CN114773353A - Carbazole-containing eight-membered ring compound and application thereof - Google Patents
Carbazole-containing eight-membered ring compound and application thereof Download PDFInfo
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- CN114773353A CN114773353A CN202210390906.3A CN202210390906A CN114773353A CN 114773353 A CN114773353 A CN 114773353A CN 202210390906 A CN202210390906 A CN 202210390906A CN 114773353 A CN114773353 A CN 114773353A
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- Prior art keywords
- substituted
- unsubstituted
- group
- carbazole
- membered ring
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 69
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 title claims abstract description 64
- 239000000463 material Substances 0.000 claims abstract description 42
- 239000010410 layer Substances 0.000 claims description 68
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 229910052760 oxygen Inorganic materials 0.000 claims description 17
- 229910052717 sulfur Inorganic materials 0.000 claims description 17
- -1 C2-C60Alkenyl radical Chemical class 0.000 claims description 15
- 125000005842 heteroatom Chemical group 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 229910052805 deuterium Inorganic materials 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 239000012044 organic layer Substances 0.000 claims description 5
- 125000003367 polycyclic group Chemical group 0.000 claims description 5
- 150000003254 radicals Chemical class 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 235000010290 biphenyl Nutrition 0.000 claims description 3
- 239000004305 biphenyl Substances 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000002950 monocyclic group Chemical group 0.000 claims description 3
- 150000002825 nitriles Chemical class 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000006745 (C2-C60) alkynyl group Chemical group 0.000 claims description 2
- 125000006751 (C6-C60) aryloxy group Chemical group 0.000 claims description 2
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 229910052796 boron Inorganic materials 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 150000007942 carboxylates Chemical class 0.000 claims description 2
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
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- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 2
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- 150000004832 aryl thioethers Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 5
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 238000000034 method Methods 0.000 description 13
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
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- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
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- 229910002027 silica gel Inorganic materials 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 101100446506 Mus musculus Fgf3 gene Proteins 0.000 description 4
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- 125000005605 benzo group Chemical group 0.000 description 4
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- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 4
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 4
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- 238000007639 printing Methods 0.000 description 4
- BMIBJCFFZPYJHF-UHFFFAOYSA-N 2-methoxy-5-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine Chemical compound COC1=NC=C(C)C=C1B1OC(C)(C)C(C)(C)O1 BMIBJCFFZPYJHF-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
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- 239000002019 doping agent Substances 0.000 description 3
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- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 3
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
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- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
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- 101000767160 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) Intracellular protein transport protein USO1 Proteins 0.000 description 2
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- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
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Abstract
The present invention relates to an eight-membered ring compound containing carbazole, an organic electroluminescent element, a display device, and a lighting device. The carbazole-containing eight-membered ring compound has higher triplet energy level and high glass transition temperature, and is suitable for being used as a material for an organic electroluminescent element. The material for organic electroluminescent elements, which contains the carbazole-containing eight-membered ring compound, has the characteristics of low starting voltage, high luminous efficiency and high brightness. The compound of the present invention has excellent thermal stability and film-forming properties, and can be used for materials for organic electroluminescent elements, display devices, and lighting devices, and can prolong the service life thereof, thereby reducing the production costs of the materials for organic electroluminescent elements, the display devices, and the lighting devices.
Description
Technical Field
The invention belongs to the technical field of organic electroluminescent materials, and particularly relates to an eight-membered ring compound containing carbazole, an organic electroluminescent element, a display device and a lighting device.
Background
In recent years, the organic electroluminescent display technology has become mature, some products have entered the market, but in the process of industrialization, many problems still need to be solved. In particular, various organic materials used for manufacturing elements have many problems that are not solved, such as carrier injection and transport properties, electroluminescent properties of the materials, service life, color purity, matching between various materials and between various electrodes, and the like. Especially, the light emitting device has not yet achieved practical requirements in terms of luminous efficiency and lifetime, which greatly limits the development of OLED technology.
Organic electroluminescence is largely divided into fluorescence and phosphorescence, but according to the spin quantum statistics theory, the probability of singlet excitons and triplet excitons is 1:3, i.e., the theoretical limit of fluorescence from radiative transition of singlet excitons is 25%, and the theoretical limit of fluorescence from radiative transition of triplet excitons is 75%. It is urgent to use 75% of the energy of the triplet excitons. Forrest et al in 1997 discovered that the phosphorescence electroluminescence phenomenon breaks through the limitation of 25% efficiency of the quantum efficiency of the organic electroluminescence material, and arouses people to pay extensive attention to the metal complex phosphorescence material. Since then, much research has been conducted on phosphorescent materials.
The present invention has been made in view of the above circumstances.
Disclosure of Invention
In order to solve the above problems of the prior art, the present invention provides a carbazole-containing eight-membered ring compound, an organic electroluminescent element, a display device, and a lighting device. The compound of the present invention is useful as a raw material for an organic electroluminescent element, and can provide a material for an organic electroluminescent element and an organic electroluminescent element which have a reduced activation voltage, a high luminous efficiency, and an improved luminance.
In order to achieve the purpose, the invention adopts the following technical scheme:
a carbazole-containing eight-membered ring compound having a structure represented by formula (I):
wherein R isa、Rb、Rc、Rd、R1、R2、R3、R4、R5、R6、R7、R8、R9The same or different, each independently selected from the group consisting of: hydrogen, deuterium, having C1~C40Straight chain alkyl of (2) having C1~C40Linear heteroalkyl group of (C)3~C40A branched or cyclic alkyl group of (2), having C3~C40A branched or cyclic heteroalkyl group of (A) having C2~C40Any adjacent two or more substituents are optionally joined or fused to form a monocyclic or polycyclic ring, with or without C, N, O or S in the ring so formed;
and R isaAnd RbOr R iscAnd RdAt least one group is substituted by a group shown in a formula (II);
ring A represents R9A substituted or unsubstituted five-membered heterocyclic ring, wherein the heteroatom is selected from O, S or one or more of N, and the atoms on the five-membered heterocyclic ring are independently selected from heteroatoms;
Ar1selected from the group consisting of: substituted or unsubstituted C6~C60Aryl, substituted or unsubstituted C2~C60Heteroaryl, substituted or unsubstituted C6~C60Arylamino, substituted or unsubstituted C2~C60A heteroaryl amino group;
l represents a single bond, substituted or unsubstituted C6~C60Arylene, substituted or unsubstituted C2~C60A heteroarylene group;
-represents the bond connecting the substituent to N.
An aryl or aromatic group in the sense of the present invention contains 5 to 60 carbon atoms and a heteroaryl group in the sense of the present invention contains 2 to 60 carbon atoms and at least one heteroatom, with the proviso that the sum of carbon atoms and heteroatoms is at least 5; the heteroatom is preferably selected from N, O or S. Aryl or heteroaryl here embraces monocyclic radicals and polycyclic systems. Polycyclic rings can have two carbons that are two contiguous rings or two or more rings in common, referred to as "fused," where at least one of the rings is aromatic, e.g., the other rings can be cycloalkyls, cycloalkenyls, aryls, heterocyclics, and/or heteroaryls. In addition, multiple aryl or heteroaryl groups may also be connected by non-aromatic units such as C, N, O or S atoms, for example, as with systems in which two or more aryl groups are connected by, for example, a short alkyl group, such as fluorene, 9' -spirobifluorene, 9-diarylfluorene, triarylamine, diarylether, dibenzofuran, or dibenzothiophene, and the like.
The alkyl group used in the present invention means a monovalent functional group obtained by removing one hydrogen atom from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms. As non-limiting examples thereof, there are methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, isopentyl, hexyl, and the like. Heteroalkyl means a hydrogen atom or-CH on an alkyl group2-substituted by at least one heteroatom selected from halogen, halogen substituted by a halogen atom, or a halogen atom,Nitrile group N, O, S or silicon, as non-limiting examples, difluoromethyl, trifluoromethyl, trifluoroethyl, pentafluoroethyl, nitrile, acetonitrile, methoxymethyl, methoxyethyl, trimethylsilyl, triisopropylsilyl and the like.
The alkenyl group used in the present invention means a monovalent functional group obtained by removing one hydrogen atom from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon double bonds. As non-limiting examples thereof, there are vinyl, allyl, isopropenyl, 2-butenyl, and the like.
The alkynyl group used in the present invention means a monovalent functional group obtained by removing one hydrogen atom from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon triple bonds. As non-limiting examples thereof, there are ethynyl, 2-propynyl and the like.
In general, the cycloalkyl group, cycloalkenyl group according to the present invention means a monovalent functional group obtained by removing one hydrogen atom from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. As non-limiting examples thereof, there may be mentioned cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, norbornyl, adamantyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptyl, cycloheptenyl, and the like, wherein one or more-CH groups2The radicals may be replaced by the radicals mentioned above; furthermore, one or more hydrogen atoms may also be replaced by deuterium atoms, halogen atoms or nitrile groups.
The heterocycloalkyl group used in the present invention refers to a monovalent functional group obtained by removing one hydrogen atom from a non-aromatic hydrocarbon having an atomic number of 3 to 40. In this case, more than one carbon, preferably 1 to 3 carbons, in the ring is substituted with a heteroatom such as N, O or S. As non-limiting examples thereof, there are tetrahydrofuran, tetrahydrothiophene, morpholine, piperazine and the like.
The aryloxy group or heteroaryloxy group used in the present invention means a monovalent functional group represented by RO-, and R mentioned above is an aryl group having 6 to 60 carbon atoms or a heteroaryl group having 5 to 60 carbon atoms. As non-limiting examples of such aryloxy or heteroaryloxy groups, there are phenoxy, naphthoxy, biphenyloxy, 2-pyridyloxy, 3-pyridyloxy, 4-pyridyloxy and the like.
The aryl or heteroaryl radicals according to the invention are, in particular, radicals derived from: benzene, naphthalene, anthracene, benzanthracene, phenanthrene, pyrene,Perylene, fluoranthene, tetracene, pentacene, benzopyrene, biphenyl, terphenyl, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis-or trans-indenofluorene, cis-or trans-indenocarbazole, cis-or trans-indolocarbazole, triindene, isotridendene, spirotriindene, spiroisotridendene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo [5,6 ] indole, perylene, anthracene, phenanthrene, perylene]Quinoline, benzo [6,7 ]]Quinoline, benzo [7,8 ]]Quinoline, phenothiazine, phenoxazine, pyrazole, indazole, imidazole, benzimidazole, naphthoimidazole, phenanthroimidazole, pyridoimidazole, pyrazinoimidazole, quinoxaloimidazole, oxazole, benzoxazole, naphthooxazole, anthraoxazole, phenanthroixazole, isoxazole, 1, 2-thiazole, 1, 3-thiazole, benzothiazole, pyridazine, hexaazatriphenylene, benzopyridazine, pyrimidine, benzopyrimidine, quinoxaline, 1, 5-diaza-thracene, 2, 7-diaza, 2, 3-diaza-pyrene, 1, 6-diaza-pyrene, 1, 8-diaza-pyrene, 4,5,9, 10-tetraazaperylene, pyrazine, phenazine, phenoxazine, phenothiazine, fluorescent red ring, naphthyridine, azacarbazole, benzocarbazine, carboline, phenanthroline, 1,2, 3-triazole, 1,2, 4-triazole, benzotriazole, 1,2, 3-oxadiazole, 1,2, 4-oxadiazole, 1,2, 5-oxadiazole, 1,3, 4-oxadiazole, 1,2, 3-thiadiazole, 1,2, 4-thiadiazole, 1,2, 5-thiadiazole, 1,3, 4-thiadiazole, 1,3, 5-triazine, 1,2, 4-triazine, 1,2, 3-triazine, tetrazole, 1,2,4, 5-tetrazine, 1,2,3, 4-tetrazine, 1,2,3, 5-tetrazine, purine, pteridine, indolizine, and benzothiadiazole, or a group derived from a combination of these systems.
As used herein, "a combination thereof" or "group" means that one or more members of the applicable list are combined to form a known or chemically stable arrangement that one of ordinary skill in the art can envision from the applicable list. For example, alkyl and deuterium can be combined to form a partially or fully deuterated alkyl; halogen and alkyl may combine to form haloalkyl substituents such as trifluoromethyl and the like; and halogen, alkyl, and aryl groups may be combined to form haloaralkyl groups.
Further, the carbazole-containing eight-membered ring compound is one of formula (I) -1 to formula (I) -6:
g is selected from O, S or NAr2;
Ar2Selected from the group consisting of: substituted or unsubstituted C6~C60Aryl, substituted or unsubstituted C2~C60Heteroaryl, substituted or unsubstituted C6~C60Arylamine, substituted or unsubstituted C2~C60A heteroaryl amine group.
Further, the carbazole-containing eight-membered ring compound is selected from the group consisting of the structures shown below:
the symbols used are as defined above.
According to an embodiment of the present invention, further, the Ra、Rb、Rc、Rd、R1、R2、R3、R4、R5、R6、R7、R8、R9Each independently of each otherIndependently selected from hydrogen or deuterium; ar (Ar)1Is substituted or unsubstituted C2~C60A heteroaryl group, said heteroaryl group containing at least one nitrogen atom.
Further, the heteroaryl is selected from the group consisting of the following groups II-1 to II-17:
wherein,
Z1、Z2each independently selected from the group consisting of hydrogen, deuterium, halogen, hydroxy, nitrile, nitro, amino, amidino, hydrazine, hydrazone, carboxy or carboxylate thereof, sulfonic or sulfonate thereof, phosphoric or phosphate thereof, C1-C60Alkyl radical, C2-C60Alkenyl radical, C2-C60Alkynyl, C1-C60Alkoxy radical, C3-C60Cycloalkyl radical, C3-C60Cycloalkenyl, substituted or unsubstituted C6-C60Aryl, substituted or unsubstituted C6-C60Aryloxy, substituted or unsubstituted C6-C60An arylsulfonyl ether group, or a substituted or unsubstituted C2-C60Heterocyclic aryl groups;
x1 represents an integer of 1 to 4; x2 represents an integer of 1 to 3; x3 represents 1 or 2; x4 represents an integer of 1 to 6; x5 represents an integer of 1 to 5;
T1representation O, S, CR’R' or NAr’;
R’R' are each independently selected from hydrogen, deuterium, C1~C60Alkyl of (C)1~C60With heteroalkyl, substituted or unsubstituted C6-C60Aryl, substituted or unsubstituted C6-C60Arylamino, or substituted or unsubstituted C2-C60Group consisting of heterocyclic aryl radicals, R’And R "may optionally be joined or fused to form one or more additional substituted or unsubstituted rings, with or without one or more heteroatoms N, P, B, O or S in the formed ring; preferably, R’R' is methyl, phenyl or fluorenyl;
Ar’is selected from the group consisting of C1~C60Alkyl of (C)1~C60Heteroalkyl group of (C)3~C60Cycloalkyl, substituted or unsubstituted C6-C60Aryl, substituted or unsubstituted C6-C60Condensed ring aryl, substituted or unsubstituted C6-C60Arylamino, or substituted or unsubstituted C2-C60Heterocyclic aryl groups; preferably, Ar' is methyl, ethyl, phenyl, biphenyl or naphthyl;
Further, the carbazole-containing eight-membered ring compound is selected from one of the following structures represented by D253 to D438:
wherein each G-is independently selected from O-, S-, or one of the following structures:
and represents a bond.
The carbazole-containing eight-membered ring compound is used in a material for an organic electroluminescent element.
Further, the carbazole-containing eight-membered ring compound is applied to a light-emitting layer material, a hole transporting/hole blocking layer material or a capping layer material.
An organic electroluminescent element comprising a first electrode, a second electrode, a capping layer and at least one organic layer interposed between the first electrode and the second electrode, at least one of the organic layer or the capping layer comprising the carbazole-containing eight-membered ring compound.
The organic electroluminescent element includes a cathode, an anode, and at least one light-emitting layer. In addition to these layers, it may also comprise further layers, for example in each case one or more hole-injecting layers, hole-transporting layers, hole-blocking layers, electron-transporting layers, electron-injecting layers, exciton-blocking layers, electron-blocking layers and/or charge-generating layers. An intermediate layer having, for example, exciton blocking function can likewise be introduced between the two light-emitting layers. However, it should be noted that each of these layers need not be present. The organic electroluminescent device described herein may include one light emitting layer, or it may include a plurality of light emitting layers. That is, a plurality of light-emitting compounds capable of emitting light are used in the light-emitting layer. Particularly preferred are systems with three light-emitting layers, wherein the three layers can exhibit blue, green and red light emission. If more than one light-emitting layer is present, at least one of these layers comprises the carbazole-containing eight-membered ring compound of the invention according to the invention.
In the other layers of the organic electroluminescent element according to the invention, in particular in the hole transport layer and in the hole blocking layer and the thin-film encapsulation layer, all materials can be used in the manner generally used according to the prior art. A person skilled in the art will thus be able to use all materials known for organic electroluminescent elements in combination with the luminescent layer according to the invention without inventive effort.
Preference is furthermore given to organic electroluminescent elements in which one or more layers are applied by means of a sublimation process in which the temperature in a vacuum sublimation apparatus is below 10-5Pa, preferably less than 10-6Pa is applied by vapor deposition. However, the initial pressure may also be even lower, e.g. below 10-7Pa。
Preference is likewise given to organic electroluminescent elements in which one or more layers are applied by means of an organic vapor deposition method or by means of carrier gas sublimation, where 10-5The material is applied under a pressure between Pa and 1 Pa. A particular example of such a process is the organic vapor jet printing processWherein the material is applied directly through a nozzle and is thus structured.
Preference is furthermore given to organic electroluminescent elements in which one or more layers are produced from solution, for example by spin coating, or by means of any desired printing method, for example screen printing, flexographic printing, offset printing, photoinitiated thermal imaging, thermal transfer, ink-jet printing or nozzle printing. Soluble compounds, for example, are obtained by appropriate substitution of a compound of formula (I). These methods are also particularly suitable for oligomers, dendrimers and polymers. Furthermore, hybrid methods are possible, in which one or more layers are applied, for example, from solution and one or more further layers are applied by vapor deposition.
Further, the organic layer may further include one or more selected from an electron injection layer, an electron transport layer, a hole blocking layer, an electron blocking layer, a hole transport layer, a hole injection layer, a light emitting layer, and a light refraction layer.
The organic electroluminescent element of the present invention may be either a top-emitting or bottom-emitting element. The structure and the production method of the organic electroluminescent element of the present invention are not limited. The organic electroluminescent element prepared by the compound can reduce the starting voltage and improve the luminous efficiency and brightness.
A display device includes the organic electroluminescent element.
An illumination device comprising the organic electroluminescent element.
The material for organic devices of the present invention contains the carbazole-containing eight-membered ring compound of the present invention. The material for organic devices may be composed of the compound of the present invention alone or may contain other compounds.
The compound of the present invention contained in the material for an organic electroluminescent element of the present invention can be used as a host material. In this case, the material for an organic electroluminescent element of the present invention may contain another compound as a dopant.
The material for an organic electroluminescent element of the present invention can also be used as a material for a hole transport layer, an enhancement layer, a light-emitting layer, an electron transport layer, a charge generation layer, an electron blocking layer, a capping layer, or a photorefractive layer.
Compared with the prior art, the invention has the beneficial effects that:
the carbazole-containing eight-membered ring compound of the present invention is a novel carbazole structure having an eight-membered ring, and has a bipolar property of transporting electrons and holes. The carbazole-containing eight-membered ring compound is suitable for use as a material for an organic electroluminescent element, and the material for an organic electroluminescent element containing the carbazole-containing eight-membered ring compound has the characteristics of low starting voltage, high luminous efficiency and high brightness. In addition, the compound of the present invention has good thermal stability and film-forming properties, and can be used in materials for organic electroluminescent elements, display devices, and lighting devices to prolong the service life thereof, thereby reducing power consumption and manufacturing cost.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the embodiments or the prior art will be briefly described below, it is obvious that the drawings in the following description are only some embodiments of the present invention, and for those skilled in the art, other drawings can be obtained according to the drawings without creative efforts.
Fig. 1 shows a schematic diagram of an organic light emitting device 100. The illustrations are not necessarily drawn to scale. The device 100 may include a substrate 101, an anode 102, a hole injection layer 103, a hole transport layer 104, an electron blocking layer 105, an emissive layer 106, a hole blocking layer 107, an electron transport layer 108, an electron injection layer 109, a cathode 110, and a capping layer (CPL) 111. The device 100 may be fabricated by sequentially depositing the described layers.
Fig. 2 shows a schematic view of an inverted organic light emitting device 200. The device comprises a substrate 201, a cathode 202, an emissive layer 203, a hole transport layer 204, and an anode 205. The device 200 may be prepared by sequentially depositing the described layers. Because the most common OLED devices have a cathode disposed over an anode, while device 200 has a cathode 202 disposed under an anode 205, device 200 may be referred to as an "inverted" organic light emitting device. In corresponding layers of the device 200, materials similar to those described with respect to the device 100 may be used. Fig. 2 provides one example of how some layers may be omitted from the structure of device 100.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the technical solutions of the present invention will be described in detail below. It is to be understood that the described embodiments are merely exemplary of the invention, and not restrictive of the full scope of the invention. All other embodiments, which can be derived by a person skilled in the art from the examples given herein without any inventive step, are within the scope of the present invention.
The following examples illustrate the performance of OLED materials and devices as follows:
OLED element performance detection conditions:
luminance and chromaticity coordinates: testing with a photosresearch PR-715 spectrum scanner;
current density and lighting voltage: testing using a digital source table Keithley 2420;
power efficiency: tested using NEWPORT 1931-C;
and (3) life test: an LTS-1004AC life test apparatus was used.
Example 1
A process for the preparation of compound D254 comprising the steps of:
the first step is as follows: preparation of intermediate Int-1
22.0mmol of 2- (2-phenylboronic acid pinacol ester) indole, 20.0mmol of 4, 5-dibromocarbazole-9-carboxylic acid tert-butyl ester, 40.0mmol of anhydrous sodium carbonate, and 0.1mmol of Pd (PPh)3)4Adding catalyst, adding 80mL of toluene, 40mL of ethanol and 40mL of water, heating, refluxing and stirring for reaction for 8 hours under the protection of nitrogen, filtering, concentrating the filtrate under reduced pressure to dryness, and separating and purifying by using a silica gel column to obtain the catalystInt-1 as a yellow solid, yield: 77 percent.
The second step: preparation of intermediate Int-2
20.0mmol of Int-1 are dissolved in 120mL of toluene and 40.0mmol of sodium tert-butoxide and 0.1mmol of Pd are added under nitrogen protection2(dba)3And 0.2mmol of Xphos, heating to 100 ℃, stirring for reaction for 12 hours, cooling to room temperature, adding 50mL of 3N dilute hydrochloric acid aqueous solution, extracting with toluene, drying an organic phase, filtering, concentrating under reduced pressure to dryness, passing through a silica gel short column, eluting with toluene, and concentrating under reduced pressure to dryness to obtain a yellow solid, wherein the yield is as follows: 60 percent.
The third step: preparation of Compound D254
Dissolving 10.0mmol of intermediate Int-2 in 50mL of dry DMF, cooling to 0 ℃ with ice water bath under the protection of nitrogen, adding 12.0mmol of 65% sodium hydride solid in batches, stirring for reaction for 1 hour, adding 12.0mmol of 2-chloro-4, 6-diphenyl-1, 3, 5-triazine, heating to 45 ℃, stirring for reaction for 12 hours, pouring the reaction solution into 250mL of ice water, filtering, washing a filter cake with water and ethanol, and separating and purifying by using a silica gel column to obtain a compound D254, a yellow solid, and the yield: 84%, MS (MALDI-TOF): m/z 588.2194[ M + H ]]+。
Example 2
A process for the preparation of compound D309 comprising the steps of:
the first step is as follows: preparation of intermediate Int-3
Referring to the first step synthesis of example 1, only the 2- (2-phenylboronic acid pinacol ester) indole of the first step of example 1 was replaced with 1- (2-phenylboronic acid pinacol ester) benzo [ d ] imidazole to obtain compound Int-3 as a yellow solid, yield: 82 percent.
The second step: preparation of intermediate Int-4
20.0mmol of Int-3 was dissolved in 120mL of toluene and 30.0mmol of sodium tert-butoxide and 0.1mmol of Pd were added under nitrogen2(dba)3And 0.4mL of 10% tri-tert-butylphosphine toluene solution, heating to 100 ℃, stirring for reaction for 12 hours, cooling to room temperature, adding 50mL of 3N dilute hydrochloric acid aqueous solution, extracting with toluene, drying the organic phase, filtering, concentrating under reduced pressure to dryness, passing through a short column of silica gel, eluting with toluene, concentrating under reduced pressure to dryness to obtain a yellow solid, and obtaining the yield: 74 percent.
With reference to the analogous synthetic methods described above, the following compounds were prepared:
the third step: preparation of Compound D309
Referring to the synthesis procedure of the third step of example 1, substituting only Int-2 of the third step of example 1 with Int-4, compound D309 was prepared as a yellow solid in yield: 86%, MS (MALDI-TOF): m/z 589.2154[ M + H ]]+。
With reference to the analogous synthetic procedures described above, the following compounds were prepared:
wherein each G is independently selected from O, S or NPh.
Example 3
Preparation of compound D388:
20.0mmol of Int-2 are dissolved in 60mL of toluene and 30.0mmol of sodium tert-butoxide, 24.0mmol of 2- (2-bromophenyl) -4, 6-diphenyl-1, 3, 5-triazine and 0.2mmol of Pd are added under nitrogen2(dba)3And 0.5mL of 10% tri-tert-butylphosphine toluene solution, heating to 100 ℃, stirring for reaction for 12 hours, cooling to room temperature, adding 20mL of water, extracting with toluene, drying the organic phase, filtering, concentrating under reduced pressure to dryness, passing through a silica gel short column, eluting with toluene-dichloromethane, and concentrating under reduced pressure to dryness to obtain a yellow solid, wherein the yield is as follows: 85 percent. MS (MALDI-TOF): m/z 664.2509[ M + H ]]+。
With reference to a similar synthetic procedure as in example 3 above, the following compounds were prepared:
wherein each G is independently selected from O, S or NPh.
Preparation of organic electroluminescent element
Comparative example 1
The following compound C was used as a hole injection material, compound D as a hole transport material, compound E as a red host material, compound F as a red dopant material, compound G as an electron transport dopant material, and LiQ as an electron transport host material.
The compound The OLED comparative element 1 was prepared by sequentially depositing ITO glass by an EL deposition machine manufactured by DOV corporation.
Comparative example 2
The compound An EL evaporator manufactured by DOV company is sequentially adopted to evaporate and plate on the ITO glass to manufacture an OLED contrast element 2;
the structure of B as the red light main body material is as follows:
test example 1
An OLED element was prepared in accordance with the procedure of comparative example 1, wherein the aforementioned Compound E was replaced with any one or more of the compounds D253 to D438 of the present invention, to prepare an organic electroluminescent element,
the organic electroluminescent element prepared by the above process was subjected to the following performance tests:
the driving voltage and current efficiency of the organic electroluminescent elements prepared in test example 1 and comparative examples 1 to 3 and the lifetime of the elements were measured at the same luminance using a digital source meter and a luminance meter. Specifically, the voltage was raised at a rate of 0.1V per second, and it was determined that the luminance of the organic electroluminescent element reached 1000cd/m2The current voltage is the driving voltage, and the current density at the moment is measured; the ratio of the brightness to the current density is the current efficiency; the LT 98% lifetime test is as follows: using a luminance meter at 1000cd/m2The luminance degradation of the organic electroluminescent element was measured to be 980cd/m by maintaining a constant current at luminance2Time in hours. The results are shown in Table 1.
TABLE 1 test results of the performance of each element
As is clear from table 1, when the carbazole-containing eight-membered ring compound of the present invention is used as a host material for an organic electroluminescent device, the current efficiency is improved, the lifetime is greatly improved, and the carbazole-containing eight-membered ring compound is a phosphorescent host material having excellent performance.
The compound B in comparative example 2 is different from the compound of the present invention in that the compound B does not contain a heterocyclic ring represented by ring a and has a weak conjugation ability as compared with a five-membered heterocyclic ring containing an unpaired electron, so that the compound of the present invention is superior to the compound B in both molecular film formation and charge transport, and therefore, charge transport in the element is more balanced and element performance is improved.
The properties of only some of the compounds in D253-D438 are listed in Table 1, and the properties of other compounds are substantially consistent with the data of the compounds listed in Table 1, and are not listed any more due to space limitation.
The above description is only for the specific embodiments of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art can easily conceive of the changes or substitutions within the technical scope of the present invention, and all the changes or substitutions should be covered within the scope of the present invention. Therefore, the protection scope of the present invention shall be subject to the protection scope of the appended claims.
Claims (10)
1. A carbazole-containing eight-membered ring compound, characterized in that the carbazole-containing eight-membered ring compound has a structure represented by formula (I):
wherein R isa、Rb、Rc、Rd、R1、R2、R3、R4、R5、R6、R7、R8、R9The same or different, each independently selected from the group consisting of: hydrogen, deuterium, having C1~C40Straight chain alkyl of (2) having C1~C40Linear heteroalkyl group of (A) having C3~C40A branched or cyclic alkyl group of (2), having C3~C40A branched or cyclic heteroalkyl group of (2), having C2~C40Any adjacent two or more substituents are optionally joined or fused to form a monocyclic or polycyclic ring, with or without C, N, O or S in the ring so formed;
and R isaAnd RbOr R iscAnd RdAt least one group is substituted by a group shown in a formula (II);
ring A represents R9A substituted or unsubstituted five-membered heterocyclic ring, wherein the heteroatom is selected from one or more of O, S or N, and the atoms on the five-membered heterocyclic ring are independently selected from heteroatoms;
Ar1selected from the group consisting of: substituted or unsubstituted C6~C60Aryl, substituted or unsubstituted C2~C60Heteroaryl, substituted or unsubstituted C6~C60Arylamine, substituted or unsubstituted C2~C60A heteroaryl amino group;
l represents a single bond, substituted or unsubstituted C6~C60Arylene, substituted or unsubstituted C2~C60A heteroarylene group;
-represents the bond of the substituent to N.
2. The carbazole-containing eight-membered ring compound according to claim 1, wherein the compound is selected from one or more of the group consisting of formula (I) -1 to formula (I) -6:
g is selected from O, S or NAr2;
Ar2Selected from the group consisting of: substituted or unsubstituted C6~C60Aryl, substituted or unsubstituted C2~C60Heteroaryl, substituted or unsubstituted C6~C60Arylamine, substituted or unsubstituted C2~C60A heteroaryl amino group;
Ra、Rb、Rc、Rd、R1、R2、R3、R4、R5、R6、R7、R8、R9has the same meaning as defined in claim 1.
3. The carbazole-containing eight-membered ring compound according to claim 1 or 2, wherein the compound is selected from the group consisting of the structures shown below:
g is selected from O, S or NAr2;
Ar2Selected from the group consisting of: substituted or unsubstituted C6~C60Aryl, substituted or unsubstituted C2~C60Heteroaryl, substituted or unsubstituted C6~C60Arylamine, substituted or unsubstituted C2~C60A heteroaryl amino group;
Ra、Rb、Rc、Rd、R1、R2、R3、R4、R5、R6、R7、R8、R9、L、Ar1has the same meaning as defined in claim 1.
4. The carbazole-containing eight-membered ring compound according to any one of claims 1 to 3, wherein R isa、Rb、Rc、Rd、R1、R2、R3、R4、R5、R6、R7、R8、R9Each independently selected from hydrogen or deuterium; ar (Ar)1Is substituted or unsubstituted C2~C60A heteroaryl group containing at least one nitrogen atom.
5. The carbazole-containing eight-membered ring compound according to any one of claims 1 to 4, wherein the heteroaryl group is selected from the group consisting of the following groups II-1 to II-17:
wherein,
Z1、Z2each independently selected from the group consisting of hydrogen, deuterium, halogen, hydroxy, nitrile, nitro, amino, amidino, hydrazine, hydrazone, carboxy or carboxylate thereof, sulfonic or sulfonate thereof, phosphoric or phosphate thereof, C1-C60Alkyl radical, C2-C60Alkenyl radical, C2-C60Alkynyl, C1-C60Alkoxy radical, C3-C60Cycloalkyl radical, C3-C60Cycloalkenyl, substituted or unsubstituted C6-C60Aryl, substituted or unsubstituted C6-C60Aryloxy, substituted or unsubstituted C6-C60An arylthioether group, or a substituted or unsubstituted C2-C60Heterocyclic aryl groups;
x1 represents an integer of 1 to 4; x2 represents an integer of 1 to 3; x3 represents 1 or 2; x4 represents an integer of 1 to 6; x5 represents an integer of 1 to 5;
T1o, S, CR 'R "or NAr';
r 'and R' are each independently selected from hydrogen, deuterium, C1~C60Alkyl of (C)1~C60With heteroalkyl, substituted or unsubstituted C6-C60Aryl, substituted or unsubstituted C6-C60Arylamino, or substituted or unsubstituted C2-C60Heterocyclic aryl, R 'and R' may optionally be joined or fused to form one or more additional substituted or unsubstituted rings, with or without one or more heteroatoms N, P, B, O or S in the ring so formed; preferably, R', R "are methyl, phenyl or fluorenyl;
ar' is selected from C1~C60Alkyl of (C)1~C60Heteroalkyl of (a), C3~C60Cycloalkyl, substituted or unsubstituted C6-C60Aryl, substituted or unsubstituted C6-C60Condensed ring aryl, substituted or unsubstituted C6-C60Arylamino, or substituted or unsubstituted C2-C60Heterocyclic aryl groups; preferably, Ar' is methyl, ethyl, phenyl, biphenyl or naphthyl;
7. Use of the carbazole-containing eight-membered ring compound according to any one of claims 1 to 6 in a material for an organic element, wherein the carbazole-containing eight-membered ring compound is used in a material for an organic electroluminescent element.
8. An organic electroluminescent element comprising a first electrode, a second electrode, a capping layer and at least one organic layer interposed between the first electrode and the second electrode, wherein at least one of the organic layer or the capping layer comprises the carbazole-containing eight-membered ring compound according to any one of claims 1 to 6.
9. A display device comprising the organic electroluminescent element according to claim 8.
10. A lighting device comprising the organic electroluminescent element according to claim 8.
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US20210320263A1 (en) * | 2020-04-06 | 2021-10-14 | Rohm And Haas Electronic Materials Korea Ltd. | Organic electroluminescent compound, a plurality of host materials, and organic electroluminescent device comprising the same |
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US20180309067A1 (en) * | 2017-04-21 | 2018-10-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
CN111875609A (en) * | 2019-08-08 | 2020-11-03 | 广州华睿光电材料有限公司 | Pyrrole group-containing compound, high polymer, mixture, composition and organic electronic device |
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