Novel compound and organic light-emitting device comprising same

Abstract

In the present disclosure, a novel compound and an organic light emitting device comprising the same are provided.

Description

Technical Field Cross-references to related applications

[0001] This application is based on and claims priority to Korean Patent Application No. 10-2023-0166618 filed on November 27, 2023 and Korean Patent Application No. 10-2023-0188163 filed on December 21, 2023, the disclosures of which are incorporated herein by reference in their entirety.

[0002] This disclosure relates to novel compounds and organic light-emitting devices incorporating the same. Background Technology

[0003] Organic light emission generally refers to the phenomenon of converting electrical energy into light energy using organic materials. Organic light-emitting devices (OLEDs) utilizing organic light emission have characteristics such as wide viewing angle, excellent contrast, fast response time, and excellent brightness, driving voltage, and response speed, and have therefore been the subject of much research.

[0004] 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.

[0005] There is a continued need to develop new organic materials for use in organic light-emitting devices as described above.

[0006] [Existing Technical Documents]

[0007] [Patent Literature]

[0008] (Patent Document 0001) Korean Unexamined Patent Publication No. 10-2000-0051826 Summary of the Invention Technical issues

[0009] This disclosure relates to providing new compounds and organic light-emitting devices incorporating the same. Technical solution

[0010] In this disclosure, compounds represented by the following chemical formula 1 are provided:

[0011] [Chemical Formula 1]

[0012]

[0013] In chemical formula 1,

[0014] Each X is independently N or CH, provided that at least one X is N;

[0015] L represents unsubstituted or deuterated C. 6-60 Alpha-aryl;

[0016] Ar1 is C with or without substitution. 6-60 Aryl;

[0017] Ar2 is C2 containing, substituted or unsubstituted C2, one or more of O and S. 2-60 Mixed aromatics;

[0018] Each R1 is independently hydrogen, deuterium, substituted or unsubstituted C. 6-60 aryl, or substituted or unsubstituted C containing any or more of N, O, and S. 2-60 heteroaryl; and

[0019] n is an integer from 1 to 8;

[0020] The condition is that at least one of L, Ar1, Ar2 or R1 is deuterium or is deuterated.

[0021] In addition, an organic light-emitting device is provided, the organic light-emitting device comprising: a first electrode; a second electrode opposite to the first electrode; and one or more organic material layers between the first electrode and the second electrode, wherein at least one of the organic material layers comprises a compound of formula 1. Beneficial effects

[0022] Compounds of Formula 1 can be used as materials for organic material layers in organic light-emitting devices, and can significantly improve lifetime characteristics and increase efficiency while maintaining the low driving voltage of organic light-emitting devices. In particular, compounds of Formula 1 can be used as materials for hole injection, hole transport, hole injection and transport, electron blocking, light emission, hole blocking, electron transport, electron injection, or electron injection and transport. Attached Figure Description

[0023] Figure 1 An example of an organic light-emitting device is shown, comprising a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4.

[0024] Figure 2An example of an organic light-emitting device is shown, comprising a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, 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

[0025] In the following sections, embodiments of the present disclosure will be described in more detail to facilitate understanding of the invention.

[0026] As used in this article, symbols , or "D" refers to the bond that is linked to another substituent, and "D" refers to deuterium.

[0027] As used herein, the terms “substituted or unsubstituted” or “unsubstituted or substituted” mean unsubstituted or substituted with one or more substituents selected from: deuterium; halogen group; nitrile group; nitro group; hydroxyl group; carbonyl group; ester group; imide group; amino group; 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 as a heteroatom, or unsubstituted or substituted with two or more substituents linked together from the substituents exemplified above. For example, “substituents linked together from two or more substituents” can be biphenyl. That is, biphenyl can be aryl, or it can also be interpreted as a substituent linked together from two phenyl groups.

[0028] In this disclosure, the number of carbon atoms in the carbonyl group is not particularly limited, but is preferably 1 to 40. Specifically, the carbonyl group can be a group having the following structural formula, but is not limited thereto:

[0029]

[0030] In this disclosure, for the ester group, the oxygen atom of the ester group may be substituted with a straight-chain, branched, or cyclic alkyl group having 1 to 25 carbon atoms, or with an aryl group having 6 to 25 carbon atoms. Specifically, the ester group may be a group having the following structural formulas, but is not limited thereto:

[0031]

[0032] 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 group having the following structural formula, but is not limited thereto:

[0033]

[0034] In this disclosure, silane specifically includes, but is not limited to, trimethylsilane, triethylsilane, tert-butyldimethylsilane, vinyldimethylsilane, propyldimethylsilane, triphenylsilane, diphenylsilane, phenylsilane, etc.

[0035] In this disclosure, boron group specifically includes, but is not limited to, trimethylboronyl, triethylboronyl, tert-butyldimethylboronyl, triphenylboronyl, phenylboronyl, etc.

[0036] Examples of halogen groups in this disclosure include fluorine, chlorine, bromine, or iodine.

[0037] In this disclosure, the alkyl group can be straight-chain or branched, and its carbon number is not particularly limited, but is preferably from 1 to 40. According to one embodiment, the alkyl group has 1 to 20 carbons. According to another embodiment, the alkyl group has 1 to 10 carbons. According to yet another embodiment, the alkyl group has 1 to 6 carbons. Specific examples of alkyl groups include, but are not limited to, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, etc.

[0038] 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 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, It includes, but is not limited to, styrene, etc.

[0039] In this disclosure, the cycloalkyl group is not particularly limited, but it is preferably composed of 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to yet another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specific examples include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, etc.

[0040] In this disclosure, the aryl group is not particularly limited, but it is preferably composed of 6 to 60 carbon atoms, and can be either a monocyclic aryl or a polycyclic aryl. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to another embodiment, the aryl group has 6 to 20 carbon atoms. Monocyclic aryl groups include, but are not limited to, phenyl, biphenyl, terphenyl, etc. Polycyclic aryl groups include naphthyl, anthraceneyl, phenanthryl, pyrene, etc. base, It includes, but is not limited to, methyl, fluorene, etc.

[0041] In this disclosure, the fluorene group can be substituted, and the two substituents can bond 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.

[0042] In this disclosure, the heterocyclic group is a heterocyclic group containing at least one of N, O, Si, and S as a heteroelement, and its carbon number is not particularly limited, but is preferably 2 to 60. Examples of heterocyclic groups include thiophene, furanyl, pyrrole, imidazolyl, and thiazolyl. azole group, Diazolyl, Triazolyl, Pyridyl, Bipyridyl, Pyrimidinyl, Triazinyl, Acridineyl, Pyridazinyl, Quinolinyl, Quinazolinyl, Quinoxalinyl, Phtharazineyl, Pyridopyrimidinyl, Pyridopyrazinyl, Pyrazenopyrazinyl, Isoquinolinyl, Indoleyl, Carbazoleyl, Benzo[] Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazole, benzothiophene, dibenzothiophene, benzofuranyl, phenanthrolinel, iso Azolyl, thiadiazolyl, phenthiazinyl, dibenzofuranyl, etc., but not limited to these.

[0043] In this disclosure, the aryl group in aralkyl, arylenyl, alkylaryl, and arylamine is the same as the aforementioned examples of aryl. In this disclosure, the alkyl group in aralkyl, alkylaryl, and alkylamine is the same as the aforementioned examples of alkyl. In this disclosure, the heteroaryl group in heteroarylamine can be described using the aforementioned description of heterocyclic groups. In this disclosure, the alkenyl group in arylenyl is the same as the aforementioned examples of alkenyl. In this disclosure, the aforementioned description of aryl can be applied, except that the arylene group is a divalent group. In this disclosure, the aforementioned description of heterocyclic groups can be applied, except that the heteroarylene group is a divalent group. In this disclosure, the aforementioned description of aryl or cycloalkyl can be applied, except that the hydrocarbon ring is not a monovalent group but is formed by combining two substituents. In this disclosure, the aforementioned description of heterocyclic groups can be applied, except that the heterocycle is not a monovalent group but is formed by combining two substituents.

[0044] In this disclosure, "deuterated or deuterated" means that at least one hydrogen atom in a compound, a divalent linker, or a monovalent substituent is replaced by deuterium.

[0045] Furthermore, "unsubstituted or deuterated" or "deuterated or unsubstituted" means from zero to the maximum number of substituted hydrogen atoms, and from 1 to that maximum number of atoms that can be substituted by deuterium. For example, given that a phenekin has up to nine substituted hydrogen atoms, the phrase "unsubstituted or deuterated phenekin" means "an unsubstituted or substituted phenekin with 1 to 9 deuterium atoms".

[0046] Furthermore, the term "deuterated structure" refers to a compound, divalent linking group, or monovalent substituent in which at least one hydrogen atom is substituted by deuterium, encompassing all such possible structures. For example, a deuterated phenyl structure refers to all monovalent substituents in which at least one of the substituted hydrogen atoms in the benzene ring is substituted by deuterium. Specifically, a deuterated phenyl structure can be, but is not limited to, groups having the following structural formulas:

[0047]

[0048] In this disclosure, the deuterium substitution rate of a compound refers to the ratio of the number of deuterium atoms substituted by the compound 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 deuterium atoms substituted by the compound), calculated as a percentage. Therefore, when the deuterium substitution rate of a compound is "K%", it means that K% of the hydrogen atoms that can be substituted by deuterium in the compound are replaced by deuterium.

[0049] 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 spectrometry) and nuclear magnetic resonance spectroscopy. 1Measuring can be done 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 "deuterium substitution rate" or "degree of deuteration" can be obtained by determining the number of deuterium atoms substituted in the compound via MALDI-TOF MS analysis, and then calculating the ratio of the number of substituted deuterium atoms to the total number of hydrogen atoms that can exist in the compound as a percentage.

[0050] [Compound]

[0051] In this disclosure, compounds represented by chemical formula 1 are provided.

[0052] The compound represented by chemical formula 1 has a structure in which a heterocycle containing at least one N and a carbazole ring are bonded to the ortho position of a benzene ring, and an aryl ring and another heterocycle containing at least one of O and S are bonded to a specific position of the above heterocycle, wherein at least one of the substituents other than the benzene ring is deuterium or deuterated.

[0053] Specifically, in chemical formula 1:

[0054] Each X is independently N or CH, provided that at least one X is N;

[0055] L represents unsubstituted or deuterated C. 6-60 Alpha-aryl;

[0056] Ar1 is C with or without substitution. 6-60 Aryl;

[0057] Ar2 is C2 containing, substituted or unsubstituted C2, one or more of O and S. 2-60 Mixed aromatics;

[0058] Each R1 is independently hydrogen, deuterium, substituted or unsubstituted C. 6-60 aryl, or substituted or unsubstituted C containing any or more of N, O, and S. 2-60 heteroaryl; and

[0059] n is an integer from 1 to 8;

[0060] The condition is that at least one of L, Ar1, Ar2 or R1 is deuterium or is deuterated.

[0061] According to one embodiment of this disclosure, the compound of Formula 1 is characterized by a structure in which a heterocycle containing at least one nitrogen atom and a carbazole ring are bonded to the ortho position of a benzene ring to form a core structural group, and a substituted or unsubstituted aryl group is introduced at a specific position of the nitrogen-containing heterocycle contained in the core structural group, and a substituted or unsubstituted heteroaryl group is introduced through an arylene linking group L. By forming this specific structure, steric hindrance is induced and enhanced, resulting in a twisted configuration between the nitrogen-containing heterocycle moiety and the carbazole moiety. In this case, the electron-donating properties of the carbazole substituent improve the overall molecular stability, and the electron distribution becomes separated, thereby conferring additional charge transfer (CT) properties. Therefore, the voltage / efficiency characteristics of organic light-emitting devices can be significantly improved.

[0062] Specifically, in compounds of Formula 1, the presence of a deuterium substitution is further characterized by either the deuterium substitution of the carbazole moiety of the core structural group, or the introduction of a deuterium substituent into an aryl ring and another heterocycle bonded at a specific position to a heterocycle containing at least one nitrogen atom, i.e., into a specific substituted or unsubstituted aryl Ar1 and into a specific substituted or unsubstituted heteroaryl Ar2 linked via an arylene linking group L. By deuterating those substituent moieties, electron distribution and balance can be effectively tuned, thereby significantly improving both device efficiency and lifetime.

[0063] Specifically, in chemical formula 1, L can be C. 6-30 aryl, or C 6-20 aryl, or C 6-12 Alpha-aryl groups, either unsubstituted or deuterated.

[0064] For example, L can be substituted with at least one deuterium, or with two or more deuteriums, or with three or more deuteriums, or with four or more deuteriums.

[0065] More specifically, L can be an unsubstituted or deuterated phenylene, or an unsubstituted or deuterated biphenylene.

[0066] For example, L can be selected from any of the following groups:

[0067]

[0068] In the above formula,

[0069] D stands for deuterium.

[0070] Each n1 is an independent integer from 1 to 4.

[0071] n2 is an integer from 1 to 3, and

[0072] n3 is an integer from 1 to 5.

[0073] In the above formula L, This indicates the connecting portion that bonds to the triazine ring and Ar2 in chemical formula 1.

[0074] Furthermore, in chemical formula 1, Ar1 can be an unsubstituted or substituted C. 6-30 aryl, or unsubstituted or substituted C 6-20 aryl, or unsubstituted or substituted C 6-12 Aryl.

[0075] For example, Ar1 can be substituted with at least one deuterium, or with two or more deuteriums, or with three or more deuteriums, or with five or more deuteriums.

[0076] More specifically, Ar1 can be an unsubstituted or deuterated phenyl, or an unsubstituted or deuterated biphenyl, or an unsubstituted or deuterated terphenyl.

[0077] For example, Ar1 can be selected from any of the following groups:

[0078]

[0079] In the above formula,

[0080] D stands for deuterium.

[0081] Each n4 is an independent integer from 1 to 5.

[0082] Each n5 is an independent integer from 1 to 4, and

[0083] n6 is an integer from 1 to 3.

[0084] In the above formula Ar1, This indicates the linker portion that is bonded to the triazine ring in chemical formula 1.

[0085] Furthermore, in chemical formula 1, Ar2 is a heteroaryl group containing one or more of O and S. Ar2 can be substituted or unsubstituted C. 2-30 heteroaryl, substituted or unsubstituted C 2-20 heteroaryl, or substituted or unsubstituted C 2-12 Mixed aromatic compounds.

[0086] For example, Ar2 can be substituted with at least one deuterium, or with two or more deuteriums, or with three or more deuteriums, or with five or more deuteriums.

[0087] More specifically, Ar2 can be an unsubstituted or deuterated dibenzofuranyl group, or an unsubstituted or deuterated dibenzothiophenyl group.

[0088] For example, Ar2 can be selected from any of the following groups:

[0089]

[0090] In the above formula,

[0091] D stands for deuterium.

[0092] Each n7 is an independent integer from 1 to 3, and

[0093] Each n8 is an independent integer from 1 to 4.

[0094] In the above formula Ar2, This indicates the linker portion that is bonded to the triazine ring or L in chemical formula 1.

[0095] Meanwhile, the compounds of Formula 1 can prevent the decrease in molecular stability that may occur due to electron deficiency by deuterating the carbazole ring in the core structural part where the heterocycle containing at least one N is connected to the carbazole ring via the central benzene ring, and thus can significantly improve the lifetime.

[0096] In chemical formula 1, at least one R1 can be deuterium; or a C1 substituted with deuterium. 6-60 aryl; or containing C selected from any one or more of N, O and S. 2-60 The heteroaryl group is deuterated.

[0097] Specifically, each R1 can be either hydrogen or deuterium.

[0098] More specifically, at least one R1 can be deuterium, or at least two R1s can be deuterium, or at least three R1s can be deuterium, or at least five R1s can be deuterium.

[0099] Meanwhile, in chemical formula 1, at least three of L, Ar1, Ar2 and R1 can be deuterium, or at least one of L, Ar1, Ar2 and R1 can be substituted with three or more deuterium.

[0100] Preferably, at least five of L, Ar1, Ar2 and R1 are deuterium, or at least one of L, Ar1, Ar2 and R1 is substituted with five or more deuterium.

[0101] Furthermore, any hydrogen atom in a compound represented by chemical formula 1 can be replaced by deuterium.

[0102] For example, compounds represented by chemical formula 1 can have one to sixty deuterium atoms.

[0103] Preferably, the compound represented by chemical formula 1 may have one to fifty deuterium atoms.

[0104] More preferably, the compound represented by Formula 1 may be substituted with two or more, or three or more, or four or more, or five or more deuterium, and may be substituted with no more than forty-five, or no more than forty-eight, or no more than thirty-six, or no more than thirty-four, or no more than thirty-two, or no more than thirty, or no more than twenty-eight, or no more than twenty-six, or no more than twenty-four, or no more than twenty-two, or no more than twenty, or no more than eighteen, or no more than sixteen, or no more than fourteen, or no more than twelve, or no more than ten deuterium.

[0105] Representative examples of compounds represented by chemical formula 1 are as follows.

[0106]

[0107]

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[0115]

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[0290]

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[0295] .

[0296] The compound may contain at least one or at least two deuterium atoms.

[0297] When the compound contains deuterium, the deuterium substitution rate of the compound can be from 1% to 100%. More specifically, the deuterium substitution rate can be at least 5%, 10%, 20%, 25%, 30%, 40% or 50%, and at most 100%, 90%, 80% or 70%.

[0298] For example, a compound can contain 2 to 30 deuterium atoms. Specifically, when a compound contains deuterium, it can contain at least 2, 3, 5, 6, 7, 8, 10, 11, 12, 15, or 18 deuterium atoms, and at most 30, 28, 26, 24, 22, or 20 deuterium atoms.

[0299] Furthermore, when used in organic light-emitting devices, the compound represented by chemical formula 1 can be used in conjunction with the compound represented by the following chemical formula 2:

[0300] [Chemical Formula 2]

[0301]

[0302] In chemical formula 2,

[0303] Ar4 and Ar5 are independently substituted or unsubstituted C. 6-60 aryl, or C, substituted or unsubstituted, containing at least one heteroatom selected from N, O, and S. 5-60 Mixed aromatics;

[0304] R2 and R3 are each independently hydrogen, deuterium, halogen, cyano, nitro, amino, substituted or unsubstituted C. 1-60 Alkyl groups, substituted or unsubstituted C 3-60 Cycloalkyl, substituted or unsubstituted C 2-60 Alkenyl, substituted or unsubstituted C 6-60 aryl, or C, substituted or unsubstituted, containing at least one heteroatom selected from N, O, and S. 5-60 heteroaryl; and

[0305] p and q are each independent integers from 0 to 7.

[0306] In particular, using the compound of Formula 2 together with the compound of Formula 1 in organic light-emitting devices is advantageous even in terms of the formation of excitocomplexes, which can further improve the characteristics of lower voltage, higher efficiency and longer lifetime.

[0307] Specifically, in chemical formula 2, Ar4 and Ar5 can each be independently phenyl, biphenyl, terphenyl, naphthyl, dibenzofuranyl, dibenzothiopheneyl or dimethylfluorenyl.

[0308] R2 and R3 can each be either hydrogen or phenyl.

[0309] p and q can each be 0 or 1.

[0310] Representative examples of compounds represented by chemical formula 2 are as follows:

[0311]

[0312]

[0313]

[0314] .

[0315] Furthermore, when the compound of Formula 2 is used together with the compound of Formula 1 in one or more organic material layers of an organic light-emitting device, the weight ratio of the compound of Formula 1 to the compound of Formula 2 can be 20:80 to 50:50, or 35:65 to 45:55, and preferably 40:60.

[0316] Meanwhile, the compound represented by chemical formula 1 can be synthesized by, for example, the preparation method shown in reaction scheme 1 below:

[0317] <Reaction Scheme 1>

[0318]

[0319] In reaction scheme 1, L, Ar1, Ar2, R1 and n are each independently defined as in chemical formula 1, and Q1 and Q are each independently halogens.

[0320] For example, Q1 and Q can each be F, Cl, Br or I; preferably F, Cl or Br; more preferably Cl or Br; and most preferably Cl.

[0321] Reaction scheme 1 covers the Suzuki coupling and amination (Buchwald-Hartwig) reaction, preferably carried out in the presence of a palladium catalyst and a base. The reaction vessel and conditions can be varied as is known in the art. The preparation method can be further illustrated in the synthetic examples described below.

[0322] In reaction scheme 1, the reaction for introducing substituent L into the core structure having carbazole-triazine group and the subsequent reaction for introducing substituent Ar2 can each be carried out in the presence of a base and a palladium catalyst, respectively.

[0323] For example, suitable bases include potassium carbonate (K₂CO₃), sodium bicarbonate (NaHCO₃), cesium carbonate (Cs₂CO₃), sodium acetate (NaOAc), potassium acetate (KOAc), sodium ethoxide (NaOEt), sodium tert-butoxide (NaOtBu), triethylamine (Et₃N), or N,N-diisopropylethylamine (EtN(iPr)₂). Preferably, the base can be potassium carbonate.

[0324] Suitable palladium catalysts include bis(tris(tert-butyl)phosphine)palladium(O) (Pd(t-Bu3P)2), tetra(triphenylphosphine)palladium(O) (Pd(PPh3)4), tris(dibenzylacetone)dipalladium(O), bis(dibenzylacetone)palladium(O) (Pd(dba)2), or palladium(II) acetate (Pd(OAc)2). Preferably, the palladium catalyst can be Pd(PPh3)4.

[0325] Organic light-emitting devices

[0326] Furthermore, this disclosure provides an organic light-emitting device comprising a compound of chemical formula 1. As an example, such an organic light-emitting device is provided, comprising: a first electrode; a second electrode disposed opposite to the first electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein at least one of the organic material layers comprises a compound of chemical formula 1.

[0327] The organic material layer of the organic light-emitting device disclosed herein can have a single-layer structure or a multilayer structure in which two or more organic material layers are stacked. For example, the organic light-emitting device of this disclosure can have a structure that includes a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer as organic material layers. However, the structure of the organic light-emitting device is not limited to this, and it may include a small number of organic layers.

[0328] In addition, the organic material layer may include a hole injection layer, a hole transport layer, or a layer that simultaneously injects and transports holes, and the hole injection layer, hole transport layer, or layer that simultaneously injects and transports holes comprises a compound of formula 1.

[0329] In addition, the organic material layer may include a hole injection layer, a hole transport layer, or a layer that simultaneously injects and transports holes, and the hole injection layer, hole transport layer, or layer that simultaneously injects and transports holes comprises a compound of formula 1.

[0330] The organic material layer may include an electron blocking layer, and the electron blocking layer contains a compound of formula 1.

[0331] The organic material layer may include a light-emitting layer, and the light-emitting layer contains a compound of formula 1.

[0332] In addition, the light-emitting layer may also contain dopant materials.

[0333] Specifically, the light-emitting layer may contain a compound of chemical formula 1 and a dopant material.

[0334] For example, the light-emitting layer may contain a compound of chemical formula 1 and a dopant in a weight ratio of 100:1 to 1:1.

[0335] The light-emitting layer may contain a compound of chemical formula 1 and a dopant in a weight ratio of 100:1 to 2:1.

[0336] In a preferred embodiment, the weight ratio of the compound of Formula 1 to the dopant (i.e., the content of the compound of Formula 1: the content of the dopant) can be 100:1 to 5:1, or 100:1 to 10:1, or 100:1 to 20:1, or 100:1 to 30:1.

[0337] For example, the dopant material can be a metal complex.

[0338] Specifically, the dopant material can be an iridium complex.

[0339] In addition, the organic material layer may include a light-emitting layer, which may contain a dopant material selected from the following:

[0340]

[0341]

[0342]

[0343] .

[0344] The dopant material can be one of the structures described above, but is not limited to them.

[0345] The organic material layer may include a hole-blocking layer, and the hole-blocking layer contains a compound of formula 1.

[0346] Furthermore, the organic material layer may include an electron transport layer or an electron injection layer, or a layer that simultaneously transports and injects electrons. The electron transport layer, electron injection layer, or layer that simultaneously transports and injects electrons comprises a compound of formula 1.

[0347] The organic material layer may include a light-emitting layer and an electron transport layer, and the electron transport layer may contain a compound of chemical formula 1.

[0348] Furthermore, the organic light-emitting device of this disclosure may also include, at least one of the organic material layers, a compound of chemical formula 2 and a compound represented by chemical formula 1. For example, such an organic light-emitting device is provided, comprising: a first electrode; a second electrode disposed opposite to the first electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein at least one of the organic material layers comprises a compound of chemical formula 1 and a compound of chemical formula 2.

[0349] The organic light-emitting device according to this disclosure can be a conventional organic light-emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate. Furthermore, the organic light-emitting device according to this disclosure can be an inverted 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, Figure 1 and Figure 2 The structure of an organic light-emitting device according to one embodiment of the present disclosure is shown in the figure.

[0350] Figure 1 An example of an organic light-emitting device comprising a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4 is shown. In this structure, a compound of formula 1 may be included in the light-emitting layer.

[0351] Figure 2 An example of an organic light-emitting device is shown, comprising a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, 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. In this structure, a compound of Formula 1 may be contained in one or more of the hole injection layer, hole transport layer, light-emitting layer, and electron injection and transport layer. Specifically, a compound of Formula 1 may, for example, be contained as a host material in the light-emitting layer.

[0352] Organic light-emitting devices according to this disclosure can be manufactured using materials and methods known in the art, except that one or more layers of organic material contain a compound of formula 1, either alone or together with a compound of formula 2. Furthermore, when the organic light-emitting device comprises a plurality of organic material layers, the organic material layers can be formed of the same material or different materials.

[0353] For example, an organic light-emitting device according to this disclosure can be fabricated by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. In this case, the organic light-emitting device can be fabricated by depositing a metal, a conductive metal oxide, or an alloy thereof on a substrate using a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation to form an anode; forming an organic material layer on the anode comprising a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, and electron injection and transport layers; and then depositing a material that can be used as a cathode on the organic material layer. Alternatively, an organic light-emitting device can be fabricated by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.

[0354] Furthermore, in the fabrication of organic light-emitting devices, compounds of Formula 1 can be formed into organic material layers using solution coating and vacuum deposition methods. In particular, compounds of Formula 1 exhibit excellent solubility in solvents used for solution coating, thus facilitating its application. In this document, solution coating refers to, but is not limited to, spin coating, dip coating, blade coating, inkjet printing, screen printing, spraying, and roll coating.

[0355] Therefore, this disclosure provides a coating composition comprising a compound of chemical formula 1 and a solvent.

[0356] The solvent is not particularly limited, as long as it is capable of dissolving or dispersing the compounds according to this disclosure. Examples may include: chlorine-based solvents, such as chloroform, dichloromethane, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, and o-dichlorobenzene; ether-based solvents, such as tetrahydrofuran and dichlorobenzene. Alkanes; solvents based on aromatic hydrocarbons, such as toluene, xylene, trimethylbenzene, and mesitylene; solvents based on aliphatic hydrocarbons, such as cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, and n-decane; solvents based on ketones, such as acetone, methyl ethyl ketone, and cyclohexanone; solvents based on esters, such as ethyl acetate, butyl acetate, and ethyl cellosolve acetate; polyols and their derivatives, such as ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, and ethylene glycol monomethyl ether. Ethers, dimethoxyethane, propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerol, and 1,2-hexanediol; alcohol-based solvents, such as methanol, ethanol, propanol, isopropanol, and cyclohexanol; sulfoxide-based solvents, such as dimethyl sulfoxide; and amide-based solvents, such as N-methyl-2-pyrrolidone and N,N-dimethylformamide; benzoic acid ester-based solvents, such as butyl benzoate and methyl 2-methoxybenzoate; tetrahydronaphthalene; 3-phenoxy-toluene, etc. Furthermore, the above solvents can be used alone or in mixtures of two or more.

[0357] Preferably, the viscosity of the coating composition is from 1 cP to 10 cP, and coating is easy within this range. The concentration of the compound according to this disclosure in the coating composition is preferably from 0.1 wt% to 20 wt% (v / v).

[0358] A method for forming a functional layer using the above-described coating composition is also provided. Specifically, it includes the steps of: coating the coating composition according to this disclosure using a solution method; and heat-treating the coated coating composition.

[0359] The heat treatment step is preferably performed at 150°C to 230°C. Furthermore, the heat treatment lasts from 1 minute to 3 hours, more preferably from 10 minutes to 1 hour. Additionally, the heat treatment is preferably performed in an inert gas atmosphere, such as argon or nitrogen.

[0360] For example, the first electrode is the anode and the second electrode is the cathode, or alternatively, the first electrode is the cathode and the second electrode is the anode.

[0361] As anode materials, materials with a large work function are generally preferred to allow holes to be smoothly injected into the organic material layer. Specific examples of anode materials include: metals, such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides, such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides, such as ZnO:Al or SnO2:Sb; conductive polymers, such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline; and so on, but are not limited thereto.

[0362] As cathode materials, materials with a small work function are generally preferred, allowing electrons to be easily injected into the organic material layer. Specific examples of cathode materials include: metals, such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer materials, such as LiF / Al or LiO2 / Al; and so on, but are not limited to these.

[0363] The hole injection layer is a layer for injecting holes from the electrode, and the hole injection material is preferably a compound that has the ability to transport holes, thus exhibiting an effect of injecting holes into the anode and an excellent hole injection effect on the light-emitting layer or light-emitting material, preventing excitons generated in the light-emitting layer from moving to the electron injection layer or electron injection material, and having excellent thin film formation ability. Preferably, the HOMO (highest occupied molecular orbital) of the hole injection material is between that of the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of hole injection materials include metalloporphyrins, oligothiophenes, arylamine-based organic materials, hexanitrile hexaazabenzophenanthrene-based organic materials, quinacridone-based organic materials, and others. Organic materials, anthraquinones, polyaniline, and polythiophene conductive polymers, etc., but not limited to these.

[0364] The hole transport layer is a layer that receives holes from the hole injection layer and transports them to the light-emitting layer. The hole transport material is suitably a material with a high hole mobility, capable of receiving holes from the anode or hole injection layer and transferring them to the light-emitting layer. Specific examples include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers containing both conjugated and non-conjugated portions. The hole transport layer may use one or more hole transport materials in one or more sublayers; for example, the first hole transport layer may contain a polycyclic arylamine derivative, and the second hole transport layer may contain a triarylamine derivative.

[0365] An electron blocking layer (also known as an electron barrier layer) is disposed between the hole transport layer and the light-emitting layer to prevent electrons injected from the cathode from passing through the light-emitting layer into the hole transport layer. The electron blocking layer preferably comprises a material having a lower electron affinity than the electron transport layer. Preferably, the electron blocking layer comprises a compound of formula 1.

[0366] Luminescent materials are suitably those capable of emitting light in the visible light region by receiving and combining holes and electrons from the hole transport layer and electron transport layer, respectively, and exhibiting good quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxyquinoline aluminum complexes (Alq3); carbazole-based compounds; dipolystyrene-based compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; and benzo[…]. Zyrazoles, benzothiazole-based and benzimidazole-based compounds; polymers based on poly(p-phenylenevinylene) (PPV); spirocyclic compounds; polyfluorene; red fluorene; etc., but not limited to these.

[0367] The luminescent layer may comprise a host material and a dopant material. The host material may be a fused aromatic ring derivative, a heterocyclic compound, etc. Specific examples of fused aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentanebenzene derivatives, phenanthrene compounds, fluoranthene compounds, etc. Examples of heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc., but are not limited to these.

[0368] Dopant materials include aromatic amine derivatives, styrene amine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, aromatic amine derivatives are fused aromatic ring derivatives with aryl amino groups, either substituted or unsubstituted, and examples include pyrene, anthracene, etc., which contain aryl amino groups. Examples include bis(indene)pyrene, etc. Styrene amine compounds are compounds in which at least one aryl vinyl group is substituted in a substituted or unsubstituted aryl amine, wherein the substituted or unsubstituted group is selected from one or more substituents of aryl, silyl, alkyl, cycloalkyl, and arylamino. Specific examples include, but are not limited to, styrene amines, styrene diamines, styrene triamines, styrene tetraamines, etc. Furthermore, metal complexes include, but are not limited to, iridium complexes, platinum complexes, etc. Preferably, iridium complexes are used as dopant materials.

[0369] The luminescent layer can be a green luminescent layer. When the compound according to this disclosure is used as the host material of the luminescent layer, it can exhibit enhanced stability to electrons and holes, efficient energy transfer to green dopants, and improved device drive voltage, luminous efficiency, and lifetime.

[0370] The electron transport layer is a layer that receives electrons from the electron injection layer and transports them to the light-emitting layer. The electron transport material is suitably a material that can effectively receive electrons from the cathode and transfer them to the light-emitting layer, and has a high electron mobility. Specific examples include Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic radical compounds; hydroxyflavonoid-metal complexes, etc., but are not limited to these. The electron transport layer can be used with any desired cathode material as used according to the related art. In particular, suitable examples of cathode materials include typical materials with low work functions, followed by an aluminum or silver layer. Specific examples include cesium, barium, calcium, ytterbium, and samarium, each followed by an aluminum or silver layer.

[0371] The electron injection layer is a layer that injects electrons from the electrode, and is preferably a compound that has the ability to transport electrons, the effect of injecting electrons from the cathode, and the excellent effect of injecting electrons into the light-emitting layer or light-emitting material, prevents excitons generated by the light-emitting layer from migrating to the hole injection layer, and also has excellent thin film formation ability. Specific examples include fluorenone, anthraquinone dimethyl ether, dibenzoquinone, thiamethoxam dioxide, etc. azole, diazole, triazole, imidazole, Tetracarboxylic acids, fluorenemethane, anthrone and their derivatives, metal complexes, nitrogen-containing 5-membered ring derivatives, etc., but not limited to these.

[0372] Examples of metal complex compounds include, but are not limited to, lithium 8-hydroxyquinoline, bis(8-hydroxyquinoline)zinc, bis(8-hydroxyquinoline)copper, bis(8-hydroxyquinoline)manganese, tris(8-hydroxyquinoline)aluminum, tris(2-methyl-8-hydroxyquinoline)aluminum, tris(8-hydroxyquinoline)gallium, bis(10-hydroxybenzo[h]quinoline)beryllium, bis(10-hydroxybenzo[h]quinoline)zinc, bis(2-methyl-8-quinoline)chlorogallium, bis(2-methyl-8-quinoline)(o-cresol)gallium, bis(2-methyl-8-quinoline)(1-naphthol)aluminum, and bis(2-methyl-8-quinoline)(2-naphthol)gallium.

[0373] In this disclosure, the "electron injection and transport layer" is a single layer that performs the functions of both an electron injection layer and an electron transport layer. The electron injection and transport layer may contain one or more materials that individually perform those functions. Preferably, the electron injection and transport layer may contain a compound of Formula 1.

[0374] The organic light-emitting device according to this disclosure can be a bottom-emitting device, a top-emitting device, or a dual-sided light-emitting device, and in particular, it can be a bottom-emitting device that requires relatively high luminous efficiency.

[0375] In addition to organic light-emitting devices, the compounds according to this disclosure may be included in organic solar cells or organic transistors.

[0376] The preparation of compounds of Formula 1 and organic light-emitting devices comprising them will be described in detail in the following examples. However, these examples are presented for illustrative purposes only and are not intended to limit the scope of this disclosure.

[0377] [Synthesis example]

[0378] Synthesis Example 1: Preparation of Compound GH1

[0379]

[0380] (1-1) Preparation of intermediate compound GH1 P-1

[0381] Under a nitrogen atmosphere, 9-(2-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-phenyl)-9H-carbazole (30 g, 69.3 mmol) and (5-chloro-[1,1'-biphenyl]-3-yl)boronic acid (16.1 g, 69.3 mmol) were added to tetrahydrofuran (THF, 600 mL), and the mixture was stirred and refluxed. Potassium carbonate (K₂CO₃, 19.2 g, 138.6 mmol) dissolved in water (28 mL) was then added, and after thorough stirring, tetra(triphenylphosphine)palladium(O) (Pd(PPh₃)₄, 2.4 g, 2.1 mmol) was introduced. After reacting for 2 hours, the mixture was cooled to room temperature, and the precipitated solid was collected by filtration. The solid was dissolved in chloroform (1660 mL), washed twice with water, and the organic layer was separated. The mixture was dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure. The residue was recrystallized from chloroform / ethyl acetate to give a white solid, compound GH1 P-1 (31.7 g, 78% yield; MS: [M+H)). + =585.2).

[0382] (1-2) Preparation of compound GH1

[0383] Under a nitrogen atmosphere, compound GH1 P-1 (30 g, 51.3 mmol) and dibenzo[b,d]furan-4-yl-d7boric acid (11.2 g, 51.3 mmol) were added to THF (600 mL), and the mixture was stirred and refluxed. Potassium carbonate (K2CO3; 14.2 g, 102.6 mmol) dissolved in water (28 mL) was then added, and after thorough stirring, Pd(PPh3)4 (1.8 g, 1.5 mmol) was introduced. After reacting for 2 hours, the mixture was cooled to room temperature, and the precipitated solid was filtered off. The solid was dissolved in chloroform (2213 mL), washed twice with water, and the organic layer was separated, dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure. Recrystallization from chloroform / ethyl acetate gave compound GH1 (29.1 g, 78% yield; MS: [M+H)) as a white solid. + =724.9).

[0384] Synthesis Example 2: Preparation of Compound GH2

[0385]

[0386] (2-1) Preparation of intermediate compound GH2 P-1

[0387] In step (1-1) of Synthetic Example 1, 9-(2-(4-chloro-6-(phenyl-d5)-1,3,5-triazin-2-yl)-phenyl)-9H-carbazole was used instead of 9-(2-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)phenyl)-9H-carbazole, and (3-chlorophenyl)boronic acid was used instead of (5-chloro-[1,1'-biphenyl]-3-yl)boronic acid; otherwise, the procedure of Synthetic Example 1-1 was followed to obtain the white solid compound GH2 P-1 (28.7 g, 82% yield; MS: [M+H)). + =514.2).

[0388] (2-2) Preparation of compound GH2

[0389] In steps (1-2) of Synthesis Example 1, compound GH2 P-1 was used instead of compound GH1 P-1, and dibenzo[b,d]furan-4-ylboronic acid (undeuterated) was used instead of dibenzo[b,d]furan-4-yl-d7boronic acid; otherwise, the steps of Synthesis Example 1-2 were followed to obtain a white solid compound GH2 (26.8 g, 71% yield; MS: [M+H)). + =646.3).

[0390] Synthesis Example 3: Preparation of Compound GH3

[0391]

[0392] (3-1) Preparation of intermediate compound GH3 P-1

[0393] In step (1-1) of Synthetic Example 1, 9-(2-(4-chloro-6-(phenyl-d5)-1,3,5-triazin-2-yl)phenyl)-9H-carbazole was used instead of 9-(2-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)phenyl)-9H-carbazole; otherwise, the procedure of Synthetic Example 1-1 was followed to obtain the white solid compound GH3 P-1 (29.8 g, 74% yield; MS: [M+H)). + =590.2).

[0394] (3-2) Preparation of compound GH3

[0395] In steps (1-2) of Synthesis Example 1, compound GH3 P-1 was used instead of compound GH1 P-1; otherwise, the steps of Synthesis Example 1-2 were followed to obtain a white solid compound GH3 (26.8 g, 71% yield; MS: [M+H)). + =646.3).

[0396] Synthesis Example 4: Preparation of Compound GH4

[0397]

[0398] (4-1) Preparation of intermediate compound GH4 P-1

[0399] In step (2-1) of Synthetic Example 2, 9-(2-(4-([1,1'-biphenyl]-4-yl-d9)-6-chloro-1,3,5-triazin-2-yl)phenyl)-9H-carbazole-1,3,4,5,6,8-d6 was used instead of 9-(2-(4-chloro-6-(phenyl-d5)-1,3,5-triazin-2-yl)phenyl)-9H-carbazole, and otherwise the procedure of Synthetic Example 2-1 was followed to give the white solid compound GH4 P-1 (27.6 g, 80% yield; MS: [M+H)). + =600.3).

[0400] (4-2) Preparation of compound GH4

[0401] In step (2-2) of Synthesis Example 2, compound GH4 P-1 was used instead of compound GH2 P-1; otherwise, the procedure of Synthesis Example 2-2 was followed to obtain a white solid compound GH4 (29.2 g, 80% yield; MS: [M+H)). + =732.4).

[0402] Synthesis Example 5: Preparation of Compound GH5

[0403]

[0404] (5-1) Preparation of intermediate compound GH5 P-1

[0405] In step (2-1) of Synthetic Example 2, (3'-chloro-[1,1'-biphenyl]-4-yl)boronic acid was used instead of (3-chlorophenyl)boronic acid; otherwise, the procedure of Synthetic Example 2-1 was followed to obtain the white solid compound GH5 P-1 (31 g, 77% yield; MS: [M+H)). + =590.2).

[0406] (5-2) Preparation of compound GH5

[0407] In step (2-2) of Synthetic Example 2, compound GH5 P-1 was used instead of compound GH2 P-1, and dibenzo[b,d]thiophene-4-ylboronic acid was used instead of dibenzo[b,d]furan-4-ylboronic acid; otherwise, the procedure of Synthetic Example 2-2 was followed to obtain a white solid compound GH5 (32 g, 85% yield; MS: [M+H)). + =738.3).

[0408] Synthesis Example 6: Preparation of Compound GH6

[0409]

[0410] (6-1) Preparation of intermediate compound GH6 P-1

[0411] In step (2-1) of Synthetic Example 2, 9-(2-(4-chloro-6-(phenyl-d5)-1,3,5-triazin-2-yl)phenyl)-9H-carbazole-1,3,4,5,6,8-d6 was used instead of 9-(2-(4-chloro-6-(phenyl-d5)-1,3,5-triazin-2-yl)phenyl)-9H-carbazole, and (5-chloro-[1,1'-biphenyl]-3-yl)boronic acid was used instead of (3-chlorophenyl)boronic acid; otherwise, the steps of Synthetic Example 2-1 were followed to obtain the white solid compound GH6 P-1 (33 g, 79% yield; MS: [M+H)). + =596.3).

[0412] (6-2) Preparation of compound GH6

[0413] In step (2-2) of Synthetic Example 2, compound GH6 P-1 was used instead of compound GH2 P-1, and (dibenzo[b,d]thiophene-4-yl-2,6,8-d3)boronic acid was used instead of dibenzo[b,d]furan-4-ylboronic acid; otherwise, the procedure of Synthetic Example 2-2 was followed to obtain a white solid compound GH6 (31 g, 82% yield; MS: [M+H)). + =747.3).

[0414] Synthesis Example 7: Preparation of Compound GH7

[0415]

[0416] (7-1) Preparation of intermediate compound GH7 P-1

[0417] In step (2-1) of Synthetic Example 2, 9-(2-(4-chloro-6-(phenyl-d5)-1,3,5-triazin-2-yl)phenyl)-9H-carbazole-1,2,3,4,5,6,7,8-d8 was used instead of 9-(2-(4-chloro-6-(phenyl-d5)-1,3,5-triazin-2-yl)phenyl)-9H-carbazole, and (3-chlorophenyl-2,4,5,6-d4)boronic acid was used instead of (3-chlorophenyl)boronic acid; otherwise, the steps of Synthetic Example 2-1 were followed to obtain the white solid compound GH7 P-1 (26.7 g, 76% yield; MS: [M+H)). + =526.3).

[0418] (7-2) Preparation of compound GH7

[0419] In step (2-2) of Synthetic Example 2, compound GH7 P-1 was used instead of compound GH2 P-1, and (dibenzo[b,d]thiophene-4-yl-d7)boronic acid was used instead of dibenzo[b,d]furan-4-ylboronic acid; otherwise, the procedure of Synthetic Example 2-2 was followed to obtain a white solid compound GH7 (31 g, 80% yield; MS: [M+H)). + =681.4).

[0420] Synthesis Example 8: Preparation of Compound GH8

[0421]

[0422] (8-1) Preparation of intermediate compound GH8 P-1

[0423] In step (2-1) of Synthetic Example 2, 9-(2-(4-chloro-6-(phenyl-d5)-1,3,5-triazin-2-yl)phenyl)-9H-carbazole-1,2,3,4,5,6,7,8-d8 was used instead of 9-(2-(4-chloro-6-(phenyl-d5)-1,3,5-triazin-2-yl)phenyl)-9H-carbazole, and (5-chloro-[1,1'-biphenyl]-3-yl-2',3',4',5',6'-d5)boronic acid was used instead of (3-chlorophenyl)boronic acid; otherwise, the procedure of Synthetic Example 2-1 was followed to obtain the white solid compound GH8 P-1 (34 g, 84% yield; MS: [M+H)). + =603.3).

[0424] (8-2) Preparation of compound GH8

[0425] In step (2-2) of Synthetic Example 2, compound GH8 P-1 was used instead of compound GH2 P-1, and (dibenzo[b,d]thiophene-4-yl-d7)boronic acid was used instead of dibenzo[b,d]furan-4-ylboronic acid; otherwise, the procedure of Synthetic Example 2-2 was followed to obtain a white solid compound GH8 (31 g, 84% yield; MS: [M+H)). + =742.4).

[0426] Synthesis Example 9: Preparation of Compound GH9

[0427]

[0428] (9-1) Preparation of intermediate compound GH9 P-1

[0429] In step (2-1) of Synthetic Example 2, 9-(2-(4-([1,1'-biphenyl]-4-yl-d9)-6-chloro-1,3,5-triazin-2-yl)phenyl)-9H-carbazole was used instead of 9-(2-(4-chloro-6-(phenyl-d5)-1,3,5-triazin-2-yl)phenyl)-9H-carbazole; otherwise, the procedure of Synthetic Example 2-1 was followed to obtain the white solid compound GH9 P-1 (28 g, 82% yield; MS: [M+H)). + =594.2).

[0430] (9-2) Preparation of compound GH9

[0431] In step (2-2) of Synthetic Example 2, compound GH9 P-1 was used instead of compound GH2 P-1, and dibenzo[b,d]thiophene-4-ylboronic acid was used instead of dibenzo[b,d]furan-4-ylboronic acid; otherwise, the procedure of Synthetic Example 2-2 was followed to obtain a white solid compound GH9 (32 g, 85% yield; MS: [M+H)). + =742.3).

[0432] Synthesis Example 10: Preparation of Compound GH10

[0433]

[0434] (10-1) Preparation of intermediate compound GH10 P-1

[0435] In step (2-1) of Synthetic Example 2, 9-(2-(4-([1,1'-biphenyl]-4-yl-d9)-6-chloro-1,3,5-triazin-2-yl)phenyl)-9H-carbazole was used instead of 9-(2-(4-chloro-6-(phenyl-d5)-1,3,5-triazin-2-yl)phenyl)-9H-carbazole, and (5-chloro-[1,1'-biphenyl]-3-yl-2',3',4',5',6'-d5)boronic acid was used instead of (3-chlorophenyl)boronic acid; otherwise, the procedure of Synthetic Example 2-1 was followed to obtain the white solid compound GH10 P-1 (29 g, 77% yield; MS: [M+H)). + =743.3).

[0436] (10-2) Preparation of compound GH10

[0437] In step (2-2) of Synthetic Example 2, compound GH10 P-1 was used instead of compound GH2 P-1, and (dibenzo[b,d]furan-4-yl-2,6,8-d3)boronic acid was used instead of dibenzo[b,d]furan-4-ylboronic acid; otherwise, the procedure of Synthetic Example 2-2 was followed to obtain a white solid compound GH10 (28 g, 79% yield; MS: [M+H)). + =878.4).

[0438] Synthesis Example 11: Preparation of Compound GH11

[0439]

[0440] (11-1) Preparation of intermediate compound GH11 P-1

[0441] In step (2-1) of Synthetic Example 2, 9-(2-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)phenyl)-9H-carbazole-1,3,4,5,6,8-d6 was used instead of 9-(2-(4-chloro-6-(phenyl-d5)-1,3,5-triazin-2-yl)phenyl)-9H-carbazole, and otherwise the method of Synthetic Example 2-1 was followed to obtain the white solid compound GH11 P-1 (26.7 g, 76% yield; MS: [M+H)). + =515.2).

[0442] (11-2) Preparation of compound GH11

[0443] In step (2-2) of Synthetic Example 2, compound GH11 P-1 was used instead of compound GH2 P-1, and dibenzo[b,d]thiophene-4-ylboronic acid was used instead of dibenzo[b,d]furan-4-ylboronic acid; otherwise, the method of Synthetic Example 2-2 was followed to obtain a white solid compound GH11 (31 g, 80% yield; MS: [M+H)). + =663.2).

[0444] Example 1

[0445] A glass substrate coated with a 100 nm thick ITO (indium tin oxide) film was immersed in distilled water containing detergent and ultrasonically cleaned. The detergent was a product manufactured by Fischer Co., 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. Following the distilled water cleaning, 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.

[0446] On the prepared ITO transparent electrode, compound HI-A was thermally vacuum-deposited to a thickness of 60 nm to form a hole injection layer. Subsequently, compound HAT was vacuum-deposited on the hole injection layer to a thickness of 5 nm to form a first hole transport layer, and compound HT-A was sequentially vacuum-deposited on the first hole transport layer to a thickness of 50 nm to form a second hole transport layer. Then, compound HT-B was thermally vacuum-deposited on the hole transport layer to a thickness of 45 nm to form an electron blocking layer. After mixing the above-prepared compound GH1 and compound GH-H at a 1:1 weight ratio, the mixture and compound GD were vacuum-deposited on the electron blocking layer at a weight ratio of 90:10 to a thickness of 40 nm to form a light-emitting layer. Then, compound ET-A was vacuum-deposited on the light-emitting layer 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 at a 1:1 weight ratio to a thickness of 35 nm to form both an electron injection and transport layer.

[0447] An organic light-emitting device is fabricated by depositing lithium fluoride (LiF) to a thickness of 1 nm on an electron injection and transport layer and sequentially depositing aluminum to a thickness of 100 nm to form a cathode.

[0448]

[0449] 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 on the cathode was maintained at 0.03 nm / s, the deposition rate of aluminum was maintained at 0.2 nm / s, and the vacuum level during deposition was maintained at 1 × 10⁻⁶. -7 Up to 5×10 -5 This allows for the fabrication of organic light-emitting devices.

[0450] Examples 2 to 11

[0451] The organic light-emitting device was manufactured in the same manner as in Example 1, except that each of the compounds GH2 to GH11 shown in Table 1 was used instead of compound GH1. In Table 1, compounds GH1 to GH11 are listed below.

[0452]

[0453] Comparative Examples 1 to 9

[0454] The organic light-emitting device was manufactured in the same manner as in Example 1, except that compound GH1 was replaced by each of the compounds GH-C1 to GH-C9 shown in Table 1. In Table 1, compounds GH-C1 to GH-C9 are listed below.

[0455]

[0456] [Experimental Example]

[0457] For the organic light-emitting devices prepared in Examples 1 to 11 and Comparative Examples 1 to 9, voltage, efficiency, and lifetime (T0) were measured by applying current. 95 The results are shown in Table 1 below. In this paper, by applying 10 mA / cm 2 The current density is used to measure voltage and efficiency. Additionally, T in Table 1 below... 95 This means at 20 mA / cm 2 The measured time it takes for the brightness to decrease to 95% of the initial brightness at a given current density.

[0458] [Table 1]

[0459]

[0460] The results in Table 1 were obtained by applying current to the organic light-emitting devices of Examples 1 to 11 and Comparative Examples 1 to 9. Specifically, as described above, the green organic light-emitting device of Example 1 was fabricated using a mixture of compound GH1 and compound GH-H, and compound GD (a material known in the art and widely used conventionally) as a dopant material for the green light-emitting layer. Furthermore, the organic light-emitting devices of Examples 2 to 11 were fabricated by replacing compound 1 with each of compounds GH2 to GH11. The organic light-emitting devices of Comparative Examples 1 to 9 were fabricated by replacing compound GH1 with each of compounds GH-C1 to GH-C9.

[0461] Referring to Table 1, it can be seen that when the compound of chemical formula 1 according to the present disclosure is applied to the light-emitting layer in an organic light-emitting device, the characteristics of low voltage, high efficiency and long lifetime can be significantly improved.

[0462] Specifically, compounds of Formula 1 according to this disclosure are designed such that, in a core structure in which a heterocycle containing at least one N is connected to a carbazole ring via a central benzene ring, an aryl substituent is introduced at a specific position on the heterocycle, and a heteroaryl substituent (each substituted or unsubstituted) is introduced via an arylene linking group L. This induces steric hindrance, resulting in a distorted conformation for both the heterocyclic and carbazole moieties. In this arrangement, the electron-donating properties of the carbazole ring enhance overall molecular stability while maintaining a spatially separated electron distribution, thereby conferring additional charge-transfer (CT) properties and enabling improved efficiency at reduced driving voltages.

[0463] Furthermore, in this case, the electron deficiency of the carbazole substituents poses a significant risk to molecular stability. To address this issue, deuterium substitution is performed on the carbazole moiety itself or at specific positions on the nitrogen-containing heterocycle (where substituted or unsubstituted heteroaryl groups are introduced via aryl and arylene linking groups L). This modulates the electron distribution and balance, resulting in significantly improved efficiency and extended device lifetime.

[0464] However, in Comparative Example 1, the structure lacked the defined aryl and arylene-linked heteroaryl substituents on the N-containing heterocycle of Formula 1; therefore, the overall molecular framework remained planar, and the aforementioned beneficial effects could not be achieved. In Comparative Examples 2 to 4, phenyl substituents were introduced at different positions, which failed to generate sufficient steric hindrance, producing only minor improvements. In Comparative Example 5, an additional carbazole substituent was introduced onto the carbazole ring itself, which impaired the expected electron-donating effect of the carbazole substituent and resulted in a decrease in both efficiency and lifetime. This demonstrates that additional substitution of the heterocycle on the carbazole core can directly disrupt the inherent electron-donating properties and produce poor device performance. In Comparative Example 6, although a fluorene substituent was introduced, it provided neither sufficient steric hindrance nor sufficient substituent stability, resulting in a sharp decrease in lifetime. In Comparative Examples 7 to 9, carbazole or dibenzofuran / dibenzothiophene substituents were introduced onto the triazine ring; however, these modifications disrupted the overall molecular stability, increased the driving voltage, and reduced efficiency and lifetime.

[0465] In summary, it can be determined that the compounds according to this disclosure can be effectively applied to the organic material layer responsible for electron injection or transport in organic light-emitting devices by means of the specific positions and types of substituents defined in the chemical formula, thereby significantly improving the characteristics of low voltage, high efficiency and long lifetime compared with comparative compounds.

[0466] [Explanation of reference numerals in the attached figures]

[0467] 1: Substrate 2: Anode

[0468] 3: Light-emitting layer 4: Cathode

[0469] 5: Hole injection layer; 6: Hole transport layer

[0470] 7: Electron blocking layer; 8: Hole blocking layer

[0471] 9: Electron Injection and Transport Layer

Claims

1. A compound represented by the following chemical formula 1: [Chemical Formula 1] ， In chemical formula 1, Each X is independently N or CH, provided that at least one X is N; L represents unsubstituted or deuterated C. 6-60 Alpha-aryl; Ar1 is C with or without substitution. 6-60 Aryl; Ar2 is a C2 group, substituted or unsubstituted, containing one or more of O and S. 2-60 Mixed aromatics; Each R1 is independently hydrogen, deuterium, substituted or unsubstituted C. 6-60 aryl, or substituted or unsubstituted C containing any or more of N, O, and S. 2-60 heteroaryl; and n is an integer from 1 to 8; The condition is that at least one of L, Ar1, Ar2 or R1 is deuterium or is deuterated.

2. The compound according to claim 1, wherein L is a phenylene or biphenylene, each independently unsubstituted or deuterated.

3. The compound according to claim 1, wherein L is selected from any of the following groups: ， In the above chemical formulas, D stands for deuterium. Each n1 is an independent integer from 1 to 4. n2 is an integer from 1 to 3, and n3 is an integer from 1 to 5.

4. The compound according to claim 1, wherein Ar1 is phenyl, biphenyl, or terphenyl, each independently unsubstituted or deuterated.

5. The compound according to claim 1, wherein Ar1 is selected from any of the following groups: ， In the above chemical formulas, D stands for deuterium. Each n4 is an independent integer from 1 to 5. Each n5 is an independent integer from 1 to 4, and n6 is an integer from 1 to 3.

6. The compound according to claim 1, wherein Ar2 is dibenzofuranyl or dibenzothiophenyl, each independently unsubstituted or deuterated.

7. The compound according to claim 1, wherein Ar2 is selected from any of the following groups: ， In the above chemical formulas, D stands for deuterium. Each n7 is an independent integer from 1 to 3, and Each n8 is an independent integer from 1 to 4.

8. The compound according to claim 1, wherein at least one R1 is deuterium; the deuterated C 6-60 aryl; or deuterated C containing any or more of N, O, and S. 2-60 Mixed aromatic compounds.

9. The compound according to claim 1, wherein at least three of L, Ar1, Ar2 and R1 are deuterium, or at least one of L, Ar1, Ar2 and R1 is substituted with three or more deuterium atoms.

10. The compound according to claim 1, wherein the compound represented by chemical formula 1 is substituted with 1 to 60 deuterium atoms.

11. The compound according to claim 1, wherein the compound represented by chemical formula 1 is selected from any of the following compounds: ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， ， 。 12. An organic light-emitting device, comprising: First electrode; The second electrode is configured to be opposite to the first electrode; as well as One or more organic material layers are disposed between the first electrode and the second electrode. At least one of the organic material layers comprises a compound according to any one of claims 1 to 11.

13. The organic light-emitting device according to claim 12, wherein the organic material layer containing the compound is a light-emitting layer.

14. The organic light-emitting device according to claim 11, wherein the light-emitting layer further comprises a compound represented by the following chemical formula 2: [Chemical Formula 2] ， In chemical formula 2, Ar4 and Ar5 are independently substituted or unsubstituted C. 6-60 aryl, or C, substituted or unsubstituted, containing at least one heteroatom selected from N, O, and S. 5-60 Mixed aromatics; R2 and R3 are each independently hydrogen, deuterium, halogen, cyano, nitro, amino, substituted or unsubstituted C. 1-60 Alkyl groups, substituted or unsubstituted C 3-60 Cycloalkyl, substituted or unsubstituted C 2-60 Alkenyl, substituted or unsubstituted C 6-60 aryl, or C, substituted or unsubstituted, containing at least one heteroatom selected from N, O, and S. 5-60 heteroaryl; and p and q are each independent integers from 0 to 7.

15. The organic light-emitting device according to claim 14, wherein Ar4 and Ar5 are each independently phenyl, biphenyl, terphenyl, naphthyl, dibenzofuranyl, dibenzothiopheneyl or dimethylfluorenyl.

16. The organic light-emitting device according to claim 14, wherein the compound represented by chemical formula 2 is selected from any of the following compounds: ， ， 。

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