CN113620860B - Organic electroluminescent compound and preparation method and application thereof - Google Patents
Organic electroluminescent compound and preparation method and application thereof Download PDFInfo
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- CN113620860B CN113620860B CN202011475226.9A CN202011475226A CN113620860B CN 113620860 B CN113620860 B CN 113620860B CN 202011475226 A CN202011475226 A CN 202011475226A CN 113620860 B CN113620860 B CN 113620860B
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- Prior art keywords
- organic electroluminescent
- electroluminescent compound
- oled device
- hole transport
- transport layer
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 52
- 238000002360 preparation method Methods 0.000 title abstract description 11
- 230000005525 hole transport Effects 0.000 claims abstract description 19
- 239000003054 catalyst Substances 0.000 claims description 19
- 238000002347 injection Methods 0.000 claims description 9
- 239000007924 injection Substances 0.000 claims description 9
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 230000009471 action Effects 0.000 claims description 6
- 230000000903 blocking effect Effects 0.000 claims description 5
- 238000005859 coupling reaction Methods 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 4
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 4
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 4
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 4
- 239000002994 raw material Substances 0.000 claims description 4
- 239000004305 biphenyl Substances 0.000 claims description 3
- 235000010290 biphenyl Nutrition 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- 239000010409 thin film Substances 0.000 claims description 3
- ICPSWZFVWAPUKF-UHFFFAOYSA-N 1,1'-spirobi[fluorene] Chemical compound C1=CC=C2C=C3C4(C=5C(C6=CC=CC=C6C=5)=CC=C4)C=CC=C3C2=C1 ICPSWZFVWAPUKF-UHFFFAOYSA-N 0.000 claims description 2
- 101100391172 Dictyostelium discoideum forA gene Proteins 0.000 claims description 2
- 101100391182 Dictyostelium discoideum forI gene Proteins 0.000 claims description 2
- 239000010408 film Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical group I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 9
- 238000005137 deposition process Methods 0.000 abstract description 2
- 238000013461 design Methods 0.000 abstract description 2
- 230000009477 glass transition Effects 0.000 abstract description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 75
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 22
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- 230000015572 biosynthetic process Effects 0.000 description 12
- 238000001816 cooling Methods 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- 238000010438 heat treatment Methods 0.000 description 11
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 10
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical group [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
- 238000001514 detection method Methods 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000012043 crude product Substances 0.000 description 8
- 238000004128 high performance liquid chromatography Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000004440 column chromatography Methods 0.000 description 7
- 239000003480 eluent Substances 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000007740 vapor deposition Methods 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- 229910052763 palladium Inorganic materials 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical group C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 125000005259 triarylamine group Chemical group 0.000 description 3
- UPJLZKCEPFAKSH-UHFFFAOYSA-N 2',7'-dibromo-9,9'-spirobi[fluorene] Chemical compound C12=CC=CC=C2C2=CC=CC=C2C21C1=CC(Br)=CC=C1C1=CC=C(Br)C=C12 UPJLZKCEPFAKSH-UHFFFAOYSA-N 0.000 description 2
- SLAMLWHELXOEJZ-UHFFFAOYSA-N 2-nitrobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1[N+]([O-])=O SLAMLWHELXOEJZ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- DKGYESBFCGKOJC-UHFFFAOYSA-N thiophen-3-amine Chemical compound NC=1C=CSC=1 DKGYESBFCGKOJC-UHFFFAOYSA-N 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- JAUCIDPGGHZXRP-UHFFFAOYSA-N 4-phenyl-n-(4-phenylphenyl)aniline Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1NC(C=C1)=CC=C1C1=CC=CC=C1 JAUCIDPGGHZXRP-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical group [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 230000032683 aging Effects 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
- -1 aromatic diamine small molecule Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- GHQCIALFYKYZGS-UHFFFAOYSA-N dibenzofuran-3-amine Chemical compound C1=CC=C2C3=CC=C(N)C=C3OC2=C1 GHQCIALFYKYZGS-UHFFFAOYSA-N 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- COLNWNFTWHPORY-UHFFFAOYSA-M lithium;8-hydroxyquinoline-2-carboxylate Chemical compound [Li+].C1=C(C([O-])=O)N=C2C(O)=CC=CC2=C1 COLNWNFTWHPORY-UHFFFAOYSA-M 0.000 description 1
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 1
- IMKMFBIYHXBKRX-UHFFFAOYSA-M lithium;quinoline-2-carboxylate Chemical compound [Li+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 IMKMFBIYHXBKRX-UHFFFAOYSA-M 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- USFPINLPPFWTJW-UHFFFAOYSA-N tetraphenylphosphonium Chemical group C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 USFPINLPPFWTJW-UHFFFAOYSA-N 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical class C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/96—Spiro-condensed ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- 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
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
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- 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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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- 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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- 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
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- 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
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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- 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
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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- 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
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- 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
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- 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
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
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- 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
- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Abstract
The invention relates to the technical field of organic electroluminescent materials, in particular to an organic electroluminescent compound, a preparation method and application thereof; the organic electroluminescent compound has a structure shown in a formula I, and has higher glass transition temperature and good thermal stability through the design of a molecular structure and a substituent, so that the organic electroluminescent compound is prevented from being degraded in a high-temperature deposition process; and the hole transport performance and stability of the OLED device as a hole transport layer are remarkably improved, so that the OLED device containing the OLED device has high luminous efficiency and long service life, and the power efficiency and the power consumption are improved.
Description
Technical Field
The invention relates to the technical field of organic electroluminescent materials, in particular to an organic electroluminescent compound, a preparation method and application thereof.
Background
Electroluminescent devices (EL devices) are self-luminous devices, which have advantages in that they have a wide viewing angle, a large contrast ratio, and a fast response time. Currently, the first organic EL device is formed by Eastman Kodak (Eastman Kodak) by using an aromatic diamine small molecule and a metal aluminum complex as a material for forming a light emitting layer [ (applied physical journal (applied. Phys. Lett.) ]) 51,913,1987].
In the prior art, hole transport materials are commonly used in hole transport layers or hole injection layers and exciton blocking layers, and commonly used hole transport materials are triarylamine derivatives containing at least two triarylamine groups or at least one triarylamine group and at least one carbazole group; the above compounds are generally derived from a diarylamino-substituted triphenylamine (TPA type), diarylamino-substituted biphenyl derivatives (TAD type) or combinations of these base compounds. The use of the above compounds in fluorescent or phosphorescent OLEDs, in particular in organic electroluminescent devices, requires improvements in terms of operating voltage, efficiency, lifetime and thermal stability during sublimation.
In view of this, the present invention has been made.
Disclosure of Invention
Aiming at the defects existing in the prior art, the invention provides an organic electroluminescent compound, and a preparation method and application thereof.
As a first object of the present invention, there is provided an organic electroluminescent compound intermediate; the intermediate can be used for synthesizing organic electroluminescent compounds.
Specifically, the organic electroluminescent compounds have a structure as shown in formula M-1:
as a second object of the present invention, there is provided a process for producing the above organic electroluminescent compound intermediate, which comprises the following synthetic route:
the method specifically comprises the following steps:
(1) Taking a compound IM-01 as a raw material, and carrying out coupling reaction with o-nitrobenzoic acid under the action of a catalyst to obtain a compound IM-02;
(2) Carrying out closed-loop reaction on a compound IM-02 under the action of a catalyst to obtain the intermediate of the organic electroluminescent compound with the structure shown as the formula M-1;
preferably, in the step (1), the catalyst is a palladium catalyst;
preferably, in the step (2), the catalyst is a phosphine catalyst;
further, in the step (1), the catalyst is tetraphenylphosphine palladium;
further, in the step (2), the catalyst is triphenylphosphine.
The palladium catalyst is more favorable for ring-closure reaction, and improves the synthesis efficiency of the intermediate of the organic electroluminescent compound.
As a third object of the present invention, there is provided an organic electroluminescent compound; the organic electroluminescent compound has good hole transmission performance and stability, and can be used for manufacturing OLED devices with longer service life.
Specifically, the organic electroluminescent compounds have a structure as shown in formula I:
wherein Ar is 1 、Ar 2 、Ar 3 Each independently represents a compound having C 6 ～C 60 Aromatic or C of (2) 6 ～C 60 Is a heteroaromatic ring system.
Preferably Ar 1 、Ar 2 、Ar 3 Each independently represents benzene, biphenyl, naphthalene, phenanthrene, fluorene, spirobifluorene, dibenzofuran or dibenzoThiophene.
Preferably, the organic electroluminescent compound is selected from one or more of the formulas H1 to H20:
as a fourth object of the present invention, there is provided a method for producing the above organic electroluminescent compound, comprising the steps of:
(1) To be used forAs raw material, with Ar 1 X is subjected to coupling reaction under the action of a catalyst to obtain
(2) To be used forIs prepared from (a) and (b) herba Cistanchis>Coupling reaction under the action of catalyst to obtain +.>
Wherein X represents halogen;
Ar 1 、Ar 2 、Ar 3 each independently having the same limitations as claim 3.
Preferably, in the step (1), the catalyst is a copper catalyst; preferably cuprous iodide;
preferably, in the step (2), the catalyst is a palladium catalyst; preferably Pd 2 (dba) 3 ；
Preferably, X represents I.
As a fifth object of the present invention, there is provided a hole transport layer for an OLED device, the hole transport layer including the above-described organic electroluminescent compound.
As a sixth object of the present invention, there is provided an OLED device including an anode, a cathode, and at least one organic thin film layer between the anode and the cathode; the organic film layer comprises a hole transport layer and any one or a combination of at least two of a hole injection layer, an electron blocking layer, a hole blocking layer, a light emitting layer, an electron transport layer and an electron injection layer;
the hole transport layer is the hole transport layer for the OLED device.
As a seventh object of the present invention, there is provided an electronic apparatus comprising the OLED device as described above.
The invention has the excellent effects that:
(1) The organic electroluminescent compound provided by the invention has a condensed ring structure, and has higher glass transition temperature and good thermal stability through the design of a molecular structure and a substituent, so that the organic electroluminescent compound is prevented from being degraded in a high-temperature deposition process; and the hole transport performance and stability of the OLED device as a hole transport layer are remarkably improved, so that the OLED device containing the OLED device has high luminous efficiency and long service life, and the power efficiency and the power consumption are improved.
(2) The organic electroluminescent compounds according to the invention are suitable for use in fluorescent OLED devices and phosphorescent OLED devices, especially phosphorescent OLED devices.
Detailed Description
The following examples are illustrative of the invention and are not intended to limit the scope of the invention.
The structure of the related compound is as follows:
example 1
The embodiment provides an organic electroluminescent compound intermediate M-1, which has the following structure:
the synthetic route of M-1 is as follows:
the method specifically comprises the following steps:
(1) Synthesis of IM-02:
to a 1000ml three-necked flask, 2, 7-dibromo-9, 9 '-spirobifluorene (47.4 g, 0.1 mol) and o-nitrobenzoic acid (16.7 g, 0.1 mol) were added, toluene (250 ml), ethanol (125 ml) and water (125 ml) were added, sodium carbonate (13.8 g, 0.13 mol) was added with stirring, and further tetrakis triphenylphosphine palladium (0.12 g, 0.00001 mol) was added, nitrogen was replaced, heating was started, the temperature was slowly raised to 80 ℃ (the reaction process kept under nitrogen protection) and the reaction was carried out for 2 hours, HPLC detection (raw material 2, 7-dibromo-9, 9' -spirobifluorene < 1%) was stopped, and the reaction was cooled to room temperature. After the reaction is finished, cooling to 25 ℃, separating liquid, and drying an organic phase by anhydrous sodium sulfate; column chromatography, using toluene as eluent; concentration gives crude product, recrystallisation from toluene: ethanol=1:2 gives 36.1g of intermediate IM-02, purity >98% yield 70%.
(2) Synthesizing M-1:
to a 1000ml three-necked flask, IM-02 (36.1 g, 0.07 mol) was added, dichlorobenzene (500 ml) was added, triphenylphosphine (36.7 g, 0.14 mol) was added, nitrogen was replaced, the temperature was gradually raised to 170℃and the reaction was stopped by HPLC detection (IM-02 < 1%) for 10 hours. Evaporating the solvent under reduced pressure, cooling to room temperature, adding ethyl acetate for dissolution, separating by column chromatography, obtaining a solid crude product by using petroleum ether ethyl acetate as an eluent, and using toluene: ethanol=1: 4, to obtain 23.7g of intermediate M-1 with purity of 98% and yield of 70%.
Example 2
The present embodiment provides an organic electroluminescent compound H1 having the following structure:
the preparation method of the H1 comprises the following steps:
(1) Synthesis of M-1-1:
to a 500ml three-necked flask, M-1 (23.7 g, 0.049 mol) and iodobenzene (10 g, 0.049 mol) were added, DMF 200ml was added, potassium hydroxide (5.4 g, 0.098 mol), cuprous iodide (9.3 g, 0.049 mol) and the mixture was stirred, and the mixture was heated to 150℃to react for 3 hours, HPLC detection (M-1<1%) and the reaction was stopped, the reaction mixture was cooled, 200ml of water was added, solids were precipitated and filtered to obtain a crude product, which was recrystallized from toluene to obtain 22g of intermediate M-1-1, purity was 98% and yield was 80%.
(2) Synthesis of H1:
into a 250ml three-necked flask, M-1-1 (5.6 g, 0.01 mol) and bis (4-biphenylyl) amine (3.2 g, 0.01 mol) were added, toluene was added in an amount of 100ml, and sodium t-butoxide (1.2 g, 0.013 mol), pd were added with stirring 2 (dba) 3 (0.046 g, 0.00005 mol), replacing nitrogen, adding 10% toluene solution of tri-tert-butylphosphine 0.2g, heating, slowly heating to 80deg.C (reaction process kept nitrogen protection), reacting for 2 hr, HPLC detection (M-1)<1 percent) stopping the reaction, and cooling to room temperature. After the reaction is finished, cooling to 25 ℃, washing with salt water for 2 times, and drying the organic phase by using anhydrous sodium sulfate; column chromatography, using toluene as eluent; concentrating to obtain crude product, recrystallizing with toluene to obtain product H1 with purity of 6.4g>99% yield 80%.
Nuclear magnetic detection was performed on the H1 compound, and the data were analyzed as follows:
1 HNMR(300MHz，CDCl 3 )δ8.55(d，1H)，δ8.22(s，1H)δ8.20(d，1H)，δ7.94～7.89(m，3H)，δ7.75～7.73(m，5H)，δ7.62～7.28(m，28H)，δ7.16(t，1H)。
example 3
The embodiment provides an organic electroluminescent compound H2 having the following structure:
the preparation method of the H2 comprises the following steps:
(1) Synthesis of M-1-1:
as in example 2.
(2) Synthesis of H2:
into a 250ml three-necked flask, M-1-1 (5.6 g, 0.01 mol) and N- [1,1' -biphenyl-4-yl were introduced]-9, 9-dimethyl-9H-fluoren-2-amine (3.6 g, 0.01 mol), toluene 100ml, sodium t-butoxide (1.2 g, 0.013 mol), pd were added with stirring 2 (dba) 3 (0.046 g, 0.00005 mol), replacing nitrogen, adding 10% toluene solution of tri-tert-butylphosphine 0.2g, heating, slowly heating to 80deg.C (reaction process kept nitrogen protection), reacting for 2 hr, and detecting by HPLC (M-1)<1 percent) stopping the reaction, and cooling to room temperature. After the reaction is finished, cooling to 25 ℃, washing with salt water for 2 times, and drying the organic phase by using anhydrous sodium sulfate; column chromatography, using toluene as eluent; concentrating to obtain crude product, recrystallizing with toluene to obtainTo product 6.7g of product H2, purity>99% yield 80%.
Nuclear magnetic detection was performed on H2 compounds, and the data were analyzed as follows:
1 HNMR(300MHz，CDCl 3 )δ8.55(d，1H)，δ8.22(s，1H)δ8.20(d，1H)，δ7.94～7.86(m，5H)，δ7.75～7.73(m，3H)，δ7.62～7.28(m，25H)，δ7.16(m，2H),δ1.69(s，6H)。
example 4
The present embodiment provides an organic electroluminescent compound H5 having the following structure:
the preparation method of the H5 comprises the following steps:
(1) Synthesis of M-1-1:
as in example 2.
(2) Synthesis of H5:
into a 50ml three-necked flask, M-1-1 (5.6 g, 0.01 mol) and N- [1,1' -biphenyl-4-yl were introduced]Dibenzo [ b, d ]]Thiophene-3-amine (3.5 g, 0.01 mol), toluene (100 ml) and sodium t-butoxide (1.2 g, 0.013 mol), pd were added with stirring 2 (dba) 3 (0.046 g, 0.00005 mol), replacing nitrogen, adding 10% toluene solution of tri-tert-butylphosphine 0.2g, heating, slowly heating to 80deg.C (reaction process kept nitrogen protection), reacting for 2 hr, and detecting by HPLC (M-1)<1 percent) stopping the reaction, and cooling to room temperature. After the reaction is finished, cooling to 25 ℃, washing with salt water for 2 times, and drying the organic phase by using anhydrous sodium sulfate; column chromatography, using toluene as eluent; concentrating to obtain crude product, recrystallizing with toluene to obtain product H5 with purity of 6.6g>99% yield 80%.
The nuclear magnetic detection is carried out on the H5 compound, and the data are analyzed as follows:
1 HNMR(300MHz，CDCl 3 )δ8.55(d，1H)，δ8.45(d，1H),δ8.22(s，1H)δ8.20(d，1H)，δ8.01(d，1H),δ7.94～7.89(m，4H)，δ7.75～7.73(m，3H)，δ7.62～7.28(m，25H)，δ7.16(t，1H)。
example 5
The present embodiment provides an organic electroluminescent compound H8 having the following structure:
the preparation method of the H8 comprises the following steps:
(1) Synthesis of M-1-1:
as in example 2.
(2) Synthesis of H8:
into a 250ml three-necked flask, M-1-1 (5.6 g, 0.01 mol) and N- (dibenzo [ b, d) were added]Thiophen-3 yl) dibenzo [ b, d]Furan-3-amine (3.65 g, 0.01 mol), toluene (100 ml) and sodium t-butoxide (1.2 g, 0.013 mol), pd were added with stirring 2 (dba) 3 (0.046 g, 0.00005 mol), replacing nitrogen, adding 10% toluene solution of tri-tert-butylphosphine 0.2g, heating, slowly heating to 80deg.C (reaction process kept nitrogen protection), reacting for 2 hr, and detecting by HPLC (M-1)<1 percent) stopping the reaction, and cooling to room temperature. After the reaction is finished, cooling to 25 ℃, washing with salt water for 2 times, and drying the organic phase by using anhydrous sodium sulfate; column chromatography, using toluene as eluent; concentrating to obtain crude product, recrystallizing with toluene to obtain product H8 with purity of 6.6g>99%, yield: 80%.
Nuclear magnetic detection was performed on H8 compounds, and the data were analyzed as follows:
1 HNMR(300MHz，CDCl 3 )δ8.55(d，1H)，δ8.22(s，1H)δ8.20(d，1H)，δ8.01～7.80(m，9H),δ7.73(s，1H)，δ7.62～7.28(m，20H)，δ7.16(t，1H),δ6.91(d，2H)。
example 6
The present embodiment provides an organic electroluminescent compound H17 having the following structure:
the preparation method of the H17 comprises the following steps:
(1) Synthesis of M-1-1:
as in example 2.
(2) Synthesis of H17:
into a 250ml three-necked flask, M-1-1 (5.6 g, 0.01 mol) and N- [1,1' -biphenyl-2-yl were introduced]Dibenzo [ b, d ]]Thiophene-3-amine (3.5 g, 0.01 mol), toluene (100 ml) and sodium t-butoxide (1.2 g, 0.013 mol), pd were added with stirring 2 (dba) 3 (0.046 g, 0.00005 mol), replacing nitrogen, adding 10% toluene solution of tri-tert-butylphosphine 0.2g, heating, slowly heating to 80deg.C (reaction process kept nitrogen protection), reacting for 2 hr, and detecting by HPLC (M-1)<1 percent) stopping the reaction, and cooling to room temperature. After the reaction is finished, cooling to 25 ℃, washing with salt water for 2 times, and drying the organic phase by using anhydrous sodium sulfate; column chromatography, using toluene as eluent; concentrating to obtain crude product, recrystallizing with toluene to obtain product H17 with purity of 6.6g>99% yield 80%.
The nuclear magnetic detection is carried out on the H17 compound, and the data are analyzed as follows:
1 HNMR(300MHz，CDCl 3 )δ8.55(d，1H)，δ8.45(d，1H),δ8.22(s，1H)δ8.20(d，1H)，δ8.10(d，1H),δ8.01(d，1H),δ7.94～7.89(m，4H)，δ7.73(s，1H)，δ7.62～7.27(m，23H)，δ7.35～7.08(m，4H)。
application example 1
The application example provides an OLED device, and the preparation method of the OLED device comprises the following steps:
(1) A transparent electrode Indium Tin Oxide (ITO) thin film (15 Ω/sq, samsung Corning, san-korea) on a glass substrate for an Organic Light Emitting Diode (OLED) device was sequentially ultrasonically cleaned with trichloroethylene, acetone, ethanol, and distilled water, and then stored in isopropyl alcohol; the ITO substrate was mounted on a substrate holder of a vacuum vapor deposition apparatus.
(2) The compound HIL was introduced into the chamber of a vacuum vapor deposition apparatus, and then the chamber pressure of the apparatus was controlled to 10 -6 A current was applied to the chamber to evaporate the above-introduced substances, thereby forming a hole injection layer having a thickness of 60nm on the ITO substrate.
(3) The organic electronic compound H1 provided by the invention is introduced into another chamber of the vacuum vapor deposition apparatus, and is evaporated by applying a current to the chamber, thereby forming a hole transport layer having a thickness of 20nm on the hole injection layer.
(4) Introducing the compound CBP into one chamber of the vacuum vapor deposition apparatus as a host material, and introducing the compound D-1 into the other chamber as a dopant; the two materials were evaporated at different rates and deposited at a doping amount of 15 wt% (based on the total weight of the host material and the dopant), thereby forming a light emitting layer having a thickness of 30nm on the hole transport layer.
(5) Introducing the compound ETL into one chamber and lithium 8-hydroxyquinolinate (lithium quinolate) into the other chamber; the two materials were evaporated at the same rate and deposited with a doping amount of 50 wt% respectively, thereby forming an electron transport layer having a thickness of 30nm on the light emitting layer.
(6) 8-hydroxyquinoline lithium with the thickness of 2nm is deposited on the electron transport layer as an electron injection layer EIL.
(7) Depositing an Al cathode with the thickness of 150nm on the electron injection layer by another vacuum vapor deposition device; the OLED device is obtained.
The OLED device is prepared by the methodThrough a process of forming a polymer film at 10 -6 Purification was carried out by vacuum sublimation under torr conditions.
Application example 2
The present application example provides an OLED device, which is different from application example 1 in that: and (3) replacing H1 in the step (3) with H2.
Application example 3
The present application example provides an OLED device, which is different from application example 1 in that: and (3) replacing H1 in the step (3) with H4.
Application example 4
The present application example provides an OLED device, which is different from application example 1 in that: and (3) replacing H1 in the step (3) with H5.
Application example 5
The present application example provides an OLED device, which is different from application example 1 in that: and (3) replacing H1 in the step (3) with H7.
Application example 6
The present application example provides an OLED device, which is different from application example 1 in that: and (3) replacing H1 in the step (3) with H8.
Application example 7
The present application example provides an OLED device, which is different from application example 1 in that: and (3) replacing H1 in the step (3) with H13.
Application example 8
The present application example provides an OLED device, which is different from application example 1 in that: and (3) replacing H1 in the step (3) with H20.
Comparative example 1
This comparative example provides an OLED device, which differs from application example 1 in that: replacing H1 in the step (3) with HTL.
Performance testing of OLED devices
The OLED-1000 multichannel accelerated aging life and photochromic performance analysis system manufactured by Hangzhou is used for testing the driving voltage, the current efficiency and the life LT90 of the OLED devices provided in application examples 1-8 and comparative example 1; where LT90 refers to the time required to keep the current density unchanged and the luminance drops to 90% of the original luminance.
The specific test results are shown in table 1:
TABLE 1
/>
As can be seen from table 1, the organic electroluminescent compounds according to the present invention have excellent properties compared to the organic electroluminescent compounds in the prior art, and thus the organic electroluminescent device provided by the present invention has high luminous efficiency and long operating life; also, the organic electroluminescent device requires a low driving voltage, thereby improving power efficiency and power consumption.
While the invention has been described in detail in the foregoing general description, embodiments and experiments, it will be apparent to those skilled in the art that modifications and improvements can be made thereto. Accordingly, such modifications or improvements may be made without departing from the spirit of the invention and are intended to be within the scope of the invention as claimed.
Claims (7)
1. An organic electroluminescent compound characterized by having a structure represented by formula I:
Ar 1 benzene, biphenyl, naphthalene or phenanthrene; ar (Ar) 2 、Ar 3 Each independently represents biphenyl, fluorene, spirobifluorene, dibenzofuran or dibenzothiophene.
2. The organic electroluminescent compound according to claim 1, wherein the organic electroluminescent compound is selected from one or more of the formulae H2 to H20:
3. the method for producing an organic electroluminescent compound as claimed in claim 1 or 2, comprising the steps of:
(1) To be used forAs raw material, with Ar 1 Coupling reaction of X under the action of catalyst to obtain +.>
(2) To be used forIs prepared from (a) and (b) herba Cistanchis>Coupling reaction under the action of catalyst to obtain
Wherein X represents halogen;
Ar 1 、Ar 2 、Ar 3 each independently having the same limitations as claim 1.
4. A process according to claim 3, wherein in step (1) the catalyst is copper iodide;
and/or in the step (2), the catalyst is Pd 2 (dba) 3 ；
And/or X represents I.
5. A hole transport layer for an OLED device, characterized in that the hole transport layer comprises the organic electroluminescent compound according to claim 1 or 2.
6. An OLED device comprising an anode, a cathode, and at least one organic thin film layer between the anode and the cathode; the organic film layer comprises a hole transport layer and any one or a combination of at least two of a hole injection layer, an electron blocking layer, a hole blocking layer, a light emitting layer, an electron transport layer and an electron injection layer;
the hole transport layer is a hole transport layer for an OLED device according to claim 5.
7. An electronic device comprising the OLED device of claim 6.
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| WO2011108901A2 (en) * | 2010-03-05 | 2011-09-09 | 덕산하이메탈(주) | Spiro-carbazole compound comprising a spiro skeleton, and an organic electronic element using the same and a terminal thereof |
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| KR20160113488A (en) * | 2015-03-20 | 2016-09-29 | 대주전자재료 주식회사 | Spyro-typed organic material and organic electroluminescent device utilizing the same |
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| KR20110068330A (en) * | 2009-12-16 | 2011-06-22 | 덕산하이메탈(주) | Spiro carbazole compound and organic electronic element using the same, terminal thereof |
| WO2011108901A2 (en) * | 2010-03-05 | 2011-09-09 | 덕산하이메탈(주) | Spiro-carbazole compound comprising a spiro skeleton, and an organic electronic element using the same and a terminal thereof |
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