Novel compound and organic light emitting device comprising same

Abstract

The present invention relates to a novel compound and an organic light emitting device comprising same. More specifically, the novel compound according to the present invention has a structure in which N-containing monocyclic rings, such as pyridine, pyrimidine, or triazine, are bonded to a benzoquinoline core through at least two or three linkers, and such a structural feature leads to excellent electron transfer characteristics, so that the novel compound is suitable for an organic material layer, particularly an electron transport layer, a hole blocking layer, or a charge generation layer, in an organic light emitting device.

Description

Novel compound and organic light-emitting device containing the same

[0001] The present invention relates to a novel compound and an organic light-emitting device comprising the same.

[0002] Recently, the technology of organic light emitting devices (OLEDs), one of the flat panel display devices, has been developing rapidly.

[0003] An organic light-emitting device is a device that has an organic thin film layer including a light-emitting layer between an anode and a cathode, and emits light when holes and electrons injected into the light-emitting layer pair up and then disappear.

[0004] Compounds used in organic light-emitting devices require improved performance.

[0005] The purpose of the present invention is to provide a novel compound and an organic light-emitting device comprising the same.

[0006] The object of the present invention is achieved by a novel compound represented by the following chemical formula 1 and an organic light-emitting device comprising the same.

[0007]

[0008] In the above chemical formula 1,

[0009] R1 to R9 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, nitrile group, substituted or unsubstituted C1~C30 alkyl group, substituted or unsubstituted C1~C30 alkenyl group, substituted or unsubstituted C1~C30 alkynyl group, substituted or unsubstituted C3~C30 cycloalkyl group, substituted or unsubstituted C1~C30 heterocycloalkyl group, substituted or unsubstituted C1~C30 alkoxy group, substituted or unsubstituted C1~C30 sulfide group, substituted or unsubstituted C6~C30 aryl group, substituted or unsubstituted C2~C30 heteroaryl group, substituted or unsubstituted C6~C30 aryloxy group, substituted or unsubstituted C2~C30 heteroaryloxy group, substituted or unsubstituted C1~C30 thio group, substituted or Selected from the group consisting of an unsubstituted C1~C30 amine group, a substituted or unsubstituted C1~C30 silyl group, and a substituted or unsubstituted C1~C30 phosphine oxide group, wherein at least one of R1 to R9 is the structural formula 1,

[0010] In the above structural formula 1,

[0011] L1 and L2 are each independently a substituted or unsubstituted C6~C30 arylene group, or a substituted or unsubstituted C2~C30 heteroarylene group,

[0012] L3 is a direct bond, a substituted or unsubstituted C6~C30 arylene group, or a substituted or unsubstituted C2~C30 heteroarylene group,

[0013] X1 to X5 are each independently N or CR, and at least one is N,

[0014] Here, R is each independently hydrogen, deuterium, halogen, cyano group, nitro group, nitrile group, substituted or unsubstituted C1~C30 alkyl group, substituted or unsubstituted C1~C30 alkenyl group, substituted or unsubstituted C1~C30 alkynyl group, substituted or unsubstituted C3~C30 cycloalkyl group, substituted or unsubstituted C1~C30 heterocycloalkyl group, substituted or unsubstituted C1~C30 alkoxy group, substituted or unsubstituted C1~C30 sulfide group, substituted or unsubstituted C6~C30 aryl group, substituted or unsubstituted C2~C30 heteroaryl group, substituted or unsubstituted C6~C30 aryloxy group, substituted or unsubstituted C2~C30 heteroaryloxy group, substituted or unsubstituted C1~C30 thio group, substituted or unsubstituted It is selected from the group consisting of a C1~C30 amine group, a substituted or unsubstituted C1~C30 silyl group, and a substituted or unsubstituted C1~C30 phosphine oxide group.

[0015] According to the present invention, a novel compound and an organic light-emitting device comprising the same are provided. The novel compound according to the present invention has excellent electron transport properties, and when applied to one or more organic layers within an organic light-emitting device, it helps realize low voltage, high efficiency, and long life of the organic light-emitting device. More specifically, the novel compound may be applied to an organic layer in which a material with electron transport properties is applied, and in one embodiment, it may be applied to an electron transport layer, a hole blocking layer, or a charge generation layer.

[0016] In this specification, when it is said that a part “includes” a certain component, this does not mean that other components are excluded, but rather that other components may be included, unless otherwise specifically stated.

[0017] In this specification, when it is said that a member is located 'on' another member, this includes not only cases where a member is in contact with another member, but also cases where another member exists between the two members.

[0018] In this specification, examples of substituents are described below, but are not limited thereto.

[0019] As used herein, the term "substitution" refers to the replacement of a hydrogen atom bonded to a carbon atom of a compound with another substituent. The position of substitution is not particularly limited as long as it is a position where substitution is possible, and when substitution is made with two or more substituents, the substituents may be the same or different.

[0020] In this specification, the term 'substituted or unsubstituted' means that it is substituted with one or more substituents selected from the group consisting of deuterium, halogen group, cyano group, nitro group, nitrile group, alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, alkoxy group, sulfide group, aryloxy group, heteroaryloxy group, thio group, amine group, silyl group, phosphine oxide group, aryl group and heteroaryl group, or is substituted with a substituent in which two or more substituents selected from the above group are connected, or has no substituents, and the selected substituents may or may not form a ring by combining with each other. An example of a substituent in which two or more substituents are connected is a biphenyl group. That is, a biphenyl group may correspond to an aryl group and at the same time correspond to a substituent having two phenyl groups connected, and at the same time correspond to an aryl group having one phenyl group substituted.

[0021] In the present specification, the alkyl group may be a straight or branched chain having 1 to 60 carbon atoms, and specific examples thereof include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 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-ethylpropyl, Examples thereof include, but are not limited to, 1,1-dimethylpropyl, isohexyl, 2-methylpentyl, 4-methylhexyl, and 5-methylhexyl. Specifically, the alkyl group may have 1 to 30 carbon atoms, and more specifically, 1 to 20 carbon atoms.

[0022] In the present specification, the alkenyl group may be a straight or branched chain having 2 to 60 carbon atoms, and specific examples thereof include, but are not limited to, a vinyl group, a 1-propenyl group, an isopropenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-pentenyl group, a 2-pentenyl group, a 3-pentenyl group, a 3-methyl-1-butenyl group, a 1,3-butadienyl group, an allyl group, a 1-phenylvinyl-1-yl group, a 2-phenylvinyl-1-yl group, a 2,2-diphenylvinyl-1-yl group, a 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl group, a 2,2-bis(diphenyl-1-yl)vinyl-1-yl group, a stilbenyl group, and a styrenyl group. Specifically, the number of carbon atoms in the alkenyl group may be 2 to 30, and more specifically, 2 to 20.

[0023] In the present specification, the alkynyl group may be a straight or branched chain having 2 to 60 carbon atoms. Specifically, the alkynyl group may have 2 to 30 carbon atoms, and more specifically, 2 to 20 carbon atoms.

[0024] In the present specification, the alkoxy group may be a straight chain, branched chain or cyclic chain having 1 to 60 carbon atoms, and specific examples thereof include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, etc. Specifically, the alkoxy group may have 1 to 30 carbon atoms, and more specifically, 1 to 20 carbon atoms.

[0025] In the present specification, the cycloalkyl group may be monocyclic or polycyclic having 3 to 60 carbon atoms, and specific examples thereof include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, and cyclooctyl. Specifically, the cycloalkyl group may have 3 to 30 carbon atoms, and more specifically, 3 to 20 carbon atoms.

[0026] In the present specification, a heterocycloalkyl group is a group that contains at least one non-carbon atom, i.e., a heteroatom, and specifically, may be a cycloalkyl group that contains at least one heteroatom selected from the group consisting of O, N, S, Se, etc., and may be a monocyclic or polycyclic group having 2 to 60 carbon atoms. Specifically, the heterocycloalkyl group may have 2 to 30 carbon atoms, and more specifically, may have 2 to 20 carbon atoms.

[0027] In the present specification, a sulfide group includes S and may have 1 to 60 carbon atoms. Specific examples include, but are not limited to, an alkyl sulfide group such as a dimethyl sulfide group, an aryl sulfide group such as diphenyl sulfide, and a heteroaryl sulfide group substituted with a heteroaryl group. Specifically, the sulfide group may have 1 to 30 carbon atoms, and more specifically, 1 to 20 carbon atoms.

[0028] In the present specification, the aryloxy group may be a substituent that contains O, and the O atom may be directly connected as a radical, and may have 6 to 60 carbon atoms. Specific examples include phenoxy groups, naphthoxy groups, biphenoxy groups, etc., which are oxy groups substituted with aryl groups, but are not limited thereto. The heteroaryloxy group is an oxy group substituted with heteroaryl groups, and may have 2 to 60 carbon atoms. Specifically, the aryloxy group may have 6 to 30 carbon atoms, and more specifically, may have 6 to 20 carbon atoms.

[0029] In the present specification, the thio group includes S and may have 1 to 60 carbon atoms. Specific examples include, but are not limited to, alkylthio groups such as methylthio, ethylthio, butylthio, pentylthio, and hexylthio, arylthio groups such as phenylthio, and naphthylthio, and heteroarylthio groups substituted with heteroaryl groups. Specifically, the thio group may have 1 to 30 carbon atoms, and more specifically, 1 to 20 carbon atoms.

[0030] In the present specification, the silyl group may be a substituent containing Si, and the Si atom may be directly connected as a radical, and may have 1 to 60 carbon atoms. Specific examples thereof include, but are not limited to, alkylsilyl groups such as trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl, and propyldimethylsilyl groups, arylsilyl groups such as triphenylsilyl, diphenylsilyl, and phenylsilyl groups, and heteroarylsilyl groups substituted with heteroaryl groups. Specifically, the silyl group may have 1 to 30 carbon atoms, and more specifically, 1 to 20 carbon atoms.

[0031] In the present specification, the phosphine oxide group includes P=O and may have 1 to 60 carbon atoms. Specific examples include, but are not limited to, an alkylphosphine oxide group such as a dimethylphosphine oxide group, an arylphosphine oxide group such as a diphenylphosphine oxide group and a dinaphthylphosphine oxide group, and a heteroarylphosphine oxide group substituted with a heteroaryl group. Specifically, the phosphine oxide group may have 1 to 30 carbon atoms, and more specifically, 1 to 20 carbon atoms.

[0032] In the present specification, the aryl group may be monocyclic or polycyclic and have 6 to 60 carbon atoms. In the case of a monocyclic aryl group, specific examples thereof include a phenyl group, a biphenyl group, a terphenyl group, etc., but are not limited thereto. In the case of a polycyclic aryl group, specific examples thereof include a naphthyl group, anthracenyl group, a phenanthrenyl group, a triphenylenyl group, a pyrenyl group, a fluorenyl group, etc., but are not limited thereto. Specifically, the aryl group may have 6 to 50 carbon atoms, and more specifically, 6 to 30 carbon atoms.

[0033] In the present specification, a heteroaryl group includes at least one non-carbon atom, i.e., a heteroatom, and may specifically include at least one heteroatom selected from the group consisting of O, N, S, and Se, and may be a monocyclic or polycyclic group having 2 to 60 carbon atoms. Specific examples include a thiophenyl group, a furanyl group, a pyrrolyl group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a pyridinyl group, a bipyridinyl group, a pyrimidinyl group, a pyrimidinyl group, a pyrazinyl group, a quinolinyl group, a quinazolyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyrazinyl group, a pyrazinopyrazinyl group, a pyridoindolyl group, a benzothienopyrimidyl group, an indenocarbazolyl group, an isoquinolinyl group, an indolyl group, a carbazolyl group, a benzoxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzocarbazolyl group, a benzothiophenyl group, Examples thereof include, but are not limited to, a dibenzothiophenyl group, a benzofuranyl group, a phenanthridinyl group, a phenanthrolinyl group, an isoxazolyl group, a thiadiazolyl group, a phenothiazinyl group, and a dibenzofuranyl group. Specifically, the heteroaryl group may have 2 to 50 carbon atoms, and more specifically, 2 to 30 carbon atoms.

[0034] In the present specification, the amine group may be selected from the group consisting of -NH2, an alkylamine group, an N-alkylarylamine group, an arylamine group, an N-arylheteroarylamine group, an N-alkylheteroarylamine group, and a heteroarylamine group.

[0035] In this specification, an arylene group refers to a divalent aryl group having two bonding positions to an aryl group, and a heteroarylene group also refers to a divalent heteroaryl group having two bonding positions to a heteroaryl group. The descriptions of the aryl group and heteroaryl group described above can be applied to these groups, except that they are each divalent groups.

[0036] In the chemical formula or structural formula in this specification, * or indicates the binding position.

[0037] The novel compound of the present invention is described below.

[0038] The novel compound of the present invention is represented by chemical formula 1.

[0039]

[0040] In the above chemical formula 1,

[0041] R1 to R9 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, nitrile group, substituted or unsubstituted C1~C30 alkyl group, substituted or unsubstituted C1~C30 alkenyl group, substituted or unsubstituted C1~C30 alkynyl group, substituted or unsubstituted C3~C30 cycloalkyl group, substituted or unsubstituted C1~C30 heterocycloalkyl group, substituted or unsubstituted C1~C30 alkoxy group, substituted or unsubstituted C1~C30 sulfide group, substituted or unsubstituted C6~C30 aryl group, substituted or unsubstituted C2~C30 heteroaryl group, substituted or unsubstituted C6~C30 aryloxy group, substituted or unsubstituted C2~C30 heteroaryloxy group, substituted or unsubstituted C1~C30 thio group, substituted or Selected from the group consisting of an unsubstituted C1~C30 amine group, a substituted or unsubstituted C1~C30 silyl group, and a substituted or unsubstituted C1~C30 phosphine oxide group, wherein at least one of R1 to R9 is the structural formula 1,

[0042] In the above structural formula 1,

[0043] L1 and L2 are each independently a substituted or unsubstituted C6~C30 arylene group, or a substituted or unsubstituted C2~C30 heteroarylene group,

[0044] L3 is a direct bond, a substituted or unsubstituted C6~C30 arylene group, or a substituted or unsubstituted C2~C30 heteroarylene group,

[0045] X1 to X5 are each independently N or CR, and at least one is N,

[0046] Here, R is each independently hydrogen, deuterium, halogen, cyano group, nitro group, nitrile group, substituted or unsubstituted C1~C30 alkyl group, substituted or unsubstituted C1~C30 alkenyl group, substituted or unsubstituted C1~C30 alkynyl group, substituted or unsubstituted C3~C30 cycloalkyl group, substituted or unsubstituted C1~C30 heterocycloalkyl group, substituted or unsubstituted C1~C30 alkoxy group, substituted or unsubstituted C1~C30 sulfide group, substituted or unsubstituted C6~C30 aryl group, substituted or unsubstituted C2~C30 heteroaryl group, substituted or unsubstituted C6~C30 aryloxy group, substituted or unsubstituted C2~C30 heteroaryloxy group, substituted or unsubstituted C1~C30 thio group, substituted or unsubstituted It can be selected from the group consisting of a C1~C30 amine group, a substituted or unsubstituted C1~C30 silyl group, and a substituted or unsubstituted C1~C30 phosphine oxide group.

[0047] The compound of the present invention is a compound that combines benzoquinoline and an N-containing monocyclic ring containing at least one N, and is characterized in that the N-containing monocyclic ring is bonded to benzoquinoline via at least two linkers. Due to these structural features, it has excellent electron transport ability, and due to the rigid structure of benzoquinoline, it has excellent durability characteristics, so an organic light-emitting device combined using these can have the advantages of low voltage, high efficiency, and long life.

[0048] Specifically, only one selected from R1 to R9 may be the structural formula 1, and the rest may each independently be hydrogen, deuterium, halogen, a cyano group, a nitro group, a nitrile group, a substituted or unsubstituted C1~C30 alkyl group, a substituted or unsubstituted C3~C30 cycloalkyl group, a substituted or unsubstituted C1~C30 heterocycloalkyl group, a substituted or unsubstituted C6~C30 aryl group, or a substituted or unsubstituted C2~C30 heteroaryl group, and more specifically, may be hydrogen, a substituted or unsubstituted C1~C20 alkyl group, a substituted or unsubstituted C6~C20 aryl group, or a substituted or unsubstituted C2~C20 heteroaryl group, and in one embodiment, may be hydrogen, a phenyl group, a pyridine group, or a naphthyl group.

[0049] According to one embodiment of the present invention, R1, R3, R4, R5, R6 or R8 may be of the structural formula 1, and more specifically, R1 located immediately next to N of benzoquinoline may be of the structural formula 1. In this case, when R1 is of the structural formula 1, R3 having a meta positional relationship with R1 may be hydrogen, a phenyl group, a pyridine group or a naphthyl group, and the rest may all be hydrogen.

[0050] Meanwhile, the above L3 may be specifically a substituted or unsubstituted C6~C30 arylene group or a substituted or unsubstituted C2~C30 heteroarylene group. That is, L3 may not be a direct bond. According to the above, in the compound of the present invention, an N-containing monocyclic ring may be bonded to benzoquinoline through at least three linkers. When the linker is expanded to three or more in this way, faster electron mobility characteristics can be expected, and materials with various refractive indices can be synthesized depending on how the linker is connected para, meta, or ortho. Therefore, when the linker is expanded to three or more in number, low-voltage, high-efficiency organic light-emitting devices can be manufactured due to the fast electron mobility characteristics, and high-performance organic light-emitting devices can be manufactured by more precisely controlling the refractive index.

[0051] According to one embodiment of the present invention, L1 to L3 may each independently be a C6 to C20 arylene group or a C2 to C20 heteroarylene group, which is unsubstituted or substituted with one or more substituents, and the substituents that may be substituted may be a C1 to C10 alkyl group, a C6 to C12 aryl group, or a C2 to C12 heteroaryl group.

[0052] More specifically, L1 to L3 may be configured to include at least one of phenylene, biphenylene, naphthylene, anthracenylene, phenanthrenylene, pyrenylene, dibenzofuranylene, dibenzothiophenylene, fluorenylene, dimethylfluorenylene, diphenylfluorenylene, spirobifluorenylene, carbazolylene, pyridinylene, pyrimidinylene, pyrazinylene, pyridazinylene, triazinylene, quinolinylene, isoquinolinylene, and naphthyridinylene, each independently substituted or unsubstituted with one or more substituents. In one embodiment, the substituent that may be substituted on L1 to L3 may include, but is not particularly limited to, a phenyl group.

[0053] In one embodiment, L1 and L2 may each independently be one selected from the structural formulae L-1 to L-51 below, and L3 may be one selected from the structural formulae L-1 to L-51 below, or may be formed by combining two or more thereof. Here, the meaning of formed by combining two or more thereof means a combination of two or more identical or different structural formulae, and in one embodiment, a case where only three structural formulae L-1 are combined, a case where structural formulae L-1 and L-2 are combined, a case where two structural formulae L-1 and one structural formula L-2 are combined, etc. may be included. The order of combinations is not particularly determined, and all possible combination cases may be included.

[0054]

[0055]

[0056] In the above structural formulas L-28 to L-37,

[0057] Y is independently O, S, CR10R11 or NR12,

[0058] Here, R10 and R11 are hydrogen, a methyl group, or a phenyl group, and may or may not be combined with each other to form a ring, and R12 may be a phenyl group or a biphenyl group. When R10 and R11 combine with each other to form fluorene, structural formulas L-28 to L-37 have the form of spirobifluorene.

[0059] According to one embodiment of the present invention, L1 to L3 may each independently be phenylene (one of structural formulae L-1 to L-3) or naphthalene (one of structural formulae L-4 to L-13). More specifically, at least one of L1 to L3 may be 1,3-phenylene (structural formula L-2) or 1,4-naphthalene (structural formula L-6). In this way, when 1,3-phenylene (structural formula L-2) or 1,4-naphthalene (structural formula L-6) is introduced into the linker, electron mobility and refractive index are optimized, which may be effective in improving the lifespan of the device when used as an electron transport layer or a hole blocking layer. According to one embodiment, 1,3-phenylene (structural formula L-2) can be introduced into one, two, or all three of L1 to L3 to realize a longer lifespan, and 1,4-naphthalene (structural formula L-6) can be introduced into L1, L2, or both L1 and L2 to realize a longer lifespan.

[0060] Meanwhile, the above structural formula 1 may be the following structural formula 1-1.

[0061]

[0062] In the above structural formula 1-1,

[0063] L1 to L3 are the same as defined in the above structural formula 1,

[0064] X1, X3 and X5 are each independently N or CH, and at least one is N,

[0065] Ar1 and Ar2 may each independently be a substituted or unsubstituted C6~C30 aryl group or a substituted or unsubstituted C2~C30 heteroaryl group, and more specifically, may be a substituted or unsubstituted C6~C20 aryl group or a substituted or unsubstituted C2~C20 heteroaryl group.

[0066] Specifically, the above structural formula 1-1 may be any one of the following structural formulas 1-1-A to 1-1-E.

[0067]

[0068] In the above structural formulas 1-1-A to 1-1-E,

[0069] L1 to L3, Ar1 and Ar2 are the same as defined in the above structural formula 1-1 and are therefore omitted.

[0070] According to one embodiment of the present invention, structural formula 1 may be structural formula 1-1-A or 1-1-C.

[0071] According to one embodiment of the present invention, Ar1 and Ar2 may each independently be selected from a phenyl group, a biphenyl group, a naphthyl group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a phenanthrene group, a fluorene group, a dimethylfluorene group, a diphenylfluorene group, a spirobifluorene group, and a carbazole group, each of which is unsubstituted or substituted with one or more substituents. According to the above, Ar1 and Ar2 may each independently be selected from the following structural formulae A-1 to A-47.

[0072]

[0073]

[0074] According to one embodiment of the present invention, Ar1 and Ar2 may be a phenyl group (structural formula A-1), a biphenyl group (structural formula A-2), a naphthyl group (structural formula A-4), or a pyridine group (one of structural formulas A-6 to A-8), and more specifically, may be a phenyl group or a pyridine group. With reference to the above, the structural formula 1-1 may be any one of the structural formulas below according to one embodiment, but is not particularly limited thereto.

[0075]

[0076] The compound according to the chemical formula 1 of the present invention may be one of the following compounds 1 to 1281.

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149] The novel compound according to the present invention described so far has a structure in which an N-containing monocyclic ring such as pyridine, pyrimidine or triazine is bonded to the core of benzoquinoline, and is bonded through at least two or three or more linkers. Due to this structural feature, the compound has excellent electron transport properties, and thus has features suitable for an organic layer in an organic light-emitting device, particularly an electron transport layer, a hole blocking layer or a charge generation layer.

[0150] Meanwhile, the novel compound of the present invention described above can be applied to at least one of the organic layers of an organic light-emitting device including a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode.

[0151] Below, the organic light-emitting device is described in more detail.

[0152] An organic light-emitting device has an organic layer positioned between first electrodes. The organic layer may be composed of one or more organic layers, and specifically, may be composed of one or more layers selected from known organic layers that constitute a light-emitting portion, such as a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer.

[0153] The hole injection layer (HIL) is a layer that injects holes from an electrode. The hole injection material is preferably a compound that has the ability to transport holes, has an excellent hole injection effect at the anode, an excellent hole injection effect for the light-emitting layer or light-emitting material, prevents the movement of excitons generated in the light-emitting layer to the electron injection layer or electron injection material, and has excellent thin film forming ability.

[0154] The hole transport layer (HTL) is a layer that receives holes from the hole injection layer and transports them to the light-emitting layer. As the hole transport material, a material with high hole mobility is suitable, as it can transport holes from the anode or the hole injection layer and move them to the light-emitting layer.

[0155] The light-emitting material used in the emission layer (EML) is a material that can emit light in the visible light range by transporting holes and electrons from the hole transport layer and the electron transport layer, respectively, and combining them. A material with good quantum efficiency for fluorescence or phosphorescence is preferable. The emission layer may include a host material and a dopant material.

[0156] The electron transport layer (ETL) is a layer that receives electrons from the electron injection layer and transports them to the light-emitting layer. The electron transport material is a material that can easily receive electrons from the cathode and transfer them to the light-emitting layer, and a material with high electron mobility is preferable.

[0157] The electron injection layer (EIL) is a layer that injects electrons from an electrode, has the ability to transport electrons, has an electron injection effect from a cathode, has an excellent electron injection effect for a light-emitting layer or light-emitting material, prevents movement of excitons generated in the light-emitting layer to the hole injection layer, and is preferably a compound having excellent thin-film forming ability.

[0158] The organic layer may further include a hole blocking layer (HBL). The HBL may be positioned between the light-emitting layer and the electron transport layer, and reduces the problem of holes in the hole injection layer invading the electron transport layer.

[0159] Among the organic layers of such organic light-emitting devices, the novel compound of the present invention is particularly preferably applied to an electron transport layer or a hole blocking layer.

[0160] Meanwhile, the composition of the organic light-emitting device can vary. For example, it can be a tandem structure in which multiple light-emitting layers (or light-emitting units) are provided, and in the case of a tandem structure, a charge generation layer (CGL) can be further included as one of the organic layers in addition to the above-mentioned organic layers. In general, the charge generation layer is composed of multiple layers including an N-type charge generation layer and a P-type charge generation layer, but is not limited thereto and can also be composed of a single layer.

[0161] The novel compound of the present invention can also be applied to a charge generation layer of such a tandem organic light-emitting device, and specifically, can be applied to an N-type charge generation layer.

[0162] An organic light-emitting device in which the novel compound according to the present invention is applied to at least one organic layer among an electron transport layer, a hole blocking layer, and a charge generation layer can realize low voltage, high efficiency, high brightness, and long life.

[0163] Hereinafter, the present invention will be described in more detail with synthetic examples, practical examples, and experimental examples. However, the following contents do not limit the scope of the present invention.

[0164] Synthetic example

[0165] Synthesis of intermediate-A

[0166]

[0167] In a 1 L round bottom flask, 1-(4-bromophenyl)ethan-1-one (25.0 g, 125.6 mmol), the following intermediate-6 (34.2 g, 138.2 mmol), and KOH (21.1 g, 376.8 mmol) were dissolved in 175 mL of toluene and 125 mL of EtOH, and the mixture was refluxed for 6 hours. After the reaction was completed, extraction was performed using DCM and water. The organic layer was dried over MgSO4 and concentrated under reduced pressure. The obtained filtrate was purified by column chromatography to obtain intermediate-A (45.7 g, 88%).

[0168] Synthesis of intermediate B

[0169]

[0170] In a 1 L round-bottom flask, intermediate-A (40.0 g, 97.5 mmol), bis(pinacolato)diboron (27.2 g, 107.2 mmol), potassium acetate (28.7 g, 363.5 mmol), and Pd(dppf)Cl2 (2.1 g, 2.9 mmol) were dissolved in 680 mL of 1,4-dioxane and stirred under reflux for 8 hours. After the reaction was completed, the mixture was cooled to room temperature and the reaction solution was filtered under reduced pressure through Celite to obtain a filtrate. The filtrate was purified by column chromatography to obtain intermediate-B (31.8 g, 71%).

[0171] Synthetic Example 1. Synthesis of Compound 51

[0172]

[0173] In a 1 L round bottom flask, add intermediate-A (12.0 g, 26.2 mmol), intermediate-B (9.7 g, 24.9 mmol), tetrakis(triphenylphophine)palladium (1.5 g, 1.3 mmol), and K2CO3 (10.9 g, 78.7 mmol), dissolve 260 mL of 1,4-dioxane and 130 mL of H2O, and reflux for 8 hours. After the reaction is complete, cool to room temperature and extract with dichloromethane and water. The organic layer was dried with MgSO4, concentrated under reduced pressure, and the resulting filtrate was recrystallized to obtain compound 51 (12.8 g, 76%).

[0174] Synthesis of intermediate-1

[0175]

[0176] In a 1 L round bottom flask, 1-(4-bromophenyl)ethan-1-one (30.0 g, 150.7 mmol), 1-amino-2-naphthaldehyde (28.4, 165.8 mmol), and KOH (25.4 g, 452.1 mmol) were dissolved in 210 mL of toluene and 150 mL of EtOH, and stirred under reflux for 6 hours. After the reaction was completed, the mixture was extracted using DCM and water. The organic layer was dried over MgSO4 and concentrated under reduced pressure. The obtained filtrate was purified by column chromatography to obtain intermediate-1 (40.6 g, 81%).

[0177] Synthesis of intermediate-2

[0178]

[0179] In a 1 L round bottom flask, intermediate-1 (40.5 g, 121.2 mmol), bis(pinacolato)diboron (33.9 g, 133.3 mmol), potassium acetate (35.7 g, 363.5 mmol), and Pd(dppf)Cl2 (2.7 g, 3.6 mmol) were dissolved in 680 mL of 1,4-dioxane and stirred under reflux for 8 hours. After the reaction was completed, the mixture was cooled to room temperature and the reaction solution was filtered under reduced pressure through Celite to obtain a filtrate. The filtrate was purified by column chromatography to obtain intermediate-2 (39.2 g, 85%).

[0180] Synthesis of intermediate-3

[0181]

[0182] In a 1 L round-bottom flask, dissolve 1-bromo-3-iodobenzene (9.0 g, 31.8 mmol), 4'-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-2,2':6',2''-terpyridine (15.2 g, 35.0 mmol), tetrakis(triphenylphophine)palladium (1.8 g, 1.6 mmol), and K2CO3 (13.2 g, 95.4 mmol) in 320 mL of 1,4-dioxane and 160 mL of H2O, and stir under reflux for 8 hours. After the reaction is complete, cool to room temperature and extract with dichloromethane and water. The organic layer was dehydrated with MgSO4 and concentrated under reduced pressure, and the resulting filtrate was purified by column chromatography to obtain intermediate-3 (13.1 g, 88%).

[0183] Synthetic Example 2. Synthesis of Compound 103

[0184]

[0185] In a 1 L round bottom flask, add intermediate-2 (11.0 g, 28.9 mmol), intermediate-3 (12.7 g, 27.4 mmol), tetrakis(triphenylphophine)palladium (1.7 g, 1.4 mmol), and K2CO3 (12.0 g, 86.6 mmol), dissolve 290 mL of 1,4-dioxane and 150 mL of H2O, and reflux for 8 hours. After the reaction is complete, cool to room temperature and extract with dichloromethane and water. The organic layer was dried with MgSO4, concentrated under reduced pressure, and the obtained filtrate was recrystallized to obtain compound 103 (13.6 g, 74%).

[0186] Synthesis of intermediate-4

[0187]

[0188] In a 1 L round-bottom flask, dissolve 1-bromo-3-iodobenzene (9.0 g, 31.8 mmol), 4,6-diphenyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine (15.2 g, 35.0 mmol), tetrakis(triphenylphophine)palladium (1.8 g, 1.6 mmol), and K2CO3 (13.2 g, 95.4 mmol) in 320 mL of 1,4-dioxane and 160 mL of H2O, and reflux for 8 hours. After the reaction is complete, cool to room temperature and extract using dichloromethane and water. The organic layer was dehydrated with MgSO4 and concentrated under reduced pressure, and the resulting filtrate was purified by column chromatography to obtain intermediate-4 (11.3 g, 77%).

[0189] Synthetic Example 3. Synthesis of Compound 104

[0190]

[0191] In a 1 L round bottom flask, add intermediate-2 (9 g, 23.6 mmol), intermediate-4 (10.4 g, 22.4 mmol), tetrakis(triphenylphophine)palladium (1.4 g, 1.2 mmol), and K2CO3 (9.8 g, 70.8 mmol), dissolve 240 mL of 1,4-dioxane and 120 mL of H2O, and reflux for 8 hours. After the reaction is complete, cool to room temperature and extract with dichloromethane and water. The organic layer was dried with MgSO4, concentrated under reduced pressure, and the obtained filtrate was recrystallized to obtain compound 104 (11.5 g, 76%).

[0192] Synthesis of intermediate-5

[0193]

[0194] In a 1 L round-bottom flask, dissolve 1-bromo-3-iodobenzene (10.0 g, 35.3 mmol), 2,4-diphenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (16.9 g, 38.9 mmol), tetrakis(triphenylphophine)palladium (2.0 g, 1.8 mmol), and K2CO3 (14.7 g, 106.0 mmol) in 350 mL of 1,4-dioxane and 175 mL of H2O, and reflux for 8 hours. After the reaction is complete, cool to room temperature and extract with dichloromethane and water. The organic layer was dehydrated with MgSO4 and concentrated under reduced pressure, and the resulting filtrate was purified by column chromatography to obtain intermediate-5 (11.3 g, 69%).

[0195] Synthetic Example 4. Synthesis of Compound 105

[0196]

[0197] In a 1 L round bottom flask, add intermediate-2 (9.0 g, 26.2 mmol), intermediate-5 (10.1 g, 22.4 mmol), tetrakis(triphenylphophine)palladium (1.4 g, 1.2 mmol), and K2CO3 (9.8 g, 70.8 mmol), dissolve 240 mL of 1,4-dioxane and 120 mL of H2O, and reflux for 8 hours. After the reaction is complete, cool to room temperature and extract with dichloromethane and water. The organic layer was dried with MgSO4, concentrated under reduced pressure, and the obtained filtrate was recrystallized to obtain compound 105 (11.1 g, 74%).

[0198] Synthesis of intermediate-6

[0199]

[0200] In a 500 mL round-bottom flask, dissolve 2-benzoyl-1-naphtol (20.0 g, 80.6 mmol) and sodium hydroxide (9.7 g, 24.2 mmol) in 120 mL of N,N-dimethylacetamide (DMA) and stir at room temperature for 1 hour. Add 2-bromoisobutylamide (40.1 g, 241.7 mmol) and stir at room temperature for an additional 5 hours. Add sodium hydroxide (29.0 g, 725.0 mmol) to the reaction solution and stir at 50°C for 1 hour. Add 60 mL of water and raise the temperature to reflux for an additional hour. After the reaction is complete, cool to room temperature and extract using ethyl acetate and water. The organic layer was dehydrated with MgSO4 and concentrated under reduced pressure, and the resulting filtrate was purified by column chromatography to obtain intermediate-6 (34.7 g, 93%).

[0201] Synthesis of intermediate-7

[0202]

[0203] In a 1 L round bottom flask, 1-(3-bromophenyl)ethan-1-one (25.0 g, 125.6 mmol), intermediate-6 (34.2 g, 138.2 mmol), and KOH (21.1 g, 376.8 mmol) were dissolved in 175 mL of toluene and 125 mL of EtOH, and stirred under reflux for 6 hours. After the reaction was completed, the mixture was extracted using DCM and water, and the organic layer was dried over MgSO4 and concentrated under reduced pressure. The obtained filtrate was purified by column chromatography to obtain intermediate-7 (44.6 g, 86%).

[0204] Synthesis of intermediate-8

[0205]

[0206] In a 1 L round-bottomed flask, intermediate-7 (40.0 g, 97.5 mmol), bis(pinacolato)diboron (27.2 g, 107.2 mmol), potassium acetate (28.7 g, 363.5 mmol), and Pd(dppf)Cl2 (2.1 g, 2.9 mmol) were dissolved in 680 mL of 1,4-dioxane and stirred under reflux for 8 hours. After the reaction was completed, the mixture was cooled to room temperature and the reaction solution was filtered under reduced pressure through Celite to obtain a filtrate. The filtrate was purified by column chromatography to obtain intermediate-8 (35.3 g, 79%).

[0207] Synthesis of intermediate-9

[0208]

[0209] In a 1 L round-bottom flask, dissolve 1-bromo-3-iodobenzene (10.0 g, 35.3 mmol), 4'-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-2,2':6',2''-terpyridine (16.9 g, 38.9 mmol), tetrakis(triphenylphophine)palladium (2.0 g, 1.8 mmol), and K2CO3 (14.7 g, 106.0 mmol) in 350 mL of 1,4-dioxane and 175 mL of H2O, and then reflux and stir for 8 hours. After the reaction is complete, cool to room temperature and extract with dichloromethane and water. The organic layer was dehydrated with MgSO4 and concentrated under reduced pressure, and the resulting filtrate was purified by column chromatography to obtain intermediate-9 (11.8 g, 72%).

[0210] Synthetic Example 5. Synthesis of Compound 175

[0211]

[0212] In a 1 L round bottom flask, add intermediate-8 (12.0 g, 26.2 mmol), intermediate-9 (11.6 g, 24.9 mmol), tetrakis(triphenylphophine)palladium (1.5 g, 1.3 mmol), and K2CO3 (10.9 g, 78.7 mmol), dissolve 260 mL of 1,4-dioxane and 130 mL of H2O, and reflux for 8 hours. After the reaction is complete, cool to room temperature and extract with dichloromethane and water. The organic layer was dried with MgSO4, concentrated under reduced pressure, and the obtained filtrate was recrystallized to obtain compound 175 (13.9 g, 74%).

[0213] Synthesis of intermediate-10

[0214]

[0215] In a 1 L round-bottom flask, dissolve 1-bromo-3-iodobenzene (8.0 g, 28.3 mmol), 4,6-diphenyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine (13.5 g, 31.1 mmol), tetrakis(triphenylphophine)palladium (1.6 g, 1.4 mmol), and K2CO3 (11.7 g, 84.8 mmol) in 280 mL of 1,4-dioxane and 140 mL of H2O, and stir under reflux for 8 hours. After the reaction is complete, cool to room temperature and extract with dichloromethane and water. The organic layer was dehydrated with MgSO4 and concentrated under reduced pressure, and the resulting filtrate was purified by column chromatography to obtain intermediate-10 (9.3 g, 71%).

[0216] Synthetic Example 6. Synthesis of Compound 176

[0217]

[0218] In a 1 L round bottom flask, add intermediate-8 (9.0 g, 19.7 mmol), intermediate-10 (8.7 g, 18.7 mmol), tetrakis(triphenylphophine)palladium (1.1 g, 1.0 mmol), and K2CO3 (8.2 g, 59.0 mmol), dissolve 200 mL of 1,4-dioxane and 100 mL of H2O, and reflux for 8 hours. After the reaction is complete, cool to room temperature and extract with dichloromethane and water. The organic layer was dried with MgSO4, concentrated under reduced pressure, and the obtained filtrate was recrystallized to obtain compound 176 (10.6 g, 75%).

[0219] Synthesis of intermediate-11

[0220]

[0221] In a 1 L round-bottom flask, dissolve 1-bromo-3-iodobenzene (8.0 g, 28.3 mmol), 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (13.5 g, 31.1 mmol), tetrakis(triphenylphophine)palladium (1.6 g, 1.4 mmol), and K2CO3 (11.7 g, 84.8 mmol) in 280 mL of 1,4-dioxane and 140 mL of H2O, and stir under reflux for 8 hours. After the reaction is complete, cool to room temperature and extract with dichloromethane and water. The organic layer was dehydrated with MgSO4 and concentrated under reduced pressure, and the resulting filtrate was purified by column chromatography to obtain intermediate-11 (10.2 g, 77%).

[0222] Synthetic Example 7. Synthesis of Compound 177

[0223]

[0224] In a 1 L round bottom flask, add intermediate-8 (10.0 g, 21.9 mmol), intermediate-11 (9.7 g, 20.8 mmol), tetrakis(triphenylphophine)palladium (1.3 g, 1.1 mmol), and K2CO3 (9.1 g, 65.6 mmol), dissolve 220 mL of 1,4-dioxane and 110 mL of H2O, and reflux for 8 hours. After the reaction is complete, cool to room temperature and extract with dichloromethane and water. The organic layer was dried with MgSO4, concentrated under reduced pressure, and the obtained filtrate was recrystallized to obtain compound 177 (12.0 g, 77%).

[0225] Synthesis of intermediate-12

[0226]

[0227] In a 1 L round bottom flask, 1-(2-bromophenyl)ethan-1-one (30.0 g, 150.7 mmol), intermediate-6 (41.0 g, 165.8 mmol), and KOH (25.4 g, 452.1 mmol) were dissolved in 210 mL of toluene and 150 mL of EtOH, and stirred under reflux for 6 hours. After the reaction was completed, the mixture was extracted using DCM and water, and the organic layer was dried over MgSO4 and concentrated under reduced pressure. The obtained filtrate was purified by column chromatography to obtain intermediate-12 (38.7 g, 63%).

[0228] Synthesis of intermediate-13

[0229]

[0230] Intermediate-12 (35.0 g, 85.3 mmol), bis(pinacolato)diboron (23.8 g, 93.8 mmol), potassium acetate (25.1 g, 363.5 mmol), and Pd(dppf)Cl2 (1.9 g, 2.6 mmol) were dissolved in 600 mL of 1,4-dioxane in a 1 L round-bottomed flask and stirred under reflux for 8 hours. After the reaction was completed, the mixture was cooled to room temperature and the reaction solution was filtered under reduced pressure through Celite to obtain a filtrate. The filtrate was purified by column chromatography to obtain intermediate-13 (31.6 g, 81%).

[0231] Synthetic Example 8. Synthesis of Compound 208

[0232]

[0233] In a 1 L round bottom flask, add intermediate-13 (8.0 g, 17.5 mmol), intermediate-9 (7.7 g, 16.6 mmol), tetrakis(triphenylphophine)palladium (1.0 g, 1.1 mmol), and K2CO3 (7.3 g, 52.5 mmol), dissolve 170 mL of 1,4-dioxane and 80 mL of H2O, and reflux for 8 hours. After the reaction is complete, cool to room temperature and extract with dichloromethane and water. The organic layer was dried with MgSO4, concentrated under reduced pressure, and the obtained filtrate was recrystallized to obtain compound 208 (8.9 g, 71%).

[0234] Synthetic Example 9. Synthesis of Compound 209

[0235]

[0236] In a 1 L round bottom flask, add intermediate-13 (9.0 g, 19.7 mmol), intermediate-10 (8.7 g, 18.7 mmol), tetrakis(triphenylphophine)palladium (1.1 g, 1.0 mmol), and K2CO3 (8.2 g, 59.0 mmol), dissolve 200 mL of 1,4-dioxane and 100 mL of H2O, and reflux for 8 hours. After the reaction is complete, cool to room temperature and extract with dichloromethane and water. The organic layer was dried over MgSO4, concentrated under reduced pressure, and the obtained filtrate was recrystallized to obtain compound 209 (10.5 g, 75%).

[0237] Synthetic Example 10. Synthesis of Compound 210

[0238]

[0239] In a 1 L round bottom flask, add intermediate-13 (10.0 g, 21.9 mmol), intermediate-11 (9.7 g, 20.8 mmol), tetrakis(triphenylphophine)palladium (1.3 g, 1.1 mmol), and K2CO3 (9.1 g, 65.6 mmol), dissolve 220 mL of 1,4-dioxane and 110 mL of H2O, and reflux for 8 hours. After the reaction is complete, cool to room temperature and extract with dichloromethane and water. The organic layer was dried with MgSO4, concentrated under reduced pressure, and the obtained filtrate was recrystallized to obtain compound 210 (12.4 g, 79%).

[0240] Synthesis of intermediate-14

[0241]

[0242] In a 1 L round bottom flask, 1-(4-bromonaphthalen-1-yl)ethan-1-one (30.0 g, 120.4 mmol), intermediate-6 (32.8 g, 132.5 mmol), and KOH (20.3 g, 361.3 mmol) were dissolved in 210 mL of toluene and 150 mL of EtOH, and stirred under reflux for 6 hours. After the reaction was completed, the mixture was extracted using DCM and water, and the organic layer was dried over MgSO4 and concentrated under reduced pressure. The obtained filtrate was purified by column chromatography to obtain intermediate-14 (32.9 g, 59%).

[0243] Synthesis of intermediate-15

[0244]

[0245] Intermediate-14 (30.0 g, 65.2 mmol), bis(pinacolato)diboron (18.2 g, 71.7 mmol), potassium acetate (19.2 g, 195.5 mmol), and Pd(dppf)Cl2 (1.4 g, 2.0 mmol) were dissolved in 500 mL of 1,4-dioxane in a 1 L round-bottomed flask and stirred under reflux for 8 hours. After the reaction was completed, the mixture was cooled to room temperature and the reaction solution was filtered under reduced pressure through Celite to obtain a filtrate. The filtrate was purified by column chromatography to obtain intermediate-15 (28.6 g, 86%).

[0246] Synthesis of intermediate-16

[0247]

[0248] In a 1 L round-bottom flask, dissolve 1-bromo-4-iodobenzene (7.0 g, 24.7 mmol), 4'-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-2,2':6',2''-terpyridine (11.9 g, 27.2 mmol), tetrakis(triphenylphophine)palladium (1.4 g, 1.2 mmol), and K2CO3 (10.3 g, 74.2 mmol) in 250 mL of 1,4-dioxane and 120 mL of H2O, and stir under reflux for 8 hours. After the reaction is complete, cool to room temperature and extract with dichloromethane and water. The organic layer was dehydrated with MgSO4 and concentrated under reduced pressure, and the resulting filtrate was purified by column chromatography to obtain intermediate-16 (8.4 g, 73%).

[0249] Synthetic Example 11. Synthesis of Compound 370

[0250]

[0251] In a 1 L round bottom flask, add intermediate-15 (9.0 g, 17.7 mmol), intermediate-16 (7.8 g, 16.8 mmol), tetrakis(triphenylphophine)palladium (1.0 g, 0.9 mmol), and K2CO3 (7.4 g, 53.2 mmol), dissolve 180 mL of 1,4-dioxane and 90 mL of H2O, and reflux for 8 hours. After the reaction is complete, cool to room temperature and extract with dichloromethane and water. The organic layer was dried over MgSO4, concentrated under reduced pressure, and the obtained filtrate was recrystallized to obtain compound 370 (10.0 g, 74%).

[0252] Synthesis of intermediate-17

[0253]

[0254] In a 1 L round-bottom flask, dissolve 1-bromo-4-iodobenzene (8.0 g, 28.3 mmol), 4,6-diphenyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine (13.5 g, 31.1 mmol), tetrakis(triphenylphophine)palladium (1.6 g, 1.4 mmol), and K2CO3 (11.7 g, 84.8 mmol) in 280 mL of 1,4-dioxane and 140 mL of H2O, and reflux for 8 hours. After the reaction is complete, cool to room temperature and extract with dichloromethane and water. The organic layer was dehydrated with MgSO4 and concentrated under reduced pressure, and the resulting filtrate was purified by column chromatography to obtain intermediate-17 (10.7 g, 82%).

[0255] Synthetic Example 12. Synthesis of Compound 371

[0256]

[0257] In a 1 L round bottom flask, add intermediate-15 (12.0 g, 23.6 mmol), intermediate-17 (10.4 g, 22.5 mmol), tetrakis(triphenylphophine)palladium (1.4 g, 1.2 mmol), and K2CO3 (9.8 g, 70.9 mmol), dissolve 240 mL of 1,4-dioxane and 120 mL of H2O, and reflux for 8 hours. After the reaction is complete, cool to room temperature and extract with dichloromethane and water. The organic layer was dried with MgSO4, concentrated under reduced pressure, and the obtained filtrate was recrystallized to obtain compound 371 (14.4 g, 80%).

[0258] Synthesis of intermediate-18

[0259]

[0260] In a 1 L round-bottom flask, dissolve 1-bromo-4-iodobenzene (8.0 g, 28.3 mmol), 2,4-diphenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (13.5 g, 31.1 mmol), tetrakis(triphenylphophine)palladium (1.6 g, 1.4 mmol), and K2CO3 (11.7 g, 84.8 mmol) in 280 mL of 1,4-dioxane and 140 mL of H2O, and stir under reflux for 8 hours. After the reaction is complete, cool to room temperature and extract with dichloromethane and water. The organic layer was dehydrated with MgSO4 and concentrated under reduced pressure, and the resulting filtrate was purified by column chromatography to obtain intermediate-18 (9.6 g, 73%).

[0261] Synthetic Example 13. Synthesis of Compound 372

[0262]

[0263] In a 1 L round bottom flask, add intermediate-15 (10.0 g, 19.7 mmol), intermediate-18 (8.7 g, 18.7 mmol), tetrakis(triphenylphophine)palladium (1.1 g, 1.0 mmol), and K2CO3 (8.2 g, 59.1 mmol), dissolve 200 mL of 1,4-dioxane and 100 mL of H2O, and reflux for 8 hours. After the reaction is complete, cool to room temperature and extract with dichloromethane and water. The organic layer was dried over MgSO4, concentrated under reduced pressure, and the resulting filtrate was recrystallized to obtain compound 372 (12.9 g, 86%).

[0264] Synthesis of intermediate-19

[0265]

[0266] In a 1 L round-bottom flask, dissolve 1-bromo-4-iodobenzene (8.0 g, 28.3 mmol), 4'-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-2,2':6',2''-terpyridine (13.5 g, 31.1 mmol), tetrakis(triphenylphophine)palladium (1.6 g, 1.4 mmol), and K2CO3 (11.7 g, 84.8 mmol) in 280 mL of 1,4-dioxane and 140 mL of H2O, and stir under reflux for 8 hours. After the reaction is complete, cool to room temperature and extract with dichloromethane and water. The organic layer was dehydrated with MgSO4 and concentrated under reduced pressure, and the resulting filtrate was purified by column chromatography to obtain intermediate-19 (10.2 g, 78%).

[0267] Synthetic Example 14. Synthesis of Compound 430

[0268]

[0269] In a 1 L round bottom flask, add intermediate-15 (11.0 g, 21.7 mmol), intermediate-19 (9.6 g, 20.6 mmol), tetrakis(triphenylphophine)palladium (1.3 g, 1.1 mmol), and K2CO3 (9.0 g, 65.0 mmol), dissolve 220 mL of 1,4-dioxane and 110 mL of H2O, and reflux for 8 hours. After the reaction is complete, cool to room temperature and extract with dichloromethane and water. The organic layer was dried over MgSO4, concentrated under reduced pressure, and the obtained filtrate was recrystallized to obtain compound 430 (13.8 g, 83%).

[0270] Synthesis of intermediate-20

[0271]

[0272] In a 1 L round-bottom flask, dissolve 1-bromo-4-iodobenzene (8.0 g, 28.3 mmol), 4,6-diphenyl-2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine (13.5 g, 31.1 mmol), tetrakis(triphenylphophine)palladium (1.6 g, 1.4 mmol), and K2CO3 (11.7 g, 84.8 mmol) in 280 mL of 1,4-dioxane and 140 mL of H2O, and stir under reflux for 8 hours. After the reaction is complete, cool to room temperature and extract with dichloromethane and water. The organic layer was dehydrated with MgSO4 and concentrated under reduced pressure, and the resulting filtrate was purified by column chromatography to obtain intermediate-20 (9.1 g, 69%).

[0273] Synthetic Example 15. Synthesis of Compound 431

[0274]

[0275] In a 1 L round bottom flask, add intermediate-15 (10.0 g, 19.7 mmol), intermediate-20 (8.7 g, 18.7 mmol), tetrakis(triphenylphophine)palladium (1.1 g, 1.0 mmol), and K2CO3 (8.2 g, 59.1 mmol), dissolve 200 mL of 1,4-dioxane and 100 mL of H2O, and reflux for 8 hours. After the reaction is complete, cool to room temperature and extract with dichloromethane and water. The organic layer was dried over MgSO4, concentrated under reduced pressure, and the obtained filtrate was recrystallized to obtain compound 431 (11.2 g, 74%).

[0276] Synthesis of intermediate-21

[0277]

[0278] In a 1 L round-bottom flask, dissolve 1-bromo-4-iodobenzene (10.0 g, 35.3 mmol), 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (16.9 g, 38.9 mmol), tetrakis(triphenylphophine)palladium (2.0 g, 1.8 mmol), and K2CO3 (14.7 g, 106.0 mmol) in 350 mL of 1,4-dioxane and 170 mL of H2O, and stir under reflux for 8 hours. After the reaction is complete, cool to room temperature and extract with dichloromethane and water. The organic layer was dehydrated with MgSO4 and concentrated under reduced pressure, and the resulting filtrate was purified by column chromatography to obtain intermediate-21 (13.3 g, 81%).

[0279] Synthetic Example 16. Synthesis of Compound 432

[0280]

[0281] In a 1 L round bottom flask, add intermediate-15 (12.0 g, 23.6 mmol), intermediate-21 (10.4 g, 22.5 mmol), tetrakis(triphenylphophine)palladium (1.4 g, 1.2 mmol), and K2CO3 (9.8 g, 70.9 mmol), dissolve 230 mL of 1,4-dioxane and 160 mL of H2O, and reflux for 8 hours. After the reaction is complete, cool to room temperature and extract with dichloromethane and water. The organic layer was dried with MgSO4, concentrated under reduced pressure, and the obtained filtrate was recrystallized to obtain compound 432 (14.9 g, 82%).

[0282] Synthesis of intermediate-22

[0283]

[0284] In a 1 L round-bottom flask, dissolve 1-bromo-4-iodonaphthalene (8.0 g, 24.0 mmol), 4'-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-2,2':6',2''-terpyridine (11.5 g, 26.4 mmol), tetrakis(triphenylphophine)palladium (1.4 g, 1.2 mmol), and K2CO3 (10.0 g, 72.1 mmol) in 240 mL of 1,4-dioxane and 120 mL of H2O, and stir under reflux for 8 hours. After the reaction is complete, cool to room temperature and extract with dichloromethane and water. The organic layer was dehydrated with MgSO4 and concentrated under reduced pressure, and the resulting filtrate was purified by column chromatography to obtain intermediate-22 (8.4 g, 68%).

[0285] Synthetic Example 17. Synthesis of Compound 451

[0286]

[0287] In a 1 L round bottom flask, add intermediate-15 (8.0 g, 15.8 mmol), intermediate-22 (7.7 g, 15.0 mmol), tetrakis(triphenylphophine)palladium (0.9 g, 0.8 mmol), and K2CO3 (6.5 g, 47.3 mmol), dissolve 160 mL of 1,4-dioxane and 120 mL of H2O, and reflux for 8 hours. After the reaction is complete, cool to room temperature and extract with dichloromethane and water. The organic layer was dried over MgSO4, concentrated under reduced pressure, and the obtained filtrate was recrystallized to obtain compound 451 (9.1 g, 71%).

[0288] Synthesis of intermediate-23

[0289]

[0290] In a 1 L round-bottom flask, dissolve 1-bromo-4-iodonaphthalene (10.0 g, 30.0 mmol), 4,6-diphenyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidine (14.4 g, 33.0 mmol), tetrakis(triphenylphophine)palladium (1.7 g, 1.5 mmol), and K2CO3 (12.5 g, 90.1 mmol) in 300 mL of 1,4-dioxane and 150 mL of H2O, and then stir under reflux for 8 hours. After the reaction is complete, cool to room temperature and extract using dichloromethane and water. The organic layer was dehydrated with MgSO4 and concentrated under reduced pressure, and the resulting filtrate was purified by column chromatography to obtain intermediate-23 (12.6 g, 82%).

[0291] Synthetic Example 18. Synthesis of Compound 452

[0292]

[0293] In a 1 L round bottom flask, add intermediate-15 (11.0 g, 21.7 mmol), intermediate-23 (10.6 g, 20.6 mmol), tetrakis(triphenylphophine)palladium (1.3 g, 1.1 mmol), and K2CO3 (9.0 g, 65.0 mmol), dissolve 220 mL of 1,4-dioxane and 160 mL of H2O, and reflux for 8 hours. After the reaction is complete, cool to room temperature and extract with dichloromethane and water. The organic layer was dried over MgSO4, concentrated under reduced pressure, and the obtained filtrate was recrystallized to obtain compound 452 (13.4 g, 76%).

[0294] Synthesis of intermediate-24

[0295]

[0296] In a 1 L round-bottom flask, dissolve 1-bromo-4-iodonaphthalene (7.0 g, 21.0 mmol), 2,4-diphenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine (10.1 g, 23.1 mmol), tetrakis(triphenylphophine)palladium (1.2 g, 1.1 mmol), and K2CO3 (8.7 g, 63.1 mmol) in 210 mL of 1,4-dioxane and 100 mL of H2O, and stir under reflux for 8 hours. After the reaction is complete, cool to room temperature and extract using dichloromethane and water. The organic layer was dehydrated with MgSO4 and concentrated under reduced pressure, and the resulting filtrate was purified by column chromatography to obtain intermediate-24 (7.9 g, 73%).

[0297] Synthetic Example 19. Synthesis of Compound 453

[0298]

[0299] In a 1 L round bottom flask, add intermediate-15 (8.0 g, 15.8 mmol), intermediate-24 (7.7 g, 15.0 mmol), tetrakis(triphenylphophine)palladium (0.9 g, 0.8 mmol), and K2CO3 (6.5 g, 47.3 mmol), dissolve 160 mL of 1,4-dioxane and 80 mL of H2O, and reflux for 8 hours. After the reaction is complete, cool to room temperature and extract with dichloromethane and water. The organic layer was dried over MgSO4, concentrated under reduced pressure, and the resulting filtrate was recrystallized to obtain compound 453 (8.7 g, 68%).

[0300] Fabrication of organic light-emitting devices

[0301] Comparative Example 1

[0302] After patterning the ITO substrate to serve as the anode so that the light-emitting area is 2 mm × 2 mm, it is cleaned with isopropyl alcohol and UV ozone, respectively. Afterwards, the ITO substrate is mounted on the substrate holder of a vacuum deposition device and the vacuum level is 1 × 10 -7 The pressure was set to 10 torr. Afterwards, plasma treatment was performed for 3 minutes under a N2 atmosphere. First, HAT-CN was vacuum-deposited to form a 7 nm thick hole injection layer. NPB material was vacuum-deposited on top of this to form a 90 nm thick hole transport layer. Then, α,β-AND material was co-deposited as a host and TPPDA material as a dopant at a mass ratio of approximately 4% to form a 25 nm thick blue light-emitting layer. BCP compound was vacuum-deposited on this light-emitting layer to form a 5 nm thick hole-blocking layer. Bphen material was vacuum-deposited on top of this to form an electron transport layer with a thickness of 20 nm. LiF material was then deposited to form an electron injection layer with a thickness of 1 nm. Al was then deposited to a thickness of 100 nm to form a cathode, thereby fabricating the final organic light-emitting device. The HAT-CN, NPB, α,β-ADN, TPPDA, BCP, and Bphen materials previously used are shown in Table 1 below.

[0303] [Table 1]

[0304] Comparison Example 2

[0305] An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that Comparative Compound 1 shown in Table 2 below was used instead of BCP as a hole-blocking layer.

[0306] [Table 2]

[0307]

[0308] Examples 1 to 19

[0309] An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that the compounds synthesized in Synthesis Examples 1 to 19 were used instead of BCP as the hole-blocking layer.

[0310] Experimental Example 1. Evaluation of Organic Light-Emitting Diodes (Application of Hole-Blocking Layer)

[0311] The operating voltage, current efficiency, and lifespan of the previously fabricated organic light-emitting device were evaluated. The evaluation results are shown in Table 3 below.

[0312] [Table 3]

[0313]

[0314] As can be seen from the results in Table 3 above, the organic light-emitting device using the compounds of the present invention as a hole-blocking layer showed lower operating voltage and improved current efficiency and lifespan compared to the organic light-emitting devices of the comparative examples. It was seen that the remaining cases using compounds combining benzoquinoline and N-containing monocyclic rings had better efficiency and lifespan than Comparative Example 1 using BCP, a phenanthroline compound. In addition, the examples in which benzoquinoline and N-containing monocyclic rings were connected by two or more linkers showed lower operating voltage and better efficiency and lifespan than Comparative Example 2 in which benzoquinoline and N-containing monocyclic rings were connected by one linker. Furthermore, it was seen that the efficiency and lifespan of the remaining examples having three linkers were better than those of Example 1 having two linkers.

[0315] Comparative Example 3

[0316] An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that Comparative Compound 1 shown in Table 2 was used instead of Bphen as the electron transport layer.

[0317] Examples 20 to 38

[0318] An organic light-emitting device was manufactured in the same manner as in Comparative Example 1, except that the compounds synthesized in Synthetic Examples 1 to 19 were used instead of Bphen as the electron transport layer.

[0319] Experimental Example 2. Evaluation of Organic Light-Emitting Diodes (Electron Transport Layer Application)

[0320] The operating voltage, current efficiency, and lifespan of the previously fabricated organic light-emitting device were evaluated. The evaluation results are shown in Table 4 below.

[0321] [Table 4]

[0322]

[0323] The results of Table 4 applied to the electron transport layer also showed that the organic light-emitting device using the compounds of the present invention had lower operating voltage and improved current efficiency and lifespan compared to the organic light-emitting devices of the comparative examples. Specifically, it was seen that the remaining cases using compounds combining benzoquinoline and N-containing monocyclic rings had better efficiency and lifespan than Comparative Example 1 using Bphen, a phenanthroline compound. In addition, the examples in which benzoquinoline and N-containing monocyclic rings were connected by two or more linkers had lower operating voltage and better efficiency and lifespan than Comparative Example 3 in which benzoquinoline and N-containing monocyclic rings were connected by one linker. Furthermore, it was seen that the efficiency and lifespan of the remaining examples having three linkers were better than that of Example 1 having two linkers. In this way, the same conclusions were shown as the results when applied to the hole blocking layer.

[0324] The compound of the present invention described so far has excellent electron transport properties, and thus can be applied to an organic layer in which a material having electron transport properties is applied among one or more organic layers in an organic light-emitting device, and in one embodiment, it is applied to an electron transport layer, a hole blocking layer, or a charge generation layer to help realize low voltage, high efficiency, and long life.

Claims

1. A novel compound represented by the following chemical formula 1: In the above chemical formula 1, R1 to R9 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, nitrile group, substituted or unsubstituted C1~C30 alkyl group, substituted or unsubstituted C1~C30 alkenyl group, substituted or unsubstituted C1~C30 alkynyl group, substituted or unsubstituted C3~C30 cycloalkyl group, substituted or unsubstituted C1~C30 heterocycloalkyl group, substituted or unsubstituted C1~C30 alkoxy group, substituted or unsubstituted C1~C30 sulfide group, substituted or unsubstituted C6~C30 aryl group, substituted or unsubstituted C2~C30 heteroaryl group, substituted or unsubstituted C6~C30 aryloxy group, substituted or unsubstituted C2~C30 heteroaryloxy group, substituted or unsubstituted C1~C30 thio group, substituted or Selected from the group consisting of an unsubstituted C1~C30 amine group, a substituted or unsubstituted C1~C30 silyl group, and a substituted or unsubstituted C1~C30 phosphine oxide group, wherein at least one of R1 to R9 is the structural formula 1, In the above structural formula 1, L1 and L2 are each independently a substituted or unsubstituted C6~C30 arylene group, or a substituted or unsubstituted C2~C30 heteroarylene group, L3 is a direct bond, a substituted or unsubstituted C6~C30 arylene group, or a substituted or unsubstituted C2~C30 heteroarylene group, X1 to X5 are each independently N or CR, and at least one is N, Here, R is each independently hydrogen, deuterium, halogen, cyano group, nitro group, nitrile group, substituted or unsubstituted C1~C30 alkyl group, substituted or unsubstituted C1~C30 alkenyl group, substituted or unsubstituted C1~C30 alkynyl group, substituted or unsubstituted C3~C30 cycloalkyl group, substituted or unsubstituted C1~C30 heterocycloalkyl group, substituted or unsubstituted C1~C30 alkoxy group, substituted or unsubstituted C1~C30 sulfide group, substituted or unsubstituted C6~C30 aryl group, substituted or unsubstituted C2~C30 heteroaryl group, substituted or unsubstituted C6~C30 aryloxy group, substituted or unsubstituted C2~C30 heteroaryloxy group, substituted or unsubstituted C1~C30 It is selected from the group consisting of a cycloalkyl group, a substituted or unsubstituted C1~C30 amine group, a substituted or unsubstituted C1~C30 silyl group, and a substituted or unsubstituted C1~C30 phosphine oxide group.

2. In paragraph 1, A novel compound, characterized in that the above L3 is a substituted or unsubstituted C6~C30 arylene group or a substituted or unsubstituted C2~C30 heteroarylene group.

3. In paragraph 2, The above L1 to L3 are each independently substituted or unsubstituted with one or more substituents, characterized in that they are composed of at least one of phenylene, biphenylene, naphthylene, anthracenylene, phenanthrenylene, pyrenylene, dibenzofuranylene, dibenzothiophenylene, fluorenylene, dimethylfluorenylene, diphenylfluorenylene, spirobifluorenylene, carbazolylene, pyridinylene, pyrimidinylene, pyrazinylene, pyridazinylene, triazinylene, quinolinylene, isoquinolinylene, and naphthyridinylene. New compound.

4. In paragraph 1, A novel compound, characterized in that the above R1, R3, R4, R5, R6 or R8 is of the above structural formula 1.

5. In paragraph 1, The above structural formula 1 is a novel compound characterized by the following structural formula 1-1: In the above structural formula 1-1, L1 to L3 are the same as defined in the above chemical formula 1, X1, X3 and X5 are each independently N or CH, and at least one is N, Ar1 and Ar2 are each independently a substituted or unsubstituted C6~C30 aryl group or a substituted or unsubstituted C2~C30 heteroaryl group.

6. In paragraph 5, The above structural formula 1-1 is a novel compound characterized by being one of the following structural formulas 1-1-A to 1-1-E: In the above structural formulas 1-1-A to 1-1-E, L1 to L3, Ar1 and Ar2 are the same as defined in the above structural formula 1-1.

7. In paragraph 1, A novel compound characterized in that the compound represented by the above chemical formula 1 is one of the following compounds 1 to 1281:

8. First electrode and second electrode; It comprises at least one organic layer positioned between the first electrode and the second electrode, At least one of the organic layers comprises a novel compound according to any one of claims 1 to 7. Organic light emitting diode.

9. In paragraph 8, An organic light-emitting device, characterized in that the organic layer containing the compound is at least one of an electron transport layer, a hole blocking layer, and a charge generation layer.

Images