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

Abstract

The present specification provides a composition for an organic light-emitting device and an organic light-emitting device including the composition for an organic light-emitting device.

Description

[0001] This application claims priority and benefit to Korean Patent Application No. 10-2023-0136034, filed on October 12, 2023, with the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference. Technical Field

[0002] The present invention relates to compositions for organic light-emitting devices and organic light-emitting devices comprising compositions for organic light-emitting devices. Background Technology

[0003] Electroluminescent devices are self-emitting display devices that offer advantages such as wide viewing angles, excellent contrast, and fast response times.

[0004] Organic light-emitting devices have a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to an organic light-emitting device with this structure, electrons and holes injected from the two electrodes recombine in the organic thin film to form exciton pairs, and light is emitted as the exciton pairs decay. The organic thin film can be formed as a single layer or multiple layers, depending on the requirements.

[0005] Depending on the requirements, the materials of organic thin films can possess light-emitting capabilities. For example, compounds capable of forming a light-emitting layer themselves can be used as materials for organic thin films, or compounds that can be used as a host or dopant in a host-dopant type light-emitting layer can be used. Furthermore, compounds capable of performing functions such as hole injection, hole transport, electron blocking, and electron transport and injection can also be used as materials for organic thin films.

[0006] Therefore, in order to improve the performance, efficiency and lifespan of organic light-emitting devices, there is an ongoing need to develop materials for organic thin films. Summary of the Invention

[0007] [Technical Issues] The object of the present invention is to provide a composition for an organic light-emitting device and an organic light-emitting device comprising the composition for an organic light-emitting device.

[0008] [Technical Solution] In one embodiment of this application, a composition for an organic light-emitting device is provided, the composition comprising a heterocyclic compound represented by the following chemical formula A, a heterocyclic compound represented by the following chemical formula B, and a heterocyclic compound represented by the following chemical formula C.

[0009] [Chemical Formula A]

[0010] In chemical formula A, X is O or S. L1 and L2 are each independently: a direct bond; a substituted or unsubstituted C6-C60 arylene; or a substituted or unsubstituted C2-C60 heteroarylene. l1 and l2 are each independent integers from 1 to 3, and when l1 or l2 is 2 or greater, the substituents in the parentheses are different from each other. Ar1 to Ar3 are each independently: substituted or unsubstituted C6-C60 aryl; or substituted or unsubstituted C2-C60 heteroaryl. R1 to R3 are each independently: hydrogen; deuterium; halogen group; cyano; substituted or unsubstituted C1-C60 alkyl; substituted or unsubstituted C3-C60 cycloalkyl; substituted or unsubstituted C2-C60 heterocycloalkyl; substituted or unsubstituted C6-C60 aryl; or substituted or unsubstituted C2-C60 heteroaryl, and r1 is an integer from 1 to 4, r2 is an integer from 0 to 4, and r3 is an integer from 1 to 4, provided that r1 + r2 + r3 equals 8; and when each of r1, r2, and r3 is 2 or greater, the substituents in parentheses are either the same or different from each other. [Chemical Formula B]

[0011] In chemical formula B, Y is either O or S. Cy1 is: a substituted or unsubstituted benzene ring; or a substituted or unsubstituted naphthalene ring. L3 and L4 are each independently: a direct bond; a substituted or unsubstituted C6-C60 arylene; or a substituted or unsubstituted C2-C60 heteroarylene. l3 and l4 are each independent integers from 1 to 3, and when l3 or l4 is 2 or greater, the substituents in parentheses can be the same or different. One of R4 and R5 is a substituted or unsubstituted heteroaryl group containing a C=N bond, and the other of R4 and R5 is a substituted or unsubstituted carbazole group or a substituted or unsubstituted amino group. R6 and R7 may be the same as or different from each other, and each independently represents: hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C3-C60 cycloalkyl group; a substituted or unsubstituted C2-C60 heterocycloalkyl group; a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group. r6 is an integer from 1 to 4 and r7 is an integer from 1 to 6, and when r6 or r7 is 2 or greater, the substituents in parentheses can be the same or different. [Chemical formula C]

[0012] In chemical formula C, Z is either O or S. One of R21 to R28 is a substituted or unsubstituted heteroaryl group containing a C=N bond, and the remaining R21 to R28 are each independently: hydrogen; deuterium; halogen group; cyano; substituted or unsubstituted C1-C60 alkyl; substituted or unsubstituted C3-C60 cycloalkyl; substituted or unsubstituted C2-C60 heterocycloalkyl; substituted or unsubstituted C6-C60 aryl; or substituted or unsubstituted C2-C60 heteroaryl.

[0013] In another embodiment of this application, 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 the composition described above for the organic light-emitting device.

[0014] [Beneficial Effects] The compositions for organic light-emitting devices according to embodiments of this application can be used as materials for organic material layers in organic light-emitting devices. The compositions for organic light-emitting devices can be used as materials for hole injection layers, hole transport layers, light-emitting layers, electron transport layers, electron injection layers, and charge generation layers in organic light-emitting devices. Specifically, the compositions for organic light-emitting devices include: a heterocyclic compound represented by Formula A as a unipolar p-host; a heterocyclic compound represented by Formula B as a bipolar p-host to improve efficiency and lifetime; and a heterocyclic compound represented by Formula C as a unipolar n-host to improve charge balance. When the heterocyclic compound represented by Formula A, the heterocyclic compound represented by Formula B, and the heterocyclic compound represented by Formula C are used in combination, the device characteristics can be improved compared to compositions obtained using conventional single or premixed materials.

[0015] Therefore, when the composition for an organic light-emitting device is used in an organic light-emitting device, the driving voltage of the device can be reduced, the luminous efficiency can be improved, and the lifespan characteristics of the device can be improved due to the thermal stability of the compound. Attached Figure Description

[0016] Figures 1 to 3 These are schematic diagrams illustrating the layer structure of an organic light-emitting device according to an embodiment of this application.

[0017] <Explanation of reference numerals and symbols in the attached drawings> 100: Base 200: Anode 300: Organic material layer 301: Hole Injection Layer 302: Hole transport layer 303: Launch Layer 304: Cavity Blocking Layer 305: Electron Transport Layer 306: Electron Injection Layer 400: Cathode [Best Implementation] This instruction manual will be described in more detail below.

[0018] In this specification, when a component is described as "including" a certain component, it means that other components may be included unless otherwise specifically stated, and other components are not excluded.

[0019] In this specification, the formula is as follows: Indicates the bonding location.

[0020] In this specification, n in Cn represents the number of carbon atoms. That is, for example, C6 to C60 means 6 to 60 carbon atoms.

[0021] In this specification, the term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is replaced by another substituent, and the position to be substituted is not limited, as long as the position is where the hydrogen atom is substituted (i.e., the position where the substituent can be substituted), and when two or more substituents are substituted, the two or more substituents may be the same as or different from each other.

[0022] In this specification, the term "substituted or unsubstituted" means that one or more substituents selected from the group consisting of: deuterium; halogen group; -CN; C1 to C60 alkyl; C2 to C60 alkenyl; C2 to C60 alkynyl; C1 to C60 haloalkyl; C1 to C60 alkoxy; C6 to C60 aryloxy; C1 to C60 alkylthio; C6 to C60 arylthio; C1 to C60 alkylsulfonyl; C6 to C60 arylsulfonyl; C3 to C60 Cycloalkyl; C2 to C60 heterocycloalkyl; C6 to C60 aryl; C2 to C60 heteroaryl; -SiRR'R"; -P(=O)RR'; and -NRR', or substituted or unsubstituted by a substituent connected to two or more substituents selected from the substituents exemplified above, wherein R, R', and R'' are each independently a substituent composed of at least one of the following groups: hydrogen; deuterium; halogen group; alkyl; alkenyl; alkoxy; cycloalkyl; heterocycloalkyl; aryl; and heteroaryl.

[0023] In this specification, "when no substituent is indicated in the formula or structure of the compound" means that the hydrogen atom is bonded to the carbon atom. However, due to deuterium ( 2H is an isotope of hydrogen, therefore some hydrogen atoms can be deuterium.

[0024] In exemplary embodiments of this application, "when no substituent is indicated in the structure of the formula or compound" can mean that all positions that the substituent can reach are hydrogen or deuterium. That is, deuterium is an isotope of hydrogen, and some hydrogen atoms can be deuterium as an isotope, and in this case, the deuterium content can be from 0% to 100%.

[0025] In an exemplary embodiment of this application, in the case where "no substituents are indicated in the formula or structure of the compound", when the content of deuterium is 0%, the content of hydrogen is 100%, and all substituents do not explicitly exclude deuterium (such as hydrogen), hydrogen and deuterium can be mixed and used in the compound.

[0026] In an exemplary embodiment of this application, deuterium is an isotope of hydrogen, an element having a deuterium nucleus consisting of one proton and one neutron, and can be represented by hydrogen-2, and the element symbol can also be represented as D or 2 H.

[0027] In exemplary embodiments of this application, an isotope means an atom having the same atomic number (Z) but different mass numbers (A), and an isotope can also be interpreted as an element having the same number of protons but different numbers of neutrons.

[0028] In an exemplary embodiment of this application, when the total number of substituents in the basic compound is defined as T1 and the number of a specific substituent among the substituents is defined as T2, the content of the specific substituent T% can be defined as T2 / T1×100=T.

[0029] That is, in the example, when the total number of substituents that a phenyl group can have (T1 in the formula) is 5 and the number of deuterium substituents (T2 in the formula) is 1, by The 20% deuterium content in a phenyl group can be represented by 20%. In other words, the 20% deuterium content in a phenyl group can be represented by the following structural formula.

[0030]

[0031] Furthermore, in an exemplary embodiment of this application, "phenyl with 0% deuterium content" may mean a phenyl that does not contain deuterium atoms, that is, a phenyl with five hydrogen atoms.

[0032] In this specification, halogen can be fluorine, chlorine, bromine or iodine.

[0033] In this specification, alkyl groups comprise straight or branched chains having 1 to 60 carbon atoms and may be additionally substituted by another substituent. The number of carbon atoms in an alkyl group may be 1 to 60, specifically 1 to 40, and more specifically 1 to 20. 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, 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, and 5-methylhexyl.

[0034] In this specification, alkenyl groups comprise straight or branched chains having 2 to 60 carbon atoms and may be further substituted with another substituent. The number of carbon atoms in an alkenyl group can be 2 to 60, specifically 2 to 40, and more specifically 2 to 20. Specific examples of alkenyl groups 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, bis(diphenyl-1-yl)vinyl-1-yl, styreneyl, and styreneyl.

[0035] In this specification, the alkynyl group comprises a straight or branched chain having 2 to 60 carbon atoms and may be further substituted by another substituent. The number of carbon atoms in the alkynyl group may be 2 to 60, specifically 2 to 40, and more specifically 2 to 20.

[0036] In this specification, alkyl halogroup refers to an alkyl group substituted with a halogen group, and specific examples of alkyl halogroups include, but are not limited to, -CF3 and -CF2CF3.

[0037] In this specification, alkoxy groups are represented by -O (R101), where R101 can be the same as the alkyl groups described above.

[0038] In this specification, aryl groups are represented by -O(R102), where R102 may be the same as the aryl group examples described above.

[0039] In this specification, alkylthio groups are represented by -S(R103), where R103 can be the same as the examples of alkyl groups described above.

[0040] In this specification, arylthio groups are represented by -S(R104), where R104 can be the same as the examples of aryl groups described above.

[0041] In this specification, alkyl sulfonyl groups are represented by -S(=O)2(R105), wherein R105 may be the same as the alkyl group in the examples described above.

[0042] In this specification, the aryl sulfonyl group is represented by -S(=O)2(R106), wherein R106 may be the same as the aryl group in the examples above.

[0043] In this specification, cycloalkyl groups include monocyclic or polycyclic groups having 3 to 60 carbon atoms and may be further substituted with another substituent. Here, polycyclic means a group in which the cycloalkyl group is directly attached to or fused with another cyclic group. This other cyclic group may be cycloalkyl, but may also be another type of cyclic group, such as heterocycloalkyl, aryl, and heteroaryl. The number of carbon atoms in a cycloalkyl group may be 3 to 60, specifically 3 to 40, and more specifically 5 to 20. Specific 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, and cyclooctyl.

[0044] In this specification, heterocyclic alkyl groups include O, S, Se, N, or Si as heteroatoms, and include monocyclic or polycyclic groups having 2 to 60 carbon atoms, and may be further substituted with another substituent. Here, polycyclic means a group in which the heterocyclic alkyl group is directly attached to or fused with another cyclic group. Here, the other cyclic group may also be a heterocyclic alkyl group, but may also be another type of cyclic group, such as cycloalkyl, aryl, and heteroaryl. The number of carbon atoms in a heterocyclic alkyl group may be 2 to 60, specifically 2 to 40, and more specifically 3 to 20.

[0045] In this specification, aryl groups include monocyclic or polycyclic groups having 6 to 60 carbon atoms, and may be further substituted with another substituent. Here, polycyclic means a group in which the aryl group is directly attached to or fused with another cyclic group. This other cyclic group may also be an aryl group, but may also be another type of cyclic group, such as cycloalkyl, heterocycloalkyl, and heteroaryl. Aryl groups include fused-ring groups. The number of carbon atoms in an aryl group may be 6 to 60, specifically 6 to 40, and more specifically 6 to 25. Specific examples of aryl groups include, but are not limited to, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, perylene, fluoranyl, phenoxide, pyrene, tetraphenyl, pentaphenyl, fluorenyl, indole, acenaphthene, benzo[a]fluorenyl, spirobisfluorenyl, 2,3-dihydro-1H-indole and their fused-ring groups.

[0046] In this specification, terphenyl may be selected from the following structural formulas.

[0047]

[0048] In this specification, the fluorene group may be substituted, and adjacent substituents may bond to each other to form a ring.

[0049] When the fluorene group is substituted, the substituent can be one of the following structural formulas, but is not limited to these.

[0050]

[0051] In this specification, heteroaryl groups include S, O, Se, N, or Si as heteroatoms, and include monocyclic or polycyclic groups having 2 to 60 carbon atoms, and may be further substituted by another substituent. Here, polycyclic means a group in which the heteroaryl group is directly attached to or fused with another cyclic group. Here, the other cyclic group may also be a heteroaryl group, but may also be another type of cyclic group, such as cycloalkyl, heterocycloalkyl, and aryl. The number of carbon atoms in a heteroaryl group may be 2 to 60, specifically 2 to 40, and more specifically 3 to 25. Specific examples of heteroaryl groups include pyridyl, pyrroloyl, pyrimidinyl, pyridazinyl, furanyl, thiophene group, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, furazonyl, oxadiazolyl, thiazolyl, dithiazolyl, tetrazolyl, pyranyl, thiaranyl, diazinyl, oxazinyl, thiazolyl, dioxinyl, triazinyl, tetrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, isoquinazolinyl, quinoxolinyl, naphridinyl, acridineyl, phenanthridinyl (group), imidazopyridyl, diazanaphthyl, triazaindyl, indole, indazinyl, benzothiazolyl, benzoxazolyl, benzoimidazolyl, benzothiophene, benzofuranyl, dibenzothiophene, dibenzofuranyl, carbazole, benzocarbazole, dibenzocarbazole, phenazinyl, dibenzothiophenolyl, spirobis(dibenzothiophenolyl), dihydrophenazinyl, phenoxazinyl, phenanthridyl group, thienyl group), indolo[2,3-a]carbazole, indolo[2,3-b]carbazole, indololino, 10,11-dihydro-dibenzo[b,f]azazolyl, 9,10-dihydroacridyl, phenanthazinyl, phenothiazinyl, phthalazinyl, phenanthrololinyl, naphthobenzofuranyl, naphthobenzothiopheneyl, benzo[c][1,2,5]thiadiazolyl, 2,3-di Hydrobenzo[b]thiophene, 2,3-dihydrobenzofuran, 5,10-dihydrodibenzo[b,e][1,4]azasilyl, pyrazolo[1,5-c]quinazolinyl, pyrido[1,2-b]inzolyl, pyrido[1,2-a]imidazo[1,2-e]indololinyl, and 5,11-dihydroindoxazo[1,2-b]carbazolyl, etc., but not limited to these.

[0052] In this specification, when the substituent is carbazolium, it means that the substituent is bonded to the nitrogen or carbon of carbazolium.

[0053] In this specification, when the carbazolium group is substituted, additional substituents may be introduced at the nitrogen or carbon of the carbazolium.

[0054] In this specification, the benzo[carbazole] group can be any of the following structural formulas.

[0055]

[0056] In this specification, the dibenzocarbazoyl group can be any of the following structural formulas.

[0057]

[0058] In this specification, the naphthobenzofuranyl group can be any of the following structural formulas.

[0059]

[0060] In this specification, the naphthobenzothiophene group can be any of the following structural formulas.

[0061]

[0062] In this specification, silyl groups comprise Si and are substituents directly linked to Si atoms as free radicals, represented by -Si(R107)(R108)(R109), where R107 to R109 may be the same as or different from each other and may each independently be a substituent consisting of at least one of the following groups: hydrogen; deuterium; halogen group; alkyl; alkenyl; alkoxy; cycloalkyl; heterocycloalkyl; aryl; and heteroaryl. Specific examples of silyl groups include... (trimethylsilyl) (triethylsilyl) (tert-butyldimethylsilyl) (Vinyl dimethylsilyl) (propyl dimethylsilyl) (Triphenylsilyl) (Diphenylsilyl) (phenylsilyl), but not limited to this.

[0063] In this specification, the phosphine oxide group is represented by -P(=O)(R110)(R111), and R110 and R111 may be the same as or different from each other, and may each independently be a substituent consisting of at least one of the following groups: hydrogen; deuterium; halogen group; alkyl; alkenyl; alkoxy; cycloalkyl; heterocycloalkyl; aryl; and heteroaryl. Specifically, the phosphine oxide group may be substituted with alkyl or aryl groups, wherein the alkyl and aryl groups may be the same as those in the examples above. Specific examples of phosphine oxide groups include, but are not limited to, dimethylphosphine oxide groups, diphenylphosphine oxide groups, and dinaphthylphosphine oxide groups.

[0064] In this specification, the amino group is represented by -N(R112)(R113), and R112 and R113 may be the same as or different from each other, and may each independently be a substituent consisting of at least one of the following groups: hydrogen; deuterium; halogen group; alkyl; alkenyl; alkoxy; cycloalkyl; heterocycloalkyl; aryl; and heteroaryl. In this specification, the amino group may be selected from the group consisting of: -NH2; monoalkylamino; monoarylamino; monoheteroarylamino; dialkylamino; diarylamino; diheteroarylamino; alkylarylamino; alkylheteroarylamino; and arylheteroarylamino, and the number of carbon atoms in the amino group is not particularly limited, but is preferably from 1 to 30. Specific examples of amino groups include, but are not limited to, methylamino, dimethylamino, ethylamino, diethylamino, phenylamino, naphthylamino, biphenylamino, diphenylamino, anthraceneamino, 9-methyl-anthraylamino, diphenylamino, phenylnaphthylamino, xylylamino, phenyltolylamino, triphenylamino, biphenylnaphthylamino, phenylbiphenylamino, biphenylfluorenylamino, phenyltriphenylamine, and biphenyltriphenylamine.

[0065] In this specification, arylene can be the same as the aryl examples described above, except that arylene is a divalent group.

[0066] In this specification, the heteroaryl group can be the same as the heteroaryl group example described above, except that the heteroaryl group is a divalent group.

[0067] In this specification, "adjacent" groups may mean a substituent that is substituted by an atom directly bonded to the atom in which the corresponding substituent is substituted, a substituent that is spatially closest to the corresponding substituent, or another substituent that is substituted by an atom in which the corresponding substituent is substituted. For example, two substituents substituted at the ortho position in a benzene ring and two substituents substituted by the same carbon atom in an aliphatic ring can be interpreted as groups that are "adjacent" to each other.

[0068] Hydrocarbon rings and heterocycles that can be formed from adjacent groups include aliphatic hydrocarbon rings, aromatic hydrocarbon rings, aliphatic heterocycles, and aromatic heterocycles, and are exemplified by the structures of the above-mentioned cycloalkyl, aryl, heterocycloalkyl, and heteroaryl groups, which can be applied to the hydrocarbon rings and heterocycles, except that the hydrocarbon rings and heterocycles are not monovalent groups.

[0069] In one embodiment of this application, a composition for an organic light-emitting device is provided, the composition comprising a heterocyclic compound represented by the following chemical formula A, a heterocyclic compound represented by the following chemical formula B, and a heterocyclic compound represented by the following chemical formula C.

[0070] [Chemical Formula A]

[0071] In chemical formula A, X is O or S. L1 and L2 are each independently: a direct bond; a substituted or unsubstituted C6-C60 arylene; or a substituted or unsubstituted C2-C60 heteroarylene. l1 and l2 are each independent integers from 1 to 3, and when l1 or l2 is 2 or greater, the substituents in the parentheses are different from each other. Ar1 to Ar3 are each independently: substituted or unsubstituted C6-C60 aryl; or substituted or unsubstituted C2-C60 heteroaryl. R1 to R3 are each independently: hydrogen; deuterium; halogen group; cyano; substituted or unsubstituted C1-C60 alkyl; substituted or unsubstituted C3-C60 cycloalkyl; substituted or unsubstituted C2-C60 heterocycloalkyl; substituted or unsubstituted C6-C60 aryl; or substituted or unsubstituted C2-C60 heteroaryl, and r1 is an integer from 1 to 4, r2 is an integer from 0 to 4, and r3 is an integer from 1 to 4, provided that r1 + r2 + r3 equals 8, and the substituents in parentheses are either the same or different from each other when each of r1, r2, and r3 is 2 or greater. [Chemical Formula B]

[0072] In chemical formula B, Y is either O or S. Cy1 is: a substituted or unsubstituted benzene ring; or a substituted or unsubstituted naphthalene ring. L3 and L4 are each independently: a direct bond; a substituted or unsubstituted C6-C60 arylene; or a substituted or unsubstituted C2-C60 heteroarylene. l3 and l4 are each independent integers from 1 to 3, and when l3 or l4 is 2 or greater, the substituents in parentheses can be the same or different. One of the groups in R4 and R5 is a substituted or unsubstituted heteroaryl group containing a C=N bond, and the other group in R4 and R5 is a substituted or unsubstituted carbazole group or a substituted or unsubstituted amino group. R6 and R7 may be the same as or different from each other, and each independently represents: hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C3-C60 cycloalkyl group; a substituted or unsubstituted C2-C60 heterocycloalkyl group; a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group. r6 is an integer from 1 to 4 and r7 is an integer from 1 to 6, and when r6 or r7 is 2 or greater, the substituents in parentheses can be the same or different. [Chemical formula C]

[0073] In chemical formula C, Z is either O or S. One of R21 to R28 is a substituted or unsubstituted heteroaryl group containing a C=N bond, and the remaining R21 to R28 are each independently: hydrogen; deuterium; halogen group; cyano; substituted or unsubstituted C1-C60 alkyl; substituted or unsubstituted C3-C60 cycloalkyl; substituted or unsubstituted C2-C60 heterocycloalkyl; substituted or unsubstituted C6-C60 aryl; or substituted or unsubstituted C2-C60 heteroaryl.

[0074] Heterocyclic compounds represented by Formula A are heterocyclic compounds containing three or more rings and including O or S, and also including amine substituents. By including amine substituents, heterocyclic compounds represented by Formula A exhibit a tendency for high hole mobility and are therefore used as unipolar p-hosts. Furthermore, the hole transport rate is increased and hole trapping is reduced, thereby improving the driving voltage and efficiency.

[0075] Furthermore, the heterocyclic compound represented by Formula B is a heterocyclic compound containing three or more rings and including O or S, and includes an amine substituent. By including an amine substituent, the heterocyclic compound represented by Formula B exhibits a high hole mobility tendency and thus serves as a bipolar p-host, and by including an azazine substituent, the heterocyclic compound represented by Formula B has a stable Tg value, thereby exhibiting properties that further improve efficiency.

[0076] Furthermore, the heterocyclic compound represented by Formula C is a heterocyclic compound containing three rings and including O or S, and has a structure in which the azazinyl and aryl groups are substituted on dibenzofuran, thus serving as a unipolar n-host with high electron mobility. When used in conjunction with heterocyclic compounds represented by Formula A and Formula B, the heterocyclic compound represented by Formula C is used to balance the charge within the device, thereby improving efficiency and lifetime. However, since the heterocyclic compound represented by Formula C has a low Tg value and may exhibit reduced thermal stability, its content is preferably limited to 25% or lower.

[0077] Therefore, when a composition for an organic light-emitting device, comprising a heterocyclic compound represented by chemical formula A, a heterocyclic compound represented by chemical formula B, and a heterocyclic compound represented by chemical formula C, is used in an organic light-emitting device, an organic light-emitting device with excellent driving characteristics, efficiency, and / or lifetime can be manufactured. Specifically, the heterocyclic compound represented by chemical formula A is characterized by low driving voltage, high efficiency, and long lifetime. By appropriately mixing the three compounds, namely, appropriately mixing the heterocyclic compound represented by chemical formula B (characterized by relatively high efficiency) and the heterocyclic compound represented by chemical formula C (characterized by relatively long lifetime and high efficiency) with the heterocyclic compound represented by chemical formula A, it has been confirmed that the effect on voltage, efficiency, and lifetime can be further improved.

[0078] In one embodiment of this application, groups not represented as substituents or groups represented by hydrogen can be understood as being substituted with deuterium. That is, hydrogen and deuterium can be interchanged.

[0079] In one embodiment of this application, the deuterium content of the heterocyclic compound represented by Formula A, the heterocyclic compound represented by Formula B, and the heterocyclic compound represented by Formula C may be the same or different from each other, and may each be independently 0% to 100%.

[0080] In one embodiment of this application, the deuterium content of the heterocyclic compound represented by Formula A, the heterocyclic compound represented by Formula B, and the heterocyclic compound represented by Formula C may be the same or different from each other, and may each be independently 10% to 100%.

[0081] In one embodiment of this application, the deuterium content of the heterocyclic compound represented by Formula A, the heterocyclic compound represented by Formula B, and the heterocyclic compound represented by Formula C may be the same or different from each other, and may each be independently 20% to 100%.

[0082] In one embodiment of this application, the deuterium content of the heterocyclic compound represented by Formula A, the heterocyclic compound represented by Formula B, and the heterocyclic compound represented by Formula C may be the same or different from each other, and may each be independently 30% to 100%.

[0083] In one embodiment of this application, the deuterium content of the heterocyclic compound represented by Formula A, the heterocyclic compound represented by Formula B, and the heterocyclic compound represented by Formula C may be the same or different from each other, and may each be independently 40% to 100%.

[0084] In one embodiment of this application, the deuterium content of the heterocyclic compound represented by Formula A, the heterocyclic compound represented by Formula B, and the heterocyclic compound represented by Formula C may be the same or different from each other, and may each be independently 50% to 100%.

[0085] In one embodiment of this application, the deuterium content of the heterocyclic compound represented by Formula A, the heterocyclic compound represented by Formula B, and the heterocyclic compound represented by Formula C may be the same or different from each other, and may each be independently 60% to 100%.

[0086] In one embodiment of this application, the deuterium content of the heterocyclic compound represented by Formula A, the heterocyclic compound represented by Formula B, and the heterocyclic compound represented by Formula C may be the same or different from each other, and may each be independently 70% to 100%.

[0087] In one embodiment of this application, the deuterium content of the heterocyclic compound represented by Formula A, the heterocyclic compound represented by Formula B, and the heterocyclic compound represented by Formula C may be the same or different from each other, and may each be independently 80% to 100%.

[0088] In one embodiment of this application, the deuterium content of the heterocyclic compound represented by Formula A, the heterocyclic compound represented by Formula B, and the heterocyclic compound represented by Formula C may be the same or different from each other, and may each be independently 90% to 100%.

[0089] Typically, compounds bonded to hydrogen and those substituted with deuterium exhibit different thermodynamic behaviors. This is because the mass of a deuterium atom is approximately twice that of hydrogen, and due to this mass difference, deuterium possesses a lower vibrational energy. Furthermore, the bond length between carbon and deuterium is shorter than that between carbon and hydrogen, and the dissociation energy required to break this bond is also higher. This may be attributed to the smaller van der Waals radius of deuterium compared to hydrogen, resulting in a narrower bond stretch between carbon and deuterium.

[0090] Among the heterocyclic compounds represented by Formula A, Formula B, and Formula C of this invention, the deuterium-substituted compounds exhibit lower ground-state energies compared to hydrogen-substituted compounds, and the molecular hard core volume decreases as the bond length between carbon and deuterium becomes shorter. As a result, the polarizability can be reduced, and intermolecular interactions may become weaker, thereby increasing the volume of the thin film in the device. These properties lead to an amorphous state of the thin film and reduced crystallinity. Therefore, the deuterium-substituted heterocyclic compounds represented by Formulas A, B, and C can further improve the thermal stability of OLED (organic light-emitting diode) devices, thereby further enhancing lifetime and driving characteristics.

[0091] In this specification, the term "OLED device" may be referred to as "organic light-emitting diode", "OLED (organic light-emitting diode)", "organic light-emitting device" or "organic electroluminescent device".

[0092] In one embodiment of this application, X is 0.

[0093] In another embodiment of this application, X is S.

[0094] In one embodiment of this application, L1 and L2 may each be independently: a direct bond; a substituted or unsubstituted C6 to C40 arylene; or a substituted or unsubstituted C2 to C40 heteroarylene.

[0095] In another embodiment of this application, L1 and L2 may each be independently: a direct bond; or a substituted or unsubstituted C6 to C40 arylene group.

[0096] In another embodiment of this application, L1 and L2 may each be independently: a direct bond; a substituted or unsubstituted phenylene; a substituted or unsubstituted biphenylene; or a substituted or unsubstituted naphthylene.

[0097] In another embodiment of this application, L1 and L2 may each be independently: a direct bond; a deuterated or unsubstituted phenylene; a deuterated or unsubstituted biphenylene; or a deuterated or unsubstituted naphthylene.

[0098] In one embodiment of this application, l1 and l2 are each independently an integer from 1 to 2, and when each is 2 or greater, the substituents in parentheses may be the same or different from each other.

[0099] In another embodiment of this application, l1 and l2 are each 1.

[0100] In one embodiment of this application, Ar1 to Ar3 may each be independently: substituted or unsubstituted C6 to C40 aryl; or substituted or unsubstituted C2 to C40 heteroaryl.

[0101] In another embodiment of this application, Ar1 to Ar3 may each be independently: substituted or unsubstituted C6 to C20 aryl; or substituted or unsubstituted C2 to C20 heteroaryl.

[0102] In another embodiment of this application, Ar1 to Ar3 may each be independently: substituted or unsubstituted phenyl; substituted or unsubstituted biphenyl; substituted or unsubstituted terphenyl; substituted or unsubstituted naphthyl; substituted or unsubstituted phenanthyl; substituted or unsubstituted fluorenyl; substituted or unsubstituted dibenzofuranyl; or substituted or unsubstituted dibenzothiopheneyl.

[0103] In another embodiment of this application, Ar1 to Ar3 may each be independently: deuterium; a deuterium-substituted or unsubstituted phenyl or a phenanthrene- or naphthyl-substituted or unsubstituted phenyl; a deuterium-substituted or unsubstituted biphenyl; a deuterium-substituted or unsubstituted terphenyl; a deuterium- or unsubstituted naphthyl; a deuterium-substituted or unsubstituted phenanthrene; dimethylfluorenyl; diphenylfluorenyl; spirobisfluorenyl; dibenzofuranyl; or a substituted or unsubstituted dibenzothiophenyl.

[0104] In another embodiment of this application, Ar1 to Ar3 may each be independently: deuterium; a deuterated or unsubstituted phenyl or a phenyl substituted with phenanthrene or naphthyl; a deuterated or unsubstituted biphenyl; terphenyl; a phenyl-substituted or unsubstituted naphthyl; a deuterated or unsubstituted phenanthrene; dimethylfluorenyl; spirobisfluorenyl; or dibenzofuranyl.

[0105] In one embodiment of this application, R1 to R3 may each be independently: hydrogen; deuterium; halogen group; cyano; substituted or unsubstituted C1 to C20 alkyl; substituted or unsubstituted C6 to C20 aryl; or substituted or unsubstituted C2 to C20 heteroaryl.

[0106] In another embodiment of this application, R1 to R3 may each be independently: hydrogen; deuterium; halogen group; cyano; substituted or unsubstituted methyl; substituted or unsubstituted propyl; substituted or unsubstituted butyl; substituted or unsubstituted phenyl; substituted or unsubstituted biphenyl; substituted or unsubstituted terphenyl; substituted or unsubstituted naphthyl; substituted or unsubstituted fluorenyl; substituted or unsubstituted dibenzofuranyl; or substituted or unsubstituted dibenzothiopheneyl.

[0107] In another embodiment of this application, R1 to R3 can each be hydrogen or deuterium independently.

[0108] In one embodiment of this application, Y is 0.

[0109] In another embodiment of this application, Y is S.

[0110] In one embodiment of this application, Cy1 can be a substituted or unsubstituted benzene ring; or a substituted or unsubstituted naphthalene ring.

[0111] In another embodiment of this application, Cy1 can be: a deuterated or unsubstituted benzene ring; or a deuterated or unsubstituted naphthalene ring.

[0112] In one embodiment of this application, L3 and L4 may each be independently: a direct bond; a substituted or unsubstituted C6 to C40 arylene; or a substituted or unsubstituted C2 to C40 heteroarylene.

[0113] In another embodiment of this application, L3 and L4 may each be independently: a direct bond; or a substituted or unsubstituted C6 to C40 arylene group.

[0114] In another embodiment of this application, L3 and L4 may each be independently: a direct bond; a substituted or unsubstituted phenylene; a substituted or unsubstituted biphenylene; or a substituted or unsubstituted naphthylene.

[0115] In another embodiment of this application, L3 and L4 may each be independently: a direct bond; a deuterated or unsubstituted phenylene group; or a deuterated or unsubstituted naphthylene group.

[0116] In one embodiment of this application, l3 and l4 are each independently an integer from 1 to 2, and when each is 2 or greater, the substituents in parentheses may be the same or different from each other.

[0117] In another embodiment of this application, l3 and l4 are each 1.

[0118] In one embodiment of this application, one of R4 and R5 is a substituted or unsubstituted heteroaryl group including a C=N bond, and the other of R4 and R5 may be a substituted or unsubstituted carbazole group or a substituted or unsubstituted amino group.

[0119] In another embodiment of this application, one of R4 and R5 is a heteroaryl group including a C=N bond and substituted by a C6 to C60 aryl group or a C2 to C60 heteroaryl group, and the other of R4 and R5 can be: a substituted or unsubstituted benzo[a]carbazolyl group; a substituted or unsubstituted dibenzo[a]carbazolyl group; or an amino group substituted by a substituted or unsubstituted C6 to C60 aryl group or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0120] In another embodiment of this application, one of R4 and R5 is a heteroaryl group including a C=N bond and substituted by a C6 to C40 aryl group or a C2 to C40 heteroaryl group, and the other of R4 and R5 can be: a substituted or unsubstituted benzo[a]carbazolyl group; a substituted or unsubstituted dibenzo[a]carbazolyl group; or an amino group substituted by a substituted or unsubstituted C6 to C40 aryl group or a substituted or unsubstituted C2 to C40 heteroaryl group.

[0121] In another embodiment of this application, one of R4 and R5 is a heteroaryl group including a C=N bond and substituted by a C6 to C20 aryl group or a C2 to C20 heteroaryl group, and the other of R4 and R5 can be: a substituted or unsubstituted benzo[a]carbazolyl group; a substituted or unsubstituted dibenzo[a]carbazolyl group; or an amino group substituted by a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0122] In another embodiment of this application, one of R4 and R5 is a heteroaryl group comprising a C=N bond and substituted with or unsubstituted phenyl, deuterated or unsubstituted biphenyl, naphthyl or dibenzofuranyl, and the other group of R4 and R5 may be: substituted with or unsubstituted deuterium, or substituted with or unsubstituted phenyl or deuterated or unsubstituted naphthyl or benzocarbazolyl; dibenzocarbazolyl; or an amino group substituted with or unsubstituted deuterium, or deuterated or unsubstituted biphenyl, terphenyl, naphthyl, dibenzofuranyl or dibenzothiophene.

[0123] In one embodiment of this application, R6 and R7 may be the same as or different from each other, and each independently represents: hydrogen; deuterium; halogen group; cyano; substituted or unsubstituted C1 to C20 alkyl; substituted or unsubstituted C3 to C20 cycloalkyl; substituted or unsubstituted C2 to C20 heterocycloalkyl; substituted or unsubstituted C6 to C20 aryl; or substituted or unsubstituted C2 to C20 heteroaryl.

[0124] In another embodiment of this application, R6 and R7 may each be independently: hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted methyl group; a substituted or unsubstituted propyl group; a substituted or unsubstituted butyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophenyl group.

[0125] In another embodiment of this application, R6 and R7 can each be hydrogen or deuterium independently.

[0126] In another embodiment of this application, Z is 0.

[0127] In another embodiment of this application, Z is S.

[0128] In another embodiment of this application, one of R21 to R28 is a heteroaryl group including a C=N bond and substituted by a C6 to C60 aryl or a C2 to C60 heteroaryl group, and the remaining of R21 to R28 may each independently be: hydrogen; deuterium; substituted or unsubstituted C6 to C60 aryl; or substituted or unsubstituted C2 to C60 heteroaryl.

[0129] In another embodiment of this application, one of R21 to R28 is a heteroaryl group including a C=N bond and substituted by a C6 to C40 aryl or a C2 to C40 heteroaryl group, and the remaining of R21 to R28 may each independently be: hydrogen; deuterium; substituted or unsubstituted C6 to C40 aryl; or substituted or unsubstituted C2 to C40 heteroaryl.

[0130] In another embodiment of this application, one of R21 to R28 is a heteroaryl group including a C=N bond and substituted by a C6 to C20 aryl or a C2 to C20 heteroaryl group, and the remaining of R21 to R28 may each be independently: hydrogen; deuterium; substituted or unsubstituted C6 to C20 aryl; or substituted or unsubstituted C2 to C20 heteroaryl.

[0131] In another embodiment of this application, one of R21 to R28 is a heteroaryl group comprising a C=N bond and substituted by a C6 to C20 aryl or a C2 to C20 heteroaryl group, and the remaining of R21 to R28 may each independently be: hydrogen; deuterium; substituted or unsubstituted phenyl; substituted or unsubstituted biphenyl; substituted or unsubstituted terphenyl; substituted or unsubstituted naphthyl; substituted or unsubstituted phenanthrene; substituted or unsubstituted triphenylene; substituted or unsubstituted phosphine oxide group; substituted or unsubstituted silyl; substituted or unsubstituted dibenzofuranyl; or substituted or unsubstituted dibenzothiopheneyl.

[0132] In another embodiment of this application, one of R21 to R28 is a heteroaryl group comprising a C=N bond and substituted with a C6 to C20 aryl group or a C2 to C20 heteroaryl group, and the remaining of R21 to R28 may each independently be: hydrogen; deuterium; a phenyl group substituted with or unsubstituted with deuterium, cyano, deuterated or unsubstituted naphthyl, trimethylsilyl or diphenylphosphine oxide group; a biphenyl group substituted with or unsubstituted with deuterium or naphthyl; a substituted or unsubstituted terphenyl; a naphthyl group substituted with or unsubstituted with deuterium or phenyl; phenanthrene; triphenylene; diphenylphosphine oxide group; triphenylsilyl; dibenzofuranyl; or dibenzothiophene.

[0133] In another embodiment of this application, chemical formula A may be represented by any of the following chemical formulas A-1 to A-5.

[0134] [Chemical Formula A-1]

[0135] [Chemical Formula A-2]

[0136] [Chemical Formula A-3]

[0137] [Chemical Formula A-4]

[0138] [Chemical Formula A-5]

[0139] In chemical formulas A-1 to A-5, The definitions of X, R1, R2, R3, L1, L2, Ar1, Ar2, Ar3, l1, l2, r1, r2, and r3 are the same as those described in Equation A above.

[0140] In another embodiment of this application, chemical formula B may be represented by any of the following chemical formulas B-1 to B-10.

[0141] [Chemical Formula B-1]

[0142] [Chemical formula B-2]

[0143] [Chemical Formula B-3]

[0144] [Chemical Formula B-4]

[0145] [Chemical Formula B-5]

[0146] [Chemical Formula B-6]

[0147] [Chemical Formula B-7]

[0148] [Chemical Formula B-8]

[0149] [Chemical Formula B-9]

[0150] [Chemical Formula B-10]

[0151] In chemical formulas B-1 to B-10 The definitions of Y, L3, L4, R6, R7, l3, l4, r6, and r7 are the same as those described in chemical formula B above, and R5 is a substituted or unsubstituted carbazole group or a substituted or unsubstituted amino group. R8 represents: hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group. r8 is an integer from 0 to 4, and when r8 is 2 or greater, the substituents in the parentheses can be the same or different from each other. N-Het1 is represented by the following structural formula 1. [Structure 1]

[0152] In structural formula 1, Indicates the connection site with another structure. Y1 to Y5 may be the same as or different from each other, and each of Y1 to Y5 is independently CRa or N, provided that at least one of Y1 to Y5 is N, and Ra is: a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group; or two or more adjacent Ra groups may be bonded to each other to form a ring.

[0153] In the chemical formulas B-1 to B-10 of this application, R5 can be: a substituted or unsubstituted benzo[a]carbazolyl group; a substituted or unsubstituted dibenzo[a]carbazolyl group; or an amine group substituted with a substituted or unsubstituted C6 to C60 aryl group or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0154] In another embodiment of this application, R5 may be: a substituted or unsubstituted benzo[a]carbazolyl group; a substituted or unsubstituted dibenzo[a]carbazolyl group; or an amine group substituted with a substituted or unsubstituted C6 to C40 aryl group or a substituted or unsubstituted C2 to C40 heteroaryl group.

[0155] In another embodiment of this application, R5 may be: a substituted or unsubstituted benzo[a]carbazolyl group; a substituted or unsubstituted dibenzo[a]carbazolyl group; or an amino group substituted with a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0156] In another embodiment of this application, R5 may be: a deuterium-substituted or unsubstituted phenyl group, or a deuterium-substituted or unsubstituted naphthyl group, or a dibenzocarbazolyl group; or an amino group substituted with a deuterium-substituted or unsubstituted phenyl group, a deuterium-substituted or unsubstituted biphenyl group, a terphenyl group, a naphthyl group, a dibenzofuranyl group, or a dibenzothiophene group.

[0157] In one embodiment of this application, R8 may be: hydrogen; deuterium; halogen group; cyano; substituted or unsubstituted C1 to C40 alkyl; substituted or unsubstituted C3 to C40 cycloalkyl; substituted or unsubstituted C2 to C40 heterocycloalkyl; substituted or unsubstituted C6 to C40 aryl; or substituted or unsubstituted C2 to C40 heteroaryl.

[0158] In another embodiment of this application, R8 may be: hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted methyl group; a substituted or unsubstituted propyl group; a substituted or unsubstituted butyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted dibenzofuranyl group; or a substituted or unsubstituted dibenzothiophenyl group.

[0159] In another embodiment of this application, R8 can be hydrogen or deuterium.

[0160] In one embodiment of this application, Y1 to Y5 may be the same as or different from each other, and each of Y1 to Y5 is independently CRa or N, provided that at least one of Y1 to Y5 is N.

[0161] In another embodiment of this application, Y1 to Y5 may be the same as or different from each other, and Y1 to Y5 are each independently CRa or N, provided that two or more of Y1 to Y5 are N.

[0162] In another embodiment of this application, Y1 to Y5 may be the same as or different from each other, and each of Y1 to Y5 is independently CRa or N, provided that three or more of Y1 to Y5 are N.

[0163] In another embodiment of this application, Ra can be: a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group; or two or more adjacent Ra groups can be bonded to each other to form a substituted or unsubstituted C2 to C40 aliphatic ring or a substituted or unsubstituted C2 to C40 aromatic ring.

[0164] In another embodiment of this application, Ra can be: a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group; or two or more adjacent Ra groups can be bonded to each other to form a substituted or unsubstituted C2 to C20 aliphatic ring or a substituted or unsubstituted C2 to C20 aromatic ring.

[0165] In another embodiment of this application, Ra can be: a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group; or two or more adjacent Ra groups can be bonded to each other to form a substituted or unsubstituted C2 to C20 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C20 aromatic heterocycle.

[0166] In another embodiment of this application, Ra can be: phenyl; biphenyl; terphenyl; naphthyl; dibenzofuranyl; or dibenzothiophene, and can be substituted with or unsubstituted by deuterium, halogen (particularly -F), methyl, tert-butyl, phenyl, biphenyl, or naphthyl. Alternatively, two or more adjacent Ra groups can be bonded to each other to form a benzene ring, a benzofuran ring, or a benzothiophene ring.

[0167] In another embodiment of this application, chemical formula C may be represented by any of the following chemical formulas C-1 to C-3.

[0168] [Chemical formula C-1]

[0169] [Chemical formula C-2]

[0170] [Chemical formula C-3]

[0171] In chemical formulas C-1 to C-3, the definition of Z is the same as that described in chemical formula C. L5 and L6 may be the same as or different from each other, and each independently consists of: a direct bond; a substituted or unsubstituted C6 to C60 arylene; or a substituted or unsubstituted C2 to C60 heteroarylene. R29 is: a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group. R30 and R31 may be the same as or different from each other, and each is independently either hydrogen or deuterium. r30 is an integer from 0 to 3. When r30 is 2 or greater, the substituents within the parentheses are either the same or different from each other. r31 is an integer from 0 to 4. When r31 is 2 or greater, the substituents within the parentheses are either the same or different from each other. l5 and l6 are each independent integers from 1 to 3, and when l5 and l6 are each 2 or greater, the substituents in parentheses can be the same or different from each other. N-Het2 is represented by the following structural formula 2. [Structure 2]

[0172] In structural formula 2, Indicates the connection site with another structure. Y6 to Y10 may be the same as or different from each other, and if at least one of Y6 to Y10 is N, then Y6 to Y10 are each independently CRb or N. Rb is: a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group; or two or more adjacent Rb groups may bond to each other to form a ring.

[0173] In one embodiment of this application, L5 and L6 may be the same as or different from each other, and each independently represents: a direct bond; a substituted or unsubstituted C6 to C20 arylene; or a substituted or unsubstituted C2 to C20 heteroarylene.

[0174] In another embodiment of this application, L5 and L6 may be the same as or different from each other, and each independently represents: a direct bond; a substituted or unsubstituted phenylene; a substituted or unsubstituted biphenylene; or a substituted or unsubstituted naphthylene.

[0175] In another embodiment of this application, L5 and L6 may be the same as or different from each other, and each independently represents: a direct bond; a deuterated or unsubstituted phenylene; a biphenylene; or a naphthylene.

[0176] In one embodiment of this application, R29 may be: a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group.

[0177] In another embodiment of this application, R29 may be: a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0178] In another embodiment of this application, R29 may be: hydrogen; deuterium; substituted or unsubstituted phenyl; substituted or unsubstituted biphenyl; substituted or unsubstituted terphenyl; substituted or unsubstituted naphthyl; substituted or unsubstituted phenanthryl; substituted or unsubstituted triphenylene; substituted or unsubstituted phosphine oxide group; substituted or unsubstituted silyl; substituted or unsubstituted dibenzofuranyl; or substituted or unsubstituted dibenzothiophenyl.

[0179] In another embodiment of this application, R29 may be: hydrogen; deuterium; a phenyl group substituted with or unsubstituted by deuterium, cyano, deuterated or unsubstituted naphthyl, trimethylsilyl or diphenylphosphine oxide; a biphenyl group substituted with or unsubstituted by deuterium or naphthyl; a substituted or unsubstituted terphenyl; a naphthyl group substituted with or unsubstituted by deuterium or phenyl; phenanthrene; triphenylene; diphenylphosphine oxide; triphenylsilyl; dibenzofuranyl; or dibenzothiophene.

[0180] In one embodiment of this application, Y6 to Y10 may be the same as or different from each other, and each of Y6 to Y10 is independently CRb or N, provided that at least one of Y6 to Y10 is N.

[0181] In another embodiment of this application, Y6 to Y10 may be the same as or different from each other, and Y6 to Y10 may each be CRb or N independently, provided that two or more of Y6 to Y10 are N.

[0182] In another embodiment of this application, Y6 to Y10 may be the same as or different from each other, and Y6 to Y10 may each be CRb or N independently, provided that three or more of Y6 to Y10 are N.

[0183] In another embodiment of this application, Rb can be: a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group; or two or more adjacent Rb groups can be bonded to each other to form a substituted or unsubstituted C2 to C40 aliphatic ring or a substituted or unsubstituted C2 to C40 aromatic ring.

[0184] In another embodiment of this application, Rb can be: a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group; or two or more adjacent Rb groups can be bonded to each other to form a substituted or unsubstituted C2 to C20 aliphatic ring or a substituted or unsubstituted C2 to C20 aromatic ring.

[0185] In another embodiment of this application, Rb can be: a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group; or two or more adjacent Rb groups can be bonded to each other to form a substituted or unsubstituted C2 to C20 aromatic hydrocarbon ring or a substituted or unsubstituted C2 to C20 aromatic heterocycle.

[0186] In another embodiment of this application, Rb can be: phenyl; biphenyl; terphenyl; naphthyl; hydroxyl; dibenzofuranyl; or dibenzothiophene, and can be substituted with or unsubstituted by deuterium, halogen (especially -F), methyl, tert-butyl, phenyl, biphenyl, or naphthyl. Alternatively, two or more adjacent Rb groups can be bonded to each other to form a benzene ring, a benzofuran ring, or a benzothiophene ring.

[0187] In one embodiment of the present invention, chemical formula A may include any of the following compounds.

[0188]

[0189]

[0190]

[0191]

[0192]

[0193] In one embodiment of the present invention, chemical formula B may include any of the following compounds.

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202] In one embodiment of the present invention, chemical formula C may include any of the following compounds.

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210] By introducing various substituents into heterocyclic compounds represented by chemical formulas A, B, and C, compounds exhibiting the inherent properties of the introduced substituents can be synthesized. For example, by incorporating substituents commonly used in the manufacture of organic light-emitting devices (substituents typically used for materials such as hole injection materials, hole transport materials, luminescent materials, electron transport materials, and electron injection materials) into the core structure, and particularly by incorporating substituents primarily used for emitting materials into the core structure, materials that meet the requirements of each organic layer can be synthesized.

[0211] In one embodiment of this application, the heterocyclic compound represented by chemical formula A, the heterocyclic compound represented by chemical formula B, and the heterocyclic compound represented by chemical formula C may be present in a molar ratio of 0.1-3:0.1-2:0.1-2.5.

[0212] In another embodiment of this application, the heterocyclic compound represented by chemical formula A, the heterocyclic compound represented by chemical formula B, and the heterocyclic compound represented by chemical formula C may be present in a molar ratio of about 0.1-2:0.1-1.5:0.1-2 or about 1-2:0.5-1.5:1-2.

[0213] Furthermore, heterocyclic compounds of formula A, formula B, and formula C exhibit excellent thermal stability, which provides driving stability and improves lifetime characteristics for organic light-emitting devices.

[0214] In one embodiment of this application, the heterocyclic compound represented by formula C may be included in an amount of less than 60%, based on the total molar number of the heterocyclic compound represented by formula A, the heterocyclic compound represented by formula B, and the heterocyclic compound represented by formula C.

[0215] In another embodiment of this application, the heterocyclic compound represented by chemical formula C may be included in an amount of 50% or less, based on the total molar number of the heterocyclic compound represented by chemical formula A, the heterocyclic compound represented by chemical formula B, and the heterocyclic compound represented by chemical formula C.

[0216] In another embodiment of this application, the heterocyclic compound represented by chemical formula C may be included in an amount of 30% or less, based on the total molar number of the heterocyclic compound represented by chemical formula A, the heterocyclic compound represented by chemical formula B, and the heterocyclic compound represented by chemical formula C.

[0217] In another embodiment of this application, the heterocyclic compound represented by chemical formula C may be included in an amount of 25% or less, based on the total molar number of the heterocyclic compound represented by chemical formula A, the heterocyclic compound represented by chemical formula B, and the heterocyclic compound represented by chemical formula C.

[0218] In another embodiment of this application, an organic light-emitting device is provided, comprising: a first electrode; a second 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 composition for the organic light-emitting device.

[0219] In one embodiment of this application, an organic light-emitting device is provided, comprising: a first electrode; a second electrode configured to face 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 composition for the organic light-emitting device.

[0220] In one embodiment of this application, the organic material layer further includes an emission layer, and the emission layer may include a composition for an organic light-emitting device.

[0221] In another embodiment of this application, the emitting layer may include a composition for an organic light-emitting device as the main body.

[0222] In one embodiment of this application, the emitting layer may include a composition for an organic light-emitting device as a red substrate.

[0223] In one embodiment of this application, the emitter layer may simultaneously include a heterocyclic compound represented by chemical formula A, a heterocyclic compound represented by chemical formula B, and a heterocyclic compound represented by chemical formula C.

[0224] In one embodiment of this application, the emitter layer may simultaneously include a heterocyclic compound represented by chemical formula A, a heterocyclic compound represented by chemical formula B, and a heterocyclic compound represented by chemical formula C as the host material.

[0225] In one embodiment of this application, the first electrode may be an anode, and the second electrode may be a cathode.

[0226] In another embodiment of this application, the first electrode may be a cathode, and the second electrode may be an anode.

[0227] The organic light-emitting device of the present invention may further include one or two or more layers selected from the group consisting of a light-emitting layer, a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer and an electron injection layer.

[0228] Figures 1 to 3 The diagram illustrates the stacking order of electrodes and organic material layers in an organic light-emitting device according to one embodiment of this application. However, the scope of this application is not intended to be limited to these figures, and structures of organic light-emitting devices known in the art can also be applied to this application.

[0229] Reference Figure 1 An organic light-emitting device is shown in which an anode (200), an organic material layer (300), and a cathode (400) are sequentially stacked on a substrate (100). However, this application is not limited to this structure, and as shown... Figure 2 As shown, an organic light-emitting device in which a cathode, an organic material layer, and an anode are sequentially stacked on a substrate can also be realized. The composition for the organic light-emitting device may be included in the organic material layer (300), and the organic material layer (300) may include one or more layers.

[0230] Figure 3 An example is shown in which the organic material layers have a multilayer structure. According to... Figure 3 The organic light-emitting device may include a hole injection layer (301), a hole transport layer (302), an emission layer (303), a hole blocking layer (304), an electron transport layer (305), and an electron injection layer (306). The composition for the organic light-emitting device may be included in the emission layer (303). However, this application is not limited to this stacked structure, and layers other than the emission layer may be omitted as needed, or additional functional layers may be included.

[0231] An organic light-emitting device according to an embodiment of this application includes: a first electrode; a first stack disposed on the first electrode and including a first emission layer; a charge-generating layer disposed on the first stack; a second stack disposed on the charge-generating layer and including a second emission layer; and a second electrode disposed on the second stack.

[0232] In an organic light-emitting device according to an embodiment of this application, when having the above-described double-stacked structure, at least one of the first emission layer (first stacked emission layer) and the second emission layer (second stacked emission layer) may include a composition for an organic light-emitting device.

[0233] Furthermore, each of the first stack and the second stack may independently include one or more of the aforementioned hole injection layer, hole transport layer, hole blocking layer, electron transport layer and electron injection layer.

[0234] The composition for an organic light-emitting device can be used to form an organic material layer of the organic light-emitting device, and more preferably, it can be used as a material for an emitting layer.

[0235] The composition can be in the form of a premixed heterocyclic compound of formula A, a heterocyclic compound of formula B, and a heterocyclic compound of formula C, and can be prepared by mixing powdered materials before forming an organic material layer of the organic light-emitting device, or by mixing liquid compounds at or above a suitable temperature. The composition is in a solid state below the melting point of each material and can be maintained in a liquid state by adjusting the temperature.

[0236] The composition may also include materials known in the art, such as solvents and additives.

[0237] In one embodiment of this application, a method for manufacturing an organic light-emitting device is provided, the method comprising: preparing a substrate; forming a first electrode on the substrate; forming one or more organic material layers on the first electrode; and forming a second electrode on the organic material layers, wherein forming the organic material layers comprises forming one or more organic material layers using a composition for an organic light-emitting device according to an embodiment of this application.

[0238] In one embodiment of this application, a method for manufacturing an organic light-emitting device is provided, wherein forming an organic material layer includes forming a heterocyclic compound represented by formula A, a heterocyclic compound represented by formula B, and a heterocyclic compound represented by formula C using a thermal vacuum deposition method.

[0239] An organic light-emitting device according to an embodiment of this application can be manufactured using conventional methods and materials for manufacturing organic light-emitting devices, except that the organic layer is formed using the aforementioned composition.

[0240] The organic light-emitting device of the present invention may further include one or two or more layers selected from the group consisting of a light-emitting layer, a hole injection layer, a hole transport layer, an electron blocking layer, an electron injection layer, an electron transport layer, a hole auxiliary layer, and a hole blocking layer.

[0241] In one embodiment of this application, the organic light-emitting device may be a blue organic light-emitting device, and the composition for the organic light-emitting device may be used as a material for the blue organic light-emitting device.

[0242] In one embodiment of this application, the organic light-emitting device may be a green organic light-emitting device, and the composition for the organic light-emitting device may be used as a material for the green organic light-emitting device.

[0243] In one embodiment of this application, the organic light-emitting device may be a red organic light-emitting device, and the composition for the organic light-emitting device may be used as a material for the red organic light-emitting device.

[0244] In the manufacture of organic light-emitting devices, heterocyclic compounds represented by Formula A, Formula B, and / or Formula C can be formed into organic material layers not only by vacuum deposition but also by solution coating. Here, solution coating methods refer to spin coating, dip coating, inkjet printing, screen printing, spray coating, and roll coating, but are not limited to these.

[0245] The organic material layer of the organic light-emitting device of the present invention can be a single-layer structure, or it can be a multilayer structure consisting of two or more stacked organic material layers. For example, the organic light-emitting device of the present invention can have a structure including a hole injection layer, a hole transport layer, a light-emitting 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 can include a smaller number of organic material layers.

[0246] In one embodiment of this application, the organic layer may include an iridium-based dopant.

[0247] In one embodiment of this application, the iridium dopant may be a green phosphorescent dopant such as Ir(ppy)3, but is not limited thereto.

[0248] In one embodiment of this application, red phosphorescent dopant (piq)2Ir(acac) can be used as an iridium-based dopant, but it is not limited thereto.

[0249] The organic light-emitting device of the present invention can be manufactured using conventional methods and materials for manufacturing organic light-emitting devices, except that one or more organic layers are formed using the aforementioned composition for organic light-emitting devices.

[0250] In the organic light-emitting device of this application, materials with relatively high work functions can be used as anode materials, and transparent conductive oxides, metals, or conductive polymers can be employed. 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.

[0251] In the organic light-emitting device of this application, materials with relatively low work functions can be used as cathode materials, and metals, metal oxides, or conductive polymers can be employed. 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; and multilayer structures such as LiF / Al or LiO2 / Al, but are not limited thereto.

[0252] In the organic light-emitting device of this application, known hole-injection materials can be used as hole-injection materials. For example, phthalocyanine compounds, such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429, can be used; or starburst-type amine derivatives described in [Advanced Materials, 6, p. 677 (1994)], such as tris(4-carbazolyl-9-ylphenyl)amine (TCTA), 4,4',4"-tris[phenyl(m-tolyl)amino]triphenylamine (m-MTDATA), and 1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene (m-MTDAPB); soluble conductive polymers, such as polyaniline / dodecylbenzenesulfonic acid, poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate), polyaniline / camphorsulfonic acid, or polyaniline / poly(4-styrenesulfonate).

[0253] In the organic light-emitting device of this application, pyrazoline derivatives, arylamine derivatives, stilbene derivatives, and triphenyldiamine derivatives can be used as hole transport materials, and low molecular weight materials or polymer materials can be used.

[0254] In the organic light-emitting device of this application, the following can be used as electron transport materials: oxadiazole derivatives; anthraquinone dimethyl ether and its derivatives; benzoquinone and its derivatives; naphthoquinone and its derivatives; anthraquinone and its derivatives; tetracyanoanthraquinone dimethyl ether and its derivatives; fluorenone derivatives; diphenyl dicyanoethylene and its derivatives; biphenylquinone derivatives; and metal complexes of 8-hydroxyquinoline and its derivatives. In addition to low molecular weight materials, polymer materials can also be used.

[0255] In the organic light-emitting device of this application, LiF is commonly used as an electron injection material, for example, in the art, but this application is not limited to this.

[0256] In the organic light-emitting device of this application, red, green, or blue light-emitting materials can also be used as the light-emitting material, and two or more light-emitting materials can be mixed and used if necessary. In this case, the two or more light-emitting materials can be deposited using separate sources, or they can be premixed and deposited using a single source. Furthermore, fluorescent materials or phosphorescent materials can be used as the light-emitting material. The light-emitting material can be a material that emits light by recombination of holes and electrons injected from the anode and cathode respectively, or a material in which the host material and dopant material participate in light emission together.

[0257] When using luminescent materials in combination, substrates of the same type or different types can be mixed and used. For example, as the substrate material for the luminescent layer, two or more materials selected from n-type or p-type substrate materials can be used.

[0258] Depending on the materials used, an organic light-emitting device according to one embodiment of this application may be a top-emitting, bottom-emitting, or dual-emitting type.

[0259] Heterocyclic compounds according to one embodiment of this application can also function in organic electronic devices (such as organic solar cells, organic photoreceptors, and organic transistors) based on principles similar to those used in organic light-emitting devices.

[0260] [Embodiments for Implementing the Invention] The present disclosure will be described in more detail below with reference to examples. However, these examples are provided for illustrative purposes only and are not intended to limit the scope of the present disclosure.

[0261] <Example> [Preparation Example 1] Preparation of Compound A26

[0262] 1) Preparation of intermediate A26-1 In a 1 L double-necked flask, 5-bromo-9-chloronaphtho[1,2-b]benzofuran (30.0 g, 90.5 mmol), phenylboronic acid (12.1 g, 99.6 mmol), Pd(pph3)4 (5.2 g, 4.5 mmol), and K2CO3 (25.0 g, 181.0 mmol) were dissolved in a mixed solvent of 1,4-dioxane / H2O (300 mL / 60 mL), and the mixture was refluxed for 1 hour. The reaction mixture was purified by recrystallization from methanol to give compound A26-1 (24.8 g, 83.3%).

[0263] 2) Preparation of compound A26 In a 500 mL two-necked flask, compound A26-1 (10.0 g, 30.4 mmol), di([1,1'-biphenyl]-4-yl)amine (11.3 g, 30.4 mmol), Pd2(dba)3 (1.4 g, 1.5 mmol), Xphos (1.4 g, 3.0 mmol), and NaOtBu (5.8 g, 60.8 mmol) were dissolved in toluene (150 mL), and the mixture was refluxed for 1 hour. The reaction mixture was purified by recrystallization from methanol to obtain the target compound A26 (17.6 g, yield: 87.2%).

[0264] The following compounds were synthesized in the same manner as those used for the preparation of compound A26, except that (A), (B) and (C) from Table 1 below were used as intermediates.

[0265] [Table 1]

[0266] [Preparation Example 2] Preparation of Compound A20

[0267] 1) Preparation of intermediate A20-1 In a 1 L double-necked flask, 5-bromo-7-chloronaphtho[1,2-b]benzofuran (30.0 g, 90.5 mmol), phenylboronic acid (12.1 g, 99.6 mmol), Pd(pph3)4 (5.2 g, 4.5 mmol), and K2CO3 (25.0 g, 181.0 mmol) were dissolved in a mixed solvent of 1,4-dioxane / H2O (300 mL / 60 mL), and the mixture was refluxed for 1 hour. The reaction mixture was purified by recrystallization from methanol to give compound A20-1 (24.8 g, 83.3%).

[0268] 2) Preparation of compound A20 In a 250 mL double-necked flask, compound A20-1 (10.0 g, 30.4 mmol), (4-([1,1'-biphenyl]-4-yl(phenyl)amino)phenyl)boronic acid (11.1 g, 30.4 mmol), Pd2(dba)3 (1.4 g, 1.5 mmol), Xphos (1.4 g, 3.0 mmol), and K2CO3 (8.4 g, 60.8 mmol) were dissolved in 1,4-dioxane / H2O (100 mL / 20 mL), and the mixture was refluxed for 1 hour. The reaction mixture was purified by recrystallization from methanol to obtain the target compound A20 (15.1 g, yield: 80.9%).

[0269] The following compounds were synthesized in the same manner as those used for the preparation of compound A20, except that (A), (B) and (C) in Table 2 below were used as intermediates.

[0270] [Table 2]

[0271] [Preparation Example 3] Preparation of Compound B89

[0272] 1) Preparation of intermediate B89-1 2-(7-chlorodibenzo[b,d]furan-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborhecyclopentane (20.0 g, 60.9 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (16.3 g, 60.9 mmol), Pd(PPh3)4 (3.52 g, 3.04 mmol), and K2CO3 (25.2 g, 183 mmol) were added to a mixed solvent of 1,4-dioxane / H2O (200 mL / 60 mL), and stirred at 100 °C for 2 hours. After cooling to room temperature, the resulting solid was filtered to give intermediate B89-1 (22.7 g, 86%).

[0273] 2) Preparation of compound B89 Intermediate B89-1 (10.0 g, 23.1 mmol), N-phenyl-[1,1'-biphenyl]-4-amine (5.69 g, 23.1 mmol), Pd2(dba)3 (1.06 g, 1.15 mmol), XPhos (1.10 g, 2.31 mmol), and NaOtBu (6.64 g, 69.1 mmol) were added to xylene (100 mL), and the mixture was stirred at 150 °C for 2 hours. After cooling to room temperature, the solid was filtered off. The crude product was purified by silica gel chromatography to give compound B89 (11.7 g, 79%).

[0274] The following compounds were synthesized in the same manner as those used for the preparation of compound B89, except that (A), (B) and (C) in Table 3 below were used as intermediates.

[0275] [Table 3]

[0276] [Preparation Example 4] Preparation of Compound B66

[0277] 1) Preparation of intermediate B66-1 2-(7-chlorodibenzo[b,d]furan-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborhecyclopentane (20.0 g, 60.9 mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (16.3 g, 60.9 mmol), Pd(pph3)4 (3.52 g, 3.04 mmol), and K2CO3 (19.4 g, 183 mmol) were added to a mixed solvent of 1,4-dioxane / H2O (200 mL / 60 mL), and stirred at 100 °C for 2 hours. After cooling to room temperature, the resulting solid was filtered to give intermediate B66-1 (21.4 g, 81%).

[0278] 2) Preparation of compound B66 Intermediate B66-1 (10.0 g, 23.1 mmol), N,N-diphenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxane-2-yl)aniline (8.56 g, 23.1 mmol), Pd2(dba)3 (1.06 g, 1.15 mmol), XPhos (1.10 g, 2.30 mmol), and NaOH (2.77 g, 69.1 mmol) were added to a mixed solvent of 1,4-dioxane / H2O (100 mL / 30 mL), and the mixture was stirred at 120 °C for 2 hours. After cooling to room temperature, the resulting solid was filtered off. The crude product was purified by silica gel filtration to give compound B66 (11.9 g, 80%).

[0279] The following compounds were synthesized in the same manner as those used for the preparation of compound B66, except that (A), (B) and (C) in Table 4 below were used as intermediates.

[0280] [Table 4]

[0281] [Preparation Example 5] Preparation of Compound C24

[0282] 1) Preparation of intermediate C24-1 2-(7-chlorodibenzo[b,d]furan-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborhecyclopentane (8 g, 24.35 mmol), 2-chloro-4-(dibenzo[b,d]furan-1-yl)-6-phenyl-1,3,5-triazine (8.62 g, 23.86 mmol), Pd(pph3)4 (1.41 g, 1.22 mmol), and K2CO3 (7.74 g, 73.04 mmol) were added to a mixed solvent of 1,4-dioxane / H2O (80 mL / 16 mL) and stirred at 110 °C for 2 hours. After cooling to room temperature, the resulting solid was filtered to give intermediate C24-1 (11 g, 86.23%).

[0283] 2) Preparation of compound C24 Intermediate C24-1 (11.0 g, 20.9 mmol), (4-(naphthyl-2-yl)phenyl)boronic acid (6.25 g, 25.19 mmol), Pd2(dba)3 (0.6 g, 1.15 mmol), XPhos (1.0 g, 2.1 mmol), and NaOH (2.52 g, 62.98 mmol) were added to a mixed solvent of 1,4-dioxane / H2O (110 mL / 22 mL), and the mixture was stirred at 120 °C for 2 hours. After cooling to room temperature, the resulting solid was filtered off. The crude product was purified by silica gel chromatography to give compound C24 (12 g, 83%).

[0284] The following compounds were synthesized in the same manner as those used for the preparation of compound C24, except that (A), (B) and (C) in Table 5 below were used as intermediates.

[0285] [Table 5]

[0286] The results of the synthesis confirmation are shown in Tables 6 and 7 below. Table 6 shows... 1 H NMR (CDCl3, 400MHz) data, and Table 7 shows the measurement results obtained by FD-mass spectrometry (FD-MS: field desorption mass spectrometry).

[0287] [Table 6]

[0288] [Table 7]

[0289] [Experimental Example] <Experimental Example 1> - Fabrication of an Organic Light-Emitting Device 1) Fabrication of organic light-emitting devices The glass substrate coated with indium tin oxide (ITO, 1,500 Å) was ultrasonically cleaned with distilled water. Following the distilled water cleaning, the substrate was further ultrasonically cleaned using solvents such as acetone, methanol, and isopropanol, and then dried. The dried substrate was then subjected to UVO (ultraviolet ozone) treatment for 5 minutes in a UV (ultraviolet) cleaner. Subsequently, the substrate was transferred to a plasma cleaner (PT), where plasma treatment under vacuum was performed to adjust the work function of the ITO and remove residual contaminants. The treated substrate was then transferred to a thermal evaporation system for organic deposition.

[0290] On an ITO transparent electrode (anode), a common layer comprising a hole injection layer of 2-TNATA (4,4',4''-tris[2-naphthyl(phenyl)amino]triphenylamine) and a hole transport layer of NPB (N,N'-di(1-naphthyl)-N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine) is sequentially formed.

[0291] The emission layer was then deposited on the common layer by thermal vacuum deposition as follows. Specifically, the compounds described in Examples A to C were used as the red host material for the emission layer, and a red phosphorescent dopant (piq)₂Ir(acac) was doped into the red host at a concentration of 3 wt% to form an emission layer with a thickness of 500 Å. Subsequently, copper bath (BCP) was deposited to a thickness of 60 Å as a hole blocking layer, and Alq₃ was deposited on the hole blocking layer to a thickness of 200 Å as an electron transport layer.

[0292] Finally, lithium fluoride (LiF) is deposited to a thickness of 10 Å on the electron transport layer to form an electron injection layer, and then an aluminum (Al) cathode is deposited to a thickness of 1,200 Å on the electron injection layer to fabricate an organic light-emitting device.

[0293] Meanwhile, all the organic compounds required to manufacture OLED devices are available for each material in 10... -6 Up to 10 -8 The material is purified by vacuum sublimation under pressure and then used in device manufacturing.

[0294] 2) Driving voltage and luminous efficiency of organic light-emitting devices For the organic light-emitting devices prepared as described above, including compounds A to C of the examples shown in Tables 1 to 5, electroluminescence (EL) characteristics were measured using the M7000 system (McScience). Based on these measurements, the lifetime measurement system (M6000, McScience) achieved a lifespan of 6,000 cd / m³. 2 The lifetime (T90) is evaluated at a reference brightness level. T90 refers to the time (in hours) required for the brightness to decrease to 90% of its initial brightness.

[0295] The characteristics of the measured organic light-emitting devices are shown in Table 8 below.

[0296] [Table 8]

[0297] The compounds D through F used in Table 8 are as follows.

[0298]

[0299] As can be seen from the results in Table 8, when the organic layer of the organic light-emitting device is formed by co-deposition of a mixture of three heterocyclic compounds according to this application, the driving voltage of the organic light-emitting device can be appropriately controlled, and the efficiency and / or lifetime characteristics are improved.

[0300] Specifically, the heterocyclic compound represented by Formula A is characterized by low drive voltage and long lifetime. Therefore, when the heterocyclic compound represented by Formula A is appropriately mixed with the heterocyclic compound represented by Formula B (which exhibits relatively high efficiency) and the heterocyclic compound represented by Formula C (which exhibits relatively high efficiency and long lifetime), it has been confirmed that the drive voltage, efficiency and lifetime characteristics can be further improved.

[0301] The heterocyclic compounds represented by Formula A and Formula B are p-type host materials containing amine substituents, and therefore exhibit high hole mobility. The heterocyclic compound represented by Formula C is a unipolar n-type host with high electron mobility. Therefore, when these materials are combined, they help to achieve charge balance within the device, thereby improving both efficiency and lifetime.

[0302] However, the heterocyclic compound represented by Formula A has a naphthobenzofuran core structure and therefore exhibits a high glass transition temperature (Tg), resulting in excellent thermal stability. The heterocyclic compound represented by Formula B has a bipolar structure including azazinyl and amine or carbazole substituents, and thus also exhibits a stable Tg value. In contrast, the heterocyclic compound represented by Formula C has a monopolar n-host structure in which the azazinyl and aryl groups are substituted on the dibenzofuran core, and therefore has a relatively low Tg, which may lead to reduced thermal stability. Therefore, it is preferable to limit the content of the heterocyclic compound represented by Formula C to 25% or less.

[0303] As shown in Comparative Examples 10 to 12, when excessive amounts of heterocyclic compounds represented by Formula C are included (60% or higher), thermal stability decreases, resulting in a shorter lifetime compared to other examples in which heterocyclic compounds represented by Formula C are included in appropriate amounts.

Claims

1. A composition for an organic light-emitting device, comprising a heterocyclic compound represented by the following chemical formula A, a heterocyclic compound represented by the following chemical formula B, and a heterocyclic compound represented by the following chemical formula C: [Chemical Formula A] In chemical formula A, X is O or S. L1 and L2 are each independently: a direct bond; a substituted or unsubstituted C6-C60 arylene; or a substituted or unsubstituted C2-C60 heteroarylene. l1 and l2 are each independent integers from 1 to 3, and when l1 or l2 is 2 or greater, the substituents in the parentheses are different from each other. Ar1 to Ar3 are each independently: substituted or unsubstituted C6-C60 aryl; or substituted or unsubstituted C2-C60 heteroaryl. R1 to R3 are each independently: hydrogen; deuterium; halogen group; cyano; substituted or unsubstituted C1-C60 alkyl; substituted or unsubstituted C3-C60 cycloalkyl; substituted or unsubstituted C2-C60 heterocycloalkyl; substituted or unsubstituted C6-C60 aryl; or substituted or unsubstituted C2-C60 heteroaryl, and r1 is an integer from 1 to 4, r2 is an integer from 0 to 4, and r3 is an integer from 1 to 4, provided that r1 + r2 + r3 equals 8; and when each of r1, r2, and r3 is 2 or greater, the substituents in parentheses are either the same or different from each other. [Chemical Formula B] In chemical formula B, Y is either O or S. Cy1 is: a substituted or unsubstituted benzene ring; or a substituted or unsubstituted naphthalene ring. L3 and L4 are each independently: a direct bond; a substituted or unsubstituted C6-C60 arylene; or a substituted or unsubstituted C2-C60 heteroarylene. l3 and l4 are each independent integers from 1 to 3, and when l3 or l4 is 2 or greater, the substituents in parentheses are the same or different. One of R4 and R5 is a substituted or unsubstituted heteroaryl group containing a C=N bond, and the other of R4 and R5 is a substituted or unsubstituted carbazole group or a substituted or unsubstituted amino group. R6 and R7 are each independently: hydrogen; deuterium; halogen group; cyano; substituted or unsubstituted C1-C60 alkyl; substituted or unsubstituted C3-C60 cycloalkyl; substituted or unsubstituted C2-C60 heterocycloalkyl; substituted or unsubstituted C6-C60 aryl; or substituted or unsubstituted C2-C60 heteroaryl, and r6 is an integer from 1 to 4 and r7 is an integer from 1 to 6, and when r6 or r7 is 2 or greater, the substituents in parentheses are the same or different. [Chemical formula C] In chemical formula C, Z is either O or S. One of R21 to R28 is a substituted or unsubstituted heteroaryl group containing a C=N bond, and The remaining members of R21 to R28 are, independently: hydrogen; deuterium; halogen group; cyano; substituted or unsubstituted C1-C60 alkyl; substituted or unsubstituted C3-C60 cycloalkyl; substituted or unsubstituted C2-C60 heterocycloalkyl; substituted or unsubstituted C6-C60 aryl; or substituted or unsubstituted C2-C60 heteroaryl.

2. The composition for an organic light-emitting device according to claim 1, in, Chemical formula A is represented by any one of the following chemical formulas A-1 to A-5: [Chemical Formula A-1] [Chemical Formula A-2] [Chemical Formula A-3] [Chemical Formula A-4] [Chemical Formula A-5] In chemical formulas A-1 to A-5, X, R1, R2, R3, L1, L2, Ar1, Ar2, Ar3, l1, l2, r1, r2, and r3 are as defined in the above chemical formula A.

3. The composition for an organic light-emitting device according to claim 1, in, Ar1 to Ar3 are each independently: substituted or unsubstituted phenyl; substituted or unsubstituted biphenyl; substituted or unsubstituted terphenyl; substituted or unsubstituted naphthyl; substituted or unsubstituted phenanthyl; substituted or unsubstituted fluorenyl; substituted or unsubstituted dibenzofuranyl; or substituted or unsubstituted dibenzothiopheneyl.

4. The composition for an organic light-emitting device according to claim 1, in, Chemical formula B is represented by any one of the following chemical formulas B-1 to B-10: [Chemical Formula B-1] [Chemical formula B-2] [Chemical Formula B-3] [Chemical Formula B-4] [Chemical Formula B-5] [Chemical Formula B-6] [Chemical Formula B-7] [Chemical Formula B-8] [Chemical Formula B-9] [Chemical Formula B-10] In chemical formulas B-1 to B-10 The definitions of Y, L3, L4, R6, R7, l3, l4, r6, and r7 are the same as those described in chemical formula B above, and R5 is a substituted or unsubstituted carbazole group or a substituted or unsubstituted amino group. R8 represents: hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group. r8 is an integer from 0 to 4, and when r8 is 2 or greater, the substituents in parentheses are either the same or different from each other. N-Het1 is represented by the following structural formula 1. [Structure 1] In structural formula 1, Indicates the connection site with another structure. Y1 to Y5 are each independently either CRa or N, provided that at least one of Y1 to Y5 is N, and Ra is: a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group; or two or more adjacent Ra groups bonded to each other to form a ring.

5. The composition for an organic light-emitting device according to claim 1, in, One of R4 and R5 is a substituted or unsubstituted heteroaryl group including a C=N bond, and the other of R4 and R5 is: a substituted or unsubstituted benzocarbazolyl group; a substituted or unsubstituted dibenzocarbazolyl group; or an amino group substituted with a substituted or unsubstituted C6 to C60 aryl group or a substituted or unsubstituted C2 to C60 heteroaryl group.

6. The composition for an organic light-emitting device according to claim 1, in, Chemical formula C is represented by any one of the following chemical formulas C-1 to C-3: [Chemical formula C-1] [Chemical formula C-2] [Chemical formula C-3] In chemical formulas C-1 to C-3 The definition of Z is the same as the definition described in equation C above. L5 and L6 are each independently: a direct bond; a substituted or unsubstituted C6 to C60 arylene; or a substituted or unsubstituted C2 to C60 heteroarylene. R29 is: a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group. R30 and R31 are each independently either hydrogen or deuterium. r30 is an integer from 0 to 3. When r30 is 2 or greater, the substituents within the parentheses are either the same or different from each other. r31 is an integer from 0 to 4. When r31 is 2 or greater, the substituents within the parentheses are either the same or different from each other. l5 and l6 are each independent integers from 1 to 3, and when l5 and l6 are each 2 or greater, the substituents in parentheses are either the same or different from each other. N-Het2 is represented by the following structural formula 2. [Structure 2] In structural formula 2, Indicates the connection site with another structure. Y6 to Y10 are each independently CRb or N, provided that at least one of Y6 to Y10 is N, and Rb is: a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group; or two or more adjacent Rb groups bonded to each other to form a ring.

7. The composition for an organic light-emitting device according to claim 6, in, R29 is: hydrogen; deuterium; substituted or unsubstituted phenyl; substituted or unsubstituted biphenyl; substituted or unsubstituted terphenyl; substituted or unsubstituted naphthyl; substituted or unsubstituted phenanthryl; substituted or unsubstituted triphenylene; substituted or unsubstituted phosphine oxide; substituted or unsubstituted silyl; substituted or unsubstituted dibenzofuranyl; or substituted or unsubstituted dibenzothiopheneyl.

8. The composition for an organic light-emitting device according to claim 1, in, Chemical formula A includes any of the following compounds: 。 9. The composition for an organic light-emitting device according to claim 1, in, Chemical formula B includes any of the following compounds: 。 10. The composition for an organic light-emitting device according to claim 1, in, Chemical formula C includes any of the following compounds: 。 11. The composition for an organic light-emitting device according to claim 1, in, The heterocyclic compound represented by chemical formula A, the heterocyclic compound represented by chemical formula B, and the heterocyclic compound represented by chemical formula C exist in a molar ratio of 0.1-3:0.1-2:0.1-2.

5.

12. The composition for an organic light-emitting device according to claim 1, in, Based on the total molar number of the heterocyclic compound represented by chemical formula A, the heterocyclic compound represented by chemical formula B, and the heterocyclic compound represented by chemical formula C, the heterocyclic compound represented by formula C is contained in an amount of less than 60%.

13. An organic light-emitting device, comprising: First electrode; The second electrode is configured to face 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 the composition for the organic light-emitting device according to any one of claims 1 to 12.

14. The organic light-emitting device according to claim 13, in, The organic material layer further includes an emission layer, and the emission layer includes the composition for the organic light-emitting device.

15. The organic light-emitting device according to claim 14, in, The emission layer simultaneously includes the heterocyclic compound represented by chemical formula A, the heterocyclic compound represented by chemical formula B, and the heterocyclic compound represented by chemical formula C.

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