CN111704580A - Benzimidazole-containing compound and application thereof in organic electroluminescent device - Google Patents
Benzimidazole-containing compound and application thereof in organic electroluminescent device Download PDFInfo
- Publication number
- CN111704580A CN111704580A CN202010509195.8A CN202010509195A CN111704580A CN 111704580 A CN111704580 A CN 111704580A CN 202010509195 A CN202010509195 A CN 202010509195A CN 111704580 A CN111704580 A CN 111704580A
- Authority
- CN
- China
- Prior art keywords
- benzimidazole
- compound
- layer
- containing compound
- organic electroluminescent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 44
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 title claims abstract description 28
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 3
- 125000003118 aryl group Chemical group 0.000 claims abstract description 3
- 150000008359 benzonitriles Chemical class 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 3
- 239000010410 layer Substances 0.000 claims description 59
- 238000002347 injection Methods 0.000 claims description 13
- 239000007924 injection Substances 0.000 claims description 13
- 239000012044 organic layer Substances 0.000 claims description 11
- 230000000903 blocking effect Effects 0.000 claims description 8
- 230000005525 hole transport Effects 0.000 claims description 7
- 150000002894 organic compounds Chemical class 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 4
- -1 phenyl,Tolyl Chemical group 0.000 claims description 4
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
- 239000000463 material Substances 0.000 description 19
- 230000032258 transport Effects 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 16
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 239000008367 deionised water Substances 0.000 description 10
- 229910021641 deionized water Inorganic materials 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- 229940125904 compound 1 Drugs 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 6
- 239000012065 filter cake Substances 0.000 description 6
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 4
- QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 229940126543 compound 14 Drugs 0.000 description 4
- 229940125846 compound 25 Drugs 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 description 3
- KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 description 3
- 229940126208 compound 22 Drugs 0.000 description 3
- 229940125877 compound 31 Drugs 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- NJSUFZNXBBXAAC-UHFFFAOYSA-N ethanol;toluene Chemical compound CCO.CC1=CC=CC=C1 NJSUFZNXBBXAAC-UHFFFAOYSA-N 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- 230000005283 ground state Effects 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 1
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 1
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- ZJVKLBBPLUXEAC-UHFFFAOYSA-N Pipethanate hydrochloride Chemical compound [Cl-].C=1C=CC=CC=1C(C=1C=CC=CC=1)(O)C(=O)OCC[NH+]1CCCCC1 ZJVKLBBPLUXEAC-UHFFFAOYSA-N 0.000 description 1
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 1
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000007611 bar coating method Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000005669 field effect Effects 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 108091008695 photoreceptors Proteins 0.000 description 1
- 230000000243 photosynthetic effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/16—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
Abstract
The invention belongs to the technical field of organic electroluminescent device display, and particularly relates to a benzimidazole-containing compound and application thereof in an organic electroluminescent device. The structural formula is shown as the following structural formula I,
structural formula I, R1Is hydrogen, C1-C4 alkyl, C6-C30 substituted or unsubstituted aryl; r2Is C6-C30 substituted or unsubstituted pyridyl, C6-C30 substituted or unsubstituted benzonitrile.
Description
The technical field is as follows:
the invention belongs to the technical field of organic electroluminescent device display, and particularly relates to a benzimidazole-containing compound and application thereof in an organic electroluminescent device.
Background art:
organic electroluminescent devices (OLEDs), which are the latest generation of display technologies, can actively emit light and can be freely switched for each pixel, so that the display response time is short and the color contrast is high; the driving voltage is low, a backlight source is not needed, and the energy consumption can be greatly reduced; the use of organic materials enables the device to be thinner, thinner and more environment-friendly; the diversified selection of the substrate provides possibility for flexible and transparent display, and the substrate is widely applied to the fields of mobile phones, flat panel displays, televisions, lighting, vehicle-mounted display and the like.
The common organic electroluminescent device adopts a sandwich type sandwich structure, namely an organic layer is sandwiched between an anode and a cathode at two sides, and the organic layer can be divided into a hole transport layer, an electron transport layer, a luminescent layer, a hole blocking layer, an electron blocking layer and the like according to different photoelectric characteristics of various materials. The light emission mechanism of the device is roughly: under the drive of external voltage, holes and electrons overcome energy barriers, are respectively injected into a hole transport layer and an electron transport layer from an anode and a cathode, then are compounded in a light-emitting layer and release energy, the energy is transferred to an organic light-emitting material, the light-emitting material is transited from a ground state to an excited state after obtaining the energy, and when excited light-emitting electrons are transited back to the ground state again, a light-emitting phenomenon is generated.
An electron transport material is a material that transports electrons from the cathode to the light emitting layer. Electron transport materials generally require better thermal stability and film-forming properties, higher electron mobility, greater electron affinity, and higher excited state energy levels.
The electron transport materials commonly used at present are mainly 8-hydroxyquinoline aluminum, TPBI, Bphen and other materials. Since most organic electroluminescent materials transport holes faster than electrons. This causes an imbalance in the number of electrons and holes in the light-emitting layer, resulting in a device emitting light away from the light-emitting layer and closer to the electrodes, which requires higher driving voltages and also reduces the efficiency and lifetime of the device. Although recent organic electroluminescent devices have been improved, materials excellent in light emitting efficiency, driving voltage, lifetime, and the like are still required, and thus, the search for a highly efficient electron transport material is still an urgent need in the industry.
The invention content is as follows:
the present invention is directed to the above problems, and provides a benzimidazole-containing compound and an application thereof in an organic electroluminescent device, aiming at overcoming the defects of low transmission efficiency, unstable device performance, short lifetime and the like in the prior art, and further aiming at providing an organic electroluminescent device which is prepared by using a novel organic electroluminescent compound in an electron transport layer or a hole blocking layer and has excellent luminous efficiency and device lifetime.
In order to overcome the problems, the benzimidazole is used as a main body and is connected with phenanthrene with different substituents, so that the electronegativity of the material is enhanced, the electron transport performance of the compound is improved, and the heat stability of the compound is improved. The structural formula of the compound is shown as the following structural formula I,
R1is hydrogen, C1-C4 alkyl, C6-C30 substituted or unsubstituted aryl;
R2is C6-C30 substituted or unsubstituted pyridyl, C6-C30 substituted or unsubstituted benzonitrile.
R1Preferably hydrogen, phenyl, tolyl, biphenyl or naphthyl, R2Preferably a pyridyl or benzonitrile.
The compound may be more preferably the following compounds (1 to 48), but is not limited thereto.
The benzimidazole-containing compound shown in the structural formula (I) can be applied to an organic electroluminescent device and used as the composition of an organic layer of the organic electroluminescent device.
The organic electroluminescent device comprises an anode, a cathode and an organic layer, wherein the organic layer is one or more than one of a light-emitting layer, a hole injection layer, a hole transport layer, a hole blocking layer, an electron injection layer and an electron transport layer. One or more of the organic layers contains a benzimidazole-containing organic compound of formula (I).
The layer containing the benzimidazole compound is a light-emitting layer as shown in the structural formula (I).
The layer containing the benzimidazole compound is an electron transport layer or an electron injection layer.
The layer containing the benzimidazole compound is a hole blocking layer as shown in the structural formula (I).
The benzimidazole-containing organic compound shown in the structural formula I can be used alone or mixed with other compounds; the benzimidazole-containing organic compound of the structural formula I can be used singly or in combination of two or more compounds of the structural formula I.
The total thickness of the organic layers of the organic electroluminescent device of the invention is 1 to 1000nm, preferably 50 to 500 nm.
When the compound with the structural formula I is used in the organic electroluminescent device, other materials such as a hole injection layer, a hole transport layer, a luminescent layer, an electron transport layer, an electron injection layer, a barrier layer and the like can be matched to obtain blue light, green light, yellow light, red light or white light.
Each of the organic layers in the organic electroluminescent element of the present invention can be produced by a vacuum evaporation method, a molecular beam evaporation method, a dip coating method in a solvent, a spin coating method, a bar coating method, an inkjet printing method, or the like, and a metal electrode can be produced by an evaporation method or a sputtering method.
The organic electroluminescent device is an organic solar cell, an organic thin film transistor, an organic photodetector, an organic field effect transistor, an organic integrated circuit or an organic photoreceptor.
The invention has the beneficial effects that:
the benzimidazole-containing organic compound as shown in the structural formula (I) is used as an electron transport material, and has the advantages of good thermal stability, high luminous efficiency and high luminous purity. The organic electroluminescent device manufactured by the organic electroluminescent compound can reduce the driving voltage, improve the luminous efficiency, has excellent color purity and prolong the service life of the device.
Description of the drawings:
fig. 1 is a hydrogen nuclear magnetic spectrum of compound 1.
Figure 2 is a hydrogen nuclear magnetic spectrum of compound 25.
Fig. 3 is a schematic structural diagram of an organic electroluminescent device.
Wherein, 110 is a glass substrate, 120 is an anode, 130 is a hole injection layer, 140 is a hole transport layer, 150 is a blocking layer, 160 is a luminescent layer, 170 is an electron transport layer, 180 is an electron injection layer, and 190 is a cathode.
The specific implementation mode is as follows:
in order to describe in more detail the organic electroluminescent compounds of the present invention, the method of synthesizing the compounds, and the organic electroluminescent properties of the device using the compounds of the present invention, the following examples are given, but these examples are only for the purpose of illustrating the present invention and are not limited to the contents of the examples.
EXAMPLE 1 Synthesis of Compound 1
The synthetic route of compound 1 is shown below,
intermediate 1-2 was first prepared. The flask was charged with compound 1-1(20.0g, 48.2mmol), pinamate 3-pyridineborate (19.8g, 96.5mmol) and potassium carbonate (20.0g, 144.7mmol), then toluene (120mL), ethanol (60mL) and deionized water (60mL) were added, bis-triphenylphosphine palladium chloride (1g, 1.4mmol) was added under nitrogen, the reaction was stopped after 15h of reflux stirring, the reaction was separated, concentrated to about 40mL, the solid precipitated by stirring, filtered, and washed with a small amount of toluene ethanol in order to give 14.5g of an off-white solid in 82% yield.
1H NMR(400MHz,CDCl3,):8.85(d,J＝1.6Hz,1H),8.64-8.66 (m,1H),8.31(d,J＝6.8Hz,1H),8.06-8.09(m,2H),7.85-7.92(m,2H), 7.52-7.60(m,4H),7.44-7.51(m,4H),7.36-7.40(m,1H).
Compound 1 was then prepared. The intermediate 1-2(2g, 5.5mmol), benzimidazole-4-borate (2.3g, 5.8mmol) and potassium carbonate (2.3g, 16.6mmol) were added to a flask, then toluene (20mL), ethanol (10mL) and deionized water (10mL) were added, palladium acetate (0.06g, 0.27mmol) and 2-dicyclohexylphosphonium-2, 4, 6-triisopropylbiphenyl (0.12g, 0.54mmol) were added under nitrogen protection, reflux reaction was carried out for 2h, a large amount of solid was precipitated, cooled, filtered, the filter cake was washed with water to neutrality, then washed with ethanol and dried. Then recrystallized once by toluene and dried to obtain 2.4g of product with 73 percent of yield.
1H NMR(400MHz,CDCl3,):8.82-8.89(m,2H),8.44-8.47(m,2H), 7.87-7.95(m,2H),7.77(d,J＝1.2Hz,1H),7.69-7.74(m,1H),7.61-7.64 (m,2H),7.47-7.55(m,8H),7.32-7.37(m,3H),7.13-7.30(m,8H).
Elemental analysis: (C)44H29N3) Theoretical value C, 88.12; h, 4.87; and N, 7.01. Found C, 88.08; h, 4.84; n,7.08. MS (ESI) M/z (M +), theoretical value 599.24; found 599.21.
EXAMPLE 2 Synthesis of Compound 7
The synthetic route of compound 7 is shown below,
the intermediate 1-2(2g, 5.5mmol), benzimidazole-3-borate (2.3g, 5.8mmol) and potassium carbonate (2.3g, 16.6mmol) were added to a flask, then toluene (20mL), ethanol (10mL) and deionized water (10mL) were added, palladium acetate (0.06g, 0.27mmol) and 2-dicyclohexylphosphonium-2, 4, 6-triisopropylbiphenyl (0.12g, 0.54mmol) were added under nitrogen protection, reflux reaction was carried out for 2h, a large amount of solid was precipitated, cooled, filtered, the filter cake was washed with water to neutrality, then washed with ethanol and dried. Then recrystallized once with toluene and dried to obtain 2.2g of product with yield of 67%.
1H NMR(400MHz,CDCl3,):8.85-8.86(m,1H),8.64-8.73(m,3H), 8.27-8.29(m,1H),7.99-8.15(m,3H),7.85-7.92(m,3H),7.68-7.71(m, 1H),7.52-7.62(m,6H),7.36-7.51(m,9H),7.29-7.31(m,2H)。
Elemental analysis: (C)44H29N3) Theoretical value C, 88.12; h, 4.87; and N, 7.01. Found C, 88.15; h, 4.83; and N, 7.02. MS (ESI) M/z (M)+) 599.24 as theoretical value; found 599.22.
EXAMPLE 3 Synthesis of Compound 14
The synthetic route for compound 14 is shown below,
intermediate 14-1 was first prepared. 1-1(20.0g, 48.2mmol), 4-cyanoboronic pinate (22.1g, 96.5mmol) and potassium carbonate (20.0g, 144.7mmol) were added to a flask, and bis-triphenylphosphine palladium chloride (1g, 1.4mmol) was added under nitrogen protection with toluene (120mL), ethanol (60mL) and deionized water (60mL), and the reaction was stopped after stirring under reflux for 15 hours, separated, concentrated to about 40mL, stirred to precipitate a solid, filtered, and washed with a small amount of toluene ethanol in order to obtain 15.0g of an off-white solid with a yield of 80%.
1H NMR(400MHz,CDCl3,):8.31(d,J＝6.8Hz,1H),8.06-8.15(m, 2H),7.86(d,J＝2.0Hz,1H),7.76-7.78(m,2H),7.52-7.61(m,6H), 7.46-7.51(m,3H),7.36-7.40(m,1H)。
Compound 14 was then prepared. The intermediate 14-1(2g, 5.1mmol), benzimidazole-4-borate (2.1g, 5.3mmol) and potassium carbonate (2.1g, 15.2mmol) were added to a flask, then toluene (20mL), ethanol (10mL) and deionized water (10mL) were added, palladium acetate (0.06g, 0.27mmol) and 2-dicyclohexylphosphonium-2, 4, 6-triisopropylbiphenyl (0.12g, 0.54mmol) were added under nitrogen protection, reflux reaction was carried out for 2h, a large amount of solid was precipitated, cooled, filtered, the filter cake was washed with water to neutrality, then washed with ethanol and dried. Then recrystallized once by toluene and dried to obtain 2.4g of product with 75 percent of yield.
1H NMR(400MHz,CDCl3,):8.68-8.72(m,2H),8.06-8.15(m,2H), 7.95-8.00(m,3H),7.76-7.87(m,3H),7.64-7.71(m,3H),7.52-7.61(m, 6H),7.45-7.50(m,4H),7.36-7.44(m,4H),7.29-7.32(m,2H)。
Elemental analysis: (C46H29N3) theoretical values C, 88.58; h, 4.69; n,6.74. Found C, 88.45; h, 4.74; n,6.81. MS (ESI) M/z (M +), theoretical value 623.24; found 623.23.
EXAMPLE 4 Synthesis of Compound 22
The synthetic route for compound 22 is shown below,
the intermediate 14-1(2g, 5.1mmol), benzimidazole-3-borate (2.1g, 5.3mmol) and potassium carbonate (2.1g, 15.2mmol) were added to a flask, then toluene (20mL), ethanol (10mL) and deionized water (10mL) were added, palladium acetate (0.06g, 0.27mmol) and 2-dicyclohexylphosphonium-2, 4, 6-triisopropylbiphenyl (0.12g, 0.54mmol) were added under nitrogen protection, reflux reaction was carried out for 2h, a large amount of solid was precipitated, cooled, filtered, the filter cake was washed with water to neutrality, then washed with ethanol and dried. Then recrystallized once by toluene and dried to obtain 2.6g of product with the yield of 81 percent.
1H NMR(400MHz,CDCl3,):8.70-8.72(m,2H),8,27-8.29(m,1H), 7.99-8.15(m,3H),7.85-7.91(m,2H),7.68-7.78(m,3H),7.52-7.62(m, 8H),7.45-7.50(m,4H),7.36-7.43(m,4H),7.29-7.31(m,2H)。
Elemental analysis: (C46H29N3) theoretical values C, 88.58; h, 4.69; n,6.74. Found C, 88.55; h, 4.67; n, 6.78. MS (ESI) M/z (M +), theoretical value 623.24; found 623.24.
EXAMPLE 5 Synthesis of Compound 25
The synthetic route for compound 25 is shown below,
the intermediate 1-2(2g, 5.5mmol), benzimidazole-4-borate (2.3g, 5.8mmol) and potassium carbonate (2.3g, 16.6mmol) were added to a flask, then toluene (20mL), ethanol (10mL) and deionized water (10mL) were added, palladium acetate (0.06g, 0.27mmol) and 2-dicyclohexylphosphonium-2, 4, 6-triisopropylbiphenyl (0.12g, 0.54mmol) were added under nitrogen protection, reflux reaction was carried out for 2h, a large amount of solid was precipitated, cooled, filtered, the filter cake was washed with water to neutrality, then washed with ethanol and dried. Then recrystallized once by toluene and dried to obtain 2.3g of product with the yield of 81 percent.
1H NMR(400MHz,CDCl3,):8.93(d,J＝8.8Hz,1H),8.87(d,J＝8.8 Hz,1H),8.46-8.48(m,2H),8.01(dd,J＝2.0,8.8Hz,1H),7.86-7.91(m, 2H),7.49-7.77(m,9H),7.15-7.37(m,13H)。
Elemental analysis: (C44H29N3) theoretical values C, 88.12; h, 4.87; and N, 7.01. Found C, 88.13; h, 4.82; and N, 7.05. MS (ESI) M/z (M +), theoretical value 599.24; found 599.25.
EXAMPLE 6 Synthesis of Compound 31
The synthetic route of compound 31 is shown below,
the intermediate CQ1-2(2g, 5.5mmol), benzimidazole-3-borate (2.3g, 5.8mmol) and potassium carbonate (2.3g, 16.6mmol) were added to a flask, then toluene (20mL), ethanol (10mL) and deionized water (10mL) were added, palladium acetate (0.06g, 0.27mmol) and 2-dicyclohexylphosphonium-2, 4, 6-triisopropylbiphenyl (0.12g, 0.54mmol) were added under nitrogen protection, reflux reaction was carried out for 2h, a large amount of solid was precipitated, cooled, filtered, the filter cake was washed with water to neutrality, washed with ethanol and dried. Then recrystallized once by toluene and dried to obtain 2.0g of product with the yield of 69 percent.
1H NMR(400MHz,CDCl3,):8.85-8.86(m,1H),8.74-8.73(m,3H), 8.06-8.15(m,2H),7.83-7.92(m,5H),7.66-7.72(m,2H),7.44-7.60(m, 12H),7.32-7.42(m,4H)。
Elemental analysis: (C44H29N3) theoretical values C, 88.12; h, 4.87; and N, 7.01. Found C, 88.17; h, 4.89; n,6.94.MS (ESI) M/z (M +): theoretical value 599.24; found 599.23.
Example 7
Preparation of an OLED Using Compound 1 prepared in example 1
The transparent conductive ITO glass substrate 110 (with the anode 120 on top) (south glass group ltd, china) was sonicated in a commercial detergent, rinsed in deionized water, sequentially washed with ethanol, acetone and deionized water, baked in a clean environment to completely remove moisture, cleaned with ultraviolet photosynthetic ozone, and treated with oxygen plasma for 30 seconds.
The glass substrate with the anode is placed in a vacuum chamber, vacuum pumping is carried out, HIL (45nm) is evaporated on ITO to be used as a hole injection layer 130, and the evaporation rate is 0.1 nm/s.
A compound NPB was deposited on the hole injection layer at a rate of 0.1nm/s to form a 50nm thick hole transport layer 140, and a TCTA was deposited at a rate of 0.1nm/s to form a 5nm thick electron blocking layer 150.
A light-emitting layer 160 with a thickness of 30nm was deposited on the hole-transporting layer, wherein RH was the host light-emitting material and 5 wt% of Ir (pq)2acac was the phosphorescent dopant guest material, at a deposition rate of 0.1 nm/s.
Compound 1 with a thickness of 30nm is evaporated on the light-emitting layer as an electron transport layer 170, the evaporation rate is 0.1nm/s, 1nm lithium fluoride is evaporated as an electron injection layer 180, and 100nm aluminum is evaporated as a device cathode 190.
Example 8
The difference from example 7 is that compound 8 is used instead of compound 1.
Example 9
The difference from example 7 is that compound 14 is used instead of compound 1.
Example 10
The difference from example 7 is that compound 22 is used instead of compound 1.
Example 11
The difference from example 7 is that compound 25 is used instead of compound 1.
Example 12
The difference from example 7 is that compound 1 is replaced by compound 31.
Comparative example 1
The difference from example 7 is that compound ET1 is used instead of compound 1 according to the invention. The structural formula of ET1 is as follows,
comparative example 2
The difference from example 7 is that compound ET2 is used instead of compound 1 according to the invention. The structural formula of ET2 is as follows,
the existing known materials of ET1 and ET2 are obtained by market purchase.
The maximum brightness of the prepared device measured by a Photo Research PR650 spectrometer is 5000cd/m2The efficiency in luminance, the lighting voltage, the CIE coordinates, are specified in table 1.
TABLE 1
As can be seen from the experimental data in Table 1, the benzimidazole-containing compound of the present invention having the chemical formula I can be applied to an organic electroluminescent device as an electron transport material. The organic electroluminescent device prepared by the benzimidazole-containing compound has lower working voltage and higher brightness than the organic electroluminescent devices prepared by the comparative examples 1 and 2 in the prior art under the same brightness, and the current efficiency, the power efficiency and the external quantum efficiency are improved. At the same time, the service life of the device prepared by the compound of the invention is greatly improved compared with the prior art comparative example under the same current density. This is because, under the same current density, the invention has better electron transmission capability, lower working voltage, less power consumption of the device, and the service life of the device can be improved.
The structural formulae of the related compounds mentioned in the examples are as follows:
the compounds are all known materials and are obtained by market purchase.
The foregoing detailed description of the preferred embodiments of the invention has been presented. It should be understood that numerous modifications and variations could be devised by those skilled in the art in light of the present teachings without departing from the inventive concepts. Therefore, the technical solutions available to those skilled in the art through logic analysis, reasoning and limited experiments based on the prior art according to the concept of the present invention should be within the scope of protection defined by the claims.
Claims (8)
1. A compound containing benzimidazole is characterized in that the structural formula is shown as the following structural formula I,
structural formula I, R1Is hydrogen, C1-C4 alkyl, C6-C30 substituted or unsubstituted aryl;
R2is C6-C30 substituted or unsubstituted pyridyl, C6-C30 substituted or unsubstituted benzonitrile.
2. The benzimidazole-containing compound of claim 1, wherein R is1Is hydrogen, phenyl,Tolyl, biphenyl or naphthyl, R2Is pyridyl or benzonitrile.
3. The application of the benzimidazole-containing compound in an organic electroluminescent device is characterized in that the benzimidazole-containing compound can be applied to the organic electroluminescent device and is used as a composition of an organic layer of the organic electroluminescent device.
4. The benzimidazole-containing compound of claim 3, wherein the organic electroluminescent device comprises an anode, a cathode and one or more organic layers selected from a light-emitting layer, a hole injection layer, a hole transport layer, a hole blocking layer, an electron injection layer and an electron transport layer, and one or more organic layers comprise the benzimidazole-containing organic compound of formula I.
5. The benzimidazole-containing compound of claim 4, wherein the layer of the benzimidazole-containing compound of formula I is a light-emitting layer.
6. The benzimidazole-containing compound of claim 4, wherein the benzimidazole-containing compound of formula I is present in an electron transport layer or an electron injection layer.
7. The benzimidazole-containing compound of claim 4, wherein the layer of the benzimidazole-containing compound of formula I is a hole-blocking layer.
8. The benzimidazole-containing compound of claim 4, wherein the benzimidazole-containing organic compound of formula I can be used alone or in combination with other compounds; the benzimidazole-containing organic compound represented by the structural formula I may be used alone or in combination of two or more compounds.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010509195.8A CN111704580A (en) | 2020-06-07 | 2020-06-07 | Benzimidazole-containing compound and application thereof in organic electroluminescent device |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010509195.8A CN111704580A (en) | 2020-06-07 | 2020-06-07 | Benzimidazole-containing compound and application thereof in organic electroluminescent device |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN111704580A true CN111704580A (en) | 2020-09-25 |
Family
ID=72539703
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202010509195.8A Pending CN111704580A (en) | 2020-06-07 | 2020-06-07 | Benzimidazole-containing compound and application thereof in organic electroluminescent device |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN111704580A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112898199A (en) * | 2021-01-26 | 2021-06-04 | 上海传勤新材料有限公司 | Organic electron transport material containing nitrogen atom heterocycle and benzonitrile and application thereof |
| CN114907321A (en) * | 2022-06-17 | 2022-08-16 | 常州强力昱镭光电材料有限公司 | Azaphenanthrene compound, electron transport material and application thereof |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102190627A (en) * | 2010-12-10 | 2011-09-21 | 吉林大学 | 9,10-phenanthroimidazole derivatives and use thereof as electroluminescent materials |
| CN102241620A (en) * | 2010-05-14 | 2011-11-16 | 国立清华大学 | Benzo(9,10)phenanthryl-containing aromatic compounds and organic light emitting diode using same |
| KR20130113357A (en) * | 2012-04-05 | 2013-10-15 | (주)씨에스엘쏠라 | New arylcarbazolylacridine-based organic electroluminescent compounds and organic electroluminescent device comprising the same |
| CN108807697A (en) * | 2017-04-26 | 2018-11-13 | 固安鼎材科技有限公司 | Organic electroluminescence device and phenanthrene derivative |
| CN110128349A (en) * | 2018-02-09 | 2019-08-16 | 北京鼎材科技有限公司 | A kind of nitrogenous heterocyclic polycyclic aromatic hydrocarbon derivative and its application and organic electroluminescence device |
-
2020
- 2020-06-07 CN CN202010509195.8A patent/CN111704580A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102241620A (en) * | 2010-05-14 | 2011-11-16 | 国立清华大学 | Benzo(9,10)phenanthryl-containing aromatic compounds and organic light emitting diode using same |
| CN102190627A (en) * | 2010-12-10 | 2011-09-21 | 吉林大学 | 9,10-phenanthroimidazole derivatives and use thereof as electroluminescent materials |
| KR20130113357A (en) * | 2012-04-05 | 2013-10-15 | (주)씨에스엘쏠라 | New arylcarbazolylacridine-based organic electroluminescent compounds and organic electroluminescent device comprising the same |
| CN108807697A (en) * | 2017-04-26 | 2018-11-13 | 固安鼎材科技有限公司 | Organic electroluminescence device and phenanthrene derivative |
| CN110128349A (en) * | 2018-02-09 | 2019-08-16 | 北京鼎材科技有限公司 | A kind of nitrogenous heterocyclic polycyclic aromatic hydrocarbon derivative and its application and organic electroluminescence device |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112898199A (en) * | 2021-01-26 | 2021-06-04 | 上海传勤新材料有限公司 | Organic electron transport material containing nitrogen atom heterocycle and benzonitrile and application thereof |
| CN114907321A (en) * | 2022-06-17 | 2022-08-16 | 常州强力昱镭光电材料有限公司 | Azaphenanthrene compound, electron transport material and application thereof |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US8173272B2 (en) | Diamine derivatives, preparation method thereof and organic electronic device using the same | |
| US6670054B1 (en) | Electroluminescent devices | |
| EP2296204B1 (en) | Light-emitting element | |
| JP5250516B2 (en) | A novel blue light emitter for use in organic electroluminescent devices | |
| JP4435990B2 (en) | Organometallic complex molecule and organic electroluminescent device using the same | |
| US6562982B1 (en) | Carbazole compounds | |
| KR100893044B1 (en) | Anthracene derivatives, organic electronic devices using the same and electronic apparatuses comprising the same | |
| KR101865606B1 (en) | Condensed aryl compounds and organic light-diode including the same | |
| JP4786917B2 (en) | Organometallic complex, luminescent solid, organic EL device and organic EL display | |
| JP2013510141A (en) | Compound for organic photoelectric device and organic photoelectric device including the same | |
| KR101732969B1 (en) | Phosphine oxide derivative compound and organic electroluminescent device using the same | |
| KR101720079B1 (en) | Quinoxaline derivative compound and organic electroluminescent device using the same | |
| JP2010531808A (en) | Organometallic complex derivative and organic light emitting device using the same | |
| JP2016520253A (en) | Organic electroluminescence device | |
| KR20130121597A (en) | Using triphenylamine as hole transporting mateial and organic electroluminescent device using the same | |
| JP6133495B2 (en) | Organic electronic materials | |
| WO2006129471A1 (en) | Material for organic electroluminescence device, organic electroluminescence device, process for producing organic electroluminescence device, lighting installation and display unit | |
| KR101694496B1 (en) | Dibenzothiophene derivative compound and organic electroluminescent device using the same | |
| JP5595082B2 (en) | Novel benzoxazolylcarbazole compound and organic light emitting device having the same | |
| CN111704580A (en) | Benzimidazole-containing compound and application thereof in organic electroluminescent device | |
| WO2018137296A1 (en) | Compound containing quinoxalinyl and biphenyl groups and organic electroluminescent device thereof | |
| WO2016190014A1 (en) | Method for producing material for organic electroluminescent elements, and organic electroluminescent element | |
| KR20100137983A (en) | New anthracene derivatives, preparation method thereof and organic electronic device using the same | |
| KR102304989B1 (en) | An electroluminescent compound and an electroluminescent device comprising the same | |
| KR102181332B1 (en) | Heterocyclic compounds and organic light emitting diode device comprising the same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination |