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] Ar1 is a substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S. 2-60 Heteroaryl,

[0016] L1 is a single bond; substituted or unsubstituted C 10-60 or a substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S; 2-60 Heteroarylene,

[0017] Ar2 is 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] Ar2 is substituted or unsubstituted C 6-60 In the case of an aryl group, L2 is a single bond; substituted or unsubstituted C 6-60 or a substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S; 2-60 Heteroarylene,

[0019] Ar2 is a substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S. 2-60 In the case of heteroaryl, L2 is a single bond; substituted or unsubstituted C 10-60 or a substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S; 2-60 Heteroarylene,

[0020] D stands for deuterium,

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

[0022] b is an integer from 0 to 3,

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

[0024] d is an integer from 0 to 8.

[0025] In addition, the present invention provides an organic light-emitting device, which includes: a first electrode, a second electrode arranged opposite to the first electrode, and one or more organic layers arranged between the first electrode and the second electrode, and one or more of the organic layers contains the compound represented by the above chemical formula 1.

[0026] Effects of the Invention

[0027] 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

[0028] 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.

[0029] 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.

[0030] Explanation of symbols

[0031] 1: Substrate 2: Anode

[0032] 3: Hole transport layer 4: Light-emitting layer

[0033] 5: Electron injection and transport layer 6: Cathode

[0034] 7: Hole injection layer 8: Electron suppression layer

[0035] 9: Hole blocking layer DETAILED DESCRIPTION

[0036] In the following, the present invention will be described in more detail to help understanding the present invention.

[0037] (Explanation of terms)

[0038] In this manual, "D" represents a bond to other substituents, and "D" represents deuterium.

[0039] 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 6-20The 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".

[0040] 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.

[0041]

[0042] 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.

[0043]

[0044] 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.

[0045]

[0046] 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 C 1-60 Haloalkyl, substituted or unsubstituted C 2-60 Alkenyl, substituted or unsubstituted C 2-60 haloalkenyl, or substituted or unsubstituted C6-60 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.

[0047] In the present specification, specific examples of the boryl group include trimethylboryl, triethylboryl, tert-butyldimethylboryl, triphenylboryl, and phenylboryl, but are not limited thereto.

[0048] In the present specification, as examples of the halogen group, there are fluorine, chlorine, bromine or iodine.

[0049] 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.

[0050] 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.

[0051] 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.

[0052] 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.

[0053] 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.

[0054] In addition, examples of the spirocyclic hydrocarbon group include spiro[3.4]octyl and spiro[5.5]undecyl, but are not limited to these.

[0055] 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.

[0056] 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.

[0057] 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.

[0058] 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.

[0059] 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.

[0060] 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.

[0061] 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.

[0062] In the present specification, "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.

[0063] In addition, "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.

[0064] 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.

[0065]

[0066] In addition, the "deuterium substitution rate" or "deuteration degree" of a compound refers to 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 substituted with deuterium in the compound and the number of deuteriums substituted) calculated as a percentage. 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.

[0067] 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 a generally known method. 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.

[0068] (Compound)

[0069] In another aspect, the present invention provides a compound represented by the above Chemical Formula 1.

[0070] Specifically, the compound represented by the above chemical formula 1 is a compound having the following structure: a carbazole group and an amine group are bonded via a biphenyl linking group, the biphenyl linking group is substituted with a "phenyl group", and the phenyl group and the carbazole group are bonded at the "ortho" position. In addition, the amino group has at least one heteroaryl group.

[0071] Compared with compounds in which the amino group is substituted only by an aryl group, the compound having the structure described above has a low HOMO energy level, facilitates hole migration, can show high efficiency characteristics, and has a higher structural stability, so it is also advantageous in terms of the life of the organic light-emitting device. In addition, the phenyl group substituted on the biphenyl linking group of the above compound exists in an ortho position with the carbazole group, so it has a more stable molecular structure, which can further improve the life of the organic light-emitting device.

[0072] Therefore, an organic light-emitting device using the above compound can not only show a low driving voltage but also improve efficiency and lifespan characteristics at the same time, compared with an organic light-emitting device using a compound having a structure different from the above.

[0073] In one embodiment, Ar1 may be a substituted or unsubstituted C containing 1 or 2 heteroatoms selected from N, O and S. 2-20 Heteroaryl.

[0074] In one embodiment, Ar1 can be a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted benzonaphthofuranyl group, a substituted or unsubstituted benzonaphthothiophenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted benzocarbazolyl group, a substituted or unsubstituted benzothiazolyl group, a substituted or unsubstituted benzo oxazolyl, or substituted or unsubstituted benzimidazolyl.

[0075] In one embodiment, Ar1 is a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted 9-phenylcarbazolyl group.

[0076] On the other hand, L1 can be a single bond, or a substituted or unsubstituted C 10-20 Arylene.

[0077] In one embodiment, L1 can be a single bond; or can be selected from deuterium, cyano, substituted or unsubstituted C 1-10 Alkyl, substituted or unsubstituted C 6-20C substituted or unsubstituted by one or more substituents of aryl, and substituted or unsubstituted silyl 10-20 Arylene.

[0078] In one embodiment, L1 may be a single bond, a substituted or unsubstituted biphenyl diyl group, or a substituted or unsubstituted naphthalene diyl group.

[0079] In one embodiment, Ar2 may be a substituted or unsubstituted C 6-20 Aryl; or substituted or unsubstituted C containing 1 or 2 heteroatoms selected from N, O and S 2-20 Heteroaryl.

[0080] In one embodiment, Ar2 can be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted dimethylfluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted 9-phenylcarbazolyl group.

[0081] In one embodiment, L2 can be a single bond; substituted or unsubstituted C 6-60 or a substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S; 2-60 However, Ar2 is a substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S. 2-60 In the case of heteroaryl, L2 is a single bond; substituted or unsubstituted C 10-60 or a substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S; 2-60 Heteroarylene.

[0082] In one embodiment, L2 may be a single bond; a substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S; 2-60 or a substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S; 2-20 Heteroarylene.

[0083] In one embodiment, L2 may be a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthalene diyl group.

[0084] Specifically, Ar2 is a substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S. 2-20 In the case of an aryl group, L2 may be a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthalenediyl group, and Ar2 may be a substituted or unsubstituted C containing one or more heteroatoms selected from N, O, and S. 2-20 In the case of a heteroaryl group, L2 may be a single bond, or a substituted or unsubstituted naphthalenediyl group.

[0085] In addition, when Ar2 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, or a substituted or unsubstituted dimethylfluorenyl group, L2 can be a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthalenediyl group, or L2 can be a single bond, or a substituted or unsubstituted naphthalenediyl group.

[0086] When Ar2 is a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted 9-phenylcarbazolyl group, L2 may be a single bond or a substituted or unsubstituted naphthalenediyl group.

[0087] In addition, L1 and L2 can both be single bonds; or

[0088] Only one of L1 and L2 can be a single bond; or

[0089] L1 and L2 may not be a single bond.

[0090] In addition, L1 and L2 may be the same as or different from each other.

[0091] In addition, in one embodiment, L1 and L2 can both be single bonds; or

[0092] L1 may be any one selected from the group consisting of the following and their deuterated structures, and L2 may be a single bond:

[0093]

[0094] In one embodiment, Ar1 may be a substituted or unsubstituted C containing 1 or 2 heteroatoms selected from N, O and S. 2-20 Heteroaryl, Ar2 can be substituted or unsubstituted C 6-20 Aryl; or

[0095] Ar1 and Ar2 can each independently be a substituted or unsubstituted C containing 1 or 2 heteroatoms selected from N, O and S. 2-20 Heteroaryl.

[0096] Here, "substituted" in Ar1, Ar2, L1 and L2 refers to being selected from deuterium, cyano, substituted or unsubstituted C 1-10 Alkyl, and substituted or unsubstituted C 6-20 The aryl group is substituted with one or more substituents.

[0097] More specifically, "substituted" in Ar1, Ar2, L1 and L2 may refer to substitution with one or more substituents selected from deuterium, cyano, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted butyl, and substituted or unsubstituted phenyl.

[0098] In addition, L1-Ar1 and L2-Ar2 may be different.

[0099] In addition, a+b+c may be 0 or 1 or more.

[0100] Specifically, a+b+c can be 0 or 1 or more, 2 or more, 3 or more, 4 or more, 5 or more, 6 or more, 7 or more, 8 or more, 9 or more and 12 or less, 11 or less, or 10 or less.

[0101] Preferably, a+b+c may be 0 or 5 or more.

[0102] In addition, d may be 0 or 1 or more.

[0103] Specifically, d may be 0, or 1 or more, 2 or more, 3 or more, 4 or more, 5 or more and 8 or less, 7 or less, or 6 or less.

[0104] More specifically, the above compound may contain no deuterium or one or more deuterium.

[0105] When the above compound contains deuterium, the deuterium substitution rate of the compound may be 1% to 100%. Specifically, the deuterium substitution rate of the above compound may 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, 8% or less, 60% or less, 40% or less, or 20% or less.

[0106] As an example, the compound may contain no deuterium or contain 1 to 50 deuteriums. More specifically, the compound may contain no deuterium or 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.

[0107] On the other hand, representative examples of the compound represented by the above Chemical Formula 1 are shown below:

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140] On the other hand, the compound represented by the above chemical formula 1 can be produced by the production method shown in the following reaction formula 1:

[0141] [Reaction formula 1]

[0142]

[0143] In the above reaction formula, the remaining groups except X' are the same as those defined in Chemical Formula 1, and X' is a halogen. Preferably, X' is chlorine or bromine.

[0144] The above reaction formula 1 is an amine substitution reaction, which is preferably carried out in the presence of a palladium catalyst and a base. The reactive group used for the amine substitution reaction can be changed according to the techniques known in the art.

[0145] On the other hand, when manufacturing a compound of chemical formula 1 containing one or more deuteriums, a starting material that already contains deuterium can be used as shown in the above reaction formula 1, or a starting material that does not contain deuterium can be used to form a carbon skeleton and then a hydrogen / deuterium substitution reaction can be performed to obtain a deuterium-substituted compound.

[0146] The above-mentioned production method can be further embodied in the production examples described below.

[0147] (Organic Light Emitting Devices)

[0148] 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, which includes: 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 includes the compound represented by the above Chemical Formula 1.

[0149] 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.

[0150] In this case, the organic layer including the above compound may be a hole transport layer or an electron suppression layer.

[0151] 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 a hole transport layer.

[0152] 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 a hole transport layer or an electron suppression layer.

[0153] In another embodiment, the above-mentioned organic layer may include a hole injection layer, a hole transport layer, an electron suppression layer, a light-emitting layer, a hole blocking layer, and an electron injection and transport layer. In this case, the organic layer containing the above-mentioned compound may be a hole transport layer or an electron suppression layer.

[0154] 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, 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 the organic layer. 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.

[0155] 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. Figure 1 and 2 .

[0156] Figure 1 The diagram shows an example of an organic light emitting device composed of a substrate 1, an anode 2, a hole transport layer 3, a light emitting layer 4, an electron 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 hole transport layer.

[0157] Figure 2The 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 hole transport layer or the electron suppression layer.

[0158] 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.

[0159] 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.

[0160] 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.

[0161] 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.

[0162] 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.

[0163] 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.

[0164] 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.

[0165] 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.

[0166] 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. A material with a large mobility of holes is suitable. As the hole transport material, a compound represented by the above chemical formula 1 can be used. In addition, an arylamine-based organic substance, a conductive polymer, and a block copolymer having both a conjugated portion and a non-conjugated portion can be used, but it is not limited thereto.

[0167] The electron suppression layer is a layer formed on the hole transport layer, preferably in contact with the light-emitting layer, which improves the efficiency of the organic light-emitting device by adjusting the hole mobility and preventing the excessive migration of electrons to increase the probability of hole-electron bonding. The electron suppression layer contains an electron suppression substance, and as an example of such an electron suppression substance, the compound represented by the above chemical formula 1 can be used. In addition, an arylamine-based organic substance can be used, but it is not limited thereto.

[0168] 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 azole, benzothiazole and benzimidazole compounds; poly(p-phenylenevinylene) (PPV) polymers; spiro compounds; polyfluorene, rubrene, etc., but are not limited thereto.

[0169] 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., as heterocyclic compounds, there are carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, etc. Pyrimidine derivatives, etc., but are not limited to these.

[0170] 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.

[0171] The hole blocking layer is a layer formed on the light-emitting layer, preferably in contact with the light-emitting layer, which improves the efficiency of the organic light-emitting device by adjusting the electron mobility and preventing the excessive migration of holes to increase the probability of hole-electron bonding. The hole blocking layer contains a hole blocking substance. Examples of such 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.

[0172] 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 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 electron injection and transport substances are substances that can well receive electrons from the cathode and transfer them to the light-emitting layer, and substances with high electron mobility are suitable. As specific examples of electron injection and transport substances, Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free radical compounds, hydroxyflavone-metal complexes, triazine derivatives, etc. can also be used, 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.

[0173] 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 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.

[0174] 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.

[0175] 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.

[0176] 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 an organic light emitting device.

[0177] 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.

[0178] [Manufacturing example]

[0179] Production Example 1

[0180]

[0181] In a 500 mL round-bottom flask under a nitrogen atmosphere, compound A (20 g, 46.52 mmol) and compound B (19.48 g, 47.45 mmol) were completely dissolved in 300 mL of xylene, and sodium tert-butoxide (NaOtBu, 6.26 g, 65.12 mmol) was added, and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.12 g, 0.23 mmol) was added, followed by heating and stirring for 3 hours. The temperature was lowered to room temperature, the alkali was removed by filtration, and xylene was concentrated under reduced pressure and recrystallized with 240 mL of ethyl acetate to produce compound 1 (33.29 g, yield: 89%).

[0182] MS[M+H] + =804

[0183] Production Example 2

[0184]

[0185] Under nitrogen atmosphere, in a 500 mL round-bottom flask, compound A (20 g, 46.52 mmol) and compound C (16.68 g, 47.45 mmol) were completely dissolved in 300 mL of xylene, and NaOtBu (6.26 g, 65.12 mmol) was added, and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (0.12 g, 0.23 mmol) was added, and heated and stirred for 3 hours. The temperature was lowered to room temperature, and after filtering to remove the alkali, the xylene was concentrated under reduced pressure and recrystallized with 240 mL of ethyl acetate to produce compound 2 (28.42 g, yield: 82%).

[0186] MS[M+H] + =745

[0187] Production Example 3

[0188]

[0189] Under nitrogen atmosphere, in a 500 mL round-bottom flask, compound A (20 g, 46.52 mmol) and compound D (16.68 g, 47.45 mmol) were completely dissolved in 300 mL of xylene, and NaOtBu (6.26 g, 65.12 mmol) was added, and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (0.12 g, 0.23 mmol) was added, and heated and stirred for 3 hours. The temperature was lowered to room temperature, and after filtering to remove the alkali, the xylene was concentrated under reduced pressure and recrystallized with 240 mL of ethyl acetate to produce compound 3 (29.46 g, yield: 85%).

[0190] MS[M+H] + =745

[0191] Production Example 4

[0192]

[0193] Under nitrogen atmosphere, in a 500 mL round-bottom flask, compound A (20 g, 46.52 mmol) and compound E (15.91 g, 47.45 mmol) were completely dissolved in 300 mL of xylene, and NaOtBu (6.26 g, 65.12 mmol) was added, and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (0.12 g, 0.23 mmol) was added, and heated and stirred for 3 hours. The temperature was lowered to room temperature, and after filtering to remove the alkali, the xylene was concentrated under reduced pressure and recrystallized with 240 mL of ethyl acetate to produce compound 4 (29.50 g, yield: 87%).

[0194] MS[M+H] + =729

[0195] Production Example 5

[0196]

[0197] Under nitrogen atmosphere, in a 500 mL round-bottom flask, compound A (20 g, 46.52 mmol) and compound F (19.52 g, 47.45 mmol) were completely dissolved in 300 mL of xylene, and NaOtBu (6.26 g, 65.12 mmol) was added, and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (0.12 g, 0.23 mmol) was added, and heated and stirred for 3 hours. The temperature was lowered to room temperature, and after filtering to remove the alkali, the xylene was concentrated under reduced pressure and recrystallized with 240 mL of ethyl acetate to produce compound 5 (34.82 g, yield: 93%).

[0198] MS[M+H] + =805

[0199] Production Example 6

[0200]

[0201] Under nitrogen atmosphere, in a 500 mL round-bottom flask, compound A (20 g, 46.52 mmol) and compound G (21.88 g, 47.45 mmol) were completely dissolved in 300 mL of xylene, and NaOtBu (6.26 g, 65.12 mmol) was added, and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (0.12 g, 0.23 mmol) was added, and heated and stirred for 3 hours. The temperature was lowered to room temperature, and after filtering to remove the alkali, the xylene was concentrated under reduced pressure and recrystallized with 240 mL of ethyl acetate to produce compound 6 (38.18 g, yield: 96%).

[0202] MS[M+H]+ =855

[0203] Production Example 7

[0204]

[0205] Under nitrogen atmosphere, in a 500 mL round-bottom flask, compound A (20 g, 46.52 mmol) and compound H (18.58 g, 47.45 mmol) were completely dissolved in 300 mL of xylene, and NaOtBu (6.26 g, 65.12 mmol) was added, and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (0.12 g, 0.23 mmol) was added, and heated and stirred for 3 hours. The temperature was lowered to room temperature, and after filtering to remove the alkali, the xylene was concentrated under reduced pressure and recrystallized with 240 mL of ethyl acetate to produce compound 7 (31.04 g, yield: 85%).

[0206] MS[M+H] + =785

[0207] Production Example 8

[0208]

[0209] Under nitrogen atmosphere, in a 500 mL round-bottom flask, compound A (20 g, 46.52 mmol) and compound I (18.29 g, 47.45 mmol) were completely dissolved in 300 mL of xylene, and NaOtBu (6.26 g, 65.12 mmol) was added, and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (0.12 g, 0.23 mmol) was added, and heated and stirred for 3 hours. The temperature was lowered to room temperature, and after filtering to remove the alkali, the xylene was concentrated under reduced pressure and recrystallized with 240 mL of ethyl acetate to produce compound 8 (31.89 g, yield: 88%).

[0210] MS[M+H] + =779

[0211] Production Example 9

[0212]

[0213] Under nitrogen atmosphere, in a 500 mL round-bottom flask, compound 1 (20 g, 24.88 mmol) was completely dissolved in 160 mL of 1,1,2,2-tetrachloroethane, and a solution (77.23 ml) of heavy water (D2O): trifluoromethanesulfonic anhydride = 5:1 was added, and the temperature was raised to 130°C, and heated and stirred for 3 hours. The temperature was lowered to room temperature, the organic layer was separated, and after post-treatment with 10% potassium carbonate aqueous solution (work up), 1,1,2,2-tetrachloroethane was concentrated under reduced pressure, and recrystallized with 240 mL of ethyl acetate, thereby producing compound 9 (16.83 g, yield: 81%).

[0214] MS[M+H] + =835

[0215] Production Example 10

[0216]

[0217] Under nitrogen atmosphere, in a 500 mL round-bottom flask, compound 7 (20 g, 24.88 mmol) was completely dissolved in 160 mL of 1,1,2,2-tetrachloroethane, and a solution of heavy water: trifluoromethanesulfonic anhydride = 5:1 (79.09 ml) was added, and the temperature was raised to 130°C, and heated and stirred for 3 hours. The temperature was lowered to room temperature, the organic layer was separated, and after post-treatment with 10% potassium carbonate aqueous solution, 1,1,2,2-tetrachloroethane was concentrated under reduced pressure and recrystallized with 240 mL of ethyl acetate to produce compound 10 (16.35 g, yield: 79%).

[0218] MS[M+H] + =812

[0219] Production Example 11

[0220]

[0221] Under nitrogen atmosphere, in a 500 mL round-bottom flask, compound 8 (20 g, 24.88 mmol) was completely dissolved in 160 mL of 1,1,2,2-tetrachloroethane, and a solution of heavy water: trifluoromethanesulfonic anhydride = 5:1 (79.70 ml) was added, and the temperature was raised to 130°C, and heated and stirred for 3 hours. The temperature was lowered to room temperature, the organic layer was separated, and after post-treatment with 10% potassium carbonate aqueous solution, 1,1,2,2-tetrachloroethane was concentrated under reduced pressure and recrystallized with 240 mL of ethyl acetate to produce compound 10 (17.18 g, yield: 83%).

[0222] MS[M+H] + =812

[0223] [Example]

[0224] Example 1-1

[0225] 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.

[0226] On the ITO transparent electrode prepared as the anode, the following compound HI1 and the following compound HI2 were mixed in a ratio of 98:2 (molar ratio) and A hole injection layer is formed by thermal vacuum deposition of a thickness of 1000 nm. On the hole injection layer, a compound represented by the following chemical formula HT1 is deposited Then, a film with a thickness of 1000 nm was deposited on the hole transport layer. Compound 1 was vacuum-deposited to form an electron suppression layer. Next, a film having a thickness of The compound represented by the following chemical formula BH and the compound represented by the following chemical formula BD were vacuum deposited at a weight ratio of 25:1 to form a light-emitting layer. A compound represented by the following chemical formula HB1 was vacuum-deposited to form a hole blocking layer. Next, a compound represented by the following chemical formula ET1 and a compound represented by the following chemical formula LiQ were vacuum-deposited at a weight ratio of 1:1 on the hole blocking layer to form a hole blocking layer. 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 .

[0227]

[0228] 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 2x10.-7 ~5ⅹ10 -6 A support is provided to produce an organic light-emitting device.

[0229] Example 1-2 to Example 1-11

[0230] An organic light-emitting device was manufactured by the same method as in Example 1-1, except that the compounds described in the following Table 1 were used instead of Compound 1.

[0231] Comparative Examples 1-1 to 1-3

[0232] An organic light-emitting device was manufactured by the same method as in Example 1-1, except that the compounds described in the following Table 1 were used instead of Compound 1.

[0233] The compounds of EB2, EB3 and EB4 in Table 1 are shown below.

[0234]

[0235] Experimental Example 1

[0236] When current was applied to the organic light emitting devices manufactured in the above examples and comparative examples, voltage, efficiency, color coordinates and lifetime were measured, and the results are shown in the following Table 1. T95 refers to the time required for the luminance to decrease from the initial luminance (1600 nits) to 95%.

[0237]

Table 1

[0238]

[0239] As shown in Table 1 above, the organic light-emitting device using the compound of the present invention as an electron suppressing layer exhibits excellent characteristics in terms of efficiency, driving voltage and stability of the organic light-emitting device.

[0240] From the results in Table 1, it can be confirmed that the compound according to the present invention has excellent electron blocking ability and can be suitably used in an electron suppression layer of an organic light-emitting device.

[0241] Examples 2-1 to 2-11 and Comparative Examples 2-1 to 2-3

[0242] An organic light-emitting device was manufactured by the same method as in Example 1-1, except that the following compound EB1 was used instead of Compound 1, and the compounds described in the following Table 2 were used instead of HT1.

[0243] The compounds HT2, HT3 and HT4 in Table 2 are shown below.

[0244]

[0245] Experimental Example 2

[0246] When current was applied to the organic light emitting devices manufactured in the above examples and comparative examples, voltage, efficiency, color coordinates and lifetime were measured, and the results are shown in the following Table 2. T95 refers to the time required for the luminance to decrease from the initial luminance (1600 nits) to 95%.

[0247]

Table 2

[0248]

[0249] As shown in Table 2 above, the organic light-emitting device using the compound of the present invention as a hole transport layer exhibits superior characteristics in terms of efficiency, driving voltage, and stability compared to the organic light-emitting devices of Comparative Examples 2-1 to 2-3.

[0250] From the results in Table 2, it can be confirmed that the compound according to the present invention has excellent hole transporting ability and can be suitably used in the hole transporting layer of an organic light-emitting device.

Claims

1. A compound represented by the following chemical formula 1: [Chemical formula 1] In the chemical formula 1, Ar1 is a substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S. 2-60 Heteroaryl, L1 is a single bond; substituted or unsubstituted C 10-60 or a substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S; 2-60 Heteroarylene, Ar2 is 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, Ar2 is substituted or unsubstituted C 6-60 In the case of an aryl group, L2 is a single bond; substituted or unsubstituted C 6-60 or a substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S; 2-60 Heteroarylene, Ar2 is a substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S. 2-60 In the case of heteroaryl, L2 is a single bond; substituted or unsubstituted C 10-60 or a substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S; 2-60 Heteroarylene, D stands for deuterium, a is an integer from 0 to 4, b is an integer from 0 to 3, c is an integer from 0 to 5, d is an integer from 0 to 8.

2. The compound according to claim 1, wherein L1 is a single bond, a substituted or unsubstituted biphenyldiyl group, or a substituted or unsubstituted naphthalenediyl group.

3. The compound according to claim 1, wherein L2 is a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthalenediyl group.

4. The compound according to claim 1, wherein Both L1 and L2 are single bonds; or L1 is any one selected from the group consisting of the following and their deuterated structures, L2 is a single bond, 5. The compound according to claim 1, wherein Ar1 is a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group, or a substituted or unsubstituted 9-phenylcarbazolyl group.

6. The compound according to claim 1, wherein Ar2 is substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted dimethylfluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted 9-phenylcarbazolyl.

7. The compound according to claim 1, wherein Ar1 is a substituted or unsubstituted C containing 1 or 2 heteroatoms selected from N, O and S. 2-20 Heteroaryl, Ar2 is substituted or unsubstituted C 6-20 Aryl, or Ar1 and Ar2 are each independently a substituted or unsubstituted C containing 1 or 2 heteroatoms selected from N, O and S. 2-20 Heteroaryl.

8. The compound according to claim 1, wherein L1-Ar1 and L2-Ar2 are different.

9. The compound according to claim 1, wherein a+b+c is 0 or 5 or more.

10. The compound according to claim 1, wherein d is 0 or 3 or more.

11. The compound according to claim 1, wherein The compound 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 provided 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 containing the compound is a hole transport layer or an electron suppression layer.

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