CN107033143A - Compound and its organic electroluminescence device containing [1,2,4] triazole [1,5 a] pyridine - Google Patents
Compound and its organic electroluminescence device containing [1,2,4] triazole [1,5 a] pyridine Download PDFInfo
- Publication number
- CN107033143A CN107033143A CN201710413701.1A CN201710413701A CN107033143A CN 107033143 A CN107033143 A CN 107033143A CN 201710413701 A CN201710413701 A CN 201710413701A CN 107033143 A CN107033143 A CN 107033143A
- Authority
- CN
- China
- Prior art keywords
- layer
- compound
- organic
- pyridine
- triazole
- 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 56
- 238000005401 electroluminescence Methods 0.000 title claims abstract description 32
- LENLQGBLVGGAMF-UHFFFAOYSA-N tributyl([1,2,4]triazolo[1,5-a]pyridin-6-yl)stannane Chemical compound C1=C([Sn](CCCC)(CCCC)CCCC)C=CC2=NC=NN21 LENLQGBLVGGAMF-UHFFFAOYSA-N 0.000 title claims abstract description 15
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 title claims description 19
- 239000010410 layer Substances 0.000 claims abstract description 106
- 230000005540 biological transmission Effects 0.000 claims abstract description 27
- 230000027756 respiratory electron transport chain Effects 0.000 claims abstract description 22
- 239000012044 organic layer Substances 0.000 claims abstract description 18
- 238000002347 injection Methods 0.000 claims abstract description 8
- 239000007924 injection Substances 0.000 claims abstract description 8
- 150000003852 triazoles Chemical class 0.000 claims abstract description 4
- 230000000903 blocking effect Effects 0.000 claims abstract description 3
- -1 5-a] pyridine Compound Chemical class 0.000 claims description 44
- 238000006467 substitution reaction Methods 0.000 claims description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000001624 naphthyl group Chemical group 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 7
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 6
- 229910052805 deuterium Inorganic materials 0.000 claims description 6
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 6
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical compound C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000005561 phenanthryl group Chemical group 0.000 claims description 4
- 125000005328 phosphinyl group Chemical group [PH2](=O)* 0.000 claims description 4
- 125000001725 pyrenyl group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 2
- IYDMICQAKLQHLA-UHFFFAOYSA-N 1-phenylnaphthalene Chemical compound C1=CC=CC=C1C1=CC=CC2=CC=CC=C12 IYDMICQAKLQHLA-UHFFFAOYSA-N 0.000 claims description 2
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 125000006267 biphenyl group Chemical group 0.000 claims description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical class C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 2
- 125000002971 oxazolyl group Chemical group 0.000 claims description 2
- 150000002979 perylenes Chemical class 0.000 claims description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 2
- 125000005493 quinolyl group Chemical group 0.000 claims description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 description 17
- 238000003786 synthesis reaction Methods 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000000463 material Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000002585 base Substances 0.000 description 7
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 6
- 238000004440 column chromatography Methods 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
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 238000010189 synthetic method Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 150000001340 alkali metals Chemical class 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 150000001342 alkaline earth metals Chemical class 0.000 description 4
- 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 4
- 229940125833 compound 23 Drugs 0.000 description 4
- 239000012043 crude product Substances 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
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- UAYWVJHJZHQCIE-UHFFFAOYSA-L zinc iodide Chemical compound I[Zn]I UAYWVJHJZHQCIE-UHFFFAOYSA-L 0.000 description 4
- 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
- 239000011521 glass Substances 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000126 substance 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
- STBLNCCBQMHSRC-BATDWUPUSA-N (2s)-n-[(3s,4s)-5-acetyl-7-cyano-4-methyl-1-[(2-methylnaphthalen-1-yl)methyl]-2-oxo-3,4-dihydro-1,5-benzodiazepin-3-yl]-2-(methylamino)propanamide Chemical compound O=C1[C@@H](NC(=O)[C@H](C)NC)[C@H](C)N(C(C)=O)C2=CC(C#N)=CC=C2N1CC1=C(C)C=CC2=CC=CC=C12 STBLNCCBQMHSRC-BATDWUPUSA-N 0.000 description 2
- 150000005768 2-amino-5-bromopyridine Chemical class 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- PSLUFJFHTBIXMW-WYEYVKMPSA-N [(3r,4ar,5s,6s,6as,10s,10ar,10bs)-3-ethenyl-10,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-6-(2-pyridin-2-ylethylcarbamoyloxy)-5,6,6a,8,9,10-hexahydro-2h-benzo[f]chromen-5-yl] acetate Chemical compound O([C@@H]1[C@@H]([C@]2(O[C@](C)(CC(=O)[C@]2(O)[C@@]2(C)[C@@H](O)CCC(C)(C)[C@@H]21)C=C)C)OC(=O)C)C(=O)NCCC1=CC=CC=N1 PSLUFJFHTBIXMW-WYEYVKMPSA-N 0.000 description 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 2
- 238000007664 blowing Methods 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
- 229940125878 compound 36 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
- 230000005611 electricity Effects 0.000 description 2
- 239000000706 filtrate Substances 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
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920000123 polythiophene Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- GOXICVKOZJFRMB-UHFFFAOYSA-N (3-phenylphenyl)boronic acid Chemical class OB(O)C1=CC=CC(C=2C=CC=CC=2)=C1 GOXICVKOZJFRMB-UHFFFAOYSA-N 0.000 description 1
- XPEIJWZLPWNNOK-UHFFFAOYSA-N (4-phenylphenyl)boronic acid Chemical class C1=CC(B(O)O)=CC=C1C1=CC=CC=C1 XPEIJWZLPWNNOK-UHFFFAOYSA-N 0.000 description 1
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- 150000005770 2-amino-4-bromopyridine Chemical class 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
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229910021589 Copper(I) bromide Inorganic materials 0.000 description 1
- IVDFJHOHABJVEH-UHFFFAOYSA-N HOCMe2CMe2OH Natural products CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-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
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-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
- 239000002253 acid Substances 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
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 150000003851 azoles Chemical class 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 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
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 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
- 238000005286 illumination Methods 0.000 description 1
- 229910052738 indium Inorganic materials 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
- 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
- 230000003287 optical effect Effects 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 150000003961 organosilicon compounds Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 238000005424 photoluminescence Methods 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
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- ABMYEXAYWZJVOV-UHFFFAOYSA-N pyridin-3-ylboronic acid Chemical class OB(O)C1=CC=CN=C1 ABMYEXAYWZJVOV-UHFFFAOYSA-N 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
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 229910001404 rare earth metal oxide Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 150000003384 small molecules Chemical class 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
-
- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
Contain [1 the invention provides one kind, 2,4] triazole [1,5 a] pyridine organic electroluminescent electron transport compound, the compound has preferable heat endurance, high-luminous-efficiency, high luminance purity, it can be used for making organic electroluminescence device, applied to organic solar batteries, OTFT or organophotoreceptorswith field.Present invention also offers a kind of organic electroluminescence device, it includes anode, negative electrode and organic layer, organic layer includes at least one layer of compound comprising just like structural formula I at least one layer in luminescent layer, hole injection layer, hole transmission layer, hole blocking layer, electron injecting layer, electron transfer layer, organic layer.
Description
Technical field
The present invention relates to field of organic electroluminescent materials, and in particular to one kind contains [1,2,4]-triazole [1,5-a] pyrrole
The compound and its organic electroluminescence device of pyridine, belong to organic electroluminescence device display technology field.
Background technology
Organic electroluminescence device (OLEDs) is by spin coating or vacuum evaporation deposition one between two metal electrodes
The device that layer organic material is prepared from, a classical three layer organic electroluminescence device includes hole transmission layer, luminescent layer
And electron transfer layer.The hole produced by anode through hole transmission layer with the electronics that is produced by negative electrode through combined with electron transfer layer
Luminescent layer formation exciton, then lights.Organic electroluminescence device can be adjusted as desired by the material of luminescent layer is changed
The light of the various needs of section transmitting.
Organic electroluminescence device is as a kind of new Display Technique, with self-luminous, wide viewing angle, low energy consumption, efficiency
High, thin, rich color, fast response time, Applicable temperature scope are wide, low driving voltage, can make flexible with it is transparent
Display panel and the particular advantages such as environment-friendly, can be applied on flat-panel monitor and a new generation's illumination, can also conduct
LCD backlight.
Since invention at the bottom of 1980s, organic electroluminescence device has industrially been applied, such as
As screens such as camera and mobile phones, but current OLED is low due to efficiency, and it is wider that the factor such as service life is short restricts it
General application, particularly 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.Applying voltage-operated additionally, due to OLED
When, Joule heat can be produced so that organic material is easily crystallized, have impact on life-span and the efficiency of device, therefore, it is also desirable to
Develop the electroluminescent organic material of stability and high efficiency.
In OLED material, due to speed of the speed than transmitting electronics of most electroluminescent organic material transporting holes
It hurry up, the electronics and number of cavities for easily causing luminescent layer are uneven, and the efficiency of such device is just than relatively low.Three (8-hydroxyquinolines)
Aluminium (Alq3) since the invention, it has been extensively studied, but as electron transport material its electron mobility still very
It is low, and the intrinsic characteristic that itself can be degraded, in the device using it as electron transfer layer, it may appear that the situation that voltage declines,
Simultaneously as relatively low electron mobility so that substantial amounts of hole enters Alq3In layer, excessive hole is with the shape of non-luminescent
Formula emittance, and when as electron transport material, due to the characteristic of its green light, be above restricted in application.Cause
This, development stability and the electron transport material with larger electron mobility are widely used to organic electroluminescence device
With great value.
The content of the invention
Present invention firstly provides a kind of organic electroluminescent electric transmission for containing [1,2,4]-triazole [1,5-a] pyridine
Compound, it is the compound with following structural formula I：
Wherein, R1-R4Separately selected from hydrogen, deuterium, halogen, cyano group, straight chain or C1-C12 alkyl with side chain, straight
Chain or C1-C8 alkoxyl, C6-C30 substitution or unsubstituted aryl with side chain, C3-C30 substitution or unsubstituted
Heteroaryl, triaryl phosphinyl；
L is selected from singly-bound, C6-C30 substitution or unsubstituted aryl, C3-C30 substitution or unsubstituted contains one
Individual or multiple heteroatomic heteroaryls；
Ar be selected from C6-C30 substitution or unsubstituted aryl, C3-C30 substitution or it is unsubstituted containing one or
The multiple heteroatomic heteroaryls of person, triaryl phosphinyl；
Py is pyridine radicals；
Ar1Selected from hydrogen, deuterium, C6-C30 substitution or unsubstituted aryl.
Preferably, R1-R4Separately it is selected from hydrogen, deuterium, fluorine, phenyl, naphthyl, phenanthryl, pyrenyl, xenyl, phenylnaphthalene
Base, naphthylphenyl, pyridine radicals, diphenyl phenyl.
Preferably, L is selected from singly-bound, phenyl, naphthyl.
Preferably, Ar1Selected from hydrogen, phenyl, naphthyl.
Preferably, Ar be selected from benzene, naphthyl, anthryl, phenanthryl, pyrenyl, perylenes base, fluoranthene base, (9,9- dialkyl group) fluorenyl, (9,
9- bis- replaces or unsubstituted aryl) fluorenyl, 9,9- Spirofluorene-based, dibenzothiophenes base, dibenzofuran group, xenyl, benzene
Base naphthyl, naphthylphenyl, diphenyl base phenyl, pyridine radicals, quinolyl, pyrimidine radicals, triazine radical, thiazolyl, oxazolyl, triazole
Base, quinoxalinyl, isoquinolyl, phenylpyridyl, pyridinylphenyl, bipyridyl, the above group can be further
C1-C10 alkyl or alkoxy substitution.
It is further preferred that the present invention contains the organic electroluminescent electric transmission of [1,2,4]-triazole [1,5-a] pyridine
Compound is following structural 1-54 compound：
The organic electroluminescent electron transport compound containing [1,2,4]-triazole [1,5-a] pyridine of the present invention can be answered
Used in organic electroluminescence device, organic solar batteries, OTFT or organophotoreceptorswith field.
Present invention also offers a kind of organic electroluminescence device, the device includes anode, negative electrode and organic layer, organic layer
Include at least one in luminescent layer, hole injection layer, hole transmission layer, hole blocking layer, electron injecting layer, electron transfer layer
Layer, wherein in the organic layer at least one layer containing containing [1,2,4]-triazole [1,5-a] pyridine as described in structural formula I
Organic electroluminescent electron transport compound：
Wherein R1-R4、A1, Ar, Py and L it is defined as described above.
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 stop
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, wherein containing the organic electroluminescent electronics of [1,2,4]-triazole [1,5-a] pyridine as described in structural formula I
Layer where transport compound is electron transfer layer or electron injecting layer.
Preferably, the organic electroluminescent electronics containing [1,2,4]-triazole [1,5-a] pyridine is passed wherein described in structural formula I
Defeated compound is structural formula 1-54 compound.
The organic electroluminescent electric transmission chemical combination containing [1,2,4]-triazole [1,5-a] pyridine as described in structural formula I
When thing is used for luminescent device preparation, it can be used alone, can also be used in mixed way with other compounds；As described in structural formula I
Electroluminescent compounds containing [1,2,4]-triazole [1,5-a] pyridine can be used alone a kind of compound therein, also may be used
With simultaneously using the two or more compounds in structural formula I.
The organic electroluminescence device of the present invention, further preferred mode is that the organic electroluminescence device includes sun
In pole, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and negative electrode, wherein electron transfer layer or electron injecting layer
Compound containing at least one structural formula I；It is further preferred that containing at least one in electron transfer layer or electron injecting layer
Structural formula 1-54 compound.
The organic electroluminescence device of the present invention, Compounds of structural formula I is as can also also serve as electronics during electron transfer layer
Implanted layer.
The gross thickness of the organic electroluminescence device organic layer of the present invention is 1-1000nm, preferably 50-500nm.
The organic electroluminescence device of the present invention is when having structural formula I compound using the present invention, and can arrange in pairs or groups makes
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, gold-tinted, 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.Small molecule can be included and macromolecular organic is closed
Thing, including but not limited to carbazole compound, triaromatic amine compound, benzidine compound, compound of fluorene class, phthalocyanines
Compound, the miscellaneous triphen (hexanitrilehexaazatriphenylene) of six cyano group six, 2,3,5,6- tetra- fluoro- 7,7', 8,8'- tetra-
Cyanogen dimethyl-parabenzoquinone (F4-TCNQ), PVK, polythiophene, polyethylene or polyphenyl sulfonic acid.
The luminescent layer of the organic electroluminescence device of the present invention, with the good characteristics of luminescence, can be adjusted as needed
The scope of visible ray.Following compound, including but not limited to naphthalene compounds, pyrene compound, fluorenes class chemical combination can be contained
Thing, luxuriant and rich with fragrance class compound, class compound in the wrong, glimmering anthracene compound, anthracene compound, pentacene class compound, perylene class compound, two
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
Thing is used.
The Organic Electron Transport Material requirement of organic electroluminescence device of the present invention has good electronic transmission performance, energy
It is enough effectively electronics from cathode transport to luminescent layer in, with very big electron mobility.There is structural formula I except the present invention
Chemical combination beyond the region of objective existence, it is also an option that or the following compound of arranging in pairs or groups, but not limited to this：Oxa- oxazole, thiazole compound, three nitrogen
Azole compounds, three nitrogen piperazine class compounds, triazine class compound, quinoline class compound, phenodiazine anthracene compound, containing sila
Cyclics, quinolines, ferrosin class compound, metallo-chelate (such as Alq3, 8-hydroxyquinoline lithium), fluorine substitution
Benzene-like compounds, benzimidazoles compound.
Electronics, effectively can be injected into organic layer by the electron injecting layer of organic electroluminescence device of the present invention from negative electrode
In, in addition to the present invention is with Compounds of structural formula I, the compound of alkali metal or alkali metal is mainly selected from, or selected from alkaline earth
The compound or alkali metal complex of metal or alkaline-earth metal, can select 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
Oxide or halide, the organic complex of alkali metal or alkaline-earth metal of 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 can be used alone can also mixture use, can also match somebody with somebody with other electroluminescent organic materials
Conjunction is used.
Each layer of organic layer in the organic electroluminescence device of the present 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.It can make for metal motor
Prepared with vapour deposition method or sputtering method.
Device experimental shows, Organic Electricity containing [1,2,4]-triazole [1,5-a] pyridine of the present invention as described in structural formula I
Photoluminescence electron transport compound has preferable heat endurance, high-luminous-efficiency, high luminance purity.Using this contain [1,2,4]-
The organic electroluminescence device that the compound of triazole [1,5-a] pyridine makes has electroluminescent efficiency well and excitation is excellent
And the advantage of long lifespan.
Brief description of the drawings
Fig. 1 is a kind of organic electroluminescence device structural representation of the invention；
Wherein, 110 glass substrate is represented as, 120 are represented as anode, and 130 are represented as hole transmission layer, and 140 are represented as hair
Photosphere, 150 are represented as electron transfer layer, and 160 are represented as electron injecting layer, and 170 are represented as negative electrode.
Embodiment
In order to describe the present invention in more detail, especially exemplified by example below, but not limited to this.
Embodiment 1
The synthesis of compound 4
Intermediate 4-1 synthesis
In flask, 2- amino -5- bromopyridines (10g, 58mmol), 4- biphenylboronic acids (11.4g, 58mmol), carbon are added
Sour potassium (16g, 118mmol), tetra-triphenylphosphine palladium (0.5g), tetrahydrofuran (100mL) and water (50mL), nitrogen protection is lower to heat
Backflow 12 hours, cooling, is extracted with dichloromethane, is dried, concentration, and crude product obtains 9g, yield 63% through column chromatography purifying.
Intermediate 4-2 synthesis
In flask, add 3,5- dibromos benzonitrile (3g, 11.6mmol), 4- (1- naphthyls)-phenyl boric acid (2.9g,
11.6mmol), potassium carbonate (4.1g, 30mmol), tetra-triphenylphosphine palladium (0.1g), tetrahydrofuran (30mL) and water (15mL),
It is heated to reflux 12 hours under nitrogen protection, cools down, extracted with dichloromethane, dried, concentration, crude product is obtained through column chromatography purifying
2.5g, yield 57%.
Intermediate 4-3 synthesis
In single port bottle, intermediate 4-1 (2.5g, 10mmol), intermediate 4-2 (3.8g, 10mmol), cuprous bromide are added
(0.18mmol, 27mg), phenanthroline (0.18mmol, 33mg), zinc iodide (0.37mmol, 118mg), o-dichlorohenzene
(30mL), 150 degree of blowing air reacts 24 hours, is cooled to after room temperature and uses dchloromethane, is filtered to remove inorganic salts, filtrate is dense
Column chromatography for separation is used after contracting, white solid 2.7g, yield 43% is obtained.
The synthesis of compound 4
In flask, add intermediate 4-3 (2.5g, 4mmol), 3- pyridine boronic acids (1g, 8mmol), potassium carbonate (1.3g,
10mmol), tetra-triphenylphosphine palladium (0.1g), tetrahydrofuran (20mL) and water (10mL), are heated to reflux 12 small under nitrogen protection
When, cooling is extracted with dichloromethane, is dried, concentration, and crude product obtains 1.9g, yield 76% through column chromatography purifying.
Embodiment 2
The synthesis of compound 23
Intermediate 23-1 synthesis
In single port bottle, intermediate 4-1 (3g, 12mmol), 3,5- dibromos benzonitrile (3.1g, 12mmol), bromination are added
Cuprous (0.18mmol, 27mg), phenanthroline (0.18mmol, 33mg), zinc iodide (0.37mmol, 118mg), o-dichlorohenzene
(30mL), 150 degree of blowing air reacts 24 hours, is cooled to after room temperature and uses dchloromethane, is filtered to remove inorganic salts, filtrate is dense
Column chromatography for separation is used after contracting, white solid 3g, yield 50% is obtained.
The synthesis of compound 23
In flask, add intermediate 23-1 (2.6g, 5.2mmol), 4- (3- pyridines)-phenyl boric acid (2.6g, 13mmol),
Potassium carbonate (2.7g, 20mmol), tetra-triphenylphosphine palladium (0.1g), tetrahydrofuran (20mL) and water (10mL), under nitrogen protection
It is heated to reflux 12 hours, cools down, extracted with dichloromethane, dry, concentration, crude product obtains 2.3g, yield through column chromatography purifying
68%.
Embodiment 3
The synthesis of compound 36
Intermediate 36-1 synthesis
Synthetic method is with intermediate 4-1, raw material is respectively 2- amino -5- bromopyridines and 3- biphenylboronic acids, and yield is
61%.
Intermediate 36-2 synthesis
Synthetic method with intermediate 36-1 with intermediate 23-1, being replaced outside intermediate 4-1, yield 52%.
The synthesis of compound 36
Synthetic method is with compound 23, raw materials used is intermediate 36-2 and 5- phenyl -2- pyridine pinacol boric acid
Ester, yield 60%.
Embodiment 4
The synthesis of compound 45
Intermediate 45-1 synthesis
Synthetic method is with intermediate 4-1, raw materials used is 2- amino -4- bromopyridines and 1- naphthalene boronic acids, yield 75%.
Intermediate 45-2 synthesis
Synthetic method is raw materials used that intermediate 4-1, yield 66% are replaced with intermediate 45-1 with intermediate 23-1.
The synthesis of compound 45
Synthetic method is with as compound 23, raw materials used is intermediate 45-2 and 3- (3- pyridine radicals)-phenyl boric acid, production
Rate 61%.
Embodiment 5-8
The preparation of organic electroluminescence device
OLED is prepared using the compound in the embodiment of the present invention.
First, by electrically conducting transparent ito glass substrate 110 (carrying anode 120 above) (the limited public affairs of South China glass group share
Department) pass through successively：Deionized water, ethanol, acetone and deionized water are cleaned, then with oxygen plasma treatment 30 seconds.
Then, NPB is deposited, the thick hole transmission layers 130 of 60nm are formed.
Then, the thick Alq of 37.5nm are deposited on hole transmission layer3Doping 1%C545T is used as luminescent layer 140.
Then, 37.5nm is deposited on luminescent layer thick as electron transfer layer 150, comprising 75% the compounds of this invention and
25% LiQ.
Finally, evaporation 1nm LiF are that electron injecting layer 160 and 100nm Al are used as device cathodes 170.
Prepared device (structural representation is shown in Fig. 1) measured with Photo Research PR650 spectrometers
20mA/cm2Current density under power efficiency it is as shown in table 1.
Comparative example
Except electron transfer layer Alq3Outside instead of the compounds of this invention, others are with embodiment 5-8.
Prepared device (structural representation is shown in Fig. 1) measured with Photo Research PR650 spectrometers
20mA/cm2Current density under power efficiency it is as shown in table 1.
| Embodiment | Compound | Power efficiency (lm/W) | Color |
| 5 | 4 | 6.4 | Green glow |
| 6 | 23 | 6.8 | Green glow |
| 7 | 36 | 7.0 | Green glow |
| 8 | 45 | 6.9 | Green glow |
| Comparative example | Alq3 | 5.4 | Green glow |
Under the same conditions, the organic electroluminescent prepared using the organic electroluminescent electron transport material of the present invention
The life-span of device is higher than comparative example, as described above, the compound of the present invention has high stability, Organic Electricity prepared by the present invention
Electroluminescence device has high life-span and optical purity.
Structural formula is as follows described in device：
Preferred embodiment of the invention described in detail above.It should be appreciated that the ordinary skill of this area is without wound
The property made work just can make many modifications and variations according to the design of the present invention.Therefore, all technical staff in the art
Pass through the available technology of logical analysis, reasoning, or a limited experiment on the basis of existing technology under this invention's idea
Scheme, all should be in the protection domain being defined in the patent claims.
Claims (10)
1. one kind contains the organic electroluminescent electron transport compound of [1,2,4]-triazole [1,5-a] pyridine, it is characterised in that
It is the compound with following structural formula I：
Wherein, R1-R4Separately selected from hydrogen, deuterium, halogen, cyano group, straight chain or C1-C12 alkyl with side chain, straight chain or
The substitution of C1-C8 alkoxyl, C6-C30 with side chain or unsubstituted aryl, C3-C30 substitution or unsubstituted miscellaneous
Aryl, triaryl phosphinyl；
L be selected from singly-bound, C6-C30 substitution or unsubstituted aryl, C3-C30 substitution or it is unsubstituted containing one or
The multiple heteroatomic heteroaryls of person；
Ar is selected from C6-C30 substitution or unsubstituted aryl, C3-C30 substitution or unsubstituted containing one or many
Individual heteroatomic heteroaryl, triaryl phosphinyl；
Py is pyridine radicals；
Ar1Selected from hydrogen, deuterium, C6-C30 substitution or unsubstituted aryl.
2. the organic electroluminescent electric transmission according to claim 1 containing [1,2,4]-triazole [1,5-a] pyridine
Compound, it is characterised in that R1-R4Separately it is selected from hydrogen, deuterium, fluorine, phenyl, naphthyl, phenanthryl, pyrenyl, xenyl, phenylnaphthalene
Base, naphthylphenyl, pyridine radicals, diphenyl phenyl.
3. the organic electroluminescent electric transmission according to claim 1 containing [1,2,4]-triazole [1,5-a] pyridine
Compound, it is characterised in that L is selected from singly-bound, phenyl, naphthyl.
4. the organic electroluminescent electric transmission according to claim 1 containing [1,2,4]-triazole [1,5-a] pyridine
Compound, it is characterised in that Ar1Selected from hydrogen, phenyl, naphthyl.
5. the organic electroluminescent electric transmission according to claim 1 containing [1,2,4]-triazole [1,5-a] pyridine
Compound, it is characterised in that Ar be selected from benzene, naphthyl, anthryl, phenanthryl, pyrenyl, perylenes base, fluoranthene base, (9,9- dialkyl group) fluorenyl, (9,
9- bis- replaces or unsubstituted aryl) fluorenyl, 9,9- Spirofluorene-based, dibenzothiophenes base, dibenzofuran group, xenyl, benzene
Base naphthyl, naphthylphenyl, diphenyl base phenyl, pyridine radicals, quinolyl, pyrimidine radicals, triazine radical, thiazolyl, oxazolyl, triazole
Base, quinoxalinyl, isoquinolyl, phenylpyridyl, pyridinylphenyl, bipyridyl, or more these groups further be C1-
C10 alkyl or alkoxy substitution.
6. the organic electroluminescent electric transmission according to claim 1 containing [1,2,4]-triazole [1,5-a] pyridine
Compound, it is characterised in that it is following structural 1-54 compound：
7. a kind of organic electroluminescence device, it includes anode, negative electrode and organic layer, and organic layer injects comprising luminescent layer, hole
At least one layer in layer, hole transmission layer, hole blocking layer, electron injecting layer, electron transfer layer, it is characterised in that in organic layer
At least one layer includes the organic electroluminescent electronics as claimed in claim 1 for containing [1,2,4]-triazole [1,5-a] pyridine
Transport compound.
8. organic electroluminescence device according to claim 7, it is characterised in that as described in structural formula I containing [1,2,
Layer where the organic electroluminescent electron transport compound of 4]-triazole [1,5-a] pyridine is electron transfer layer or electron injection
Layer.
9. organic electroluminescence device according to claim 7, it is characterised in that as described in structural formula I containing [1,2,
A kind of compound therein is used alone in the organic electroluminescent electron transport compound of 4]-triazole [1,5-a] pyridine, or simultaneously
Use the two or more compounds in structural formula I.
10. organic electroluminescence device according to claim 7, it includes anode, hole transmission layer, luminescent layer, electronics
Transport layer, electron injecting layer and negative electrode, it is characterised in that contain at least one structural formula I in electron transfer layer or electron injecting layer
Compound.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710413701.1A CN107033143A (en) | 2017-06-05 | 2017-06-05 | Compound and its organic electroluminescence device containing [1,2,4] triazole [1,5 a] pyridine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710413701.1A CN107033143A (en) | 2017-06-05 | 2017-06-05 | Compound and its organic electroluminescence device containing [1,2,4] triazole [1,5 a] pyridine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN107033143A true CN107033143A (en) | 2017-08-11 |
Family
ID=59540566
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201710413701.1A Pending CN107033143A (en) | 2017-06-05 | 2017-06-05 | Compound and its organic electroluminescence device containing [1,2,4] triazole [1,5 a] pyridine |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN107033143A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108047087A (en) * | 2018-01-18 | 2018-05-18 | 河南省科学院化学研究所有限公司 | 3 '-(4- bromonaphthalene -1- bases) [1,1 '-xenyl] -4- nitriles and its synthetic method |
| CN108084180A (en) * | 2017-12-26 | 2018-05-29 | 南京高光半导体材料有限公司 | A kind of novel electroluminescent compound and the organic electroluminescence device using the organic electroluminescent compounds |
| CN110590770A (en) * | 2019-08-22 | 2019-12-20 | 武汉尚赛光电科技有限公司 | Triazolopyridine-based organic electroluminescent material and organic electroluminescent device |
| KR20200126198A (en) * | 2019-04-29 | 2020-11-06 | 주식회사 엘지화학 | Novel hetero-cyclic compound and organic light emitting device comprising the same |
| CN115207228A (en) * | 2021-04-08 | 2022-10-18 | 常州强力昱镭光电材料有限公司 | Organic electroluminescent element |
| CN116082369A (en) * | 2019-08-22 | 2023-05-09 | 武汉尚赛光电科技有限公司 | Organic electroluminescent material based on triazolopyridine and organic electroluminescent device |
| EP4434987A1 (en) * | 2023-03-24 | 2024-09-25 | Affirma Biotech S. L. | Novel pd-l1 inhibitors |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106632325A (en) * | 2017-01-25 | 2017-05-10 | 上海道亦化工科技有限公司 | Azacycle-containing compound and organic electroluminescence device thereof |
| CN106749234A (en) * | 2016-11-24 | 2017-05-31 | 上海道亦化工科技有限公司 | Organic electroluminescent electron transport compound and its luminescent device based on anthracene |
-
2017
- 2017-06-05 CN CN201710413701.1A patent/CN107033143A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106749234A (en) * | 2016-11-24 | 2017-05-31 | 上海道亦化工科技有限公司 | Organic electroluminescent electron transport compound and its luminescent device based on anthracene |
| CN106632325A (en) * | 2017-01-25 | 2017-05-10 | 上海道亦化工科技有限公司 | Azacycle-containing compound and organic electroluminescence device thereof |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108084180A (en) * | 2017-12-26 | 2018-05-29 | 南京高光半导体材料有限公司 | A kind of novel electroluminescent compound and the organic electroluminescence device using the organic electroluminescent compounds |
| CN108047087A (en) * | 2018-01-18 | 2018-05-18 | 河南省科学院化学研究所有限公司 | 3 '-(4- bromonaphthalene -1- bases) [1,1 '-xenyl] -4- nitriles and its synthetic method |
| KR20200126198A (en) * | 2019-04-29 | 2020-11-06 | 주식회사 엘지화학 | Novel hetero-cyclic compound and organic light emitting device comprising the same |
| KR102521449B1 (en) | 2019-04-29 | 2023-04-12 | 주식회사 엘지화학 | Novel hetero-cyclic compound and organic light emitting device comprising the same |
| CN110590770A (en) * | 2019-08-22 | 2019-12-20 | 武汉尚赛光电科技有限公司 | Triazolopyridine-based organic electroluminescent material and organic electroluminescent device |
| CN116082369A (en) * | 2019-08-22 | 2023-05-09 | 武汉尚赛光电科技有限公司 | Organic electroluminescent material based on triazolopyridine and organic electroluminescent device |
| CN115207228A (en) * | 2021-04-08 | 2022-10-18 | 常州强力昱镭光电材料有限公司 | Organic electroluminescent element |
| EP4434987A1 (en) * | 2023-03-24 | 2024-09-25 | Affirma Biotech S. L. | Novel pd-l1 inhibitors |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN105669467B (en) | A kind of compound and its organic electroluminescence device based on fluoranthene | |
| CN105153130B (en) | Triazine derivative electron transport compound and its organic electroluminescence device | |
| CN107033143A (en) | Compound and its organic electroluminescence device containing [1,2,4] triazole [1,5 a] pyridine | |
| CN107954922A (en) | A kind of two carbazole derivates of xenyl and application thereof and organic electroluminescence device | |
| CN105294663B (en) | One kind containing pyridine compounds and its organic electroluminescence device | |
| CN107987009A (en) | A kind of carbazole derivates and application thereof and organic electroluminescence device | |
| CN107721979A (en) | A kind of organic electroluminescent compounds and its organic electroluminescence device based on pyridine and triazine | |
| CN105601612B (en) | Phosphorescence host compound containing indolyl radical and its organic electroluminescence device | |
| CN109535093A (en) | A kind of trisubstituted benzene based compound and organic electroluminescence device | |
| CN107382992A (en) | A kind of carbazoles organic electroluminescent compounds and its organic electroluminescence device | |
| CN107253954A (en) | Compound and its organic electroluminescence device containing pyridine groups | |
| CN108299388A (en) | A kind of phenanthrene derivatives and application thereof and organic electroluminescence device | |
| CN108997239A (en) | A kind of compound of cyano-containing and application thereof and organic electroluminescence device | |
| CN106977514A (en) | A kind of organic electroluminescent compounds and its luminescent device containing carbazole derivates | |
| CN107935914A (en) | A kind of two carbazole benzene derivatives and application thereof and organic electroluminescence device | |
| CN106883204A (en) | Organic electroluminescent compounds and luminescent device based on benzo [b] naphtho- [1,2 d] furans | |
| CN108912099A (en) | A kind of compound containing triazine and carbazole and application thereof and organic electroluminescence device | |
| CN106518882A (en) | Helical structural organic light emitting material and organic light emitting device thereof | |
| CN108299389A (en) | A kind of compound based on phenanthrene and carbazole and application thereof and organic electroluminescence device | |
| CN107417677A (en) | A kind of carbazole pyridines organic electroluminescent compounds and its organic electroluminescence device | |
| CN106711351A (en) | Compound containing quinoxaline and biphenyl groups and organic electroluminescence device thereof | |
| CN108752317A (en) | One kind is containing anthracene derivant and application thereof and luminescent device | |
| CN107641126A (en) | A kind of organic electroluminescent compounds based on Imidazopyridazine and application thereof and organic electroluminescence device | |
| CN106749234A (en) | Organic electroluminescent electron transport compound and its luminescent device based on anthracene | |
| CN106831798A (en) | Compound and its organic electroluminescence device containing five-membered ring structure |
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 | ||
| WD01 | Invention patent application deemed withdrawn after publication | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20170811 |