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.

[0009] Meanwhile, recently, organic light-emitting diodes (OLEDs) are being developed using solution processes, particularly inkjet processes, instead of conventional deposition processes to reduce process costs. In the early stages, there were attempts to develop OLEDs by coating all OLED layers using a solution process, but due to limitations in current technology, research is underway on a hybrid process in which only HIL, HTL, and EML are processed using a solution process, while subsequent processes utilize conventional deposition processes.

[0011] Accordingly, the present invention provides a novel organic light-emitting diode material that can be used in organic light-emitting diodes and simultaneously in solution processes. Prior art literature

[0012] Korean Patent Publication No. 10-2000-0051826 The problem to be solved

[0013] The present invention relates to a novel compound and an organic light-emitting device containing the same. means of solving the problem

[0015] The present invention provides a compound represented by the following chemical formula 1:

[0016] [Chemical Formula 1]

[0017]

[0018] In the above chemical formula 1,

[0019] L1 to L8 are each independently a single bond; phenylene; or naphthylene, and

[0020] However, at least one of L1 to L4 is one of the divalent linkers represented by the following chemical formulas 2a to 2e, and

[0021]

[0022] Ar1 and Ar2 are each independently phenyl or naphthyl.

[0024] 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

[0025] 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 also be used in a solution process and can improve efficiency and lifespan characteristics in an organic light-emitting device. Brief explanation of the drawing

[0027] FIG. 1 illustrates an example of an organic light-emitting device comprising a substrate (1), an anode (2), a light-emitting layer (3), and a cathode (4). FIG. 2 illustrates an example of an organic light-emitting device comprising a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), a light-emitting layer (3), an electron injection and transport layer (7), and a cathode (4). Specific details for implementing the invention

[0028] The present invention will be described in more detail below to aid in understanding.

[0030] (Definition of Terms)

[0031] In this specification, and means a bond connected to another substituent.

[0033] 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."

[0035] 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.

[0036]

[0038] In the present specification, the oxygen 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.

[0039]

[0041] 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.

[0042]

[0044] 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.

[0046] In this specification, boron groups specifically include trimethylboron groups, triethylboron groups, t-butyldimethylboron groups, triphenylboron groups, phenylboron groups, etc., but are not limited thereto.

[0048] In this specification, examples of halogen groups include fluoro, chloro, bromo, or iodo.

[0050] 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, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, 1-ethyl-propyl, 1,1-dimethylpropyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, isohexyl, 1-methylhexyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 5-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 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.

[0052] 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.

[0054] In the present specification, the cycloalkyl group is not particularly limited, but it is preferable that it has 3 to 60 carbon atoms, and 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 another embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 6. Specifically, 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. are used, but are not limited thereto.

[0056] 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.

[0058] In the present specification, the heteroaryl is a heteroaryl comprising one or more of O, N, Si and S as heteroelements, and while the number of carbon atoms is not particularly limited, it is preferable that the number of carbon atoms be 2 to 60. Examples of heteroaryls include thiophene, furan, pyrrole, imidazole, thiazole, oxazole, oxadiazole, triazole, pyridyl, bipyridyl, pyrimidyl, triazine, acryl, pyridazine, pyrazinyl, quinolinyl, quinazolin, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinoline, indole, carbazole, benzoxazole, benzimidazole, benzothiazole, benzocarbazole, benzothiophen, dibenzothiophen, benzofuranyl, phenanthroline, isooxazolyl, thiadiazole, phenothiazinyl, and There are dibenzofuranyl groups, etc., but are not limited thereto.

[0060] 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.

[0062] In this specification, the term "deuterated or substituted with deuterium" means that at least one available hydrogen in each chemical formula is substituted with deuterium. Specifically, in the definition of each chemical formula or substituent, being substituted with deuterium means that at least one of the positions where hydrogen can be bonded within the molecule is substituted with deuterium.

[0064] Additionally, in this specification, the term "deuterium substitution rate" means the percentage of the number of substituted deuterium atoms relative to the total number of hydrogen atoms that may exist in each chemical formula.

[0066] (compound)

[0067] The present invention provides a compound represented by the above chemical formula 1.

[0069] The compound represented by the above chemical formula 1 is a compound having a structure in which three 9,10-anthracenylenes are connected by one or more phenylene or naphthylene linkers, wherein at least one of the linkers L1 to L4 connecting two 9,10-anthracenylenes is one of the divalent linkers represented by the following chemical formulas 2a to 2e.

[0070] .

[0072] The above-mentioned compound having such a structure has superior structural stability compared to a compound having a structure in which L1 to L4 are single bonds, phenylene, 1,4-naphthylene, 2,3-naphthylene, 2,6-naphthylene, 2,7-naphthylene, or 1,5-naphthylene, so material stability can be increased.

[0074] Accordingly, an organic light-emitting device employing the above compound can not only exhibit a lower driving voltage compared to an organic light-emitting device employing a compound having a structure different from that of the present invention, but can also simultaneously improve efficiency and lifespan characteristics.

[0076] In addition, the compound represented by the above chemical formula 1 has high solubility in organic solvents used in solution processes, such as cyclohexanone, and is suitable for use in large-area solution processes such as inkjet coating methods using solvents with high boiling points.

[0078] Preferably, at least two of L1 to L8 are not single bonds. Also preferably, at least two of L1 to L4 are not single bonds. Also preferably, L1 and L2 are not single bonds.

[0080] Additionally, specifically, one or two of L1 to L4 may be one of the divalent linkers represented by the above chemical formulas 2a to 2e.

[0082] More specifically,

[0083] L1 and L2 are each independently one of the divalent linkers represented by the chemical formulas 2a to 2e, and L3 and L4 are single bonds;

[0084] One of L1 and L2 is one of the divalent linkers represented by the above chemical formulas 2a to 2e, and the other of L1 and L2 is one of the divalent linkers represented by the following chemical formulas 2f to 2j, and L3 and L4 are single bonds;

[0085] L1 and L4 are each independently one of the divalent linkers represented by the formulas 2a to 2e, L2 is phenylene, and L3 is a single bond; or

[0086] One of L1 and L4 is one of the divalent linkers represented by the above chemical formulas 2a to 2e, and the other of L1 and L4 is one of the divalent linkers represented by the following chemical formulas 2f to 2j, L2 is phenylene, and L3 may be a single bond:

[0087] .

[0089] Additionally, *-L1-L3-*' and *-L2-L4-*' may each be any one selected from a group consisting of independently:

[0090]

[0091] In the above,

[0092] * indicates the binding site with anthracene, and *' indicates the binding site with L3 or L4.

[0094] In this case, *-L1-L3-*' and *-L2-L4-*' may be identical or different from each other.

[0096] In addition, the above may be any one selected from the divalent linkers represented by the following chemical formulas Core 1 to Core 25:

[0097]

[0098]

[0099] .

[0101] In addition, L5 and L6 may each independently be a single bond, 1,3-phenylene, or 1,4-phenylene.

[0103] In this case, L5 and L6 can be identical to each other.

[0105] And, L7 and L8 may each independently be a single bond or any one selected from the divalent linkers represented by the following chemical formulas 3a to 3m.

[0106] .

[0108] Preferably, L7 and L8 may each independently be a single bond, 1,3-phenylene, 1,4-phenylene, or 1,4-naphthyl.

[0110] In this case, L7 and L8 can be identical to each other.

[0112] In addition, Ar1 and Ar2 are each independently phenyl, 1-naphthyl, or 2-naphthyl.

[0113] In this case, Ar1 and Ar2 can be identical to each other.

[0115] For example, Ar1 and Ar2 are both phenyl or;

[0116] Ar1 and Ar2 are both 1-naphthyl; or

[0117] Ar1 and Ar2 can both be 2-naphthyl.

[0119] In addition, the above and above They can be identical to each other.

[0121] The above and above Each is independently selected from any one of the substituents represented by the following chemical formulas R1 to R22:

[0123]

[0124]

[0126] Meanwhile, the compound represented by the above chemical formula 1 is any one selected from the group consisting of compounds represented by the following chemical formula 1':

[0127] [Chemical Formula 1']

[0128]

[0129] In the above chemical formula 1',

[0130] The Core is any one selected from the divalent linkers represented by the following chemical formulas Core 1 to Core 25, and

[0132]

[0133]

[0134] R is any one selected from the substituents represented by the following chemical formulas R1 to R22, and

[0136]

[0137]

[0138] The compound represented by the above chemical formula 1' is as follows:

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154] .

[0156] In the above chemical formula 1', "Core" is of the above chemical formula 1. Corresponds to, and "R" is and It corresponds to.

[0158] Meanwhile, the compound represented by the above chemical formula 1 is, for example, and If they are identical, they can be manufactured using the manufacturing method shown in Reaction Scheme 1 below:

[0159] [Reaction Equation 1]

[0160]

[0161] In the above reaction scheme 1, the definitions for each substituent are as previously explained, and BPin means a boronic pinacol ester group.

[0162] Specifically, the compound represented by the above chemical formula 1 can be prepared through steps a and b.

[0163] First, step a above is a step of preparing compound 1-2 by introducing a -OTf(-O3SCF3) group, which is a reactor group for the Suzuki coupling reaction, into compound 1-1 using Tf2O (Trifluoromethanesulfonic anhydride).

[0164] Next, step b is a step of preparing the compound represented by Formula 1 through a Suzuki coupling reaction of compounds 1-2 and 1-3. It is preferable to perform these Suzuki coupling reactions in the presence of a palladium catalyst and a base, respectively. Additionally, the reactor for the Suzuki coupling reaction can be appropriately modified, and the method for preparing the compound represented by Formula 1 can be further specified in the preparation examples described later.

[0166] Meanwhile, the compound represented by the above chemical formula 1 has high solubility in organic solvents used in solution processes, such as cyclohexanone, and is suitable for use in large-area solution processes such as inkjet coating methods that use solvents with high boiling points.

[0168] An organic layer containing a compound according to the present invention can be formed using various methods such as vacuum deposition and solution processes, and the solution process is described in detail below.

[0170] (Coating composition)

[0171] Meanwhile, the compound according to the present invention can form an organic layer, particularly a light-emitting layer, of an organic light-emitting device through a solution process. Specifically, the compound can be used as a host material for the light-emitting layer. To this end, the present invention provides a coating composition comprising the compound according to the present invention and a solvent as described above.

[0173] The above solvent is not particularly limited as long as it is a solvent capable of dissolving or dispersing the compound according to the present invention, and examples include chlorine-based solvents such as chloroform, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, o-dichlorobenzene; ether-based solvents such as tetrahydrofuran, dioxane; aromatic hydrocarbon-based solvents such as toluene, xylene, trimethylbenzene, mesitylene, 1-methylnaphthalene, 2-methylnaphthalene; aliphatic hydrocarbon-based solvents such as cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, n-decane; ketone-based solvents such as acetone, methyl ethyl ketone, cyclohexanone; and ester-based solvents such as ethyl acetate, butyl acetate, ethyl cellosolve acetate. Examples include polyhydric alcohols and their derivatives such as ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxyethane, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerin, and 1,2-hexanediol; alcohol-based solvents such as methanol, ethanol, propanol, isopropanol, and cyclohexanol; sulfoxide-based solvents such as dimethyl sulfoxide; and amide-based solvents such as N-methyl-2-pyrrolidone and N,N-dimethylformamide; benzoate-based solvents such as butyl benzoate, methyl-2-methoxybenzoate, and ethyl benzoate; phthalate-based solvents such as dimethyl phthalate, diethyl phthalate, and diphenyl phthalate; tetralin; and solvents such as 3-phenoxytoluene. In addition, the aforementioned solvent may be used alone or a mixture of two or more solvents may be used. Preferably, cyclohexanone may be used as the solvent.

[0175] In addition, the coating composition may further include a compound used as a dopant material, and a description of the compound used in the host material will be provided later.

[0177] In addition, the viscosity of the coating composition is preferably 1 cP or higher. Furthermore, considering the ease of coating the coating composition, the viscosity of the coating composition is preferably 10 cP or lower. In addition, the concentration of the compound according to the present invention in the coating composition is preferably 0.1 wt / v% or higher. Furthermore, to ensure that the coating composition can be coated optimally, the concentration of the compound according to the present invention in the coating composition is preferably 20 wt / v% or lower.

[0179] In addition, the solubility (wt%) of the compound represented by Chemical Formula 1 at room temperature and pressure may be 0.1 wt% or more based on the solvent cyclohexanone, more specifically 0.1 wt% to 5 wt%. Accordingly, a coating composition comprising the compound represented by Chemical Formula 1 and a solvent may be used in a solution process.

[0181] In addition, the present invention provides a method for forming a light-emitting layer using the coating composition described above. Specifically, the method comprises the steps of: coating the light-emitting layer according to the present invention described above onto an anode or onto a hole transport layer formed on an anode using a solution process; and heat-treating the coated coating composition.

[0183] The above solution process uses the coating composition according to the present invention described above and includes spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, etc., but is not limited to these.

[0185] In the above heat treatment step, the heat treatment temperature is preferably 150 to 230°C. In addition, the heat treatment time is 1 minute to 3 hours, and more preferably 10 minutes to 1 hour. Furthermore, it is preferable to perform the heat treatment in an inert gas atmosphere such as argon or nitrogen.

[0187] (Organic light-emitting diode)

[0188] 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.

[0190] 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, 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.

[0192] In one embodiment, the organic layer may include a light-emitting layer, and the organic layer containing the compound may be a light-emitting layer.

[0194] In another 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 a light-emitting layer or an electron injection and transport layer.

[0196] In another embodiment, the organic layer may include a hole injection layer, a hole transport layer, an electron suppression layer, a light-emitting layer, and an electron injection and transport layer, wherein the organic layer containing the compound may be a light-emitting layer or an electron injection and transport layer.

[0198] In another embodiment, the organic layer may include a hole injection layer, a hole transport layer, an electron suppression layer, an emitting layer, an electron blocking layer, and an electron injection and transport layer, wherein the organic layer containing the compound may be an emitting layer or an electron injection and transport layer.

[0200] 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.

[0202] 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.

[0204] FIG. 1 illustrates an example of an organic light-emitting device comprising a substrate (1), an anode (2), a light-emitting layer (3), and a cathode (4). In such a structure, a compound represented by Chemical Formula 1 may be included in the light-emitting layer.

[0206] FIG. 2 illustrates an example of an organic light-emitting device comprising a substrate (1), an anode (2), a hole injection layer (5), a hole transport layer (6), a light-emitting layer (3), an electron injection and transport layer (7), and a cathode (4). In such a structure, a compound represented by the chemical formula 1 may be included in the light-emitting layer.

[0208] The organic light-emitting device according to the present invention can be manufactured using materials and methods known in the art, except that the light-emitting layer comprises a compound according to the present invention and is manufactured as described above.

[0210] For example, an organic light-emitting device according to the present invention can be manufactured by sequentially stacking an anode, an organic layer, and a cathode 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 or 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 thereon, and finally depositing a material that can be used as a cathode thereon.

[0212] 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.

[0214] 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.

[0216] As for the anode material, a material with a large work function is generally preferred to facilitate hole injection into the organic layer. 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; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited to these.

[0218] 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 materials such as LiF / Al or LiO2 / Al, but are not limited to these.

[0220] The hole injection layer above is a layer that injects holes from the electrode, and as the 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 metal porphyrin, oligothiophene, arylamine-based organic materials, hexanitrile-hexaazatriphenylene-based organic materials, quinacridone-based organic materials, perylene-based organic materials, anthraquinone, and conductive polymers of polyaniline and polythiophene series, but are not limited to these.

[0222] The hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the emissive layer. Suitable hole transport materials are materials capable of receiving holes from the anode or the hole injection layer and transferring them to the emissive layer, and materials with high mobility for holes are suitable. As the hole transport material, a compound represented by Chemical Formula 1 may be used, or 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.

[0224] Meanwhile, the above-described organic light-emitting device may have an electron suppression layer between the hole transport layer and the light-emitting layer. The electron suppression layer is formed on the hole transport layer and, preferably, is provided in contact with the light-emitting layer. It refers to a layer that improves the efficiency of the organic light-emitting device by controlling hole mobility and preventing excessive electron movement to increase the probability of hole-electron coupling. The electron suppression layer includes an electron blocking material. Examples of such electron blocking materials may include a compound represented by Chemical Formula 1 or an arylamine-based organic material, but are not limited thereto.

[0226] The above-described light-emitting layer may include a host material and a dopant material. A compound represented by Chemical Formula 1 may be used as the host material. Additionally, a condensed aromatic ring derivative or a heterocyclic compound containing the like may be used together with the compound represented by Chemical Formula 1 as the host material. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc., but are not limited thereto.

[0228] In addition, 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.

[0230] Meanwhile, the above-described organic light-emitting device may have a hole blocking layer between the light-emitting layer and the electron transport layer. 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 the 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 includes a hole blocking material, and examples of such hole blocking materials may include compounds with introduced electron-absorbing groups such as azine derivatives including triazine; triazole derivatives; oxadiazole derivatives; phenanthroline derivatives; and phosphine oxide derivatives, but are not limited thereto.

[0232] 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, preolenylidene methane, anthrone, etc., their derivatives, metal complex compounds, or nitrogen-containing five-membered ring derivatives, but is not limited thereto.

[0234] 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.

[0236] 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-hydroxyquinolinato)chlorogallium, bis(2-methyl-8-hydroxyquinolinato)(o-cresolato)gallium, Bis(2-methyl-8-hydroxyquinolinato)(1-naphtolato)aluminum, bis(2-methyl-8-hydroxyquinolinato)(2-naphtolato)gallium, etc., are included but are not limited thereto.

[0238] In addition to the materials described above, the light-emitting layer, hole injection layer, hole transport layer, electron transport layer, and electron injection layer may further include inorganic compounds such as quantum dots or polymer compounds.

[0240] The above quantum dots may be, for example, colloidal quantum dots, alloy quantum dots, core-shell quantum dots, or core quantum dots. They may be quantum dots containing elements belonging to Group 2 and Group 16, elements belonging to Group 13 and Group 15, elements belonging to Group 13 and Group 17, elements belonging to Group 11 and Group 17, or elements belonging to Group 14 and Group 15, and quantum dots containing elements such as cadmium (Cd), selenium (Se), zinc (Zn), sulfur (S), phosphorus (P), indium (In), tellurium (Te), lead (Pb), gallium (Ga), and arsenic (As) may be used.

[0242] 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.

[0244] In addition, the compound according to the present invention may be included in organic solar cells or organic transistors in addition to organic light-emitting devices.

[0246] 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.

[0248] Preparation Example 1: Preparation of Compound 3-2

[0249]

[0250] Compound 1-a (1.0 eq.) and Compound 1-b (2.1 eq.) were placed in a round-bottom flask and dissolved in THF:PhMe 1:1 (v / v). Na2CO3 (6.0 eq.) dissolved in water was added. Pd(PPh3)4 (10 mol%) was added dropwise at a bath temperature of 130°C and stirred overnight. After the reaction, the reaction mixture was cooled to room temperature, sufficiently diluted with EtOAc, and the organic layer was separated by washing with EtOAc / brine. Water was removed with MgSO4 and passed through a Celite-Florisil-Silica pad. The passed solution was concentrated under reduced pressure and purified by column chromatography to prepare Compound 1-c (67% yield).

[0252] Compound 1-c (1.0 eq.) was placed in a round-bottom flask and dissolved in anhydrous CH2Cl2. Subsequently, pyridine (4.0 eq.) was added dropwise at room temperature, and the bath temperature was lowered to 0°C and stirred for 10 minutes. Then, Tf2O (2.4 eq.) dissolved in anhydrous CH2Cl2 was slowly added dropwise to the mixture using a dropping funnel, the bath temperature was gradually raised from 0°C to room temperature, and the mixture was stirred overnight. After the reaction, the reaction mixture was sufficiently diluted in CH2Cl2 and washed with CH2Cl2 / brine to separate the organic layer. Water was removed with MgSO4 and passed through a Celite-Florisil-Silica pad. The passed solution was concentrated under reduced pressure and purified by column chromatography to prepare compound 1-d (98% yield).

[0254] Compound 1-d (1.0 eq.) and Compound 1-e (2.1 eq.) were placed in a round-bottom flask and dissolved in THF:PhMe 1:1 (v / v). Na2CO3 (6.0 eq.) dissolved in water was added. Pd(PPh3)4 (10 mol%) was added dropwise at a bath temperature of 130°C and stirred overnight. After the reaction, the reaction mixture was cooled to room temperature, sufficiently diluted with EtOAc, and the organic layer was separated by washing with EtOAc / brine. Water was removed with MgSO4 and passed through a Celite-Florisil-Silica pad. The passed solution was concentrated under reduced pressure and purified by column chromatography to prepare Compound 3-2 (87% yield).

[0255] m / z [M+H] + 1087.5

[0257] Preparation Example 2: Preparation of Compound 3-3

[0258]

[0259] Compound 3-3 was prepared in the same manner as the method for preparing compound 3-2, except that compound 2-a was used instead of compound 1-e.

[0260] m / z [M+H] + 1087.5

[0262] Preparation Example 3: Preparation of Compound 3-5

[0263]

[0264] Compound 3-5 was prepared in the same manner as the method for preparing compound 3-2, except that compound 3-a was used instead of compound 1-e.

[0265] m / z [M+H] + 1187.6

[0267] Preparation Example 4: Preparation of Compounds 3-6

[0268]

[0269] Compound 3-6 was prepared in the same manner as the method of preparing compound 3-2, except that compound 4-a was used instead of compound 1-e.

[0270] m / z [M+H] + 1187.6

[0272] Preparation Example 5: Preparation of Compounds 3-8

[0273]

[0274] Compound 3-8 was prepared in the same manner as the method of preparing compound 3-2, except that compound 5-a was used instead of compound 1-e.

[0275] m / z [M+H] + 1187.6

[0277] Preparation Example 6: Preparation of Compound 3-9

[0278]

[0279] Compound 3-9 was prepared in the same manner as the method of preparing compound 3-2, except that compound 6-a was used instead of compound 1-e.

[0280] m / z [M+H] + 1187.5

[0282] Preparation Example 7: Preparation of Compound 3-7

[0283]

[0284] Compound 3-7 was prepared in the same manner as the method of preparing compound 3-2, except that compound 7-a was used instead of compound 1-e.

[0285] m / z [M+H] + 1035.4

[0287] Preparation Example 8: Preparation of Compounds 3-4

[0288]

[0289] Compound 3-4 was prepared in the same manner as the method for preparing compound 3-2, except that compound 8-a was used instead of compound 1-e.

[0290] m / z [M+H] + 1035.3

[0292] Preparation Example 9: Preparation of Compound 3-14

[0293]

[0294] Compound 3-14 was prepared in the same manner as the method of preparing compound 3-2, except that compound 9-a was used instead of compound 1-e.

[0295] m / z [M+H] + 1339.4

[0297] Preparation Example 10: Preparation of Compounds 3-15

[0298]

[0299] Compound 3-15 was prepared in the same manner as the method of preparing compound 3-2, except that compound 10-a was used instead of compound 1-e.

[0300] m / z [M+H] + 1339.5

[0302] Preparation Example 11: Preparation of Compound 3-11

[0303]

[0304] Compound 3-11 was prepared in the same manner as the method for preparing compound 3-2, except that compound 11-a was used instead of compound 1-e.

[0305] m / z [M+H] + 1339.4

[0307] Preparation Example 12: Preparation of Compound 3-12

[0308]

[0309] Compound 3-12 was prepared in the same manner as the method for preparing compound 3-2, except that compound 12-a was used instead of compound 1-e.

[0310] m / z [M+H] + 1339.6

[0312] Preparation Example 13: Preparation of Compounds 3-10

[0313]

[0314] Compound 3-10 was prepared in the same manner as the method of preparing compound 3-2, except that compound 13-a was used instead of compound 1-e.

[0315] m / z [M+H] + 1187.5

[0317] Preparation Example 14: Preparation of Compound 3-13

[0318]

[0319] Compound 3-13 was prepared in the same manner as the method of preparing compound 3-2, except that compound 14-a was used instead of compound 1-e.

[0320] m / z [M+H] + 1187.5

[0322] Preparation Example 15: Preparation of Compound 3-16

[0323]

[0324] Compound 3-16 was prepared in the same manner as the method of preparing compound 3-2, except that compound 15-a was used instead of compound 1-e.

[0325] m / z [M+H] + 1187.6

[0327] Preparation Example 16: Preparation of Compound 3-17

[0328]

[0329] Compound 3-17 was prepared in the same manner as the method of preparing compound 3-2, except that compound 16-a was used instead of compound 1-e.

[0330] m / z [M+H] + 1339.4

[0332] Preparation Example 17: Preparation of Compound 3-18

[0333]

[0334] Compound 3-18 was prepared in the same manner as the method of preparing compound 3-2, except that compound 17-a was used instead of compound 1-e.

[0335] m / z [M+H] + 1339.4

[0337] Preparation Example 18: Preparation of Compound 3-19

[0338]

[0339] Compound 3-19 was prepared in the same manner as the method of preparing compound 3-2, except that compound 18-a was used instead of compound 1-e.

[0340] m / z [M+H] + 1187.6

[0342] Preparation Example 19: Preparation of Compounds 3-20

[0343]

[0344] Compound 3-20 was prepared in the same manner as the method of preparing compound 3-2, except that compound 19-a was used instead of compound 1-e.

[0345] m / z [M+H] + 1339.6

[0347] Preparation Example 20: Preparation of Compound 3-21

[0348]

[0349] Compound 3-21 was prepared in the same manner as the method of preparing compound 3-2, except that compound 20-a was used instead of compound 1-e.

[0350] m / z [M+H] + 1339.4

[0352] Preparation Example 21: Preparation of Compound 3-22

[0353]

[0354] Compound 3-22 was prepared in the same manner as the method of preparing compound 3-2, except that compound 21-a was used instead of compound 1-e.

[0355] m / z [M+H] + 1187.5

[0357] Preparation Example 22: Preparation of Compound 3-1

[0358]

[0359] Compound 3-1 was prepared in the same manner as the method for preparing compound 3-2, except that compound 22-a was used instead of compound 1-e.

[0360] m / z [M+H] + 935.4

[0362] Preparation Example 23: Preparation of Compounds 1-6

[0363]

[0364] Compound 1-6 was prepared in the same manner as the method for preparing compound 3-2, except that compound 23-a was used instead of compound 1-b and compound 4-a was used instead of 1-e.

[0365] m / z [M+H] + 1187.6

[0368] Preparation Example 24: Preparation of Compound 1-9

[0369]

[0370] Compound 1-9 was prepared in the same manner as the method of preparing compound 1-6, except that compound 6-a was used instead of compound 4-a.

[0371] m / z [M+H] + 1187.5

[0373] Preparation Example 25: Preparation of Compound 1-17

[0374]

[0375] Compound 1-17 was prepared in the same manner as the method of preparing compound 1-6, except that compound 16-a was used instead of compound 4-a.

[0376] m / z [M+H] + 1339.6

[0378] Preparation Example 26: Preparation of Compound 1-18

[0379]

[0380] Compound 1-18 was prepared in the same manner as the method of preparing compound 1-6, except that compound 17-a was used instead of compound 4-a.

[0381] m / z [M+H] + 1339.6

[0383] Preparation Example 27: Preparation of Compounds 1-20

[0384]

[0385] Compound 1-20 was prepared in the same manner as the method of preparing compound 1-6, except that compound 19-a was used instead of compound 4-a.

[0386] m / z [M+H] + 1339.5

[0388] Preparation Example 28: Preparation of Compound 1-21

[0389]

[0390] Compound 1-21 was prepared in the same manner as the method of preparing compound 1-6, except that compound 20-a was used instead of compound 4-a.

[0391] m / z [M+H] + 1339.4

[0393] Preparation Example 29: Preparation of Compound 2-6

[0394]

[0395] Compound 2-6 was prepared in the same manner as the method for preparing compound 3-2, except that compound 35-a was used instead of compound 1-b and compound 4-a was used instead of 1-e.

[0396] m / z [M+H] + 1187.5

[0398] Preparation Example 30: Preparation of Compound 2-18

[0399]

[0400] Compound 2-18 was prepared in the same manner as the method for preparing compound 2-6, except that compound 17-a was used instead of compound 4-a.

[0401] m / z [M+H] + 1339.5

[0403] Preparation Example 31: Preparation of Compound 2-21

[0404]

[0405] Compound 2-21 was prepared in the same manner as the method for preparing compound 2-6, except that compound 20-a was used instead of compound 4-a.

[0406] m / z [M+H] + 1339.6

[0408] Preparation Example 32: Preparation of Compound 6-6

[0409]

[0410] Compound 6-6 was prepared in the same manner as the method for preparing compound 3-2, except that compound 38-a was used instead of compound 1-a and compound 4-a was used instead of 1-e.

[0411] m / z [M+H] + 1263.5

[0413] Preparation Example 33: Preparation of Compound 6-18

[0414]

[0415] Compound 6-18 was prepared in the same manner as the method for preparing compound 6-6, except that compound 17-a was used instead of compound 4-a.

[0416] m / z [M+H] + 1415.6

[0418] Preparation Example 34: Preparation of Compound 6-21

[0419]

[0420] Compound 6-21 was prepared in the same manner as the method for preparing compound 6-6, except that compound 20-a was used instead of compound 4-a.

[0421] m / z [M+H] + 1415.5

[0423] Preparation Example 35: Preparation of Compound 9-6

[0424]

[0425] Compound 9-6 was prepared in the same manner as the method of preparing compound 3-2, except that compound 41-a was used instead of compound 1-a and compound 4-a was used instead of 1-e.

[0426] m / z [M+H] + 1263.4

[0428] Preparation Example 36: Preparation of Compound 9-18

[0429]

[0430] Compound 9-18 was prepared in the same manner as the method of preparing compound 9-6, except that compound 17-a was used instead of compound 4-a.

[0431] m / z [M+H] + 1415.6

[0433] Preparation Example 37: Preparation of Compound 9-21

[0434]

[0435] Compound 9-21 was prepared in the same manner as the method for preparing compound 9-6, except that compound 20-a was used instead of compound 4-a.

[0436] m / z [M+H] + 1415.4

[0438] Preparation Example 38: Preparation of Compound 25-6

[0439]

[0440] Compound 1-a (1.0 eq.) and Compound 1-b (1.05 eq.) were placed in a round-bottom flask and dissolved in THF:PhMe 1:1 (v / v). Na2CO3 (3.0 eq.) dissolved in water was added. Pd(PPh3)4 (5 mol%) was added dropwise under a bath temperature of 80°C and stirred for 4 hours. After the reaction, the reaction mixture was cooled to room temperature, sufficiently diluted with EtOAc, and the organic layer was separated by washing with EtOAc / brine. Water was removed with MgSO4 and passed through a Celite-Florisil-Silica pad. The passed solution was concentrated under reduced pressure and purified by column chromatography to prepare Compound 44-a (52% yield).

[0442] Compound 44-a (1.0 eq.) and Compound 44-b (1.05 eq.) were placed in a round-bottom flask and dissolved in THF:PhMe 1:1 (v / v). Na2CO3 (6.0 eq.) dissolved in water was added. Pd(PPh3)4 (10 mol%) was added dropwise at a bath temperature of 130°C and stirred overnight. After the reaction, the reaction mixture was cooled to room temperature, sufficiently diluted with EtOAc, and the organic layer was separated by washing with EtOAc / brine. Water was removed with MgSO4 and passed through a Celite-Florisil-Silica pad. The passed solution was concentrated under reduced pressure and purified by column chromatography to prepare Compound 44-c (60% yield).

[0444] Compound 44-c (1.0 eq.) was placed in a round-bottom flask and dissolved in anhydrous CH2Cl2. Subsequently, pyridine (4.0 eq.) was added dropwise at room temperature, and the bath temperature was lowered to 0°C and stirred for 10 minutes. Then, Tf2O (2.4 eq.) dissolved in anhydrous CH2Cl2 was slowly added dropwise to the mixture using a dropping funnel, the bath temperature was gradually raised from 0°C to room temperature, and the mixture was stirred overnight. After the reaction, the reaction mixture was sufficiently diluted in CH2Cl2 and washed with CH2Cl2 / brine to separate the organic layer. Water was removed with MgSO4 and passed through a Celite-Florisil-Silica pad. The passed solution was concentrated under reduced pressure and purified by column chromatography to prepare compound 44-d (99% yield).

[0446] Compound 44-d (1.0 eq.) and Compound 4-a (2.1 eq.) were placed in a round-bottom flask and dissolved in THF:PhMe 1:1 (v / v). Na2CO3 (6.0 eq.) dissolved in water was added. Pd(PPh3)4 (10 mol%) was added dropwise at a bath temperature of 130°C and stirred overnight. After the reaction, the reaction mixture was cooled to room temperature, sufficiently diluted with EtOAc, and the organic layer was separated by washing with EtOAc / brine. Water was removed with MgSO4 and passed through a Celite-Florisil-Silica pad. The passed solution was concentrated under reduced pressure and purified by column chromatography to prepare Compound 25-6 (79% yield).

[0447] m / z [M+H] + 1187.5

[0449] Preparation Example 39: Preparation of Compounds 25-18

[0450]

[0451] Compound 25-18 was prepared in the same manner as the method for preparing compound 25-6, except that compound 17-a was used instead of compound 4-a.

[0452] m / z [M+H] + 1339.5

[0454] Preparation Example 40: Preparation of Compounds 25-21

[0455]

[0456] Compound 25-21 was prepared in the same manner as the method for preparing compound 25-6, except that compound 20-a was used instead of compound 4-a.

[0457] m / z [M+H] + 1339.4

[0459] Comparative Manufacturing Example 1: Preparation of Compound A

[0460]

[0461] Compound A was prepared in the same manner as the method for preparing Compound 3-2, except that Compound 29-a was used instead of Compound 1-b and Compound 4-a was used instead of 1-e.

[0462] m / z [M+H] + 1187.5

[0464] Comparative Manufacturing Example 2: Preparation of Compound B

[0465]

[0466] Compound B was prepared in the same manner as the method of preparing compound A, except that compound 17-a was used instead of compound 4-a.

[0467] m / z [M+H] + 1339.6

[0469] Comparative Manufacturing Example 3: Preparation of Compound C

[0470]

[0471] Compound C was prepared in the same manner as the method of preparing compound A, except that compound 20-a was used instead of compound 4-a.

[0472] m / z [M+H] + 1339.4

[0474] Comparative Manufacturing Example 4: Preparation of Compound D

[0475]

[0476] Compound D was prepared in the same manner as the method of preparing compound 3-2, except that compound 32-a was used instead of compound 1-b and compound 4-a was used instead of 1-e.

[0477] m / z [M+H] + 1187.5

[0479] Comparative Preparation Example 5: Preparation of Compound E

[0480]

[0481] Compound E was prepared in the same manner as the method of preparing compound D, except that compound 17-a was used instead of compound 4-a.

[0482] m / z [M+H] + 1339.6

[0484] Comparative Manufacturing Example 6: Preparation of Compound F

[0485]

[0486] Compound F was prepared in the same manner as the method of preparing compound D, except that compound 20-a was used instead of compound 4-a.

[0487] m / z [M+H] + 1339.4

[0489] Comparative Preparation Example 7: Preparation of Comparative Compound G

[0490]

[0491] Compound Fa (1.0 eq.) and Compound Fb (2.2 eq.) were placed in a round-bottom flask and dissolved in THF:PhMe 1:1 (v / v). Na2CO3 (6.0 eq.) dissolved in water was added. Pd(PPh3)4 (10 mol%) was added dropwise at a bath temperature of 130°C and stirred overnight. After the reaction, the reaction mixture was cooled to room temperature, sufficiently diluted with EtOAc, and the organic layer was separated by washing with EtOAc / brine. Water was removed with MgSO4 and passed through a Celite-Florisil-Silica pad. The passed solution was concentrated under reduced pressure and purified by column chromatography to prepare Compound G (86% yield).

[0492] m / z [M+H] + 935.4

[0494] Experimental Example 1: Solubility measurement

[0495] It was determined whether the compounds prepared in Preparation Examples 1 to 41 and comparative compounds A to K could each be dissolved in cyclohexanone at a concentration of 1.3 wt% at 25°C, and the results are shown in Table 1. At this time, the structures of comparative compounds H to K are as follows.

[0496]

[0498] compound Solubility (1.3 wt%) compound Solubility (1.3 wt%) Compound 3-2 O Compound 1-20 O Compound 3-3 O Compound 1-21 O Compound 3-5 O Compound 2-6 O Compound 3-6 O Compound 2-18 O Compound 3-8 O Compound 2-21 O Compound 3-9 O Compound 6-6 O Compound 3-7 O Compound 6-18 O Compound 3-4 O Compound 6-21 O Compound 3-14 O Compound 9-6 O Compound 3-15 O Compound 9-18 O Compound 3-11 O Compound 9-21 O Compound 3-12 O Compound 25-6 O Compound 3-10 O Compound 25-18 O Compound 3-13 O Compound 25-21 O Compound 3-16 O Compound A X Compound 3-17 O Compound B X Compound 3-18 O Compound C X Compound 3-19 O Compound D X Compound 3-20 O Compound E X Compound 3-21 O Compound F X Compound 3-22 O Compound G O Compound 3-1 O Compound H X Compound 1-6 O Compound I X Compound 1-9 O Compound J O Compound 1-17 O Compound K O Compound 1-18 O

[0499] As can be seen from Table 1 above, all compounds represented by Chemical Formula 1 were soluble in cyclohexanone at a concentration of 1.3 wt%, but some comparative compounds were not soluble, so it can be seen that they cannot be used as compounds forming the organic layer when manufacturing the organic layer of an organic light-emitting diode using a solution process.

[0501] Example 1

[0502] A glass substrate coated with a thin film of indium tin oxide (ITO) to a thickness of 500 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 Millipore Co. filter was used. After washing the ITO for 30 minutes, ultrasonic cleaning was performed for 10 minutes, repeating the process twice with distilled water. After the distilled water washing was completed, the substrate was ultrasonically cleaned with a solvent of isopropyl and acetone and dried. Subsequently, the substrate was cleaned for 5 minutes and then transported to a glove box.

[0503]

[0504] On the above ITO transparent electrode, a coating composition in which the above compound O and compound P (weight ratio of 2:8) were dissolved in cyclohexanone at 20 wt / v% was spin-coated (4000 rpm) and heat-treated (cured) at 200 ℃ for 30 minutes to form a hole injection layer with a thickness of 400 Å.

[0505]

[0506] A coating composition in which the compound Q (Mn: 27,900; Mw: 35,600; measured by GPC using PC Standard with Agilent 1200 series) was dissolved in toluene at 6 wt / v% was spin-coated (4000 rpm) on the hole injection layer and heat-treated at 200 ℃ for 30 minutes to form a hole transport layer with a thickness of 200 Å.

[0507]

[0508] A coating composition comprising the light-emitting layer host compound 3-2 prepared in Preparation Example 1 and the light-emitting layer dopant compound R (weight ratio of 98:2) dissolved in cyclohexanone at 1.3 wt / v% was spin-coated (4000 rpm) on the hole transport layer above and heat-treated at 180°C for 30 minutes to form a light-emitting layer with a thickness of 400 Å.

[0509]

[0510] After transferring to a vacuum deposition machine, the compound S was vacuum deposited to a thickness of 350 Å on the light-emitting layer to form an electron injection and transport layer. A cathode was formed by sequentially depositing LiF to a thickness of 10 Å and aluminum to a thickness of 1000 Å on the electron injection and transport layer.

[0511] In the above process, the deposition rate of the organic material was maintained at 0.4 to 0.7 Å / sec, while the deposition rates for LiF and aluminum were maintained at 0.3 Å / sec and 2 Å / sec, respectively, and the vacuum level during deposition was 2×10⁻⁶ -7 Up to 5*10 -8 maintained torr.

[0513] Examples 2 to 40

[0514] An organic light-emitting device was prepared in the same manner as in Example 1, except that a compound listed in Table 2 below was used instead of compound 1 as the host of the light-emitting layer.

[0516] Comparative example 1 to Comparative example 3

[0517] An organic light-emitting device was prepared in the same manner as in Example 1, except that a compound listed in Table 2 below was used instead of compound 1 as the host of the light-emitting layer.

[0519] Experimental Example 2: Characterization of Organic Light Emitting Devices

[0520] When current was applied to the organic light-emitting diodes prepared in the above examples and comparative examples, 10 mA / cm 2 The results of measuring the driving voltage, external quantum efficiency (EQE), and lifetime at the current density are shown in Table 2 below. In this case, the external quantum efficiency (EQE) was calculated as "(number of emitted photons) / (number of injected charge carriers) * 100", and T90 represents the time required for the brightness to decrease from the initial brightness (500 nit) to 90%.

[0522] division Emissive layer host Driving voltage (V @10mA / cm) 2 ) EQE(% @10mA / cm 2 ) Lifespan (hr) (T90 @500 nit) Example 1 Compound 3-2 6.9 5.20 690 Example 2 Compound 3-3 7.1 5.32 705 Example 3 Compound 3-5 7.2 5.00 732 Example 4 Compound 3-6 7.0 5.50 810 Example 5 Compound 3-8 7.1 5.25 769 Example 6 Compound 3-9 7.2 5.40 752 Example 7 Compound 3-7 7.0 5.42 725 Example 8 Compound 3-4 6.9 5.30 705 Example 9 Compound 3-14 6.8 5.28 704 Example 10 Compound 3-15 7.1 5.31 735 Example 11 Compound 3-11 7.0 5.42 700 Example 12 Compound 3-12 7.2 5.30 689 Example 13 Compound 3-10 7.3 5.15 745 Example 14 Compound 3-13 6.7 5.15 768 Example 15 Compound 3-16 7.2 5.25 773 Example 16 Compound 3-17 6.9 5.29 745 Example 17 Compound 3-18 6.8 5.32 783 Example 18 Compound 3-19 7.0 5.40 745 Example 19 Compound 3-20 7.2 5.32 705 Example 20 Compound 3-21 7.0 5.15 765 Example 21 Compound 3-22 7.1 5.05 685 Example 22 Compound 3-1 6.8 5.04 724 Example 23 Compound 1-6 6.9 5.12 734 Example 24 Compound 1-9 7.1 5.22 748 Example 25 Compound 1-17 7.0 5.31 746 Example 26 Compound 1-18 7.2 5.35 684 Example 27 Compound 1-20 7.0 5.40 748 Example 28 Compound 1-21 7.2 5.24 743 Example 29 Compound 2-6 7.1 5.18 648 Example 30 Compound 2-18 7.2 5.21 679 Example 31 Compound 2-21 7.0 5.01 699 Example 32 Compound 6-6 7.0 5.13 705 Example 33 Compound 6-18 6.7 5.24 735 Example 34 Compound 6-21 6.8 5.21 752 Example 35 Compound 9-6 7.1 5.18 747 Example 36 Compound 9-18 6.9 5.41 748 Example 37 Compound 9-21 6.8 5.30 699 Example 38 Compound 25-6 7.0 5.52 785 Example 39 Compound 25-18 7.0 5.12 754 Example 40 Compound 25-21 7.1 5.09 776 Comparative Example 1 Compound G 6.9 4.01 420 Comparative Example 2 Compound J 7.0 3.02 185 Comparative Example 3 Compound K 7.0 3.09 201

[0523] As shown in Table 2 above, it is confirmed that the organic light-emitting device containing the compound of the present invention in the light-emitting layer has improved efficiency and lifespan compared to the device of the comparative example.

[0525] Specifically, the organic light-emitting device of the example using the compound represented by Chemical Formula 1 as the host of the light-emitting layer showed improved efficiency and lifespan compared to the organic light-emitting devices of Comparative Examples 1 to 3 using comparative compounds G, J, and K as the hosts of the light-emitting layer, respectively. This is believed to be because the material stability was improved by essentially including a specific linker structure in the case of the compound represented by Chemical Formula 1.

[0527] Therefore, it can be seen that when a compound represented by the above chemical formula 1 is adopted as a host material for an organic light-emitting device, the external quantum efficiency and lifetime characteristics of the organic light-emitting device can be improved simultaneously. Explanation of the symbols

[0530] 1: Substrate 2: Anode 3: Emitting layer 4: Cathode 5: Hole Injection Layer 6: Hole Transport Layer 7: Electron injection and transport layer

Claims

Claim 1 Compound represented by the following chemical formula 1: [Chemical Formula 1] In the above Chemical Formula 1, L1 to L8 are each independently a single bond; phenylene; or naphthylene, provided that at least one of L1 to L4 is one of the divalent linkers represented by the following Chemical Formulas 2a to 2e, and at least two are not single bonds. Ar1 and Ar2 are each independently phenyl or naphthyl. Claim 2 A compound according to claim 1, wherein one or two of L1 to L4 are one of the divalent linkers represented by the chemical formulas 2a to 2e. Claim 3 A compound according to claim 1, wherein L1 and L2 are each independently one of the divalent linkers represented by the formulas 2a to 2e, and L3 and L4 are single bonds; one of L1 and L2 is one of the divalent linkers represented by the formulas 2a to 2e, and the other of L1 and L2 is one of the divalent linkers represented by the following formulas 2f to 2j, and L3 and L4 are single bonds; L1 and L4 are each independently one of the divalent linkers represented by the formulas 2a to 2e, L2 is phenylene, and L3 is a single bond; or one of L1 and L4 is one of the divalent linkers represented by the formulas 2a to 2e, and the other of L1 and L4 is one of the divalent linkers represented by the following formulas 2f to 2j, L2 is phenylene, and L3 is a single bond: . Claim 4 A compound according to claim 1, wherein *-L1-L3-*' and *-L2-L4-*' are each independently selected from the group consisting of: . Claim 5 In paragraph 1, the above A compound selected from any one of the divalent linkers represented by the following chemical formulas core1 to core25: . Claim 6 In paragraph 1, L5 and L6 are each independently compounds having a single bond, 1,3-phenylene, or 1,4-phenylene. Claim 7 In paragraph 1, L7 and L8 are each independently a compound having a single bond, 1,3-phenylene, 1,4-phenylene, or 1,4-naphthyl. Claim 8 A compound according to claim 1, wherein Ar1 and Ar2 are both phenyl; Ar1 ​​and Ar2 are both 1-naphthyl; or Ar1 and Ar2 are both 2-naphthyl. Claim 9 In paragraph 1, the above and above are identical compounds. Claim 10 In claim 1, the compound represented by Chemical Formula 1 is any one selected from the group consisting of compounds represented by Chemical Formula 1' below, compound: [Chemical Formula 1'] In the above chemical formula 1', Core is any one selected from the divalent linkers represented by the following chemical formulas Core 1 to Core 25, and R is any one selected from the substituents represented by the following chemical formulas R1 to R22, and The compound represented by the above chemical formula 1' is as follows: . Claim 11 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 to 10. Claim 12 An organic light-emitting device according to claim 11, wherein the organic layer containing the above compound is a light-emitting layer.

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