CN113444090A - Compound and application thereof - Google Patents
Compound and application thereof Download PDFInfo
- Publication number
- CN113444090A CN113444090A CN202010212494.5A CN202010212494A CN113444090A CN 113444090 A CN113444090 A CN 113444090A CN 202010212494 A CN202010212494 A CN 202010212494A CN 113444090 A CN113444090 A CN 113444090A
- Authority
- CN
- China
- Prior art keywords
- substituted
- unsubstituted
- compound
- formula
- aryl
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 121
- 239000000463 material Substances 0.000 claims abstract description 52
- 125000001424 substituent group Chemical group 0.000 claims abstract description 24
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims abstract description 8
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims abstract description 8
- 125000000732 arylene group Chemical group 0.000 claims abstract description 5
- 125000005549 heteroarylene group Chemical group 0.000 claims abstract description 5
- 239000010410 layer Substances 0.000 claims description 92
- -1 cyano, carbonyl Chemical group 0.000 claims description 46
- 230000005525 hole transport Effects 0.000 claims description 19
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 125000001072 heteroaryl group Chemical group 0.000 claims description 13
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 239000002346 layers by function Substances 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000001769 aryl amino group Chemical group 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 5
- 239000010409 thin film Substances 0.000 claims description 5
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 5
- 230000005669 field effect Effects 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 description 41
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- 238000002347 injection Methods 0.000 description 25
- 239000007924 injection Substances 0.000 description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- 238000002360 preparation method Methods 0.000 description 20
- 238000001704 evaporation Methods 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 230000008020 evaporation Effects 0.000 description 15
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 14
- 238000004440 column chromatography Methods 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 11
- 238000005516 engineering process Methods 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- 230000002950 deficient Effects 0.000 description 10
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 10
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000010408 film Substances 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 8
- 239000012043 crude product Substances 0.000 description 8
- 238000001035 drying Methods 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- 239000011368 organic material Substances 0.000 description 8
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 8
- 230000000903 blocking effect Effects 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000002019 doping agent Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 238000007363 ring formation reaction Methods 0.000 description 6
- 239000002356 single layer Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 4
- 230000009471 action Effects 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 238000002386 leaching Methods 0.000 description 4
- 238000013508 migration Methods 0.000 description 4
- 230000005012 migration Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 4
- 235000011056 potassium acetate Nutrition 0.000 description 4
- 238000002390 rotary evaporation Methods 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- BMIBJCFFZPYJHF-UHFFFAOYSA-N 2-methoxy-5-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine Chemical compound COC1=NC=C(C)C=C1B1OC(C)(C)C(C)(C)O1 BMIBJCFFZPYJHF-UHFFFAOYSA-N 0.000 description 3
- IDASOVSVRKONFS-UHFFFAOYSA-N 3-phenylprop-2-ynal Chemical compound O=CC#CC1=CC=CC=C1 IDASOVSVRKONFS-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 3
- 238000006069 Suzuki reaction reaction Methods 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 238000006555 catalytic reaction Methods 0.000 description 3
- 238000010549 co-Evaporation Methods 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- ZOCHARZZJNPSEU-UHFFFAOYSA-N diboron Chemical compound B#B ZOCHARZZJNPSEU-UHFFFAOYSA-N 0.000 description 3
- 238000005401 electroluminescence Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 229920000767 polyaniline Polymers 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 2
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 description 2
- DDGPPAMADXTGTN-UHFFFAOYSA-N 2-chloro-4,6-diphenyl-1,3,5-triazine Chemical compound N=1C(Cl)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC=C1 DDGPPAMADXTGTN-UHFFFAOYSA-N 0.000 description 2
- RZJPBQGRCNJYBU-UHFFFAOYSA-N 3-chloropyridin-2-amine Chemical compound NC1=NC=CC=C1Cl RZJPBQGRCNJYBU-UHFFFAOYSA-N 0.000 description 2
- MAGFQRLKWCCTQJ-UHFFFAOYSA-M 4-ethenylbenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C(C=C)C=C1 MAGFQRLKWCCTQJ-UHFFFAOYSA-M 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 2
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- RIWNFZUWWRVGEU-UHFFFAOYSA-N isocyanomethylbenzene Chemical compound [C-]#[N+]CC1=CC=CC=C1 RIWNFZUWWRVGEU-UHFFFAOYSA-N 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 125000001725 pyrenyl group Chemical group 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 description 1
- 125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 description 1
- 125000004529 1,2,3-triazinyl group Chemical group N1=NN=C(C=C1)* 0.000 description 1
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 description 1
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 description 1
- 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 description 1
- 125000004530 1,2,4-triazinyl group Chemical group N1=NC(=NC=C1)* 0.000 description 1
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 description 1
- 125000004506 1,2,5-oxadiazolyl group Chemical group 0.000 description 1
- 125000004517 1,2,5-thiadiazolyl group Chemical group 0.000 description 1
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 description 1
- 125000003363 1,3,5-triazinyl group Chemical group N1=C(N=CN=C1)* 0.000 description 1
- UNRNSTIWJVLLMX-UHFFFAOYSA-N 1-chloro-4-(isocyanomethyl)benzene Chemical compound ClC1=CC=C(C[N+]#[C-])C=C1 UNRNSTIWJVLLMX-UHFFFAOYSA-N 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- BUTGVBZBUDLKCM-UHFFFAOYSA-N 1h-benzimidazole;pyridine Chemical compound C1=CC=NC=C1.C1=CC=C2NC=NC2=C1 BUTGVBZBUDLKCM-UHFFFAOYSA-N 0.000 description 1
- DGAROTKDMYJPCD-UHFFFAOYSA-N 1h-benzimidazole;pyrimidine Chemical compound C1=CN=CN=C1.C1=CC=C2NC=NC2=C1 DGAROTKDMYJPCD-UHFFFAOYSA-N 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 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
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- ICTIUBGTUKTAID-UHFFFAOYSA-N 3-(3-chlorophenyl)prop-2-ynal Chemical compound ClC1=CC=CC(C#CC=O)=C1 ICTIUBGTUKTAID-UHFFFAOYSA-N 0.000 description 1
- MAXBVGJEFDMHNV-UHFFFAOYSA-N 5-chloropyridin-2-amine Chemical compound NC1=CC=C(Cl)C=N1 MAXBVGJEFDMHNV-UHFFFAOYSA-N 0.000 description 1
- FKIFDWYMWOJKTQ-UHFFFAOYSA-N 9-bromo-10-naphthalen-2-ylanthracene Chemical compound C12=CC=CC=C2C(Br)=C(C=CC=C2)C2=C1C1=CC=C(C=CC=C2)C2=C1 FKIFDWYMWOJKTQ-UHFFFAOYSA-N 0.000 description 1
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 101000930898 Cryphonectria parasitica Glyceraldehyde-3-phosphate dehydrogenase Proteins 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N Li2O Inorganic materials [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 101000766357 Ruditapes philippinarum Big defensin Proteins 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- JHYLKGDXMUDNEO-UHFFFAOYSA-N [Mg].[In] Chemical compound [Mg].[In] JHYLKGDXMUDNEO-UHFFFAOYSA-N 0.000 description 1
- IUSXYORAKPLJKJ-UHFFFAOYSA-N [chloro(isocyano)methyl]benzene Chemical compound [C-]#[N+]C(Cl)C1=CC=CC=C1 IUSXYORAKPLJKJ-UHFFFAOYSA-N 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy 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
- 230000003321 amplification Effects 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 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 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- LPTWEDZIPSKWDG-UHFFFAOYSA-N benzenesulfonic acid;dodecane Chemical compound OS(=O)(=O)C1=CC=CC=C1.CCCCCCCCCCCC LPTWEDZIPSKWDG-UHFFFAOYSA-N 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000005874 benzothiadiazolyl group Chemical group 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 125000004803 chlorobenzyl group Chemical group 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- 239000011162 core material Substances 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 1
- XUCJHNOBJLKZNU-UHFFFAOYSA-M dilithium;hydroxide Chemical compound [Li+].[Li+].[OH-] XUCJHNOBJLKZNU-UHFFFAOYSA-M 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000012761 high-performance material Substances 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
- 125000005990 isobenzothienyl group Chemical group 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 229910052744 lithium 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
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- 125000005244 neohexyl group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000003933 pentacenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C12)* 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 238000007725 thermal activation Methods 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 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
- C07D471/12—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 three hetero rings
- C07D471/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
-
- 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
Abstract
The invention relates to a compound and application thereof, wherein the compound has a structure shown in any one of a formula (1-1), a formula (1-2) or a formula (1-3), and R is1Represents a single substituent to the maximum permissible substituent, and L is selected from one of a single bond, a substituted or unsubstituted arylene group having C6-C60, and a substituted or unsubstituted heteroarylene group having C3-C60; ar is selected from one of substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C3-C60 heteroaryl; and the-L-Ar is not carbazolyl, dicarbazolyl or a substituent group containing a carbazole group. When the compound provided by the invention is applied to an OLED device, the efficiency of the device can be effectively improved, the driving voltage is reduced, and the compound is an electron transport material with good performance.
Description
Technical Field
The invention relates to the technical field of organic electroluminescence, in particular to a compound and application thereof.
Background
Organic Light Emission Diodes (OLED) devices are a kind of devices with sandwich-like structure, which includes positive and negative electrode films and Organic functional material layers sandwiched between the electrode films. And applying voltage to the electrodes of the OLED device, injecting positive charges from the positive electrode and injecting negative charges from the negative electrode, and transferring the positive charges and the negative charges in the organic layer under the action of an electric field to meet for composite luminescence. Because the OLED device has the advantages of high brightness, fast response, wide viewing angle, simple process, flexibility and the like, the OLED device is concerned in the field of novel display technology and novel illumination technology. At present, the technology is widely applied to display panels of products such as novel lighting lamps, smart phones and tablet computers, and further expands the application field of large-size display products such as televisions, and is a novel display technology with fast development and high technical requirements.
With the continuous advance of OLEDs in both lighting and display areas, much attention has been paid to the research on their core materials. This is because an efficient, long-lived OLED device is generally the result of an optimized configuration of the device structure and various organic materials, which provides great opportunities and challenges for chemists to design and develop functional materials with various structures. Common functionalized organic materials are: hole injection materials, hole transport materials, hole blocking materials, electron injection materials, electron transport materials, electron blocking materials, and light emitting host materials and light emitting objects (dyes), and the like.
The OLED light-emitting device with lower driving voltage, better light-emitting efficiency and longer service life is prepared, the performance of the OLED device is continuously improved, the structure and the manufacturing process of the OLED device are required to be innovated, and the photoelectric functional material in the OLED device is required to be continuously researched and innovated, so that the functional material with higher performance is prepared. Based on this, the OLED material industry has been working on developing new organic electroluminescent materials to achieve low starting voltage, high luminous efficiency and better lifetime of the device.
In order to further satisfy the continuously increasing demand for the photoelectric properties of OLED devices and the energy saving demand of mobile electronic devices, new and efficient OLED materials need to be continuously developed, wherein the development of new electron transport materials with high electron injection capability and high mobility is of great significance.
Disclosure of Invention
The object of the present invention is to provide a compound having a higher electron injection ability and a higher electron mobility.
In order to achieve the purpose, the invention adopts the following technical scheme:
the present invention provides a compound having a structure represented by any one of formula (1-1), formula (1-2), or formula (1-3):
in the formula (1-1), the formula (1-2) and the formula (1-3), R is1Represents one of single substituent to maximum allowable substituent, and is independently selected from hydrogen, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, halogen, cyano, alkenyl, alkynyl, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl, and when R is1When there are plural, adjacent R1Are not fused;
the L is selected from one of single bond, substituted or unsubstituted arylene of C6-C60 and substituted or unsubstituted heteroarylene of C3-C60;
ar is selected from one of substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C3-C60 heteroaryl;
and in the formula (1-1), the formula (1-2) and the formula (1-3), the-L-Ar is not a carbazolyl group, a bicarbazolyl group or a substituent group containing a carbazole group;
when the substituent group exists in the groups, the substituent group is selected from one or a combination of at least two of halogen, cyano, carbonyl, chain alkyl of C1-C12, cycloalkyl of C3-C12, alkenyl of C2-C10, alkoxy or thioalkoxy of C1-C10, arylamino of C6-C30, heteroarylamino of C3-C30, monocyclic aryl or condensed ring aryl of C6-C30, monocyclic heteroaryl or condensed ring heteroaryl of C3-C30.
Further preferably, the compound represented by formula (1-1), formula (1-2) or formula (1-3) of the present invention has a structure represented by the following formula (2-1) to formula (2-6):
in the formulae (2-1) to (2-6), Ar and L are as defined in the formula (1-1),
the R is2、R3Represents a single substituent to the maximum permissible substituent, R2、R3And R4Each independently selected from one of hydrogen, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, halogen, cyano, alkenyl, alkynyl, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl, and when R is2Or R3When there are plural, adjacent R2Between non-condensed linkages, adjacent R3Are not fused;
when the substituent group exists in the groups, the substituent group is selected from one or a combination of at least two of halogen, cyano, carbonyl, chain alkyl of C1-C12, cycloalkyl of C3-C12, alkenyl of C2-C10, alkoxy or thioalkoxy of C1-C10, arylamino of C6-C30, heteroarylamino of C3-C30, monocyclic aryl or condensed ring aryl of C6-C30, monocyclic heteroaryl or condensed ring heteroaryl of C3-C30.
Preferably, said R is1、R2、R3And R4Each independently selected from one of substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl.
Preferably, the L is selected from one of single bond, substituted or unsubstituted arylene of C6-C30 and substituted or unsubstituted heteroarylene of C3-C30.
Preferably, Ar is selected from one of substituted or unsubstituted aryl of C6-C30 and substituted or unsubstituted heteroaryl of C3-C30.
More preferably, in the above formula, Ar is a structure of the following formula a:
in the formula A, the Y1-Y6Selected from the group consisting of CR5Or N, R5Independently selected from one of hydrogen, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, halogen, cyano, alkenyl, alkynyl, substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C3-C60 heteroaryl, and two adjacent R5May be fused to form a ring.
Still further preferably, Ar is selected from the group consisting of substituted or unsubstituted structural formulas:
still more preferably, R is as defined above1、R2、R3、R4、R5Each independently selected from hydrogen or the following substituents: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2, 2-trifluoroethyl, phenyl, naphthyl, anthracenyl, benzanthryl, phenanthryl, benzophenanthryl, pyrenyl, grottoyl, perylenyl, anthrylenyl, tetracenyl, pentacenyl, benzopyrenyl, biphenyl, idophenyl, terphenyl, quaterphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis-or trans-indenylenyl, trimeric indenyl, isotridecylinyl, trimeric spiroindenyl, spiromesityl, spiroisotridecylinyl, furanyl, isobenzofuranyl, phenyl, terphenyl, anthryl, terphenyl, pyrenyl, terphenyl, etc., p-o, etc Dibenzofuranyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridyl, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, benzo-5, 6-quinolyl, benzoquinonyl-6, 7-quinolyl, benzo-7, 8-quinolyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthroimidazoyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxaloimidazolyl, oxazolyl, benzoxazolyl, naphthooxazolyl, anthraoxazolyl, phenanthroizolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyrazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1, 5-diazoanthrenyl, 2, 7-diazapyl, 2, 3-diazapyl, 1, 6-diazapyl, 1, 8-diazapyl, 4,5,9, 10-tetraazazapyryl, pyrazinyl, phenazinyl, phenothiazinyl, Naphthyridinyl, azacarbazolyl, benzocarbazinyl, phenanthrolinyl, 1,2, 3-triazolyl, 1,2, 4-triazolyl, benzotriazolyl, 1,2, 3-oxadiazolyl, 1,2, 4-oxadiazolyl, 1,2, 5-oxadiazolyl, 1,2, 3-thiadiazolyl, 1,2, 4-thiadiazolyl, 1,2, 5-thiadiazolyl, 1,3, 4-thiadiazolyl, 1,3, 5-triazinyl, 1,2, 4-triazinyl, 1,2, 3-triazinyl, tetrazolyl, 1,2,4, 5-tetrazinyl, 1,2,3, 4-tetrazinyl, 1,2,3, 5-tetrazinyl, purinyl, pteridinyl, indolizinyl, benzothiadiazolyl, or a combination of two of the foregoing.
Furthermore, the compounds described by the general formula of the present invention may preferably be compounds of the following specific structures represented by C1-C70, which are merely representative:
the second object of the present invention is to provide the use of the compound according to the first object for the application in organic electronic devices.
Preferably, the organic electronic device includes an organic electroluminescent device, an optical sensor, a solar cell, a lighting element, an organic thin film transistor, an organic field effect transistor, an organic thin film solar cell, an information label, an electronic artificial skin sheet, a sheet type scanner, or electronic paper, preferably an organic electroluminescent device.
Preferably, the compound is used as an electron transport material in the organic electroluminescent device.
The compound of the present invention has high electron affinity, so that the compound has strong electron accepting capacity and is suitable for use as electron transporting material, but is not limited to this.
The invention also provides an organic electroluminescent device, which comprises a first electrode, a second electrode and one or more luminescent functional layers which are inserted between the first electrode and the second electrode, wherein the luminescent functional layers contain the compound with the general formula of the invention shown in any one of the formulas (1-1), (1-2), (1-3) and (2-1) to (2-6) or the compound with the specific structural formula shown in each formula.
The OLED device prepared by the compound has low starting voltage, high luminous efficiency and better service life, and can meet the requirements of current panel manufacturing enterprises on high-performance materials.
Specifically, one embodiment of the present invention provides an organic electroluminescent device including a substrate, and an anode layer, a plurality of light emitting functional layers, and a cathode layer sequentially formed on the substrate; the light-emitting functional layer comprises a hole injection layer, a hole transport layer, a light-emitting layer and an electron transport layer, wherein the hole injection layer is formed on the anode layer, the hole transport layer is formed on the hole injection layer, the cathode layer is formed on the electron transport layer, and the light-emitting layer is arranged between the hole transport layer and the electron transport layer; wherein the electron transport layer contains the compound of the general formula of the present invention represented by any one of the above formulae (1-1), (1-2), (1-3) and formulae (2-1) to (2-6).
More specifically, the organic electroluminescent device will be described in detail.
The OLED includes first and second electrodes, and an organic material layer between the electrodes. The organic material may in turn be divided into a plurality of regions. For example, the organic material layer may include a hole transport region, a light emitting layer, and an electron transport region.
In a specific embodiment, a substrate may be used below the first electrode or above the second electrode. The substrate is a glass or polymer material having excellent mechanical strength, thermal stability, water resistance, and transparency. In addition, a Thin Film Transistor (TFT) may be provided on a substrate for a display.
The first electrode may be formed by sputtering or depositing a material used as the first electrode on the substrate. When the first electrode is used as an anode, Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), tin dioxide (SnO) may be used2) And transparent conductive oxide materials such as zinc oxide (ZnO), and any combination thereof. When the first electrode is used as a cathode, a metal or an alloy such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof can be used.
The organic material layer may be formed on the electrode by vacuum thermal evaporation, spin coating, printing, or the like. The compound used as the organic material layer may be an organic small molecule, an organic large molecule, and a polymer, and a combination thereof.
The hole transport region is located between the anode and the light emitting layer. The hole transport region may be a Hole Transport Layer (HTL) of a single layer structure including a single layer containing only one compound and a single layer containing a plurality of compounds. The hole transport region may also be a multilayer structure including at least one of a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), and an Electron Blocking Layer (EBL).
The material of the hole transport region may be selected from, but is not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylenevinylene, polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA), poly (3, 4-ethylenedioxythiophene)/poly (4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphorsulfonic acid (Pani/CSA), polyaniline/poly (4-styrenesulfonate) (Pani/PSS), aromatic amine derivatives such as compounds shown below in HT-1 to HT-34; or any combination thereof.
The hole injection layer is located between the anode and the hole transport layer. The hole injection layer may be a single compound material or a combination of a plurality of compounds. For example, the hole injection layer may employ one or more compounds of HT-1 to HT-34 described above, or one or more compounds of HI-1 to HI-3 described below; one or more of the compounds HT-1 to HT-34 may also be used to dope one or more of the compounds HI-1 to HI-3 described below.
The light-emitting layer includes a light-emitting dye (i.e., dopant) that can emit different wavelength spectra, and may also include a Host material (Host). The light emitting layer may be a single color light emitting layer emitting a single color of red, green, blue, or the like. The single color light emitting layers of a plurality of different colors may be arranged in a planar manner in accordance with a pixel pattern, or may be stacked to form a color light emitting layer. When the light emitting layers of different colors are stacked together, they may be spaced apart from each other or may be connected to each other. The light-emitting layer may be a single color light-emitting layer capable of emitting red, green, blue, or the like at the same time.
According to different technologies, the luminescent layer material can be different materials such as fluorescent electroluminescent material, phosphorescent electroluminescent material, thermal activation delayed fluorescent luminescent material, and the like. In an OLED device, a single light emitting technology may be used, or a combination of a plurality of different light emitting technologies may be used. These technically classified different luminescent materials may emit light of the same color or of different colors.
In one aspect of the invention, the light-emitting layer employs a fluorescent electroluminescence technique. The luminescent layer fluorescent host material may be selected from, but not limited to, the combination of one or more of BFH-1 through BFH-17 listed below.
In one aspect of the invention, the light-emitting layer employs a fluorescent electroluminescence technique. The luminescent layer fluorescent dopant may be selected from, but is not limited to, combinations of one or more of BFD-1 through BFD-12 listed below.
In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescent technology. The host material of the light emitting layer is selected from, but not limited to, one or more of GPH-1 to GPH-80.
In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescent technology. The phosphorescent dopant of the light emitting layer can be selected from, but is not limited to, one or more of GPD-1 to GPD-47 listed below.
Wherein D is deuterium.
In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescent technology. The phosphorescent dopant of the light emitting layer thereof may be selected from, but not limited to, a combination of one or more of RPD-1 to RPD-28 listed below.
In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescent technology. The phosphorescent dopant of the light-emitting layer can be selected from, but is not limited to, one or more of YPD-1 to YPD-11 listed below.
The organic electroluminescent device of the present invention includes an electron transport region between the light emitting layer and the cathode. The electron transport region may be an Electron Transport Layer (ETL) of a single-layer structure including a single-layer electron transport layer containing only one compound and a single-layer electron transport layer containing a plurality of compounds. The electron transport region may also be a multilayer structure including at least one of an Electron Injection Layer (EIL), an Electron Transport Layer (ETL), and a Hole Blocking Layer (HBL).
The electron transport region may also be formed using the compound of the present invention for a multilayer structure including at least one of an Electron Injection Layer (EIL), an Electron Transport Layer (ETL), and a Hole Blocking Layer (HBL), although the material of the electron transport region may also be combined with one or more of ET-1 to ET-57 listed below.
An electron injection layer may also be included in the device between the electron transport layer and the cathode, the electron injection layer material including, but not limited to, combinations of one or more of the following:
Liq、LiF、NaCl、CsF、Li2O、Cs2CO3、BaO、Na、Li、Ca。
the specific reason why the above-mentioned compound of the present invention is excellent in performance is not clear, and it is presumed that the following reasons may be:
the compound with the general formula adopts a pyrido-imidazopyridine electron-deficient group to bridge electron-deficient groups such as triazine, pyrimidine and quinazoline to form a novel electron-transporting material. The formed new electron transport material has stronger electron affinity and more proper molecular dipole moment, and is beneficial to the injection of electrons. In addition, the electron transport material has larger plane conjugation and good evaporation film-forming property, can form compact contact with other organic layer molecules, and is favorable for improving the mobility of electrons. The structural characteristics of the two aspects can make the molecule show good electron injection and migration performance. Therefore, when the compound is used as an electron transport layer material in an organic electroluminescent device, the electron injection and migration efficiency in the device can be effectively improved, so that the excellent effects of high luminous efficiency and low starting voltage of the device are ensured.
In addition, the preparation process of the compound is simple and feasible, the raw materials are easy to obtain, and the compound is suitable for mass production and amplification.
Detailed Description
The technical solution of the present invention is further explained by the following embodiments. It should be understood by those skilled in the art that the examples are only for the understanding of the present invention and should not be construed as the specific limitations of the present invention.
The basic chemical materials used in the following synthesis examples, such as ethanol, sodium sulfate, 1, 4-dioxane, tetrahydrofuran, dichloromethane, and potassium carbonate, were purchased from Shanghai Tantake technology Co., Ltd and Xiong chemical Co., Ltd. The mass spectrometer used for determining the following compounds was a ZAB-HS type mass spectrometer measurement (manufactured by Micromass, UK).
Synthesizing a general formula I:
firstly, 2-aminopyridine or derivatives thereof, phenylalkynyl formaldehyde or derivatives thereof and chlorobenzyl isocyanide are stirred at room temperature under the catalysis of perchloric acid and subjected to ring closing reaction by taking methanol as a solvent to generate an intermediate M1-1; in the second step, the intermediate M1-1 is heated, refluxed and subjected to ring closing reaction under the action of 2 equivalents of tetrabutylammonium bromide (TBAB) by taking DMF as a solvent to generate an intermediate M1-2; thirdly, reacting the intermediate M1-2 with pinacol ester diboron to generate an intermediate M1-3; in the fourth step, intermediate M1-3 reacts with aryl heteroaryl chloride through Suzuki reaction to generate target compound Cx.
Firstly, stirring 2-aminopyridine or derivatives thereof, chlorobenzyl alkynylaldehyde and benzyl isocyanide or derivatives thereof at room temperature under the catalysis of perchloric acid by using methanol as a solvent to perform a ring closing reaction to generate an intermediate M2-1; in the second step, the intermediate M2-1 is heated, refluxed and subjected to ring closing reaction under the action of 2 equivalents of tetrabutylammonium bromide (TBAB) by taking DMF as a solvent to generate an intermediate M2-2; thirdly, reacting the intermediate M2-2 with pinacol ester diboron to generate an intermediate M2-3; in the fourth step, intermediate M2-3 reacts with aryl heteroaryl chloride through Suzuki reaction to generate target compound Cx.
Firstly, chloro-2-aminopyridine, chloro-phenyl alkynyl formaldehyde and benzyl isocyanide or derivatives thereof are stirred at room temperature under the catalysis of perchloric acid and subjected to ring closing reaction by taking methanol as a solvent to generate an intermediate M3-1; in the second step, the intermediate M3-1 is heated, refluxed and subjected to ring closing reaction under the action of 2 equivalents of tetrabutylammonium bromide (TBAB) by taking DMF as a solvent to generate an intermediate M3-2; thirdly, reacting the intermediate M3-2 with pinacol ester diboron to generate an intermediate M3-3; in the fourth step, intermediate M3-3 reacts with aryl heteroaryl chloride through Suzuki reaction to generate target compound Cx.
Synthesis 1:
synthesis of Compound C1
(1) Preparation of Compound 1-1
2-aminopyridine (93g, 1mol), phenylpropargylaldehyde (130g, 1mol), 4-chlorobenzyl isocyanide (152g, 1mol) were dissolved in a 2L methanol flask, and 1ml perchloric acid was added dropwise. After the addition was completed, the reaction was stirred at room temperature for 3 hours, and the completion of the reaction was monitored by TLC. And filtering the separated solid, washing with water and ethanol respectively, and drying in the air, wherein the obtained crude product 1-1 is directly used for the next reaction.
(2) Preparation of Compounds 1-2
Compound 1-1 obtained in the above step was added to a flask containing 3L of DMF, tetrabutylammonium bromide (644g, 2mol) was added with stirring at room temperature, and after completion of the addition, the reaction was warmed to reflux for 4 hours, and TLC showed completion of the reaction. Cooling to room temperature, pouring the reaction system into a large amount of water, filtering the precipitated solid by suction, respectively leaching with water and ethanol, drying, and purifying the crude product by column chromatography to obtain the compound 1-2(230g, 65%).
(3) Preparation of Compounds 1-3
Compound 1-2(35.5g, 100mmol), pinacol diboron ester (38g, 150mmol) and potassium acetate (29.4g, 300mmol) were charged into a flask containing 1, 4-dioxane (500mL), and after replacing nitrogen with stirring at room temperature, palladium acetate (450mg, 2mmol) and SPhos (1.6g, 4mmol) were added. After the addition was complete, the reaction was refluxed with stirring for 12 hours, and the end of the reaction was monitored by TLC. The 1, 4-dioxane was removed by rotary evaporation, the mixture was separated with water and dichloromethane, the organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, and purified by column chromatography to give compound 1-3(34.4g, yield 77%).
(5) Preparation of Compound C1
Compounds of 1-3(8.1g, 18mmol), 2-chloro-4, 6-diphenyl-1, 3, 5-triazine (4.8g, 18mmol), potassium carbonate (7.45g, 54mmol), pd (dppf) Cl2(132mg, 0.18mmol) was added to a flask containing 100mL tetrahydrofuran and 25mL water, the nitrogen was replaced and the reaction was heated to reflux under nitrogen for 10 hours and TLC indicated completion of the reaction. The precipitated solid was filtered, rinsed with water and ethanol, respectively, dried and purified by column chromatography to give compound C1(8.0g, yield 81%). Calculated molecular weight: 552.21, found C/Z: 552.2.
synthesis example 2:
synthesis of Compound C16
(1) Preparation of Compound 2-1
2-aminopyridine (93g, 1mol), 3-chlorophenylpropynal (164g, 1mol), benzyl isocyan (118g, 1mol) were dissolved in a 2L methanol flask, and 1ml perchloric acid was added dropwise. After the addition was completed, the reaction was stirred at room temperature for 4 hours, and the completion of the reaction was monitored by TLC. And filtering the separated solid, washing with water and ethanol respectively, and drying in the air, wherein the obtained crude product 2-1 is directly used for the next reaction.
(2) Preparation of Compound 2-2
Compound 2-1 obtained in the above step was added to a flask containing 3L of DMF, tetrabutylammonium bromide (644g, 2mol) was added at room temperature with stirring, and after completion of the addition, the reaction was warmed to reflux for 3 hours, and TLC showed completion of the reaction. Cooling to room temperature, pouring the reaction system into a large amount of water, filtering the precipitated solid by suction, respectively leaching with water and ethanol, drying, and purifying the crude product by column chromatography to obtain a compound 2-2(221g, 62%).
(3) Preparation of Compounds 2-3
Compound 2-2(35.5g, 100mmol), pinacol diboron ester (38g, 150mmol) and potassium acetate (29.4g, 300mmol) were charged into a flask containing 1, 4-dioxane (500mL), and after replacing nitrogen with stirring at room temperature, palladium acetate (450mg, 2mmol) and SPhos (1.6g, 4mmol) were added. After the addition was complete, the reaction was stirred at reflux for 18 hours and the end of the reaction was monitored by TLC. The 1, 4-dioxane was removed by rotary evaporation, and the mixture was separated with water and dichloromethane, and the organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, and purified by column chromatography to give compound 2-3(35.7g, yield 80%).
(5) Preparation of Compound C16
Compounds of 2-3(8.1g, 18mmol), 2-chloro-4, 6-diphenyl-1, 3, 5-triazine (4.8g, 18mmol), potassium carbonate (7.45g, 54mmol), pd (dppf) Cl2(132mg, 0.18mmol) was added to a flask containing 100mL of tetrahydrofuran and 25mL of water, the nitrogen was replaced and the reaction was heated under reflux under nitrogen for 10 hours, and TLC showed the reactionAnd (4) completing. The precipitated solid was filtered, rinsed with water and ethanol, respectively, dried and purified by column chromatography to give compound C16(8.2g, yield 83%). Calculated molecular weight: 552.21, found C/Z: 552.2.
synthesis example 3:
synthesis of Compound C31
(1) Preparation of Compound 3-1
2-amino-5-chloropyridine (128g, 1mol), phenylpropargylaldehyde (130g, 1mol), and benzyl isocyan (118g, 1mol) were dissolved in a 2L methanol flask, and 1ml of perchloric acid was added dropwise. After the addition was completed, the reaction was stirred at room temperature for 3 hours, and the completion of the reaction was monitored by TLC. And filtering the separated solid, washing with water and ethanol respectively, and drying in the air, wherein the obtained crude product 3-1 is directly used for the next reaction.
(2) Preparation of Compound 3-2
Compound 3-1 obtained in the above step was added to a flask containing 3L of DMF, tetrabutylammonium bromide (644g, 2mol) was added at room temperature with stirring, and after completion of the addition, the reaction was warmed to reflux for 5 hours, and TLC showed completion of the reaction. Cooling to room temperature, pouring the reaction system into a large amount of water, filtering the precipitated solid by suction, respectively leaching with water and ethanol, drying, and purifying the crude product by column chromatography to obtain a compound 3-2(199g, 56%).
(3) Preparation of Compound 3-3
Compound 3-2(35.5g, 100mmol), pinacol diboron ester (38g, 150mmol) and potassium acetate (29.4g, 300mmol) were charged into a flask containing 1, 4-dioxane (500mL), and after replacing nitrogen with stirring at room temperature, palladium acetate (450mg, 2mmol) and SPhos (1.6g, 4mmol) were added. After the addition was complete, the reaction was refluxed with stirring for 10 hours, and the end of the reaction was monitored by TLC. The 1, 4-dioxane was removed by rotary evaporation, the mixture was separated with water and dichloromethane, the organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, and purified by column chromatography to give compound 3-3(36.2g, yield 81%).
(5) Preparation of Compound C31
Compound 3-3(8.1g, 18mmol), 2- (4-bromophenyl) -4, 6-diphenyl-1, 3, 5-triazine (7g, 18mmol), potassium carbonate (7.45g, 54mmol), pd (PPh3)4(208mg, 0.18mmol) were added to a flask containing toluene/ethanol/water 100mL/20mL/20mL, the nitrogen was replaced and the reaction was heated under nitrogen at reflux for 5 hours, and TLC showed completion of the reaction. The precipitated solid was filtered, rinsed with water and ethanol, respectively, dried and purified by column chromatography to obtain compound C31(10.5g, yield 86%). Calculated molecular weight: 628.24, found C/Z: 628.2.
synthesis example 4:
synthesis of Compound C62
(1) Preparation of Compound 4-1
2-amino-3-chloropyridine (128g, 1mol), phenylpropargylaldehyde (130g, 1mol), 4-cyanobenzylisocyan (143g, 1mol) were dissolved in a 2L methanol flask, and 1ml of perchloric acid was added dropwise. After the addition was completed, the reaction was stirred at room temperature for 6 hours, and the completion of the reaction was monitored by TLC. And filtering the separated solid, washing with water and ethanol respectively, and drying in the air, wherein the obtained crude product 4-1 is directly used for the next reaction.
(2) Preparation of Compound 4-2
Compound 4-1 obtained in the above step was added to a flask containing 3L of DMF, tetrabutylammonium bromide (644g, 2mol) was added at room temperature with stirring, and after completion of the addition, the reaction was warmed to reflux for 8 hours, and TLC showed completion of the reaction. Cooling to room temperature, pouring the reaction system into a large amount of water, filtering the precipitated solid by suction, respectively leaching with water and ethanol, drying, and purifying the crude product by column chromatography to obtain a compound 4-2(163g, 43%).
(3) Preparation of Compound 4-3
Compound 4-2(38g, 100mmol), pinacol diboron ester (38g, 150mmol) and potassium acetate (29.4g, 300mmol) were charged into a flask containing 1, 4-dioxane (500mL), and after replacing nitrogen with stirring at room temperature, palladium acetate (450mg, 2mmol), SPhos (1.6g, 4mmol) were added. After the addition was complete, the reaction was refluxed with stirring for 11 hours, and the end of the reaction was monitored by TLC. The 1, 4-dioxane was removed by rotary evaporation, the mixture was separated with water and dichloromethane, the organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, and purified by column chromatography to give compound 4-3(35.4g, yield 75%).
(5) Preparation of Compound C62
Compound 4-3(8.5g, 18mmol), 2-boronic acid-9, 9-spirobifluorene (6.5g, 18mmol), potassium carbonate (7.45g, 54mmol), pd (PPh3)4(208mg, 0.18mmol) were added to a flask containing toluene/ethanol/water 100mL/20mL/20mL, the nitrogen was replaced and the reaction was heated under reflux under nitrogen for 8 hours, TLC indicated completion of the reaction. The precipitated solid was filtered, rinsed with water and ethanol, respectively, dried and purified by column chromatography to obtain compound C62(10.5g, yield 86%). Calculated molecular weight: 660.23, found C/Z: 660.2.
synthesis example 5:
synthesis of Compound C67
(1) Preparation of Compound C67
Compound 1-3(8.1g, 18mmol), 9-bromo-10- (2-naphthyl) anthracene (7.6g, 20mmol), potassium carbonate (7.45g, 54mmol), pd (PPh3)4(208mg, 0.18mmol) were added to a flask containing toluene/ethanol/water 100mL/20mL/20mL, the reaction was refluxed for 10 hours under nitrogen atmosphere, and TLC showed completion of the reaction. The precipitated solid was filtered, rinsed with water and ethanol, respectively, dried and purified by column chromatography to give compound C67(8.7g, yield 78%). Calculated molecular weight: 623.24, found C/Z: 623.2.
device example 1
The embodiment provides a preparation method of an organic electroluminescent device, which comprises the following specific steps:
the glass plate coated with the ITO transparent conductive layer was sonicated in a commercial detergent, rinsed in deionized water, washed in acetone: ultrasonically removing oil in an ethanol mixed solvent, baking in a clean environment until the water is completely removed, cleaning by using ultraviolet light and ozone, and bombarding the surface by using low-energy cationic beams;
placing the glass substrate with the anode in a vacuum chamber, and vacuumizing until the pressure is less than 10-5Pa, performing vacuum evaporation on the anode layer film by using a multi-source co-evaporation method to obtain HI-3 as a hole injection layer, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 10 nm;
evaporating HT-4 on the hole injection layer in vacuum to serve as a first hole transport layer of the device, wherein the evaporation rate is 0.1nm/s, and the total evaporation film thickness is 40 nm;
evaporating HT-14 on the first hole transport layer in vacuum to serve as a second hole transport layer of the device, wherein the evaporation rate is 0.1nm/s, and the total evaporation film thickness is 10 nm;
a luminescent layer of the device is vacuum evaporated on the second hole transport layer, the luminescent layer comprises a main material and a dye material, the evaporation rate of the main material BFH-4 is adjusted to be 0.1nm/s, the evaporation rate of the dye BFD-4 is set in a proportion of 5%, and the total film thickness of evaporation is 20nm by using a multi-source co-evaporation method;
vacuum evaporating ET-17 on the luminescent layer to be used as a hole blocking layer of the device, wherein the evaporation rate is 0.1nm/s, and the total film thickness is 5 nm;
evaporating an electron transport layer on the hole blocking layer by using a multi-source co-evaporation method, adjusting the evaporation rate of the compound C1 to be 0.1nm/s, setting the proportion of the evaporation rate to the evaporation rate of ET-57 to be 100%, and setting the total film thickness of evaporation to be 23 nm;
LiF with the thickness of 1nm is vacuum-evaporated on the Electron Transport Layer (ETL) to be used as an electron injection layer, and an Al layer with the thickness of 80nm is used as a cathode of the device.
Device examples 2 to 5 differ from device example 1 only in that the electron transport layer material was replaced by compound C1 of the present invention for other compounds of the present invention, as specified in table 1.
Comparative device example 1
The difference from device example 1 is that the electron transport layer material was replaced by compound C1 according to the invention with compound D-1 according to the prior art.
Comparative device example 2
The difference from device example 1 is that the electron transport layer material was replaced by compound C1 according to the invention with compound D-2 according to the prior art.
Comparative device example 3
The difference from device example 1 is that the electron transport layer material was replaced by compound C1 according to the invention with compound D-3 according to the prior art.
And (3) performance testing:
the driving voltage and current efficiency of the organic electroluminescent devices prepared in examples 1 to 5 and comparative examples 1 to 3 were measured at the same brightness using a Photo radiometer model PR 750 from Photo Research, a brightness meter model ST-86LA (photoelectric instrument factory, university of beijing) and a Keithley4200 test system. Specifically, the voltage was raised at a rate of 0.1V per second, and it was determined that the luminance of the organic electroluminescent device reached 1000cd/m2The current density is measured at the same time as the driving voltage; the ratio of the brightness to the current density is the current efficiency;
the results of the performance tests are shown in table 1.
Table 1:
as can be seen from table 1, in the case that the material schemes and the preparation processes of other functional layers in the organic electroluminescent device structure are completely the same, compared with the comparative example, the organic electroluminescent devices provided in examples 1 to 5 of the present invention have higher current efficiency and lower driving voltage, and in examples 1 to 5, the device current efficiency is 8.21 to 8.77cd/a and the device driving voltage is 3.95 to 4.33V.
The compound of the present invention has a significant advantage in photoelectric properties as compared with the compound D-1 used in comparative example 1, and it is presumed that the reason is that the compound D-1 used in comparative example 1 has a new molecular structure in which an electron-deficient group of pyridoimidazopyridine is bonded to an electron-donating carbazole, although the group also contains the electron-deficient group of pyridoimidazopyridine. The introduction of the carbazole group for electron donation reduces the electron affinity of the whole molecule, which is not favorable for electron injection. Therefore, the compound of the present invention has relatively higher electron injection capability, and thus exhibits lower voltage and higher current efficiency as an electron transport material for use in devices.
Compared with the compound D-2 adopted in the comparative example 2 and the compound D-3 adopted in the comparative example 3, the compound of the invention has certain photoelectric property advantages, presumably because the electron-deficient group of benzimidazole pyrimidine is adopted to bridge other electron-deficient groups in the molecular structure of the compound D-2 in the comparative example 2 to form a new molecule, and the electron-deficient group of benzimidazole pyridine is adopted to bridge other electron-deficient groups at the ortho-position in the molecular structure of the compound D-3 in the comparative example 3 to form a new molecule, the dipole moment of the whole molecule is slightly poor compared with the compound of the invention, so that the electron injection capability is lower than that of the compound of the invention. In addition, the film-forming property and the degree of compactness of the contact with other organic layers of the compound D-2 and the compound D-3 are less than those of the compound of the invention, so that the compound of the invention has relatively higher electron migration capability, thereby showing better performance when being used as an electron transport material in a device. Therefore, the pyridoimidazopyridine in the compound is used as a large conjugated electron-deficient group, and the novel electron transport material constructed by combining the pyridoimidazopyridine with the electron-deficient groups such as triazine and pyrimidine has higher electron injection and migration performances, so that a device has higher current efficiency and lower driving voltage.
The experimental data show that the novel organic material is an organic luminescent functional material with good performance as an electron transport material of an organic electroluminescent device, and has wide application prospect.
The present invention is illustrated in detail by the examples described above, but the present invention is not limited to the details described above, i.e., it is not intended that the present invention be implemented by relying on the details described above. It should be understood by those skilled in the art that any modification of the present invention, equivalent substitutions of the raw materials of the product of the present invention, addition of auxiliary components, selection of specific modes, etc., are within the scope and disclosure of the present invention.
Claims (8)
1. A compound of the general formula (la) having a structure represented by any one of the formulae (1-1), (1-2) or (1-3):
in the formula (1-1), the formula (1-2) and the formula (1-3), R is1Represents one of single substituent to maximum allowable substituent, and is independently selected from hydrogen, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, halogen, cyano, alkenyl, alkynyl, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl, and when R is1When there are plural, adjacent R1Are not fused;
the L is selected from one of single bond, substituted or unsubstituted arylene of C6-C60 and substituted or unsubstituted heteroarylene of C3-C60;
ar is selected from one of substituted or unsubstituted aryl of C6-C60 and substituted or unsubstituted heteroaryl of C3-C60;
and in the formula (1-1), the formula (1-2) and the formula (1-3), the-L-Ar is not a carbazolyl group, a bicarbazolyl group or a substituent group containing a carbazole group;
when the substituent group exists in the groups, the substituent group is selected from one or a combination of at least two of halogen, cyano, carbonyl, chain alkyl of C1-C12, cycloalkyl of C3-C12, alkenyl of C2-C10, alkoxy or thioalkoxy of C1-C10, arylamino of C6-C30, heteroarylamino of C3-C30, monocyclic aryl or condensed ring aryl of C6-C30, monocyclic heteroaryl or condensed ring heteroaryl of C3-C30.
2. The compound of claim 1, having a structure represented by formula (2-1) to formula (2-6):
in the formulae (2-1) to (2-6), Ar and L are as defined in the formula (1-1),
the R is2、R3Represents a single substituent to the maximum permissible substituent, R2、R3And R4Each independently selected from one of hydrogen, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, halogen, cyano, alkenyl, alkynyl, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl, and when R is2Or R3When there are plural, adjacent R2Between non-condensed linkages, adjacent R3Are not fused;
when the substituent group exists in the groups, the substituent group is selected from one or a combination of at least two of halogen, cyano, carbonyl, chain alkyl of C1-C12, cycloalkyl of C3-C12, alkenyl of C2-C10, alkoxy or thioalkoxy of C1-C10, arylamino of C6-C30, heteroarylamino of C3-C30, monocyclic aryl or condensed ring aryl of C6-C30, monocyclic heteroaryl or condensed ring heteroaryl of C3-C30.
3. A compound according to claim 1 or 2, said R1、R2、R3And R4Each independently selected from one of substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl;
the L is selected from one of single bond, substituted or unsubstituted arylene of C6-C30 and substituted or unsubstituted heteroarylene of C3-C30;
ar is selected from one of substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl.
4. The compound of claim 1 or 2, wherein Ar is of formula a:
in the formula A, the Y1-Y6Selected from the group consisting of CR5Or N, R5Independently selected from one of hydrogen, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, halogen, cyano, alkenyl, alkynyl, substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C3-C60 heteroaryl, and two adjacent R5May be fused to form a ring.
5. The compound of claim 1 or 2, wherein Ar is selected from the group consisting of substituted or unsubstituted structural formulas:
when the substituent group exists in the groups, the substituent group is selected from one or a combination of at least two of halogen, cyano, carbonyl, chain alkyl of C1-C12, cycloalkyl of C3-C12, alkenyl of C2-C10, alkoxy or thioalkoxy of C1-C10, arylamino of C6-C30, heteroarylamino of C3-C30, monocyclic aryl or condensed ring aryl of C6-C30, monocyclic heteroaryl or condensed ring heteroaryl of C3-C30.
6. The compound of claim 1, having the structure shown below:
7. use of a compound according to any one of claims 1 to 6 as a functional material in an organic electronic device comprising an organic electroluminescent device, an optical sensor, a solar cell, a lighting element, an organic thin film transistor, an organic field effect transistor, an organic thin film solar cell, an information label, an electronic artificial skin sheet, a sheet-type scanner or electronic paper;
preferably, the compound is used as an electron transport material in an organic electroluminescent device.
8. An organic electroluminescent device comprising a first electrode, a second electrode and one or more light-emitting functional layers interposed between the first electrode and the second electrode, wherein the light-emitting functional layers contain the compound according to any one of claims 1 to 6;
preferably, the light-emitting functional layer comprises a hole transport region, a light-emitting layer and an electron transport region, the hole transport region is formed on the anode layer, the cathode layer is formed on the electron transport region, and the light-emitting layer is arranged between the hole transport region and the electron transport region; wherein the electron transport region comprises an electron transport layer containing the compound of any one of claims 1 to 6.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010212494.5A CN113444090B (en) | 2020-03-24 | 2020-03-24 | Compound and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010212494.5A CN113444090B (en) | 2020-03-24 | 2020-03-24 | Compound and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN113444090A true CN113444090A (en) | 2021-09-28 |
| CN113444090B CN113444090B (en) | 2024-04-16 |
Family
ID=77806457
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202010212494.5A Active CN113444090B (en) | 2020-03-24 | 2020-03-24 | Compound and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN113444090B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115232128A (en) * | 2022-08-15 | 2022-10-25 | 中国科学技术大学 | Imidazopyridinyl lipid compound and preparation method and application thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102119158A (en) * | 2008-11-03 | 2011-07-06 | 株式会社Lg化学 | Novel nitrogen-containing heterocyclic compound and organic electronic device using the same |
| KR20180023928A (en) * | 2014-12-03 | 2018-03-07 | 주식회사 엘지화학 | Organic light emitting device |
| KR20190033218A (en) * | 2017-09-21 | 2019-03-29 | 주식회사 두산 | Organic compounds and organic electro luminescence device comprising the same |
-
2020
- 2020-03-24 CN CN202010212494.5A patent/CN113444090B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102119158A (en) * | 2008-11-03 | 2011-07-06 | 株式会社Lg化学 | Novel nitrogen-containing heterocyclic compound and organic electronic device using the same |
| KR20180023928A (en) * | 2014-12-03 | 2018-03-07 | 주식회사 엘지화학 | Organic light emitting device |
| KR20190033218A (en) * | 2017-09-21 | 2019-03-29 | 주식회사 두산 | Organic compounds and organic electro luminescence device comprising the same |
Non-Patent Citations (2)
| Title |
|---|
| ACS: "STN REGISTRY", 《STN REGISTRY》, pages 1 * |
| YONG YI等: "Diversity-Oriented Synthesis of Imidazo-Dipyridines with Anticancer Activity via the Groebke-Blackburn-Bienayme and TBAB-Mediated Cascade Reaction in One Pot", 《JOURNAL OF ORGANIC CHEMISTRY》, vol. 84, no. 19, pages 12635 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115232128A (en) * | 2022-08-15 | 2022-10-25 | 中国科学技术大学 | Imidazopyridinyl lipid compound and preparation method and application thereof |
| CN115232128B (en) * | 2022-08-15 | 2024-03-29 | 中国科学技术大学 | Imidazo-pyridinyl lipid compound, and preparation method and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN113444090B (en) | 2024-04-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN110407859B (en) | Luminescent material, application thereof and organic electroluminescent device comprising luminescent material | |
| CN111333671B (en) | Luminescent material, application thereof and organic electroluminescent device comprising luminescent material | |
| CN110872316B (en) | Novel compound, application thereof and organic electroluminescent device using compound | |
| CN111153919B (en) | Luminescent material, application thereof and organic electroluminescent device comprising luminescent material | |
| CN112174992B (en) | Luminescent material, application thereof and organic electroluminescent device comprising luminescent material | |
| JP2023540114A (en) | Organic electroluminescent devices and display devices | |
| CN111808082B (en) | Luminescent material and application thereof | |
| CN112409276A (en) | Compound and application thereof | |
| CN112442037B (en) | Luminescent material and application thereof | |
| CN113444090B (en) | Compound and application thereof | |
| CN111285877A (en) | Organic electroluminescent material and device | |
| CN110746425B (en) | Organic compound and application thereof | |
| CN111763208B (en) | Luminescent material and application thereof | |
| CN111253373A (en) | Organic electroluminescent material, application and device using organic electroluminescent material | |
| CN112442035A (en) | Compound for organic light emitting material and organic electroluminescent device containing the same | |
| CN112778281A (en) | Compound and application thereof | |
| CN112661760B (en) | Compound for organic electronic material and organic electroluminescent device containing the same | |
| CN111377904A (en) | Organic electroluminescent material and device | |
| CN112442012B (en) | Compound and application thereof and device containing compound | |
| CN115368384B (en) | Organic compound, application thereof and organic electroluminescent device comprising same | |
| CN113402556A (en) | Compound and application thereof | |
| CN111909132A (en) | Organic material and organic electroluminescent device using same | |
| CN113968848A (en) | Organic compound for organic electroluminescent device and application thereof | |
| CN113461673A (en) | Compound and application thereof | |
| CN113402521A (en) | Compound and application thereof |
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 | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |