Composition for organic material layer of organic light-emitting device, and organic light-emitting device comprising same

Abstract

The present specification provides a composition for an organic material layer of an organic light-emitting device, and an organic light-emitting device comprising same, the composition 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. When used in an organic light-emitting device, the composition for an organic material layer of an organic light-emitting device, disclosed in the present specification, can lower the driving voltage of the device, improve luminous efficiency, and improve lifespan characteristics of the device.

Description

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

[0001] The present specification relates to a composition for an organic layer of an organic light-emitting device and an organic light-emitting device comprising the same.

[0002] <Cross-reference to related applications>

[0003] This application claims the benefit of Korean Patent Application No. 10-2023-0150160, filed with the Korean Intellectual Property Office on November 2, 2023, the entire contents of which are incorporated herein by reference.

[0004] Light-emitting elements are a type of self-luminous display element that have the advantages of a wide viewing angle, excellent contrast, and a fast response speed.

[0005] Organic light-emitting devices have a structure in which an organic thin film is placed between two electrodes. When voltage is applied to an organic light-emitting device of this structure, electrons and holes injected from the two electrodes combine in the organic thin film, forming pairs and then disappearing, emitting light. The organic thin film may be composed of a single layer or multiple layers, as needed.

[0006] The material of the organic thin film may have a light-emitting function as needed. For example, the organic thin film material may be a compound that can form a light-emitting layer on its own, or a compound that can act as a host or dopant in a host-dopant light-emitting layer. In addition, the material of the organic thin film may be a compound that can perform roles such as hole injection, hole transport, electron blocking, hole blocking, electron transport, and electron injection.

[0007] To improve the performance, lifespan, or efficiency of organic light-emitting devices, the development of materials for organic thin films is continuously required.

[0008] [Prior Art Document] (Patent Document 1) U.S. Patent No. 4,356,429

[0009] The present specification provides a composition for an organic layer of an organic light-emitting device and an organic light-emitting device including the same.

[0010] One embodiment of the present specification provides a composition for an organic layer of 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.

[0011] [Chemical Formula A]

[0012]

[0013] [Chemical Formula B]

[0014]

[0015] [Chemical Formula C]

[0016]

[0017] In the above chemical formulas A, B and C,

[0018] X1 to X3 are the same or different from each other, and are each independently O; or S,

[0019] L1 to L4 and L6 are the same or different from each other, and each independently represents a direct bond; a substituted or unsubstituted C6 to C60 arylene group; a substituted or unsubstituted C2 to C60 heteroarylene group; or a combination thereof,

[0020] Ar1 to Ar4 are the same or different from each other, and are each independently a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; or a combination thereof,

[0021] R1 to R8 are the same or different from each other, and are each independently 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; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)RR'; -SiRR'R"; or a combination thereof,

[0022] The above R, R' and R" are the same or different from each other, and each independently represents hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0023] l1 to l4 and l6 are the same or different from each other, and are each independently an integer from 1 to 3, and when l1 to l4 and l6 are each an integer of 2 or more, the substituents in the parentheses are the same or different from each other,

[0024] r1, r3, r4, r6 and r8 are the same or different from each other and are each independently an integer from 0 to 4,

[0025] r2 and r5 are the same or different from each other, and are each independently an integer from 0 to 2,

[0026] r7 is an integer from 0 to 3,

[0027] If each of r1 to r8 is an integer greater than or equal to 2, the substituents in parentheses are the same or different from each other,

[0028] N-Het1 and N-Het2 are each represented by the structural formula N below,

[0029] [Structural formula N]

[0030]

[0031] In the above structural formula N,

[0032] refers to the part that is connected to L3 and L6 respectively,

[0033] Y1 to Y5 are the same or different from each other, and are each independently CRa or N, but at least one is N,

[0034] Ra is a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; or a combination thereof.

[0035] Another embodiment of the present invention provides an organic light-emitting device comprising a first electrode; a second electrode provided opposite the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein at least one of the organic layers comprises the composition for an organic layer of the organic light-emitting device described above.

[0036] An organic layer composition according to an exemplary embodiment of the present specification can be used as an organic layer material of an organic light-emitting device. In particular, the organic layer composition comprises a heterocyclic compound represented by chemical formula A as a P-Type Host having a long-life characteristic, a heterocyclic compound represented by chemical formula B as an N-Type Host having a high-efficiency characteristic, and a heterocyclic compound represented by chemical formula C as an N-Type Host having a fast electron mobility and excellent voltage characteristics, which has the effect of improving device characteristics compared to a case where one type of compound, two types of compounds are pre-mixed, or a case where two or more compounds are pre-mixed in a combination different from the exemplary embodiment of the present specification.

[0037] Accordingly, when the composition for the organic layer is used in an organic light-emitting device, the driving voltage of the device can be lowered, the light efficiency can be improved, the thermal stability of the compound can be improved, and the lifespan characteristics of the device can be improved.

[0038] Figures 1 to 3 are drawings each exemplifying a laminated structure of an organic light-emitting device according to one embodiment of the present specification.

[0039] [Explanation of symbols]

[0040] 100: Substrate

[0041] 200: Bipolar

[0042] 300: Organic layer

[0043] 301: Hole injection layer

[0044] 302: Hole transport layer

[0045] 303: Emissive layer

[0046] 304: Hole-blocking layer

[0047] 305: Electron transport layer

[0048] 306: Electron injection layer

[0049] 400: Cathode

[0050] Hereinafter, the present specification will be described in more detail.

[0051] In this specification, when a part is said to "include" a component, this means that it may include other components, but not to the exclusion of other components, unless specifically stated otherwise.

[0052] In this specification, the chemical formula means the position where it is combined.

[0053] The term "substitution" above means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position of substitution is not limited as long as it is a position where a hydrogen atom is replaced, i.e. a position where a substituent can be replaced, and when two or more are replaced, the two or more substituents may be the same or different from each other.

[0054] In this specification, “substituted or unsubstituted” means substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium; a halogen group; a cyano group; a C1 to C60 alkyl group; a C2 to C60 alkenyl group; a C2 to C60 alkynyl group; a C3 to C60 cycloalkyl group; a C2 to C60 heterocycloalkyl group; a C6 to C60 aryl group; a C2 to C60 heteroaryl group; a silyl group; a phosphine oxide group; and an amine group, or a substituent in which two or more substituents selected from the above-mentioned substituents are linked.

[0055] In this specification, “when no substituent is indicated in the chemical formula or compound structure” means that a hydrogen atom is bonded to a carbon atom. However, deuterium ( 2 H, Deuterium) is an isotope of hydrogen, so some hydrogen atoms may be deuterium.

[0056] In one embodiment of the present specification, “when no substituent is indicated in the chemical formula or compound structure” may mean that all positions that can be substituted are hydrogen or deuterium. That is, in the case of deuterium, it is an isotope of hydrogen, and some hydrogen atoms may be the isotope deuterium, and in this case, the deuterium content may be 0% to 100%.

[0057] In one embodiment of the present specification, in the case where “no substituent is indicated in the chemical formula or compound structure,” if the content of deuterium is 0%, the content of hydrogen is 100%, and all substituents are hydrogen, etc., and deuterium is not explicitly excluded, hydrogen and deuterium may be used in combination in the compound.

[0058] In one embodiment of the present specification, deuterium is an element having a deuteron, which is one of the isotopes of hydrogen and is composed of one proton and one neutron, as its nucleus, and can be expressed as hydrogen-2, and its element symbol is D or 2 It can also be written as H.

[0059] In one embodiment of the present specification, an isotope means an atom having the same atomic number (Z) but a different mass number (A). An isotope can also be interpreted as an element having the same number of protons but a different number of neutrons.

[0060] In one embodiment of the present specification, the content T% of a specific substituent can be defined as T2 / T1×100 = T% when the total number of substituents that the basic compound can have is defined as T1, and the number of specific substituents among them is defined as T2.

[0061] in other words, For example, in the case of a phenyl group represented by , a content of 20% of deuterium here means that the total number of substituents that the phenyl group can have is 5 (T1 in the formula), and if the number of deuterium among them is 1 (T2 in the formula), it can be expressed as 20%. In other words, a content of 20% of deuterium in the phenyl group can be expressed by the structural formula below.

[0062]

[0063] Additionally, in one embodiment of the present specification, “a phenyl group having a deuterium content of 0%” may mean a phenyl group that does not contain a deuterium atom, i.e., has 5 hydrogen atoms.

[0064] In this specification, the halogen may be fluorine, chlorine, bromine or iodine.

[0065] In the present specification, the alkyl group includes a straight or branched chain having 1 to 60 carbon atoms, and may be further substituted by another substituent. The alkyl group may have 1 to 60 carbon atoms, specifically 1 to 40 carbon atoms, and more specifically 1 to 20 carbon atoms. Specific examples include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methyl-butyl group, 1-ethyl-butyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl-2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, cyclopentylmethyl group, cyclohexylmethyl group, octyl group, n-octyl group, tert-octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, Examples include, but are not limited to, 2,2-dimethylheptyl group, 1-ethyl-propyl group, 1,1-dimethyl-propyl group, isohexyl group, 2-methylpentyl group, 4-methylhexyl group, and 5-methylhexyl group.

[0066] In the present specification, the alkenyl group includes a straight or branched chain having 2 to 60 carbon atoms, and may be further substituted by another substituent. The alkenyl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, and more specifically 2 to 20 carbon atoms. Specific examples include, but are not limited to, a vinyl group, a 1-propenyl group, an isopropenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-pentenyl group, a 2-pentenyl group, a 3-pentenyl group, a 3-methyl-1-butenyl group, a 1,3-butadienyl group, an allyl group, a 1-phenylvinyl-1-yl group, a 2-phenylvinyl-1-yl group, a 2,2-diphenylvinyl-1-yl group, a 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl group, a 2,2-bis(diphenyl-1-yl)vinyl-1-yl group, a stilbenyl group, and a styrenyl group.

[0067] In the present specification, the alkynyl group includes a straight or branched chain having 2 to 60 carbon atoms, and may be further substituted by another substituent. The alkynyl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, and more specifically 2 to 20 carbon atoms.

[0068] In the present specification, the alkoxy group may be straight chain, branched chain, or cyclic. The carbon number of the alkoxy group is not particularly limited, but is preferably 1 to 20 carbon atoms. Specifically, it may be methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc., but is not limited thereto.

[0069] In the present specification, the cycloalkyl group includes a monocyclic or polycyclic group having 3 to 60 carbon atoms, and may be further substituted by another substituent. Here, polycyclic means a group in which a cycloalkyl group is directly connected to or condensed with another ring group. Here, the other ring group may be a cycloalkyl group, but may also be another type of ring group, such as a heterocycloalkyl group, an aryl group, a heteroaryl group, etc. The cycloalkyl group may have 3 to 60 carbon atoms, specifically 3 to 40 carbon atoms, and more specifically 5 to 20 carbon atoms. Specifically, there are, but are not limited to, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a 3-methylcyclopentyl group, a 2,3-dimethylcyclopentyl group, a cyclohexyl group, a 3-methylcyclohexyl group, a 4-methylcyclohexyl group, a 2,3-dimethylcyclohexyl group, a 3,4,5-trimethylcyclohexyl group, a 4-tert-butylcyclohexyl group, a cycloheptyl group, a cyclooctyl group, etc.

[0070] In the present specification, the heterocycloalkyl group includes O, S, Se, N or Si as a heteroatom, and includes a monocyclic or polycyclic group having 2 to 60 carbon atoms, and may be further substituted by another substituent. Here, polycyclic means a group in which a heterocycloalkyl group is directly connected to or condensed with another ring group. Here, the other ring group may be a heterocycloalkyl group, but may also be another type of ring group, such as a cycloalkyl group, an aryl group, a heteroaryl group, etc. The heterocycloalkyl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, and more specifically 3 to 20 carbon atoms.

[0071] In the present specification, the aryl group includes a monocyclic or polycyclic ring having 6 to 60 carbon atoms, and may be further substituted by another substituent. Here, polycyclic means a group in which an aryl group is directly connected to or condensed with another ring group. Here, the other ring group may be an aryl group, but may also be another type of ring group, such as a cycloalkyl group, a heterocycloalkyl group, a heteroaryl group, etc. The aryl group includes a spiro group. The aryl group may have 6 to 60 carbon atoms, specifically 6 to 40 carbon atoms, and more specifically 6 to 25 carbon atoms. Specific examples of the above aryl group include, but are not limited to, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthryl group, a chrysenyl group, a phenanthrenyl group, a perylenyl group, a fluoranthenyl group, a triphenylenyl group, a phenalenyl group, a pyrenyl group, a tetracenyl group, a pentacenyl group, a fluorenyl group, an indenyl group, an acenaphthylenyl group, a benzofluorenyl group, a spirobifluorenyl group, a 2,3-dihydro-1H-indenyl group, and condensed ring groups thereof.

[0072] In this specification, the terphenyl group may be selected from the following structures.

[0073]

[0074] In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be combined with each other to form a ring.

[0075] When the above fluorenyl group is substituted, it may be selected from the following structures, but is not limited thereto.

[0076]

[0077] In the present specification, the heteroaryl group includes S, O, Se, N or Si as a heteroatom, and includes a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may be further substituted by another substituent. Here, the polycyclic ring means a group in which a heteroaryl group is directly connected to or condensed with another ring group. Here, the other ring group may be a heteroaryl group, but may also be another type of ring group, such as a cycloalkyl group, a heterocycloalkyl group, an aryl group, etc. The heteroaryl group may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, and more specifically 3 to 25 carbon atoms.Specific examples of the above heteroaryl group include a pyridyl group, a pyrrolyl group, a pyrimidyl group, a pyridazinyl group, a furanyl group, a thiophene group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, a furazanyl group, an oxadiazolyl group, a thiadiazolyl group, a dithiazolyl group, a tetrazolyl group, a pyranyl group, a thiopyranyl group, a diazinyl group, an oxazinyl group, a thiazinyl group, a deoxynyl group, a triazinyl group, a tetrazinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, an isoquinazolinyl group, a quinozolinyl group, a naphthyridyl group, an acridinyl group, a phenanthridinyl group, an imidazopyridinyl group, a diazanaphthalenyl group, Triazindene group, indolyl group, indolizinyl group, benzothiazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiophene group, benzofuran group, dibenzothiophene group, dibenzofuran group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, phenazinyl group, dibenzosilole group, spirobi(dibenzosilole) group, dihydrophenazinyl group, phenoxazinyl group, phenanthridyl group, imidazopyridinyl group, thienyl group, indolo[2,3-a]carbazolyl group, indolo[2,3-b]carbazolyl group, indolinyl group, 10,11-dihydro-dibenzo[b,f]azepine group, 9,10-dihydroacridinyl group, phenanthrazinyl group, phenothiathiazinyl group, Examples thereof include, but are not limited to, a phthalazinyl group, a naphthyridinyl group, a phenanthrolinyl group, a benzo[c][1,2,5]thiadiazolyl group, a 2,3-dihydrobenzo[b]thiophene group, a 2,3-dihydrobenzofuran group, a 5,10-dihydrodibenzo[b,e][1,4]azasilinyl group, a pyrazolo[1,5-c]quinazolinyl group, a pyrido[1,2-b]indazolyl group, a pyrido[1,2-a]imidazo[1,2-e]indolinyl group, and a 5,11-dihydroindeno[1,2-b]carbazolyl group.

[0078] In the present specification, when the substituent is a carbazole group, it means that it is bonded to the nitrogen or carbon of the carbazole.

[0079] In the present specification, when a carbazole group is substituted, an additional substituent may be substituted on the nitrogen or carbon of the carbazole.

[0080] In the present specification, the benzocarbazole group may have any of the following structures.

[0081]

[0082] In the present specification, the dibenzocarbazole group may have any of the following structures.

[0083]

[0084] In the present specification, the naphthobenzofuran group may have any of the following structures.

[0085]

[0086] In the present specification, the naphthobenzothiophene group may have any of the following structures.

[0087]

[0088] In the present specification, a silyl group is a substituent that contains Si and is directly connected to the Si atom as a radical, and is represented by -Si(R101)(R102)(R103), and R101 to R103 are the same as or different from each other, and may each independently be a substituent composed of at least one of hydrogen; deuterium; a halogen group; an alkyl group; an alkenyl group; an alkoxy group; a cycloalkyl group; a heterocycloalkyl group; an aryl group; and a heteroaryl group.

[0089] A specific example of a cylinder is (trimethylsilyl group), (triethylsilyl group), (t-butyldimethylsilyl group), (vinyldimethylsilyl group), (propyldimethylsilyl group), (triphenylsilyl group), (diphenylsilyl group), (phenylsilyl group), but is not limited thereto.

[0090] In the present specification, the phosphine oxide group is represented by -P(=O)(R104)(R105), and R104 and R105 are the same or different from each other, and can each independently be a substituent composed of at least one of hydrogen; deuterium; a halogen group; an alkyl group; an alkenyl group; an alkoxy group; a cycloalkyl group; a heterocycloalkyl group; an aryl group; and a heteroaryl group. Specifically, it can be substituted with an alkyl group or an aryl group, and the above-described examples can be applied to the alkyl group and the aryl group. For example, the phosphine oxide group includes, but is not limited to, a dimethylphosphine oxide group, a diphenylphosphine oxide group, a dinaphthylphosphine oxide group, and the like.

[0091] In the present specification, the amine group is represented by -N(R106)(R107), and R106 and R107 are the same or different from each other, and can each independently be a substituent composed of at least one of hydrogen; deuterium; a halogen group; an alkyl group; an alkenyl group; an alkoxy group; a cycloalkyl group; a heterocycloalkyl group; an aryl group; and a heteroaryl group. The amine group can be selected from the group consisting of -NH2; a monoalkylamine group; a monoarylamine group; a monoheteroarylamine group; a dialkylamine group; a diarylamine group; a diheteroarylamine group; an alkylarylamine group; an alkylheteroarylamine group; and an arylheteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the above amine group include, but are not limited to, a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, a dibiphenylamine group, anthracenylamine group, a 9-methyl-anthracenylamine group, a diphenylamine group, a phenylnaphthylamine group, a ditolylamine group, a phenyltolylamine group, a triphenylamine group, a biphenylnaphthylamine group, a phenylbiphenylamine group, a biphenylfluorenylamine group, a phenyltriphenylenylamine group, and a biphenyltriphenylenylamine group.

[0092] In this specification, the arylene group may be applied to the examples of the aryl group described above, except that it is a divalent group.

[0093] In this specification, the heteroarylene group may be applied to the examples of the heteroaryl group described above, except that it is a divalent group.

[0094] As used herein, the term "adjacent" may refer to a substituent substituted on an atom directly connected to the atom substituted by the substituent, a substituent sterically closest to the substituent, or another substituent substituted on the atom substituted by the substituent. For example, two substituents substituted at ortho positions in a benzene ring and two substituents substituted on the same carbon in an aliphatic ring may be interpreted as "adjacent" to each other.

[0095] Hydrocarbon rings and heterocycles that adjacent groups can form include aliphatic hydrocarbon rings, aromatic hydrocarbon rings, aliphatic heterocycles, and aromatic heterocycles, and structures exemplified by the aforementioned cycloalkyl groups, aryl groups, heterocycloalkyl groups, and heteroaryl groups can be applied to the rings, except that they are not monovalent groups.

[0096] <Composition for organic layer of organic light-emitting device>

[0097] Hereinafter, a composition for an organic layer of an organic light-emitting device according to the present specification will be described.

[0098] A composition for an organic layer of an organic light-emitting device according to one embodiment of the present specification includes a heterocyclic compound represented by the following chemical formula A.

[0099] [Chemical Formula A]

[0100]

[0101] In the above chemical formula A, the description of each substituent is as described above.

[0102] The heterocyclic compound represented by the above chemical formula A has an amine substituent (-(L1)l1-N(Ar1)(Ar2)) with strong hole transport properties, which facilitates hole movement when used in a hole transport layer in the future, and thus can have long-life characteristics. However, when used alone, hole trapping is not easy, which limits efficiency increase.

[0103] A composition for an organic layer of an organic light-emitting device according to one embodiment of the present specification includes a heterocyclic compound represented by the following chemical formula B.

[0104] [Chemical Formula B]

[0105]

[0106] In the above chemical formula B, the description of each substituent is as described above.

[0107] The heterocyclic compound represented by the above chemical formula B has a substituent with strong electron transfer properties, which facilitates electron transfer and thus has high efficiency properties.

[0108] A composition for an organic layer of an organic light-emitting device according to one embodiment of the present specification includes a heterocyclic compound represented by the following chemical formula C.

[0109] [Chemical Formula C]

[0110]

[0111] In the above chemical formula C, the description of each substituent is as described above.

[0112] The heterocyclic compound represented by the above chemical formula C has a very fast electron transfer rate, so it can provide an effect of improving driving characteristics compared to the above chemical formula B, but it has been confirmed that there is a limitation in increasing the lifespan when used except for the chemical formula B alone.

[0113] The present inventors have discovered that not only does the heterocyclic compound represented by the chemical formula B or C compensate for the hole trapping problem of the heterocyclic compound represented by the chemical formula A, but also that the combination of the heterocyclic compound represented by the chemical formula B and the heterocyclic compound represented by the chemical formula C helps to increase the lifespan by maintaining appropriate current characteristics.

[0114] The composition for an organic layer of an organic light-emitting device according to the above embodiment is a combination of a heterocyclic compound represented by the above chemical formula A, a heterocyclic compound represented by the above chemical formula B, and a heterocyclic compound represented by the above chemical formula C, and when used in an organic light-emitting device in the future, it can have low driving voltage, high luminous efficiency, and / or long life characteristics due to the balance of current and electron movement.

[0115] In one embodiment of the present specification, the chemical formula A may be represented by any one of the following chemical formulas A-1 to A-3.

[0116] [Chemical Formula A-1]

[0117]

[0118] [Chemical Formula A-2]

[0119]

[0120] [Chemical Formula A-3]

[0121]

[0122] In the above chemical formulas A-1 to A-3,

[0123] Each of X1, L1, L2, Ar1 to Ar3, R1 to R3, l1, l2 and r1 to r3 is as defined in the above chemical formula A.

[0124] In one embodiment of the present specification, the chemical formula A may be represented by any one of the following chemical formulas A-11 to A-14.

[0125] [Chemical Formula A-11]

[0126]

[0127] [Chemical Formula A-12]

[0128]

[0129] [Chemical Formula A-13]

[0130]

[0131] [Chemical Formula A-14]

[0132]

[0133] In the above chemical formulas A-11 to A-14,

[0134] Each of X1, L1, L2, Ar1 to Ar3, R1 to R3, l1, l2, r2 and r3 is as defined in the above chemical formula A,

[0135] r1' is an integer from 0 to 3,

[0136] r1" is an integer from 0 to 2,

[0137] r2' is 0 or 1,

[0138] When each of r1' and r1" is 2 or more than 2, the substituents within the parentheses are the same or different.

[0139] In one embodiment of the present specification, the chemical formula A-1 may be represented by any one of the following chemical formulas A-101 to A-118, but is not limited thereto unless it departs from the scope of the present invention.

[0140]

[0141]

[0142]

[0143] In the above chemical formulas A-101 to A-118, the definition of each substituent is as described above, r1' is an integer from 0 to 3, r1" is an integer from 0 to 2, and when each of r1' and r1" is 2 or 2 or more, the substituents in parentheses are the same or different from each other.

[0144] In one embodiment of the present specification, the chemical formula A-2 may be represented by any one of the following chemical formulas A-201 to A-210, but is not limited thereto unless it departs from the scope of the present invention.

[0145]

[0146]

[0147] In the above chemical formulas A-201 to A-210, the definition of each substituent is as described above, r1' is an integer from 0 to 3, r1" is an integer from 0 to 2, and when each of r1' and r1" is 2 or 2 or more, the substituents in parentheses are the same or different from each other.

[0148] In one embodiment of the present specification, the chemical formula A-3 may be represented by any one of the following chemical formulas A-301 to A-318, but is not limited thereto unless it deviates from the scope of the present invention.

[0149]

[0150]

[0151]

[0152] In the above chemical formulas A-301 to A-318, the definition of each substituent is as described above, r1' is an integer from 0 to 3, r1" is an integer from 0 to 2, and when each of r1' and r1" is 2 or 2 or more, the substituents in parentheses are the same or different from each other.

[0153] In one embodiment of the present specification, the chemical formula B may be represented by any one of the following chemical formulas B-1 to B-3.

[0154] [Chemical Formula B-1]

[0155]

[0156] [Chemical Formula B-2]

[0157]

[0158] [Chemical Formula B-3]

[0159]

[0160] In the above chemical formulas B-1 to B-3,

[0161] Each of X2, L3, L4, Ar4, R4 to R6, N-Het1, l3, l4 and r4 to r6 is as defined in the above chemical formula B.

[0162] In one embodiment of the present specification, the chemical formula B may be represented by any one of the following chemical formulas B-11 to B-14.

[0163] [Chemical Formula B-11]

[0164]

[0165] [Chemical Formula B-12]

[0166]

[0167] [Chemical Formula B-13]

[0168]

[0169] [Chemical Formula B-14]

[0170]

[0171] In the above chemical formulas B-11 to B-14,

[0172] Each of X2, L3, L4, Ar4, R4 to R6, N-Het1, l3, l4, r5 and r6 are as defined in the above chemical formula B,

[0173] Each of r4' and r6' is an integer from 0 to 3,

[0174] r4" is an integer from 0 to 2,

[0175] r5' is 0 or 1,

[0176] When each of r4', r4" and r6' is 2 or an integer greater than or equal to 2, the substituents within the parentheses are the same or different.

[0177] In one embodiment of the present specification, the chemical formula B-1 may be represented by any one of the following chemical formulas B-101 to B-125, but is not limited thereto unless it departs from the scope of the present invention.

[0178]

[0179]

[0180]

[0181] In the above chemical formulas B-101 to B-125, the definition of each substituent is as described above,

[0182] r4' is an integer from 0 to 3,

[0183] r4" is an integer from 0 to 2,

[0184] When each of r4' and r4" is 2 or more than 2, the substituents within the parentheses are the same or different.

[0185] In one embodiment of the present specification, the chemical formula B-2 may be represented by any one of the following chemical formulas B-201 to B-211, but is not limited thereto unless it deviates from the scope of the present invention.

[0186]

[0187]

[0188] In the above chemical formulas B-201 to B-211, the definition of each substituent is as described above,

[0189] Each of r4' and r6' is an integer from 0 to 3,

[0190] r4" is an integer from 0 to 2,

[0191] When each of r4', r4" and r6' is 2 or more than 2, the substituents in the parentheses are the same or different.

[0192] In one embodiment of the present specification, the chemical formula B-3 may be represented by any one of the following chemical formulas B-301 to B-312.

[0193]

[0194]

[0195] In the above chemical formulas B-301 to B-312, the definition of each substituent is as described above,

[0196] r4" is an integer from 0 to 2,

[0197] When r4" is 2, the substituents in parentheses are the same or different.

[0198] In one embodiment of the present specification, the chemical formula C may be represented by the following chemical formula C-1 or C-2.

[0199] [Chemical Formula C-1]

[0200]

[0201] [Chemical Formula C-2]

[0202]

[0203] In the above chemical formulas C-1 and C-2,

[0204] Each of X3, N-Het2, L6 and l6 is as defined in the above chemical formula C,

[0205] L5 is a direct bond; a substituted or unsubstituted C6 to C60 arylene group; a substituted or unsubstituted C2 to C60 heteroarylene group; or a combination thereof,

[0206] Ar5 is a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; or a combination thereof,

[0207] R7' and R8' are the same or different, and each independently represent 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; -P(=O)RR'; -SiRR'R"; or a combination thereof,

[0208] The above R, R' and R" are the same or different from each other, and each independently represents hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0209] l5 is an integer from 1 to 3, and if l5 is an integer greater than or equal to 2, L5 are equal or different,

[0210] r7' is an integer from 0 to 3, r8' is an integer from 0 to 4, and when each of r7' and r8' is an integer greater than or equal to 2, the substituents in the parentheses are the same or different.

[0211] In one embodiment of the present specification, the chemical formula C-2 may be represented by the following chemical formula C-21 or C-22.

[0212] [Chemical Formula C-21]

[0213]

[0214] [Chemical Formula C-22]

[0215]

[0216] In the above chemical formulas C-21 and C-22,

[0217] Each of X3, N-Het2, L6, and l6 is as defined in the above chemical formula C,

[0218] Each of L5, Ar5, R7', R8', l5, r7' and r8' is as defined in the above chemical formula C-2,

[0219] r7" is an integer from 0 to 2, r8" is an integer from 0 to 3, and when each of r7' and r8' is 2 or an integer greater than or equal to 2, the substituents in the parentheses are the same or different.

[0220] In one embodiment of the present specification, the chemical formula C-1 may be represented by any one of the following chemical formulas C-101 to C-104.

[0221]

[0222] In the above chemical formulas C-101 to C-104, the definition of each substituent is as described above.

[0223] In one embodiment of the present specification, the chemical formula C-2 may be represented by any one of the following chemical formulas C-201 to C-228.

[0224]

[0225]

[0226]

[0227] In the above chemical formulas C-201 to C-228, the definition of each substituent is as described above.

[0228] In one embodiment of the present specification, L1 to L6 may be the same as or different from each other, and may each independently be a direct bond; a substituted or unsubstituted C6 to C40 arylene group; a substituted or unsubstituted C2 to C40 heteroarylene group; or a combination thereof.

[0229] In one embodiment of the present specification, L1 to L6 may be the same as or different from each other, and may each independently be a direct bond; a substituted or unsubstituted C6 to C30 arylene group; a substituted or unsubstituted C2 to C30 heteroarylene group; or a combination thereof.

[0230] In one embodiment of the present specification, L1 to L6 may be the same or different from each other, and may each independently be a direct bond; a substituted or unsubstituted C6 to C20 arylene group; a substituted or unsubstituted C2 to C20 heteroarylene group; or a combination thereof.

[0231] In one embodiment of the present specification, L1 to L6 may be the same as or different from each other, and may each independently be a direct bond; a substituted or unsubstituted C6 to C20 arylene group; or a combination thereof.

[0232] In one embodiment of the present specification, L1 to L6 may be the same as or different from each other, and may each independently be a direct bond; a C6 to C20 arylene group substituted or unsubstituted with deuterium; or a combination thereof.

[0233] In one embodiment of the present specification, L1 to L6 may be the same as or different from each other, and may each independently be a direct bond; a phenylene group substituted or unsubstituted with deuterium; a naphthylene group substituted or unsubstituted with deuterium; or a combination thereof.

[0234] In one embodiment of the present specification, Ar1 to Ar4 may be the same as or different from each other, and may each independently be a substituted or unsubstituted C6 to C40 aryl group; a substituted or unsubstituted C2 to C40 heteroaryl group; or a combination thereof.

[0235] In one embodiment of the present specification, Ar1 to Ar4 may be the same as or different from each other, and may each independently be a substituted or unsubstituted C6 to C30 aryl group; a substituted or unsubstituted C2 to C30 heteroaryl group; or a combination thereof.

[0236] In one embodiment of the present specification, Ar1 to Ar4 may be the same as or different from each other, and may each independently be a C6 to C30 aryl group unsubstituted or substituted with a substituent selected from the group consisting of deuterium, a cyano group, a halogen group, an alkyl group, a silyl group, a phosphine oxide group, and an aryl group; a C2 to C30 heteroaryl group unsubstituted or substituted with a substituent selected from the group consisting of deuterium, a cyano group, a halogen group, an alkyl group, a silyl group, a phosphine oxide group, and an aryl group; or a combination thereof.

[0237] In one embodiment of the present specification, Ar1 to Ar4 may be the same or different from each other, and may each independently be a phenyl group; a biphenyl group; a terphenyl group; a naphthyl group; a fluorenyl group; a spirobifluorenyl group; a phenanthrenyl group; a triphenyl group; a chrysenyl group; a dibenzofuranyl group; a dibenzothiophenyl group; a carbazolyl group; or a combination thereof, which may each independently be substituted or unsubstituted with a substituent selected from the group consisting of deuterium, a cyano group, a halogen group, an alkyl group, a silyl group, a phosphine oxide group, and an aryl group.

[0238] In one embodiment of the present specification, R1 to R8 may be the same or different, and each independently represent hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C40 alkyl group; a substituted or unsubstituted C3 to C40 cycloalkyl group; a substituted or unsubstituted C2 to C40 heterocycloalkyl group; a substituted or unsubstituted C6 to C40 aryl group; a substituted or unsubstituted C2 to C40 heteroaryl group; -P(=O)RR'; -SiRR'R"; or a combination thereof.

[0239] In one embodiment of the present specification, R1 to R8 may be the same or different, and each independently represent hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C30 alkyl group; a substituted or unsubstituted C3 to C30 cycloalkyl group; a substituted or unsubstituted C2 to C30 heterocycloalkyl group; a substituted or unsubstituted C6 to C30 aryl group; a substituted or unsubstituted C2 to C30 heteroaryl group; -P(=O)RR'; -SiRR'R"; or a combination thereof.

[0240] In one embodiment of the present specification, R1 to R8 may be the same or different from each other, and each independently represent hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C3 to C20 cycloalkyl group; a substituted or unsubstituted C2 to C20 heterocycloalkyl group; a substituted or unsubstituted C6 to C20 aryl group; a substituted or unsubstituted C2 to C20 heteroaryl group; -P(=O)RR'; -SiRR'R"; or a combination thereof.

[0241] In one embodiment of the present specification, R1 to R6 are the same or different from each other, and are each independently hydrogen; or deuterium, and R7 and R8 are the same or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted C6 to C30 aryl group; a substituted or unsubstituted C2 to C30 heteroaryl group; -P(=O)RR'; -SiRR'R"; or a combination thereof.

[0242] In one embodiment of the present specification, R1 to R6 are the same or different from each other, and are each independently hydrogen; or deuterium, and R7 and R8 are the same or different from each other, and are each independently hydrogen; deuterium; a C6 to C30 aryl group unsubstituted or substituted with a substituent selected from the group consisting of deuterium, a cyano group, a halogen group, an alkyl group, a silyl group, a phosphine oxide group, and an aryl group; a C2 to C30 heteroaryl group unsubstituted or substituted with a substituent selected from the group consisting of deuterium, a cyano group, a halogen group, an alkyl group, a silyl group, a phosphine oxide group, and an aryl group; -P(=O)RR'; -SiRR'R"; or a combination thereof.

[0243] In one embodiment of the present specification, R1 to R6 are the same or different from each other, and are each independently hydrogen; or deuterium, and R7 and R8 are the same or different from each other, and are each independently hydrogen; deuterium; phenyl group; biphenyl group; terphenyl group; naphthyl group; fluorenyl group; spirobifluorenyl group; phenanthrenyl group; triphenyl group; chrysenyl group; dibenzofuranyl group; dibenzothiophenyl group; carbazolyl group; -P(=O)RR'; -SiRR'R"; or a combination thereof, and the phenyl group; biphenyl group; terphenyl group; naphthyl group; fluorenyl group; spirobifluorenyl group; phenanthrenyl group; triphenyl group; chrysenyl group; dibenzofuranyl group; dibenzothiophenyl group; and carbazolyl group may each be independently substituted or unsubstituted with a substituent selected from the group consisting of deuterium, cyano group, halogen group, alkyl group, silyl group, phosphine oxide group, and aryl group.

[0244] In one embodiment of the present specification, the structural formula N may be represented by any one of the following structural formulas.

[0245]

[0246]

[0247] In the above structural formula, And the definitions of Y1 to Y5 are as defined in structural formula N.

[0248] In one embodiment of the present specification, the structural formula N may be represented by the following structure.

[0249]

[0250] In the above structural formula, And the definitions of Y2 and Y4 are as defined in structural formula N.

[0251] In one embodiment of the present specification, Ra may be a substituted or unsubstituted C6 to C40 aryl group; a substituted or unsubstituted C2 to C40 heteroaryl group; or a combination thereof.

[0252] In one embodiment of the present specification, Ra may be a substituted or unsubstituted C6 to C30 aryl group; a substituted or unsubstituted C2 to C30 heteroaryl group; or a combination thereof.

[0253] In one embodiment of the present specification, Ra may be a C6 to C30 aryl group unsubstituted or substituted with a substituent selected from the group consisting of deuterium, a cyano group, a halogen group, an alkyl group, a silyl group, a phosphine oxide group, an aryl group, and a heteroaryl group; a C2 to C30 heteroaryl group unsubstituted or substituted with a substituent selected from the group consisting of deuterium, a cyano group, a halogen group, an alkyl group, a silyl group, a phosphine oxide group, an aryl group, and a heteroaryl group; or a combination thereof.

[0254] In one embodiment of the present specification, Ra may be a phenyl group; a biphenyl group; a terphenyl group; a naphthyl group; a fluorenyl group; a spirobifluorenyl group; a phenanthrenyl group; a triphenyl group; a chrysenyl group; a dibenzofuranyl group; a dibenzothiophenyl group; a carbazolyl group; or a combination thereof, each of which may be independently substituted or unsubstituted with a substituent selected from the group consisting of deuterium, a cyano group, a halogen group, an alkyl group, a silyl group, a phosphine oxide group, an aryl group, and a heteroaryl group.

[0255] In one embodiment of the present specification, Ar5 may be a substituted or unsubstituted C6 to C40 aryl group; a substituted or unsubstituted C2 to C40 heteroaryl group; or a combination thereof.

[0256] In one embodiment of the present specification, Ar5 may be a substituted or unsubstituted C6 to C30 aryl group; a substituted or unsubstituted C2 to C30 heteroaryl group; or a combination thereof.

[0257] In one embodiment of the present specification, Ar5 may be a C6 to C30 aryl group unsubstituted or substituted with a substituent selected from the group consisting of deuterium, a cyano group, a halogen group, an alkyl group, a silyl group, a phosphine oxide group, and an aryl group; a C2 to C30 heteroaryl group unsubstituted or substituted with a substituent selected from the group consisting of deuterium, a cyano group, a halogen group, an alkyl group, a silyl group, a phosphine oxide group, and an aryl group; or a combination thereof.

[0258] In one embodiment of the present specification, Ar5 may be a phenyl group; a biphenyl group; a terphenyl group; a naphthyl group; a fluorenyl group; a spirobifluorenyl group; a phenanthrenyl group; a triphenyl group; a chrysenyl group; a dibenzofuranyl group; a dibenzothiophenyl group; a carbazolyl group; or a combination thereof, and the phenyl group; a biphenyl group; a terphenyl group; a naphthyl group; a fluorenyl group; a spirobifluorenyl group; a phenanthrenyl group; a triphenyl group; a chrysenyl group; a dibenzofuranyl group; a dibenzothiophenyl group; and a carbazolyl group may each be independently unsubstituted or substituted with a substituent selected from the group consisting of a deuterium group, a cyano group, a halogen group, an alkyl group, a silyl group, a phosphine oxide group, and an aryl group.

[0259] In one embodiment of the present specification, R7' and R8' may be the same as or different from each other, and each independently represent hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C40 alkyl group; a substituted or unsubstituted C3 to C40 cycloalkyl group; a substituted or unsubstituted C2 to C40 heterocycloalkyl group; -P(=O)RR'; -SiRR'R"; or a combination thereof.

[0260] In one embodiment of the present specification, R7' and R8' may be the same as or different from each other, and each independently represent hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C3 to C20 cycloalkyl group; a substituted or unsubstituted C2 to C20 heterocycloalkyl group; -P(=O)RR'; -SiRR'R"; or a combination thereof.

[0261] In one embodiment of the present specification, R7' and R8' may be the same or different from each other, and may each independently be hydrogen; deuterium; -P(=O)RR'; or -SiRR'R".

[0262] In one embodiment of the present specification, “substituted or unsubstituted” means substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium; a halogen group; a cyano group; a C1 to C40 alkyl group; a C2 to C40 alkenyl group; a C2 to C40 alkynyl group; a C3 to C40 cycloalkyl group; a C2 to C40 heterocycloalkyl group; a C6 to C40 aryl group; a C2 to C40 heteroaryl group; a silyl group (-SiRR'R"); a phosphine oxide group (-P(=O)RR'); and an amine group (-NRR'), or a substituent in which two or more substituents selected from the above substituents are connected.

[0263] In one embodiment of the present specification, “substituted or unsubstituted” means substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium; a halogen group; a cyano group; a C1 to C20 alkyl group; a C2 to C20 alkenyl group; a C2 to C20 alkynyl group; a C3 to C20 cycloalkyl group; a C2 to C20 heterocycloalkyl group; a C6 to C20 aryl group; a C2 to C20 heteroaryl group; a silyl group (-SiRR'R"); a phosphine oxide group (-P(=O)RR'); and an amine group (-NRR'), or a substituent in which two or more substituents selected from the above substituents are connected.

[0264] In one embodiment of the present specification, R, R' and R" are the same as or different from each other, and each independently may be hydrogen; deuterium; a substituted or unsubstituted C1 to C40 alkyl group; a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group.

[0265] In one embodiment of the present specification, R, R' and R" are the same as or different from each other, and each independently may be hydrogen; deuterium; a substituted or unsubstituted C1 to C30 alkyl group; a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0266] In one embodiment of the present specification, R, R' and R" are the same as or different from each other, and each independently may be hydrogen; deuterium; a substituted or unsubstituted C1 to C20 alkyl group; a substituted or unsubstituted C6 to C20 aryl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0267] In one embodiment of the present specification, the deuterium contents of the heterocyclic compound represented by the chemical formula A; the heterocyclic compound represented by the chemical formula B; and the heterocyclic compound represented by the chemical formula C may be the same as or different from each other, and may each independently be 0% or 1% to 100%.

[0268] In one embodiment of the present specification, the deuterium contents of the heterocyclic compound represented by the chemical formula A; the heterocyclic compound represented by the chemical formula B; and the heterocyclic compound represented by the chemical formula C may be the same as or different from each other, and may each independently be 0% or 10% to 100%.

[0269] In one embodiment of the present specification, the deuterium contents of the heterocyclic compound represented by the chemical formula A; the heterocyclic compound represented by the chemical formula B; and the heterocyclic compound represented by the chemical formula C may be the same as or different from each other, and may each independently be 0% or 20% to 100%.

[0270] In one embodiment of the present specification, the deuterium contents of the heterocyclic compound represented by the chemical formula A; the heterocyclic compound represented by the chemical formula B; and the heterocyclic compound represented by the chemical formula C may be the same as or different from each other, and may each independently be 0% or 30% to 100%.

[0271] In one embodiment of the present specification, the deuterium contents of the heterocyclic compound represented by the chemical formula A; the heterocyclic compound represented by the chemical formula B; and the heterocyclic compound represented by the chemical formula C may be the same as or different from each other, and may each independently be 0% or 60% to 100%.

[0272] In one embodiment of the present specification, the deuterium contents of the heterocyclic compound represented by the chemical formula A; the heterocyclic compound represented by the chemical formula B; and the heterocyclic compound represented by the chemical formula C may be the same as or different from each other, and may each independently be 0% or 80% to 100%.

[0273] In one embodiment of the present specification, the deuterium contents of the heterocyclic compound represented by the chemical formula A; the heterocyclic compound represented by the chemical formula B; and the heterocyclic compound represented by the chemical formula C may be the same as or different from each other, and may each independently be 0% or 90% to 100%.

[0274] In one embodiment of the present specification, the chemical formula A may be represented by any one of the following heterocyclic compounds.

[0275]

[0276]

[0277]

[0278]

[0279]

[0280]

[0281]

[0282]

[0283] In one embodiment of the present specification, the chemical formula B may be represented by any one of the following heterocyclic compounds.

[0284]

[0285]

[0286]

[0287]

[0288]

[0289]

[0290] In one embodiment of the present specification, the chemical formula C may be represented by any one of the following heterocyclic compounds.

[0291]

[0292]

[0293]

[0294]

[0295]

[0296]

[0297]

[0298]

[0299] By introducing various substituents into the structures represented by the above chemical formulas A, B, and / or C, compounds having unique properties of the introduced substituents can be synthesized. For example, by introducing substituents that are mainly used in hole injection layer materials, hole transport layer materials, hole transport auxiliary layer materials, light-emitting layer materials, electron transport layer materials, electron transport auxiliary layer materials, and charge generation layer materials used in the manufacture of organic light-emitting devices into the core structure, a material that satisfies the conditions required for each organic layer can be synthesized.

[0300] In addition, by introducing various substituents into the structure of the above chemical formulas A, B, and / or C, it is possible to finely control the energy band gap, while improving the properties at the interface between organic substances and diversifying the uses of the material.

[0301] In one embodiment of the present specification, the molar ratio of the heterocyclic compound represented by the chemical formula A, the heterocyclic compound represented by the chemical formula B, and the heterocyclic compound represented by the chemical formula C may be 0.1 to 3: 0.1 to 2: 0.1 to 2.

[0302] In one embodiment of the present specification, the molar ratio of the heterocyclic compound represented by the chemical formula A, the heterocyclic compound represented by the chemical formula B, and the heterocyclic compound represented by the chemical formula C may be 1 to 3: 1 to 2: 1 to 2.

[0303] In addition, the composition for an organic layer comprising the heterocyclic compound of the above chemical formula A, the heterocyclic compound of the chemical formula B, and the heterocyclic compound of the chemical formula C provides excellent thermal stability when used in an organic light-emitting device, and such thermal stability can not only provide operating stability to the organic light-emitting device in the future, but also improve lifespan characteristics.

[0304] Organic light-emitting device

[0305] Hereinafter, an organic light-emitting device according to the present specification will be described.

[0306] Another embodiment of the present specification provides an organic light-emitting device comprising a first electrode; a second electrode provided opposite the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein at least one of the organic layers comprises the composition for an organic layer of the organic light-emitting device described above.

[0307] In one embodiment of the present specification, the organic layer further includes an emission layer, and the emission layer may include the composition for an organic light-emitting element.

[0308] In another embodiment of the present specification, the light-emitting layer may include the composition for an organic light-emitting element as a host.

[0309] In one embodiment of the present specification, the light-emitting layer may include the composition for an organic light-emitting element as a red host.

[0310] In one embodiment of the present specification, the first electrode may be an anode, and the second electrode may be a cathode.

[0311] In one embodiment of the present specification, the first electrode may be a cathode, and the second electrode may be an anode.

[0312] In one embodiment of the present specification, the organic light-emitting device may be a blue organic light-emitting device, and the composition for an organic layer of the organic light-emitting device may be used as a material for the blue organic light-emitting device.

[0313] In one embodiment of the present specification, the organic light-emitting device may be a green organic light-emitting device, and the composition for an organic layer of the organic light-emitting device may be used as a material of the green organic light-emitting device.

[0314] In one embodiment of the present specification, the organic light-emitting device may be a red organic light-emitting device, and the composition for an organic layer of the organic light-emitting device may be used as a material of the red organic light-emitting device.

[0315] The organic layer of the organic light-emitting device of the present specification may be formed as a single-layer structure, but may also be formed as a multi-layer structure in which two or more organic layers are laminated. For example, the organic light-emitting device of the present specification may have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, etc. as the organic layers. However, the structure of the organic light-emitting device is not limited thereto and may include a smaller or larger number of organic layers.

[0316] In one embodiment of the present specification, the organic layer may include an iridium-based dopant.

[0317] In one embodiment of the present specification, the iridium-based dopant may be a green phosphorescent dopant, Ir(ppy)3, but is not limited thereto.

[0318] In one embodiment of the present specification, the iridium-based dopant may be a red phosphorescent dopant, (piq)2(Ir)(acac), but is not limited thereto.

[0319] In the organic light-emitting device of the present specification, materials having a relatively large work function can be used as the anode material, and transparent conductive oxides, metals, or conductive polymers can be used. Specific examples of the anode material include, but are not limited to, 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.

[0320] In the organic light-emitting device of the present specification, materials having a relatively low work function can be used as the cathode material, and metals, metal oxides, or conductive polymers can be used. Specific examples of the cathode material include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayered materials such as LiF / Al or LiO2 / Al, and the like.

[0321] In the organic light emitting device of the present specification, a known hole injection material may be used as the hole injection material, for example, a phthalocyanine compound such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429, or a starburst amine derivative described in the literature [Advanced Material, 6, p. 677 (1994)], such as tris(4-carbazoyl-9-ylphenyl)amine (TCTA), 4,4',4"-tri[phenyl(m-tolyl)amino]triphenylamine (m-MTDATA), 1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene (m-MTDAPB), a soluble conductive polymer such as polyaniline / dodecylbenzenesulfonic acid, or Poly(3,4-ethylenedioxythiophene) / Poly(4-styrenesulfonate), polyaniline / camphor sulfonic acid, or polyaniline / poly(4-styrene-sulfonate) can be used.

[0322] In the organic light-emitting device of the present specification, a pyrazoline derivative, an arylamine derivative, a stilbene derivative, a triphenyldiamine derivative, etc. may be used as a hole transport material, and a low-molecular or high-molecular material may also be used.

[0323] In the organic light-emitting device of the present specification, as the electron transport material, metal complexes of oxadiazole derivatives, anthraquinodimethane and derivatives thereof, benzoquinone and derivatives thereof, naphthoquinone and derivatives thereof, anthraquinone and derivatives thereof, tetracyanoanthraquinodimethane and derivatives thereof, fluorenone derivatives, diphenyldicyanoethylene and derivatives thereof, diphenoquinone derivatives, 8-hydroxyquinoline and derivatives thereof, etc. may be used, and not only low-molecular substances but also high-molecular substances may be used.

[0324] In the organic light-emitting device of this specification, LiF is typically used as an electron injection material in the art, but the present application is not limited thereto.

[0325] In the organic light-emitting device of the present specification, a red, green, or blue light-emitting material may be additionally used as the light-emitting material, and if necessary, two or more light-emitting materials may be mixed and used. At this time, the two or more light-emitting materials may be deposited and used as individual sources, or may be premixed and deposited and used as a single source. In addition, a fluorescent material may be used as the light-emitting material, but it may also be used as a phosphorescent material. A material that emits light by combining holes and electrons injected from the anode and cathode, respectively, may be used as the light-emitting material alone, but materials in which both the host material and the dopant material participate in light emission may also be used.

[0326] When using a mixture of hosts for light-emitting materials, hosts of the same series may be mixed and used, or hosts of different series may be mixed and used. For example, two or more types of materials, either N-Type host materials or P-Type host materials, may be selected and used as the host materials for the light-emitting layer.

[0327] An organic light-emitting device according to one embodiment of the present specification may be a front-emitting, back-emitting, or double-sided emitting device depending on the material used.

[0328] The heterocyclic compound according to one embodiment of the present specification can function in organic electronic devices, including organic solar cells, organic photoconductors, organic transistors, etc., by a similar principle to that applied to organic light-emitting devices.

[0329] The organic light-emitting device of the present specification 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, a hole transport auxiliary layer, an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer.

[0330] The stacking order of electrodes and organic layers of an organic light-emitting device according to one embodiment of the present disclosure is exemplified in Figures 1 to 3. However, the scope of the present application is not intended to be limited by these drawings, and the structure of an organic light-emitting device known in the art may also be applied to the present application.

[0331] According to FIG. 1, an organic light-emitting device is illustrated in which an anode (200), an organic layer (300), and a cathode (400) are sequentially laminated on a substrate (100). However, the present invention is not limited to this structure, and an organic light-emitting device in which a cathode, an organic layer, and an anode are sequentially laminated on a substrate may also be implemented, as shown in FIG. 2. The composition for the organic light-emitting device may be included in the organic layer (300), and the organic layer (300) may be one or more layers.

[0332] Fig. 3 illustrates a case where the organic layer is multilayered. The organic light-emitting device according to Fig. 3 includes a hole injection layer (301), a hole transport layer (302), a light-emitting 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 light-emitting layer (303). However, the scope of the present application is not limited by such a laminated structure, and, if necessary, layers other than the light-emitting layer may be omitted, and other necessary functional layers may be further added.

[0333] An organic light-emitting device according to one embodiment of the present specification includes: a first electrode; a first stack provided on the first electrode and including a first light-emitting layer; a charge generation layer provided on the first stack; a second stack provided on the charge generation layer and including a second light-emitting layer; and a second electrode provided on the second stack.

[0334] In an organic light-emitting device according to one embodiment of the present specification, when the device has a two-stack structure as described above, at least one layer among the first light-emitting layer (first stack light-emitting layer) and the second light-emitting layer (second stack light-emitting layer) may include the composition for an organic light-emitting device.

[0335] In addition, the first stack and the second stack may each independently additionally include one or more of the aforementioned hole injection layer, hole transport layer, hole blocking layer, electron transport layer, electron injection layer, etc.

[0336] The composition for the organic layer of the above organic light-emitting device can be used when forming the organic layer of the organic light-emitting device, and can be particularly preferably used as a light-emitting layer material.

[0337] The composition for the organic layer is in a form in which the heterocyclic compound of the above chemical formula A, the heterocyclic compound of the above chemical formula B, and the heterocyclic compound of the above chemical formula C are each pre-mixed. Before forming the organic layer of the organic light-emitting device, materials in a powder state may be mixed, or compounds in a liquid state at an appropriate temperature or higher may be mixed. 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.

[0338] The composition for the organic layer may additionally include materials known in the art, such as solvents and additives.

[0339] <Method for manufacturing organic light-emitting devices>

[0340] In one embodiment of the present application, a method for manufacturing an organic light-emitting device is provided, comprising: a step of preparing a substrate; a step of forming a first electrode on the substrate; a step of forming one or more organic layers on the first electrode; and a step of forming a second electrode on the organic layer, wherein the step of forming the organic layer includes a step of forming one or more organic layers using a composition for an organic layer of an organic light-emitting device according to one embodiment of the present specification.

[0341] In one embodiment of the present specification, the step of forming the organic layer may be performed by forming a heterocyclic compound represented by the chemical formula A, a heterocyclic compound represented by the chemical formula B, and a heterocyclic compound represented by the chemical formula C using a thermal vacuum deposition method.

[0342] An organic light-emitting device according to one embodiment of the present disclosure can be manufactured using a conventional method and material for manufacturing an organic light-emitting device, except that an organic layer is formed using the composition for an organic layer of the organic light-emitting device described above.

[0343] Specifically, the method for forming the organic layer is such that the heterocyclic compound of the above chemical formula A, the heterocyclic compound of the above chemical formula B, and / or the heterocyclic compound of the above chemical formula C can be formed by a solution coating method as well as a vacuum deposition method during the manufacture of an organic light-emitting device. Here, the solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited thereto.

[0344] Hereinafter, the present specification will be described in more detail through examples, but these are only intended to illustrate the present application and are not intended to limit the scope of the present application.

[0345] Manufacturing example

[0346] <Manufacturing Example 1> Preparation of Compound A1

[0347]

[0348] 1) Preparation of compound A1-1

[0349] In a 1 L two-neck flask, 30.0 g (90.5 mmol) of 5-bromo-8-chloronaphtho[1,2-b]benzofuran, 12.1 g (99.6 mmol) of phenylboronic acid, 45.2 g (4.5 mmol) of Pd(pph3), and 25.0 g (181.0 mmol) of K2CO3 were dissolved in 1,4-Dioxane / H2O (300 ml / 60 ml), and refluxed for 2 hours.

[0350] After the reaction was completed, the precipitated compound was filtered and recrystallized using methanol, obtaining 24.8 g of compound A1-1 (yield 83.3%).

[0351] 2) Preparation of compound A1

[0352] In a 1 L two-neck flask, 10.0 g (30.4 mmol) of compound A1-1, 11.3 g (30.4 mmol) of di([1,1'-biphenyl]-4-yl)amine (C), 1.4 g (1.5 mmol) of Pd2dba, 1.4 g (3.0 mmol) of Xphos, and 5.8 g (60.8 mmol) of NaOtBu were added, dissolved in toluene (150 ml), and refluxed for 1 hour.

[0353] After the reaction was completed, extraction was performed using MC and distilled water. After concentrating the solvent of the organic layer, it was dissolved in MC, purified with silica, and recrystallized using MC / Hexane to obtain 17.6 g (87% yield) of the target compound A1.

[0354] <Manufacturing Example 2> Preparation of compounds A22, A35, A41, A44, A72, and A92

[0355] The following target compound was synthesized in the same manner as in Manufacturing Example 1, except that intermediate A in Table 1 was used instead of 5-bromo-8-chloronaphtho[1,2-b]benzofuran (A) in the above Manufacturing Example 1, intermediate B in Table 1 was used instead of phenylboronic acid (B), and intermediate C in Table 1 was used instead of di([1,1'-biphenyl]-4-yl)amine (C).

[0356]

[0357]

[0358] <Manufacturing Example 3> Preparation of compound A17

[0359]

[0360] 1) Preparation of compound A17-1

[0361] In a 1 L two-neck flask, 30.0 g (90.5 mmol) of 5-bromo-7-chloronaphtho[1,2-b]benzofuran, 12.1 g (99.6 mmol) of phenylboronic acid, 45.2 g (4.5 mmol) of Pd(pph3), and 25.0 g (181.0 mmol) of K2CO3 were dissolved in 1,4-Dioxane / H2O (300 ml / 60 ml), and refluxed for 1 hour.

[0362] After the reaction was completed, the precipitated compound was filtered and recrystallized using methanol, obtaining 24.8 g of compound A17-1 (yield 83.3%).

[0363] 2) Preparation of compound A17-2

[0364] In a 1 L two-neck flask, 24.8 g (75.43 mmol) of compound A17-1, 28.73 g (113 mmol) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane), 33.45 g (3.77 mmol) of Pd2dba, 3.6 g (7.54 mmol) of Xphos, and 20.8 g (150.8 mmol) of KOAc were added, dissolved in 1,4-dioxane (250 ml), and refluxed for 4 hours.

[0365] After the reaction was completed, extraction was performed using MC and distilled water. After concentrating the solvent of the organic layer, it was dissolved in MC, purified by silica, and recrystallized using MC / methanol to obtain 26 g of compound A17-2 (yield 82%).

[0366] 3) Preparation of compound A17

[0367] In a 1 L two-neck flask, 9.0 g (21.41 mmol) of compound A17-2, 13 g (23.6 mmol) of N-([1,1'-biphenyl]-3-yl)-N-(4-bromophenyl)-[1,1':4',1''-terphenyl]-4-amine (C), 41.24 g (1.07 mmol) of Pd(pph3), and 5.9 g (42.8 mmol) of K2CO3 were dissolved in 1,4-Dioxane / H2O (100 ml / 20 ml), and refluxed for 2 hours.

[0368] After the reaction was completed, extraction was performed using MC and distilled water. After concentrating the solvent of the organic layer, it was dissolved in MC, purified with silica, and recrystallized using MC / methanol to obtain 15 g (91% yield) of the target compound A17.

[0369] <Manufacturing Example 4> Preparation of compounds A37, B1, B14, B37, B53, B59, B64, B98, C24, C61, C89, and C149

[0370] The following target compound was synthesized in the same manner as in Manufacturing Example 3, except that intermediate A in Table 2 was used instead of 5-bromo-7-chloronaphtho[1,2-b]benzofuran (A) in the above Manufacturing Example 3, intermediate B in Table 2 was used instead of phenylboronic acid (B), and intermediate C in Table 2 was used instead of N-([1,1'-biphenyl]-3-yl)-N-(4-bromophenyl)-[1,1':4',1''-terphenyl]-4-amine (C).

[0371]

[0372]

[0373]

[0374] <Manufacturing Example 5> Preparation of compound A128

[0375]

[0376] 1) Preparation of compound A128-1

[0377] In a 1 L two-neck flask, 7 g (21.1 mmol) of 5-bromo-9-chloronaphtho[2,1-b]benzofuran, 8.99 g (24.2 mmol) of N-(4-(naphthalen-2-yl)phenyl)-[1,1'-biphenyl]-4-amine, 30.97 g (1.06 mmol) of Pd2dba, 1.01 g (2.11 mmol) of Xphos, and 4.06 g (42.2 mmol) of NaOtBu were dissolved in toluene (100 ml) and refluxed for 3 hours.

[0378] After the reaction was completed, extraction was performed using MC and distilled water. After concentrating the solvent of the organic layer, it was dissolved in MC, purified with silica, and recrystallized using MC / Hexane to obtain 12.1 g (yield 92%) of the target compound A128-1.

[0379] 2) Preparation of compound A128

[0380] In a 1 L two-neck flask, 12.1 g (19.45 mmol) of compound A128-1, 2.42 g (19.45 mmol) of phenylboronic acid, 0.89 g (0.97 mmol) of Pd2dba, 0.93 g (1.94 mmol) of Xphos, and 5.38 g (38.9 mmol) of K2CO3 were added, dissolved in 1,4-Dioxane / H2O (150 ml / 30 ml), and refluxed for 6 hours.

[0381] After the reaction was completed, extraction was performed using MC and distilled water. After concentrating the solvent of the organic layer, it was dissolved in MC, purified by silica, and recrystallized using MC / Methanol to obtain 8.1 g (yield 63%) of the target compound A128.

[0382] <Manufacturing Example 6> Preparation of compound C126

[0383]

[0384] In a 1 L two-neck flask, 5.0 g (17 mmol) of 2-(dibenzo[b,d]furan-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (A), 7.9 g (17.85 mmol) of 2-chloro-4-(naphthalen-2-yl)-6-(4-(naphthalen-2-yl)phenyl)-1,3,5-triazine (B), 40.98 g (0.85 mmol) of Pd(pph3), and 4.7 g (34 mmol) of K2CO3 were dissolved in 1,4-Dioxane / H2O (100 ml / 20 ml), and refluxed for 1 hour.

[0385] After the reaction was completed, extraction was performed using MC and distilled water. After concentrating the solvent of the organic layer, it was dissolved in MC, purified with silica, and purified using acetone to obtain 8.4 g (yield 86%) of the target compound C126.

[0386] <Manufacturing Example 7> Preparation of compounds C135 and C158

[0387] Except that intermediate A in Table 3 below was used instead of 2-(dibenzo[b,d]furan-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (A) in Manufacturing Example 6 above, and intermediate B in Table 3 below was used instead of 2-chloro-4-(naphthalen-2-yl)-6-(4-(naphthalen-2-yl)phenyl)-1,3,5-triazine (B), the following target compound was synthesized in the same manner as Manufacturing Example 6 above.

[0388]

[0389] <Manufacturing Example 8> Preparation of compound B77

[0390]

[0391] Compound B53 (10 g, 15.34 mmol) synthesized according to the method described in Preparation Example 4 above was dissolved in 100 mL of benzene-d6. Then, after adjusting the temperature to 0°C using an ice bath, 9.6 mL (107.4 mmol) of trifluoromethanesulfonic acid was slowly added dropwise. The mixture was then stirred at room temperature for 5 hours.

[0392] After the reaction mixture was cooled to room temperature, an ice bath was installed, and the mixture was neutralized with a K3PO4 aqueous solution. Then, extraction was performed with DCM and distilled water, and the organic layer was treated with MgSO4, concentrated, dissolved in DCM, purified with silica, and the solid was precipitated with methanol and filtered to obtain 8 g (80%) of compound B77.

[0393] <Manufacturing Example 9> Preparation of compound C141

[0394] The target compound was synthesized in the same manner as in Manufacturing Example 8, except that compound E of Table 4 below was used instead of compound B53.

[0395]

[0396] Tables 5 and 6 below show the compounds 1 These are H NMR and FD-MS data, and the synthesis of the target compound can be confirmed through the data below.

[0397] Target compound number 1<h2 style=";text-align:left;direction:ltr">H NMR(CDCl3, 400MHz)A1δ = 8.55 (1H, s), 8.18 (1H, d), 7.79 (2H, d), 7.71 (1H, d), 7.65 (1H, d), 7.55 (2H, d), 7.54 (4H, d), 7.52 (4H, d), 7.51 (6H, d), 7.41 (4H, dd), 6.69 (4H, d), 6.39 (1H, d)A17δ = 8.55 (1H, s), 8.18 (1H, d), 7.79 (2H, d), 7.75 (1H, d), 7.71 (1H, d), 7.62 (1H, d), 7.55 (2H, d), 7.54 (4H, d), 7.52 (4H, d), 7.51 (6H, dd), 7.44 (2H, d), 7.41 (3H, d), 7.25 (4H, dd), 6.89 (1H, dd), 6.88 (1H, s), 6.69 (4H, t), 6.59 (1H, t)A22δ = 8.97(1H, d), 8.62(1H, d), 8.22~8.18(3H, m), 7.75(4H, d), 7.74(1H, s), 7.64~7.31(24H, m), 7.25(1H, d), 7.20(1H, t), 6.91(1H, d)A35δ = 8.97(1H, d), 8.22(1H, s), 8.18(1H, d), 8.03(1H, s), 7.98(1H, d), 7.80~7.75(5H, m), 7.64~7.31(17H, m), 6.97(1H, d), 6.91(1H, d)A37δ = 8.97(1H, d), 8.18(1H, d), 7.70(1H, s), 7.64~7.41(7H, m), 7.30(4H, s), 7.11(2H, s)A41δ = 8.55 (2H, s), 7.79 (2H, d), 7.64 (2H, d), 7.55 (2H, d), 7.54 (4H, d), 7.52 (4H, d), 7.51 (6H, d), 7.43 (1H, d), 7.41 (3H, d), 6.69 (4H, dd), 6.33 (1H, d)A44δ = 8.97(2H, d), 8.03(1H, s), 7.80(1H, d), 7.79(2H, d), 7.59(2H, t), 7.46~7.41(3H, m), 7.30(3H, s), 7.24(2H, t), 7.08~6.91(4H, m)A72δ = 8.97(2H, d), 8.22(1H, s), 7.75(6H, d), 7.59~7.25(25H, m), 6.97(1H, d)A92δ = 8.45(1H, d), 8.28(1H, d), 8.20(1H, s), 8.13(1H, s), 8.11(1H, d), 8.01(1H, d), 7.93(1H, d), 7.79~7.64(7H, m), 7.56~7.41(12H, m), 7.27(1H, s), 7.18~7.17(2H, d)A128δ = 8.97(1H, d), 8.09~7.99(6H, m), 7.82~7.74(6H, m), 7.63~7.37(20H, m)B1δ = 8.36(2H, d), 8.28(1H, s), 8.11~7.96(5H, m), 7.75~7.69(4H, m), 7.51~7.41(13H, m), 7.25(2H, d)B14δ = 8.36(4H, d), 8.28(1H, d), 8.11(1H, d), 7.97(2H, d), 7.86(1H, s), 7.81~7.69(5H, m), 7.61(2H, s), 7.50~7.40(13H, m)B37δ = 8.36(2H, d), 8.16~7.96(7H, m), 7.86~7.41(18H, m), 7.25(2H, d)B53δ = 8.97(1H, s), 8.36(4H, d), 8.18(1H, d), 8.09~7.99(3H, m), 7.82(1H, d), 7.69~7.50(13H, m), 7.38(1H, s), 7.25(1H, s)B59δ = 9.09(1H, s), 8.97(1H, d), 8.49(1H, d), 8.36(2H, d), 8.18~7.99(8H, m), 7.83(1H, s), 7.82(1H, d), 7.76(1H, s), 7.64~7.50(10H, m), 7.38(1H, d)B64δ = 8.16~7.99(7H, m), 7.84(1H, d), 7.69~7.55(5H, m), 7.48(1H, d), 7.38(1H, d), 7.25(4H, s)B98δ = 9.02(1H, d), 8.95(1H, d), 8.36(4H, d), 8.06(1H, d), 7.84(1H, d), 7.52~7.41(13H, m)C24δ = 8.28 (2H, s), 8 (2H, d), 7.92 (1H, d), 7.89 (2H, d), 7.75 (1H, d), 7.73 (1H, d), 7.66 (2H, d), 7.62 (1H, d), 7.6 (1H, d), 7.59 (2H, dd), 7.58 (1H, d), 7.57 (1H, d), 7.51 (2H, dd), 7.44 (1H, dd), 7.41 (1H, s), 7.38 (2H, t), 7.32 (2H, t), 7.25 (4H, dd)C61δ = 9.11(1H, d), 8.92(1H, d), 8.84(1H, d), 8.46(1H, s), 8.36(2H, d), 8.21(1H, d), 8.09(1H, d), 8.03(1H, d), 7.92~7.41(18H, m)C89δ = 9.09(1H, s), 8.49(1H, d), 8.09~7.98(8H, m), 7.82~7.54(14H, m), 7.39~7.31(3H, m)C126δ = 9.09(1H, s), 8.49(1H, d), 8.16~7.96(9H, m), 7.82(1H, d), 7.69~7.54(8H, m), 7.39~7.25(5H, m)C135δ = 9.09(1H, s), 8.95(1H, d), 8.50(1H, d), 8.49(1H, d), 8.20~7.77(12H, m), 7.61~7.52(4H, m), 7.39~7.25(5H, m)C149δ = 9.09(1H, s), 8.49(1H, d), 8.16~7.98(8H, m), 7.82(3H, d), 7.69~7.54(9H, m), 7.39~7.31(3H, m)C158δ = 9.09(1H, s), 8.49(1H, d), 8.16~7.96(8H, m), 7.63~7.<h2 style=";text-align:left;direction:ltr">55(5H, m), 7.38(1H, d), 7.25(2H, d).<h2 style=";text-align:left;direction:ltr"> <h2 style=";text-align:left;direction:ltr">

[0398] <h2 style=";text-align:left;direction:ltr"> 목적화합물번호FD-MS목적화합물번호FD-MSA1m / z= 613.24 (C46H31NO, 613.74)B59m / z= 625.22 (C45H27N3O, A17m / z= 765.30 (C58H39NO, 765.94)B64m / z= 661.29 (C47H19D10N3O, 661.83) 680.41 (C47D29N3O, A35m / z= 627.22 (C46H29NO2, 627.74)B98m / z= 680.95 (C47H21D8N3O, 659.82) 691.23 (C49H29N3O2, 691.77)A41m / z= 613.24 (C46H31NO,613.74)C61m / z= 625.22 (C45H27N3O, 625.73)A44m / z= 624.31 (C46H20D11NO, C89m / z= 665.21 (C47H27N3O2, 665.75)A72m / z= 624.83 (C52H35NO, 689.86)C126m / z= 575.20 (C41H25N3O, 575.67)A92m / z= 643.20 (C46H29NOS, 643.80)C135m / z= 575.20 (C41H25N3O, 575.67)A128m / z= 663.26 (C50H33NO, 663.82)C141m / z= 548.33 (C37D23N3O, 548.75)B1m / z= 601.22 (C43H27N3O, 601.71)C149m / z= 667.22 (C47H25D2N3O2, 667.76)B14m / z= 651.23 (C47H29N3O, 651.77)C158m / z= 582.24 (C41H18D7N3O, 582.71)B37m / z= 651.23 (C47H29N3O, 651.77)B53m / z= 651.23 (C47H29N3O, 651.77)<h2 style=";text-align:left;direction:ltr">

[0399] Experimental example.

[0400] <Experimental Example 1> Fabrication of an organic light-emitting device

[0401] A glass substrate coated with a 1,500 Å thick indium tin oxide (ITO) film was ultrasonically cleaned in distilled water. After the distilled water cleaning, it was ultrasonically cleaned with solvents such as acetone, methanol, and isopropyl alcohol, dried, and then treated with UVO (Ultraviolet Ozone) for 5 minutes using UV (Ultraviolet) in a UV (Ultraviolet) cleaner. After that, the substrate was transferred to a plasma cleaner (PT), and plasma treated in a vacuum to remove the ITO work function and residual film, and then transferred to a thermal evaporation equipment for organic vapor deposition.

[0402] A common layer, a hole injection layer 2-TNATA (4,4',4"-Tris[2-naphthyl(phenyl)amino] triphenylamine) and a hole transport layer NPB (N,N'-diphenyl-(1,1'-biphenyl)-4,4'-diamine), were formed on the ITO transparent electrode (anode).

[0403] On top of that, a light-emitting layer was thermally vacuum-deposited as follows. The light-emitting layer was deposited to a thickness of 500 Å by doping the host with 3% of (piq)2(Ir)(acac) using the compounds described in Table 7 below as a red host (pre-mixed in the case of two or more compounds) and (piq)2(Ir)(acac) as a red phosphorescent dopant.

[0404] Afterwards, BCP was deposited as a hole blocking layer with a thickness of 60Å, and Alq3 was deposited as an electron transport layer with a thickness of 200Å thereon. Afterwards, BCP was deposited as a hole blocking layer with a thickness of 60Å, and Alq3 was deposited as an electron transport layer with a thickness of 200Å thereon. Finally, lithium fluoride (LiF) was deposited as a hole blocking layer with a thickness of 10Å on the electron transport layer to form an electron injection layer, and then an aluminum (Al) cathode was deposited as a cathode with a thickness of 1,200Å on the electron injection layer to form an organic electroluminescent device.

[0405] Meanwhile, all organic compounds required for OLED device production are 10 for each material. -8 ~10 -6 It was purified by vacuum sublimation under 10 torr and used in OLED production.

[0406] The electroluminescence (EL) characteristics of the organic electroluminescent device manufactured as described above were measured using M7000 from Max Science, and the standard luminance was determined to be 6,000 cd / m using the life measurement equipment (M6000) manufactured by Max Science based on the measurement results. 2 When, T 90 was measured. The above T 90 refers to the lifespan (unit: h, hours), which is the time it takes for the initial brightness to drop to 90%.

[0407] The characteristics of the organic electroluminescent device of the present invention are as shown in Table 7 below. Compounds X1, X2, X3, X4, X5, X6, X7, X8, and X9 used in Table 7 below are as follows, respectively.

[0408]

[0409] No. 1st host (P) 2nd host (N) 3rd host (N) Ratio (P:N:N) Driving voltage (V) Efficiency (cd / A) Lifespan (T) 90)(h) Example 1 A1B98C611:1:13.3764.3466 Example 2 A1B98C611:1:23.3763.5407 Example 3 A1B98C611:2:13.3965.2461 Example 4 A1B98C612:1:13.3664.8481 Example 5 A17B14C241:1:13.2868.9498 Example 6 A17B14C242:1:13.1969.1512 Example 7 A17B14C243:1:13.3766.7497 Example 8A17B64C1412:1:13.2469.1630 Example 9A22B53C241:1:13.3167.4494 Example 10A22B53C242:1:13.2868.7508 Example 11A22B1C242:1:13.2668.2513 Example 12A35B37C1262:1:13.2966.2502 Example 13A35B98C612:1:13.3466.1499 Example 14A37B64C892:1:13.3067.4592 Example 15A41B77C1412:1:13.2665.8621 Example 16A44B77C1352:1:13.2764.6587 Example 17A44B14C242:1:13.3965.2523 Example 18A72B59C1582:1:13.3962.3514 Example 19A72B1C892:1:13.3666.7492 Example 20A92B14C1492:1:13.4065.1568 Example 21A92B98C612:1:13.4264.9486 Example 22A128B53C242:1:13.3762.7503Comparative Example 1A1-5.7327.6140Comparative Example 2A17-5.2129.1158Comparative Example 3A22-5.3328.7157Comparative Example 4A35-5.2830.2137Comparative Example 5A37-5.2629.8191Comparative Example 6A41-4.9919.6153Comparative Example 7A44-4.9819.3179Comparative Example 8A72-5.0419.9124Comparative Example 9A92-6.0222.8144Comparative Example 10A128-6.0325.4126Comparative Example 11X1-6.0117.698Comparative example 12X2-6.2718.7103Comparative example 13X3-6.2217.696Comparative example 14X4-6.3618.157Comparative example 15B1-4.0152.442Comparative example 16B14-3.9855.260Comparative Example 17B37-4.5249.39Comparative Example 18B53-4.3354.631Comparative Example 19B59-4.6058.932Comparative Example 20B64-3.9954.353Comparative Example 21B77-4.3154.172Comparative Example 22B98-4.5749.168Comparative Example 23X5-4.9246.28Comparative Example 24X6-4.8945.74Comparative Example 25X7-5.0341.76Comparative Example 26C24-3.4438.713Comparative Example 27C61-3.0832.17Comparative Example 28C89-3.2932.411Comparative Example 29C126-3.1836.920Comparative example 30C135-3.2634.114Comparative example 31C141-3.4237.635Comparative example 32C149-3.2832.436Comparative example 33C158-3.3031.818Comparative example 34X8-5.9818.27Comparative example 35X9-5.8819.18Comparative example 36A1B14-1:1:-3.9759.2274Comparative example 37A17B1-1:1:-3.9960.1291Comparative example 38A41B59-1:1:-4.5459.8275Comparative example 39A92B37-1:1:-4.4352.7269Comparative example 40X1B64-1:1:-3.8956.7232Comparative example 41X4B98-1:1:-4.5757.3189Comparative example 42A22-C241:-:13.4242.3218Comparative example 43A35-C891:-:13.3445.2263Comparative example 44A37-C1581:-:13.2844.9237Comparative example 45A128-C1411:-:13.3747.2206Comparative example 46X2-C611:-:13.4240.6175Comparative example 47X3-C1491:-:13.2942.1206Comparative example 48A35X81:-:15.2930.7129Comparative example 49A44X7-1:1:-4.8648.7200Comparative example 50A72X5-1:1:-4.8850.1183Comparative example 51A128X6-1:1:-4.7949.9203Comparative example 52-B53C135-:1:13.8857.836Comparative example 53-B59C126-:1:13.7758.632Comparative example 54-B77C141-:1:13.6755.281Comparative example 55-X5C24-:1:13.8347.119Comparative example 56-B53X9-:1:14.3250.128Comparative example 57X1B64C892:1:13.5459.4299Comparison example 58A72X5C242:1:13.7852.1274Comparison example 59A35B53X92:1:14.4253.8268.

[0410] As can be seen from the results in Table 7 above, it was confirmed that the example group in which the organic layer of the organic light-emitting device was deposited by mixing three types of heterocyclic compounds according to the present specification exhibited lower driving voltage, higher efficiency, and longer lifespan characteristics than the comparative example group in which the organic layer was not deposited.

[0411] Specifically, Comparative Examples 11 to 14 are organic light-emitting devices including 4-cyclic heterocycles (X1 to X4, respectively) that do not satisfy the 2-substitution characteristic of Chemical Formula A, and it was confirmed that the driving voltage was very high at 6 V or more and the efficiency was very low at less than 19 cd / A compared to other Comparative Example groups. In addition, Comparative Examples 23 to 25 are organic light-emitting devices including 4-cyclic heterocycles (X5 to X7, respectively) that do not satisfy the 2-substitution characteristic of Chemical Formula B, and it was found that the lifespan was shorter compared to other Comparative Example groups. It is believed that the Example group that satisfies the 2-substitution characteristic improved the device characteristics by expanding the conjugation and increasing the hole or electron mobility compared to the Comparative Example group that uses a 1-substituted compound. In addition, Comparative Examples 34 and 35 are organic light-emitting devices including a tricyclic heterocycle (X8 and X9, respectively) in which N-Het2 of chemical formula C does not satisfy structural formula N, and were shown to have the shortest lifespan compared to other comparative example groups.

[0412] Comparative Examples 1 to 10, when containing only the heterocyclic compound represented by the chemical formula A, exhibited relatively long-life characteristics compared to other comparative examples, but the remaining device characteristics were weakened, and Comparative Examples 15 to 22, when containing only the heterocyclic compound represented by the chemical formula B, or Comparative Examples 26 to 33, when containing only the heterocyclic compound represented by the chemical formula C, exhibited low operating voltage and high efficiency characteristics, but the remaining device characteristics were weakened.

[0413] In addition, in Comparative Examples 36 to 39, 42 to 45, and 52 to 54, organic light-emitting devices were formed by depositing only two materials among the heterocyclic compounds of Chemical Formula A, Chemical Formula B, and Chemical Formula C, and the driving voltage, efficiency, and lifespan tended to increase compared to the case where only one material was deposited. However, even so, the efficiency and lifespan did not reach the level of the examples in which three types of compounds were mixed.

[0414] The heterocyclic compound represented by the above chemical formula A is a p-Host containing an amine substituent, and thus exhibits fast hole mobility. The heterocyclic compound represented by the above chemical formula B or C is a unipolar n-Host with fast electron mobility, and thus it can be confirmed that by appropriately combining them, charge balance within the device is maintained, thereby improving operation, efficiency, and lifespan.

[0415] Comparative Examples 57 to 59 include three different heterocyclic compounds, but in cases where any one of the chemical formulae A to C does not satisfy the embodiment according to the present invention, it can be confirmed that the device characteristics are improved compared to the case where two or fewer different heterocyclic compounds are included, but the device characteristics are weakened compared to the organic light-emitting device including three different heterocyclic compounds according to one embodiment of the present invention.

[0416] The present invention is not limited to the above-described embodiments, but can be manufactured in a variety of different forms. Those skilled in the art will appreciate that the present invention can be implemented in other specific forms without altering the technical spirit or essential characteristics of the present invention. Therefore, the embodiments described above should be understood as illustrative in all respects and not restrictive.

Claims

1. A composition for an organic layer of 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] [Chemical Formula B] [Chemical Formula C] In the above chemical formulas A, B and C, X1 to X3 are the same or different from each other, and are each independently O; or S, L1 to L4 and L6 are the same or different from each other, and each independently represents a direct bond; a substituted or unsubstituted C6 to C60 arylene group; a substituted or unsubstituted C2 to C60 heteroarylene group; or a combination thereof, Ar1 to Ar4 are the same or different from each other, and are each independently a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; or a combination thereof, R1 to R8 are the same or different from each other, and are each independently 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; a substituted or unsubstituted C2 to C60 heteroaryl group; -P(=O)RR'; -SiRR'R"; or a combination thereof, The above R, R' and R" are the same or different from each other, and each independently represents hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, l1 to l4 and l6 are the same or different from each other, and are each independently an integer from 1 to 3, and when l1 to l4 and l6 are each an integer of 2 or more, the substituents in the parentheses are the same or different from each other, r1, r3, r4, r6 and r8 are the same or different from each other and are each independently an integer from 0 to 4, r2 and r5 are the same or different from each other, and are each independently an integer from 0 to 2, r7 is an integer from 0 to 3, If each of r1 to r8 is an integer greater than or equal to 2, the substituents in parentheses are the same or different from each other, N-Het1 and N-Het2 are each represented by the structural formula N below, [Structural formula N] In the above structural formula N, refers to the parts connected to L3 and L6 respectively, Y1 to Y5 are the same or different from each other, and are each independently CRa or N, but at least one is N, Ra is a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; or a combination thereof.

2. In claim 1, The above chemical formula A is a composition for an organic layer of an organic light-emitting device represented by any one of the following chemical formulas A-1 to A-3: [Chemical Formula A-1] [Chemical Formula A-2] [Chemical Formula A-3] In the above chemical formulas A-1 to A-3, Each of X1, L1, L2, Ar1 to Ar3, R1 to R3, l1, l2 and r1 to r3 is as defined in the above chemical formula A.

3. In claim 1, The above chemical formula B is a composition for an organic layer of an organic light-emitting device represented by any one of the following chemical formulas B-1 to B-3: [Chemical Formula B-1] [Chemical Formula B-2] [Chemical Formula B-3] In the above chemical formulas B-1 to B-3, Each of X2, L3, L4, Ar4, R4 to R6, N-Het1, l3, l4 and r4 to r6 is as defined in the above chemical formula B.

4. In claim 1, The above chemical formula C is a composition for an organic layer of an organic light-emitting device represented by the following chemical formula C-1 or C-2: [Chemical Formula C-1] [Chemical Formula C-2] In the above chemical formulas C-1 and C-2, Each of X3, N-Het2, L6 and l6 is as defined in the above chemical formula C, L5 is a direct bond; a substituted or unsubstituted C6 to C60 arylene group; a substituted or unsubstituted C2 to C60 heteroarylene group; or a combination thereof, Ar5 is a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; or a combination thereof, R7' and R8' are the same or different, and each independently 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, -P(=O)RR'; -SiRR'R"; or a combination thereof, The above R, R' and R" are the same or different from each other, and each independently represents hydrogen; deuterium; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group, l5 is an integer from 1 to 3, and if l5 is an integer greater than or equal to 2, L5 are equal or different, r7' is an integer from 0 to 3, r8' is an integer from 0 to 4, and when each of r7' and r8' is an integer greater than or equal to 2, the substituents in the parentheses are the same or different.

5. In claim 1, The above chemical formula A is a composition for an organic layer of an organic light-emitting device represented by any one of the following chemical formulas A-11 to A-14: [Chemical Formula A-11] [Chemical Formula A-12] [Chemical Formula A-13] [Chemical Formula A-14] In the above chemical formulas A-11 to A-14, Each of X1, L1, L2, Ar1 to Ar3, R1 to R3, l1, l2, r2 and r3 is as defined in the above chemical formula A, r1' is an integer from 0 to 3, r1" is an integer from 0 to 2, r2' is 0 or 1, When each of r1' and r1" is 2 or more than 2, the substituents within the parentheses are the same or different.

6. In claim 1, The above chemical formula B is a composition for an organic layer of an organic light-emitting device represented by any one of the following chemical formulas B-11 to B-14: [Chemical Formula B-11] [Chemical Formula B-12] [Chemical Formula B-13] [Chemical Formula B-14] In the above chemical formulas B-11 to B-14, Each of X2, L3, L4, Ar4, R4 to R6, N-Het1, l3, l4, r5 and r6 are as defined in the above chemical formula B, Each of r4' and r6' is an integer from 0 to 3, r4" is an integer from 0 to 2, r5' is 0 or 1, When each of r4', r4" and r6' is 2 or an integer greater than or equal to 2, the substituents within the parentheses are the same or different.

7. In claim 4, The above chemical formula C-2 is a composition for an organic layer of an organic light-emitting device represented by the following chemical formula C-21 or C-22: [Chemical Formula C-21] [Chemical Formula C-22] In the above chemical formulas C-21 and C-22, Each of X3, N-Het2, L6, and l6 is as defined in the above chemical formula C, Each of L5, Ar5, R7', R8', l5, r7' and r8' is as defined in the above chemical formula C-2, r7" is an integer from 0 to 2, r8" is an integer from 0 to 3, If each of r7' and r8' is 2 or an integer greater than or equal to 2, the substituents within the parentheses are the same or different.

8. In claim 1, R1 to R6 are the same or different from each other, and are each independently hydrogen; or deuterium, A composition for an organic layer of an organic light-emitting device, wherein R7 and R8 are the same or different and each independently hydrogen; deuterium; a substituted or unsubstituted C6 to C30 aryl group; a substituted or unsubstituted C2 to C30 heteroaryl group; -P(=O)RR'; -SiRR'R"; or a combination thereof.

9. In claim 4, A composition for an organic layer of an organic light-emitting device, wherein L1 to L6 are the same or different from each other, and each independently represents a direct bond; a substituted or unsubstituted C6 to C30 arylene group; a substituted or unsubstituted C2 to C30 heteroarylene group; or a combination thereof.

10. In claim 1, A composition for an organic layer of an organic light-emitting device, wherein Ar1 to Ar4 are the same or different and each independently represent a substituted or unsubstituted C6 to C30 aryl group; a substituted or unsubstituted C2 to C30 heteroaryl group; or a combination thereof.

11. In claim 1, A composition for an organic layer of an organic light-emitting device, wherein Ra is a substituted or unsubstituted C6 to C30 aryl group; a substituted or unsubstituted C2 to C30 heteroaryl group; or a combination thereof.

12. In claim 1, A composition for an organic layer of an organic light-emitting device, wherein the deuterium contents of the heterocyclic compound represented by the above chemical formula A; the heterocyclic compound represented by the above chemical formula B; and the heterocyclic compound represented by the above chemical formula C are the same or different from each other, and are each independently 0% or 1% to 100%.

13. In claim 1, The above chemical formula A is a composition for an organic layer of an organic light-emitting device represented by any one of the following heterocyclic compounds: .

14. In claim 1, The above chemical formula B is a composition for an organic layer of an organic light-emitting device represented by any one of the following heterocyclic compounds: .

15. In claim 1, The above chemical formula C is a composition for an organic layer of an organic light-emitting device represented by any one of the following heterocyclic compounds: .

16. In claim 1, A composition for an organic layer of an organic light-emitting device, wherein the molar ratio of the heterocyclic compound represented by the above chemical formula A, the heterocyclic compound represented by the above chemical formula B, and the heterocyclic compound represented by the above chemical formula C is 0.1 to 3: 0.1 to 2: 0.1 to 2.

17. An organic light-emitting device comprising a first electrode; a second electrode provided opposite the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein at least one of the organic layers comprises a composition for an organic layer of an organic light-emitting device according to any one of claims 1 to 16.

18. In claim 17, An organic light-emitting device, wherein the organic layer further includes an emission layer, and the emission layer includes the composition for an organic light-emitting device.

19. In claim 17, An organic light-emitting device further comprising one or more layers selected from the group consisting of a light-emitting layer, a hole injection layer, a hole transport layer, a hole transport auxiliary layer, an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer.

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