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] X1 and X2 are each independently O or S,

[0016] A1 is a benzene ring fused with an adjacent five-membered ring and a benzene ring,

[0017] A2 is a naphthalene ring fused to an adjacent five-membered ring,

[0018] L1 to L3 are each independently a single bond, or a substituted or unsubstituted C 6-60 Arylene,

[0019] Ar is substituted or unsubstituted C 6-60 Aryl; substituted or unsubstituted C containing O or S heteroatom 2-60 or a substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S; 2-60 Heteroaryl,

[0020] R1 and R2 are each independently hydrogen, deuterium, halogen, cyano, or substituted or unsubstituted C 1-60 alkyl,

[0021] a and b are each independently an integer from 0 to 9.

[0022] 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.

[0023] Effects of the Invention

[0024] 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

[0025] 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.

[0026] Figure 2 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 blocking layer 8, a light-emitting layer 4, a hole blocking layer 9, an electron injection and transport layer 5, and a cathode 6 is shown.

[0027] Explanation of symbols

[0028] 1: Substrate 2: Anode

[0029] 3: Hole transport layer 4: Light-emitting layer

[0030] 5: Electron injection and transport layer 6: Cathode

[0031] 7: Hole injection layer 8: Electron blocking layer

[0032] 9: Hole blocking layer DETAILED DESCRIPTION

[0033] In the following, the present invention will be described in more detail to help understanding the present invention.

[0034] (Definition of terms)

[0035] In this manual, and "D" represents a bond to other substituents, and "D" represents deuterium.

[0036] 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, a 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, silyl, C 1-10 Alkyl, C 1-10 Alkoxy and C 6-20 The term "substituted with one or more substituents in an aryl group" may be understood as "substituted with one to the maximum number of replaceable hydrogen atoms". Alternatively, the term "substituted with one or more substituents" may be understood as "substituted with one to five substituents" or "substituted with one or two substituents".

[0037] 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.

[0038]

[0039] 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.

[0040]

[0041] 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.

[0042]

[0043] In this specification, silyl 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 C 6-60 According to one embodiment, Z1, Z2 and Z3 can each independently be hydrogen, deuterium, substituted or unsubstituted C 1-10 Alkyl, substituted or unsubstituted C 1-10 haloalkyl, 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.

[0044] In the present specification, specific examples of the boryl group include trimethylboryl, triethylboryl, tert-butyldimethylboryl, triphenylboryl, and phenylboryl, but are not limited thereto.

[0045] In the present specification, as examples of the halogen group, there are fluorine, chlorine, bromine or iodine.

[0046] 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.

[0047] 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.

[0048] 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.

[0049] 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.

[0050] 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.

[0051] In addition, examples of the spirocyclic hydrocarbon group include spiro[3.4]octyl and spiro[5.5]undecyl, but are not limited to these.

[0052] 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.

[0053] 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.

[0054] 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.

[0055] 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.

[0056] 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 represents a substituent having aromaticity. According to one embodiment, the number of carbon atoms of the heteroaryl group is 2 to 60. According to another embodiment, the number of carbon atoms of the heteroaryl group is 2 to 30. According to another embodiment, the number of carbon atoms of the heteroaryl group is 2 to 20. According to another embodiment, the number of carbon atoms of the heteroaryl group is 2 to 12. According to another embodiment, the number of carbon atoms of the heteroaryl group is 2 to 10. According to another embodiment, the number of carbon atoms of the heteroaryl group is 2 to 8. 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.

[0057] 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.

[0058] 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.

[0059] 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.

[0060] In addition, "unsubstituted or substituted with deuterium" or "substituted or unsubstituted with deuterium" means "unsubstituted or substituted with one to a maximum of substitutable hydrogen atoms being substituted with deuterium". As an example, the term "phenanthryl group unsubstituted or substituted with deuterium" can be understood to mean "phenanthryl group unsubstituted or substituted with one to nine deuterium atoms" when considering that the maximum number of hydrogen atoms that can be substituted with deuterium in the structure of the phenanthryl group is nine.

[0061] In addition, the meaning of "deuterated structure" refers to compounds, divalent linking groups or monovalent substituents including all structures in which at least one hydrogen is replaced by deuterium. As an example, the deuterated structure of phenyl shown below can be understood as referring to all structures in which at least one substitutable hydrogen in phenyl is replaced by deuterium and monovalent substituents.

[0062]

[0063] In addition, the "deuterium substitution rate" or "deuteration degree" of a compound refers to the value calculated as a percentage of the ratio of the number of deuterium substituted in the compound to the total number of hydrogen that can exist (the sum of the number of hydrogen that can be substituted with deuterium in the compound and the number of deuterium substituted). Therefore, the "deuterium substitution rate" or "deuteration degree" of a compound as "K%" means that K% of the hydrogen that can be substituted with deuterium in the compound is substituted with deuterium.

[0064] 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 commonly 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.

[0065] (Compound)

[0066] In another aspect, the present invention provides a compound represented by the above Chemical Formula 1.

[0067] Specifically, the compound represented by the above chemical formula 1 is a tertiary amine compound having two benzonaphthofuran / benzonaphthothiophene substituents, and the above compound has a structure in which one of the benzonaphthofuran / benzonaphthothiophene substituents is connected to the nitrogen atom of the amino group via a benzene ring, and the other of the benzonaphthofuran / benzonaphthothiophene substituents is connected to the nitrogen atom of the amino group via an outer benzene ring of a naphthalene ring. The compound represented by the above chemical formula 1 having the above structure has a superior hole transport capability compared to compounds having different structures and can be used as a hole transport material. In addition, it contributes to the stabilization of excitons and has an excellent energy transfer capability to a dopant, and can therefore also be used as a host material.

[0068] Therefore, the organic light-emitting device using the above compound not only shows a lower driving voltage than the organic light-emitting device using the compound having a structure different from that of the present application, but also can improve efficiency and lifespan characteristics at the same time.

[0069] On the other hand, the above compound can be represented by any one of the following chemical formulas 1A to 1C according to the fusion position of the A1 ring:

[0070] [Chemical Formula 1A]

[0071]

[0072] [Chemical formula 1B]

[0073]

[0074] [Chemical formula 1C]

[0075]

[0076] In the above chemical formulas 1A to 1C,

[0077] L1 is linked to one of the carbon at the *1 position, the carbon at the *2 position, the carbon at the *3 position, and the carbon at the *4 position,

[0078] X1, X2, A2, L1 to L3, Ar, R1, R2, a and b are the same as defined in the above Chemical Formula 1.

[0079] In one specific example, X1 and X2 may both be 0; or

[0080] X1 and X2 can both be S; or

[0081] X1 may be O, X2 may be S; or

[0082] X1 can be S, and X2 can be O.

[0083] in addition, is any one of the substituents represented by the following chemical formulas 2a to 21:

[0084]

[0085] In the above chemical formulae 2a to 21,

[0086] X1, R1 and a are the same as defined in the above Chemical Formula 1.

[0087] in addition, is any one of the substituents represented by the following chemical formulas 3a to 31:

[0088]

[0089] In the above chemical formulae 3a to 31,

[0090] X2, R2 and b are the same as defined in the above Chemical Formula 1.

[0091] In one embodiment, L1 and L2 are each independently a single bond, or a substituted or unsubstituted C 6-20 Arylene.

[0092] In another specific example, L1 and L2 are each independently a single bond; or a C 6-20 Arylene.

[0093] In another specific example, L1 and L2 can each independently be a single bond, or a substituted or unsubstituted C 6-12 Arylene.

[0094] In another specific example, L1 and L2 can each independently be a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenyldiyl group, or a substituted or unsubstituted naphthylene group.

[0095] In another specific example, L1 and L2 are each independently a single bond, a phenylene group, a biphenylene group or a naphthylene group,

[0096] The above-mentioned phenylene group, biphenyldiyl group or naphthylene group may be unsubstituted or substituted with deuterium.

[0097] For example, L1 and L2 can each independently be a single bond, or any one selected from the following groups and their deuterated structures:

[0098]

[0099] More specifically, for example, L1 and L2 may each independently be a single bond, or a substituted or unsubstituted 1,4-phenylene group.

[0100] In another specific example, at least one of L1 and L2 may be a single bond.

[0101] At this time, L1 and L2 may be the same as each other. Alternatively, L1 and L2 may be different.

[0102] For example, L1 and L2 may both be single bonds; or

[0103] L1 can be a single bond, and L2 can be a substituted or unsubstituted C 6-12 an arylene group; or

[0104] L1 can be substituted or unsubstituted C 6-12 In the arylene group, L2 may be a single bond.

[0105] For example, L1 and L2 may both be single bonds; or

[0106] L1 can be a single bond, and L2 can be a substituted or unsubstituted C 6-10 an arylene group; or

[0107] L1 can be substituted or unsubstituted C 6-10 In the arylene group, L2 may be a single bond.

[0108] In another embodiment, L3 can be a single bond, or a substituted or unsubstituted C 6-20 Arylene.

[0109] In another specific example, L3 may be a single bond; or a C 6-20 Arylene.

[0110] In another specific example, L3 may be a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenyldiyl group, or a substituted or unsubstituted naphthylene group.

[0111] For example, L3 may be a single bond, or a substituted or unsubstituted phenylene group.

[0112] In another embodiment, Ar can be substituted or unsubstituted C 6-20 aryl, or substituted or unsubstituted C containing O or S heteroatom 2-20 Heteroaryl.

[0113] In another embodiment, Ar is phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl, or benzonaphthothiophenyl,

[0114] Here, Ar may be substituted or unsubstituted.

[0115] In another embodiment, Ar is phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl, or benzonaphthothiophenyl,

[0116] Ar may be unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, halogen, cyano, phenyl substituted or unsubstituted by deuterium, biphenyl substituted or unsubstituted by deuterium, and naphthyl substituted or unsubstituted by deuterium.

[0117] For example, Ar may be any one selected from the following groups and their deuterated structures, but is not limited thereto:

[0118]

[0119]

[0120] Here, a refers to the number of R1, and when a is 2 or more, the two or more R1 may be the same or different. Specifically, a is 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9.

[0121] In addition, b refers to the number of R2, and when b is 2 or more, the two or more R2 may be the same or different from each other. Specifically, b is 0, 1, 2, 3, 4, 5, 6, 7, 8 or 9.

[0122] For example, R1 and R2 can each independently be hydrogen or deuterium.

[0123] For example, R1 and R2 may both be hydrogen, or both be deuterium.

[0124] In addition, the above compound can be represented by any one of the following chemical formulas 1-1 to 1-9:

[0125] [Chemical formula 1-1]

[0126]

[0127] [Chemical formula 1-2]

[0128]

[0129] [Chemical formula 1-3]

[0130]

[0131] [Chemical formula 1-4]

[0132]

[0133] [Chemical formula 1-5]

[0134]

[0135] [Chemical formula 1-6]

[0136]

[0137] [Chemical formula 1-7]

[0138]

[0139] [Chemical formula 1-8]

[0140]

[0141] [Chemical formula 1-9]

[0142]

[0143] In the above chemical formulas 1-1 to 1-9,

[0144] X1, X2, L1 to L3, Ar, R1, R2, a and b are the same as defined in the above Chemical Formula 1.

[0145] Furthermore, the above-mentioned compound may contain no deuterium, or may contain one or more deuteriums.

[0146] When the compound contains deuterium, the deuterium substitution rate of the compound may be 1% to 100%. Specifically, the deuterium substitution rate of the compound may be 5% or more, 10% or more, 20% or more, 30% or more, 40% or more, 50% or more, 60% or more, 70% or more, 75% or more, 80% or more, or 90% or more and 100% or less.

[0147] As an example, the above compound may contain no deuterium, or may contain 1 to 50 deuteriums. More specifically, the above compound may contain no deuterium, or may contain 1 or more, 2 or more, 3 or more, 4 or more, 5 or more, 6 or more, 7 or more, 8 or more, or 9 or more and 50 or less, 40 or less, 30 or less, 28 or less, 26 or less, 24 or less, 22 or less, 20 or less, 18 or less, 16 or less, 14 or less, 13 or less, 12 or less, 11 or less, or 10 or less deuteriums.

[0148] At this time, when expressing the number of deuterium substitutions in the above compound, it can be represented by the following chemical formula 1D:

[0149] [Chemical formula 1D]

[0150]

[0151] In the above chemical formula 1D,

[0152] Dn means n hydrogens are replaced by deuterium.

[0153] Wherein, n is an integer greater than 0,

[0154] L 1a To L 3a ,Ar a , R 1a and R 2a Each refers to L1 to L3, Ar, R1 and R2 substituents which are not substituted by deuterium.

[0155] On the other hand, representative examples of the compound represented by the above Chemical Formula 1 are shown below:

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184] Among the above compounds,

[0185] Dn means n hydrogens are replaced by deuterium.

[0186] Here, n is an integer greater than or equal to 1.

[0187] On the other hand, as an example, the compound represented by the above Chemical Formula 1 can be produced by the production method shown in the following Reaction Formula 1:

[0188] [Reaction 1]

[0189]

[0190] In the above reaction formula 1, Y is a halogen, preferably bromine or chlorine, and the definitions of other substituents are the same as those described above.

[0191] Specifically, the above compound can be produced by an amine substitution reaction of starting materials A1 and A2. Such an amine substitution reaction is preferably carried out in the presence of a palladium catalyst and a base, and the reactive group used in the above amine substitution reaction can be appropriately changed.

[0192] (Organic Light Emitting Devices)

[0193] 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.

[0194] The organic layer including the compound represented by the above Chemical Formula 1 may be a hole transport layer, an electron blocking layer or a light emitting layer.

[0195] Specifically, the organic layer of the organic light-emitting device of the present invention may be formed of a single-layer structure or 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 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.

[0196] In a specific example, the organic layer may include a light-emitting layer. In this case, the organic layer including the compound may be the light-emitting layer.

[0197] In another specific example, 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, an electron blocking layer or a light-emitting layer.

[0198] In another specific example, the above-mentioned organic layer may include a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting 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, an electron blocking layer or a light-emitting layer.

[0199] In another specific example, the above-mentioned organic layer may include a hole injection layer, a hole transport layer, an electron blocking 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 can be a hole transport layer, an electron blocking layer or a light-emitting layer.

[0200] 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 .

[0201] 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 hole transport layer or the light emitting layer.

[0202] 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 blocking 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, the electron blocking layer or the light-emitting layer.

[0203] 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.

[0204] 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.

[0205] 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.

[0206] 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.

[0207] 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.

[0208] 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.

[0209] 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.

[0210] The hole injection layer is a layer for injecting holes from the electrode. As the hole injection material, the following compounds are preferred: having the ability to transport holes, having the effect of injecting holes from the anode, having an excellent hole injection effect for the light-emitting layer or the light-emitting material, preventing the excitons generated in the light-emitting layer from migrating to the electron injection layer or the electron injection material, and having excellent thin film forming ability. The HOMO (highest occupied molecular orbital) of the hole injection material is preferably between the work function of the anode material and the HOMO of the surrounding organic layer. As specific examples of the hole injection material, there are compounds represented by the above chemical formula 1, metal porphyrin, oligothiophene, arylamine organic matter, hexanitrile hexaazatriphenylene organic matter, quinacridone organic matter, perylene organic matter, anthraquinone and polyaniline and polythiophene conductive polymers, but are not limited thereto.

[0211] 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, or 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.

[0212] The electron blocking layer (electron blocking layer) is a layer formed on the hole transport layer, preferably disposed in contact with the light-emitting layer, and 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 blocking layer includes an electron blocking substance. As an example of such an electron blocking substance, a compound represented by the above chemical formula 1 or an arylamine-based organic substance can be used, but it is not limited thereto.

[0213] 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-hydroxyquinoline aluminum complex (Alq3); 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.

[0214] The light-emitting layer may include a host material and a dopant material. As such a host material, a compound represented by the above chemical formula 1 may be used. In addition, as the host material, in addition to the compound represented by the above chemical formula 1, an aromatic condensed ring derivative or a heterocyclic compound may be included. Specifically, as the aromatic condensed ring derivative, there are anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and as the heterocyclic compound, there are carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds. Pyrimidine derivatives, etc., but are not limited to these.

[0215] 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 a metal complex, there are iridium complexes, platinum complexes, etc., but not limited thereto.

[0216] 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 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.

[0217] 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. Specific examples of electron injection and transport substances include Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free radical compounds, hydroxyflavone-metal complexes, triazine derivatives, etc., but are not limited to these. Alternatively, it can also be combined with fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, Azoles, Oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylene methane, anthrone and the like, and derivatives thereof, metal coordination compounds, or nitrogen-containing five-membered ring derivatives and the like can be used together, but are not limited thereto.

[0218] 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.

[0219] 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.

[0220] 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.

[0221] 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.

[0222] (synthesis example)

[0223] Synthesis example 1

[0224]

[0225] Under nitrogen atmosphere, substance (sub) 1 (15 g, 59.4 mmol), amine 1 (24 g, 62.3 mmol), sodium tert-butoxide (8.6 g, 89 mmol) were added to 300 mL of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, and the organic layer was separated, treated with anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 24.6 g of compound 1 (yield 69%, MS: [M+H] + =603).

[0226] Synthesis example 2

[0227]

[0228] Under nitrogen atmosphere, substance 1 (15 g, 59.4 mmol), amine 2 (24.9 g, 62.3 mmol), sodium tert-butoxide (8.6 g, 89 mmol) were added to 300 mL of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 24.9 g of compound 2 (yield 68%, MS: [M+H] + =617).

[0229] Synthesis example 3

[0230]

[0231] Under nitrogen atmosphere, substance 2 (15 g, 55.8 mmol), amine 3 (26.5 g, 58.6 mmol), sodium tert-butoxide (8 g, 83.7 mmol) were added to 300 mL of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 21.8 g of compound 3 (yield 57%, MS: [M+H] + =685).

[0232] Synthesis example 4

[0233]

[0234] Substance 3 (15 g, 59.4 mmol) and amine 4 (37.1 g, 62.3 mmol) were added to 300 ml of THF, stirred and refluxed. Then, potassium carbonate (24.6 g, 178.1 mmol) was dissolved in 100 ml of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium (0) (0.3 g, 0.6 mmol) was added. After reacting for 5 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 dissolved in chloroform again, 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 purified by silica gel column chromatography to produce 32.8 g of compound 4 (yield 72%, MS: [M+H] + =769).

[0235] Synthesis example 5

[0236]

[0237] Under nitrogen atmosphere, substance 3 (15 g, 59.4 mmol), amine 5 (28.8 g, 62.3 mmol), sodium tert-butoxide (8.6 g, 89 mmol) were added to 300 mL of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 25.3 g of compound 5 (yield 63%, MS: [M+H] + =679).

[0238] Synthesis example 6

[0239]

[0240] Substance 4 (15 g, 59.4 mmol) and amine 6 (36.2 g, 62.3 mmol) were added to 300 ml of THF, stirred and refluxed. Then, potassium carbonate (24.6 g, 178.1 mmol) was dissolved in 100 ml of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 4 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 dissolved in chloroform again, 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 purified by silica gel column chromatography to produce 31.8 g of compound 6 (yield 71%, MS: [M+H] + =755).

[0241] Synthesis Example 7

[0242]

[0243] Under nitrogen atmosphere, substance 5 (15 g, 59.4 mmol), amine 7 (28.6 g, 62.3 mmol), sodium tert-butoxide (8.6 g, 89 mmol) were added to 300 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 20.9 g of compound 7 (yield 52%, MS: [M+H] + =677).

[0244] Synthesis example 8

[0245]

[0246] Under nitrogen atmosphere, substance 5 (15 g, 59.4 mmol), amine 8 (24 g, 62.3 mmol), sodium tert-butoxide (8.6 g, 89 mmol) were added to 300 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 25 g of compound 8 (yield 70%, MS: [M+H] + =603).

[0247] Synthesis example 9

[0248]

[0249] Under nitrogen atmosphere, substance 5 (15 g, 59.4 mmol), amine 9 (24 g, 62.3 mmol), sodium tert-butoxide (8.6 g, 89 mmol) were added to 300 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 20.4 g of compound 9 (yield 57%, MS: [M+H] + =603).

[0250] Synthesis example 10

[0251]

[0252] Substance 6 (15 g, 59.4 mmol) and amine 10 (34.6 g, 62.3 mmol) were added to 300 ml of THF, stirred and refluxed. Then, potassium carbonate (24.6 g, 178.1 mmol) was dissolved in 100 ml of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 6 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 dissolved in chloroform again, 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 purified by silica gel column chromatography to produce 26.4 g of compound 10 (yield 61%, MS: [M+H] + =729).

[0253] Synthesis example 11

[0254]

[0255] Under nitrogen atmosphere, substance 6 (15 g, 59.4 mmol), amine 11 (24 g, 62.3 mmol), sodium tert-butoxide (8.6 g, 89 mmol) were added to 300 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 18.9 g of compound 11 (yield 53%, MS: [M+H] + =603).

[0256] Synthesis example 12

[0257]

[0258] Under nitrogen atmosphere, substance 6 (15 g, 59.4 mmol), amine 9 (24 g, 62.3 mmol), sodium tert-butoxide (8.6 g, 89 mmol) were added to 300 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 22.9 g of compound 12 (yield 64%, MS: [M+H] + =603).

[0259] Synthesis example 13

[0260]

[0261] Under nitrogen atmosphere, substance 6 (15 g, 59.4 mmol), amine 12 (24 g, 62.3 mmol), sodium tert-butoxide (8.6 g, 89 mmol) were added to 300 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 22.5 g of compound 13 (yield 63%, MS: [M+H] + =603).

[0262] Synthesis example 14

[0263]

[0264] Under nitrogen atmosphere, substance 6 (15 g, 59.4 mmol), amine 13 (24 g, 62.3 mmol), sodium tert-butoxide (8.6 g, 89 mmol) were added to 300 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 24.6 g of compound 14 (yield 69%, MS: [M+H] + =603).

[0265] Synthesis Example 15

[0266]

[0267] Under nitrogen atmosphere, substance 6 (15 g, 59.4 mmol), amine 14 (24 g, 62.3 mmol), sodium tert-butoxide (8.6 g, 89 mmol) were added to 300 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 21.1 g of compound 15 (yield 59%, MS: [M+H] + =603).

[0268] Synthesis Example 16

[0269]

[0270] Under nitrogen atmosphere, substance 6 (15 g, 59.4 mmol), amine 15 (24.9 g, 62.3 mmol), sodium tert-butoxide (8.6 g, 89 mmol) were added to 300 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 19.4 g of compound 16 (yield 53%, MS: [M+H] + =617).

[0271] Synthesis Example 17

[0272]

[0273] Substance 6 (15 g, 59.4 mmol) and amine 16 (31.5 g, 62.3 mmol) were added to 300 ml of THF, stirred and refluxed. Then, potassium carbonate (24.6 g, 178.1 mmol) was dissolved in 100 ml of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After reacting for 6 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 dissolved in chloroform again, 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 purified by silica gel column chromatography to produce 29.8 g of compound 17 (yield 69%, MS: [M+H] + =729).

[0274] Synthesis Example 18

[0275]

[0276] Substance 7 (15 g, 59.4 mmol) and amine 17 (37.1 g, 62.3 mmol) were added to 300 ml of THF, stirred and refluxed. Then, potassium carbonate (24.6 g, 178.1 mmol) was dissolved in 100 ml of water and added. After sufficient stirring, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 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 dissolved in chloroform again, 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 purified by silica gel column chromatography to produce 30.6 g of compound 18 (yield 76%, MS: [M+H] + =679).

[0277] Synthesis example 19

[0278]

[0279] Under nitrogen atmosphere, substance 7 (15 g, 59.4 mmol), amine 18 (25 g, 62.3 mmol), sodium tert-butoxide (8.6 g, 89 mmol) were added to 300 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 22.7 g of compound 19 (yield 62%, MS: [M+H] + =619).

[0280] Synthesis example 20

[0281]

[0282] Under nitrogen atmosphere, substance 7 (15 g, 59.4 mmol), amine 12 (24 g, 62.3 mmol), sodium tert-butoxide (8.6 g, 89 mmol) were added to 300 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 17.9 g of compound 20 (yield 50%, MS: [M+H] + =603).

[0283] Synthesis Example 21

[0284]

[0285] Under nitrogen atmosphere, substance 7 (15 g, 59.4 mmol), amine 19 (24.9 g, 62.3 mmol), sodium tert-butoxide (8.6 g, 89 mmol) were added to 300 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.3 g, 0.6 mmol) was added. After 5 hours, the reaction was completed, cooled to room temperature, and the solvent was removed under reduced pressure. Then, the compound was completely dissolved in chloroform again, washed with water twice, the organic layer was separated, filtered after treatment with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to obtain 19 g of compound 21 (yield 52%, MS: [M+H] + =617).

[0286] Synthesis example 22

[0287]

[0288] In a shaking tube, compound 3 (10 g, 14.6 mmol), PtO2 (1 g, 4.4 mmol), and 73 ml of D2O were added, and the tube was sealed and heated at 250°C and 600 psi for 12 hours. When the reaction was completed, chloroform was added, and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO4, concentrated, and the sample was purified by silica gel column chromatography to produce 5.1 g of compound 22 (yield 50%, MW = 701).

[0289] Synthesis example 23

[0290]

[0291] In a shaking tube, compound 11 (10 g, 16.6 mmol), PtO2 (1.1 g, 5 mmol), and 83 ml of D2O were added, and the tube was sealed and heated at 250°C and 600 psi for 12 hours. When the reaction was completed, chloroform was added, and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO4, concentrated, and the sample was purified by silica gel column chromatography to produce 4.9 g of compound 23 (yield 48%, MW = 618).

[0292] Synthesis example 24

[0293]

[0294] In a shaking tube, compound 12 (10 g, 16.6 mmol), PtO2 (1.1 g, 5 mmol), and 83 ml of D2O were added, and the tube was sealed and heated at 250°C and 600 psi for 12 hours. When the reaction was completed, chloroform was added and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO4 and concentrated, and the sample was purified by silica gel column chromatography to produce 5.4 g of compound 24 (yield 53%, MW = 619).

[0295] Synthesis example 25

[0296]

[0297] In a shaking tube, compound 13 (10 g, 16.6 mmol), PtO2 (1.1 g, 5 mmol), and 83 ml of D2O were added, and the tube was sealed and heated at 250°C and 600 psi for 12 hours. When the reaction was completed, chloroform was added, and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO4, concentrated, and the sample was purified by silica gel column chromatography to produce 5 g of compound 25 (yield 49%, MW = 621).

[0298] Synthesis Example 26

[0299]

[0300] In a shaking tube, compound 17 (10 g, 13.7 mmol), PtO2 (0.9 g, 4.1 mmol), and 69 ml of D2O were added, and the tube was sealed and heated at 250°C and 600 psi for 12 hours. When the reaction was completed, chloroform was added, and the reaction solution was transferred to a separatory funnel for extraction. The extract was dried over MgSO4, concentrated, and the sample was purified by silica gel column chromatography to produce 4.9 g of compound 26 (yield 48%, MW = 743).

[0301] (Examples and Comparative Examples)

[0302] Example 1

[0303] 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.

[0304] On the ITO transparent electrode prepared in this way, as a hole injection layer, the following HI-1 compound was added in the form of The following PD compound was p-doped at a concentration of 1.5%. On the hole injection layer, the following HT-1 compound was vacuum-deposited to form a film with a thickness of Next, on the hole transport layer, a layer with a film thickness of The following EB-1 compound was vacuum-deposited to form an electron blocking layer (electron blocking layer).

[0305] Next, on the EB-1 vapor-deposited film, the RH-1 compound as the first host compound, the compound 1 prepared in the above Synthesis Example 1 as the second host compound, and the following RD compound were vacuum-deposited at a weight ratio of 49:49:2 to form Thickness of the red emitting layer.

[0306] On the above-mentioned light-emitting layer, the film thickness is The following HB-1 compound was vacuum-deposited to form a hole blocking layer. Next, the following ET-1 compound and the following LiQ compound were vacuum-deposited at a weight ratio of 2:1 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 .

[0307]

[0308] In the above process, the evaporation rate of organic matter is maintained Lithium fluoride at the 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.

[0309] Examples 2 to 26

[0310] An organic light-emitting device was produced by the same method as in Example 1, except that the compounds listed in Table 1 below were used instead of Compound 1 as the second host compound of the light-emitting layer.

[0311] Comparative Examples 1 to 9

[0312] An organic light-emitting device was prepared by the same method as in Example 1, except that compounds C1 to C9 shown in Table 1 below were used as the second host compound of the light-emitting layer instead of compound 1. Compounds C1 to C9 are shown below.

[0313]

[0314] (Experimental example)

[0315] Current was applied to the organic light emitting devices prepared in Examples 1 to 26 and Comparative Examples 1 to 9, and voltage, efficiency and lifetime were measured. The results are shown in Table 1. T95 is the time required for the luminance to decrease from the initial luminance to 95%.

[0316]

Table 1

[0317]

[0318] As shown in Table 1, it can be confirmed that the organic light-emitting device of the embodiment using the compound represented by Chemical Formula 1 as the host material of the light-emitting layer shows excellent performance in terms of efficiency and life compared with the organic light-emitting device of the comparative example using a compound having a different structure.

[0319] As described above, it was confirmed that the compound of the present invention exhibits superior characteristics in terms of efficiency and lifespan, depending on the position of the substituent and the type of the substituent, compared with the comparative example compound.

Claims

1. A compound represented by the following chemical formula 1: [Chemical formula 1] In the chemical formula 1, X1 and X2 are each independently O or S, A1 is a benzene ring fused with an adjacent five-membered ring and a benzene ring, A2 is a naphthalene ring fused to an adjacent five-membered ring, L1 to L3 are each independently a single bond, or a substituted or unsubstituted C 6-60 Arylene, Ar is substituted or unsubstituted C 6-60 Aryl; substituted or unsubstituted C containing O or S heteroatom 2-60 or a substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S; 2-60 Heteroaryl, R1 and R2 are each independently hydrogen, deuterium, halogen, cyano, or substituted or unsubstituted C 1-60 alkyl, a and b are each independently an integer from 0 to 9.

2. The compound according to claim 1, wherein X1 and X2 are both O; or X1 and X2 are both S; or X1 is O, X2 is S; or X1 is S and X2 is O.

3. The compound according to claim 1, wherein is any one of the substituents represented by the following chemical formulas 2a to 21: In the chemical formulae 2a to 21, X1, R1 and a are the same as defined in claim 1.

4. The compound according to claim 1, wherein is any one of the substituents represented by the following chemical formulas 3a to 31: In the chemical formulae 3a to 31, X2, R2 and b are the same as defined in claim 1.

5. The compound according to claim 1, wherein L1 and L2 are each independently a single bond, or a substituted or unsubstituted C 6-12 Arylene.

6. The compound according to claim 5, wherein L1 and L2 are both single bonds; or L1 is a single bond, L2 is a substituted or unsubstituted C 6-12 an arylene group; or L1 is substituted or unsubstituted C 6-12 Arylene group, L2 is a single bond.

7. The compound according to claim 1, wherein L3 is a single bond or a substituted or unsubstituted phenylene group.

8. The compound according to claim 1, wherein Ar is substituted or unsubstituted C 6-20 aryl, or substituted or unsubstituted C containing O or S heteroatom 2-20 Heteroaryl.

9. The compound according to claim 1, wherein Ar is phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, dibenzofuranyl, dibenzothiophenyl, benzonaphthofuranyl, or benzonaphthothiophenyl, Ar is unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, halogen, cyano, phenyl substituted or unsubstituted by deuterium, biphenyl substituted or unsubstituted by deuterium, and naphthyl substituted or unsubstituted by deuterium.

10. The compound according to claim 1, wherein R1 and R2 are each independently hydrogen or deuterium.

11. The compound according to claim 1, wherein The compound is represented by any one of the following chemical formulas 1-1 to 1-9: [Chemical formula 1-1] [Chemical formula 1-2] [Chemical formula 1-3] [Chemical formula 1-4] [Chemical formula 1-5] [Chemical formula 1-6] [Chemical formula 1-7] [Chemical formula 1-8] [Chemical formula 1-9] In the chemical formulas 1-1 to 1-9, X1, X2, L1 to L3, Ar, R1, R2, a and b are the same as defined in claim 1.

12. The compound according to claim 1, wherein The compound is any one selected from the following compounds: In the compound, Dn means n hydrogens are replaced by deuterium. Here, n is an integer greater than or equal to 1.

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

14. The organic light emitting device according to claim 13, wherein: The organic layer containing the compound is a hole transport layer, an electron blocking layer or a light emitting layer.

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