Novel compound and organic light emitting device comprising the same

Abstract

The present invention provides a novel compound and an organic light-emitting device using the same.

Description

Technology Field

[0001] The present invention relates to a novel compound and an organic light-emitting device containing the same. Background Technology

[0003] Generally, organic light emission refers to the phenomenon of converting electrical energy into light energy using organic materials. Organic light-emitting diodes (OLEDs) utilizing this phenomenon possess wide viewing angles, excellent contrast, and fast response times, and are being extensively researched due to their superior characteristics in terms of brightness, driving voltage, and response speed.

[0005] Organic light-emitting diodes generally have a structure comprising an anode, a cathode, and an organic layer between the anode and the cathode. To increase the efficiency and stability of the organic light-emitting diode, the organic layer is often composed of a multilayer structure made of different materials, such as a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. In the structure of such an organic light-emitting diode, when a voltage is applied between the two electrodes, holes are injected into the organic layer from the anode and electrons are injected into the organic layer from the cathode. When the injected holes and electrons meet, an exciton is formed, and light is emitted when this exciton falls back to the ground state.

[0007] There is a continuous demand for the development of new materials for organic materials used in organic light-emitting devices as described above. Prior art literature

[0009] Korean Patent Publication No. 10-2000-0051826 The problem to be solved

[0010] The present invention relates to a novel compound and an organic light-emitting device containing the same. means of solving the problem

[0012] The present invention provides a compound represented by the following chemical formula 1:

[0013] [Chemical Formula 1]

[0014]

[0015] In the above chemical formula 1,

[0016] Ar is substituted or unsubstituted C 6-60 aryl; or C comprising one or more heteroatoms selected from the group consisting of N, O, and S, substituted or unsubstituted 2-60 It is heteroaryl, and

[0017] L1 to L3 are each independently single bonds; substituted or unsubstituted C 6-60 Arrylene; or C comprising one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O, and S. 2-60 It is a heteroarylene,

[0018] R1 is hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C 1-60 Alkyl; substituted or unsubstituted C 6-60 aryl; or C comprising one or more heteroatoms selected from the group consisting of N, O, and S, substituted or unsubstituted 2-60 It is heteroaryl, and

[0019] R2 is a deuterium-substituted or unsubstituted phenyl, and

[0020] p is an integer from 0 to 7, and

[0021] q is an integer from 1 to 9, and

[0022] Dn represents the number of deuterium substitutions in the compound, where n is an integer greater than or equal to 0, and

[0023] The above L3 is bonded to a carbon at the C1 or C2 position of the phenanthrene structure, provided that when L3 is bonded to a carbon at the C2 position of the phenanthrene structure, R1 is a substituted or unsubstituted C 6-60 It is an aryl, and p is an integer from 1 to 7.

[0025] In addition, the present invention provides an organic light-emitting device comprising: a first electrode; a second electrode provided opposite to the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers comprise a compound represented by Chemical Formula 1. Effects of the invention

[0027] The compound represented by the chemical formula 1 described above can be used as a material for the organic layer of an organic light-emitting device, and can improve efficiency, low driving voltage, and / or lifespan characteristics in the organic light-emitting device. Brief explanation of the drawing

[0029] FIG. 1 illustrates an example of an organic light-emitting device comprising a substrate (1), an anode (2), a hole transport layer (3), a light-emitting layer (4), an electron injection and transport layer (5) and a cathode (6). FIG. 2 illustrates an example of an organic light-emitting device comprising a substrate (1), an anode (2), a hole injection layer (7), a hole transport layer (3), an electron blocking layer (8), a light-emitting layer (4), a hole blocking layer (9), an electron injection and transport layer (5), and a cathode (6). Specific details for implementing the invention

[0030] The present invention will be described in more detail below to aid in understanding.

[0032] (Definition of Terms)

[0033] In this specification, and means a bond connected to another substituent.

[0035] Also, in this specification, D is deuterium, and in Chemical Formula 1, D n This means that the hydrogen in the compound has been replaced by n deuterium atoms. However, if n is an integer of 0, it means that it has not been substituted.

[0037] In this specification, the term “substituted or unsubstituted” means substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, halogen group, cyano group, nitro group, hydroxyl group, carbonyl group, ester group, imide group, amino group, phosphine oxide group, alkoxy group, aryloxy group, alkyl thioxy group, aryl thioxy group, alkyl sulfoxy group, aryl sulfoxy group, silyl group, boron group, alkyl group, cycloalkyl group, alkenyl group, aryl group, aralkyl group, aralkenyl group, alkylaryl group, alkylamine group, aralkylamine group, heteroarylamine group, arylamine group, arylphosphine group, or heteroaryl comprising one or more of N, O and S atoms; or substituted or unsubstituted with two or more of the exemplified substituents connected. For example, “substituents connected with two or more substituents” may be biphenyl groups. In other words, a biphenyl group can be an aryl group, or it can be interpreted as a substituent consisting of two connected phenyl groups. For example, the term "substituted or unsubstituted" refers to "unsubstituted, or deuterium, halogen, C 1-10 Alkyl, C 1-10 Alkoxy and C 6-20 It may be understood to mean "substituted with one or more substituents selected from the group consisting of aryls, for example, one to five substituents." Additionally, in this specification, the term "substituted with one or more substituents" may be understood to mean, for example, "substituted with one to five substituents" or "substituted with one or two substituents."

[0039] In this specification, the number of carbon atoms in the carbonyl group is not particularly limited, but it is preferred to have 1 to 40 carbon atoms. Specifically, it may be a substituent having the following structure, but is not limited thereto.

[0040]

[0042] In the present specification, the hydrogen of the ester group may be substituted with a straight-chain, branched-chain, 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 of the following structural formula, but is not limited thereto.

[0043]

[0045] In the present specification, the number of carbon atoms in the imide group is not particularly limited, but it is preferred to have 1 to 25 carbon atoms. Specifically, it may be a substituent having the following structure, but is not limited thereto.

[0046]

[0048] In this specification, the silyl groups specifically include, but are not limited to, trimethylsilyl groups, triethylsilyl groups, t-butyldimethylsilyl groups, vinyldimethylsilyl groups, propyldimethylsilyl groups, triphenylsilyl groups, diphenylsilyl groups, phenylsilyl groups, etc.

[0050] In the present specification, boron groups specifically include dimethylboron groups, diethylboron groups, t-butylmethylboron groups, diphenylboron groups, phenylboron groups, etc., but are not limited thereto.

[0052] In this specification, examples of halogen groups include fluoro, chloro, bromo, or iodo.

[0054] In the present specification, the alkyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited but is preferably 1 to 40. According to one embodiment, the number of carbon atoms 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 another embodiment, specific examples of the alkyl group include methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethylbutyl, iso-pentyl, n-pentyl, neo-pentyl, tert-pentyl, 1-ethyl-propyl, 1,1-dimethylpropyl, n-hexyl, iso-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, iso-hexyl, 1-methylhexyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 5-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, n-octyl, iso-octyl, tert-octyl, 1-methylheptyl, Examples include 2-ethylhexyl, 2,4,4-trimethyl-1-pentyl, 2,4,4-trimethyl-2-pentyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, but are not limited thereto.

[0056] In the present specification, the alkenyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms of the alkenyl group is 2 to 20. According to another embodiment, the number of carbon atoms of the alkenyl group is 2 to 10. According to yet another embodiment, the number of carbon atoms of the alkenyl group is 2 to 6. Specific examples 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, stilbenyl group, styrenyl group, etc., but are not limited thereto.

[0058] In this specification, the alicyclic group refers to a substituent derived from a saturated or unsaturated hydrocarbon ring compound that contains only carbon as a ring-forming atom and does not have aromaticity, and is understood to encompass both monocyclic and condensed polycyclic compounds. According to one embodiment, the number of carbon atoms of the alicyclic group is 3 to 60. According to another embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 30. According to yet another embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 20. Examples of such alicyclic groups include monocyclic groups such as cycloalkyl groups, bridged hydrocarbon groups, spiro hydrocarbon groups, and substituents derived from hydrogenated derivatives of aromatic hydrocarbon compounds.

[0060] Specifically, examples of the cycloalkyl groups include, but are not limited to, 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.

[0062] In addition, examples of the above-mentioned cross-linked hydrocarbon groups include, but are not limited to, bicyclo[1.1.0]butyl, bicyclo[2.2.1]heptyl, bicyclo[4.2.0]octa-1,3,5-trienyl, adamantyl, decalinyl, etc.

[0064] In addition, examples of the above-mentioned spiro-cyclic hydrocarbon groups include spiro[3.4]octyl and spiro[5.5]undecanyl, but are not limited thereto.

[0066] In addition, the substituent derived from the hydrogenated derivative of the above aromatic hydrocarbon compound refers to a substituent derived from a compound in which hydrogen is added to a portion of the unsaturated bonds of a monocyclic or polycyclic aromatic hydrocarbon compound, and an example of such a substituent is 1 H -Indenil, 2 H -Indenil, 4 H -Indenyl, 2,3-Dihydro-1 H -Indenyl, 1,4-Dihydronaphthalenyl, 1,2,3,4-Tetrahydronaphthalenyl, 6,7,8,9-Tetrahydro-5 H -Benzo[7]Anulenyl(6,7,8,9-tetrahydro-5 H -benzo[7]annulenyl), 6,7-dehydro-5 H Examples include benzocycloheptenyl, but are not limited to these.

[0068] In this specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms and may be a monocyclic or polycyclic aryl group having aromaticity. 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 a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto. As a polycyclic aryl group, the aryl group may be a naphthyl group, anthracenyl group, phenanthrenyl group, triphenylenyl group, pyrenyl group, perylenyl group, chrysenyl group, etc., but is not limited thereto.

[0070] In this specification, a heterocyclic group refers to a substituent derived from a monocyclic or condensed polycyclic compound comprising, in addition to carbon as a ring-forming atom, one or more heteroatoms selected from O, N, Si, and S, and is understood to encompass both aromatic and non-aromatic substituents. According to one embodiment, the number of carbon atoms in the heterocyclic group is 2 to 60. According to another embodiment, the number of carbon atoms in the heterocyclic group is 2 to 30. According to yet another embodiment, the number of carbon atoms in the heterocyclic group is 2 to 20. Examples of such heterocyclic groups include an aromatic heteroaryl group and a substituent derived from a hydrogenated derivative of a heteroaromatic compound.

[0072] Specifically, examples of the above heteroaryl groups include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, acryl group, pyridazine group, pyrazinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazinopyrazinyl group, isoquinoline group, indole group, carbazole group, benzoxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophen group, dibenzothiophen group, benzofuranyl group, phenanthroline group, isooxazolyl group, thiadiazole group, phenothiazinyl group, There are dibenzofuranyl groups, etc., but are not limited thereto.

[0074] In addition, the substituent derived from the hydrogenated derivative of the above heteroaromatic compound refers to a substituent derived from a compound in which hydrogen is added to a portion of the unsaturated bonds of a monocyclic or polycyclic heteroaromatic compound, and examples of such substituents include 1,3-dihydroisobenzofuranyl, 2,3-dihydrobenzofuranyl, 1,3-dihydrobenzo[ c ]thiophenyl(1,3-dihydrobenzo[ c ]thiophenyl), 2,3-dehydro[ b ]thiophenyl(2,3-dihydro[ b ]thiophenyl, etc., are included, but are not limited to these.

[0076] In this specification, the aryl group among the aralkyl group, ar alkenyl group, alkylaryl group, arylamine group, and arylsilyl group is the same as the examples of aryl groups described above. In this specification, the alkyl group among the aralkyl group, alkylaryl group, and alkylamine group is the same as the examples of alkyl groups described above. In this specification, the description of the heteroaryl group described above may be applied to the heteroaryl group among the heteroaryl amines. In this specification, the alkenyl group among the ar alkenyl group is the same as the examples of alkenyl groups described above. In this specification, the description of the aryl group described above may be applied to the arylene group except that it is a divalent group. In this specification, the description of the heteroaryl group described above may be applied to the heteroaryl group except that the heteroarylene group is a divalent group. In this specification, the description of the aryl group or cycloalkyl group described above may be applied except that the hydrocarbon ring is not monovalent and is formed by the combination of two substituents. In this specification, the description of the aforementioned heteroaryl may apply except that the heterocycle is not monovalent and is formed by the combination of two substituents.

[0078] (compound)

[0079] Meanwhile, the present invention provides a compound represented by the above chemical formula 1.

[0081] Specifically, the compound represented by Chemical Formula 1 has a structure in which a phenyl-substituted phenanthrene ring and a dibenzofuran ring are bonded at controlled bonding positions, either directly or through a linker. Accordingly, an organic light-emitting device employing the compound can exhibit a lower driving voltage compared to an organic light-emitting device employing a compound having a different structure, and can simultaneously improve efficiency and lifespan characteristics. Furthermore, if substituted with deuterium, the lifespan characteristics of the organic light-emitting device can be further improved.

[0083] In the above Chemical Formula 1, Ar is specifically a substituted or unsubstituted C 6-30aryl; or C comprising one or more heteroatoms selected from the group consisting of N, O, and S, substituted or unsubstituted 2-30 It is a heteroaryl.

[0085] More specifically, Ar is phenyl, naphthyl, biphenyl, dibenzofuranyl, or dibenzothiophenyl, and said Ar may be unsubstituted or substituted with one or more deuterium atoms.

[0087] More specifically, Ar is phenyl, naphthyl, biphenyl, dibenzofuranyl, or dibenzothiophenyl, and said Ar may be unsubstituted, or substituted with 1 to 4 deuterium, or completely substituted with deuterium.

[0089] Also, in the above Chemical Formula 1, L1 to L3 are each independently a single bond; or substituted or unsubstituted C 6-20 It could be arylene,

[0090] The above L1 to L3 may each be independently unsubstituted or substituted with one or more deuterium atoms.

[0092] In addition, when L1 to L3 are substituted with deuterium, each may be independently substituted with 1 to 4 deuterium atoms, or completely substituted with deuterium atoms.

[0094] More specifically, L1 can be a single bond.

[0096] More specifically, L2 and L3 may each be independently a single combination, or any one selected from the group consisting of:

[0097]

[0098] In the above chemical formula, the dotted line indicates the bonding position.

[0100] Also, in the above Chemical Formula 1, R1 is specifically hydrogen; deuterium; halogen; cyano; substituted or unsubstituted C 1-20 Alkyl; substituted or unsubstituted C 6-20aryl; or C comprising one or more heteroatoms selected from the group consisting of N, O, and S, substituted or unsubstituted 2-20 It can be heteroaryl.

[0102] More specifically, R1 is hydrogen, deuterium, phenyl, or naphthyl, and

[0103] The above phenyl and naphthyl may be unsubstituted or substituted with one or more deuterium atoms.

[0105] More specifically, R1 is hydrogen, deuterium, phenyl, or naphthyl, and

[0106] The above phenyl and naphthyl may be unsubstituted, substituted with 1 to 5 deuterium atoms, or completely substituted with deuterium atoms.

[0108] Also, in the above chemical formula 1, R2 is specifically phenyl, and

[0109] The above phenyl may be unsubstituted or substituted with 1 to 5 deuterium atoms.

[0111] Also, in the above Chemical Formula 1, when L3 is bonded to the carbon at the C2 position of the phenanthrene structure, R1 is specifically C 6-20 It is an aryl, and the aryl may be unsubstituted, substituted with 1 to 5 deuterium atoms, or completely substituted with deuterium atoms. Also, p is an integer from 1 to 7, and more specifically, an integer of 1.

[0113] More specifically, in the above chemical formula 1, when L3 is bonded to the carbon at the C2 position of the phenanthrene structure, R1 is phenyl or naphthyl, and the phenyl or naphthyl may be unsubstituted, substituted with 1 to 5 deuterium atoms, or completely substituted with deuterium atoms. In this case, p is an integer from 1 to 7, and more specifically, an integer of 1.

[0115] In addition, the compound represented by the above chemical formula 1 may have at least one of the hydrogen atoms in the compound substituted with deuterium or unsubstituted. That is, in chemical formula 1, Dn represents the number of deuterium substitutions in the compound, and n is an integer greater than or equal to 0.

[0117] Specifically, if the above compound is not substituted with deuterium, n is an integer of 0.

[0119] Also, when the above compound is substituted with deuterium, at least one of R1 in Formula 1 is deuterium, or Ar, L1 to L3, R1 and At least one of R2 may be substituted with one or more deuterium atoms. In this case, n in Chemical Formula 1 is an integer greater than or equal to 1.

[0121] More specifically, when the compound is deuterium-substituted, n in Formula 1 may be 1 or more, or 5 or more, or 8 or more, and may be an integer of 50 or less, or 30 or less, or 28 or less.

[0123] Specifically, the compound represented by the above chemical formula 1 may be a compound represented by the following chemical formula 1-1 or 1-2:

[0124] [Chemical Formula 1-1]

[0125]

[0126] [Chemical Formula 1-2]

[0127]

[0128] In the above chemical formulas 1-1 and 1-2.

[0129] Ar, L1 to L3, R1, R2, p, q, and Dn are as previously defined.

[0131] Specifically, the compound represented by the above chemical formula 1 may be a compound represented by any one of the following chemical formulas 1-a to 1-h:

[0132]

[0133] In the above chemical formulas 1-a to 1-h.

[0134] Ar, L1 to L3, R1, R2, p, Dn, C1 and C2 are as previously defined.

[0136] Meanwhile, representative examples of compounds represented by the above chemical formula 1 are as follows:

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149] In the above chemical formula, Dn is as previously defined.

[0151] The compound represented by the above chemical formula 1 can be prepared by a manufacturing method such as the following reaction formula 1, for example, and the remaining compounds can be prepared in a similar manner.

[0152] [Reaction Equation 1]

[0153]

[0154] In the above reaction scheme 1, Ar, L1 to L3, R1, R2, p, and q are as defined in Chemical Formula 1 above. Also, Y is a boron-containing organic group, specifically a boronic acid group, a boronic acid ester group, or a boronic acid pinacol ester group. Also, X is a halogen group, specifically X is chloro or bromo.

[0156] The above reaction scheme 1 is a Suzuki coupling reaction, which is preferably carried out in the presence of a palladium catalyst and a base, and the reactor for the Suzuki coupling reaction can be modified as known in the art. The above manufacturing method can be further specified in the manufacturing examples described below.

[0158] In addition, the compound represented by the above chemical formula 1 can be prepared, for example, by further performing a manufacturing method such as that in the following reaction formula 2 after the step in the above reaction formula 1.

[0159] [Reaction Equation 2]

[0160]

[0161] In the above reaction scheme 2, Ar, L1 to L3, R1, R2, p, q, and Dn are as previously defined.

[0163] The above step is a deuterium substitution reaction, and it is preferable to perform the deuterium reaction by using a solution containing deuterium oxide and an organic compound hydrolyzable by said deuterium oxide to prepare the compound prepared by the Suzuki coupling reaction in Reaction Scheme 1, and heating may be performed to facilitate the deuterium reaction. Meanwhile, examples of organic compounds hydrolyzable by said deuterium oxide include trifluoromethanesulfonic anhydride, trifluoroacetic anhydride, acetic anhydride, or methanesulfonic anhydride, and any one or more of these may be used. In addition, solvents that can be used when preparing said solution include 1,2,4-trichlorobenzene, but are not limited thereto. The above manufacturing method may be further specified in the manufacturing examples to be described later.

[0165] (Organic light-emitting diode)

[0166] Meanwhile, the present invention provides an organic light-emitting device comprising a compound represented by Chemical Formula 1. For example, the present invention provides an organic light-emitting device comprising a first electrode; a second electrode provided opposite to the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers comprise a compound represented by Chemical Formula 1.

[0168] The organic layer of the organic light-emitting device of the present invention may be formed as a single layer structure, but may also be formed as a multilayer structure in which two or more organic layers are stacked. For example, the organic light-emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, an electron injection and transport layer, etc., as organic layers. However, the structure of the organic light-emitting device is not limited thereto and may include a smaller number of organic layers.

[0170] At this time, the organic layer containing the above compound may be an electron injection layer, or an electron injection and transport layer.

[0172] In one embodiment, the organic layer may include a hole injection layer, a hole transport layer, a light-emitting layer, and an electron injection and transport layer, wherein the organic layer containing the compound may be an electron injection and transport layer.

[0174] In another embodiment, the organic layer may include a hole injection layer, a hole transport layer, an electron blocking layer, an emitting layer, and an electron injection and transport layer, wherein the organic layer containing the compound may be an electron injection and transport layer.

[0176] In another embodiment, the organic layer may include a hole injection layer, a hole transport layer, an electron blocking layer, an emitting layer, a hole blocking layer, and an electron injection and transport layer, wherein the organic layer containing the compound may be a hole blocking layer or an electron injection and transport layer.

[0178] In another embodiment, the organic layer may include a hole injection layer, a hole transport layer, an electron blocking layer, an emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer, wherein the organic layer containing the compound may be a hole blocking layer, an electron transport layer, or an electron injection layer.

[0180] The organic layer of the organic light-emitting device of the present invention may be formed as a single layer structure, but may also be formed as a multilayer structure in which two or more organic layers are stacked. For example, the organic light-emitting device of the present invention may have a structure that further includes, in addition to the emitting layer as an organic layer, a hole injection layer and a hole transport layer between the first electrode and the emitting layer, and an electron transport layer and an electron injection layer between the emitting layer and the second electrode. However, the structure of the organic light-emitting device is not limited thereto and may include a smaller or larger number of organic layers.

[0182] In addition, the organic light-emitting device according to the present invention may be an organic light-emitting device of a normal type structure in which a positive electrode, one or more organic layers, and a negative electrode are sequentially stacked on a substrate, wherein the first electrode is a positive electrode and the second electrode is a negative electrode. In addition, the organic light-emitting device according to the present invention may be an organic light-emitting device of an inverted type structure in which a negative electrode, one or more organic layers, and a positive electrode are sequentially stacked on a substrate, wherein the first electrode is a negative electrode and the second electrode is a positive electrode. For example, the structure of an organic light-emitting device according to one embodiment of the present invention is illustrated in FIGS. 1 and 2.

[0184] FIG. 1 illustrates an example of an organic light-emitting device comprising a substrate (1), an anode (2), a hole transport layer (3), a light-emitting layer (4), an electron injection and transport layer (5), and a cathode (6). In such a structure, a compound represented by the chemical formula 1 may be included in the hole transport layer.

[0186] FIG. 2 illustrates an example of an organic light-emitting device comprising a substrate (1), an anode (2), a hole injection layer (7), a hole transport layer (3), an electron blocking layer (8), a light-emitting layer (4), a hole blocking layer (9), an electron injection and transport layer (5), and a cathode (6). In such a structure, a compound represented by the chemical formula 1 may be included in the hole injection layer, the hole transport layer, or the electron blocking layer.

[0188] The organic light-emitting device according to the present invention may be manufactured using materials and methods known in the art, except that one or more of the organic layers comprise a compound represented by Chemical Formula 1. Additionally, when the organic light-emitting device comprises a plurality of organic layers, the organic layers may be formed of the same material or different materials.

[0190] For example, an organic light-emitting device according to the present invention can be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. At this time, a physical vapor deposition (PVD) method, such as sputtering or electron beam evaporation, can be used to form an anode by depositing a metal, a conductive metal oxide, or an alloy thereof on a substrate, and then forming an organic layer including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer on top of it, and finally depositing a material that can be used as a cathode on top of it. In addition to this method, an organic light-emitting device can be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.

[0192] In addition, the compound represented by Chemical Formula 1 above can be formed as an organic layer by vacuum deposition as well as solution coating when manufacturing an organic light-emitting device. Here, solution coating refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited to these.

[0194] In addition to this method, an organic light-emitting diode can be manufactured by sequentially depositing an organic layer and an anode material from a cathode material onto a substrate (WO 2003 / 012890). However, the manufacturing method is not limited to this.

[0196] For example, the first electrode is a positive electrode and the second electrode is a negative electrode, or the first electrode is a negative electrode and the second electrode is a positive electrode.

[0198] As for the anode material, a material with a large work function is generally preferred so that hole injection into the organic layer can be smooth. Specific examples of the anode material 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 metal and oxide 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.

[0200] The above-mentioned cathode material is preferably a material with a small work function to facilitate electron injection into an organic layer. Specific examples of the above-mentioned cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer structural materials such as LiF / Al or LiO2 / Al, but are not limited thereto.

[0202] The hole injection layer above is a layer that injects holes from an electrode, and as a hole injection material, a compound having the ability to transport holes, having an excellent hole injection effect on the anode, the emissive layer, or the emissive material, preventing the movement of excitons generated in the emissive layer to the electron injection layer or the electron injection material, and also having excellent thin film formation ability is preferred. It is preferable that 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 layer. Specific examples of hole injection materials include, but are not limited to, metal porphyrins, oligothiophenes, arylamine-based organic materials, hexanitrile-hexaazatriphenylene-based organic materials, quinacridone-based organic materials, perylene-based organic materials, anthraquinones, and polyaniline and polythiophene-based conductive polymers.

[0204] The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light-emitting layer. As a hole transport material, a material capable of receiving holes from the anode or the hole injection layer and transferring them to the light-emitting layer, and having high mobility for holes, is suitable. As the hole transport material, a compound represented by Chemical Formula 1, an arylamine-based organic material, a conductive polymer, and a block copolymer having both conjugated and non-conjugated portions may be used, but are not limited thereto.

[0206] The above electron blocking layer is formed on the hole transport layer and, preferably, is provided in contact with the light-emitting layer, and refers to a layer that improves the efficiency of an organic light-emitting device by controlling hole mobility and preventing excessive movement of electrons to increase the probability of hole-electron coupling. The above electron blocking layer includes an electron blocking material, and examples of such electron blocking materials may include arylamine-based organic materials, but are not limited thereto.

[0208] The above-mentioned luminescent material is a material capable of emitting light in the visible light region by receiving and combining holes and electrons from a hole transport layer and an electron transport layer, respectively, and is preferably a material with good quantum efficiency for fluorescence or phosphorescence. Specific examples include, but are not limited to, 8-hydroxy-quinoline aluminum complex (Alq3); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; compounds of the benzoxazole, benzthiazole, and benzimidazole series; polymers of the poly(p-phenylenevinylene) (PPV) series; spiro compounds; polyfluorene, rubrene, etc.

[0210] The above-mentioned light-emitting layer may include a host material and a dopant material. As such a host material, a condensed aromatic ring derivative or a heterocyclic compound may be used. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene derivatives, fluoranthene derivatives, etc., and heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, ladder-type furan derivatives, pyrimidine derivatives, etc., but are not limited thereto.

[0212] Dopant materials include aromatic amine derivatives, styramine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, aromatic amine derivatives are condensed aromatic ring derivatives having substituted or unsubstituted arylamino groups, such as pyrene, anthracene, chrysene, and periplantene having arylamino groups; styramine compounds are compounds in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, wherein one or more substituents selected from the group consisting of aryl groups, silyl groups, alkyl groups, cycloalkyl groups, and arylamino groups are substituted or unsubstituted. Specifically, styramine, styryldiamine, styryltriamine, styryltetraamine, etc. are examples, but are not limited thereto. In addition, metal complexes include iridium complexes, platinum complexes, etc., but are not limited thereto.

[0214] Specific examples of the above-mentioned dopant include the following compounds, but are not limited thereto:

[0215]

[0216]

[0217]

[0218] The hole blocking layer is formed on the light-emitting layer, preferably in contact with the light-emitting layer, and refers to a layer that improves the efficiency of an organic light-emitting device by controlling electron mobility and preventing excessive movement of holes, thereby increasing the probability of hole-electron coupling. The hole blocking layer comprises a hole blocking material, and examples of such hole blocking materials may include compounds with electron-absorbing groups such as azine derivatives including triazine; triazole derivatives; oxadiazole derivatives; phenanthroline derivatives; and phosphine oxide derivatives, but are not limited thereto.

[0220] The electron injection and transport layer is a layer that simultaneously performs the roles of an electron transport layer and an electron injection layer, injecting electrons from the electrode and transporting the received electrons to the light-emitting layer, and is formed on the light-emitting layer or the hole blocking layer. Suitable electron injection and transport materials are those that can effectively receive electrons from the cathode and transfer them to the light-emitting layer, and materials with high electron mobility are suitable. Specific examples of electron injection and transport materials include, but are not limited to, Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic radical compounds; hydroxyflavone-metal complexes; and triazine derivatives. Alternatively, it may be used with fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidene methane, anthrone, etc., their derivatives, metal complex compounds, or nitrogen-containing five-membered ring derivatives, but is not limited thereto.

[0222] The electron injection and transport layer may also be formed as separate layers, such as an electron injection layer and an electron transport layer. In such cases, the electron transport layer is formed on the light-emitting layer or the hole-blocking layer, and the electron injection and transport material described above may be used as the electron transport material included in the electron transport layer. Additionally, the electron injection layer is formed on the electron transport layer, and the electron injection material included in the electron injection layer may be LiF, NaCl, CsF, Li2O, BaO, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidene methane, anthrone, etc., and their derivatives, metal complex compounds, and nitrogen-containing five-membered ring derivatives.

[0224] The above metal complex compounds include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h]quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)(o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, Examples include bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, but are not limited to these.

[0226] The organic light-emitting device according to the present invention may be a bottom-emission device, a top-emission device, or a double-sided light-emitting device, and in particular may be a bottom-emission device for which relatively high light-emitting efficiency is required.

[0228] In addition, the compound represented by the above chemical formula 1 may be included in organic solar cells or organic transistors in addition to organic light-emitting devices.

[0230] The preparation of the compound represented by Chemical Formula 1 above and the organic light-emitting device containing the same is described in detail in the following examples. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited by them.

[0231] Unless otherwise noted in this specification, at room temperature (ordinary temperature) means the standard laboratory temperature of 23±5℃.

[0232] Synthesis Example 1

[0233]

[0234] Trz1 (15 g, 41.9 mmol) and sub1 (16.7 g, 44 mmol) were added to 300 ml of THF and stirred and refluxed. To the resulting reaction mixture, potassium carbonate (17.4 g, 125.8 mmol) dissolved in 100 ml of water was added and stirred thoroughly, after which bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.4 mmol) was added. After reacting for 2 hours, the mixture was cooled to room temperature, the organic and water layers were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added and stirred, followed by filtration and vacuum distillation of the filtrate. The resulting concentrate was purified by silica gel column chromatography to prepare 16.4 g of Compound 1. (Yield 68%, MS: [M+H]+= 576)

[0236] Synthesis Example 2

[0237]

[0238] Trz1 (15 g, 41.9 mmol) and sub2 (16.7 g, 44 mmol) were added to 300 ml of THF and stirred and refluxed. To the resulting reaction mixture, potassium carbonate (17.4 g, 125.8 mmol) dissolved in 100 ml of water was added and stirred thoroughly, after which bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.4 mmol) was added. After reacting for 5 hours, the mixture was cooled to room temperature, the organic and water layers were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, separated the organic layer, anhydrous magnesium sulfate was added and stirred, filtered, and the filtrate was distilled under reduced pressure. The resulting concentrate was purified by silica gel column chromatography to prepare 15.2 g of Compound 2. (Yield 63%, MS: [M+H]+= 576)

[0240] Synthesis Example 3

[0241]

[0242] Trz1 (15 g, 41.9 mmol) and sub3 (20.1 g, 44 mmol) were added to 300 ml of THF and stirred and refluxed. To the resulting reaction mixture, potassium carbonate (17.4 g, 125.8 mmol) dissolved in 100 ml of water was added and stirred thoroughly, after which bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.4 mmol) was added. After reacting for 2 hours, the mixture was cooled to room temperature, the organic and water layers were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, separated the organic layer, anhydrous magnesium sulfate was added and stirred, filtered, and the filtrate was distilled under reduced pressure. The resulting concentrate was purified by silica gel column chromatography to prepare 17.7 g of Compound 3. (Yield 65%, MS: [M+H]+= 652)

[0244] Synthesis Example 4

[0245]

[0246] Trz2 (15 g, 34.6 mmol) and sub2 (13.8 g, 36.3 mmol) were added to 300 ml of THF and stirred and refluxed. To the resulting reaction mixture, potassium carbonate (14.3 g, 103.7 mmol) dissolved in 100 ml of water was added and stirred thoroughly, after which bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.3 mmol) was added. After reacting for 4 hours, the mixture was cooled to room temperature, the organic and water layers were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, separated the organic layer, anhydrous magnesium sulfate was added and stirred, filtered, and the filtrate was distilled under reduced pressure. The resulting concentrate was purified by silica gel column chromatography to prepare 16 g of Compound 4. (Yield 71%, MS: [M+H]+= 652)

[0248] Synthesis Example 5

[0249]

[0250] Trz3 (15 g, 33.5 mmol) and sub4 (16 g, 35.2 mmol) were added to 300 ml of THF and stirred and refluxed. To the resulting reaction mixture, potassium carbonate (13.9 g, 100.5 mmol) dissolved in 100 ml of water was added and stirred thoroughly, after which bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.3 mmol) was added. After reacting for 4 hours, the mixture was cooled to room temperature, the organic and water layers were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, separated the organic layer, anhydrous magnesium sulfate was added and stirred, filtered, and the filtrate was distilled under reduced pressure. The resulting concentrate was purified by silica gel column chromatography to prepare 19.1 g of Compound 5. (Yield 77%, MS: [M+H]+= 742)

[0252] Synthesis Example 6

[0253]

[0254] Trz3 (15 g, 33.5 mmol) and sub5 (13.4 g, 35.2 mmol) were added to 300 ml of THF and stirred and refluxed. To the resulting reaction mixture, potassium carbonate (13.9 g, 100.5 mmol) dissolved in 100 ml of water was added and stirred thoroughly, after which bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.3 mmol) was added. After reacting for 5 hours, the mixture was cooled to room temperature, the organic and water layers were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, separated the organic layer, anhydrous magnesium sulfate was added and stirred, filtered, and the filtrate was distilled under reduced pressure. The resulting concentrate was purified by silica gel column chromatography to prepare 17.6 g of Compound 6. (Yield 79%, MS: [M+H]+= 666)

[0256] Synthesis Example 7

[0257]

[0258] Trz3 (15 g, 33.5 mmol) and sub2 (13.4 g, 35.2 mmol) were added to 300 ml of THF and stirred and refluxed. To the resulting reaction mixture, potassium carbonate (13.9 g, 100.5 mmol) dissolved in 100 ml of water was added and stirred thoroughly, after which bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.3 mmol) was added. After reacting for 5 hours, the mixture was cooled to room temperature, the organic and water layers were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added and stirred, followed by filtration and vacuum distillation of the filtrate. The resulting concentrate was purified by silica gel column chromatography to prepare 16.3 g of Compound 7. (Yield 73%, MS: [M+H]+= 666)

[0260] Synthesis Example 8

[0261]

[0262] Trz4 (15 g, 33.5 mmol) and sub6 (13.4 g, 35.2 mmol) were added to 300 ml of THF and stirred and refluxed. To the resulting reaction mixture, potassium carbonate (13.9 g, 100.5 mmol) dissolved in 100 ml of water was added and stirred thoroughly, after which bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.3 mmol) was added. After reacting for 4 hours, the mixture was cooled to room temperature, the organic and water layers were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, separated the organic layer, anhydrous magnesium sulfate was added and stirred, filtered, and the filtrate was distilled under reduced pressure. The resulting concentrate was purified by silica gel column chromatography to prepare 14.7 g of Compound 8. (Yield 66%, MS: [M+H]+= 666)

[0264] Synthesis Example 9

[0265]

[0266] Trz5 (15 g, 32.3 mmol) and sub7 (12.9 g, 33.9 mmol) were added to 300 ml of THF and stirred and refluxed. To the resulting reaction mixture, potassium carbonate (13.4 g, 97 mmol) dissolved in 100 ml of water was added and stirred thoroughly, after which bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.3 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, the organic and water layers were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, separated the organic layer, anhydrous magnesium sulfate was added and stirred, filtered, and the filtrate was distilled under reduced pressure. The resulting concentrate was purified by silica gel column chromatography to prepare 17.4 g of Compound 9. (Yield 79%, MS: [M+H]+= 682)

[0268] Synthesis Example 10

[0269]

[0270] Trz6 (15 g, 32.3 mmol) and sub6 (12.9 g, 33.9 mmol) were added to 300 ml of THF and stirred and refluxed. To the resulting reaction mixture, potassium carbonate (13.4 g, 97 mmol) dissolved in 100 ml of water was added and stirred thoroughly, after which bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.3 mmol) was added. After reacting for 2 hours, the mixture was cooled to room temperature, the organic and water layers were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, separated the organic layer, anhydrous magnesium sulfate was added and stirred, filtered, and the filtrate was distilled under reduced pressure. The resulting concentrate was purified by silica gel column chromatography to prepare 16.1 g of Compound 10. (Yield 73%, MS: [M+H]+= 682)

[0272] Synthesis Example 11

[0273]

[0274] Trz7 (15 g, 34.6 mmol) and sub7 (13.8 g, 36.3 mmol) were added to 300 ml of THF and stirred and refluxed. To the resulting reaction mixture, potassium carbonate (14.3 g, 103.7 mmol) dissolved in 100 ml of water was added and stirred thoroughly, after which bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.3 mmol) was added. After reacting for 5 hours, the mixture was cooled to room temperature, the organic and water layers were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, separated the organic layer, anhydrous magnesium sulfate was added and stirred, filtered, and the filtrate was distilled under reduced pressure. The resulting concentrate was purified by silica gel column chromatography to prepare 16.2 g of Compound 11. (Yield 72%, MS: [M+H]+= 652)

[0276] Synthesis Example 12

[0277]

[0278] Trz8 (15 g, 31 mmol) and sub8 (12.4 g, 32.5 mmol) were added to 300 ml of THF and stirred and refluxed. To the resulting reaction mixture, potassium carbonate (12.9 g, 93 mmol) dissolved in 100 ml of water was added and stirred thoroughly, after which bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.3 mmol) was added. After reacting for 5 hours, the mixture was cooled to room temperature, the organic and water layers were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, separated the organic layer, anhydrous magnesium sulfate was added and stirred, filtered, and the filtrate was distilled under reduced pressure. The resulting concentrate was purified by silica gel column chromatography to prepare 15.4 g of Compound 12. (Yield 71%, MS: [M+H]+= 702)

[0280] Synthesis Example 13

[0281]

[0282] Trz9 (15 g, 34.6 mmol) and sub9 (16.6 g, 36.3 mmol) were added to 300 ml of THF and stirred and refluxed. To the resulting reaction mixture, potassium carbonate (14.3 g, 103.7 mmol) dissolved in 100 ml of water was added and stirred thoroughly, after which bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.3 mmol) was added. After reacting for 2 hours, the mixture was cooled to room temperature, the organic and water layers were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, separated the organic layer, anhydrous magnesium sulfate was added and stirred, filtered, and the filtrate was distilled under reduced pressure. The resulting concentrate was purified by silica gel column chromatography to prepare 19.9 g of Compound 13. (Yield 79%, MS: [M+H]+= 728)

[0284] Synthesis Example 14

[0285]

[0286] Trz10 (15 g, 31 mmol) and sub10 (12.4 g, 32.5 mmol) were added to 300 ml of THF and stirred and refluxed. To the resulting reaction mixture, potassium carbonate (12.9 g, 93 mmol) dissolved in 100 ml of water was added and stirred thoroughly, after which bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.3 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, the organic and water layers were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, separated the organic layer, anhydrous magnesium sulfate was added and stirred, filtered, and the filtrate was distilled under reduced pressure. The resulting concentrate was purified by silica gel column chromatography to prepare 15.4 g of Compound 14. (Yield 71%, MS: [M+H]+= 702)

[0288] Synthesis Example 15

[0289]

[0290] Trz11 (15 g, 34.6 mmol) and sub11 (13.8 g, 36.3 mmol) were added to 300 ml of THF and stirred and refluxed. To the resulting reaction mixture, potassium carbonate (14.3 g, 103.7 mmol) dissolved in 100 ml of water was added and stirred thoroughly, after which bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.3 mmol) was added. After reacting for 4 hours, the mixture was cooled to room temperature, the organic and water layers were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, separated the organic layer, anhydrous magnesium sulfate was added and stirred, filtered, and the filtrate was distilled under reduced pressure. The resulting concentrate was purified by silica gel column chromatography to prepare 14.6 g of Compound 15. (Yield 65%, MS: [M+H]+= 652)

[0292] Synthesis Example 16

[0293]

[0294] Trz12 (15 g, 34.6 mmol) and sub8 (13.8 g, 36.3 mmol) were added to 300 ml of THF and stirred and refluxed. To the resulting reaction mixture, potassium carbonate (14.3 g, 103.7 mmol) dissolved in 100 ml of water was added and stirred thoroughly, after which bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.3 mmol) was added. After reacting for 5 hours, the mixture was cooled to room temperature, the organic and water layers were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, separated the organic layer, anhydrous magnesium sulfate was added and stirred, filtered, and the filtrate was distilled under reduced pressure. The resulting concentrate was purified by silica gel column chromatography to prepare 14 g of Compound 16. (Yield 62%, MS: [M+H]+= 652)

[0296] Synthesis Example 17

[0297]

[0298] Trz13 (15 g, 29.4 mmol) and sub12 (11.7 g, 30.9 mmol) were added to 300 ml of THF and stirred and refluxed. To the resulting reaction mixture, potassium carbonate (12.2 g, 88.2 mmol) dissolved in 100 ml of water was added and stirred thoroughly, after which bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.3 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, the organic and water layers were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added and stirred, followed by filtration and vacuum distillation of the filtrate. The resulting concentrate was purified by silica gel column chromatography to prepare 16.5 g of Compound 17. (Yield 77%, MS: [M+H]+= 728)

[0300] Synthesis Example 18

[0301]

[0302] Trz14 (15 g, 34.6 mmol) and sub5 (13.8 g, 36.3 mmol) were added to 300 ml of THF and stirred and refluxed. To the resulting reaction mixture, potassium carbonate (14.3 g, 103.7 mmol) dissolved in 100 ml of water was added and stirred thoroughly, after which bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.3 mmol) was added. After reacting for 5 hours, the mixture was cooled to room temperature, the organic and water layers were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, separated the organic layer, anhydrous magnesium sulfate was added and stirred, filtered, and the filtrate was distilled under reduced pressure. The resulting concentrate was purified by silica gel column chromatography to prepare 15.1 g of Compound 18. (Yield 67%, MS: [M+H]+= 652)

[0304] Synthesis Example 19

[0305]

[0306] Trz15 (15 g, 31 mmol) and sub13 (12.4 g, 32.5 mmol) were added to 300 ml of THF and stirred and refluxed. To the resulting reaction mixture, potassium carbonate (12.9 g, 93 mmol) dissolved in 100 ml of water was added and stirred thoroughly, after which bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.3 mmol) was added. After reacting for 2 hours, the mixture was cooled to room temperature, the organic and water layers were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, separated the organic layer, anhydrous magnesium sulfate was added and stirred, filtered, and the filtrate was distilled under reduced pressure. The resulting concentrate was purified by silica gel column chromatography to prepare 16.7 g of Compound 19. (Yield 77%, MS: [M+H]+= 702)

[0308] Synthesis Example 20

[0309]

[0310] Trz16 (15 g, 31 mmol) and sub14 (12.4 g, 32.5 mmol) were added to 300 ml of THF and stirred and refluxed. To the resulting reaction mixture, potassium carbonate (12.9 g, 93 mmol) dissolved in 100 ml of water was added and stirred thoroughly, after which bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.3 mmol) was added. After reacting for 4 hours, the mixture was cooled to room temperature, the organic and water layers were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, separated the organic layer, anhydrous magnesium sulfate was added and stirred, filtered, and the filtrate was distilled under reduced pressure. The resulting concentrate was purified by silica gel column chromatography to prepare 16.7 g of Compound 20. (Yield 77%, MS: [M+H]+= 702)

[0312] Synthesis Example 21

[0313]

[0314] Trz17 (15 g, 31 mmol) and sub15 (12.4 g, 32.5 mmol) were added to 300 ml of THF and stirred and refluxed. To the resulting reaction mixture, potassium carbonate (12.9 g, 93 mmol) dissolved in 100 ml of water was added and stirred thoroughly, after which bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.3 mmol) was added. After reacting for 4 hours, the mixture was cooled to room temperature, the organic and water layers were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, separated the organic layer, anhydrous magnesium sulfate was added and stirred, filtered, and the filtrate was distilled under reduced pressure. The resulting concentrate was purified by silica gel column chromatography to prepare 13.7 g of Compound 21. (Yield 63%, MS: [M+H]+= 702)

[0316] Synthesis Example 22

[0317]

[0318] Trz18 (15 g, 31 mmol) and sub13 (12.4 g, 32.5 mmol) were added to 300 ml of THF and stirred and refluxed. To the resulting reaction mixture, potassium carbonate (12.9 g, 93 mmol) dissolved in 100 ml of water was added and stirred thoroughly, after which bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.3 mmol) was added. After reacting for 5 hours, the mixture was cooled to room temperature, the organic and water layers were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, separated the organic layer, anhydrous magnesium sulfate was added and stirred, filtered, and the filtrate was distilled under reduced pressure. The resulting concentrate was purified by silica gel column chromatography to prepare 15.4 g of Compound 22. (Yield 71%, MS: [M+H]+= 702)

[0320] Synthesis Example 23

[0321]

[0322] Trz19 (15 g, 31 mmol) and sub8 (12.4 g, 32.5 mmol) were added to 300 ml of THF and stirred and refluxed. To the resulting reaction mixture, potassium carbonate (12.9 g, 93 mmol) dissolved in 100 ml of water was added and stirred thoroughly, after which bis(tri-tert-butylphosphine)palladium (0) (0.2 g, 0.3 mmol) was added. After reacting for 2 hours, the mixture was cooled to room temperature, the organic and water layers were separated, and the organic layer was distilled. This was dissolved again in chloroform, washed twice with water, separated the organic layer, anhydrous magnesium sulfate was added and stirred, filtered, and the filtrate was distilled under reduced pressure. The resulting concentrate was purified by silica gel column chromatography to prepare 14.1 g of Compound 23. (Yield 65%, MS: [M+H]+= 702)

[0324] Synthesis Example 24

[0325]

[0326] Compound 1 (10 g, 17.4 mmol) was added to 200 ml of 1,2,4-trichlorobenzene and stirred at room temperature. In another container, at 0°C, Deuterium oxide (8.7 g, 434.3 mmol) was added to Trifluoromethanesulfonic anhydride (24.5 g, 86.9 mmol) and stirred for 5 hours to prepare a solution. Subsequently, the mixed solution of Trifluoromethanesulfonic anhydride and Deuterium oxide was added dropwise to the prepared mixed solution of 1,2,4-trichlorobenzene, and the temperature was raised to 140°C and maintained while stirring. After reacting for 2 hours, the mixture was cooled to room temperature and the organic and water layers were separated. Afterward, the organic layer was neutralized with an aqueous potassium carbonate solution. After washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added and stirred, and the mixture was filtered; the filtrate was then subjected to vacuum distillation. The resulting concentrate was purified by silica gel column chromatography to obtain 6.2 g of Compound 24. (Yield 61%, MS: [M+H]+= 586)

[0328] Synthesis Example 25

[0329]

[0330] Compound 2 (10 g, 17.4 mmol) was added to 200 ml of 1,2,4-trichlorobenzene and stirred at room temperature. In another container, at 0°C, Deuterium oxide (8.7 g, 434.3 mmol) was added to Trifluoromethanesulfonic anhydride (24.5 g, 86.9 mmol) and stirred for 5 hours to prepare a solution. Subsequently, the mixed solution of Trifluoromethanesulfonic anhydride and Deuterium oxide was added dropwise to the prepared mixed solution of 1,2,4-trichlorobenzene, and the temperature was raised to 140°C and maintained while stirring. After reacting for 3 hours, the mixture was cooled to room temperature and the organic and water layers were separated. The organic layer was then neutralized with an aqueous potassium carbonate solution. After washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added and stirred, and the mixture was filtered; the filtrate was then subjected to vacuum distillation. The resulting concentrate was purified by silica gel column chromatography to obtain 5.1 g of compound 25. (Yield 50%, MS: [M+H]+= 585)

[0332] Synthesis Example 26

[0333]

[0334] Compound 6 (10 g, 15 mmol) was added to 200 ml of 1,2,4-trichlorobenzene and stirred at room temperature. In another container, at 0°C, Deuterium oxide (7.5 g, 375.5 mmol) was added to Trifluoromethanesulfonic anhydride (21.2 g, 75.1 mmol) and stirred for 5 hours to prepare a solution. Subsequently, the mixed solution of Trifluoromethanesulfonic anhydride and Deuterium oxide was added dropwise to the prepared mixed solution of 1,2,4-trichlorobenzene, and the temperature was raised to 140°C and maintained while stirring. After reacting for 2 hours, the solution was cooled to room temperature and the organic and water layers were separated. The organic layer was then neutralized with an aqueous potassium carbonate solution. After washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added and stirred, and the mixture was filtered; the filtrate was then subjected to vacuum distillation. The resulting concentrate was purified by silica gel column chromatography to obtain 6.1 g of compound 26. (Yield 60%, MS: [M+H]+= 676)

[0336] Synthesis Example 27

[0337]

[0338] Compound 8 (10 g, 15 mmol) was added to 200 ml of 1,2,4-trichlorobenzene and stirred at room temperature. In another container, at 0°C, Deuterium oxide (7.5 g, 375.5 mmol) was added to Trifluoromethanesulfonic anhydride (21.2 g, 75.1 mmol) and stirred for 5 hours to prepare a solution. Subsequently, the mixed solution of Trifluoromethanesulfonic anhydride and Deuterium oxide was added dropwise to the prepared mixed solution of 1,2,4-trichlorobenzene, and the temperature was raised to 140°C and maintained while stirring. After reacting for 3 hours, the solution was cooled to room temperature and the organic and water layers were separated. The organic layer was then neutralized with an aqueous potassium carbonate solution. After washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added and stirred, and the mixture was filtered; the filtrate was then subjected to vacuum distillation. The resulting concentrate was purified by silica gel column chromatography to obtain 7.1 g of Compound 27. (Yield 70%, MS: [M+H]+= 674)

[0340] Synthesis Example 28

[0341]

[0342] Compound 11 (10 g, 15.3 mmol) was added to 200 ml of 1,2,4-trichlorobenzene and stirred at room temperature. In another container, at 0°C, Deuterium oxide (7.7 g, 383.6 mmol) was added to Trifluoromethanesulfonic anhydride (21.6 g, 76.7 mmol) and stirred for 5 hours to prepare a solution. Subsequently, the mixed solution of Trifluoromethanesulfonic anhydride and Deuterium oxide was added dropwise to the prepared mixed solution of 1,2,4-trichlorobenzene, and the temperature was raised to 140°C and maintained while stirring. After reacting for 3 hours, the solution was cooled to room temperature and the organic and water layers were separated. The organic layer was then neutralized with an aqueous potassium carbonate solution. After washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added and stirred, and the mixture was filtered; the filtrate was then subjected to vacuum distillation. The resulting concentrate was purified by silica gel column chromatography to obtain 5.4 g of compound 28. (Yield 53%, MS: [M+H]+= 665)

[0344] Synthesis Example 29

[0345]

[0346] Compound 16 (10 g, 15.3 mmol) was added to 200 ml of 1,2,4-trichlorobenzene and stirred at room temperature. In another container, at 0°C, Deuterium oxide (7.7 g, 383.6 mmol) was added to Trifluoromethanesulfonic anhydride (21.6 g, 76.7 mmol) and stirred for 5 hours to prepare a solution. Subsequently, the mixed solution of Trifluoromethanesulfonic anhydride and Deuterium oxide was added dropwise to the prepared mixed solution of 1,2,4-trichlorobenzene, and the temperature was raised to 140°C and maintained while stirring. After reacting for 2 hours, the solution was cooled to room temperature and the organic and water layers were separated. The organic layer was then neutralized with an aqueous potassium carbonate solution. After washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added and stirred, and the mixture was filtered; the filtrate was then subjected to vacuum distillation. The resulting concentrate was purified by silica gel column chromatography to obtain 6.6 g of Compound 29. (Yield 65%, MS: [M+H]+= 664)

[0348] Synthesis Example 30

[0349]

[0350] Compound 18 (10 g, 15.3 mmol) was added to 200 ml of 1,2,4-trichlorobenzene and stirred at room temperature. In another container, at 0°C, Deuterium oxide (7.7 g, 383.6 mmol) was added to Trifluoromethanesulfonic anhydride (21.6 g, 76.7 mmol) and stirred for 5 hours to prepare a solution. Subsequently, the mixed solution of Trifluoromethanesulfonic anhydride and Deuterium oxide was added dropwise to the prepared mixed solution of 1,2,4-trichlorobenzene, and the temperature was raised to 140°C and maintained while stirring. After reacting for 2 hours, the solution was cooled to room temperature and the organic and water layers were separated. The organic layer was then neutralized with an aqueous potassium carbonate solution. After washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added and stirred, and the mixture was filtered; the filtrate was then subjected to vacuum distillation. The resulting concentrate was purified by silica gel column chromatography to obtain 6.2 g of Compound 30. (Yield 61%, MS: [M+H]+= 662)

[0352] Synthesis Example 31

[0353]

[0354] Compound 20 (10 g, 14.2 mmol) was added to 200 ml of 1,2,4-trichlorobenzene and stirred at room temperature. In another container, at 0°C, Deuterium oxide (7.1 g, 356.2 mmol) was added to Trifluoromethanesulfonic anhydride (20.1 g, 71.2 mmol) and stirred for 5 hours to prepare a solution. Subsequently, the mixed solution of Trifluoromethanesulfonic anhydride and Deuterium oxide was added dropwise to the prepared mixed solution of 1,2,4-trichlorobenzene, and the temperature was raised to 140°C and maintained while stirring. After reacting for 3 hours, the solution was cooled to room temperature and the organic and water layers were separated. The organic layer was then neutralized with an aqueous potassium carbonate solution. After washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added and stirred, and the mixture was filtered; the filtrate was then subjected to vacuum distillation. The resulting concentrate was purified by silica gel column chromatography to obtain 5.4 g of Compound 31. (Yield 53%, MS: [M+H]+= 715)

[0356] Synthesis Example 32

[0357]

[0358] Compound 3 (10 g, 15.3 mmol) was added to 200 ml of 1,2,4-trichlorobenzene and stirred at room temperature. In another container, at 0°C, Deuterium oxide (11.1 g, 552.3 mmol) was added to Trifluoromethanesulfonic anhydride (34.6 g, 122.7 mmol) and stirred for 5 hours to prepare a solution. Subsequently, the mixed solution of Trifluoromethanesulfonic anhydride and Deuterium oxide was added dropwise to the prepared mixed solution of 1,2,4-trichlorobenzene, and the temperature was raised to 140°C and maintained while stirring. After reacting for 11 hours, the solution was cooled to room temperature and the organic and water layers were separated. The organic layer was then neutralized with an aqueous potassium carbonate solution. After washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added and stirred, and the mixture was filtered; the filtrate was then subjected to vacuum distillation. The resulting concentrate was purified by silica gel column chromatography to obtain 5.5 g of Compound 32. (Yield 53%, MS: [M+H]+= 674)

[0360] Synthesis Example 33

[0361]

[0362] Compound 7 (10 g, 15 mmol) was added to 200 ml of 1,2,4-trichlorobenzene and stirred at room temperature. In another container, at 0°C, Deuterium oxide (10.8 g, 540.7 mmol) was added to Trifluoromethanesulfonic anhydride (33.9 g, 120.2 mmol) and stirred for 5 hours to prepare a solution. Subsequently, the mixed solution of Trifluoromethanesulfonic anhydride and Deuterium oxide was added dropwise to the prepared mixed solution of 1,2,4-trichlorobenzene, and the temperature was raised to 140°C and maintained while stirring. After reacting for 12 hours, the solution was cooled to room temperature and the organic and water layers were separated. The organic layer was then neutralized with an aqueous potassium carbonate solution. After washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added and stirred, and the mixture was filtered; the filtrate was then subjected to vacuum distillation. The resulting concentrate was purified by silica gel column chromatography to obtain 5.9 g of Compound 33. (Yield 57%, MS: [M+H]+= 689)

[0364] Synthesis Example 34

[0365]

[0366] Compound 10 (10 g, 14.7 mmol) was added to 200 ml of 1,2,4-trichlorobenzene and stirred at room temperature. In another container, at 0°C, Deuterium oxide (10.6 g, 528 mmol) was added to Trifluoromethanesulfonic anhydride (33.1 g, 117.3 mmol) and stirred for 5 hours to prepare a solution. Subsequently, the mixed solution of Trifluoromethanesulfonic anhydride and Deuterium oxide was added dropwise to the prepared mixed solution of 1,2,4-trichlorobenzene, and the temperature was raised to 140°C and maintained while stirring. After reacting for 11 hours, the solution was cooled to room temperature and the organic and water layers were separated. The organic layer was then neutralized with an aqueous potassium carbonate solution. After washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added and stirred, and the mixture was filtered; the filtrate was then subjected to vacuum distillation. The resulting concentrate was purified by silica gel column chromatography to obtain 5.6 g of Compound 34. (Yield 54%, MS: [M+H]+= 705)

[0368] Synthesis Example 35

[0369]

[0370] Compound 14 (10 g, 14.2 mmol) was added to 200 ml of 1,2,4-trichlorobenzene and stirred at room temperature. In another container, at 0°C, Deuterium oxide (10.3 g, 512.9 mmol) was added to Trifluoromethanesulfonic anhydride (32.2 g, 114 mmol) and stirred for 5 hours to prepare a solution. Subsequently, the mixed solution of Trifluoromethanesulfonic anhydride and Deuterium oxide was added dropwise to the prepared mixed solution of 1,2,4-trichlorobenzene, and the temperature was raised to 140°C and maintained while stirring. After reacting for 11 hours, the mixture was cooled to room temperature and the organic and water layers were separated. The organic layer was then neutralized with an aqueous potassium carbonate solution. After washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added and stirred, and the mixture was filtered; the filtrate was then subjected to vacuum distillation. The resulting concentrate was purified by silica gel column chromatography to obtain 5.7 g of Compound 35. (Yield 55%, MS: [M+H]+= 729)

[0372] Synthesis Example 36

[0373]

[0374] Compound 17 (10 g, 13.7 mmol) was added to 200 ml of 1,2,4-trichlorobenzene and stirred at room temperature. In another container, at 0°C, Deuterium oxide (9.9 g, 494.6 mmol) was added to Trifluoromethanesulfonic anhydride (31 g, 109.9 mmol) and stirred for 5 hours to prepare a solution. Subsequently, the mixed solution of Trifluoromethanesulfonic anhydride and Deuterium oxide was added dropwise to the prepared mixed solution of 1,2,4-trichlorobenzene, and the temperature was raised to 140°C and maintained while stirring. After reacting for 12 hours, the mixture was cooled to room temperature and the organic and water layers were separated. The organic layer was then neutralized with an aqueous potassium carbonate solution. After washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added and stirred, and the mixture was filtered; the filtrate was then subjected to vacuum distillation. The resulting concentrate was purified by silica gel column chromatography to obtain 5.4 g of compound 36. (Yield 52%, MS: [M+H]+= 756)

[0376] Synthesis Example 37

[0377]

[0378] Compound 21 (10 g, 14.2 mmol) was added to 200 ml of 1,2,4-trichlorobenzene and stirred at room temperature. In another container, at 0°C, Deuterium oxide (10.3 g, 512.9 mmol) was added to Trifluoromethanesulfonic anhydride (32.2 g, 114 mmol) and stirred for 5 hours to prepare a solution. Subsequently, the mixed solution of Trifluoromethanesulfonic anhydride and Deuterium oxide was added dropwise to the prepared mixed solution of 1,2,4-trichlorobenzene, and the temperature was raised to 140°C and maintained while stirring. After reacting for 10 hours, the solution was cooled to room temperature and the organic and water layers were separated. The organic layer was then neutralized with an aqueous potassium carbonate solution. After washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added and stirred, and the mixture was filtered; the filtrate was then subjected to vacuum distillation. The resulting concentrate was purified by silica gel column chromatography to obtain 5.7 g of Compound 37. (Yield 55%, MS: [M+H]+= 730)

[0380] Synthesis Example 38

[0381]

[0382] Compound 22 (10 g, 14.2 mmol) was added to 200 ml of 1,2,4-trichlorobenzene and stirred at room temperature. In another container, at 0°C, Deuterium oxide (10.3 g, 512.9 mmol) was added to Trifluoromethanesulfonic anhydride (32.2 g, 114 mmol) and stirred for 5 hours to prepare a solution. Subsequently, the mixed solution of Trifluoromethanesulfonic anhydride and Deuterium oxide was added dropwise to the prepared mixed solution of 1,2,4-trichlorobenzene, and the temperature was raised to 140°C and maintained while stirring. After reacting for 11 hours, the mixture was cooled to room temperature and the organic and water layers were separated. The organic layer was then neutralized with an aqueous potassium carbonate solution. After washing twice with water, the organic layer was separated, anhydrous magnesium sulfate was added and stirred, and the mixture was filtered; the filtrate was then subjected to vacuum distillation. The resulting concentrate was purified by silica gel column chromatography to obtain 6.4 g of Compound 38. (Yield 62%, MS: [M+H]+= 729)

[0384] Example 1

[0385] A glass substrate coated with an indium tin oxide (ITO) thin film to a thickness of 1,000 Å was placed in distilled water containing dissolved detergent and cleaned using ultrasound. Fischer Co. products were used as the detergent, and distilled water that had been filtered twice using a Millerpore Co. filter was used. After cleaning the ITO for 30 minutes, ultrasonic cleaning was performed for 10 minutes, repeating the process twice with distilled water. After the distilled water cleaning was completed, the substrate was ultrasonically cleaned using isopropyl alcohol, acetone, and methanol as solvents, dried, and then transported to a plasma cleaner. Additionally, the substrate was cleaned using oxygen plasma for 5 minutes and then transported to a vacuum deposition machine.

[0386] On the ITO transparent electrode prepared in this way, the following HI-1 compound was formed as a hole injection layer with a thickness of 1150 Å, while p-doping with the following A-1 compound at a concentration of 1.5%. The following HT-1 compound was vacuum-deposited on the hole injection layer to form a hole transport layer with a film thickness of 800 Å. Subsequently, the following EB-1 compound was vacuum-deposited on the hole transport layer with a film thickness of 150 Å to form an electron blocking layer. Subsequently, the following compound, prepared in Synthesis Example 1 as a host, and the Dp-7 compound as a dopant were vacuum-deposited on the electron blocking layer in a weight ratio of 98:2 to form a red emitting layer with a thickness of 400 Å. The following HB-1 compound was vacuum-deposited on the emitting layer with a film thickness of 30 Å to form a hole blocking layer. Next, the following ET-1 compound and the following LiQ compound were vacuum deposited in a weight ratio of 2:1 on the hole blocking layer to form an electron injection and transport layer with a thickness of 300 Å. A cathode was formed by sequentially depositing lithium fluoride (LiF) with a thickness of 12 Å and aluminum with a thickness of 1,000 Å on the electron injection and transport layer.

[0387]

[0388] In the above process, the deposition rate of the organic material was maintained at 0.4–0.7 Å / sec, while the deposition rates for the cathode lithium fluoride and aluminum were maintained at 0.3 Å / sec and 2 Å / sec, respectively, and the vacuum level during deposition was 2 × 10⁻¹⁰ -7 ~ 5 x 10 -6 An organic light-emitting diode was fabricated by maintaining torr.

[0390] Examples 2 to 38

[0391] An organic light-emitting diode was manufactured in the same manner as in Example 1, except that a compound listed in Table 1 below was used as a host in the organic light-emitting diode of Example 1.

[0393] Comparative Examples 1 to 6

[0394] An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compound listed in Table 3 below was used as the host in the organic light-emitting device of Example 1.

[0395] Compounds B-1 to B-6 used in Comparative Examples 1 to 6 are as follows:

[0396]

[0398] Experimental Example

[0399] When current was applied to the organic light-emitting diodes prepared in the above examples and comparative examples, the voltage and efficiency were measured (15 mA / cm²). 2 The results were obtained based on the criteria and are shown in Tables 1 to 3 below. Life T95 refers to the time required for the luminance to decrease to 95% from the initial luminance (6,000 nit).

[0401] Example No. Host Driving voltage (V) Efficiency (cd / A) Life T95(hr) luminous color 1 Compound 1 3.66 18.99 147 red 2 Compound 2 3.63 19.26 151 red 3 Compound 3 3.61 18.43 144 red 4 Compound 4 3.49 20.08 146 red 5 Compound 5 3.48 19.79 171 red 6 Compound 6 3.49 20.35 148 red 7 Compound 7 3.41 18.99 181 red 8 Compound 8 3.52 18.93 168 red 9 Compound 9 3.57 16.71 153 red 10 Compound 10 3.56 17.29 149 red 11 Compound 11 3.58 20.70 164 red 12 Compound 12 3.50 20.88 166 red 13 Compound 13 3.51 20.93 163 red 14 Compound 14 3.52 20.14 164 red 15 Compound 15 3.44 20.70 152 red 16 Compound 16 3.40 20.28 151 red 17 Compound 17 3.47 21.05 163 red 18 Compound 18 3.52 20.55 153 red 19 Compound 19 3.42 20.24 156 red 20 Compound 20 3.60 20.21 179 red

[0403] Example No. Host Driving voltage (V) Efficiency (cd / A) Life T95(hr) luminous color 21 Compound 21 3.60 20.37 162 red 22 Compound 22 3.60 20.63 184 red 23 Compound 23 3.52 20.36 168 red 24 Compound 24 3.68 18.96 168 red 25 Compound 25 3.67 19.23 184 red 26 Compound 26 3.43 20.38 186 red 27 Compound 27 3.56 18.98 203 red 28 Compound 28 3.60 20.67 197 red 29 Compound 29 3.43 20.25 184 red 30 Compound 30 3.54 20.56 192 red 31 Compound 31 3.58 20.23 206 red 32 Compound 32 3.63 18.40 187 red 33 Compound 33 3.39 19.03 237 red 34 Compound 34 3.52 17.31 189 red 35 Compound 35 3.56 20.12 218 red 36 Compound 36 3.50 21.07 211 red 37 Compound 37 3.62 20.34 203 red 38 Compound 38 3.59 20.66 225 red

[0405] Comparative Example No. Host Driving voltage (V) Efficiency (cd / A) Life T95(hr) luminous color 1 Compound B-1 4.08 15.32 73 red 2 Compound B-2 4.02 15.78 78 red 3 Compound B-3 3.93 16.02 102 red 4 Compound B-4 4.15 14.87 34 red 5 Compound B-5 3.81 16.45 127 red 6 Compound B-6 3.87 16.17 115 red

[0407] As a result of the experiment, the organic light-emitting device of the example using the compound according to the present invention as the red light-emitting layer showed a decrease in driving voltage and an increase in efficiency and lifespan compared to the comparative example. In addition, the organic light-emitting devices of Examples 24 to 38 containing a compound substituted with deuterium exhibited improved lifespan characteristics. These results indicate that when the compound according to the present invention is used as the host of the red light-emitting layer, energy transfer to the red dopant within the light-emitting layer is well achieved, and electrons and holes within the light-emitting layer combine more stably and in a balanced manner to form excitons, thereby significantly improving the efficiency and lifespan characteristics of the organic light-emitting device.

[0408] From these results, the compound according to the present invention can significantly improve driving voltage, luminous efficiency, and lifespan characteristics when applied to an organic light-emitting diode. Explanation of the symbols

[0410] 1: Substrate 2: Anode 3: Hole transport layer 4: Emissive layer 5: Electron injection and transport layer 6: Cathode 7: Hole injection layer 8: Electron blocking layer 9: Poison blockade layer

Claims

Claim 1 Compounds represented by any one of the following chemical formulas 1-a to 1-h: In the above formulas 1-a to 1-e, 1-g, and 1-h, Ar is phenyl, naphthyl, biphenyl, dibenzofuranyl, or dibenzothiophenyl, said Ar is unsubstituted or substituted with one or more deuterium atoms, L1 is a single bond, L2 and L3 are each independently a single bond or are selected from the group consisting of, said L2 and L3 are each independently unsubstituted or substituted with one or more deuterium atoms, and In the above chemical formula, the dotted line indicates the bonding position, and R1 is hydrogen; deuterium; or is phenyl or naphthyl, wherein the phenyl or naphthyl is unsubstituted or substituted with one or more deuterium atoms, R2 is phenyl substituted with deuterium or unsubstituted, p is an integer from 0 to 7, Dn represents the number of deuterium substitutions in the compound, and n is an integer from 5 to 30, wherein L3 is bonded to a carbon at the C1 or C2 position of a phenanthrene structure, provided that when L3 is bonded to a carbon at the C2 position of a phenanthrene structure, R1 is phenyl or naphthyl substituted with one or more deuterium atoms or unsubstituted, and p is an integer from 1 to 7, wherein in the above formula 1-f, Ar is phenyl, naphthyl, biphenyl, dibenzofuranyl, or dibenzothiophenyl, wherein Ar is unsubstituted or substituted with one or more deuterium atoms, L1 is a single bond, and L2 and L3 are each independently single bonds or any selected from the group consisting of There is one, and the above L2 and L3 are each independently unsubstituted or substituted with one or more deuterium atoms, and In the above chemical formula, the dotted line indicates the bonding position, R1 is deuterium; or phenyl or naphthyl, said phenyl or naphthyl is unsubstituted or substituted with one or more deuteriums, R2 is phenyl substituted with deuterium or unsubstituted, p is an integer from 1 to 7, Dn indicates the number of deuterium substitutions in the compound, n is an integer from 5 to 30, said L3 is bonded to a carbon at the C1 or C2 position of the phenanthrene structure, provided that when L3 is bonded to a carbon at the C2 position of the phenanthrene structure, R1 is phenyl or naphthyl substituted with one or more deuteriums or unsubstituted, and p is an integer from 1 to 7. Claim 2 delete Claim 3 delete Claim 4 delete Claim 5 delete Claim 6 delete Claim 7 In claim 1, the compound is any one selected from the group consisting of the following compounds: In the above chemical formula, Dn is as defined in claim 1. Claim 8 An organic light-emitting device comprising: a first electrode; a second electrode provided opposite to the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers comprise a compound according to any one of claims 1 and 7. Claim 9 An organic light-emitting device according to claim 8, wherein the organic layer is a light-emitting layer.

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