CN106711351B - Compound and its organic electroluminescence device containing quinoxaline and biphenyl group - Google Patents
Compound and its organic electroluminescence device containing quinoxaline and biphenyl group Download PDFInfo
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- CN106711351B CN106711351B CN201710055470.1A CN201710055470A CN106711351B CN 106711351 B CN106711351 B CN 106711351B CN 201710055470 A CN201710055470 A CN 201710055470A CN 106711351 B CN106711351 B CN 106711351B
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 62
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 title claims abstract description 38
- 238000005401 electroluminescence Methods 0.000 title claims abstract description 34
- 125000006267 biphenyl group Chemical group 0.000 title claims abstract description 18
- 239000010410 layer Substances 0.000 claims abstract description 104
- 230000027756 respiratory electron transport chain Effects 0.000 claims abstract description 22
- 230000005540 biological transmission Effects 0.000 claims abstract description 18
- 239000012044 organic layer Substances 0.000 claims abstract description 17
- 238000002347 injection Methods 0.000 claims abstract description 9
- 239000007924 injection Substances 0.000 claims abstract description 9
- 230000000903 blocking effect Effects 0.000 claims abstract description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 7
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 4
- 239000004305 biphenyl Substances 0.000 claims description 4
- 235000010290 biphenyl Nutrition 0.000 claims description 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 210000004209 hair Anatomy 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 239000010409 thin film Substances 0.000 abstract description 2
- -1 carbazole compound Chemical class 0.000 description 19
- 239000000543 intermediate Substances 0.000 description 13
- 239000000463 material Substances 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 239000011368 organic material Substances 0.000 description 6
- 238000010189 synthetic method Methods 0.000 description 6
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 150000001340 alkali metals Chemical class 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 150000001342 alkaline earth metals Chemical class 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 4
- 238000001819 mass spectrum Methods 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- BWGRDBSNKQABCB-UHFFFAOYSA-N 4,4-difluoro-N-[3-[3-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1-thiophen-2-ylpropyl]cyclohexane-1-carboxamide Chemical compound CC(C)C1=NN=C(C)N1C1CC2CCC(C1)N2CCC(NC(=O)C1CCC(F)(F)CC1)C1=CC=CS1 BWGRDBSNKQABCB-UHFFFAOYSA-N 0.000 description 3
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 3
- 230000004888 barrier function Effects 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 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 3
- SKLNPGGDKRKWKC-UHFFFAOYSA-N (2-chlorophenoxy)boronic acid Chemical compound OB(O)OC1=CC=CC=C1Cl SKLNPGGDKRKWKC-UHFFFAOYSA-N 0.000 description 2
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 2
- WDBQJSCPCGTAFG-QHCPKHFHSA-N 4,4-difluoro-N-[(1S)-3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-pyridin-3-ylpropyl]cyclohexane-1-carboxamide Chemical compound FC1(CCC(CC1)C(=O)N[C@@H](CCN1CCC(CC1)N1C(=NN=C1C)C(C)C)C=1C=NC=CC=1)F WDBQJSCPCGTAFG-QHCPKHFHSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- KGNDCEVUMONOKF-UGPLYTSKSA-N benzyl n-[(2r)-1-[(2s,4r)-2-[[(2s)-6-amino-1-(1,3-benzoxazol-2-yl)-1,1-dihydroxyhexan-2-yl]carbamoyl]-4-[(4-methylphenyl)methoxy]pyrrolidin-1-yl]-1-oxo-4-phenylbutan-2-yl]carbamate Chemical compound C1=CC(C)=CC=C1CO[C@H]1CN(C(=O)[C@@H](CCC=2C=CC=CC=2)NC(=O)OCC=2C=CC=CC=2)[C@H](C(=O)N[C@@H](CCCCN)C(O)(O)C=2OC3=CC=CC=C3N=2)C1 KGNDCEVUMONOKF-UGPLYTSKSA-N 0.000 description 2
- 229910052792 caesium Inorganic materials 0.000 description 2
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 2
- 229940125797 compound 12 Drugs 0.000 description 2
- 229940125833 compound 23 Drugs 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920000123 polythiophene Polymers 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- 150000002910 rare earth metals Chemical class 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- SDEAGACSNFSZCU-UHFFFAOYSA-N (3-chlorophenyl)boronic acid Chemical compound OB(O)C1=CC=CC(Cl)=C1 SDEAGACSNFSZCU-UHFFFAOYSA-N 0.000 description 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 1
- AYHGAQGOMUQMTR-UHFFFAOYSA-N 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine Chemical compound C1=CC(Br)=CC=C1C1=NC(C=2C=CC=CC=2)=NC(C=2C=CC=CC=2)=N1 AYHGAQGOMUQMTR-UHFFFAOYSA-N 0.000 description 1
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 1
- BWCDLEQTELFBAW-UHFFFAOYSA-N 3h-dioxazole Chemical compound N1OOC=C1 BWCDLEQTELFBAW-UHFFFAOYSA-N 0.000 description 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- QRXMUCSWCMTJGU-UHFFFAOYSA-N 5-bromo-4-chloro-3-indolyl phosphate Chemical compound C1=C(Br)C(Cl)=C2C(OP(O)(=O)O)=CNC2=C1 QRXMUCSWCMTJGU-UHFFFAOYSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- 150000004325 8-hydroxyquinolines Chemical class 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- MSDMPJCOOXURQD-UHFFFAOYSA-N C545T Chemical compound C1=CC=C2SC(C3=CC=4C=C5C6=C(C=4OC3=O)C(C)(C)CCN6CCC5(C)C)=NC2=C1 MSDMPJCOOXURQD-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- IIRVBNFPODABQL-UHFFFAOYSA-N N,N-diphenylaniline ethene Chemical group C1(=CC=CC=C1)N(C1=CC=CC=C1)C1=CC=CC=C1.C=C IIRVBNFPODABQL-UHFFFAOYSA-N 0.000 description 1
- MOFINMJRLYEONQ-UHFFFAOYSA-N [N].C=1C=CNC=1 Chemical class [N].C=1C=CNC=1 MOFINMJRLYEONQ-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000004411 aluminium Substances 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
- BBEAQIROQSPTKN-UHFFFAOYSA-N antipyrene Natural products C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 1
- 229940111121 antirheumatic drug quinolines Drugs 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 150000003851 azoles Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- ZOQCZTRFTARYGJ-UHFFFAOYSA-N chlorooxy(phenyl)borinic acid Chemical compound ClOB(O)C1=CC=CC=C1 ZOQCZTRFTARYGJ-UHFFFAOYSA-N 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 1
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 230000003760 hair shine Effects 0.000 description 1
- 230000005525 hole transport Effects 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- IDBFBDSKYCUNPW-UHFFFAOYSA-N lithium nitride Chemical compound [Li]N([Li])[Li] IDBFBDSKYCUNPW-UHFFFAOYSA-N 0.000 description 1
- 229910001947 lithium oxide Inorganic materials 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- ORUIBWPALBXDOA-UHFFFAOYSA-L magnesium fluoride Chemical compound [F-].[F-].[Mg+2] ORUIBWPALBXDOA-UHFFFAOYSA-L 0.000 description 1
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 150000003961 organosilicon compounds Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 1
Classifications
-
- 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]
- H10K50/17—Carrier injection layers
- H10K50/171—Electron injection layers
-
- 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
- H10K50/16—Electron transporting layers
-
- 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
- H10K85/10—Organic polymers or oligomers
-
- 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
Landscapes
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Electroluminescent Light Sources (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
The present invention provides a kind of organic electroluminescent compounds containing quinoxaline and biphenyl group, the compound has preferable thermal stability, high life, high luminance purity, it can be used for making organic electroluminescence device, be applied to organic solar batteries, Organic Thin Film Transistors or organophotoreceptorswith field.The present invention also provides a kind of organic electroluminescence devices, it includes anode, cathode and organic layer, organic layer includes one layer or more in luminescent layer, hole injection layer, hole transmission layer, hole blocking layer, electron injecting layer, electron transfer layer, at least one layer of compound comprising just like structural formula I in organic layer.
Description
Technical field
The present invention relates to field of organic electroluminescent materials, and in particular to a kind of organic containing quinoxaline and biphenyl group
Electroluminescent compounds and its organic electroluminescence device belong to organic electroluminescence device field of display technology.
Background technique
Organic electroluminescence device (OLEDs) is between two metal electrodes by spin coating or vacuum evaporation deposition one
The device that layer organic material is prepared, a classical three layer organic electroluminescence device include hole transmission layer, luminescent layer
And electron transfer layer.The electronics generated by cathode is followed to be incorporated in through electron transfer layer through hole transmission layer in the hole generated by anode
Luminescent layer forms exciton, then shines.Organic electroluminescence device can according to need the material by changing luminescent layer to adjust
Section emits the light of various needs.
Organic electroluminescence device has self-luminous, wide viewing angle, low energy consumption, efficiency as a kind of novel display technology
High, thin, rich in color, fast response time, Applicable temperature range be wide, low driving voltage, can make flexible and transparent
Display panel and the particular advantages such as environmental-friendly can be applied on flat-panel monitor and a new generation's illumination, be can also be used as
The backlight of LCD.
Since the invention at the bottom of the 1980s, organic electroluminescence device is industrially applied, such as
As screens such as camera and mobile phones, but current OLED device, due to low efficiency, it is wider that the factors such as service life is short restrict it
General application, especially large screen display, it is therefore desirable to improve the efficiency of device.And restrict one of key factor just
It is the performance of the electroluminescent organic material in organic electroluminescence device.It is voltage-operated in application additionally, due to OLED device
When, Joule heat can be generated, so that organic material is easy to happen crystallization, affects service life and the efficiency of device, therefore, it is also desirable to
Develop the electroluminescent organic material of stability and high efficiency.
Speed in OLED material, due to the speed of most electroluminescent organic material transporting holes than transmitting electronics
Fastly, it be easy to cause the electrons and holes quantity of luminescent layer uneven, the efficiency of such device is with regard to relatively low.Three (8-hydroxyquinolines)
Aluminium (Alq3) since the invention, it has been extensively studied, but still very as electron transport material its electron mobility
Intrinsic characteristic that is low, and itself can degrading, in using its device as electron transfer layer, it may appear that the case where voltage declines,
Simultaneously as lower electron mobility, so that a large amount of hole enters Alq3In layer, excessive hole is with non-luminescent shape
Formula radiation energy, and when as electron transport material, due to the characteristic of its green light, above it is restricted in application.Cause
This, organic electroluminescence device is widely used in development stability and the electron transport material with larger electron mobility
With great value.
Summary of the invention
Present invention firstly provides a kind of organic electroluminescent compounds containing quinoxaline and biphenyl group, for such as
The compound of flowering structure Formulas I:
Wherein, Ar1-Ar4Separately it is selected from the substitution or unsubstituted of C1-C8 alkyl, C1-C8 alkoxyl, C6-C30
Aryl, C3-C30 substitution or the unsubstituted hetero atom aryl containing one or more；L is biphenyl；X1And X2Respectively
Independently selected from N and CH.
Preferably, Ar1-Ar4Separately it is selected from phenyl, xenyl, naphthalene, fluorenyl, dibenzofuran group, dibenzo
Thienyl, the above group can further replace for the alkyl of C1-C10 or alkoxy.
It is further preferred that the compound of the invention containing quinoxaline and biphenyl group is the change of following structural 1-24
Close object:
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Organic electroluminescent compounds containing quinoxaline and biphenyl group of the invention can be applied to be sent out in organic electroluminescence
Optical device, organic solar batteries, Organic Thin Film Transistors or organophotoreceptorswith field.
The present invention also provides a kind of organic electroluminescence device, which includes anode, cathode and organic layer, organic layer
Comprising one layer in luminescent layer, hole injection layer, hole transmission layer, hole blocking layer, electron injecting layer, electron transfer layer with
On, wherein at least one layer Organic Electricity containing quinoxaline and biphenyl group contained as described in structural formula I in the organic layer
Electro luminescent compounds:
Wherein Ar1-Ar4、X1、X2It is defined as described above with L.
Wherein organic layer is luminescent layer and electron transfer layer；
Or organic layer is luminescent layer, hole injection layer, hole transmission layer and electron transfer layer；
Or organic layer is luminescent layer, hole injection layer, hole transmission layer, electron transfer layer and electron injecting layer；
Or organic layer is luminescent layer, hole injection layer, hole transmission layer, electron transfer layer, electron injecting layer and blocking
Layer；
Or organic layer is luminescent layer, hole transmission layer, electron transfer layer, electron injecting layer and barrier layer；
Or organic layer is luminescent layer, hole transmission layer, electron injecting layer and barrier layer.
Preferably, contain layer where the organic electroluminescent compounds of quinoxaline and biphenyl group as described in structural formula I
For electron transfer layer and/or electron injecting layer.
Preferably, the organic electroluminescent compounds containing quinoxaline and biphenyl group as described in structural formula I are structure
The compound of formula 1-24.
The organic electroluminescent compounds containing quinoxaline and biphenyl group as described in structural formula I are used for luminescent device system
When standby, it can be used alone, can also be used in mixed way with other compounds；Contain quinoxaline and biphenyl as described in structural formula I
The organic electroluminescent compounds of group can be used alone one such compound, can also be simultaneously using in structural formula I
Two or more compounds.
Organic electroluminescence device of the invention, further preferred mode are that the organic electroluminescence device includes sun
Pole, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and cathode, wherein electron transfer layer and/or electron injection
Compound containing structural formula I in layer；It is further preferred that containing structural formula 1- in electron transfer layer and/or electron injecting layer
24 compound.
In organic electroluminescence device of the invention, it can also be also served as when Compounds of structural formula I is as electron transfer layer
Electron injecting layer.
The overall thickness of organic electroluminescence device organic layer of the invention is 1-1000nm, preferably 50-500nm.
When having the compound of structural formula I using the present invention, can arrange in pairs or groups makes organic electroluminescence device of the invention
With other materials, such as in hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and barrier layer
Deng, and obtain blue and green light, yellow light, feux rouges or white light.
The hole transmission layer and hole injection layer of organic electroluminescence device of the present invention, material requested have good hole
Transmission performance can effectively be transferred to hole on luminescent layer from anode.It may include that other small molecules and macromolecule are organic
Compound, including but not limited to carbazole compound, triaromatic amine compound, benzidine compound, compound of fluorene class, phthalocyanine
Class compound, the miscellaneous triphen (hexanitrilehexaazatriphenylene) of six cyano six, 2,3,5,6- tetra- fluoro- 7,7', 8,
Tetra- cyanogen dimethyl-parabenzoquinone (F4-TCNQ) of 8'-, polyvinyl carbazole, polythiophene, polyethylene or polyphenyl sulfonic acid.
The luminescent layer of organic electroluminescence device of the invention has the good characteristics of luminescence, can be adjusted according to the needs
The range of visible light.Following compound, including but not limited to naphthalene compounds, pyrene compound, fluorenes class chemical combination can be contained
Object, bends class compound, glimmering anthracene compound, anthracene compound, pentacene class compound, class compound, two at luxuriant and rich with fragrance class compound
Aromatic ethylene class compound, triphenylamine ethylene compounds, aminated compounds, carbazole compound, benzimidazoles compound, furan
Class of muttering compound, metal organic fluorescence complex compound, metal Phosphorescent complex compound (such as Ir, Pt, Os, Cu, Au), polyethylene click
The organic polymer luminescent materials such as azoles, poly-organosilicon compound, polythiophene, they can be used alone, and a variety of can also mix
Object uses.
The Organic Electron Transport Material of organic electroluminescence device of the present invention requires good electronic transmission performance, energy
It reaches in effectively electronics from cathode transport to luminescent layer, there is very big electron mobility.Except of the invention has structural formula I
Outside compound, it is also an option that the following compound of collocation, but not limited to this: oxa- oxazole, thiazole compound, three nitrogen
Azole compounds, triazine class compound, quinoline class compound, phenodiazine anthracene compound, contain sila at three nitrogen piperazine class compounds
Cyclics, quinolines, ferrosin class compound, metallo-chelate (such as Alq3, 8-hydroxyquinoline lithium), fluorine replace
Benzene-like compounds, benzimidazoles compound.
Electronics effectively can be injected into organic layer from cathode by the electron injecting layer of organic electroluminescence device of the present invention
In, except it is of the invention there is Compounds of structural formula I in addition to, be mainly selected from the compound of alkali metal or alkali metal, or be selected from alkaline earth
The compound or alkali metal complex of metal or alkaline-earth metal, can choose following compound, but not limited to this: alkali gold
Category, alkaline-earth metal, rare earth metal, the oxide of alkali metal or halide, the oxide of alkaline-earth metal or halide, rare earth
The organic complex of the oxide or halide of metal, alkali metal or alkaline-earth metal；Preferably lithium, lithium fluoride, lithia,
Lithium nitride, 8-hydroxyquinoline lithium, caesium, cesium carbonate, 8-hydroxyquinoline caesium, calcium, calcirm-fluoride, calcium oxide, magnesium, magnesium fluoride, magnesium carbonate,
Magnesia, these compounds, which can be used alone, to be used with mixture, can also match with other electroluminescent organic materials
It closes and uses.
Each layer of organic layer in organic electroluminescence device of the invention can be steamed by vacuum vapour deposition, molecular beam
It is prepared by the modes such as plating method, the dip coating for being dissolved in solvent, spin-coating method, stick coating method or inkjet printing.Metal motor can be made
It is prepared with vapour deposition method or sputtering method.
Device experimental shows organic electroluminescent containing quinoxaline and biphenyl group of the present invention as described in structural formula I
Compound has preferable thermal stability, high life, high luminance purity.Using the organic of organic electroluminescent compounds production
Electroluminescent device has the advantages that electroluminescent efficiency is good and excitation purity is excellent and the service life is long.
Detailed description of the invention
Fig. 1 is a kind of organic electroluminescence device structural schematic diagram of the invention；
Wherein, 110 it is represented as glass substrate, 120 are represented as anode, and 130 are represented as hole transmission layer, and 140 are represented as sending out
Photosphere, 150 are represented as electron transfer layer, and 160 are represented as electron injecting layer, and 170 are represented as cathode.
Specific embodiment
In order to describe the present invention in more detail, spy lifts following example, and but not limited to this.
Embodiment 1
The synthesis of compound 3
The synthesis of intermediate 3-1
In three-necked flask, it is added to chlorophenylboronic acid (2g, 12.8mmol), 2- (4- bromophenyl) -4,6- diphenyl -1,3,
5- triazine (5g, 12.8mmol), potassium carbonate (3.5g, 25.6mmol), tetra-triphenylphosphine palladium (0.2g), tetrahydrofuran (50ml) and
Water (15ml) is heated to reflux 10 hours under nitrogen protection, cooling, is concentrated, and filtering, crude product tetrahydrofuran and ethyl alcohol are tied again
Crystalline substance obtains yield 4.9g, yield 91%.
The synthesis of compound 3
In three-necked flask, intermediate 3-1 (3g, 7.2mmol), 2,3- diphenyl -6- (4,4,5,5- tetramethyls-is added
Bis- oxygroups of 1,3,2--boryl)-quinoxaline (2.9g, 7.2mmol), potassium carbonate (2g, 15mmol), palladium acetate (0.2g), X-phos
(0.4g), tetrahydrofuran (50ml) and water (15ml), are heated to reflux 10 hours under nitrogen protection, cooling, are concentrated, filtering, slightly
Product tetrahydrofuran and ethyl alcohol recrystallization obtain yield 3.9g, yield 82%.Mass spectrum 665.51.
Embodiment 2
The synthesis of compound 5
Intermediate 5-1
For synthetic method as intermediate 3-1, raw materials used is the chloro- phenyl boric acid of 3- and 4- (4- bromophenyl) -2,6- hexichol
Yl pyrimidines, yield 87%.
The synthesis of compound 5
Synthetic method replaces intermediate 3-1, yield 71% as compound 3, with intermediate 5-1.Mass spectrum 664.71.
Embodiment 3
The synthesis of compound 12
The synthesis of intermediate 12-1
For synthetic method as intermediate 3-1, raw materials used is the chloro- phenyl boric acid of 3- and 4- (3- bromophenyl) -2,6- hexichol
Base -1,3,5-triazines, yield 93%.
The synthesis of compound 12
Synthetic method is as compound 3, other than replacing intermediate 3-1 with intermediate 12-1, yield 75%.Mass spectrum
665.49。
Embodiment 4
The synthesis of compound 23
The synthesis of intermediate 23-1
For synthetic method as intermediate 3-1, raw materials used is 3- chlorophenylboronic acid and 2- phenyl -4- (4- xenyl) -6-
(3- bromophenyl)-pyrimidine, yield 86%.
The synthesis of compound 23
Synthetic method is as the synthesis of compound 3, other than useful intermediates 23-1 replaces 3-1, yield 87%.Mass spectrum
740.31。
Embodiment 5-8
The preparation of organic electroluminescence device
OLED is prepared using the compound of the present invention.
Firstly, by electrically conducting transparent ito glass substrate 110 (having anode 120 above) (the limited public affairs of South China glass group share
Department) successively pass through: deionized water, ethyl alcohol, acetone and deionized water were cleaned, then with oxygen plasma treatment 30 seconds.
Then, NPB is deposited, forms the hole transmission layer 130 of 60nm thickness.
Then, the Alq of 37.5nm thickness is deposited on the hole transport layer31%C-545T is adulterated as luminescent layer 140.
Then, on the light-emitting layer vapor deposition 37.5nm thickness be used as electron transfer layer 150, comprising 75% the compounds of this invention with
25% LiQ.
Finally, vapor deposition 1nm LiF is electron injecting layer 160 and 100nm Al as device cathodes 170.
Comparative example
In addition to electron transfer layer Alq3Outside instead of the compounds of this invention, others are as embodiment 5-8.
Prepared device (structural schematic diagram is shown in Fig. 1) is in 6000cd/m2Service life such as table 1 after working under brightness 24 hours
It is shown.
Table 1
| Embodiment | Compound | Service life | Color |
| 5 | 3 | 82% | Green light |
| 6 | 5 | 83% | Green light |
| 7 | 12 | 84% | Green light |
| 8 | 23 | 84% | Green light |
| Comparative example | Alq3 | 75% | Green light |
Under the same conditions, the organic electroluminescence device prepared using organic electroluminescent compounds of the invention
Service life is all higher than comparative example, as described above, the compound of the present invention has high stability, organic electroluminescence hair prepared by the present invention
Optical device has high service life and optical purity.
The structural formula of compound described in device is as follows:
The preferred embodiment of the present invention has been described in detail above.It should be appreciated that those skilled in the art without
It needs creative work according to the present invention can conceive and makes many modifications and variations.Therefore, all technologies in the art
Personnel are available by logical analysis, reasoning, or a limited experiment on the basis of existing technology under this invention's idea
Technical solution, all should be within the scope of protection determined by the claims.
Claims (7)
1. a kind of organic electroluminescent compounds containing quinoxaline and biphenyl group, it is characterised in that it is to have the following structure
The compound of Formulas I:
Wherein, Ar1-Ar4It is further separately C1- selected from phenyl, xenyl, naphthalene, fluorenyl or the above group
The alkyl of C10 replaces；L is biphenyl；X1And X2Separately it is selected from N and CH.
2. the organic electroluminescent compounds according to claim 1 containing quinoxaline and biphenyl group, it is characterised in that
It is the compound of following structural 1-24:
。
3. a kind of organic electroluminescence device comprising anode, cathode and organic layer, organic layer include luminescent layer, hole injection
Layer, hole transmission layer, hole blocking layer, electron injecting layer, one layer or more in electron transfer layer, it is characterised in that the electronics
Transport layer and/or electron injecting layer contain the organic electroluminescent containing quinoxaline and biphenyl group as described in claim 1
Compound.
4. organic electroluminescence device according to claim 3, it is characterised in that contain quinoxaline as described in structural formula I
The compound that organic electroluminescent compounds with biphenyl group are the structural formula 1-24 as shown in claim 2.
5. organic electroluminescence device according to claim 3, it is characterised in that contain quinoxaline as described in structural formula I
It is used alone with the organic electroluminescent compounds of biphenyl group, or is used in mixed way with other compounds.
6. organic electroluminescence device according to claim 3, it is characterised in that contain quinoxaline as described in structural formula I
One such compound is used alone with the organic electroluminescent compounds of biphenyl group, or simultaneously using in structural formula I
Two or more compounds.
7. organic electroluminescence device according to claim 3, it is characterised in that it includes anode, hole transmission layer, hairs
Photosphere, electron transfer layer, electron injecting layer and cathode, it is characterised in that contain knot in electron transfer layer and/or electron injecting layer
The compound of structure Formulas I.
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| CN114628599A (en) * | 2020-12-11 | 2022-06-14 | 常州强力昱镭光电材料有限公司 | Organic electroluminescent element |
| CN115260157B (en) * | 2021-04-29 | 2023-09-29 | 常州强力昱镭光电材料有限公司 | Stereo ring quinoxaline compound, organic electroluminescent device, display device and application |
| WO2024026687A1 (en) * | 2022-08-02 | 2024-02-08 | 苏州大学 | High-efficiency orange-red electroluminescent device |
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| WO2012071414A3 (en) * | 2010-11-22 | 2012-08-16 | Board Of Regents Of The University Of Nebraska | Quinoxaline compounds and uses thereof |
| CN105461685A (en) * | 2016-02-03 | 2016-04-06 | 上海道亦化工科技有限公司 | Compound containing quinoxaline perssad and organic electroluminescence device of compound |
| CN105622581A (en) * | 2016-02-03 | 2016-06-01 | 上海道亦化工科技有限公司 | Compound containing quinoxaline group and organic electroluminescent device thereof |
| CN105753849A (en) * | 2016-02-03 | 2016-07-13 | 上海道亦化工科技有限公司 | Compound containing quinoxaline and pyridine groups and organic electroluminescent device thereof |
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| EP1905768B1 (en) * | 2006-09-29 | 2014-03-05 | Semiconductor Energy Laboratory Co., Ltd. | Quinoxaline derivative, and light-emitting device, electronic device using the quinoxaline derivative |
| JP5748948B2 (en) * | 2008-10-03 | 2015-07-15 | 東ソー株式会社 | 1,3,5-triazine derivative, method for producing the same, and organic electroluminescent device comprising the same |
| KR102229862B1 (en) * | 2013-01-22 | 2021-03-22 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof |
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| WO2012071414A3 (en) * | 2010-11-22 | 2012-08-16 | Board Of Regents Of The University Of Nebraska | Quinoxaline compounds and uses thereof |
| CN105461685A (en) * | 2016-02-03 | 2016-04-06 | 上海道亦化工科技有限公司 | Compound containing quinoxaline perssad and organic electroluminescence device of compound |
| CN105622581A (en) * | 2016-02-03 | 2016-06-01 | 上海道亦化工科技有限公司 | Compound containing quinoxaline group and organic electroluminescent device thereof |
| CN105753849A (en) * | 2016-02-03 | 2016-07-13 | 上海道亦化工科技有限公司 | Compound containing quinoxaline and pyridine groups and organic electroluminescent device thereof |
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