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] A compound represented by the following Chemical Formula 1.

[0013] [Chemical formula 1]

[0014]

[0015] In the above chemical formula 1,

[0016] Y is O or S,

[0017] R1 to R4 are each independently hydrogen; deuterium; substituted or unsubstituted C 6-60 Aryl; or a substituted or unsubstituted C containing any one or more heteroatoms selected from N, O and S 2-60 Heteroaryl,

[0018] a and b are each independently an integer from 1 to 3,

[0019] c and d are each independently an integer from 1 to 4,

[0020] e and f are each independently an integer from 1 to 2,

[0021] At least one of R3 or R4 is deuterium,

[0022] L1 is a direct bond; substituted or unsubstituted C 6-60 or a substituted or unsubstituted C containing any one or more heteroatoms selected from N, O and S 2-60 Heteroarylene,

[0023] L2 is phenylene, biphenylene, (diphenyl)phenylene, anthracene, 9,9-dimethylfluorenylene, dibenzothienylene or triphenylene,

[0024] The above L2 is substituted with one or more deuterium or is unsubstituted,

[0025] Ar1 and Ar2 are each independently substituted or unsubstituted C 6-60 Aryl; or a substituted or unsubstituted C containing any one or more heteroatoms selected from N, O and S 2-60 Heteroaryl.

[0026] 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.

[0027] Effects of the Invention

[0028] The compound represented by the above chemical formula 1 can be used as a material for an organic layer of an organic light-emitting device, in which improved efficiency, lower driving voltage and / or improved life characteristics can be achieved. In particular, the compound represented by the above chemical formula 1 can be used as a material for hole injection, hole transport, hole injection and transport, electron blocking, luminescence, electron transport, hole blocking, electron injection, or electron transport and injection. BRIEF DESCRIPTION OF THE DRAWINGS

[0029] Figure 1The figure shows an example of an organic light-emitting device composed of a substrate 1 , an anode 2 , a light-emitting layer 3 , and a cathode 4 .

[0030] Figure 2 An example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light-emitting layer 3, a hole blocking layer 8, an electron transport and injection layer 9, and a cathode 4 is shown.

[0031] Explanation of symbols

[0032] 1: Substrate 2: Anode

[0033] 3: Light-emitting layer 4: Cathode

[0034] 5: Hole injection layer 6: Hole transport layer

[0035] 7: Electron blocking layer 8: Hole blocking layer

[0036] 9: Electron transport and injection layer DETAILED DESCRIPTION

[0037] In the following, the present invention will be described in more detail to help understanding the present invention.

[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 nitrile 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. That is, for example, it can mean substituted or unsubstituted with one or more deuterium. 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 selected from deuterium, halogen, C 1-10 Alkyl, C 1-10 Alkoxy and C 6-20In the present specification, the term “substituted by one or more substituents” may be understood as meaning, for example, “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, 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, as examples of the halogen group, there are fluorine, chlorine, bromine or iodine.

[0048] 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, the number of carbon atoms in the alkyl group is 1 to 6. 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-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, and 5-methylhexyl, but are not limited thereto.

[0049] 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.

[0050] In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, there are cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, etc., but are not limited thereto.

[0051] In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the carbon number of the aryl group is 6 to 30. According to one embodiment, the carbon number of the aryl group is 6 to 20. Regarding the aryl group, as a monocyclic aryl group, it may be phenyl, biphenyl, terphenyl, etc., but it is not limited thereto. As the polycyclic aryl group, it may be naphthyl, anthracenyl, phenanthrenyl, pyrenyl, peryl, phenylene, fluorenyl, triphenylene, etc., but are not limited to these.

[0052] 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.

[0053] In the present specification, the heterocyclic group is a heterocyclic group containing one or more of O, N, Si and S as hetero elements, and the number of carbon atoms is not particularly limited, but preferably the number of carbon atoms is 2 to 60. Examples of the heterocyclic group include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, Azolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, benzo oxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothiophenyl, dibenzothiophenyl, benzofuranyl, phenanthroline, isothiophene oxazolyl, thiadiazolyl, phenothiazinyl and dibenzofuranyl, but are not limited thereto.

[0054] In the present specification, the aryl group in aralkyl, aralkenyl, alkylaryl, and arylamine is the same as the examples of the aryl group described above. In the present specification, the alkyl group in aralkyl, alkylaryl, and alkylamine is the same as the examples of the alkyl group described above. In the present specification, the heteroaryl group in heteroarylamine can be applied to the above-mentioned description of the heterocyclic group. In the present specification, the alkenyl group in aralkenyl is the same as the examples of the alkenyl group described above. In the present specification, the arylene group is a divalent group, and the above-mentioned description of the aryl group can be applied. In the present specification, the heteroarylene group is a divalent group, and the above-mentioned description of the heterocyclic group can be applied. In the present specification, the hydrocarbon ring is not a monovalent group, but two substituents are combined, and the above-mentioned description of the aryl group or cycloalkyl group can be applied. In the present specification, the heterocycle is not a monovalent group, but two substituents are combined, and the above-mentioned description of the heterocyclic group can be applied.

[0055] 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.

[0056] In addition, “substituted or unsubstituted with deuterium” means “one to a maximum number of substitutable hydrogen atoms are substituted or unsubstituted with deuterium”. As an example, the term “naphthalene substituted or unsubstituted with deuterium” can be understood to mean “naphthalene substituted or unsubstituted with one to eight deuterium atoms” when considering that the maximum number of hydrogen atoms that can be substituted with deuterium in the naphthalene structure is eight.

[0057] 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 monovalent substituents in which at least one hydrogen that can be replaced in phenyl is replaced by deuterium.

[0058]

[0059] In addition, the "deuterium substitution rate" or "deuteration degree" of a compound refers to the value calculated as a percentage of the ratio of the number of deuterium substituted in the compound to the total number of hydrogens that can exist (the sum of the number of hydrogens that can be replaced by deuterium in the compound and the number of deuteriums that have been replaced). Therefore, the "deuterium substitution rate" or "deuteration degree" of a compound as "K%" means that K% of the hydrogens that can be replaced by deuterium in the compound are replaced by deuterium.

[0060] In this case, the above-mentioned "deuterium substitution rate" or "deuteration degree" can be measured by MALDI-TOF MS (Matrix-Assisted Laser Desorption / Ionization Time-of-Flight Mass Spectrometer), nuclear magnetic resonance spectroscopy ( 1 H NMR), TLC / MS (Thin-Layer Chromatography / Mass Spectrometry), or GC / MS (Gas Chromatography / Mass Spectrometry), etc., and are measured according to generally known methods. More specifically, when MALDI-TOF MS is used, the above-mentioned "deuterium substitution rate" or "deuteration degree" can be determined by analyzing the number of deuterium substituted in the compound through MALDI-TOF MS, and then calculating the ratio of the number of deuterium substituted in the compound to the total number of hydrogen that can exist as a percentage.

[0061] (Compound)

[0062] The present invention provides a compound represented by the above Chemical Formula 1.

[0063] R1 to R4 are each independently hydrogen; deuterium; substituted or unsubstituted C 6-60 Aryl; or a substituted or unsubstituted C containing any one or more heteroatoms selected from N, O and S 2-60 In the heteroaryl group, at least one of R3 and R4 is deuterium.

[0064] Specifically, R1 and R2 can each independently be hydrogen or deuterium.

[0065] In addition, R3 and R4 can each independently be hydrogen, deuterium, phenyl, biphenyl or terphenyl. When R3 or R4 is phenyl, biphenyl or terphenyl, the phenyl, biphenyl or terphenyl can be substituted or unsubstituted with one or more deuteriums, and at least one of R3 or R4 is deuterium.

[0066] a and b may each independently be an integer from 1 to 3, c and d may each independently be an integer from 1 to 4. e and f may each independently be an integer from 1 to 2.

[0067] L1 is a direct bond; substituted or unsubstituted C 6-60 or a substituted or unsubstituted C containing any one or more heteroatoms selected from N, O and S 2-60 Heteroarylene.

[0068] Specifically, L1 is a direct bond, a phenylene group, a biphenylene group, a naphthylene group, a dibenzofuranyl group or a dibenzothiophenylene group. When L1 is a phenylene group, a biphenylene group, a naphthylene group, a dibenzofuranyl group or a dibenzothiophenylene group, the above-mentioned phenylene group, biphenylene group, naphthylene group, a dibenzofuranyl group or a dibenzothiophenylene group may be substituted or unsubstituted by one or more deuterium or phenyl groups.

[0069] Specifically, L1 may be a direct bond or any of the linking groups shown below.

[0070]

[0071] The above-mentioned linking group may be substituted with one or more deuterium or may be unsubstituted.

[0072] Ar1 and Ar2 are each independently substituted or unsubstituted C 6-60 Aryl; or a substituted or unsubstituted C containing any one or more heteroatoms selected from N, O and S 2-60 Heteroaryl.

[0073] Specifically, Ar1 and Ar2 are each independently phenyl, biphenyl, terphenyl, naphthyl, dibenzofuranyl, dibenzothienyl or 9,9-dimethylfluorenyl, wherein Ar1 and Ar2 may be substituted with one or more deuterium or may be unsubstituted.

[0074] It can be any one selected from the following groups:

[0075]

[0076] The definitions of Y, R1 and R2 are the same as those in Chemical Formula 1.

[0077] L2 is phenylene, biphenylene, (diphenyl)phenylene, anthracene, 9,9-dimethylfluorenylene, dibenzothienylene or triphenylene,

[0078] The above L2 may be substituted with one or more deuterium or may not be substituted.

[0079] However, the "biphenylene" in L2 above may refer to (wherein D is deuterium and k is each independently an integer from 0 to 4).

[0080] Specifically, L2 can be any one of the following linking groups:

[0081]

[0082]

[0083] The above substituents It may be any of the following substituents:

[0084] R3 and R4 have the same meanings as in Chemical Formula 1.

[0085] The compound represented by the above Chemical Formula 1 is a compound represented by one of the group consisting of the following compounds.

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123] In addition, the above-mentioned compound may contain no deuterium, or may contain one or more deuterium.

[0124] When the above compound contains deuterium, the deuterium substitution rate of the compound can be 1% to 100%. Specifically, the deuterium substitution rate of the above compound can be 5% or more, 10% or more, 20% or more, 25% or more, 30% or more, 40% or more, or 50% or more and 100% or less, 90% or less, 80% or less, or 70% or less.

[0125] As an example, the compound may not contain deuterium, or may contain 1 to 40 deuteriums. Specifically, when the compound contains deuterium, the compound may contain 1 or more, 3 or more, 5 or more, 6 or more, 7 or more, 8 or more, 10 or more, 11 or more, 12 or more, 15 or more, 18 or more, 20 or more, 22 or more, or 25 or more and 40 or less, 38 or less, 36 or less, 34 or less, 32 or less, 30 or less, 28 or less, or 26 or less of deuterium.

[0126] In addition, the present invention provides a method for producing the compound represented by the above Chemical Formula 1 as shown in the following Reaction Formula 1.

[0127] [Reaction 1]

[0128]

[0129] In the above Reaction Formula 1, the definitions of L1, L2, Ar1, Ar2, R1 to R4, Y and a to f are the same as those in Chemical Formula 1.

[0130] Step 1 of the above reaction formula is a Suzuki coupling reaction, preferably carried out in the presence of a palladium catalyst, and the reactive group for the Suzuki coupling reaction can be changed according to a technique known in the art. Step 2 is carried out under alkaline conditions, and the base can preferably be cesium carbonate, which can be changed according to a technique known in the art. The above-mentioned production method can be more specifically described in the production examples and synthesis examples described later.

[0131] (Organic Light Emitting Devices)

[0132] In addition, the present invention provides an organic light-emitting device including the compound represented by the above chemical formula 1. As an example, the present invention provides an organic light-emitting device, which includes: a first electrode, a second electrode disposed opposite to the above first electrode, and one or more organic layers disposed between the above first electrode and the above second electrode, wherein one or more of the organic layers includes the compound represented by the above chemical formula 1.

[0133] The organic layer of the organic light-emitting device of the present invention may be formed by 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. 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 injection and transport layer as organic layers.

[0134] In addition, the organic layer may include a light-emitting layer, and the light-emitting layer includes the compound represented by the chemical formula 1. In particular, the compound according to the present invention may be used as a host of the light-emitting layer. In particular, the compound according to the present invention may be used as a green host of the light-emitting layer.

[0135] In addition, the organic layer may include a light emitting layer, an electron transport layer, or an electron injection layer. The light emitting layer, the electron transport layer, or the electron injection layer may include the compound represented by Chemical Formula 1.

[0136] In addition, the light emitting layer, the electron transport layer, the electron injection layer, or the layer that simultaneously transports and injects electrons may include the compound represented by Chemical Formula 1.

[0137] In addition, the organic layer includes a light emitting layer, an electron blocking layer, and an electron transport and injection layer. The light emitting layer or the electron transport and injection layer may include the compound represented by Chemical Formula 1.

[0138] In addition, the organic layer includes a light emitting layer, a hole injection layer, a hole transport layer and a hole blocking layer. The light emitting layer, the hole injection layer, the hole transport layer or the hole blocking layer may contain the compound represented by the chemical formula 1.

[0139] In addition, the organic light-emitting device according to the present invention may be an organic light-emitting device having a structure (normal type) in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate. In addition, the organic light-emitting device according to the present invention may be an organic light-emitting device having an inverse structure (inverted type) in which a cathode, one or more organic layers, and an anode are sequentially stacked on a substrate. For example, the structure of an organic light-emitting device according to one embodiment of the present invention is shown in FIG. Figure 1 and 2 .

[0140] Figure 1 The figure shows an example of an organic light emitting device composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4. In the above structure, the compound represented by the above Chemical Formula 1 may be contained in the above light emitting layer.

[0141] Figure 2 The diagram shows an example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light-emitting layer 3, a hole blocking layer 8, an electron transport and injection layer 9, and a cathode 4. In the structure described above, the compound represented by the above chemical formula 1 may be contained in one or more of the above hole injection layer, hole transport layer, light-emitting layer, and electron transport layer.

[0142] 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.

[0143] 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.

[0144] 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.

[0145] 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.

[0146] 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.

[0147] 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.

[0148] 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.

[0149] 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.

[0150] The hole transport layer is a layer that receives holes from the hole injection layer and transfers the holes to the light-emitting layer. The hole transport material is a material that can receive holes from the anode or the hole injection layer and transfer them to the light-emitting layer. Materials with high hole mobility are suitable. Specific examples include arylamine organic substances, conductive polymers, and block copolymers having both conjugated and non-conjugated parts, but are not limited thereto.

[0151] The electron blocking layer is a layer placed between the hole transport layer and the light-emitting layer to prevent the electrons injected from the cathode from being transferred to the hole transport layer without being recombined in the light-emitting layer, and is also called an electron suppression layer. In the electron blocking layer, it is preferred to use a substance with a lower electrophilicity than the electron transport layer. The electron blocking layer includes an electron blocking substance, and as an example of such an electron blocking substance, an arylamine-based organic substance can be used, but it is not limited thereto.

[0152] The luminescent material is a material that can receive holes and electrons from the hole transport layer and the electron transport layer respectively and combine them to emit light in the visible light region, and is preferably a material with high quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq3); carbazole compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo Compounds of the oxazole, benzothiazole and benzimidazole series; poly(p-phenylene vinylene) (PPV) series polymers; spiro compounds; polyfluorene, rubrene, etc., but are not limited to these.

[0153] The above-mentioned light-emitting layer may include a host material and a dopant material. The host material includes an aromatic fused ring derivative or a heterocyclic compound. Specifically, as an aromatic fused ring derivative, there are anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., as heterocyclic compounds, there are carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, etc. Pyrimidine derivatives, etc., but are not limited to these.

[0154] 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.

[0155] The hole blocking layer is a layer that prevents holes from reaching the cathode and can usually be formed using the same conditions as the hole injection layer. Examples of the compound include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, and aluminum complexes.

[0156] The electron transport layer is a layer that receives electrons from the electron injection layer and transfers the electrons to the light-emitting layer. The electron transport material is a material that can well receive electrons from the cathode and transfer them to the light-emitting layer. Materials with large electron mobility are suitable. As specific examples, there are Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free radical compounds, hydroxyflavone-metal complexes, etc., but are not limited to these. The electron transport layer can be used with any desired cathode material as used in the prior art. In particular, examples of suitable cathode materials are common materials with low work function and accompanied by an aluminum layer or a silver layer. Specifically, cesium, barium, calcium, ytterbium and samarium, in each case accompanied by an aluminum layer or a silver layer.

[0157] The electron injection layer is a layer for injecting electrons from the electrode, and preferably uses the following compounds: compounds that have the ability to transport electrons, have the effect of injecting electrons from the cathode, have an excellent electron injection effect on the light-emitting layer or the light-emitting material, prevent the excitons generated in the light-emitting layer from migrating to the hole injection layer, and have excellent thin film forming ability. Specifically, there are fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, Azoles, Examples include, but are not limited to, diazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylene methane, anthrone, and derivatives thereof, metal coordination compounds, and nitrogen-containing five-membered ring derivatives.

[0158] 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-quinoline) gallium chloride, bis(2-methyl-8-quinoline)(o-cresol) gallium, bis(2-methyl-8-quinoline)(1-naphthol) aluminum, and bis(2-methyl-8-quinoline)(2-naphthol) gallium.

[0159] On the other hand, in the present invention, the "electron transport and injection layer" is a layer that plays the role of both the above-mentioned electron transport layer and the above-mentioned electron injection layer, and the substances that play the role of the above-mentioned layers can be used alone or in combination, but are not limited to this. Preferably, the compound represented by the above-mentioned chemical formula 1 can be included as the substance of the electron transport and injection layer.

[0160] 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.

[0161] 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.

[0162] 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.

[0163] [Synthesis example]

[0164] Synthesis Example 1: Synthesis of Compound 1

[0165]

[0166] (Synthesis of Intermediate 1-1)

[0167] Under nitrogen atmosphere, 1-bromo-6-chlorodibenzo[b,d]furan (33.5 g, 119 mmol) and bis(pinacolato)diboron (30.5 g, 130.9 mmol) were added to dibromo[b,d]furan. Diox (670ml), stirred and refluxed. Then, potassium acetate (34.3g, 357mmol) was added, and after sufficient stirring, [1,1'-Bis(diphenyl phosphino)ferrocene]dichloropalladium(II) (2.6g, 3.6mmol) was added. After reacting for 7 hours, the mixture was cooled to room temperature, and the organic layer was filtered to remove the salt, and the filtered organic layer was distilled. It was added to chloroform (391ml) again to dissolve, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, and the mixture was filtered after stirring. The filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to produce a gray solid compound 1-1 (34g, yield: 87%, MS: [M+H] + =329.6).

[0168] (Synthesis of Intermediate 1-2)

[0169] Under nitrogen atmosphere, compound 1-1 (37 g, 112.6 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (30.1 g, 112.6 mmol) were added to THF (740 ml), stirred and refluxed. Then, potassium carbonate (46.7 g, 337.8 mmol) was dissolved in water (47 ml) and added. After sufficient stirring, tetrakis (triphenylphosphine) palladium (0) (3.9 g, 3.4 mmol) was added. After reacting for 8 hours, the mixture was cooled to room temperature and the generated solid was filtered. The solid was added to chloroform (1466 ml) and dissolved. After washing with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce a yellow solid compound 1-2 (34.2 g, yield: 70%, MS: [M+H] + =434.9).

[0170] (Synthesis of Intermediate 1-3)

[0171] Under nitrogen atmosphere, compound 1-2 (34.2 g, 78.8 mmol) and bis(pinacolato)diboron (22 g, 86.7 mmol) were added to distilled water. oxane (684 ml), stirred and refluxed. Then, potassium acetate (22.7 g, 236.5 mmol) was added, and after sufficient stirring, [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (1.7 g, 2.4 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, and the organic layer was filtered to remove the salt, and the filtered organic layer was distilled. It was again added to chloroform (414 ml) and dissolved. After washing with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was filtered after stirring. The filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to produce a gray solid compound 1-3 (28.2 g, yield: 68%, MS: [M+H] + =526.4).

[0172] (Synthesis of Intermediate 1-4)

[0173] Under nitrogen atmosphere, compound 1-3 (28.2 g, 53.7 mmol) and 1-chloro-2-fluorobenzene (7 g, 53.7 mmol) were added to THF (564 ml), stirred and refluxed. Then, potassium carbonate (22.3 g, 161 mmol) was dissolved in water (22 ml) and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium (0) (1.9 g, 1.6 mmol) was added. After reacting for 8 hours, the mixture was cooled to room temperature and the generated solid was filtered. The solid was added to chloroform (795 ml) and dissolved. After washing with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce a white solid compound 1-4 (16.7 g, yield: 63%, MS: [M+H] + =494.5).

[0174] (Synthesis of Compound 1)

[0175] Under nitrogen atmosphere, compound 1-4 (16.7 g, 33.8 mmol) and 9H-carbazole-1,3,4,5,6,8-d6 (5.9 g, 33.8 mmol) were added to dimethylformamide (334 ml), stirred and refluxed. Then, cesium carbonate (33.1 g, 101.5 mmol) was added, stirred thoroughly, reacted for 3 hours, cooled to room temperature, and the generated solid was filtered. The solid was added to toluene (657 ml) and dissolved, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from toluene and ethyl acetate to produce a white solid compound 1 (11.4 g, yield: 52%, MS: [M+H] + =647.8).

[0176] Synthesis Example 2: Synthesis of Compound 2

[0177]

[0178] (Synthesis of Intermediate 2-1)

[0179] Under nitrogen atmosphere, compound 1-3 (40 g, 76.1 mmol) and 1-chloro-3-fluorobenzene (9.9 g, 76.1 mmol) were added to THF (800 ml), stirred and refluxed. Then, potassium carbonate (31.6 g, 228.4 mmol) was dissolved in water (32 ml) and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium (0) (2.6 g, 2.3 mmol) was added. After reacting for 5 hours, the mixture was cooled to room temperature and the generated solid was filtered. The solid was dissolved in chloroform (1127 ml), washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce a white solid compound 2-1 (23.7 g, yield: 63%, MS: [M+H] + =494.5).

[0180] (Synthesis of Compound 2)

[0181] Under nitrogen atmosphere, compound 2-1 (23.7 g, 48 mmol) and 9H-carbazole-1,3,4,5,6,8-d6 (8.3 g, 48 mmol) were added to dimethylformamide (474 ​​ml), stirred and refluxed. Then, cesium carbonate (46.9 g, 144.1 mmol) was added, stirred thoroughly, reacted for 4 hours, cooled to room temperature, and the generated solid was filtered. The solid was added to toluene (932 ml) and dissolved, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from toluene and ethyl acetate to produce a white solid compound 2 (20.8 g, yield: 67%, MS: [M+H] + =647.8).

[0182] Synthesis Example 3: Synthesis of Compound 3

[0183]

[0184] (Synthesis of Intermediate 3-1)

[0185] Under nitrogen atmosphere, compound 1-3 (41 g, 78 mmol) and 3-chloro-3'-fluoro-1,1'-biphenyl (16.1 g, 78 mmol) were added to THF (820 ml), stirred and refluxed. Then, potassium carbonate (32.4 g, 234.1 mmol) was dissolved in water (32 ml) and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium (0) (2.7 g, 2.3 mmol) was added. After reacting for 5 hours, the mixture was cooled to room temperature and the generated solid was filtered. The solid was dissolved in chloroform (1334 ml), washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce a white solid compound 3-1 (33.3 g, yield: 75%, MS: [M+H] + =570.6).

[0186] (Synthesis of Compound 3)

[0187] Under nitrogen atmosphere, compound 3-1 (33.3 g, 58.5 mmol) and 9H-carbazole-1,3,4,5,6,8-d6 (10.1 g, 58.5 mmol) were added to dimethylformamide (666 ml), stirred and refluxed. Then, cesium carbonate (57.1 g, 175.4 mmol) was added, stirred thoroughly, reacted for 5 hours, cooled to room temperature, and the generated solid was filtered. The solid was added to toluene (1268 ml) and dissolved, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from toluene and ethyl acetate to produce a white solid compound 3 (26.2 g, yield: 62%, MS: [M+H] + =723.9).

[0188] Synthesis Example 4: Synthesis of Compound 4

[0189]

[0190] (Synthesis of Intermediate 4-1)

[0191] Under nitrogen atmosphere, 1-bromo-6-chlorodibenzo[b,d]furan-2,3,4,7,8,9-d6 (52 g, 180.8 mmol) and bis(pinacolato)diboron (46.4 g, 198.9 mmol) were added to dichloromethane. oxane (1040ml), stirred and refluxed. Then, potassium acetate (52.1g, 542.5mmol) was added, and after sufficient stirring, [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (4g, 5.4mmol) was added. After reacting for 7 hours, the mixture was cooled to room temperature, and the organic layer was filtered to remove the salt, and the filtered organic layer was distilled. It was again added to chloroform (605ml) and dissolved. After washing with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was filtered after stirring. The filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to produce a gray solid compound 4-1 (53.3g, yield: 88%, MS: [M+H] + =335.6).

[0192] (Synthesis of Intermediate 4-2)

[0193] Under nitrogen atmosphere, compound 4-1 (53.3 g, 159.3 mmol) and 2-([1,1'-biphenyl]-2-yl)-4-chloro-6-phenyl-1,3,5-triazine (54.8 g, 159.3 mmol) were added to THF (1066 ml), stirred and refluxed. Then, potassium carbonate (66 g, 477.8 mmol) was dissolved in water (66 ml) and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (5.5 g, 4.8 mmol) was added. After reacting for 6 hours, the mixture was cooled to room temperature and the generated solid was filtered. The solid was added to chloroform (2466 ml) and dissolved. After washing with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce a yellow solid compound 4-2 (64.9 g, yield: 79%, MS: [M+H] + =517).

[0194] (Synthesis of Intermediate 4-3)

[0195] Under nitrogen atmosphere, compound 4-2 (64.9 g, 125.8 mmol) and bis(pinacolato)diboron (35.1 g, 138.3 mmol) were added to distilled water. oxane (1298 ml), stirred and refluxed. Then, potassium acetate (36.3 g, 377.3 mmol) was added, and after sufficient stirring, [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (2.8 g, 3.8 mmol) was added. After reacting for 6 hours, the mixture was cooled to room temperature, and the organic layer was filtered to remove the salt, and the filtered organic layer was distilled. It was added to chloroform (764 ml) again to dissolve, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, and the mixture was filtered after stirring. The filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to produce a gray solid compound 4-3 (55.8 g, yield: 73%, MS: [M+H] + =608.6).

[0196] (Synthesis of Intermediate 4-4)

[0197] Under nitrogen atmosphere, compound 4-3 (55.8 g, 91.8 mmol) and 4-chloro-4'-fluoro-1,1'-biphenyl (19 g, 91.8 mmol) were added to THF (1116 ml), stirred and refluxed. Then, potassium carbonate (38.1 g, 275.5 mmol) was dissolved in water (38 ml) and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium (0) (3.2 g, 2.8 mmol) was added. After reacting for 8 hours, the mixture was cooled to room temperature and the generated solid was filtered. The solid was added to chloroform (1796 ml) and dissolved. After washing with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce a white solid compound 4-4 (35.9 g, yield: 60%, MS: [M+H] + =652.8).

[0198] (Synthesis of Compound 4)

[0199] Under nitrogen atmosphere, compound 4-4 (35.9 g, 55.1 mmol) and 9H-carbazole-1,3,4,5,6,8-d6 (9.5 g, 55.1 mmol) were added to dimethylformamide (718 ml), stirred and refluxed. Then, cesium carbonate (53.8 g, 165.2 mmol) was added, stirred thoroughly, reacted for 3 hours, cooled to room temperature, and the generated solid was filtered. The solid was added to toluene (1330 ml) and dissolved, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from toluene and ethyl acetate to produce a white solid compound 4 (35.5 g, yield: 80%, MS: [M+H] + =806).

[0200] Synthesis Example 5: Synthesis of Compound 5

[0201]

[0202] (Synthesis of Intermediate 5-1)

[0203] Under nitrogen atmosphere, compound 1-1 (40 g, 121.7 mmol) and 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (47.3 g, 121.7 mmol) were added to THF (800 ml), stirred and refluxed. Then, potassium carbonate (50.5 g, 365.2 mmol) was dissolved in water (50 ml) and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (4.2 g, 3.7 mmol) was added. After reacting for 7 hours, the mixture was cooled to room temperature and the generated solid was filtered. The solid was dissolved in chloroform (1862 ml), washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce a white solid compound 5-1 (31 g, yield: 50%, MS: [M+H] + =511).

[0204] (Synthesis of Intermediate 5-2)

[0205] Under nitrogen atmosphere, compound 5-1 (31 g, 60.8 mmol) and bis(pinacolato)diboron (17 g, 66.9 mmol) were added to distilled water. oxane (620ml), stirred and refluxed. Then, potassium acetate (17.5g, 182.4mmol) was added, and after sufficient stirring, [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (1.3g, 1.8mmol) was added. After reacting for 4 hours, the mixture was cooled to room temperature, and the organic layer was filtered to remove the salt, and the filtered organic layer was distilled. It was added to chloroform (366ml) again to dissolve, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, and the mixture was filtered after stirring. The filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to produce a gray solid compound 5-2 (27.1g, yield: 74%, MS: [M+H] + =602.5).

[0206] (Synthesis of Intermediate 5-3)

[0207] Under nitrogen atmosphere, compound 5-2 (27.1 g, 45.1 mmol) and 1-chloro-3-fluorobenzene (5.9 g, 45.1 mmol) were added to THF (542 ml), stirred and refluxed. Then, potassium carbonate (18.7 g, 135.2 mmol) was dissolved in water (19 ml) and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium (0) (1.6 g, 1.4 mmol) was added. After reacting for 7 hours, the reaction mixture was cooled to room temperature and the generated solid was filtered. The solid was dissolved in chloroform (792 ml), washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce a white solid compound 5-3 (15.3 g, yield: 58%, MS: [M+H] + =587.1).

[0208] (Synthesis of Compound 5)

[0209] Under nitrogen atmosphere, compound 5-3 (15.3 g, 26.1 mmol) and 9H-carbazole-1,2,3,4,5,6,7,8-d8 (4.6 g, 26.1 mmol) were added to dimethylformamide (306 ml), stirred and refluxed. Then, cesium carbonate (25.5 g, 78.3 mmol) was added, stirred thoroughly, reacted for 7 hours, cooled to room temperature, and the generated solid was filtered. The solid was added to toluene (568 ml) and dissolved, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from toluene and ethyl acetate to produce a white solid compound 5 (9.7 g, yield: 51%, MS: [M+H] + =725.9).

[0210] Synthesis Example 6: Synthesis of Compound 6

[0211]

[0212] (Synthesis of Intermediate 6-1)

[0213] Under nitrogen atmosphere, compound 1-1 (38 g, 115.6 mmol) and 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (41.4 g, 115.6 mmol) were added to THF (760 ml), stirred and refluxed. Then, potassium carbonate (47.9 g, 346.9 mmol) was dissolved in water (48 ml) and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (4 g, 3.5 mmol) was added. After reacting for 6 hours, the mixture was cooled to room temperature and the generated solid was filtered. The solid was dissolved in chloroform (1818 ml), washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce a white solid compound 6-1 (43 g, yield: 71%, MS: [M+H] + =525).

[0214] (Synthesis of Intermediate 6-2)

[0215] Under nitrogen atmosphere, compound 6-1 (43 g, 82.1 mmol) and bis(pinacolato)diboron (22.9 g, 90.3 mmol) were added to distilled water. oxane (860ml), stirred and refluxed. Then, potassium acetate (23.7g, 246.2mmol) was added, and after sufficient stirring, [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (1.8g, 2.5mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, and the organic layer was filtered to remove the salt, and the filtered organic layer was distilled. It was added to chloroform (505ml) again to dissolve, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, and the mixture was filtered after stirring. The filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to produce a gray solid compound 6-2 (33.3g, yield: 66%, MS: [M+H] + =616.5).

[0216] (Synthesis of Intermediate 6-3)

[0217] Under nitrogen atmosphere, compound 6-2 (33.3 g, 54.1 mmol) and 2-chloro-4'-fluoro-1,1'-biphenyl (11.2 g, 54.1 mmol) were added to THF (666 ml), stirred and refluxed. Then, potassium carbonate (22.4 g, 162.3 mmol) was dissolved in water (22 ml) and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium (0) (1.9 g, 1.6 mmol) was added. After reacting for 4 hours, the mixture was cooled to room temperature and the generated solid was filtered. The solid was dissolved in chloroform (1071 ml), washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce a white solid compound 6-3 (20.7 g, yield: 58%, MS: [M+H] + =660.7).

[0218] (Synthesis of Compound 6)

[0219] Under nitrogen atmosphere, compound 6-3 (20.7 g, 31.4 mmol) and 9H-carbazole-1,3,4,5,6,8-d6 (5.4 g, 31.4 mmol) were added to dimethylformamide (414 ml), stirred and refluxed. Then, cesium carbonate (30.7 g, 94.1 mmol) was added, stirred thoroughly, reacted for 6 hours, cooled to room temperature, and the generated solid was filtered. The solid was added to toluene (765 ml) and dissolved, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from toluene and ethyl acetate to produce a white solid compound 6 (15.8 g, yield: 62%, MS: [M+H] + =814).

[0220] Synthesis Example 7: Synthesis of Compound 7

[0221]

[0222] (Synthesis of Intermediate 7-1)

[0223] Under nitrogen atmosphere, compound 1-1 (57 g, 173.5 mmol) and 2-(4-bromophenyl)-4-(dibenzo[b,d]thiophen-3-yl)-6-phenyl-1,3,5-triazine (85.8 g, 173.5 mmol) were added to THF (1140 ml), stirred and refluxed. Then, potassium carbonate (71.9 g, 520.4 mmol) was dissolved in water (72 ml) and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (6 g, 5.2 mmol) was added. After reacting for 8 hours, the mixture was cooled to room temperature and the generated solid was filtered. The solid was dissolved in chloroform (3206 ml), washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, stirred, and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce a white solid compound 7-1 (73.7 g, yield: 69%, MS: [M+H] + =617.1).

[0224] (Synthesis of Intermediate 7-2)

[0225] Under nitrogen atmosphere, compound 7-1 (73.7 g, 119.6 mmol) and bis(pinacolato)diboron (33.4 g, 131.6 mmol) were added to distilled water. oxane (1474 ml), stirred and refluxed. Then, potassium acetate (34.5 g, 358.8 mmol) was added, and after sufficient stirring, [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (2.6 g, 3.6 mmol) was added. After reacting for 5 hours, the mixture was cooled to room temperature, and the organic layer was filtered to remove the salt, and the filtered organic layer was distilled. It was again added to chloroform (846 ml) and dissolved. After washing with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was filtered after stirring. The filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to produce a gray solid compound 7-2 (68.6 g, yield: 81%, MS: [M+H] + =708.7).

[0226] (Synthesis of Intermediate 7-3)

[0227] Under nitrogen atmosphere, compound 7-2 (68.6 g, 96.9 mmol) and 1-chloro-4-fluorobenzene (1-chloro-4-fluorobenzene) (12.7 g, 96.9 mmol) were added to THF (1372 ml), stirred and refluxed. Then, potassium carbonate (40.2 g, 290.8 mmol) was dissolved in water (40 ml) and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium (0) (3.4 g, 2.9 mmol) was added. After reacting for 9 hours, the reaction was cooled to room temperature and the generated solid was filtered. The solid was added to chloroform (1965 ml) and dissolved. After washing with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was filtered after stirring. The filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce a white solid compound 7-3 (51.1 g, yield: 78%, MS: [M+H] + =676.8).

[0228] (Synthesis of Compound 7)

[0229] Under nitrogen atmosphere, compound 7-3 (51.1 g, 75.6 mmol) and 9H-carbazole-1,3,4,5,6,8-d6 (13.1 g, 75.6 mmol) were added to dimethylformamide (1022 ml), stirred and refluxed. Then, cesium carbonate (73.9 g, 226.8 mmol) was added, stirred thoroughly, reacted for 3 hours, cooled to room temperature, and the generated solid was filtered. The solid was added to toluene (1881 ml) and dissolved, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from toluene and ethyl acetate to produce a white solid compound 7 (37.6 g, yield: 60%, MS: [M+H] + =830).

[0230] Synthesis Example 8: Synthesis of Compound 8

[0231]

[0232] (Synthesis of Intermediate 8-1)

[0233] Under nitrogen atmosphere, 1-bromo-6-chlorodibenzo[b,d]thiophene (36 g, 121 mmol) and bis(pinacolato)diboron (33.8 g, 133.1 mmol) were added to dibromo-6-chlorodibenzo[b,d]thiophene. oxane (720ml), stirred and refluxed. Then, potassium acetate (34.9g, 362.9mmol) was added, and after sufficient stirring, [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (2.7g, 3.6mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, and the organic layer was filtered to remove the salt, and the filtered organic layer was distilled. It was added to chloroform (417ml) again to dissolve, washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, and the mixture was filtered after stirring. The filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to produce a gray solid compound 8-1 (30g, yield: 72%, MS: [M+H] + =345.7).

[0234] (Synthesis of Intermediate 8-2)

[0235] Under nitrogen atmosphere, compound 8-1 (30 g, 87 mmol) and 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (2-(2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine) were added to the mixture. azine)(29.9 g, 87 mmol) was added to THF(600 ml), stirred and refluxed. Potassium carbonate (36.1 g, 261.1 mmol) was then dissolved in water (36 ml) and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium(0) (3 g, 2.6 mmol) was added. After reacting for 8 hours, the mixture was cooled to room temperature and the generated solid was filtered. The solid was dissolved in chloroform (1374 ml), washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce a yellow solid compound 8-2 (27 g, yield: 59%, MS: [M+H] + =527.1).

[0236] (Synthesis of Intermediate 8-3)

[0237] Under nitrogen atmosphere, compound 8-2 (27 g, 51.3 mmol) and bis(pinacolato)diboron (14.3 g, 56.5 mmol) were added to distilled water. oxane (540ml), stirred and refluxed. Then, potassium acetate (14.8g, 154mmol) was added, and after sufficient stirring, [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (1.1g, 1.5mmol) was added. After reacting for 7 hours, the mixture was cooled to room temperature, and the organic layer was filtered to remove the salt, and the filtered organic layer was distilled. It was again added to chloroform (317ml) and dissolved. After washing with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, and the mixture was filtered after stirring. The filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethanol to produce a gray solid compound 8-3 (20.6g, yield: 65%, MS: [M+H] + =618.6).

[0238] (Synthesis of Intermediate 8-4)

[0239] Under nitrogen atmosphere, compound 8-3 (20.6 g, 33.4 mmol) and 1-chloro-3-fluorobenzene (4.4 g, 33.4 mmol) were added to THF (412 ml), stirred and refluxed. Then, potassium carbonate (13.8 g, 100.1 mmol) was dissolved in water (14 ml) and added. After sufficient stirring, tetrakis(triphenylphosphine)palladium (0) (1.2 g, 1 mmol) was added. After reacting for 9 hours, the solid was cooled to room temperature and filtered. The solid was dissolved in chloroform (586 ml), washed with water twice, and the organic layer was separated. Anhydrous magnesium sulfate was added, stirred and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce a white solid compound 8-4 (12.3 g, yield: 63%, MS: [M+H] + =586.7).

[0240] (Synthesis of Compound 8)

[0241] Under nitrogen atmosphere, compound 8-4 (12.3 g, 21 mmol) and 9H-carbazole-1,3,4,5,6,8-d6 (3.6 g, 21 mmol) were added to dimethylformamide (246 ml), stirred and refluxed. Then, cesium carbonate (20.5 g, 63 mmol) was added, stirred thoroughly, reacted for 6 hours, cooled to room temperature, and the generated solid was filtered. The solid was added to toluene (466 ml) and dissolved, washed with water twice, the organic layer was separated, anhydrous magnesium sulfate was added, filtered after stirring, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from toluene and ethyl acetate to produce a white solid compound 8 (11.9 g, yield: 77%, MS: [M+H] + =739.9).

[0242] [Example]

[0243] Example 1

[0244] ITO (Indium Tin Oxide) 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.

[0245] On the ITO transparent electrode prepared in this way, as a hole injection layer, the following compound HT-A and the following compound PD were mixed at a weight ratio of 95:5 and at a ratio of 1:1. Then, only the following compound HT-A was deposited with a thickness of The hole transport layer was formed by evaporation of a thickness of 1000 nm. On the hole transport layer, the following compound HT-B was deposited at a thickness of On the electron blocking layer, the compound 1 prepared in the above-mentioned synthesis example 1 and the following compound GD were added in a weight ratio of 85:15 and 1:1. The following compound ET-A was deposited on the luminescent layer in a thickness of On the hole blocking layer, the following compound ET-B and the following Liq compound were added at a weight ratio of 2:1 and at a thickness of 1:1. Then, LiF and magnesium were deposited at a weight ratio of 1:1. The electron transport and injection layer is formed by vacuum evaporation of a thickness of 1:1. On the electron transport and injection layer, magnesium and silver are deposited in a weight ratio of 1:4 and A cathode is formed by evaporation with a thickness of , thereby manufacturing an organic light-emitting device.

[0246]

[0247] In the above process, the evaporation rate of organic matter is maintained Lithium fluoride at cathode maintains The evaporation rate of silver and magnesium is maintained The evaporation speed is 2×10 -7~5×10 -6 A support is provided to produce an organic light-emitting device.

[0248] Examples 2 to 11

[0249] An organic light-emitting device was manufactured by the same method as in Example 1, except that the compounds described in the following Table 1 were used instead of Compound 1.

[0250] For reference, in Examples 9 to 11, organic light-emitting devices were prepared by using the compounds described in Table 1 below in a weight ratio of 1:1 instead of Compound 1. Taking Example 8 as an example, Compound 1 and Compound H-2 were used in a weight ratio of 1:1 instead of Compound 1 in Example 1.

[0251] Comparative Examples 1 to 8

[0252] An organic light-emitting device was manufactured by the same method as in Example 1, except that the compounds described in the following Table 1 were used instead of Compound 1.

[0253] For reference, in Comparative Examples 5 to 8, organic light-emitting devices were manufactured using compounds described in Table 1 below in a weight ratio of 1:1 instead of Compound 1. Taking Comparative Example 4 as an example, Compound C1 and Compound H-2 were used in a weight ratio of 1:1 instead of Compound 1 of Example 1.

[0254] The structures of compounds H-2 and C1 to C4 in Table 1 below are shown below.

[0255]

[0256] Experimental example

[0257] Current was applied to the organic light-emitting devices manufactured in the above-mentioned Examples and Comparative Examples, and the voltage, efficiency, and life (T95) were measured. The results are shown in Table 1 below. At this time, the voltage and efficiency were measured when 10 mA / cm 2 In addition, T95 in Table 1 below refers to the current density of 20 mA / cm 2 The time required for the initial brightness to decrease to 95% was measured.

[0258]

Table 1

[0259]

[0260] Examples 1 to 8 and Comparative Examples 1 to 4 are device examples using a single host in the light emitting layer. The compound of Chemical Formula 1 is a compound characterized by containing deuterium-substituted carbazole. It can be seen that the lifetime is increased compared to Comparative Example 1 or 2.

[0261] In particular, Comparative Example 3 has a structure of carbazole substituted with deuterium, but the bonding position is different, so it can be confirmed that the thermal characteristics of the material vary greatly depending on the bonding position, and the physical properties show differences. When the material is arranged at the para position based on the dibenzofuran structure, the sublimation temperature is greatly increased, and the possibility of process problems is high, so the physical properties show disadvantages when applied to organic light-emitting devices.

[0262] In addition, Examples 9 to 11 are device examples using two types of hosts in the light-emitting layer. It can be confirmed that when two types of hosts are used in the light-emitting layer, the devices of Examples 9 to 11 using the compounds of the present invention have higher efficiency than the devices of Comparative Examples 5 to 8, and particularly significantly improved life characteristics.

[0263] Therefore, as shown in Table 1, it can be confirmed that when the compound of Chemical Formula 1 is used as a host of an organic light-emitting device, it exhibits characteristics of low voltage, high efficiency, and long life.

Claims

1. A compound represented by the following chemical formula 1: [Chemical formula 1] In the chemical formula 1, Y is O or S, R1 to R4 are each independently hydrogen; deuterium; substituted or unsubstituted C 6-60 Aryl; or a substituted or unsubstituted C containing any one or more heteroatoms selected from N, O and S 2-60 Heteroaryl, a and b are each independently an integer from 1 to 3, c and d are each independently an integer from 1 to 4, e and f are each independently an integer from 1 to 2, At least one of R3 or R4 is deuterium, L1 is a direct bond; substituted or unsubstituted C 6-60 or a substituted or unsubstituted C containing any one or more heteroatoms selected from N, O and S 2-60 Heteroarylene, L2 is phenylene, biphenylene, (diphenyl)phenylene, anthracene, 9,9-dimethylfluorenylene, dibenzothienylene or triphenylene, The L2 is substituted with one or more deuterium or is unsubstituted, Ar1 and Ar2 are each independently substituted or unsubstituted C 6-60 Aryl; or a substituted or unsubstituted C containing any one or more heteroatoms selected from N, O and S 2-60 Heteroaryl.

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

3. The compound according to claim 1, wherein is any one selected from the following groups: The definitions of Y, R1 and R2 are the same as those in claim 1.

4. The compound according to claim 1, wherein R3 and R4 are each independently hydrogen, deuterium, phenyl, biphenyl or terphenyl, When R3 or R4 is phenyl, biphenyl or terphenyl, the phenyl, biphenyl or terphenyl is substituted with one or more deuterium or is unsubstituted, At least one of R3 or R4 is deuterium.

5. The compound according to claim 1, wherein L1 is a direct bond, a phenylene group, a biphenylene group, a naphthylene group, a dibenzofuranyl group or a dibenzothiophenylene group, When L1 is phenylene, biphenylene, naphthylene, dibenzofuranylene or dibenzothiophenylene, the phenylene, biphenylene, naphthylene, dibenzofuranylene and dibenzothiophenylene groups are substituted with one or more deuterium groups or with one or more phenyl groups or are unsubstituted.

6. The compound according to claim 1, wherein Ar1 and Ar2 are each independently phenyl, biphenyl, terphenyl, naphthyl, dibenzofuranyl, dibenzothienyl or 9,9-dimethylfluorenyl, Here, Ar1 and Ar2 are phenyl groups which may be unsubstituted or substituted with one or more deuterium groups.

7. The compound according to claim 1, wherein The substituent is any one of the substituents shown below: R3 and R4 have the same meanings as in claim 1.

8. The compound according to claim 1, wherein L1 is a direct bond or any of the following linking groups, The linking group is substituted with one or more deuterium or is unsubstituted.

9. The compound according to claim 1, wherein L2 is any one of the following linking groups:

10. The compound according to claim 1, wherein The compound represented by the chemical formula 1 is one of the following compounds:

11. 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 10.

12. The organic light emitting device according to claim 11, wherein: The organic layer containing the compound is a light-emitting layer.

Images