New compound and organic light-emitting device containing the same

Abstract

The present invention provides novel compounds and organic light-emitting devices comprising the same.

Description

Technical Field

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims the benefit of the filing dates of Korean Patent Application No. 10-2018-0098141, filed on August 22, 2018, in the Korean Intellectual Property Office, and Korean Patent Application No. 10-2019-0102578, filed on August 21, 2019, in the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference.

[0003] The present invention relates to novel compounds and organic light-emitting devices comprising 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, and excellent brightness, driving voltage, and response speed, and therefore, many studies have been conducted on them.

[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 continuous 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 Patent Publication No. 10-2000-0051826. Summary of the invention

[0010] Technical issues

[0011] An object of the present invention is to provide novel compounds and organic light-emitting devices comprising the same.

[0012] Technical Solution

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

[0014] [Chemical formula 1]

[0015]

[0016] Wherein, in Chemical Formula 1,

[0017] Y1 is O or S,

[0018] L1 and L2 are each independently a single bond, a substituted or unsubstituted C 6-60 arylene, or a substituted or unsubstituted C containing one or more heteroatoms selected from O, N and S 2-60 Heteroarylene,

[0019] Provided that L2 is bonded to any one of positions *1, *2 and *3,

[0020] A is represented by any one of Chemical Formulas 2 to 4,

[0021] [Chemical formula 2]

[0022]

[0023] [Chemical formula 3]

[0024]

[0025] [Chemical formula 4]

[0026]

[0027] Wherein, in Chemical Formulas 2 to 4,

[0028] X1 to X3 are each independently N or CH, provided that at least two of X1 to X3 are N,

[0029] X4 and X5 are each independently N or CH, provided that at least one of X4 and X5 is N,

[0030] X6 and X7 are each independently N or CH, provided that at least one of X6 and X7 is N,

[0031] Y2 is O or S, and

[0032] Ar1 to Ar4 are each independently substituted or unsubstituted C 6-60 aryl, or a substituted or unsubstituted C 2-60 Heteroaryl,

[0033] Provided that when L2 is bonded to position *3 and A is represented by Chemical Formula 2, Ar2 is a substituted or unsubstituted C 10-60aryl, or a substituted or unsubstituted C 2-60 Heteroaryl.

[0034] In another aspect of the present invention, 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 layers of the organic material layers contain a compound represented by Chemical Formula 1.

[0035] Beneficial Effects

[0036] The compound represented by Chemical Formula 1 may be used as a material of an organic material layer of an organic light-emitting device, and may improve efficiency in the organic light-emitting device, and achieve low driving voltage and / or improve lifespan characteristics. BRIEF DESCRIPTION OF THE DRAWINGS

[0037] 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.

[0038] 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. DETAILED DESCRIPTION

[0039] Hereinafter, embodiments of the present invention will be described in more detail to help understanding of the present invention.

[0040] As used in this article, the symbol It means a bond connecting to another substituent, and a single bond means that there is no separate atom at the portion indicated as L1 and L2.

[0041] As used herein, the term "substituted or unsubstituted" means unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, halogen groups, cyano groups, nitro groups, hydroxyl groups, carbonyl groups, ester groups, imide groups, amino groups, phosphine oxide groups, alkoxy groups, aryloxy groups, alkylthio groups, arylthio groups, alkylsulfonyl groups, arylsulfonyl groups, silyl groups, boron groups, alkyl groups, cycloalkyl groups, alkenyl groups, aryl groups, aralkyl groups, aralkenyl groups, alkylaryl groups, alkylamino groups, aralkylamino groups, heteroarylamine groups, arylamine groups, arylphosphino groups, and heteroaryl groups containing at least one of N, O, and S atoms, or unsubstituted or substituted with substituents connected to two or more of the substituents exemplified above. For example, "substituents connected to two or more substituents" can be biphenyl groups. That is, biphenyl groups can also be aryl groups and can be interpreted as substituents connected to two phenyl groups.

[0042] In the present specification, the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40.

[0043] Specifically, the carbonyl group may be a compound having the following structural formula, but is not limited thereto.

[0044]

[0045] In the present specification, 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, the ester group may be a compound having the following structural formula, but is not limited thereto.

[0046]

[0047] In the present specification, the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25. Specifically, the imide group may be a compound having the following structural formula, but is not limited thereto.

[0048]

[0049] In the present specification, the silyl group specifically includes trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl and the like, but is not limited thereto.

[0050] In the present specification, 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.

[0051] In the present specification, examples of the halogen group include fluorine, chlorine, bromine, or iodine.

[0052] In the present specification, the alkyl group may be linear or branched, and the number of carbon atoms thereof is not particularly limited, but is preferably 1 to 40. According to one embodiment, the number of carbon atoms of the alkyl group is 1 to 20. According to another embodiment, the number of carbon atoms of the alkyl group is 1 to 10. According to yet another embodiment, the number of carbon atoms of 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, 5-methylhexyl and the like, but are not limited thereto.

[0053] In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms thereof 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 yet another embodiment, the number of carbon atoms 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, stilbene, styryl, etc., but are not limited thereto.

[0054] In the present specification, the cycloalkyl group is not particularly limited, but the number of carbon atoms thereof is preferably 3 to 60. According to one embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 30. According to another embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 20. According to yet another embodiment, the number of carbon atoms 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, etc., but are not limited thereto.

[0055] In the present specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and it may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the number of carbon atoms of the aryl group is 6 to 30. According to one embodiment, the number of carbon atoms 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, pyrenyl, peryl, fluorenyl, etc., but are not limited thereto.

[0056] In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spirocyclic structure. In the case where the fluorenyl group is substituted, etc. However, the structure is not limited thereto.

[0057] In the present specification, the heteroaryl group is a heteroaryl group containing one or more of O, N, Si and S as a heteroatom, and the number of carbon atoms 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.

[0058] In this specification, the aryl in aralkyl, aralkenyl, alkylaryl and arylamine is the same as the above-mentioned example of aryl. In this specification, the alkyl in aralkyl, alkylaryl and alkylamine is the same as the above-mentioned example of alkyl. In this specification, the heteroaryl in heteroarylamine can apply the above-mentioned description of heteroaryl. In this specification, the alkenyl in aralkenyl is the same as the above-mentioned example of alkenyl. In this specification, the above-mentioned description of aryl can be applied, except that arylene is a divalent group. In this specification, the above-mentioned description of heteroaryl can be applied, except that heteroarylene is a divalent group. In this specification, the above-mentioned 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 this specification, the above-mentioned description of heteroaryl can be applied, except that the heterocyclic group is not a monovalent group but is formed by combining two substituents.

[0059] On the other hand, one embodiment of the present invention provides a compound represented by Chemical Formula 1. The compound represented by Chemical Formula 1 has a structure in which one side of the benzene ring of the dibenzofuran / dibenzothiophene core is substituted with a substituent A, and the other side of the benzene ring is substituted with a triphenylene group at the remaining portion except for a position symmetrical with respect to a position substituted with the substituent A.

[0060] In addition, in Chemical Formula 1, when L2 is bonded to position *3 and A is represented by Chemical Formula 2, Ar2 is a substituted or unsubstituted C 10-60 Aryl; or a substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S 2-60 Heteroaryl.

[0061] The compound represented by Chemical Formula 1 can be preferably used as a host of a light-emitting layer of an organic light-emitting device, for example, as an n-type host used with a p-type host material. Compared with a compound substituted with a triphenylene group at a symmetrical position relative to a position substituted with a substituent A and a compound in which L2 is bonded to position *3, A is represented by Chemical Formula 2, and both Ar1 and Ar2 are phenyl groups, when the compound represented by Chemical Formula 1 is used as an n-type host, it has an excellent ability to stabilize electrons and thus can maintain the balance of holes and electrons in the light-emitting layer. Therefore, an organic light-emitting device using the compound of the present invention can simultaneously improve efficiency and life characteristics.

[0062] In addition, L1 and L2 can each independently be a single bond or a C 6-20 Arylene.

[0063] For example, L1 and L2 may each independently be a single bond, a phenylene group, or a biphenylene group.

[0064] In this case, at least one of L1 and L2 may be a single bond.

[0065] In addition, when A is represented by Chemical Formula 2, L2 may be bonded to the position *1 or *2. Alternatively, L2 may be bonded to the position *1 or *2.

[0066] In addition, in Chemical Formula 2, X1 to X3 are N; X1 and X2 are N and X3 is CH; or X2 and X3 are N and X1 is CH,

[0067] In Chemical Formula 3, X4 and X5 are N, and

[0068] In Chemical Formula 4, X6 and X7 may be N.

[0069] The compound represented by Chemical Formula 1 can be represented as follows according to the bonding position of L2. Specifically, when L2 is bonded to position *1, Chemical Formula 1 is represented by the following Chemical Formula 1A, when L2 is bonded to position *2, Chemical Formula 1 is represented by the following Chemical Formula 1B, and when L2 is bonded to position *3, Chemical Formula 1 is represented by the following Chemical Formula 1C:

[0070] [Chemical Formula 1A]

[0071]

[0072] [Chemical formula 1B]

[0073]

[0074] [Chemical formula 1C]

[0075]

[0076] Wherein, in Chemical Formulas 1A to 1C,

[0077] Definitions of A, Y1, L1 and L2 are the same as those defined in Chemical Formula 1.

[0078] Furthermore, in Chemical Formula 1A, A may be represented by any one of Chemical Formulas 2 to 4, in Chemical Formula 1B, A may be represented by any one of Chemical Formulas 2 to 4, and in Chemical Formula 1C, A may be represented by Chemical Formula 2 or 3.

[0079] In Chemical Formula 1A,

[0080] Y1 is O or S,

[0081] L1 and L2 are each independently a single bond or C 6-20 arylene, and

[0082] A is represented by any one of Chemical Formulas 2 to 4,

[0083] In Chemical Formula 1B,

[0084] Y1 is O or S,

[0085] L1 and L2 are each independently a single bond or C 6-20 arylene, and

[0086] A is represented by any one of Chemical Formulas 2 to 4,

[0087] In Chemical Formula 1C,

[0088] Y1 is O or S,

[0089] L1 and L2 are each independently a single bond or C 6-20 arylene, and

[0090] A is represented by any one of Chemical Formulas 2 to 4, and

[0091] In chemical formula 2,

[0092] Ar1 can be C 6-20 Aryl; or C containing one atom of O or S 2-20 Heteroaryl, and Ar2 can be C 10-20 Aryl; or C containing one atom of O or S 2-20 Heteroaryl.

[0093] In addition, Ar1 to Ar4 may each independently be C 6-20 Aryl; or C containing one atom of O or S 2-20 However, when L2 is bonded to position *3 and A is represented by Chemical Formula 2, Ar1, Ar3 and Ar4 are each independently C 6-20 Aryl; or C containing one atom of O or S 2-20 Heteroaryl, and Ar2 can be C 10-20 Aryl; or C containing one atom of O or S 2-20 Heteroaryl.

[0094] For example, Ar1 to Ar4 may be each independently a phenyl group, a biphenyl group, a dibenzofuranyl group, or a dibenzothiophenyl group. However, when L2 is bonded to position *3 and A is represented by Chemical Formula 2, Ar1, Ar3, and Ar4 may be each independently a phenyl group, a biphenyl group, a dibenzofuranyl group, or a dibenzothiophenyl group, and Ar2 may be a biphenyl group, a dibenzofuranyl group, or a dibenzothiophenyl group.

[0095] Specifically, for example,

[0096] In Chemical Formula 1A,

[0097] Ar1 to Ar4 are each independently phenyl, biphenyl, dibenzofuranyl, or dibenzothiophenyl,

[0098] In Chemical Formula 1B,

[0099] Ar1 to Ar4 are each independently phenyl, biphenyl, dibenzofuranyl, or dibenzothiophenyl, and

[0100] In Chemical Formula 1C,

[0101] Ar1, Ar3 and Ar4 are each independently phenyl, biphenyl, dibenzofuranyl, or dibenzothiophenyl, and

[0102] Ar2 is a biphenyl group, a dibenzofuranyl group, or a dibenzothiophenyl group.

[0103] In addition, the compound represented by Chemical Formula 1 can be represented as follows according to the structure of A. Specifically, when A is Chemical Formula 2, Chemical Formula 1 is represented by the following Chemical Formula 1D, when A is Chemical Formula 3, Chemical Formula 1 is represented by the following Chemical Formula 1E, and when A is Chemical Formula 4, Chemical Formula 1 is represented by the following Chemical Formula 1F.

[0104] [Chemical formula 1D]

[0105]

[0106] [Chemical formula 1E]

[0107]

[0108] [Chemical formula 1F]

[0109]

[0110] Wherein, in Chemical Formulas 1D to 1F,

[0111] Definitions of Y1, Y2, L1, L2, X1 to X7, and Ar1 to Ar4 are the same as those defined in Chemical Formula 1.

[0112] According to one embodiment, in Formula 1D, L2 is bonded to position *1 or *2, and

[0113] In Formula 1E, L2 is bonded to position *1, *2, or *3,

[0114] In Chemical Formula 1F, L2 may be bonded to position *1, *2, or *3.

[0115] According to one embodiment, Ar1, Ar3 and Ar4 are each independently C 6-20 Aryl; or C containing one atom of O or S 2-20 Heteroaryl, and

[0116] Ar2 can be C 10-20 Aryl; or C containing one atom of O or S 2-20 Heteroaryl.

[0117] For example, in Chemical Formulas 1D to 1F,

[0118] Ar1, Ar3 and Ar4 are each independently a phenyl group, a biphenyl group, a dibenzofuranyl group, or a dibenzothiophenyl group, and Ar2 may be a biphenyl group, a dibenzofuranyl group, or a dibenzothiophenyl group, but is not limited thereto.

[0119] In addition, the above compound may be represented by any one of the following Chemical Formulas 1-1 to 1-6:

[0120]

[0121]

[0122] Among them, in Chemical Formulas 1-1 to 1-6,

[0123] X1 to X3 are N; or X1 and X2 are N, and X3 is CH; or X2 and X3 are N, and X1 is CH,

[0124] Definitions of Y1, L1, L2, Ar1 and Ar2 are the same as those defined in Chemical Formula 1.

[0125] Furthermore, in Chemical Formulas 1-1 to 1-4,

[0126] Ar1 and Ar2 are each independently phenyl, biphenyl, dibenzofuranyl, or dibenzothiophenyl,

[0127] In Chemical Formulas 1-5 and 1-6,

[0128] Ar1 is phenyl, biphenyl, dibenzofuranyl, or dibenzothiophenyl,

[0129] Ar2 may be a biphenyl group, a dibenzofuranyl group, or a dibenzothiophenyl group.

[0130] In addition, the above compound may be represented by any one of Chemical Formulae 1-1 to 1-4.

[0131] For example, the compound may be any one selected from the following compounds:

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139] Meanwhile, the compound represented by Chemical Formula 1 can be prepared, for example, according to a preparation method as shown in the following Reaction Scheme 1. The preparation method can be further illustrated in the preparation examples described below.

[0140] [Reaction Scheme 1]

[0141]

[0142] Wherein, in Reaction Scheme 1, each X is independently a halogen, preferably bromine or chlorine, and the remaining substituents are defined the same as those defined above.

[0143] The above reaction is a step of preparing a compound represented by Chemical Formula 1 via a Suzuki coupling reaction by introducing a substituent A into a raw material. 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 reaction can be changed to a reactive group known in the art. The above preparation method can be further illustrated in the preparation examples described below.

[0144] In another embodiment of the present invention, an organic light-emitting device comprising the compound represented by Chemical Formula 1 is provided. As an example, an organic light-emitting device is provided, which includes: 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 comprises the compound represented by Chemical Formula 1.

[0145] The organic material layer of the organic light-emitting device of the present invention 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 invention may have a structure including a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. as an organic material layer. However, the structure of the organic light-emitting device is not limited thereto, and it may include a smaller number of organic layers.

[0146] In addition, the organic material layer may include a light emitting layer, wherein the light emitting layer includes the compound represented by Chemical Formula 1. In particular, the compound according to the present invention may be used as a host of the light emitting layer. Specifically, the compound according to the present invention may be used as a green phosphorescent host of the light emitting layer.

[0147] In addition, the organic material layer may include a light emitting layer and the light emitting layer may include two or more types of hosts, wherein one of the hosts may be the compound represented by Chemical Formula 1.

[0148] In addition, the organic material layer may include an electron transport layer or an electron injection layer, wherein the electron transport layer or the electron injection layer may include the compound represented by Chemical Formula 1.

[0149] The organic material layer of the organic light-emitting device according to the present invention 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 invention may have a structure in which, in addition to the light-emitting layer, it also includes a hole injection layer and a hole transport layer disposed between the first electrode and the light-emitting layer, and an electron transport layer and an electron injection layer disposed between the light-emitting layer and the second electrode. However, the structure of the organic light-emitting device is not limited thereto, and it may include a smaller number of organic layers or a larger number of organic layers.

[0150] The organic light-emitting device according to the present invention may be a normal type 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 the anode and the second electrode is the cathode. In addition, the organic light-emitting device according to the present invention may be an inverted type 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 the cathode and the second electrode is the 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 2 middle.

[0151] 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.

[0152] 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 one or more layers of the hole injection layer, the hole transport layer, the light-emitting layer and the electron transport layer. Preferably, the compound represented by Chemical Formula 1 may be contained in the light-emitting layer.

[0153] The organic light emitting device according to the present invention can be manufactured by materials and methods known in the art, except that one or more of the organic material layers contain 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.

[0154] For example, the organic light-emitting device according to the present invention 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.

[0155] 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. Here, the solution coating method means spin coating, dip coating, blade coating, inkjet printing, screen printing, spraying, roller coating, etc., but is not limited thereto.

[0156] In addition to such a method, an organic light emitting device may 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.

[0157] As an example, the first electrode is an anode and the second electrode is a cathode, or the first electrode is a cathode and the second electrode is an anode.

[0158] As the anode material, generally, it is 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 polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

[0159] As the cathode material, generally, it is 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 the cathode material include: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; and multilayer structure materials such as LiF / Al or LiO2 / Al, etc., but are not limited thereto.

[0160] The hole injection layer is a layer for injecting holes from the electrode, and the hole injection material is preferably such a compound: it has the ability to transport holes, so it has the effect of injecting holes in the anode and the excellent effect of injecting holes into 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 having excellent film forming ability. The HOMO (highest occupied molecular orbital) of the preferred 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.

[0161] 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, and it can receive holes from the anode or the hole injection layer and transfer the holes to the light-emitting layer. Specific examples thereof include organic materials based on arylamine, conductive polymers, block copolymers in which conjugated parts and non-conjugated parts exist simultaneously, etc., but are not limited thereto.

[0162] The electron blocking layer refers to a layer formed on the hole transport layer and preferably arranged in contact with the light-emitting layer to adjust the hole mobility, prevent the electrons from moving excessively, and increase the possibility of hole-electron combination, thereby improving the efficiency of the organic light-emitting element. The electron blocking layer contains an electron blocking material, and examples of such electron blocking materials include, but are not limited to, an arylamine-based organic material and the like.

[0163] The light-emitting material is preferably a material that can receive holes and electrons respectively transferred from the hole transport layer and the electron transport layer, and combine the holes with the electrons to emit light in the visible light region, and has good quantum efficiency for fluorescence or phosphorescence. Specific examples thereof include 8-hydroxy-quinoline aluminum complex (Alq3); carbazole-based compounds; diphenylethylene compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo-based azole-, benzothiazole-, and benzimidazole-based compounds; poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; polyfluorene; rubrene, and the like, but are not limited thereto.

[0164] The light-emitting layer may include a host material and a dopant material as described above. The host material may include a compound represented by Chemical Formula 1. Alternatively, the light-emitting layer includes two or more hosts, one of which is a compound represented by Chemical Formula 1, and the other host material may be a fused aromatic ring derivative, a heterocyclic compound, 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. For example, the light-emitting layer may include two hosts, wherein the two hosts may be a compound represented by Chemical Formula 1 and a biscarbazole derivative, respectively.

[0165] The dopant material may be an aromatic amine derivative, a styrylamine compound, a boron complex, a fluoranthene compound, a metal complex, 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. The styrylamine compound is a compound 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, the metal complex includes iridium complex, platinum complex, etc., but are not limited thereto.

[0166] 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 the electron transport material is suitably a material that can well receive electrons from the cathode and transfer the electrons to the light-emitting layer and has a large electron mobility. Specific examples thereof include: Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic free radical compounds; hydroxyflavone-metal complexes, etc., but are not limited thereto. The electron transport layer can be used with any desired cathode material as used according to the related art. In particular, suitable examples of cathode materials are typical materials with a small work function, followed by an aluminum layer or a silver layer. Specific examples thereof include cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum layer or a silver layer.

[0167] The electron injection layer is a layer that injects electrons from the electrode, and is preferably a compound that has the ability to transport electrons, has an effect of injecting electrons from the cathode, and has an excellent effect of injecting electrons into the light-emitting layer or the light-emitting material, prevents the excitons generated by the light-emitting layer from moving to the hole injection layer, and also has excellent thin film forming ability. Specific examples thereof include fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, Azoles, The examples include, but are not limited to, diazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylmethane, anthrone, and derivatives thereof, metal complex compounds, nitrogen-containing 5-membered ring derivatives, and the like.

[0168] Examples of metal complex compounds include 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, bis(2-methyl-8-quinoline)(2-naphthol) gallium, and the like, but are not limited thereto.

[0169] The organic light emitting device according to the present invention may be a front-side emission type, a rear-side emission type, or a double-side emission type according to the materials used.

[0170] 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.

[0171] 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 given for illustrative purposes only and are not intended to limit the scope of the present invention.

[0172] Preparation Example A: Preparation of Intermediate Compound P-6

[0173] 1) Preparation of compound P-1

[0174]

[0175] 1-Bromo-2-fluoro-3-iodobenzene (100g, 333.5mmol) and (4-chloro-2-methoxyphenyl)boric acid (62.2g, 333.5mmol) are dissolved in 800ml tetrahydrofuran (THF). 2M sodium carbonate (Na2CO3) solution (500mL), tetrakis (triphenylphosphine) palladium (0) [Pd(PPh3)4] (7.7g, 6.7mmol) are added thereto and refluxed for 12 hours. After the reaction is complete, the reaction mixture is cooled to room temperature and extracted with water and toluene three times. The toluene layer is separated, dried over magnesium sulfate and filtered. The filtrate is distilled under reduced pressure, and the resulting mixture is recrystallized three times using chloroform and ethanol to obtain compound P-1 (53.7g, yield: 51%).

[0176] MS:[M+H] + =314

[0177] 2) Preparation of compound P-2

[0178]

[0179] Compound P-1 (50.0 g, 158.5 mmol) was dissolved in dichloromethane (600 ml) and then cooled to 0 ° C. Boron tribromide (15.8 ml, 166.4 mmol) was slowly added dropwise and then stirred for 12 hours. After the reaction was completed, the reaction mixture was washed three times with water, dried over magnesium sulfate and filtered. The filtrate was distilled under reduced pressure and purified by column chromatography to obtain compound P-2 (47.4 g, yield: 99%).

[0180] MS:[M+H] + =300

[0181] 3) Preparation of compound P-3

[0182]

[0183] Compound P-2 (40.0 g, 132.7 mmol) was dissolved in distilled dimethylformamide (DMF) (400 ml). The resulting solution was cooled to 0 ° C and sodium hydride (3.5 g, 145.9 mmol) was slowly added dropwise thereto. After stirring for 20 minutes, the reaction mixture was stirred at 100 ° C for 1 hour. After the reaction was completed, the reaction product was cooled to room temperature and 100 ml of ethanol was slowly added thereto. The mixture was distilled under reduced pressure and then recrystallized from chloroform and ethyl acetate to obtain compound P-3 (30.3 g, yield: 81%).

[0184] MS:[M+H] + =280

[0185] 4) Preparation of Compound P-4

[0186]

[0187] After compound P-3 (30.0 g, 106.6 mmol) was dissolved in tetrahydrofuran (300 ml), the reaction temperature was lowered to -78 ° C, and 1.7 M tert-butyl lithium (t-BuLi) (62.7 ml, 106.6 mmol) was slowly added thereto. After stirring at the same temperature for 1 hour, triisopropyl borate (B (OiPr) 3) (28.3 ml, 213.1 mmol) was added thereto. The mixture was stirred for 3 hours while the temperature was gradually raised to room temperature. 2N aqueous hydrochloric acid solution (200 ml) was added to the reaction mixture and then stirred at room temperature for 1.5 hours. The resulting precipitate was filtered, washed sequentially with water and ether, and then dried in a vacuum. After drying, the resulting product was dispersed in ether, stirred for 2 hours, then filtered and dried to prepare compound P-4 (24.4 g, yield: 93%).

[0188] MS:[M+H] + =247

[0189] 5) Preparation of Compound P-5

[0190]

[0191] Compound P-4 (20.0 g, 81.3 mmol) and 2-bromotriphenylene (24.9 g, 81.3 mmol) were dispersed in tetrahydrofuran (200 ml), then 2M potassium carbonate aqueous solution (K2CO3 aqueous solution) (122 ml, 243.9 mmol) was added, and tetrakis (triphenylphosphine) palladium [Pd(PPh3)4] (2.8 g, 3 mol%) was added, then the mixture was stirred and refluxed for 5 hours. The reaction temperature was lowered to room temperature, and the resulting solid was filtered. The filtered solid was recrystallized with chloroform and ethyl acetate, filtered and dried to obtain compound P-5 (23.0 g, yield: 66%).

[0192] MS:[M+H] + =429

[0193] 6) Preparation of Compound P-6

[0194]

[0195] Compound P-5 (20.0 g, 46.7 mmol), bis(pinacolato)diboron (13.0 g, 51.4 mmol) and potassium acetate (9.2 g, 93.4 mmol) were mixed under a nitrogen atmosphere, and the mixture was added to 200 ml of distilled water. alkane, heating and stirring. Add bis(dibenzylideneacetone)palladium (0.8g, 1.4mmol) and tricyclohexylphosphine (0.8g, 2.8mmol) thereto under reflux, and heat and stir the mixture for 3 hours. After the reaction is complete, the reaction mixture is cooled to room temperature and then filtered. Water is poured into the filtrate and extracted with chloroform. The organic layer is dried over anhydrous magnesium sulfate. After distillation under reduced pressure, recrystallization from ethanol produces compound P-6 (18.2g, 75%).

[0196] MS:[M+H] + =521

[0197] Preparation Example B: Preparation of Intermediate Compound T-6

[0198] 1) Preparation of compound T-1

[0199]

[0200] Compound T-1 (65.3 g, yield: 62%) was prepared in the same manner as in the preparation of compound P-1 in Preparation Example A, except that (4-chloro-2-methoxyphenyl)boric acid (62.2 g, 333.5 mmol) was used instead of (5-chloro-2-methoxyphenyl)boric acid (62.2 g, 333.5 mmol).

[0201] MS:[M+H] + =314

[0202] 2) Preparation of compound T-2

[0203]

[0204] Compound T-2 (43.0 g, yield: 90%) was prepared in the same manner as compound P-2 in Preparation Example A, except that compound T-1 (50.0 g, 158.5 mmol) was used instead of compound P-1 (50.0 g, 158.5 mmol).

[0205] MS:[M+H] + =300

[0206] 3) Preparation of compound T-3

[0207]

[0208] Compound T-3 (30.6 g, yield: 82%) was prepared in the same manner as in the preparation of compound P-3 in Preparation Example A, except that compound T-2 (40.0 g, 132.7 mmol) was used instead of compound P-2 (40.0 g, 132.7 mmol).

[0209] MS:[M+H] + =280

[0210] 4) Preparation of compound T-4

[0211]

[0212] Compound T-4 (25.0 g, yield: 95%) was prepared in the same manner as in the preparation of compound P-4 in Preparation Example A, except that compound T-3 (30.0 g, 106.6 mmol) was used instead of compound P-3 (30.0 g, 106.6 mmol).

[0213] MS:[M+H] + =247

[0214] 5) Preparation of Compound T-5

[0215]

[0216] After dispersing compound T-4 (20.0 g, 81.3 mmol) and 2-bromotriphenylene (24.9 g, 81.3 mmol) in tetrahydrofuran (200 ml), 2M potassium carbonate aqueous solution (K2CO3 aqueous solution) (122 ml, 243.9 mmol) was added, and tetrakis (triphenylphosphine) palladium [Pd (PPh3) 4] (2.8 g, 3 mol%) was added, and then the mixture was stirred and refluxed for 5 hours. The reaction temperature was lowered to room temperature and the obtained solid was filtered. The filtered solid was recrystallized with chloroform and ethyl acetate, filtered, and then dried to prepare compound T-5 (27.8 g, yield: 80%)

[0217] MS:[M+H] + =429

[0218] 6) Preparation of Compound T-6

[0219]

[0220] Compound T-5 (20.0 g, 46.7 mmol), bis(pinacolato)diboron (13.0 g, 51.4 mmol) and potassium acetate (9.2 g, 93.4 mmol) were mixed under nitrogen atmosphere, and the mixture was added to 200 ml of distilled water. alkane, heating and stirring. Add bis(dibenzylideneacetone)palladium (0.8g, 1.4mmol) and tricyclohexylphosphine (0.8g, 2.8mmol) thereto under reflux, and heat and stir the mixture for 3 hours. After the reaction is complete, the reaction mixture is cooled to room temperature and then filtered. Water is poured into the filtrate and extracted with chloroform, and the organic layer is dried over anhydrous magnesium sulfate. After distillation under reduced pressure, recrystallization with ethanol produces compound T-6 (16.8g, 69%).

[0221] MS:[M+H] + =521

[0222] Preparation Example C: Preparation of Intermediate Compound Q-6

[0223] 1) Preparation of compound Q-1

[0224]

[0225] 1-Bromo-4-fluoro-3-iodobenzene (50g, 166.6mmol) and (4-chloro-2-methoxyphenyl) boric acid (31.1g, 166.6mmol) are dissolved in 800ml tetrahydrofuran (THF). 2M sodium carbonate (Na2CO3) solution (250mL) and tetrakis (triphenylphosphine) palladium (0) [Pd(PPh3)4] (3.8g, 3mol%) are added thereto, and refluxed for 12 hours. After the reaction is complete, the reaction mixture is cooled to room temperature and extracted with water and toluene three times. The toluene layer is separated, dried over magnesium sulfate and filtered. The filtrate is distilled under reduced pressure, and the resulting mixture is recrystallized three times using chloroform and ethanol to obtain compound Q-1 (27.5g, yield: 51%).

[0226] MS:[M+H] + =314

[0227] 2) Preparation of compound Q-2

[0228]

[0229] Compound Q-1 (25.0 g, 150 mmol) was dissolved in dichloromethane (300 ml) and then cooled to 0 ° C. Boron tribromide (7.9 ml, 83.2 mmol) was slowly added dropwise thereto and then stirred for 12 hours. After the reaction was completed, the reaction mixture was washed three times with water, dried over magnesium sulfate and filtered. The filtrate was distilled under reduced pressure and purified by column chromatography to obtain compound Q-2 (23.7 g, yield: 99%).

[0230] MS:[M+H] + =300

[0231] 3) Preparation of compound Q-3

[0232]

[0233] Compound Q-2 (20.0 g, 66.4 mmol) was dissolved in distilled dimethylformamide (DMF) (200 ml). The resulting solution was cooled to 0 ° C and sodium hydride (1.8 g, 72.9 mmol) was slowly added dropwise thereto. After stirring for 20 minutes, the resulting mixture was stirred at 100 ° C for 1 hour. After the reaction was completed, the reaction mixture was cooled to room temperature and 100 ml of ethanol was slowly added thereto. The mixture was distilled under reduced pressure and recrystallized with chloroform and ethyl acetate to obtain compound Q-3 (15.2 g, yield: 81%).

[0234] MS:[M+H] + =280

[0235] 4) Preparation of compound Q-4

[0236]

[0237] After compound Q-3 (15.0 g, 53.3 mmol) was dissolved in tetrahydrofuran (150 ml), the temperature was lowered to -78 ° C, and 1.7 M tert-butyl lithium (t-BuLi) (31.8 ml, 53.3 mmol) was slowly added thereto. After stirring at the same temperature for one hour, triisopropyl borate (B (OiPr) 3) (14.2 ml, 107.0 mmol) was added thereto. The mixture was stirred for 3 hours while the temperature was gradually raised to room temperature. 2N aqueous hydrochloric acid solution (100 ml) was added to the reaction mixture, which was then stirred at room temperature for 1.5 hours. The resulting precipitate was filtered, washed sequentially with water and ether, and then dried in vacuo. After drying, the resultant was dispersed in ether, stirred for 2 hours, filtered and dried to obtain compound Q-4 (12.2 g, yield: 93%).

[0238] MS:[M+H] + =247

[0239] 5) Preparation of Compound Q-5

[0240]

[0241] After compound Q-4 (20.0 g, 81.3 mmol) and 2-bromotriphenylene (24.9 g, 81.3 mmol) were dispersed in tetrahydrofuran (200 ml), 2M potassium carbonate aqueous solution (K2CO3 aqueous solution) (122 ml, 243.9 mmol) was added, and tetrakis (triphenylphosphine) palladium [Pd(PPh3)4] (2.8 g, 3 mol%) was added, and the mixture was stirred and refluxed for 5 hours. The reaction temperature was lowered to room temperature and the obtained solid was filtered. The filtered solid was recrystallized with chloroform and ethyl acetate, filtered and dried to obtain compound Q-5 (25.4 g, yield: 73%).

[0242] MS:[M+H] + =429

[0243] 6) Preparation of Compound Q-6

[0244]

[0245] Compound Q-5 (20.0 g, 46.7 mmol), bis(pinacolato)diboron (13.0 g, 51.4 mmol) and potassium acetate (9.2 g, 93.4 mmol) were mixed under nitrogen atmosphere, and the mixture was added to 200 ml of distilled water. alkane, heating and stirring. Add bis(dibenzylideneacetone)palladium (0.8g, 1.4mmol) and tricyclohexylphosphine (0.8g, 2.8mmol) thereto under reflux, and heat and stir the mixture for 3 hours. After the reaction is complete, the reaction mixture is cooled to room temperature and filtered. Water is poured into the filtrate and extracted with chloroform, and the organic layer is dried over anhydrous magnesium sulfate. After distillation under reduced pressure, recrystallization with ethanol produces compound Q-6 (17.0g, yield: 70%).

[0246] MS:[M+H] + =521

[0247] Preparation Example D: Preparation of Intermediate Compound R-6

[0248] 1) Preparation of compound R-1

[0249]

[0250] 1-Bromo-3-fluoro-4-iodobenzene (50g, 166.6mmol) and (5-chloro-2-methoxyphenyl)boric acid (31.1g, 166.6mmol) are dissolved in 800ml tetrahydrofuran (THF). 2M sodium carbonate (Na2CO3) solution (250mL) and tetrakis (triphenylphosphine) palladium (0) [Pd(PPh3)4] (3.8g, 3mol%) are added thereto and refluxed for 12 hours. After the reaction is complete, the reaction mixture is cooled to room temperature and extracted with water and toluene three times. The toluene layer is separated, dried over magnesium sulfate and filtered. The filtrate is distilled under reduced pressure, and the resulting mixture is recrystallized three times using chloroform and ethanol to obtain compound R-1 (27.5g, yield: 51%).

[0251] MS:[M+H] + =314

[0252] 2) Preparation of compound R-2

[0253]

[0254] Compound R-1 (25.0 g, 150 mmol) was dissolved in dichloromethane (300 ml) and then cooled to 0 ° C. Boron tribromide (7.9 ml, 83.2 mmol) was slowly added dropwise thereto and then stirred for 12 hours. After the reaction was completed, the reaction mixture was washed three times with water, dried over magnesium sulfate and filtered. The filtrate was distilled under reduced pressure and purified by column chromatography to obtain compound R-2 (23.7 g, yield: 99%).

[0255] MS:[M+H] + =300

[0256] 3) Preparation of compound R-3

[0257]

[0258] Compound R-2 (20.0 g, 66.4 mmol) was dissolved in distilled dimethylformamide (DMF) (200 ml). The resulting solution was cooled to 0 ° C, and sodium hydride (1.8 g, 72.9 mmol) was slowly added dropwise thereto. After stirring for 20 minutes, the mixture was stirred at 100 ° C for 1 hour. After the reaction was completed, the reaction mixture was cooled to room temperature, and 100 ml of ethanol was slowly added thereto. The resulting mixture was distilled under reduced pressure, and then recrystallized from chloroform and ethyl acetate to obtain compound R-3 (15.2 g, yield: 81%).

[0259] MS:[M+H] + =280

[0260] 4) Preparation of compound R-4

[0261]

[0262] After compound R-3 (15.0 g, 53.3 mmol) was dissolved in tetrahydrofuran (150 ml), the reaction temperature was lowered to -78 ° C and 1.7 M tert-butyl lithium (t-BuLi) (31.8 ml, 53.3 mmol) was slowly added thereto. After stirring at the same temperature for one hour, triisopropyl borate (B (OiPr) 3) (14.2 ml, 107.0 mmol) was added and stirred for 3 hours while the temperature was gradually raised to room temperature. 2N aqueous hydrochloric acid solution (100 ml) was added to the reaction mixture and then stirred at room temperature for 1.5 hours. The obtained precipitate was filtered, washed with water and ether sequentially, and dried in a vacuum. After drying, the obtained product was dispersed in ether, stirred for 2 hours, filtered and dried to prepare compound R-4 (12.2 g, yield: 93%).

[0263] MS:[M+H] + =247

[0264] 5) Preparation of Compound R-5

[0265]

[0266] After compound R-4 (20.0 g, 81.3 mmol) and 2-bromotriphenylene (24.9 g, 81.3 mmol) were dispersed in tetrahydrofuran (200 ml), 2M potassium carbonate aqueous solution (K2CO3 aqueous solution) (122 ml, 243.9 mmol) was added and tetrakis (triphenylphosphine) palladium [Pd(PPh3)4] (2.8 g, 3 mol%) was added, and the mixture was stirred and refluxed for 5 hours. The reaction temperature was cooled to room temperature and the obtained solid was filtered. The filtered solid was recrystallized with chloroform and ethyl acetate, filtered and dried to obtain compound R-5 (21.6 g, yield: 62%).

[0267] MS:[M+H] + =429

[0268] 6) Preparation of Compound R-6

[0269]

[0270] Compound R-5 (20.0 g, 46.7 mmol), bis(pinacolato)diboron (13.0 g, 51.4 mmol) and potassium acetate (9.2 g, 93.4 mmol) were mixed under a nitrogen atmosphere and the mixture was added to 200 ml of distilled water. alkane, heating and stirring. Add bis(dibenzylideneacetone)palladium (0.8g, 1.4mmol) and tricyclohexylphosphine (0.8g, 2.8mmol) thereto under reflux, and heat and stir the mixture for 3 hours. After the reaction is complete, the reaction mixture is cooled to room temperature and then filtered. Water is poured into the filtrate and extracted with chloroform, and the organic layer is dried over anhydrous magnesium sulfate. After distillation under reduced pressure, recrystallization with ethanol produces compound R-6 (19.9g, yield: 82%).

[0271] MS:[M+H] + =521

[0272] Preparation Example 1: Preparation of Compound 1

[0273]

[0274] Compound P-6 (15.0g, 28.8mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (7.7g, 28.8mmol) are added to 200ml tetrahydrofuran under a nitrogen atmosphere, and the mixture is stirred and refluxed. Then, potassium carbonate (12.0g, 86.5mmol) is dissolved in 30ml water, the solution is added and stirred thoroughly, and tetrakis (triphenylphosphine) palladium (1.0g, 3mol%) is added. After reacting for 4 hours, the reaction mixture is cooled to room temperature and filtered. The filtrate is dissolved in chloroform and extracted with water, and then the organic layer is dried with magnesium sulfate. The organic layer is dried and then recrystallized from ethyl acetate to obtain compound 1 (7.0g, yield: 39%).

[0275] MS:[M+H] + =626

[0276] Preparation Example 2: Preparation of Compound 2

[0277]

[0278] Compound R-6 (15.0g, 28.8mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (7.7g, 28.8mmol) are added to 200ml tetrahydrofuran under a nitrogen atmosphere, and the mixture is stirred and refluxed. Then, potassium carbonate (12.0g, 86.5mmol) is dissolved in 30ml water, the solution is added and stirred thoroughly, and tetrakis (triphenylphosphine) palladium (1.0g, 3mol%) is added. After reacting for 4 hours, the reaction mixture is cooled to room temperature and filtered. The filtrate is dissolved in chloroform and extracted with water, and then the organic layer is dried with magnesium sulfate. The organic layer is dried and then recrystallized from ethyl acetate to obtain compound 2 (10.5g, yield: 58%).

[0279] MS:[M+H] + =626

[0280] Preparation Example 3: Preparation of Compound 3

[0281]

[0282] Compound Q-6 (15.0 g, 28.8 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (7.7 g, 28.8 mmol) were added to 200 ml tetrahydrofuran under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (12.0 g, 86.5 mmol) was then dissolved in 30 ml water, the solution was added and stirred thoroughly, and tetrakis (triphenylphosphine) palladium (1.0 g, 3 mol%) was added. After reacting for 4 hours, the reaction mixture was cooled to room temperature and then filtered. The filtrate was dissolved in chloroform and extracted with water, and the organic layer was then dried with magnesium sulfate. The organic layer was then dried and recrystallized with ethyl acetate to obtain compound 3 (9.4 g, yield: 52%).

[0283] MS:[M+H] + =626

[0284] Preparation Example 4: Preparation of Compound 4

[0285]

[0286] Compound T-6 (15.0 g, 28.8 mmol) and 2-chloro-4-(dibenzo[b, d]furan-4-yl)-6-phenyl-1,3,5-triazine (10.3 g, 28.8 mmol) were added to 200 ml tetrahydrofuran under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (12.0 g, 86.5 mmol) was then dissolved in 30 ml water, the solution was added and stirred thoroughly, and tetrakis(triphenylphosphine)palladium (1.0 g, 3 mol%) was added. After reacting for 4 hours, the reaction mixture was cooled to room temperature and then filtered. The filtrate was dissolved in chloroform and extracted with water, and the organic layer was then dried with magnesium sulfate. The organic layer was then dried and recrystallized with ethyl acetate to obtain compound 4 (13.2 g, 64%).

[0287] MS:[M+H] + =626

[0288] Preparation Example 5: Preparation of Compound 5

[0289]

[0290] Compound T-6 (15.0 g, 28.8 mmol) and 2-chloro-4-(dibenzo[b, d]thiophene-4-yl)-6-phenyl-1,3,5-triazine (10.8 g, 28.8 mmol) were added to 200 ml tetrahydrofuran under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (12.0 g, 86.5 mmol) was then dissolved in 30 ml water, the solution was added and stirred thoroughly, and tetrakis(triphenylphosphine)palladium (1.0 g, 3 mol%) was added. After reacting for 4 hours, the reaction mixture was cooled to room temperature and then filtered. The filtrate was dissolved in chloroform and extracted with water, and the organic layer was then dried with magnesium sulfate. The organic layer was then dried and recrystallized with ethyl acetate to obtain compound 5 (10.5 g, 50%).

[0291] MS:[M+H] + =626

[0292] Preparation Example 6: Preparation of Compound 6

[0293]

[0294] Compound T-6 (15.0 g, 28.8 mmol) and 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (9.9 g, 28.8 mmol) were added to 200 ml tetrahydrofuran under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (12.0 g, 86.5 mmol) was then dissolved in 30 ml water, the solution was added and stirred thoroughly, and tetrakis(triphenylphosphine)palladium (1.0 g, 3 mol%) was added. After reacting for 4 hours, the reaction mixture was cooled to room temperature and then filtered. The filtrate was dissolved in chloroform and extracted with water, and the organic layer was then dried with magnesium sulfate. The organic layer was then dried and recrystallized with ethyl acetate to obtain compound 6 (9.1 g, 45%).

[0295] MS:[M+H] + =702

[0296] Preparation Example 7: Preparation of Compound 7

[0297]

[0298] Compound T-6 (15.0 g, 28.8 mmol) and 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (9.9 g, 28.8 mmol) were added to 200 ml tetrahydrofuran under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (12.0 g, 86.5 mmol) was then dissolved in 30 ml water, the solution was added and stirred thoroughly, and tetrakis(triphenylphosphine)palladium (1.0 g, 3 mol%) was added. After reacting for 4 hours, the reaction mixture was cooled to room temperature and then filtered. The filtrate was dissolved in chloroform and extracted with water, and the organic layer was then dried with magnesium sulfate. The organic layer was then dried and recrystallized with ethyl acetate to obtain compound 7 (14.4 g, 71%).

[0299] M:[M+H] + =702

[0300] Preparation Example 8: Preparation of Compound 8

[0301]

[0302] Compound T-6 (15.0 g, 28.8 mmol) and 9-(4-chloro-6-phenyl-1,3,5-triazine-2-yl)-9H-carbazole (9.9 g, 28.8 mmol) were added to 200 ml of tetrahydrofuran under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (12.0 g, 86.5 mmol) was then dissolved in 30 ml of water, the solution was added and stirred thoroughly, and tetrakis(triphenylphosphine)palladium (1.0 g, 3 mol%) was added. After reacting for 4 hours, the reaction mixture was cooled to room temperature and then filtered. The filtrate was dissolved in chloroform and extracted with water, and the organic layer was then dried with magnesium sulfate. The organic layer was then dried and recrystallized with ethyl acetate to obtain compound 8 (12.2 g, 59%).

[0303] MS:[M+H] + =715

[0304] Preparation Example 9: Preparation of Compound 9

[0305]

[0306] Compound T-6 (15.0 g, 28.8 mmol) and 2- (3- bromophenyl) -4,6- diphenyl -1,3,5- triazine (11.2 g, 28.8 mmol) were added to 200 ml tetrahydrofuran under a nitrogen atmosphere, and the mixture was stirred and refluxed. Potassium carbonate (12.0 g, 86.5 mmol) was then dissolved in 30 ml water, the solution was added and stirred thoroughly, and tetrakis (triphenylphosphine) palladium (1.0 g, 3 mol%) was added. After reacting for 4 hours, the reaction mixture was cooled to room temperature and then filtered. The filtrate was dissolved in chloroform and extracted with water, and the organic layer was then dried with magnesium sulfate. The organic layer was then dried and recrystallized with ethyl acetate to obtain compound 9 (8.9 g, 44%).

[0307] MS:[M+H] + =702

[0308] Example 1: Fabrication of an organic light-emitting device

[0309] A thin coating having a thickness of The glass substrate of ITO (indium tin oxide) is put into the distilled water dissolved with detergent therein, and ultrasonic cleaning is carried out. In this case, the product manufactured by Fischer Co. is used as detergent, and as distilled water, the distilled water filtered twice by the filter manufactured by Millipore Co. is used. After ITO is cleaned for 30 minutes, ultrasonic cleaning is repeated twice with distilled water for 10 minutes. After cleaning with distilled water, the substrate is ultrasonically cleaned with isopropyl alcohol, acetone and methanol solvent, dried, and then transferred to a plasma cleaner. In addition, oxygen plasma is used to clean the substrate for 5 minutes, and then transferred to a vacuum depositor.

[0310] On the thus prepared ITO transparent electrode, the following compound HI-1 was thermally vacuum deposited onto The following compounds HT-1 to HT-2 were thermally vacuum deposited on the hole injection layer. To form a hole transport layer, the following compounds HT-2 to HT-3 were vacuum deposited on the hole transport layer. to form an electron blocking layer.

[0311] The compound 1 prepared in the previous preparation example 1, the following compound YGH-1 and the phosphorescent dopant YGD-1 were co-deposited on the electron blocking layer in a weight ratio of 44:44:12 to form a The thickness of the light-emitting layer.

[0312] The following compounds ET-1 to ET-2 were vacuum deposited on the light-emitting layer. The thickness of the electron transport layer is 98:2, and the following compound ET-2 and Li are vacuum deposited on the electron transport layer to form a Aluminum is deposited on the electron injection layer to a thickness of to form a cathode.

[0313]

[0314] In the above process, the vapor deposition rate of organic materials is maintained at / second to / sec, the aluminum deposition rate is maintained at / sec, and the vacuum degree during deposition was maintained at 1 × 10 -7 Up to 5×10 -8 Entrust.

[0315] Examples 2 to 9

[0316] An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compounds shown in the following Table 1 were used instead of Compound 1 of Preparation Example 1.

[0317] Comparative Examples 1 to 5

[0318] An organic light emitting device was manufactured in the same manner as in Example 1, except that the compounds shown in the following Table 1 were used instead of Compound 1 of Preparation Example 1. The structures of the compounds CE1, CE2, CE3, CE4, and CE5 used in Table 1 are as follows.

[0319]

[0320] Experimental Example 1

[0321] The organic light emitting devices manufactured in the examples and comparative examples were measured by applying a current at 10 mA / cm 2 The voltage and efficiency, color coordinates at current density of 50 mA / cm 2 Lifespan at current density (LT 95 ), and the results are shown in Table 1 below. At this time, the lifespan (LT 95 ) means the time required for the brightness to decrease to 95% of the initial brightness.

[0322] [Table 1]

[0323]

[0324] As shown in Table 1, the organic light emitting device using the compound of the present invention as a host material in the light emitting layer exhibits significantly improved lifespan characteristics while exhibiting higher efficiency compared to the organic light emitting device using the comparative example material as a host material in the light emitting layer.

[0325] Specifically, it can be seen that the substitution positions of the two substituents bonded to dibenzofuran / dibenzothiophene affect the characteristics of the organic light-emitting device. This is believed to be due to the increased electronic stability of the compound represented by Chemical Formula 1 compared to Compound CE2 substituted with a triphenylene group at a symmetrical position relative to the triazine group, Compound CE3 and Compound CE4 having a triphenylene group at a position different from the present invention, and Compound CE5 in which the triphenylene group is bonded at position *3 and all substituents of the triazine group are phenyl groups.

[0326] Therefore, in general, considering that the luminous efficiency and lifespan characteristics of an organic light-emitting device have a trade-off relationship with each other, it can be seen that the organic light-emitting device using the compound represented by Chemical Formula 1 exhibits significantly improved device characteristics compared to the device of the comparative example.

[0327] [Explanation of Reference Numerals]

[0328] 1: Substrate 2: Anode

[0329] 3: Light-emitting layer 4: Cathode

[0330] 5: Hole injection layer 6: Hole transport layer

[0331] 7: Electron blocking layer 8: Electron transport layer

[0332] 9: Electron injection layer

Claims

1. A compound wherein The compound is any one selected from the following compounds:

2. 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 disposed between the first electrode and the second electrode, wherein one or more of the organic material layers contains the compound according to claim 1 .

3. The organic light emitting device according to claim 2, wherein The organic material layer containing the compound is a light-emitting layer, The light-emitting layer comprises two or more hosts, and One of the hosts is the compound.

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