hole injection layer, the following compounds HAT were sequentially deposited: hexaazatriphenylene, ) and the following compound HT-A Then, a film with a thickness of 1000 nm was deposited on the hole transport layer. The following compounds BH and BD were vacuum deposited at a weight ratio of 25:1 to form a light-emitting layer.

[0206] On the light-emitting layer, the compound E1 prepared in the above-mentioned Preparation Example 1 and the following compound [LiQ] (lithium quinolate) were vacuum-deposited at a weight ratio of 1:1, thereby forming a On the electron transport and injection layer, lithium fluoride (LiF) is sequentially added with The thickness of the aluminum A cathode is formed by evaporation with a thickness of .

[0207]

[0208] In the above process, the evaporation rate of organic matter is maintained Lithium fluoride at cathode maintains The evaporation speed of aluminum is maintained The evaporation speed is 1*10 -7 ~5*10 -8 A support is provided to produce an organic light-emitting device.

[0209] Examples 2 to 11

[0210] An organic light-emitting device was manufactured by the same method as in Example 1, except that the compounds described in the following Table 1 were used instead of Compound E1 of Example 1.

[0211] Comparative Examples 1 and 2

[0212] An organic light-emitting device was manufactured by the same method as in Example 1, except that the compounds described in the following Table 1 were used instead of Compound E1 of Example 1. In the following Table 1, the compounds of ET-1 and ET-2 are as follows.

[0213]

[0214] Experimental example

[0215] For the organic light emitting devices manufactured in the above Examples 1 to 10 and Comparative Examples 1 and 2, the 2 The driving voltage, luminous efficiency and color coordinates were measured at a current density of 20 mA / cm 2 The time (T90) until the initial luminance reaches 90% was measured at a current density of . The results are shown in Table 1 below.

[0216]

Table 1

[0217]

[0218] As described in Table 1, it can be confirmed that the organic light emitting device using the compound represented by Chemical Formula 1 of the present invention exhibits excellent characteristics in voltage, efficiency, and lifespan (T90).

Claims

1. A compound represented by the following chemical formula 1: [Chemical formula 1] In the chemical formula 1, X is independently N, CH or CD, and two or more of X are N, L is a single bond, or a substituted or unsubstituted C 6-60 Arylene, Ar1 and Ar2 are each independently substituted or unsubstituted C 6-60 Aryl, Ar3 and Ar4 are each independently a substituent represented by the following Chemical Formula 2, [Chemical formula 2] In the chemical formula 2, o and p are each independently 0 or 1, q is an integer from 0 to 4, r is an integer from 0 to 7, s is an integer from 0 to 5, However, o+p+r is an integer from 0 to 7. Any one of Ar1 to Ar4 is substituted by a cyano group, HAr is each independently selected from deuterium, substituted or unsubstituted C 1-60 Alkyl, and substituted or unsubstituted C 6-60 1 to 3 substituents in aryl substituted with pyrimidinyl; 2 substituted or unsubstituted C 6-60 triazine substituted with aryl; or substituted or unsubstituted with 1 C 6-60 Aryl substituted quinazolinyl, a and b are each independently an integer from 0 to 4, n and m are each independently 0 or 1, However, n+m is 1, a+n is an integer from 0 to 4, b+m is an integer from 0 to 4.

2. The compound according to claim 1, wherein The chemical formula 1 is represented by any one of the following chemical formulas 1-1 to 1-3: [Chemical formula 1-1] [Chemical formula 1-2] [Chemical formula 1-3] In the chemical formulas 1-1 to 1-3, X, L, Ar1, Ar2, Ar3, Ar4, a, b, n and m are as defined in claim 1, Y is N or CR', and two or more of Y are N, R' is hydrogen, deuterium, substituted or unsubstituted C 1-60 Alkyl, or substituted or unsubstituted C 6-60 Aryl, R1 and R2 are each independently substituted or unsubstituted C 6-60 Aryl, c is an integer from 0 to 4.

3. The compound according to claim 1, wherein The chemical formula 1 is represented by any one of the following chemical formulas 1-4 to 1-9: [Chemical formula 1-4] [Chemical formula 1-5] [Chemical formula 1-6] [Chemical formula 1-7] [Chemical formula 1-8] [Chemical formula 1-9] In the chemical formulas 1-4 to 1-9, X, L, Ar1, Ar2, Ar3, Ar4, a and b are the same as defined in claim 1.

4. The compound according to claim 1, wherein L is a single bond, a phenylene group or a biphenyl diyl group, The phenylene group and the biphenyldiyl group are unsubstituted or substituted with one or more deuterium groups.

5. The compound according to claim 1, wherein Ar1 is a phenyl group which is unsubstituted or substituted with any one or more of deuterium and methyl.

6. The compound according to claim 1, wherein Ar2 is phenyl, biphenyl or naphthyl, The Ar2 is unsubstituted or substituted with one or more deuteriums.

7. The compound according to claim 1, wherein L is phenylene or biphenyl diyl, wherein said L is unsubstituted or substituted with one or more deuteriums, Ar2 is a phenyl group substituted by a cyano group, or a naphthyl group substituted by a cyano group, wherein Ar2 is substituted by deuterium or is not substituted.

8. The compound according to claim 1, wherein L is a single bond, Ar2 is phenyl, biphenyl or naphthyl, wherein Ar2 is unsubstituted or substituted by any one or more of deuterium and methyl, Any one of Ar3 and Ar4 is any one selected from the following groups and their deuterated structures:

9. The compound according to claim 2, wherein R' is hydrogen, deuterium, methyl or phenyl, The methyl group and the phenyl group are unsubstituted or substituted with one or more deuterium groups.

10. The compound according to claim 2, wherein R1 and R2 are each independently phenyl or biphenyl, The R1 and R2 are unsubstituted or substituted with one or more deuterium.

11. The compound according to claim 1, wherein The compound represented by the chemical formula 1 is any one selected from the following compounds:

12. An organic light emitting device, comprising: A first electrode, a second electrode disposed opposite to the first electrode, and one or more organic layers disposed between the first electrode and the second electrode, wherein one or more of the organic layers comprises the compound according to any one of claims 1 to 11.

13. The organic light emitting device according to claim 12, wherein: The organic layer including the compound is an electron transport layer, an electron injection layer, or an electron transport and injection layer.

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