Novel compounds and organic light emitting devices comprising the same

Abstract

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

Description

Technical Field

[0001] Cross-references to related applications

[0002] This application claims the benefit and priority of Korean Patent Application No. 10-2021-0030815, filed with the Korean Intellectual Property Office on March 9, 2021, the contents of which are incorporated herein by reference in their entirety.

[0003] This disclosure relates to novel compounds and organic light-emitting devices incorporating the same. Background Technology

[0004] Organic light emission generally refers to the phenomenon of converting electrical energy into light energy using organic materials. Organic light-emitting devices (OLEDs) utilizing organic light emission have characteristics such as wide viewing angle, excellent contrast, fast response time, and excellent brightness, driving voltage, and response speed, and therefore have been the subject of much research.

[0005] Organic light-emitting devices (OLEDs) typically have a structure comprising an anode, a cathode, and an organic material layer between the anode and cathode. The organic material layer often has a multilayer structure containing different materials to improve the efficiency and stability of the OLED. For example, the organic material layer can be formed from 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 an OLED, if a voltage is applied between the two electrodes, holes are injected from the anode into the organic material layer, and electrons are injected from the cathode into the organic material layer. When the injected holes and electrons meet, excitons are formed, and light is emitted when the excitons return to the ground state.

[0006] For organic materials used in organic light-emitting devices as described above, there is a continuous need to develop new materials.

[0007] Meanwhile, to reduce process costs, organic light-emitting devices (OLEDs) using solution methods, particularly inkjet printing, have recently been developed to replace conventional deposition methods. In the initial stages of development, attempts were made to develop OLEDs by coating all OLED layers via solution methods, but current technology has limitations. Therefore, only HIL, HTL, and EML are processed using solution methods, and a hybrid method utilizing conventional deposition techniques is being investigated as a subsequent approach.

[0008] Therefore, this disclosure provides new materials for organic light-emitting devices that can be used in both organic light-emitting devices and solution processing.

[0009] [Existing technical documents]

[0010] [Patent Literature]

[0011] (Patent Document 1) Korean Unexamined Patent Publication No. 10-2000-0051826 Summary of the Invention

[0012] Technical issues

[0013] The purpose of this disclosure is to provide new compounds and organic light-emitting devices incorporating them.

[0014] Technical solution

[0015] According to one aspect of this disclosure, a compound represented by the following chemical formula 1 is provided:

[0016] [Chemical Formula 1]

[0017]

[0018] In chemical formula 1,

[0019] A1 is C 6-60 Fangzu Ring,

[0020] A2 is C 6-60 Aromatic rings, or C containing any of N, O, and S 2-60 Mixed Fragrances Ring

[0021] A3 is C 6-60 Aromatic rings, or C containing any of N, O, and S 2-60 Mixed Fragrances Ring

[0022] A4 is C 6-60 Fangzu Ring,

[0023] X is NR, where R is substituted or unsubstituted C. 6-60 Aryl,

[0024] Y is B, and

[0025] n is an integer from 1 to 4.

[0026] According to another aspect of this disclosure, an organic light-emitting device is provided, comprising: a first electrode; a second electrode disposed opposite to the first electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein one or more of the organic material layers contain a compound represented by chemical formula 1.

[0027] Beneficial effects

[0028] The compound represented by the above chemical formula 1 can be used as a material for the organic material layer of organic light-emitting devices, can be used in solution processing, and can improve efficiency, achieve low driving voltage and / or improve lifetime characteristics in organic light-emitting devices. Attached Figure Description

[0029] Figure 1An example of an organic light-emitting device is shown, comprising a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4.

[0030] Figure 2 An example of an organic light-emitting device is shown, comprising a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 7, an electron injection and transport layer 8, and a cathode 4. Detailed Implementation

[0031] In the following sections, embodiments of the present disclosure will be described in more detail to facilitate understanding of the invention.

[0032] (Definition of the term)

[0033] As used in this article, symbols and This refers to a bond that is connected to another substituent.

[0034] As used herein, the term "substituted or unsubstituted" means unsubstituted or substituted with one or more substituents selected from: deuterium; halogen group; cyano; nitro; hydroxyl; carbonyl; ester group; imide group; amino; phosphine oxide group; alkoxy group; aryloxy group; alkyl thio group; aryl thio group; alkyl sulfonyl group; aryl sulfonyl group; silyl group; boron group; alkyl group; cycloalkyl group; alkenyl group; aryl group; aralkyl group; arylenyl group; alkylamino group; aralkylamino group; heteroarylamino group; arylamino group; arylphosphine group; and heteroaryl group containing at least one of N, O, and S atoms, or unsubstituted or substituted with two or more substituents linked together from the substituents exemplified above. For example, "substituents linked together from two or more substituents" can be biphenyl. That is, biphenyl can be aryl, or it can also be interpreted as a substituent linked together from two phenyl groups.

[0035] In this disclosure, the number of carbon atoms in the carbonyl group is not particularly limited, but is preferably from 1 to 40. Specifically, the carbonyl group can be a substituent having the following structural formula, but is not limited thereto.

[0036]

[0037] In this disclosure, the ester group may have a structure in which the oxygen of the ester group is substituted by a straight-chain, branched, or cyclic alkyl group having 1 to 25 carbon atoms, or by an aryl group having 6 to 25 carbon atoms. Specifically, the ester group may be a substituent having the following structural formulas, but is not limited thereto.

[0038]

[0039] In this disclosure, the number of carbon atoms in the imide group is not particularly limited, but is preferably 1 to 25.

[0040] Specifically, the imide group can be a substituent having the following structural formula, but is not limited thereto.

[0041]

[0042] In this disclosure, silane specifically includes, but is not limited to, trimethylsilane, triethylsilane, tert-butyldimethylsilane, vinyldimethylsilane, propyldimethylsilane, triphenylsilane, diphenylsilane, phenylsilane, etc.

[0043] In this disclosure, boron group specifically includes, but is not limited to, trimethylboronyl, triethylboronyl, tert-butyldimethylboronyl, triphenylboronyl, and phenylboronyl.

[0044] Examples of halogen groups in this disclosure include fluorine, chlorine, bromine, or iodine.

[0045] In this disclosure, the alkyl group can be straight-chain or branched, and its carbon number is not particularly limited, but is preferably from 1 to 40. According to one embodiment, the alkyl group has 1 to 20 carbons. According to another embodiment, the alkyl group has 1 to 10 carbons. According to yet another embodiment, the alkyl group has 1 to 6 carbons. Specific examples of alkyl groups include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, etc.

[0046] In this disclosure, the alkenyl group can be straight-chain or branched, and its carbon number is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbons. According to another embodiment, the alkenyl group has 2 to 10 carbons. According to yet another embodiment, the alkenyl group has 2 to 6 carbons. Specific examples include, but are not limited to, 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, styryl, styryl, etc.

[0047] In this disclosure, the cycloalkyl group is not particularly limited, but it is preferably composed of 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to yet another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specific examples 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.

[0048] In this disclosure, the aryl group is not particularly limited, but it is preferably composed of 6 to 60 carbon atoms, and can be either a monocyclic aryl or a polycyclic aryl. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to another embodiment, the aryl group has 6 to 20 carbon atoms. As a monocyclic aryl group, the aryl group can be phenyl, biphenyl, terphenyl, etc., but is not limited thereto. Polycyclic aryl groups include naphthyl, anthraceneyl, phenanthryl, pyrene, perylene, etc. It includes, but is not limited to, methyl, fluorene, etc.

[0049] In this disclosure, the fluorene group can be substituted, and two substituents can be linked together to form a spirocyclic structure. When the fluorene group is substituted, a spirocyclic structure can be formed. However, the structure is not limited to this.

[0050] In this disclosure, the heteroaryl group is a heteroaryl group containing at least one of O, N, Si, and S as a heteroatom, and its carbon number is not particularly limited, but is preferably 2 to 60. Examples of heteroaryl groups include... Ton, thioxanthyl, thiophene, furanyl, pyrrolyl, imidazole, thiazolyl azole group, Diazolyl, Triazolyl, Pyridyl, Bipyridyl, Pyrimidinyl, Triazinyl, Acridineyl, Pyridazinyl, Quinolinyl, Quinazolinyl, Quinoxalinyl, Phtharazineyl, Pyridopyrimidinyl, Pyridopyrazinyl, Pyrazenopyrazinyl, Isoquinolinyl, Indoleyl, Carbazoleyl, Benzo[] Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazole, benzothiophene, dibenzothiophene, benzofuranyl, phenanthrolinel, iso Azolyl, thiadiazolyl, phenthiazinyl, dibenzofuranyl, etc., but not limited to these.

[0051] In this disclosure, the aryl group in aralkyl, arylenyl, alkylaryl, arylamino, and arylsilyl is the same as the aryl group described above. In this disclosure, the alkyl group in aralkyl, alkylaryl, and alkylamino is the same as the alkyl group described above. In this disclosure, the heteroaryl group in heteroarylamine can be described using the above-described description of heteroaryl. In this disclosure, the alkenyl group in arylenyl is the same as the alkenyl group described above. In this disclosure, the above-described description of aryl can be applied, except that the arylene group is a divalent group. In this disclosure, the above-described description of heteroaryl can be applied, except that the heteroarylene group is a divalent group. In this disclosure, the above-described description of aryl or cycloalkyl can be applied, except that the hydrocarbon ring is not a monovalent group but is formed by combining two substituents. In this disclosure, the above-described description of heteroaryl can be applied, except that the heterocycle is not a monovalent group but is formed by combining two substituents.

[0052] (compound)

[0053] This disclosure provides compounds represented by chemical formula 1.

[0054] Preferably, A1, A2, A3 and A4 are each independently a substituted or unsubstituted benzene ring.

[0055] Preferably, chemical formula 1 is represented by the following chemical formula 1':

[0056] [Chemical Formula 1']

[0057]

[0058] In chemical formula 1',

[0059] n is an integer from 1 to 4.

[0060] Each R1 is independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C. 1-60 Alkyl, substituted or unsubstituted C 6-60 aryl, substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S 2-60A heteroaryl group, or a substituent represented by the following chemical formula 2; or two adjacent R1 groups linked together to form a substituted or unsubstituted C1 group. 3-10 cycloalkyl,

[0061] Each R2 is independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C. 1-60 Alkyl, substituted or unsubstituted C 6-60 aryl, substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S 2-60 A heteroaryl group, or a substituent represented by the following chemical formula 2; or two adjacent R2 groups linked together to form a substituted or unsubstituted C2 group. 3-10 cycloalkyl, or substituted or unsubstituted C 6-60 Fangzu Ring,

[0062] Each R3 is independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C. 1-60 Alkyl, substituted or unsubstituted C 6-60 aryl, or substituted or unsubstituted C containing one or more heteroatoms selected from N, O, and S. 2-60 Heteroaryl; or two adjacent R3 groups linked together to form substituted or unsubstituted C. 3-10 Cycloalkyl, or -O-(CH2) m -O-, where m is an integer from 1 to 4.

[0063] R4 is hydrogen, deuterium, or substituted or unsubstituted C. 1-60 Alkyl, substituted or unsubstituted C 3-60 cycloalkyl, substituted or unsubstituted C 6-60 aryl, substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S 2-60 Heteroaryl groups, or substituents represented by the following chemical formula 2,

[0064] R5 is hydrogen, deuterium, or substituted or unsubstituted C. 1-60 Alkyl, substituted or unsubstituted C 3-60 cycloalkyl, substituted or unsubstituted C 6-60 aryl, substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S 2-60 Mixed aromatics,

[0065] [Chemical Formula 2]

[0066]

[0067] In chemical formula 2,

[0068] L is a single bond, or C is substituted or unsubstituted.6-60 Alpha-aryl

[0069] L1 and L2 are each independently a single-bonded, substituted, or unsubstituted C bond. 6-60 aryl, or substituted or unsubstituted C containing one or more heteroatoms selected from N, O, and S. 2-60 Hybrid aryl,

[0070] Ar1 and Ar2 are each independently substituted or unsubstituted C. 6-60 aryl, or substituted or unsubstituted C containing one or more heteroatoms selected from N, O, and S. 2-60 Mixed aromatics,

[0071] n1 is an integer from 0 to 4, and

[0072] n2 is an integer from 0 to 5.

[0073] Preferably, chemical formula 1' is represented by any one of the following chemical formulas 1-1 to 1-6:

[0074]

[0075] In chemical formulas 1-1 to 1-6,

[0076] R1 to R5, n1 and n2 are as defined above.

[0077] Preferably, n is 1, 2, or 3.

[0078] Preferably, n1 is 1, and R1 is hydrogen, deuterium, substituted or unsubstituted C. 1-10 Alkyl, substituted or unsubstituted C 6-10 aryl, substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S 8-12 heteroaryl, or di(substituted or unsubstituted C) 6-10 (Aryl)amino.

[0079] Preferably, n1 is 1, and R1 is hydrogen, deuterium, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, phenyl, tert-butyl-substituted phenyl, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, or diphenylamino.

[0080] Preferably, n1 is 2, and R1 are connected to each other to form substituted or unsubstituted C. 5-6 Cycloalkyl.

[0081] Preferably, n1 is 2, and R1 are connected to each other to form a substituent represented by any of the following:

[0082]

[0083] Preferably, n2 is 1, and R2 is hydrogen, deuterium, substituted or unsubstituted C. 1-10 Alkyl, substituted or unsubstituted C 6-10 aryl, substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S 8-12 heteroaryl, or di(substituted or unsubstituted C) 6-10 (Aryl)amino.

[0084] Preferably, n2 is 1, and R2 is hydrogen, deuterium, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, phenyl, tert-butyl-substituted phenyl, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, or diphenylamino.

[0085] Preferably, n2 is 2, and R2 are connected to each other to form a substituent represented by any of the following:

[0086]

[0087] Preferably, n3 is 1 or 2, and each R3 is independently hydrogen, deuterium, substituted or unsubstituted C. 1-10 Alkyl, substituted or unsubstituted C 6-10 aryl, substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S 8-12 heteroaryl, or di(substituted or unsubstituted C) 6-10 (Aryl)amino.

[0088] Preferably, n3 is 1 or 2, and each R3 is independently hydrogen, deuterium, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, phenyl, tert-butyl-substituted phenyl, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, or diphenylamino.

[0089] Preferably, n3 is 2, and R3 are connected to each other to form substituted or unsubstituted C. 5-6 Cycloalkyl, or -O-(CH2) m -O-, where m is an integer from 1 to 3.

[0090] Preferably, n3 is 2, and R3 are connected to each other to form substituents represented by any of the following:

[0091]

[0092] Preferably, R4 is substituted or unsubstituted C. 1-10 Alkyl, substituted or unsubstituted C 6-30Aryl, or substituent represented by chemical formula 2.

[0093] Preferably, R4 is methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, dimethylfluorenyl, diphenylfluorenyl, or selected from any of the following:

[0094]

[0095] Preferably, R5 is hydrogen, deuterium, or substituted or unsubstituted C. 1-10 Alkyl, or substituted or unsubstituted C 6-10 Aryl.

[0096] Preferably, R5 is hydrogen, deuterium, or phenyl.

[0097] Representative examples of compounds represented by chemical formula 1 are as follows:

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113] Furthermore, this disclosure provides as an example a method for preparing compounds represented by chemical formula 1', as shown in reaction scheme 1 below, and compounds represented by chemical formula 1 can also be prepared by reference thereto.

[0114] [Reaction Scheme 1]

[0115]

[0116] In reaction scheme 1, the remaining substituents other than X are defined in the same way as those defined above, and X is a halogen, preferably bromine or chlorine.

[0117] Step 1 is an amine substitution reaction, preferably carried out in the presence of a palladium catalyst and a base, and the reactive group used for the amine substitution reaction can be modified as known in the art. Step 2 is a reaction with BI3, preferably carried out in the presence of a base. The above preparation methods can be further illustrated in the preparation examples described below.

[0118] (Coating Composition)

[0119] On the other hand, the compounds according to this disclosure can be used to form organic material layers, particularly light-emitting layers, of organic light-emitting devices via solution processing. For this purpose, this disclosure provides coating compositions comprising the aforementioned compounds according to this disclosure and solvents.

[0120] The solvent is not particularly limited, as long as it is capable of dissolving or dispersing the compounds according to this disclosure. Examples of solvents may include chlorine-based solvents, such as chloroform, dichloromethane, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, and o-dichlorobenzene; and ether-based solvents, such as tetrahydrofuran and dichlorobenzene. Alkanes; solvents based on aromatic hydrocarbons, such as toluene, xylene, trimethylbenzene, and mesitylene; solvents based on aliphatic hydrocarbons, such as cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, and n-decane; solvents based on ketones, such as acetone, methyl ethyl ketone, and cyclohexanone; solvents based on esters, such as ethyl acetate, butyl acetate, and ethyl cellosolve acetate; polyols, such as ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, and dimethoxyethyl ether. Alkanes, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerol, and 1,2-hexanediol, and their derivatives; alcohol-based solvents, such as methanol, ethanol, propanol, isopropanol, and cyclohexanol; sulfoxide-based solvents, such as dimethyl sulfoxide; amide-based solvents, such as N-methyl-2-pyrrolidone and N,N-dimethylformamide; benzoate-based solvents, such as butyl benzoate and methyl-2-methoxybenzoate; tetrahydronaphthalene; 3-phenoxy-toluene; and so on. Furthermore, the above solvents can be used alone or in combination of two or more solvents.

[0121] Furthermore, the coating composition may also contain a compound used as a host material, and compounds used as host materials will be described later. Additionally, the coating composition may contain a compound used as a dopant material, and compounds used as dopant materials will be described later.

[0122] Furthermore, the viscosity of the coating composition is preferably from 1 cP to 10 cP, and coating is easily performed within this range. Additionally, the concentration of the compound according to this disclosure in the coating composition is preferably from 0.1 wt% to 20 wt% (v / v).

[0123] In another embodiment of this disclosure, a method for forming a light-emitting layer using the above-described coating composition is provided. Specifically, the method includes the steps of: coating an anode with the above-described coating composition according to this disclosure by a solution method; and heat-treating the coated composition.

[0124] The solution method uses the coating composition described above according to this disclosure, and includes, but is not limited to, spin coating, dip coating, blade coating, inkjet printing, screen printing, spraying, roller coating, etc.

[0125] The heat treatment temperature in the heat treatment step is preferably from 150°C to 230°C. Furthermore, the heat treatment time can be from 1 minute to 3 hours, more preferably from 10 minutes to 1 hour. Additionally, the heat treatment is preferably carried out in an inert gas atmosphere, such as argon or nitrogen.

[0126] (Organic light-emitting devices)

[0127] In another embodiment of this disclosure, an organic light-emitting device comprising a compound represented by Formula 1 is provided. In one example, this disclosure provides an organic light-emitting device comprising: a first electrode; a second electrode disposed opposite to the first electrode; and one or more layers of organic material disposed between the first electrode and the second electrode, wherein one or more layers of organic material comprise a compound represented by Formula 1.

[0128] The organic material layer of the organic light-emitting device disclosed herein can have a single-layer structure, or it can have a multilayer structure in which two or more organic material layers are stacked. For example, the organic light-emitting device of this disclosure can have a structure that includes a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc., as organic material layers. However, the structure of the organic light-emitting device is not limited to this, and it may include a small number of organic material layers.

[0129] Furthermore, the organic material layer may include a light-emitting layer, wherein the light-emitting layer may contain a compound represented by Chemical Formula 1. In particular, the compound according to this disclosure may be used as a dopant in the light-emitting layer.

[0130] Furthermore, the organic light-emitting device according to this disclosure can be a normal type organic light-emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate. Additionally, the organic light-emitting device according to this disclosure can be an inverted type organic light-emitting device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate. For example, the structure of an organic light-emitting device according to one embodiment of this disclosure is... Figure 1 and Figure 2 As shown in the image.

[0131] Figure 1 An example of an organic light-emitting device comprising a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4 is shown. In such a structure, a compound represented by chemical formula 1 can be contained in the light-emitting layer.

[0132] Figure 2 An example of an organic light-emitting device is shown, comprising a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light-emitting layer 7, an electron injection and transport layer 8, and a cathode 4. In such a structure, a compound represented by chemical formula 1 may be included in the light-emitting layer.

[0133] The organic light-emitting device according to this disclosure can be manufactured using materials and methods known in the art, except that at least one of the organic material layers comprises a compound represented by chemical formula 1. Furthermore, when the organic light-emitting device comprises a plurality of organic material layers, the organic material layers can be formed from the same material or different materials.

[0134] For example, an organic light-emitting device according to this disclosure can be fabricated by sequentially stacking an anode, an organic material layer, and a cathode on a substrate. In this case, the organic light-emitting device can be fabricated by depositing a metal, a conductive metal oxide, or an alloy thereof on a substrate using a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation to form an anode, forming an organic material layer on the anode including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer, and then depositing a material that can be used as a cathode on the organic material layer.

[0135] In addition to this method, organic light-emitting devices can also be fabricated by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate (International Publication WO2003 / 012890). However, the fabrication method is not limited to this.

[0136] In one instance, the first electrode is the anode and the second electrode is the cathode, or alternatively, the first electrode is the cathode and the second electrode is the anode.

[0137] As anode materials, materials with a large work function are generally preferred, allowing holes to be smoothly injected into the organic material layer. Specific examples of anode materials include: metals, such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides, such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides, such as ZnO:Al or SnO2:Sb; conductive compounds, such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxo)thiophene] (PEDOT), polypyrrole, and polyaniline; and so on, but are not limited thereto.

[0138] As cathode materials, materials with a small work function are generally preferred, allowing electrons to be easily injected into the organic material layer. Specific examples of cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer materials such as LiF / Al or LiO2 / Al, etc., but are not limited to these.

[0139] A hole injection layer is a layer used to inject holes from the electrode, and the hole injection material is preferably a compound that has the ability to transport holes, thus exhibiting the effect of injecting holes into the anode and excellent hole injection effect on the light-emitting layer or light-emitting material, preventing excitons generated in the light-emitting layer from moving to the electron injection layer or electron injection material, and further exhibiting excellent ability to form thin films. Preferably, the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of hole injection materials include, but are not limited to, metalloporphyrins, oligothiophenes, arylamine-based organic materials, hexanitrile hexaazabenzophenanthrene-based organic materials, quinacridone-based organic materials, perylene-based organic materials, anthraquinones, conductive polymers based on polyaniline and polythiophene.

[0140] A hole transport layer is a layer that receives holes from a hole injection layer and transports them to a light-emitting layer. The hole transport material is suitably a material with a high hole mobility, capable of receiving holes from the anode or hole injection layer and transferring them to the light-emitting layer. Specific examples include, but are not limited to, arylamine-based organic materials, conductive compounds, and block copolymers containing both conjugated and non-conjugated portions.

[0141] The luminescent layer may comprise a host material and a dopant material. The host material may be a fused aromatic ring derivative, a heterocyclic compound, etc. Specific examples of fused aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentanebenzene derivatives, phenanthrene compounds, fluoranthene compounds, etc. Examples of heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc., but are not limited to these.

[0142] Examples of dopant materials include aromatic amine derivatives, styrene amine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, aromatic amine derivatives are fused aromatic ring derivatives with aryl amino groups, either substituted or unsubstituted, and examples include pyrene, anthracene, etc., with aryl amino groups. Examples include periflanthene, etc. Styrene amine compounds are compounds in which at least one aryl vinyl group is substituted in a substituted or unsubstituted aryl amine, wherein one or more substituents selected from aryl, silyl, alkyl, cycloalkyl, and arylamino groups are substituted or unsubstituted. Specific examples include, but are not limited to, styrene amines, styrene diamines, styrene triamines, and styrene tetraamines. Furthermore, metal complexes include, but are not limited to, iridium complexes, platinum complexes, etc.

[0143] The electron injection and transport layer is a layer that simultaneously functions as 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 electron conditioning layer. The electron injection and transport material is suitably a material that can effectively receive electrons from the cathode and transfer them to the light-emitting layer, and has a high electron mobility. Specific examples of electron injection and transport materials include: Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic free radical compounds; hydroxyflavonoid-metal complexes, triazine derivatives, etc., but are not limited to these. Alternatively, LiF, NaF, NaCl, CsF, Li2O, BaO, fluorenone, anthraquinone dimethyl ether, biphenylquinone, thiamethoxam dioxide, etc., can be used. azole, Diazoles, triazoles, imidazoles, perylenetetracarboxylic acid, fluorenemethane, anthrones, and their derivatives, metal complexes, nitrogen-containing 5-membered ring derivatives, etc., but not limited to these.

[0144] Examples of metal complex compounds include, but are not limited to, lithium 8-hydroxyquinoline, bis(8-hydroxyquinoline)zinc, bis(8-hydroxyquinoline)copper, bis(8-hydroxyquinoline)manganese, tris(8-hydroxyquinoline)aluminum, tris(2-methyl-8-hydroxyquinoline)aluminum, tris(8-hydroxyquinoline)gallium, bis(10-hydroxybenzo[h]quinoline)beryllium, bis(10-hydroxybenzo[h]quinoline)zinc, bis(2-methyl-8-quinoline)chlorogallium, bis(2-methyl-8-quinoline)(o-cresol)gallium, bis(2-methyl-8-quinoline)(1-naphthol)aluminum, and bis(2-methyl-8-quinoline)(2-naphthol)gallium.

[0145] Depending on the materials used, the organic light-emitting device according to this disclosure can be a front-emitting, rear-emitting, or dual-emitting type.

[0146] In addition to organic light-emitting devices, the compounds according to this disclosure may also be included in organic solar cells or organic transistors.

[0147] The following examples will specifically describe the preparation of compounds represented by Formula 1 and organic light-emitting devices comprising them. However, the following examples are provided for illustrative purposes only and are not intended to limit the scope of this disclosure.

[0148] [Example]

[0149] Example 1: Preparation of Compound 1

[0150]

[0151] Compound 1-a (1.0 equivalent), NaOt-Bu (4.0 equivalent), and compound 1-b (1.05 equivalent) were placed in a round-bottom flask and dissolved in anhydrous toluene (0.1 M). Pd(t-Bu3P)2 (5 mol%) was added dropwise at a bath temperature of 100 °C, and the mixture was stirred for 4 hours. After the reaction, the reaction mixture was cooled to room temperature, thoroughly diluted in CH2Cl2, and then washed with CH2Cl2 / salt water. The organic layer was separated, water was removed with MgSO4, and the solution was passed through a diatomaceous earth-Florida-silica pad. The passed solution was concentrated under reduced pressure and then purified by column chromatography to prepare compound 1-c (yield: 73%).

[0152] Compound 1-d (1.0 equivalent) and compound 1-e (1.05 equivalent) were placed in a round-bottom flask and dissolved in anhydrous THF (0.12 M). K₂CO₃ (aqueous solution) (1.5 equivalent) was added dropwise to the reaction solution. Pd(PPh₃)₄ (1.5 mol%) was added dropwise at a bath temperature of 80 °C, and the mixture was stirred for 4 hours. After the reaction, the reaction mixture was cooled to room temperature, thoroughly diluted in CH₂Cl₂, and then washed with CH₂Cl₂ / salt water. The organic layer was separated, water was removed with MgSO₄, and the solution was passed through a diatomaceous earth-Florida-silica pad. The passed solution was concentrated under reduced pressure and then purified by column chromatography to prepare compound 1-f (yield: 70%).

[0153] Compound 1-f (1.0 equivalent), NaOt-Bu (4.0 equivalent), and compound 1-g (1.03 equivalent) were placed in a round-bottom flask and dissolved in anhydrous toluene (0.1 M). Pd(t-Bu3P)2 (5 mol%) was added dropwise at a bath temperature of 120 °C, and the mixture was stirred for 4 hours. After the reaction, the reaction mixture was cooled to room temperature, thoroughly diluted in CH2Cl2, and then washed with CH2Cl2 / salt water. The organic layer was separated, water was removed with MgSO4, and the solution was passed through a diatomaceous earth-Florida-silica pad. The passed solution was concentrated under reduced pressure and then purified by column chromatography to prepare compound 1-h (yield: 83%).

[0154] Compound 1-h (1.05 equivalents), NaOt-Bu (4.0 equivalents), and compound 1-c (1.0 equivalents) were placed in a round-bottom flask and dissolved in anhydrous toluene (0.1 M). Pd(t-Bu3P)2 (5 mol%) was added dropwise at a bath temperature of 120 °C, and the mixture was stirred overnight. After the reaction, the reaction mixture was cooled to room temperature, thoroughly diluted in CH2Cl2, and then washed with CH2Cl2 / salt water. The organic layer was separated, water was removed with MgSO4, and the solution was passed through a diatomaceous earth-Florida silica-dioxide pad. The passed solution was concentrated under reduced pressure and then purified by column chromatography to prepare compound 1-i (yield: 67%).

[0155] Compound 1-i (1.0 equivalent) was placed in a round-bottom flask and dissolved in anhydrous toluene (0.03 M). BI3 (2.0 equivalent) was slowly added dropwise to the reaction solution, and the mixture was stirred overnight at a bath temperature of 80 °C. After the reaction, the reaction mixture was allowed to cool sufficiently at room temperature and diluted with CH2Cl2. EtNi-Pr2 (15.0 equivalent) and saturated Na2S2O3 (aqueous solution) were added dropwise sequentially to the reaction mixture, and the mixture was washed with CH2Cl2 / H2O. The organic layer was separated, water was removed with MgSO4, and the solution was passed through a diatomaceous earth-Florida-silica pad. The passed solution was concentrated under reduced pressure and then purified by column chromatography to prepare compound 1 (yield: 70%).

[0156] m / z[M+H] + 737.3

[0157] Example 2: Preparation of Compound 2

[0158]

[0159] Compound 2 was prepared in the same manner as compound 1, except that compound 2-a was used instead of compound 1-g.

[0160] m / z[M+H]+ 757.6

[0161] Example 3: Preparation of Compound 3

[0162]

[0163] Compound 3 was prepared in the same manner as compound 1, except that compound 3-a was used instead of compound 1-g.

[0164] m / z[M+H] + 757.6

[0165] Example 4: Preparation of Compound 4

[0166]

[0167] Compounds 4-a (1.0 equivalent) and 4-b (1.05 equivalent) were placed in a round-bottom flask and dissolved in anhydrous THF (0.12 M). K₂CO₃ (aqueous solution) (1.5 equivalent) was added dropwise to the reaction solution. Pd(PPh₃)₄ (1.5 mol%) was added dropwise at a bath temperature of 80 °C, and the mixture was stirred for 4 hours. After the reaction, the reaction mixture was cooled to room temperature, thoroughly diluted in CH₂Cl₂, and then washed with CH₂Cl₂ / salt water. The organic layer was separated, water was removed with MgSO₄, and the solution was passed through a diatomaceous earth-Florida-silica pad. The passed solution was concentrated under reduced pressure and then purified by column chromatography to prepare compound 4-c (yield: 82%).

[0168] Then, compound 4 was prepared in the same manner as compound 1, except that compound 4-c was used instead of compound 1-g.

[0169] m / z[M+H] + 797.4

[0170] Example 5: Preparation of Compound 5

[0171]

[0172] Compound 5 was prepared in the same manner as compound 4, except that compound 5-a was used instead of compound 4-a.

[0173] m / z[M+H] + 797.4

[0174] Example 6: Preparation of Compound 6

[0175]

[0176] Compound 6 was prepared in the same manner as in the preparation of compound 1, except that compound 6-a was used instead of compound 1-g.

[0177] m / z[M+H] + 791.6

[0178] Example 7: Preparation of Compound 7

[0179]

[0180] Compound 7 was prepared in the same manner as in the preparation of compound 1, except that compound 7-a was used instead of compound 1-g.

[0181] m / z[M+H] + 749.5

[0182] Example 8: Preparation of Compound 8

[0183]

[0184] Compound 8 was prepared in the same manner as in the preparation of compound 1, except that compound 8-a was used instead of compound 1-g.

[0185] m / z[M+H] + 797.3

[0186] Example 9: Preparation of Compound 9

[0187]

[0188] Compound 9 was prepared in the same manner as in the preparation of compound 1, except that compound 9-a was used instead of compound 1-g.

[0189] m / z[M+H] + 731.4

[0190] Example 10: Preparation of Compound 10

[0191]

[0192] Compound 10-a (1.0 equivalent), NaOt-Bu (4.0 equivalent), and compound 1-b (1.05 equivalent) were placed in a round-bottom flask and dissolved in anhydrous toluene (0.1 M). Pd(t-Bu3P)2 (5 mol%) was added dropwise at a bath temperature of 120 °C, and the mixture was stirred for 3 hours. After the reaction, the reaction mixture was cooled to room temperature, thoroughly diluted in CH2Cl2, and then washed with CH2Cl2 / salt water. The organic layer was separated, water was removed with MgSO4, and the solution was passed through a diatomaceous earth-Florida-silica pad. The passed solution was concentrated under reduced pressure and then purified by column chromatography to prepare compound 10-b (yield: 63%).

[0193] Compound 10-c (1.0 equivalent), NaOt-Bu (4.0 equivalent), and compound 10-d (1.05 equivalent) were placed in a round-bottom flask and dissolved in anhydrous toluene (0.1 M). Pd(t-Bu3P)2 (5 mol%) was added dropwise at a bath temperature of 120 °C, and the mixture was stirred for 4 hours. After the reaction, the reaction mixture was cooled to room temperature, thoroughly diluted in CH2Cl2, and then washed with CH2Cl2 / salt water. The organic layer was separated, water was removed with MgSO4, and the solution was passed through a diatomaceous earth-Florida-silica pad. The passed solution was concentrated under reduced pressure and then purified by column chromatography to prepare compound 10-e (yield: 69%).

[0194] Compound 10-b (1.0 equivalent), NaOt-Bu (4.0 equivalent), and compound 10-e (1.03 equivalent) were placed in a round-bottom flask and dissolved in anhydrous toluene (0.1 M). Pd(t-Bu3P)2 (5 mol%) was added dropwise at a bath temperature of 120 °C, and the mixture was stirred for 4 hours. After the reaction, the reaction mixture was cooled to room temperature, thoroughly diluted in CH2Cl2, and then washed with CH2Cl2 / salt water. The organic layer was separated, water was removed with MgSO4, and the solution was passed through a diatomaceous earth-Florida-silica pad. The passed solution was concentrated under reduced pressure and then purified by column chromatography to prepare compound 10-f (yield: 79%).

[0195] Compound 10-f (1.0 equivalent) was placed in a round-bottom flask and dissolved in anhydrous toluene (0.03 M). BI3 (2.0 equivalent) was slowly added dropwise to the reaction solution, and the mixture was stirred overnight at a bath temperature of 80 °C. After the reaction, the reaction mixture was allowed to cool sufficiently at room temperature and diluted with CH2Cl2. EtNi-Pr2 (15.0 equivalent) and saturated Na2S2O3 (aqueous solution) were added dropwise sequentially to the reaction mixture, and the mixture was washed with CH2Cl2 / H2O. The organic layer was separated, water was removed with MgSO4, and the solution was passed through a diatomaceous earth-Florida-silica pad. The passed solution was concentrated under reduced pressure and then purified by column chromatography to prepare compound 10 (yield: 73%).

[0196] m / z[M+H] + 661.5

[0197] Example 11: Preparation of Compound 11

[0198]

[0199] Compound 11 was prepared in the same manner as in the preparation of compound 10, except that compound 11-a was used instead of compound 10-c.

[0200] m / z[M+H] + 647.4

[0201] Example 12: Preparation of Compound 12

[0202]

[0203] Compound 12 was prepared in the same manner as in the preparation of compound 10, except that compound 12-a was used instead of compound 10-c.

[0204] m / z[M+H] + 675.3

[0205] Example 13: Preparation of Compound 13

[0206]

[0207] Compound 13 was prepared in the same manner as in the preparation of compound 10, except that compound 13-a was used instead of compound 10-c.

[0208] m / z[M+H] + 661.5

[0209] Example 14: Preparation of Compound 14

[0210]

[0211] Compound 10-a (1.0 equivalent), NaOt-Bu (4.0 equivalent), and compound 13-b (1.05 equivalent) were placed in a round-bottom flask and dissolved in anhydrous toluene (0.1 M). Pd(t-Bu3P)2 (5 mol%) was added dropwise at a bath temperature of 120 °C, and the mixture was stirred for 2 hours. After the reaction, the reaction mixture was cooled to room temperature, thoroughly diluted in CH2Cl2, and then washed with CH2Cl2 / salt water. The organic layer was separated, water was removed with MgSO4, and the solution was passed through a diatomaceous earth-Florida-silica pad. The passed solution was concentrated under reduced pressure and then purified by column chromatography to prepare compound 14-a (yield: 72%).

[0212] Compound 14-b (1.0 equivalent), NaOt-Bu (4.0 equivalent), and compound 1-g (1.03 equivalent) were placed in a round-bottom flask and dissolved in anhydrous toluene (0.1 M). Pd(t-Bu3P)2 (5 mol%) was added dropwise at a bath temperature of 120 °C, and the mixture was stirred for 4 hours. After the reaction, the reaction mixture was cooled to room temperature, thoroughly diluted in CH2Cl2, and then washed with CH2Cl2 / salt water. The organic layer was separated, water was removed with MgSO4, and the solution was passed through a diatomaceous earth-Florida-silica pad. The passed solution was concentrated under reduced pressure and then purified by column chromatography to prepare compound 14-c (yield: 83%).

[0213] Compound 14-c (1.05 equivalents), NaOt-Bu (4.0 equivalents), and compound 14-a (1.0 equivalents) were placed in a round-bottom flask and dissolved in anhydrous toluene (0.1 M). Pd(t-Bu3P)2 (5 mol%) was added dropwise at a bath temperature of 120 °C, and the mixture was stirred overnight. After the reaction, the reaction mixture was cooled to room temperature, thoroughly diluted in CH2Cl2, and then washed with CH2Cl2 / salt water. The organic layer was separated, water was removed with MgSO4, and the solution was passed through a diatomaceous earth-Florida-silica pad. The passed solution was concentrated under reduced pressure and then purified by column chromatography to prepare compound 14-d (yield: 82%).

[0214] Compound 14-d (1.0 equivalent) was placed in a round-bottom flask and dissolved in anhydrous toluene (0.03 M). BI3 (2.0 equivalent) was slowly added dropwise to the reaction solution, and the mixture was stirred overnight at a bath temperature of 80 °C. After the reaction, the reaction mixture was allowed to cool sufficiently at room temperature and diluted with CH2Cl2. EtNi-Pr2 (15.0 equivalent) and saturated Na2S2O3 (aqueous solution) were added dropwise sequentially to the reaction mixture, and the mixture was washed with CH2Cl2 / H2O. The organic layer was separated, water was removed with MgSO4, and the solution was passed through a diatomaceous earth-Florida-silica pad. The passed solution was concentrated under reduced pressure and then purified by column chromatography to prepare compound 14 (yield: 76%).

[0215] m / z[M+H] + 869.5

[0216] Example 15: Preparation of Compound 15

[0217]

[0218] Compound 15-a (1.0 equivalent) and compound 4-b (2.05 equivalent) were placed in a round-bottom flask and dissolved in anhydrous THF (0.12 M). K₂CO₃ (aqueous solution) (1.5 equivalent) was added dropwise to the reaction solution. Pd(PPh₃)₄ (1.5 mol%) was added dropwise at a bath temperature of 80 °C, and the mixture was stirred overnight. After the reaction, the reaction mixture was cooled to room temperature, thoroughly diluted in CH₂Cl₂, and then washed with CH₂Cl₂ / salt water. The organic layer was separated, water was removed with MgSO₄, and the solution was passed through a diatomaceous earth-Florida-silica pad. The passed solution was concentrated under reduced pressure and then purified by column chromatography to prepare compound 15-b (yield: 82%).

[0219] Then, compound 15 was prepared in the same manner as compound 14, except that compound 15-b was used instead of compound 14-b.

[0220] m / z[M+H] + 837.5

[0221] Example 16: Preparation of Compound 16

[0222]

[0223] Compound 15-a (1.0 equivalent) and compound 4-b (1.05 equivalent) were placed in a round-bottom flask and dissolved in anhydrous THF (0.12 M). K₂CO₃ (aqueous solution) (1.5 equivalent) was added dropwise to the reaction solution. Pd(PPh₃)₄ (1.5 mol%) was added dropwise at a bath temperature of 80 °C, and the mixture was stirred for 4 hours. After the reaction, the reaction mixture was cooled to room temperature, thoroughly diluted in CH₂Cl₂, and then washed with CH₂Cl₂ / salt water. The organic layer was separated, water was removed with MgSO₄, and the solution was passed through a diatomaceous earth-Florida-silica pad. The passed solution was concentrated under reduced pressure and then purified by column chromatography to prepare compound 16-a (yield: 64%).

[0224] Compounds 16-a (1.0 equivalent) and 16-b (1.05 equivalent) were placed in a round-bottom flask and dissolved in anhydrous THF (0.12 M). K₂CO₃ (aqueous solution) (1.5 equivalent) was added dropwise to the reaction solution. Pd(PPh₃)₄ (1.5 mol%) was added dropwise at a bath temperature of 80 °C, and the mixture was stirred for 4 hours. After the reaction, the reaction mixture was cooled to room temperature, thoroughly diluted in CH₂Cl₂, and then washed with CH₂Cl₂ / salt water. The organic layer was separated, water was removed with MgSO₄, and the solution was passed through a diatomaceous earth-Florida-silica pad. The passed solution was concentrated under reduced pressure and then purified by column chromatography to prepare compound 16-c (yield: 78%).

[0225] Then, compound 16 was prepared in the same manner as compound 14, except that compound 16-c was used instead of compound 14-b.

[0226] m / z[M+H] + 913.5

[0227] Example 17: Preparation of Compound 17

[0228]

[0229] Compound 17 was prepared in the same manner as in the preparation of compound 14, except that compound 17-a was used instead of compound 14-c.

[0230] m / z[M+H] + 769.5

[0231] Example 18: Preparation of Compound 18

[0232]

[0233] Compound 18 was prepared in the same manner as in the preparation of compound 14, except that compound 18-a was used instead of compound 14-c.

[0234] m / z[M+H] + 685.4

[0235] Example 19: Preparation of Compound 19

[0236]

[0237] Compound 1-a (1.0 equivalent), NaOt-Bu (4.0 equivalent), and compound 1-h (2.2 equivalent) were placed in a round-bottom flask and dissolved in anhydrous toluene (0.1 M). Pd(t-Bu3P)2 (5 mol%) was added dropwise at a bath temperature of 120 °C, and the mixture was stirred overnight. After the reaction, the reaction mixture was cooled to room temperature, thoroughly diluted in CH2Cl2, and then washed with CH2Cl2 / salt water. The organic layer was separated, water was removed with MgSO4, and the solution was passed through a diatomaceous earth-Florida-silica pad. The passed solution was concentrated under reduced pressure and then purified by column chromatography to prepare compound 19-a (yield: 68%).

[0238] Compound 19-a (1.0 equivalent) was placed in a round-bottom flask and dissolved in anhydrous toluene (0.03 M). BI3 (2.0 equivalent) was slowly added dropwise to the reaction solution, and the mixture was stirred overnight at a bath temperature of 80 °C. After the reaction, the reaction mixture was allowed to cool sufficiently at room temperature and diluted with CH2Cl2. EtNi-Pr2 (15.0 equivalent) and saturated Na2S2O3 (aqueous solution) were added dropwise sequentially to the reaction mixture, and the mixture was washed with CH2Cl2 / H2O. The organic layer was separated, water was removed with MgSO4, and the solution was passed through a diatomaceous earth-Florida-silica pad. The passed solution was concentrated under reduced pressure and then purified by column chromatography to prepare compound 19 (yield: 73%).

[0239] m / z[M+H] + 815.5

[0240] Example 20: Preparation of Compound 20

[0241]

[0242] Compound 20-a (1.0 equivalent), NaOt-Bu (4.0 equivalent), and compound 1-h (2.2 equivalent) were placed in a round-bottom flask and dissolved in anhydrous toluene (0.1 M). Pd(t-Bu3P)2 (5 mol%) was added dropwise at a bath temperature of 120 °C, and the mixture was stirred overnight. After the reaction, the reaction mixture was cooled to room temperature, thoroughly diluted in CH2Cl2, and then washed with CH2Cl2 / salt water. The organic layer was separated, water was removed with MgSO4, and the solution was passed through a diatomaceous earth-Florida-silica pad. The passed solution was concentrated under reduced pressure and then purified by column chromatography to prepare compound 20-b (yield: 62%).

[0243] Compound 20-b (1.0 equivalent), NaOt-Bu (4.0 equivalent), and compound 20-c (1.03 equivalent) were placed in a round-bottom flask and dissolved in anhydrous toluene (0.1 M). Pd(t-Bu3P)2 (5 mol%) was added dropwise at a bath temperature of 120 °C, and the mixture was stirred for 4 hours. After the reaction, the reaction mixture was cooled to room temperature, thoroughly diluted in CH2Cl2, and then washed with CH2Cl2 / salt water. The organic layer was separated, water was removed with MgSO4, and the solution was passed through a diatomaceous earth-Florida-silica pad. The passed solution was concentrated under reduced pressure and then purified by column chromatography to prepare compound 20-d (yield: 70%).

[0244] Compound 20-d (1.0 equivalent) was placed in a round-bottom flask and dissolved in anhydrous toluene (0.03 M). BI3 (2.0 equivalent) was slowly added dropwise to the reaction solution, and the mixture was stirred overnight at a bath temperature of 80 °C. After the reaction, the reaction mixture was allowed to cool sufficiently at room temperature and diluted with CH2Cl2. EtNi-Pr2 (15.0 equivalent) and saturated Na2S2O3 (aqueous solution) were added dropwise sequentially to the reaction mixture, and the mixture was washed with CH2Cl2 / H2O. The organic layer was separated, water was removed with MgSO4, and the solution was passed through a diatomaceous earth-Florida-silica pad. The passed solution was concentrated under reduced pressure and then purified by column chromatography to prepare compound 20 (yield: 76%).

[0245] m / z[M+H] + 1190.30

[0246] Example 21 Preparation of Compound 21

[0247]

[0248] Compound 20-b (1.0 equivalent) and compound 17-a (1.3 equivalent) were placed in a round-bottom flask and dissolved in anhydrous THF (0.12 M). K₂CO₃ (aqueous solution) (2.6 equivalent) was added dropwise to the reaction solution. Pd(t-Bu₃P)₂ (3 mol%) was added dropwise at a bath temperature of 120 °C, and the mixture was stirred overnight. After the reaction, the reaction mixture was cooled to room temperature, thoroughly diluted in CH₂Cl₂, and then washed with CH₂Cl₂ / salt water. The organic layer was separated, water was removed with MgSO₄, and the solution was passed through a diatomaceous earth-Florida-silica pad. The passed solution was concentrated under reduced pressure and then purified by column chromatography to prepare compound 21-a (yield: 72%).

[0249] Compound 21-a (1.0 equivalent) was placed in a round-bottom flask and dissolved in anhydrous toluene (0.03 M). BI3 (2.0 equivalent) was slowly added dropwise to the reaction solution, and the mixture was stirred overnight at a bath temperature of 80 °C. After the reaction, the reaction mixture was allowed to cool sufficiently at room temperature and diluted with CH2Cl2. EtNi-Pr2 (15.0 equivalent) and saturated Na2S2O3 (aqueous solution) were added dropwise sequentially to the reaction mixture, and the mixture was washed with CH2Cl2 / H2O. The organic layer was separated, water was removed with MgSO4, and the solution was passed through a diatomaceous earth-Florida-silica pad. The passed solution was concentrated under reduced pressure and then purified by column chromatography to prepare compound 21 (yield: 82%).

[0250] m / z[M+H] + 1236.7

[0251] Comparative Example 1: Comparison of the preparation of compound F

[0252]

[0253] Compound 1-a (1.0 equivalent), NaOt-Bu (4.0 equivalent), and compound 1-b (2.05 equivalent) were placed in a round-bottom flask and dissolved in anhydrous toluene (0.1 M). Pd(t-Bu3P)2 (5 mol%) was added dropwise at a bath temperature of 120 °C, and the mixture was stirred overnight. After the reaction, the reaction mixture was cooled to room temperature, thoroughly diluted in CH2Cl2, and then washed with CH2Cl2 / salt water. The organic layer was separated, water was removed with MgSO4, and the solution was passed through a diatomaceous earth-Florida-silica pad. The passed solution was concentrated under reduced pressure and then purified by column chromatography to prepare compound F-1 (yield: 75%).

[0254] Compound F-1 (1.0 equivalent) was placed in a round-bottom flask and dissolved in anhydrous toluene (0.03 M). BI3 (2.0 equivalent) was slowly added dropwise to the reaction solution, and the mixture was stirred overnight at a bath temperature of 80 °C. After the reaction, the reaction mixture was allowed to cool sufficiently at room temperature and diluted with CH2Cl2. EtNi-Pr2 (15.0 equivalent) and saturated Na2S2O3 (aqueous solution) were added dropwise sequentially to the reaction mixture, and the mixture was washed with CH2Cl2 / H2O. The organic layer was separated, water was removed with MgSO4, and the solution was passed through a diatomaceous earth-Florida-silica pad. The passed solution was concentrated under reduced pressure and then purified by column chromatography to prepare compound F (yield: 87%).

[0255] m / z[M+H] + =659.6

[0256] Comparative Example 2: Preparation of Comparative Compound G

[0257]

[0258] Compound G was prepared in the same manner as in Comparative Example 1, except that compound G-1 was used instead of compound 1-b.

[0259] m / z[M+H] + =659.5

[0260] Comparative Example 3: Comparison of the preparation of compound H

[0261]

[0262] Compound 1-c (1.0 equivalent), NaOt-Bu (4.0 equivalent), and compound H-1 (1.05 equivalent) were placed in a round-bottom flask and dissolved in anhydrous toluene (0.1 M). Pd(t-Bu3P)2 (5 mol%) was added dropwise at a bath temperature of 120 °C, and the mixture was stirred for 4 hours. After the reaction, the reaction mixture was cooled to room temperature, thoroughly diluted in CH2Cl2, and then washed with CH2Cl2 / salt water. The organic layer was separated, water was removed with MgSO4, and the solution was passed through a diatomaceous earth-Florida-silica pad. The passed solution was concentrated under reduced pressure and then purified by column chromatography to prepare compound H-2 (yield: 79%).

[0263] Compound H-2 (1.0 equivalent) was placed in a round-bottom flask and dissolved in anhydrous toluene (0.03 M). BI3 (2.0 equivalent) was slowly added dropwise to the reaction solution, and the mixture was stirred overnight at a bath temperature of 80 °C. After the reaction, the reaction mixture was allowed to cool sufficiently at room temperature and diluted with CH2Cl2. EtNi-Pr2 (15.0 equivalent) and saturated Na2S2O3 (aqueous solution) were added dropwise sequentially to the reaction mixture, and the mixture was washed with CH2Cl2 / H2O. The organic layer was separated, water was removed with MgSO4, and the solution was passed through a diatomaceous earth-Florida-silica pad. The passed solution was concentrated under reduced pressure and then purified by column chromatography to prepare compound H (yield: 73%).

[0264] m / z[M+H] + =725.5

[0265] [Experimental Example]

[0266] Experimental Example 1

[0267] It is coated with a thickness of The ITO (indium tin oxide) glass substrate, used as the thin film, was immersed in distilled water containing a cleaning agent and ultrasonically cleaned. A product manufactured by Fischer Co. was used as the cleaning agent, and the distilled water was filtered twice using a filter manufactured by Millipore Co. After cleaning the ITO for 30 minutes, ultrasonic cleaning was repeated twice for 10 minutes each time with distilled water. After cleaning with distilled water, the substrate was ultrasonically cleaned with isopropanol, acetone, and methanol solvents, dried, and then cleaned for 5 minutes before being transferred to a glove box.

[0268] A coating composition in which compound O and compound P (weight ratio 2:8) dissolved in cyclohexanone at 20 wt / vol% was spin-coated (4000 rpm) onto an ITO transparent electrode, and then heat-treated (cured) at 200°C for 30 minutes to form a thickness of [missing information]. A hole injection layer was formed. A coating composition containing the following compound Q (Mn: 27,900; Mw: 35,600; measured using PC standards via GPC (Agilent 1200 series)) dissolved in toluene was spin-coated (4000 rpm) onto the hole injection layer at 6 wt / volume rpm and heat-treated at 200°C for 30 minutes to form a thickness of [missing information]. A hole transport layer was formed. A coating composition in which previously prepared compound 1 and the following compound R (weight ratio 2:98) dissolved in cyclohexanone at 2 weight / volume % was spin-coated (4000 rpm) onto the hole transport layer, and then heat-treated at 180°C for 30 minutes to form a thickness of [missing information]. The luminescent layer. After being transferred to a vacuum evaporator, the following compound S is vacuum deposited on the luminescent layer to form a thickness of [thickness missing]. Electron injection and transport layers. Sequential deposition of electron injection and transport layers. and aluminum To form a cathode.

[0269]

[0270] In the above process, the vapor deposition rate of organic materials is maintained at to Maintain the LiF deposition rate at Maintain the aluminum deposition rate And the vacuum level during deposition was maintained at 2×10⁻⁶. -7 Up to 5×10 -8 Entrust.

[0271] Experimental Examples 2 to 21

[0272] Organic light-emitting devices were fabricated in the same manner as in Experimental Example 1, except that compounds shown in Table 1 below were used instead of compound 1 as dopants for the light-emitting layer.

[0273] Comparative Experiment Examples 1 to 3

[0274] Organic light-emitting devices were fabricated in the same manner as in Experimental Example 1, except that compounds shown in Table 1 below were used instead of compound 1 as dopants for the light-emitting layer.

[0275] By applying 10 mA / cm² to the organic light-emitting devices fabricated in the experimental and comparative experimental examples... 2 The driving voltage, external quantum efficiency (EQE), and lifetime were measured using the current, and the results are shown in Table 1 below. Here, the external quantum efficiency (EQE) is calculated as "(number of emitted photons) / (number of injected charge carriers) × 100", and T90 refers to the time required for the brightness to decrease to 90% of the initial brightness (500 nits).

[0276] [Table 1]

[0277]

[0278] As shown in Table 1 above, organic light-emitting devices using compounds containing the present disclosure as dopants for the light-emitting layer exhibit excellent characteristics in terms of efficiency, driving voltage, and lifetime.

[0279] [Explanation of reference numerals in the attached figures]

[0280] 1: Substrate 2: Anode

[0281] 3: Light-emitting layer 4: Cathode

[0282] 5: Hole injection layer; 6: Hole transport layer

[0283] 7: Light-emitting layer; 8: Electron injection and transport layer

Claims

1. A compound represented by the following chemical formula 1': [Chemical Formula 1'] In chemical formula 1', n is an integer from 1 to 4. Each R1 is independently hydrogen, deuterium, substituted or unsubstituted C. 1-10 Alkyl, substituted or unsubstituted C 6-60 aryl, substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S 8-12 heteroaryl, or di(substituted or unsubstituted C) 6-10 (aryl)amino; or two adjacent R1s linked together to form a substituted or unsubstituted C. 5-6 cycloalkyl, Each R2 is independently hydrogen, deuterium, substituted or unsubstituted C. 1-10 Alkyl, substituted or unsubstituted C 6-60 aryl, substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S 8-12 heteroaryl, or di(substituted or unsubstituted C) 6-10 (aryl)amino; or two adjacent R2 groups linked together to form a substituted or unsubstituted C2 group. 3-10 cycloalkyl, or substituted or unsubstituted C 6-60 Fangzu Ring, Each R3 is independently hydrogen, deuterium, substituted or unsubstituted C. 1-10 Alkyl, substituted or unsubstituted C 6-60 aryl, substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S 8-12 heteroaryl, or di(substituted or unsubstituted C) 6-10 (aryl)amino; or two adjacent R3s linked together to form a substituted or unsubstituted C 5-6 Cycloalkyl, or -O-(CH2) m -O-, where m is an integer from 1 to 3. R4 is hydrogen, deuterium, or substituted or unsubstituted C. 1-10 Alkyl, substituted or unsubstituted C 6-30 aryl, or a substituent represented by the following chemical formula 2, R5 is hydrogen, deuterium, or substituted or unsubstituted C. 1-10 Alkyl, or substituted or unsubstituted C 6-10 Aryl, [Chemical Formula 2] In chemical formula 2, L is a single bond, or C is substituted or unsubstituted. 6-60 Alpha-aryl L1 and L2 are each independently C bonds, whether single-bonded, substituted, or unsubstituted. 6-60 aryl, or substituted or unsubstituted C containing one or more heteroatoms selected from N, O, and S. 2-60 heteroaryl, Ar1 and Ar2 are each independently substituted or unsubstituted C. 6-60 aryl, or substituted or unsubstituted C containing one or more heteroatoms selected from N, O, and S. 2-60 Mixed aromatics, n1 is an integer from 0 to 4. n2 is an integer from 0 to 5, and n3 is 1 or 2. "Substituted or unsubstituted" means unsubstituted or substituted with one or more of the following substituents: deuterium; halogen group; cyano; nitro; hydroxyl; carbonyl; ester group; imide group; amino; phosphine oxide group; alkoxy group; aryloxy group; alkyl thio group; aryl thio group; alkyl sulfonyl group; aryl sulfonyl group; silyl group; boron group; alkyl group; cycloalkyl group; alkenyl group; aryl group; aralkyl group; aryl-alkenyl group; alkylaryl group; alkylamine group; aralkylamine group; heteroarylamine group; arylamine group; arylphosphine group; and heteroaryl group containing at least one of N, O and S atoms.

2. The compound according to claim 1, wherein: Chemical formula 1' is represented by any of the following chemical formulas 1-1 to 1-6: In chemical formulas 1-1 to 1-6, R1 to R5 and n1 to n3 are as defined in claim 1.

3. The compound according to claim 1, wherein: n is 1, 2, or 3.

4. The compound according to claim 1, wherein: n1 is 1, and R1 is hydrogen, deuterium, or substituted or unsubstituted C. 1-10 Alkyl, substituted or unsubstituted C 6-10 aryl, substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S 8-12 heteroaryl, or di(substituted or unsubstituted C) 6-10 (Aryl)amino.

5. The compound according to claim 1, wherein: n1 is 1, and R1 is hydrogen, deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, phenyl, tert-butyl-substituted phenyl, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, or diphenylamino.

6. The compound according to claim 1, wherein: n1 is 2, and R1s are linked together to form substituents represented by any of the following: 。 7. The compound according to claim 1, wherein: n2 is 1, and R2 is hydrogen, deuterium, or substituted or unsubstituted C. 1-10 Alkyl, substituted or unsubstituted C 6-10 aryl, substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S 8-12 heteroaryl, or di(substituted or unsubstituted C) 6-10 (Aryl)amino.

8. The compound according to claim 1, wherein: n2 is 1, and R2 is hydrogen, deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, phenyl, tert-butyl-substituted phenyl, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, or diphenylamino.

9. The compound according to claim 1, wherein: n2 is 2, and R2 groups are linked together to form substituents represented by any of the following: 。 10. The compound according to claim 1, wherein: n3 is 1 or 2, and Each R3 is independently hydrogen, deuterium, substituted or unsubstituted C. 1-10 Alkyl, substituted or unsubstituted C 6-10 aryl, substituted or unsubstituted C containing one or more heteroatoms selected from N, O and S 8-12 heteroaryl, or di(substituted or unsubstituted C) 6-10 (Aryl)amino.

11. The compound according to claim 1, wherein: n3 is 1 or 2, and Each R3 is independently hydrogen, deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, phenyl, tert-butyl-substituted phenyl, benzofuranyl, dibenzofuranyl, benzothiophenyl, dibenzothiophenyl, or diphenylamino.

12. The compound according to claim 1, wherein: n3 is 2, and R3 groups are linked together to form substituents represented by any of the following: 。 13. The compound according to claim 1, wherein: R4 is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, dimethylfluorenyl, diphenylfluorenyl, or selected from any of the following: 。 14. The compound according to claim 1, wherein: R5 can be hydrogen, deuterium, or phenyl.

15. The compound according to claim 1, wherein: The compound represented by chemical formula 1' is selected from any of the following: 。 16. An organic light-emitting device, comprising: First electrode; The second electrode is configured to be opposite to the first electrode; And one or more organic material layers disposed between the first electrode and the second electrode, wherein one or more of the organic material layers contain a compound according to any one of claims 1 to 15.

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

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