Organic light-emitting devices

Abstract

The present invention provides an organic light-emitting device.

Description

Technical Field

[0001] This application claims the priority based on Korean Patent Application No. 10-2019-0030168 filed on March 15, 2019 and Korean Patent Application No. 10-2020-0030989 filed on March 12, 2020, and incorporates all the contents disclosed in the documents of the Korean patent applications as a part of this specification.

[0002] The invention relates to an organic light emitting device with low driving voltage, high luminous efficiency and excellent lifespan. Background Art

[0003] 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.

[0004] 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.

[0005] As for organic substances used for organic light-emitting devices as described above, development of new materials continues to be required.

[0006] Prior art literature

[0007] Patent Literature

[0008] (Patent Document 0001) Korean Patent Publication No. 10-2000-0051826 Summary of the invention

[0009] Technical issues

[0010] The invention relates to an organic light emitting device with low driving voltage, high luminous efficiency and excellent lifespan.

[0011] Solution to the problem

[0012] In order to solve the above-mentioned problems, the present invention provides the following organic light-emitting device.

[0013] The organic light emitting device according to the present invention comprises:

[0014] a first electrode;

[0015] a second electrode disposed opposite to the first electrode; and

[0016] A light-emitting layer is provided between the first electrode and the second electrode,

[0017] The light-emitting layer includes a first compound represented by the following chemical formula 1 and a second compound represented by the following chemical formula 2.

[0018] [Chemical formula 1]

[0019]

[0020] In the above chemical formula 1,

[0021] X 1 To X 3 are each independently N or CH, X 1 To X 3 At least two of them are N,

[0022] Ar 1 and Ar 2 are each independently 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,

[0023] Z is independently hydrogen or deuterium, or two adjacent Zs can combine with each other to form C 6-60 An aromatic ring or a C 2-60 Aromatic heterocyclic rings,

[0024] Here, the above C 6-60 Aromatic ring and the above C 2-60 The aromatic heterocyclic ring is unsubstituted or substituted with deuterium,

[0025] n is an integer from 0 to 6,

[0026] A is a substituent represented by the following chemical formula 1-1,

[0027] [Chemical formula 1-1]

[0028]

[0029] In the above chemical formula 1-1,

[0030] R 1 To R 4 are each independently hydrogen or deuterium, or R1 To R 4 Two adjacent ones can combine with each other to form C 6-60 An aromatic ring or a C 2-60 Aromatic heterocyclic rings,

[0031] Here, the above C 6-60 Aromatic ring and the above C 2-60 The aromatic heterocyclic ring is unsubstituted or substituted with deuterium,

[0032] D refers to deuterium,

[0033] m is an integer from 0 to 6,

[0034] [Chemical formula 2]

[0035]

[0036] In the above chemical formula 2,

[0037] T 1 To T 4 are each independently a substituted or unsubstituted C 6-60 Aromatic ring; or a substituted or unsubstituted C containing any one or more heteroatoms selected from N, O and S 2-60 Aromatic heterocyclic rings,

[0038] L 1 and L 2 are each independently a single 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,

[0039] Ar 3 and Ar 4 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.

[0040] Effects of the Invention

[0041] The organic light-emitting device comprises both the first compound and the second compound as host substances in the light-emitting layer, thereby exhibiting low driving voltage, high light-emitting efficiency and long life characteristics. BRIEF DESCRIPTION OF THE DRAWINGS

[0042] Figure 1 The diagram shows an organic light-emitting device composed of a substrate 1 , an anode 2 , a light-emitting layer 3 and a cathode 4 .

[0043] Figure 2 The diagram shows an example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 3, an electron suppression layer 7, a hole blocking layer 8, an electron injection and transport layer 9, and a cathode 4. DETAILED DESCRIPTION

[0044] In the following, the present invention will be described in more detail to help understanding the present invention.

[0045] (Definition of terms)

[0046] In this manual, and It represents the bond to other substituents.

[0047] 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 ( alkyl thioxy); arylthio aryl thioxy); alkylsulfonyl ( alkyl sulfoxy); arylsulfonyl ( The present invention may be substituted or unsubstituted with one or more substituents of heteroaryl groups 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" may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may also be interpreted as a substituent formed by connecting two phenyl groups.

[0048] 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 group may have the following structure, but is not limited thereto.

[0049]

[0050] 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 group may be a group of the following structural formula, but is not limited thereto.

[0051]

[0052] 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 group may have the following structure, but is not limited thereto.

[0053]

[0054] 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.

[0055] In the present specification, specific examples of the boryl group include trimethylboryl, triethylboryl, tert-butyldimethylboryl, triphenylboryl, and phenylboryl, but are not limited thereto.

[0056] In the present specification, as examples of the halogen group, there are fluorine, chlorine, bromine or iodine.

[0057] 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.

[0058] 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.

[0059] 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.

[0060] 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, yl, fluorenyl, etc., but are not limited to these.

[0061] In the present specification, the fluorenyl group may be substituted, and two substituents may be combined with each other to form a spiro structure. etc. However, the present invention is not limited thereto.

[0062] In the present specification, the heteroaryl group is a heteroaryl group containing one or more of O, N, Si and S as heteroatoms, and the number of carbon atoms is not particularly limited, but preferably the number of carbon atoms is 2 to 60. Examples of the heteroaryl 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.

[0063] The term "aromatic ring" used in this specification is understood to include not only a monocyclic or fused polycyclic ring containing only carbon atoms as ring atoms and the entire molecule having aromaticity, but also a fused polycyclic ring formed by connecting a plurality of monocyclic rings with aromaticity such as a fluorene ring and adjacent substituents. At this time, the number of carbon atoms in the above-mentioned aromatic ring is 6 to 60, or 6 to 30, or 6 to 20, but is not limited thereto. In addition, as the above-mentioned aromatic ring, a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a pyrene ring, a fluorene ring, etc. can be used, but are not limited thereto.

[0064] The term "aromatic heterocycle (heterocyclic ring)" used in this specification refers to a heteromonocyclic ring or condensed heteropolycyclic ring containing one or more heteroatoms selected from O, N and S as ring atoms in addition to carbon atoms, and the entire molecule has aromaticity. The number of carbon atoms in the above heterocycle is 2 to 60, or 2 to 30, or 2 to 20, but is not limited thereto. In addition, as the above heterocycle, a benzofuran ring, a benzothiophene ring, a dibenzofuran ring, a dibenzothiophene ring, etc. can be used, but it is not limited thereto.

[0065] In this specification, the aryl group in aralkyl, aralkenyl, alkylaryl, and arylamine is the same as the examples of the above-mentioned aryl group. In this specification, the alkyl group in aralkyl, alkylaryl, and alkylamine is the same as the examples of the above-mentioned alkyl group. In this specification, the heteroaryl group in heteroarylamine can be applied to the above-mentioned description of the heteroaryl group. In this specification, the alkenyl group in aralkenyl is the same as the examples of the above-mentioned alkenyl group. In this specification, the arylene group is a divalent group, and the above-mentioned description of the aryl group can be applied. In this specification, the heteroarylene group is a divalent group, and the above-mentioned description of the heteroaryl group can be applied. In this specification, the hydrocarbon ring is not a monovalent group, but is formed by combining two substituents, and the above-mentioned description of the aryl group or the cycloalkyl group can be applied. In this specification, the heterocycle is not a monovalent group, but is formed by combining two substituents, and the above-mentioned description of the heteroaryl group can be applied.

[0066] Hereinafter, the present invention will be described in detail according to each configuration.

[0067] The first electrode and the second electrode

[0068] According to one embodiment, an organic light-emitting device includes a first electrode and a second electrode on a substrate that is opposite to the first electrode. In this case, when the first electrode is an anode, the second electrode is a cathode, and when the first electrode is a cathode, the second electrode is an anode.

[0069] Specifically, the organic light-emitting device may be an organic light-emitting device of a forward structure (normal type) in which an anode, a light-emitting layer and a cathode are sequentially stacked on a substrate. Alternatively, the organic light-emitting device may be an organic light-emitting device of a reverse structure (inverted type) in which a cathode, a light-emitting layer and an anode are sequentially stacked on a substrate.

[0070] As the above-mentioned anode material, in order to enable holes to be smoothly injected into the organic layer, it is preferred to use a material with a large work function. Specific examples of the above-mentioned anode material include metals such as vanadium, chromium, copper, zinc, gold, or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO:Al or SnO 2 : Combinations of metals such as Sb and oxides; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole and polyaniline, etc., but are not limited to these.

[0071] The cathode material is preferably a material with a small work function in order to facilitate electron injection into the organic layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; LiF / Al or LiO 2 / Al and other multilayer structure materials, but not limited to these.

[0072] Luminescent layer

[0073] According to one embodiment, an organic light-emitting device includes a light-emitting layer between the first electrode and the second electrode, which is a layer that emits light in the visible light region by combining holes and electrons transported from the hole transport layer and the electron transport layer, and the light-emitting layer contains the first compound represented by the chemical formula 1 and the second compound represented by the chemical formula 2.

[0074] At this time, in the light-emitting layer, the first compound and the second compound are both used as host materials. Specifically, the first compound is an N-type host material, and the second compound is a P-type host material. When the light-emitting layer of the organic light-emitting device contains both such an N-type host material and a P-type host material, compared with the case of using a single material host, it can show an improved effect in terms of efficiency and life.

[0075] In particular, the first compound has a structure in which both the N-hexacyclic group and the A substituent (benzocarbazolyl substituent) are bonded to one benzene ring of the dibenzothiophene core. The first compound having such a structure has high stability to electrons and holes, and can stably maintain the balance of electrons and holes, compared with a compound having a structure in which the N-hexacyclic group and the A substituent (benzocarbazolyl substituent) are bonded to different benzene rings of the dibenzothiophene core, and a compound in which a substituted / unsubstituted carbazolyl substituent is bonded instead of the A substituent (benzocarbazolyl substituent). Therefore, the organic light-emitting device using the above-mentioned first compound shows the characteristics of low driving voltage, high efficiency and long life compared with (1) a compound having a structure in which a hexacyclic N-containing heterocyclic group and an A substituent (benzocarbazolyl-based substituent) are respectively bonded to different benzene rings of a dibenzothiophene-based core and (2) an organic light-emitting device using a compound bonded with a substituted / unsubstituted carbazolyl substituent instead of the above-mentioned A substituent (benzocarbazolyl-based substituent).

[0076] Preferably, the first compound is represented by any one of the following chemical formulas 1A to 1D according to the binding position of the N-containing six-membered heterocyclic group in the dibenzothiophene core:

[0077]

[0078]

[0079] In the above chemical formulas 1A to 1D,

[0080] The explanation of each substituent is the same as that in the above Chemical Formula 1.

[0081] Preferably, X 1 To X 3 Both are N.

[0082] Preferably, Z is independently hydrogen or deuterium, or two adjacent Zs may combine with each other to form an unsubstituted or deuterated C 6-20 Aromatic ring, for example, benzene ring.

[0083] At this time, n indicating the number of Z is 0, 1, 2, 3, 4, 5 or 6.

[0084] More specifically, the first compound may be represented by any one of the following chemical formulas 1A-1 to 1D-1:

[0085]

[0086] In the above chemical formulas 1A-1 to 1D-1,

[0087] Z 1 To Z 3 One of them is a substituent A represented by the above chemical formula 1-1, and the others are each independently hydrogen or deuterium, or Z 1 To Z 3 Two adjacent rings can combine with each other to form an unsubstituted or deuterium-substituted benzene ring.

[0088] Z 4 To Z 7 are each independently hydrogen or deuterium, or Z 4 To Z 7 Two adjacent rings can combine with each other to form an unsubstituted or deuterium-substituted benzene ring.

[0089] Ar 1 and Ar 2 Same as defined in the above Chemical Formula 1.

[0090] Specifically, in the above chemical formula 1A-1,

[0091] Z 1 A, Z 2 and Z 3 are each independently hydrogen or deuterium, or Z 2 and Z 3 The two are combined with each other to form an unsubstituted or deuterium-substituted benzene ring; or

[0092] Z 2 A, Z 1 and Z 3 are each independently hydrogen or deuterium; or

[0093] Z 3 A, Z 1 and Z 2 are each independently hydrogen or deuterium, or Z 1 and Z 2 The two combine with each other to form a benzene ring that is unsubstituted or substituted with deuterium.

[0094] In addition, in the above chemical formula 1B-1,

[0095] Z 1 A, Z 2 and Z 3 are each independently hydrogen or deuterium, or Z2 and Z 3 The two are combined with each other to form an unsubstituted or deuterium-substituted benzene ring; or

[0096] Z 2 A, Z 1 and Z 3 are each independently hydrogen or deuterium; or

[0097] Z 3 A, Z 1 and Z 2 may each independently be hydrogen or deuterium.

[0098] In addition, in the above chemical formula 1C-1,

[0099] Z 1 A, Z 2 and Z 3 are each independently hydrogen or deuterium; or

[0100] Z 2 A, Z 1 and Z 3 are each independently hydrogen or deuterium; or

[0101] Z 3 A, Z 1 and Z 2 are each independently hydrogen or deuterium, or Z 1 and Z 2 The two combine with each other to form a benzene ring that is unsubstituted or substituted with deuterium.

[0102] Specifically, in the above chemical formula 1D-1,

[0103] Z 1 A, Z 2 and Z 3 are each independently hydrogen or deuterium, or Z 2 and Z 3 The two are combined with each other to form an unsubstituted or deuterium-substituted benzene ring; or

[0104] Z 2 A, Z 1 and Z 3 are each independently hydrogen or deuterium; or

[0105] Z 3 A, Z 1 and Z 2 are each independently hydrogen or deuterium, or Z 1 and Z 2 The two combine with each other to form a benzene ring that is unsubstituted or substituted with deuterium.

[0106] In addition, the first compound may be represented by any one of the following chemical formulas 3-1 to 3-7:

[0107]

[0108] In the above chemical formulas 3-1 to 3-7,

[0109] R is each independently hydrogen or deuterium,

[0110] A. Ar 1 and Ar 2 Same as defined in the above Chemical Formula 1.

[0111] Preferably, Ar 1 and Ar 2 are independently unsubstituted, or substituted with deuterium or C 6-20 Aryl substituted C 6-20 Aryl.

[0112] More preferably, Ar 1 and Ar 2 are each independently phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, dibenzothienyl, dibenzofuranyl or carbazolyl,

[0113] Here, Ar 1 and Ar 2 may be unsubstituted or independently selected from deuterium and C 6-20 The aryl group is substituted with 1 to 5 substituents.

[0114] Most preferably, Ar 1 and Ar 2 Each is independently selected from any one of the following groups:

[0115]

[0116] At this time, Ar 1 and Ar 2 can be the same as each other, or Ar 1 and Ar 2 Can be different.

[0117] In addition, in the substituent A represented by the above chemical formula 1-1, R 1 To R 4 are each independently hydrogen or deuterium, or R 1 To R 4 Two adjacent rings can combine with each other to form an unsubstituted or deuterium-substituted benzene ring.

[0118] In this case, m indicating the number of deuterium (D) is 0, 1, 2, 3, 4, 5 or 6.

[0119] For example, A is any one of the substituents represented by the following chemical formulas a1 to a4:

[0120]

[0121] Specific examples of the first compound are as follows:

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[0434] On the other hand, as an example, the compound represented by the above Chemical Formula 1 can be produced by a production method as shown in the following Reaction Formula 1.

[0435] [Reaction 1]

[0436]

[0437] In the above reaction formula 1, X is independently a halogen, preferably bromine or chlorine, and the definitions of other substituents are the same as those described above.

[0438] Specifically, the compound represented by the above chemical formula 1 is manufactured by combining the starting materials SM1 and SM2 through an amine substitution reaction. Such an amine substitution reaction is preferably carried out in the presence of a palladium catalyst and a base. In addition, the reactive group used for the above amine substitution reaction can be appropriately changed, and the manufacturing method of the compound represented by chemical formula 1 can be more specifically described in the synthesis example described later.

[0439] On the other hand, the second compound is a bicarbazole compound, preferably having T 1 To T 4 Each independently is C 6-20 More preferably, T 1 To T 4 is an unsubstituted or deuterium-substituted benzene ring, or an unsubstituted or deuterium-substituted naphthalene ring.

[0440] Most preferably, T 1 To T 4 All of them are benzene rings. In this case, the second compound is represented by the following chemical formula 2-1:

[0441] [Chemical formula 2-1]

[0442]

[0443] In the above chemical formula 2-1,

[0444] D refers to deuterium,

[0445] r and s are each independently an integer from 0 to 7,

[0446] The explanation of each substituent is the same as that defined in the above Chemical Formula 2.

[0447] Preferably, L 1 and L 2 are each independently a single bond, or an unsubstituted C 6-20 Arylene.

[0448] More preferably, L 1 and L 2 Each is independently a single bond, a phenylene group or a naphthylene group.

[0449] Preferably, Ar 3 and Ar 4 Each is independently unsubstituted or replaced by C 1-10 Alkyl or C 6-20 Aryl substituted C 6-20 Aryl; or C containing O or S 2-20 Heteroaryl.

[0450] More preferably, Ar 3 and Ar 4 each independently represents phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, spirobifluorenyl, fluoranthenyl, dibenzothienyl, or dibenzofuranyl,

[0451] Here, Ar 3 and Ar 4 may be unsubstituted or each independently selected from C 1-10 Alkyl and C 6-20 The aryl group is substituted with 1 to 4 substituents.

[0452] Most preferably, Ar 3 and Ar 4 Each is independently selected from any one of the following groups:

[0453]

[0454] At this time, Ar 3 and Ar 4 can be the same as each other, or Ar 3 and Ar 4 Can be different.

[0455] Preferably, the second compound is represented by the following chemical formula 2-2:

[0456] [Chemical formula 2-2]

[0457]

[0458] In the above chemical formula 2-2,

[0459] L 1 and L 2 are each independently a single bond, a phenylene group or a naphthylene group,

[0460] Ar 3 and Ar 4 Same as defined in the above Chemical Formula 2.

[0461] Specific examples of the second compound are as follows:

[0462]

[0463]

[0464]

[0465]

[0466]

[0467]

[0468]

[0469]

[0470]

[0471]

[0472]

[0473]

[0474]

[0475]

[0476]

[0477]

[0478]

[0479]

[0480]

[0481]

[0482]

[0483] On the other hand, as an example, the compound represented by the above Chemical Formula 2 can be produced by a production method as shown in the following Reaction Formula 2.

[0484] [Reaction 2]

[0485]

[0486] In the above reaction formula 2, X is independently a halogen, preferably bromine or chlorine, and the definitions of other substituents are the same as described above.

[0487] Specifically, the compound represented by the above chemical formula 2 is manufactured by combining starting materials SM3 and SM4 through Suzuki coupling reaction. Such Suzuki coupling reaction is preferably carried out in the presence of a palladium catalyst and a base. In addition, the reactive group for the above Suzuki coupling reaction can be appropriately changed, and the manufacturing method of the compound represented by the above chemical formula 2 can be more specifically described in the synthesis example described later.

[0488] It is preferable that the first compound and the second compound are contained in the light-emitting layer in a weight ratio of 99:1 to 1:99, more preferably in a weight ratio of 50:50, in order to achieve a high efficiency and a long lifetime of the device.

[0489] On the other hand, the light-emitting layer further comprises a dopant material in addition to the host material. Such dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like. Specifically, aromatic amine derivatives are aromatic fused ring derivatives having substituted or unsubstituted arylamino groups, such as pyrene, anthracene, The styrylamine compound is a compound in which at least one arylvinyl group is substituted in 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.

[0490] Preferably, the light emitting layer may include an iridium complex as shown below as a dopant material, but is not limited thereto.

[0491]

[0492]

[0493]

[0494] Hole injection layer

[0495] The organic light-emitting device according to an embodiment may further include a hole injection layer on the anode. The hole injection layer is formed of a hole injection substance, and the hole injection substance is preferably a compound that has the ability to transport holes, has the effect of injecting holes from the anode, has an excellent hole injection effect for the light-emitting layer or the light-emitting material, prevents the excitons generated in the light-emitting layer from migrating to the electron injection layer or the electron injection material, and has excellent thin film forming ability.

[0496] Specific examples of the hole injection material include metal porphyrin, oligothiophene, aromatic amine organic matter, hexanitrile hexaazatriphenylene organic matter, quinacridone organic matter, perylene organic matter, anthraquinone, polyaniline and polythiophene conductive polymers, but are not limited to these.

[0497] Hole transport layer

[0498] The organic light-emitting device according to an embodiment may further include a hole transport layer on the anode or the hole injection layer formed on the anode. The hole transport layer is a layer that receives holes from the anode or the hole injection layer formed on the anode and transports the holes to the light-emitting layer. The hole transport substance contained in the hole transport layer is a substance that can receive holes from the anode or the hole injection layer and transfer them to the light-emitting layer, and is suitable for substances with large hole mobility.

[0499] Specific examples of the hole transport material include arylamine-based organic substances, conductive polymers, and block copolymers having both a conjugated portion and a non-conjugated portion, but the present invention is not limited thereto.

[0500] Electron suppression layer

[0501] The organic light-emitting device according to an embodiment may further include an electron suppression layer on the hole transport layer. The electron suppression layer is formed on the hole transport layer, preferably in contact with the light-emitting layer, and improves the efficiency of the organic light-emitting device by adjusting the hole mobility and preventing the excessive migration of electrons to increase the probability of hole-electron bonding. The electron suppression layer contains an electron blocking substance. As an example of such an electron blocking substance, a compound represented by the above chemical formula 1 is used, or an arylamine-based organic substance or the like can be used, but it is not limited thereto.

[0502] Hole blocking layer

[0503] According to an embodiment, the organic light-emitting device may further include a hole blocking layer on the light-emitting layer. The hole blocking layer is 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 hole-electron mobility, preventing excessive migration of holes, and increasing the probability of hole-electron bonding. The hole blocking layer contains a hole blocking substance. As examples of such a hole blocking substance, 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.

[0504] Electron transport layer

[0505] The organic light-emitting device according to one embodiment may include an electron transport layer on the light-emitting layer or the hole blocking layer. The electron transport layer is a layer that receives electrons from the cathode or the electron injection layer described later and transports the electrons to the light-emitting layer. As the electron transport material contained in the electron transport layer, a material that can well receive electrons from the cathode and transfer them to the light-emitting layer and has a high mobility for electrons is suitable.

[0506] Specific examples of the electron transport material include pyridine derivatives, pyrimidine derivatives, triazole derivatives, Al complexes of 8-hydroxyquinoline, Alq 3 The electron transport layer can be used together with any desired cathode material as used in the prior art. In particular, examples of suitable cathode materials are conventional materials with a low work function and accompanied by an aluminum layer or a silver layer. Specifically, cesium, barium, calcium, ytterbium and samarium, and in each case accompanied by an aluminum layer or a silver layer.

[0507] Electron injection layer

[0508] The organic light-emitting device according to one embodiment may further include an electron injection layer between the electron transport layer and the cathode. The electron injection layer is a layer for injecting electrons from the cathode, and the electron injection material contained in the electron injection layer is preferably a compound that has the ability to transport electrons, has the effect of injecting electrons from the cathode, has an excellent electron injection effect for the light-emitting layer or the light-emitting material, prevents the excitons generated in the light-emitting layer from migrating to the hole injection layer, and has excellent thin film forming ability.

[0509] Specific examples of materials that can be used as the electron injection layer include LiF, NaCl, CsF, Li 2 O, BaO, 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.

[0510] 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.

[0511] On the other hand, the electron transport layer and the electron injection layer may be provided in the form of an electron injection and transport layer that simultaneously performs the functions of the electron transport layer and the electron injection layer to transport the received electrons to the light-emitting layer.

[0512] Organic light-emitting devices

[0513] According to one embodiment, the structure of the organic light emitting device in which the first electrode is an anode and the second electrode is a cathode is shown in Figure 1 . 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 first compound and the second compound may be contained in the light-emitting layer.

[0514] According to another embodiment, the structure of the organic light emitting device in which the first electrode is an anode and the second electrode is a cathode is shown in Figure 2 . Figure 2The diagram shows an example of an organic light-emitting device composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 3, an electron suppression layer 7, a hole blocking layer 8, an electron injection and transport layer 9, and a cathode 4. In the above structure, the first compound and the second compound may be contained in the light-emitting layer.

[0515] The organic light-emitting device according to the present invention can be manufactured by stacking the above-mentioned structures in sequence. In this case, it can be manufactured as follows: using a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation (e-beam evaporation) to vapor-deposit a metal or a conductive metal oxide or an alloy thereof on a substrate to form an anode, and then forming the above-mentioned layers on the anode, and then vapor-depositing a substance that can be used as a cathode on the layer to manufacture. In addition to this method, an organic light-emitting device can also be manufactured by vapor-depositing a cathode substance, an organic layer, and an anode substance on a substrate in sequence. In addition, the light-emitting layer can be formed not only by vacuum evaporation, but also by solution coating to form a main body and a dopant. Here, the so-called solution coating method refers to spin coating, dip coating, blade coating, inkjet printing, screen printing, spraying, roller coating, etc., but is not limited to this.

[0516] 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 (WO2003 / 012890). However, the manufacturing method is not limited to this.

[0517] On the other hand, the organic light emitting device according to the present invention may be a top emission type, a bottom emission type, or a bi-directional emission type according to the materials used.

[0518] The production of the organic light-emitting device 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.

[0519] Synthesis Example 1-1: Preparation of Compound 1-1

[0520]

[0521] Under nitrogen atmosphere, intermediate 1-1-1 (10 g, 22.2 mmol), compound a (5.3 g, 24.4 mmol), sodium tert-butoxide (4.3 g, 44.4 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 3 hours, when the reaction was completed, the mixture was 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 produce 7.3 g of compound 1-1 (yield: 52%, MS: [M+H] + =631).

[0522] Synthesis Example 1-2: Preparation of Compound 1-2

[0523]

[0524] Under nitrogen atmosphere, intermediate 1-2-1 (10 g, 20 mmol), compound a (4.8 g, 22 mmol), sodium tert-butoxide (3.8 g, 40 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 3 hours, when the reaction was over, the mixture was 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 produce 6.9 g of compound 1-2 (yield: 51%, MS: [M+H] + =681).

[0525] Synthesis Example 1-3: Preparation of Compound 1-3

[0526]

[0527] Under nitrogen atmosphere, intermediate 1-3-1 (10 g, 16.3 mmol), compound a (3.9 g, 17.9 mmol), sodium tert-butoxide (3.1 g, 32.5 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 3 hours, when the reaction was over, the mixture was 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 produce 8.9 g of compound 1-3 (yield: 69%, MS: [M+H] + =796).

[0528] Synthesis Example 1-4: Preparation of Compound 1-4

[0529]

[0530] Under nitrogen atmosphere, intermediate 1-4-1 (10 g, 17.1 mmol), compound a (4.1 g, 18.8 mmol), sodium tert-butoxide (3.3 g, 34.2 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 3 hours, when the reaction was over, the mixture was 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 produce 7.1 g of compound 1-4 (yield: 54%, MS: [M+H] + =765).

[0531] Synthesis Example 1-5: Preparation of Compound 1-5

[0532]

[0533] Under nitrogen atmosphere, intermediate 1-5-1 (10 g, 17.9 mmol), compound a (4.3 g, 19.6 mmol), sodium tert-butoxide (3.4 g, 35.7 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 3 hours, when the reaction was over, the mixture was 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 produce 8.9 g of compound 1-5 (yield: 67%, MS: [M+H]+ =741).

[0534] Synthesis Example 1-6: Preparation of Compound 1-6

[0535]

[0536] Under nitrogen atmosphere, intermediate 1-6-1 (10 g, 15.4 mmol), compound a (3.7 g, 16.9 mmol), sodium tert-butoxide (3 g, 30.8 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours, when the reaction was over, the mixture was 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 produce 7.4 g of compound 1-6 (yield: 58%, MS: [M+H] + =831).

[0537] Synthesis Example 1-7: Preparation of Compound 1-7

[0538]

[0539] Under nitrogen atmosphere, intermediate 1-7-1 (10 g, 16.4 mmol), compound d (4.8 g, 18 mmol), sodium tert-butoxide (3.2 g, 32.8 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 3 hours, when the reaction was over, the mixture was 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 produce 7 g of compound 1-7 (yield: 51%, MS: [M+H] + =841).

[0540] Synthesis Example 1-8: Preparation of Compound 1-8

[0541]

[0542] Under nitrogen atmosphere, intermediate 1-8-1 (10 g, 16 mmol), compound d (4.7 g, 17.6 mmol), sodium tert-butoxide (3.1 g, 32 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 3 hours, when the reaction was over, the mixture was 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 produce 6.8 g of compound 1-8 (yield: 50%, MS: [M+H] + =855).

[0543] Synthesis Example 1-9: Preparation of Compound 1-9

[0544]

[0545] Under nitrogen atmosphere, intermediate 1-9-1 (10 g, 14.6 mmol), compound c (4.3 g, 16.1 mmol), sodium tert-butoxide (2.8 g, 29.2 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 2 hours, when the reaction was over, the mixture was 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 produce 6.7 g of compound 1-9 (yield: 50%, MS: [M+H] + =915).

[0546] Synthesis Example 1-10: Preparation of Compound 1-10

[0547]

[0548] Under nitrogen atmosphere, intermediate 1-10-1 (10 g, 17.4 mmol), compound b (5.1 g, 19.2 mmol), sodium tert-butoxide (3.3 g, 34.8 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours, when the reaction was over, the mixture was 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 produce 8.8 g of compound 1-10 (yield: 63%, MS: [M+H]+ =805).

[0549] Synthesis Example 1-11: Preparation of Compound 1-11

[0550]

[0551] Under nitrogen atmosphere, intermediate 1-11-1 (10 g, 16.5 mmol), compound a (3.9 g, 18.1 mmol), sodium tert-butoxide (3.2 g, 33 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours, when the reaction was over, the mixture was 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 produce 8.4 g of compound 1-11 (yield: 65%, MS: [M+H] + =787).

[0552] Synthesis Example 1-12: Preparation of Compound 1-12

[0553]

[0554] Under nitrogen atmosphere, intermediate 1-12-1 (10 g, 19 mmol), compound a (4.5 g, 20.9 mmol), sodium tert-butoxide (3.7 g, 38 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 3 hours, when the reaction was over, the mixture was 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 produce 7.1 g of compound 1-12 (yield: 53%, MS: [M+H] + =707).

[0555] Synthesis Example 1-13: Preparation of Compound 1-13

[0556]

[0557] Under nitrogen atmosphere, intermediate 1-13-1 (10 g, 15.4 mmol), compound a (3.7 g, 16.9 mmol), sodium tert-butoxide (3 g, 30.8 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 3 hours, when the reaction was over, the mixture was 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 produce 6.8 g of compound 1-13 (yield: 53%, MS: [M+H] + =831).

[0558] Synthesis Example 1-14: Preparation of Compound 1-14

[0559]

[0560] Under nitrogen atmosphere, intermediate 1-14-1 (10 g, 20 mmol), compound b (5.9 g, 22 mmol), sodium tert-butoxide (3.8 g, 40 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 3 hours, when the reaction was over, the mixture was 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 produce 7.9 g of compound 1-14 (yield: 54%, MS: [M+H] + =731).

[0561] Synthesis Example 1-15: Preparation of Compound 1-15

[0562]

[0563] Under nitrogen atmosphere, intermediate 1-15-1 (10 g, 15.3 mmol), compound c (4.5 g, 16.9 mmol), sodium tert-butoxide (2.9 g, 30.7 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 3 hours, when the reaction was over, the mixture was 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. The mixture was treated with anhydrous magnesium sulfate and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 9.3 g of compound 1-15 (yield: 69%, MS: [M+H]+ =883).

[0564] Synthesis Example 1-16: Preparation of Compound 1-16

[0565]

[0566] Under nitrogen atmosphere, intermediate 1-16-1 (10 g, 14.4 mmol), compound a (3.4 g, 15.8 mmol), sodium tert-butoxide (2.8 g, 28.7 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 3 hours, when the reaction was over, the mixture was 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 produce 6.4 g of compound 1-16 (yield: 51%, MS: [M+H] + =877).

[0567] Synthesis Example 1-17: Preparation of Compound 1-17

[0568]

[0569] Under nitrogen atmosphere, intermediate 1-17-1 (10 g, 20 mmol), compound a (4.8 g, 22 mmol), sodium tert-butoxide (3.8 g, 40 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, when the reaction was over, the mixture was 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 produce 7.9 g of compound 1-17 (yield: 58%, MS: [M+H] + =681).

[0570] Synthesis Example 1-18: Preparation of Compound 1-18

[0571]

[0572] Under nitrogen atmosphere, intermediate 1-18-1 (10 g, 16 mmol), compound b (4.7 g, 17.6 mmol), sodium tert-butoxide (3.1 g, 31.9 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours, when the reaction was over, the mixture was 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 produce 7.2 g of compound 1-18 (yield: 53%, MS: [M+H] + =857).

[0573] Synthesis Example 1-19: Preparation of Compound 1-19

[0574]

[0575] Under nitrogen atmosphere, intermediate 1-19-1 (10 g, 15.2 mmol), compound c (4.5 g, 16.8 mmol), sodium tert-butoxide (2.9 g, 30.5 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours, when the reaction was over, the mixture was 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 produce 8.5 g of compound 1-19 (yield: 63%, MS: [M+H] + =887).

[0576] Synthesis Example 1-20: Preparation of Compound 1-20

[0577]

[0578] Under nitrogen atmosphere, intermediate 1-20-1 (10 g, 15.2 mmol), compound d (4.5 g, 16.8 mmol), sodium tert-butoxide (2.9 g, 30.5 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours, when the reaction was over, the mixture was 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 produce 7.4 g of compound 1-20 (yield: 55%, MS: [M+H]+ =887).

[0579] Synthesis Example 1-21: Preparation of Compound 1-21

[0580]

[0581] Under nitrogen atmosphere, intermediate 1-21-1 (10 g, 19 mmol), compound a (4.5 g, 20.9 mmol), sodium tert-butoxide (3.7 g, 38 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, when the reaction was over, the mixture was 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 produce 9.4 g of compound 1-21 (yield: 70%, MS: [M+H] + =707).

[0582] Synthesis Example 1-22: Preparation of Compound 1-22

[0583]

[0584] Under nitrogen atmosphere, intermediate 1-22-1 (10 g, 22.2 mmol), compound a (5.3 g, 24.4 mmol), sodium tert-butoxide (4.3 g, 44.4 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, when the reaction was over, the mixture was 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 produce 7.1 g of compound 1-22 (yield: 51%, MS: [M+H] + =631).

[0585] Synthesis Example 1-23: Preparation of Compound 1-23

[0586]

[0587] Under nitrogen atmosphere, intermediate 1-23-1 (10 g, 16.2 mmol), compound a (3.9 g, 17.9 mmol), sodium tert-butoxide (3.1 g, 32.5 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 3 hours, when the reaction was over, the mixture was 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 produce 6.8 g of compound 1-23 (yield: 53%, MS: [M+H] + =797).

[0588] Synthesis Example 1-24: Preparation of Compound 1-24

[0589]

[0590] Under nitrogen atmosphere, intermediate 1-24-1 (10 g, 16 mmol), compound b (4.7 g, 17.6 mmol), sodium tert-butoxide (3.1 g, 31.9 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 3 hours, when the reaction was over, the mixture was 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 produce 8.3 g of compound 1-24 (yield: 61%, MS: [M+H] + =857).

[0591] Synthesis Example 1-25: Preparation of Compound 1-25

[0592]

[0593] Under nitrogen atmosphere, intermediate 1-25-1 (10 g, 15 mmol), compound d (4.4 g, 16.5 mmol), sodium tert-butoxide (2.9 g, 30 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 3 hours, when the reaction was over, the mixture was 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 produce 8.7 g of compound 1-25 (yield: 65%, MS: [M+H]+ =897).

[0594] Synthesis Example 1-26: Preparation of Compound 1-26

[0595]

[0596] Under nitrogen atmosphere, intermediate 1-26-1 (10 g, 20 mmol), compound a (4.8 g, 22 mmol), sodium tert-butoxide (3.8 g, 40 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, when the reaction was over, the mixture was 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 produce 6.9 g of compound 1-26 (yield: 51%, MS: [M+H] + =681).

[0597] Synthesis Example 1-27: Preparation of Compound 1-27

[0598]

[0599] Under nitrogen atmosphere, intermediate 1-27-1 (10 g, 16.7 mmol), compound a (4 g, 18.3 mmol), sodium tert-butoxide (3.2 g, 33.3 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours, when the reaction was over, the mixture was 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 produce 6.6 g of compound 1-27 (yield: 51%, MS: [M+H] + =781).

[0600] Synthesis Example 1-28: Preparation of Compound 1-28

[0601]

[0602] Under nitrogen atmosphere, intermediate 1-28-1 (10 g, 15.4 mmol), compound c (4.5 g, 16.9 mmol), sodium tert-butoxide (3 g, 30.8 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 3 hours, when the reaction was over, the mixture was 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 produce 7 g of compound 1-28 (yield: 52%, MS: [M+H] + =881).

[0603] Synthesis Example 1-29: Preparation of Compound 1-29

[0604]

[0605] Under nitrogen atmosphere, intermediate 1-29-1 (10 g, 16.7 mmol), compound a (4 g, 18.3 mmol), sodium tert-butoxide (3.2 g, 33.3 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours, when the reaction was over, the mixture was 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 produce 6.9 g of compound 1-29 (yield: 53%, MS: [M+H] + =781).

[0606] Synthesis Example 1-30: Preparation of Compound 1-30

[0607]

[0608] Under nitrogen atmosphere, intermediate 1-30-1 (10 g, 14 mmol), compound a (3.4 g, 15.4 mmol), sodium tert-butoxide (2.7 g, 28.1 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 2 hours, when the reaction was over, the mixture was 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 produce 7.1 g of compound 1-30 (yield: 57%, MS: [M+H]+ =893).

[0609] Synthesis Example 1-31: Preparation of Compound 1-31

[0610]

[0611] Under nitrogen atmosphere, intermediate 1-31-1 (10 g, 22.2 mmol), compound a (5.3 g, 24.4 mmol), sodium tert-butoxide (4.3 g, 44.4 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, when the reaction was over, the mixture was 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 produce 7.8 g of compound 1-31 (yield: 56%, MS: [M+H] + =631).

[0612] Synthesis Example 1-32: Preparation of Compound 1-32

[0613]

[0614] Under nitrogen atmosphere, intermediate 1-32-1 (10 g, 16.6 mmol), compound a (4 g, 18.3 mmol), sodium tert-butoxide (3.2 g, 33.3 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 3 hours, when the reaction was over, the mixture was 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 produce 8.1 g of compound 1-32 (yield: 62%, MS: [M+H] + =783).

[0615] Synthesis Example 1-33: Preparation of Compound 1-33

[0616]

[0617] Under nitrogen atmosphere, intermediate 1-33-1 (10 g, 19 mmol), compound a (4.6 g, 20.9 mmol), sodium tert-butoxide (3.7 g, 38.1 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, when the reaction was over, the mixture was 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 produce 7 g of compound 1-33 (yield: 52%, MS: [M+H] + =707).

[0618] Synthesis Example 1-34: Preparation of Compound 1-34

[0619]

[0620] Under nitrogen atmosphere, intermediate 1-34-1 (10 g, 18.2 mmol), compound a (4.4 g, 20 mmol), sodium tert-butoxide (3.5 g, 36.4 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 3 hours, when the reaction was over, the mixture was 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 produce 8.2 g of compound 1-34 (yield: 62%, MS: [M+H] + =731).

[0621] Synthesis Example 1-35: Preparation of Compound 1-35

[0622]

[0623] Under nitrogen atmosphere, intermediate 1-35-1 (10 g, 15.6 mmol), compound d (4.6 g, 17.2 mmol), sodium tert-butoxide (3 g, 31.3 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 3 hours, when the reaction was over, the mixture was 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 produce 9.4 g of compound 1-35 (yield: 69%, MS: [M+H]+ =871).

[0624] Synthesis Example 1-36: Preparation of Compound 1-36

[0625]

[0626] Under nitrogen atmosphere, intermediate 1-36-1 (10 g, 22.3 mmol), compound c (6.5 g, 24.5 mmol), sodium tert-butoxide (4.3 g, 44.5 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 3 hours, when the reaction was over, the mixture was 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. The mixture was treated with anhydrous magnesium sulfate and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 8 g of compound 1-36 (yield: 53%, MS: [M+H] + =681).

[0627] Synthesis Example 1-37: Preparation of Compound 1-37

[0628]

[0629] Under nitrogen atmosphere, intermediate 1-37-1 (10 g, 18.2 mmol), compound b (5.4 g, 20 mmol), sodium tert-butoxide (3.5 g, 36.4 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 2 hours, when the reaction was over, the mixture was 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 produce 379 g of compound 1-37 (yield: 63%, MS: [M+H] + =781).

[0630] Synthesis Example 1-38: Preparation of Compound 1-38

[0631]

[0632] Under nitrogen atmosphere, intermediate 1-38-1 (10 g, 14.7 mmol), compound c (4.3 g, 16.2 mmol), sodium tert-butoxide (2.8 g, 29.4 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours, when the reaction was over, the mixture was 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 produce 8.6 g of compound 1-38 (yield: 64%, MS: [M+H] + =913).

[0633] Synthesis Example 1-39: Preparation of Compound 1-39

[0634]

[0635] Under nitrogen atmosphere, intermediate 1-39-1 (10 g, 16 mmol), compound b (4.7 g, 17.6 mmol), sodium tert-butoxide (3.1 g, 32 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 3 hours, when the reaction was over, the mixture was 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. The mixture was treated with anhydrous magnesium sulfate and filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 9.3 g of compound 1-39 (yield: 68%, MS: [M+H] + =857).

[0636] Synthesis Example 1-40: Preparation of Compound 1-40

[0637]

[0638] Under nitrogen atmosphere, intermediate 1-40-1 (10 g, 18.2 mmol), compound a (4.4 g, 20 mmol), sodium tert-butoxide (3.5 g, 36.4 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.4 mmol) was added. After 3 hours, when the reaction was over, the mixture was 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 produce 8 g of compound 1-40 (yield: 60%, MS: [M+H]+ =731).

[0639] Synthesis Example 1-41: Preparation of Compound 1-41

[0640]

[0641] Under nitrogen atmosphere, intermediate 1-41-1 (10 g, 16.5 mmol), compound d (4.9 g, 18.2 mmol), sodium tert-butoxide (3.2 g, 33.1 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.2 g, 0.3 mmol) was added. After 2 hours, when the reaction was over, the mixture was 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 produce 8.2 g of compound 1-41 (yield: 59%, MS: [M+H] + =837).

[0642] Synthesis Example 1-42: Preparation of Compound 1-42

[0643]

[0644] Under nitrogen atmosphere, intermediate 1-42-1 (10 g, 14.4 mmol), compound c (4.2 g, 15.8 mmol), sodium tert-butoxide (2.8 g, 28.8 mmol) were added to 200 ml of xylene, stirred and refluxed. Then, bis(tri-tert-butylphosphine)palladium(0) (0.1 g, 0.3 mmol) was added. After 3 hours, when the reaction was over, the mixture was 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 produce 7.1 g of compound 1-42 (yield: 53%, MS: [M+H] + =927).

[0645] Synthesis Example 2-1: Preparation of Compound 2-1

[0646]

[0647] Under nitrogen atmosphere, intermediate 2-1-1 (10 g, 25.2 mmol) and intermediate 2-1-2 (8 g, 27.7 mmol) were added to 200 ml of THF and stirred. Potassium carbonate (13.9 g, 100.7 mmol) was dissolved in water and added. After sufficient stirring and reflux, bis(tri-tert-butylphosphine)palladium (0) (0.1 g, 0.3 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The obtained product was dissolved in chloroform again, washed with water twice, 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 purified by silica gel column chromatography to produce 9 g of compound 2-1 (yield: 64%, MS: [M+H] + =561).

[0648] Synthesis Example 2-2: Preparation of Compound 2-2

[0649]

[0650] Under a nitrogen atmosphere, intermediate 2-2-1 (10 g, 25.2 mmol) and intermediate 2-2-2 (8 g, 27.7 mmol) were added to 200 ml of THF and stirred. Potassium carbonate (13.9 g, 100.7 mmol) was dissolved in water and added. After sufficient stirring, the mixture was refluxed. Then, bis(tri-tert-butylphosphine)palladium (0) (0.1 g, 0.3 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. The obtained product was dissolved in chloroform again, washed with water twice, 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 purified by silica gel column chromatography to produce 10.6 g of compound 2-2 (yield: 66%, MS: [M+H] + =637).

[0651] Synthesis Example 2-3: Preparation of Compound 2-3

[0652]

[0653] Under nitrogen atmosphere, intermediate 2-3-1 (10 g, 25.2 mmol) and intermediate 2-3-2 (10.1 g, 27.7 mmol) were added to 200 ml of THF and stirred. Potassium carbonate (13.9 g, 100.7 mmol) was dissolved in water and added. After sufficient stirring, the mixture was refluxed. Then, bis(tri-tert-butylphosphine)palladium (0) (0.1 g, 0.3 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. The obtained product was dissolved in chloroform again, washed with water twice, 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 purified by silica gel column chromatography to produce 9 g of compound 2-3 (yield: 56%, MS: [M+H] + =637).

[0654] Synthesis Example 2-4: Preparation of Compound 2-4

[0655]

[0656] Under nitrogen atmosphere, intermediate 2-4-1 (10 g, 25.2 mmol) and intermediate 2-4-2 (9.3 g, 27.7 mmol) were added to 200 ml of THF and stirred. Potassium carbonate (13.9 g, 100.7 mmol) was dissolved in water and added. After sufficient stirring, the mixture was refluxed. Then, bis(tri-tert-butylphosphine)palladium (0) (0.1 g, 0.3 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. The obtained product was dissolved in chloroform again, washed with water twice, 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 purified by silica gel column chromatography to produce 7.8 g of compound 2-4 (yield: 51%, MS: [M+H] + =611).

[0657] Synthesis Example 2-5: Preparation of Compound 2-5

[0658]

[0659] Under nitrogen atmosphere, intermediate 2-5-1 (10 g, 25.2 mmol) and intermediate 2-5-2 (10.1 g, 27.7 mmol) were added to 200 ml of THF and stirred. Potassium carbonate (13.9 g, 100.7 mmol) was dissolved in water and added. After sufficient stirring, the mixture was refluxed. Then, bis(tri-tert-butylphosphine)palladium (0) (0.1 g, 0.3 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. The obtained product was dissolved in chloroform again, washed with water twice, 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 purified by silica gel column chromatography to produce 10.4 g of compound 2-5 (yield: 65%, MS: [M+H] + =637).

[0660] Synthesis Example 2-6: Preparation of Compound 2-6

[0661]

[0662] Under nitrogen atmosphere, intermediate 2-6-1 (10 g, 25.2 mmol) and intermediate 2-6-2 (11.4 g, 27.7 mmol) were added to 200 ml of THF and stirred. Potassium carbonate (13.9 g, 100.7 mmol) was dissolved in water and added. After sufficient stirring, the mixture was refluxed. Then, bis(tri-tert-butylphosphine)palladium (0) (0.1 g, 0.3 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. The obtained product was dissolved in chloroform again, washed with water twice, 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 purified by silica gel column chromatography to produce 10.5 g of compound 2-6 (yield: 61%, MS: [M+H] + =687).

[0663] Synthesis Example 2-7: Preparation of Compound 2-7

[0664]

[0665] Under nitrogen atmosphere, intermediate 2-7-1 (10 g, 22.4 mmol) and intermediate 2-7-2 (10.2 g, 24.6 mmol) were added to 200 ml of THF and stirred. Potassium carbonate (12.4 g, 89.5 mmol) was dissolved in water and added. After sufficient stirring, the mixture was refluxed. Then, bis(tri-tert-butylphosphine)palladium (0) (0.1 g, 0.2 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The obtained product was dissolved in chloroform again, washed with water twice, 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 purified by silica gel column chromatography to produce 11 g of compound 2-7 (yield: 67%, MS: [M+H] + =737).

[0666] Synthesis Example 2-8: Preparation of Compound 2-8

[0667]

[0668] Under nitrogen atmosphere, intermediate 2-8-1 (10 g, 17.9 mmol) and intermediate 2-8-2 (5.6 g, 19.7 mmol) were added to 200 ml of THF and stirred. Potassium carbonate (9.9 g, 71.5 mmol) was dissolved in water and added. After sufficient stirring, the mixture was refluxed. Then, bis(tri-tert-butylphosphine)palladium (0) (0.1 g, 0.2 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The obtained product was dissolved in chloroform again, washed with water twice, 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 purified by silica gel column chromatography to produce 7.8 g of compound 2-8 (yield: 60%, MS: [M+H] + =723).

[0669] Synthesis Example 2-9: Preparation of Compound 2-9

[0670]

[0671] Under nitrogen atmosphere, intermediate 2-9-1 (10 g, 21.1 mmol) and intermediate 2-9-2 (6.7 g, 23.3 mmol) were added to 200 ml of THF and stirred. Potassium carbonate (11.7 g, 84.6 mmol) was dissolved in water and added. After sufficient stirring, the mixture was refluxed. Then, bis(tri-tert-butylphosphine)palladium (0) (0.1 g, 0.2 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The obtained product was dissolved in chloroform again, washed with water twice, 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 purified by silica gel column chromatography to produce 7.4 g of compound 2-9 (yield: 55%, MS: [M+H] + =637).

[0672] Synthesis Example 2-10: Preparation of Compound 2-10

[0673]

[0674] Under nitrogen atmosphere, intermediate 2-10-1 (10 g, 27 mmol) and intermediate 2-10-2 (10 g, 29.6 mmol) were added to 200 ml of THF and stirred. Potassium carbonate (14.9 g, 107.8 mmol) was dissolved in water and added. After sufficient stirring, the mixture was refluxed. Then, bis(tri-tert-butylphosphine)palladium (0) (0.1 g, 0.3 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. The obtained product was dissolved in chloroform again, washed with water twice, 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 purified by silica gel column chromatography to produce 11 g of compound 2-10 (yield: 70%, MS: [M+H] + =585).

[0675] Synthesis Example 2-11: Preparation of Compound 2-11

[0676]

[0677] Under a nitrogen atmosphere, intermediate 2-11-1 (10 g, 27 mmol) and intermediate 2-11-2 (11.5 g, 29.6 mmol) were added to 200 ml of THF and stirred. Potassium carbonate (14.9 g, 107.8 mmol) was dissolved in water and added. After sufficient stirring, the mixture was refluxed. Then, bis(tri-tert-butylphosphine)palladium (0) (0.1 g, 0.3 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. The obtained product was dissolved in chloroform again, washed with water twice, 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 purified by silica gel column chromatography to produce 11.5 g of compound 2-11 (yield: 67%, MS: [M+H] + =635).

[0678] Synthesis Example 2-12: Preparation of Compound 2-12

[0679]

[0680] Under a nitrogen atmosphere, intermediate 2-12-1 (10 g, 23.8 mmol) and intermediate 2-12-2 (8.8 g, 26.1 mmol) were added to 200 ml of THF and stirred. Potassium carbonate (13.1 g, 95 mmol) was dissolved in water and added. After sufficient stirring, the mixture was refluxed. Then, bis(tri-tert-butylphosphine)palladium (0) (0.1 g, 0.2 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The obtained product was dissolved in chloroform again, washed with water twice, 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 purified by silica gel column chromatography to produce 10.4 g of compound 2-12 (yield: 69%, MS: [M+H] + =635).

[0681] Synthesis Example 2-13: Preparation of Compound 2-13

[0682]

[0683] Under a nitrogen atmosphere, intermediate 2-13-1 (10 g, 24.3 mmol) and intermediate 2-13-2 (11.1 g, 26.8 mmol) were added to 200 ml of THF and stirred. Potassium carbonate (13.5 g, 97.3 mmol) was dissolved in water and added. After sufficient stirring, the mixture was refluxed. Then, bis(tri-tert-butylphosphine)palladium (0) (0.1 g, 0.2 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. The obtained product was dissolved in chloroform again, washed with water twice, 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 purified by silica gel column chromatography to produce 9 g of compound 2-13 (yield: 53%, MS: [M+H] + =701).

[0684] Synthesis Example 2-14: Preparation of Compound 2-14

[0685]

[0686] Under a nitrogen atmosphere, intermediate 2-14-1 (10 g, 24.3 mmol) and intermediate 2-14-2 (7.7 g, 26.8 mmol) were added to 200 ml of THF and stirred. Potassium carbonate (13.5 g, 97.3 mmol) was dissolved in water and added. After sufficient stirring, the mixture was refluxed. Then, bis(tri-tert-butylphosphine)palladium (0) (0.1 g, 0.2 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The obtained product was dissolved in chloroform again, washed with water twice, 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 purified by silica gel column chromatography to produce 8.9 g of compound 2-14 (yield: 64%, MS: [M+H] + =575).

[0687] Synthesis Example 2-15: Preparation of Compound 2-15

[0688]

[0689] Under a nitrogen atmosphere, intermediate 2-15-1 (10 g, 24.3 mmol) and intermediate 2-15-2 (9 g, 26.8 mmol) were added to 200 ml of THF and stirred. Potassium carbonate (13.5 g, 97.3 mmol) was dissolved in water and added. After sufficient stirring, the mixture was refluxed. Then, bis(tri-tert-butylphosphine)palladium (0) (0.1 g, 0.2 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. The obtained product was dissolved in chloroform again, washed with water twice, 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 purified by silica gel column chromatography to produce 8.4 g of compound 2-15 (yield: 55%, MS: [M+H] + =625).

[0690] Synthesis Example 2-16: Preparation of Compound 2-16

[0691]

[0692] Under a nitrogen atmosphere, intermediate 2-16-1 (10 g, 24.3 mmol) and intermediate 2-16-2 (11.1 g, 26.8 mmol) were added to 200 ml of THF and stirred. Potassium carbonate (13.5 g, 97.3 mmol) was dissolved in water and added. After sufficient stirring, the mixture was refluxed. Then, bis(tri-tert-butylphosphine)palladium (0) (0.1 g, 0.2 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. The obtained product was dissolved in chloroform again, washed with water twice, 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 purified by silica gel column chromatography to produce 11.2 g of compound 2-16 (yield: 66%, MS: [M+H] + =701).

[0693] Synthesis Example 2-17: Preparation of Compound 2-17

[0694]

[0695] Under a nitrogen atmosphere, intermediate 2-17-1 (10 g, 24.3 mmol) and intermediate 2-17-2 (10.1 g, 26.8 mmol) were added to 200 ml of THF and stirred. Potassium carbonate (13.5 g, 97.3 mmol) was dissolved in water and added. After sufficient stirring, the mixture was refluxed. Then, bis(tri-tert-butylphosphine)palladium (0) (0.1 g, 0.2 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The obtained product was dissolved in chloroform again, washed with water twice, 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 purified by silica gel column chromatography to produce 10 g of compound 2-17 (yield: 62%, MS: [M+H] + =665).

[0696] Synthesis Example 2-18: Preparation of Compound 2-18

[0697]

[0698] Under a nitrogen atmosphere, intermediate 2-18-1 (10 g, 24.3 mmol) and intermediate 2-18-2 (10.5 g, 26.8 mmol) were added to 200 ml of THF and stirred. Potassium carbonate (13.5 g, 97.3 mmol) was dissolved in water and added. After sufficient stirring, the mixture was refluxed. Then, bis(tri-tert-butylphosphine)palladium (0) (0.1 g, 0.2 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. The obtained product was dissolved in chloroform again, washed with water twice, 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 purified by silica gel column chromatography to produce 9.8 g of compound 2-18 (yield: 59%, MS: [M+H] + =681).

[0699] Synthesis Example 2-19: Preparation of Compound 2-19

[0700]

[0701] Under a nitrogen atmosphere, intermediate 2-19-1 (10 g, 24.3 mmol) and intermediate 2-19-2 (10.5 g, 26.8 mmol) were added to 200 ml of THF and stirred. Potassium carbonate (13.5 g, 97.3 mmol) was dissolved in water and added. After sufficient stirring, the mixture was refluxed. Then, bis(tri-tert-butylphosphine)palladium (0) (0.1 g, 0.2 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The obtained product was dissolved in chloroform again, washed with water twice, 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 purified by silica gel column chromatography to produce 11.4 g of compound 2-19 (yield: 69%, MS: [M+H] + =681).

[0702] Synthesis Example 2-20: Preparation of Compound 2-20

[0703]

[0704] Under nitrogen atmosphere, intermediate 2-20-1 (10 g, 23.4 mmol) and intermediate 2-20-2 (9.4 g, 25.8 mmol) were added to 200 ml of THF and stirred. Potassium carbonate (12.9 g, 93.7 mmol) was dissolved in water and added. After sufficient stirring, the mixture was refluxed. Then, bis(tri-tert-butylphosphine)palladium (0) (0.1 g, 0.2 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. The obtained product was dissolved in chloroform again, washed with water twice, 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 purified by silica gel column chromatography to produce 9 g of compound 2-20 (yield: 58%, MS: [M+H] + =667).

[0705] Synthesis Example 2-21: Preparation of Compound 2-21

[0706]

[0707] Under a nitrogen atmosphere, intermediate 2-21-1 (10 g, 23.4 mmol) and intermediate 2-21-2 (10.6 g, 25.8 mmol) were added to 200 ml of THF and stirred. Potassium carbonate (12.9 g, 93.7 mmol) was dissolved in water and added. After sufficient stirring, the mixture was refluxed. Then, bis(tri-tert-butylphosphine)palladium (0) (0.1 g, 0.2 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. The obtained product was dissolved in chloroform again, washed with water twice, 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 purified by silica gel column chromatography to produce 10.7 g of compound 2-21 (yield: 64%, MS: [M+H] + =717).

[0708] Synthesis Example 2-22: Preparation of Compound 2-22

[0709]

[0710] Under a nitrogen atmosphere, intermediate 2-22-1 (10 g, 23.4 mmol) and intermediate 2-22-2 (11.3 g, 25.8 mmol) were added to 200 ml of THF and stirred. Potassium carbonate (12.9 g, 93.7 mmol) was dissolved in water and added. After sufficient stirring, the mixture was refluxed. Then, bis(tri-tert-butylphosphine)palladium (0) (0.1 g, 0.2 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, the organic layer and the aqueous layer were separated, and the organic layer was distilled. The obtained product was dissolved in chloroform again, washed with water twice, 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 purified by silica gel column chromatography to produce 9 g of compound 2-22 (yield: 52%, MS: [M+H] + =743).

[0711] Synthesis Example 2-23: Preparation of Compound 2-23

[0712]

[0713] Under a nitrogen atmosphere, intermediate 2-23-1 (10 g, 23.4 mmol) and intermediate 2-23-2 (10.1 g, 25.8 mmol) were added to 200 ml of THF and stirred. Potassium carbonate (12.9 g, 93.7 mmol) was dissolved in water and added. After sufficient stirring, the mixture was refluxed. Then, bis(tri-tert-butylphosphine)palladium (0) (0.1 g, 0.2 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. The obtained product was dissolved in chloroform again, washed with water twice, 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 purified by silica gel column chromatography to produce 9.1 g of compound 2-23 (yield: 56%, MS: [M+H] + =697).

[0714] Comparative Example 1: Fabrication of an organic light-emitting device

[0715] 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.

[0716] 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 A-1 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 electron suppression layer was formed by vacuum deposition of the following EB-1 compound.

[0717] Next, the compound 1-1 prepared in the above-mentioned synthesis example 1-1 and the following Dp-7 compound were vacuum-deposited at a weight ratio of 98:2 on the above-mentioned EB-1 vapor-deposited film to form Thickness of the red emitting layer.

[0718] 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 thickness of is evaporated to form a cathode.

[0719]

[0720] In the above process, the evaporation rate of organic matter is maintained / sec, the lithium fluoride at the cathode maintains / sec evaporation speed, aluminum maintains The evaporation speed is 2×10 / sec. During evaporation, the vacuum degree is maintained at 2×10 -7 ~5×10 -6 A support is provided to produce an organic light-emitting device.

[0721] Comparative Examples 2 to 15

[0722] An organic light-emitting device was manufactured by the same method as in Comparative Example 1, except that the compounds described in Table 1 below were used instead of Compound 1-1.

[0723] Example 1 to Example 120

[0724] In the organic light-emitting device of Comparative Example 1, the organic light-emitting device was manufactured by the same method as Comparative Example 1, except that the compound of Chemical Formula 1 as the first host and the compound of Chemical Formula 2 as the second host described in Tables 2 to 4 were co-evaporated in a weight ratio of 1:1 instead of Compound 1-1.

[0725] Comparative Examples 16 to 63

[0726] In the organic light-emitting device of Comparative Example 1, the organic light-emitting device was manufactured by the same method as the above-mentioned Comparative Example 1, except that the comparative compounds C-1 to C-12 compounds recorded in the following Tables 5 and 6 as the first host and the compound of Chemical Formula 2 as the second host were co-evaporated in a 1:1 ratio instead of compound 1-1.

[0727]

[0728] Experimental Example 1: Device Characteristics Evaluation

[0729] When current was applied to the organic light-emitting devices prepared in Examples 1 to 120 and Comparative Examples 1 to 63, the results (15 mA / cm 2 The voltage, efficiency and lifespan were measured (baseline), and the results are shown in the following Tables 1 to 6. The lifespan T95 refers to the time required for the luminance to decrease from the initial luminance (10,000 nits) to 95%.

[0730] [Table 1]

[0731] distinguish main body Driving voltage(V) Efficiency (cd / A) Lifespan T95(hr) Emitting color Comparative Example 1 Compound 1-1 3.91 16.0 141 red Comparative Example 2 Compound 1-2 3.84 16.1 143 red Comparative Example 3 Compound 1-3 3.76 17.5 141 red Comparative Example 4 Compound 1-12 3.97 16.3 144 red Comparative Example 5 Compound 1-13 3.93 16.1 147 red Comparative Example 6 Compound 1-14 3.94 16.1 140 red Comparative Example 7 Compound 1-22 4.02 16.5 141 red Comparative Example 8 Compound 1-23 3.98 15.3 145 red Comparative Example 9 Compound 1-24 4.04 16.1 137 red Comparative Example 10 Compound 1-32 3.82 16.3 134 red Comparative Example 11 Compound 1-33 3.98 17.4 153 red Comparative Example 12 Compound 1-34 3.91 17.2 151 red Comparative Example 13 Compound 1-36 3.94 18.4 157 red Comparative Example 14 Compound 1-37 3.92 17.7 157 red Comparative Example 15 Compound 1-40 3.93 18.7 160 red

[0732] [Table 2]

[0733]

[0734]

[0735] [Table 3]

[0736]

[0737]

[0738] [Table 4]

[0739]

[0740]

[0741] [Table 5]

[0742]

[0743]

[0744] [Table 6]

[0745]

[0746] As shown in the above table, the organic light-emitting device of the embodiment using both the first compound represented by the above chemical formula 1 and the second compound represented by the above chemical formula 2 as the main material of the light-emitting layer shows the same or superior luminous efficiency, low driving voltage and significantly improved life characteristics compared with the organic light-emitting device of the comparative example using only one of the compounds represented by the above chemical formulas 1 and 2, or neither of them.

[0747] Specifically, the device according to the embodiment shows high efficiency and long life compared with the device of the comparative example using the compound represented by the above chemical formula 1 as a single host. In addition, the device according to the embodiment also improves efficiency and life characteristics compared with the device of the comparative example using the comparative example compounds C-1 to C-12 as the first host and the compound represented by the above chemical formula 2 as the second host. It is thus confirmed that when the combination of the first compound represented by the above chemical formula 1 and the second compound represented by the above chemical formula 2 is used as a common host, energy transfer to the red dopant is effectively achieved in the red light-emitting layer. It can be judged that this is because the first compound has high stability for electrons and holes. In addition, it is judged that because the second compound is used at the same time, the amount of holes increases, and at the same time, electrons and holes maintain a more stable balance in the red light-emitting layer.

[0748] Therefore, it can be confirmed that when the first compound and the second compound are used as the host material of the organic light-emitting device at the same time, the driving voltage, luminous efficiency and / or life characteristics of the organic light-emitting device can be improved. In this regard, considering that the luminous efficiency and life characteristics of the organic light-emitting device are usually in a trade-off relationship with each other, it can be considered that the organic light-emitting device using the combination of the compounds of the present invention shows significantly improved device characteristics compared with the comparative example device.

[0749] [Explanation of symbols]

[0750] 1: Substrate 2: Anode

[0751] 3: Light-emitting layer 4: Cathode

[0752] 5: Hole injection layer 6: Hole transport layer

[0753] 7: Electron suppression layer 8: Hole blocking layer

[0754] 9: Electron injection and transport layer.

Claims

1. An organic light-emitting device, wherein: include: a first electrode; a second electrode disposed opposite to the first electrode; as well as A light-emitting layer is provided between the first electrode and the second electrode, The light-emitting layer includes a first compound represented by the following Chemical Formula 1 and a second compound represented by the following Chemical Formula 2: Chemical formula 1 In the chemical formula 1, X1 to X3 are each independently N or CH, provided that at least two of X1 to X3 are N, Ar1 and Ar2 are each independently substituted or unsubstituted C 6-30 aryl; or substituted or unsubstituted heteroaryl, Z is independently hydrogen or deuterium, or two adjacent Zs are combined with each other to form a benzene ring which is unsubstituted or substituted with deuterium, n is an integer from 0 to 6, and A is a substituent represented by the following chemical formula 1-1, Chemical formula 1-1 In the chemical formula 1-1, R1 to R4 are each independently hydrogen or deuterium, or two adjacent ones of R1 to R4 are combined with each other to form a benzene ring which is unsubstituted or substituted with deuterium, D refers to deuterium, and m is an integer from 0 to 6, Chemical formula 2 In the chemical formula 2, T1 to T4 are each independently an unsubstituted or deuterium-substituted benzene ring, L1 and L2 are each independently a single bond; or an unsubstituted or deuterated C 6-20 Arylene, Ar3 and Ar4 are each independently substituted or unsubstituted C 6-30 aryl; or substituted or unsubstituted heteroaryl, and In the chemical formulas 1 and 2, the heteroaryl group is a dibenzofuranyl group, a dibenzothiophenyl group or a carbazolyl group, and The term "substituted or unsubstituted" refers to a substituted or unsubstituted 1-10 The alkyl group and the phenyl group may be substituted or unsubstituted with one or more substituents, or may be substituted or unsubstituted with a substituent in which two or more substituents among the substituents exemplified above are linked together.

2. The organic light emitting device according to claim 1, wherein: X1 to X3 are all N.

3. The organic light emitting device according to claim 1, wherein: The first compound is represented by any one of the following chemical formulas 3-1 to 3-7: In the chemical formulas 3-1 to 3-7, R is each independently hydrogen or deuterium, and A, Ar1 and Ar2 are the same as defined in claim 1.

4. The organic light emitting device according to claim 1, wherein: Ar1 and Ar2 are each independently selected from any one of the following groups:

5. The organic light emitting device according to claim 1, wherein: A is any one of the substituents represented by the following chemical formulas a1 to a4:

6. The organic light emitting device according to claim 1, wherein: The first compound is any one selected from the following compounds:

7. The organic light emitting device according to claim 1, wherein: The second compound is represented by the following chemical formula 2-1: Chemical formula 2-1 In the chemical formula 2-1, D refers to deuterium, r and s are each independently an integer from 0 to 7, and The definitions of L1, L2, Ar3 and Ar4 are the same as those in claim 1.

8. The organic light emitting device according to claim 1, wherein: L1 and L2 are each independently a single bond, a phenylene group or a naphthylene group.

9. The organic light emitting device according to claim 1, wherein: Ar3 and Ar4 are each independently selected from any one of the following groups:

10. The organic light emitting device according to claim 1, wherein: The second compound is represented by the following chemical formula 2-2: Chemical formula 2-2 In the chemical formula 2-2, L1 and L2 are each independently a single bond, a phenylene group or a naphthylene group, and Ar3 and Ar4 are the same as defined in claim 1.

11. The organic light emitting device according to claim 1, wherein: The second compound is any one selected from the following compounds:

12. The organic light emitting device according to claim 1, wherein: The first compound and the second compound are included in a weight ratio of 99:1 to 1:99.

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