Novel compounds and organic light-emitting devices containing them

Abstract

This invention provides novel compounds and organic light-emitting devices utilizing the same.

Description

Technical Field

[0001] Cross-reference with related applications

[0002] This application claims priority based on Korean Patent Application No. 10-2021-0075599, dated June 10, 2021, the entire contents of which are disclosed in the document and are incorporated herein by reference.

[0003] This invention relates to novel compounds and organic light-emitting devices containing the same. Background Technology

[0004] Organic light emission typically refers to the phenomenon of converting electrical energy into light energy using organic materials. Organic light-emitting devices (OLEDs) utilizing organic light emission exhibit wide viewing angles, excellent contrast ratios, fast response times, and superior brightness, driving voltage, and response speed characteristics, thus attracting extensive research.

[0005] Organic light-emitting devices (OLEDs) typically have a structure comprising an anode and a cathode, and an organic layer located between the anode and cathode. To improve the efficiency and stability of OLEDs, the organic layer is often formed by a multilayer structure composed of different materials, such as a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. In such an OLED structure, if a voltage is applied between the two electrodes, holes are injected into the organic layer from the anode, and electrons are injected into the organic layer from the cathode. When the injected holes and electrons meet, they form excitons, which emit light when they re-enter the ground state.

[0006] For organic materials used in organic light-emitting devices as described above, there is a continuous need to develop new materials.

[0007] Existing technical documents

[0008] Patent documents

[0009] (Patent Document 0001) Korean Patent Publication No. 10-2000-0051826 Summary of the Invention

[0010] Technical issues

[0011] This invention relates to novel compounds and organic light emitters containing the same.

[0012] Solution to the problem

[0013] This invention provides compounds represented by the following chemical formula 1:

[0014] [Chemical Formula 1]

[0015]

[0016] In the above chemical formula 1,

[0017] Two adjacent R1 atoms bond together to form a benzene ring, which is then substituted or unsubstituted with hydrogen, deuterium, or C atoms. 6-60 aryl; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O, and S. 2-60 heteroaryl substitution,

[0018] The remaining R1s are hydrogen; deuterium; substituted or unsubstituted C. 6-60 aryl; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O, and S. 2-60 Mixed aromatics,

[0019] R2 is hydrogen; deuterium; substituted or unsubstituted C. 6-60 aryl; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O, and S. 2-60 Mixed aromatics,

[0020] R a R b and R c Each is independently hydrogen; deuterium; substituted or unsubstituted C. 6-60 aryl; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O, and S. 2-60 Mixed aromatics,

[0021] n1 and n2 are each integers from 0 to 3.

[0022] n3 is an integer from 0 to 4.

[0023] L1 and L2 are each independent single bonds; substituted or unsubstituted C 6-60 aryl; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O, and S. 2-60 Hybrid aryl,

[0024] One of Ar1 and Ar2 has the following chemical formula 2, and the other is a substituted or unsubstituted C. 6-60 Aryl,

[0025] [Chemical Formula 2]

[0026]

[0027] In the above chemical formula 2,

[0028] X is O or S.

[0029] R d Each is independently hydrogen; deuterium; substituted or unsubstituted C.6-60 aryl; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O, and S. 2-60 Mixed aromatics,

[0030] n4 is an integer from 0 to 7.

[0031] In addition, the present invention provides an organic light-emitting device, comprising: a first electrode, a second electrode disposed opposite to the first electrode, and an organic layer of one or more disposed between the first electrode and the second electrode, wherein one or more of the organic layers comprises a compound represented by the above chemical formula 1.

[0032] Invention Effects

[0033] The compounds represented by the above-described chemical formula 1 can be used as materials for the organic layer of organic light-emitting devices, thereby achieving improved efficiency, lower driving voltage, and / or improved lifetime characteristics in organic light-emitting devices. In particular, the compounds represented by the above-described chemical formula 1 can be used as materials for hole injection, hole transport, hole injection and transport, electron blocking, light emission, hole blocking, electron transport, electron injection, or electron injection and transport. Attached Figure Description

[0034] Figure 1 The illustration shows an example of an organic light-emitting device consisting of a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4.

[0035] Figure 2 The illustration shows an example of an organic light-emitting device consisting of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light-emitting layer 3, an electron injection and transport layer 8, and a cathode 4. Detailed Implementation

[0036] The invention will now be described in more detail to aid in understanding.

[0037] In this instruction manual, This indicates a bond that is linked to other substituents.

[0038] In this specification, the term "substituted or unsubstituted" refers to a group selected from deuterium; halogen group; nitrile group; nitro group; hydroxyl group; carbonyl group; ester group; imide group; amino group; phosphine oxide group; alkoxy group; aryloxy group; alkyl thio group. aryl thiols alkylsulfonyl arylsulfonyl Silyl; boronyl; alkyl; cycloalkyl; alkenyl; aryl; aralkyl; arylene; alkylaryl; alkylamino; aralkylamino; heteroarylamino; arylamino; arylphosphinyl; or a substituent formed by connecting two or more of the above-exemplified substituents, either substituted or unsubstituted. For example, "a substituent formed by connecting two or more substituents" can be biphenyl. That is, biphenyl can be aryl, or it can be interpreted as a substituent formed by connecting two phenyl groups.

[0039] In this specification, the number of carbon atoms in the carbonyl group is not particularly limited, but it is preferred to have 1 to 40 carbon atoms. Specifically, it can be a compound with the following structure, but is not limited thereto.

[0040]

[0041] In this specification, the oxygen in the ester group can be replaced by a straight-chain, branched, or cyclic alkyl group having 1 to 25 carbon atoms, or an aryl group having 6 to 25 carbon atoms. Specifically, it can be a compound with the following structural formula, but is not limited thereto.

[0042]

[0043] In this specification, the number of carbon atoms in the imide group is not particularly limited, but it is preferred to have 1 to 25 carbon atoms. Specifically, it can be a compound with the following structure, but is not limited thereto.

[0044]

[0045] In this specification, silanes specifically include trimethylsilane, triethylsilane, tert-butyldimethylsilane, vinyldimethylsilane, propyldimethylsilane, triphenylsilane, diphenylsilane, phenylsilane, etc., but are not limited to these.

[0046] In this specification, boron groups specifically include trimethylboronyl, triethylboronyl, tert-butyldimethylboronyl, triphenylboronyl, phenylboronyl, etc., but are not limited to these.

[0047] Examples of halogen groups in this specification include fluorine, chlorine, bromine, or iodine.

[0048] In this specification, the alkyl group can be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. According to yet another embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of alkyl groups include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl, etc., but are not limited to these.

[0049] In this specification, the alkenyl group can be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to yet another embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, styryl, styryl, etc., but are not limited to these.

[0050] In this specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group with 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, etc., are used, but are not limited to these.

[0051] In this specification, the aryl group is not particularly limited, but is preferably an aryl group with 6 to 60 carbon atoms, and can be a monocyclic aryl or polycyclic aryl. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to another embodiment, the aryl group has 6 to 20 carbon atoms. Regarding the aforementioned aryl group, as a monocyclic aryl group, it can be phenyl, biphenyl, terphenyl, etc., but is not limited to these. As the aforementioned polycyclic aryl group, it can be naphthyl, anthraceneyl, phenanthryl, pyrene, perylene, etc. It includes bases, fluorenes, etc., but is not limited to these.

[0052] In this specification, the fluorene group can be substituted, and two substituents can combine with each other to form a spirostructure. When the fluorene group is substituted as described above, it can be used to... Etc. But it is not limited to this.

[0053] In this specification, a heterocyclic group is a heterocyclic group containing one or more of O, N, Si, and S as heteroelements. The number of carbon atoms is not particularly limited, but is preferably 2 to 60. Examples of heterocyclic groups include thiophene, furanyl, pyrrole, imidazole, and thiazolyl. azole group, Diazolyl, Triazolyl, Pyridyl, Bipyridyl, Pyrimidinyl, Triazinyl, Acridineyl, Pyridazinyl, Quinolinyl, Quinazolinyl, Quinoxalinyl, Phtharazineyl, Pyridopyrimidinyl, Pyridopyrazinyl, Pyrazenopyrazinyl, Isoquinolinyl, Indoleyl, Carbazoleyl, Benzo[] Azolyl, benzimidazolyl, benzothiazolyl, benzocarbazole, benzothiophene, dibenzothiophene, benzofuranyl, phenanthroline, iso Azolyl, thiadiazolyl, phenthiazinyl, and dibenzofuranyl groups, but not limited to these.

[0054] In this specification, the aryl groups in aralkyl, aryl-alkenyl, alkylaryl, and arylamine are the same as those exemplified above. In this specification, the alkyl groups in aralkyl, alkylaryl, and alkylamine are the same as those exemplified above. In this specification, the heteroaryl groups in heteroarylamines are subject to the above description of heterocyclic groups. In this specification, the alkenyl groups in aryl-alkenyl are the same as those exemplified above. In this specification, arylene is a divalent group; otherwise, the above description of aryl groups applies. In this specification, heteroarylene is a divalent group; otherwise, the above description of heterocyclic groups applies. In this specification, the hydrocarbon ring is not a monovalent group but is formed by the combination of two substituents; otherwise, the above description of aryl or cycloalkyl groups applies. In this specification, the heterocycle is not a monovalent group but is formed by the combination of two substituents; otherwise, the above description of heterocyclic groups applies.

[0055] The present invention provides compounds represented by the above chemical formula 1.

[0056] The compound represented by the above chemical formula 1 can improve the characteristics of organic light-emitting devices by incorporating heterocycles containing O or S on the nitrogen atoms of the benzocarbazole ring and the nitrogen atom of the carbazole ring in the parent nucleus structure where the carbazole group is bonded to a specific position of the benzocarbazole group.

[0057] In particular, the compounds represented by the above chemical formula 1 have structures containing dibenzofuran or dibenzothiophene attached to the nitrogen atom of the carbazole or benzocarbazole structure, which facilitates the transport and injection of holes and can block the migration of electrons since there are no units that attract electrons.

[0058] Furthermore, the benzo[a]carbazole formed by the fusion of the substituents in Formula 1 at specific positions of adjacent R1 serves as a p-type host, possessing appropriate HOMO energy levels and triplet energy, thus exhibiting a structure that can smoothly transfer energy to the red dopant by mixing with other hosts.

[0059] Therefore, compared to the case of an electron blocking layer that is in contact with the light-emitting layer to inject holes or a host that transports holes within the light-emitting layer, better light-emitting characteristics can be exhibited, thereby improving quantum efficiency and lifetime together with low voltage characteristics.

[0060] Specifically, the present invention provides compounds represented by the following chemical formula 1.

[0061] [Chemical Formula 1]

[0062]

[0063] In the above chemical formula 1,

[0064] Two adjacent R1 atoms bond together to form a benzene ring, which is then substituted or unsubstituted with hydrogen, deuterium, or C atoms. 6-60 aryl; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O, and S. 2-60 heteroaryl substitution,

[0065] The remaining R1s are hydrogen; deuterium; substituted or unsubstituted C. 6-60 aryl; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O, and S. 2-60 Mixed aromatics,

[0066] R2 is hydrogen; deuterium; substituted or unsubstituted C. 6-60 aryl; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O, and S. 2-60 Mixed aromatics,

[0067] Ra R b and R c Each is independently hydrogen; deuterium; substituted or unsubstituted C. 6-60 aryl; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O, and S. 2-60 Mixed aromatics,

[0068] n1 and n2 are each integers from 0 to 3.

[0069] n3 is an integer from 0 to 4.

[0070] L1 and L2 are each independently a single bond, or a substituted or unsubstituted C bond. 6-60 Alpha-aryl

[0071] One of Ar1 and Ar2 has the following chemical formula 2, and the other is a substituted or unsubstituted C. 6-60 Aryl,

[0072] [Chemical Formula 2]

[0073]

[0074] In the above chemical formula 2,

[0075] X is O or S.

[0076] R d Each is independently hydrogen; deuterium; substituted or unsubstituted C. 6-60 aryl; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O, and S. 2-60 Mixed aromatics,

[0077] n4 is an integer from 0 to 7.

[0078] More specifically, in the above chemical formula 1, depending on the specific position of the naphthalene ring attached to the benzo[a]carbazole group, the compound represented by the above chemical formula 1 can be represented by the following chemical formula 1-1 or 1-2:

[0079] [Chemical Formula 1-1]

[0080]

[0081] [Chemical Formula 1-2]

[0082]

[0083] In the above chemical formulas 1-1 and 1-2,

[0084] R a R b R cL1, L2, Ar1, and Ar2 are the same as defined in claim 1.

[0085] R' can be hydrogen; deuterium; or substituted or unsubstituted C. 6-60 aryl; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O, and S. 2-60 Mixed aromatics,

[0086] n' is an integer from 0 to 6.

[0087] Furthermore, the compound represented by the above chemical formula 1 can be represented by any one of the following chemical formulas 1-3 to 1-10:

[0088] [Chemical Formulas 1-3]

[0089]

[0090] [Chemical Formulas 1-4]

[0091]

[0092] [Chemical Formulas 1-5]

[0093]

[0094] [Chemical Formulas 1-6]

[0095]

[0096] [Chemical Formulas 1-7]

[0097]

[0098] [Chemical Formulas 1-8]

[0099]

[0100] [Chemical Formulas 1-9]

[0101]

[0102] [Chemical Formulas 1-10]

[0103]

[0104] In the above chemical formulas 1-3 to 1-10,

[0105] R a R b R c L1, L2, Ar1, Ar2, R' and n' are the same as those defined in the above chemical formulas 1-1 and 1-2.

[0106] More specifically, compounds represented by the above chemical formula 1 can be represented by the following chemical formulas 1-11 or 1-12:

[0107] [Chemical Formula 1-11]

[0108]

[0109] [Chemical Formula 1-12]

[0110]

[0111] In the above chemical formulas 1-11 and 1-12,

[0112] R a R b R c L1, L2, Ar1, Ar2, R' and n' are the same as those defined in the above chemical formulas 1-1 and 1-2.

[0113] Furthermore, the compound represented by the above chemical formula 1 can be represented by any one of the following chemical formulas 1-11a to 1-11c and chemical formulas 1-12a to 1-12c:

[0114] [Chemical Formula 1-11a]

[0115]

[0116] [Chemical Formula 1-11b]

[0117]

[0118] [Chemical Formula 1-11c]

[0119]

[0120] [Chemical Formula 1-12a]

[0121]

[0122] [Chemical Formula 1-12b]

[0123]

[0124] [Chemical Formula 1-12c]

[0125]

[0126] In the above chemical formulas 1-11a to 1-11c and chemical formulas 1-12a to 1-12c,

[0127] L1, L2, Ar1, and Ar2 are the same as those defined in chemical formulas 1-1 and 1-2 above.

[0128] R e Each is independently either hydrogen or deuterium.

[0129] R f Each is independently hydrogen; deuterium; substituted or unsubstituted C. 6-60 aryl; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O, and S. 2-60 Mixed aromatic compounds.

[0130] On the other hand, in the above chemical formula 1, specifically, two adjacent R1 atoms combine with each other to form a benzene ring, which can be substituted or unsubstituted by hydrogen, deuterium, or C atoms. 6-30 Aryl, or C 6-28 Aryl, or C 6-25 Aryl, or C 6-12 aryl; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O, and S. 5-30 heteroaryl, or C 8-20 heteroaryl, or C 12-18 heteroaryl substitution.

[0131] Additionally, the remaining element in R1 that does not form a benzene ring can be hydrogen; deuterium; or a substituted or unsubstituted C. 6-30 Aryl, or C 6-28 Aryl, or C 6-25 Aryl, or C 6-12 aryl; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O, and S. 5-30 heteroaryl, or C 8-20 heteroaryl, or C 12-18 Mixed aromatic compounds.

[0132] Preferably, in the above chemical formula 1, two adjacent R1s are bonded together to form a benzene ring substituted with hydrogen or deuterium, and the remaining R1s can be hydrogen or deuterium.

[0133] On the other hand, in the above chemical formula 1, specifically, R2 can be hydrogen; deuterium; substituted or unsubstituted C. 6-30 Aryl, or C 6-28 Aryl, or C 6-25 Aryl, or C 6-12 aryl; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O, and S. 5-30 heteroaryl, or C 8-20 heteroaryl, or C 12-18 Mixed aromatic compounds.

[0134] Preferably, in the above chemical formula 1, R2 can be hydrogen, deuterium, phenyl, or a phenyl substituted with deuterium.

[0135] On the other hand, in the aforementioned chemical formula 1 and chemical formulas 1-1 to 1-12, specifically, R a R b and R c Each can be hydrogen; deuterium; substituted or unsubstituted C. 6-30 Aryl, or C 6-28 Aryl, or C 6-25 Aryl, or C 6-12 aryl; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O, and S. 5-30 heteroaryl, or C 8-20 heteroaryl, or C 12-18 Mixed aromatic compounds.

[0136] Preferably, in the above chemical formula 1 and chemical formulas 1-1 and 1-12, R a R b and R c Each can be hydrogen, deuterium, phenyl, or a phenyl substituted with deuterium.

[0137] In addition, n1 and n2 can each be an integer from 0 to 2, or 0 or 1.

[0138] In addition, n3 can be an integer from 0 to 3, an integer from 0 to 2, or 0 or 1.

[0139] On the other hand, in the above chemical formulas 1-1 to 1-12, specifically, R' can each be hydrogen; deuterium; substituted or unsubstituted C. 6-30 Aryl, or C 6-28 Aryl, or C 6-25 Aryl, or C 6-12 aryl; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O, and S. 5-30 heteroaryl, or C 8-20 heteroaryl, or C 12-18 Mixed aromatic compounds.

[0140] Preferably, in the above chemical formulas 1-1 to 1-12, R' can be hydrogen, deuterium, phenyl, or a phenyl substituted with deuterium.

[0141] In addition, in the above chemical formulas 1-1 to 1-12, n' can be an integer from 0 to 5, or an integer of 0 or 4, or an integer from 0 to 3, an integer from 0 to 2, or 0 or 1.

[0142] On the other hand, in the aforementioned chemical formulas 1 and 1-1 to 1-12, 1-11a to 1-11c and 1-12a to 1-12c, specifically, L1 and L2 can each be a single bond; or a substituted or unsubstituted C. 6-30 aryl, or C6-28 aryl, or C 6-25 aryl, or C 6-12 Alpha-aryl.

[0143] More specifically, L1 and L2 can each be a single bond; or a phenylene, biphenylene, terphenylene, tetraphenylene, or naphthylene.

[0144] As an example, L1 and L2 can each be a single bond or represented by any of the groups selected from the following groups.

[0145]

[0146] Preferably, L1 and L2 can each be a single bond, or a phenylene or naphthylene group.

[0147] On the other hand, in the aforementioned chemical formulas 1 and 1-1 to 1-12, 1-11a to 1-11c and 1-12a to 1-12c, specifically, one of Ar1 and Ar2 is the aforementioned chemical formula 2, and the remaining Ar1 and Ar2 can be substituted or unsubstituted C. 6-30 Aryl, or C 6-28 Aryl, or C 6-25 Aryl, or C 6-12 Aryl.

[0148] Furthermore, in the above chemical formula 2, R d Each can be hydrogen; deuterium; substituted or unsubstituted C. 6-30 Aryl, or C 6-28 Aryl, or C 6-25 Aryl, or C 6-12 aryl; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O, and S. 5-30 heteroaryl, or C 8-20 heteroaryl, or C 12-18 Mixed aromatic compounds.

[0149] Preferably, in the above chemical formula 2, R d Each can be either hydrogen or deuterium.

[0150] Specifically, n4 can be an integer from 0 to 7, or an integer from 0 to 4, an integer from 0 to 2, or 0 or 1.

[0151] More specifically, one of Ar1 and Ar2 is a dibenzofuranyl, dibenzothiophenyl, deuterated dibenzofuranyl, or deuterated dibenzothiophenyl, represented by the above chemical formula 2, and the remainder of Ar1 and Ar2 can be substituted or unsubstituted C. 6-30 Aryl.

[0152] Preferably, one of Ar1 and Ar2 is dibenzofuranyl, dibenzothiophenyl, deuterated dibenzofuranyl, or deuterated dibenzothiophenyl, and the remainder can be phenyl, naphthyl-substituted phenyl, biphenyl, naphthyl, naphthyl-substituted phenyl, or deuterated phenyl.

[0153] On the other hand, in the above chemical formulas 1-11a to 1-11c and 1-12a to 1-12c, R e Each is either hydrogen or deuterium.

[0154] Furthermore, in the aforementioned chemical formulas 1-11a to 1-11c and chemical formulas 1-12a to 1-12c, specifically, R f Each can be hydrogen; deuterium; substituted or unsubstituted C. 6-30 Aryl, or C 6-28 Aryl, or C 6-25 Aryl, or C 6-12 aryl; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O, and S. 5-30 heteroaryl, or C 8-20 heteroaryl, or C 12-18 Mixed aromatic compounds.

[0155] Preferably, R f Each can be hydrogen, deuterium, phenyl, or a phenyl substituted with deuterium.

[0156] On the other hand, the compound represented by the above chemical formula 1 can be a compound with no deuterium substitution or with 1 to 44 deuterium substitutions. As an example, the compound represented by the above chemical formula 1 can be with no deuterium substitution, or can be with 2 to 42, 2 to 40, 2 to 36, 3 to 32, 3 to 25, 3 to 20, or 3 to 10 deuterium substitutions.

[0157] As an example, in the compound represented by the above chemical formula 1, the deuterated dibenzofuranyl or the deuterated dibenzothiophene group can each be substituted with 3 to 7 deuterates, and the deuterated phenyl group can be substituted with 5 deuterates.

[0158] Representative examples of compounds represented by the above chemical formula 1 are shown below.

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193] On the other hand, when the compound represented by the above chemical formula 1 is used in an organic light-emitting device, it can be used together with the compound represented by the following chemical formula 3.

[0194] [Chemical Formula 3]

[0195]

[0196] In the above chemical formula 3,

[0197] R3 and R4 are each independently hydrogen; deuterium; substituted or unsubstituted C. 6-60 aryl; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O, and S. 2-60 Mixed aromatics,

[0198] p is an integer from 0 to 10.

[0199] q is an integer from 0 to 7.

[0200] L1 and L2 are each independently a single bond, or a substituted or unsubstituted C bond. 6-60 Alpha-aryl

[0201] One of Ar1 and Ar2 is represented by the following chemical formula 4 or 5, and the others are substituted or unsubstituted C2. 6-60 Aryl,

[0202] [Chemical Formula 4]

[0203]

[0204] [Chemical Formula 5]

[0205]

[0206] In the above chemical formulas 4 and 5,

[0207] R5 and R6 are independently substituted or unsubstituted C. 6-60 Aryl.

[0208] In particular, when the compound represented by the above chemical formula 3 is used together with the compound represented by the above chemical formula 1 in an organic light-emitting device, it is also beneficial to form an exciplex, which can better exhibit the effects of low voltage, high efficiency and long lifetime characteristics.

[0209] Specifically, in the above chemical formula 3, R3 and R4 can each independently be hydrogen; deuterium; or substituted or unsubstituted C. 6-30 Aryl, or C 6-28 Aryl, or C 6-25 Aryl, or C 6-12 aryl; or substituted or unsubstituted C containing one or more heteroatoms selected from N, O, and S. 5-30 heteroaryl, or C 8-20 heteroaryl, or C 12-18 Mixed aromatic compounds.

[0210] Preferably, in the above chemical formula 1, R3 and R4 can each be hydrogen, deuterium, phenyl, or a phenyl substituted with deuterium.

[0211] Additionally, p can be an integer from 0 to 8, or an integer from 0 to 5, or an integer from 0 to 4, or an integer from 0 to 3, or an integer from 0 to 2, or 0 or 1.

[0212] Additionally, q can be an integer from 0 to 6, or an integer from 0 to 5, or an integer from 0 to 4, or an integer from 0 to 3, or an integer from 0 to 2, or 0 or 1.

[0213] Specifically, in the above chemical formula 3, one of Ar3 and Ar4 is either chemical formula 4 or 5, and the remaining Ar3 and Ar4 can be substituted or unsubstituted C. 6-30 Aryl, or C 6-28 Aryl or C 6-25 Aryl, or C 6-12 Aryl.

[0214] More specifically, one of Ar3 and Ar4 is a quinazoline or a quinazoline substituted with deuterium, and the remaining one of Ar3 and Ar4 can be a substituted or unsubstituted C. 6-30 Aryl.

[0215] Preferably, one of Ar3 and Ar4 is a quinazoline or a quinazoline substituted with deuterium, and the others can be phenyl, phenyl substituted with naphthyl, biphenyl, naphthyl, naphthyl substituted with phenyl, or phenyl substituted with deuterium.

[0216] Representative examples of compounds represented by the above chemical formula 3 are shown below.

[0217]

[0218] Furthermore, when the compound represented by the above chemical formula 1 and the compound represented by the above chemical formula 3 are used together in one or more organic layers of an organic light-emitting device, the weight ratio of the compound represented by the above chemical formula 1 to the compound represented by the above chemical formula 3 can be 20:80 to 80:20, or 30:70 to 70:30, or 35:65 to 65:35, or 40:60 to 60:40, preferably 45:55 to 55:45, or 50:50.

[0219] On the other hand, the compound represented by the above chemical formula 1 can be manufactured by the method shown in reaction formula 1 or reaction formula 2 below. The above manufacturing method can be further specified in the synthesis examples described later.

[0220] [Reaction Formula 1]

[0221]

[0222] [Reaction 2]

[0223]

[0224] In the above reaction equations 1 and 2, R1, R2, R a R b R c L1, L2, Ar1, Ar2, n1, n2 and n3 are defined in the same way as in the above chemical formula 1, and Q1 and Q2 are each a halogen group, preferably Cl, Br or I, more preferably Cl or Br.

[0225] Specifically, the reactions in Formulas 1 and 2 above utilize the Buchwald-Hartwig reaction and can be carried out in the presence of palladium catalysts such as bis(tri-(tert-butyl)phosphine)palladium(0), Pd(P-tBu3)2 or tetrakis(triphenylphosphine)palladium(0), Pd(PPh3)4.

[0226] In addition, the above reaction can be carried out in the presence of one or more organic solvents such as dichloromethane, ethyl acetate, diethyl ether, acetonitrile, isopropanol, propanol, tetrahydrofuran (THF), N,N-dimethylformamide (DMF), dimethyl sulfoxide (DMSO), toluene, or xylene, together with one or more basic catalysts such as sodium tert-butoxide (NaOtBu), potassium carbonate (K2CO3), or cesium carbonate (Cs2CO3).

[0227] On the other hand, the present invention provides an organic light-emitting device comprising a compound represented by the above-described chemical formula 1. As an example, the present invention provides an organic light-emitting device comprising: a first electrode, a second electrode disposed opposite to the first electrode, and one or more organic layers disposed between the first electrode and the second electrode, wherein one or more of the organic layers comprises a compound represented by the above-described chemical formula 1.

[0228] The organic layer of the organic light-emitting device of the present invention can be formed as a single layer or as a multilayer structure with two or more organic layers stacked on top of each other. For example, the organic light-emitting device of the present invention can have a structure including a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer as organic layers. However, the structure of the organic light-emitting device is not limited to this and may include fewer organic layers.

[0229] On the other hand, the organic light-emitting device according to the present invention may also contain a compound represented by chemical formula 3 together with the compound represented by chemical formula 1. As an example, the organic light-emitting device according to the present invention includes: a first electrode, a second electrode disposed opposite to the first electrode, and one or more organic layers disposed between the first electrode and the second electrode, wherein one or more of the organic layers may also contain a compound represented by chemical formula 3 together with the compound represented by chemical formula 1.

[0230] In addition, the aforementioned organic layer may include a hole injection layer, a hole transport layer, or a layer that performs both hole injection and transport simultaneously, and the aforementioned hole injection layer, hole transport layer, or layer that performs both hole injection and transport simultaneously may contain a compound represented by the aforementioned chemical formula 1.

[0231] In addition, the aforementioned organic layer may include an electron blocking layer comprising a compound represented by the aforementioned chemical formula 1.

[0232] In addition, the aforementioned organic layer may include a light-emitting layer comprising a compound represented by Chemical Formula 1. For example, a compound represented by Chemical Formula 1 may be included as the host material of the light-emitting layer.

[0233] On the other hand, the aforementioned luminescent layer may also contain a compound represented by chemical formula 3 together with the compound represented by chemical formula 1. In this case, the weight ratio of the compound represented by chemical formula 1 to the compound represented by chemical formula 3 is as described above.

[0234] In addition, the aforementioned light-emitting layer also contains dopant compounds.

[0235] In addition, the above-mentioned light-emitting layer contains a compound of chemical formula 1 and a dopant.

[0236] In addition, the light-emitting layer contains compounds of chemical formula 1 and chemical formula 3, as well as dopants.

[0237] As an example, the aforementioned light-emitting layer comprises a compound of chemical formula 1 and a dopant, in a weight ratio of 100:1 to 1:1.

[0238] In addition, the light-emitting layer comprises a compound of chemical formula 1 and a compound of chemical formula 3, and a dopant, in a weight ratio of 100:1 to 1:1, comprising the combined weight of the compound of chemical formula 1 and the compound of chemical formula 3 and the weight of the dopant.

[0239] In addition, the above-mentioned light-emitting layer contains a compound of chemical formula 1 and a dopant, in a weight ratio of 100:1 to 2:1.

[0240] In addition, the light-emitting layer comprises a compound of chemical formula 1 and a compound of chemical formula 3, and a dopant, in a weight ratio of 100:1 to 2:1, comprising the sum of the weights of the compound of chemical formula 1 and the compound of chemical formula 3 and the dopant.

[0241] In addition, the above-mentioned light-emitting layer contains a compound of chemical formula 1 and a dopant, in a weight ratio of 100:1 to 5:1.

[0242] In addition, the light-emitting layer comprises a compound of chemical formula 1 and a compound of chemical formula 3, and a dopant, in a weight ratio of 100:1 to 5:1, comprising the combined weight of the compound of chemical formula 1 and the compound of chemical formula 3 and the weight of the dopant.

[0243] In addition, the above-mentioned light-emitting layer contains a compound of chemical formula 1 and a dopant, in a weight ratio of 100:1 to 95:5.

[0244] In addition, the light-emitting layer comprises a compound of chemical formula 1 and a compound of chemical formula 3, and a dopant, in a weight ratio of 100:1 to 95:5, comprising the weight of the compound of chemical formula 1 and the compound of chemical formula 3 plus the weight of the dopant.

[0245] As an example, the dopant mentioned above is a metal complex.

[0246] Specifically, the dopants mentioned above are iridium complexes.

[0247] In addition, the organic layer mentioned above includes a light-emitting layer, which contains a dopant, and the dopant material is selected from the following structural formula.

[0248]

[0249]

[0250]

[0251] The structures described above are dopant compounds, but are not limited to them.

[0252] In addition, the aforementioned organic layer may include a hole-blocking layer comprising a compound represented by the aforementioned chemical formula 1.

[0253] In addition, the aforementioned organic layer may include an electron transport layer, an electron injection layer, or a layer that simultaneously performs electron injection and transport, wherein the aforementioned electron transport layer, electron injection layer, or layer that simultaneously performs electron injection and transport contains a compound represented by the aforementioned chemical formula 1.

[0254] In addition, the aforementioned organic layer includes a light-emitting layer and an electron-blocking layer, and the light-emitting layer or electron-blocking layer may contain a compound represented by the aforementioned chemical formula 1.

[0255] Furthermore, the organic light-emitting device according to the present invention can be a structure (normal type) in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate. Additionally, the organic light-emitting device according to the present invention can be a reverse structure (inverted type) in which a cathode, one or more organic layers, and an anode are sequentially stacked on a substrate. For example, the structure of an organic light-emitting device according to an embodiment of the present invention is illustrated below. Figure 1 and Figure 2 middle.

[0256] Figure 1 The illustration shows an example of an organic light-emitting device consisting of a substrate 1, an anode 2, a light-emitting layer 3, and a cathode 4. In the structure described above, the compound represented by the above chemical formula 1 may be included in the light-emitting layer.

[0257] Figure 2 The illustration shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light-emitting layer 3, an electron injection and transport layer 8, and a cathode 4. In the structure described above, the compound represented by Chemical Formula 1 may be included in one or more of the hole injection layer, hole transport layer, electron blocking layer, light-emitting layer, and electron injection and transport layer. Specifically, the compound represented by Chemical Formula 1 may be included in the light-emitting layer or the electron blocking layer; for example, it may be included as the host material of the light-emitting layer or the material of the electron blocking layer.

[0258] The organic light-emitting device according to the present invention, except that one or more of the organic layers contain a compound represented by the above-described chemical formula 1, can be manufactured using materials and methods known in the art. Furthermore, when the organic light-emitting device comprises a plurality of organic layers, the organic layers can be formed from the same substance or different substances.

[0259] For example, the organic light-emitting device according to the present invention can be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. This can be achieved by: depositing a metal or a conductive metal oxide or alloy thereof onto the substrate using a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation to form an anode; then forming an organic layer on the anode, including a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer; and finally depositing a material suitable for use as a cathode onto the organic layer. Alternatively, the organic light-emitting device can also be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material onto the substrate.

[0260] Furthermore, the compound represented by the above chemical formula 1 can be used to form an organic layer in the manufacture of organic light-emitting devices not only by vacuum evaporation but also by solution coating. In particular, the compound represented by the above chemical formula 1 has excellent solubility in solvents used in solution coating, thus making it easy to apply solution coating methods. Here, solution coating methods refer to, but are not limited to, spin coating, dip coating, blade coating, inkjet printing, screen printing, spray coating, and roll coating.

[0261] Hereinafter, the present invention provides compounds represented by the above chemical formula 1 and coating compositions containing solvents.

[0262] The solvents described above are not particularly limited as long as they can dissolve or disperse the compounds according to the present invention. Examples include chloroform, dichloromethane, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, o-dichlorobenzene, and other chlorinated solvents; tetrahydrofuran, dichloromethane, dichlorobenzene, and other chlorinated solvents. Ether solvents such as alkanes; aromatic hydrocarbon solvents such as toluene, xylene, trimethylbenzene, and mesitylene; aliphatic hydrocarbon solvents such as cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane, and n-decane; ketone solvents such as acetone, methyl ethyl ketone, and cyclohexanone; ester solvents such as ethyl acetate, butyl acetate, and ethyl cellosol acetate; ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether, dimethoxyethane, propylene glycol, and diethoxymethane. Polyols such as triethylene glycol monoethyl ether, glycerol, and 1,2-hexanediol and their derivatives; alcohol solvents such as methanol, ethanol, propanol, isopropanol, and cyclohexanol; sulfoxide solvents such as dimethyl sulfoxide; amide solvents such as N-methyl-2-pyrrolidone and N,N-dimethylformamide; benzoate solvents such as butyl benzoate and methyl 2-methoxybenzoate; and solvents such as tetrahydronaphthalene and 3-phenoxy-toluene. Furthermore, one of the above solvents may be used alone, or two or more solvents may be used in combination.

[0263] Furthermore, the viscosity of the above-described coating composition is preferably from 1 cP to 10 cP, within which it is easily applied. Additionally, the concentration of the compound according to the invention in the above-described coating composition is preferably from 0.1 wt / v% to 20 wt / v%.

[0264] Furthermore, the present invention provides a method for forming a functional layer using the above-described coating composition. Specifically, it includes: applying the above-described coating composition according to the present invention through a solution process; and heat-treating the applied coating composition.

[0265] In the above heat treatment step, the heat treatment temperature is preferably between 150°C and 230°C. Furthermore, the heat treatment time is between 1 minute and 3 hours, more preferably between 10 minutes and 1 hour. Additionally, the heat treatment is preferably performed in an atmosphere of inert gas such as argon or nitrogen.

[0266] As an example, the first electrode is the anode and the second electrode is the cathode, or the first electrode is the cathode and the second electrode is the anode.

[0267] As the aforementioned anode material, a material with a high work function is preferred in order to facilitate the injection of holes into the organic layer. Specific examples of the aforementioned anode materials include 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-(ethylidene-1,2-dioxo)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited to these.

[0268] As the cathode material described above, a material with a low work function is generally preferred in order to facilitate the injection of electrons into the organic layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or their alloys; multilayer structures such as LiF / Al or LiO2 / Al, etc., but are not limited to these.

[0269] The aforementioned hole injection layer is a layer that injects holes from the electrode. Preferably, the hole injection material is a compound that possesses the ability to transport holes, the effect of injecting holes from the anode, excellent hole injection performance for the light-emitting layer or light-emitting material, prevents excitons generated in the light-emitting layer from migrating to the electron injection layer or electron injection material, and exhibits excellent thin film formation capability. Preferably, the HOMO (highest occupied molecular orbital) of the hole injection material is between that of the anode material and the HOMO of the surrounding organic layer. Specific examples of hole injection materials include, but are not limited to, metalloporphyrins, oligothiophenes, arylamine-based organic compounds, hexanitrile hexaazabenzophenanthrene-based organic compounds, quinacridone-based organic compounds, perylene-based organic compounds, anthraquinones, and conductive polymers based on polyaniline and polythiophene.

[0270] The aforementioned hole transport layer is a layer that receives holes from the hole injection layer and transports them to the light-emitting layer. The hole transport material is a substance capable of receiving holes from the anode or hole injection layer and transferring them to the light-emitting layer; substances with high hole mobility are suitable. Specific examples include aryl amine-based organic compounds, conductive polymers, and block copolymers that simultaneously contain conjugated and non-conjugated portions, but are not limited to these.

[0271] The aforementioned luminescent material is capable of receiving holes and electrons from the hole transport layer and electron transport layer, respectively, and combining them to emit light in the visible light region. Preferably, it is a material with high quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxyquinoline aluminum complex (Alq3); carbazole compounds; diluted styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; and benzo[…]. Compounds including azoles, benzothiazoles and benzimidazoles; poly(p-phenylenevinylene) (PPV) polymers; spiro compounds; polyfluorene, fluorene, etc., but not limited to these.

[0272] The aforementioned luminescent layer may comprise a host material and a dopant material. The host material may be an aromatic fused-ring derivative or a heterocyclic compound. Specifically, aromatic fused-ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentane derivatives, phenanthrene compounds, and fluoranthene compounds; heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, and ladder-type furan compounds. Pyrimidine derivatives, etc., but not limited thereto. Preferably, the compound according to the invention is used as the main material. Furthermore, the compound according to the invention may also be included together with the compound according to the invention represented by chemical formula 1 as the main material.

[0273] As dopant materials, there are aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, aromatic amine derivatives are aromatic fused-ring derivatives with substituted or unsubstituted aryl amino groups, such as pyrene, anthracene, etc. Diindrone pyrene, etc., styrylamine compounds are compounds in which at least one aryl vinyl group is substituted on a substituted or unsubstituted arylamine, and is substituted or unsubstituted by one or more substituents selected from aryl, silyl, alkyl, cycloalkyl, and arylamino groups. Specifically, there are styrylamines, styryldiamines, styryltriamines, styryltetraamines, etc., but they are not limited to these. In addition, as metal complexes, there are iridium complexes, platinum complexes, etc., but they are not limited to these. Preferably, iridium-based metal complexes are used as the above-mentioned dopant materials.

[0274] The aforementioned light-emitting layer can be a red light-emitting layer. When the compound according to the present invention is used as the host material, the stability of electrons and holes is increased, and the energy transfer from the host to the red dopant is well formed, which can improve the characteristics related to the driving voltage, luminous efficiency and lifetime of organic light-emitting devices.

[0275] The aforementioned electron transport layer is the layer that receives electrons from the electron injection layer and transports them to the light-emitting layer. The electron transport material is one that can effectively receive electrons from the cathode and transfer them to the light-emitting layer; materials with high electron mobility are suitable. Specific examples include Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free radical compounds, hydroxyflavonoid-metal complexes, etc., but are not limited to these. The electron transport layer can be used with any desired cathode material as used in the prior art. In particular, examples of suitable cathode materials are common materials with low work functions and accompanied by an aluminum or silver layer. Specifically, these are cesium, barium, calcium, ytterbium, and samarium, each accompanied by an aluminum or silver layer.

[0276] The aforementioned electron injection layer is a layer that injects electrons from the electrode. Preferably, compounds are those that possess electron transport capabilities, effectively inject electrons from the cathode, exhibit excellent electron injection performance for the light-emitting layer or material, prevent excitons generated in the light-emitting layer from migrating to the hole injection layer, and demonstrate excellent thin-film formation ability. Specifically, these include fluorenone, anthraquinone dimethyl ether, biphenylquinone, thiamethoxam dioxide, etc. azole, Diazoles, triazoles, imidazoles, perylenetetracarboxylic acid, fluorenemethane, anthrones, and their derivatives, metal coordination compounds, and nitrogen-containing five-membered ring derivatives, but not limited to these.

[0277] Examples of the aforementioned metal coordination compounds include lithium 8-hydroxyquinoline, bis(8-hydroxyquinoline)zinc, bis(8-hydroxyquinoline)copper, bis(8-hydroxyquinoline)manganese, tris(8-hydroxyquinoline)aluminum, tris(2-methyl-8-hydroxyquinoline)aluminum, tris(8-hydroxyquinoline)gallium, bis(10-hydroxybenzo[h]quinoline)beryllium, bis(10-hydroxybenzo[h]quinoline)zinc, bis(2-methyl-8-quinoline)gallium chloride, bis(2-methyl-8-quinoline)(o-cresol)gallium, bis(2-methyl-8-quinoline)(1-naphthol)aluminum, and bis(2-methyl-8-quinoline)(2-naphthol)gallium, but are not limited to these.

[0278] The organic light-emitting device according to the present invention can be a bottom-emission device, a top-emission device, or a bidirectional light-emitting device, and in particular, it can be a bottom-emission device that requires relatively high luminous efficiency.

[0279] In addition, the compounds according to the present invention can be included not only in organic light-emitting devices, but also in organic solar cells or organic transistors.

[0280] The manufacture of compounds represented by the above chemical formula 1 and organic light-emitting devices containing them is specifically described in the following examples. However, the following examples are for illustrative purposes only and the scope of the invention is not limited thereto.

[0281] [Synthesis example]

[0282] Synthesis Example 1. Synthesis of Compound 1

[0283] Step 1) Synthesis of Compound 1-1

[0284]

[0285] Under a nitrogen atmosphere, (11-phenyl-11H-benzo[a]carbazol-8-yl)boronic acid (15.0 g, 44.5 mmol) and 3-bromo-9H-carbazole (12.0 g, 48.9 mmol) were added to 300 mL of tetrahydrofuran (THF), stirred, and refluxed. Then, potassium carbonate (K₂CO₃, 24.6 g, 177.9 mmol) dissolved in 74 mL of water was added, and after thorough stirring, tetra(triphenylphosphine)palladium(O) (Pd(PPh₃)₄, 1.5 g, 1.3 mmol) was added. After reacting for 8 hours, the mixture was cooled to room temperature, and the organic and aqueous layers were separated by distillation of the organic layer. The compound was redissolved in chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography to produce 14.9 g of compound 1-1. (Yield 73%, MS: [M+H)) + =460)

[0286] Step 2) Synthesis of Compound 1

[0287]

[0288] Under a nitrogen atmosphere, compound 1-1 (15.0 g, 31.0 mmol) and 2-bromodibenzo[b,d]furan (8.4 g, 34.1 mmol) were added to 300 mL of toluene, stirred, and refluxed. Then, sodium tert-butoxide (NaOBu, 4.5 g, 46.5 mmol) and bis(tri-tert-butylphosphine)palladium(0) (0.5 g, 0.9 mmol) were added. After reacting for 6 hours, the mixture was cooled to room temperature, and the organic layer was separated using chloroform and water, followed by distillation. The organic layer was redissolved in chloroform, washed twice with water, separated again, and anhydrous magnesium sulfate was added. After stirring, the mixture was filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was purified by silica gel column chromatography, and then purified by sublimation to produce 7.6 g of compound 1. (Yield 39%, MS: [M+H]) + =626)

[0289] Synthesis Example 2. Synthesis of Compound 2

[0290]

[0291] In Synthesis Example 1, (11-phenyl-11H-benzo[a]carbazol-8-yl)boronic acid was replaced with (11-([1,1'-biphenyl]-4-yl)-11H-benzo[a]carbazol-8-yl)boronic acid ((11-([1,1'-biphenyl]-4-yl)-11H-benzo[a]carbazol-8-yl)boronic acid), and 2-bromodibenzo[b,d]furan was replaced with 1-chlorodibenzo[b,d]furan. Otherwise, compound 2 was prepared by the same method as in Synthesis Example 1 described above. (MS:[M+H) + =702)

[0292] Synthesis Example 3. Synthesis of Compound 3

[0293]

[0294] In Synthesis Example 1, (11-phenyl-11H-benzo[a]carbazol-8-yl)boronic acid was changed to (5-(naphthalen-2-yl)-5H-benzo[b]carbazol-2-yl)boronic acid, and 2-bromodibenzo[b,d]furan was changed to 3-bromodibenzo[b,d]furan.

[0295] Compound 3 was prepared by means of the synthetic method described in Synthetic Example 1 above, except that it was used with bromodibenzo[b,d]furan. (MS:[M+H) + =676)

[0296] Synthesis Example 4. Synthesis of Compound 4

[0297]

[0298] In Synthesis Example 1, (11-phenyl-11H-benzo[a]carbazol-8-yl)boronic acid was replaced with (5-([1,1'-biphenyl]-3-yl)-5H-benzo[b]carbazol-2-yl)boronic acid, and 2-bromodibenzo[b,d]furan was replaced with 4-chlorodibenzo[b,d]thiophene. Otherwise, compound 4 was prepared by the same method as in Synthesis Example 1 described above. (MS:[M+H) + =718)

[0299] Synthesis Example 5. Synthesis of Compound 5

[0300]

[0301] In Synthesis Example 1, (11-phenyl-11H-benzo[a]carbazol-8-yl)boronic acid was replaced with (6-phenyl-11-(phenyl-d5)-11H-benzo[a]carbazol-8-yl)boronic acid, and compound 5 was otherwise prepared by the same method as in Synthesis Example 1 above. (MS:[M+H) + =707)

[0302] Synthesis Example 6. Synthesis of Compound 6

[0303]

[0304] In Synthesis Example 1, 3-bromo-9H-carbazole was replaced with 3-bromo-5-phenyl-9H-carbazole, and 2-bromodibenzo[b,d]furan was replaced with 3-bromodibenzo[b,d]thiophene. Otherwise, compound 6 was prepared by the same method as in Synthesis Example 1. (MS:[M+H) + =718)

[0305] Synthesis Example 7. Synthesis of Compound 7

[0306]

[0307] In Synthesis Example 1, (11-phenyl-11H-benzo[a]carbazole-8-yl)boronic acid was replaced with (9-phenyl-9H-carbazole-3-yl)boronic acid, 3-bromo-9H-carbazole was replaced with 8-bromo-11H-benzo[a]carbazole, and 2-bromodibenzo[b,d]furan was replaced with 4-chlorodibenzo[b,d]furan. Otherwise, compound 7 was prepared by the same method as in Synthesis Example 1 described above. (MS:[M+H) + =626)

[0308] Synthesis Example 8. Synthesis of Compound 8

[0309]

[0310] In Synthesis Example 1, (11-phenyl-11H-benzo[a]carbazole-8-yl)boronic acid was replaced with (9-(naphthalen-1-yl)-9H-carbazole-3-yl)boronic acid ((9-(naphthalen-1-yl)-9H-carbazol-3-yl)boronic acid), 3-bromo-9H-carbazole was replaced with 2-bromo-5H-benzo[b]carbazole, and 2-bromodibenzo[b,d]furan was replaced with 2-bromodibenzo[b,d]thiophene. Otherwise, compound 8 was prepared by the same method as in Synthesis Example 1 described above. (MS:[M+H) + =692)

[0311] Synthesis Example 9. Synthesis of Compound 9

[0312]

[0313] In Synthesis Example 1, (11-phenyl-11H-benzo[a]carbazole-8-yl)boronic acid was replaced with (7,9-diphenyl-9H-carbazole-3-yl)boronic acid, 3-bromo-9H-carbazole was replaced with 2-bromo-5H-benzo[b]carbazole, and 2-bromodibenzo[b,d]furan was replaced with 1-chlorodibenzo[b,d]thiophene. Otherwise, compound 9 was prepared by the same method as in Synthesis Example 1 described above. (MS:[M+H) + =718)

[0314] Synthesis Example 10. Synthesis of Compound 10

[0315]

[0316] In Synthesis Example 1, (11-phenyl-11H-benzo[a]carbazole-8-yl)boronic acid was replaced with (9-phenyl-9H-carbazole-3-yl)boronic acid, 3-bromo-9H-carbazole was replaced with 2-bromo-5H-benzo[b]carbazole, and 2-bromodibenzo[b,d]furan was replaced with 1-(3-chlorophenyl)dibenzo[b,d]furan. Otherwise, compound 10 was prepared by the same method as in Synthesis Example 1 described above. (MS:[M+H) + =702)

[0317] [Example]

[0318] Example 1-1

[0319] ITO (Indium Tin Oxide) was applied at 1400 angstroms ( A glass substrate with an angstrom-like thickness coated as a thin film is immersed in distilled water containing detergent and washed using ultrasound. The detergent used is Decon from Fischer Co. TMFor CON705 products, distilled water was used that had been filtered twice using a 0.22μm sterilizing filter manufactured by Millipore Co. After washing the ITO for 30 minutes, it was ultrasonically washed twice with distilled water for 10 minutes each. After the distilled water washing, the substrate was ultrasonically washed for 10 minutes each with isopropanol, acetone, and methanol, respectively, and then dried before being transferred to a plasma cleaner. Furthermore, the substrate was cleaned with oxygen plasma for 5 minutes before being transferred to a vacuum evaporation machine.

[0320] On the prepared ITO transparent electrode, the following compounds HI-A and LG-101 were sequentially applied... A hole injection layer is formed by thermal vacuum evaporation to a thickness of [amount missing]. On the aforementioned hole injection layer, as a hole transport layer, the following compound HT-A is [deposited / applied / contained / etc.]. After vacuum evaporation to a thickness of [amount], the following compound EB-A is used as an electron blocking layer. The thickness was then subjected to thermal vacuum evaporation. Next, on the aforementioned EB-A evaporated film, a mixture of compound RH-A and compound 1 in a 1:1 weight ratio was used as the light-emitting layer substrate, and compound RD-A was used as the dopant. The substrate and dopant were mixed in a 98:2 weight ratio and... A red luminescent layer was formed by vacuum evaporation to a thickness of [thickness value missing]. Next, as an electron injection and transport layer, the following compounds, ET-A and Liq, were mixed in a 1:1 ratio and [missing information - likely a specific chemical process]. The thickness is subjected to thermal vacuum evaporation, and then the following compound Liq is applied... Vacuum evaporation was performed on the aforementioned electron injection and transport layer to achieve a thickness of [missing information]. Magnesium and silver were sequentially deposited in a 10:1 ratio [missing information]. The aluminum is vapor-deposited to a thickness of [amount missing], using [method missing] to deposit [material missing]. The cathode is formed by vapor deposition of a certain thickness.

[0321]

[0322] During the above process, the evaporation rate of organic matter is maintained. / seconds / second, lithium fluoride at the cathode maintains Evaporation rate per second, aluminum retention A vapor deposition rate of / second is achieved, while maintaining a vacuum level of 2x10 during vapor deposition. -7 Up to 5x10 -6 This led to the creation of organic light-emitting devices.

[0323] Examples 1-2 to 1-10

[0324] In the organic light-emitting devices of Examples 1-1 above, compounds 2 to 10 listed in Table 1 below were used instead of compound 1. Otherwise, organic light-emitting devices of Examples 1-2 to 1-10 were manufactured by the same method as in Examples 1-1 above. In this case, a mixture of any one of compounds 2 to 10 and compound RH-A at a weight ratio of 1:1 was used as the main body of the light-emitting layer. The numbers in parentheses in Table 1 below indicate the weight ratio between the main compounds.

[0325]

[0326] Comparative Examples 1-1 to 1-5

[0327] In the organic light-emitting device of Example 1-1, compounds A to E as described in Table 1 below were used instead of compound 1. Otherwise, the organic light-emitting devices of Comparative Examples 1-1 to 1-5 were manufactured by the same method as in Example 1-1. In this case, a mixture of any one of the compounds A to E and compound RH-A in a 1:1 weight ratio was used as the main body of the light-emitting layer. The numbers in parentheses in Table 1 below indicate the weight ratio between the main compounds. Furthermore, compounds A, B, C, D, and E used in Table 1 below are shown below.

[0328]

[0329] Examples 2-1 to 2-10

[0330] In the organic light-emitting device of Example 1-1, compounds 1 to 10 listed in Table 2 below were used instead of compound EB-A as the electron blocking layer, and only compound RH-A without being mixed with compound 1 was used as the main body of the light-emitting layer. Otherwise, the organic light-emitting devices of Examples 2-1 to 2-10 were manufactured by the same method as in Example 1-1.

[0331] Comparative Examples 2-1 to 2-5

[0332] In the organic light-emitting device of Example 1-1, compounds A to E as described in Table 2 below were used instead of compound EB-A as the electron blocking layer, and only compound RH-A without being mixed with compound 1 was used as the main body of the light-emitting layer. Otherwise, the organic light-emitting devices of Comparative Examples 2-1 to 2-5 were manufactured by the same method as in Example 1-1.

[0333] [Experimental Example]

[0334] Experimental Example 1

[0335] The organic light-emitting devices fabricated in Examples 1-1 to 1-10 and Comparative Examples 1-1 to 1-5 were subjected to current, and their voltage, efficiency, and lifetime were measured. The results are shown in Table 1 below. In this case, the voltage and efficiency were measured when an applied current was applied at 10 mA / cm². 2 The value is determined by the current density; LT97 refers to a value at 20 mA / cm². 2 The time (hr) required for the initial luminance (6000 nits) to decrease to 97% at the given current density.

[0336] [Table 1]

[0337]

[0338] As shown in Table 1 above, in the case of organic light-emitting devices manufactured using the compounds of the present invention as materials for the light-emitting layer, excellent characteristics are exhibited in terms of efficiency, driving voltage, and / or stability (lifetime) of the organic light-emitting devices.

[0339] An organic light-emitting device according to an embodiment of the present invention, by bonding a heterocycle containing O or S to the nitrogen atom of a core structure formed by bonding a carbazole group at a specific position corresponding to the benzene ring in the benzocarbazole group, thereby exhibiting lower driving voltage and higher efficiency and longer lifetime characteristics compared to organic light-emitting devices manufactured by using compound A (with a carbazole group attached at the position corresponding to the naphthyl ring in the benzocarbazole group), compound B (without a heterocycle), compound C (with a carbazole ring containing N instead of a heterocycle containing O or S), compound D (with a benzofuran ring contained in a linking group between the benzocarbazole group and the carbazole group), or compound E (with a different position of the naphthyl ring in the core structure of the benzocarbazole group) as the material of the light-emitting layer.

[0340] Experimental Example 2

[0341] The organic light-emitting devices fabricated in Examples 2-1 to 2-10 and Comparative Examples 2-1 to 2-5 were subjected to current, and their voltage, efficiency, and lifetime were measured. The results are shown in Table 2 below. In this case, the voltage and efficiency were measured when an applied current of 10 mA / cm² was applied. 2 The value is determined by the current density; LT97 refers to a current density of 20 mA / cm². 2 The time (hr) required for the initial luminance (6000 nits) to decrease to 97% at a current density.

[0342] [Table 2]

[0343]

[0344] As shown in Table 2 above, in the case of organic light-emitting devices manufactured using the compounds of the present invention as materials for electron blocking layers, excellent characteristics are exhibited in terms of efficiency, driving voltage, and / or stability (lifetime) of the organic light-emitting devices.

[0345] An organic light-emitting device according to an embodiment of the present invention, by bonding a heterocycle containing O or S to the nitrogen atom of a core structure formed by bonding a carbazole group at a specific position corresponding to the benzene ring in the benzocarbazole group, exhibits lower driving voltage and higher efficiency and longer lifetime compared to organic light-emitting devices manufactured by using compound A (with a carbazole group attached at the position corresponding to the naphthyl ring in the benzocarbazole group), compound B (without a heterocycle), compound C (with a carbazole ring containing N instead of a heterocycle containing O or S), compound D (with a benzofuran ring contained in a linking group between the benzocarbazole group and the carbazole group), or compound E (with a different position of the naphthyl ring in the core structure of the benzocarbazole group) as the material for the electron blocking layer.

[0346] [Symbol Explanation]

[0347] 1: Substrate 2: Anode

[0348] 3: Light-emitting layer 4: Cathode

[0349] 5: Hole injection layer; 6: Hole transport layer

[0350] 7: Electron blocking layer; 8: Electron injection and transport layer.

Claims

1. A compound represented by the following chemical formula 1: [Chemical Formula 1] In the chemical formula 1, Two adjacent R1 atoms bond together to form a benzene ring, which is substituted with hydrogen or deuterium. The remaining R1 is either hydrogen or deuterium. R2 is hydrogen, deuterium, or a C that is either deuterated or unsubstituted. 6-30 Aryl, R a R b and R c Each is independently hydrogen, deuterium, or C that is either deuterated or unsubstituted. 6-30 Aryl, n1 and n2 are both integers from 0 to 3. n3 is an integer from 0 to 4. L1 and L2 are each independently a single bond, or a C bond that is either deuterated or unsubstituted. 6-30 Alpha-aryl One of Ar1 and Ar2 has the following chemical formula 2, and the other is a C1 or C2 that is either deuterated or unsubstituted. 6-30 Aryl, Chemical formula 2 In the chemical formula 2, X is O or S. R d Each can be independently hydrogen or deuterium. n4 is an integer from 0 to 7.

2. The compound according to claim 1, wherein, Compounds represented by chemical formula 1 are represented by chemical formula 1-1 or 1-2. [Chemical Formula 1-1] [Chemical Formula 1-2] In the chemical formulas 1-1 and 1-2, R a R b R c L1, L2, n1, n2, n3, Ar1, and Ar2 are the same as defined in claim 1. R' can be either hydrogen or deuterium. n' is an integer from 0 to 6, each of which is independent.

3. The compound according to claim 1, wherein, The compound represented by chemical formula 1 is represented by any one of the following chemical formulas 1-3 to 1-10. [Chemical Formulas 1-3] [Chemical Formulas 1-4] [Chemical Formulas 1-5] [Chemical Formulas 1-6] [Chemical Formulas 1-7] [Chemical Formulas 1-8] [Chemical Formulas 1-9] [Chemical Formulas 1-10] In the chemical formulas 1-3 and 1-10, R a R b R c L1, L2, n1, n2, n3, Ar1, and Ar2 are the same as defined in claim 1. R' can be either hydrogen or deuterium. n' is an integer from 0 to 6, each of which is independent.

4. The compound according to claim 1, wherein, The compound represented by the chemical formula 1 is selected from any one of the following compounds: 。 5. An organic light-emitting device, wherein, include: A first electrode, a second electrode disposed opposite to the first electrode, and an organic layer of one or more layers disposed between the first electrode and the second electrode, wherein one or more of the organic layers comprises a compound according to any one of claims 1 to 4.

6. The organic light-emitting device according to claim 5, wherein, The organic layer containing the compound is a light-emitting layer or an electron-blocking layer.

Images