Novel compound and organic light-emitting device using same

Abstract

The invention provides a novel compound and an organic light-emitting device using the same.

Description

Technical Field

[0001] The present invention relates to novel compounds and organic light-emitting devices comprising the same. Background Art

[0002] 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.

[0003] 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.

[0004] As for organic substances used for organic light-emitting devices as described above, development of new materials continues to be required.

[0005] Prior art literature

[0006] Patent Literature

[0007] (Patent Document 0001) Korean Patent Publication No. 10-2000-0051826 Summary of the invention

[0008] Technical issues

[0009] The present invention relates to novel compounds and organic light-emitting devices comprising the same.

[0010] Solution to the problem

[0011] The present invention provides a compound represented by the following Chemical Formula 1:

[0012] [Chemical formula 1]

[0013]

[0014] In the above chemical formula 1,

[0015] X 1 To X 3 Each independently is N or CR, but X 1 To X 3At least two of them are N,

[0016] X 4 To X 6 Each independently is N or CR, but X 4 To X 6 At least two of them are N,

[0017] wherein R is independently hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C 1-60 Alkyl; substituted or unsubstituted C 6-60 Aryl; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S 2-60 Heteroaryl,

[0018] L 1 and L 2 are each independently a single bond, or a substituted or unsubstituted C 6-60 Arylene,

[0019] Ar 1 To Ar 4 are each independently substituted or unsubstituted C 6-60 Aryl; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S 2-60 Heteroaryl,

[0020] Ar 5 and Ar 6 are each independently substituted or unsubstituted C 6-60 Aryl,

[0021] But, 5 and Ar 6 At least one of them is substituted by a cyano group,

[0022] n and m are each independently an integer from 0 to 4,

[0023] However, if n+m is greater than 1,

[0024] R 1 and R 2 are each independently deuterium, halogen, cyano, or substituted or unsubstituted C 1-60 Alkyl, or two adjacent substituents are combined with each other to form a substituted or unsubstituted C 6-20 Aromatic ring,

[0025] However, two or more adjacent R 1 or R 2 When they are bonded to each other to form an unsubstituted benzene ring fused to an adjacent ring, n+m is 2 or more,

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

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

[0028] 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.

[0029] Effects of the Invention

[0030] The compound represented by the above Chemical Formula 1 may be used as a material of an organic layer of an organic light-emitting device, and may achieve improved efficiency, lower driving voltage, and / or improved lifespan characteristics in the organic light-emitting device. BRIEF DESCRIPTION OF THE DRAWINGS

[0031] Figure 1 An example of an organic light-emitting device composed of a substrate 1 , an anode 2 , a hole transport layer 3 , a light-emitting layer 4 , an electron injection and transport layer 5 , and a cathode 6 is shown.

[0032] 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 7, a hole transport layer 3, an electron suppression layer 8, a light-emitting layer 4, a hole blocking layer 9, an electron injection and transport layer 5, and a cathode 6.

[0033] Figure 3 An example of an organic light-emitting device composed of a substrate 1 , an anode 2 , a hole injection layer 7 , a hole transport layer 3 , a light-emitting layer 4 , an electron injection and transport layer 5 , and a cathode 6 is shown.

[0034] Explanation of symbols

[0035] 1: Substrate 2: Anode

[0036] 3: Hole transport layer 4: Light-emitting layer

[0037] 5: Electron injection and transport layer 6: Cathode

[0038] 7: Hole injection layer 8: Electron suppression layer

[0039] 9: Hole blocking layer DETAILED DESCRIPTION

[0040] In the following, the present invention will be described in more detail to help understanding the present invention.

[0041] (Definition of terms)

[0042] In this manual, and "D" represents a bond to other substituents, and "D" represents deuterium.

[0043] 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 The term "substituted or unsubstituted" means "substituted with one or more substituents selected from deuterium, halogen, cyano, methyl, ethyl, phenyl, biphenyl, naphthyl, pyridyl and pyrimidyl". 1-10 Alkyl, C 1-10 Alkoxy, C 3-7 Cycloalkyl, C 6-20 Aryl, pyridyl, pyrimidinyl, dibenzofuranyl, dibenzothiophenyl, benzo The term "substituted by one or more substituents" in the present specification may be understood as "substituted by 1 to the maximum number of replaceable hydrogen atoms". Alternatively, the term "substituted by one or more substituents" in the present specification may be understood as "substituted by 1 to 5 substituents" or "substituted by 1 or 2 substituents".

[0044] In the present specification, the number of carbon atoms in the carbonyl group is not particularly limited, but preferably the number of carbon atoms is 1 to 40. Specifically, the substituent may be a substituent of the following structure, but the substituent is not limited thereto.

[0045]

[0046] 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.

[0047]

[0048] 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.

[0049]

[0050] In this specification, a substituted or unsubstituted silyl group refers to -Si(Z 1 )(Z 2 )(Z 3 ), here, Z 1 , Z 2 and Z 3 Each independently may be hydrogen, deuterium, 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, Z 1 , Z 2 and Z 3 Each independently may 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.

[0051] In the present specification, specific examples of the boryl group include trimethylboryl, triethylboryl, tert-butyldimethylboryl, triphenylboryl, and phenylboryl, but are not limited thereto.

[0052] In the present specification, as examples of the halogen group, there are fluorine, chlorine, bromine or iodine.

[0053] 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.

[0054] 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.

[0055] 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.

[0056] 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.

[0057] 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.

[0058] In addition, examples of the spirocyclic hydrocarbon group include spiro[3.4]octyl and spiro[5.5]undecyl, but are not limited to these.

[0059] 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.

[0060] 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.

[0061] 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.

[0062] 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.

[0063] 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.

[0064] 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 substituents include, but are not limited to, 1,3-dihydroisobenzofuranyl, 2,3-dihydrobenzofuranyl, 1,3-dihydrobenzo[c]thiophenyl, and 2,3-dihydro[b]thiophenyl.

[0065] 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.

[0066] 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.

[0067] In addition, the meaning of "unsubstituted or substituted with deuterium" or "substituted or unsubstituted with deuterium" means "unsubstituted or substituted with 1 to 9 deuteriums in the substitutable 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 substituted with deuteriums is 9.

[0068] In addition, the meaning of "deuterated structure" refers to a compound, a divalent linking group or a monovalent substituent 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 referring to all structures in which at least one substitutable hydrogen in phenyl is replaced by deuterium and a monovalent substituent.

[0069]

[0070] 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 deuteriums substituted in the compound to the total number of hydrogens that can exist (the sum of the number of hydrogens that can be substituted with deuterium in the compound and the number of deuteriums substituted). Therefore, the "deuterium substitution rate" or "deuteration degree" of a compound as "K%" means that K% of the hydrogens that can be substituted with deuterium in the compound are substituted with deuterium.

[0071] 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.

[0072] (Compound)

[0073] In another aspect, the present invention provides a compound represented by the above Chemical Formula 1.

[0074] Specifically, the compound represented by the above chemical formula 1 is a compound in which a six-membered heterocyclic group containing two or more N is connected by a "biphenyl" connecting group, and each is connected at the ortho-ortho position of the biphenyl connecting group, and the above biphenyl connecting group has at least one or more aryl substituents substituted by a cyano group.

[0075] The compound having the above structure has a lower LUMO energy level than a compound having no cyano group (CN), thereby showing a long life characteristic and smoothly adjusting the electron mobility, and is therefore suitable as an electron transport material.

[0076] Thus, an organic light-emitting device using the above compound can not only show a lower driving voltage but also improve efficiency and lifespan characteristics at the same time, compared with an organic light-emitting device using a compound having no cyano (CN) group.

[0077] On the other hand, in this specification, “Ar 5 and Ar 6 At least one of them is substituted by a cyano group" means that Ar 5 Any one of them is substituted by one or more cyano groups, or Ar 6 Any one of them is substituted by one or more cyano groups.

[0078] In one embodiment, X 1 To X 3 All are N; or

[0079] X 1 and X 2 N, X 3 is CR; or

[0080] X 1 and X 3 N, X 2 For CR,

[0081] Wherein, R can be hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C 1-10 Alkyl, or substituted or unsubstituted C 6-20 Aryl.

[0082] In addition, X 4 To X 6 All are N; or

[0083] X 4 and X 5 N, X 6 is CR; or

[0084] X 4 and X 6 N, X 5 For CR,

[0085] Wherein, R can be hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C 1-10 Alkyl, or substituted or unsubstituted C 6-20 Aryl.

[0086] More specifically, R may be hydrogen, deuterium, halogen, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, or substituted or unsubstituted phenyl.

[0087] L 1 and L 2 Each independently may be a single bond, or a substituted or unsubstituted C 6-20 Arylene.

[0088] In another embodiment, L 1 and L 2 Each independently may be a single bond; or be selected from deuterium, cyano, C 1-10 Alkyl, C 6-60 Aryl, pyridyl, pyrimidinyl, dibenzofuranyl, dibenzothiophenyl, benzo One or more substituents in oxazolyl and benzothiazolyl may be substituted or unsubstituted C 6-20 Arylene,

[0089] Wherein, the above substituent C 1-10 Alkyl, C 6-60 Aryl, dibenzofuranyl, dibenzothiophenyl, benzo The oxazolyl and benzothiazolyl groups may be unsubstituted or substituted by deuterium or cyano.

[0090] In another embodiment, L 1 and L 2 each independently represents a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenyldiyl group, a substituted or unsubstituted terphenyldiyl group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted pyrene group, or a substituted or unsubstituted fluoranthenylene group,

[0091] Here, "substituted" means being selected from deuterium, cyano, C 1-10 Alkyl, C 6-20 Aryl, pyridyl, pyrimidinyl, dibenzofuranyl, dibenzothiophenyl, benzo substituted with one or more substituents of oxazolyl and benzothiazolyl,

[0092] The above substituent C 1-10 Alkyl, C 6-60 Aryl, dibenzofuranyl, dibenzothiophenyl, benzo The oxazolyl group and the benzothiazolyl group may each independently be substituted or unsubstituted with a substituent selected from the group consisting of deuterium, cyano and halogen.

[0093] More specifically, L 1 and L 2The term "substituted" as used herein means a substituted group selected from deuterium, cyano, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, phenyl, biphenyl, terphenyl, naphthyl, pyridyl, pyrimidyl, dibenzofuranyl, dibenzothiophenyl, benzo substituted with one or more substituents of oxazolyl and benzothiazolyl,

[0094] The above substituents include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, phenyl, biphenyl, terphenyl, naphthyl, pyridyl, pyrimidyl, dibenzofuranyl, dibenzothiophenyl, benzo The oxazolyl group and the benzothiazolyl group may each independently be substituted or unsubstituted with a substituent selected from the group consisting of deuterium, cyano and halogen.

[0095] Alternatively, it can be L 1 and L 2 are all single bonds; or

[0096] L 1 and L 2 is a single bond; or

[0097] L 1 and L 2 None of them are single bonds.

[0098] In addition, L 1 and L 2 May be the same as or different from each other.

[0099] In one embodiment, Ar 1 To Ar 4 Each independently may be substituted or unsubstituted C 6-20 Aryl; or substituted or unsubstituted C containing 1 or 2 heteroatoms selected from N, O and S 2-60 Heteroaryl.

[0100] In another embodiment, Ar 1 To Ar 4 The phenyl radicals may be independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted benzonaphthofuranyl, substituted or unsubstituted benzonaphthothiophenyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted benzo substituted or unsubstituted carbazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted pyridyl, or substituted or unsubstituted pyrimidinyl.

[0101] Among them, Ar1 To Ar 4 The term "substituted" refers to being selected from deuterium, halogen, cyano, C 1-10 Alkyl, C 1-10 Alkoxy, C 3-7 Cycloalkyl, C 6-20 Aryl, pyridyl, pyrimidinyl, dibenzofuranyl, dibenzothiophenyl, benzo substituted with one or more substituents of oxazolyl and benzothiazolyl,

[0102] The above substituent C 1-10 Alkyl, C 1-10 Alkoxy, C 3-7 Cycloalkyl, C 6-60 Aryl, dibenzofuranyl, dibenzothiophenyl, benzo The oxazolyl group and the benzothiazolyl group may each independently be substituted or unsubstituted with a substituent selected from the group consisting of deuterium, cyano and halogen.

[0103] More specifically, Ar 1 To Ar 4 The term "substituted" as used herein refers to a radical selected from the group consisting of deuterium, halogen, cyano, methyl, trifluoromethyl, methoxy, trifluoromethoxy, phenyl, naphthyl, phenanthrenyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, benzothiazolyl and benzo[1,2-d]. The oxazolyl group is substituted with one or more substituents,

[0104] The above substituents deuterium, halogen, cyano, methyl, trifluoromethyl, methoxy, trifluoromethoxy, phenyl, naphthyl, phenanthrenyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, benzothiazolyl and benzo Each oxazolyl group may be independently substituted or unsubstituted with a substituent selected from deuterium, cyano and halogen.

[0105] In addition, the substituent Can be different.

[0106] In one embodiment, Ar 5 and Ar 6 Each independently may be substituted or unsubstituted C 6-20 Aryl.

[0107] Among them, Ar 5 and Ar 6 It may be substituted or unsubstituted by a substituent selected from the group consisting of deuterium, cyano and halogen.

[0108] In another embodiment, Ar 5 and Ar 6Each independently may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted quaterphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, or a substituted or unsubstituted triphenylene group.

[0109] In another embodiment, Ar 5 and Ar 6 Each independently may be phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, anthracenyl, phenanthryl or triphenylene,

[0110] Among them, Ar 5 and Ar 6 It may be substituted or unsubstituted by one or more substituents selected from the group consisting of deuterium, cyano, halogen, phenyl, naphthyl, and phenanthryl.

[0111] In another embodiment, Ar substituted with cyano 5 and Ar 6 each independently represents phenyl substituted by 1 to 3 cyano groups, biphenyl substituted by 1 to 3 cyano groups, terphenyl substituted by 1 to 3 cyano groups, naphthyl substituted by 1 to 3 cyano groups, (triphenyl)phenyl substituted by 1 to 3 cyano groups, or (phenyl)naphthyl substituted by 1 to 3 cyano groups,

[0112] Among them, Ar substituted by cyano 5 and Ar 6 It may be deuterium substituted or unsubstituted.

[0113] In addition, when n is 2 or more, two or more Ar 5 are the same or different from each other, and when m is 2 or more, two or more Ar 6 The same as or different from each other.

[0114] Therefore, as an example, when n is 2, it can be 1 Ar 5 is replaced by cyano, and the remaining Ar 5 Not substituted by cyano; or 2 Ar 5 are substituted by cyano; or 2 Ar 5 None of them are substituted by cyano groups. 6 It can be understood in the same way.

[0115] More specifically, it can be

[0116] 1Ar 5 is substituted by one or more cyano groups, and the remaining Ar 5 and Ar 6 is not substituted with deuterium; or

[0117] 2Ar 5is substituted by one or more cyano groups, and the remaining Ar 5 and Ar 6 is not substituted with deuterium; or

[0118] 1Ar 5 Substituted with one or more cyano groups, one Ar 6 is substituted by one or more cyano groups, and the remaining Ar 5 and Ar 6 Not substituted with deuterium.

[0119] In addition, Ar 5 and Ar 6 At least one of the may be substituted by 1, 2, 3 or 4 cyano groups.

[0120] Preferably, in order to have a suitable LUMO energy level relative to the adjacent light-emitting layer, Ar 5 and Ar 6 At least one of them may be substituted with one or more cyano groups.

[0121] Alternatively, it can be 1 Ar 5 is substituted by 1, 2 or 3 cyano groups, the remaining Ar 5 and Ar 6 is not substituted with deuterium; or

[0122] 2Ar 5 is substituted by 1, 2 or 3 cyano groups, the remaining Ar 5 and Ar 6 is not substituted with deuterium; or

[0123] 1 Ar5 is substituted by 1, 2 or 3 cyano groups, 1 Ar 6 is replaced by one cyano group, and the remaining Ar 5 and Ar 6 Not substituted with deuterium.

[0124] For example, it can be 1 Ar 5 is replaced by one cyano group, and the remaining Ar 5 and Ar 6 is not substituted with deuterium; or

[0125] 2Ar 5 is replaced by one cyano group, and the remaining Ar 5 and Ar 6 is not substituted with deuterium; or

[0126] 1Ar 5 Replaced by 1 cyano, 1 Ar 6 is replaced by one cyano group, and the remaining Ar 5 and Ar 6 Not substituted with deuterium.

[0127] Where n can be 1 and m can be 0; or

[0128] n is 1, m is 1; or

[0129] n is 1, m is 2; or

[0130] n is 1, m is 3; or

[0131] n is 2, m is 2; or

[0132] n is 3, m is 0; or

[0133] n is 4 and m is 0.

[0134] In addition, n+m can be 1, 2, 3, 4 or 5.

[0135] In addition, in one embodiment, R 1 and R 2 Each independently may be deuterium, halogen, cyano, substituted or unsubstituted methyl, or substituted or unsubstituted ethyl, or

[0136] Two or more adjacent R 1 or R 2 They may be combined with each other to form a substituted or unsubstituted benzene, naphthalene or phenanthrene ring fused to the adjacent ring.

[0137] At this time, two or more adjacent R 1 or R 2 When they are bonded to each other to form an unsubstituted benzene ring fused to an adjacent ring, n+m may be 2, 3 or 4.

[0138] When a is 2 or more, 2 or more R 1 are the same or different from each other, and when b is 2 or more, two or more R 2 The same as or different from each other.

[0139] In addition, a is 0, 1, 2, 3 or 4, and b is 0, 1, 2, 3 or 4.

[0140] In addition, the above compound may have 1, 2, 3 or 4 cyano groups.

[0141] In addition, the above-mentioned compound may contain no deuterium, or may contain one or more deuterium.

[0142] When the above compound contains deuterium, the deuterium substitution rate of the compound can be 1% to 100%. Specifically, the deuterium substitution rate of the above compound can be 4% or more, 6% or more, 8% or more, 10% or more, 12% or more, 14% or more, 16% or more, or 18% or more and 100% or less, 80% or less, 60% or less, 40% or less, or 20% or less.

[0143] As an example, the compound may contain no deuterium, or may contain 1 to 50 deuteriums. More specifically, the compound may contain no deuterium, or may contain 1 or more, 2 or more, 3 or more, 4 or more, or 5 or more and 30 or less, 20 or less, 15 or less, 10 or less, 9 or less, 8 or less, 7 or less, or 6 or less deuteriums.

[0144] On the other hand, representative examples of the compound represented by the above Chemical Formula 1 are shown below:

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169] The compound represented by the above chemical formula 1 can be produced by the production method shown in the following reaction formula 1:

[0170] [Reaction formula 1]

[0171]

[0172] In the above reaction formula 1, the rest except X' is the same as the definition in chemical formula 1, and X' is a halogen. Preferably, X' is chlorine or bromine.

[0173] The above reaction formula 1 is a Suzuki coupling reaction, which is preferably carried out in the presence of a palladium catalyst and a base. The reactive group used for the Suzuki coupling reaction can be changed according to the techniques known in the art.

[0174] The method for producing the compound of the above Chemical Formula 1 can be further embodied in the synthesis examples described below.

[0175] (Organic Light Emitting Devices)

[0176] On the other hand, 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.

[0177] 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, 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.

[0178] In this case, the organic layer including the above-mentioned compound may be an electron transport layer or an electron injection and transport layer.

[0179] Alternatively, the organic light emitting device may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron injection and transport layer, etc. as organic layers.

[0180] In this case, the organic layer including the above-mentioned compound may be an electron transport layer or an electron injection and transport layer.

[0181] Specifically, in one embodiment, the organic layer may include a hole injection layer, a hole transport layer, a light emitting layer, and an electron injection and transport layer. In this case, the organic layer containing the compound may be an electron injection and transport layer.

[0182] In another embodiment, the organic layer may include a hole injection layer, a hole transport layer, an electron suppression layer, a light emitting layer, and an electron injection and transport layer. In this case, the organic layer containing the compound may be an electron injection and transport layer.

[0183] In another embodiment, the organic layer may include a hole injection layer, a hole transport layer, an electron suppression layer, a light-emitting layer, an electron blocking layer, and an electron injection and transport layer. In this case, the organic layer containing the compound may be an electron injection and transport layer.

[0184] The organic layer of the organic light-emitting device of the present invention may be formed of a single-layer structure, but may also be formed of a multilayer 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 that includes, in addition to the light-emitting layer, a hole injection layer and a hole transport layer between the first electrode and the light-emitting layer, and an electron transport layer and an electron injection layer between the light-emitting layer and the second electrode as organic layers. However, the structure of the organic light-emitting device is not limited thereto, and may include a smaller number or a larger number of organic layers.

[0185] In addition, the organic light-emitting device according to the present invention may be an organic light-emitting device of a structure (normal type) in which the first electrode is an anode, the second electrode is a cathode, and an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate. In addition, the organic light-emitting device according to the present invention may be an organic light-emitting device of an inverted structure (inverted type) in which the first electrode is a cathode, the second electrode is an anode, and a cathode, one or more organic layers, and an anode are sequentially stacked on a substrate. For example, the structure of an organic light-emitting device according to one embodiment of the present invention is shown in FIG. Figures 1 to 3 .

[0186] Figure 1The diagram shows an example of an organic light emitting device composed of a substrate 1, an anode 2, a hole transport layer 3, a light emitting layer 4, an electron injection and transport layer 5, and a cathode 6. In the above structure, the compound represented by the above Chemical Formula 1 may be contained in the above electron injection and transport layer.

[0187] 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 7, a hole transport layer 3, an electron suppression layer 8, a light-emitting layer 4, a hole blocking layer 9, an electron injection and transport layer 5, and a cathode 6. In the structure described above, the compound represented by the above chemical formula 1 may be contained in the above electron injection and transport layer.

[0188] Figure 3 The diagram shows an example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole injection layer 7, a hole transport layer 3, a light-emitting layer 4, an electron injection and transport layer 5, and a cathode 6. In the structure described above, the compound represented by the above Chemical Formula 1 may be contained in the above electron injection and transport layer.

[0189] 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.

[0190] 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.

[0191] 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.

[0192] 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.

[0193] 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.

[0194] As the above-mentioned anode material, in order to enable holes to be smoothly injected into the organic layer, it is preferred to use a material with a large work function. 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); ZnO:Al or SnO 2 : Combinations of metals such as Sb and oxides; 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.

[0195] The cathode material is preferably a material with a small work function in order to facilitate electron injection into the organic layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; LiF / Al or LiO 2 / Al and other multilayer structure materials, but are not limited to these.

[0196] 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.

[0197] 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 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. As the hole transport material, arylamine organic matter, conductive polymers, and block copolymers having both conjugated and non-conjugated parts can be used, but it is not limited thereto.

[0198] The electron suppression layer is a layer formed on the hole transport layer, preferably in contact with the light-emitting layer, and improves the efficiency of the organic light-emitting device by adjusting the hole mobility, preventing the excessive migration of electrons, and increasing the probability of the combination between holes and electrons. The electron suppression layer includes an electron blocking substance. As an example of such an electron blocking substance, an arylamine organic substance can be used, but it is not limited thereto.

[0199] The above-mentioned luminescent material is a material that can receive holes and electrons from the hole transport layer and the electron transport layer respectively and combine them to emit light in the visible light region, and is preferably a material with high quantum efficiency for fluorescence or phosphorescence. As a specific example, there is 8-hydroxy-quinoline aluminum complex (Alq 3 ); carbazole compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo The present invention includes, but is not limited to, oxazole, benzothiazole and benzimidazole series compounds; poly(p-phenylenevinylene) (PPV) series polymers; spiro compounds; polyfluorene, rubrene, etc.

[0200] The above-mentioned light-emitting layer may include a host material and a dopant material. Such a host material may include an aromatic fused ring derivative or a heterocyclic compound. Specifically, as an aromatic fused ring derivative, there are anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and as a heterocyclic compound, there are carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, etc. Pyrimidine derivatives, etc., but are not limited to these.

[0201] 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.

[0202] The hole blocking layer is a layer formed on the light-emitting layer, preferably in contact with the light-emitting layer, and improves the efficiency of the organic light-emitting device by adjusting the electron mobility, preventing the excessive migration of holes, and increasing the probability of the combination between holes and electrons. The hole blocking layer contains a hole blocking substance. Examples of such a hole blocking substance include azine derivatives containing triazine, triazole derivatives, Compounds into which an electron-withdrawing group is introduced include, but are not limited to, oxadiazole derivatives, phenanthroline derivatives, phosphine oxide derivatives, and the like.

[0203] 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 acts as both an electron transport layer and an electron injection layer, and is formed on the light-emitting layer or the hole blocking layer. Such an electron injection and transport material is a material that can well receive electrons from the cathode and transfer them to the light-emitting layer, and a material with a high electron mobility is suitable. As a specific example of an electron injection and transport material, a compound represented by the above chemical formula 1 can be used. In addition, as an electron injection and transport material, an Al complex of 8-hydroxyquinoline, an Alq complex containing 3 The invention can be used in combination 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.

[0204] 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 this case, the electron transport layer is formed on the light-emitting layer or the hole blocking layer, and the electron injection and transport substances mentioned above can be used as the electron transport substances contained in the electron transport layer. In addition, the electron injection layer is formed on the electron transport layer, and LiF, NaCl, CsF, Li 2O, 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.

[0205] 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.

[0206] In one embodiment, the electron injection and transport layer or the electron transport layer of the organic light emitting device may include both the compound represented by the chemical formula 1 and the metal coordination compound. In this case, the electron injection and transport layer or the electron transport layer may include the compound represented by the chemical formula 1 and the 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.

[0207] 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.

[0208] In addition, the compound represented by the above Chemical Formula 1 may be included in an organic solar cell or an organic transistor in addition to being included in an organic light-emitting device.

[0209] 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.

[0210] <Synthesis example>

[0211] Synthesis Example 1: Synthesis of Compound 1

[0212]

[0213] Step 1) Synthesis of compound 1-a

[0214] Under a nitrogen atmosphere, 2-(5-bromo-2-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (50 g, 118.3 mmol) and (4-cyanophenyl)boric acid (17.4 g, 118.3 mmol) were added to 1000 ml of tetrahydrofuran, stirred and refluxed. Then, potassium carbonate (49 g, 354.9 mmol) was dissolved in 49 ml of water and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium (4.1 g, 3.5 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was again added to 1051 mL of toluene and dissolved, 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 toluene and ethyl acetate to produce a white solid compound 1-a (40.4 g, 77%, MS: [M+H] + =445.1).

[0215] Step 2) Synthesis of Compound 1

[0216] Under nitrogen atmosphere, compound 1-a (20 g, 445.2 mmol) and 2,4-diphenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (193.8 g, 445.2 mmol) were added to 400 ml of 1,4-diphenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine. alkane, stirring and reflux. Then, potassium phosphate (283.5 g, 1335.7 mmol) was dissolved in 284 ml of water and added. After sufficient stirring, dibenzylideneacetone palladium (7.7 g, 13.4 mmol) and tricyclohexylphosphine (7.5 g, 26.7 mmol) were added. After reacting for 7 hours, the reaction mixture was cooled to room temperature and the generated solid was filtered. The solid was added into 9580 mL of chloroform and dissolved. After washing with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce a white solid compound 1 (242.7 g, 76%, MS: [M+H] + =718.3).

[0217] Synthesis Example 2: Synthesis of Compound 2

[0218]

[0219] In Synthesis Example 1, 2-(5-bromo-2-chlorophenyl)-4,6-diphenyl-1,3,5-triazine and 2,4-diphenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine were replaced with 2-(5-bromo-2-chlorophenyl)-4,6-bis(phenyl-d5)-1,3,5-triazine and 2,4-bis(phenyl-d5)-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine. Compound 2 (MS[M+H]) was prepared by the same production method as that of Compound 1. + =738.4).

[0220] Synthesis Example 3: Synthesis of Compound 3

[0221]

[0222] In Synthesis Example 1, 2-(5-bromo-2-chlorophenyl)-4,6-diphenyl-1,3,5-triazine, (4-cyanophenyl)boronic acid and 2,4-diphenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine were replaced with 2-([1,1'-biphenyl]-4-yl)-4-(2-bromo-6-chlorophenyl)- Compound 3 (MS[M+H]) was prepared by the same method as that of Compound 1 except that 2-([1,1'-biphenyl]-2-yl)-4-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine was used. + =870.3).

[0223] Synthesis Example 4: Synthesis of Compound 4

[0224]

[0225] In Synthesis Example 1, 2-(5-bromo-2-chlorophenyl)-4,6-diphenyl-1,3,5-triazine and 2,4-diphenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine were replaced with 2-(3-bromo-2-chlorophenyl)-4,6-diphenyl-1,3,5-triazine and 2,4-diphenyl-6-(5'-phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1':3',1"-terphenyl]-3-yl)-1,3,5-triazine. Compound 4 (MS[M+H] + =946.4).

[0226] Synthesis Example 5: Synthesis of Compound 5

[0227]

[0228] In Synthesis Example 1, (4-cyanophenyl)boric acid and 2,4-diphenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine were replaced with (3-cyanophenyl)boric acid and 2-(dibenzo[b,d]thiophen-4-yl)-4-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine. Compound 5 (MS[M+H]) was prepared by the same production method as that of Compound 1. + =824.3).

[0229] Synthesis Example 6: Synthesis of Compound 6

[0230]

[0231] In Synthesis Example 1, except that 2-(5-bromo-2-chlorophenyl)-4,6-diphenyl-1,3,5-triazine and (4-cyanophenyl)boric acid were replaced with 1-(4-(4-(3-bromo-2-chlorophenyl)-6-phenyl-1,3,5-triazine-2-yl)phenyl)-2-phenyl-1H-benzo[d]imidazole and (2-cyanophenyl)boric acid, a compound 6 (MS[M+H]) was prepared by the same production method as the production method of compound 1. + =910.3).

[0232] Synthesis Example 7: Synthesis of Compound 7

[0233]

[0234] Step 1) Synthesis of compound 7-a

[0235] Under nitrogen atmosphere, 2-(2-bromo-4-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (50 g, 118.3 mmol) and bis(pinacol)diboron (30 g, 118.3 mmol) were added to 1000 ml of 1,4-diphenyl-1,3,5-triazine. alkane, stirring and reflux. Then, potassium acetate (75.3 g, 354.9 mmol) was added, and after sufficient stirring, bis(dibenzylideneacetone)palladium (0.7 g, 1.2 mmol) and dicyclohexylphosphine (0.5 g, 2.4 mmol) were added. After reacting for 4 hours, the mixture was cooled to room temperature, and the organic layer was filtered to remove the salt, and the filtered organic layer was distilled. It was again put into 10 times 555 mL of chloroform to dissolve, washed with water twice, and 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 ethanol to produce a white solid compound 7-a (43.3 g, 78%, MS: [M+H] + =470.2).

[0236] Step 2) Synthesis of compound 7-b

[0237] Under nitrogen atmosphere, compound 7-a (50g, 106.4mmol) and 2-(2-bromo-4-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (45g, 106.4mmol) were added to 1000ml of tetrahydrofuran, stirred and refluxed. Then, potassium carbonate (44.1g, 319.3mmol) was dissolved in 44mL of water and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium (3.7g, 3.2mmol) was added. After reacting for 3 hours, the organic layer and the aqueous layer were separated after cooling to room temperature, and the organic layer was distilled. It was again added to 20 times 1456mL of toluene to dissolve, washed with water twice, separated the organic layer, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from toluene and ethyl acetate to produce a white solid compound 7-b (57.5g, 79%, MS: [M+H] + =685.2).

[0238] Step 3) Synthesis of Compound 7

[0239] Under nitrogen atmosphere, compound 7-b (20 g, 29.2 mmol) and (2-cyanophenyl)boronic acid (8.6 g, 58.4 mmol) were added to 400 ml of 1,4-dihydroquinone. alkane, stirring and reflux. Then, potassium phosphate (18.6 g, 87.5 mmol) was dissolved in 19 ml of water and added. After sufficient stirring, dibenzylideneacetone palladium (0.5 g, 0.9 mmol) and tricyclohexylphosphine (0.5 g, 1.8 mmol) were added. After reacting for 8 hours, the reaction was cooled to room temperature and the generated solid was filtered. The solid was dissolved in 30 times 717 mL 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 white solid compound 7 (15.5 g, 65%, MS: [M+H] + =819.9).

[0240] Synthesis Example 8: Synthesis of Compound 8

[0241]

[0242] In Synthesis Example 1, except that 2-(2'-bromo-6'-chloro-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine was used instead of 2-(5-bromo-2-chlorophenyl)-4,6-diphenyl-1,3,5-triazine, a compound 8 (MS[M+H] + =794.3).

[0243] Synthesis Example 9: Synthesis of Compound 9

[0244]

[0245] Step 1) Synthesis of compound 9-a

[0246] Under a nitrogen atmosphere, 2-chloro-4,6-diphenyl-1,3,5-triazine (50 g, 186.8 mmol) and (3-chloro-5-cyanophenyl)boric acid (33.9 g, 186.8 mmol) were added to 1000 ml of tetrahydrofuran, stirred and refluxed. Then, potassium carbonate (77.4 g, 560.3 mmol) was dissolved in 77 ml of water and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium (6.5 g, 5.6 mmol) was added. After reacting for 2 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. It was again added to 1378 mL of toluene and dissolved. After washing with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was filtered after stirring. The filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from toluene and ethyl acetate to produce a white solid compound 9-a (62.7 g, 91%, MS: [M+H] + =369.8).

[0247] Step 2) Synthesis of compound 9-b

[0248] Under nitrogen atmosphere, compound 9-a (50 g, 135.6 mmol) and bis(pinacolato)diboron (34.4 g, 135.6 mmol) were added to 1000 ml of 1,4-dihydro-1,4-diol. alkane, stirring and reflux. Then, potassium acetate (86.3 g, 406.7 mmol) was added, and after sufficient stirring, bis(dibenzylideneacetone)palladium (0.8 g, 1.4 mmol) and dicyclohexylphosphine (0.5 g, 2.7 mmol) were added. After reacting for 4 hours, the mixture was cooled to room temperature, and the organic layer was filtered to remove the salt, and the filtered organic layer was distilled. It was again added to 624 mL of chloroform to dissolve, and after washing with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to produce a white solid compound 9-b (45.5 g, 73%, MS: [M+H] + =461.2).

[0249] Step 3) Synthesis of compound 9-c

[0250] Under a nitrogen atmosphere, compound 9-b (50g, 108.6mmol) and 2'-bromo-3'-chloro-[1,1'-biphenyl]-3-carbonitrile (31.8g, 108.6mmol) were added to 1000ml of tetrahydrofuran, stirred and refluxed. Then, potassium carbonate (45g, 325.8mmol) was dissolved in 45ml of water and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium (3.8g, 3.3mmol) was added. After reacting for 1 hour, the organic layer and the aqueous layer were separated after cooling to room temperature, and the organic layer was distilled. It was put into 20 times 1184mL of toluene again and dissolved. After washing with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, and the filtrate was filtered after stirring. The filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from toluene and ethyl acetate to produce a white solid compound 9-c (37.9g, 64%, MS: [M+H] + =546.1).

[0251] Step 4) Synthesis of Compound 9

[0252] Under nitrogen atmosphere, 9-c (20 g, 36.6 mmol) and 2,4-diphenyl-6-(4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1':2',1"-terphenyl]-3'-yl)-1,3,5-triazine (21.5 g, 36.6 mmol) were added to 400 ml of 1,4-diphenyl-6-(4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1':2',1"-terphenyl]-3'-yl)-1,3,5-triazine. alkane, stirring and reflux. Then, potassium phosphate (23.3 g, 109.9 mmol) was dissolved in 23 mL of water and added. After sufficient stirring, dibenzylideneacetone palladium (0.6 g, 1.1 mmol) and tricyclohexylphosphine (0.6 g, 2.2 mmol) were added. After reacting for 8 hours, the reaction was cooled to room temperature and the generated solid was filtered. The solid was dissolved in 30 times 1067 mL 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 white solid compound 9 (20.6 g, 58%, MS: [M+H] + =971.4).

[0253] Synthesis Example 10: Synthesis of Compound 10

[0254]

[0255] Compound 10 (MS [M + H]) was prepared by the same method as the method for preparing compound 1, except that 2-(5-bromo-2-chlorophenyl)-4,6-diphenyl-1,3,5-triazine, (4-cyanophenyl)boric acid and 2,4-diphenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine were used instead of 2-(2-bromo-6-chlorophenyl)-4,6-diphenylpyrimidine, (4-cyanophenyl)boric acid and 2-(dibenzo[b,d]furan-3-yl)-4-phenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine in Synthesis Example 1. + =807.3).

[0256] Synthesis Example 11: Synthesis of Compound 11

[0257]

[0258] Compound 11 (MS [M+H]) was prepared by the same method as Compound 1 except that 2-(4-bromo-2-chlorophenyl)-4,6-diphenyl-1,3,5-triazine and (4-cyanophenyl)boric acid were used instead of 2-(4-bromo-2-chlorophenyl)-4,6-diphenyl-1,3,5-triazine and (4-cyanonaphthalen-1-yl)boric acid in Synthesis Example 1. + =768.3).

[0259] Synthesis Example 12: Synthesis of Compound 12

[0260]

[0261] Step 1) Synthesis of compound 12-a

[0262] Under a nitrogen atmosphere, 2-(4,5-dibromo-2-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (50g, 99.7mmol) and (4-cyanophenyl)boric acid (29.2g, 199.4mmol) were added to 1000ml of tetrahydrofuran, stirred and refluxed. Then, potassium carbonate (41.3g, 299mmol) was dissolved in 41ml of water and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium (3.5g, 3mmol) was added. After reacting for 1 hour, the organic layer and the aqueous layer were separated after cooling to room temperature, and the organic layer was distilled. It was again added to 20 times 1089mL of toluene to dissolve, washed with water twice, separated the organic layer, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from toluene and ethyl acetate to produce a white solid compound 12-a (47.4g, 87%, MS: [M+H] + =546.1).

[0263] Step 2) Synthesis of compound 12

[0264] Compound 12 (MS [M + H]) was prepared by the same production method as in step 2 of compound 1, except that 2,4-diphenyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine was used instead of 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-2-yl)-1,3,5-triazine. + =869.3).

[0265] Example 1

[0266] 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.

[0267] 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 mm / s. On the hole injection layer, hexanitrile hexaazatriphenylene (HAT, ) and the following compound HT-A Vacuum deposition was sequentially performed to form a hole transport layer.

[0268] Next, on the hole transport layer, a film with a thickness of The following compounds BH and BD were vacuum deposited at a weight ratio of 25:1 to form a light-emitting layer.

[0269] On the above-mentioned light-emitting layer, the compound 1 prepared in Synthesis Example 1 and the following compound [LiQ] (Lithium quinolate) were vacuum-deposited at a weight ratio of 1:1, thereby On the electron injection and transport layer, lithium fluoride (LiF) is sequentially added with The thickness of the aluminum A cathode is formed by evaporation with a thickness of .

[0270]

[0271] 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 5×10 -8 ~1×10 -7 A support is provided to produce an organic light-emitting device.

[0272] Examples 2 to 12

[0273] An organic light-emitting device was manufactured by the same method as in Example 1, except that the compound shown in Table 1 below was used instead of Compound 1 as the electron injection and transport layer compound.

[0274] Comparative Examples 1 to 4

[0275] An organic light-emitting device was manufactured by the same method as in Example 1, except that the compound shown in Table 1 below was used instead of Compound 1 as the electron injection and transport layer compound.

[0276] The compounds ET-1 to ET-4 used in the following Table 1 are as follows.

[0277]

[0278] Experimental example

[0279] For the organic light-emitting devices manufactured in the above embodiments and comparative examples, 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.

[0280]

Table 1

[0281]

[0282] As described in Table 1, it was confirmed that the organic light-emitting devices of Examples 1 to 12 using the compound represented by Chemical Formula 1 of the present invention exhibited excellent characteristics in voltage, efficiency, and lifespan (T90).

[0283] That is, the compound represented by Chemical Formula 1 has a distorted structure due to the substitution of two six-membered heterocyclic groups containing two or more N groups at the ortho position on the biphenyl linking group, which is beneficial for electron transport, and due to the cyano group substituted on the aromatic group, electron injection and migration are regulated, thereby showing excellent characteristics in terms of voltage, efficiency and life span of the organic light-emitting device.

[0284] In addition, from the comparison between Example 12 and Comparative Example 1, it can be confirmed that in Chemical Formula 1, the substituent R 1 or R 2 When the cyano groups are bonded to each other to form an unsubstituted benzene ring fused to an adjacent ring, two or more cyano groups are introduced to facilitate electron injection, thereby improving the voltage and life characteristics of the organic light-emitting device.

[0285] In addition, it can be confirmed that Ar 5 and Ar 6 Comparative Examples 3 and 4, which do not contain a cyano group, show significantly lower efficiency and life characteristics compared to the examples.

Claims

1. A compound represented by the following chemical formula 1: [Chemical formula 1] In the chemical formula 1, X1 to X3 are each independently N or CR, but at least two of X1 to X3 are N, X4 to X6 are each independently N or CR, but at least two of X4 to X6 are N, in, R is independently hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C 1-60 Alkyl; substituted or unsubstituted C 6-60 Aryl; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S 2-60 Heteroaryl, L1 and L2 are each independently a single bond, or a substituted or unsubstituted C 6-60 Arylene, Ar1 to Ar4 are each independently substituted or unsubstituted C 6-60 Aryl; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S 2-60 Heteroaryl, Ar5 and Ar6 are each independently substituted or unsubstituted C 6-60 Aryl, However, at least one of Ar5 and Ar6 is substituted by a cyano group, n and m are each independently an integer from 0 to 4, However, if n+m is greater than 1, R1 and R2 are each independently deuterium, halogen, cyano, or substituted or unsubstituted C 1-60 Alkyl, or two adjacent substituents are combined with each other to form a substituted or unsubstituted C 6-20 Aromatic ring, However, when two or more adjacent R1 or R2 are bonded to each other to form an unsubstituted benzene ring fused to the adjacent ring, n+m is 2 or more, a is an integer from 0 to 4-n, b is an integer from 0 to 4-m.

2. The compound according to claim 1, wherein X1 to X3 are all N; or X1 and X2 are N, and X3 is CR; or X1 and X3 are N, X2 is CR, Wherein R is hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C 1-10 Alkyl, or substituted or unsubstituted C 6-20 Aryl.

3. The compound according to claim 1, wherein X4 to X6 are all N; or X4 and X5 are N, and X6 is CR; or X4 and X6 are N, X5 is CR, Wherein R is hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C 1-10 Alkyl, or substituted or unsubstituted C 6-20 Aryl.

4. The compound according to claim 1, wherein L1 and L2 are each independently a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenyldiyl group, a substituted or unsubstituted terphenyldiyl group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted pyrene group, or a substituted or unsubstituted fluoranthenylene group, Wherein, "substituted" refers to being selected from deuterium, cyano, C 1-10 Alkyl, C 6-20 Aryl, pyridyl, pyrimidinyl, dibenzofuranyl, dibenzothiophenyl, benzo substituted with one or more substituents of oxazolyl and benzothiazolyl, The substituent C 1-10 Alkyl, C 6-60 Aryl, dibenzofuranyl, dibenzothiophenyl, benzo The oxazolyl group and the benzothiazolyl group are each independently substituted or unsubstituted with a substituent selected from the group consisting of deuterium, cyano and halogen.

5. The compound according to claim 1, wherein Ar1 to Ar4 are each independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted benzonaphthofuranyl, substituted or unsubstituted benzonaphthothiophenyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted benzothiophenyl ...furanyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted substituted or unsubstituted carbazolyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted pyridyl, or substituted or unsubstituted pyrimidinyl.

6. The compound according to claim 5, wherein "Substituted" means being selected from deuterium, halogen, cyano, C 1-10 Alkyl, C 1-10 Alkoxy, C 3-7 Cycloalkyl, C 6-20 Aryl, pyridyl, pyrimidinyl, dibenzofuranyl, dibenzothiophenyl, benzo substituted with one or more substituents of oxazolyl and benzothiazolyl, The substituent C 1-10 Alkyl, C 1-10 Alkoxy, C 3-7 Cycloalkyl, C 6-60 Aryl, dibenzofuranyl, dibenzothiophenyl, benzo The oxazolyl group and the benzothiazolyl group are each independently substituted or unsubstituted with a substituent selected from the group consisting of deuterium, cyano and halogen.

7. The compound according to claim 1, wherein Substituents different.

8. The compound according to claim 1, wherein Ar5 and Ar6 are each independently phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, anthracenyl, phenanthryl or triphenylene, Wherein, Ar5 and Ar6 are substituted with one or more substituents selected from deuterium, cyano, halogen, phenyl, naphthyl, and phenanthryl, or are unsubstituted.

9. The compound according to claim 1, wherein Ar5 and Ar6 substituted by cyano groups are each independently phenyl substituted by 1 to 3 cyano groups, biphenyl substituted by 1 to 3 cyano groups, terphenyl substituted by 1 to 3 cyano groups, naphthyl substituted by 1 to 3 cyano groups, (triphenyl)phenyl substituted by 1 to 3 cyano groups, or (phenyl)naphthyl substituted by 1 to 3 cyano groups, Here, Ar5 and Ar6 substituted with cyano are substituted with deuterium or are unsubstituted.

10. The compound according to claim 1, wherein 1 Ar5 is substituted by 1 cyano, and the remaining Ar5 and Ar6 are not substituted by deuterium; or 2 Ar5 are substituted by 1 cyano, and the remaining Ar5 and Ar6 are not substituted by deuterium; or One Ar5 is substituted by one cyano group, one Ar6 is substituted by one cyano group, and the remaining Ar5 and Ar6 are not substituted by deuterium.

11. The compound according to claim 1, wherein n is 1, m is 0; or n is 1, m is 1; or n is 1, m is 2; or n is 1, m is 3; or n is 2, m is 2; or n is 3, m is 0; or n is 4 and m is 0.

12. The compound according to claim 1, wherein R1 and R2 are each independently deuterium, halogen, cyano, substituted or unsubstituted methyl, or substituted or unsubstituted ethyl, or Two or more adjacent R1 or R2 are bonded to each other to form a substituted or unsubstituted benzene, naphthalene or phenanthrene ring condensed with the adjacent ring.

13. The compound according to claim 1, wherein The compound has 1, 2, 3 or 4 cyano groups.

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

15. 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 14.

16. The organic light emitting device according to claim 15, wherein: The organic layer containing the compound is an electron injection and transport layer.

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