CN115197252A - Organic compound and application thereof - Google Patents
Organic compound and application thereof Download PDFInfo
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- CN115197252A CN115197252A CN202210832655.XA CN202210832655A CN115197252A CN 115197252 A CN115197252 A CN 115197252A CN 202210832655 A CN202210832655 A CN 202210832655A CN 115197252 A CN115197252 A CN 115197252A
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- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 17
- 150000001875 compounds Chemical class 0.000 claims abstract description 134
- 239000010410 layer Substances 0.000 claims description 353
- -1 naphthooxazolyl Chemical group 0.000 claims description 135
- 239000000463 material Substances 0.000 claims description 122
- 230000005525 hole transport Effects 0.000 claims description 65
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 31
- 229910052760 oxygen Inorganic materials 0.000 claims description 29
- 229910052717 sulfur Inorganic materials 0.000 claims description 29
- 125000003118 aryl group Chemical group 0.000 claims description 22
- 125000001072 heteroaryl group Chemical group 0.000 claims description 20
- 125000001624 naphthyl group Chemical group 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 14
- 229910052711 selenium Inorganic materials 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 10
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
- 125000003363 1,3,5-triazinyl group Chemical group N1=C(N=CN=C1)* 0.000 claims description 8
- 239000004215 Carbon black (E152) Substances 0.000 claims description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
- 229930195733 hydrocarbon Natural products 0.000 claims description 8
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims description 7
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 7
- 125000004104 aryloxy group Chemical group 0.000 claims description 7
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 7
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 7
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 7
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 150000004982 aromatic amines Chemical class 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 6
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 6
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 6
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 claims description 6
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 5
- 125000005577 anthracene group Chemical group 0.000 claims description 5
- 125000001769 aryl amino group Chemical group 0.000 claims description 5
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 5
- 125000002883 imidazolyl group Chemical group 0.000 claims description 5
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 5
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 5
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 5
- 239000002346 layers by function Substances 0.000 claims description 5
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 125000005493 quinolyl group Chemical group 0.000 claims description 5
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 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 4
- 125000005874 benzothiadiazolyl group Chemical group 0.000 claims description 4
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims description 4
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims description 4
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 4
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 claims description 4
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims description 4
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims description 4
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 4
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 4
- 239000010409 thin film Substances 0.000 claims description 4
- 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 claims description 3
- 125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 claims description 3
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims description 3
- 125000004506 1,2,5-oxadiazolyl group Chemical group 0.000 claims description 3
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical compound C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 claims description 3
- 229960005544 indolocarbazole Drugs 0.000 claims description 3
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 claims description 3
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 3
- 229930192474 thiophene Natural products 0.000 claims description 3
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims description 2
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims description 2
- HIYWOHBEPVGIQN-UHFFFAOYSA-N 1h-benzo[g]indole Chemical compound C1=CC=CC2=C(NC=C3)C3=CC=C21 HIYWOHBEPVGIQN-UHFFFAOYSA-N 0.000 claims description 2
- NFWATNMVZVJXMW-UHFFFAOYSA-N 9h-carbazole;dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1.C1=CC=C2C3=CC=CC=C3OC2=C1 NFWATNMVZVJXMW-UHFFFAOYSA-N 0.000 claims description 2
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 2
- 125000005264 aryl amine group Chemical group 0.000 claims description 2
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 229910052805 deuterium Inorganic materials 0.000 claims description 2
- 230000005669 field effect Effects 0.000 claims description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 125000004529 1,2,3-triazinyl group Chemical group N1=NN=C(C=C1)* 0.000 claims 2
- 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 claims 2
- 125000004530 1,2,4-triazinyl group Chemical group N1=NC(=NC=C1)* 0.000 claims 2
- 125000004517 1,2,5-thiadiazolyl group Chemical group 0.000 claims 2
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 claims 2
- BLFLLBZGZJTVJG-UHFFFAOYSA-N benzocaine Chemical compound CCOC(=O)C1=CC=C(N)C=C1 BLFLLBZGZJTVJG-UHFFFAOYSA-N 0.000 claims 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims 1
- 229960005274 benzocaine Drugs 0.000 claims 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims 1
- 238000001228 spectrum Methods 0.000 abstract description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 138
- 238000006243 chemical reaction Methods 0.000 description 135
- 238000002347 injection Methods 0.000 description 107
- 239000007924 injection Substances 0.000 description 107
- 239000000243 solution Substances 0.000 description 91
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 90
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 90
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 90
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 90
- 239000002904 solvent Substances 0.000 description 90
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 90
- 230000015572 biosynthetic process Effects 0.000 description 60
- 238000003786 synthesis reaction Methods 0.000 description 60
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 50
- 239000010405 anode material Substances 0.000 description 50
- 239000010406 cathode material Substances 0.000 description 49
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 46
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 46
- 239000003208 petroleum Substances 0.000 description 46
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 45
- 150000001793 charged compounds Chemical class 0.000 description 45
- 238000000921 elemental analysis Methods 0.000 description 45
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 45
- 239000012299 nitrogen atmosphere Substances 0.000 description 45
- 239000002243 precursor Substances 0.000 description 45
- 239000000741 silica gel Substances 0.000 description 45
- 229910002027 silica gel Inorganic materials 0.000 description 45
- 239000007787 solid Substances 0.000 description 45
- 238000003756 stirring Methods 0.000 description 45
- 238000010268 HPLC based assay Methods 0.000 description 25
- 238000004128 high performance liquid chromatography Methods 0.000 description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 8
- 239000011669 selenium Substances 0.000 description 8
- 238000001704 evaporation Methods 0.000 description 7
- 230000008020 evaporation Effects 0.000 description 6
- 239000002356 single layer Substances 0.000 description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000011368 organic material Substances 0.000 description 5
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- DRYAPKHYIPMFTP-UHFFFAOYSA-N [N].[B].[N] Chemical compound [N].[B].[N] DRYAPKHYIPMFTP-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000009987 spinning Methods 0.000 description 4
- 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 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 229920000767 polyaniline Polymers 0.000 description 3
- 125000001725 pyrenyl group Chemical group 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 3
- 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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 150000001555 benzenes Chemical group 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 230000003111 delayed effect Effects 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 description 2
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 230000002093 peripheral effect Effects 0.000 description 2
- 125000005561 phenanthryl group Chemical group 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- 238000007738 vacuum evaporation Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 description 1
- 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
- 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
- HTFNVAVTYILUCF-UHFFFAOYSA-N 2-[2-ethoxy-4-[4-(4-methylpiperazin-1-yl)piperidine-1-carbonyl]anilino]-5-methyl-11-methylsulfonylpyrimido[4,5-b][1,4]benzodiazepin-6-one Chemical compound CCOc1cc(ccc1Nc1ncc2N(C)C(=O)c3ccccc3N(c2n1)S(C)(=O)=O)C(=O)N1CCC(CC1)N1CCN(C)CC1 HTFNVAVTYILUCF-UHFFFAOYSA-N 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- CPDDXQJCPYHULE-UHFFFAOYSA-N 4,5,14,16-tetrazapentacyclo[9.7.1.12,6.015,19.010,20]icosa-1(18),2,4,6,8,10(20),11(19),12,14,16-decaene Chemical group C1=CC(C2=CC=CC=3C2=C2C=NN=3)=C3C2=CC=NC3=N1 CPDDXQJCPYHULE-UHFFFAOYSA-N 0.000 description 1
- BGEVROQFKHXUQA-UHFFFAOYSA-N 71012-25-4 Chemical compound C12=CC=CC=C2C2=CC=CC=C2C2=C1C1=CC=CC=C1N2 BGEVROQFKHXUQA-UHFFFAOYSA-N 0.000 description 1
- ZHQNDEHZACHHTA-UHFFFAOYSA-N 9,9-dimethylfluorene Chemical compound C1=CC=C2C(C)(C)C3=CC=CC=C3C2=C1 ZHQNDEHZACHHTA-UHFFFAOYSA-N 0.000 description 1
- VIJYEGDOKCKUOL-UHFFFAOYSA-N 9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 VIJYEGDOKCKUOL-UHFFFAOYSA-N 0.000 description 1
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
- HKMTVMBEALTRRR-UHFFFAOYSA-N Benzo[a]fluorene Chemical compound C1=CC=CC2=C3CC4=CC=CC=C4C3=CC=C21 HKMTVMBEALTRRR-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- JTPHKHUWLNQSSU-UHFFFAOYSA-N C1=CC=CC=2C=CC=3C=4C=CC=CC4NC3C21.C2(=CC=CC1=CC=CC=C21)N2C1=CC=CC=C1C=1C=CC=CC21 Chemical compound C1=CC=CC=2C=CC=3C=4C=CC=CC4NC3C21.C2(=CC=CC1=CC=CC=C21)N2C1=CC=CC=C1C=1C=CC=CC21 JTPHKHUWLNQSSU-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-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
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical group C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical group [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-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
- 230000009471 action Effects 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 230000003321 amplification Effects 0.000 description 1
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical group C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 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
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 125000006269 biphenyl-2-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(*)C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000006616 biphenylamine group Chemical group 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000010549 co-Evaporation Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 239000004020 conductor Substances 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
- 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
- 239000003599 detergent Substances 0.000 description 1
- 238000011161 development Methods 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
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000001194 electroluminescence spectrum Methods 0.000 description 1
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 1
- 238000002189 fluorescence spectrum Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000012761 high-performance material Substances 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000005990 isobenzothienyl group Chemical group 0.000 description 1
- 238000004020 luminiscence type Methods 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
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 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
- 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
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 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
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
- 125000004437 phosphorous atom Chemical group 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
- 229920000642 polymer Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000004044 response Effects 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
- 238000000926 separation method Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000007725 thermal activation Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 238000012795 verification 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
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C07F7/0816—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring comprising Si as a ring atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6581—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms
- C07F9/6584—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms having one phosphorus atom as ring hetero atom
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
- C09K2211/1055—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with other heteroatoms
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
- C09K2211/107—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms with other heteroatoms
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- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Health & Medical Sciences (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Plural Heterocyclic Compounds (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The present invention relates to an organic compound, and also relates to an organic electroluminescent device using the organic compound. The organic compound has the structure shown in the formula (1), has the advantages of high luminous efficiency, narrow spectrum emission and high stability, and an organic electroluminescent device adopting the compound has excellent device performance and stability.
Description
Technical Field
The present invention relates to an organic compound, and more particularly, to a compound useful for an organic electroluminescent device, and also to an organic electroluminescent device using the same.
Background
Organic Light Emission Diodes (OLED) 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.
In the aspect of selection of OLED luminescent materials, the singlet luminescent fluorescent material has the advantages of long service life, low price and low efficiency; triplet-emitting phosphorescent materials are efficient, but expensive, and the problem of lifetime of blue materials has not been solved. Adachi at kyushu university of japan proposes a new class of organic light emitting materials, i.e., thermally Activated Delayed Fluorescence (TADF) materials. The material utilizes the separation of a donor receptor to obtain a smaller singlet-triplet energy gap (delta E) ST )(<0.3 eV) so that triplet excitons may be converted into singlet excitons through reverse intersystem crossing (RISC) to emit light, and thus the internal quantum efficiency of the device may reach 100%.
In the prior art, a new structural compound design is performed by adopting a multiple resonance induced thermal activation delayed fluorescence (MR-TADF) strategy, for example, patent applications CN107851724, CN108431984, CN110407858 and the like design polycyclic aromatic compounds formed by connecting a plurality of aromatic rings by boron atoms and nitrogen atoms or oxygen atoms, i.e., a special rigid molecular system containing boron (B) atoms and nitrogen (N) atoms is constructed. Compared with a donor-receptor type TADF compound, the MR-TADF molecule has high radiative transition rate and narrower half-peak width, but most of the existing BN-type MR molecule light color is in a sky blue-green light region, the half-peak width is mostly about 30nm, and the requirements of a new generation ultra-high definition video standard BT.2020 cannot be met.
Disclosure of Invention
In one aspect, the present invention provides an organic compound having a structure represented by formula (1):
in formula (1): ring Ar 1 Ring Ar 2 Ring Ar 3 And ring Ar 4 Each independently selected from C6-C60 aromatic ring or C3-C60 heteroaromatic ring;
ring Ar 3 With ring Ar 4 Are not connected with each other, or are connected through a C-C single bond, or are connected through O, S or Se, or are connected through CR 7 R 8 、SiR 9 R 10 Or NR 11 Connecting;
ring Ar 1 With ring Ar 2 Are not connected with each other, or are connected through C-C single bond, or are connected through O, S or Se, or are connected through CR 7 R 8 、SiR 9 R 10 Or NR 11 Connecting;
X 1 is a single bond, O, S, se, CR 12 R 13 、SiR 14 R 15 、NR 16 Or PR 17 (ii) a m is 0 or 1;
R 1 、R 2 、R 3 、R 4 、R 5 and R 6 Each independently selected from one of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C2-C30 aliphatic chain hydrocarbon amino, substituted or unsubstituted C4-C30 cyclic aliphatic chain hydrocarbon amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroaryl amino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C60 arylboron, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl;
n1, n2, n3, n4 and n5 are each independently selected from integers from 0 to 10;
when n1, n2, n3, n4 and n5 are each independently integers greater than 1, a corresponding plurality of R 1 Between, a plurality of R 2 Between, a plurality of R 3 Between, a plurality of R 4 Between, a plurality of R 5 Each being the same or different, and a plurality of R 1 Are not connected or connected in a ring, a plurality of R 2 Are not connected or connected in a ring, a plurality of R 3 Are not connected or connected in a ring, a plurality of R 4 Are not connected or connected in a ring, a plurality of R 5 Are not connected or connected to form a ring;
R 7 、R 8 、R 9 、R 10 、R 11 、R 12 、R 13 、R 14 、R 15 、R 16 and R 17 Each independently selected from one of substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C2-C30 aliphatic chain hydrocarbon amino, substituted or unsubstituted C4-C30 cyclic aliphatic chain hydrocarbon amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroaryl amino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C3-C60 heteroaryl;
when R is as defined above 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、R 11 、R 12 、R 13 、R 14 、R 15 、R 16 And R 17 When the above substituents independently exist, each substituent is independently selected from one or a combination of two of halogen, cyano, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C10 alkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C6-C30 aryl, substituted or unsubstituted C6-C60 arylboron group, and C3-C30 heteroaryl.
Further preferably, in the above formula (1): m is 1, said X 1 Is a single bond, O, S, se, CR 12 R 13 、SiR 14 R 15 、NR 16 Or PR 17 ；
Said R is 12 、R 13 、R 14 、R 15 、R 16 And R 17 Each independently selected from one of C1-C6 chain alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 arylamine and substituted or unsubstituted C3-C30 heteroaryl;
preferably, said X 1 Is O, S, se, CR 12 R 13 、SiR 14 R 15 (ii) a More preferably, X is 1 Is O, S, CR 12 R 13 、SiR 14 R 15 (ii) a Most preferably, X is 1 Is S, CR 12 R 13 。
Preferably, said R is 12 、R 13 、R 14 、R 15 、R 16 And R 17 Each independently selected from any one of C1-C4 chain alkyl, substituted or unsubstituted benzene ring, naphthalene ring and anthracene ring; most preferably, said R 12 、R 13 、R 14 、R 15 、R 16 And R 17 Each independently a substituted or unsubstituted benzene ring.
Still preferably, in the above formula (1): the ring Ar 3 With ring Ar 4 Are connected through a C-C single bond, or through O, S or Se, or through CR 7 R 8 、SiR 9 R 10 Or NR 11 Connecting;
the ring Ar 1 With ring Ar 2 Are connected through a C-C single bond, or through O, S or Se, or through CR 7 R 8 、SiR 9 R 10 Or NR 11 Connecting;
the R is 7 、R 8 、R 9 、R 10 、R 11 Each independently selected from substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C6-C30 aralkyl, substituted or unsubstituted C6-C30 arylamine, substituted or unsubstituted C6-C60 aryl,One of substituted or unsubstituted C3-C60 heteroaryl;
preferably, the ring Ar 3 With ring Ar 4 Are connected through a C-C single bond, or through O, S or Se, or through CR 7 R 8 、SiR 9 R 10 Connecting; still more preferably, the ring Ar 3 With ring Ar 4 Are connected by a C-C single bond, or are connected by O or S, or are connected by CR 7 R 8 、SiR 9 R 10 Connecting; more preferably, the ring Ar 3 With ring Ar 4 Are connected by a C-C single bond, or are connected by S, or are connected by CR 7 R 8 、SiR 9 R 10 Connecting; most preferably, the ring Ar 3 With ring Ar 4 Are connected through a C-C single bond;
preferably, the ring Ar 1 With ring Ar 2 Are connected through a C-C single bond, or through O, S or Se, or through CR 7 R 8 、SiR 9 R 10 Connecting; still more preferably, the ring Ar 1 With ring Ar 2 Are connected by a C-C single bond, or are connected by O or S, or are connected by CR 7 R 8 、SiR 9 R 10 Connecting; more preferably, the ring Ar 1 With ring Ar 2 Are connected by a C-C single bond, or are connected by S, or are connected by CR 7 R 8 、SiR 9 R 10 Connecting; most preferably, the ring Ar 1 With ring Ar 2 Are connected through a C-C single bond;
preferably, R 7 、R 8 、R 9 、R 10 、R 11 Each independently selected from one of substituted or unsubstituted C1-C6 chain alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 arylamine and substituted or unsubstituted C3-C30 heteroaryl.
Still preferably, the organic compound represented by the above formula (1) has a structure represented by the following structural formula (1-1):
wherein R is 1 -R 6 、Ar 1 -Ar 4 And n1 to n4 are each as defined in formula (1).
Still preferably, the organic compound represented by the above formula (1) has a structure represented by any one of the following structural formulae (1-2), (1-3), (1-4), (1-5), (1-6), (1-7) or (1-8):
wherein R is 1 -R 11 、Ar 1 -Ar 4 And n1 to n4 are each as defined in the formula (1).
Still preferably, in the above formula (1), formula (1-1), (1-2), (1-3), (1-4), (1-5), (1-6), (1-7) or (1-8): said ring Ar 1 Ring Ar 2 Ring Ar 3 Ring Ar 4 And ring Ar 5 Each independently selected from C6-C60 aromatic ring or C3-C30 heteroaromatic ring; preferably, ring Ar 1 Ring Ar 2 Ring Ar 3 And ring Ar 4 Each independently selected from C6-C30 aromatic ring or C3-C20 heteroaromatic ring; more preferably, ring Ar 1 Ring Ar 2 Ring Ar 3 And ring Ar 4 Each independently selected from any one of benzene ring, naphthalene ring, anthracene ring, fluorene ring, furan, benzofuran, dibenzofuran, indole, benzindole, carbazole, indolocarbazole, benzothiophene, dibenzothiophene or thiophene; more preferably, the ring Ar 1 Ring Ar 2 Ring Ar and ring Ar 4 Each independently is any one of a benzene ring, a naphthalene ring, dibenzofuran carbazole or dibenzothiophene; most preferably, the ring Ar 1 Ring Ar 2 Ring Ar and ring Ar 4 Each independently a benzene ring.
Still preferably, in the above formula (1), formula (1-1), (1-2), (1-3), (1-4), (1-5), (1-6), (1-7) or (1-8): n1, n2, n3 and n4 are each independently selected from integers from 1 to 5;
the R is 1 、R 2 、R 3 、R 4 、R 5 、R 6 Each independently selected from 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-trifluoroethyl, cyano, halogen, phenyl, naphthyl, anthracyl, benzanthryl, phenanthryl, benzophenanthryl, pyrenyl, bornyl, perylenyl, fluoranthenyl, tetracenyl, pentacenyl, benzopyrenyl, biphenyl, idophenyl, terphenyl, quaterphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis-or trans-indenofluorenyl, trimeric indenyl, isotridecyl, spirotrimeric indenyl, spiroisotridemic indenyl, furyl, benzofuryl, isobenzofuryl, dibenzofuryl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridyl, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, benzo-5, 6-quinolyl, benzo-6, 7-quinolyl, benzo-7, 8-quinolyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalimidazolyl, kanilino, benzoxazolyl, naphthoxazolyl, anthraoxazolyl, phenanthroizolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyrazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalyl, 1, 5-diazahnthraninyl, 2, 7-diazpyrenyl group, 2, 3-diazpyrenyl group, 1, 6-diazpyrenyl group, 1, 8-diazpyrenyl group, 4,5,9, 10-tetraazaperylene group, pyrazinyl group, phenazinyl group, phenothiazinyl group, naphthyridinyl group, azacarbazolyl group, benzocarbazinyl group, phenanthrolinyl group, 1,2, 3-triazobenyl groupOne or a combination selected from among an azole group, a1, 2, 4-triazolyl group, a benzotriazolyl group, a1, 2, 3-oxadiazolyl group, a1, 2, 4-oxadiazolyl group, a1, 2, 5-oxadiazolyl group, a1, 2, 3-thiadiazolyl group, a1, 2, 5-thiadiazolyl group, a1, 3, 4-thiadiazolyl group, a1, 3, 5-triazinyl group, a1, 2, 4-triazinyl group, a1, 2, 3-triazinyl group, a tetrazolyl group, a1, 2,4, 5-tetrazinyl group, a1, 2,3, 4-tetrazinyl group, a purinyl group, a pteridinyl group, an indolizinyl group, a benzothiadiazolyl group, a diphenylboryl group, a dimyridylboryl group, a dipentafluorophenylboryl group, a bis (2, 4, 6-triisopropylphenyl) boryl group;
preferably, said R is 6 Is selected from hydrogen, said R 1 、R 2 、R 3 、R 4 、R 5 Each independently represents one of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, trifluoromethyl, pentafluoroethyl, cyano, halogen, phenyl, naphthyl, anthracenyl, fluorenyl, spirobifluorenyl, dihydrophenanthrenyl, dihydropyrenyl, tetrahydropyrenyl, cis-or trans-indenofluorenyl, furyl, benzofuryl, thienyl, benzothienyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridyl, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyrazinyl, pyrimidinyl, benzopyrimidinyl, 1,3, 5-triazinyl, diphenylboryl, dimyridylboronyl, dipentafluorophenylboryl, bis (2, 4, 6-triisopropylphenyl) boryl, or a combination selected from the two of the foregoing groups;
still more preferably, said R 6 Is selected from hydrogen, said R 1 、R 2 、R 3 、R 4 、R 5 Each independently represents one of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, trifluoromethyl, pentafluoroethyl, cyano, halogen, phenyl, naphthyl, anthracenyl, fluorenyl, spirobifluorenyl, carbazolyl, 1,3, 5-triazinyl, diphenylboryl, dimyridylboryl, dipentafluorophenylboryl, bis (2, 4, 6-triisopropylphenyl) boryl, or a combination of two of the above groups.
Still preferably, in the above formula (1), formula (1-1), (1-2), (1-3), (1-4), (1-5), (1-6), (1-7) or (1-8): the R is 7 、R 8 、R 9 、R 10 、R 11 Each independently selected from the following substituents: <xnotran> , , , , , , , ,2- , , , , , , , , , , , ,2- , , ,2,2,2- , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , -5,6- , -6,7- , -7,8- , , , , , , , , , , , , , , ,1,2- ,1,3- , , , , , , ,1,5- ,2,7- , </xnotran> 2, 3-diazenyl group, 1, 6-diazenyl group, 1, 8-diazenyl group, 4,5,9, 10-tetraazaphenyl group, pyrazinyl group, phenazinyl group, phenothiazinyl group, naphthyridinyl group, azacarbazolyl group, benzocarbazinyl group, phenanthrolinyl group, 1,2, 3-triazolyl group, 1,2, 4-triazolyl group, benzotriazolyl group, 1,2, 3-oxadiazolyl group, 1,2, 4-oxadiazolyl group, 1,2, 5-oxadiazolyl group, 1,2, 3-thiadiazolyl group, and the likeOne of a oxadiazolyl group, a1, 2, 4-thiadiazolyl group, a1, 2, 5-thiadiazolyl group, a1, 3, 4-thiadiazolyl group, a1, 3, 5-triazinyl group, a1, 2, 4-triazinyl group, a1, 2, 3-triazinyl group, a tetrazolyl group, a1, 2,4, 5-tetrazinyl group, a1, 2,3, 4-tetrazinyl group, a1, 2,3, 5-tetrazinyl group, a purinyl group, a pteridinyl group, an indolizinyl group, a benzothiadiazolyl group, or a combination selected from the two groups;
preferably, R 7 、R 8 、R 9 、R 10 、R 11 Each independently selected from the following substituents: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, trifluoromethyl, pentafluoroethyl, cyano, halo, phenyl, naphthyl, anthracenyl, fluorenyl, spirobifluorenyl, dihydrophenanthrenyl, dihydropyrenyl, tetrahydropyrenyl, cis-or trans-indenofluorenyl, furyl, benzofuryl, thienyl, benzothienyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridyl, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, pyrimidinyl, benzopyrimidinyl, 1,3, 5-triazinyl, diphenylboryl, dimyridylboronyl, dipentafluorophenylboryl, bis (2, 4, 6-triisopropylphenyl) boryl, or a combination selected from the two or more thereof;
further preferably, R 7 、R 8 、R 9 、R 10 、R 11 Each independently selected from the following substituents: one of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, phenyl, naphthyl, anthryl, fluorenyl and spirobifluorenyl, or a combination of two of the above groups.
In the present specification, the "substituted or unsubstituted" group may be substituted with one substituent, or may be substituted with a plurality of substituents, and when a plurality of substituents are present, different substituents may be selected from the group.
In the present specification, the expression of Ca to Cb means that the group has carbon atoms of a to b, and the carbon atoms do not generally include the carbon atoms of the substituents unless otherwise specified.
In the present specification, "independently" means that when a plurality of subjects are present, they may be the same or different from each other.
In the present specification, examples of the halogen include: fluorine, chlorine, bromine, iodine, and the like.
In the present specification, unless otherwise specified, both aryl and heteroaryl groups include monocyclic and fused rings. The monocyclic aryl group means that the molecule contains one or at least two phenyl groups, and when the molecule contains at least two phenyl groups, the phenyl groups are independent of each other and are connected by a single bond, such as phenyl, biphenylyl, terphenylyl, and the like, for example; the fused ring aryl group means that at least two benzene rings are contained in the molecule, but the benzene rings are not independent of each other, but common ring sides are fused with each other, and exemplified by naphthyl, anthryl and the like; monocyclic heteroaryl refers to a compound having at least one heteroaryl group in the molecule, and when a heteroaryl group and other groups (e.g., aryl, heteroaryl, alkyl, etc.) are present in the molecule, the heteroaryl and other groups are independently linked by a single bond, illustratively pyridine, furan, thiophene, etc.; fused ring heteroaryl refers to a fused ring of at least one phenyl group and at least one heteroaryl group, or, fused ring of at least two heteroaryl rings, illustratively quinoline, isoquinoline, benzofuran, dibenzofuran, benzothiophene, dibenzothiophene, and the like.
In the specification, the C6-C60 aryl group, preferably the C6-C30 aryl group, preferably the aryl group is selected from phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, indenyl, fluorenyl and derivatives thereof, fluoranthryl, triphenylene, pyrenyl, perylenyl, perylene, and the like,
A group of the group consisting of a phenyl group and a tetracenyl group. The biphenyl group is selected from the group consisting of 2-biphenyl, 3-biphenyl, and 4-biphenyl; the terphenyl group includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenylBiphenyl-4-yl, m-terphenyl-3-yl and m-terphenyl-2-yl; the naphthyl group includes a 1-naphthyl group or a 2-naphthyl group; the anthracene group is selected from the group consisting of 1-anthracene group, 2-anthracene group, and 9-anthracene group; the fluorenyl group is selected from the group consisting of 1-fluorenyl group, 2-fluorenyl group, 3-fluorenyl group, 4-fluorenyl group and 9-fluorenyl group; the fluorene derivative is selected from the group consisting of 9,9 '-dimethylfluorene, 9' -spirobifluorene and benzofluorene; the pyrenyl group is selected from the group consisting of 1-pyrenyl, 2-pyrenyl and 4-pyrenyl; the tetracenyl is selected from the group consisting of 1-tetracenyl, 2-tetracenyl, and 9-tetracenyl.
In the present specification, the C3-C60 heteroaryl group is preferably a C4-C30 heteroaryl group, and preferably the heteroaryl group is a furyl group, a thienyl group, a pyrrolyl group, a benzofuryl group, a benzothienyl group, an isobenzofuryl group, an indolyl group, a dibenzofuryl group, a dibenzothienyl group, a carbazolyl group and derivatives thereof, wherein the carbazolyl derivative is preferably 9-phenylcarbazole, 9-naphthylcarbazole benzocarbazole, dibenzocarbazole, or indolocarbazole.
The aryloxy group in the present specification includes a monovalent group composed of the above-mentioned aryl group, heteroaryl group and oxygen.
Examples of the alkoxy group in the present specification include the above-mentioned linear alkyl group or a monovalent group composed of a cycloalkyl group and oxygen.
Examples of the C6 to C60 arylamine group mentioned in the present specification include: phenylamino, methylphenylamino, naphthylamino, anthracylamino, phenanthrylamino, biphenylamino and the like.
Examples of the C6 to C60 heteroarylamino group mentioned in the present specification include: pyridylamino, pyrimidylamino, dibenzofuranylamino and the like.
10. Further, the compound represented by the general formula (1) of the present invention may preferably be a compound having the following specific structure: a-1 to C1-135, C2-1 to C2-78, C3-1 to C3-78, C4-1 to C4-43, C5-1 to C5-43, C6-1 to C6-43, these compounds being representative only:
the structural characteristics of the compounds of the invention are as follows: the structure of the formula (1) is adopted as a mother nucleus, and specific X is introduced into a meta position of a boron atom in a benzene ring at the center of the mother nucleus 1 X of the formula 1 May be a single bond, X 1 May be a carbon atom, silicon atom, nitrogen atom, phosphorus atom, or oxygen atomA sulfur atom or a selenium atom.
X in the parent nucleus structure of the compounds of the invention 1 The introduction of the nitrogen-boron-nitrogen compound effectively locks the donor on the left side in the parent nucleus structure, thereby effectively eliminating the repulsion between hydrogen atoms on the central benzene ring and the hydrogen atoms on the peripheral benzene rings in the nitrogen-boron-nitrogen structure, enabling the central benzene ring and the peripheral aromatic rings to be almost coplanar, effectively reducing the deformation and vibration relaxation of the excited state of the molecule, and improving the stability and color purity of the molecule. Meanwhile, X is introduced into the parent nucleus structure of the compound 1 The basic multiple resonance characteristic of the nitrogen-boron-nitrogen structure is not influenced, so that the characteristics of high quantum efficiency and narrow spectrum of the multiple resonance dye are maintained. While due to X 1 The atoms designed as C, si, N, P, O, S and Se can use different electronegativities to adjust the luminescent colors of the compounds of the invention from blue light (single bond), blue-green light (C, si), green light (O, S and Se) to red light (N and P). As can be seen from representative application verification examples of the present invention, the compounds of the present invention have a relatively greatly narrowed half-peak width (14 to 20 nm) when used as a luminescent dye, and organic photoelectric devices using the compounds of the present invention exhibit relatively higher lifetimes, as compared to existing BN dye molecules.
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.
In a second aspect of the present invention, there is also provided a use of a compound represented by any one of the above general formula (1) and general formulae (1-1) to (1-8) 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 an organic electroluminescent device.
In a third aspect, the present invention also provides an organic electroluminescent device comprising a substrate including a first electrode, a second electrode, and one or more organic layers interposed between the first electrode and the second electrode, wherein the organic layers contain a compound represented by any one of the above general formula (1), general formula (1-1) to (1-8).
Specifically, one embodiment of the present invention provides an organic electroluminescent device comprising 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 light-emitting layer contains the compound represented by the general formula (1) of the present invention.
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.
Detailed Description
The specific production method of the above-mentioned novel compound of the present invention will be described in detail below by taking a plurality of synthesis examples as examples, but the production method of the present invention is not limited to these synthesis examples.
The basic chemical materials of various chemicals used in the present invention, such as petroleum ether, ethyl acetate, sodium sulfate, toluene, tetrahydrofuran, dichloromethane, acetic acid, potassium carbonate, etc., are commercially available from Shanghai Tantake technology Co., ltd. And Xilonga chemical Co., ltd. The mass spectrometer used for determining the following compounds used was a ZAB-HS type mass spectrometer (manufactured by Micromass, UK).
The synthesis of the compounds of the present invention is briefly described below.
Synthetic examples
Representative synthetic route:
more specifically, the following gives synthetic methods of representative compounds of the present invention.
Synthetic examples
Synthesis example 1:
synthesis of Compound A1
Under a nitrogen atmosphere, a pentane solution of n-butyllithium (24mL, 2.50M, 60mmol) was slowly added to a solution of Br generation precursor (8.49g, 15mmol) in t-butylbenzene (150 mL) at 0 ℃ and then heated to 25 ℃ for 1 hour. After the reaction is finished, the temperature is reduced to minus 30 ℃, boron tribromide (15.04g, 60mmol) is slowly added, the temperature is increased to 60 ℃, and the stirring is continued for 2 hours. N, N-diisopropylethylamine (15.52g, 120mmol) was added at room temperature and the reaction was continued at 130 ℃ for 12 hours and stopped, the solvent was dried in vacuo and passed through a silica gel column (developing solvent: dichloromethane: petroleum ether =1 10) to give the target compound a-1 (33% yield, HPLC analytical purity 99%) as a yellow solid. MALDI-TOF-MS results: molecular ion peaks: 430.13 elemental analysis results: theoretical value: c,83.74; h,3.51; b,2.51; n,6.51; experimental values: c,83.72; h,3.52; b,2.50; and N,6.53.
Synthesis example 2:
synthesis of Compound A-4
Under the nitrogen atmosphere, a pentane solution (60 mmol) of n-butyllithium was slowly added to a solution of a Br-substituted precursor (15 mmol) in tert-butylbenzene (150 mL) at 0 ℃, and then the temperature was raised to 25 ℃ for reaction for 1 hour. After the reaction is finished, the temperature is reduced to minus 30 ℃, boron tribromide (60 mmol) is slowly added, the temperature is increased to 60 ℃, and the stirring is continued for 2 hours. N, N-diisopropylethylamine (120 mmol) was added at room temperature, and the reaction was continued at 130 ℃ for 12 hours and then stopped, and the solvent was dried in vacuo and passed through a silica gel column (developing solvent: dichloromethane: petroleum ether =1: 10) to give the objective compound a-4 (35% yield, HPLC assay purity 99%) as a yellow solid. MALDI-TOF-MS results: molecular ion peaks: 654.38 elemental analysis results: theoretical value: 84.39; h,7.24; b,1.65; n,4.28; experimental values: 84.41; h,7.25; b,1.66; and N,4.25.
Synthetic example 3:
synthesis of Compound A8
Under a nitrogen atmosphere, a pentane solution of n-butyllithium (60 mmol) was slowly added to a solution of Br precursor (15 mmol) in t-butylbenzene (150 mL) at 0 deg.C, and then the temperature was raised to 25 deg.C for reaction for 1 hour. After the reaction is finished, the temperature is reduced to minus 30 ℃, boron tribromide (60 mmol) is slowly added, the temperature is increased to 60 ℃, and the stirring is continued for 2 hours. N, N-diisopropylethylamine (120 mmol) was added at room temperature, and the reaction was continued at 130 ℃ for 12 hours and then stopped, and the solvent was dried in vacuo and passed through a silica gel column (developing solvent: dichloromethane: petroleum ether =1 10) to obtain the objective compound a-8 (34% yield, HPLC analytical purity 99%) as a yellow solid. MALDI-TOF-MS results: molecular ion peaks: 958.50 elemental analysis results: theoretical values are as follows: c,87.66; h,6.62; b,1.13; n,2.92; experimental values: c,87.65; h,6.61; b,1.14; and N,2.94.
Synthetic example 4:
synthesis of Compound A10
Under a nitrogen atmosphere, a pentane solution of n-butyllithium (60 mmol) was slowly added to a solution of Br precursor (15 mmol) in t-butylbenzene (150 mL) at 0 deg.C, and then the temperature was raised to 25 deg.C for reaction for 1 hour. After the reaction is finished, the temperature is reduced to minus 30 ℃, boron tribromide (60 mmol) is slowly added, the temperature is increased to 60 ℃, and the stirring is continued for 2 hours. N, N-diisopropylethylamine (120 mmol) was added at room temperature, and the reaction was continued at 130 ℃ for 12 hours and then stopped, and the solvent was dried in vacuo and passed through a silica gel column (developing solvent: dichloromethane: petroleum ether =1: 10) to give the target compound a-10 (28% yield, HPLC assay purity 99%) as a yellow solid. MALDI-TOF-MS results: molecular ion peaks: 1098.42 results of elemental analysis: theoretical value: c,85.24; h,4.68; b,0.98; n,7.65; experimental values: c,85.25; h,4.70; b,0.99; and N,7.63.
Synthesis example 5:
synthesis of Compound A-13
Under the nitrogen atmosphere, a pentane solution (60 mmol) of n-butyllithium was slowly added to a solution of a Br-substituted precursor (15 mmol) in tert-butylbenzene (150 mL) at 0 ℃, and then the temperature was raised to 25 ℃ for reaction for 1 hour. After the reaction is finished, the temperature is reduced to minus 30 ℃, boron tribromide (60 mmol) is slowly added, the temperature is increased to 60 ℃, and the stirring is continued for 2 hours. N, N-diisopropylethylamine (120 mmol) was added at room temperature and the reaction was continued at 130 ℃ for 12 hours and stopped, the solvent was dried in vacuo and passed through a silica gel column (developing solvent: dichloromethane: petroleum ether =1: 10) to give the target compound a-8 (31% yield, 99% HPLC assay purity) as an orange-yellow solid. MALDI-TOF-MS results: molecular ion peaks: 630.19 elemental analysis results: theoretical value: c,87.63; h,3.68; b,1.71; n,4.44; experimental values: c,87.65; h,3.67; b,1.72; n,4.41.
Synthetic example 6:
synthesis of Compound A-17
Under the nitrogen atmosphere, a pentane solution (60 mmol) of n-butyllithium was slowly added to a solution of a Br-substituted precursor (15 mmol) in tert-butylbenzene (150 mL) at 0 ℃, and then the temperature was raised to 25 ℃ for reaction for 1 hour. After the reaction is finished, the temperature is reduced to minus 30 ℃, boron tribromide (60 mmol) is slowly added, the temperature is increased to 60 ℃, and the stirring is continued for 2 hours. N, N-diisopropylethylamine (120 mmol) was added at room temperature and the reaction was continued at 130 ℃ for 12 hours and stopped, the solvent was dried in vacuo and passed through a silica gel column (developing solvent: dichloromethane: petroleum ether =1: 10) to give the title compound a-17 (32% yield, 99% purity by HPLC) as an orange-yellow solid. MALDI-TOF-MS results: molecular ion peaks: 658.41 elemental analysis results: theoretical values are as follows: c,83.87; h,7.80; b,1.64; n,4.25; (ii) a Experimental values: c,83.89; h,7.81; b,1.61; n,4.25; .
Synthetic example 7:
synthesis of Compound A-21
Under the nitrogen atmosphere, a pentane solution (60 mmol) of n-butyllithium was slowly added to a solution of a Br-substituted precursor (15 mmol) in tert-butylbenzene (150 mL) at 0 ℃, and then the temperature was raised to 25 ℃ for reaction for 1 hour. After the reaction is finished, the temperature is reduced to-30 ℃, boron tribromide (60 mmol) is slowly added, the temperature is increased to 60 ℃, and the stirring is continued for 2 hours. N, N-diisopropylethylamine (120 mmol) was added at room temperature and the reaction was continued at 130 ℃ for 12 hours and stopped, the solvent was dried in vacuo and passed through a silica gel column (developing solvent: dichloromethane: petroleum ether =1: 10) to give the target compound a-21 (31% yield, 99% HPLC assay purity) as an orange-yellow solid. MALDI-TOF-MS results: molecular ion peaks: 760.24 elemental analysis results: theoretical value: c,85.27; h,3.84; b,1.42; n,7.37; experimental values: c,85.26; h,3.85; b,1.40; and N,7.35.
Synthesis example 8:
synthesis of Compound A-24
Under a nitrogen atmosphere, a pentane solution of n-butyllithium (60 mmol) was slowly added to a solution of Br precursor (15 mmol) in t-butylbenzene (150 mL) at 0 deg.C, and then the temperature was raised to 25 deg.C for reaction for 1 hour. After the reaction is finished, the temperature is reduced to-30 ℃, boron tribromide (60 mmol) is slowly added, the temperature is increased to 60 ℃, and the stirring is continued for 2 hours. N, N-diisopropylethylamine (120 mmol) was added at room temperature and the reaction was continued at 130 ℃ for 12 hours and stopped, the solvent was dried in vacuo and passed through a silica gel column (developing solvent: dichloromethane: petroleum ether =1: 10) to give the title compound a-24 (22% yield, 99% HPLC assay purity) as an orange-yellow solid. MALDI-TOF-MS results: molecular ion peaks: 760.24 elemental analysis results: theoretical values are as follows: c,85.27; h,3.84; b,1.42; n,7.37; experimental values: c,85.27; h,3.83; b,1.44; n,7.37.
Synthetic example 9:
synthesis of Compound A-44
Under the nitrogen atmosphere, a pentane solution (60 mmol) of n-butyllithium was slowly added to a solution of a Br-substituted precursor (15 mmol) in tert-butylbenzene (150 mL) at 0 ℃, and then the temperature was raised to 25 ℃ for reaction for 1 hour. After the reaction is finished, the temperature is reduced to minus 30 ℃, boron tribromide (60 mmol) is slowly added, the temperature is increased to 60 ℃, and the stirring is continued for 2 hours. N, N-diisopropylethylamine (120 mmol) was added at room temperature and the reaction was continued at 130 ℃ for 12 hours and stopped, the solvent was dried in vacuo and passed through a silica gel column (developing solvent: dichloromethane: petroleum ether =1: 10) to give the title compound a-44 (35% yield, 99% purity by HPLC) as an orange-yellow solid. MALDI-TOF-MS results: molecular ion peaks: 760.24 elemental analysis results: theoretical values are as follows: c,85.27; h,3.84; b,1.42; n,7.37; experimental values: c,85.28; h,3.86; b,1.40; and N,7.36.
Synthetic example 10:
synthesis of Compound A-55
Under the nitrogen atmosphere, a pentane solution (60 mmol) of n-butyllithium was slowly added to a solution of a Br-substituted precursor (15 mmol) in tert-butylbenzene (150 mL) at 0 ℃, and then the temperature was raised to 25 ℃ for reaction for 1 hour. After the reaction is finished, the temperature is reduced to-30 ℃, boron tribromide (60 mmol) is slowly added, the temperature is increased to 60 ℃, and the stirring is continued for 2 hours. N, N-diisopropylethylamine (120 mmol) was added at room temperature and the reaction was continued at 130 ℃ for 12 hours. After 6 hours of reaction by adding a tetrahydrofuran solution (60 mmol) of phenylmagnesium bromide at room temperature, the solvent was stopped from being spin-dried in vacuo and passed through a silica gel column (developing solvent: dichloromethane: petroleum ether =1 10) to obtain the objective compound a-55 (33% yield, 99% purity by HPLC) as an orange-yellow solid. MALDI-TOF-MS results: molecular ion peaks: 758.25 elemental analysis results: theoretical value: c,88.66; h,4.12; b,1.42; n,3.69; experimental values: c,88.65; h,4.14; b,1.41; and N,3.66.
Synthetic example 11:
synthesis of Compound A-65
Under the nitrogen atmosphere, a pentane solution (60 mmol) of n-butyllithium was slowly added to a solution of a Br-substituted precursor (15 mmol) in tert-butylbenzene (150 mL) at 0 ℃, and then the temperature was raised to 25 ℃ for reaction for 1 hour. After the reaction is finished, the temperature is reduced to-30 ℃, boron tribromide (60 mmol) is slowly added, the temperature is increased to 60 ℃, and the stirring is continued for 2 hours. N, N-diisopropylethylamine (120 mmol) was added at room temperature and the reaction was continued at 130 ℃ for 12 hours and stopped, the solvent was dried in vacuo and passed through a silica gel column (developing solvent: dichloromethane: petroleum ether =1: 10) to give the title compound a-65 (35% yield, 99% purity by HPLC) as an orange-yellow solid. MALDI-TOF-MS results: molecular ion peaks: 582.19 elemental analysis results: theoretical values are as follows: c,86.61; h,3.98; b,1.86; n,4.81; experimental values: c,86.65; h,4.01; b,1.86; and N,4.84.
Synthetic example 12:
synthesis of Compound A-70
Under the nitrogen atmosphere, a pentane solution (60 mmol) of n-butyllithium was slowly added to a solution of a Br-substituted precursor (15 mmol) in tert-butylbenzene (150 mL) at 0 ℃, and then the temperature was raised to 25 ℃ for reaction for 1 hour. After the reaction is finished, the temperature is reduced to-30 ℃, boron tribromide (60 mmol) is slowly added, the temperature is increased to 60 ℃, and the stirring is continued for 2 hours. N, N-diisopropylethylamine (120 mmol) was added at room temperature and the reaction was continued at 130 ℃ for 12 hours and then stopped, the solvent was dried by spinning in vacuo and passed through a silica gel column (developing solvent: dichloromethane: petroleum ether =1 10) to obtain the target compound a-70 (33% yield, HPLC analytical purity 99%) as an orange-yellow solid. MALDI-TOF-MS results: molecular ion peaks: 668.39 elemental analysis results: theoretical value: 84.42; h,7.39; b,1.62; n,4.19; experimental values: 84.44; h,7.35; b,1.60; n,4.21.
Synthetic example 13:
synthesis of Compound A-80
Under the nitrogen atmosphere, a pentane solution (60 mmol) of n-butyllithium was slowly added to a solution of a Br-substituted precursor (15 mmol) in tert-butylbenzene (150 mL) at 0 ℃, and then the temperature was raised to 25 ℃ for reaction for 1 hour. After the reaction is finished, the temperature is reduced to minus 30 ℃, boron tribromide (60 mmol) is slowly added, the temperature is increased to 60 ℃, and the stirring is continued for 2 hours. N, N-diisopropylethylamine (120 mmol) was added at room temperature and the reaction was continued at 130 ℃ for 12 hours and stopped, the solvent was dried in vacuo and passed through a silica gel column (developing solvent: dichloromethane: petroleum ether =1: 10) to give the target compound a-80 (35% yield, 99% HPLC assay purity) as an orange-yellow solid. MALDI-TOF-MS results: molecular ion peaks: 462.12 elemental analysis results: theoretical value: c,77.95; h,3.27; b,2.34; n,6.06; experimental values: c,77.98; h,3.26; b,2.32; and N,6.05.
Synthesis example 14:
synthesis of Compound A-81
Under a nitrogen atmosphere, a pentane solution of n-butyllithium (60 mmol) was slowly added to a solution of Br precursor (15 mmol) in t-butylbenzene (150 mL) at 0 deg.C, and then the temperature was raised to 25 deg.C for reaction for 1 hour. After the reaction is finished, the temperature is reduced to minus 30 ℃, boron tribromide (60 mmol) is slowly added, the temperature is increased to 60 ℃, and the stirring is continued for 2 hours. N, N-diisopropylethylamine (120 mmol) was added at room temperature, and the reaction was continued at 130 ℃ for 12 hours and then stopped, and the solvent was dried in vacuo and passed through a silica gel column (developing solvent: dichloromethane: petroleum ether =1: 10) to give the target compound a-81 (30% yield, HPLC assay purity 99%) as an orange-yellow solid. MALDI-TOF-MS results: molecular ion peaks: 494.07 elemental analysis results: theoretical value: c,72.88; h,3.06; b,2.19; n,5.67; s,12.97 experimental values: c,72.87; h,3.08; b,2.21; n,5.66; and S,12.99.
Synthetic example 15:
synthesis of Compound A-82
Under the nitrogen atmosphere, a pentane solution (60 mmol) of n-butyllithium was slowly added to a solution of a Br-substituted precursor (15 mmol) in tert-butylbenzene (150 mL) at 0 ℃, and then the temperature was raised to 25 ℃ for reaction for 1 hour. After the reaction is finished, the temperature is reduced to minus 30 ℃, boron tribromide (60 mmol) is slowly added, the temperature is increased to 60 ℃, and the stirring is continued for 2 hours. N, N-diisopropylethylamine (120 mmol) was added at room temperature and the reaction was continued at 130 ℃ for 12 hours and stopped, the solvent was dried in vacuo and passed through a silica gel column (developing solvent: dichloromethane: petroleum ether =1: 10) to give the title compound a-82 (25% yield, 99% purity by HPLC) as an orange-yellow solid. MALDI-TOF-MS results: molecular ion peaks: 589.96 elemental analysis results: theoretical value: c,61.26; h,2.57; b,1.84; n,4.76; se,26.85 experimental value: c,61.25; h,2.55; b,1.85; n,4.73; se,26.89.
Synthetic example 16:
synthesis of Compound A-85
Under the nitrogen atmosphere, a pentane solution (60 mmol) of n-butyllithium was slowly added to a solution of a Br-substituted precursor (15 mmol) in tert-butylbenzene (150 mL) at 0 ℃, and then the temperature was raised to 25 ℃ for reaction for 1 hour. After the reaction is finished, the temperature is reduced to-30 ℃, boron tribromide (60 mmol) is slowly added, the temperature is increased to 60 ℃, and the stirring is continued for 2 hours. N, N-diisopropylethylamine (120 mmol) was added at room temperature and the reaction was continued at 130 ℃ for 12 hours and stopped, the solvent was dried in vacuo and passed through a silica gel column (developing solvent: dichloromethane: petroleum ether =1: 10) to give the target compound a-85 (31% yield, 99% purity by HPLC) as an orange-yellow solid. MALDI-TOF-MS results: molecular ion peaks: 794.24 elemental analysis results: theoretical values are as follows: c,81.60; h,4.44; b,1.36; n,3.52; si,7.07; experimental values: c,81.55; h,4.46; b,1.37; n,3.50; si,7.10.
Synthetic example 17:
synthesis of Compound A-87
Under the nitrogen atmosphere, a pentane solution (60 mmol) of n-butyllithium was slowly added to a solution of a Br-substituted precursor (15 mmol) in tert-butylbenzene (150 mL) at 0 ℃, and then the temperature was raised to 25 ℃ for reaction for 1 hour. After the reaction is finished, the temperature is reduced to minus 30 ℃, boron tribromide (60 mmol) is slowly added, the temperature is increased to 60 ℃, and the stirring is continued for 2 hours. N, N-diisopropylethylamine (120 mmol) was added at room temperature and the reaction was continued at 130 ℃ for 12 hours and stopped, the solvent was dried in vacuo and passed through a silica gel column (developing solvent: dichloromethane: petroleum ether =1, 10) to give the target compound a-87 (34% yield, HPLC assay purity 99%) as an orange solid. MALDI-TOF-MS results: molecular ion peaks: 466.12 elemental analysis results: theoretical value: c,80.74; h,3.39; b,2.42; n,6.28; experimental values: c,80.77; h,3.38; b,2.40; and N,6.29.
Synthetic example 18:
synthesis of Compound A-94
Under the nitrogen atmosphere, a pentane solution (60 mmol) of n-butyllithium was slowly added to a solution of a Br-substituted precursor (15 mmol) in tert-butylbenzene (150 mL) at 0 ℃, and then the temperature was raised to 25 ℃ for reaction for 1 hour. After the reaction is finished, the temperature is reduced to-30 ℃, boron tribromide (60 mmol) is slowly added, the temperature is increased to 60 ℃, and the stirring is continued for 2 hours. N, N-diisopropylethylamine (120 mmol) was added at room temperature and the reaction was continued at 130 ℃ for 12 hours and stopped, the solvent was dried in vacuo and passed through a silica gel column (developing solvent: dichloromethane: petroleum ether =1: 10) to give the target compound a-87 (34% yield, 99% HPLC assay purity) as an orange-yellow solid. MALDI-TOF-MS results: molecular ion peaks: 610.17 elemental analysis results: theoretical values are as follows: c,82.62; h,3.80; b,1.77; n,4.59; si,4.60 experimental value: c,82.60; h,3.82; b,1.80; n,4.55; si,4.62.
Synthetic example 19:
synthesis of Compound A-155
Under the nitrogen atmosphere, a pentane solution (60 mmol) of n-butyllithium was slowly added to a solution of a Br-substituted precursor (15 mmol) in tert-butylbenzene (150 mL) at 0 ℃, and then the temperature was raised to 25 ℃ for reaction for 1 hour. After the reaction is finished, the temperature is reduced to-30 ℃, boron tribromide (60 mmol) is slowly added, the temperature is increased to 60 ℃, and the stirring is continued for 2 hours. N, N-diisopropylethylamine (120 mmol) was added at room temperature and the reaction was continued at 130 ℃ for 12 hours and stopped, the solvent was dried in vacuo and passed through a silica gel column (developing solvent: dichloromethane: petroleum ether =1: 10) to give the title compound a-155 (32% yield, 99% HPLC assay purity) as an orange-yellow solid. MALDI-TOF-MS results: molecular ion peaks: 536.12 elemental analysis results: theoretical value: c,80.61; h,3.19; b,2.02; n,5.22; s,5.98 experimental values: c,80.60; h,3.15; b,2.04; n,5.23; and S,6.03.
Synthesis example 20:
synthesis of Compound A-179
Under the nitrogen atmosphere, a pentane solution (60 mmol) of n-butyllithium was slowly added to a solution of a Br-substituted precursor (15 mmol) in tert-butylbenzene (150 mL) at 0 ℃, and then the temperature was raised to 25 ℃ for reaction for 1 hour. After the reaction is finished, the temperature is reduced to minus 30 ℃, boron tribromide (60 mmol) is slowly added, the temperature is increased to 60 ℃, and the stirring is continued for 2 hours. N, N-diisopropylethylamine (120 mmol) was added at room temperature and the reaction was continued at 130 ℃ for 12 hours and then stopped, the solvent was dried in vacuo and passed through a silica gel column (developing solvent: dichloromethane: petroleum ether =1 10) to give the target compound a-179 (28% yield, HPLC assay purity 99%) as an orange-yellow solid. MALDI-TOF-MS results: molecular ion peaks: 694.30 elemental analysis results: theoretical value C,84.72; h,5.37; b,1.56; n,6.05 experimental values: c,84.74; h,5.38; b,1.52; and N,6.06.
Synthetic example 21:
synthesis of Compound A-180
Under the nitrogen atmosphere, a pentane solution (60 mmol) of n-butyllithium was slowly added to a solution of a Br-substituted precursor (15 mmol) in tert-butylbenzene (150 mL) at 0 ℃, and then the temperature was raised to 25 ℃ for reaction for 1 hour. After the reaction is finished, the temperature is reduced to minus 30 ℃, boron tribromide (60 mmol) is slowly added, the temperature is increased to 60 ℃, and the stirring is continued for 2 hours. N, N-diisopropylethylamine (120 mmol) was added at room temperature and the reaction was continued at 130 ℃ for 12 hours and then stopped, the solvent was dried by spinning in vacuo and passed through a silica gel column (developing solvent: dichloromethane: petroleum ether =1 10) to obtain the target compound a-180 (34% yield, HPLC analytical purity 99%) as an orange-yellow solid. MALDI-TOF-MS results: molecular ion peaks: 694.30 elemental analysis results: theoretical value C,84.72; h,5.37; b,1.56; n,6.05; experimental values: c,84.73; h,5.38; b,1.57; and N,6.01.
Synthesis example 22:
synthesis of Compound A-181
Under a nitrogen atmosphere, a pentane solution of n-butyllithium (60 mmol) was slowly added to a solution of Br precursor (15 mmol) in t-butylbenzene (150 mL) at 0 deg.C, and then the temperature was raised to 25 deg.C for reaction for 1 hour. After the reaction is finished, the temperature is reduced to minus 30 ℃, boron tribromide (60 mmol) is slowly added, the temperature is increased to 60 ℃, and the stirring is continued for 2 hours. N, N-diisopropylethylamine (120 mmol) was added at room temperature and the reaction was continued at 130 ℃ for 12 hours and stopped, the solvent was dried in vacuo and passed through a silica gel column (developing solvent: dichloromethane: petroleum ether =1: 10) to give the title compound a-181 (31% yield, 99% HPLC assay purity) as an orange-yellow solid. MALDI-TOF-MS results: molecular ion peaks: 694.30 elemental analysis results: theoretical value C,84.72; h,5.37; b,1.56; n,6.05; experimental values: c,84.70; h,5.35; b,1.58; and N,6.07.
Synthetic example 23:
synthesis of Compound A-182
Under the nitrogen atmosphere, a pentane solution (60 mmol) of n-butyllithium was slowly added to a solution of a Br-substituted precursor (15 mmol) in tert-butylbenzene (150 mL) at 0 ℃, and then the temperature was raised to 25 ℃ for reaction for 1 hour. After the reaction is finished, the temperature is reduced to minus 30 ℃, boron tribromide (60 mmol) is slowly added, the temperature is increased to 60 ℃, and the stirring is continued for 2 hours. N, N-diisopropylethylamine (120 mmol) was added at room temperature and the reaction was continued at 130 ℃ for 12 hours and stopped, the solvent was dried in vacuo and passed through a silica gel column (developing solvent: dichloromethane: petroleum ether =1: 10) to give the target compound a-182 (32% yield, 99% HPLC assay purity) as an orange-yellow solid. MALDI-TOF-MS results: molecular ion peaks: 694.30 elemental analysis results: theoretical value C,84.72; h,5.37; b,1.56; n,6.05; experimental values: c,84.74; h,5.38; b,1.53; and N,6.04.
Synthetic example 24:
synthesis of Compound A-183
Under the nitrogen atmosphere, a pentane solution (60 mmol) of n-butyllithium was slowly added to a solution of a Br-substituted precursor (15 mmol) in tert-butylbenzene (150 mL) at 0 ℃, and then the temperature was raised to 25 ℃ for reaction for 1 hour. After the reaction is finished, the temperature is reduced to minus 30 ℃, boron tribromide (60 mmol) is slowly added, the temperature is increased to 60 ℃, and the stirring is continued for 2 hours. N, N-diisopropylethylamine (120 mmol) was added at room temperature and the reaction was continued at 130 ℃ for 12 hours and stopped, the solvent was dried in vacuo and passed through a silica gel column (developing solvent: dichloromethane: petroleum ether =1: 10) to give the target compound a-183 (29% yield, 99% HPLC assay purity) as an orange-yellow solid. MALDI-TOF-MS results: molecular ion peaks: 694.30 elemental analysis results: theoretical value C,84.72; h,5.37; b,1.56; n,6.05; experimental values: c,84.70; h,5.40; b,1.54; and N,6.05.
Synthetic example 25:
synthesis of Compound A-184
Under the nitrogen atmosphere, a pentane solution (60 mmol) of n-butyllithium was slowly added to a solution of a Br-substituted precursor (15 mmol) in tert-butylbenzene (150 mL) at 0 ℃, and then the temperature was raised to 25 ℃ for reaction for 1 hour. After the reaction is finished, the temperature is reduced to minus 30 ℃, boron tribromide (60 mmol) is slowly added, the temperature is increased to 60 ℃, and the stirring is continued for 2 hours. N, N-diisopropylethylamine (120 mmol) was added at room temperature and the reaction was continued at 130 ℃ for 12 hours and then stopped, the solvent was dried by spinning in vacuo and passed through a silica gel column (developing solvent: dichloromethane: petroleum ether =1 10) to give the target compound a-184 (37% yield, HPLC analytical purity 99%) as an orange-yellow solid. MALDI-TOF-MS results: molecular ion peaks: 694.30 elemental analysis results: theoretical value C,84.72; h,5.37; b,1.56; n,6.05; experimental values: c,84.74; h,5.35; b,1.54; and N,6.08.
Synthetic example 26:
synthesis of Compound A-185
Under the nitrogen atmosphere, a pentane solution (60 mmol) of n-butyllithium was slowly added to a solution of a Br-substituted precursor (15 mmol) in tert-butylbenzene (150 mL) at 0 ℃, and then the temperature was raised to 25 ℃ for reaction for 1 hour. After the reaction is finished, the temperature is reduced to minus 30 ℃, boron tribromide (60 mmol) is slowly added, the temperature is increased to 60 ℃, and the stirring is continued for 2 hours. N, N-diisopropylethylamine (120 mmol) was added at room temperature and the reaction was continued at 130 ℃ for 12 hours and then stopped, the solvent was dried by vacuum, and the mixture was passed through a silica gel column (developing solvent: dichloromethane: petroleum ether =1 10) to obtain the target compound a-185 (30% yield, HPLC analytical purity 99%) as an orange-yellow solid. MALDI-TOF-MS results: molecular ion peaks: 694.30 elemental analysis results: theoretical value C,84.72; h,5.37; b,1.56; n,6.05; experimental values: c,84.71; h,5.40; b,1.59; and N,6.03.
Synthesis example 27:
synthesis of Compound A-186
Under the nitrogen atmosphere, a pentane solution (60 mmol) of n-butyllithium was slowly added to a solution of a Br-substituted precursor (15 mmol) in tert-butylbenzene (150 mL) at 0 ℃, and then the temperature was raised to 25 ℃ for reaction for 1 hour. After the reaction is finished, the temperature is reduced to-30 ℃, boron tribromide (60 mmol) is slowly added, the temperature is increased to 60 ℃, and the stirring is continued for 2 hours. N, N-diisopropylethylamine (120 mmol) was added at room temperature and the reaction was continued at 130 ℃ for 12 hours and stopped, the solvent was dried in vacuo and passed through a silica gel column (developing solvent: dichloromethane: petroleum ether =1: 10) to give the title compound a-186 (33% yield, 99% HPLC assay purity) as an orange-yellow solid. MALDI-TOF-MS results: molecular ion peaks: 694.30 elemental analysis results: theoretical value C,84.72; h,5.37; b,1.56; n,6.05; experimental values: c,84.70; h,5.38; b,1.54; and N,6.04.
Synthetic example 28:
synthesis of Compound B-4
Under a nitrogen atmosphere, a pentane solution of n-butyllithium (60 mmol) was slowly added to a solution of Br precursor (15 mmol) in t-butylbenzene (150 mL) at 0 deg.C, and then the temperature was raised to 25 deg.C for reaction for 1 hour. After the reaction is finished, the temperature is reduced to minus 30 ℃, boron tribromide (60 mmol) is slowly added, the temperature is increased to 60 ℃, and the stirring is continued for 2 hours. N, N-diisopropylethylamine (120 mmol) was added at room temperature and the reaction was continued at 130 ℃ for 12 hours and then stopped, the solvent was dried by spinning in vacuo and passed through a silica gel column (developing solvent: dichloromethane: petroleum ether =1 10) to give the target compound B-4 (33% yield, HPLC analytical purity 99%) as an orange-yellow solid. MALDI-TOF-MS results: molecular ion peaks: 638.38 elemental analysis results: theoretical value C,86.50; h,7.42; b,1.69; n,4.39; experimental values: c,86.52; h,7.45; b,1.68; n,4.34.
Synthetic example 29:
synthesis of Compound B-57
Under the nitrogen atmosphere, a pentane solution (60 mmol) of n-butyllithium was slowly added to a solution of a Br-substituted precursor (15 mmol) in tert-butylbenzene (150 mL) at 0 ℃, and then the temperature was raised to 25 ℃ for reaction for 1 hour. After the reaction is finished, the temperature is reduced to-30 ℃, boron tribromide (60 mmol) is slowly added, the temperature is increased to 60 ℃, and the stirring is continued for 2 hours. N, N-diisopropylethylamine (120 mmol) was added at room temperature and the reaction was continued at 130 ℃ for 12 hours and stopped, the solvent was dried in vacuo and passed through a silica gel column (developing solvent: dichloromethane: petroleum ether =1: 10) to give the target compound B-57 (32% yield, 99% HPLC assay purity) as an orange-yellow solid. MALDI-TOF-MS results: molecular ion peaks: 583.22 elemental analysis results: theoretical value C,86.45; h,4.49; b,1.85; n,7.20 experimental values: c,86.47; h,4.45; b,1.86; and N,7.18.
Synthetic example 30:
synthesis of Compound C-4
Under the nitrogen atmosphere, a pentane solution (60 mmol) of n-butyllithium was slowly added to a solution of a Br-substituted precursor (15 mmol) in tert-butylbenzene (150 mL) at 0 ℃, and then the temperature was raised to 25 ℃ for reaction for 1 hour. After the reaction is finished, the temperature is reduced to minus 30 ℃, boron tribromide (60 mmol) is slowly added, the temperature is increased to 60 ℃, and the stirring is continued for 2 hours. N, N-diisopropylethylamine (120 mmol) was added at room temperature and the reaction was continued at 130 ℃ for 12 hours and stopped, the solvent was dried in vacuo and passed through a silica gel column (developing solvent: dichloromethane: petroleum ether =1: 10) to give the target compound C-4 (30% yield, HPLC assay purity 99%) as an orange-yellow solid. MALDI-TOF-MS results: molecular ion peaks: 788.44 elemental analysis results: theoretical value C,83.74; h,7.41; b,1.37; n,3.55; p,3.93; experimental values: c,83.70; h,7.45; b,1.36; n,3.58; p,3.88.
Synthetic example 31:
synthesis of Compound D-4
Under a nitrogen atmosphere, a pentane solution of n-butyllithium (60 mmol) was slowly added to a solution of Br precursor (15 mmol) in t-butylbenzene (150 mL) at 0 deg.C, and then the temperature was raised to 25 deg.C for reaction for 1 hour. After the reaction is finished, the temperature is reduced to minus 30 ℃, boron tribromide (60 mmol) is slowly added, the temperature is increased to 60 ℃, and the stirring is continued for 2 hours. N, N-diisopropylethylamine (120 mmol) was added at room temperature and the reaction was continued at 130 ℃ for 12 hours and stopped, the solvent was dried in vacuo and passed through a silica gel column (developing solvent: dichloromethane: petroleum ether =1: 10) to give the target compound D-4 (34% yield, HPLC assay purity 99%) as an orange-yellow solid. MALDI-TOF-MS results: molecular ion peaks: 670.36 elemental analysis results: theoretical value C,82.37; h,7.06; b,1.61; n,4.18; s,4.78; experimental values: c,82.32; h,7.05; b,1.63; n,4.14; and S,4.81.
Synthetic example 32:
synthesis of Compound E-4
Under a nitrogen atmosphere, a pentane solution of n-butyllithium (60 mmol) was slowly added to a solution of Br precursor (15 mmol) in t-butylbenzene (150 mL) at 0 deg.C, and then the temperature was raised to 25 deg.C for reaction for 1 hour. After the reaction is finished, the temperature is reduced to minus 30 ℃, boron tribromide (60 mmol) is slowly added, the temperature is increased to 60 ℃, and the stirring is continued for 2 hours. N, N-diisopropylethylamine (120 mmol) was added at room temperature and the reaction was continued at 130 ℃ for 12 hours and stopped, the solvent was dried in vacuo and passed through a silica gel column (developing solvent: dichloromethane: petroleum ether =1: 10) to give the title compound E-4 (33% yield, 99% purity by HPLC) as an orange-yellow solid. MALDI-TOF-MS results: molecular ion peaks: 718.30 elemental analysis results: theoretical value C,76.99; h,6.60; b,1.51; n,3.90; se,11.00; experimental values: c,7.02; h,6.57; b,1.54; n,3.88; se,11.05.
Synthetic example 33:
synthesis of Compound F-4
Under the nitrogen atmosphere, a pentane solution (60 mmol) of n-butyllithium was slowly added to a solution of a Br-substituted precursor (15 mmol) in tert-butylbenzene (150 mL) at 0 ℃, and then the temperature was raised to 25 ℃ for reaction for 1 hour. After the reaction is finished, the temperature is reduced to minus 30 ℃, boron tribromide (60 mmol) is slowly added, the temperature is increased to 60 ℃, and the stirring is continued for 2 hours. N, N-diisopropylethylamine (120 mmol) was added at room temperature and the reaction was continued at 130 ℃ for 12 hours and then stopped, the solvent was dried in vacuo and passed through a silica gel column (developing solvent: dichloromethane: petroleum ether =1 10) to give the target compound F-4 (37% yield, HPLC analytical purity 99%) as an orange-yellow solid. MALDI-TOF-MS results: molecular ion peaks: 729.43 elemental analysis results: theoretical value C,85.58; h,7.18; b,1.48; n,5.76; experimental values: c,85.66; h,7.14; b,1.52; n,5.71.
Synthesis example 34:
synthesis of Compound G-4
Under a nitrogen atmosphere, a pentane solution of n-butyllithium (60 mmol) was slowly added to a solution of Br precursor (15 mmol) in t-butylbenzene (150 mL) at 0 deg.C, and then the temperature was raised to 25 deg.C for reaction for 1 hour. After the reaction is finished, the temperature is reduced to minus 30 ℃, boron tribromide (60 mmol) is slowly added, the temperature is increased to 60 ℃, and the stirring is continued for 2 hours. N, N-diisopropylethylamine (120 mmol) was added at room temperature, and the reaction was continued at 130 ℃ for 12 hours and then stopped, and the solvent was dried in vacuo and passed through a silica gel column (developing solvent: dichloromethane: petroleum ether =1: 10) to give the target compound G-4 (37% yield, HPLC assay purity 99%) as a yellow solid. MALDI-TOF-MS results: molecular ion peaks: 804.46 elemental analysis results: theoretical value C,88.04; h,7.14; b,1.34; n,3.48; experimental values: c,88.05; h,7.16; b,1.36; n,3.44.
Synthetic example 35:
synthesis of Compound H-4
Under a nitrogen atmosphere, a pentane solution of n-butyllithium (60 mmol) was slowly added to a solution of Br precursor (15 mmol) in t-butylbenzene (150 mL) at 0 deg.C, and then the temperature was raised to 25 deg.C for reaction for 1 hour. After the reaction is finished, the temperature is reduced to minus 30 ℃, boron tribromide (60 mmol) is slowly added, the temperature is increased to 60 ℃, and the stirring is continued for 2 hours. N, N-diisopropylethylamine (120 mmol) was added at room temperature and the reaction was continued at 130 ℃ for 12 hours and stopped, the solvent was dried in vacuo and passed through a silica gel column (developing solvent: dichloromethane: petroleum ether =1: 10) to give the title compound H-4 (38% yield, 99% purity by HPLC) as a yellow solid. MALDI-TOF-MS results: molecular ion peaks: 820.44 elemental analysis results: theoretical value C,84.85; h,7.00; b,1.32; n,3.41; si,3.42; experimental value C,84.82; h,7.02; b,1.33; n,3.40; si,3.44.
Synthetic example 36:
synthesis of Compound D-162
Under the nitrogen atmosphere, a pentane solution (60 mmol) of n-butyllithium was slowly added to a solution of a Br-substituted precursor (15 mmol) in tert-butylbenzene (150 mL) at 0 ℃, and then the temperature was raised to 25 ℃ for reaction for 1 hour. After the reaction is finished, the temperature is reduced to minus 30 ℃, boron tribromide (60 mmol) is slowly added, the temperature is increased to 60 ℃, and the stirring is continued for 2 hours. N, N-diisopropylethylamine (120 mmol) was added at room temperature and the reaction was continued at 130 ℃ for 12 hours and stopped, the solvent was dried in vacuo and passed through a silica gel column (developing solvent: dichloromethane: petroleum ether =1: 10) to give the title compound D-162 (35% yield, 99% purity by HPLC) as an orange-yellow solid. MALDI-TOF-MS results: molecular ion peaks: 664.22 elemental analysis results: theoretical value C,79.51; h,5.00; b,1.63; n,4.21; s,9.65; experimental values: c,79.53; h,5.02; b,1.60; n,4.20; s,9.69.
Synthetic example 37:
synthesis of Compound D-186
Under the nitrogen atmosphere, a pentane solution (60 mmol) of n-butyllithium was slowly added to a solution of a Br-substituted precursor (15 mmol) in tert-butylbenzene (150 mL) at 0 ℃, and then the temperature was raised to 25 ℃ for reaction for 1 hour. After the reaction is finished, the temperature is reduced to minus 30 ℃, boron tribromide (60 mmol) is slowly added, the temperature is increased to 60 ℃, and the stirring is continued for 2 hours. N, N-diisopropylethylamine (120 mmol) was added at room temperature and the reaction was continued at 130 ℃ for 12 hours and stopped, the solvent was dried in vacuo and passed through a silica gel column (developing solvent: dichloromethane: petroleum ether =1: 10) to give the target compound D-186 (37% yield, 99% HPLC assay purity) as an orange-yellow solid. MALDI-TOF-MS results: molecular ion peaks: 723.29 elemental analysis results: theoretical value C,82.98; h,5.29; b,1.49; n,5.81; s,4.43; experimental values: c,82.97; h,5.30; b,1.50; n,5.80; and S,4.45.
Synthetic example 38:
synthesis of Compound G-45
Under the nitrogen atmosphere, a pentane solution (60 mmol) of n-butyllithium was slowly added to a solution of a Br-substituted precursor (15 mmol) in tert-butylbenzene (150 mL) at 0 ℃, and then the temperature was raised to 25 ℃ for reaction for 1 hour. After the reaction is finished, the temperature is reduced to minus 30 ℃, boron tribromide (60 mmol) is slowly added, the temperature is increased to 60 ℃, and the stirring is continued for 2 hours. N, N-diisopropylethylamine (120 mmol) was added at room temperature, and the reaction was continued at 130 ℃ for 12 hours and then stopped, and the solvent was dried in vacuo and passed through a silica gel column (developing solvent: dichloromethane: petroleum ether =1 10) to obtain the target compound G-45 (27% yield, HPLC analytical purity 99%) as a yellow solid. MALDI-TOF-MS results: molecular ion peaks: 798.32 elemental analysis results: theoretical value C,85.70; h,5.43; b,1.35; n,3.51; s,4.01; experimental values: c,85.67; h,5.40; b,1.32; n,3.54; and S,4.07.
Synthetic example 39:
synthesis of Compound G-58
Under the nitrogen atmosphere, a pentane solution (60 mmol) of n-butyllithium was slowly added to a solution of a Br-substituted precursor (15 mmol) in tert-butylbenzene (150 mL) at 0 ℃, and then the temperature was raised to 25 ℃ for reaction for 1 hour. After the reaction is finished, the temperature is reduced to-30 ℃, boron tribromide (60 mmol) is slowly added, the temperature is increased to 60 ℃, and the stirring is continued for 2 hours. N, N-diisopropylethylamine (120 mmol) was added at room temperature, and the reaction was continued at 130 ℃ for 12 hours and then stopped, and the solvent was dried by vacuum, passed through a silica gel column (developing solvent: dichloromethane: petroleum ether =1 10) to obtain the objective compound G-58 (30% yield, HPLC analytical purity 99%) as a yellow solid. MALDI-TOF-MS results: molecular ion peaks: 857.39 elemental analysis results: theoretical value C,88.20; h,5.64; b,1.26; n,4.90; experimental values: c, C,88.20; h,5.65; b,1.25; and N,4.88.
Synthetic example 40:
synthesis of Compound G-59
Under a nitrogen atmosphere, a pentane solution of n-butyllithium (60 mmol) was slowly added to a solution of Br precursor (15 mmol) in t-butylbenzene (150 mL) at 0 deg.C, and then the temperature was raised to 25 deg.C for reaction for 1 hour. After the reaction is finished, the temperature is reduced to minus 30 ℃, boron tribromide (60 mmol) is slowly added, the temperature is increased to 60 ℃, and the stirring is continued for 2 hours. N, N-diisopropylethylamine (120 mmol) was added at room temperature, and the reaction was continued at 130 ℃ for 12 hours and then stopped, and the solvent was dried in vacuo and passed through a silica gel column (developing solvent: dichloromethane: petroleum ether =1 10) to obtain the target compound G-59 (33% yield, HPLC analytical purity 99%) as a yellow solid. MALDI-TOF-MS results: molecular ion peaks: 796.31 results of elemental analysis: theoretical value C,85.92; h,5.19; b,1.36; n,3.52; s,4.02; experimental values: c,85.95; h,5.17; b,1.35; n,3.53; s,4.00.
Synthesis example 41:
synthesis of Compound G-60
Under the nitrogen atmosphere, a pentane solution (60 mmol) of n-butyllithium was slowly added to a solution of a Br-substituted precursor (15 mmol) in tert-butylbenzene (150 mL) at 0 ℃, and then the temperature was raised to 25 ℃ for reaction for 1 hour. After the reaction is finished, the temperature is reduced to minus 30 ℃, boron tribromide (60 mmol) is slowly added, the temperature is increased to 60 ℃, and the stirring is continued for 2 hours. N, N-diisopropylethylamine (120 mmol) was added at room temperature, and the reaction was continued at 130 ℃ for 12 hours and then stopped, and the solvent was dried in vacuo and passed through a silica gel column (developing solvent: dichloromethane: petroleum ether =1: 10) to give the target compound G-60 (37% yield, HPLC assay purity 99%) as a yellow solid. MALDI-TOF-MS results: molecular ion peaks: 855.38 elemental analysis results: theoretical value C,88.41; h,5.42; b,1.26; n,4.91; experimental values: c,88.38; h,5.40; b,1.27; and N,4.95.
Synthesis example 42:
synthesis of Compound H-45
Under the nitrogen atmosphere, a pentane solution (60 mmol) of n-butyllithium was slowly added to a solution of a Br-substituted precursor (15 mmol) in tert-butylbenzene (150 mL) at 0 ℃, and then the temperature was raised to 25 ℃ for reaction for 1 hour. After the reaction is finished, the temperature is reduced to-30 ℃, boron tribromide (60 mmol) is slowly added, the temperature is increased to 60 ℃, and the stirring is continued for 2 hours. N, N-diisopropylethylamine (120 mmol) was added at room temperature, and the reaction was continued at 130 ℃ for 12 hours and then stopped, and the solvent was dried in vacuo and passed through a silica gel column (developing solvent: dichloromethane: petroleum ether =1: 10) to give the objective compound H-45 (29% yield, HPLC assay purity 99%) as a yellow solid. MALDI-TOF-MS results: molecular ion peaks: 814.30 elemental analysis results: theoretical value C,82.54; h,5.32; b,1.33; n,3.44; s,3.93; si,3.45; experimental values: c,82.55; h,5.33; b,1.31; n,3.45; s,3.95; si,3.42.
Synthetic example 43:
synthesis of Compound H-58
Under the nitrogen atmosphere, a pentane solution (60 mmol) of n-butyllithium was slowly added to a solution of a Br-substituted precursor (15 mmol) in tert-butylbenzene (150 mL) at 0 ℃, and then the temperature was raised to 25 ℃ for reaction for 1 hour. After the reaction is finished, the temperature is reduced to minus 30 ℃, boron tribromide (60 mmol) is slowly added, the temperature is increased to 60 ℃, and the stirring is continued for 2 hours. N, N-diisopropylethylamine (120 mmol) was added at room temperature, and the reaction was continued at 130 ℃ for 12 hours and then stopped, and the solvent was dried in vacuo and passed through a silica gel column (developing solvent: dichloromethane: petroleum ether =1: 10) to give the objective compound H-58 (33% yield, HPLC assay purity 99%) as a yellow solid. MALDI-TOF-MS results: molecular ion peaks: 873.37 elemental analysis results: theoretical value C,85.21; h,5.54; b,1.24; n,4.81; si,3.21; experimental values: c,85.20; h,5.57; b,1.23; n,4.82; si,3.18.
Synthetic example 44:
synthesis of Compound H-59
Under the nitrogen atmosphere, a pentane solution (60 mmol) of n-butyllithium was slowly added to a solution of a Br-substituted precursor (15 mmol) in tert-butylbenzene (150 mL) at 0 ℃, and then the temperature was raised to 25 ℃ for reaction for 1 hour. After the reaction is finished, the temperature is reduced to minus 30 ℃, boron tribromide (60 mmol) is slowly added, the temperature is increased to 60 ℃, and the stirring is continued for 2 hours. N, N-diisopropylethylamine (120 mmol) was added at room temperature, and the reaction was continued at 130 ℃ for 12 hours and then stopped, and the solvent was dried in vacuo and passed through a silica gel column (developing solvent: dichloromethane: petroleum ether =1: 10) to give the objective compound H-59 (34% yield, HPLC assay purity 99%) as a yellow solid. MALDI-TOF-MS results: molecular ion peaks: 812.29 results of elemental analysis: theoretical value C,82.74; h,5.08; b,1.33; n,3.45; s,3.94; si,3.45; experimental values: c,82.75; h,5.09; b,1.37; n,3.41; s,3.95; si,3.42.
Synthetic example 45:
synthesis of Compound H-60
Under a nitrogen atmosphere, a pentane solution of n-butyllithium (60 mmol) was slowly added to a solution of Br precursor (15 mmol) in t-butylbenzene (150 mL) at 0 deg.C, and then the temperature was raised to 25 deg.C for reaction for 1 hour. After the reaction is finished, the temperature is reduced to minus 30 ℃, boron tribromide (60 mmol) is slowly added, the temperature is increased to 60 ℃, and the stirring is continued for 2 hours. N, N-diisopropylethylamine (120 mmol) was added at room temperature, and the reaction was continued at 130 ℃ for 12 hours and then stopped, and the solvent was dried in vacuo and passed through a silica gel column (developing solvent: dichloromethane: petroleum ether =1: 10) to give the objective compound H-60 (35% yield, HPLC assay purity 99%) as a yellow solid. MALDI-TOF-MS results: molecular ion peaks: 871.36 elemental analysis results: theoretical value C,85.40; h,5.32; b,1.24; n,4.82; si,3.22; experimental values: c,85.40; h,5.33; b,1.22; n,4.80; si,3.25.
The photophysical properties of representative fused ring compounds of the present invention prepared in the above synthesis examples of the present invention are shown in Table 1.
Table 1:
note that in Table 1, the quantum efficiency is the ratio of the average number of photons generated per unit time at a specific wavelength to the number of incident photons, and the quantum efficiency is determined by mixing the compound at 10 -5 The mol/L concentration is dissolved in toluene to prepare a sample to be measured, and the sample is measured after the sample is deoxidized by nitrogen. The instrument is Edinburg FLS1000 (UK); half-peak width is the width of the peak at half of the peak height of the fluorescence spectrum at room temperature, i.e. a straight line parallel to the bottom of the peak is drawn through the midpoint of the peak height and the straight line intersects with the two points on both sides of the peak at a distance of 10 deg.C -5 The samples were prepared by dissolving the samples in toluene at a mol/L concentration and tested by means of a fluorescence spectrometer (Edinburg FLS1000 (UK)).
As can be seen from table 1, the fused ring compounds in the examples provided by the present invention have higher quantum efficiency (> 85%), while the luminescent compounds provided by the present invention exhibit narrower half-peak width (< 20 nm).
The technical effects and advantages of the invention are shown and verified by testing practical use performance by specifically applying the compound of the invention to an organic electroluminescent device.
The organic electroluminescent device includes a first electrode, a second electrode, and an organic material layer between the two electrodes. The organic material may 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.
As a material of the anode, an oxide transparent conductive material such as Indium Tin Oxide (ITO), indium Zinc Oxide (IZO), tin dioxide (SnO 2), or zinc oxide (ZnO), or any combination thereof may be used. The cathode may be made of magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any 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, and the like.
The light emitting layer includes a light emitting dye (i.e., dopant) that can emit different wavelength spectra, and may also include both a sensitizer (sensitizer) and 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.
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).
Specifically, the preparation method of the organic electroluminescent device comprises the following steps:
1. the anode material coated glass plate 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;
2. placing the glass plate with the anode in a vacuum chamber, and vacuumizing to 1 × 10 -5 ～8×10 -4 Pa, forming a hole injection layer by vacuum evaporation of a hole injection material on the anode layer film, wherein the evaporation rate is 0.1-0.5nm/s;
3. vacuum evaporating a hole transport material on the hole injection layer to form a hole transport layer, wherein the evaporation rate is 0.1-0.5nm/s;
4. an organic light-emitting layer of the device is evaporated on the hole transport layer in vacuum, the organic light-emitting layer comprises a main material, a sensitizer and dye, and the evaporation rate of the main material, the evaporation rate of the sensitizer material and the evaporation rate of the dye are adjusted by a multi-source co-evaporation method to enable the dye to reach a preset doping proportion;
5. forming an electron transport layer on the organic light-emitting layer by vacuum evaporation of an electron transport material of the device, wherein the evaporation rate is 0.1-0.5nm/s;
6. LiF is evaporated on the electron transport layer in vacuum at a speed of 0.1-0.5nm/s to serve as an electron injection layer, and an Al layer is evaporated on the electron transport layer in vacuum at a speed of 0.5-1nm/s to serve as a cathode of the device.
The embodiment of the invention also provides a display device which comprises the organic electroluminescent device provided as above. The display device can be specifically a display device such as an OLED display, and any product or component with a display function including the display device, such as a television, a digital camera, a mobile phone, a tablet computer, and the like. The display device has the same advantages as the organic electroluminescent device compared with the prior art, and the description is omitted here.
The organic electroluminescent device according to the invention is further illustrated by the following specific examples.
Device example 1
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:2wt％A-1(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30nm; host is a main body material with wide band gap of the organic light-emitting layer, the Sensitizer is a Sensitizer and has a doping concentration of 20wt%, A-1 is a dye and has a doping concentration of 2wt%, the thickness of the organic light-emitting layer is generally 1-200nm, in this embodiment 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30nm; the electron injection layer and the cathode material are selected from LiF (0.5 nm) and metallic aluminum (150 nm).
Device example 2
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:2wt％A-4(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30nm; host is a main body material with wide band gap of the organic light-emitting layer, the Sensitizer is a Sensitizer and has a doping concentration of 20wt%, A-4 is a dye and has a doping concentration of 2wt%, the thickness of the organic light-emitting layer is generally 1-200nm, in this embodiment 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30nm; the electron injection layer and the cathode material are selected from LiF (0.5 nm) and metallic aluminum (150 nm).
Device example 3
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:2wt％A-8(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein, the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30nm; host is the Host material with wide band gap of the organic light-emitting layer, sensizer is Sensitizer and has a doping concentration of 20wt%, A-8 is dye and has a doping concentration of 2wt%, the thickness of the organic light-emitting layer is generally 1-200nm, in this embodiment 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30nm; the electron injection layer and the cathode material are selected from LiF (0.5 nm) and metallic aluminum (150 nm).
Device example 4
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:2wt％A-10(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30nm; host is a main body material with wide band gap of the organic light-emitting layer, the Sensitizer is a Sensitizer and has a doping concentration of 20wt%, A-10 is a dye and has a doping concentration of 2wt%, the thickness of the organic light-emitting layer is generally 1-200nm, in this embodiment 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30nm; the electron injection layer and the cathode material are selected from LiF (0.5 nm) and metallic aluminum (150 nm).
Device example 5
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:2wt％A-13(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein, the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30nm; host is the Host material with wide band gap of the organic light-emitting layer, sensizer is Sensitizer and has a doping concentration of 20wt%, A-13 is dye and has a doping concentration of 2wt%, the thickness of the organic light-emitting layer is generally 1-200nm, in this embodiment 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30nm; the electron injection layer and the cathode material are selected from LiF (0.5 nm) and metallic aluminum (150 nm).
Device example 6
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:2wt％A-17(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein, the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30nm; host is the Host material with wide band gap of the organic light-emitting layer, sensizer is Sensitizer and has a doping concentration of 20wt%, A-17 is dye and has a doping concentration of 2wt%, the thickness of the organic light-emitting layer is generally 1-200nm, in this embodiment 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30nm; the electron injection layer and the cathode material are selected from LiF (0.5 nm) and metallic aluminum (150 nm).
Device example 7
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:2wt％A-21(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30nm; host is the Host material with wide band gap of the organic light-emitting layer, sensizer is Sensitizer and has a doping concentration of 20wt%, A-21 is dye and has a doping concentration of 2wt%, the thickness of the organic light-emitting layer is generally 1-200nm, in this embodiment 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30nm; the electron injection layer and the cathode material are selected from LiF (0.5 nm) and metallic aluminum (150 nm).
Device example 8
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:2wt％A-24(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30nm; host is the Host material with wide band gap of the organic light-emitting layer, sensizer is Sensitizer and has a doping concentration of 20wt%, A-24 is dye and has a doping concentration of 2wt%, the thickness of the organic light-emitting layer is generally 1-200nm, in this embodiment 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30nm; the electron injection layer and the cathode material are selected from LiF (0.5 nm) and metallic aluminum (150 nm).
Device example 9
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:2wt％A-44(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30nm; host is the Host material with wide band gap of the organic light-emitting layer, sensizer is Sensitizer and has a doping concentration of 20wt%, A-44 is dye and has a doping concentration of 2wt%, the thickness of the organic light-emitting layer is generally 1-200nm, in this embodiment 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30nm; the electron injection layer and the cathode material are selected from LiF (0.5 nm) and metallic aluminum (150 nm).
Device example 10
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:2wt％A-55(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30nm; host is a main body material with wide band gap of the organic light-emitting layer, the Sensitizer is a Sensitizer and has a doping concentration of 20wt%, A-55 is a dye and has a doping concentration of 2wt%, the thickness of the organic light-emitting layer is generally 1-200nm, in this embodiment 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30nm; the electron injection layer and the cathode material are selected from LiF (0.5 nm) and metallic aluminum (150 nm).
Device example 11
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:2wt％A-65(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30nm; host is the Host material with wide band gap of the organic light-emitting layer, sensizer is Sensitizer and has a doping concentration of 20wt%, A-65 is dye and has a doping concentration of 2wt%, the thickness of the organic light-emitting layer is generally 1-200nm, in this embodiment 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30nm; the electron injection layer and the cathode material are selected from LiF (0.5 nm) and metallic aluminum (150 nm).
Device example 12
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:2wt％A-70(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein, the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30nm; host is the Host material with wide band gap of the organic light-emitting layer, sensizer is Sensitizer and has a doping concentration of 20wt%, A-70 is dye and has a doping concentration of 2wt%, the thickness of the organic light-emitting layer is generally 1-200nm, in this embodiment 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30nm; the electron injection layer and the cathode material are selected from LiF (0.5 nm) and metallic aluminum (150 nm).
Device example 13
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:2wt％A-80(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein, the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30nm; host is the Host material with wide band gap of the organic light-emitting layer, sensizer is Sensitizer and has a doping concentration of 20wt%, A-80 is dye and has a doping concentration of 2wt%, the thickness of the organic light-emitting layer is generally 1-200nm, in this embodiment 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30nm; the electron injection layer and the cathode material are selected from LiF (0.5 nm) and metallic aluminum (150 nm).
Device example 14
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:2wt％A-81(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30nm; host is the Host material with wide band gap of the organic light-emitting layer, sensizer is Sensitizer and has a doping concentration of 20wt%, A-81 is dye and has a doping concentration of 2wt%, the thickness of the organic light-emitting layer is generally 1-200nm, in this embodiment 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30nm; the electron injection layer and the cathode material are selected from LiF (0.5 nm) and metallic aluminum (150 nm).
Device example 15
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:2wt％A-82(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30nm; host is the Host material with wide band gap of the organic light-emitting layer, sensizer is Sensitizer and has a doping concentration of 20wt%, A-82 is dye and has a doping concentration of 2wt%, the thickness of the organic light-emitting layer is generally 1-200nm, in this embodiment 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30nm; the electron injection layer and the cathode material are selected from LiF (0.5 nm) and metallic aluminum (150 nm).
Device example 16
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:2wt％A-85(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30nm; host is the Host material with wide band gap of the organic light-emitting layer, sensizer is Sensitizer and has a doping concentration of 20wt%, A-85 is dye and has a doping concentration of 2wt%, the thickness of the organic light-emitting layer is generally 1-200nm, in this embodiment 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30nm; the electron injection layer and the cathode material are selected from LiF (0.5 nm) and metallic aluminum (150 nm).
Device example 17
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:2wt％A-87(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein, the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30nm; host is the Host material with wide band gap of the organic light-emitting layer, sensizer is Sensitizer and has a doping concentration of 20wt%, A-87 is dye and has a doping concentration of 2wt%, the thickness of the organic light-emitting layer is generally 1-200nm, in this embodiment 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30nm; the electron injection layer and the cathode material are selected from LiF (0.5 nm) and metallic aluminum (150 nm).
Device example 18
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:2wt％A-94(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30nm; host is the Host material with wide band gap of the organic light-emitting layer, sensizer is Sensitizer and has a doping concentration of 20wt%, A-94 is dye and has a doping concentration of 2wt%, the thickness of the organic light-emitting layer is generally 1-200nm, in this embodiment 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30nm; the electron injection layer and the cathode material are selected from LiF (0.5 nm) and metallic aluminum (150 nm).
Device example 19
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:2wt％A-155(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30nm; host is the Host material with wide band gap of the organic light emitting layer, sensizer is Sensitizer and has a doping concentration of 20wt%, A-155 is dye and has a doping concentration of 2wt%, the thickness of the organic light emitting layer is generally 1-200nm, in this embodiment 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30nm; the electron injection layer and the cathode material are selected from LiF (0.5 nm) and metallic aluminum (150 nm).
Device example 20
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:2wt％A-179(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30nm; host is a Host material with wide band gap of the organic light-emitting layer, sensizer is a Sensitizer and has a doping concentration of 20wt%, A-179 is a dye and has a doping concentration of 2wt%, the thickness of the organic light-emitting layer is generally 1-200nm, in this embodiment 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30nm; the electron injection layer and the cathode material are selected from LiF (0.5 nm) and metallic aluminum (150 nm).
Device example 21
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:2wt％A-180(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein, the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30nm; host is a Host material with wide band gap of the organic light-emitting layer, sensor is Sensitizer and has a doping concentration of 20wt%, A-180 is dye and has a doping concentration of 2wt%, the thickness of the organic light-emitting layer is generally 1-200nm, in this embodiment 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30nm; the electron injection layer and the cathode material are selected from LiF (0.5 nm) and metallic aluminum (150 nm).
Device example 22
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:2wt％A-181(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30nm; host is a main body material with wide band gap of the organic light-emitting layer, the Sensitizer is a Sensitizer and has a doping concentration of 20wt%, A-181 is a dye and has a doping concentration of 2wt%, the thickness of the organic light-emitting layer is generally 1-200nm, in this embodiment 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30nm; the electron injection layer and the cathode material are selected from LiF (0.5 nm) and metallic aluminum (150 nm).
Device example 23
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:2wt％A-182(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30nm; host is the Host material with wide band gap of the organic light-emitting layer, sensizer is Sensitizer and has a doping concentration of 20wt%, A-182 is dye and has a doping concentration of 2wt%, the thickness of the organic light-emitting layer is generally 1-200nm, in this embodiment 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30nm; the electron injection layer and the cathode material are selected from LiF (0.5 nm) and metallic aluminum (150 nm).
Device example 24
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:2wt％A-183(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30nm; host is the Host material with wide band gap of the organic light-emitting layer, sensizer is Sensitizer and doping concentration is 20wt%, A-183 is dye and doping concentration is 2wt%, the thickness of the organic light-emitting layer is generally 1-200nm, in this embodiment 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30nm; the electron injection layer and the cathode material are selected from LiF (0.5 nm) and metallic aluminum (150 nm).
Device example 25
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:2wt％A-184(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30nm; host is the Host material with wide band gap of the organic light-emitting layer, sensizer is the Sensitizer and has a doping concentration of 20wt%, A-184 is the dye and has a doping concentration of 2wt%, the thickness of the organic light-emitting layer is generally 1-200nm, in this embodiment 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30nm; the electron injection layer and the cathode material are selected from LiF (0.5 nm) and metallic aluminum (150 nm).
Device example 26
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:2wt％A-185(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30nm; host is the Host material with wide band gap of the organic light-emitting layer, sensizer is Sensitizer and has a doping concentration of 20wt%, A-185 is dye and has a doping concentration of 2wt%, the thickness of the organic light-emitting layer is generally 1-200nm, in this embodiment 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30nm; the electron injection layer and the cathode material are selected from LiF (0.5 nm) and metallic aluminum (150 nm).
Device example 27
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:2wt％A-186(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein, the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30nm; host is the Host material with wide band gap of the organic light-emitting layer, sensizer is Sensitizer and has a doping concentration of 20wt%, A-186 is dye and has a doping concentration of 2wt%, the thickness of the organic light-emitting layer is generally 1-200nm, in this embodiment 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30nm; the electron injection layer and the cathode material are selected from LiF (0.5 nm) and metallic aluminum (150 nm).
Device example 28
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:2wt％B-4(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30nm; host is the Host material with wide band gap of the organic light-emitting layer, sensizer is Sensitizer and has a doping concentration of 20wt%, B-4 is dye and has a doping concentration of 2wt%, the thickness of the organic light-emitting layer is generally 1-200nm, in this embodiment 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30nm; the electron injection layer and the cathode material are selected from LiF (0.5 nm) and metallic aluminum (150 nm).
Device example 29
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:2wt％B-57(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30nm; host is the Host material with wide band gap of the organic light-emitting layer, sensizer is Sensitizer and doping concentration is 20wt%, B-57 is dye and doping concentration is 2wt%, the thickness of the organic light-emitting layer is generally 1-200nm, in this embodiment 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30nm; the electron injection layer and the cathode material are selected from LiF (0.5 nm) and metallic aluminum (150 nm).
Device example 30
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:2wt％C-4(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein, the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30nm; host is the Host material with wide band gap of the organic light emitting layer, sensizer is the Sensitizer and has a doping concentration of 20wt%, C-4 is the dye and has a doping concentration of 2wt%, the thickness of the organic light emitting layer is generally 1-200nm, in this embodiment 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30nm; the electron injection layer and the cathode material are selected from LiF (0.5 nm) and metallic aluminum (150 nm).
Device example 31
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:2wt％D-4(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30nm; host is the Host material with wide band gap of the organic light-emitting layer, sensitizer is Sensitizer and doping concentration is 20wt%, D-4 is dye and doping concentration is 2wt%, the thickness of the organic light-emitting layer is generally 1-200nm, in this embodiment 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30nm; the electron injection layer and the cathode material are selected from LiF (0.5 nm) and metallic aluminum (150 nm).
Device example 32
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:2wt％E-4(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30nm; host is the Host material with wide band gap of the organic light-emitting layer, sensizer is Sensitizer and has a doping concentration of 20wt%, E-4 is dye and has a doping concentration of 2wt%, the thickness of the organic light-emitting layer is generally 1-200nm, in this embodiment 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30nm; the electron injection layer and the cathode material are selected from LiF (0.5 nm) and metallic aluminum (150 nm).
Device example 33
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:2wt％F-4(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30nm; host is the Host material with wide band gap of the organic light-emitting layer, sensitizer is Sensitizer and doping concentration is 20wt%, F-4 is dye and doping concentration is 2wt%, the thickness of the organic light-emitting layer is generally 1-200nm, in this embodiment 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30nm; the electron injection layer and the cathode material are selected from LiF (0.5 nm) and metallic aluminum (150 nm).
Device example 34
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:2wt％G-4(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30nm; host is the Host material with wide band gap of the organic light-emitting layer, sensitizer is Sensitizer and doping concentration is 20wt%, G-4 is dye and doping concentration is 2wt%, the thickness of the organic light-emitting layer is generally 1-200nm, in this embodiment 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30nm; the electron injection layer and the cathode material are selected from LiF (0.5 nm) and metallic aluminum (150 nm).
Device example 35
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:2wt％H-4(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30nm; host is a main body material with wide band gap of the organic light-emitting layer, the Sensitizer is a Sensitizer and has a doping concentration of 20wt%, H-4 is a dye and has a doping concentration of 2wt%, the thickness of the organic light-emitting layer is generally 1-200nm, in this embodiment 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30nm; the electron injection layer and the cathode material are selected from LiF (0.5 nm) and metallic aluminum (150 nm).
Device example 36
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:2wt％D-162(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein, the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30nm; host is a Host material with wide band gap of the organic light-emitting layer, sensor is Sensitizer and has a doping concentration of 20wt%, D-162 is dye and has a doping concentration of 2wt%, the thickness of the organic light-emitting layer is generally 1-200nm, in this embodiment 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30nm; the electron injection layer and the cathode material are selected from LiF (0.5 nm) and metallic aluminum (150 nm).
Device example 37
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:2wt％D-186(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30nm; host is a Host material with wide band gap of the organic light-emitting layer, sensor is Sensitizer and has a doping concentration of 20wt%, D-186 is dye and has a doping concentration of 2wt%, the thickness of the organic light-emitting layer is generally 1-200nm, in this embodiment 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30nm; the electron injection layer and the cathode material are selected from LiF (0.5 nm) and metallic aluminum (150 nm).
Device example 38
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:2wt％G-45(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30nm; host is the Host material with wide band gap of the organic light-emitting layer, sensitizer is Sensitizer and doping concentration is 20wt%, G-45 is dye and doping concentration is 2wt%, the thickness of the organic light-emitting layer is generally 1-200nm, in this embodiment 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30nm; the electron injection layer and the cathode material are selected from LiF (0.5 nm) and metallic aluminum (150 nm).
Device example 39
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:2wt％G-58(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30nm; host is the Host material with wide band gap of the organic light-emitting layer, sensizer is Sensitizer and doping concentration is 20wt%, G-58 is dye and doping concentration is 2wt%, the thickness of the organic light-emitting layer is generally 1-200nm, in this embodiment 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30nm; the electron injection layer and the cathode material are selected from LiF (0.5 nm) and metallic aluminum (150 nm).
Device example 40
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:2wt％G-59(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30nm; host is a Host material with wide band gap of the organic light-emitting layer, sensor is Sensitizer and has a doping concentration of 20wt%, G-59 is dye and has a doping concentration of 2wt%, the thickness of the organic light-emitting layer is generally 1-200nm, in this embodiment 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30nm; the electron injection layer and the cathode material are selected from LiF (0.5 nm) and metallic aluminum (150 nm).
Device example 41
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:2wt％G-60(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30nm; host is the Host material with wide band gap of the organic light-emitting layer, sensizer is Sensitizer and has a doping concentration of 20wt%, G-60 is dye and has a doping concentration of 2wt%, the thickness of the organic light-emitting layer is generally 1-200nm, in this embodiment 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30nm; the electron injection layer and the cathode material are selected from LiF (0.5 nm) and metallic aluminum (150 nm).
Device example 42
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:2wt％H-45(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30nm; host is the Host material with wide band gap of the organic light-emitting layer, sensitizer is Sensitizer and doping concentration is 20wt%, H-45 is dye and doping concentration is 2wt%, the thickness of the organic light-emitting layer is generally 1-200nm, in this embodiment 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30nm; the electron injection layer and the cathode material are selected from LiF (0.5 nm) and metallic aluminum (150 nm).
Device example 43
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:2wt％H-58(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30nm; host is a Host material with wide band gap of the organic light-emitting layer, the Sensitizer is a Sensitizer and has a doping concentration of 20wt%, H-58 is a dye and has a doping concentration of 2wt%, the thickness of the organic light-emitting layer is generally 1-200nm, in this embodiment 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30nm; the electron injection layer and the cathode material are selected from LiF (0.5 nm) and metallic aluminum (150 nm).
Device example 44
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:2wt％H-59(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30nm; host is a Host material with wide band gap of the organic light-emitting layer, sensor is a Sensitizer with doping concentration of 20wt%, H-59 is a dye with doping concentration of 2wt%, the thickness of the organic light-emitting layer is generally 1-200nm, in this embodiment 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30nm; the electron injection layer and the cathode material are selected from LiF (0.5 nm) and metallic aluminum (150 nm).
Device example 45
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:2wt％H-60(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein, the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30nm; host is the Host material with wide band gap of the organic light-emitting layer, sensizer is Sensitizer and has a doping concentration of 20wt%, H-60 is dye and has a doping concentration of 2wt%, the thickness of the organic light-emitting layer is generally 1-200nm, in this embodiment 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30nm; the electron injection layer and the cathode material are selected from LiF (0.5 nm) and metallic aluminum (150 nm).
Comparative device example 1
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:2wt％C1(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein, the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30nm; host is the Host material with wide band gap of the organic light emitting layer, sensitizer is Sensitizer and doping concentration is 20wt%, C1 is dye and doping concentration is 2wt%, the thickness of the organic light emitting layer is generally 1-200nm, in this embodiment 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30nm; the electron injection layer and the cathode material are selected from LiF (0.5 nm) and metallic aluminum (150 nm).
Comparative device example 2
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:2wt％C2(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein, the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30nm; host is the Host material with wide band gap of the organic light emitting layer, sensitizer is Sensitizer and doping concentration is 20wt%, C2 is dye and doping concentration is 2wt%, the thickness of the organic light emitting layer is generally 1-200nm, in this embodiment 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30nm; the electron injection layer and the cathode material are selected from LiF (0.5 nm) and metallic aluminum (150 nm).
Comparative device example 3
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:2wt％C3(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30nm; host is the Host material with wide band gap of the organic light emitting layer, sensitizer is Sensitizer and doping concentration is 20wt%, C3 is dye and doping concentration is 2wt%, the thickness of the organic light emitting layer is generally 1-200nm, in this embodiment 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30nm; the electron injection layer and the cathode material are selected from LiF (0.5 nm) and metallic aluminum (150 nm).
Comparative device example 4
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(5nm)/HT(30nm)/Host:20wt％Sensitizer:2wt％C4(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein, the anode material is ITO; the hole injection layer is made of HI, and the total thickness is generally 5-30nm, in this embodiment 5nm; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, in this embodiment 30nm; host is a Host material with wide band gap of the organic light-emitting layer, sensor is Sensitizer and has a doping concentration of 20wt%, C4 is dye and has a doping concentration of 2wt%, the thickness of the organic light-emitting layer is generally 1-200nm, in this embodiment 30nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30nm; the electron injection layer and the cathode material are selected from LiF (0.5 nm) and metallic aluminum (150 nm).
The structural formulas of the various organic materials used in the above examples are as follows:
the above C1-C4 as comparative compounds are compounds in the prior art, and the synthesis methods thereof can be found in patent applications CN107851724, CN108431984, CN110407858, CN110776509, etc., and are not described herein again.
The properties of the organic electroluminescent devices prepared in the above examples and comparative examples are shown in table 2 below.
Table 2:
in the case of examples 1 to 45 and comparative examples 1 to 4, the compounds according to the present invention have a narrower electroluminescence spectrum in the case where other materials are the same in the structure of the organic electroluminescence device. Meanwhile, compared with the multiple resonance TADF dye with a nitrogen-boron-nitrogen structure in a comparative example, the compound provided by the invention has the advantages that the external quantum efficiency of a device prepared from the compound is higher, and the service life of the device is longer. The compound related to the invention forms a planar rigid skeleton structure with a central benzene ring by introducing a newly added single bond or a donor with an atom locked side, and can reduce the relaxation degree of an excited state structure, so that a target molecule has the advantages of high luminous efficiency, narrow spectral emission and high stability.
The experimental data show that the novel organic material is used as a light-emitting object of an organic electroluminescent device, is an organic light-emitting functional material with good performance, and is expected to be popularized and applied commercially.
Although the invention has been described in connection with the embodiments, the invention is not limited to the embodiments described above, and it should be understood that various modifications and improvements can be made by those skilled in the art within the spirit of the invention, and the scope of the invention is outlined by the appended claims.
It should be understood that the above examples are only for clarity of illustration and are not intended to limit the embodiments. Other variations and modifications will be apparent to persons skilled in the art in light of the above description. This need not be, nor should it be exhaustive of all embodiments. And obvious variations or modifications therefrom are within the scope of the invention.
Claims (11)
1. An organic compound having a structure represented by formula (1):
wherein:
ring Ar 1 Ring Ar 2 Ring Ar 3 And ring Ar 4 Each independently selected from C6-C60 aromatic ring or C3-C60 heteroaromatic ring;
ring Ar 3 With ring Ar 4 Are not connected with each other, or are connected through C-C single bond, or are connected through O, S or Se, or are connected through CR 7 R 8 、SiR 9 R 10 Or NR 11 Connecting;
ring Ar 1 With ring Ar 2 Are not connected with each other, or are connected through C-C single bond, or are connected through O, S or Se, or are connected through CR 7 R 8 、SiR 9 R 10 Or NR 11 Connecting;
X 1 is a single bond, O, S, se, CR 12 R 13 、SiR 14 R 15 、NR 16 Or PR 17 (ii) a m is 0 or 1;
R 1 、R 2 、R 3 、R 4 、R 5 and R 6 Each independently selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1-C30 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C2-C30 aliphatic chain hydrocarbon amino, substituted or unsubstituted C4-C30 cyclic aliphatic chain hydrocarbon amino, substituted or unsubstituted C6-C30 aryl aminoOr one of unsubstituted C3-C30 heteroaryl amido, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C60 arylboron, substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C3-C60 heteroaryl;
n1, n2, n3, n4 and n5 are each independently selected from integers from 0 to 10;
when n1, n2, n3, n4 and n5 are each independently integers greater than 1, a corresponding plurality of R 1 Between, a plurality of R 2 Between, a plurality of R 3 Between, a plurality of R 4 Between, a plurality of R 5 Each being the same or different, and a plurality of R 1 Are not connected or connected in a ring, a plurality of R 2 Are not connected or connected in a ring, a plurality of R 3 Are not connected or connected in a ring, a plurality of R 4 Are not connected or connected in a ring, a plurality of R 5 Are not connected or connected into a ring;
R 7 、R 8 、R 9 、R 10 、R 11 、R 12 、R 13 、R 14 、R 15 、R 16 and R 17 Each independently selected from one of substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C2-C30 aliphatic chain hydrocarbon amino, substituted or unsubstituted C4-C30 cyclic aliphatic chain hydrocarbon amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroaryl amino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl;
when R is as defined above 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、R 11 、R 12 、R 13 、R 14 、R 15 、R 16 And R 17 When the above substituents independently exist, the substituents are independently selected from halogen, cyano, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1One or a combination of two of alkoxy of C10, aryl amino of C6 to C30, heteroaryl amino of C3 to C30, aryloxy of C6 to C30, aryl boron group of substituted or unsubstituted C6 to C60 and heteroaryl of C3 to C30.
2. The organic compound of claim 1, m is 1, and X is 1 Is a single bond, O, S, se, CR 12 R 13 、SiR 14 R 15 、NR 16 Or PR 17 ；
The R is 12 、R 13 、R 14 、R 15 、R 16 And R 17 Each independently selected from one of C1-C6 chain alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 arylamine and substituted or unsubstituted C3-C30 heteroaryl;
preferably, said X 1 Is O, S, se, CR 12 R 13 、SiR 14 R 15 (ii) a More preferably, X is 1 Is O, S, CR 12 R 13 、SiR 14 R 15 (ii) a Most preferably, said X 1 Is S, CR 12 R 13 。
Preferably, said R is 12 、R 13 、R 14 、R 15 、R 16 And R 17 Each independently selected from any one of C1-C4 chain alkyl, substituted or unsubstituted benzene ring, naphthalene ring and anthracene ring; most preferably, said R 12 、R 13 、R 14 、R 15 、R 16 And R 17 Each independently a substituted or unsubstituted benzene ring.
3. The organic compound according to claim 1 or 2, the ring Ar 3 With ring Ar 4 Are connected through a C-C single bond, or through O, S or Se, or through CR 7 R 8 、SiR 9 R 10 Or NR 11 Connecting;
the ring Ar 1 With ring Ar 2 Are connected through a C-C single bond or through O, S or SeOr by CR 7 R 8 、SiR 9 R 10 Or NR 11 Connecting;
the R is 7 、R 8 、R 9 、R 10 、R 11 Each independently selected from one of substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C6-C30 aralkyl, substituted or unsubstituted C6-C30 arylamine, substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C3-C60 heteroaryl;
preferably, the ring Ar 3 With ring Ar 4 Are connected through a C-C single bond, or through O, S or Se, or through CR 7 R 8 、SiR 9 R 10 Connecting; still more preferably, the ring Ar 3 With ring Ar 4 Are connected through a C-C single bond, or through O or S, or through CR 7 R 8 、SiR 9 R 10 Connecting; more preferably, the ring Ar 3 With ring Ar 4 Are connected through a C-C single bond, or through S, or through CR 7 R 8 、SiR 9 R 10 Connecting; most preferably, the ring Ar 3 With ring Ar 4 Are connected through a C-C single bond;
preferably, the ring Ar 1 With ring Ar 2 Are connected through a C-C single bond, or through O, S or Se, or through CR 7 R 8 、SiR 9 R 10 Connecting; still more preferably, the ring Ar 1 With ring Ar 2 Are connected through a C-C single bond, or through O or S, or through CR 7 R 8 、SiR 9 R 10 Connecting; more preferably, the ring Ar 1 With ring Ar 2 Are connected through a C-C single bond, or through S, or through CR 7 R 8 、SiR 9 R 10 Connecting; most preferably, the ring Ar 1 With ring Ar 2 Are connected through a C-C single bond;
preferably, R 7 、R 8 、R 9 、R 10 、R 11 Each independently selected from substituted or unsubstituted C1 to C6One of a chain alkyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C6-C30 arylamine group, and a substituted or unsubstituted C3-C30 heteroaryl group.
4. The organic compound according to claim 1, having a structure of the following structural formula (1-1):
wherein R is 1 -R 6 、Ar 1 -Ar 4 And n1 to n4 are each as defined in formula (1).
5. The organic compound according to claim 1, having a structure represented by any one of the following structural formulae (1-2), (1-3), (1-4), (1-5), (1-6), (1-7), or (1-8):
wherein R is 1 -R 11 、Ar 1 -Ar 4 And n1 to n4 are each as defined in the formula (1).
6. The organic compound according to any one of claims 1 to 5, the ring Ar 1 Ring Ar 2 Ring Ar 3 Ring Ar 4 And ring Ar 5 Each independently selected from C6-C60 aromatic ring or C3-C30 heteroaromatic ring;
preferably, ring Ar 1 Ring Ar 2 Ring Ar 3 And ring Ar 4 Each independently selected from C6-C30 aromatic ring or C3-C20 heteroaromatic ring;
more preferably, ring Ar 1 Ring Ar 2 Ring Ar 3 And ring Ar 4 Each independently selected from the group consisting of benzene ring, naphthalene ring, anthracene ring, fluorene ring, furan, benzofuran, dibenzofuran, indole, benzindole,Any one of carbazole, indolocarbazole, benzothiophene, dibenzothiophene, or thiophene;
more preferably, the ring Ar 1 Ring Ar 2 Ring Ar and ring Ar 4 Each independently is any one of a benzene ring, a naphthalene ring, dibenzofuran carbazole or dibenzothiophene;
most preferably, the ring Ar 1 Ring Ar 2 Ring Ar and ring Ar 4 Each independently a benzene ring.
7. The organic compound of any one of claims 1-5, wherein n1, n2, n3, and n4 are each independently selected from an integer from 1-5;
the R is 1 、R 2 、R 3 、R 4 、R 5 、R 6 Each independently selected from the following substituents: <xnotran> , , , , , , , ,2- , , , , , , , , , , , ,2- , , ,2,2,2- , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , -5,6- , -6,7- , -7,8- , , , , , , , , , , , </xnotran>Benzoxazolyl, naphthooxazolyl, anthracenyl, phenanthrenyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyrazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1, 5-diazenanthrenyl, 2, 7-diazpyrenyl, 2, 3-diazpyrenyl, 1, 6-diazpyrenyl, 1, 8-diazpyrenyl, 4,5,9, 10-tetraazapyridyl, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, benzocaine, phenanthroline, 1,2, 3-triazolyl, 1,2, 4-triazolyl one of a benzotriazolyl group, 1,2, 3-oxadiazolyl group, 1,2, 4-oxadiazolyl group, 1,2, 5-oxadiazolyl group, 1,2, 3-thiadiazolyl group, 1,2, 4-thiadiazolyl group, 1,2, 5-thiadiazolyl group, 1,3, 4-thiadiazolyl group, 1,3, 5-triazinyl group, 1,2, 4-triazinyl group, 1,2, 3-triazinyl group, tetrazolyl group, 1,2,4, 5-tetrazinyl group, 1,2,3, 4-tetrazinyl group, 1,2,3, 5-tetrazinyl group, purinyl group, pteridinyl group, indolizinyl group, benzothiadiazolyl group, diphenylboryl group, dimyridylboronyl group, dipentafluorophenylboroyl group, bis (2, 4, 6-triisopropylphenyl) boroyl group, or a combination of two selected from the above;
preferably, said R 6 Is selected from hydrogen, said R 1 、R 2 、R 3 、R 4 、R 5 Each independently represents one of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, trifluoromethyl, pentafluoroethyl, cyano, halogen, phenyl, naphthyl, anthracenyl, fluorenyl, spirobifluorenyl, dihydrophenanthrenyl, dihydropyrenyl, tetrahydropyrenyl, cis-or trans-indenofluorenyl, furyl, benzofuryl, thienyl, benzothienyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridyl, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyrazinyl, pyrimidinyl, benzopyrimidinyl, 1,3, 5-triazinyl, diphenylboryl, dimyridylboronyl, dipentafluorophenylboryl, bis (2, 4, 6-triisopropylphenyl) boryl, or a combination selected from the two of the foregoing groups;
still more preferably, said R 6 Is selected from hydrogen, said R 1 、R 2 、R 3 、R 4 、R 5 Each independently represents one of methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, trifluoromethyl, pentafluoroethyl, cyano, halogen, phenyl, naphthyl, anthracenyl, fluorenyl, spirobifluorenyl, carbazolyl, 1,3, 5-triazinyl, diphenylboryl, dimyridylboryl, dipentafluorophenylboryl, bis (2, 4, 6-triisopropylphenyl) boryl, or a combination of two of the foregoing.
8. The organic compound of any one of claims 1-5, wherein R 7 、R 8 、R 9 、R 10 、R 11 Each independently selected from the following substituents: <xnotran> , , , , , , , ,2- , , , , , , , , , , , ,2- , , ,2,2,2- , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , -5,6- , -6,7- , -7,8- , , , , , , , , , , , , , , ,1,2- ,1,3- , </xnotran>A benzothiazolyl group, a pyridazinyl group, a benzopyridazinyl group, a pyrimidinyl group, a benzopyrimidinyl group, a quinoxalinyl group, a1, 5-diazanenthyl group, a 2, 7-diazpyrene group, a 2, 3-diazenepyrenyl group, a1, 6-diazenepyrenyl group, a1, 8-diazenepyrenyl group, a 4,5,9, 10-tetraazapyrienyl group, a pyrazinyl group, a phenazinyl group, a phenothiazinyl group, a naphthyridinyl group, an azacarbazolyl group, a benzocarbazinyl group, a phenanthrolinyl group, a1, 2, 3-triazolyl group, a1, 2, 4-triazolyl group, a phenanthridinyl group, a1, 2, 4-triazolyl group, a one of 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 selected from the above;
preferably, R 7 、R 8 、R 9 、R 10 、R 11 Each independently selected from the following substituents: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, trifluoromethyl, pentafluoroethyl, cyano, halogen, phenyl, naphthyl, anthracenyl, fluorenyl, spirobifluorenyl, dihydrophenanthrenyl, dihydropyrenyl, tetrahydropyrenyl, cis-or trans-indenofluorenyl, furyl, benzofuryl, thienyl, benzothienyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridyl, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, pyrimidinyl, benzopyrimidinyl, 1,3, 5-triazinyl, diphenylboryl, dimyridylboryl, dipentafluorophenylboryl, bis (2, 4, 6-triisopropylphenyl) boryl, or a combination selected from the two or more thereof;
further preferably, R 7 、R 8 、R 9 、R 10 、R 11 Each independently selected from the following substituents: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, phenyl, naphthyl, anthryl, fluorenyl, spirobifluorenylOr a combination of two selected from the above.
9. The compound of claim 1, selected from the compounds of the following specific structures:
10. use of a compound according to any one of claims 1 to 9 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;
further, the compound is applied to be used as a luminescent layer material in an organic electroluminescent device, and particularly used as a luminescent material in a luminescent layer.
11. 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 therein a compound according to any one of claims 1 to 9;
furthermore, the light-emitting functional layer comprises a hole transport region, a light-emitting layer and an electron transport region, wherein 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 light-emitting layer contains the compound according to any one of claims 1 to 9.
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| WO2024012365A1 (en) * | 2022-07-14 | 2024-01-18 | 清华大学 | Organic compound and use thereof |
| WO2024125653A1 (en) * | 2022-12-15 | 2024-06-20 | 华为技术有限公司 | Boron-containing resonance-type organic compound and organic electroluminescent device comprising same |
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| WO2024174813A1 (en) * | 2023-02-23 | 2024-08-29 | 清华大学 | Organic compound and use thereof |
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| WO2023190159A1 (en) * | 2022-04-01 | 2023-10-05 | 東レ株式会社 | Compound, light-emitting element material and light-emitting element obtained using same, photoelectric conversion element material, color conversion composition, color conversion sheet, light source unit, display device, and lighting device |
| WO2024012365A1 (en) * | 2022-07-14 | 2024-01-18 | 清华大学 | Organic compound and use thereof |
| WO2024125653A1 (en) * | 2022-12-15 | 2024-06-20 | 华为技术有限公司 | Boron-containing resonance-type organic compound and organic electroluminescent device comprising same |
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| WO2024174813A1 (en) * | 2023-02-23 | 2024-08-29 | 清华大学 | Organic compound and use thereof |
| CN116444547A (en) * | 2023-03-10 | 2023-07-18 | 浙江八亿时空先进材料有限公司 | Naphthalene boron-nitrogen compound and application thereof |
| CN116444547B (en) * | 2023-03-10 | 2024-02-02 | 浙江八亿时空先进材料有限公司 | Naphthalene boron-nitrogen compound and application thereof |
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