Compound and organic light-emitting device containing the same

Abstract

The present disclosure provides compounds and organic light-emitting devices including the same.

Description

Technical Field

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims the benefit of Korean Patent Application No. 10-2021-0023634 filed in the Korean Intellectual Property Office on February 22, 2021, and Korean Patent Application No. 10-2022-0022275 filed in the Korean Intellectual Property Office on February 21, 2022, the entire contents of which are incorporated herein by reference.

[0003] The present disclosure relates to compounds and organic light-emitting devices including the same. Background Art

[0004] Generally, the organic light emitting phenomenon refers to the phenomenon of converting electrical energy into light energy by using organic materials. Organic light emitting devices using the organic light emitting phenomenon have characteristics such as wide viewing angle, excellent contrast, fast response time, excellent brightness, driving voltage and response speed, and therefore many studies have been conducted.

[0005] An organic light-emitting device generally has a structure including an anode, a cathode, and an organic material layer between the anode and the cathode. The organic material layer often has a multilayer structure including different materials to improve the efficiency and stability of the organic light-emitting device. For example, the organic material layer may be formed of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. In the structure of the organic light-emitting device, if a voltage is applied between two electrodes, holes are injected from the anode into the organic material layer, and electrons are injected from the cathode into the organic material layer, and when the injected holes and electrons meet each other, excitons are formed, and light is emitted when the excitons fall to the ground state again.

[0006] There is a continuing need to develop new materials for organic materials used in organic light emitting devices as described above.

[0007] [Prior art literature]

[0008] [Patent Document]

[0009] (Patent Document 0001) Korean Unexamined Patent Publication No. 10-2000-0051826 Summary of the invention

[0010] Technical issues

[0011] An object of the present disclosure is to provide a compound and an organic light-emitting device including the same.

[0012] Technical Solution

[0013] According to one aspect of the present disclosure, a compound represented by the following Chemical Formula 1 is provided:

[0014] [Chemical formula 1]

[0015]

[0016] Wherein, in Chemical Formula 1,

[0017] L is a single bond; substituted or unsubstituted C 6-60 or a substituted or unsubstituted C containing one or more heteroatoms of N, O and S 2-60 Heteroarylene,

[0018] L1 and L2 are each independently a single bond; or a substituted or unsubstituted C 6-60 Arylene,

[0019] Ar1 and Ar2 are each independently substituted or unsubstituted C 6-60 or a substituted or unsubstituted C containing one or more heteroatoms of N, O and S 2-60 Heteroaryl,

[0020] L' is a single bond; or a substituted or unsubstituted C 6-60 Arylene,

[0021] Q is substituted or unsubstituted C 6-60 Aryl,

[0022] R is deuterium; or a phenyl group substituted with deuterium, and

[0023] n is an integer of 1 to 8.

[0024] According to another aspect of the present disclosure, an organic light-emitting device is provided, which includes: a first electrode; a second electrode arranged opposite to the first electrode; and one or more organic material layers arranged between the first electrode and the second electrode, wherein one or more of the organic material layers contains a compound represented by Chemical Formula 1.

[0025] Beneficial Effects

[0026] The compound represented by Chemical Formula 1 may be used as a material of an organic material layer in an organic light-emitting device, and may improve efficiency, achieve low driving voltage, and / or improve lifespan characteristics in the organic light-emitting device. BRIEF DESCRIPTION OF THE DRAWINGS

[0027] Figure 1 An example of an organic light emitting device including a substrate 1, an anode 2, a light emitting layer 3 and a cathode 4 is shown.

[0028] Figure 2An example of an organic light emitting device including a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light emitting layer 3, an electron transport layer 8, an electron injection layer 9 and a cathode 4 is shown. DETAILED DESCRIPTION

[0029] Hereinafter, embodiments of the present disclosure will be described in more detail to facilitate understanding of the present invention.

[0030] (Definition of terms)

[0031] As used in this article, the symbol It refers to the bond to another substituent.

[0032] As used herein, the term "substituted or unsubstituted" means unsubstituted or substituted with one or more substituents selected from the following: deuterium, halogen group, nitro, hydroxyl, carbonyl, ester group, imide group, amino, phosphine oxide group, alkoxy, aryloxy, alkylthio, arylthio, alkylsulfonyl, arylsulfonyl, silyl, boron, alkyl, cycloalkyl, alkenyl, aryl, aralkyl, aralkenyl, alkylaryl, alkylamino, aralkylamino, heteroarylamine, arylamine, arylphosphino, and heteroaryl containing at least one of N, O and S atoms, or unsubstituted or substituted with substituents connected by two or more substituents in the substituents exemplified above. For example, "substituents connected by two or more substituents" can be biphenyl. That is, the biphenyl can be an aryl, or it can also be interpreted as a substituent connected by two phenyls. In one example, the term "substituted or unsubstituted" can be understood to mean "unsubstituted or substituted with a moiety selected from deuterium, halogen, nitrile, C 1-10 Alkyl, C 1-10 Alkoxy and C 6-20 In addition, the term "substituted with one or more substituents" may be understood to mean, for example, "substituted with 1 to 5 substituents", or "substituted with 1 to 2 substituents".

[0033] In the present disclosure, the carbon number of the carbonyl group is not particularly limited, but is preferably 1 to 40. Specifically, it may be a substituent having the following structure, but is not limited thereto.

[0034]

[0035] In the present disclosure, the ester group may have a structure in which 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, it may be a substituent having the following structure, but is not limited thereto.

[0036]

[0037] In the present disclosure, the carbon number of the imide group is not particularly limited, but is preferably 1 to 25.

[0038] Specifically, it may be a substituent having the following structure, but is not limited thereto.

[0039]

[0040] In the present disclosure, the silyl group specifically includes trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl and the like, but is not limited thereto.

[0041] In the present disclosure, the boryl group specifically includes a trimethylboryl group, a triethylboryl group, a tert-butyldimethylboryl group, a triphenylboryl group, and a phenylboryl group, but is not limited thereto.

[0042] In the present disclosure, examples of halogen groups include fluorine, chlorine, bromine, or iodine.

[0043] In the present disclosure, the alkyl group may be linear or branched, and the carbon number thereof is not particularly limited, but is preferably 1 to 40. According to one embodiment, the carbon number of the alkyl group is 1 to 20. According to another embodiment, the carbon number of the alkyl group is 1 to 10. According to another embodiment, specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, 1-ethyl-propyl, 1,1-dimethylpropyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, isohexyl, 1-methylhexyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 5-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2,4,4-trimethyl-1-pentyl, 2,4,4-trimethyl-2-pentyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, etc., but are not limited thereto.

[0044] In the present disclosure, the alkenyl group may be linear or branched, and the carbon number thereof is not particularly limited, but is preferably 2 to 40. According to one embodiment, the carbon number of the alkenyl group is 2 to 20. According to another embodiment, the carbon number of the alkenyl group is 2 to 10. According to yet another embodiment, the carbon number of the alkenyl group is 2 to 6. Specific examples thereof include 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-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, phenyl group, styryl group, etc., but are not limited thereto.

[0045] In the present disclosure, the cycloalkyl group is not particularly limited, but its carbon number is preferably 3 to 60. According to one embodiment, the carbon number of the cycloalkyl group is 3 to 30. According to another embodiment, the carbon number of the cycloalkyl group is 3 to 20. According to yet another embodiment, the carbon number of the cycloalkyl group is 3 to 6. Specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and the like, but are not limited thereto.

[0046] In the present disclosure, the aryl group is not particularly limited, but its carbon number is preferably 6 to 60, and it may be a monocyclic aryl group or a polycyclic aryl group having aromaticity. 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. As a monocyclic aryl group, the aryl group may be phenyl, biphenyl, terphenyl, etc., but is not limited thereto. Polycyclic aryl groups include naphthyl, anthracenyl, phenanthrenyl, triphenylene, pyrenyl, base, etc., but not limited thereto.

[0047] In the present disclosure, the heteroaryl group is a heteroaryl group containing one or more hetero atoms of O, N, Si and S as hetero atoms, and the carbon number thereof is not particularly limited, but is preferably 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, dibenzofuranyl and the like, but are not limited thereto.

[0048] In the present disclosure, the aryl in aralkyl, aralkenyl, alkylaryl, arylamine and arylsilyl is the same as the aforementioned example of aryl. In the present disclosure, the alkyl in aralkyl, alkylaryl and alkylamine is the same as the aforementioned example of alkyl. In the present disclosure, the heteroaryl in heteroarylamine applies the aforementioned description of heteroaryl. In the present disclosure, the alkenyl in aralkenyl is the same as the aforementioned example of alkenyl. In the present disclosure, the aforementioned description of aryl can be applied, except that arylene is a divalent group. In the present disclosure, the aforementioned description of heteroaryl can be applied, except that heteroarylene is a divalent group. In the present disclosure, the aforementioned description of aryl or cycloalkyl can be applied, except that the hydrocarbon ring is not a monovalent group but is formed by combining two substituents. In the present disclosure, the aforementioned description of heteroaryl can be applied, except that the heterocyclic ring is not a monovalent group but is formed by combining two substituents.

[0049] (Compound)

[0050] Meanwhile, the present disclosure provides a compound represented by Chemical Formula 1.

[0051] Specifically, the compound represented by Chemical Formula 1 has a structure in which the 1-position of the benzene ring is substituted with a carbazole-9-yl group, the 3-position is substituted with a triazine group, and the 5-position is substituted with an aryl group. In addition, the compound may have a structure in which the carbon at the 8-position of dibenzofuran / dibenzothiophene is unsubstituted or substituted with a deuterium-substituted aryl group.

[0052] In particular, the compound has a structure in which the carbazole-9-yl substituent is substituted with at least one deuterium or a deuterium-substituted phenyl group and the carbons at the 2-position, 4-position, and 6-position of the benzene ring are not substituted with deuterium. Such a compound may have increased intramolecular electronic stability compared to a compound having no deuterium in the molecule and a compound in which at least one of the carbons at the 2-position, 4-position, and 6-position of the benzene ring is substituted with deuterium. In addition, since the compound has a carbazole-9-yl structure substituted with deuterium or a deuterium-substituted phenyl group, the compound has a stronger bond energy in the molecule than a compound having no deuterium due to the characteristic that the bond energy of the CD bond is greater than the bond energy of the CH bond, thereby improving material stability.

[0053] Therefore, an organic light emitting device using the compound may not only exhibit low driving voltage but also improve lifespan characteristics.

[0054] In one embodiment, L can be a single bond; unsubstituted or deuterated C 6-20 or an unsubstituted or deuterated C containing one heteroatom of O and S 2-20 Heteroarylene.

[0055] Specifically, L may be a single bond, a phenylene group, a biphenyldiyl group, a naphthylene group, or a dibenzofuranyl group or a dibenzothiophenylene group.

[0056] For example, L is a single bond or one selected from the following:

[0057]

[0058] In addition, in one embodiment, L1 and L2 can each independently be a single bond or an unsubstituted or deuterated C 6-20 Arylene.

[0059] Specifically, L1 and L2 may each independently be a single bond or a phenylene group. In other words, L1 and L2 may each independently be a single bond, a 1,2-phenylene group, a 1,3-phenylene group, or a 1,4-phenylene group.

[0060] For example, L1 and L2 are both single bonds; or

[0061] One of L1 and L2 is a single bond and the other may be 1,2-phenylene, 1,3-phenylene, or 1,4-phenylene.

[0062] Here, L1 and L2 may be the same as each other. Alternatively, L1 and L2 may be different.

[0063] Furthermore, in one embodiment, Ar1 and Ar2 are each independently unsubstituted or selected from deuterium, C 1-10 Alkyl and C 6-20 One or more substituents in the aryl group replace the C 6-20 Aryl; or unsubstituted or selected from deuterium, C 1-10 Alkyl and C 6-20 One or more substituents in the aryl group substituted with one or more heteroatoms of N, O and S 2-60 Heteroaryl.

[0064] Specifically, Ar1 and Ar2 are each independently a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group, a triphenylene group, a fluorenyl group, a dibenzofuranyl group, a dibenzothienyl group, or a carbazolyl group,

[0065] Wherein Ar1 and Ar2 may be unsubstituted or substituted with one or more substituents selected from deuterium, methyl and phenyl.

[0066] Specifically, Ar1 and Ar2 are each independently a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group, a triphenylene group, a fluorenyl group, a dibenzofuranyl group, a dibenzothienyl group, or a carbazolyl group,

[0067] wherein Ar1 and Ar2 may be unsubstituted or substituted with 1 to 5 substituents selected from deuterium, methyl and phenyl.

[0068] More specifically, Ar1 and Ar2 may each independently be a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group, a triphenylene group, a 9,9-dimethylfluorenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, or a 9-phenylcarbazolyl group.

[0069] For example, Ar1 and Ar2 may each independently be any one selected from the following, but are not limited thereto:

[0070]

[0071] Here, Ar1 and Ar2 may be the same as each other. Alternatively, Ar1 and Ar2 may be different.

[0072] In addition, in one embodiment, at least one of Ar1 and Ar2 may be an unsubstituted or deuterium-substituted C 6-12 Aryl.

[0073] For example, at least one of Ar1 and Ar2 may be

[0074] In one embodiment, when L is not a single bond, both Ar1 and Ar2 may be phenyl.

[0075] More specifically, L is a single bond, and Ar1 and Ar2 are each independently phenyl, phenyl substituted with 5 deuteriums, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, 9,9-dimethylfluorenyl, dibenzofuranyl, dibenzothiophenyl, carbazolyl or 9-phenylcarbazolyl; or

[0076] L is C 6-20 Arylene or C containing one heteroatom of O and S 2-20 The heteroarylene group, as well as Ar1 and Ar2, may both be phenyl.

[0077] Furthermore, in one embodiment, L' can be a single bond, or an unsubstituted or deuterated C 6-20 Arylene.

[0078] More specifically, L' may be a single bond or a phenylene group. In other words, L' may be a single bond, a 1,2-phenylene group, a 1,3-phenylene group, or a 1,4-phenylene group.

[0079] Furthermore, in one embodiment, Q may be unsubstituted or selected from deuterium, C 1-10 Alkyl and C 6-20 One or more substituents in the aryl group replace the C 6-24 Aryl.

[0080] Specifically, Q is a phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group, a triphenylene group, a triphenylene group, or a 9,9-dimethylfluorenyl group.

[0081] wherein Q may be unsubstituted or substituted with deuterium.

[0082] Alternatively, wherein Q may be unsubstituted or substituted with at least one deuterium. More specifically, Q may be unsubstituted, or all carbons in the molecule may be substituted with deuterium.

[0083] For example, Q can be any one selected from the following, but is not limited thereto:

[0084]

[0085] Furthermore, in one embodiment, R may be deuterium or phenyl substituted with 1 to 5 deuteriums.

[0086] For example, R can be deuterium or

[0087] Wherein, n means the number of R, and when n is 2 or more, two or more R may be the same or different from each other. For example, n may be 1, 2, 3, 4, 5, 6, 7 or 8.

[0088] also, Can be any one selected from the following:

[0089]

[0090] In addition, the compound may be represented by any one of the following Chemical Formulas 1-1 to 1-3:

[0091] [Chemical formula 1-1]

[0092]

[0093] [Chemical formula 1-2]

[0094]

[0095] [Chemical formula 1-3]

[0096]

[0097] Among them, in Chemical Formulas 1-1 to 1-3,

[0098] D is deuterium,

[0099] m is 1, 2, 3, 4, 5, or 7, and

[0100] L, L1, L2, Ar1, Ar2, L' and Q are as defined in Chemical Formula 1. Meanwhile, representative examples of the compound represented by Chemical Formula 1 are as follows:

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118] Meanwhile, as an example, the compound represented by Chemical Formula 1 may be prepared by a preparation method as shown in the following Reaction Scheme 1.

[0119] [Reaction Scheme 1]

[0120]

[0121] In Reaction Scheme 1, X is halogen, more preferably bromine or chlorine, and the remaining substituents are the same as defined above.

[0122] Specifically, the compound represented by Chemical Formula 1 can be prepared by Suzuki coupling reaction of reaction materials A1 and A2. At this time, the Suzuki coupling reaction is preferably carried out in the presence of a palladium catalyst and a base, and the reactive group used for the Suzuki coupling reaction can be appropriately changed to a reactive group known in the art. Such a preparation method can be further presented in the preparation examples described below.

[0123] (Organic Light Emitting Devices)

[0124] Meanwhile, the present disclosure provides an organic light-emitting device including the compound represented by Chemical Formula 1. In one example, the present disclosure provides an organic light-emitting device including: a first electrode; a second electrode disposed opposite to the first electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein one or more of the organic material layers includes the compound represented by Chemical Formula 1.

[0125] The organic material layer of the organic light-emitting device of the present disclosure may have a single-layer structure, or it may have a multilayer structure in which two or more organic material layers are stacked. For example, the organic light-emitting device of the present disclosure may have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. as organic material layers. However, the structure of the organic light-emitting device is not limited thereto, and it may include a smaller number of organic material layers.

[0126] In one embodiment, the organic material layer may include a light-emitting layer, wherein the organic material layer including the compound may be the light-emitting layer.

[0127] In another embodiment, the organic material layer may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer, wherein the organic material layer including the compound may be a light emitting layer or an electron transport layer.

[0128] In another embodiment, the organic material layer may include a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, an electron transport layer and an electron injection layer, wherein the organic material layer including the compound may be a light emitting layer or an electron transport layer.

[0129] In yet another embodiment, the organic material layer may include a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer and an electron injection layer, wherein the organic material layer containing the compound may be a light emitting layer or an electron transport layer.

[0130] The organic material layer of the organic light-emitting device of the present disclosure may have a single-layer structure, or it may have a multilayer structure in which two or more organic material layers are stacked. For example, the organic light-emitting device of the present disclosure may have a structure that includes, in addition to the light-emitting layer, a hole injection layer and a hole transport layer between the first electrode and the light-emitting layer, and an electron transport layer and an electron injection layer between the light-emitting layer and the second electrode as organic material layers. However, the structure of the organic light-emitting device is not limited thereto, and it may include a smaller number of organic material layers or a larger number of organic material layers.

[0131] In addition, the organic light-emitting device according to the present disclosure may be a normal organic light-emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate, wherein the first electrode is an anode and the second electrode is a cathode. In addition, the organic light-emitting device according to the present disclosure may be an inverted organic light-emitting device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate, wherein the first electrode is a cathode and the second electrode is an anode. For example, the structure of an organic light-emitting device according to one embodiment of the present disclosure is shown in Figure 1 and Figure 2 middle.

[0132] Figure 1 An example of an organic light emitting device including a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4 is shown. In such a structure, the compound represented by Chemical Formula 1 may be contained in the light emitting layer.

[0133] Figure 2 An example of an organic light emitting device including a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light emitting layer 3, an electron transport layer 8, an electron injection layer 9 and a cathode 4 is shown. In such a structure, the compound represented by Chemical Formula 1 may be contained in the light emitting layer.

[0134] The organic light emitting device according to the present disclosure can be manufactured by materials and methods known in the art, except that at least one of the organic material layers contains the compound represented by Chemical Formula 1. In addition, when the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.

[0135] For example, an organic light-emitting device according to the present disclosure can be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. In this case, the organic light-emitting device can be manufactured as follows: a metal, a conductive metal oxide, or an alloy thereof is deposited on a substrate using a PVD (physical vapor deposition) method such as a sputtering method or an electron beam evaporation method to form an anode, an organic material layer including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer is formed on the anode, and then a material that can be used as a cathode is deposited on the organic material layer. In addition to such a method, an organic light-emitting device can also be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

[0136] In addition, when manufacturing an organic light-emitting device, the compound represented by Chemical Formula 1 can be formed into an organic layer by a solution coating method and a vacuum deposition method. Herein, the solution coating method means spin coating, dip coating, blade coating, inkjet printing, screen printing, spray coating, roller coating, etc., but is not limited thereto.

[0137] In addition to such a method, an organic light emitting device can also be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate (International Publication WO2003 / 012890). However, the manufacturing method is not limited thereto.

[0138] As an example, the first electrode is an anode and the second electrode is a cathode, or alternatively, the first electrode is a cathode and the second electrode is an anode.

[0139] As the anode material, it is generally preferred to use a material with a large work function so that holes can be smoothly injected into the organic material layer. Specific examples of anode materials include: metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; conductive compounds such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline; etc., but are not limited thereto.

[0140] As the cathode material, it is generally preferred to use a material having a small work function so that electrons can be easily injected into the organic material layer. Specific examples of cathode materials include: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer structure materials such as LiF / Al or LiO2 / Al; etc., but are not limited thereto.

[0141] In addition, the hole injection layer is a layer for injecting holes from the electrode, and the hole injection material is preferably a compound that has the ability to transport holes, so it has the effect of injecting holes in the anode and has an excellent hole injection effect on the light-emitting layer or the light-emitting material, preventing the excitons generated in the light-emitting layer from moving to the electron injection layer or the electron injection material, and is also excellent in the ability to form a thin film. Preferably, the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of hole injection materials include metal porphyrins, oligothiophenes, organic materials based on arylamines, organic materials based on hexanitrile hexaazatriphenylene, organic materials based on quinacridone, organic materials based on perylene, anthraquinone, conductive polymers based on polyaniline and based on polythiophene, etc., but are not limited thereto.

[0142] In addition, the hole transport layer is a layer that receives holes from the hole injection layer and transfers the holes to the light-emitting layer. The hole transport material is suitably a material having a large hole mobility, which can receive holes from the anode or the hole injection layer and transfer the holes to the light-emitting layer. The hole transport material includes an organic material based on arylamine, a conductive polymer, a block copolymer having both a conjugated part and a non-conjugated part, etc., but is not limited thereto.

[0143] In addition, the electron blocking layer refers to a layer that is formed on the hole transport layer, preferably disposed in contact with the light-emitting layer, and is used to adjust the hole mobility, prevent excessive movement of electrons, and increase the possibility of hole-electron coupling, thereby improving the efficiency of the organic light-emitting device. The electron blocking layer includes an electron blocking material, and examples of such an electron blocking material may include an organic material based on arylamine, etc., but are not limited thereto.

[0144] In addition, the light-emitting layer may include a host material and a dopant material. A compound represented by Chemical Formula 1 may be used as such a host material. In addition, in addition to the compound represented by Chemical Formula 1, the host material may also include fused aromatic ring derivatives, heterocyclic compounds, and the like. Specific examples of fused aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like. Examples of heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.

[0145] In one embodiment, the light emitting layer may further include a compound represented by the following Chemical Formula 2 in addition to the compound represented by Chemical Formula 1:

[0146] [Chemical formula 2]

[0147]

[0148] Wherein, in Chemical Formula 2,

[0149] Ar'1 and Ar'2 are each independently substituted or unsubstituted C 6-60 or a substituted or unsubstituted C containing one or more heteroatoms of N, O and S 2-60 Heteroaryl,

[0150] R'1 and R'2 are each independently hydrogen; deuterium; C 1-60 Alkyl; C 6-60 or a C containing one or more heteroatoms of N, O and S 2-60 Heteroaryl, and

[0151] r and s are each independently an integer from 0 to 7.

[0152] When the organic light-emitting device also includes the compound represented by Chemical Formula 2, the compound can effectively transfer holes from the host material used for the light-emitting layer to the dopant material, and the possibility of recombination between holes and electrons in the light-emitting layer increases with the compound represented by Chemical Formula 1 having excellent electron transport ability, thereby being able to improve the efficiency and life of the organic light-emitting device.

[0153] According to one embodiment, the compound represented by Chemical Formula 2 may be represented by the following Chemical Formula 2':

[0154] [Chemical Formula 2']

[0155]

[0156] Wherein, in chemical formula 2',

[0157] Ar'1, Ar'2, R'1, R'2, r and s are as defined in Chemical Formula 2.

[0158] In addition, in Chemical Formula 2, Ar'1 and Ar'2 are each independently C 6-20 Aryl, or C containing one heteroatom of N, O and S 2-20 Heteroaryl,

[0159] Ar'1 may be unsubstituted or selected from deuterium and C 6-20 The aryl group is substituted with one or more substituents.

[0160] For example, Ar'1 and Ar'2 can each independently be phenyl, biphenyl, terphenyl, naphthyl, dibenzofuranyl or dibenzothiophenyl.

[0161] Ar'1 may be unsubstituted or selected from deuterium and C 6-20 The aryl group is substituted with one or more substituents.

[0162] In this case, at least one of Ar'1 and Ar'2 may be a phenyl group or a biphenyl group.

[0163] In addition, in Chemical Formula 2, R'1 and R'2 can each independently be hydrogen, deuterium, or C 6-20 Aryl.

[0164] For example, R'1 and R'2 may each independently be hydrogen, deuterium or phenyl, but are not limited thereto.

[0165] Furthermore, r and s, each representing the number of R'1 and R'2, may be 0, 1, 2, 3, 4, 5, 6 or 7, each independently.

[0166] More specifically, r and s may each independently be 0, 1 or 7.

[0167] For example, r+s can be 0 or 1.

[0168] Representative examples of the compound represented by Chemical Formula 2 are as follows:

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177] The compound represented by Chemical Formula 1 and the compound represented by Chemical Formula 2, which are two host materials, may be included in the light emitting layer in a weight ratio of 10:90 to 90:10, for example, in a weight ratio of 50:50.

[0178] Examples of dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, the aromatic amine derivative is a substituted or unsubstituted fused aromatic ring derivative having an arylamino group, and examples thereof include pyrene, anthracene, Diindenopyrene, etc. Styrylamine compounds are compounds in which at least one arylvinyl group is substituted in a substituted or unsubstituted arylamine, wherein one or two or more substituents selected from aryl, silyl, alkyl, cycloalkyl and arylamino are substituted or unsubstituted. Specific examples thereof include styrylamine, styryldiamine, styryltriamine, styryltetramine, etc., but are not limited thereto. In addition, metal complexes include iridium complexes, platinum complexes, etc., but are not limited thereto.

[0179] In addition, the hole blocking layer refers to a layer that is formed on the light-emitting layer, preferably disposed in contact with the light-emitting layer, and is thus used to control electron mobility to prevent excessive movement of holes and increase the possibility of hole-electron combination, thereby improving the efficiency of the organic light-emitting device. The hole blocking layer includes a hole blocking material, and as an example of such a hole blocking material, a compound into which an electron-withdrawing group is introduced, such as an azine derivative including triazine; a triazole derivative; Oxadiazole derivatives; phenanthroline derivatives; phosphine oxide derivatives, but not limited thereto.

[0180] In addition, the electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light-emitting layer, and is formed on the light-emitting layer and the hole blocking layer. The electron transport layer contains an electron transport material, and such an electron transport material is suitably a material having a large electron mobility. Specific examples of electron transport materials include: Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic free radical compounds; hydroxyflavone-metal complexes, etc., but are not limited thereto. Alternatively, fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, Azoles, Oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylene methane, anthrone, and the like and derivatives thereof, metal complex compounds, nitrogen-containing five-membered ring derivatives, and the like may be used together as the electron transport material, but are not limited thereto.

[0181] The electron injection layer is a layer that injects electrons from the electrode and is formed on the electron transport layer. Examples of the electron injection material contained in the electron injection layer include LiF, NaCl, CsF, Li2O, BaO, fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, Azoles, Oxadiazole, thiopyran dioxide, Azoles, Oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenyl methane, anthrone and the like and their derivatives; metal complex compounds; nitrogen-containing 5-membered ring derivatives, etc., but not limited thereto.

[0182] Here, the metal complex compound includes 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) chlorogallium, bis(2-methyl-8-quinoline)(o-cresol) gallium, bis(2-methyl-8-quinoline)(1-naphthol) aluminum, bis(2-methyl-8-quinoline)(2-naphthol) gallium, and the like, but is not limited thereto.

[0183] The organic light emitting device according to the present disclosure may be a bottom emission type device, a top emission type device, or a double-sided emission type device, and in particular, the organic light emitting device may be a bottom emission type light emitting device requiring relatively high light emission efficiency.

[0184] Furthermore, the compound represented by Chemical Formula 1 may be included in an organic solar cell or an organic transistor in addition to an organic light emitting device.

[0185] The preparation of the compound represented by Chemical Formula 1 and an organic light-emitting device including the same will be described in detail in the following examples. However, these examples are provided for illustrative purposes only and are not intended to limit the scope of the present disclosure.

[0186] Preparation Example 1: Preparation of Compound A-3

[0187] 1) Preparation of Compound A-1

[0188]

[0189] Under nitrogen atmosphere, bromobenzene (100g, 641.2mmol) and (3-chloro-5-fluorophenyl) boronic acid (111.6g, 641.2mmol) are added to 2000mL tetrahydrofuran, and the mixture is stirred and refluxed. Then, potassium carbonate (265.9g, 1923.6mmol) is dissolved in 266mL water and added thereto, and the mixture is fully stirred, and then tetratriphenylphosphine palladium (22.2g, 19.2mmol) is added. After reacting for 1 hour, the reaction mixture is cooled to room temperature, and then the organic layer and the water layer are separated, and the organic layer is distilled. It is added again to 2642mL chloroform, dissolved and washed with water twice, and then the organic layer is separated, anhydrous magnesium sulfate is added, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is recrystallized from chloroform and ethyl acetate to prepare gray solid compound A-1 (80.6g, 61%, MS:[M+H] + =207).

[0190] 2) Preparation of Compound A-2

[0191]

[0192] A-1 (100 g, 485.4 mmol) and 9H-carbazole-1,3,4,5,6,8-d6 (84 g, 485.4 mmol) were added to 2000 mL of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, sodium tert-butoxide (140 g, 1456.1 mmol) was added thereto, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium (7.4 g, 14.6 mmol) was added. After reacting for 4 hours, the reaction mixture was cooled to room temperature, and the resulting solid was filtered. The solid was added to 5229 mL of chloroform, dissolved, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column using chloroform and ethyl acetate to prepare a white solid compound A-2 (111.6 g, 64%, MS: [M+H] + =360.1).

[0193] 3) Preparation of Compound A-3

[0194]

[0195] A-2 (50 g, 139.2 mmol) and bis(pinacolato)diboron (38.9 g, 153.1 mmol) were added to 1000 mL of 1,4-diborane under nitrogen atmosphere. alkane, and the mixture is stirred and refluxed. Then, potassium acetate (40.1g, 417.7mmol) is added thereto, and the mixture is fully stirred, and then palladium dibenzylideneacetone palladium (2.4g, 4.2mmol) and tricyclohexylphosphine (2.3g, 8.4mmol) are added. After reacting for 5 hours, the reaction mixture is subjected to filtration treatment to remove salt, and the filtered organic layer is then distilled. It is added again to 628mL chloroform, dissolved and washed with water twice. The organic layer is then separated, anhydrous magnesium sulfate is added, stirred and then filtered. The filtrate is distilled under reduced pressure. The concentrated compound is recrystallized from chloroform and ethanol to prepare gray solid compound A-3 (51.5g, 82%, MS: [M+H] + =452.3).

[0196] Preparation Example 2: Preparation of Compound B-3

[0197] 1) Preparation of compound B-1

[0198]

[0199] Under nitrogen atmosphere, 1- bromobenzene -2,3,4,5,6-d5 (100g, 621.2mmol) and (3- chloro-5-fluorophenyl) boronic acid (108.1g, 621.2mmol) are added to 2000mL tetrahydrofuran, and the mixture is stirred and refluxed. Then, potassium carbonate (257.6g, 1863.5mmol) is dissolved in 258mL water and added thereto, and the mixture is fully stirred, and tetratriphenyl-phosphine palladium (21.5g, 18.6mmol) is then added. After reacting for 1 hour, the reaction mixture is cooled to room temperature, and then the organic layer and the water layer are separated, and the organic layer is distilled. It is added again to 2622mL chloroform, dissolved, and washed twice with water, and then the organic layer is separated, anhydrous magnesium sulfate is added, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare a gray solid compound B-1 (80 g, 61%, MS: [M+H] + =212.1).

[0200] 2) Preparation of compound B-2

[0201]

[0202] B-1 (100 g, 473.8 mmol) and 9H-carbazole-1,3,4,5,6,8-d6 (82 g, 473.8 mmol) were added to 2000 mL of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, sodium tert-butoxide (136.6 g, 1421.4 mmol) was added thereto, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium (7.3 g, 14.2 mmol) was added. After reacting for 1 hour, the reaction mixture was cooled to room temperature, and the resulting solid was filtered. The solid was added to 5176 mL of chloroform, dissolved, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column using chloroform and ethyl acetate to prepare a white solid compound B-2 (103.5 g, 60%, MS: [M+H] + =365.2).

[0203] 3) Preparation of compound B-3

[0204]

[0205] B-2 (50 g, 137.3 mmol) and bis(pinacolato)diboron (38.4 g, 151 mmol) were added to 1000 mL of 1,4-diborane under nitrogen atmosphere. alkane, and the mixture is stirred and refluxed. Then, potassium acetate (39.6g, 411.9mmol) is added thereto, and the mixture is fully stirred, and then palladium dibenzylideneacetone palladium (2.4g, 4.1mmol) and tricyclohexylphosphine (2.3g, 8.2mmol) are added. After reacting for 4 hours, the reaction mixture is subjected to filtration treatment to remove salt, and the filtered organic layer is then distilled. It is added again to 626mL chloroform, dissolved and washed with water twice. The organic layer is then separated, anhydrous magnesium sulfate is added, stirred and then filtered. The filtrate is distilled under reduced pressure. The concentrated compound is recrystallized from chloroform and ethanol to prepare gray solid compound B-3 (32g, 51%, MS: [M+H] + =457.3).

[0206] Preparation Example 3: Preparation of Compound C-3

[0207] 1) Preparation of Compound C-2

[0208]

[0209] B-1 (100 g, 473.8 mmol) and 9H-carbazole-1,2,3,4,5,6,7,8-d8 (83 g, 473.8 mmol) were added to 2000 mL of xylene under a nitrogen atmosphere, and the mixture was stirred and refluxed. Then, sodium tert-butoxide (136.6 g, 1421.4 mmol) was added thereto, and the mixture was fully stirred, and then bis(tri-tert-butylphosphine)palladium (7.3 g, 14.2 mmol) was added. After reacting for 5 hours, the reaction mixture was cooled to room temperature, and the resulting solid was filtered. The solid was added to 5205 mL of chloroform, dissolved, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by a silica gel column using chloroform and ethyl acetate to prepare a white solid compound C-2 (131.9 g, 76%, MS: [M+H] + =367.2).

[0210] 2) Preparation of Compound C-3

[0211]

[0212] C-2 (50 g, 137.3 mmol) and bis(pinacolato)diboron (38.4 g, 151 mmol) were added to 1000 mL of 1,4-diborane under nitrogen atmosphere. alkane, and the mixture is stirred and refluxed. Then, potassium acetate (39.6g, 411.9mmol) is added thereto, and the mixture is fully stirred, and then palladium dibenzylideneacetone palladium (2.4g, 4.1mmol) and tricyclohexylphosphine (2.3g, 8.2mmol) are added. After reacting for 5 hours, the reaction mixture is subjected to filtration treatment to remove salt, and the filtered organic layer is then distilled. It is added again to 626mL chloroform, dissolved and washed with water twice. The organic layer is then separated, anhydrous magnesium sulfate is added, stirred, and then filtered. The filtrate is distilled under reduced pressure. The concentrated compound is recrystallized from chloroform and ethanol to prepare gray solid compound C-3 (48.9g, 78%, MS: [M+H] + =457.3).

[0213] Preparation Example 4: Preparation of Compound D-3

[0214] 1) Preparation of compound D-1

[0215]

[0216] 2- chloro-4,6-diphenyl-1,3,5-triazine (100g, 200.3mmol) and (3- chloro-5-fluorophenyl) boronic acid (68.7g, 200.3mmol) are added to 2000mL tetrahydrofuran under a nitrogen atmosphere, and the mixture is stirred and refluxed. Then, potassium carbonate (83.1g, 601mmol) is dissolved in 83mL water and added thereto, and the mixture is fully stirred, and tetrakis triphenyl-phosphine palladium (6.9g, 6mmol) is then added. After reacting for 2 hours, the reaction mixture is cooled to room temperature, and the organic layer and the water layer are separated, and the organic layer is distilled. It is added again to 1447mL chloroform, dissolved, and washed twice with water, and then the organic layer is separated, anhydrous magnesium sulfate is added, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is recrystallized from chloroform and ethyl acetate to prepare gray solid compound D-1 (41.2g, 57%, MS: [M+H] + =362.1).

[0217] 2) Preparation of compound D-2

[0218]

[0219] D-1 (30 g, 83.1 mmol) and 9H-carbazole-1,3,4,5,6,8-d6 (14.4 g, 83.1 mmol) were added to 600 mL of dimethylformamide under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium triphosphate (52.9 g, 249.3 mmol) was then added thereto, and the mixture was fully stirred. After reacting for 5 hours, the reaction mixture was cooled to room temperature, and the organic layer was subjected to filtration to remove salts, and the filtered organic layer was then distilled. It was added again to 427 mL of chloroform, dissolved and washed twice with water. The organic layer was then separated, anhydrous magnesium sulfate was added, stirred, and then filtered. The filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare a gray solid compound D-2 (25.6 g, 60%, MS: [M+H] + =515.2).

[0220] 3) Preparation of compound D-3

[0221]

[0222] D-2 (50 g, 97.2 mmol) and bis(pinacolato)diboron (27.2 g, 107 mmol) were added to 1000 mL of 1,4-diborane under nitrogen atmosphere. alkane, and the mixture is stirred and refluxed. Then, potassium acetate (28g, 291.7mmol) is added thereto, and the mixture is fully stirred, and then palladium dibenzylideneacetone palladium (1.7g, 2.9mmol) and tricyclohexylphosphine (1.6g, 5.8mmol) are added. After reacting for 7 hours, the reaction mixture is subjected to filtration treatment to remove salt, and the filtered organic layer is then distilled. It is added again to 590mL chloroform, dissolved and washed with water twice. The organic layer is then separated, anhydrous magnesium sulfate is added, stirred, and then filtered. The filtrate is distilled under reduced pressure. The concentrated compound is recrystallized from chloroform and ethanol to prepare gray solid compound D-3 (35.4g, 60%, MS: [M+H] + =607.3).

[0223] Synthesis Example 1: Preparation of Compound 1

[0224]

[0225] A-3 (20g, 44.3mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (11.8g, 44.3mmol) are added to 400mL tetrahydrofuran under a nitrogen atmosphere, and the mixture is stirred and refluxed. Then, potassium carbonate (18.4g, 133mmol) is dissolved in 18mL water and added thereto, and the mixture is fully stirred, and tetrakis triphenylphosphine palladium (1.5g, 1.3mmol) is then added. After reacting for 3 hours, the reaction mixture is cooled to room temperature, and then the organic layer and the water layer are separated, and the organic layer is distilled. It is added again to 1233mL chloroform, dissolved, and washed twice with water, and then the organic layer is separated, anhydrous magnesium sulfate is added, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is recrystallized from chloroform and ethyl acetate to prepare gray solid compound 1 (19.2g, 78%, MS: [M+H] + =557.3).

[0226] Synthesis Example 2: Preparation of Compound 2

[0227]

[0228] A-3 (20g, 44.3mmol) and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (15.2g, 44.3mmol) are added to 400mL tetrahydrofuran under a nitrogen atmosphere, and the mixture is stirred and refluxed. Then, potassium carbonate (18.4g, 133mmol) is dissolved in 18mL water and added thereto, and the mixture is fully stirred, and then tetrakis triphenylphosphine palladium (1.5g, 1.3mmol) is added. After reacting for 2 hours, the reaction mixture is cooled to room temperature, and then the organic layer and the aqueous layer are separated, and the organic layer is distilled. It is added again to 1401mL chloroform, dissolved and washed twice with water, and then the organic layer is separated, anhydrous magnesium sulfate is added, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is recrystallized from chloroform and ethyl acetate to prepare gray solid compound 2 (17.1g, 61%, MS: [M+H] + =633.3).

[0229] Synthesis Example 3: Preparation of Compound 3

[0230]

[0231] A-3 (20g, 44.3mmol) and 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (15.2g, 44.3mmol) are added to 400mL tetrahydrofuran under a nitrogen atmosphere, and the mixture is stirred and refluxed. Then, potassium carbonate (18.4g, 133mmol) is dissolved in 18mL water and added thereto, and the mixture is fully stirred, and then tetratriphenyl-phosphine palladium (1.5g, 1.3mmol) is added. After reacting for 3 hours, the reaction mixture is cooled to room temperature, and the organic layer and the aqueous layer are separated, and the organic layer is distilled. It is added again to 1401mL chloroform, dissolved and washed twice with water, and then the organic layer is separated, anhydrous magnesium sulfate is added, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is recrystallized from chloroform and ethyl acetate to prepare gray solid compound 3 (15.7g, 56%, MS: [M+H] + =633.3).

[0232] Synthesis Example 4: Preparation of Compound 4

[0233]

[0234] A-3 (20g, 44.3mmol) and 2-chloro-4-(dibenzo [b, d] furan-4-yl) -6-phenyl -1,3,5- triazine (15.8g, 44.3mmol) are added to 400mL tetrahydrofuran under a nitrogen atmosphere, and the mixture is stirred and refluxed. Then, potassium carbonate (18.4g, 133mmol) is dissolved in 18mL water and added thereto, and the mixture is fully stirred, and tetrakis triphenylphosphine palladium (1.5g, 1.3mmol) is then added. After reacting for 3 hours, the reaction mixture is cooled to room temperature, and the organic layer and the aqueous layer are separated, and the organic layer is distilled. It is added again to 1432mL chloroform, dissolved and washed twice with water, and the organic layer is separated, anhydrous magnesium sulfate is added, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is recrystallized from chloroform and ethyl acetate to prepare gray solid compound 4 (14.9g, 52%, MS: [M+H] + =647.3).

[0235] Synthesis Example 5: Preparation of Compound 5

[0236]

[0237] A-3 (20g, 44.3mmol) and 2-chloro-4-(dibenzo[b, d]thiophene-4-yl)-6-phenyl-1,3,5-triazine (16.5g, 44.3mmol) are added to 400mL tetrahydrofuran under a nitrogen atmosphere, and the mixture is stirred and refluxed. Then, potassium carbonate (18.4g, 133mmol) is dissolved in 18mL water and added thereto, and the mixture is fully stirred, and tetratriphenylphosphine palladium (1.5g, 1.3mmol) is then added. After reacting for 3 hours, the reaction mixture is cooled to room temperature, and the organic layer and the aqueous layer are separated, and the organic layer is distilled. It is added again to 1468mL chloroform, dissolved, and washed twice with water, and then the organic layer is separated, anhydrous magnesium sulfate is added, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is recrystallized from chloroform and ethyl acetate to prepare gray solid compound 5 (21.1g, 72%, MS: [M+H] + =663.2).

[0238] Synthesis Example 6: Preparation of Compound 6

[0239]

[0240] A-3 (20g, 44.3mmol) and 2-chloro-4-(naphthalene-2-yl)-6-phenyl-1,3,5-triazine (14.1g, 44.3mmol) are added to 400mL tetrahydrofuran under a nitrogen atmosphere, and the mixture is stirred and refluxed. Then, potassium carbonate (18.4g, 133mmol) is dissolved in 18mL water and added thereto, and the mixture is fully stirred, and tetrakis triphenylphosphine palladium (1.5g, 1.3mmol) is then added. After reacting for 3 hours, the reaction mixture is cooled to room temperature, and the organic layer and the water layer are separated, and the organic layer is distilled. It is added again to 1344mL chloroform, dissolved, and washed twice with water, and then the organic layer is separated, anhydrous magnesium sulfate is added, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is recrystallized from chloroform and ethyl acetate to prepare gray solid compound 6 (19.1g, 71%, MS: [M+H] + =607.3).

[0241] Synthesis Example 7: Preparation of Compound 7

[0242]

[0243] A-3 (20g, 44.3mmol) and 2-chloro-4-(4-(naphthalene-1-yl)phenyl)-6-phenyl-1,3,5-triazine (17.4g, 44.3mmol) are added to 400mL tetrahydrofuran under a nitrogen atmosphere, and the mixture is stirred and refluxed. Then, potassium carbonate (18.4g, 133mmol) is dissolved in 18mL water and added thereto, and the mixture is fully stirred, and tetrakis triphenylphosphine palladium (1.5g, 1.3mmol) is then added. After reacting for 2 hours, the reaction mixture is cooled to room temperature, and the organic layer and the aqueous layer are separated, and the organic layer is distilled. It is added again to 1512mL chloroform, dissolved and washed twice with water, and the organic layer is separated, anhydrous magnesium sulfate is added, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is recrystallized from chloroform and ethyl acetate to prepare gray solid compound 7 (23.6g, 78%, MS: [M+H] + =683.3).

[0244] Synthesis Example 8: Preparation of Compound 8

[0245]

[0246] A-3 (20g, 44.3mmol) and 2-chloro-4-(dibenzo [b, d] furan-3-yl) -6-phenyl -1,3,5- triazine (15.8g, 44.3mmol) are added to 400mL tetrahydrofuran under a nitrogen atmosphere, and the mixture is stirred and refluxed. Then, potassium carbonate (18.4g, 133mmol) is dissolved in 18mL water and added thereto, and the mixture is fully stirred, and tetrakis triphenylphosphine palladium (1.5g, 1.3mmol) is then added. After reacting for 3 hours, the reaction mixture is cooled to room temperature, and the organic layer and the water layer are separated, and the organic layer is distilled. It is added again to 1432mL chloroform, dissolved, and washed twice with water, and then the organic layer is separated, anhydrous magnesium sulfate is added, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is recrystallized from chloroform and ethyl acetate to prepare gray solid compound 8 (18.9g, 66%, MS: [M + H] + =647.3).

[0247] Synthesis Example 9: Preparation of Compound 9

[0248]

[0249] A-3 (20g, 44.3mmol) and 2- (3- bromophenyl) -4,6- diphenyl -1,3,5- triazine (17.2g, 44.3mmol) are added to 400mL tetrahydrofuran under a nitrogen atmosphere, and the mixture is stirred and refluxed. Then, potassium carbonate (18.4g, 133mmol) is dissolved in 18mL water and added thereto, and the mixture is fully stirred, and tetrakis triphenyl-phosphine palladium (1.5g, 1.3mmol) is then added. After reacting for 3 hours, the reaction mixture is cooled to room temperature, and the organic layer and the aqueous layer are separated, and the organic layer is distilled. It is added again to 1401mL chloroform, dissolved, and washed twice with water, and then the organic layer is separated, anhydrous magnesium sulfate is added, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is recrystallized from chloroform and ethyl acetate to prepare gray solid compound 9 (15.4g, 55%, MS: [M + H] + =633.3).

[0250] Synthesis Example 10: Preparation of Compound 10

[0251]

[0252] A-3 (20g, 44.3mmol) and 2-chloro-4-phenyl-6-(phenyl-d5)-1,3,5-triazine (12.3g, 44.3mmol) are added to 400mL tetrahydrofuran under a nitrogen atmosphere, and the mixture is stirred and refluxed. Then, potassium carbonate (18.4g, 133mmol) is dissolved in 18mL water and added thereto, and the mixture is fully stirred, and tetrakis triphenylphosphine palladium (1.5g, 1.3mmol) is then added. After reacting for 1 hour, the reaction mixture is cooled to room temperature, and the organic layer and the water layer are separated, and the organic layer is distilled. It is added again to 1244mL chloroform, dissolved and washed twice with water, and then the organic layer is separated, anhydrous magnesium sulfate is added, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is recrystallized from chloroform and ethyl acetate to prepare gray solid compound 10 (15.7g, 63%, MS: [M+H] + =562.3).

[0253] Synthesis Example 11: Preparation of Compound 11

[0254]

[0255] B-3 (20g, 43.8mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (11.7g, 43.8mmol) are added to 400mL tetrahydrofuran under a nitrogen atmosphere, and the mixture is stirred and refluxed. Then, potassium carbonate (18.2g, 131.5mmol) is dissolved in 18mL water and added thereto, and the mixture is fully stirred, and tetrakis triphenylphosphine palladium (1.5g, 1.3mmol) is then added. After reacting for 3 hours, the reaction mixture is cooled to room temperature, and then the organic layer and the water layer are separated, and the organic layer is distilled. It is added again to 1230mL chloroform, dissolved, and washed twice with water, and then the organic layer is separated, anhydrous magnesium sulfate is added, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is recrystallized from chloroform and ethyl acetate to prepare gray solid compound 11 (18.2g, 74%, MS: [M+H] + =562.3).

[0256] Synthesis Example 12: Preparation of Compound 12

[0257]

[0258] B-3 (20g, 43.8mmol) and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (15g, 43.8mmol) are added to 400mL tetrahydrofuran under a nitrogen atmosphere, and the mixture is stirred and refluxed. Then, potassium carbonate (18.2g, 131.5mmol) is dissolved in 18mL water and added thereto, and the mixture is fully stirred, and tetrakis triphenylphosphine palladium (1.5g, 1.3mmol) is then added. After reacting for 2 hours, the reaction mixture is cooled to room temperature, and the organic layer and the aqueous layer are separated, and the organic layer is distilled. It is added again to 1397mL chloroform, dissolved and washed twice with water, and the organic layer is separated, anhydrous magnesium sulfate is added, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is recrystallized from chloroform and ethyl acetate to prepare gray solid compound 12 (15.4g, 55%, MS: [M+H] + =638.3).

[0259] Synthesis Example 13: Preparation of Compound 13

[0260]

[0261] B-3 (20g, 43.8mmol) and 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (15g, 43.8mmol) are added to 400mL tetrahydrofuran under a nitrogen atmosphere, and the mixture is stirred and refluxed. Then, potassium carbonate (18.2g, 131.5mmol) is dissolved in 18mL water and added thereto, and the mixture is fully stirred, and tetrakis triphenylphosphine palladium (1.5g, 1.3mmol) is then added. After reacting for 2 hours, the reaction mixture is cooled to room temperature, and the organic layer and the aqueous layer are separated, and the organic layer is distilled. It is added again to 1397mL chloroform, dissolved and washed twice with water, and the organic layer is separated, anhydrous magnesium sulfate is added, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is recrystallized from chloroform and ethyl acetate to prepare gray solid compound 13 (14.8g, 53%, MS: [M+H] + =638.3).

[0262] Synthesis Example 14: Preparation of Compound 14

[0263]

[0264] B-3 (20g, 43.8mmol) and 2-chloro-4-(dibenzo [b, d] furan-4-yl) -6-phenyl -1,3,5- triazine (15.7g, 43.8mmol) are added to 400mL tetrahydrofuran under a nitrogen atmosphere, and the mixture is stirred and refluxed. Then, potassium carbonate (18.2g, 131.5mmol) is dissolved in 18mL water and added thereto, and the mixture is fully stirred, and then tetratriphenyl-phosphine palladium (1.5g, 1.3mmol) is added. After reacting for 1 hour, the reaction mixture is cooled to room temperature, and then the organic layer and the water layer are separated, and the organic layer is distilled. It is added again to 1427mL chloroform, dissolved and washed twice with water, and then the organic layer is separated, anhydrous magnesium sulfate is added, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare a gray solid compound 14 (22.3 g, 78%, MS: [M+H] + =652.3).

[0265] Synthesis Example 15: Preparation of Compound 15

[0266]

[0267] B-3 (20g, 43.8mmol) and 2-chloro-4-(dibenzo [b, d] thiophene-4-yl) -6-phenyl -1,3,5-triazine (16.4g, 43.8mmol) are added to 400mL tetrahydrofuran under a nitrogen atmosphere, and the mixture is stirred and refluxed. Then, potassium carbonate (18.2g, 131.5mmol) is dissolved in 18mL water and added thereto, and the mixture is fully stirred, and then tetratriphenyl-phosphine palladium (1.5g, 1.3mmol) is added. After reacting for 1 hour, the reaction mixture is cooled to room temperature, and then the organic layer and the water layer are separated, and the organic layer is distilled. It is added again to 1462mL chloroform, dissolved and washed twice with water, and then the organic layer is separated, anhydrous magnesium sulfate is added, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare a gray solid compound 15 (17.8 g, 61%, MS: [M+H] + =668.2).

[0268] Synthesis Example 16: Preparation of Compound 16

[0269]

[0270] B-3 (20g, 43.8mmol) and 2-chloro-4-(naphthalene-2-yl)-6-phenyl-1,3,5-triazine (13.9g, 43.8mmol) are added to 400mL tetrahydrofuran under a nitrogen atmosphere, and the mixture is stirred and refluxed. Then, potassium carbonate (18.2g, 131.5mmol) is dissolved in 18mL water and added thereto, and the mixture is fully stirred, and tetrakis triphenylphosphine palladium (1.5g, 1.3mmol) is then added. After reacting for 2 hours, the reaction mixture is cooled to room temperature, and the organic layer and the water layer are separated, and the organic layer is distilled. It is added again to 1340mL chloroform, dissolved and washed twice with water, and then the organic layer is separated, anhydrous magnesium sulfate is added, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is recrystallized from chloroform and ethyl acetate to prepare gray solid compound 16 (13.9g, 52%, MS: [M+H] + =612.3).

[0271] Synthesis Example 17: Preparation of Compound 17

[0272]

[0273] B-3 (20g, 43.8mmol) and 2-chloro-4-(4-(naphthalene-1-yl)phenyl)-6-phenyl-1,3,5-triazine (17.2g, 43.8mmol) are added to 400mL tetrahydrofuran under a nitrogen atmosphere, and the mixture is stirred and refluxed. Then, potassium carbonate (18.2g, 131.5mmol) is dissolved in 18mL water and added thereto, and the mixture is fully stirred, and tetrakis triphenylphosphine palladium (1.5g, 1.3mmol) is then added. After reacting for 3 hours, the reaction mixture is cooled to room temperature, and the organic layer and the aqueous layer are separated, and the organic layer is distilled. It is added again to 1506mL chloroform, dissolved and washed twice with water, and the organic layer is separated, anhydrous magnesium sulfate is added, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is recrystallized from chloroform and ethyl acetate to prepare gray solid compound 17 (16.3g, 54%, MS: [M+H] + =688.3).

[0274] Synthesis Example 18: Preparation of Compound 18

[0275]

[0276] Under nitrogen atmosphere, B-3 (20g, 43.8mmol) and 2-chloro-4-(dibenzo [b, d] furan-3-yl) -6-phenyl -1,3,5- triazine (15.7g, 43.8mmol) are added to 400mL tetrahydrofuran, and the mixture is stirred and refluxed. Then, potassium carbonate (18.2g, 131.5mmol) is dissolved in 18mL water and added thereto, and the mixture is fully stirred, and then tetratriphenyl-phosphine palladium (1.5g, 1.3mmol) is added. After reacting for 2 hours, the reaction mixture is cooled to room temperature, and then the organic layer and the water layer are separated, and the organic layer is distilled. It is added again to 1427mL chloroform, dissolved and washed with water twice, and then the organic layer is separated, anhydrous magnesium sulfate is added, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare a gray solid compound 18 (15.1 g, 53%, MS: [M+H] + =652.3).

[0277] Synthesis Example 19: Preparation of Compound 19

[0278]

[0279] B-3 (20g, 43.8mmol) and 2- (3- bromophenyl) -4,6- diphenyl -1,3,5- triazine (17g, 43.8mmol) are added to 400mL tetrahydrofuran under a nitrogen atmosphere, and the mixture is stirred and refluxed. Then, potassium carbonate (18.2g, 131.5mmol) is dissolved in 18mL water and added thereto, and the mixture is fully stirred, and tetrakis triphenyl-phosphine palladium (1.5g, 1.3mmol) is then added. After reacting for 3 hours, the reaction mixture is cooled to room temperature, and the organic layer and the aqueous layer are separated, and the organic layer is distilled. It is added again to 1408mL chloroform, dissolved, and washed twice with water, and then the organic layer is separated, anhydrous magnesium sulfate is added, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is recrystallized from chloroform and ethyl acetate to prepare gray solid compound 19 (22.5g, 80%, MS: [M + H] + =643.3).

[0280] Synthesis Example 20: Preparation of Compound 20

[0281]

[0282] B-3 (100g, 219.2mmol) and 9-(4-chloro-6-phenyl-1,3,5-triazine-2-yl)-9H-carbazole (78g, 219.2mmol) are added to 2000mL tetrahydrofuran under a nitrogen atmosphere, and the mixture is stirred and refluxed. Then, potassium carbonate (90.9g, 657.5mmol) is dissolved in 91mL water and added thereto, and the mixture is fully stirred, and then tetratriphenylphosphine palladium (7.6g, 6.6mmol) is added. After reacting for 2 hours, the reaction mixture is cooled to room temperature, and the organic layer and the aqueous layer are separated, and the organic layer is distilled. It is added again to 2850mL chloroform, dissolved and washed twice with water, and then the organic layer is separated, anhydrous magnesium sulfate is added, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is recrystallized from chloroform and ethyl acetate to prepare gray solid compound 20 (102.6g, 72%, MS: [M+H] + =651.3).

[0283] Synthesis Example 21: Preparation of Compound 21

[0284]

[0285] C-3 (20g, 43.6mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (11.7g, 43.6mmol) are added to 400mL tetrahydrofuran under a nitrogen atmosphere, and the mixture is stirred and refluxed. Then, potassium carbonate (18.1g, 130.9mmol) is dissolved in 18mL water and added thereto, and the mixture is fully stirred, and tetrakis triphenylphosphine palladium (1.5g, 1.3mmol) is then added. After reacting for 2 hours, the reaction mixture is cooled to room temperature, and then the organic layer and the water layer are separated, and the organic layer is distilled. It is added again to 1229mL chloroform, dissolved, and washed twice with water, and then the organic layer is separated, anhydrous magnesium sulfate is added, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is recrystallized from chloroform and ethyl acetate to prepare gray solid compound 21 (13g, 53%, MS: [M+H] + =564.3).

[0286] Synthesis Example 22: Preparation of Compound 22

[0287]

[0288] D-3 (20g, 32.9mmol) and 4-bromo-1,1'-biphenyl (7.6g, 32.9mmol) are added to 400mL tetrahydrofuran under a nitrogen atmosphere, and the mixture is stirred and refluxed. Then, potassium carbonate (13.6g, 98.6mmol) is dissolved in 14mL water and added thereto, and the mixture is fully stirred, and tetrakis triphenylphosphine palladium (1.1g, 1mmol) is then added. After reacting for 1 hour, the reaction mixture is cooled to room temperature, and then the organic layer and the aqueous layer are separated, and the organic layer is distilled. It is added again to 1040mL chloroform, dissolved and washed twice with water, and then the organic layer is separated, anhydrous magnesium sulfate is added, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is recrystallized from chloroform and ethyl acetate to prepare gray solid compound 22 (13.3g, 64%, MS: [M+H] + =633.3).

[0289] Synthesis Example 23: Preparation of Compound 23

[0290]

[0291] D-3 (20g, 32.9mmol) and 3-bromo-1,1'-biphenyl (7.6g, 32.9mmol) are added to 400mL tetrahydrofuran under a nitrogen atmosphere, and the mixture is stirred and refluxed. Then, potassium carbonate (13.6g, 98.6mmol) is dissolved in 14mL water and added thereto, and the mixture is fully stirred, and tetrakis triphenylphosphine palladium (1.1g, 1mmol) is then added. After reacting for 2 hours, the reaction mixture is cooled to room temperature, and then the organic layer and the water layer are separated, and the organic layer is distilled. It is added again to 1040mL chloroform, dissolved and washed twice with water, and then the organic layer is separated, anhydrous magnesium sulfate is added, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is recrystallized from chloroform and ethyl acetate to prepare gray solid compound 23 (16.2g, 78%, MS: [M+H] + =633.3).

[0292] Synthesis Example 24: Preparation of Compound 24

[0293]

[0294] Under nitrogen atmosphere, D-3 (20g, 32.9mmol) and 2-bromonaphthalene (6.8g, 32.9mmol) are added to 400mL tetrahydrofuran, and the mixture is stirred and refluxed. Then, potassium carbonate (13.6g, 98.6mmol) is dissolved in 14mL water and added thereto, and the mixture is fully stirred, and then tetratriphenylphosphine palladium (1.1g, 1mmol) is added. After reacting for 3 hours, the reaction mixture is cooled to room temperature, and then the organic layer and the water layer are separated, and the organic layer is distilled. It is added again in 997mL chloroform, dissolved and washed with water twice, and then the organic layer is separated, anhydrous magnesium sulfate is added, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is recrystallized from chloroform and ethyl acetate to prepare gray solid compound 24 (13g, 65%, MS:[M+H] + =607.3).

[0295] Synthesis Example 25: Preparation of Compound 25

[0296]

[0297] Under nitrogen atmosphere, D-3 (20g, 32.9mmol) and 9-bromophenanthrene (8.4g, 32.9mmol) are added to 400mL tetrahydrofuran, and the mixture is stirred and refluxed. Then, potassium carbonate (13.6g, 98.6mmol) is dissolved in 14mL water and added thereto, and the mixture is fully stirred, and then tetratriphenylphosphine palladium (1.1g, 1mmol) is added. After reacting for 3 hours, the reaction mixture is cooled to room temperature, and then the organic layer and water layer are separated, and the organic layer is distilled. It is added again in 1079mL chloroform, dissolved and washed with water twice, and then the organic layer is separated, anhydrous magnesium sulfate is added, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is recrystallized from chloroform and ethyl acetate to prepare gray solid compound 25 (13.6g, 63%, MS:[M+H] + =657.3).

[0298] Synthesis Example 26: Preparation of Compound 26

[0299]

[0300] Under nitrogen atmosphere, D-3 (20g, 32.9mmol) and 2- (4- bromophenyl) naphthalene (9.3g, 32.9mmol) are added to 400mL tetrahydrofuran, and the mixture is stirred and refluxed. Then, potassium carbonate (13.6g, 98.6mmol) is dissolved in 14mL water and added thereto, and the mixture is fully stirred, then tetratriphenyl-phosphine palladium (1.1g, 1mmol) is added. After reacting for 3 hours, the reaction mixture is cooled to room temperature, then the organic layer and the water layer are separated, and the organic layer is distilled. It is added again in 1122mL chloroform, dissolved, and washed twice with water, then the organic layer is separated, anhydrous magnesium sulfate is added, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is recrystallized from chloroform and ethyl acetate to prepare gray solid compound 26 (15g, 67%, MS: [M+H] + =683.3).

[0301] Synthesis Example 27: Preparation of Compound 27

[0302]

[0303] D-3 (20g, 32.9mmol) and 2-bromotriphenylene (11.7g, 32.9mmol) are added to 400mL tetrahydrofuran under nitrogen atmosphere, and the mixture is stirred and refluxed. Then, potassium carbonate (13.6g, 98.6mmol) is dissolved in 14mL water and added thereto, and the mixture is fully stirred, and then tetratriphenyl-phosphine palladium (1.1g, 1mmol) is added. After reacting for 1 hour, the reaction mixture is cooled to room temperature, and then the organic layer and water layer are separated, and the organic layer is distilled. It is added again in 1161mL chloroform, dissolved and washed with water twice, and then the organic layer is separated, anhydrous magnesium sulfate is added, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is recrystallized from chloroform and ethyl acetate to prepare gray solid compound 27 (16.7g, 72%, MS:[M+H] + =707.3).

[0304] Synthesis Example 28: Preparation of Compound 28

[0305]

[0306] D-3 (20g, 32.9mmol) and 4-bromo-1,1'-biphenyl-2',3',4',5',6'-d5 (7.8g, 32.9mmol) are added to 400mL tetrahydrofuran under a nitrogen atmosphere, and the mixture is stirred and refluxed. Then, potassium carbonate (13.6g, 98.6mmol) is dissolved in 14mL water and added thereto, and the mixture is fully stirred, and tetrakis triphenylphosphine palladium (1.1g, 1mmol) is then added. After reacting for 3 hours, the reaction mixture is cooled to room temperature, and then the organic layer and the water layer are separated, and the organic layer is distilled. It is added again to 1048mL chloroform, dissolved, and washed twice with water, and then the organic layer is separated, anhydrous magnesium sulfate is added, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound is recrystallized from chloroform and ethyl acetate to prepare gray solid compound 28 (11.1g, 53%, MS: [M+H] + =638.3).

[0307] Synthesis Example 29: Preparation of Compound 29

[0308]

[0309] A-3 (20g, 44.3mmol) and 2-(8-bromodibenzo [b, d] furan-1-yl) -4,6-diphenyl -1,3,5-triazine (21.1g, 44.3mmol) are added to 400mL tetrahydrofuran under a nitrogen atmosphere, and the mixture is stirred and refluxed. Then, potassium carbonate (18.4g, 133mmol) is dissolved in 18mL water and added thereto, and the mixture is fully stirred, and then tetratriphenyl-phosphine palladium (1.5g, 1.3mmol) is added. After reacting for 3 hours, the reaction mixture is cooled to room temperature, and then the organic layer and the water layer are separated, and the organic layer is distilled. It is added again to 1601mL chloroform, dissolved, and washed twice with water, and then the organic layer is separated, anhydrous magnesium sulfate is added, stirred, then filtered, and the filtrate is distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to prepare a gray solid compound 29 (23.4 g, 73%, MS: [M+H] + =723.3).

[0310] Example 1: Fabrication of an organic light-emitting device

[0311] It is coated with a thickness of The glass substrate of ITO (indium tin oxide) film is put into the distilled water that comprises the cleaning agent dissolved therein, and by ultrasonic cleaning.In this case, the cleaning agent used is the product commercially available from Fischer Co., and distilled water is the distilled water filtered twice by using the filter commercially available from Millipore Co..ITO was cleaned 30 minutes, then repeated ultrasonic cleaning twice for 10 minutes by using distilled water.After finishing with distilled water cleaning, with isopropyl alcohol, acetone and methanol solvent, substrate is carried out ultrasonic cleaning and drying, and is transferred to plasma cleaning machine afterwards.Then, substrate was cleaned 5 minutes with oxygen plasma, then transferred to vacuum evaporator.

[0312] On the thus prepared ITO transparent electrode, the following compound HI-1 was thermally vacuum deposited onto The following compound HT-1 was thermally vacuum deposited onto the hole injection layer. The hole transport layer is formed by vacuum depositing the following compound HT-2 on the HT-1 deposition layer. to form a hole blocking layer.

[0313] Then, the compound 1 prepared in the previous synthesis example 1, the following compound YGH-1 and the following phosphorescent dopant YGD-1 as the light-emitting layer were vacuum deposited at a weight ratio of 44:44:12 on the HT-2 deposition layer to form a layer with a thickness of of the luminous layer.

[0314] The following compounds ET-1 to ET-2 were vacuum deposited on the light-emitting layer. To form an electron transport layer, the following compound ET-2 and LiF were vacuum deposited on the electron transport layer at a weight ratio of 8:2 to form a film with a thickness of Aluminum is deposited on the electron injection layer to to form a cathode.

[0315]

[0316] During the above process, the deposition rate of the organic material is maintained at to The aluminum deposition rate was kept at The vacuum degree during deposition was maintained at 1×10 -7 Up to 5×10 -8 Entrust.

[0317] Examples 2 to 29

[0318] An organic light-emitting device was manufactured in the same manner as in Example 1, except that a compound shown in Table 1 below was used as one of the host materials for the light-emitting layer in Example 1 instead of Compound 1 of Synthesis Example 1.

[0319] At this time, the structures of the compounds used in Examples 1 to 29 are as follows.

[0320]

[0321]

[0322]

[0323] Comparative Examples 1 to 4

[0324] An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compounds shown in Table 1 below were used instead of Compound 1 of Synthesis Example 1 as one of the host materials for the light-emitting layer in Example 1. At this time, Compounds CE1 to CE4 of Table 1 below were as follows.

[0325]

[0326] Experimental Example 1: Evaluation of device characteristics

[0327] At 10mA / cm 2 The voltage and efficiency of the organic light-emitting devices manufactured in the embodiments and comparative examples were measured at a current density of 50 mA / cm 2The lifespan was measured at a current density of . The results are shown in Table 1 below. At this time, LT95 means the time required for the luminance to decrease to 95% of the initial luminance.

[0328] [Table 1]

[0329]

[0330]

[0331] As shown in Table 1, it can be determined that the organic light-emitting device of the embodiment using the compound represented by Chemical Formula 1 as a host material of the light-emitting layer exhibits significantly improved life characteristics without reducing efficiency, compared with the organic light-emitting device of the comparative example using a compound having a structure different from the compound represented by Chemical Formula 1. Therefore, considering that the luminous efficiency and life characteristics of the organic light-emitting device generally have a trade-off relationship, it can be determined that the compound of the present disclosure can improve the characteristics of the organic light-emitting device compared with the compound of the comparative example.

[0332] [Explanation of Reference Numerals]

[0333] 1: Substrate 2: Anode

[0334] 3: Light-emitting layer 4: Cathode

[0335] 5: Hole injection layer 6: Hole transport layer

[0336] 7: Electron blocking layer 8: Electron transport layer

[0337] 9: Electron injection layer

Claims

1. A compound represented by the following chemical formula 1: [Chemical formula 1] in, In Chemical Formula 1, L is a single bond; unsubstituted or deuterated C 6-20 or an unsubstituted or deuterated C containing one heteroatom of O and S 2-20 Heteroarylene, L1 and L2 are each independently a single bond; or an unsubstituted or deuterated C 6-20 Arylene, Ar1 and Ar2 are each independently unsubstituted or selected from deuterium, C 1-10 Alkyl and C 6-20 One or more substituents in the aryl group replace the C 6-20 Aryl; or unsubstituted or selected from deuterium, C 1-10 Alkyl and C 6-20 One or more substituents in the aryl group substituted with one or more heteroatoms of N, O and S 2-60 Heteroaryl, L' is a single bond; or unsubstituted or deuterated C 6-20 Arylene, Q is unsubstituted or selected from deuterium, C 1-10 Alkyl and C 6-20 One or more substituents in the aryl group replace the C 6-24 Aryl, R is deuterium; or a phenyl group substituted with deuterium, and n is an integer of 1 to 8.

2. The compound according to claim 1, wherein: L is a single bond, a phenylene group, a biphenyldiyl group, a naphthylene group, a dibenzofuranyl group, or a dibenzothiophenylene group.

3. The compound according to claim 1, wherein: L1 and L2 are each independently a single bond or a phenylene group.

4. The compound according to claim 1, wherein: Ar1 and Ar2 are each independently a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a phenanthryl group, a triphenylene group, a fluorenyl group, a dibenzofuranyl group, a dibenzothienyl group, or a carbazolyl group, wherein the Ar1 and the Ar2 are unsubstituted or substituted with one or more substituents selected from deuterium, methyl and phenyl.

5. The compound according to claim 4, wherein: Ar1 and Ar2 are each independently selected from any one of the following:

6. The compound according to claim 1, wherein: At least one of Ar1 and Ar2 is unsubstituted or deuterated C 6-12 Aryl.

7. The compound according to claim 1, wherein: L is a single bond, and Ar1 and Ar2 are each independently phenyl, phenyl substituted with 5 deuteriums, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, 9,9-dimethylfluorenyl, dibenzofuranyl, dibenzothienyl, carbazolyl or 9-phenylcarbazolyl; or L is C 6-20 Arylene or C containing one heteroatom of O and S 2-20 heteroarylene, and both Ar1 and Ar2 are phenyl.

8. The compound according to claim 1, wherein: L' is a single bond or a phenylene group.

9. The compound according to claim 1, wherein: Q is phenyl, biphenyl, naphthyl, phenanthryl, triphenylene, triphenylene or 9,9-dimethylfluorenyl, wherein Q is unsubstituted or substituted with deuterium.

10. The compound according to claim 9, wherein: Q is any one selected from the following:

11. The compound according to claim 1, wherein: R is deuterium, or 12. The compound according to claim 1, wherein: Any one selected from the following:

13. The compound according to claim 1, wherein: The compound is represented by any one of the following chemical formulas 1-1 to 1-3: [Chemical formula 1-1] [Chemical formula 1-2] [Chemical formula 1-3] Among them, in Chemical Formulas 1-1 to 1-3, D is deuterium, m is 1, 2, 3, 4, 5, or 7, and L, L1, L2, Ar1, Ar2, L' and Q are as defined in claim 1.

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

15. An organic light emitting device, comprising: a first electrode; a second electrode disposed opposite to the first electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein one or more of the organic material layers comprises the compound according to any one of claims 1 to 14.

16. The organic light emitting device according to claim 15, wherein: The organic material layer including the compound is a light-emitting layer.

17. The organic light emitting device according to claim 16, wherein: The light-emitting layer further comprises a compound represented by the following Chemical Formula 2: [Chemical formula 2] Wherein, in Chemical Formula 2, Ar'1 and Ar'2 are each independently substituted or unsubstituted C 6-60 or a substituted or unsubstituted C containing one or more heteroatoms of N, O and S 2-60 Heteroaryl, R'1 and R'2 are each independently hydrogen; deuterium; C 1-60 Alkyl; C 6-60 or a C containing one or more heteroatoms of N, O and S 2-60 Heteroaryl, and r and s are each independently an integer from 0 to 7.

18. The organic light emitting device according to claim 17, wherein: The compound represented by Chemical Formula 2 is any one selected from the following compounds:

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