CN114685353A - Organic compound for organic light emitting device, organic electroluminescent device - Google Patents
Organic compound for organic light emitting device, organic electroluminescent device Download PDFInfo
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- CN114685353A CN114685353A CN202011583036.9A CN202011583036A CN114685353A CN 114685353 A CN114685353 A CN 114685353A CN 202011583036 A CN202011583036 A CN 202011583036A CN 114685353 A CN114685353 A CN 114685353A
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- 150000002894 organic compounds Chemical class 0.000 title claims description 22
- 150000001875 compounds Chemical class 0.000 claims abstract description 61
- 239000000463 material Substances 0.000 claims abstract description 31
- -1 nitro, hydroxyl Chemical group 0.000 claims description 85
- 239000010410 layer Substances 0.000 claims description 64
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 239000002346 layers by function Substances 0.000 claims description 7
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 6
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 3
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 2
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 2
- 125000003172 aldehyde group Chemical group 0.000 claims description 2
- 125000001769 aryl amino group Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims description 2
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 2
- 230000005284 excitation Effects 0.000 abstract description 4
- 230000000694 effects Effects 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 description 40
- 238000003786 synthesis reaction Methods 0.000 description 39
- PHKYYUQQYARDIU-UHFFFAOYSA-N 3-methyl-9h-carbazole Chemical compound C1=CC=C2C3=CC(C)=CC=C3NC2=C1 PHKYYUQQYARDIU-UHFFFAOYSA-N 0.000 description 20
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 15
- PWJYOTPKLOICJK-UHFFFAOYSA-N 3-methylcarbazole Natural products C1=CC=C2C3=CC=C(C)C=C3NC2=C1 PWJYOTPKLOICJK-UHFFFAOYSA-N 0.000 description 12
- 238000004949 mass spectrometry Methods 0.000 description 12
- 239000011368 organic material Substances 0.000 description 12
- 230000000903 blocking effect Effects 0.000 description 11
- 230000005525 hole transport Effects 0.000 description 11
- 238000002347 injection Methods 0.000 description 11
- 239000007924 injection Substances 0.000 description 11
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
- 239000000376 reactant Substances 0.000 description 10
- 239000010408 film Substances 0.000 description 9
- 239000000975 dye Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 6
- 239000002356 single layer Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 125000001624 naphthyl group Chemical group 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 239000003086 colorant Substances 0.000 description 4
- 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 4
- 230000003111 delayed effect Effects 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 230000002093 peripheral effect Effects 0.000 description 4
- 125000001725 pyrenyl group Chemical group 0.000 description 4
- 239000010409 thin film Substances 0.000 description 4
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 4
- AIFRHYZBTHREPW-UHFFFAOYSA-N β-carboline Chemical compound N1=CC=C2C3=CC=CC=C3NC2=C1 AIFRHYZBTHREPW-UHFFFAOYSA-N 0.000 description 4
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 230000005540 biological transmission Effects 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 230000002349 favourable effect Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 230000005693 optoelectronics Effects 0.000 description 3
- 229910052760 oxygen Inorganic materials 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
- 229920000767 polyaniline Polymers 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 238000002207 thermal evaporation Methods 0.000 description 3
- 125000004506 1,2,5-oxadiazolyl group Chemical group 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 2
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 2
- 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 2
- MAGFQRLKWCCTQJ-UHFFFAOYSA-M 4-ethenylbenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C(C=C)C=C1 MAGFQRLKWCCTQJ-UHFFFAOYSA-M 0.000 description 2
- BPMFPOGUJAAYHL-UHFFFAOYSA-N 9H-Pyrido[2,3-b]indole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=N1 BPMFPOGUJAAYHL-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-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
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 229910052769 Ytterbium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical group C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 125000005577 anthracene group Chemical group 0.000 description 2
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- 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 2
- 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 2
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 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 2
- 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 2
- 238000013461 design Methods 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 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
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
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- 125000002541 furyl group Chemical group 0.000 description 2
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- 125000001041 indolyl group Chemical group 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
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- 125000002950 monocyclic group Chemical group 0.000 description 2
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- 229910052757 nitrogen Inorganic materials 0.000 description 2
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- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 2
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- 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 2
- 230000001235 sensitizing effect Effects 0.000 description 2
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- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
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- 238000012546 transfer Methods 0.000 description 2
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- 125000000923 (C1-C30) alkyl 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
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical compound C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 1
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- 125000004529 1,2,3-triazinyl group Chemical group N1=NN=C(C=C1)* 0.000 description 1
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- 125000004530 1,2,4-triazinyl group Chemical group N1=NC(=NC=C1)* 0.000 description 1
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- 125000004517 1,2,5-thiadiazolyl group Chemical group 0.000 description 1
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 description 1
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- IOQMWOBRUDNEOA-UHFFFAOYSA-N 2,3,5,6-tetrafluorobenzonitrile Chemical compound FC1=CC(F)=C(F)C(C#N)=C1F IOQMWOBRUDNEOA-UHFFFAOYSA-N 0.000 description 1
- HNACKJNPFWWEKI-UHFFFAOYSA-N 3,6-dimethyl-9h-carbazole Chemical group C1=C(C)C=C2C3=CC(C)=CC=C3NC2=C1 HNACKJNPFWWEKI-UHFFFAOYSA-N 0.000 description 1
- OYFFSPILVQLRQA-UHFFFAOYSA-N 3,6-ditert-butyl-9h-carbazole Chemical group C1=C(C(C)(C)C)C=C2C3=CC(C(C)(C)C)=CC=C3NC2=C1 OYFFSPILVQLRQA-UHFFFAOYSA-N 0.000 description 1
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- VYFQVFUSFYTTAJ-UHFFFAOYSA-N 3-propan-2-yl-9h-carbazole Chemical group C1=CC=C2C3=CC(C(C)C)=CC=C3NC2=C1 VYFQVFUSFYTTAJ-UHFFFAOYSA-N 0.000 description 1
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- GNPUIRFDBYALRI-UHFFFAOYSA-N 4-methyl-9h-carbazole Chemical group N1C2=CC=CC=C2C2=C1C=CC=C2C GNPUIRFDBYALRI-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
- 239000005964 Acibenzolar-S-methyl Substances 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
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N Li2O Inorganic materials [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-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
- 230000001133 acceleration Effects 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 230000003321 amplification Effects 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-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
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 239000001045 blue dye Substances 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
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- DUEPRVBVGDRKAG-UHFFFAOYSA-N carbofuran Chemical compound CNC(=O)OC1=CC=CC2=C1OC(C)(C)C2 DUEPRVBVGDRKAG-UHFFFAOYSA-N 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 229910052729 chemical element Inorganic materials 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
- 229920001940 conductive polymer Polymers 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 150000004696 coordination complex Chemical class 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
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- XUCJHNOBJLKZNU-UHFFFAOYSA-M dilithium;hydroxide Chemical compound [Li+].[Li+].[OH-] XUCJHNOBJLKZNU-UHFFFAOYSA-M 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 239000012761 high-performance material Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
- 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 description 1
- 229960005544 indolocarbazole Drugs 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 150000002503 iridium Chemical class 0.000 description 1
- 125000005990 isobenzothienyl group Chemical group 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- 125000005244 neohexyl group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 238000013086 organic photovoltaic Methods 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 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
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 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
- 125000005592 polycycloalkyl group Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229910052711 selenium Inorganic materials 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
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 238000007725 thermal activation Methods 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention provides a compound and application thereof, wherein the compound has a structure shown in a formula (1), and when the compound is used in an organic electroluminescent device, particularly as a luminescent dye material, the compound can effectively reduce the excitation voltage of the device, improve the luminous efficiency of the device and achieve the best effect.
Description
Technical Field
The invention relates to the technical field of organic electroluminescence, in particular to an organic compound and application thereof, and also relates to an organic electroluminescent device.
Background
In recent years, optoelectronic devices based on organic materials have become increasingly popular. The inherent flexibility of organic materials makes them well suited for fabrication on flexible substrates, allowing for the design and production of aesthetically pleasing and crunchy optoelectronic products, with unparalleled advantages over inorganic materials. Examples of such organic optoelectronic devices include Organic Light Emitting Diodes (OLEDs), organic field effect transistors, organic photovoltaic cells, organic sensors, and the like. Among them, OLEDs are particularly rapidly developed and have been commercially successful in the field of information displays. The OLED can provide three colors of red, green and blue with high saturation, and a full-color display device manufactured by using the OLED does not need an additional backlight source and has the advantages of colorful, light, thin and soft color and the like.
The core of the OLED device is a thin film structure containing various organic functional materials. Common functionalized organic materials are: hole injection materials, hole transport materials, hole blocking materials, electron injection materials, electron transport materials, electron blocking materials, and light emitting host materials and light emitting objects (dyes), and the like. When electricity is applied, electrons and holes are injected, transported to the light emitting region, and recombined therein, respectively, thereby generating excitons and emitting light.
People have developed various organic materials, and the organic materials are combined with various peculiar device structures, so that the carrier mobility can be improved, the carrier balance can be regulated, the electroluminescent efficiency can be broken through, and the attenuation of the device can be delayed. For quantum mechanical reasons, common fluorescent luminophores mainly utilize singlet excitons generated when electrons and air are combined to emit light, and are still widely applied to various OLED products. Some metal complexes, such as iridium complexes, can emit light using both triplet excitons and singlet excitons, which are called phosphorescent emitters, and the energy conversion efficiency can be increased by up to four times as compared with conventional fluorescent emitters. The thermal excitation delayed fluorescence (TADF) technology can still effectively utilize triplet excitons to achieve higher luminous efficiency without using a metal complex by promoting the conversion of triplet excitons to singlet excitons. Thermal excitation sensitized fluorescence (TASF) technology also achieves higher luminous efficiency by sensitizing the emitter by energy transfer using TADF-like materials. Especially in the blue light-emitting field which is difficult to effectively improve the light-emitting efficiency, the method has very wide application prospect.
In the field of blue light emission of OLEDs, the following thermally excitable sensitizing luminescent dyes (CN110759851A) have been developed, which achieve higher luminous efficiency using triplet excitons.
However, as OLED products gradually enter the market, there are higher and higher requirements on the performance of such products, and the above-mentioned OLED materials and device structures cannot completely solve the problems of efficiency, lifetime, cost, etc. of OLED products, and there is still room for further improvement.
Disclosure of Invention
Through intensive research, researchers of the invention find a smart molecular design scheme, and obtain the luminescent dye material with better product efficiency. The compound disclosed by the invention is very suitable for being applied to an OLED (organic light emitting diode) and improving the performance of a device, and is particularly suitable for being used as a blue dye material.
Specifically, the present invention provides an organic compound characterized by having a structure represented by formula (1);
wherein:
D1、D2each independently selected from the group represented by formula (2):
X1～X8independently selected from N or CR1，R1Independently selected from hydrogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C20 silyl, substituted or unsubstitutedOne of substituted or unsubstituted C6 to C60 arylamino, substituted or unsubstituted C3 to C60 heteroarylamino, substituted or unsubstituted C6 to C60 aryl, and substituted or unsubstituted C3 to C60 heteroaryl,
D3、D4independently selected from the group represented by formula (3):
Y1～Y8independently selected from CH or N;
r is selected from one of hydrogen, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C3-C60 heteroaryl;
the substituent group is one or more groups selected from halogen, cyano, C1-C17 amino, C1-C17 carboxyl, C1-C17 aldehyde group, C1-C17 ester group, C1-C12 chain alkyl, C3-C12 cycloalkyl, C2-C10 alkenyl, C1-C10 alkoxy or thioalkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryl, and C3-C30 heteroaryl.
In the present specification, the expression of Ca to Cb represents that the group has carbon atoms a to b, and the carbon atoms do not generally include the carbon atoms of the substituents unless otherwise specified. In the present invention, unless otherwise specified, the chemical element expression generally includes the concept of the same chemical isotope, for example, the expression "hydrogen" also includes the concept of the same chemical "deuterium" or "tritium", and the carbon (C) includes12C、13C, etc., will not be described in detail.
In the structural formulae disclosed in the present specification, the expression of the "-" underlined loop structure indicates that the linking site is located at an arbitrary position on the loop structure where the linking site can form a bond.
In the present specification, unless otherwise specified, both aryl and heteroaryl groups include monocyclic and fused rings. The monocyclic aryl group means that at least one phenyl group is contained in the molecule, and when at least two phenyl groups are contained in the molecule, the phenyl groups are independent of each other and are linked by a single bond, illustratively, a phenyl group, a biphenylyl group, a terphenylyl group, or the like; 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 means that the molecule contains at least one heteroaryl group, and when the molecule contains one heteroaryl group and other groups (e.g., aryl, heteroaryl, alkyl, etc.), the heteroaryl and other groups are independent of each other and are 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 present specification, substituted or unsubstituted C6～C30Aryl is preferably C6～C20More preferably, the aryl group is a group selected from the group consisting of phenyl, naphthyl, anthracenyl, benzanthracenyl, phenanthrenyl, phenylphenanthracenyl, pyrenyl, perylenyl, anthrylenyl, tetracenyl, benzopyrenyl, biphenylyl, idophenyl, terphenyl, quaterphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthrenyl, dihydropyrenyl, tetrahydropyrenyl, cis-or trans-indenofluorenyl, trimeric indenyl, isotridecylindenyl, spirotrimeric indenyl, spiroisoindenylidene. Specifically, the biphenyl group is selected from 2-biphenyl, 3-biphenyl, and 4-biphenyl; terphenyl includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-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 1-anthracene group, 2-anthracene group and 9-anthracene group; the fluorenyl is selected from the group consisting of 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenylAnd 9-fluorenyl; the pyrenyl group is selected from 1-pyrenyl, 2-pyrenyl and 4-pyrenyl; the tetracene group is selected from the group consisting of 1-tetracene, 2-tetracene, and 9-tetracene. Preferred examples of the aryl group in the present invention include phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, indenyl, fluorenyl and derivatives thereof, anthryl, triphenylenyl, 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-terphenyl-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, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl; the fluorenyl derivative is selected from the group consisting of 9, 9-dimethylfluorene, 9-spirobifluorene and benzofluorene; the pyrenyl group is selected from a group consisting of a 1-pyrenyl group, a 2-pyrenyl group and a 4-pyrenyl group; the tetracene group is selected from the group consisting of 1-tetracene, 2-tetracene, and 9-tetracene.
The heteroatom in the present invention is generally referred to as being selected from N, O, S, P, Si and Se, preferably from N, O, S.
In the present specification, the substituted or unsubstituted C3 to C30 heteroaryl group is preferably a C4 to C20 heteroaryl group, more preferably a nitrogen-containing heteroaryl group, an oxygen-containing heteroaryl group, a sulfur-containing heteroaryl group, and the like, and specific examples thereof include: furyl, thienyl, pyrrolyl, pyridyl, benzofuryl, benzothienyl, isobenzofuryl, isobenzothienyl, indolyl, isoindolyl, dibenzofuryl, dibenzothienyl, carbazolyl and derivatives thereof, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, benzo-5, 6-quinolyl, benzo-6, 7-quinolyl, benzo-7, 8-quinolyl, phenothiazinyl, phenazinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalimidazolyl, oxazolyl, benzoxazolyl, naphthooxazolyl, anthraoxazolyl, phenanthroizolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, A benzopyridazinyl group, a pyrimidyl group, a benzopyrimidinyl group, a quinoxalinyl group, a 1, 5-diazananthracenyl group, a 2, 7-diazepanyl group, a 2, 3-diazepanyl group, a 1, 6-diazepanyl group, a 1, 8-diazepanyl group, a 4, 5, 9, 10-tetraazaperyl group, a pyrazinyl group, a phenazinyl group, a phenothiazinyl group, a naphthyridinyl group, an azacarbazolyl group, a benzocarbazinyl group, a phenanthrolinyl group, a 1, 2, 3-triazolyl group, a 1, 2, 4-triazolyl group, a benzotriazolyl group, a 1, 2, 3-oxadiazolyl group, a 1, 2, 5-oxadiazolyl group, a 1, 2, 4-oxadiazolyl group, a 1, 2, 5-oxadiazolyl group, a 1, 3, 4-thiadiazolyl group, a 1, 2, 5-thiadiazolyl group, 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, benzothiadiazole, and the like. Preferred examples of the heteroaryl group in the present invention include furyl, thienyl, pyrrolyl, benzofuryl, benzothienyl, isobenzofuryl, indolyl, dibenzofuryl, dibenzothienyl, carbazolyl and derivatives thereof, wherein the carbazolyl derivative is preferably 9-phenylcarbazole, 9-naphthylcarbazole benzocarbazole, dibenzocarbazole or indolocarbazole.
In the present specification, examples of the C1 to C30 alkyl group include: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, n-hexyl, cyclohexyl, adamantyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2, 2, 2-trifluoroethyl and the like.
In the present specification, cycloalkyl includes monocycloalkyl and polycycloalkyl, and may be, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like.
In the present specification, examples of the C1 to C30 alkoxy group include: methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, pentoxy, isopentoxy, hexoxy, heptoxy, octoxy, nonoxy, decyloxy, undecyloxy, dodecyloxy and the like, among which methoxy, ethoxy, n-propoxy, isopropoxy, tert-butoxy, sec-butoxy, isobutoxy, isopentoxy are preferred, and methoxy is more preferred.
Examples of the C1-C30 silyl group in the present specification include silyl groups substituted with the groups listed for the C1-C30 alkyl groups, and specifically include: methylsilyl, dimethylsilyl, trimethylsilyl, ethylsilyl, diethylsilyl, triethylsilyl, t-butyldimethylsilyl, t-butyldiphenylsilyl and the like.
In the present specification, examples of the halogen include: fluorine, chlorine, bromine, iodine, and the like.
In the present invention, the "substituted or unsubstituted" group may be substituted with one substituent or a plurality of substituents, and when a plurality of substituents are present, different substituents may be selected from the group.
Of great importance in the present invention is D mentioned above3、D4Independently selected from the group represented by formula (3), i.e. D3、D4Is an unsubstituted carbazole or an unsubstituted N-hybrid carbazole. The inventors have found that if such a group is selected, the luminous efficiency can be increased and the excitation voltage can be decreased accordingly. The specific reason why these compounds can further achieve excellent technical effects is not clear, and the following is the presumption of the inventors: when the cyano meta-position adopts a carbazole structure without peripheral substituent groups, the conformation of molecules is more favorable for accumulating a state with high carrier transmission performance during film forming, so that the corresponding transmission efficiency is improved, and the voltage is reduced. If D is3、D4If the substituent is present, film formation may be disadvantageous for charge transport due to steric hindrance. The above reasons are only presumed, but these are only presumedIt is not presumed that the scope of the present invention is limited.
D is preferably used from the viewpoint of ease of synthesis and further excellent photoelectric properties3And D4Are the same group.
D of great importance in the invention3、D4Preferably, the carbazole groups are all selected, but the carbazole groups may be replaced by 1-2N hybrids, i.e., wherein Y is1～Y8All are CH, or 1 or 2 of them are N, and the rest are all CH. Further preferably, Y is1～Y41 or 2 of N and the remainder are CH, where Y is5～Y81 or 2 of them are N and the rest are CH. An excessive amount of N-hybridized product may cause D3、D4The electron-withdrawing ability of the compound is too strong, which is not beneficial to improving the electron cloud density of the benzonitrile mother nucleus and damaging the carrier transport property.
In general, D3、D4Preferably selected from the group consisting of:
more preferred are the following groups:
d of great importance in the invention1、D2X in the formula (2)1～X8Independently selected from N, CH, CR1’Or CR2As R therein1’Groups that allow a slight increase in the electron cloud on the carbazole group and provide suitable steric hindrance are preferred.
Such groups are, as exemplified above, substituted or unsubstituted C4-C20 alkyl groups, substituted or unsubstituted C1-C20 alkoxy groups, amino and substituted amino groups, and substituted or unsubstituted C1-C20 silyl groups. Among them, a substituted or unsubstituted C1 to C20 saturated alkyl group is particularly preferable, and thus, a carbazole structure substituted with a saturated alkyl group at the ortho position of the cyano group is adopted, and the electron donating ability of the peripheral substituent group of carbazole is in a suitably weak state, which is advantageous for blue shift of light emission, so that the light color of the compound of the present invention is more excellent.
Wherein R is2Is a group represented by the following formula (4),
wherein R isa、Rb、RcEach independently selected from hydrogen and one of alkyl of C1-C9, Ra、Rb、RcAre connected with or not connected with each other to form a ring, Ra、Rb、RcAt least one of them is hydrogen, and represents the connecting end with formula (2). Through the preferable range, the steric hindrance of the peripheral substituent group is relatively small and is in a proper state, and a proper stacking structure can be formed during film forming, so that the carrier transport performance can be improved, the voltage can be reduced, meanwhile, the active site on carbazole can be protected, the energy transfer of Dexter can be inhibited, and the stability can be improved. As further preferred R2Examples of the (b) include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2, 2, 2-trifluoroethyl and the like, and one of methyl, ethyl, propyl, isopropyl, isobutyl, cyclopentyl and cyclohexyl is more preferable. When R is2When these radicals are present, in contrast to R2In the case of a tertiary carbon substituent, the effect of the present invention is further improved.
X1～X4At least 1 of which is CR2；
Preferably X1～X4Wherein 1 or 2 is CR2；
Preferably X1～X4Wherein 1 is CR2。
As a further preferable range, X1～X8Each independently selected from CH or CR2Wherein X is1～X41 or 2 of (a) are CR2，X5～X8All are CH, or 1-2 of them are CR2Further, X is preferable1～X41 in (a) is CR2，X5～X8Are all CH, or 1 of them is CR2。
X1～X41 in (a) is CR2，X5～X81 in (a) is CR2(ii) a Preferably, X1～X41 in (a) is CR2，X5～X81 in (a) is CR2And said R is2The same groups are chosen.
As described above, as D1、D2A group of the formula (2), X1～X8Of these, X is preferred3And/or X6Is CR2And other groups are CH, so that the substituted position is more favorable for ensuring the proper electron cloud density of the carbazole group, the luminous efficiency is more excellent, and a proper stacking structure can be formed during film forming, so that the carrier transmission performance can be improved.
The inventor's research also found that when R is2In the case of a tertiary carbon-containing group such as a tert-butyl group or a tert-amyl group, the sublimation temperature of the entire compound is very high, and the film formation is not favorable2Preferably not a substituent containing a tertiary carbon atom.
As D1、D2Preferred groups of (3) include the following groups.
Further, as D1、D2Preferable examples of the group of (b) include the following groups.
R in the compounds of the invention is preferably a hydrogen atom.
Further, D3And D4Are the same group;
further, Y1～Y8All are CH, or 1 of them is N and the rest are CH.
Further, Y1～Y4Are both CH, or wherein Y1～Y41 or 2 of which are N and the remainder are CH,
further, Y5～Y8Are both CH, or wherein Y5～Y81 or 2 of them are N and the rest are CH.
Further, the group represented by the formula (3) is selected from the group consisting of,
further, the organic compound of the present invention may preferably be a compound having a specific structure shown below, and these compounds are merely representative and do not limit the scope of the present invention.
In addition, the preparation process of the compound is simple and easy to implement, the raw materials are easy to obtain, and the compound is suitable for mass production amplification and is very suitable for industrial application.
The above-mentioned compound of the present invention has excellent light emitting properties, can realize high light emitting efficiency by giving triplet excitons, and is suitable for use as a light emitting dye, particularly a blue light emitting dye, based on its excellent carrier transport efficiency. Of course, since the compound of the present invention can also be used as a sensitizer to realize a good light-emitting layer together with a host material and a dye. The device to which it is applied includes, but is not limited to, 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, and is preferably an organic electroluminescent device.
The invention also provides an organic electroluminescent device which comprises a first electrode, a second electrode and at least one or more light-emitting functional layers which are inserted between the first electrode and the second electrode, wherein the light-emitting functional layers contain at least one compound disclosed by the invention.
The organic electroluminescent device of the invention has a structure consistent with the existing device, and comprises an anode layer, a plurality of light-emitting functional layers and a cathode layer; the plurality of light-emitting functional layers include at least a light-emitting layer containing the above organic compound 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 and display manufacturing enterprises on high-performance materials.
Detailed Description
The technical means of the present invention will be described in more detail below. It should be understood by those skilled in the art that the examples are only for the understanding of the present invention and should not be construed as the specific limitations of the present invention.
Method for obtaining the Compound of the present invention
The compound represented by the general formula (1) of the present invention can be obtained by a known method, for example, by a known organic synthesis method. Exemplary synthetic routes are given below, but may be obtained by other methods known to those skilled in the art.
Synthetic scheme
The organic electroluminescent element of the present invention has a known structure, and is characterized in that the compound of the present invention is used in a light-emitting layer. The organic electroluminescent device will be described in detail below.
The OLED includes first and second electrodes, and an organic material layer between the electrodes. The organic material may in turn be divided into a plurality of regions. For example, the organic material layer may include a hole transport region, a light emitting layer, and an electron transport region.
In a specific embodiment, a substrate may be used under the first electrode or over the second electrode. The substrate is a glass or polymer material having excellent mechanical strength, thermal stability, water resistance, and transparency. In addition, a Thin Film Transistor (TFT) may be provided on a substrate for a display.
The first electrode may be formed by sputtering or depositing a material used as the first electrode on the substrate. When the first electrode is used as an anode, an oxide transparent conductive material such as Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), tin dioxide (SnO2), zinc oxide (ZnO), or any combination thereof may be used. When the first electrode is used as a cathode, a metal or an alloy such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), ytterbium (Yb), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof can be used.
The organic material layer may be formed on the electrode by vacuum thermal evaporation, spin coating, printing, or the like. The compound used as the organic material layer may be an organic small molecule, an organic large molecule, and a polymer, and a combination thereof.
The hole transport region is located between the anode and the light emitting layer. The hole transport region may be a Hole Transport Layer (HTL) of a single layer structure including a single layer containing only one compound and a single layer containing a plurality of compounds. The hole transport region may also be a multi-layer structure including at least one of a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), and an Electron Blocking Layer (EBL); wherein the HIL is located between the anode and the HTL and the EBL is located between the HTL and the light emitting layer.
The material of the hole transport region may be selected from, but is not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylenevinylene, polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA), poly (3, 4-ethylenedioxythiophene)/poly (4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphorsulfonic acid (Pani/CSA), polyaniline/poly (4-styrenesulfonate) (Pani/PSS), aromatic amine derivatives such as compounds shown below in HT-1 to HT-51; or any combination thereof.
The hole injection layer is located between the anode and the hole transport layer. The hole injection layer may be a single compound material or a combination of a plurality of compounds. For example, the hole injection layer may employ one or more compounds of HT-1 to HT-50 described above, or one or more compounds of HI-1-HI-3 described below; one or more of the compounds HT-1 to HT-51 may also be used to dope one or more of the compounds HI-1-HI-3 described below.
The light-emitting layer includes a light-emitting dye (i.e., dopant) that can emit different wavelength spectra, and may also include a Host material (Host). The light emitting layer may be a single color light emitting layer emitting a single color of red, green, blue, or the like. The single color light emitting layers of a plurality of different colors may be arranged in a planar manner in accordance with a pixel pattern, or may be stacked to form a color light emitting layer. When the light emitting layers of different colors are stacked together, they may be spaced apart from each other or may be connected to each other. The light-emitting layer may be a single color light-emitting layer capable of emitting red, green, blue, or the like at the same time.
According to different technologies, the luminescent layer material can be different materials such as fluorescent electroluminescent material, phosphorescent electroluminescent material, thermal activation delayed fluorescent luminescent material, and the like. In an OLED device, a single light emitting technology may be used, or a combination of a plurality of different light emitting technologies may be used. These technically classified different luminescent materials may emit light of the same color or of different colors.
In one aspect of the invention, the light-emitting layer employs a thermally activated delayed fluorescence emission technique. The host material of the light-emitting layer is selected from, but not limited to, one or more of PH-1 to PH-85.
In one aspect of the invention, an Electron Blocking Layer (EBL) is located between the hole transport layer and the light emitting layer. The electron blocking layer may be, but is not limited to, one or more compounds of HT-1 to HT-51 described above, or one or more compounds of PH-47 to PH-77 described above; mixtures of one or more compounds from HT-1 to HT-51 and one or more compounds from PH-47 to PH-77 may also be used, but are not limited thereto.
The OLED organic material layer may further include an electron transport region between the light emitting layer and the cathode. The electron transport region may be an Electron Transport Layer (ETL) of a single-layer structure including a single-layer electron transport layer containing only one compound and a single-layer electron transport layer containing a plurality of compounds. The electron transport region may also be a multilayer structure including at least one of an Electron Injection Layer (EIL), an Electron Transport Layer (ETL), and a Hole Blocking Layer (HBL).
In one aspect of the invention, the electron transport layer material may be selected from, but is not limited to, the combination of one or more of ET-1 through ET-65 listed below.
In one aspect of the invention, a Hole Blocking Layer (HBL) is located between the electron transport layer and the light emitting layer. The hole blocking layer can adopt, but is not limited to, one or more compounds from ET-1 to ET-65 or one or more compounds from PH-1 to PH-46; mixtures of one or more compounds from ET-1 to ET-65 with one or more compounds from PH-1 to PH-46 may also be used, but are not limited thereto.
An electron injection layer may also be included in the device between the electron transport layer and the cathode, the electron injection layer materials including, but not limited to, combinations of one or more of the following.
LiQ、LiF、NaCl、CsF、Li2O、Cs2CO3、BaO、Na、Li、Ca、Yb、Mg。
Examples
Hereinafter, the organic compound of the present invention is typically synthesized, and the organic compound is applied to an organic electroluminescent device together with a corresponding comparative compound, and device performance under the same conditions is tested.
The present invention provides a specific synthetic method of a representative compound as exemplified by the following synthetic examples, and the solvents and reagents, intermediates, and chemical reagents such as ethyl acetate, methanol, and ethanol, which are used in the following synthetic examples, can be purchased or customized from the domestic chemical product market, for example, from the national drug group reagent company, Sigma-Aldrich company, and carbofuran reagent company.
In addition, the mass spectrum characterization data in the following synthetic examples were obtained by testing a ZAB-HS type mass spectrometer manufactured by Micromass, UK under the following test conditions: directly feeding sample, an EI source, an ionization voltage of 70eV, an ionization temperature of 250 ℃, an acceleration voltage of 6kv and a resolution of 1000.
Synthetic examples
Synthesis example 1: synthesis of T1
Synthesis of intermediate T1-1:
2,3, 5, 6-Tetrafluorobenzonitrile (1.75g, 10.0mmol), 3-methylcarbazole (3.8g, 21.0mmol) and sodium carbonate (2.65g, 25mmol), DMF (120ml) were added to a 250ml single-neck flask at room temperature, purged with nitrogen and protected, and reacted overnight at room temperature.
Stopping the reaction, injecting the reaction solution into water, adding a certain amount of ammonium chloride solid, and stirring until solid is separated out; after suction filtration and column chromatography, 3.8g of white solid was obtained with a yield of 77.5%. Mass spectrometric analysis determined molecular mass: 497.6 (theoretical value: 497.1).
Synthesis of T1:
a100 ml three-necked flask was charged with T1-1(3.0g, 6.03mmol), carbazole (2.52g, 15.07mmol), and sodium carbonate (1.92g, 18.09mmol) dissolved in 50ml of DMF. The nitrogen was replaced 3 times and protected. The temperature is increased to 80 ℃ and the reaction lasts for 16 h.
Stopping the reaction, injecting the reaction solution into water, adding a certain amount of ammonium chloride solid, and stirring until solid is separated out; suction filtration, column chromatography and recrystallization gave 1.51g of a yellow solid with a yield of 31.5%. Mass spectrometric analysis determined molecular mass: 791.6 (theoretical value: 791.3).
In synthesis examples 2 to 6, compounds T2, T6, T7, T9 and T12 were synthesized, respectively, in a similar manner to synthesis example 1.
Synthesis example 2
The reactant 3-methylcarbazole of synthesis example 1 was replaced with 3, 6-dimethylcarbazole; in the same manner as in synthesis example 1, T2 was synthesized. Mass spectrometric analysis determined molecular mass: 819.5 (theoretical value: 819.3).
Synthesis example 3
The reactant 3-methylcarbazole of synthesis example 1 was replaced with 3-isopropylcarbazole; in the same manner as in synthesis example 1, T6 was synthesized. Mass spectrometric analysis determined molecular mass: 847.4 (theoretical value: 847.3).
Synthesis example 4
The reactant 3-methylcarbazole of synthesis example 1 was replaced with 3-methyl-6-ethylcarbazole; in the same manner as in synthesis example 1, T7 was synthesized. Mass spectrometric analysis determined molecular mass: 847.4 (theoretical value: 847.3).
Synthesis example 5
The reactant 3-methylcarbazole of synthesis example 1 was replaced with 3-methyl-6-isobutylcarbazole; in the same manner as in synthesis example 1, T9 was synthesized. Mass spectrometric analysis determined molecular mass: 903.5 (theoretical value: 903.4).
Synthesis example 6
The reactant 3-methylcarbazole of synthesis example 1 was replaced with 3-ethylcarbazole; t12 was synthesized in the same manner as in synthesis example 1. Mass spectrometric analysis determined molecular mass: 819.6 (theoretical value: 819.3).
Synthesis example 7
The reactant 3-methylcarbazole of synthesis example 1 was replaced with 3, 6-di-tert-butylcarbazole; t161 was synthesized in the same manner as in synthesis example 1. Mass spectrometric analysis determined molecular mass: 987.8 (theoretical value: 987.5).
Synthesis example 8
The reactant 3-methylcarbazole of synthesis example 1 was replaced with 4-methylcarbazole; replacing carbazole with 9H-pyrido [2,3-B ] indole; t162 was synthesized in the same manner as in synthesis example 1. Mass spectrometric analysis determined molecular mass: 793.6 (theoretical value: 793.3).
Synthesis example 9
The reactant 3-methylcarbazole of synthesis example 1 was replaced with 2-methylcarbazole; (ii) a T165 was synthesized in the same manner as in synthesis example 1. Mass spectrometric analysis determined molecular mass: 791.8 (theoretical value: 791.3).
Synthesis example 10
Replacing the reactant carbazole of synthesis example 1 with 9H-pyrido [3,4-B ] indole; t121 was synthesized in the same manner as in synthesis example 1. Mass spectrometric analysis determined molecular mass: 793.6 (theoretical value: 793.3).
Synthesis example 11
The reactant 3-methylcarbazole of synthesis example 1 was replaced with 3-propylcarbazole; t126 was synthesized in the same manner as in synthesis example 1 by replacing carbazole with 9H-pyrido [3,4-B ] indole. Mass spectrometric analysis determined molecular mass: 849.7 (theoretical value: 849.3).
Synthesis example (comparative Compound)
Reference is made to CN110759851A for a synthesis method of comparative compound S2, the specific structure is as follows:
example 1
Device example 1 was fabricated, and the organic electroluminescent device was prepared as follows:
the glass plate coated with the ITO transparent conductive layer was sonicated in a commercial detergent, rinsed in deionized water, washed in acetone: ultrasonically removing oil in an ethanol mixed solvent, baking in a clean environment until the water is completely removed, cleaning by using ultraviolet light and ozone, and bombarding the surface by using low-energy cationic beams;
placing the glass substrate with the anode in a vacuum chamber, and vacuumizing to<1×10-5Pa, performing vacuum thermal evaporation on the anode layer film to obtain a film, wherein the vacuum thermal evaporation is performed on the anode layer film to obtain a film with the thickness of 10nm HT-4: HI-3(97/3, w/w) mixture as hole injection layer, 60nm compound HT-4 as hole transport layer, 5nm compound HT-51 as electron blocking layer; compound PH54 at 40 nm: t1 (100: 40, w/w) binary mixture as light-emitting layer; pH-28 at 5nm as hole blocking layer, compound ET-69 at 25 nm: ET-57(50/50, w/w) mixture as electron transport layer, 1nm LiF as electron injection layer, 150nm metallic aluminum as cathode. The total evaporation rate of all the organic layers and LiF is controlled at 0.1 nm/s, and the evaporation rate of the metal electrode is controlled at 1 nm/s.
Device examples 2 to 14 and comparative example 1 were prepared in the same manner as in device example 1 except that T1 in the light-emitting layer was replaced with a compound shown in Table 1 below.
The organic electroluminescent device prepared by the above process was subjected to the following performance measurement:
the driving voltage and external quantum efficiency of the organic electroluminescent devices prepared in the compounds and the comparative materials were measured at the same brightness using a digital source meter, a luminance meter and PR 650. Specifically, the voltage was raised at a rate of 0.1V per second, and it was determined that the luminance of the organic electroluminescent device reached 1000cd/m2The voltage at time, i.e., the drive voltage, while the external quantum efficiency (EQE%) of the resulting device can be tested directly on PR 650. .
Table 1: the properties of the organic electroluminescent device are shown in the following table
As can be seen from Table 2, when the compound of the present invention was used as a dye, the voltage was reduced and the device efficiency was improved, showing excellent device properties, as compared to the comparative compound. This is probably because the reduction of peripheral alkyl groups favors the carrier transport, which results in a reduction in the device voltage and also in an improvement in the balance of carrier transport, resulting in an increase in the device efficiency. This is advantageous for practical application of the compound of the present invention.
The experimental data show that the novel organic material is obviously improved compared with the prior art as an electron blocking material of an organic electroluminescent device, is an organic luminescent functional material with good performance, and has wide application prospect.
The present invention is illustrated in detail by the examples described above, but the present invention is not limited to the details described above, i.e., it is not intended that the present invention be implemented by relying on the details described above. It should be understood by those skilled in the art that any modification of the present invention, equivalent substitutions of the raw materials of the product of the present invention, addition of auxiliary components, selection of specific modes, etc., are within the scope and disclosure of the present invention.
Claims (18)
1. An organic compound characterized by having a structure represented by the formula (1),
wherein:
D1、D2each independently selected from the group represented by formula (2):
X1～X8independently selected from N or CR1，R1Independently selected from one of hydrogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl,
D3、D4independently selected from the group represented by formula (3):
Y1～Y8independently selected from CH or N;
r is selected from one of hydrogen, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroaryl amino, substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C3-C60 heteroaryl;
the substituent group is one or more groups selected from halogen, cyano, C1-C17 amino, C1-C17 carboxyl, C1-C17 aldehyde group, C1-C17 ester group, C1-C12 chain alkyl, C3-C12 cycloalkyl, C2-C10 alkenyl, C1-C10 alkoxy or thioalkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryl, and C3-C30 heteroaryl.
2. The organic compound according to claim 1,
X1～X8each independently selected from N, CH, CR1’Or CR2，
R1’Independently selected from one of substituted or unsubstituted C4-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, halogen, cyano, nitro, hydroxyl, amino, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl,
R2is a group represented by the following formula (4),
wherein R isa、Rb、RcEach independently selected from hydrogen and one of alkyl of C1-C9, Ra、Rb、RcAre connected with or not connected with each other to form a ring, Ra、Rb、RcAt least one of which is hydrogen, represents the connection end with the formula (2),
X1～X4at least 1 of which is CR2；
Preferably X1～X4Wherein 1 or 2 is CR2；
Preferably X1～X4Wherein 1 is CR2。
3. The organic compound according to claim 1,
X1～X8each independently selected from CH or CR2，R2Is a group represented by the following formula (4),
wherein R isa、Rb、RcEach independently selected from one of hydrogen and alkyl of C1-C9, Ra、Rb、RcAre connected with or not connected with each other to form a ring, Ra、Rb、RcAt least one of them is hydrogen, represents a connecting terminal with the formula (2), X1～X41 or 2 of (a) are CR2；
Preferably X5～X8All are CH, or 1-2 of them are CR2。
4. The organic compound according to claim 3,
X1～X41 in (a) is CR2，X5～X8Are all CH or 1 of them is CR2。
5. The organic compound according to claim 4,
X1～X41 in (a) is CR2，X5～X81 in (a) is CR2；
Preferably, X1～X41 in (a) is CR2，X5～X81 in (a) is CR2And said R is2The same groups are chosen.
6. The organic compound according to any one of claims 2 to 5, wherein R2Is selected from methyl, ethyl, propyl, isopropyl, isobutyl, cyclopentyl and cyclohexylOne of the groups;
R2preferential substituents: methyl and isopropyl.
7. The organic compound according to claim 1 or 2, wherein the group represented by formula (2) is selected from the group consisting of,
8. the organic compound according to claim 2,
X3and/or X6Is CR2。
9. The organic compound of claim 1, wherein D3And D4Are the same group.
10. The organic compound according to claim 1, wherein Y is1～Y8All are CH, or 1 of them is N and the rest are CH.
11. The organic compound according to claim 1,
Y1～Y4are both CH, or wherein Y1～Y41 or 2 of which are N and the remainder are CH,
Y5～Y8are both CH, or wherein Y5～Y81 or 2 of them are N and the rest are CH.
12. The organic compound according to claim 1, wherein the group represented by formula (3) is selected from the group consisting of,
13. the organic compound according to claim 1, wherein the compound of the general formula (1) is a compound having the following specific structure:
14. an organic electroluminescent material which is a compound as described in claim 1 to 13.
15. A luminescent dye material which is a compound as claimed in claim 1 to 13.
16. Use of a compound according to any one of claims 1 to 13 as a luminescent dye.
17. 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 layer contains the compound according to any one of claims 1 to 13.
18. The organic electroluminescent device according to claim 17, wherein the plurality of light-emitting functional layers include a light-emitting layer containing the organic compound according to any one of claims 1 to 13.
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