Compounds and organic light-emitting devices containing them

Abstract

The present specification relates to a compound of Chemical Formula 1 and an organic light-emitting device including the compound.

Description

[Technical Field]

[0001] This specification relates to compounds and organic light-emitting devices containing the same.

[0002] This specification asserts the rights as of the filing date of Korean Patent Application No. 10-2020-0154756, filed with the Korean Intellectual Property Office on November 18, 2020, and all its contents are contained herein. [Background technology]

[0003] Electroluminescent elements are a type of self-emissive display element that has the advantages of a wide viewing angle, excellent contrast, and fast response speed.

[0004] An organic light-emitting element has a structure in which an organic thin film is placed between two electrodes. When a voltage is applied to such an organic light-emitting element, electrons and holes injected from the two electrodes combine in the organic thin film, forming pairs that annihilate each other and emit light. The organic thin film can be composed of a single layer or multiple layers, as needed.

[0005] The material for 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 constitute a light-emitting layer on its own, or a compound that can play the role of a host or dopant in a host-dopant light-emitting layer. In addition, the organic thin film material may be a compound that can perform roles such as hole injection, hole transport, electron blockade, hole blockade, electron transport, and electron injection.

[0006] To improve the performance, lifespan, or efficiency of organic light-emitting devices, there is a constant demand for the development of organic thin-film materials. [Overview of the project] [Problems that the invention aims to solve]

[0007] This specification aims to provide compounds and organic light-emitting devices containing them. [Means for solving the problem]

[0008] In one embodiment of this specification, a compound of the following chemical formula 1 is provided. [ka]

[0009] In the aforementioned chemical formula 1, X is O; or S, Ar is a substituted or unsubstituted C6-C60 aryl group; a substituted or unsubstituted C2-C60 heteroaryl group containing O or S; or a substituted or unsubstituted C2-C60 heteroaryl group containing C=N. L1, L2, L11, and L12 are each independently directly bonded; or substituted or unsubstituted C6-C60 arylene groups. R11 and R12 are, independently, substituted or unsubstituted C1-C60 alkyl groups; substituted or unsubstituted C3-C60 cycloalkyl groups; substituted or unsubstituted C6-C60 aryl groups; or substituted or unsubstituted C2-C60 heteroaryl groups. If R11 is a dimethylfluorenyl group, then R11 and R12 are different from each other. R1 is hydrogen; deuterium; halogen group; cyano group; substituted or unsubstituted C1-C60 alkyl group; substituted or unsubstituted C3-C60 cycloalkyl group; substituted or unsubstituted C6-C60 aryl group; or substituted or unsubstituted C2-C60 heteroaryl group. l1, l2, l11, and l12 are integers from 1 to 5, and if each is 2 or greater, the substituents in parentheses are either identical or different from each other. r is an integer between 0 and 8, and if r is 2 or greater, R1 is either the same or different.

[0010] In another embodiment, there is provided an organic light-emitting device including a first electrode, a second electrode provided opposite to the first electrode, and an organic layer provided between the first electrode and the second electrode, wherein the organic layer contains the compound of Chemical Formula 1.

Advantages of the Invention

[0011] The compounds described herein may be used as materials for the organic layer of an organic light-emitting device. The compounds can serve as hole injection materials, hole transport materials, light-emitting materials, electron transport materials, electron injection materials, charge generation materials, etc. in an organic light-emitting device. In particular, the compounds can be used as materials for the hole transport layer, electron blocking layer, or prime layer of an organic light-emitting device.

[0012] When the compound of Chemical Formula 1 is used as a material for the hole transport layer, electron blocking layer, or prime layer of an organic light-emitting device, an organic light-emitting device excellent in terms of driving voltage and lifetime can be provided.

[0013] Specifically, when two substituents containing an amine group are substituted on a benzene ring in which the benzene ring is not further condensed in the fluorene skeleton like the compound of Chemical Formula 1, the HOLE characteristics are enhanced, and by adjusting the energy level values of the band gap and the T1 value (triplet state), when used as a material for the hole transport layer, electron blocking layer, or prime layer, there is an effect of providing an organic light-emitting device having excellent efficiency. In particular, when an aryl group is substituted together with the amine group, by increasing the hole mobility, an organic light-emitting device having a low driving voltage, high luminous efficiency, and long lifetime can be provided.

Brief Description of the Drawings

[0014] [Figure 1] It is a diagram exemplarily showing the stacked structure of an organic light-emitting device according to an embodiment of the present specification. [Figure 2] It is a diagram exemplarily showing the stacked structure of an organic light-emitting device according to an embodiment of the present specification. [Figure 3]It is a diagram exemplarily showing a stacked structure of an organic light-emitting device according to an embodiment of this specification. [Figure 4] It is a diagram exemplarily showing a stacked structure of an organic light-emitting device according to an embodiment of this specification. [Figure 5] It is a diagram exemplarily showing a stacked structure of an organic light-emitting device according to an embodiment of this specification.

Mode for Carrying Out the Invention

[0015] Hereinafter, this specification will be described in more detail.

[0016] In this specification, when a certain part "includes" a certain component, this means that, unless otherwise stated to the contrary, it does not exclude other components, but may further include other components.

[0017] The term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is replaced by another substituent, and the position to be substituted is not limited as long as it is the position where the hydrogen atom is substituted, that is, the position where the substituent can be substituted. When two or more substitutions are made, the two or more substituents may be the same or different from each other.

[0018] In this specification, "substituted or unsubstituted" means being substituted by at least one substituent selected from the group consisting of deuterium; halogen group; cyano group; C1-C60 alkyl group; C2-C60 alkenyl group; C2-C60 alkynyl group; C3-C60 cycloalkyl group; C2-C60 heterocycloalkyl group; C6-C60 aryl group; C2-C60 heteroaryl group; silyl group; phosphine oxide group; and amine group, or being substituted by a substituent in which at least two substituents selected from the exemplified substituents are linked, or being unsubstituted.

[0019] In this specification, "when no substituent is shown in the chemical formula or compound structure" means that a hydrogen atom is bonded to a carbon atom. However, deuterium ( 2Since H (Deuterium) is an isotope of hydrogen, some hydrogen atoms may be deuterium.

[0020] In one embodiment of this application, "where no substituents are shown in the chemical formula or compound structure" can mean that all positions that could be substituents are hydrogen or deuterium. That is, in the case of deuterium, it is an isotope of hydrogen, and some of the hydrogen atoms may be the isotope deuterium, in which case the deuterium content may be 0% to 100%.

[0021] In one embodiment of this application, in cases where "substituents are not indicated in the chemical formula or compound structure," if the deuterium content is 0%, the hydrogen content is 100%, and none of the substituents explicitly exclude deuterium such as hydrogen, then hydrogen and deuterium may be used together in the compound.

[0022] In one embodiment of this application, deuterium is an isotope of hydrogen, having a deuteron as its nucleus, which consists of one proton and one neutron, and can be represented as hydrogen-2, with the element symbol D or 2 It can be represented by H.

[0023] In one embodiment of this application, isotopes are atoms that have the same atomic number (Z) but different mass numbers (A). Isotopes can also be interpreted as elements that have the same number of protons but different numbers of neutrons.

[0024] In one embodiment of this application, the meaning of the content T% of a specific substituent can be defined as T2 / T1X100 = T% when T1 is defined as the total number of substituents that the basic compound may have, and T2 is defined as the number of specific substituents among them.

[0025] In other words, in one example, [ka] In a phenyl group represented by the formula shown, a deuterium content of 20% can be expressed as 20% when the total number of substituents that the phenyl group can have is 5 (T1 in the formula), and of these substituents, the number of deuterium atoms is 1 (T2 in the formula). In other words, a phenyl group with a deuterium content of 20% can be represented by the following structural formula. [ka]

[0026] Furthermore, in one embodiment of this application, the term "phenyl group with a deuterium content of 0%" can mean a phenyl group that does not contain a deuterium atom, i.e., a phenyl group having five hydrogen atoms.

[0027] In this specification, the alkyl group may include a linear or branched chain and may be further substituted with other substituents. The number of carbon atoms in the alkyl group may be 1 to 60, more specifically 1 to 40, and more specifically 1 to 20. 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, Examples include, but are not limited to, 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, 1-ethyl-propyl group, 1,1-dimethyl-propyl group, isohexyl group, 2-methylpentyl group, 4-methylhexyl group, and 5-methylhexyl group.

[0028] In this specification, the alkenyl group may include a linear or branched chain and may be further substituted with other substituents. The number of carbon atoms in the alkenyl group may be 2 to 60, more specifically 2 to 40, and more specifically 2 to 20. Specific examples include, but are not limited to, vinyl group, 1-propenyl group, isopropenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 3-methyl-1-butenyl group, 1,3-butadienyl group, allyl group, 1-phenylvinyl-1-yl group, 2-phenylvinyl-1-yl group, 2,2-diphenylvinyl-1-yl group, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl group, 2,2-bis(diphenyl-1-yl)vinyl-1-yl group, stilbenyl group, and styrenyl group.

[0029] In this specification, the alkynyl group may include a straight chain or a branched chain and may be further substituted with other substituents. The number of carbon atoms in the alkynyl group may be 2 to 60, more specifically 2 to 40, and more specifically 2 to 20.

[0030] In this specification, the cycloalkyl group may be monocyclic or polycyclic and may be further substituted with other substituents. Here, polycyclic means a group in which the cycloalkyl group is directly linked or fused with another ring group. Here, the other ring group may be a cycloalkyl group, but may also be other types of ring groups, such as a heterocycloalkyl group, an aryl group, a heteroaryl group, etc. The number of carbon atoms in the cycloalkyl group may be 3 to 60, more specifically 3 to 40, and more specifically 5 to 20. Specifically, examples include, but are not limited to, cyclopropyl group, cyclobutyl group, cyclopentyl group, 3-methylcyclopentyl group, 2,3-dimethylcyclopentyl group, cyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 2,3-dimethylcyclohexyl group, 3,4,5-trimethylcyclohexyl group, 4-tert-butylcyclohexyl group, cycloheptyl group, and cyclooctyl group.

[0031] In this specification, the heterocycloalkyl group comprises O, S, Se, N, or Si as a heteroatom, and may be monocyclic or polycyclic, and may be further substituted with other substituents. Here, polycyclic means a group in which the heterocycloalkyl group is directly linked or fused with another ring group. Here, the other ring group may be a heterocycloalkyl group, but may also be other types of ring groups, such as a cycloalkyl group, an aryl group, or a heteroaryl group. The number of carbon atoms in the heterocycloalkyl group may be 2 to 60, more specifically 2 to 40, and more specifically 3 to 20.

[0032] In this specification, the aryl group may include a monocyclic or polycyclic group and may be further substituted with other substituents. Here, polycyclic means a group in which the aryl group is directly linked or fused with another ring group. Here, the other ring group may be an aryl group, but may also be other types of ring groups, such as a cycloalkyl group, a heterocycloalkyl group, or a heteroaryl group. The aryl group may include a spiro group. The number of carbon atoms in the aryl group may be 6 to 60, more specifically 6 to 40, and more specifically 6 to 25. If the aryl group has two or more rings, the number of carbon atoms may be 8 to 60, 8 to 40, or 8 to 30. Specific examples of the aryl group include, but are not limited to, phenyl, biphenyl, terphenyl, naphthyl, anthryl, crisenyl, phenantrenyl, ferylenyl, fluoranthenyl, triphenylenyl, phenalenyl, pyrenyl, tetracenyl, pentacenyl, fluorenyl, indenyl, acenaphthirenyl, benzofluorenyl, spirobifluorenyl, 2,3-dihydro-1H-indenyl, and their fused ring groups.

[0033] In this specification, the terphenyl group may be selected from the following structures. [ka]

[0034] In this specification, the fluorenyl group may be substituted, and adjacent substituents may bond to each other to form a ring.

[0035] When the fluorenyl group is substituted, it may be, but is not limited to, the following compounds. [ka]

[0036] In this specification, the heteroaryl group comprises O, S, SO2, Se, N, or Si as a heteroatom, and may be monocyclic or polycyclic, and may be further substituted with other substituents. Here, polycyclic means a group in which the heteroaryl group is directly linked or fused with another ring group. Here, the other ring group may be a heteroaryl group, but may also be other types of ring groups, such as cycloalkyl groups, heterocycloalkyl groups, or aryl groups. The number of carbon atoms in the heteroaryl group may be 2 to 60, specifically 2 to 40, and more specifically 3 to 25. If the heteroaryl group has two or more rings, the number of carbon atoms may be 4 to 60, 4 to 40, or 4 to 25. Specific examples of the heteroaryl group include pyridyl group, pyrrolyl group, pyrimidyl group, pyridadinyl group, furanyl group, thiophene group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, triazolyl group, furazanyl group, oxadiazolyl group, thiadiazolyl group, dithiazolyl group, tetrazolyl group, pyranyl group, thiopyranyl group, diazinyl group, oxazinyl group, thiadinyl group, dioxynyl group, triazinyl group, tetradinyl group, quinolyl group, isoquinolyl group, quinazolinyl group, isoquinazolinyl group, quinozolilyl group, naphthyridyl group, acridinyl group, phenantridinyl group, imidazopyridinyl group, diazanaphthalenyl group, triazaidene group, indolyl group, indolidinyl group, benzothiazolyl group, and benzoxazolyl group. Group, benzimidazolyl group, benzothiophene group, benzofuran group, dibenzothiophene group, dibenzofuran group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, phenazinyl group, dibenzosilol group, spirovi(dibenzosilol), dihydrophenazinyl group, phenoxadinyl group, phenanthridine group, thienyl group, indro[2,3-a]carbazolyl group, indro [2,3-b]carbazolyl group, indolinyl group, 10,11-dihydro-dibenzo[b,f]azepine group, 9,10-dihydroacridinyl group, phenanthrazinyl group, phenothiazinyl group, phthalazinyl group, naphthilidinyl group, phenanthrolinyl group, benzo[c][1,2,5]thiadiazolyl group, 5,10-dihydrodibenzo[b,e][1,4]azacylinyl, pyrazolo[1,5-c]Quinazolinyl group, pyrido[1,2-b]indazolyl group, pyrido[1,2-a]imidazo[1,2-e]indolinyl group, benzoflo[2,3-d]pyrimidyl group; benzothieno[2,3-d]pyrimidyl group; benzoflo[2,3-a]carbazolyl group, benzothieno[2,3-a]carbazolyl group, 1,3-dihydroindro[2,3-a]carbazolyl group, benzoflo[3, 2-a]carbazolyl group, benzothieno[3,2-a]carbazolyl group, 1,3-dihydroindro[3,2-a]carbazolyl group, benzoflo[2,3-b]carbazolyl group, benzothieno[2,3-b]carbazolyl group, 1,3-dihydroindro[2,3-b]carbazolyl group, benzoflo[3,2-b]carbazolyl group, benzothieno[3,2-b]carbazolyl group, 1,3-dihydro Droindro[3,2-b]carbazolyl group, benzoflo[2,3-c]carbazolyl group, benzothieno[2,3-c]carbazolyl group, 1,3-dihydroindro[2,3-c]carbazolyl group, benzoflo[3,2-c]carbazolyl group, benzothieno[3,2-c]carbazolyl group, 1,3-dihydroindro[3,2-c]carbazolyl group, 1,3-dihydroindeno[2,1-b Examples include, but are not limited to, the carbazolyl group, 5,11-dihydroindeno[1,2-b]carbazolyl group, 5,12-dihydroindeno[1,2-c]carbazolyl group, 5,8-dihydroindeno[2,1-c]carbazolyl group, 7,12-dihydroindeno[1,2-a]carbazolyl group, and 11,12-dihydroindeno[2,1-a]carbazolyl group.

[0037] In this specification, a silyl group is a substituent containing Si, to which the Si atom is directly linked as a radical, and is represented as -Si(R101)(R102)(R103), where R101 to R103 may be the same or different from each other, and each may independently consist of at least one of the following substituents: hydrogen; deuterium; halogen group; alkyl group; alkenyl group; alkoxy group; cycloalkyl group; aryl group; and heteroaryl group. Specific examples of silyl groups include, but are not limited to, trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, and phenylsilyl group.

[0038] In this specification, the phosphine oxide group is represented as -P(=O)(R104)(R105), where R104 and R105 may be identical or different from each other and each may independently consist of at least one substituent from among hydrogen, deuterium, halogen groups, alkyl groups, alkenyl groups, alkoxy groups, cycloalkyl groups, aryl groups, and heteroaryl groups. Specifically, it may be substituted with alkyl groups or aryl groups, and the alkyl and aryl groups described above can be applied. For example, the phosphine oxide group may be, but is not limited to, dimethylphosphine oxide, diphenylphosphine oxide, or dinaphthylphosphine oxide.

[0039] In this specification, the amine group is represented as -N(R106)(R107), where R106 and R107 are identical or different, and each may independently be a substituent consisting of at least one of hydrogen, deuterium, halogen group, alkyl group, alkenyl group, alkoxy group, cycloalkyl group, aryl group, and heteroaryl group. The amine group may be selected from the group consisting of -NH2, monoalkylamine group, monoarylamine group, monoheteroarylamine group, dialkylamine group, diarylamine group, diheteroarylamine group, alkylarylamine group, alkylheteroarylamine group, and arylheteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include, but are not limited to, methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, dibiphenylamine group, anthracenylamine group, 9-methyl-anthracenylamine group, diphenylamine group, phenylnaphthylamine group, ditolylamine group, phenyltolylamine group, triphenylamine group, biphenylnaphthylamine group, phenylbiphenylamine group, biphenylfluorenylamine group, phenyltriphenylenylamine group, and biphenyltriphenylenylamine group.

[0040] In this specification, the above-mentioned examples of aryl groups can be applied, except that the arylene group is a divalent group.

[0041] In one embodiment of this specification, X may be O.

[0042] In one embodiment of this specification, X may be S.

[0043] In one embodiment of this specification, the chemical formula 1 may be represented by any of the following chemical formulas 1-1 to 1-3. [ka] [ka] [ka]

[0044] In the above chemical formulas 1-1 to 1-3, The definitions of X, L1, L2, L11, L12, R11, R12, Ar, l1, l2, l11 and l12 are the same as the definitions in Chemical Formula 1 above. H1 to H3 are hydrogen; or deuterium, respectively. h1 to h3 are integers from 0 to 8, and if each is 2 or greater, the substituents in parentheses are either identical or different from each other.

[0045] In one embodiment of this specification, the chemical formula 1 may be represented by the following chemical formula 2-1 or 2-2. [ka] [ka]

[0046] In the above chemical formulas 2-1 and 2-2, the definitions of each substituent are the same as those in chemical formula 1.

[0047] In one embodiment of this specification, L1 and L2 may each be independently directly bonded; or they may be deuterium-substituted or unsubstituted C6-C60 arylene groups.

[0048] In one embodiment of this specification, L1 and L2 may each be independently directly bonded; or they may be deuterium-substituted or unsubstituted C6-C30 arylene groups.

[0049] In one embodiment of this specification, L1 and L2 may be independently directly bonded; or they may be C6-C60 arylene groups.

[0050] In one embodiment of this specification, L1 and L2 may both be directly coupled.

[0051] In the embodiments of this specification, L1 may be a direct bond, and L2 may be a deuterium-substituted or unsubstituted C6-C30 arylene group.

[0052] In the embodiments of this specification, L1 may be a direct bond, and L2 may be a deuterium-substituted or unsubstituted phenylene group.

[0053] In embodiments of this specification, L1 may be a direct bond, and L2 may be a C6-C30 arylene group.

[0054] In embodiments of this specification, L1 may be a direct bond, and L2 may be a phenylene group.

[0055] In embodiments of this specification, L1 may be a deuterium-substituted or unsubstituted C6-C30 arylene group, and L2 may be directly bonded.

[0056] In embodiments of this specification, L1 may be a C6-C30 arylene group, and L2 may be directly bonded.

[0057] In embodiments of this specification, L1 may be a deuterium-substituted or unsubstituted phenylene group; a deuterium-substituted or unsubstituted biphenylene group; a deuterium-substituted or unsubstituted naphthylene group; or a deuterium-substituted or unsubstituted dimethylfluorenylene group, and L2 may be a deuterium-substituted or unsubstituted phenylene group.

[0058] In embodiments of this specification, L1 may be a phenylene group; a biphenylene group; a naphthylene group; or a dimethylfluorenylene group, and L2 may be a phenylene group.

[0059] In one embodiment of this specification, L11 and L12 may each be independently directly bonded; or they may be deuterium-substituted or unsubstituted C6-C60 arylene groups.

[0060] In one embodiment of this specification, L11 and L12 may be independently directly bonded; or they may be C6-C60 arylene groups.

[0061] In one embodiment of this specification, both L11 and L12 may be directly coupled.

[0062] In the embodiments of this specification, L11 may be a deuterium-substituted or unsubstituted C6-C60 arylene group, and L12 may be directly bonded.

[0063] In embodiments of this specification, L11 may be a deuterium-substituted or unsubstituted C6-C30 arylene group, and L12 may be directly bonded.

[0064] In embodiments of this specification, L11 may be a deuterium-substituted or unsubstituted phenylene group, and L12 may be directly bonded.

[0065] In embodiments of this specification, L11 may be a C6-C60 arylene group, and L12 may be directly bonded.

[0066] In embodiments of this specification, L11 may be a C6-C30 arylene group, and L12 may be directly bonded.

[0067] In embodiments of this specification, L11 may be a phenylene group, and L12 may be directly bonded.

[0068] In the embodiments of this specification, L11 may be a direct bond, and L12 may be a deuterium-substituted or unsubstituted C6-C60 arylene group.

[0069] In the embodiments of this specification, L11 may be a direct bond, and L12 may be a deuterium-substituted or unsubstituted C6-C30 arylene group.

[0070] In the embodiments of this specification, L11 may be a direct bond, and L12 may be a deuterium-substituted or unsubstituted phenylene group.

[0071] In the embodiments of this specification, L11 may be a direct bond, and L12 may be a C6-C60 arylene group.

[0072] In embodiments of this specification, L11 may be a direct bond, and L12 may be a C6-C30 arylene group.

[0073] In embodiments of this specification, L11 may be a direct bond, and L12 may be a phenylene group.

[0074] In one embodiment of this specification, L11 and L12 may both be deuterium-substituted or unsubstituted C6-C60 arylene groups.

[0075] In one embodiment of this specification, L11 and L12 may both be deuterium-substituted or unsubstituted C6-C30 arylene groups.

[0076] In one embodiment of this specification, L11 and L12 may both be deuterium-substituted or unsubstituted C6-C10 arylene groups.

[0077] In one embodiment of this specification, L11 and L12 may both be deuterium-substituted or unsubstituted phenylene groups.

[0078] In one embodiment of this specification, L11 and L12 may both be C6-C60 arylene groups.

[0079] In one embodiment of this specification, L11 and L12 may both be C6-C30 arylene groups.

[0080] In one embodiment of this specification, L11 and L12 may both be C6-C10 arylene groups.

[0081] In one embodiment of this specification, both L11 and L12 may be phenylene groups.

[0082] In one embodiment of this specification, R11 and R12 are, independently, a substituted or unsubstituted C3-C60 cycloalkyl group; a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group.

[0083] In one embodiment of this specification, R11 and R12 are, independently, a substituted or unsubstituted C3-C40 cycloalkyl group; a substituted or unsubstituted C6-C40 aryl group; or a substituted or unsubstituted C2-C40 heteroaryl group.

[0084] In one embodiment of this specification, R11 and R12 are, independently, a substituted or unsubstituted C3-C30 cycloalkyl group; a substituted or unsubstituted C6-C30 aryl group; or a substituted or unsubstituted C2-C20 heteroaryl group.

[0085] In one embodiment of this specification, R11 and R12 are, independently, a substituted or unsubstituted adamantane group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted dibenzothiophene group; or a substituted or unsubstituted naphthobenzofuran group.

[0086] In one embodiment of this specification, R11 and R12 are, independently, a deuterium-substituted or unsubstituted adamantane group; a phenyl group substituted or unsubstituted with at least one substituent from deuterium, a cycloalkyl group, an aryl group, and a heteroaryl group; a deuterium-substituted or unsubstituted biphenyl group; a deuterium-substituted or unsubstituted terphenyl group; a deuterium-substituted or unsubstituted naphthyl group; a fluorenyl group substituted or unsubstituted with at least one substituent from deuterium, an alkyl group, and an aryl group; a deuterium-substituted or unsubstituted 9,9'-spirobi[fluorene]; a deuterium-substituted or unsubstituted dibenzofuran group; a deuterium-substituted or unsubstituted dibenzothiophene group; or a deuterium-substituted or unsubstituted naphthobenzofuran group.

[0087] In one embodiment of this specification, R11 is a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group containing O or S, and R12 may be a substituted or unsubstituted C3-C60 cycloalkyl group; a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group containing O or S.

[0088] In one embodiment of this specification, R11 is a substituted or unsubstituted C6-C30 aryl group; or a substituted or unsubstituted C2-C30 heteroaryl group containing O or S, and R12 may be a substituted or unsubstituted C3-C30 cycloalkyl group; a substituted or unsubstituted C6-C30 aryl group; or a substituted or unsubstituted C2-C30 heteroaryl group containing O or S.

[0089] In one embodiment of this specification, R11 is a C6-C30 aryl group substituted or unsubstituted with at least one substituent from deuterium, alkyl groups, and aryl groups; or a C2-C30 heteroaryl group substituted or unsubstituted with deuterium and containing O or S, and R12 may be a C3-C30 cycloalkyl group substituted or unsubstituted with deuterium; a C6-C30 aryl group substituted or unsubstituted with at least one substituent from deuterium, alkyl groups, aryl groups, and heteroaryl groups; or a C2-C30 heteroaryl group substituted or unsubstituted with deuterium and containing O or S.

[0090] In one embodiment of this specification, R11 is 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 anthracenyl group; a substituted or unsubstituted fluorenyl group; or a substituted or unsubstituted dibenzofuran group; or a substituted or unsubstituted dibenzothiophene group.

[0091] In one embodiment of this specification, R11 is a deuterium-substituted or unsubstituted phenyl group; a deuterium-substituted or unsubstituted biphenyl group; a deuterium-substituted or unsubstituted terphenyl group; a deuterium-substituted or unsubstituted naphthyl group; a deuterium-substituted or unsubstituted anthracenyl group; a fluorenyl group substituted or unsubstituted with at least one substituent from deuterium, an alkyl group, and an aryl group; or a deuterium-substituted or unsubstituted dibenzofuran group; or a deuterium-substituted or unsubstituted dibenzothiophene group.

[0092] In one embodiment of this specification, R12 is a substituted or unsubstituted adamantane 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 anthracenyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted dibenzothiophene group; or a substituted or unsubstituted naphthobenzofuran group.

[0093] In one embodiment of this specification, R12 is a phenyl group substituted or unsubstituted with at least one substituent from deuterium and a heteroaryl group; a biphenyl group substituted or unsubstituted with deuterium; a terphenyl group substituted or unsubstituted with deuterium; a naphthyl group substituted or unsubstituted with deuterium; an anthracenyl group substituted or unsubstituted with deuterium; a fluorenyl group substituted or unsubstituted with at least one substituent from deuterium, an alkyl group and an aryl group; a 9,9'-spirobi[fluorene] group substituted or unsubstituted with deuterium; a dibenzofuran group substituted or unsubstituted with deuterium; a dibenzothiophene group substituted or unsubstituted with deuterium; or a naphthobenzofuran group substituted or unsubstituted with deuterium.

[0094] In one embodiment of this specification, when R11 is a dimethylfluorenyl group, R11 and R12 are different from each other.

[0095] In one embodiment of this specification, if R11 is a dimethylfluorenyl group, then R12 is a C3-C30 cycloalkyl group; a substituted or unsubstituted C6-C12 aryl group; a deuterium-substituted or unsubstituted diphenylfluorenyl group; a deuterium-substituted or unsubstituted 9,9'-spirobi[fluorene]; a deuterium-substituted or unsubstituted C18-C60 aryl group; or a deuterium-substituted or unsubstituted heteroaryl group.

[0096] In one embodiment of this specification, if R11 is a dimethylfluorenyl group, then R12 cannot be a dimethylfluorenyl group. In other words, R11 and R12 cannot both be dimethylfluorenyl groups.

[0097] In one embodiment of this specification, the chemical formula 1 [ka] The structure may also be represented by the following chemical formulas 3-1 or 3-2. [ka] [ka]

[0098] In the above chemical formulas 3-1 and 3-2, The definitions of L1, L11, L12, l1, l11, and l12 are the same as the definitions in Chemical Formula 1 above. H11 is hydrogen; or deuterium. h11 is an integer between 0 and 7, and if it is 2 or greater, H11 is either the same or different. R31 is a substituted or unsubstituted C6-C12 aryl group; or a substituted or unsubstituted C2-C30 heteroaryl group containing O or S. R32 is a substituted or unsubstituted C3-C30 cycloalkyl group; a substituted or unsubstituted C6-C30 aryl group; or a substituted or unsubstituted C2-C30 heteroaryl group containing O or S. R33 is a C13-C30 aryl group substituted or unsubstituted with deuterium or an aryl group; or a C2-C30 heteroaryl group substituted or unsubstituted and containing O or S. R41 and R42 are, independently, deuterium-substituted or unsubstituted C1-C10 alkyl groups. [ka] This indicates the position where it bonds with chemical formula 1.

[0099] In one embodiment of this specification, the Ar is a substituted or unsubstituted C6-C30 aryl group; a substituted or unsubstituted C2-C30 heteroaryl group containing O or S; or a substituted or unsubstituted C2-C30 heteroaryl group containing C=N.

[0100] In one embodiment of this specification, Ar is a substituted or unsubstituted C6-C30 aryl group; or a substituted or unsubstituted C2-C30 heteroaryl group containing O or S.

[0101] In one embodiment of this specification, Ar is a deuterium-substituted or unsubstituted C6-C30 aryl group; or a deuterium-substituted or unsubstituted C2-C30 heteroaryl group containing O or S.

[0102] In one embodiment of this specification, Ar is a phenyl group substituted or unsubstituted with deuterium or a heteroaryl group; a biphenyl group substituted or unsubstituted with deuterium; a terphenyl group substituted or unsubstituted with deuterium; a naphthyl group substituted or unsubstituted with deuterium; a phenantrenyl group substituted or unsubstituted with deuterium; a phenalenyl group substituted or unsubstituted with at least one substituent from deuterium, an alkyl group, and an aryl group; a 9,9'-spirobi[fluorene] group substituted or unsubstituted with deuterium; a dibenzofuran group substituted or unsubstituted with deuterium; or a dibenzothiophene group substituted or unsubstituted with deuterium.

[0103] In one embodiment of this specification, Ar is a phenyl group substituted or unsubstituted with deuterium or a heteroaryl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenantrenyl group; a substituted or unsubstituted phenalenyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted dibenzofuran group; or a substituted or unsubstituted dibenzothiophene group.

[0104] In one embodiment of this specification, Ar is a phenyl group; biphenyl group; terphenyl group; naphthyl group; phenantrenyl group; phenalenyl group; dimethylfluorenyl group; diphenylfluorenyl group; 9,9'-spirobio[fluorene]; dibenzofuran group; or dibenzothiophene, substituted or unsubstituted with deuterium or a dibenzofuran group.

[0105] In one embodiment of this specification, R1 is hydrogen; deuterium; a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group.

[0106] In one embodiment of this specification, R1 is hydrogen; or deuterium.

[0107] In one embodiment of this specification, the chemical formula 1 [ka] and [ka] teeth, [ka] It is joined at positions 1 and 4. For example, [ka] but [ka] If it is joined to the first position, [ka] teeth, [ka] It can be joined at position 4, or vice versa.

[0108] In another embodiment, the chemical formula 1 [ka] and [ka] teeth, [ka] It will be joined at positions 1 and 3.

[0109] In another embodiment, the chemical formula 1 [ka] and [ka] teeth, [ka] It will be joined at positions 1 and 2.

[0110] In another embodiment, the chemical formula 1 [ka] and [ka] teeth, [ka] It is joined at positions 2 and 4.

[0111] In another embodiment, the chemical formula 1 [ka] and [ka] teeth, [ka] It is joined to positions 2 and 3.

[0112] In another embodiment, the chemical formula 1 [ka] and [ka] teeth, [ka] It is joined at positions 3 and 4.

[0113] In one embodiment of this specification, the chemical formula 1 is represented by the chemical formula 1-1 or 1-2, [ka] and [ka] but, [ka] When joined at positions 1 and 4, any of the following i to iv can be satisfied.

[0114] i) R11 and R12 are independently a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted dibenzofuran group; or a substituted or unsubstituted dibenzothiophene group. ii) R11 and R12 are independently a substituted or unsubstituted adamantane group; a phenyl group substituted or unsubstituted with deuterium or an aryl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; or a substituted or unsubstituted anthracenyl group. iii) L1 is a substituted or unsubstituted arylene group having 10 to 60 carbon atoms, and iv) [ka] and [ka] One of them contains deuterium.

[0115] In one embodiment of this specification, the chemical formula 1 is represented by the chemical formulas 1-3, [ka] and [ka] but [ka] When bonded to one of numbers 1 and 4, R11 and R12 may independently be a substituted or unsubstituted adamantane 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 anthracenyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted dibenzothiophene group; or a substituted or unsubstituted naphthobenzofuran group.

[0116] In one embodiment of this specification, the deuterium content of chemical formula 1 is 0% to 100%.

[0117] In one embodiment of this specification, the deuterium content of the chemical formula 1 may be 0%.

[0118] In one embodiment of this specification, the deuterium content of the chemical formula 1 may be greater than 0% and less than or equal to 100%.

[0119] In one embodiment of this specification, the deuterium content of the chemical formula 1 may be 5% to 100%.

[0120] In one embodiment of this specification, the deuterium content of the chemical formula 1 may be 10% to 100%.

[0121] In one embodiment of this specification, the deuterium content of the chemical formula 1 may be 20% to 100%.

[0122] In one embodiment of this specification, the deuterium content of the chemical formula 1 may be 50% to 100%.

[0123] In one embodiment of this specification, the deuterium content of chemical formula 1 may be 0%, or 5% to 100%.

[0124] In one embodiment of this specification, the deuterium content of chemical formula 1 may be 0%, or 10% to 100%.

[0125] In one embodiment of this specification, the deuterium content of chemical formula 1 may be 0%, or 20% to 100%.

[0126] In one embodiment of this specification, the deuterium content of chemical formula 1 may be 0%, or 50% to 100%.

[0127] In one embodiment of this specification, the chemical formula 1 can be represented by any of the following compounds, but is not limited thereto.

change

[0128] Furthermore, by introducing various substituents into the structure of chemical formula 1, compounds having the unique properties 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, materials that satisfy the requirements for each organic layer can be synthesized.

[0129] Furthermore, by introducing various substituents into the structure of chemical formula 1, it becomes possible to finely adjust the energy band gap, while simultaneously improving the properties at the interface between organic materials and diversifying the applications of the material.

[0130] In one embodiment of this specification, an organic light-emitting element 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 one or more of the organic layers contain the compound of chemical formula 1.

[0131] In one embodiment of this specification, the first electrode may be an anode and the second electrode may be a cathode.

[0132] In other embodiments of this specification, the first electrode may be a cathode and the second electrode may be an anode.

[0133] In one embodiment of this specification, the organic light-emitting element is a blue organic light-emitting element, and the compound of chemical formula 1 may be used as a material for the blue organic light-emitting element. For example, the compound of chemical formula 1 may be included in the hole transport layer or electron blocking layer of the blue organic light-emitting element.

[0134] In one embodiment of this specification, the organic light-emitting element is a green organic light-emitting element, and the compound of chemical formula 1 may be used as a material for the green organic light-emitting element. For example, the compound of chemical formula 1 may be included in the hole transport layer or electron blocking layer of the green organic light-emitting element.

[0135] In one embodiment of this specification, the organic light-emitting element is a red organic light-emitting element, and the compound of chemical formula 1 may be used as a material for the red organic light-emitting element. For example, the compound of chemical formula 1 may be included in the hole transport layer or electron blocking layer of the red organic light-emitting element.

[0136] The organic light-emitting element described herein may be manufactured by conventional methods and materials for manufacturing organic light-emitting elements, except that one or more organic layers are formed using the aforementioned compound.

[0137] The aforementioned compound may be formed on the organic layer not only by vacuum deposition during the manufacture of the organic light-emitting element, but also by a solution coating method. Here, solution coating methods include, but are not limited to, spin coating, dip coating, inkjet printing, screen printing, spray coating, and roll coating.

[0138] The organic layers of the organic light-emitting element described herein may consist of a single layer, or they may consist of a multilayer structure in which two or more organic layers are stacked. For example, the organic light-emitting element of the present invention may have a structure in which the organic layers include a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and so on. However, the structure of the organic light-emitting element is not limited thereto and may include fewer organic layers.

[0139] In the organic light-emitting device of this specification, the organic layer includes a hole transport layer, and the hole transport layer may include the compound of chemical formula 1.

[0140] In the organic light-emitting device of this specification, the organic layer includes an electron blocking layer, and the electron blocking layer may include the compound of chemical formula 1.

[0141] In the organic light-emitting element of this specification, the organic layer includes a prime layer, and the prime layer may include the compound of chemical formula 1. The prime layer is provided between the hole transport layer and the light-emitting layer and is also called a hole transport auxiliary layer. By forming a prime layer between the hole transport layer and the light-emitting layer, holes are transported more smoothly from the hole transport layer to the light-emitting layer, and excitons are confined within the light-emitting layer to prevent light leakage, thus enabling the realization of an organic electroluminescent element with excellent luminescence efficiency.

[0142] The organic light-emitting element of the present invention may further include one or more layers selected from the group consisting of an emissive layer, a hole injection layer, a hole transport layer, a prime layer, an electron injection layer, an electron transport layer, an electron blocking layer, and a hole blocking layer.

[0143] Figures 1 to 5 illustrate the stacking sequence of electrodes and organic layers in an organic light-emitting element according to one embodiment of this specification. However, these figures are not intended to limit the scope of this application, and organic light-emitting element structures known in the art may also be applicable to this application.

[0144] Figure 1 shows an organic light-emitting element in which an anode 200, an organic material layer 300, and a cathode 400 are sequentially stacked on a substrate 100. However, the structure is not limited to this, and an organic light-emitting element may be realized in which the cathode, organic material layer, and anode are sequentially stacked on a substrate, as shown in Figure 2.

[0145] Figures 3 to 5 illustrate cases where the organic layers are multilayered. The organic light-emitting device according to Figure 3 includes a hole injection layer 301, a hole transport layer 302, an emissive layer 305, an electron transport layer 306, and an electron injection layer 307. The organic light-emitting device according to Figure 4 includes a hole injection layer 301, a hole transport layer 302, an electron blocking layer 303, an emissive layer 305, an electron transport layer 306, and an electron injection layer 307. The organic light-emitting device according to Figure 5 includes a hole injection layer 301, a hole transport layer 302, a prime layer 304, an emissive layer 305, an electron transport layer 306, and an electron injection layer 307. However, the scope of this application is not limited by such a layered structure, and the remaining layers excluding the emissive layer may be omitted as needed, or other necessary functional layers may be added.

[0146] The organic layer containing the compound of chemical formula 1 may further contain other substances as needed.

[0147] In an organic light-emitting device according to one embodiment of this specification, materials other than the compound of chemical formula 1 are exemplified below, but these are for illustrative purposes only and do not limit the scope of this application, and may be replaced with materials known in the art.

[0148] As the anode material, a material with a relatively large work function can be used, 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 their alloys; 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.

[0149] As the cathode material, a material with a relatively low work function can be used, such as a metal, metal oxide, or conductive polymer. Specific examples of the cathode material include, but are not limited to, metals or alloys thereof such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead; and multilayer materials such as LiF / Al or LiO2 / Al.

[0150] As the hole injection material, known hole injection materials can be used, for example, phthalocyanine compounds such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429, or starburst-type amine derivatives 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), or polyaniline / dodecylbenzenesulfonic acid, a soluble conductive polymer. Poly(3,4-ethylenedioxythiophene) / Poly(4-styrenesulfonate), polyaniline / camphor sulfonic acid, or polyaniline / poly(4-styrenesulfonate) can be used.

[0151] As hole transport materials, pyrazoline derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, etc., may be used, and low molecular weight or high molecular weight materials may also be used.

[0152] As electron transport materials, metal complexes of oxadiazole derivatives, anthraquinodimethane and its derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, tetracyanoanthraquinodimethane and its derivatives, fluorenone derivatives, diphenyldicyanoethylene and its derivatives, diphenoquinone derivatives, 8-hydroxyquinoline and its derivatives can be used, and not only low molecular weight substances but also high molecular weight substances may be used.

[0153] LiF is a typical electron injection material used in this art, for example, but this application is not limited to it.

[0154] As the light-emitting material, red, green, or blue light-emitting materials may be used, and if necessary, two or more light-emitting materials may be mixed and used. In this case, the two or more light-emitting materials may be deposited from separate sources or pre-mixed and deposited from a single source. Furthermore, fluorescent materials may be used as light-emitting materials, but phosphorescent materials may also be used. As the light-emitting material, a material that emits light by combining holes and electrons injected from the anode and cathode, respectively, may be used, but a material in which both the host material and the dopant material are involved in light emission may also be used.

[0155] In one embodiment of this specification, the host material may be a compound containing anthracene, but is not limited thereto.

[0156] In one embodiment of this specification, the dopant material may be a pyrene derivative containing a diamine, but is not limited thereto.

[0157] When using a mixture of hosts for the light-emitting material, hosts from the same series may be mixed, or hosts from different series may be mixed. For example, two or more types of N-type host materials or P-type host materials can be selected and used as the host material for the light-emitting layer.

[0158] An organic light-emitting element according to one embodiment of this specification may be a front-emitting type, a rear-emitting type, or a double-sided emitting type, depending on the material used.

[0159] A compound according to one embodiment of this specification can also operate in organic electronic devices, including organic solar cells, organic photoreceptors, and organic transistors, using the same principles as those applied to organic light-emitting devices. [Examples]

[0160] The Specification will be described in more detail below through examples, which are for illustrative purposes only and not intended to limit the scope of this application.

[0161] [Manufacturing Example 1] Manufacturing of Compound 19 [ka]

[0162] (1) Preparation of compound 19-2 2-iodonaphthalen-1-ol (E) (10 g, 44.8 mmol) and (6-bromo-3-chloro-2-fluorophenyl)boronic acid (F) (11.35 g, 44.8 mmol) were dispersed in toluene (110 ml), ethanol (20 ml), and water (20 ml). Then, K2CO3 (12.3 g, 89.6 mmol) was added, followed by tetrakis(triphenylphosphine)palladium (0) [Pd(PPh3)4] (0.51 g, 1 mol%), and the mixture was stirred under reflux for 6 hours. The temperature was lowered to room temperature, the aqueous layer was separated, and the organic layer was washed once more with water to separate the organic layer. Anhydrous magnesium sulfate was added to the collected organic layer, and after slurrying, it was filtered and concentrated under reduced pressure. The oily compound was separated by silica chromatography using a combination of hexane and ethyl acetate to produce compound 19-2 (19.3 g, yield 65%).

[0163] (2) Preparation of compound 19-3 Compound 19-2 (9.28 g, 26 mmol) was diluted in 50 ml of N-methyl-2-pyrrolidone (NMP), and potassium carbonate (5.47 g, 39.6 mmol) was added and the mixture was heated to 140°C. After about 1 hour, the reaction mixture was cooled to room temperature and slowly added to 500 ml of water. The precipitated solid was filtered, dissolved in tetrahydrofuran (THF), treated with anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The concentrated compound was slurryed with a small amount of tetrahydrofuran and an excess of hexane and filtered. To purify the filtered compound, it was separated by silica chromatography with hexane and ethyl acetate to prepare compound 19-3 (5.2 g, 63%).

[0164] (3) Preparation of compound 19-4 Compound 19-3 (5.2 g, 15.6 mmol) and phenylboronic acid (G) (2 g, 17 mmol) were dissolved in 50 ml of 1,4-dioxane and 10 ml of H2O. Then, Pd(PPh3)4 (0.9 g, 0.78 mmol) and K2CO3 (5.38 g, 39 mol) were added and the mixture was stirred under reflux for 5 hours. After the reaction was complete, 100 ml of methylene chloride (MC) and 150 ml of water were added to the reaction mixture and worked up. The organic layer was then separated using a fractionation funnel. The organic layer was dried over anhydrous MgSO4, the solvent was removed using a rotary evaporator, and then purified by column chromatography (MC:Hexane = 1:3) to obtain compound 19-4 (4.35 g, 85%).

[0165] (4) Preparation of compound 19 Compound 19-4 (4.35 g, 13.2 mmol) and di([1,1'-biphenyl]-4-yl)amine (I) (4.67 g, 14.5 mmol) were dissolved in 80 ml of xylene, and then tris(dibenzylideneacetone)dipalladium(0)[Pd2(dba)3] (0.6 g, 0.66 mmol) and tri-t-butylphosphine [P(t-Bu) 3) (0.6 ml, 1.32 mmol) and sodium tart-butoxide [NaOt-Bu] (3.8 g, 39 mol) were added, and the mixture was stirred under reflux at 125°C for 5 hours. After the reaction was complete, MC was added to the reaction mixture to dissolve it, then extracted with distilled water. The organic layer was dried over anhydrous magnesium sulfate, the solvent was removed using a rotary evaporator, and the compound was purified by column chromatography (MC:Hexane = 1:3) to obtain compound 19 (5.1 g, 63%).

[0166] In the above-mentioned Production Example 1, target compound A was synthesized in the same manner using intermediates E, F, G, and I shown in Table 1 below, instead of (E), (F), (G), and (I).

[0167] [Table 1] TIFF0007876250000086.tif238170 TIFF0007876250000087.tif124170

[0168] [Manufacturing Example 2] Manufacturing of Compound 652 [ka]

[0169] (1) Preparation of compound 652-3 2-iodonaphthalen-1-ol (30 g, 111.08 mmol) (A), (3-bromo-6-chloro-2-fluorophenyl)boronic acid (30.95 g, 122.19 mmol) (B), Pd(PPh3)4 (389.84 g, 555.41 mmol), and potassium carbonate (46.06 g, 333.25 mmol) were added to toluene (600 mL), ethanol (150 mL), and water (150 mL), and the mixture was stirred and refluxed for 6 hours. The temperature was lowered to room temperature, the aqueous layer was separated, and the organic layer was washed once more with water to separate the organic layer. Anhydrous magnesium sulfate was added to the collected organic layer, and after slurrying, it was filtered and concentrated under reduced pressure. The oily compound was separated by silica chromatography using a combination of hexane and ethyl acetate to obtain compound 652-3. (30 g, 85.324 mmol, 76.812% yield)

[0170] (2) Preparation of compound 652-2 Compound 652-3 (30 g, 85.32 mmol) and potassium carbonate (17.69 g, 127.99 mmol) were placed in NMP (150 mL) and heated to 140°C. After about 1 hour, the reaction mixture was cooled to room temperature and slowly added to 500 mL of water. The precipitated solid was filtered, dissolved in THF, treated with anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The concentrated compound was slurryed with a small amount of THF and an excess of hexane and filtered. To purify the filtered compound, it was separated by silica chromatography with hexane and ethyl acetate to obtain compound 652-2 (28 g, 84.442 mmol, 98.966% yield).

[0171] (3) Preparation of compound 652-1 Compound 652-2 (28 g, 84.44 mmol), [1,1'-biphenyl]-4-ylboronic acid (18.39 g, 92.89 mmol) (C), Pd(PPh3)4 (2.96 g, 4.22 mmol), and potassium carbonate (35.01 g, 253.32 mmol) were placed in 1,4-dioxane (600 mL) and water (150 mL), and the mixture was refluxed and stirred for 5 hours. After completion of the reaction, 100 mL of MC and 150 mL of water were added to the reaction solution for work-up, and then the mixture was placed in a separatory funnel to separate the organic layer. The organic layer was dried over anhydrous MgSO4, the solvent was removed using a rotary evaporator, and then the residue was purified by column chromatography (MC:Hexane = 1:3) to obtain Compound 652-1. (30 g, 74.094 mmol, 87.746% yield)

[0172] (4) Preparation of Compound 652 Compound 652-1 (30 g, 74.09 mmol), 3,5-diphenyl-N-(4-phenylphenyl)aniline (25.52 g, 64.1 mmol), Pd2(dba)3 (2.6 g, 3.7 mmol), Xphos (2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl) (4.01 mL, 7.41 mmol), and NaOt-Bu (21.81 g, 222.28 mmol) were placed in xylene (150 mL), and the mixture was refluxed and stirred at 125 °C for 5 hours. After completion of the reaction, MC was added to the reaction solution to dissolve it, followed by extraction with distilled water. The organic layer was dried over anhydrous magnesium sulfate, the solvent was removed using a rotary evaporator, and then the residue was purified by column chromatography (MC:Hexane = 1:3) to obtain Compound 652. (42 g, 60.884 mmol, 82.171% yield)

[0173] In Production Example 2 above, the compound was synthesized in the same manner using Intermediate A, B, C, and D in Table 2 below instead of (A), (B), (C), and (D).

[0174]

Table 2

[0175] [Manufacturing Example 3] Manufacturing of Compound 984 [ka]

[0176] After dissolving compound 652 (10 g, 0.013 mol) and trifluoromethanesulfonic acid (triflic acid) (8.78 mL, 99.46 mmol) in D6-benzene (100 ml), 、 The mixture was stirred at 60°C for 4 hours. After the reaction was complete, it was neutralized with an aqueous K3PO4 solution at room temperature, and then extracted with dichloromethane (DCM) and distilled water (H2O).

[0177] The reaction product extracted again was purified by column chromatography (DCM:Hex=1:1) and recrystallized with methanol to obtain compound 984. (9g, 0.0111mol, 85.7% yield)

[0178] Here, Hex refers to hexane (Hexane), and DCM:Hex refers to the volume ratio.

[0179] [Manufacturing Example 4] Manufacturing of Compound 1013 [ka]

[0180] Compound 971 (10 g, 0.014 mol) and Triflic acid (8.78 mL, 99.46 mmol) were dissolved in D6-benzene (D 6- benzene) (100 ml), and then stirred at 60 °C for 4 hours. After the reaction was completed, it was neutralized with an aqueous K3PO4 solution at room temperature and then extracted with DCM and water (H2O).

[0181] The reactant extracted again was purified by column chromatography (DCM:Hex = 1:1 volume ratio), recrystallized with methanol, and extracted with dichloromethane / H2O. The reactant was purified by column chromatography (DCM:Hex = 1:1) and recrystallized with methanol to obtain Compound 1013. (8 g, 0.0112 mol, 80% yield)

[0182] Compounds were produced in the same manner as in Production Examples 1 to 4, and the results of synthesis confirmation are shown in Tables 3 and 4. Table 3 is 1 the measured value of 1H NMR (CDCl3, 200 Mz), and Table 4 is the measured value of FD-mass spectrometer (FD-MS: Field desorption mass spectrometry).

[0183]

Table 3

[0184]

Table 4

[0185] [Experimental Example] <Experimental Example 1> 1) Fabrication of organic light-emitting devices Comparative Example 1 A transparent electrode indium tin oxide (ITO) thin film obtained from OLED glass (manufactured by Samsung Corning) was ultrasonically cleaned for 5 minutes each using trichloroethylene, acetone, ethanol, and distilled water in sequence, then stored in isopropanol before use. Next, the ITO substrate was placed in a substrate holder of a vacuum deposition system, and the following 4,4',4''-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA) was placed in a cell within the vacuum deposition system. [ka]

[0186] Next, the vacuum level inside the chamber is 10 -6 After evacuating until the torr level was reached, an electric current was applied to the cell to evaporate 2-TNATA, depositing a 600 Å thick hole injection layer onto the ITO substrate. In another cell within the vacuum deposition equipment, N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) was placed, and an electric current was applied to the cell to evaporate it, depositing a 300 Å thick hole transport layer on top of the hole injection layer. [ka]

[0187] After forming the hole injection layer and hole transport layer in this manner, a blue light-emitting material with the following structure was deposited on top of them as a light-emitting layer. Specifically, a blue light-emitting host material, H1, was vacuum-deposited to a thickness of 200 Å into one cell of the vacuum deposition equipment, and a blue light-emitting dopant material, D1, was vacuum-deposited on top of it at a density of 5% relative to the host material. [ka]

[0188] Subsequently, a compound of the following structural formula E1 was vapor-deposited to a thickness of 300 Å as an electron transport layer.

Chemical formula

[0189] Lithium fluoride (LiF) was vapor-deposited to a thickness of 10 Å as an electron injection layer, and an Al cathode was formed to a thickness of 1,000 Å to fabricate an OLED device. On the other hand, all the organic compounds required for fabricating the OLED device were vacuum sublimation purified at 10 -6 ~10 -8 torr and used for fabricating the OLED.

[0190] Comparative Examples 2-7 and Examples 1-56 An organic electroluminescent device was fabricated in the same manner as in Comparative Example 1, except that the compound shown in Table 5 below was used instead of NPB used in forming the hole transport layer in Comparative Example 1.

Chemical formula

[0191] 2) Evaluation of organic light-emitting device For the organic light-emitting device manufactured as described above, the electroluminescence (EL) characteristics were measured using M7000 of Mac Science Co., Ltd., and based on the measurement results, the reference luminance was 700 cd / m 2 when passing through the life measurement equipment (M6000) manufactured by Mac Science Co., Ltd., T 95 was measured.

[0192] The measured results of the driving voltage, luminous efficiency, color coordinates (CIE), and life (T 95 ) of the blue organic light-emitting device manufactured according to the present invention were as shown in Table 5.

[0193]

Table 5

[0194] As can be seen from the results in Table 5 above, the organic light-emitting device using the hole transport layer material of the blue organic light-emitting device of the present invention was found to have a lower driving voltage and significantly improved luminous efficiency and lifetime compared to the comparative example.

[0195] In particular, when an amine derivative was used as a hole transport layer for the compound of this invention, the lone pair of electrons in the amine improved the flow of holes, thereby enhancing the hole transport capacity of the hole transport layer. Furthermore, the bonding of substituents with enhanced hole properties to the amine moiety increased the planarity and glass transition temperature of the amine derivative, thereby improving the thermal stability of the compound.

[0196] Furthermore, it was confirmed that adjusting the band gap and T1 value (the energy level of the triple state) improves hole transfer capability and molecular stability, thereby lowering the device's driving voltage, improving optical efficiency, and enhancing the device's lifetime characteristics through the thermal stability of the compound.

[0197] Specifically, when a compound having two substituents on one phenyl group of a naphthobenzofuran core, such as the compound represented by Chemical Formula 1 of this application, namely an amine group with one or more aryl groups substituted and an aryl group, or an amine group with one or more aryl groups substituted and a heteroaryl group containing O or S, is used as the hole transport layer, it has been confirmed that the aryl groups substituted on the amine group delocalize the HOMO (Highest Occupied Molecular Orbital) energy level of the compound, thereby stabilizing the HOMO energy and resulting in excellent luminescence efficiency and lifetime.

[0198] <Experimental Example 2> 1) Fabrication of organic light-emitting devices Comparative Examples 8-13 and Examples 57-76 An organic electroluminescent device was fabricated in the same manner as in Comparative Example 1, except that after forming a hole transport layer (NPB) with a thickness of 250 Å, an electron blocking layer with a thickness of 50 Å was formed on top of the hole transport layer using the compound shown in Table 6 below. [ka]

[0199] 2) Evaluation of organic light-emitting devices For the organic light-emitting element manufactured as described above, the electroluminescent (EL) characteristics were measured using MacScience's M7000, and the measurement results were used to determine that the reference brightness was 700 cd / m² via a lifetime measurement device (M6000) manufactured by MacScience. 2 At that time, T 95 We measured it.

[0200] The driving voltage, luminous efficiency, color coordinate (CIE), and lifetime of the blue organic light-emitting element manufactured according to the present invention were measured and the results are shown in Table 6 below.

[0201] [Table 6]

[0202] As can be seen from the results in Table 6 above, the organic light-emitting element using the electron-blocking layer material of the blue organic light-emitting element of the present invention exhibited a lower driving voltage and significantly improved luminous efficiency and lifetime compared to the comparative example. In the case of electrons, if they are not coupled in the light-emitting layer and proceed to the anode via the hole transport layer, a phenomenon occurs in which the efficiency and lifetime of the OLED element decrease. To prevent such a phenomenon, if a compound with a high LUMO level is used as the electron-blocking layer, electrons attempting to proceed to the anode via the light-emitting layer are blocked by the energy barrier of the electron-blocking layer. This increases the probability that holes and electrons will form an exciton, and the likelihood of light being emitted from the light-emitting layer increases, so the compound of the present invention is judged to be superior in all aspects of driving, efficiency, and lifetime.

[0203] In particular, when the compound of Chemical Formula 1 of this application is used as an electron blocking layer, it is possible to suppress the degradation of the hole transport material caused by electrons entering the hole transport layer. Furthermore, it was confirmed that the bonding of substituents with enhanced hole properties to the amine moiety increases the planarity and glass transition temperature of the amine derivative, thereby improving the thermal stability of the compound.

[0204] Furthermore, it was confirmed that adjusting the band gap and T1 value improves hole transfer capability and enhances molecular stability, thereby lowering the device's driving voltage, improving optical efficiency, and enhancing the device's lifetime characteristics through the thermal stability of the compound.

[0205] <Experimental Example 3> 1) Fabrication of organic light-emitting devices Comparative Examples 14-19 and Examples 77-124 A glass substrate coated with a thin ITO film to a thickness of 1500 Å was cleaned using distilled water ultrasonic cleaning. After distilled water cleaning, ultrasonic cleaning was performed with solvents such as acetone, methanol, and isopropyl alcohol, followed by drying. Then, UVO treatment was performed using UV light in a UV cleaning machine for 5 minutes. Subsequently, the substrate was transferred to a plasma cleaning machine (PT), where plasma treatment was performed under vacuum to determine the ITO work function and remove any remaining film. Finally, it was transferred to a thermal deposition equipment for organic deposition.

[0206] Next, the vacuum level inside the chamber is 10 -6 After evacuating until the torr temperature was reached, an electric current was applied to the cell to evaporate 2-TNATA, thereby depositing a 600 Å thick hole injection layer onto the ITO substrate. [ka]

[0207] N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) was placed in another cell within the vacuum deposition equipment, and an electric current was applied to the cell to evaporate it, thereby depositing a 300 Å thick hole transport layer on the hole injection layer. [ka]

[0208] Subsequently, the compounds listed in Table 7 below were deposited at a depth of 100 Å to form a prime layer. [ka]

[0209] A light-emitting layer was then deposited on top of it using thermal vacuum deposition as follows: The light-emitting layer consisted of a 400 Å deposition of the compound (9-[4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]-9'-phenyl-3,3'-Bi-9h-carbazole) as the host, and a 7% doping of Ir(ppy)3 as the green phosphorescent dopant. Subsequently, a 60 Å deposition of BCP was used as a hole blocking layer, and on top of that, a 200 Å deposition of Alq3 was used as an electron transport layer.

[0210] Finally, an organic light-emitting diode was fabricated by depositing lithium fluoride (LiF) to a thickness of 10 Å onto the electron transport layer to form an electron injection layer, and then depositing an aluminum (Al) cathode to a thickness of 1,200 Å onto the electron injection layer to form the cathode.

[0211] On the other hand, all organic compounds required for the manufacture of organic light-emitting devices are 10 each for each material. -8~ 10 -6 The organic light-emitting element was purified by vacuum sublimation under Torr conditions and used in the manufacture of organic light-emitting elements.

[0212] 2) Evaluation of organic light-emitting devices The electroluminescent (EL) characteristics of the organic light-emitting elements of Comparative Examples 14-19 and Examples 77-124, manufactured as described above, were measured using MacScience's M7000, and the reference brightness was set to 6,000 cd / m² using the measurement results via a lifetime measurement device (M6000) manufactured by MacScience. 2 At that time, the lifetime T is the time it takes for the brightness to reach 90% of its initial brightness. 90 The measurement time (in h) was measured, and the results are shown in Table 7 below.

[0213] [Table 7] TIFF0007876250000117.tif225170

[0214] From the results in Table 7, it was confirmed that in the case of organic light-emitting devices of Examples 77 to 124, in which the compound according to this application was used during the formation of the prime layer, the structure in which two specific substituents containing amine groups are substituted on naphthobenzofuran delocalizes the homo (HOMO, Highest Occupied Molecular Orbital) energy level and stabilizes the homo energy, thereby effectively preventing electrons from crossing from the opposite side of the electron transport layer. As a result, it was confirmed that these devices exhibit superior luminous efficiency and lifetime compared to organic light-emitting devices of Comparative Examples 14 to 19, in which the compound according to this application was not used during the formation of the prime layer. [Explanation of symbols]

[0215] 100 ··· circuit board 200...Anode 300...organic layer 301 ···Hole injection layer 302 ···Hole transport layer 303...electron blocking layer 304 ···Prime Layer 305 ···Luminous layer 306...electron transport layer 307 ··· Electron Injection Layer 400 ··· Cathode

Claims

1. A compound represented by any one of the following chemical formulas 1-1 to 1-3: 【Chemistry 1】 【Chemistry 2】 【Transformation 3】 In the above chemical formulas 1-1 to 1-3, X is O; or S, Ar is a substituted or unsubstituted C6-C30 aryl group; a substituted or unsubstituted C2-C30 heteroaryl group containing O or S; or a substituted or unsubstituted C2-C30 heteroaryl group containing C=N. L1, L2, L11, and L12 are each independently directly bonded; or substituted or unsubstituted C6-C30 arylene groups. When L1 is a substituted or unsubstituted C6-C30 arylene group, Ar is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted phenantrenyl group, a substituted or unsubstituted phenalenyl group, a substituted or unsubstituted fluorenyl group, or a substituted or unsubstituted dibenzothiophene group. R11 and R12 are, independently, substituted or unsubstituted C6-C30 aryl groups; or substituted or unsubstituted C2-C30 heteroaryl groups. If R11 is a dimethylfluorenyl group, then R11 and R12 are different from each other. If R11 in chemical formula 1-2 is a dimethylfluorenyl group, then R12 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a diphenylfluorenyl group, or a substituted or unsubstituted C2-C30 heteroaryl group. l1, l2, l11, and l12 are integers from 1 to 5, and if each is 2 or greater, the substituents in parentheses are either identical or different from each other. H1 to H3 are hydrogen; or deuterium, h1 to h3 are integers from 0 to 8, and if each is 2 or greater, the substituents in parentheses are either identical or different from each other. and The terms "substituted or unsubstituted" above mean that the molecule is substituted with at least one substituent selected from the group consisting of deuterium; C1-C60 alkyl groups; C6-C60 aryl groups; C2-C60 heteroaryl groups containing O or S as a heteroatom; and substituents in which at least two substituents selected from the above substituents are linked together, or that the molecule is unsubstituted.

2. In the case of chemical formula 1-1 or 1-2, 【Chemistry 4】 and 【Transformation 5】 but 【Transformation 6】 When bonded at positions 1 and 4, the compound according to claim 1 satisfies any of the following i to iv: i) R11 and R12 are independently a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted dibenzofuran group; or a substituted or unsubstituted dibenzothiophene group. ii) R11 and R12 are independently a substituted or unsubstituted adamantane group; a substituted or unsubstituted phenyl group with deuterium or a C6-C30 aryl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; or a substituted or unsubstituted anthracenyl group. iii) L1 is a substituted or unsubstituted arylene group having 10 to 30 carbon atoms, and iv) 【Transformation 7】 and 【Transformation 8】 One of them contains deuterium.

3. In the case of chemical formulas 1-3, 【Chemistry 9】 and 【Chemistry 10】 but 【Chemistry 11】 The compound according to claim 1, wherein when bonded at positions 1 and 4, R11 and R12 are, independently, a substituted or unsubstituted adamantane 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 anthracenyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted dibenzothiophene group; or a substituted or unsubstituted naphthobenzofuran group.

4. The compound according to claim 1, wherein Ar is a substituted or unsubstituted C6-C30 aryl group; or a substituted or unsubstituted C2-C30 heteroaryl group containing O or S.

5. The R11 is a substituted or unsubstituted C6-C30 aryl group; or a substituted or unsubstituted C2-C30 heteroaryl group containing O or S. The compound according to claim 1, wherein R12 is a substituted or unsubstituted C6-C30 aryl group; or a substituted or unsubstituted C2-C30 heteroaryl group containing O or S.

6. The compound according to claim 1, wherein the deuterium content of each of the compounds of chemical formulas 1-1 to 1-3 is 0% or 5% to 100%.

7. The compound according to claim 1, wherein the compound of chemical formula 1-1 to 1-3 is any of the compounds represented by the following chemical formulas: 【Chemistry 12】 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】 【Chemistry 16】 【Chemistry 17】 [Chemistry 18] 【Chemistry 19】 【Chemistry 20】 【Chemistry 21】 【Chemistry 22】 【Chemistry 23】 【Chemistry 24】 【Chemistry 25】 【Chemistry 26】 【Chemistry 27】 【Chemistry 28】 【Chemistry 29】 【Transformation 30】 【Chemistry 31】 【Chemistry 32】 【Transformation 33】 【Transformation 34】 【Chemistry 35】 【Transformation 36】 【Chemistry 37】 【Transformation 38】 【Chemistry 39】 【Chemistry 40】 【Chemistry 41】 【Chemistry 42】 【Chemistry 43】 【Chemistry 44】 【Chemistry 45】 【Chemistry 46】 【Chemistry 47】 【Chemistry 48】 【Chemistry 49】 [Transformation 50] 。

8. An organic light-emitting element comprising a first electrode; a second electrode; and an organic layer provided between the first electrode and the second electrode, The organic light-emitting element comprises an organic layer containing a compound according to any one of claims 1 to 7.

9. The aforementioned organic layer includes a hole transport layer, The hole transport layer comprises the compound, according to claim 8, for the organic light-emitting element.

10. The aforementioned organic layer includes an electron blocking layer. The organic light-emitting element according to claim 8, wherein the electron blocking layer comprises the compound.

11. The aforementioned organic layer includes a prime layer, The organic light-emitting element according to claim 8, wherein the prime layer comprises the compound.

Images