Heterocyclic compound, organic light-emitting device, and composition for organic material layer of organic light-emitting device

Abstract

The present specification relates to a heterocyclic compound of chemical formula 1, an organic light-emitting device comprising the same, and a composition for an organic material layer of the organic light-emitting device.

Description

Heterocyclic compound, organic light-emitting device and composition for organic layer of organic light-emitting device

[0001] The present specification relates to a heterocyclic compound, an organic light-emitting device, and a composition for an organic layer of an organic light-emitting device.

[0002] This application claims the benefit of Korean Patent Application No. 10-2023-0130400, filed with the Korean Intellectual Property Office on September 27, 2023, the entire contents of which are incorporated herein by reference.

[0003] Electroluminescent 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.

[0004] 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.

[0005] 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.

[0006] To improve the performance, lifespan, or efficiency of organic light-emitting devices, the development of materials for organic thin films is continuously required.

[0007] <Prior Art Literature>

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

[0009] The present specification provides a heterocyclic compound, an organic light-emitting device, and a composition for an organic layer of an organic light-emitting device.

[0010] In one embodiment of the present specification, a heterocyclic compound of the following chemical formula 1 is provided.

[0011] [Chemical Formula 1]

[0012]

[0013] In the above chemical formula 1,

[0014] X is O or S,

[0015] Ar1 is a C6 to C60 aryl group substituted or unsubstituted with one or more substituents selected from deuterium, a halogen group, an alkyl group, a cycloalkyl group, an aryl group, and a heteroaryl group,

[0016] Ar2 is a substituted or unsubstituted C6 to C60 aryl group,

[0017] R1 to R4 are each independently hydrogen; deuterium; 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; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0018] D is deuterium, d1 is an integer from 1 to 4, d2 is an integer from 1 to 8,

[0019] r1 and r2 are integers from 1 to 3, respectively.

[0020] r3 is an integer from 0 to 3, and the sum of d1 and r3 is 4,

[0021] r4 is an integer from 0 to 7, and the sum of d2 and r4 is 8.

[0022] When r1 to r4 are each 2 or more, the substituents in parentheses are the same or different.

[0023] In another embodiment of the present specification, an organic light-emitting device is provided, comprising: a first electrode; a second electrode; and at least one organic layer provided between the first electrode and the second electrode, wherein at least one of the organic layers includes at least one type of the heterocyclic compound.

[0024] In another embodiment of the present specification, a composition for an organic layer of an organic light-emitting device comprising the heterocyclic compound is provided.

[0025] The heterocyclic compound described herein, when used in an organic light-emitting device, can lower the driving voltage of the device, improve the luminous efficiency, and enhance the lifespan characteristics of the device.

[0026] Specifically, the heterocyclic compound of the present invention is characterized by including a phenylene group in which the nitrogen of a triazine and a carbazole group is bonded in an ortho position as shown in Chemical Formula 1, a dibenzofuran / dibenzothiophene group in which an aryl group is substituted at a specific position as another substituent of the triazine, and an aryl group, and the carbazole group and the phenylene group necessarily contain deuterium. By substituting the triazine and the carbazole group at the ortho position, structural distortion is aggravated, facilitating charge transfer, and by including a bulky and rigid structure due to the substituent substituted at a specific position of the dibenzofuran / dibenzothiophene group, it can have a high T1 energy level. In addition, by including deuterium at a specific position, it helps to improve heat resistance, thereby improving the life characteristics of the device.

[0027] Figures 1 to 3 are diagrams each exemplifying a laminated structure of an organic light-emitting device according to one embodiment of the present specification.

[0028] <Explanation of symbols>

[0029] 100: Substrate

[0030] 200: Bipolar

[0031] 300: Organic layer

[0032] 301: Hole injection layer

[0033] 302: Hole transport layer

[0034] 303: Emissive layer

[0035] 304: Hole blocking layer

[0036] 305: Electron transport layer

[0037] 306: Electron injection layer

[0038] 400: Cathode

[0039] Hereinafter, the present specification will be described in more detail.

[0040] In this specification, when a part is said to "include" a component, this does not mean that it excludes other components, but rather that it may include other components, unless specifically stated otherwise.

[0041] In this specification, “N to N'” means N or more and N' or less.

[0042] In this specification, the chemical formula means the position where it is combined.

[0043] The term "substitution" above means that a hydrogen atom bonded to a carbon atom or nitrogen 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.

[0044] In this specification, "substituted or unsubstituted" means deuterium; halogen group; -CN; C1 to C60 alkyl group; C2 to C60 alkenyl group; C2 to C60 alkynyl group; C1 to C60 haloalkyl group; C1 to C60 alkoxy group; C6 to C60 aryloxy group; C1 to C60 alkylthioxy group; C6 to C60 arylthioxy group; C1 to C60 alkylsulfoxy group; C6 to C60 arylsulfoxy group; C3 to C60 cycloalkyl group; C2 to C60 heterocycloalkyl group; C6 to C60 aryl group; C2 to C60 heteroaryl group; silyl group; phosphine oxide group; And it means that it is substituted with one or more substituents selected from the group consisting of amine groups, or a substituent in which two or more substituents selected from the above substituents are connected, or is unsubstituted.

[0045] 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.

[0046] In one embodiment of the present application, "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, in which case the deuterium content may be 0% to 100%, and the deuterium content may also be expressed as a deuterium substitution ratio.

[0047] In one embodiment of the present application, in the case where “no substituent is indicated in the chemical formula or compound structure,” if deuterium is not explicitly excluded, such as “the deuterium content is 0%, the hydrogen content is 100%,” or “all substituents are hydrogen,” hydrogen and deuterium may be used in combination in the compound.

[0048] In one embodiment of the present application, 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.

[0049] In one embodiment of the present application, 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.

[0050] In one embodiment of the present application, the meaning of the substitution rate T% of a specific substituent can be defined as T2 / T1Х100 = T%, where 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.

[0051] That is, in one example, In the phenyl group represented by , a deuterium substitution rate of 20% means that the total number of substituents that the phenyl group can have is 5 (T1 in the formula), and if the number of deuteriums among them is 1 (T2 in the formula), it can be expressed as 20%. In other words, a deuterium substitution rate of 20% in the phenyl group can be expressed by the structural formula below.

[0052]

[0053] Additionally, in one embodiment of the present application, the term "phenyl group having a deuterium substitution rate of 0%" may mean a phenyl group that does not contain a deuterium atom as a substituent, i.e., has 5 hydrogen atoms.

[0054] In this specification, halogen may be fluorine, chlorine, bromine or iodine.

[0055] In the present specification, an 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, octyl group, n-octyl group, tert-octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2,2-dimethylheptyl group, Examples include, but are not limited to, 1-ethyl-propyl group, 1,1-dimethyl-propyl group, isohexyl group, 2-methylpentyl group, 4-methylhexyl group, and 5-methylhexyl group.

[0056] 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.

[0057] In the present specification, an 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.

[0058] In this specification, a haloalkyl group means an alkyl group substituted with a halogen group, and specific examples include, but are not limited to, -CF3, -CF2CF3, etc.

[0059] In this specification, an alkoxy group is represented as -O(R101), and examples of the alkyl group described above can be applied to R101.

[0060] In this specification, the aryloxy group is represented as -O(R102), and R102 can be applied to the examples of the aryl group described above.

[0061] In this specification, the alkylthioxy group is represented as -S(R103), and examples of the alkyl group described above can be applied to R103.

[0062] In this specification, the arylthioxy group is represented as -S(R104), and R104 can be applied to the examples of the aryl group described above.

[0063] In this specification, an alkylsulfoxy group is represented as -S(=0)2(R105), and examples of the alkyl group described above can be applied to R105.

[0064] In this specification, an arylsulfoxy group is represented as -S(=0)2(R106), and examples of the aryl group described above can be applied to R106.

[0065] In the present specification, a 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.

[0066] In the present specification, a 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.

[0067] In the present specification, an 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.

[0068] In this specification, the terphenyl group may be selected from the following structures.

[0069]

[0070] In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be combined with each other to form a ring.

[0071] When the above fluorenyl group is substituted, the structures below can be formed, but are not limited thereto.

[0072]

[0073] In the present specification, a 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 pyridine group, a pyrrole group, a pyrimidine group, a pyridazine group, a furan group, a thiophene group, an imidazole group, a pyrazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, a triazole group, a furazan group, an oxadiazole group, a thiadiazole group, a dithiazole group, a tetrazolyl group, a pyran group, a thiopyran group, a diazine group, an oxazine group, a thiazine group, a dioxin group, a triazine group, a tetrazine group, a quinoline group, an isoquinoline group, a quinazoline group, an isoquinazoline group, a quinozoline group, a naphthyridine group, an acridine group, a phenanthridine group, an imidazopyridine group, a diazanaphthalene group, a triazaindene group, an indole group, an indolizine group, a benzothiazole group, Benzoxazole group, benzimidazole group, benzothiophene group, benzofuran group, dibenzothiophene group, dibenzofuran group, carbazole group, benzocarbazole group, dibenzocarbazole group, phenazine group, dibenzosilole group, spirobi(dibenzosilole), dihydrophenazine group, phenoxazine group, phenanthridine group, thienyl group, indolo[2,3-a]carbazole group, indolo[2,3-b]carbazole group, indoline group, 10,11-dihydro-dibenzo[b,f]azepine group, 9,10-dihydroacridine group, phenanthrazine group, phenothiathiazine group, phthalazine group, phenanthroline group, naphthobenzofuran group, naphthobenzothiophene group, benzo[c][1,2,5]thiadiazole group, Examples thereof include, but are not limited to, 2,3-dihydrobenzo[b]thiophene group, 2,3-dihydrobenzofuran group, 5,10-dihydrodibenzo[b,e][1,4]azacillin group, pyrazolo[1,5-c]quinazoline group, pyrido[1,2-b]indazole group, pyrido[1,2-a]imidazo[1,2-e]indolin group, and 5,11-dihydroindeno[1,2-b]carbazole group.

[0074] In the present specification, the benzocarbazole group may have any of the following structures.

[0075]

[0076] In the present specification, the dibenzocarbazole group may have any of the following structures.

[0077]

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

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

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

[0081]

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

[0083]

[0084] 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(R107)(R108)(R109), and R107 to R109 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.

[0085] The above silyl group may include an alkylsilyl group, an arylsilyl group, a heteroarylsilyl group, an alkylarylsilyl group, an arylheteroarylsilyl group, etc., depending on the substituent bonded to the Si element. An alkylsilyl group, an arylsilyl group, or a heteroarylsilyl group means that the Si element of a silyl group is substituted with an alkyl group, an aryl group, or a heteroaryl group, respectively, an alkylarylsilyl group means that the Si element of a silyl group is substituted with an alkyl group and an aryl group, and an arylheteroarylsilyl group means that the Si element of a silyl group is substituted with an aryl group and a heteroaryl group.

[0086] Specific examples of silyl groups include, but are not limited to, the following structures.

[0087] (trimethylsilyl group), (triethylsilyl group), (t-butyldimethylsilyl group), (vinyldimethylsilyl group), (propyldimethylsilyl group), (triphenylsilyl group), (diphenylsilyl group), (phenylsilyl group)

[0088] In the present specification, a phosphine oxide group is represented by -P(=O)(R110)(R111), and R110 and R111 are the same as 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, and dinaphthylphosphine oxide.

[0089] In the present specification, an amine group is represented by -N(R112)(R113), and R112 and R113 are the same as 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.

[0090] In this specification, the description of the aryl group described above may be applied, except that the arylene group is divalent.

[0091] In this specification, the description of the heteroaryl group described above may be applied, except that the heteroarylene group is divalent.

[0092] One embodiment of the present specification provides a heterocyclic compound of the following chemical formula 1.

[0093] [Chemical Formula 1]

[0094]

[0095] In the above chemical formula 1,

[0096] X is O or S,

[0097] Ar1 is a C6 to C60 aryl group substituted or unsubstituted with one or more substituents selected from deuterium, a halogen group, an alkyl group, a cycloalkyl group, an aryl group, and a heteroaryl group,

[0098] Ar2 is a substituted or unsubstituted C6 to C60 aryl group,

[0099] R1 to R4 are each independently hydrogen; deuterium; 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; or a substituted or unsubstituted C2 to C60 heteroaryl group,

[0100] D is deuterium, d1 is an integer from 1 to 4, d2 is an integer from 1 to 8,

[0101] r1 and r2 are integers from 1 to 3, respectively.

[0102] r3 is an integer from 0 to 3, and the sum of d1 and r3 is 4,

[0103] r4 is an integer from 0 to 7, and the sum of d2 and r4 is 8.

[0104] When r1 to r4 are each 2 or more, the substituents in parentheses are the same or different.

[0105] In one embodiment of the present specification, X may be O.

[0106] In one embodiment of the present specification, X may be S.

[0107] In one embodiment of the present specification, the chemical formula 1 may be represented by any one of the following chemical formulas 1-1 to 1-4.

[0108] [Chemical Formula 1-1]

[0109]

[0110] [Chemical Formula 1-2]

[0111]

[0112] [Chemical Formula 1-3]

[0113]

[0114] [Chemical Formula 1-4]

[0115]

[0116] In the above chemical formulas 1-1 to 1-4,

[0117] The definition of each substituent is the same as that in the chemical formula 1 above.

[0118] In one embodiment of the present specification, the chemical formula 1 may be represented by the following chemical formula 1-O or 1-S.

[0119] [Chemical formula 1-O]

[0120]

[0121] [Chemical Formula 1-S]

[0122]

[0123] In the above chemical formulas 1-O and 1-S,

[0124] The definition of each substituent is the same as that in the chemical formula 1 above.

[0125] In one embodiment of the present specification, R1 to R4 may each independently be hydrogen; deuterium; 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; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0126] In one embodiment of the present specification, R1 to R4 may each independently be hydrogen; deuterium; a substituted or unsubstituted C1 to C10 alkyl group; a substituted or unsubstituted C3 to C20 cycloalkyl group; a substituted or unsubstituted C2 to C20 heterocycloalkyl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0127] In one embodiment of the present specification, R1 to R4 may each independently be hydrogen; deuterium; a substituted or unsubstituted C1 to C30 alkyl group; or a substituted or unsubstituted C3 to C30 cycloalkyl group.

[0128] In one embodiment of the present specification, R1 to R4 may each independently be hydrogen or deuterium.

[0129] In one embodiment of the present specification, R1 to R4 may be hydrogen.

[0130] In one embodiment of the present specification, R1 and R2 may each independently be hydrogen; deuterium; 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; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0131] In one embodiment of the present specification, R1 and R2 may each independently be hydrogen; deuterium; a substituted or unsubstituted C1 to C10 alkyl group; a substituted or unsubstituted C3 to C20 cycloalkyl group; a substituted or unsubstituted C2 to C20 heterocycloalkyl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0132] In one embodiment of the present specification, R1 and R2 may each independently be hydrogen; deuterium; a substituted or unsubstituted C1 to C30 alkyl group; or a substituted or unsubstituted C3 to C30 cycloalkyl group.

[0133] In one embodiment of the present specification, R1 and R2 may each independently be hydrogen or deuterium.

[0134] In one embodiment of the present specification, R1 and R2 may be hydrogen.

[0135] In one embodiment of the present specification, R3 and R4 may each independently be hydrogen; 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; or a substituted or unsubstituted C2 to C60 heteroaryl group.

[0136] In one embodiment of the present specification, R3 and R4 may each independently be hydrogen; 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; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0137] In one embodiment of the present specification, R3 and R4 may each independently be hydrogen; a substituted or unsubstituted C1 to C10 alkyl group; a substituted or unsubstituted C3 to C20 cycloalkyl group; a substituted or unsubstituted C2 to C20 heterocycloalkyl group; or a substituted or unsubstituted C2 to C20 heteroaryl group.

[0138] In one embodiment of the present specification, R3 and R4 may each independently be hydrogen; a substituted or unsubstituted C1 to C30 alkyl group; or a substituted or unsubstituted C3 to C30 cycloalkyl group.

[0139] In one embodiment of the present specification, R3 and R4 may be hydrogen.

[0140] In one embodiment of the present specification, D is deuterium, d1 is an integer from 1 to 4, and d2 is an integer from 1 to 8.

[0141] That is, the above chemical formula 1 must contain at least one deuterium in each of the phenylene group and the carbazole group.

[0142] In general, compounds substituted with only hydrogen and compounds substituted with deuterium show differences in thermodynamic behavior due to differences in atomic mass, van der Waals radius, etc. Deuterium has lower vibrational energy than hydrogen, and the bond between carbon and deuterium is shorter and has stronger dissociation energy compared to the bond between carbon and hydrogen. Accordingly, compounds substituted with deuterium have the characteristic of having a lower ground state energy than compounds substituted with only hydrogen, and the molecular hardcore volume is reduced, which can reduce electrical polarizability. In addition, it has the effect of increasing the volume of the device thin film by weakening the intermolecular interaction, and lowering the crystallinity by creating an amorphous state of the thin film. Therefore, when the heterocyclic compound of the present invention is used as a material for an OLED device, the device efficiency and lifespan characteristics can be improved.

[0143] In one embodiment of the present specification, r3 and r4 may be 0.

[0144] In one embodiment of the present specification, the chemical formula 1 may be represented by the following chemical formula 1-1-1.

[0145] [Chemical Formula 1-1-1]

[0146]

[0147] In the above chemical formula 1-1-1,

[0148] The definition of each substituent is the same as that in the chemical formula 1 above.

[0149] In one embodiment of the present specification, the chemical formula 1 may be represented by the following chemical formula 1-D.

[0150] [Chemical Formula 1-D]

[0151]

[0152] In the above chemical formula 1-D,

[0153] The definition of each substituent is the same as that in the chemical formula 1 above.

[0154] In one embodiment of the present specification, the deuterium substitution rate of the chemical formula 1 may be from more than 0% to 100%.

[0155] In one embodiment of the present specification, the deuterium substitution rate of the chemical formula 1 may be 10% to 90%.

[0156] In one embodiment of the present specification, the deuterium substitution rate of the chemical formula 1 may be 20% to 80%.

[0157] In one embodiment of the present specification, the deuterium substitution rate of the chemical formula 1 may be 30% to 60%.

[0158] In this specification, the deuterium substitution rate of the chemical formula 1 refers to the substitution rate of deuterium with respect to the total number of hydrogens and deuteriums contained in the chemical formula 1. For example, if there are 20 hydrogens and 20 deuteriums contained in the chemical formula 1, the substitution rate of 20 deuteriums with respect to the total of 40 hydrogens and deuteriums is 50%.

[0159] In one embodiment of the present specification, when the deuterium substitution rate of the heterocyclic compound of the chemical formula 1 satisfies the above range, the photochemical characteristics of the compound not containing deuterium and the compound containing deuterium are almost similar, but when deposited on a thin film, the material containing deuterium tends to be packed with a narrower intermolecular distance.

[0160] Accordingly, by fabricating an EOD (Electron Only Device) and a HOD (Hole Only Device) and checking the current density according to the voltage, it can be confirmed that the heterocyclic compound of chemical formula 1 of the present invention exhibits much more balanced charge transport characteristics than a compound that does not contain deuterium.

[0161] Additionally, when looking at the surface of the thin film with an atomic force microscope (AFM), it can be confirmed that the thin film made of a compound containing deuterium is deposited with a more uniform surface without any aggregated areas.

[0162] Additionally, since the single bond dissociation energy of carbon and deuterium is higher than the single bond dissociation energy of carbon and hydrogen, in the case of the heterocyclic compound of chemical formula 1 of the present invention, the stability of the entire molecule increases, thereby improving the device lifespan.

[0163] In one embodiment of the present specification, the chemical formula 1 includes structures of the following chemical formulas A and B, and the deuterium substitution rate of the chemical formula A may be greater than 0% and less than or equal to 100%, and the deuterium substitution rate of the chemical formula B may be from 0% to 100%.

[0164] [Chemical Formula A]

[0165]

[0166] [Chemical Formula B]

[0167]

[0168] In the above chemical formulas A and B,

[0169] is the position where chemical formulas A and B are combined,

[0170] The definition of each substituent is the same as that in the chemical formula 1 above.

[0171] In this specification, the deuterium substitution rate of the chemical formula A or B means the substitution rate of deuterium with respect to the total number of hydrogens and deuteriums contained in the chemical formula A or B.

[0172] In one embodiment of the present specification, the deuterium substitution rate of the chemical formula A may be 10% to 100%, and the deuterium substitution rate of the chemical formula B may be 0% to 80%.

[0173] In one embodiment of the present specification, the deuterium substitution rate of the chemical formula A may be 30% to 100%, and the deuterium substitution rate of the chemical formula B may be 0% to 50%.

[0174] In one embodiment of the present specification, the deuterium substitution rate of the chemical formula A may be 100%, and the deuterium substitution rate of the chemical formula B may be 0%.

[0175] In one embodiment of the present specification, Ar1 may be a C6 to C30 aryl group substituted or unsubstituted with one or more substituents selected from deuterium, a halogen group, an alkyl group, a cycloalkyl group, an aryl group, and a heteroaryl group.

[0176] In one embodiment of the present specification, Ar1 may be a C6 to C20 aryl group substituted or unsubstituted with one or more substituents selected from deuterium, a halogen group, an alkyl group, a cycloalkyl group, an aryl group, and a heteroaryl group.

[0177] In one embodiment of the present specification, Ar1 is a phenyl group unsubstituted or substituted with one or more substituents selected from among deuterium, a halogen group, an alkyl group, a cycloalkyl group, an aryl group, and a heteroaryl group; a biphenyl group unsubstituted or substituted with one or more substituents selected from among deuterium, a halogen group, an alkyl group, a cycloalkyl group, an aryl group, and a heteroaryl group; a terphenyl group unsubstituted or substituted with one or more substituents selected from among deuterium, a halogen group, an alkyl group, a cycloalkyl group, an aryl group, and a heteroaryl group; a naphthyl group unsubstituted or substituted with one or more substituents selected from among deuterium, a halogen group, an alkyl group, a cycloalkyl group, an aryl group, and a heteroaryl group; a phenanthrenyl group unsubstituted or substituted with one or more substituents selected from among deuterium, a halogen group, an alkyl group, a cycloalkyl group, an aryl group, and a heteroaryl group; Or it may be a triphenylenyl group substituted or unsubstituted with one or more substituents selected from deuterium, a halogen group, an alkyl group, a cycloalkyl group, an aryl group, and a heteroaryl group.

[0178] In one embodiment of the present specification, Ar1 may be an aryl group of C6 to C60.

[0179] In one embodiment of the present specification, Ar1 may be an aryl group having C6 to C30.

[0180] In one embodiment of the present specification, Ar1 may be an aryl group having C6 to C20.

[0181] In one embodiment of the present specification, Ar2 may be a substituted or unsubstituted C6 to C30 aryl group.

[0182] In one embodiment of the present specification, Ar2 may be a substituted or unsubstituted C6 to C20 aryl group.

[0183] In one embodiment of the present specification, Ar2 may be a substituted or unsubstituted C6 to C15 aryl group.

[0184] In one embodiment of the present specification, Ar2 may be a substituted or unsubstituted phenyl group; or a substituted or unsubstituted biphenyl group.

[0185] In one embodiment of the present specification, Ar2 may be an aryl group of C6 to C60.

[0186] In one embodiment of the present specification, Ar2 may be an aryl group having C6 to C30.

[0187] In one embodiment of the present specification, Ar2 may be an aryl group having C6 to C20.

[0188] In one embodiment of the present specification, Ar2 may be an aryl group having C6 to C15.

[0189] In one embodiment of the present specification, Ar1 is a C6 to C20 aryl group substituted or unsubstituted with one or more substituents selected from deuterium, a halogen group, an alkyl group, a cycloalkyl group, an aryl group, and a heteroaryl group, and Ar2 may be a substituted or unsubstituted C6 to C15 aryl group.

[0190] In one embodiment of the present specification, Ar1 and Ar2 may not contain deuterium.

[0191] In one embodiment of the present specification, Ar1 and Ar2 may each independently be an aryl group having C6 to C60.

[0192] In one embodiment of the present specification, Ar1 and Ar2 may each independently be an aryl group having C6 to C30.

[0193] In one embodiment of the present specification, Ar1 and Ar2 may each independently be an aryl group having C6 to C20.

[0194] In one embodiment of the present specification, Ar1 may be an aryl group having C6 to C20, and Ar2 may be an aryl group having C6 to C15.

[0195] In one embodiment of the present specification, the chemical formula 1 may be represented by any one of the following compounds.

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204] In addition, by introducing various substituents into the structure of the above chemical formula 1, compounds having the unique characteristics of the introduced substituents can be synthesized. For example, by introducing substituents mainly used in hole injection layer materials, hole transport layer materials, light-emitting layer materials, electron transport layer materials, and charge generation layer materials used in the manufacture of organic light-emitting devices into the core structure, a material satisfying the conditions required for each organic layer can be synthesized.

[0205] In addition, by introducing various substituents into the structure of the above chemical formula 1, 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.

[0206] In another embodiment of the present specification, an organic light-emitting device is provided, comprising: a first electrode; a second electrode; and at least one organic layer provided between the first electrode and the second electrode, wherein at least one layer of the organic layer comprises at least one heterocyclic compound of the chemical formula 1.

[0207] In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer may include one or more types of the heterocyclic compound.

[0208] In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer may include one type of the heterocyclic compound.

[0209] In one embodiment of the present specification, the organic layer includes a light-emitting layer, the light-emitting layer includes a host, and the host may include one or more of the heterocyclic compounds.

[0210] In one embodiment of the present specification, the organic layer includes a light-emitting layer, the light-emitting layer includes a host, and the host may include one type of the heterocyclic compound.

[0211] In one embodiment of the present specification, the organic layer includes a light-emitting layer, the light-emitting layer includes a host, the host includes a green host, and the green host may include one or more of the heterocyclic compounds.

[0212] In one embodiment of the present specification, the organic layer includes a light-emitting layer, the light-emitting layer includes a host, the host includes a red host, and the red host may include one or more of the heterocyclic compounds.

[0213] In one embodiment of the present specification, the organic layer includes a light-emitting layer, the light-emitting layer includes a host, the host includes a blue host, and the blue host may include one or more of the heterocyclic compounds.

[0214] In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer may include the heterocyclic compound as an N-type host.

[0215] In one embodiment of the present specification, the organic layer including the heterocyclic compound may further include a compound of the following chemical formula 2 or 3.

[0216] [Chemical Formula 2]

[0217]

[0218] [Chemical Formula 3]

[0219]

[0220] In the above chemical formulas 2 and 3,

[0221] R11, R12, R21 and R22 are each independently selected from the group consisting of hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy 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; a substituted or unsubstituted silyl group; a substituted or unsubstituted phosphine oxide group; and a substituted or unsubstituted amine group,

[0222] L11, L12, L21 and L22 are each independently a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group,

[0223] Ar11, Ar12, Ar21 and Ar22 are each independently a cyano group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; or a substituted or unsubstituted silyl group,

[0224] r11 and r12 are integers from 1 to 7, respectively,

[0225] r21 is an integer from 1 to 6,

[0226] r22 is an integer from 1 to 4,

[0227] l11, l12, l21 and l22 are integers from 1 to 3, respectively.

[0228] When r11, r12, r21, r22, l11, l12, l21, and l22 are each 2 or more, the substituents in parentheses are the same or different.

[0229] In one embodiment of the present specification, the organic layer includes a light-emitting layer, and the light-emitting layer may further include a compound of the chemical formula 2 or 3.

[0230] In one embodiment of the present specification, the organic layer includes a light-emitting layer, the light-emitting layer includes a host, and the host may further include a compound of the chemical formula 2 or 3.

[0231] In one embodiment of the present specification, the light-emitting layer may further include a compound of the above chemical formula 2 as a P-type host.

[0232] In one embodiment of the present specification, R11 and R12 may each independently be selected from the group consisting of 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; and a substituted or unsubstituted C2 to C60 heteroaryl group.

[0233] In one embodiment of the present specification, R11 and R12 may each independently be selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted C6 to C60 aryl group; and a substituted or unsubstituted C2 to C60 heteroaryl group.

[0234] In one embodiment of the present specification, R11 and R12 may each independently be hydrogen or deuterium.

[0235] In one embodiment of the present specification, L11 and L12 may each independently be a direct bond; or a substituted or unsubstituted C6 to C60 arylene group.

[0236] In one embodiment of the present specification, L11 and L12 may each independently be a direct bond; or a substituted or unsubstituted C6 to C30 arylene group.

[0237] In one embodiment of the present specification, L11 and L12 may each independently be a direct bond; or a substituted or unsubstituted C6 to C15 arylene group.

[0238] In one embodiment of the present specification, L11 and L12 may each independently be a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted biphenylene group.

[0239] In one embodiment of the present specification, L11 and L12 may each independently be a direct bond; or a substituted or unsubstituted phenylene group.

[0240] In one embodiment of the present specification, L11 and L12 may each independently be a direct bond; or an arylene group having C6 to C60 substituted or unsubstituted with deuterium.

[0241] In one embodiment of the present specification, L11 and L12 may each independently be a direct bond; or a C6 to C30 arylene group substituted or unsubstituted with deuterium.

[0242] In one embodiment of the present specification, L11 and L12 may each independently be a direct bond; or a C6 to C15 arylene group substituted or unsubstituted with deuterium.

[0243] In one embodiment of the present specification, Ar11 and Ar12 may each independently be a cyano group; a substituted or unsubstituted C6 to C30 aryl group; a substituted or unsubstituted C2 to C30 heteroaryl group; or a substituted or unsubstituted C1 to C30 silyl group.

[0244] In one embodiment of the present specification, Ar11 and Ar12 may each independently be a substituted or unsubstituted C6 to C30 aryl group; a substituted or unsubstituted C2 to C30 heteroaryl group; or a substituted or unsubstituted C1 to C30 silyl group.

[0245] In one embodiment of the present specification, Ar11 and Ar12 may each independently be a cyano group; a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C6 to C30 arylsilyl group.

[0246] In one embodiment of the present specification, Ar11 and Ar12 may each independently be a cyano group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted triphenylenyl group; a substituted or unsubstituted fluorenyl group; or a substituted or unsubstituted triphenylsilyl group.

[0247] In one embodiment of the present specification, Ar11 and Ar12 may each independently be a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C6 to C30 arylsilyl group.

[0248] In one embodiment of the present specification, Ar11 and Ar12 may each independently be a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted triphenylenyl group; a substituted or unsubstituted fluorenyl group; or a substituted or unsubstituted triphenylsilyl group.

[0249] In one embodiment of the present specification, Ar11 and Ar12 may each independently be a C6 to C30 aryl group unsubstituted or substituted with one or more substituents selected from deuterium, a cyano group, an alkyl group, and an aryl group; or a C6 to C30 arylsilyl group unsubstituted or substituted with deuterium.

[0250] In one embodiment of the present specification, the chemical formula 2 may be selected from the following compounds.

[0251]

[0252]

[0253]

[0254]

[0255]

[0256]

[0257] In one embodiment of the present specification, the light-emitting layer may further include a compound of the above chemical formula 3 as a P-type host.

[0258] In one embodiment of the present specification, R21 and R22 may each independently be selected from the group consisting of 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; and a substituted or unsubstituted C2 to C60 heteroaryl group.

[0259] In one embodiment of the present specification, R21 and R22 may each independently be selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted C6 to C60 aryl group; and a substituted or unsubstituted C2 to C60 heteroaryl group.

[0260] In one embodiment of the present specification, R21 and R22 may each independently be hydrogen or deuterium.

[0261] In one embodiment of the present specification, L21 and L22 may each independently be a direct bond; a substituted or unsubstituted C6 to C30 arylene group; or a substituted or unsubstituted C2 to C30 heteroarylene group.

[0262] In one embodiment of the present specification, L21 and L22 may each independently be a direct bond; a substituted or unsubstituted C6 to C15 arylene group; or a substituted or unsubstituted C2 to C15 heteroarylene group.

[0263] In one embodiment of the present specification, L21 and L22 may each independently be a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; or a substituted or unsubstituted divalent dibenzofuran group.

[0264] In one embodiment of the present specification, L21 and L22 may each independently be a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted divalent dibenzofuran group.

[0265] In one embodiment of the present specification, L21 and L22 may each independently be a direct bond; a C6 to C30 arylene group substituted or unsubstituted with deuterium; or a C2 to C30 heteroarylene group substituted or unsubstituted with deuterium.

[0266] In one embodiment of the present specification, L21 and L22 may each independently be a direct bond; a C6 to C15 arylene group substituted or unsubstituted with deuterium; or a C2 to C15 heteroarylene group substituted or unsubstituted with deuterium.

[0267] In one embodiment of the present specification, Ar21 and Ar22 may each independently be a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

[0268] In one embodiment of the present specification, Ar21 and Ar22 may each independently be a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted triphenylenyl group; a substituted or unsubstituted dibenzofuran group; or a substituted or unsubstituted dibenzothiophene group.

[0269] In one embodiment of the present specification, Ar21 and Ar22 may each independently be a C6 to C30 aryl group substituted or unsubstituted with deuterium; or a C2 to C30 heteroaryl group substituted or unsubstituted with deuterium.

[0270] In one embodiment of the present specification, the chemical formula 3 may be selected from the following compounds.

[0271]

[0272]

[0273]

[0274]

[0275]

[0276]

[0277] The organic layer of the organic light-emitting device of the present invention 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 invention 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 number of organic layers.

[0278] In one embodiment of the present specification, the first electrode may be an anode, and the second electrode may be a cathode.

[0279] In another embodiment of the present specification, the first electrode may be a cathode and the second electrode may be an anode.

[0280] An organic light-emitting device according to one embodiment of the present specification can be manufactured using a conventional method and material for manufacturing an organic light-emitting device, except that one or more organic layers are formed using the heterocyclic compound of the above-described chemical formula 1.

[0281] The heterocyclic compound of the above chemical formula 1 can be formed into an organic layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light-emitting device. Here, the solution coating method refers to, but is not limited to, spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc.

[0282] In one embodiment of the present specification, the organic light-emitting device may be a blue organic light-emitting device, and the heterocyclic compound of the chemical formula 1 may be used as a material of the blue organic light-emitting device. For example, the heterocyclic compound of the chemical formula 1 may be included in a light-emitting layer of the blue organic light-emitting device.

[0283] In another embodiment of the present specification, the organic light-emitting device may be a green organic light-emitting device, and the heterocyclic compound of the chemical formula 1 may be used as a material of the green organic light-emitting device. For example, the heterocyclic compound of the chemical formula 1 may be included in a light-emitting layer of the green organic light-emitting device.

[0284] In another embodiment of the present specification, the organic light-emitting device may be a red organic light-emitting device, and the heterocyclic compound of the chemical formula 1 may be used as a material of the red organic light-emitting device. For example, the heterocyclic compound of the chemical formula 1 may be included in a light-emitting layer of the red organic light-emitting device.

[0285] The organic light-emitting device of the present invention may further include one or more layers selected from the group consisting of a light-emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer.

[0286] 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.

[0287] 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, as shown in FIG. 2, may also be implemented.

[0288] 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). However, the scope of the present application is not limited by such a laminated structure, and, if necessary, the remaining layers except for the light-emitting layer may be omitted, and other necessary functional layers may be further added.

[0289] The organic layer containing the heterocyclic compound of the above chemical formula 1 may additionally contain other substances as needed.

[0290] In an organic light-emitting device according to one embodiment of the present specification, materials other than the heterocyclic compound of the above chemical formula 1 are exemplified below, but these are only for exemplification and are not intended to limit the scope of the present application, and may be replaced with materials known in the art.

[0291] 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.

[0292] Materials with relatively low work functions can be used as cathode materials, and metals, metal oxides, or conductive polymers can be used. Specific examples of the cathode materials include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayered materials such as LiF / Al or LiO2 / Al.

[0293] As the hole injection material, a known hole injection material may be used, 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-styrenesulfonate) can be used.

[0294] Pyrazoline derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, etc. can be used as hole transport materials, and low molecular weight or high molecular weight materials can also be used.

[0295] 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. can be used, and not only low molecular weight substances but also high molecular weight substances can be used.

[0296] For example, LiF is a representative material used in the art, but the present application is not limited thereto.

[0297] Red, green, or blue light-emitting materials may be used as the light-emitting material, and if necessary, two or more light-emitting materials may be mixed and used. At this time, 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, but materials in which both the host material and the dopant material participate in light emission may also be used.

[0298] 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.

[0299] 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.

[0300] 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.

[0301] In addition, by introducing various substituents into the structure of the above chemical formula 1, 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.

[0302] Another embodiment of the present specification provides a composition for an organic layer comprising the heterocyclic compound.

[0303] In one embodiment of the present specification, the composition for the organic layer may further include a compound of the chemical formula 2 or 3.

[0304] In one embodiment of the present specification, the composition for the organic layer may include the heterocyclic compound and the compound of the chemical formula 2 or 3 in a weight ratio of 1:10 to 10:1.

[0305] In one embodiment of the present specification, the composition for the organic layer may include the heterocyclic compound and the compound of the chemical formula 2 or 3 in a weight ratio of 1:8 to 8:1, 1:5 to 5:1, or 1:3 to 3:1.

[0306] In one embodiment of the present specification, the composition for the organic layer may include the heterocyclic compound and the compound of the chemical formula 2 or 3 in a weight ratio of 1:1 to 5:1, or 1:1 to 3:1.

[0307] Another embodiment of the present specification provides a method for manufacturing an organic light-emitting device, comprising the steps of: preparing a substrate; forming a first electrode on the substrate; forming one or more organic layers on the first electrode; and forming a second electrode on the organic layer, wherein the step of forming the organic layer includes the step of forming one or more organic layers using the organic layer composition described above.

[0308] In one embodiment of the present specification, the step of forming the organic layer may include a step of premixing a composition for the organic layer of the organic light-emitting device and depositing it using one supply source.

[0309] The above pre-mixing means that the heterocyclic compound of the above chemical formula 1 and the compound of the above chemical formula 2 or 3 are mixed in one container before being deposited on the organic layer. In the case of pre-mixing, there is an advantage in that the process is simpler because one deposition source is used instead of two or more deposition sources.

[0310] When premixing the composition for the above organic layer, the inherent thermal properties of each material can significantly affect deposition conditions, such as the deposition rate, when depositing the premixed material. Therefore, the inherent thermal properties of each material to be premixed must be confirmed. If the thermal properties of the materials are not similar, repeatability and reproducibility in the deposition process cannot be maintained, and uniform OLED devices cannot be manufactured.

[0311] To overcome this, the electrical properties of each material can be tuned by appropriately combining the basic structure and substituents of each material, while thermal properties can also be controlled based on the morphology of the molecular structure. By manipulating the thermal properties of each material, a variety of host-to-host premixed deposition processes can be secured. This allows for the creation of diverse premixed deposition processes utilizing not only two compounds as hosts, but also three or more host materials.

[0312] In one embodiment of the present specification, the composition for the organic layer may include a host other than the compound of the chemical formula 2 or 3.

[0313] In one embodiment of the present specification, the composition for the organic layer includes a compound of the chemical formula 2 or 3, and may further include another host.

[0314] 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.

[0315] <Manufacturing Example>

[0316] <Manufacturing Example 1> Preparation of compound 1-1-1

[0317]

[0318] 1) Preparation of compound 1-1-1-a

[0319] 10 g (31.0 mM) of compound 9-(2-bromophenyl)-9H-carbazole, 100 ml of D6-benzene, and 14.7 ml (155 mM) of CF3SO3H(triflic acid) were placed in a reactor and refluxed at 50°C for 2 hours. After the reaction was completed, the mixture was neutralized using a supersaturated aqueous solution of K3PO4, and distilled water and dichloromethane (DCM) were added at room temperature to extract the organic layer. The separated organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (DCM:Hexane=1:4) to obtain 9.8 g (yield 95%) of compound 1-1-1-a.

[0320] 2) Preparation of compound 1-1-1-b

[0321] Compound 1-1-1-a 9.8 g (29.3 mM), Pd(dppf)Cl2([1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II)) 1.07 g (1.47 mM), and KOAc(Potassium Acetate) 5.75 g (58.6 mM) were placed in a reactor and dissolved in 100 mL of 1,4-dioxane, followed by refluxing at 101°C for 4 hours. After the reaction was completed, distilled water and DCM were added at room temperature to extract the mixture, and the organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (DCM:Hexane=1:1) to obtain compound 1-1-1-b 8 g (yield 72%).

[0322] 3) Preparation of compound 1-1-1-c

[0323] Compound [A] (1-bromo-6-chlorodibenzo[b,d]furan) 10 g (35.5 mM), compound [B] (Phenyl boronic acid) 4.42 g (35.5 mM), Pd(PPh3)4(Tetrakis(triphenylphosphine)palladium(0)) 2.05 g (1.8 mM), and K2CO3 9.82 g (71 mM) were placed in a reactor and dissolved in 1,4-dioxane / H2O 100 mL / 20 mL, and refluxed at 101℃ for 5 hours. After the reaction was completed, distilled water and DCM were added at room temperature to extract, and the organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (DCM:Hexane=1:2) to obtain compound 1-1-1-c 9.5 g (yield 96%).

[0324] 4) Preparation of compound 1-1-1-d

[0325] Compound 1-1-1-c 9.5 g (34.1 mM), Bis(pinacolato)diboron 13.0 g (51.2 mM), Pd2(dba) 33.12 g (3.41 mM), and KOAc 8.37 g (85.3 mM) were placed in a reactor and dissolved in 100 mL of 1,4-dioxane, followed by refluxing at 101°C for 4 hours. After the reaction was completed, distilled water and DCM were added at room temperature to extract the mixture, and the organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (DCM:Hexane=1:1) to obtain compound 1-1-1-d 11 g (yield 87%).

[0326] 5) Preparation of compound 1-1-1-e

[0327] Compound 1-1-1-d 11 g (29.7 mM), compound [C] (2,4-dichloro-6-phenyl-1,3,5-triazine) 6.7 g (29.7 mM), Pd(PPh3) 41.7 g (1.49 mM), and K2CO3 10.3 g (74.3 mM) were placed in a reactor and dissolved in 1,4-dioxane / H2O 110 mL / 22 mL, and refluxed at 101°C for 5 hours. After the reaction was completed, distilled water and DCM were added at room temperature to extract, and the organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (DCM:Hexane=1:3) to obtain compound 1-1-1-e 10.1 g (yield 78%).

[0328] 6) Preparation of compound 1-1-1

[0329] Compound 1-1-1-b 8 g (21.0 mM), compound 1-1-1-e 9.1 g (21.0 mM), Pd(PPh3) 41.8 g (1.55 mM), and K2CO3 7.3 g (52.5 mM) were placed in a reactor and dissolved in 1,4-Dioxane / H2O 100 mL / 20 mL, and refluxed at 101°C for 5 hours. After the reaction was completed, distilled water and DCM were added at room temperature to extract, and the organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (DCM:Hexane=1:2) to obtain compound 1-1-1 9.0 g (yield 66%).

[0330] The target compound of Table 1 was synthesized in the same manner as in Manufacturing Example 1, except that Intermediate A of Table 1 below was used instead of Compound [A] in Manufacturing Example 1, Intermediate B of Table 1 below was used instead of Compound [B], and Intermediate C of Table 1 below was used instead of Compound [C].

[0331] [Table 1]

[0332]

[0333]

[0334]

[0335]

[0336]

[0337]

[0338]

[0339]

[0340]

[0341]

[0342]

[0343] <Manufacturing Example 2> Preparation of compound 2-3

[0344]

[0345] Compound [a] (3-bromo-1,1'-bipheny) 3.7 g (15.8 mM), compound [b] (9-phenyl-9H,9'H-3,3'-bicarbazole) 6.5 g (15.8 mM), CuI 0.3 g (1.58 mM), trans-1,2-diaminocyclohexane 0.19 mL (1.58 mM), and K3PO4 3.3 g (31.6 mM) were dissolved in 100 mL of 1,4-dioxane and refluxed at 110℃ for 12 hours. After the reaction was completed, distilled water and DCM were added at room temperature to extract, and the organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (DCM:Hexane = 1:3) and recrystallized from methanol to obtain 7.5 g (yield 85%) of compound 2-3.

[0346] The target compound of Table 2 was synthesized by the same method as in Manufacturing Example 2, except that intermediate a of Table 2 below was used instead of compound [a] in Manufacturing Example 2 and intermediate b of Table 2 below was used instead of compound [b].

[0347] [Table 2]

[0348]

[0349] <Manufacturing Example 3> Preparation of compound 2-98

[0350]

[0351] 1) Preparation of compound 2-98-1

[0352] In a one-neck round bottom flask, 10 g (0.030 mol) of 9H,9'H-3,3'-bicarbazole, 7.26 g (0.030 mol) of compound [c] (4-bromo-1,1'-biphenyl-2,2',3,3',4',5,5',6,6'-D9), 0.57 g (0.003 mol) of CuI, 0.34 g (0.003 mol) of trans-1,2-diaminocyclohexane, and 12.7 g (0.060 mol) of K3PO4 were dissolved in 100 ml of 1,4-dioxane, and refluxed at 110°C for 8 hours. After the reaction was completed, the mixture was cooled, extracted with DCM, and dried over MgSO4. The filtered organic layer was concentrated under reduced pressure and separated by column chromatography to obtain 13.92 g (yield 94%) of compound 2-98-1.

[0353] 2) Preparation of compound 2-98

[0354] In a one-neck round bottom flask, 13.92 g (0.028 mol) of compound 2-98-1, 6.83 g (0.028 mol) of compound [d] (4-bromo-1,1'-biphenyl-2,2',3,3',4',5,5',6,6'-D9), 0.53 g (0.0028 mol) of CuI, 0.32 g (0.0028 mol) of trans-1,2-diaminocyclohexane, and 11.89 g (0.056 mol) of K3PO4 were dissolved in 140 ml of 1,4-dioxane, and refluxed at 110°C for 8 hours. After the reaction was completed, the mixture was cooled, extracted with DCM, and dried over MgSO4. The filtered organic layer was concentrated under reduced pressure and separated by column chromatography to obtain 16.14 g (yield 88%) of compound 2-98.

[0355] In the above Manufacturing Example 3, the target compound of Table 3 below was synthesized in the same manner as Manufacturing Example 3 above, except that intermediate c of Table 3 below was used instead of compound [c], and intermediate d of Table 3 below was used instead of compound [d].

[0356] When intermediate c and intermediate d are the same, the target compound can be directly synthesized by adding 2 equivalents of intermediate c in the manufacturing method of compound 2-98-1 of Manufacturing Example 3.

[0357] [Table 3]

[0358]

[0359] <Manufacturing Example 4> Preparation of compound 2-106

[0360]

[0361] 1) Preparation of compound 2-106-1

[0362] A mixture of 10 g (0.030 mol) of 9H,9'H-3,3'-biscarbazole, 34 g (0.023 mol) of triflic acid, and 100 ml of D6-benzene was refluxed in a one-neck round-bottom flask at 50°C for 2 hours. After cooling, the mixture was extracted with DCM and dried over MgSO4. The residue was purified by column chromatography to obtain 7.07 g (yield 68%) of compound 2-106-1.

[0363] 2) Preparation of compound 2-106-2

[0364] In a one-neck round bottom flask, 7.07 g (0.02 mol) of compound 2-106-1, 0.38 g (0.002 mol) of CuI, 4.66 g (0.02 mol) of compound [e] (4-bromo-1,1'-biphenyl), 0.23 g (0.002 mol) of trans-1,4-diaminocyclohexane, and 8.49 g (0.04 mol) of K3PO4 were dissolved in 70 ml of 1,4-dioxane and refluxed at 110°C for 8 hours. After completion of the reaction, distilled water and DCM were added at room temperature to extract, and the organic layer was dried over MgSO4 and the solvent was removed using a rotary evaporator. The reactant was purified by column chromatography (DCM:Hexane=1:3) and recrystallized from methanol to obtain 8.28 g (yield 83%) of compound 2-106-2.

[0365] 3) Preparation of compound 2-106

[0366] In a one-neck round bottom flask, 8.28 g (0.017 mol) of compound 2-106-2, 0.32 g (0.0017 mol) of CuI, 3.96 g (0.017 mol) of compound [f] (4-bromo-1,1'-biphenyl), 0.19 g (0.0017 mol) of trans-1,4-diaminocyclohexane, and 7.22 g (0.034 mol) of K3PO4 were dissolved in 80 ml of 1,4-dioxane and refluxed at 110°C for 8 hours. After completion of the reaction, distilled water and DCM were added at room temperature to extract the organic layer, and the solvent was removed using a rotary evaporator after drying the organic layer over MgSO4. The reactant was purified by column chromatography (DCM:Hexane=1:3) and recrystallized from methanol to obtain 8.63 g (yield 78%) of compound 2-106.

[0367] In the above Manufacturing Example 4, the target compound of Table 4 below was synthesized in the same manner as Manufacturing Example 4 above, except that the intermediate e of Table 4 below was used instead of the compound [e], and the intermediate f of Table 4 below was used instead of the compound [f].

[0368] When intermediate e and intermediate f are the same, the target compound can be directly synthesized by adding 2 equivalents of intermediate e in the manufacturing method of 2-106-1 of Manufacturing Example 4.

[0369] [Table 4]

[0370]

[0371] <Manufacturing Example 5> Preparation of compound 2-110

[0372]

[0373] A mixture of compound [g] (compound 2-42) (12.17 g, 0.017 mol), triflic acid (40.8 g, 0.27 mol), and D6-benzene (120 ml) was refluxed at 50°C for 2 hours in a one-neck round-bottom flask. The mixture was extracted with DCM and water, and the organic layer was dried over MgSO4, concentrated, and filtered through silica gel. After concentration, the residue was recrystallized from methanol to obtain 8.87 g (yield 78%) of compound 2-110.

[0374] In the above Manufacturing Example 5, the target compound of Table 5 below was synthesized in the same manner as Manufacturing Example 5 above, except that the intermediate g of Table 5 below was used instead of compound [g].

[0375] [Table 5]

[0376]

[0377] <Manufacturing Example 6> Preparation of compound 3-5

[0378]

[0379] 1) Preparation of compound 3-5-1

[0380] 20 g (78.03 mmol) of compound 5,8-dihydroindolo[2,3-c]carbazole and 18.18 g (78.03 mmol) of compound [h] (4-bromo-1,1'-biphenyl) were dissolved in 200 mL of toluene, and then 3.57 g (3.90 mmol) of Pd2(dba)3(Tris(dibenzylideneacetone)dipalladium(0)), 18.75 g (195.08 mmol) of sodium t-butoxide, and 3.72 g (7.8 mmol) of Xphos(2-Dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl) were added, and the mixture was stirred under reflux at 101°C for 6 hours. After the reaction was completed, ethyl acetate was added to the reaction solution to dissolve it, then extracted with distilled water. The organic layer was dried over anhydrous MgSO4, and the solvent was removed using a rotary evaporator. Afterwards, the residue was purified by column chromatography using DCM and hexane as developing solvents to obtain 21.7 g (yield 68%) of compound 3-5-1.

[0381] 2) Preparation of compounds 3-5

[0382] 21.7 g (53.12 mmol) of compound 3-5-1 and 12.38 g (53.12 mmol) of compound [i] (3-bromo-1,1'-biphenyl) were dissolved in 220 mL of toluene, and then 32.43 g (2.66 mmol) of Pd2(dba), 12.76 g (132.80 mmol) of sodium t-butoxide, and 2.53 g (5.31 mmol) of Xphos were added and stirred under reflux at 101℃ for 6 hours. After completion of the reaction, ethyl acetate was added to the reaction solution to dissolve it, extracted with distilled water, and the organic layer was dried over anhydrous MgSO4 and the solvent was removed using a rotary evaporator. Afterwards, 20.9 g (yield 70%) of compound 3-5 was obtained by purification by column chromatography using DCM and hexane as a developing solvent.

[0383] The target compound of Table 6 below was synthesized in the same manner as in Manufacturing Example 6 above, except that intermediate h of Table 6 below was used instead of compound [h] in Manufacturing Example 6 above, and intermediate i of Table 6 below was used instead of compound [i].

[0384] [Table 6]

[0385]

[0386] <Manufacturing Example 7> Preparation of compound 3-78

[0387]

[0388] A mixture of compound [j] (compound 3-5) (10 g, 17.83 mmol), triflic acid (50 g), and D6-benzene (500 mL) was stirred in a round-bottom flask at 50°C for 1 hour. After completion of the reaction, the mixture was neutralized using a supersaturated aqueous solution of Na2CO3 dissolved in distilled water. After quenching, DCM was added to the mixture to dissolve it, and the organic layer was separated, dried over anhydrous MgSO4, and the solvent was removed using a rotary evaporator. The residue was purified by column chromatography using DCM and hexane as developing solvents to obtain 7.4 g (yield 70%) of compound 3-78.

[0389] The target compound in Table 7 below was synthesized in the same manner as in Manufacturing Example 7 above, except that Compound J in Table 7 below was used instead of Compound [j] used in Manufacturing Example 7 above.

[0390] [Table 7]

[0391]

[0392] The compounds synthesized in the above manufacturing examples 1 to 7 were analyzed using an FD-mass spectrometer and 1The synthesis of the desired compound was confirmed through H-NMR. The measured values ​​of FD-mass spectrometry (FD-MS: Field desorption mass spectrometry) are shown in Table 8 below. 1 The measured values ​​of H-NMR (CDCl3, 400 MHz) are listed in Table 9 below.

[0393] Compound FD-Mass Compound FD-Mass 1-1-1 m / z = 652.30 (C 45 H 16 D 12 N4O=652.82)1-4-5m / z= 728.33(C 51 H 20 D 12 N4O=728.92)1-1-2m / z= 728.33(C 51 H 20 D 12 N4O=728.92)1-4-9m / z= 804.36(C 57 H 24 D 12 N4O=805.02)1-1-3m / z= 728.33(C 51 H 20 D 12 N4O=728.92)1-4-10m / z=804.36(C 57 H 24 D 12 N4O=805.02)1-1-5m / z= 728.33(C 51 H 20 D 12 N4O=728.92)1-4-17m / z=804.36(C 57 H 24 D 12 N4O=805.02)1-1-9m / z= 804.36(C 57 H 24 D 12 N4O=805.02)1-4-21m / z=668.28(C 45 H 16 D 12 N4S=668.88)1-1-13m / z=804.36(C 57 H 24 D 12 N4O=805.02)1-4-22m / z=744.31(C51 H 20 D 12 N4S=744.98)1-1-21m / z= 668.28(C 45 H 16 D 12 N4S=668.88)1-4-23m / z= 744.31(C 51 H 20 D 12 N4S=744.98)1-1-22m / z= 744.31(C 51 H 20 D 12 N4S=744.98)1-4-25m / z= 744.31(C 51 H 20 D 12 N4S=744.98)1-1-23m / z= 744.31(C 51 H 20 D 12 N4S=744.98)1-4-33m / z= 820.34(C 57 H 24 D 12 N4S=821.08)1-1-26m / z= 744.31(C 51 H 20 D 12 N4S=744.98)1-4-35m / z= 820.34(C 57 H 24 D 12 N4S=821.08)1-1-29m / z= 820.34(C 57 H 24 D 12 N4S=821.08)2-3m / z= 560.23(C 42 H 28 N2=560.70)1-1-35m / z= 820.34(C 57 H 24 D 12 N4S=821.08)2-4m / z= 560.23(C 42 H 28 N2=560.70)1-2-1m / z= 652.30(C 45 H 16 D 12 N4O=652.82)2-5m / z= 636.26(C 48 H 32N2=636.80)1-2-2m / z= 728.33(C 51 H 20 D 12 N4O=728.92)2-7m / z= 636.26(C 48 H 32 N2=636.80)1-2-5m / z= 728.33(C 51 H 20 D 12 N4O=728.92)2-31m / z= 636.26(C 48 H 32 N2=636.80)1-2-6m / z= 728.33(C 51 H 20 D 12 N4O=728.92)2-32m / z= 636.26(C 48 H 32 N2=636.80)1-2-8m / z= 702.32 (C 49 H 18 D 12 N4O=702.88)2-42m / z= 636.26(C 48 H 32 N2=636.80)1-2-10m / z= 804.36(C 57 H 24 D 12 N4O=805.02)2-98m / z= 654.37(C 48 H 14 D 18 N2=654.91)1-2-13m / z= 804.36(C 57 H 24 D 12 N4O=805.02)2-99m / z= 574.31(C 42 H 14 D 14 N2=574.79)1-2-20m / z= 752.33(C 53 H 20 D 12 N4O=752.94)2-101m / z= 654.37(C 48 H 14 D 18 N2=654.91)1-2-21m / z= 668.28(C 45 H 16 D 12N4S=668.88)2-102m / z= 654.37(C 48 H 14 D 18 N2=654.91)1-2-22m / z= 744.31(C 51 H 20 D 12 N4S=744.98)2-104m / z= 734.43(C 54 H 14 D 22 N2=735.03)1-2-25m / z= 744.31(C 51 H 20 D 12 N4S=744.98)2-106m / z= 650.34(C 48 H 18 D 14 N2=650.88)1-2-29m / z= 820.34(C 57 H 24 D 12 N4S=821.08)2-107m / z= 574.31(C 42 H 14 D 14 N2=574.79)1-2-35m / z= 820.34(C 57 H 24 D 12 N4S=821.08)2-108m / z= 648.33(C 48 H 16 D 14 N2=648.87)1-2-38m / z= 820.34(C 57 H 24 D 12 N4S=821.08)2-110m / z= 668.46(C 48 D 32 N2=668.99)1-3-1m / z= 652.30(C 45 H 16 D 12 N4O=652.82)2-111m / z= 588.40(C 42 D 28 N2=588.87)1-3-2m / z= 728.33(C 51 H 20 D 12 N4O=728.92)2-113m / z= 668.46(C 48 D32 N2=668.99)1-3-5m / z= 728.33(C 51 H 20 D 12 N4O=728.92)2-114m / z= 668.46(C 48 D 32 N2=668.99)1-3-8m / z= 702.32(C 49 H 18 D 12 N4O=702.88)2-115m / z= 748.51(C 54 D 32 N2=749.12)1-3-9m / z= 804.36(C 57 H 24 D 12 N4O=805.02)2-116m / z= 748.51(C 54 D 32 N2=749.12)1-3-16m / z= 804.36(C 57 H 24 D 12 N4O=805.02)3-4m / z= 560.23(C 42 H 28 N2=560.70)1-3-19m / z= 802.35(C 57 H 22 D 12 N4O=803.00)3-5m / z= 560.23(C 42 H 28 N2=560.70)1-3-20m / z= 752.33(C 53 H 20 D 12 N4O=752.94)3-6m / z= 636.26(C 48 H 32 N2=636.80)1-3-21m / z= 668.28(C 45 H 16 D 12 N4S=668.88)3-13m / z= 636.26(C 48 H 32 N2=636.80)1-3-22m / z= 744.31(C 51 H 20 D 12 N4S=744.98)3-15m / z= 558.21(C 42 H26 N2=558.68)1-3-25m / z= 744.31(C 51 H 20 D 12 N4S=744.98)3-77m / z= 588.40(C 42 D 28 N2=588.87)1-3-29m / z= 820.34(C 57 H 24 D 12 N4S= 821.08)3-78m / z= 588.40(C 42 D 28 N2=588.87)1-3-30m / z= 820.34(C 57 H 24 D 12 N4S=821.08)3-80m / z= 668.46(C 48 D 32 N2=668.99)1-3-34m / z= 820.34(C 57 H 24 D 12 N4S=821.08)3-81m / z= 584.37(C 42 D 26 N2=584.84)1-4-1m / z= 652.30(C 45 H 16 D 12 N4O=652.82)3-91m / z= 668.46(C 48 D 32 N2=668.99)1-4-2m / z= 728.33(C 51 H 20 D 12 N4O=728.92)

[0394] 화합물 1H NMR(CDCl3, 400MHz)1-1-1δ= 8.36 (2H, d), 8.08 (1H, d), 7.88-7.79 (4H, m), 7.69 (1H, d), 7.57-7.41 (8H, m)1-1-2δ= 8.08 (1H, d), 7.96-7.75 (9H, m), 7.57-7.41 (8H, m), 7.25 (2H, d)1-1-3δ= 8.38 (1H, d), 8.08 (1H, d), 7.94-7.41 (18H, m)1-1-5δ= 8.08 (1H, d), 7.96-7.79 (8H, m), 7.69 (1H, d), 7.60-7.41 (10H, m)1-1-9δ= 8.08 (1H, d), 7.96 (2H, d), 7.88-7.69 (7H, m), 7.57-7.41 (8H, m), 7.25 (6H, m)1-1-13δ= 8.36 (2H, d), 8.08-8.04 (4H, m), 7.88-7.69 (7H, m), 7.57-7.41 (11H, m)1-1-21δ= 8.55 (1H, d), 8.36 (2H, d), 8.03 (1H, d), 7.94-7.92 (2H, m), 7.79-7.68 (4H, m), 7.50-7.41 (6H, m)1-1-22δ= 8.55 (1H, d), 8.03-7.92 (5H, m), 7.79-7.68 (6H, m), 7.49-7.41 (6H, m), 7.25 (2H, d)1-1-23δ= 8.55 (1H, d), 8.38 (1H, d), 8.03 (1H, d), 7.94-7.92 (3H, m), 7.79-7.61 (8H, m), 7.49-7.41 (6H, m)1-1-26δ= 8.55 (1H, d), 8.38 (2H, d), 8.03 (1H, d), 7.94-7.92 (3H, m), 7.79-7.61 (7H, m), 7.50-7.41 (6H, m)1-1-29δ= 8.55 (1H, d), 8.03-7.92 (5H, m), 7.75-7.68 (6H, m), 7.49-7.41 (6H, m), 7.25 (6H, m)1-1-35δ= 8.55 (1H, d), 8.<h2 style=";text-align:left;direction:ltr">36 (2H, d), 8.03 (1H, d), 7.94-7.92 (3H, m), 7.75-7.61 (7H, m), 7.50-7.41 (6H, m), 7.25 (4H, d)1-2-1δ= 8.36 (2H, d), 8.03 (1H, d), 7.82-7.69 (6H, m), 7.57-7.41 (7H, m)1-2-2δ= 8.03-7.96 (3H, m), 7.82-7.69 (8H, m), 7.57-7.41 (7H, m), 7.25 (2H, d)1-2-5δ= 8.36 (2H, d), 8.03 (1H, d), 7.82-7.69 (6H, m), 7.57-7.41 (7H, m), 7.25 (4H, m)1-2-6δ= 8.36 (2H, d), 8.03 (1H, d), 7.94 (1H, s), 7.82-7.41 (16H, m)1-2-8δ= 8.95 (1H, d), 8.50 (1H, d), 8.36 (2H, d), 8.20 (1H, d), 8.09-8.03 (2H, m), 7.82-7.69 (5H, m), 7.57-7.50 (5H, m), 7.39(1H, t)1-2-10δ= 8.03-7.94 (4H, m), 7.82-7.69 (9H, m), 7.61-7.41 (9H, m), 7.25 (2H, m)1-2-13δ= 8.36 (2H, d), 8.04-8.03 (4H, m), 7.82-7.69 (8H, m), 7.57-7.41 (10H, m)1-2-20δ= 9.11 (1H, d), 8.70 (1H, d), 8.46-8.36 (4H, m), 8.03 (1H, d), 7.90-7.50 (13H, m)1-2-21δ= 8.36 (2H, d), 8.20 (2H, m), 8.03 (1H, d), 7.94 (2H, m), 7.79 (2H, d), 7.68 (1H, t), 7.50-7.41 (6H, m)1-2-22δ= 8.24-8.20 (2H, m), 8.03-7.94 (5H, m), 7.79-7.68 (5H, m), 7.49-7.41 (6H, m), 7.25 (2H, d)1-2-25δ= 8.36 (2H, d), 8.24-8.20 (2H, m), 8.03 (1H, d), 7.94 (2H, m), 7.75-7.68 (3H, m), 7.50-7.41 (6H, m), 7.25 (4H, m)1-2-29δ= 8.24-8.20 (2H, m), 8.03-7.94 (5H, m), 7.75-7.68 (5H, m), 7.49-7.41 (6H, m), 7.25 (6H, m)1-2-35δ= 8.36 (2H, d), 8.24-8.20 (2H, m), 8.03 (1H, d), 7.94 (3H, m), 7.75-7.68 (6H, m), 7.50-7.41 (6H, m), 7.25 (4H, m)1-2-38δ= 8.36 (2H, d), 8.24-8.20 (2H, m), 8.03-7.94 (5H, m), 7.75-7.68 (5H, m), 7.50-7.41 (6H, m), 7.25 (4H, m)1-3-1δ= 8.36 (2H, d), 7.88-7.79 (6H, m), 7.69 (1H, d), 7.57-7.41 (7H, m)1-3-2δ= 7.96-7.69 (11H, m), 7.57-7.41 (7H, m), 7.25 (2H, d)1-3-5δ= 8.36 (2H, d), 7.88-7.69 (7H, m), 7.57-7.41 (7H, m), 7.25 (4H, m)1-3-8δ= 8.95 (1H, d), 8.50 (1H, d), 8.36 (2H, d), 8.20 (1H, d), 8.09 (1H, d), 7.88-7.69 (6H, m), 7.57-7.50 (5H, m), 7.39(1H, t)1-3-9δ= 7.96 (2H, d), 7.88-7.69 (9H, m), 7.57-7.41 (7H, m), 7.25 (6H, m)1-3-16δ= 8.36 (2H, d), 7.88-7.69 (18H, m), 7.25 (4H, m)1-3-19δ= 9.27 (1H, s), 8.79 (1H, d), 8.37-8.30 (6H, m), 7.88-7.50 (14H, m)1-3-20δ= 9.11 (1H, d), 8.70 (1H, d), 8.46-8.36 (4H, m), 7.90-7.50 (14H, m)1-3-21δ= 8.36 (2H, d), 8.12 (1H, s), 8.03-7.92 (4H, m), 7.79 (2H, d), 7.68 (1H, t), 7.50-7.41 (6H, m)1-3-22δ= 8.12 (1H, s), 8.03-7.92 (6H, m), 7.79-7.68 (5H, m), 7.49-7.41 (6H, m), 7.25 (2H, m)1-3-25δ= 8.36 (2H, d), 8.12 (1H, s), 8.03-7.92 (4H, m), 7.75-7.68 (3H, m), 7.50-7.41 (6H, m), 7.25 (4H, m)1-3-29δ= 8.12 (1H, s), 8.03-7.92 (6H, m), 7.75-7.68 (5H, m), 7.49-7.41 (6H, m), 7.25 (6H, m)1-3-30δ= 8.12 (1H, s), 8.03-7.92 (7H, m), 7.75-7.61 (8H, m), 7.49-7.41 (6H, m), 7.25 (2H, d)1-3-34δ= 8.36 (2H, d), 8.12 (1H, s), 8.03-7.92 (4H, m), 7.75-7.68 (3H, m), 7.50-7.41 (6H, m), 7.25 (8H, m)1-4-1δ= 8.36 (2H, d), 7.82-7.79 (4H, m), 7.69 (2H, m), 7.57-7.41 (8H, m)1-4-2δ= 7.96 (2H, d), 7.82-7.69 (8H, m), 7.57-7.41 (8H, m), 7.25 (2H, d)1-4-5δ= 8.36 (2H, d), 7.82-7.69 (6H, m), 7.57-7.41 (8H, m), 7.25 (4H, m)1-4-9δ= 7.96 (2H, d), 7.82-7.69 (8H, m), 7.57-7.41 (8H, m), 7.25 (6H, m)1-4-10δ= 7.96-7.94 (3H, m), 7.82-7.41 (19H, m), 7.25 (2H, d)1-4-17δ= 8.36 (2H, d), 7.94 (2H, m), 7.82-7.41 (20H, m)1-4-21δ= 8.36 (2H, d), 8.03 (2H, m), 7.94 (2H, m), 7.79 (2H, d), 7.68 (2H, m), 7.50-7.41 (6H, m)1-4-22δ= 8.03-7.94 (6H, m), 7.79-7.68 (6H, m), 7.49-7.41 (6H, m), 7.25 (2H, d)1-4-23δ= 8.38 (1H, d), 8.03-7.94 (5H, m), 7.79-7.68 (8H, m), 7.49-7.41 (6H, m)1-4-25δ= 8.36 (2H, d), 8.03 (2H, m), 7.94 (2H, m), 7.75-7.68 (4H, m), 7.50-7.41 (6H, m), 7.25 (4H, m)1-4-33δ= 8.36 (2H, d), 8.04-8.03 (5H, m), 7.94 (2H, m), 7.75-7.68 (6H, m), 7.50-7.41 (9H, m)1-4-35δ= 8.36 (2H, d), 8.03 (2H, m), 7.94 (3H, m), 7.75-7.61 (7H, m), 7.50-7.41 (6H, m), 7.25 (4H, m)2-3δ= 8.55 (1H, d), 8.30 (1H, d), 8.21-8.13 (3H, m), 7.99-7.89 (4H, m), 7.77-7.35 (17H, m), 7.20-7.16 (2H, m)2-4δ= 8.55 (1H, d), 8.30(1H, d), 8.19-8.13(2H, m), 7.99-7.89(8H, m), 7.77-7.75 (3H, m), 7.62-7.35 (11H, m), 7.20-7.16 (2H, m)2-5δ= 8.55 (1H, d), 8.30(1H, d), 8.21-8.13(3H, m), 7.99-7.94(2H, m), 7.89(2H, s), 7.77-7.35 (17H, m), 7.25-7.16 (6H, m)2-7δ= 8.55 (1H, d), 8.31-8.30 (3H, d), 8.19-8.13 (2H, m), 7.99-7.89 (5H, m), 7.77-7.75 (5H, m), 7.62-7.35 (14H, m), 7.20-7.16 (2H, m)2-31δ= 8.55 (1H, d), 8.30 (1H, d), 8.21-8.13 (4H, m), 7.99-7.89 (4H, m), 7.77-7.35 (20H, m), 7.20-7.16 (2H, m)2-32δ= 8.55 (1H, d), 8.30 (1H, d), 8.21-8.13 (3H, m), 7.99-7.89 (8H, m), 7.77-7.35 (17H, m), 7.20-7.16 (2H, m)2-42δ= 8.55 (1H, d), 8.30 (1H, d), 8.19(1H, d) 8.13 (1H, d), 7.99-7.89 (12H, m), 7.77-7.75 (5H, m), 7.50-7.35 (8H, m), 7.20-7.16 (2H, m)2-98δ = 8.55 (1H, d), 8.30 (1H, d), 8.19-8.13 (2H, m), 7.99-7.89 (4H, m), 7.77 (1H, d), 7.58-7.50 (2H, m), 7.35 (1H, t), 7.20-7.16 (2H, t)2-99δ = 8.55 (1H, d), 8.30 (1H, d), 8.19-8.13 (2H, m), 7.99-7.89 (4H, m), 7.77 (1H, d), 7.58-7.50 (2H, m), 7.35 (1H, t), 7.20-7.16 (2H, t)2-101δ = 8.55 (1H, d), 8.30 (1H, d), 8.19-8.13 (2H, m), 7.99-7.89 (4H, m), 7.77 (1H, d), 7.58-7.50 (2H, m), 7.35 (1H, t), 7.20-7.16 (2H, t)2-102δ = 8.55 (1H, d), 8.30 (1H, d), 8.19-8.13 (2H, m), 7.99-7.89 (4H, m), 7.77 (1H, d), 7.58-7.50 (2H, m), 7.35 (1H, t), 7.20-7.16 (2H, t)2-104δ = 8.55 (1H, d), 8.30 (1H, d), 8.19-8.13 (2H, m), 7.99-7.89 (4H, m), 7.77 (1H, d), 7.58-7.50 (2H, m), 7.35 (1H, t), 7.20-7.16 (2H, t)2-106δ = 7.92-7.91 (8H, m), 7.75 (4H, d), 7.49-7.41 (6H, m)2-107δ = 8.21 (1H, s), 7.41-7.68 (13H, m)2-108δ = 9.05 (1H, s), 8.33-8.25 (4H, m), 7.94 (1H, d), 7.70-7.50 (10H, m)2-110δ = 100% deuterium content. 1 No H NMR peak 2-111δ = 100% deuterium content 1 No H NMR peak 2-113δ = 100% deuterium content 1 No H NMR peak 2-114δ = 100% deuterium content 1 No H NMR peak 2-116δ = 100% deuterium content 1No H NMR peak3-4δ= 8.55 (2H, d), 7.94-7.91 (10H, m), 7.75 (4H, d), 7.49-7.35 (10H, m), 7.12 (2H, t)3-5δ= 8.55 (2H, d), 8.21 (1H, s), 7.94-7.91 (6H, m), 7.75-7.35 (16H, m), 7.26 (1H, d), 7.16 (2H, t)3-6δ= 8.55 (2H, d), 7.94-7.91 (11H, m), 7.75-7.73 (5H, m), 7.61-7.58 (3H, m), 7.49-7.35 (8H, m), 7.26 (1H, d), 7.16 (2H, t)3-13δ= 8.55 (2H, d), 8.21 (1H, s), 7.94-7.91 (6H, m), 7.75-7.16 (23H, m)3-15δ= 9.05 (1H, s), 8.55 (2H, d), 8.33-8.25 (4H, m), 7.94 (3H, m), 7.70-7.50 (11H, m)3-77δ = No 1H NMR peak with 100% deuterium content3-78δ = No 1H NMR peak with 100% deuterium content 1 No H NMR peak 3-80δ = 100% deuterium content 1 No H NMR peak 3-81δ = 100% deuterium content 1 No H NMR peak 3-91δ = 100% deuterium content 1 No H NMR peak

[0395] <Experimental Example>

[0396] Experimental Example 1

[0397] (1) Fabrication of organic light-emitting devices

[0398] 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 (ultraviolettozone) for 5 minutes using UV 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.

[0399] 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′-Di(1-naphthyl)-N,N′-diphenyl-(1,1′-biphenyl)-4,4′-diamine), were formed on the ITO transparent electrode (anode).

[0400] On top of that, a light-emitting layer was thermally vacuum-deposited as follows. The light-emitting layer was deposited with 400Å of one compound described in Table 10 as a host, and a green phosphorescent dopant was deposited by doping Ir(ppy)3 with 7%. Then, BCP was deposited with 60Å as a hole-blocking layer, and Alq3 was deposited with 200Å as an electron-transporting layer thereon. Finally, lithium fluoride (LiF) was deposited with a thickness of 10Å on the electron-transporting layer to form an electron-injection layer, and then an aluminum (Al) cathode was deposited with a thickness of 1,200Å on the electron-injection layer to form a cathode, thereby manufacturing an organic electroluminescent device.

[0401] 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.

[0402] The compounds used in Comparative Examples 1 to 14 described in Table 10 below are as follows.

[0403]

[0404] (2) Measurement of driving voltage, luminous efficiency, and lifespan of organic light-emitting devices

[0405] The electroluminescence (EL) characteristics of the organic light-emitting device manufactured as described above were measured using MacScience's M7000, and the standard luminance was determined to be 6,000 cd / m using the lifespan measuring equipment (M6000) manufactured by MacScience based on the measurement results. 2 When, T 90 was measured, and the measurement results are shown in Table 10 below.

[0406] Light-emitting layer compound driving voltage (V) efficiency (cd / A) color coordinate (x, y) lifespan (T) 90) Comparative example 1A6.3142.1Green53Comparative example 2B6.1846.3Green56Comparative example 3C6.3046.5Green57Comparative example 4D6.1750.3Green60Comparative example 5E5.2138.3Green45Comparative example 6F5.2737.5Green48Comparative example 7G4.8861.8Green68Comparative example 8H5.9857.3Green55Comparative example 9I6.3054.8Green52Comparative example 10J5.6841.7Green53Comparative example 11K5.5245.4Green49Comparative example 12L5.8252.1Green48Comparative example 13M6.2843.7Green61Comparative example 14N6.1247.2 Green 64 Example 11-1-12.77111.4 Green 143 Example 21-1-22.78113.1 Green 141 Example 31-1-32.82114.7 Green 145 Example 41-1-52.82112.5 Green 144 Example 51-1-92.75112.6 Green 148 Example 61-1-132.82112.5 Green 142 Example 71-1-212.85113.6 Green 146 Example 81-1-222.84111.7 Green 147 Example 91-1-232.86115.4 Green 145 Example 101-1-292.88114.7 Green 142 Example 111-2-12.98113.3 Green 158 Example 121-2-22.97113.5 Green 161 Example 131-2-52.94114.5 Green 157 Example 141-2-63.01116.2 Green 162 Example 151-2-102.91115.7 Green 155 Example 161-2-132.96113.8 Green 159 Example 171-2-212.95115.4 Green 157 Example 181-2-222.99116.2 Green 161 Example 191-2-253.02117.5 Green 160 Example 201-2-292.93112.4Green159Example 211-3-13.02123.4Green142Example 221-3-23.05122.7Green143Example 231-3-53.11123.1Green145Example 241-3-93.09126.4Green146Example 251-3-163.06126.6Green146Example 261-3-213.10125.2Green143Example 271-3-223.13125.3Green142Example 281-3-253.07125.6Green146Example 291-3-293.06128.4 Green 142 Example 301-3-303.12124.1 Green 141 Example 311-4-13.32108.2 Green 135 Example 321-4-23.35110.1 Green 132 Example 331-4-53.34107.5 Green 131 Example 341-4-93.36104.3 Green 132 Example 351-4-103.42106.5 Green 128 Example 361-4-213.38105.9 Green 127 Example 371-4-223.31106.2 Green 136 Example 381-4-233.40107.3 Green 133 Example 391-4-253.35104.3 Green 134 Example 401-4-333.33108.1 Green 135 Example 411-2-82.97115.2 Green 158 Example 421-2-202.94114.6 Green 156 Example 431-3-83.07125.4 Green 147 Example 441-3-193.11126.3 Green 145 Example 451-3-203.09125.8 Green 149.

[0407] According to Table 10 above, in the case of Examples 1 to 45 corresponding to Chemical Formula 1 of the present invention, the structural features in which the carbazole and triazine groups are bonded in the ortho position in the phenyl linker and substituted with deuterium, and a heteroaryl group is introduced and an additional aryl substituent is bonded to have a bulkier structure. When a triazine group is substituted in the ortho position of the carbazole in the phenyl linker, structural distortion may be aggravated, which may facilitate charge transfer. In addition, when an additional aryl group is introduced at position 1 of the heteroaryl group, it has an expanded, wide π-conjugation region, which can also be utilized as an auxiliary means for controlling the energy band gap. Since it has a bulkier and rigid structure due to the influence of the added aryl group, there is also an advantage in that it can maintain a high T1 energy level.

[0408] Comparative compounds A to D used in Comparative Examples 1 to 4 are structurally similar to those of the present invention, but exhibit high operating voltage, low efficiency, and low lifespan. Comparative compounds A to D differ from the present invention in that the triazine group and the carbazole group are substituted in the meta or para positions on the phenyl linker, which increases bond rotation and increases the vibrational energy of the molecule, thereby lowering the stability of the molecular structure and resulting in inferior device lifespan and operating characteristics. In addition, it was confirmed through the device results of Comparative Examples 1 to 4 that the deuterium substitution effect of the carbazole substituent in the meta and para positions of the phenyl linker was minimal.

[0409] In the case of comparative compounds E and F used in comparative examples 5 and 6, there is a difference from the present invention in that an aryl substituent is not introduced at the terminal of the heteroaryl group, and due to the molecular structure excluding the aryl group, bond rotation is facilitated, which reduces the stability of the molecular structure, increases the driving voltage, and reduces the lifespan.

[0410] In the case of comparative compound G of comparative example 7, it is structurally similar to that of the present invention, but it is different from that of the present invention in that the phenyl linker and carbazole substituents are composed of deuterium. When the device results of comparative example 7 and example 11 were compared, it was confirmed that the structure of the present invention had better driving voltage, efficiency, and lifespan characteristics of the device due to the deuterium substitution effect. The material of the present invention substituted with deuterium was able to confirm the improvement in the driving and lifespan of the device due to the stability and amorphousness of the molecule compared to comparative compound G, and it was able to improve efficiency by minimizing energy loss with low vibration energy and facilitating energy transfer to the dopant.

[0411] Comparative compounds H and I of Comparative Examples 8 and 9 differ from the present invention in that the triazine group has a structure with two heteroaryl substituents. Substances with strong electronegativity, such as the O and S atoms of dibenzofuran or dibenzothiophene, have an advantageous aspect of increasing charge mobility, but also have a disadvantage of affecting the stability of the molecule itself as the mobility of electrons increases. It was confirmed that when the triazine group is excessively substituted with a heteroaryl group, the stability decreases significantly, resulting in a decrease in the lifespan and efficiency of the device.

[0412] Comparative compounds J and K used in Comparative Examples 10 and 11 differ from the present invention in that they have a structure in which aryl groups are substituted at positions 2 and 4, rather than position 1, of dibenzofuran and dibenzothiophene, and a carbazole group is substituted at the meta position of the phenyl linker. It was confirmed that comparative compounds J and K have a structure in which the steric hindrance between substituents is alleviated, which increases bond rotation and increases the vibrational energy of the molecule, thereby lowering the stability of the molecular structure, resulting in inferior device lifespan and operating characteristics.

[0413] In the case of comparative compound L of comparative example 12, there is a difference in the structure from the present invention in that a nitrile (-CN) substituent is bonded to the terminal of the aryl group. The nitrile substituent is a substituent with a characteristic electron withdrawing property, and the electron donating property is weakened in the direction of the same electron withdrawing unit, triazine, so that the electron flow within the molecule is reduced and a stronger voltage is required, resulting in a lower luminous efficiency. In addition, non-radiative recombination occurs due to charge accumulation within the luminescent layer by the strong voltage, and the compound has a short lifetime.

[0414] Comparative compounds M and N used in Comparative Examples 13 and 14 differ from the present invention in that they have a structure in which a carbazole condensed with an additional heterocycle is substituted. The carbazole condensation derivative type substituent is bulky compared to the carbazole substituent and expands the HOMO region of the molecule, resulting in a decrease in operating voltage and efficiency.

[0415] In general, compounds bonded with hydrogen and compounds substituted with deuterium exhibit different thermodynamic behaviors. This is because the mass of a deuterium atom is twice that of hydrogen, and due to the difference in atomic mass, deuterium has the characteristic of having lower vibrational energy. Furthermore, the bond length between carbon and deuterium is shorter than that between carbon and hydrogen, and the dissociation energy required to break the bond is also stronger. This is because the van der Waals radius of deuterium is smaller than that of hydrogen, which narrows the elongation amplitude of the carbon-deuterium bond.

[0416] Compounds substituted with deuterium have lower ground-state energy compared to compounds substituted only with hydrogen. Furthermore, as the carbon-deuterium bond length decreases, the molecular core volume decreases. This can reduce electrical polarizability and weaken intermolecular interactions, increasing the volume of the device film. These characteristics induce an amorphous state in the film, which induces a lower crystallinity. In conclusion, deuterium substitution can be effective in improving the heat resistance of OLED devices, which can improve the device's lifetime characteristics.

[0417] Experimental Example 2

[0418] (1) Fabrication of organic light-emitting devices

[0419] 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 (ultraviolettozone) for 5 minutes using UV 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.

[0420] 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′-Di(1-naphthyl)-N,N′-diphenyl-(1,1′-biphenyl)-4,4′-diamine), were formed on the ITO transparent electrode (anode).

[0421] On top of that, a light-emitting layer was thermally vacuum deposited as follows. The light-emitting layer was prepared by pre-mixing two compounds described in Table 11 as hosts in the weight ratios described in Table 11 below, and then depositing 400Å in one hole after preliminary mixing, and the green phosphorescent dopant was doped with 7% Ir(ppy)3 and deposited. Then, 60Å of BCP was deposited as a hole-blocking layer, and 200Å of Alq3 was deposited as an electron-transporting layer thereon. Finally, lithium fluoride (LiF) was deposited with a thickness of 10Å on the electron-transporting layer to form an electron injection layer, and then an aluminum (Al) cathode was deposited with a thickness of 1,200Å on the electron injection layer to form a cathode, thereby manufacturing an organic electroluminescent device.

[0422] Meanwhile, all organic compounds required for OLED device production are 10 for each material. -8 ~10 -6It was purified by vacuum sublimation under 10 torr and used in OLED production.

[0423] (2) Measurement of driving voltage, luminous efficiency, and lifespan of organic light-emitting devices

[0424] The electroluminescence (EL) characteristics of the organic light-emitting device manufactured as described above were measured using MacScience's M7000, and the standard luminance was determined to be 6,000 cd / m using the lifespan measuring equipment (M6000) manufactured by MacScience based on the measurement results. 2 When, T 90 was measured, and the measurement results are shown in Table 11 below.

[0425] [Table 11]

[0426]

[0427]

[0428]

[0429] Looking at the results of Examples 46 to 132 of Table 11 above, when the compound represented by Chemical Formula 1 (n-type) according to the present invention is used together with the compound represented by Chemical Formula 2 (p-type), better efficiency and lifespan effects are observed. This result is because an exciplex phenomenon occurs when both compounds are included simultaneously.

[0430] The exciplex phenomenon is a phenomenon in which energy is released in the size of the HOMO energy level of the donor (p-host) and the LUMO energy level of the acceptor (n-host) due to the exchange of electrons between two molecules. When the exciplex phenomenon occurs between two molecules, reverse intersystem crossing (RISC) occurs, and this can increase the internal quantum efficiency of fluorescence emission to 100%.

[0431] When a donor (p-host) with good hole transport capability and an acceptor (n-host) with good electron transport capability are used as hosts for the light-emitting layer, holes are injected into the p-host and electrons are injected into the n-host. At this time, excitons are not quenched due to intermolecular electron exchange, and the lifetime of excitons that can have energy increases. As a result, the overall current efficiency is improved and the lifespan of the device can be improved. In the present invention, it was confirmed that when the compound of the above chemical formula 1 acts as an acceptor and the compound of the above chemical formula 2 acts as a donor and they are used together as a host for the light-emitting layer, excellent device characteristics are exhibited.

[0432] When the heterocyclic compound of the above chemical formula 1 and the compound of the above chemical formula 2 are mixed and used as a light-emitting layer material, not only can the current efficiency of the light-emitting layer be improved to some extent, but a device having a long lifespan can be constructed. When the exciplex phenomenon occurs, the driving voltage may sometimes increase, and this is because an imbalance of holes and electrons occurs in the light-emitting layer of the device. This is a problem caused by the difference in hole and electron mobility of each material between the mixed hosts. Therefore, a device exhibiting optimal performance can be constructed only when the balance of electron flow within the device is appropriately maintained, and this problem can be solved by adjusting the ratio between the acceptor and the donor.

[0433] Experimental Example 3

[0434] (1) Fabrication of organic light-emitting devices

[0435] 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 (ultraviolettozone) for 5 minutes using UV 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.

[0436] 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′-Di(1-naphthyl)-N,N′-diphenyl-(1,1′-biphenyl)-4,4′-diamine), were formed on the ITO transparent electrode (anode).

[0437] On top of that, a light-emitting layer was thermally vacuum deposited as follows. The light-emitting layer was pre-mixed with the two compounds described in Table 12 below as hosts in the weight ratios described in Table 12 below, and then deposited at 400Å in one hole after preliminary mixing, and the green phosphorescent dopant was doped with 7% Ir(ppy)3 and deposited. Then, 60Å of BCP was deposited as a hole-blocking layer, and 200Å of Alq3 was deposited as an electron-transporting layer thereon. Finally, lithium fluoride (LiF) was deposited on the electron-transporting layer to a thickness of 10Å to form an electron injection layer, and then an aluminum (Al) cathode was deposited on the electron injection layer to a thickness of 1,200Å to form a cathode, thereby manufacturing an organic electroluminescent device.

[0438] Meanwhile, all organic compounds required for OLED device production are 10 for each material. -8 ~10 -6It was purified by vacuum sublimation under 10 torr and used in OLED production.

[0439] (2) Measurement of driving voltage, luminous efficiency, and lifespan of organic light-emitting devices

[0440] The electroluminescence (EL) characteristics of the organic light-emitting device manufactured as described above were measured using MacScience's M7000, and the standard luminance was determined to be 6,000 cd / m using the lifespan measuring equipment (M6000) manufactured by MacScience based on the measurement results. 2 When, T 90 was measured, and the measurement results are shown in Table 12 below.

[0441] [Table 12]

[0442]

[0443]

[0444]

[0445] Comparing the results of Table 12 above with the results of Table 10, it can be confirmed that when the heterocyclic compound of Chemical Formula 1 of the present invention and the compound of Chemical Formula 3 are simultaneously used as a host for the light-emitting layer, the driving voltage, luminous efficiency, and lifespan are all improved. From this, it can be expected that an exciplex phenomenon occurs when the compound of Chemical Formula 1 and the compound of Chemical Formula 3 are simultaneously included. The description of the exciplex phenomenon is the same as that described in relation to Examples 46 to 132 of Experimental Example 2, but in the case of Examples 133 to 219, it was confirmed that the compound of Chemical Formula 3 served as a donor and the heterocyclic compound of Chemical Formula 1 served as an acceptor, and when the two compounds were used together as a host for the light-emitting layer, excellent device characteristics were exhibited.

[0446] That is, when the heterocyclic compound of chemical formula 1 of the present invention and the compound of chemical formula 3 are simultaneously used as a host for the light-emitting layer, it can be confirmed that the driving voltage, light-emitting efficiency, and lifespan are significantly superior.

Claims

1. A heterocyclic compound of the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, X is O or S, Ar1 is a C6 to C60 aryl group substituted or unsubstituted with one or more substituents selected from deuterium, a halogen group, an alkyl group, a cycloalkyl group, an aryl group, and a heteroaryl group, Ar2 is a substituted or unsubstituted C6 to C60 aryl group, R1 to R4 are each independently hydrogen; deuterium; 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; or a substituted or unsubstituted C2 to C60 heteroaryl group, D is deuterium, d1 is an integer from 1 to 4, d2 is an integer from 1 to 8, r1 and r2 are integers from 1 to 3, respectively. r3 is an integer from 0 to 3, and the sum of d1 and r3 is 4, r4 is an integer from 0 to 7, and the sum of d2 and r4 is 8. When r1 to r4 are each 2 or more, the substituents in parentheses are the same or different.

2. In claim 1, the chemical formula 1 includes the structures of the following chemical formulas A and B, and the deuterium substitution rate of the chemical formula A is 30% to 100%, and the deuterium substitution rate of the chemical formula B is 0% to 50%, a heterocyclic compound: [Chemical Formula A] [Chemical Formula B] In the above chemical formulas A and B, is the position where chemical formulas A and B are combined, The definition of each substituent is the same as that in the chemical formula 1 above.

3. In claim 1, the chemical formula 1 is a heterocyclic compound represented by the following chemical formula 1-D: [Chemical Formula 1-D] In the above chemical formula 1-D, The definition of each substituent is the same as that in the chemical formula 1 above.

4. A heterocyclic compound according to claim 1, wherein Ar1 is a C6 to C30 aryl group substituted or unsubstituted with one or more substituents selected from deuterium, a halogen group, an alkyl group, a cycloalkyl group, an aryl group, and a heteroaryl group.

5. A heterocyclic compound according to claim 1, wherein R1 to R4 are each independently hydrogen or deuterium.

6. In claim 1, the chemical formula 1 is a heterocyclic compound represented by any one of the following compounds:

7. An organic light-emitting device comprising a first electrode; a second electrode; and at least one organic layer provided between the first electrode and the second electrode, An organic light-emitting device, wherein at least one of the organic layers comprises at least one heterocyclic compound according to any one of claims 1 to 6.

8. An organic light-emitting device according to claim 7, wherein the organic layer includes a light-emitting layer, and the light-emitting layer includes at least one heterocyclic compound.

9. An organic light-emitting device according to claim 8, wherein the light-emitting layer comprises a host, and the host comprises at least one heterocyclic compound.

10. In claim 7, the organic layer including the heterocyclic compound further includes a compound of the following chemical formula 2 or 3: [Chemical Formula 2] [Chemical Formula 3] In the above chemical formulas 2 and 3, R11, R12, R21 and R22 are each independently selected from the group consisting of hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy 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; a substituted or unsubstituted silyl group; a substituted or unsubstituted phosphine oxide group; and a substituted or unsubstituted amine group, L11, L12, L21 and L22 are each independently a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group, Ar11, Ar12, Ar21 and Ar22 are each independently a cyano group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; or a substituted or unsubstituted silyl group, r11 and r12 are integers from 1 to 7, respectively, r21 is an integer from 1 to 6, r22 is an integer from 1 to 4, l11, l12, l21 and l22 are integers from 1 to 3, respectively. When r11, r12, r21, r22, l11, l12, l21, and l22 are each 2 or more, the substituents in parentheses are the same or different.

11. In claim 10, the organic light-emitting device wherein the chemical formula 2 is selected from the following compounds:

12. In claim 10, the organic light-emitting device wherein the chemical formula 3 is selected from the following compounds:

13. A heterocyclic compound according to any one of claims 1 to 6; and; A composition for an organic layer of an organic light-emitting device comprising a compound of the following chemical formula 2 or 3: [Chemical Formula 2] [Chemical Formula 3] In the above chemical formulas 2 and 3, R11, R12, R21 and R22 are each independently selected from the group consisting of hydrogen; deuterium; a halogen group; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy 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; a substituted or unsubstituted silyl group; a substituted or unsubstituted phosphine oxide group; and a substituted or unsubstituted amine group, L11, L12, L21 and L22 are each independently a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group, Ar11, Ar12, Ar21 and Ar22 are each independently a cyano group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; or a substituted or unsubstituted silyl group, r11 and r12 are integers from 1 to 7, respectively, r21 is an integer from 1 to 6, r22 is an integer from 1 to 4, l11, l12, l21 and l22 are integers from 1 to 3, respectively. When r11, r12, r21, r22, l11, l12, l21, and l22 are each 2 or more, the substituents in parentheses are the same or different.

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