Composition for organic light-emitting device and organic light-emitting device comprising same

Abstract

The present disclosure provides a composition for an organic light emitting device and an organic light emitting device comprising the same.

Description

Compositions for organic light-emitting devices and organic light-emitting devices comprising the same. Technical Field

[0001] Cross-references to related applications

[0002] This application claims priority and benefit to Korean Patent Application No. 10-2024-0149673, filed with the Korean Intellectual Property Office on October 29, 2024, the entire contents of which are incorporated herein by reference.

[0003] This disclosure relates to compositions for use in organic light-emitting devices and organic light-emitting devices comprising 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 exhibit characteristics such as wide viewing angle, excellent contrast, fast response time, and superior brightness, driving voltage, and response speed, and have therefore 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, and for example, it can be formed from a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. In the structure of 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 each other, excitons are formed, and light is emitted when the excitons return to the ground state.

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

[0007] [Existing technical documents]

[0008] [Patent Literature]

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

[0010] Technical issues

[0011] One object of this disclosure is to provide a composition for an organic light-emitting device, the composition comprising two types of compounds contained in an organic material layer of the organic light-emitting device, and capable of improving the efficiency and lifetime characteristics of the organic light-emitting device.

[0012] Furthermore, one object of this disclosure is to provide an organic light-emitting device comprising the composition described above for an organic light-emitting device.

[0013] Furthermore, one objective of this disclosure is to provide an organic light-emitting device comprising the two types of compounds described above.

[0014] Technical solution

[0015] According to this disclosure, a composition for an organic light-emitting device is provided, comprising a first compound represented by the following chemical formula 1 and a second compound represented by the following chemical formula 2:

[0016] [Chemical Formula 1]

[0017]

[0018] In chemical formula 1,

[0019] Ar1 and Ar2 are each independently substituted or unsubstituted C. 6-60 aryl; or substituted or unsubstituted C containing any or more of N, O, and S. 2-60 Mixed aromatics,

[0020] L1 and L2 are each independent single bonds; or C bonds that are substituted or unsubstituted. 6-60 Alpha-aryl

[0021] R 11 R 12 and R 13 Each is independently a deuterium.

[0022] a and c are each independent integers from 0 to 4.

[0023] b is an integer from 0 to 2, and

[0024] [Chemical Formula 2]

[0025]

[0026] In chemical formula 2,

[0027] Ar3 and Ar4 are each independently substituted or unsubstituted C. 6-15 Aryl,

[0028] R a and R d Each is independently hydrogen; deuterium; or substituted or unsubstituted C. 6-60 Aryl,

[0029] R b It is hydrogen or deuterium.

[0030] R c It is hydrogen; deuterium; or C, either unsubstituted or deuterated. 6-60 Aryl,

[0031] R 21 To R 28 Each is independently hydrogen; deuterium; or substituted or unsubstituted C. 6-60 aryl, condition R 21 To R 28 At least one of them is deuterium or deuterated C. 6-60 Aryl, and

[0032] The second compound is substituted with six or more deuterium atoms.

[0033] According to another aspect of this disclosure, an organic light-emitting device is provided, comprising: an anode; a cathode; and one or more layers of organic material disposed between the anode and the cathode, wherein one or more layers of organic material contain the composition for the organic light-emitting device.

[0034] According to another aspect of this disclosure, an organic light-emitting device is provided, comprising: an anode, a cathode, and a light-emitting layer between the anode and the cathode, wherein the light-emitting layer comprises a first compound represented by the following chemical formula 1 and a second compound represented by the following chemical formula 2:

[0035] [Chemical Formula 1]

[0036]

[0037] In chemical formula 1,

[0038] Ar1 and Ar2 are each independently substituted or unsubstituted C. 6-60 aryl; or substituted or unsubstituted C containing any or more of N, O, and S. 2-60 Mixed aromatics,

[0039] L1 and L2 are each independent single bonds; or C bonds that are substituted or unsubstituted. 6-60 Alpha-aryl

[0040] R 11 R 12 and R 13 Each is independently a deuterium.

[0041] a and c are each independent integers from 0 to 4.

[0042] b is an integer from 0 to 2, and

[0043] [Chemical Formula 2]

[0044]

[0045] In chemical formula 2,

[0046] Ar3 and Ar4 are each independently substituted or unsubstituted C. 6-15 Aryl,

[0047] R a and R d Each is independently hydrogen; deuterium; or substituted or unsubstituted C. 6-60 Aryl,

[0048] R b It is hydrogen or deuterium.

[0049] R c It is hydrogen; deuterium; or C, either unsubstituted or deuterated. 6-60 Aryl,

[0050] R 21 To R 28 Each is independently hydrogen; deuterium; or substituted or unsubstituted C. 6-60 aryl, condition R 21 To R 28 At least one of them is deuterium or deuterated C. 6-60 Aryl, and

[0051] The second compound is substituted with six or more deuterium atoms.

[0052] Beneficial effects

[0053] The above-mentioned composition for organic light-emitting devices can improve the efficiency, driving voltage and / or lifetime characteristics of organic light-emitting devices by including two host compounds with specific structures. Attached Figure Description

[0054] Figure 1 shows an example of an organic light-emitting device including a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4.

[0055] Figure 2 shows 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, an electron blocking layer 7, a light-emitting layer 3, a hole blocking layer 8, an electron injection and transport layer 9, and a cathode 4. Detailed Implementation

[0056] In the following sections, embodiments of the present disclosure will be described in more detail to facilitate understanding of the invention.

[0057] (Definition of the term)

[0058] As used in this article, symbols This refers to a bond that is connected to another substituent.

[0059] In this disclosure, 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 heterocyclic 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 with two or more substituents linked together" can be biphenyl. That is, biphenyl can be aryl, or it can be interpreted as a substituent formed by linking two phenyl groups. In one instance, the term "substituted or unsubstituted" can be understood to mean "unsubstituted or substituted from deuterium, halogen, cyano, silyl, C 1-10 Alkyl, C 1-10 Alkoxy and C 6-20 "Substituted with one or more substituents of the aryl group", or "unsubstituted or substituted with one or more substituents selected from deuterium, halogen, cyano, methyl, ethyl, phenyl, biphenyl, and naphthyl". Furthermore, as used herein, the term "substituted with one or more substituents" can be understood to mean "substituted with a single to a maximum number of substitutable hydrogens". Alternatively, as used herein, the term "substituted with one or more substituents" can be understood to mean "substituted with 1 to 5 substituents", or "substituted with one or two substituents".

[0060] 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.

[0061]

[0062] 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.

[0063]

[0064] In this disclosure, the number of carbon atoms in the imide group is not particularly limited, but is preferably 1 to 25. Specifically, the imide group can be a substituent having the following structural formula, but is not limited thereto.

[0065]

[0066] In this disclosure, silyl group refers to -Si(Z1)(Z2)(Z3), wherein Z1, Z2, and Z3 are each independently hydrogen, deuterium, substituted or unsubstituted C. 1-60 Alkyl, substituted or unsubstituted C 1-60 Halogenated alkyl, substituted or unsubstituted C 2-60 alkenyl, substituted or unsubstituted C 2-60 Haloalkenyl, or substituted or unsubstituted C 6-60 Aryl. According to one embodiment, Z1, Z2, and Z3 can each independently be hydrogen, deuterium, substituted or unsubstituted C. 1-10 Alkyl, substituted or unsubstituted C 1-10 Halogenated alkyl groups, or substituted or unsubstituted C4 groups 6-20 Aryl. Specific examples of silyl groups include, but are not limited to, trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, etc.

[0067] In this disclosure, boron group specifically includes, but is not limited to, trimethylboronyl, triethylboronyl, tert-butyldimethylboronyl, triphenylboronyl, and phenylboronyl.

[0068] Examples of halogen groups in this disclosure include fluorine, chlorine, bromine, or iodine.

[0069] 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 5 carbons. Specific examples of alkyl groups include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, 1-ethyl-propyl, 1,1-dimethylpropyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethyl Butyl, heptyl, n-heptyl, isohexyl, 1-methylhexyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 5-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2,4,4-trimethyl-1-pentyl, 2,4,4-trimethyl-2-pentyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, etc., but not limited to these.

[0070] 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.

[0071] In this disclosure, an alicyclic group refers to a monovalent substituent derived from a saturated or unsaturated cyclic hydrocarbon compound containing only carbon as the cyclizing atom but lacking aromaticity; it should be understood to encompass both monocyclic compounds and fused polycyclic compounds. According to one embodiment, the alicyclic group has 3 to 60 carbon atoms. According to another embodiment, the alicyclic group has 3 to 30 carbon atoms. According to yet another embodiment, the alicyclic group has 3 to 20 carbon atoms. According to yet another embodiment, the alicyclic group has 5 to 10 carbon atoms. Examples of alicyclic groups include monocyclic groups such as cycloalkyl groups, bridging hydrocarbon groups, spirocyclic hydrocarbon groups, substituents derived from hydrogenated derivatives of aromatic hydrocarbon compounds, etc.

[0072] Specifically, examples of cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, etc.

[0073] In addition, examples of bridging hydrocarbon groups include, but are not limited to, bicyclo[1.1.0]butyl, bicyclo[2.2.1]heptyl, bicyclo[4.2.0]octyl-1,3,5-trienyl, adamantyl, decalinyl, etc.

[0074] In addition, examples of spirocyclic hydrocarbon groups include, but are not limited to, spiro[3.4]octyl, spiro[5.5]undecyl, etc.

[0075] Furthermore, substituents in hydrogenated derivatives of aromatic hydrocarbons refer to substituents derived from monocyclic or polycyclic aromatic hydrocarbons in which a portion of the compound has been hydrogenated. Examples of such substituents include, but are not limited to, 1H-indenyl, 2H-indenyl, 4H-indenyl, 2,3-dihydro-1H-indenyl, 1,4-dihydronaphthyl, 1,2,3,4-tetrahydronaphthyl, 6,7,8,9-tetrahydro-5H-benzo[7]annulenyl, 6,7-dihydro-5H-benzocycloheptenyl, etc.

[0076] In this disclosure, aryl is understood to mean a substituent derived from a monocyclic or fused polycyclic compound containing only carbon as a cyclic atom and also possessing aromaticity, and its carbon number is not particularly limited, but is preferably 6 to 60. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. According to one embodiment, the aryl group has 6 to 12 carbon atoms. According to one embodiment, the aryl group has 10 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.

[0077] 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.

[0078] In this disclosure, a heterocyclic group refers to a monovalent substituent derived from a monocyclic or fused polycyclic compound containing at least one heteroatom selected from O, N, Si, and S as a cyclic atom in addition to carbon, and is understood to encompass both aromatic and non-aromatic substituents. According to one embodiment, the heterocyclic group has 2 to 60 carbon atoms. According to another embodiment, the heterocyclic group has 2 to 30 carbon atoms. According to yet another embodiment, the heterocyclic group has 2 to 20 carbon atoms. Examples of such heterocyclic groups include heteroaryl groups, substituents of hydrogenated derivatives derived from heteroaromatic compounds, etc.

[0079] Specifically, a heteroaryl group refers to a substituent derived from a monocyclic or fused polycyclic compound containing at least one heteroatom selected from N, O, and S as a cyclic atom in addition to carbon, and is an aromatic substituent. According to one embodiment, the heteroaryl group has 2 to 60 carbon atoms. According to another embodiment, the heteroaryl group has 2 to 30 carbon atoms. According to another embodiment, the heteroaryl group has 2 to 20 carbon atoms. According to another embodiment, the heteroaryl group has 2 to 12 carbon atoms. According to another embodiment, the heteroaryl group has 2 to 10 carbon atoms. According to another embodiment, the heteroaryl group has 2 to 8 carbon atoms. According to another embodiment, the heteroaryl group has 10 to 20 carbon atoms. Examples of heteroaryl groups include thiophene, furanyl, pyrrole, imidazolyl, thiazolyl, etc. azole group, Diazolyl, Triazolyl, Pyridyl, Bipyridyl, Pyrimidinyl, Triazinyl, Acridineyl, Pyridazinyl, Quinolinyl, Quinazolinyl, Quinoxalinyl, Phtharazineyl, Pyridopyrimidinyl, Pyridopyrazinyl, Isoquinolinyl, Indoleyl, Carbazoleyl, Benzo[] Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazole, benzothiophene, dibenzothiophene, benzofuranyl, dibenzofuranyl, phenanthrolinel, iso Azolyl, thiadiazole, phenthiazinyl, etc., but not limited to these.

[0080] Furthermore, substituents in hydrogenated derivatives derived from heteroaromatic compounds refer to substituents derived from monocyclic or polycyclic heteroaromatic compounds in which some of the unsaturated bonds are hydrogenated. Examples of such substituents include, but are not limited to, 1,3-dihydroisobenzofuranyl, 2,3-dihydrobenzofuranyl, 1,3-dihydrobenzo[c]thiophenyl, and 2,3-dihydro[b]thiophenyl.

[0081] In this disclosure, the aryl groups in aralkyl, arylenyl, alkylaryl, arylamino, and arylsilyl are the same as examples of aryl groups as defined above. In this disclosure, the alkyl groups in aralkyl, alkylaryl, and alkylamino are the same as examples of alkyl groups as defined above. In this disclosure, the heteroaryl groups in heteroarylamines can be described using the heteroaryl group as defined above. In this disclosure, the alkenyl groups in arylenyl are the same as examples of alkenyl groups as defined above. In this disclosure, the aryl groups as defined above can be described, except that the arylene group is a divalent group. In this disclosure, the heteroaryl groups as defined above can be described, except that the heteroaryl group is a divalent group. In this disclosure, the aryl or cycloalkyl groups as defined above can be described, except that the hydrocarbon ring is not a monovalent group, but is formed by combining two substituents. In this disclosure, the description of heteroaryl groups as defined above can be applied, except that the heterocycle is not a monovalent group, but is formed by combining two substituents.

[0082] In this disclosure, the term "deuterated or deuterated" means that at least one of the substituted hydrogen atoms in a compound, a divalent linker, or a monovalent substituent is replaced by deuterium.

[0083] Furthermore, the terms "unsubstituted or deuterated" or "deuterated or unsubstituted" mean "unsubstituted or a single to a maximum number of substituted hydrogen atoms are replaced by deuterium." In one instance, given that the maximum number of hydrogen atoms that can be replaced by deuterium in a phenanthrene structure is 9, the term "unsubstituted or deuterated phenanthrene" can be understood to mean "unsubstituted or phenanthrene with 1 to 9 deuterium atoms."

[0084] Furthermore, "deuterated structure" refers to compounds, divalent linking groups, or monovalent substituents in which at least one hydrogen atom is replaced by deuterium. As an example, the deuterated structure of a phenyl group can be understood as all monovalent substituents in which at least one substituted hydrogen atom in the phenyl group is replaced by deuterium, as follows.

[0085]

[0086] Furthermore, the "deuterium substitution rate" or "degree of deuteration" of a compound refers to the percentage calculated as the ratio of the number of substituted deuterium atoms to the total number of hydrogen atoms that can exist in the compound (the sum of the number of hydrogen atoms that can be substituted by deuterium and the number of substituted deuterium atoms). Therefore, when the "deuterium substitution rate" or "degree of deuteration" of a compound is "K%", it means that K% of the hydrogen atoms in the compound that can be substituted by deuterium are replaced by deuterium.

[0087] At this point, the "deuterium substitution rate" or "degree of deuteration" can be determined using known methods such as MALDI-TOF MS (Matrix-Assisted Laser Desorption / Ionization Time-of-Flight Mass Spectrometer) and nuclear magnetic resonance spectroscopy. 1 The degree of deuteration can be determined using methods such as ¹H NMR, TLC / MS (Thin-Layer Chromatography / Mass Spectrometry), and GC / MS (Gas Chromatography / Mass Spectrometry). More specifically, when using MALDI-TOF MS, the "deuteration rate" or "degree of deuteration" can be obtained by determining the number of substituted deuterons in the compound via MALDI-TOF MS analysis, and then calculating the ratio of the number of substituted deuterons to the total number of hydrogen atoms that can be present in the compound as a percentage.

[0088] Furthermore, the above descriptions related to deuterium can be applied to "tritium structure", "tritium substitution rate" or "degree of tritium", except that tritium, rather than deuterium, is used for substitution.

[0089] The contents of this disclosure will be described in detail below.

[0090] Compositions for organic light-emitting devices

[0091] One embodiment of this disclosure provides a composition for an organic light-emitting device comprising a first compound represented by Chemical Formula 1 and a second compound represented by Chemical Formula 2. The first and second compounds can act as hosts in the emissive layer of the organic light-emitting device. Specifically, the first compound acts as a p-type host material in which hole transport capability is superior to electron transport capability, and the second compound acts as an n-type host material in which electron transport capability is superior to hole transport capability, thereby forming an exciton complex. Therefore, excitons can be emitted uniformly throughout the emissive layer, enabling simultaneous improvement in the luminous efficiency and lifetime characteristics of the organic light-emitting device.

[0092] Specifically, the first compound, serving as the p-type host material, possesses an indolo[2,3-c]carbazole structure in indolocarbazole, thereby exhibiting superior hole characteristics and, as a result, improving the lifetime characteristics of organic light-emitting devices. However, to maximize the superior hole characteristics of indolocarbazole, the use of an n-type host material exhibiting rapid electron transport characteristics is necessary. But if electron injection is too fast, it may disrupt the electron / hole balance, thus requiring assistance from hole injection characteristics. In this regard, in this disclosure, a second compound having a structure in which carbazole and triazine are ortho-bonded about a benzene ring, and whereby the carbazole and triazine are sterically distorted and further substituted with deuterium to a certain level or higher. Since the carbazole and triazine in the second compound are ortho-bonded about a benzene ring, this contributes to hole injection characteristics, and as a result, significantly improves luminous efficiency. Furthermore, the twisted structures of carbazole and triazine allow the electronic properties of triazine and the hole properties of carbazole to function independently without canceling each other out. In addition, a certain level or higher of deuterium substitution can further improve lifetime properties.

[0093] (First compound)

[0094] The first compound is represented by Chemical Formula 1. Specifically, the first compound has a structure in which an aryl, dibenzofuran, or dibenzothiophene group is substituted on the indolo[2,3-c]carbazole core structure, thereby enabling it to effectively transfer holes to the dopant material. In particular, among the various structures of indolo[2,3-c]carbazole, it has an indolo[2,3-c]carbazole structure, thus exhibiting superior hole properties, and as a result, it can increase the recombination probability of holes and electrons in the luminescent layer together with the second compound, which has excellent electron transport capabilities.

[0095] Furthermore, in one embodiment, Ar1 and Ar2 can each be independently substituted or unsubstituted C. 6-20 aryl; or substituted or unsubstituted C containing at least one of N, O and S. 2-20 Mixed aromatic compounds.

[0096] In another implementation, Ar1 and Ar2 can each be independently C 6-20 Aryl, dibenzofuranyl, dibenzothiophenyl, carbazole, or 9-phenylcarbazole

[0097] Ar1 and Ar2 can be either unsubstituted or substituted by one or more deuterium atoms.

[0098] In another embodiment, Ar1 and Ar2 can each independently be phenyl, biphenyl, terphenyl, triphenylene, dibenzofuranyl, dibenzothiophenyl, carbazole, or 9-phenylcarbazole.

[0099] Ar1 and Ar2 can be either unsubstituted or substituted by one or more deuterium atoms.

[0100] For example, Ar1 and Ar2 can each be independently selected from any of the following structures and their deuterated structures:

[0101]

[0102] In another embodiment, one of Ar1 and Ar2 can be an unsubstituted or substituted C with one or more deuterium atoms. 6-20 Monocyclic aryl.

[0103] In another embodiment, one of Ar1 and Ar2 may be phenyl, biphenyl, or terphenyl, and the remainder may be phenyl, biphenyl, terphenyl, triphenylene, dibenzofuranyl, dibenzothiophenyl, carbazoleyl, or 9-phenylcarbazole.

[0104] Ar1 and Ar2 can be either unsubstituted or substituted by one or more deuterium atoms.

[0105] In another implementation, Ar1 and Ar2 can be either unsubstituted or substituted with five or more deuterium atoms.

[0106] In another implementation, one or both of Ar1 and Ar2 may be completely replaced by deuterium.

[0107] In another implementation, Ar1 and Ar2 may be the same as or different from each other.

[0108] In another implementation, L1-Ar1 and L2-Ar2 may be the same as or different from each other.

[0109] In one implementation, L1 and L2 can each be independently a single bond, or a substituted or unsubstituted C bond. 6-20 Alpha-aryl.

[0110] In another implementation, L1 and L2 can each be independently a single bond, substituted or unsubstituted C. 6-18 Monocyclic aryl, or substituted or unsubstituted C 10-20 Polycyclic aryl groups.

[0111] In another embodiment, L1 and L2 can each independently be a single bond, phenylene, biphenyl diyl, terphenyl diyl, or naphthylene.

[0112] Among them, L1 and L2, which are not single bonds, can be unsubstituted or substituted by one or more deuterium atoms.

[0113] In another embodiment, L1 and L2 can each be independently a single bond or a phenylene group.

[0114] The phenylene group may be unsubstituted or substituted with one or more deuterium atoms.

[0115] For example, L1 and L2 can each be independently a single bond, a 1,2-phenylene substituted with one or more deuterium atoms or unsubstituted, a 1,3-phenylene substituted with one or more deuterium atoms or unsubstituted, or a 1,4-phenylene substituted with one or more deuterium atoms or unsubstituted.

[0116] Furthermore, when phenylene can be substituted with deuterium, it can be substituted with one or more deuterium atoms or with four deuterium atoms.

[0117] In one implementation, R 11 R 12 and R 13 Each can be a deuterium.

[0118] In addition, 'a' means R. 11 The number of, and can be an integer of 0, 1, 2, 3, or 4.

[0119] When a is 0, this means that it does not contain the substituent R. 11 That is, it is something that has not been replaced.

[0120] In addition, b means R 12 The number of, and can be an integer of 0, 1, or 2.

[0121] When b is 0, this means that it does not contain the substituent R. 12 That is, it is something that has not been replaced.

[0122] In addition, c means R 13 The number of, and can be an integer of 0, 1, 2, 3, or 4.

[0123] When c is 0, this means that it does not contain the substituent R. 13 That is, it is something that has not been replaced.

[0124] In one implementation, a, b, and c can all be 0.

[0125] In another implementation, a and c can each be 4, and b can be 2.

[0126] In one embodiment, the first compound may not contain deuterium, or it may contain one or more deuterium atoms.

[0127] When the first compound contains deuterium, the deuterium substitution rate of the first compound can be from 1% to 100%. Specifically, the deuterium substitution rate of the first compound can be 5% or more, 10% or more, 20% or more, 30% or more, 40% or more, 50% or more, 60% or more, 70% or more, 75% or more, 80% or more, or 90% or more, and 100% or less.

[0128] As an example, the first compound may not contain deuterium, or it may contain 1 to 50 deuterium atoms. More specifically, the first compound may not contain deuterium, or it may contain 1 or more, 2 or more, 3 or more, 4 or more, 5 or more, 6 or more, 7 or more, 8 or more, or 9 or more, and 50 or fewer, 40 or fewer, 30 or fewer, 28 or fewer, 26 or fewer, 24 or fewer, 22 or fewer, 20 or fewer, 18 or fewer, 16 or fewer, 14 or fewer, 13 or fewer, 12 or fewer, 11 or fewer, or 10 or fewer deuterium atoms.

[0129] Meanwhile, deuterium has a higher mass value than hydrogen, resulting in a lower potential energy level and a lower zero-point energy. Furthermore, due to its greater atomic weight, its vibrational modes are smaller, leading to a lower vibrational energy level than hydrogen. Therefore, when hydrogen atoms in a compound are replaced by deuterium, intermolecular van der Waals forces are reduced, and the reduction in quantum efficiency caused by collisions due to intermolecular vibrations can be prevented.

[0130] Furthermore, because deuterium lowers the zero-point energy with carbon, the bond energy of the CD bond becomes higher than that of the CH bond. Therefore, when a compound contains deuterium, it has stronger intramolecular bond energies, which can thus improve the stability of the material.

[0131] Representative examples of compounds represented by chemical formula 1 are as follows:

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141] Meanwhile, for example, the first compound represented by chemical formula 1 can be prepared by a preparation method such as the following reaction scheme 1.

[0142] [Reaction Scheme 1]

[0143]

[0144] In reaction scheme 1, Ar1, Ar2, L1, L2, R 11 R 12 R 13 a, b, and c are as defined in chemical formula 1, and X is a halogen, and preferably X is fluorine, chlorine, or bromine.

[0145] As another example, the first compound represented by chemical formula 1 can be prepared by a preparation method such as the following reaction scheme 2.

[0146] [Reaction Scheme 2]

[0147]

[0148] In reaction scheme 2, R 11 R 12 R 13 a, b, and c are as defined in chemical formula 1.

[0149] In addition, Y is Furthermore, Ar1, Ar2, L1, and L2 are as defined in Formula 1. In addition, Z is a halogen, and preferably Z is fluorine, chlorine, or bromine.

[0150] Both reaction schemes 1 and 2 are amine substitution reactions, and are preferably carried out in the presence of a palladium catalyst and a base. The reactor used for the amine substitution reaction can be modified as is known in the art.

[0151] As another example, a first compound having at least one deuterium can be prepared by a preparation method such as the following reaction scheme 3.

[0152] [Reaction Scheme 3]

[0153]

[0154] In reaction scheme 3, L'1, L'2, Ar'1, Ar'2, and R' 11 To R' 13 Each refers to an undeuterated L1, L2, Ar1, Ar2, and R1 to R3 substituent, and the remaining substituents are defined as described above.

[0155] Specifically, a first compound having at least one deuterium can be prepared by deuterating an unsubstituted deuterium-containing first compound. In this case, the deuteration reaction can be carried out by adding the unsubstituted deuterium-containing first compound to a deuterating solvent such as a benzene-D6 (C6D6) solution, and then reacting it with TfOH (trifluoromethanesulfonic acid).

[0156] The other compounds can be prepared similarly.

[0157] The method for preparing the first compound represented by chemical formula 1 can be described in more detail in the preparation examples described below.

[0158] (Second compound)

[0159] The second compound is represented by chemical formula 2. Specifically, the second compound exhibits excellent electron transport capabilities because carbazole and triazine are ortho-bonded about the benzene ring, and the carbazole and triazine are sterically distorted. As a result, it can effectively transfer electrons to the dopant material, thereby increasing the recombination probability of electrons and holes in the light-emitting layer. Furthermore, due to its structure in which the substituent Rc is para-bonded relative to carbazole, it exhibits rapid electron transport characteristics and also contributes to hole injection characteristics, further maximizing the hole transport characteristics of the first compound. In addition, since six or more hydrogen atoms in the second compound are replaced by deuterium, the vibrational energy of the radical anion state is reduced, allowing it to have a stable energy, and thus the formed excitocomplex can also be in a more stable state. As a result, the lifetime characteristics of organic light-emitting devices can be further improved.

[0160] In one implementation, Ar3 and Ar4 can each be independently substituted or unsubstituted C. 6-14 Aryl.

[0161] In another embodiment, Ar3 and Ar4 can each be independently phenyl or biphenyl.

[0162] Ar3 and Ar4 can be independently unsubstituted or substituted with one or more or five or more deuterium atoms.

[0163] In another embodiment, one of Ar3 and Ar4 may be phenyl, and the other may be phenyl or biphenyl.

[0164] Ar3 and Ar4 can be independently unsubstituted or substituted with one or more or five or more deuterium atoms.

[0165] In another implementation, Ar3 and Ar4 may be the same as or different from each other.

[0166] In one implementation, R a and R d They can each be hydrogen, deuterium, or carbon independently. 6-20 Aryl,

[0167] Among them, C 6-20 The aryl group can be unsubstituted or substituted with one or more deuterium atoms.

[0168] In another implementation, R a and R d Each of these can independently be hydrogen, deuterium, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, or triphenylene, and

[0169] Phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, and triphenylene can each be independently unsubstituted or substituted with one or more, or five or more, deuterium atoms.

[0170] For example, R a and R d Each can be independently selected from hydrogen, deuterium, the following structures and their deuterated structures:

[0171]

[0172] In another implementation, R a and R d They can be the same as or different from each other.

[0173] In one implementation, R c It can be hydrogen; deuterium; or unsubstituted or deuterated C. 6-20 Aryl.

[0174] In another implementation, R c It can be hydrogen, deuterium, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, or triphenylene.

[0175] Among them, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene and triphenylene can each be independently unsubstituted or substituted with one or more, or five or more deuterium atoms.

[0176] In another implementation, R c It can be unsubstituted phenyl, unsubstituted biphenyl, unsubstituted terphenyl, unsubstituted naphthyl, unsubstituted anthraceneyl, unsubstituted phenanthryl, or unsubstituted triphenylene.

[0177] In one implementation, R 21 To R 28 Each can be hydrogen; deuterium; or substituted or unsubstituted C, independently. 6-20 aryl, condition R 21 To R 28 At least one of them can be deuterium, or deuterium-substituted C. 6-20 Aryl.

[0178] In another implementation, R 21 To R 28 Each can be independently hydrogen, deuterium, unsubstituted phenyl, or phenyl substituted with 1 to 5 deuterium atoms, provided that R 21 To R 28 At least one of them can be deuterium or a phenyl substituted with 1 to 5 deuterium atoms.

[0179] In another implementation, R 21 To R 28 Four or more of them can be deuterium, and the remainder can be hydrogen, unsubstituted phenyl, or phenyl substituted with 1 to 5 deuterium atoms.

[0180] In another implementation, R 21 To R 28 Four to six of them can be deuterium, and the rest can be hydrogen.

[0181] In another implementation, R 21 To R 28 Each can be a deuterium.

[0182] In another implementation, R 21 To R 28 One of them can be a phenyl group substituted with 1 to 5 deuterium atoms, and the others can be hydrogen or deuterium.

[0183] In another implementation, R 21 To R 28 Each can be independently hydrogen, deuterium, unsubstituted phenyl, or phenyl substituted with 1 to 5 deuterium atoms, provided that R 25 and R 26 Either of them can be a phenyl group substituted with 1 to 5 deuterium atoms.

[0184] In another implementation, R21 To R 28 Each can be independently hydrogen, deuterium, or a phenyl group substituted with 3 to 5 deuterium atoms, provided that R... 25 and R 26 Either of them can be a phenyl group substituted with 3 to 5 deuterium atoms.

[0185] In another implementation, R 21 To R 28 Each can be independently hydrogen, deuterium, or a phenyl substituted with 1 to 5 deuterium atoms, provided that R 21 To R 28 Of these, 4 to 6 can be deuterium, and R 25 and R 26 Either of them can be a phenyl group substituted with 3 to 5 deuterium atoms.

[0186] In one embodiment, the second compound may contain six or more deuterium atoms.

[0187] More specifically, the second compound may contain 6 or more, 7 or more, 8 or more, or 9 or more, and 50 or fewer, 40 or fewer, 30 or fewer, 28 or fewer, 26 or fewer, 24 or fewer, 22 or fewer, 20 or fewer, 18 or fewer, 16 or fewer, 14 or fewer, 13 or fewer, 12 or fewer, 11 or fewer, or 10 or fewer deuterium atoms.

[0188] Representative examples of the second compound are as follows:

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208] Meanwhile, for example, the second compound can be prepared by a method such as reaction scheme 4 below, and the remaining compounds can be prepared similarly:

[0209] [Reaction Scheme 4]

[0210]

[0211] In reaction scheme 4, Ar3, Ar4, and R a To R d and R 21 To R 28 As defined in chemical formula 2, and X is a halogen, and preferably X is fluorine or chlorine.

[0212] Specifically, reaction scheme 4 is an amine substitution reaction, preferably carried out in the presence of a palladium catalyst and a base, and the reactor used for the amine substitution reaction can be modified as is known in the art. The preparation method can be described in more detail in the preparation examples described below.

[0213] Simultaneously, the first compound and the second compound may be included in the composition at a weight ratio of 1:99 to 99:1. Furthermore, from the perspective of further improving the voltage, efficiency, and lifetime of the device by balancing holes and electrons, the first compound and the second compound may be included at a weight ratio of 10:90 to 90:10, or 20:80 to 50:50. More specifically, the first compound and the second compound may be included in the composition at a weight ratio of 40:60 to 50:50.

[0214] In addition, the composition can be a mixture or an organic alloy.

[0215] In one embodiment, the composition can be a mixture in which the first compound and the second compound are simply mixed. Such a mixture is one in which the compounds are physically and homogeneously mixed without separate pretreatment, and can be prepared using mixers known in the art.

[0216] Therefore, when the first and second compounds are applied to an organic light-emitting device in the form of a mixture, the process can be simplified because each compound is supplied from a single source rather than separate sources during the formation of the organic material layer, as no process control steps for multiple sources are required.

[0217] In another embodiment, the composition may be an organic alloy in which the first and second compounds have a chemical interaction through pretreatment. Pretreatment may be, for example, cooling following a heat treatment process (e.g., heating and / or sublimation of the mixture of compounds), but is not limited thereto.

[0218] Furthermore, when the first and second compounds are applied to organic light-emitting devices in the form of an organic alloy composition,

[0219] During the formation of the organic material layer, all compounds are supplied from a single source, which not only simplifies the process but also ensures the uniformity and consistency of the deposited material. Therefore, when multiple organic material layers are formed in a continuous process, organic material layers with substantially the same component ratios can be produced continuously, thus improving the reproducibility and reliability of the organic material layers.

[0220] Organic light-emitting devices

[0221] Meanwhile, another embodiment of this disclosure provides a light-emitting device comprising: an anode; a cathode disposed opposite to the anode; and one or more organic material layers disposed between the anode and the cathode, wherein one or more of the organic material layers contains the composition for the organic light-emitting device. In such an organic light-emitting device, the composition can be supplied from a single source during the formation of the organic material layers.

[0222] In this document, the organic material layer comprising the composition may be a light-emitting layer.

[0223] Furthermore, another embodiment of this disclosure provides an organic light-emitting device comprising: an anode; a cathode disposed opposite to the anode; and one or more organic material layers disposed between the anode and the cathode, wherein one or more of the organic material layers comprises a compound represented by Chemical Formula 1 and a compound represented by Chemical Formula 2. In such an organic light-emitting device, the first compound and the second compound can be supplied from separate sources during the formation of the organic material layers. For example, in an organic light-emitting device, the organic material layer comprising the first compound and the second compound can be formed by co-deposition of the first compound and the second compound.

[0224] In this paper, the organic material layer containing the first compound and the second compound can be a light-emitting layer.

[0225] Furthermore, another embodiment of this disclosure provides an organic light-emitting device comprising: an anode; a cathode disposed opposite to the anode; and a light-emitting layer disposed between the anode and the cathode, wherein the light-emitting layer comprises a first compound represented by chemical formula 1 and a second compound represented by chemical formula 2.

[0226] In this case, the descriptions of the first compound, the second compound, and the composition are as described above.

[0227] Furthermore, the organic material layer of an organic light-emitting device can have a single-layer structure, but it can also have a multi-layer 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 can include fewer or more organic material layers.

[0228] In one embodiment, the organic material layer may include a light-emitting layer, and in this case, the organic material layer containing the first compound and the second compound may be a light-emitting layer.

[0229] In another embodiment, the organic material layer may include a hole injection layer, a hole transport layer, a light-emitting layer, and an electron injection and transport layer, and in this case, the organic material layer containing the composition may be a light-emitting layer.

[0230] In another embodiment, the organic material layer may include a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, and an electron injection and transport layer, and in this case, the organic material layer containing the composition may be a light-emitting layer.

[0231] In another embodiment, the organic material layer may include a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer, and in this case, the organic material layer containing the composition may be a light-emitting layer.

[0232] 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, Figures 1 and 2 show the structure of an organic light-emitting device according to one embodiment of this disclosure.

[0233] Figure 1 shows an example of an organic light-emitting device consisting of a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4. In such a structure, the composition, or the first and second compounds, may be contained within the light-emitting layer.

[0234] Figure 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, an electron blocking layer 7, a light-emitting layer 3, a hole blocking layer 8, an electron transport and injection layer 9, and a cathode 4. In such a structure, the composition or the first and second compounds may be contained within the light-emitting layer.

[0235] As an example, an organic light-emitting device according to this disclosure may consist of a substrate, an anode, a hole injection layer, a first hole transport layer, a second hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron injection and transport layer, and a cathode. In such a structure, the composition or the first and second compounds may be contained within the light-emitting layer.

[0236] Furthermore, organic light-emitting devices can be manufactured using materials and methods known in the art, the difference being that one or more of the organic material layers comprise the composition or the first and second compounds. Additionally, when an 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.

[0237] 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, conductive metal oxide, or an alloy thereof on the substrate using a PVD method such as sputtering or electron beam evaporation to form an anode, then 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 finally depositing a material that can serve as a cathode on the organic material layer. In addition to this method, the organic light-emitting device can also be fabricated by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate (WO 2003 / 012890). However, the fabrication method is not limited to this.

[0238] Furthermore, one or more of the organic material layers can be formed by solution coating. Here, solution coating means, but is not limited to, spin coating, dip coating, doctor blade coating, inkjet printing, screen printing, spraying, or roll coating.

[0239] Furthermore, organic light-emitting devices can be bottom-emitting devices, top-emitting devices, or dual-sided emitting devices, and in particular, they can be bottom-emitting devices that require relatively high luminous efficiency.

[0240] The components of an organic light-emitting device will be described in detail below.

[0241] Anode and cathode

[0242] As used in this disclosure, anode and cathode refer to electrodes used in organic light-emitting devices.

[0243] Materials with a large work function are generally preferred as anode materials, allowing for smooth hole injection 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; and conductive polymers, such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

[0244] Materials with a small work function are generally preferred as cathode materials, making it easy to inject electrons into the organic material layer. Specific examples of cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; and multilayer materials such as LiF / Al or LiO2 / Al.

[0245] Hole injection layer

[0246] Organic light-emitting devices according to this disclosure may optionally include a hole injection layer between the anode and the hole transport layer described below.

[0247] The hole injection layer is a layer positioned on the anode and injecting holes from the anode, and contains a hole injection material. As such a hole injection material, a compound is preferred that possesses the ability to transport holes, exhibits excellent hole injection effect from the anode to the luminescent layer or luminescent material, prevents excitons generated in the luminescent layer from migrating to the electron injection layer or electron injection material, and also possesses excellent thin film formation capabilities. In particular, the HOMO (highest occupied molecular orbital) of the hole injection material is suitable between the work function of the anode material and the HOMO of the surrounding organic material layer.

[0248] Specific examples of hole injection materials include, but are not limited to, compounds represented by chemical formula 1, metalloporphyrins, oligothiophenes, arylamine-based organic materials, hexanitrile hexaazabenzophenanthrene-based organic materials, quinacridone-based organic materials, perylene-based organic materials, anthraquinones, polyaniline, and polythiophene-based conductive polymers.

[0249] Hole transport layer

[0250] Organic light-emitting devices according to this disclosure may optionally include one or more hole transport layers between the anode and the light-emitting layer.

[0251] The hole transport layer is a layer that receives holes from the anode or from a hole injection layer formed on the anode and transports the holes to the light-emitting layer, and includes a hole transport material. The hole transport material is suitably a material with a high hole mobility that can receive holes from the anode or the hole injection layer and transfer the holes to the light-emitting layer. Specific examples include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers in which conjugated and non-conjugated portions coexist.

[0252] Electron blocking layer

[0253] The organic light-emitting device according to this disclosure may optionally include an electron blocking layer between the hole transport layer and the light-emitting layer. An electron blocking layer is a layer formed on the hole transport layer, preferably positioned in contact with the light-emitting layer, and used to modulate hole mobility, prevent excessive electron movement, and increase the likelihood of hole-electron coupling, thereby improving the efficiency of the organic light-emitting device. The electron blocking layer comprises an electron blocking material, and examples of such electron blocking materials may include, but are not limited to, arylamine-based organic materials.

[0254] Emissive layer

[0255] The organic light-emitting device according to this disclosure includes a light-emitting layer between the anode and the cathode.

[0256] The luminescent layer refers to the layer that emits light in the visible light region by combining holes and electrons received from the anode and cathode. Typically, the luminescent layer consists of a host material and dopant materials.

[0257] As the main material, the above-described composition or the first and second compounds can be used simultaneously. Furthermore, the main material may also include fused aromatic ring derivatives or heterocyclic compounds. Specific examples of fused aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentane derivatives, phenanthrene compounds, and fluoranthene compounds. Examples of heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, and pyrimidine derivatives, but are not limited to these.

[0258] Examples of dopant materials include aromatic amine derivatives, styrylamine 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. Diindrone pyrene, etc. Styrenicoamine compounds are compounds in which at least one aryl vinyl group is substituted in a substituted or unsubstituted aryl amine, wherein one or two or more substituents selected from aryl, silyl, alkyl, cycloalkyl, and arylamino groups are substituted or unsubstituted. Specific examples include, but are not limited to, styrenicoamines, styrenicodiamines, styrenicotriamines, styrenicotetraamines, etc. Furthermore, metal complexes include, but are not limited to, iridium complexes, platinum complexes, etc.

[0259] More specifically, compounds such as, but not limited to, can be used as dopant materials:

[0260]

[0261]

[0262]

[0263] Cavity barrier

[0264] Organic light-emitting devices according to this disclosure may optionally include a hole-blocking layer between the light-emitting layer and the electron injection and transport layer, or the electron transport layer, or the electron injection layer described below.

[0265] A hole-blocking layer is a layer formed on a light-emitting layer and preferably positioned in contact with it, thus serving to control electron mobility to prevent excessive hole movement and increase the likelihood of hole-electron binding, thereby improving the efficiency of organic light-emitting devices. The hole-blocking layer comprises a hole-blocking material, and as an example of such a material, a compound incorporating electron-withdrawing groups, such as azazine derivatives including triazines and triazole derivatives, can be used. Diazole derivatives; phenanthrene-rholine derivatives; phosphine oxide derivatives, but not limited to these.

[0266] Electron injection and transport layer, electron transport layer, electron injection layer

[0267] The organic light-emitting device according to this disclosure may optionally include an electron injection and transport layer, or an electron transport layer, or an electron injection layer between the light-emitting layer or hole-blocking layer and the cathode. The electron injection and transport layer is a layer that simultaneously functions as an electron transport layer and an electron injection layer for injecting electrons from the electrode and transporting the received electrons to the light-emitting layer, and is formed on the light-emitting layer or hole-blocking layer. The electron injection and transport material is suitably a material that can effectively receive electrons from the cathode and transfer electrons to the light-emitting layer, and has a high electron mobility. 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; hydroxyflavonoid-metal complexes, triazine derivatives, etc. Alternatively, it may be combined with fluorenone, anthraquinone dimethyl ether, biphenylquinone, thiamethoxam dioxide, etc. azole, Diazoles, triazoles, imidazoles, perylenetetracarboxylic acid, fluorenemethane, anthrones, and their derivatives, metal complexes, nitrogen-containing 5-membered ring derivatives, etc., may be used together, but are not limited to these.

[0268] The electron injection and transport layers can 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 hole-blocking layer, and the aforementioned electron injection and transport materials can be used as the electron transport material contained in the electron transport layer. Furthermore, examples of electron injection materials formed on the electron transport layer and contained in the electron injection layer include LiF, NaCl, CsF, Li₂O, BaO, fluorenone, anthraquinone dimethane, biphenylquinone, thiamethoxam dioxide, etc. azole, diazole, thiamethoxam dioxide, azole, Diazoles, triazoles, imidazoles, perylenetetracarboxylic acid, fluorenemethane, anthrones, and their derivatives, metal complexes, nitrogen-containing 5-membered ring derivatives, etc.

[0269] Metal complex compounds include 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, bis(2-methyl-8-quinoline)(2-naphthol)gallium, etc., but are not limited to these.

[0270] Organic light-emitting devices according to this disclosure can exhibit superior efficiency, driving voltage, and / or lifetime characteristics by including a first compound and a second compound having a specific structure, or a composition containing them, in an organic material layer.

[0271] Preferred embodiments are presented below to aid in understanding this disclosure. However, these embodiments are provided merely for the purpose of facilitating understanding of this disclosure, and the content of this disclosure is not limited thereto.

[0272] Preparation Example 1-1. Preparation of Compound 1-1

[0273]

[0274] Under a nitrogen atmosphere, 5-([1,1'-biphenyl]-4-yl)-5,8-dihydroindolo[2,3-c]carbazole (10 g, 24.5 mmol) and 4-bromo-1,1'-biphenyl (5.7 g, 24.5 mmol) were added to 200 mL of xylene, stirred, and refluxed. Sodium tert-butoxide (7.1 g, 73.4 mmol) was added to the resulting mixture and stirred thoroughly, followed by bis(tri-tert-butylphosphine)palladium (0.4 g, 0.7 mmol). After reacting for 3 hours, the mixture was cooled to room temperature (23 °C ± 5 °C), and the resulting solid was filtered. The filtered solid was added to 412 mL of chloroform and dissolved. After washing the resulting solution twice with water, the organic layer was separated. Anhydrous magnesium sulfate was added to the separated organic layer and stirred, followed by filtration. The filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to obtain a white solid compound 1-1 (8.6 g, 63%, MS: [M+H]+=561.7).

[0275] Preparation Example 1-2. Preparation of Compound 1-2

[0276]

[0277] White solid compound 1-2 was prepared by the same method as in Preparation Example 1-1, except that 3-bromo-1,1'-biphenyl was used instead of 4-bromo-1,1'-biphenyl (6.6 g, 48%, MS: [M+H]+=561.7).

[0278] Preparation Examples 1-3. Preparation of Compounds 1-3

[0279]

[0280] White solid compounds 1-3 were prepared by the same method as in Preparation Example 1-1, except that 5-([1,1'-biphenyl]-3-yl)-5,8-dihydroindolo[2,3-c]carbazole was used instead of 5-([1,1'-biphenyl]-4-yl)-5,8-dihydroindolo[2,3-c]carbazole, and 3-bromo-1,1'-biphenyl was used instead of 4-bromo-1,1'-biphenyl (7.5 g, 55%, MS: [M+H]+=561.7).

[0281] Preparation Examples 1-4. Preparation of Compounds 1-4

[0282]

[0283] White solid compounds 1-4 were prepared by the same method as in Preparation Example 1-1, except that 1-bromodibenzo[b,d]furan was used instead of 4-bromo-1,1'-biphenyl (8.6 g, 61%, MS: [M+H]+=575.7).

[0284] Preparation Examples 1-5. Preparation of Compounds 1-5

[0285]

[0286] White solid compounds 1-5 were prepared by the same method as in Preparation Example 1-1, except that 5-([1,1'-biphenyl]-3-yl)-5,8-dihydroindolo[2,3-c]carbazole was used instead of 5-([1,1'-biphenyl]-4-yl)-5,8-dihydroindolo[2,3-c]carbazole, and 2-bromodibenzo[b,d]furan was used instead of 4-bromo-1,1'-biphenyl (5.8 g, 41%, MS: [M+H]+=575.7).

[0287] Preparation Examples 1-6. Preparation of Compounds 1-6

[0288]

[0289] White solid compounds 1-6 were prepared by the same method as in Preparation Example 1-1, except that 2-bromotriene was used instead of 4-bromo-1,1'-biphenyl (11 g, 71%, MS: [M+H]+ = 635.8).

[0290] Preparation Examples 1-7. Preparation of Compounds 1-7

[0291]

[0292] White solid compounds 1-7 were prepared by the same method as in Preparation Example 1-1, except that 2-bromo-1,1':3',1”-terphenyl was used instead of 4-bromo-1,1'-biphenyl (8.3 g, 53%, MS: [M+H]+=637.8).

[0293] Preparation Examples 1-8. Preparation of Compounds 1-8

[0294]

[0295] Under a nitrogen atmosphere, compound 1-1 (10 g, 17.8 mmol) and TfOH (2 ml) were added to C6D6 (100 ml) and stirred at 40 °C for 4 hours. After the reaction was complete, the temperature of the resulting product was lowered to room temperature, D2O (20 ml) was added and stirred for 30 minutes, followed by the dropwise addition of trimethylamine (2.4 ml). The resulting reaction solution was transferred to a separatory funnel, extracted with water and chloroform, and then anhydrous magnesium sulfate was added and stirred. The resulting reaction product was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to obtain a white solid compound 1-8 (7.9 g, 76%, MS: [M+H]+=587).

[0296] Preparation Examples 1-9. Preparation of Compounds 1-9

[0297]

[0298] White solid compounds 1-9 were prepared by the same method as in Preparation Examples 1-8, except that compound 1-2 was used instead of compound 1-1 (7.4 g, 71%, MS: [M+H]+=587).

[0299] Preparation Examples 1-10. Preparation of Compounds 1-10

[0300]

[0301] White solid compounds 1-10 were prepared by the same method as in Preparation Examples 1-8, except that compound 1-3 was used instead of compound 1-1 (7.2 g, 69%, MS: [M+H]+=587).

[0302] Preparation Example 1-11. Preparation of Compound 1-11

[0303]

[0304] Under a nitrogen atmosphere, 5,8-dihydroindolo[2,3-c]carbazole-1,2,3,4,6,7,9,10,11,12-d10 (10 g, 37.8 mmol) and 4-bromo-1,1'-biphenyl (17.6 g, 75.6 mmol) were added to 200 mL of xylene, stirred, and refluxed. Sodium tert-butoxide (21.8 g, 227.0 mmol) was added to the resulting product. After thorough stirring, bis(tri-tert-butylphosphine)palladium (2 g, 3.8 mmol) was added. After reacting for 3 hours, the resulting product was cooled to room temperature, and the resulting solid was filtered. The obtained solid was added to 645 mL of chloroform and dissolved. After washing the resulting solution twice with water, the organic layer was separated. Anhydrous magnesium sulfate was added to the separated organic layer, stirred, and then filtered. The filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to obtain a white solid compound 1-11 (17.2 g, 80%, MS: [M+H]+ = 569.8).

[0305] Synthesis Example 1. Preparation of Compound A1

[0306]

[0307] Step 1) Preparation of compound A1-1

[0308] Under a nitrogen atmosphere, (5-chloro-2-fluorophenyl)boronic acid (40 g, 229.4 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (61.4 g, 229.4 mmol) were added to 400 mL of tetrahydrofuran, stirred, and refluxed. Potassium carbonate (95.1 g, 688.2 mmol) was dissolved in 95 mL of water and added to the resulting mixture. After thorough stirring, [1,1'-bis(diphenylphosphine)ferrocene]dichloropalladium(II) (3.4 g, 4.6 mmol) was added, and the reaction was carried out for 11 hours. After the reaction was complete, the resulting product was cooled to room temperature to separate the organic and aqueous layers, and the organic layer was distilled. The obtained product was added to 830 mL of toluene and dissolved. After washing the resulting solution twice with water, the organic layer was separated. Anhydrous magnesium sulfate was added to the separated organic layer and stirred, then filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography using toluene and ethyl acetate to obtain a gray solid compound A1-1 (58.9 g, 71%, MS: [M+H]+ = 362.8).

[0309] Step 2) Preparation of compound A1

[0310] Under a nitrogen atmosphere, compound A1-1 (50 g, 138.2 mmol) prepared in step 1 and bis(pinacol)diboron (38.7 g, 165.8 mmol) were added to 750 mL of Diox, stirred, and refluxed. Potassium acetate (39.9 g, 414.6 mmol) was added to the resulting mixture. After thorough stirring, palladium dibenzylacetone palladium (2.4 g, 4.1 mmol) and tricyclohexylphosphine (2.3 g, 8.3 mmol) were added. After reacting for 5 hours, the resulting product was cooled to room temperature to separate the organic layer. The separated organic layer was filtered to remove salts, and then the filtered organic layer was distilled. The obtained product was added to 626 mL of chloroform and dissolved. After washing the resulting solution twice with water, the organic layer was separated. Anhydrous magnesium sulfate was added to the separated organic layer and stirred, and then filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography using chloroform and ethyl acetate to prepare a yellow solid compound A1 (53.3 g, 85%, MS: [M+H]+ = 454.3).

[0311] Synthesis Example 2. Preparation of Compound B1

[0312]

[0313] Compound B1 was prepared by the same method as in Synthesis Example 1, except that 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine (35.3 g, 73%, MS: [M+H]+=530.4).

[0314] Synthesis Example 3. Preparation of Compound C1

[0315]

[0316] Compound C1 was prepared by the same method as in Synthesis Example 1, except that 2-chloro-4,6-bis(phenyl-2,3,4,5-d4)-1,3,5-triazine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine (30.5 g, 70%, MS: [M+H]+=461.2).

[0317] Synthesis Example 4. Preparation of Compound D1

[0318]

[0319] Compound D1 was prepared by the same method as in Synthesis Example 1, except that 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine (35.8 g, 77%, MS: [M+H]+=529).

[0320] Preparation Example 2-1. Preparation of Compound 2-1

[0321]

[0322] Step 1) Preparation of compound Sub 1

[0323] Under a nitrogen atmosphere, compound A1 (36 g, 79.4 mmol) and 3-bromo-1,1'-biphenyl (18.5 g, 79.4 mmol) were placed in 720 mL of tetrahydrofuran, stirred, and refluxed. Potassium carbonate (32.9 g, 238.2 mmol) was dissolved in 33 mL of water and added to the resulting mixture. After thorough stirring, bis(tri-tert-butylphosphine)palladium (0.8 g, 1.6 mmol) was added, and the reaction was carried out for 3 hours. After the reaction was complete, the product was cooled to room temperature, and the resulting solid was filtered. The obtained solid was added to 1904 mL of chloroform and dissolved. After washing the resulting solution twice with water, the organic layer was separated. Anhydrous magnesium sulfate was added to the separated organic layer, stirred, and then filtered. The filtrate was distilled under reduced pressure. The resulting concentrated compound was purified by silica gel column chromatography using chloroform and ethyl acetate to obtain a gray solid, compound Sub 1 (28.9 g, 76%, MS: [M+H]+ = 480.6).

[0324] Step 2) Preparation of compound 2-1

[0325] Under a nitrogen atmosphere, compound Sub 1 (40 g, 83.4 mmol) prepared in step 1 and 9H-carbazole-1,3,4,5,6,8-d6 (14.5 g, 83.4 mmol) were added to 320 mL of dimethylacetamide, stirred, and refluxed. Potassium phosphate (53.1 g, 250.2 mmol) was added to the resulting mixture, and the mixture was stirred thoroughly and reacted for 1 hour. After the reaction was complete, the resulting product was cooled to room temperature and the organic layer was separated. The separated organic layer was filtered to remove salts, and then the filtered organic layer was distilled. The obtained product was added to 1583 mL of chloroform and dissolved. After washing the resulting solution twice with water, the organic layer was separated. Anhydrous magnesium sulfate was added to the separated organic layer and stirred, and then filtered. The filtrate was distilled under reduced pressure. The resulting concentrated compound was purified by silica gel column chromatography using chloroform and ethyl acetate to obtain a yellow solid compound 2-1 (30.1 g, 57%, MS: [M+H]+ = 633.8).

[0326] Preparation Example 2-2. Preparation of Compound 2-2

[0327]

[0328] Step 1) Preparation of compound Sub 2

[0329] Under a nitrogen atmosphere, compound A1 (36 g, 79.4 mmol) and 4-iodo-1,1'-biphenyl (22.2 g, 79.4 mmol) were placed in 720 mL of tetrahydrofuran, stirred, and refluxed. Potassium carbonate (32.9 g, 238.2 mmol) was dissolved in 33 mL of water and added to the resulting mixture. After thorough stirring, bis(tri-tert-butylphosphine)palladium (0.8 g, 1.6 mmol) was added, and the reaction was carried out for 4 hours. After the reaction was complete, the product was cooled to room temperature, and the resulting solid was filtered. The obtained solid was added to 1904 mL of chloroform and dissolved. After washing the resulting solution twice with water, the organic layer was separated. Anhydrous magnesium sulfate was added to the separated organic layer, stirred, and then filtered. The filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to obtain a red solid, compound Sub 2 (34.7 g, 91%, MS: [M+H]+ = 480.6).

[0330] Step 2) Preparation of compound 2-2

[0331] Under a nitrogen atmosphere, compound Sub 2 (40 g, 83.4 mmol) prepared in step 1 and 9H-carbazole-1,3,4,5,6,8-d6 (14.5 g, 83.4 mmol) were added to 320 mL of dimethylacetamide, stirred, and refluxed. Potassium phosphate (53.1 g, 250.2 mmol) was added to the resulting mixture, and the mixture was stirred thoroughly and reacted for 1 hour. After the reaction was complete, the resulting product was cooled to room temperature, and the organic layer was separated. The separated organic layer was filtered to remove salts, and then the filtered organic layer was distilled. The obtained product was added to 1583 mL of chloroform and dissolved. After washing the resulting solution twice with water, the organic layer was separated. Anhydrous magnesium sulfate was added to the separated organic layer and stirred, and then filtered. The filtrate was distilled under reduced pressure. The resulting concentrated compound was purified by silica gel column chromatography using chloroform and ethyl acetate to obtain a yellow solid compound 2-2 (41.7 g, 79%, MS: [M+H]+ = 633.8).

[0332] Preparation Example 2-3. Preparation of Compound 2-3

[0333]

[0334] Step 1) Preparation of compound Sub 3

[0335] Under a nitrogen atmosphere, compound A1 (36 g, 79.4 mmol) and 5'-bromo-1,1':3',1”-terphenyl (24.6 g, 79.4 mmol) were placed in 720 mL of tetrahydrofuran, stirred, and refluxed. Potassium carbonate (32.9 g, 238.2 mmol) was dissolved in 33 mL of water and added to the resulting mixture. After thorough stirring, bis(tri-tert-butylphosphine)palladium (0.8 g, 1.6 mmol) was added, and the reaction was carried out for 3 hours. After the reaction was complete, the product was cooled to room temperature, and the resulting solid was filtered. The obtained solid was added to 2206 mL of chloroform and dissolved. After washing the resulting solution twice with water, the organic layer was separated. Anhydrous magnesium sulfate was added to the separated organic layer, stirred, and then filtered. The filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to obtain a gray solid, compound Sub. 3 (27.4 g, 62%, MS: [M+H]+=556.7).

[0336] Step 2) Preparation of compounds 2-3

[0337] Under a nitrogen atmosphere, compound Sub 3 (40 g, 72 mmol) prepared in step 1 and 9H-carbazole-1,3,4,5,6,8-d6 (12.5 g, 72 mmol) were added to 320 mL of dimethylacetamide, stirred, and refluxed. Potassium phosphate (45.8 g, 216 mmol) was added to the resulting mixture, and the mixture was stirred thoroughly and reacted for 2 hours. After the reaction was complete, the resulting product was cooled to room temperature, and the organic layer was separated. The separated organic layer was filtered to remove salts, and then the filtered organic layer was distilled. The obtained product was added to 1531 mL of chloroform and dissolved. After washing the resulting solution twice with water, the organic layer was separated. Anhydrous magnesium sulfate was added to the separated organic layer, stirred, and then filtered. The filtrate was distilled under reduced pressure. The resulting concentrated compound was purified by silica gel column chromatography using chloroform and ethyl acetate to obtain a yellow solid compound 2-3 (40.8 g, 80%, MS: [M+H]+ = 709.9).

[0338] Preparation Example 4. Preparation of Compounds 2-4

[0339]

[0340] Step 1) Preparation of compound Sub 4

[0341] Under a nitrogen atmosphere, compound A1 (30 g, 66.2 mmol) and bromobenzene (10.4 g, 66.2 mmol) were placed in 300 mL of tetrahydrofuran, stirred, and refluxed. Potassium carbonate (27.4 g, 198.5 mmol) was dissolved in 27 mL of water and added to the resulting mixture. After thorough stirring, bis(tri-tert-butylphosphine)palladium (0.7 g, 1.3 mmol) was added, and the reaction was carried out for 3 hours. After the reaction was complete, the product was cooled to room temperature, and the resulting solid was filtered. The obtained solid was added to 1335 mL of chloroform and dissolved. After washing the resulting solution twice with water, the organic layer was separated. Anhydrous magnesium sulfate was added to the separated organic layer, stirred, and then filtered. The filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to obtain a gray solid, compound Sub 4 (19.5 g, 73%, MS: [M+H]+ = 404.5).

[0342] Step 2) Preparation of compounds 2-4

[0343] Under a nitrogen atmosphere, compound Sub 4 (30 g, 74.4 mmol) prepared in step 1 and 3-(phenyl-2,4,6-d3)-9H-carbazole-1,2,4,5,6,8-d6 (18.8 g, 74.4 mmol) were added to 240 mL of dimethylacetamide, stirred, and refluxed. Potassium phosphate (47.4 g, 223.1 mmol) was added to the resulting mixture, and after thorough stirring, the mixture was allowed to react for 1 hour. After the reaction was complete, the resulting product was cooled to room temperature, and the organic layer was separated. The separated organic layer was filtered to remove salts, and then the filtered organic layer was distilled. The obtained product was added to 1418 mL of chloroform and dissolved. After washing the resulting solution twice with water, the organic layer was separated. Anhydrous magnesium sulfate was added to the separated organic layer, stirred, and then filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography using chloroform and ethyl acetate to obtain a yellow solid compound 2-4 (32.1 g, 68%, MS: [M+H]+ = 636.8).

[0344] Preparation Example 2-5. Preparation of Compound 2-5

[0345]

[0346] Step 1) Preparation of compound Sub 5

[0347] Under a nitrogen atmosphere, compound B1 (30 g, 56.7 mmol) and bromobenzene (8.9 g, 56.7 mmol) were placed in 450 mL of tetrahydrofuran, stirred, and refluxed. Potassium carbonate (23.5 g, 170 mmol) was dissolved in 23 mL of water and added to the resulting mixture. After thorough stirring, [1,1'-bis(diphenylphosphine)ferrocene]dichloropalladium(II) (0.8 g, 1.1 mmol) was added, and the reaction was carried out for 12 hours. After the reaction was complete, the resulting product was cooled to room temperature to separate an organic layer and an aqueous layer. The organic layer was distilled. The obtained product was added to 272 mL of toluene and dissolved. After washing the resulting solution twice with water, the organic layer was separated. Anhydrous magnesium sulfate was added to the separated organic layer, and the mixture was stirred and filtered. The filtrate was distilled under reduced pressure. The resulting concentrated compound was purified by silica gel column chromatography using toluene and ethyl acetate to obtain a gray solid compound Sub 5 (16.6 g, 61%, MS: [M+H]+ = 480.6).

[0348] Step 2) Preparation of compounds 2-5

[0349] Under a nitrogen atmosphere, compound Sub 5 (30 g, 62.6 mmol) prepared in step 1 and 9H-carbazole-d8 (11 g, 62.6 mmol) were added to 240 mL of dimethylacetamide, stirred, and refluxed. Potassium phosphate (39.8 g, 187.7 mmol) was added to the resulting mixture, and the mixture was stirred thoroughly and reacted for 1 hour. After the reaction was complete, the resulting product was cooled to room temperature and the organic layer was separated. The separated organic layer was filtered to remove salts, and then the filtered organic layer was distilled. The obtained product was added to 1191 mL of chloroform and dissolved. After washing the resulting solution twice with water, the organic layer was separated. Anhydrous magnesium sulfate was added to the separated organic layer, and the mixture was stirred and filtered. The filtrate was distilled under reduced pressure. The resulting concentrated compound was purified by silica gel column chromatography using chloroform and ethyl acetate to obtain a yellow solid compound 2-5 (20.7 g, 52%, MS: [M+H]+ = 635.8).

[0350] Preparation Example 2-6. Preparation of Compound 2-6

[0351]

[0352] Compound 2-6 was prepared by the same method as in Preparation Example 2-2, except that 9H-carbazole-d8 was used instead of 9H-carbazole-1,3,4,5,6,8-d6 (21.5 g, 70%, MS: [M+H]+=634).

[0353] Preparation Example 2-7. Preparation of Compound 2-7

[0354]

[0355] Step 1) Preparation of compound G1

[0356] Compound G1 was prepared by the same method as in Synthesis Example 1, except that 2-chloro-4,6-bis(phenyl-2,3,4,5-d4)-1,3,5-triazine was used instead of 2-chloro-4,6-diphenyl-1,3,5-triazine (30.5 g, 70%, MS: [M+H]+=461.2).

[0357] Step 2) Preparation of compound Sub 6

[0358] Under a nitrogen atmosphere, compound G1 (35 g, 75.9 mmol) prepared in step 1 and 4-iodo-1,1'-biphenyl (21.2 g, 75.9 mmol) were placed in 350 mL of tetrahydrofuran, stirred, and refluxed. Potassium carbonate (31.5 g, 227.6 mmol) was dissolved in 31 mL of water and added to the resulting mixture. After thorough stirring, bis(tri-tert-butylphosphine)palladium (0.8 g, 1.5 mmol) was added, and the reaction was carried out for 5 hours. After the reaction was complete, the resulting product was cooled to room temperature, and the solid was filtered. The obtained solid was added to 1850 mL of chloroform and dissolved. After washing the resulting solution twice with water, the organic layer was separated. Anhydrous magnesium sulfate was added to the separated organic layer, and the mixture was stirred and filtered. The filtrate was distilled under reduced pressure. The resulting concentrated compound was purified by silica gel column chromatography using chloroform and ethyl acetate to obtain a gray solid compound Sub 6 (27 g, 73%, MS: [M+H]+ = 488).

[0359] Step 3) Preparation of compounds 2-7

[0360] Under a nitrogen atmosphere, compound Sub 6 (25 g, 51.3 mmol) prepared in step 2 and 9H-carbazole-1,2,3,4,5,6,8-d7 (8.9 g, 51.3 mmol) were added to 200 mL of dimethylacetamide, stirred, and refluxed. Potassium phosphate (32.6 g, 153.8 mmol) was added to the resulting mixture, and the mixture was stirred thoroughly and reacted for 1 hour. After the reaction was complete, the resulting product was cooled to room temperature and the organic layer was separated. The separated organic layer was filtered to remove salts, and then the filtered organic layer was distilled. The obtained product was added to 987 mL of chloroform and dissolved. After washing the resulting solution twice with water, the organic layer was separated. Anhydrous magnesium sulfate was added to the separated organic layer, and the mixture was stirred and filtered. The filtrate was distilled under reduced pressure. The resulting concentrated compound was purified by silica gel column chromatography using chloroform and ethyl acetate to obtain a yellow solid compound 2-7 (17.4 g, 53%, MS: [M+H]+ = 642).

[0361] Preparation Example 2-8. Preparation of Compound 2-8

[0362]

[0363] Step 1) Preparation of compound Sub 7

[0364] Under a nitrogen atmosphere, compound G1 (35 g, 75.9 mmol) and 3-bromo-1,1'-biphenyl (17.7 g, 75.9 mmol) were placed in 350 mL of tetrahydrofuran, stirred, and refluxed. Potassium carbonate (31.5 g, 227.6 mmol) was dissolved in 31 mL of water and added to the resulting mixture. After thorough stirring, bis(tri-tert-butylphosphine)palladium (0.8 g, 1.5 mmol) was added, and the reaction was carried out for 4 hours. After the reaction was complete, the product was cooled to room temperature, and the resulting solid was filtered. The obtained solid was added to 1850 mL of chloroform and dissolved. After washing the resulting solution twice with water, the organic layer was separated. Anhydrous magnesium sulfate was added to the separated organic layer, and the mixture was stirred and filtered. The filtrate was distilled under reduced pressure. The resulting concentrated compound was purified by silica gel column chromatography using chloroform and ethyl acetate to obtain a gray solid, compound Sub 7 (29.2 g, 79%, MS: [M+H]+ = 488.6).

[0365] Step 2) Preparation of compounds 2-8

[0366] Under a nitrogen atmosphere, compound Sub 7 (25 g, 51.3 mmol) prepared in step 1 and 4-(phenyl-d5)-9H-carbazole-1,5,6,8-d4 (12.9 g, 51.3 mmol) were added to 200 mL of dimethylacetamide, stirred, and refluxed. Potassium phosphate (32.6 g, 153.8 mmol) was added to the resulting mixture, and the mixture was stirred thoroughly and reacted for 2 hours. After the reaction was complete, the resulting product was cooled to room temperature and the organic layer was separated. The separated organic layer was filtered to remove salts, and the filtered organic layer was distilled. The obtained product was added to 1093 mL of chloroform and dissolved. After washing the resulting solution twice with water, the organic layer was separated. Anhydrous magnesium sulfate was added to the separated organic layer, and the mixture was stirred and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography using chloroform and ethyl acetate to obtain a yellow solid compound 2-8 (23.7 g, 65%, MS: [M+H]+ = 720).

[0367] Preparation Example 2-9. Preparation of Compound 2-9

[0368]

[0369] Step 1) Preparation of compound Sub 8

[0370] Under a nitrogen atmosphere, compound D1 (35 g, 66.1 mmol) and bromobenzene (10.4 g, 66.1 mmol) were placed in 350 mL of tetrahydrofuran, stirred, and refluxed. Potassium carbonate (27.4 g, 198.3 mmol) was dissolved in 27 mL of water and added to the resulting mixture. After thorough stirring, bis(tri-tert-butylphosphine)palladium (0.7 g, 1.3 mmol) was added, and the reaction was carried out for 3 hours. After the reaction was complete, the product was cooled to room temperature, and the resulting solid was filtered. The obtained solid was added to 1585 mL of chloroform and dissolved. After washing the resulting solution twice with water, the organic layer was separated. Anhydrous magnesium sulfate was added to the separated organic layer, stirred, and then filtered. The filtrate was distilled under reduced pressure. The resulting concentrated compound was purified by silica gel column chromatography using chloroform and ethyl acetate to obtain a gray solid, compound Sub 8 (25.4 g, 80%, MS: [M+H]+ = 480.6).

[0371] Step 2) Preparation of compounds 2-9

[0372] Under a nitrogen atmosphere, compound Sub 8 (25 g, 52.1 mmol) prepared in step 1 and 4-(phenyl-d5)-9H-carbazole-2,5,6,8-d4 (13.2 g, 52.1 mmol) were added to 200 mL of dimethylacetamide, stirred, and refluxed. Potassium phosphate (33.2 g, 156.4 mmol) was added to the resulting mixture, which was stirred thoroughly and reacted for 3 hours. After the reaction was complete, the resulting product was cooled to room temperature, and the organic layer was separated. The separated organic layer was filtered to remove salts, and then the filtered organic layer was distilled. The obtained product was added to 1099 mL of chloroform and dissolved. After washing the resulting solution twice with water, the organic layer was separated. Anhydrous magnesium sulfate was added to the separated organic layer, which was then stirred and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography using chloroform and ethyl acetate to obtain a yellow solid compound 2-9 (23.1 g, 63%, MS: [M+H]+ = 712).

[0373] Preparation Example 2-10: Preparation of Compound 2-10

[0374]

[0375] Step 1) Preparation of compound H1-1

[0376] Under a nitrogen atmosphere, (3-chloro-2-fluorophenyl)boronic acid (40 g, 229.4 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (61.4 g, 229.4 mmol) were added to 400 mL of tetrahydrofuran, stirred, and refluxed. Potassium carbonate (95.1 g, 688.2 mmol) was then dissolved in 95 mL of water and added to the resulting mixture. After thorough stirring, [1,1'-bis(diphenylphosphine)ferrocene]dichloropalladium(II) (3.4 g, 4.6 mmol) was added. After reacting for 11 hours, the mixture was cooled to room temperature to separate the organic and aqueous layers. The organic layer was distilled. The resulting product was added to 830 mL of toluene and dissolved. After washing the resulting solution twice with water, the organic layer was separated. Anhydrous magnesium sulfate was added to the separated organic layer, and the mixture was stirred and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by passing it through a silica gel column using toluene and ethyl acetate to prepare a gray solid compound H1-1.

[0377] Step 2) Preparation of compound H1

[0378] Under a nitrogen atmosphere, H1-1 (50 g, 138.2 mmol) and bis(pinacol)diboron (38.7 g, 165.8 mmol) were added to 750 mL of Diox, then stirred and refluxed. Potassium acetate (39.9 g, 414.6 mmol) was then added to the resulting mixture. After thorough stirring, palladium dibenzylacetone palladium (2.4 g, 4.1 mmol) and tricyclohexylphosphine (2.3 g, 8.3 mmol) were added. After reacting for 5 hours, the mixture was cooled to room temperature. The organic layer was filtered to remove salts, and then the filtered organic layer was distilled. The resulting product was added to 626 mL of chloroform and dissolved. After washing the resulting solution twice with water, the organic layer was separated. Anhydrous magnesium sulfate was added to the separated organic layer, then stirred and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography using chloroform and ethyl acetate to prepare a yellow solid compound H1 (39 g, 62%, MS: [M+H]+ = 453.3).

[0379] Step 3) Preparation of compound Sub 11

[0380] Under a nitrogen atmosphere, compound H1 (35 g, 77.2 mmol) and 3-bromo-1,1'-biphenyl (18 g, 77.2 mmol) were placed in 350 mL of tetrahydrofuran, stirred, and refluxed. Potassium carbonate (32 g, 231.6 mmol) was then dissolved in 27 mL of water and added to the resulting mixture. After thorough stirring, bis(tri-tert-butylphosphine)palladium (0.8 g, 1.5 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, and the resulting solid was filtered. The solid was added to 1834 mL of chloroform and dissolved. After washing the resulting solution twice with water, the organic layer was separated. Anhydrous magnesium sulfate was added to the separated organic layer, and the mixture was stirred and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography using chloroform and ethyl acetate to prepare the gray solid compound Sub 11 (22.9 g, 62%, MS: [M+H]+ = 481).

[0381] Step 4) Preparation of Compounds 2-10

[0382] Under a nitrogen atmosphere, compound Sub 11 (20 g, 41.7 mmol) and 9H-carbazole-d8 (7.3 g, 41.7 mmol) were added to 200 mL of dimethylacetamide, stirred, and refluxed. Potassium phosphate (26.6 g, 125.1 mmol) was then added to the resulting mixture, and the mixture was stirred thoroughly. After reacting for 2 hours, the product was cooled to room temperature, and the organic layer was separated. The organic layer was filtered to remove salts, and then distilled. The product was added to 1000 mL of chloroform and dissolved. After washing the resulting solution twice with water, the organic layer was separated. Anhydrous magnesium sulfate was added to the separated organic layer, and the mixture was stirred and then filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography using chloroform and ethyl acetate to prepare a yellow solid compound 2-10 (19.1 g, 72%, MS: [M+H]+ = 636).

[0383] Preparation Example 2-11: Preparation of Compound 2-11

[0384]

[0385] Step 1) Preparation of compound Sub 12

[0386] Under a nitrogen atmosphere, compound A1 (36 g, 79.4 mmol) and 2-bromonaphthalene (16.44 g, 79.4 mmol) were placed in 720 mL of tetrahydrofuran, stirred, and refluxed. Potassium carbonate (32.9 g, 238.2 mmol) was dissolved in 33 mL of water and added to the resulting mixture. After thorough stirring, bis(tri-tert-butylphosphine)palladium (0.8 g, 1.6 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, and the resulting solid was filtered. The solid was added to 1904 mL of chloroform and dissolved. After washing the resulting solution twice with water, the organic layer was separated. Anhydrous magnesium sulfate was added, and the mixture was stirred and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography using chloroform and ethyl acetate to prepare the gray solid compound Sub 12 (20 g, 56%, MS: [M+H]+ = 454.5).

[0387] Step 2) Preparation of compound 2-11

[0388] Under a nitrogen atmosphere, compound Sub 12 (20 g, 44.1 mmol) and 9H-carbazole-d8 (7.7 g, 42.7 mmol) were added to 200 mL of dimethylacetamide, stirred, and refluxed. Potassium phosphate (28.1 g, 132.2 mmol) was added to the resulting mixture and stirred thoroughly. After reacting for 2 hours, the product was cooled to room temperature, and the organic layer was separated. The organic layer was filtered to remove salts, and then the filtered organic layer was distilled. The product was added to 1000 mL of chloroform and dissolved. After washing the resulting solution twice with water, the organic layer was separated. Anhydrous magnesium sulfate was added to the separated organic layer, and the mixture was stirred and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography using chloroform and ethyl acetate to prepare a yellow solid compound 2-11 (16.9 g, 63%, MS: [M+H]+ = 610).

[0389] Preparation Example 2-12: Preparation of Compound 2-12

[0390]

[0391] Step 1) Preparation of compound Sub 13

[0392] Compound Sub 13 was prepared by the same method as that used for Compound Sub 12, except that 1-bromoanthracene was used instead of 2-bromonaphthalene (15.3 g, 69%, MS: [M+H]+=505) in step 1 of Preparation Example 2-11.

[0393] Step 2) Preparation of compound 2-12

[0394] Under a nitrogen atmosphere, compound Sub 13 (20 g, 39.7 mmol) and 9H-carbazole-d8 (7 g, 39.7 mmol) were added to 200 mL of dimethylacetamide, stirred, and refluxed. Potassium phosphate (25.3 g, 119.1 mmol) was added to the resulting mixture and stirred thoroughly. After reacting for 2 hours, the product was cooled to room temperature and the organic layer was separated. The organic layer was filtered to remove salts, and then the filtered organic layer was distilled. The product was added to 1000 mL of chloroform and dissolved. After washing the resulting solution twice with water, the organic layer was separated. Anhydrous magnesium sulfate was added to the separated organic layer, and then the mixture was stirred and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography using chloroform and ethyl acetate to prepare a yellow solid compound 2-12 (17.8 g, 68%, MS: [M+H]+ = 660).

[0395] Preparation Example 2-13: Preparation of Compound 2-13

[0396]

[0397] Step 1) Preparation of compound Sub 14

[0398] Compound Sub 14 was prepared by the same method as that used for Compound Sub 12, except that 3-bromophenanthrene was used instead of 2-bromonaphthalene (16.4 g, 74%, MS: [M+H]+=505) in step 1 of Preparation Example 2-11.

[0399] Step 2) Preparation of compound 2-13

[0400] Under a nitrogen atmosphere, compound Sub 14 (20 g, 39.7 mmol) and 9H-carbazole-d8 (7 g, 39.7 mmol) were added to 200 mL of dimethylacetamide, stirred, and refluxed. Potassium phosphate (25.3 g, 119.1 mmol) was added to the resulting mixture and stirred thoroughly. After reacting for 2 hours, the product was cooled to room temperature and the organic layer was separated. The organic layer was filtered to remove salts, and then the filtered organic layer was distilled. The product was added to 1000 mL of chloroform and dissolved. After washing the resulting solution twice with water, the organic layer was separated. Anhydrous magnesium sulfate was added and stirred, and then filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography using chloroform and ethyl acetate to prepare a yellow solid compound 2-13 (20.7 g, 79%, MS: [M+H]+ = 660).

[0401] Preparation Example 2-14: Preparation of Compound 2-14

[0402]

[0403] Step 1) Preparation of compound Sub 15

[0404] Compound Sub 15 was prepared by the same method used for compound Sub 12, except that 2-bromotriene was used instead of 2-bromonaphthalene (17.1 g, 70%, MS: [M+H]+=555) in step 1 of preparation example 2-11.

[0405] Step 2) Preparation of compound 2-14

[0406] Under a nitrogen atmosphere, compound Sub 15 (20 g, 36 mmol) and 9H-carbazole-d8 (6.3 g, 36 mmol) were added to 200 mL of dimethylacetamide, stirred, and refluxed. Potassium phosphate (22.9 g, 108 mmol) was added to the resulting mixture and stirred thoroughly. After reacting for 2 hours, the resulting product was cooled to room temperature, and the organic layer was separated. The separated organic layer was filtered to remove salts, and then the filtered organic layer was distilled. The resulting product was added to 1000 mL of chloroform and dissolved. After washing the resulting solution twice with water, the organic layer was separated. Anhydrous magnesium sulfate was added to the separated organic layer, stirred, and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography using chloroform and ethyl acetate to prepare a yellow solid compound 2-14 (18.6 g, 73%, MS: [M+H]+=710).

[0407] Example 1

[0408] 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 transferred to a plasma cleaner. Additionally, the substrate was cleaned with oxygen plasma for 5 minutes before being transferred to a vacuum deposition unit.

[0409] On the ITO transparent electrode thus prepared, the following compound HI-A is thermally vacuum deposited to a thickness of 60 nm to form a hole injection layer.

[0410] On the hole injection layer, the following compound HAT is vacuum deposited to form a first hole transport layer with a thickness of 5 nm, and the following compound HT-A is vacuum deposited on the first hole transport layer to form a second hole transport layer with a thickness of 50 nm.

[0411] On the second hole transport layer, compound HT-B was thermally vacuum-deposited to a thickness of 45 nm to form an electron blocking layer. On the electron blocking layer, previously prepared compounds 1-1 and 2-1 were mixed in a 1:1 weight ratio, and then the mixture and compound GD were vacuum-deposited in a 90:10 weight ratio to a thickness of 40 nm to form a light-emitting layer. On the light-emitting layer, compound ET-A was vacuum-deposited to a thickness of 5 nm to form a hole blocking layer. On the hole blocking layer, compounds ET-B and LiQ were vacuum-deposited in a 1:1 weight ratio to form an electron injection and transport layer with a thickness of 35 nm.

[0412] In an organic light-emitting device, lithium fluoride (LiF) is deposited to a thickness of 1 nm on an electron injection and transport layer, and then aluminum is deposited to a thickness of 100 nm to form a cathode.

[0413]

[0414] In the above process, the deposition rate of organic materials was maintained between 0.04 nm / s and 0.09 nm / s, the deposition rate of lithium fluoride was maintained at 0.03 nm / s, and the deposition rate of aluminum was maintained at 0.2 nm / s. The vacuum level during deposition was maintained at 1*10 -7 Up to 5*10 -5 Entrust.

[0415] Examples 2 to 37 and Comparative Examples 1 to 10

[0416] Organic light-emitting devices were manufactured in the same manner as in Example 1, except that compounds listed in Table 1 below were used instead of compounds 1-1 or 2-1 in Example 1.

[0417] Meanwhile, the structures of compounds GH1 to GH10 in Table 1 are as follows.

[0418] Experimental Example

[0419] Voltage, efficiency, and lifetime were measured by applying current to the organic light-emitting devices fabricated in the examples and comparative examples, and the results are shown in Tables 1 to 3 below. In this case, a current of 10 mA / cm² was applied. 2 The current density is used to measure voltage and efficiency, and T95 indicates a current density of 20 mA / cm². 2 The time (in hours) required for the brightness to decrease to 95% of the initial brightness at a given current density.

[0420] [Table 1]

[0421]

[0422] [Table 2]

[0423]

[0424] [Table 3]

[0425]

[0426] [Table 4]

[0427]

[0428] As a result of the experiment, compared with the comparative example, the organic light-emitting devices of the embodiments containing the first compound represented by Formula 1 and the second compound represented by Formula 2 of the present disclosure in the light-emitting layer exhibited superior efficiency, driving voltage and lifetime characteristics.

[0429] [Explanation of reference numerals in the attached figures]

[0430] 1: Substrate 2: Anode

[0431] 3: Light-emitting layer 4: Cathode

[0432] 5: Hole injection layer; 6: Hole transport layer

[0433] 7: Electron blocking layer; 8: Hole blocking layer

[0434] 9: Electron Injection and Transport Layer

Claims

1. A composition for use in an organic light-emitting device, comprising a first compound represented by chemical formula 1 and a second compound represented by chemical formula 2: [Chemical Formula 1] In the aforementioned chemical formula 1, Ar1 and Ar2 are each independently substituted or unsubstituted C. 6-60 aryl; or substituted or unsubstituted C containing any or more of N, O, and S. 2-60 Heteroaryl groups, where L1 and L2 are each independently single bonds; or substituted or unsubstituted C... 6-60 Alpha-aryl, R 11 R 12 and R 13 Each is independently deuterium, a and c are independently integers from 0 to 4, b is an integer from 0 to 2, and [Chemical Formula 2] In chemical formula 2, Ar3 and Ar4 are each independently substituted or unsubstituted C. 6-15 Aryl, R a and R d Each is independently hydrogen; deuterium; or substituted or unsubstituted C. 6-60 Aryl, R b For hydrogen or deuterium, R c It is hydrogen; deuterium; or C, either unsubstituted or deuterated. 6-60 Aryl, R 21 To R 28 Each is independently hydrogen; deuterium; or substituted or unsubstituted C. 6-60 aryl, condition R 21 To R 28 At least one of them is deuterium or deuterated C. 6-60 The aryl group, and the second compound being substituted with six or more deuterium groups.

2. The composition for an organic light-emitting device according to claim 1, wherein: Ar1 and Ar2 are each independently phenyl, biphenyl, terphenyl, triphenylene, dibenzofuranyl, dibenzothiophenyl, carbazoyl, or 9-phenylcarbazoyl, and each of Ar1 and Ar2 is independently unsubstituted or substituted with one or more deuterium atoms.

3. The composition for an organic light-emitting device according to claim 1, wherein: One of Ar1 and Ar2 is phenyl, biphenyl, or terphenyl, and the other is phenyl, biphenyl, terphenyl, triphenylene, dibenzofuranyl, dibenzothiophenyl, carbazoyl, or 9-phenylcarbazoyl, and each of Ar1 and Ar2 is independently unsubstituted or substituted with one or more deuterium atoms.

4. The composition for an organic light-emitting device according to claim 1, wherein: L1 and L2 are each independently a single bond or a phenylene group, and the phenylene group is either unsubstituted or substituted with one or more deuterium atoms.

5. The composition for an organic light-emitting device according to claim 1, wherein: a and c are each 4, and b is 2.

6. The composition for an organic light-emitting device according to claim 1, wherein: The first compound is selected from any of the following compounds:

7. The composition for an organic light-emitting device according to claim 1, wherein: One of Ar3 and Ar4 is phenyl, and the other is phenyl or biphenyl, and each of Ar3 and Ar4 is independently unsubstituted or substituted with one or more deuterium atoms.

8. The composition for an organic light-emitting device according to claim 1, wherein: R a and R d Each of the following is independently hydrogen, deuterium, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthryl, or triphenylene, and each of the phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthryl, and triphenylene is independently unsubstituted or substituted with one or more deuterium atoms.

9. The composition for an organic light-emitting device according to claim 1, wherein: R c It is hydrogen, deuterium, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthryl, or triphenylene, and each of the phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthryl, and triphenylene is independently unsubstituted or substituted with one or more deuterium atoms.

10. The composition for an organic light-emitting device according to claim 1, wherein: R 21 To R 28 Each is independently hydrogen, deuterium, unsubstituted phenyl, or phenyl substituted with 1 to 5 deuterium atoms, provided that R 21 To R 28 At least one of them is deuterium, or a phenyl group substituted with 1 to 5 deuterium atoms.

11. The composition for an organic light-emitting device according to claim 1, wherein: The second compound is selected from any of the following compounds:

12. The composition for an organic light-emitting device according to claim 1, wherein: The weight ratio of the first compound to the second compound is 90:10 to 10:

90.

13. The composition for an organic light-emitting device according to claim 1, wherein: The composition is a mixture or an organic alloy.

14. An organic light-emitting device, comprising: anode; The cathode is configured to be opposite the anode; and one or more organic material layers disposed between the anode and the cathode, wherein one or more of the organic material layers comprises the composition for an organic light-emitting device according to claim 1.

15. The organic light-emitting device according to claim 14, wherein: The organic material layer comprising the composition for the organic light-emitting device is a light-emitting layer.

16. An organic light-emitting device, comprising: anode; The cathode is configured to be opposite the anode; and a light-emitting layer disposed between the anode and the cathode; The light-emitting layer comprises a first compound represented by the following chemical formula 1 and a second compound represented by the following chemical formula 2: [Chemical Formula 1] In the aforementioned chemical formula 1, Ar1 and Ar2 are each independently substituted or unsubstituted C. 6-60 aryl; or substituted or unsubstituted C containing any or more of N, O, and S. 2-60 Heteroaryl groups, where L1 and L2 are each independently single bonds; or substituted or unsubstituted C... 6-60 Alpha-aryl, R 11 R 12 and R 13 Each is independently deuterium, a and c are independently integers from 0 to 4, b is an integer from 0 to 2, and [Chemical Formula 2] In chemical formula 2, Ar3 and Ar4 are each independently substituted or unsubstituted C. 6-15 Aryl, R a and R d Each is independently hydrogen; deuterium; or substituted or unsubstituted C. 6-60 Aryl, R b For hydrogen or deuterium, R c It is hydrogen; deuterium; or C, either unsubstituted or deuterated. 6-60 Aryl, R 21 To R 28 Each is independently hydrogen; deuterium; or substituted or unsubstituted C. 6-60 aryl, condition R 21 To R 28 At least one of them is deuterium or deuterated C. 6-60 The aryl group, and the second compound being substituted with six or more deuterium groups.

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