CN116903641A - Organic compound and organic electroluminescent device using same - Google Patents
Organic compound and organic electroluminescent device using same Download PDFInfo
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- CN116903641A CN116903641A CN202210356045.7A CN202210356045A CN116903641A CN 116903641 A CN116903641 A CN 116903641A CN 202210356045 A CN202210356045 A CN 202210356045A CN 116903641 A CN116903641 A CN 116903641A
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- heteroaryl
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- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 33
- 239000000463 material Substances 0.000 claims abstract description 54
- -1 C1-C20 alkyl silicon Chemical compound 0.000 claims description 132
- 239000010410 layer Substances 0.000 claims description 88
- 229910052739 hydrogen Inorganic materials 0.000 claims description 45
- 239000001257 hydrogen Substances 0.000 claims description 45
- 125000004104 aryloxy group Chemical group 0.000 claims description 31
- 229910052736 halogen Inorganic materials 0.000 claims description 31
- 150000002367 halogens Chemical class 0.000 claims description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- 125000001769 aryl amino group Chemical group 0.000 claims description 29
- 125000001072 heteroaryl group Chemical group 0.000 claims description 29
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 29
- 125000001424 substituent group Chemical group 0.000 claims description 29
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 28
- 150000002431 hydrogen Chemical class 0.000 claims description 28
- 125000003118 aryl group Chemical group 0.000 claims description 25
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 25
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims description 21
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 230000005525 hole transport Effects 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 239000000126 substance Substances 0.000 claims description 13
- 230000000903 blocking effect Effects 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 238000002347 injection Methods 0.000 claims description 11
- 239000007924 injection Substances 0.000 claims description 11
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 11
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 229910052710 silicon Inorganic materials 0.000 claims description 11
- 239000010703 silicon Substances 0.000 claims description 11
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 10
- 125000003282 alkyl amino group Chemical group 0.000 claims description 7
- 239000002346 layers by function Substances 0.000 claims description 6
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 5
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 4
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 239000010409 thin film Substances 0.000 claims description 3
- 230000003287 optical effect Effects 0.000 claims description 2
- 230000005669 field effect Effects 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 63
- 239000000975 dye Substances 0.000 abstract description 8
- 238000004020 luminiscence type Methods 0.000 abstract description 2
- 239000000543 intermediate Substances 0.000 description 51
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 38
- 238000003786 synthesis reaction Methods 0.000 description 27
- 230000015572 biosynthetic process Effects 0.000 description 26
- 238000010438 heat treatment Methods 0.000 description 26
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 22
- 229910052757 nitrogen Inorganic materials 0.000 description 20
- 238000004440 column chromatography Methods 0.000 description 19
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 18
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 17
- 238000001704 evaporation Methods 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 16
- 238000000034 method Methods 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 11
- 230000008020 evaporation Effects 0.000 description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 9
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000008096 xylene Substances 0.000 description 9
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 8
- 239000011368 organic material Substances 0.000 description 8
- 230000005540 biological transmission Effects 0.000 description 7
- 239000002019 doping agent Substances 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 239000007850 fluorescent dye Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000002356 single layer Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 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 5
- 239000003086 colorant Substances 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
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 5
- 125000001624 naphthyl group Chemical group 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- 235000010290 biphenyl Nutrition 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- 239000010408 film Substances 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 125000001725 pyrenyl group Chemical group 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 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
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 3
- 238000004364 calculation method Methods 0.000 description 3
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 230000006872 improvement Effects 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
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 3
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 3
- 229920000767 polyaniline Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 3
- 125000001544 thienyl group Chemical group 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- FDXXHPYFJDKWJS-UHFFFAOYSA-N 1-bromo-3-tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC(Br)=C1 FDXXHPYFJDKWJS-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
- 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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 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
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 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
- 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
- 229910052796 boron Inorganic materials 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000010549 co-Evaporation Methods 0.000 description 2
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 2
- 229940045803 cuprous chloride Drugs 0.000 description 2
- 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 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 230000003111 delayed effect Effects 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
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 125000001041 indolyl group Chemical group 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- 125000005561 phenanthryl group Chemical group 0.000 description 2
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 2
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 125000000168 pyrrolyl group Chemical group 0.000 description 2
- IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 2
- 239000012414 tert-butyl nitrite 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
- 125000006736 (C6-C20) aryl 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
- 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 description 1
- 125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 description 1
- 125000004529 1,2,3-triazinyl group Chemical group N1=NN=C(C=C1)* 0.000 description 1
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 description 1
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 description 1
- 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 description 1
- 125000004530 1,2,4-triazinyl group Chemical group N1=NC(=NC=C1)* 0.000 description 1
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 description 1
- 125000004506 1,2,5-oxadiazolyl group Chemical group 0.000 description 1
- 125000004517 1,2,5-thiadiazolyl group Chemical group 0.000 description 1
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 description 1
- 125000003363 1,3,5-triazinyl group Chemical group N1=C(N=CN=C1)* 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 1
- NQVLOHKMEASTMW-UHFFFAOYSA-N 4-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1C1=CC=C(N)C=C1 NQVLOHKMEASTMW-UHFFFAOYSA-N 0.000 description 1
- HQSCPPCMBMFJJN-UHFFFAOYSA-N 4-bromobenzonitrile Chemical compound BrC1=CC=C(C#N)C=C1 HQSCPPCMBMFJJN-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
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-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
- 229910018068 Li 2 O Inorganic materials 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
- 239000004793 Polystyrene Substances 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
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- CKUAXEQHGKSLHN-UHFFFAOYSA-N [C].[N] Chemical compound [C].[N] CKUAXEQHGKSLHN-UHFFFAOYSA-N 0.000 description 1
- JHYLKGDXMUDNEO-UHFFFAOYSA-N [Mg].[In] Chemical compound [Mg].[In] JHYLKGDXMUDNEO-UHFFFAOYSA-N 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
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000004429 atom Chemical group 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
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000006267 biphenyl group Chemical group 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
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 1
- 150000001768 cations Chemical class 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
- 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
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 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
- 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
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000005238 degreasing Methods 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
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 230000005284 excitation Effects 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
- 125000005842 heteroatom Chemical group 0.000 description 1
- 239000012761 high-performance material Substances 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 239000012535 impurity Substances 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
- 230000003993 interaction Effects 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
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- CSJDCSCTVDEHRN-UHFFFAOYSA-N methane;molecular oxygen Chemical compound C.O=O CSJDCSCTVDEHRN-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 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
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 125000003933 pentacenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C12)* 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 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
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 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
- 125000005592 polycycloalkyl group Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 238000003077 quantum chemistry computational method Methods 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 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
- 230000001105 regulatory effect Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 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
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000010189 synthetic method Methods 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
- 238000002207 thermal evaporation Methods 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 230000036962 time dependent Effects 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
- 238000012795 verification Methods 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
- 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
-
- 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
- C07F7/0814—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 is substituted at a C ring atom by Si
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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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/05—Isotopically modified compounds, e.g. labelled
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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
- 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
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
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- 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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- 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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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
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Abstract
The invention relates to an organic compound, and belongs to the technical field of organic luminescent materials. The organic compound of the present invention has a structure represented by formula (I). The compounds of the invention have good luminescence properties when used as luminescent materials, in particular as dyes. The organic electroluminescent device prepared by the compound has the advantages of low voltage and long service life。
Description
Technical Field
The invention relates to an organic compound, and belongs to the technical field of organic luminescent materials. In particular to a B-N structure organic photoelectric material taking cyclo [3.3.3] azine or cyclo [2.2.3] azine as a basic framework. The invention also relates to application of the organic compound in an organic electroluminescent device and the organic electroluminescent device adopting the compound.
Background
Currently, optoelectronic devices employing organic materials are becoming increasingly popular. Most materials used to make such devices are more cost effective (organic materials are inexpensive) than inorganic devices. At present, in the structure of an organic electroluminescent device in the field of display and illumination, blue fluorescence is generally adopted to match red and green phosphorescence materials. Recently, patent documents CN111333671A, CN112279872a and CN110790782a report an ultrapure red fluorescent compound of TADF (Thermally Activated Delayed Fluorescence ) based on a B-N resonance structure, which comprises B, N and a benzene ring to form a rigid polycyclic aromatic skeleton. The nitrogen atom has a resonance effect opposite to that of the boron atom, and the opposite resonance effect is enhanced at the position of its para-position. Thus, this effect can significantly separate HOMO and LUMO orbitals and thus has certain TADF characteristics.
Although the series of materials have shorter service life as fluorescent dyes, higher device voltage and difficult practicality, the organic electroluminescent materials have great room for improvement in light-emitting performance, and development of new luminescent material systems is needed in the industry to meet the commercial demands.
Disclosure of Invention
In order to solve the technical problems, the invention provides a B-N structure organic photoelectric material taking a ring [3.3.3] azine or a ring [2.2.3] azine as a basic framework, wherein a heterocyclic structure containing N atoms is introduced into a rigid ring, and the compound can enhance the carrier transmission efficiency (especially a hole) of the material by adopting a specific structure and reduce the voltage. Meanwhile, the service life of the organic electroluminescent device prepared by adopting the compound disclosed by the invention as fluorescent dye is obviously prolonged.
Specifically, the present invention provides an organic compound having a structure represented by formula (1):
ring A is connected with ring B condensed ring, ring A and ring B independently represent any one of substituted or unsubstituted C5-C60 aromatic ring and substituted or unsubstituted C4-C60 heteroaromatic ring;
ring C, ring D, ring E, ring F each independently represent one of a substituted or unsubstituted C5-C60 aromatic ring, a substituted or unsubstituted C3-C60 heterocyclic ring; by single bond, -O-, -S-, -CR between ring D and ring C 1 R 2 -or-NR 3 R 4 Connection or disconnection between ring D and ring C, E ring and F ring being connected by a single bond, -O-, -S-, -CR 1 R 2 -or-NR 3 R 4 The E ring is connected with the F ring or the E ring is not connected with the F ring; r is R 1 、R 2 、R 3 、R 4 Each independently selected from one or two combinations of halogen, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkyl silicon base, C1-C20 alkyl amino, cyano, nitro, hydroxyl, amino, C6-C30 aryl amino, C3-C30 heteroaryl amino, C6-C30 aryloxy, C3-C30 heteroaryl oxy, C6-C60 aryl and C3-C60 heteroaryl;
the substituent groups in the ring A, the ring B, the ring C, the ring D, the ring E and the ring F are respectively and independently selected from at least one of halogen, unsubstituted or R ' substituted C1-C20 chain alkyl, unsubstituted or R ' substituted C3-C20 cycloalkyl, unsubstituted or R ' substituted C1-C20 alkoxy, unsubstituted or R ' substituted C1-C20 alkyl silicon base, unsubstituted or R ' substituted C1-C20 alkylamino, cyano, nitro, hydroxyl, amino, unsubstituted or R ' substituted C6-C30 arylamino, unsubstituted or R ' substituted C3-C30 heteroaryl amino, unsubstituted or R ' substituted C6-C30 aryloxy, unsubstituted or R ' substituted C3-C30 heteroaryl, unsubstituted or R ' substituted C6-C60 aryl and unsubstituted or R ' substituted C3-C60 heteroaryl;
R' is selected from one or two of halogen, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkyl silicon base, cyano, nitro, hydroxyl, amino, C6-C30 aryl amino, C3-C30 heteroaryl amino, C6-C30 aryloxy, C3-C30 heteroaryl oxy, C6-C60 aryl and C3-C60 heteroaryl;
the substituents in ring A, ring B, ring C, ring D, ring E, ring F are each independently unconnected, or adjacent two substituents are connected by a chemical bond to form a ring.
Further, in the formula (1), the ring A and the ring B each independently represent any one of a substituted or unsubstituted C5-C14 aromatic ring and a substituted or unsubstituted C4-C20 heteroaromatic ring, and the ring C, the ring D, the ring E and the ring F each independently represent one of a substituted or unsubstituted C5-C14 aromatic ring and a substituted or unsubstituted C3-C14 heteroaromatic ring.
Still further, in the formula (1), at least one of the ring D and the ring E has a structure represented by the formula (a), and at least one of the ring C and the ring F has a structure represented by the formula (b):
in formula (a), c represents a shared bond position of formula (a) to formula (1), and in formula (b), represents a group attachment site;
The Z is 1 、Z 2 、Z 3 、Z 4 、Z 5 、Z 6 、Z 7 、Z 8 And Z 9 Are independently selected from CR 1 Or N, the R 1 At least one selected from the group consisting of hydrogen, halogen, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C1-C20 alkylamino, cyano, nitro, hydroxy, amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl; the R is 1 Are not independently connected, or adjacent two R 1 Is connected into a ring through a chemical bond;
R 1 wherein each of the substituted substituents is independently selected from the group consisting of halogen, C1-C20 chain alkyl, C3-C20 cycloalkylOne or two of C1-C20 alkoxy, C1-C20 alkyl silicon, cyano, nitro, hydroxy, amino, C6-C30 aryl amino, C3-C30 heteroaryl amino, C6-C30 aryloxy, C3-C30 heteroaryl oxy, C6-C60 aryl and C3-C60 heteroaryl.
Still more preferably, the organic compound of the present invention has a structure represented by the formula (1-1):
the Z is 1’ 、Z 2’ 、Z 3’ 、Z 4’ 、Z 5’ 、Z 6’ 、Z 7’ 、Z 8’ And Z 9’ Definition of (1) and Z 1 、Z 2 、Z 3 、Z 4 、Z 5 、Z 6 、Z 7 、Z 8 And Z 9 The definition of the ring A and the ring B are the same as those in the formula (1);
the ring D and the ring C are connected through a single bond, -O-, -S-, -CR 1 R 2 -or-NR 3 R 4 Linking or not linking ring D to ring C, said E ring being linked to F ring by a single bond, -O-, -S-, -CR 1 R 2 -or-NR 3 R 4 The E ring and the F ring are connected or not connected.
Preferably, the organic compound has a structure represented by the formula (1-2):
in the formula (1-2), the dotted line represents the connection or disconnection.
Still further, in the formulae (1-1) and (1-2), the ring A and the ring B are each independently selected from the structures represented by the following formula (c) or formula (d):
in the formulas (c) and (d), the dotted line represents the position of the shared chemical bond connected to the formula (1), and "N'" represents "N" in the formula (1);
the Z is 11 、Z 12 、Z 13 、Z 14 、Z 15 Are independently selected from CR 2 Or N, the R 2 At least one selected from the group consisting of hydrogen, halogen, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C1-C20 alkylamino, cyano, nitro, hydroxy, amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl;
R 2 Wherein each of the substituted substituents is independently selected from one or a combination of two of halogen, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, cyano, nitro, hydroxy, amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, C3-C60 heteroaryl;
further preferably, the organic compound of the present invention has a structure represented by the formula (1-3) or the formula (1-4):
in the formula (1-3), the formula (1-4) and the formula (1-3-2), the ring D and the ring C are formed by single bond, -O-, -S-, -CR 1 R 2 -or-NR 3 R 4 Linking or not linking ring D to ring C, said E ring being linked to F ring by a single bond, -O-, -S-, -CR 1 R 2 -or-NR 3 R 4 The E ring is connected with the F ring or the E ring is not connected with the F ring;
the Z is 11 、Z 12 、Z 13 、Z 11’ 、Z 12’ 、Z1 3’ 、Z 14 、Z 15 、Z 14’ 、Z 15’ 、Z 16 、Z 17 、Z 18 Are independently selected from CR 2 Or N, the R 2 At least one selected from the group consisting of hydrogen, halogen, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C1-C20 alkylamino, cyano, nitro, hydroxy, amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl;
R 2 Wherein each of the substituted substituents is independently selected from one or a combination of two of halogen, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, cyano, nitro, hydroxy, amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, C3-C60 heteroaryl;
preferably, the organic compound has a structure represented by formula (1-5) or formula (1-6):
in the formula (1-5) or the formula (1-6), the dotted line represents the connection or disconnection. Preferably, in the above formula (1-3), formula (1-4), formula (1-5) or formula (1-6), the Z 1 、Z 2 、Z 3 、Z 4 、Z 5 、Z 6 、Z 7 、Z 8 、Z 9 、Z 1’ 、Z 2’ 、Z 3’ 、Z 4’ 、Z 5’ 、Z 6’ 、Z 7’ 、Z 8’ And Z 9’ Are independently selected from CR 1 Or N, said Z 11 、Z 12 、Z 13 、Z 11’ 、Z 12’ 、Z 13’ 、Z 14 、Z 15 、Z 14’ 、Z 15’ Are independently selected from CR 2 Or N;
the R is 1 、R 2 Each independently selected from at least one of hydrogen, halogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C1-C10 alkylsilyl, substituted or unsubstituted C1-C10 alkylamino, cyano, nitro, hydroxy, amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl;
R 1 、R 2 The substituted substituents of the above are each independently selected from one or two of halogen, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 alkyl silicon base, cyano, nitro, hydroxyl, amino, C6-C30 aryl amino, C3-C30 heteroaryl amino, C6-C30 aryloxy, C3-C30 heteroaryl oxy, C6-C30 aryl and C3-C30 heteroaryl.
Still more preferably, the organic compound of the present invention,
has a structure as shown in the formula (1-7) or the formula (1-8):
in the formulae (1-7) and (1-8), the dotted line represents the connection or disconnection;
r2 and R3 respectively and independently represent substituent groups with single substituent groups up to the maximum allowable number, R2 and R3 respectively and independently represent at least one of hydrogen, halogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkylamino, cyano, nitro, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroaryl amino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryl oxy, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl;
The substituent groups of the substituents R2 and R3 are independently selected from one or two of chain halogen, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkyl silicon base, cyano, nitro, hydroxyl, amino, C6-C30 aryl amino, C3-C30 heteroaryl amino, C6-C30 aryloxy, C3-C30 heteroaryl oxy, C6-C60 aryl and C3-C60 heteroaryl;
preferably, R2, R3 are each independently selected from hydrogen;
preferably, in the formulas (1-7) and (1-8), the broken line is not connected.
In the formulae (1-7) and (1-8), the Z 1 、Z 2 、Z 3 、Z 4 、Z 1’ 、Z 2’ 、Z 3’ 、Z 4’ Are independently selected from CR 1 ；
Preferably, the Z 1 、Z 2 、Z 3 、Z 4 、Z 1’ 、Z 2’ 、Z 3’ 、Z 4’ Are independently selected from CR 1 The R is 1 Independently selected from at least one of hydrogen, C1-C10 chain alkyl and C3-C10 cycloalkyl;
still preferably, the Z 1 、Z 2 、Z 3 、Z 4 、Z 1’ 、Z 2’ 、Z 3’ 、Z 4’ Are independently selected from CR 1 The R is 1 Independently selected from hydrogen or C1-C10 chain alkyl, said Z 5 、Z 6 、Z 7 、Z 8 、Z 9 、Z 5’ 、Z 6’ 、Z 7’ 、Z 8’ And Z 9’ Are independently selected from CR 1’ Or N, the R 1’ Independently selected from hydrogen, halogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1At least one of C10 alkoxy, substituted or unsubstituted C1-C10 alkylsilyl, substituted or unsubstituted C1-C10 alkylamino, cyano, nitro, hydroxy, amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl;
Further preferably, the Z 1 、Z 2 、Z 3 、Z 4 、Z 1’ 、Z 2’ 、Z 3’ 、Z 4’ Are independently selected from CR 1 The R is 1 Independently selected from hydrogen, methyl, ethyl, isopropyl, tert-butyl, isobutyl or tert-pentyl, said Z 5 、Z 6 、Z 7 、Z 8 、Z 9 、Z 5’ 、Z 6’ 、Z 7’ 、Z 8’ And Z 9’ Are independently selected from CR 1’ Or N, the R 1’ Independently selected from at least one of hydrogen, C1-C10 chain alkyl and C3-C10 cycloalkyl. In the formulae (1-7) and (1-8), the Z 1 、Z 2 、Z 3 、Z 4 One of them is selected from CR 1 The R is 1 Independently selected from at least one of C1-C10 chain alkyl and C3-C10 cycloalkyl, and Z at the same time 1 、Z 2 、Z 3 、Z 4 Three other of (a) are selected from CR 1 Said R is 1 Is hydrogen; and Z 1’ 、Z 2’ 、Z 3’ 、Z 4’ One of them is selected from CR 1’ The R is 1’ Independently selected from at least one of C1-C10 chain alkyl and C3-C10 cycloalkyl, and Z at the same time 1’ 、Z 2’ 、Z 3’ 、Z 4’ Three other of (a) are selected from CR 1’ Said R is 1’ Is hydrogen;
preferably, Z 2 Selected from CR 1 The R is 1 Selected from one of C1-C10 chain alkyl and C3-C10 cycloalkyl, and Z at the same time 1 、Z 3 、Z 4 Selected from CR 1 Said R is 1 Is hydrogen, and Z 2’ Selected from CR 1’ The R is 1’ Selected from one of C1-C10 chain alkyl and C3-C10 cycloalkyl, and Z at the same time 1’ 、Z 3’ 、Z 4’ Selected from CR 1’ Said R is 1’ Is hydrogen;
or preferably, Z 3 Selected from CR 1 The R is 1 Selected from one of C1-C10 chain alkyl and C3-C10 cycloalkyl, and Z at the same time 1 、Z 2 、Z 4 Selected from CR 1 Said R is 1 Is hydrogen, and Z 3’ Selected from CR 1’ The R is 1’ Selected from one of C1-C10 chain alkyl and C3-C10 cycloalkyl, and Z at the same time 1’ 、Z 2’ 、Z 4’ Selected from CR 1’ Said R is 1’ Is hydrogen;
more preferably, Z 2 Selected from CR 1 The R is 1 Selected from methyl, ethyl, isopropyl, tert-butyl, isobutyl or tert-pentyl, and at the same time Z 1 、Z 3 、Z 4 Selected from CR 1 Said R is 1 Is hydrogen, and Z 2’ Selected from CR 1’ The R is 1’ Selected from methyl, ethyl, isopropyl, tert-butyl, isobutyl or tert-pentyl, and at the same time Z 1’ 、Z 3’ 、Z 4’ Selected from CR 1’ Said R is 1’ Is hydrogen;
or preferably, Z 3 Selected from CR 1 The R is 1 Selected from methyl, ethyl, isopropyl, tert-butyl, isobutyl or tert-pentyl, and at the same time Z 1 、Z 2 、Z 4 Selected from CR 1 Said R is 1 Is hydrogen, and Z 3’ Selected from CR 1’ The R is 1’ Selected from methyl, ethyl, isopropyl, tert-butyl, isobutyl or tert-pentyl, and at the same time Z 1’ 、Z 2’ 、Z 4’ Selected from CR 1’ Said R is 1’ Is hydrogen.
In the present invention, the "substituted or unsubstituted" group may be substituted with one substituent or may be substituted with a plurality of substituents, and when the number of substituents is plural, the substituents may be selected from different substituents, and the same meaning is given when the same expression mode is involved in the present invention, and the selection ranges of the substituents are not repeated as shown above.
In the present invention, the "chemical bond" is a generic term for strong interaction force between two or more adjacent atoms in a molecule, and the types of chemical bonds include carbon-carbon single bonds, carbon-carbon double bonds, carbon-nitrogen single bonds, carbon-oxygen single bonds, and the like.
In the present specification, unless otherwise specified, both aryl and heteroaryl include cases of single rings and condensed rings. By monocyclic aryl is meant that the molecule contains at least one phenyl group, and when the molecule contains at least two phenyl groups, the phenyl groups are independent of each other and are linked by a single bond, such as phenyl, biphenyl, terphenyl, and the like; condensed ring aryl means that the molecule contains at least two benzene rings, but the benzene rings are not independent of each other, but the common ring edges are condensed with each other, such as naphthyl, anthracenyl 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 (such as aryl, heteroaryl, alkyl, etc.), the heteroaryl group and the other groups are independent of each other and are connected by a single bond, such as pyridine, furan, thiophene, etc.; fused ring heteroaryl means fused from at least one phenyl group and at least one heteroaryl group, or fused from at least two heteroaryl rings, such as, for example, quinoline, isoquinoline, benzofuran, dibenzofuran, benzothiophene, dibenzothiophene, and the like.
In the present specification, the expression of Ca to Cb means that the group has a carbon number of a to b, and unless otherwise specified, the carbon number generally excludes the carbon number of a substituent.
In the present specification, the substituted or unsubstituted C6-C60 aryl group is preferably a substituted or unsubstituted C6-C30 aryl group, more preferably a C6-C20 aryl group, and still more preferably a group selected from the group consisting of phenyl, naphthyl, anthryl, benzanthracenyl, phenanthryl, benzophenanthryl, pyrenyl, hole-yl, perylene, fluoranthenyl, tetracenyl, pentacenyl, benzopyrenyl, biphenyl, terphenyl, tripolyphenyl, and tetrabenzoylA group selected from the group consisting of a fluorenyl group, a spirobifluorenyl group, a dihydrophenanthrenyl group, a dihydropyrenyl group, a tetrahydropyrenyl group, a cis-or trans-indenofluorenyl group, a trimeric indenyl group, a heterotrimeric indenyl group, a spirotrimeric indenyl group, and a spiroheterotrimeric indenyl group. Specifically, the biphenyl group is selected from the group consisting of 2-biphenyl group, 3-biphenyl group and 4-biphenyl group; 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 comprises 1-naphthyl or 2-naphthyl; the anthracenyl is selected from the group consisting of 1-anthracenyl, 2-anthracenyl and 9-anthracenyl; the fluorenyl group is selected from the group consisting of 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, and 9-fluorenyl; the pyrenyl group is selected from 1-pyrenyl, 2-pyrenyl and 4-pyrenyl; and the tetracenyl is selected from the group consisting of 1-tetracenyl, 2-tetracenyl and 9-tetracenyl. Preferred examples of the aryl group in the present invention include a group selected from the group consisting of phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, indenyl, fluorenyl and derivatives thereof, fluoranthenyl, triphenylenyl, pyrenyl, perylenyl, A group selected from the group consisting of a radical and a tetracenyl radical. The biphenyl is selected from 2-biphenyl, 3-biphenyl and 4-biphenyl; the terphenyl group comprises 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 comprises 1-naphthyl or 2-naphthyl; the anthracenyl is selected from the group consisting of 1-anthracenyl, 2-anthracenyl and 9-anthracenyl; 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 the group consisting of 1-pyrenyl, 2-pyrenyl, and 4-pyrenyl; the tetracenyl group is selected from the group consisting of 1-tetracenyl, 2-tetracenyl and 9-tetracenyl.
Heteroatoms in the present description are generally selected from N, O, S, P, si and Se, preferably from N, O, S.
In the present specification, the substituted or unsubstituted C3 to C60 heteroaryl group is preferably a substituted or unsubstituted C3 to C30 heteroaryl group, more preferably a C4 to C20 heteroaryl group, and still more preferably a nitrogen-containing heteroaryl group, an oxygen-containing heteroaryl group, a sulfur-containing heteroaryl group, or the like, and specific examples thereof include: furyl, thienyl, pyrrolyl, pyridyl, benzofuryl, benzothienyl, isobenzofuryl, isobenzothienyl, indolyl, isoindolyl, dibenzofuryl, dibenzothienyl, carbazolyl, derivatives thereof, quinolinyl, isoquinolinyl, acridinyl, phenanthridinyl, benzo-5, 6-quinolinyl, benzo-6, 7-quinolinyl, benzo-7, 8-quinolinyl, phenothiazinyl, phenazinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthyridinyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinoimidazolyl, thienyl, benzoxazolyl, naphthyridinyl, anthracenooxazolyl, phenanthroizolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1, 5-diazaanthracenyl, 2,7, 2,3, 6, 4-dipyrene, 1, 4-dipyrene, 4, 5-dipyrene, 10-tetraazaperylene, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, benzocarboline, phenanthroline, 1,2, 3-triazolyl, 1,2, 4-triazolyl, benzotriazole, 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, benzothiadiazole, and the like. As preferable examples of the heteroaryl group in the present invention, for example, furyl, thienyl, pyrrolyl, benzofuryl, benzothienyl, isobenzofuryl, indolyl, dibenzofuryl, dibenzothienyl, carbazolyl and derivatives thereof are mentioned, wherein the carbazolyl derivative is preferably 9-phenylcarbazole, 9-naphthylcarbazole benzocarbazole, dibenzocarbazole, or indolocarbazole.
Examples of the aryloxy group in the present specification include monovalent groups composed of the above aryl group, heteroaryl group and oxygen.
In the present specification, examples of the C1-C20 alkyl group include: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, adamantyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2-trifluoroethyl and the like.
In the present specification, the C3-C20 cycloalkyl group includes a monocycloalkyl group and a polycycloalkyl group, and for example, may be cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or the like.
In the present specification, examples of the C1 to C20 alkoxy group include: methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, pentyloxy, isopentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy and the like are preferred, methoxy, ethoxy, n-propoxy, isopropoxy, tert-butoxy, sec-butoxy, isobutoxy, isopentyloxy are more preferred.
In the present specification, examples of the C1-C20 silyl group include silyl groups substituted with the groups exemplified for the C1-C20 alkyl groups described above, and specific examples include: and methylsilyl, dimethylsilyl, trimethylsilyl, ethylsilyl, diethylsilyl, triethylsilyl, t-butyldimethylsilyl, t-butyldiphenylsilyl, and the like.
In the present specification, examples of halogen include: fluorine, chlorine, bromine, iodine, and the like.
Further, the organic compound of the present invention may preferably be a compound of the specific structure shown below, which is merely representative and does not limit the scope of the present invention:
the organic compound can be used as a TADF material, a light-emitting layer guest material or a doping agent, is suitable for a TADF OLED or a TASF OLED device, and can effectively improve the performance of the device. The OLED device has good carrier transmission performance and high luminous efficiency, and has potential application in solving the problem of efficiency roll-off of the OLED device under high current density and prolonging the service life of the device.
The specific reasons for the excellent properties of the compounds of the present invention as luminescent dyes and/or sensitizer materials in the light-emitting layer of an organic electroluminescent device are not clear, and presumably the following reasons:
The organic compound adopts a highly condensed large pi framework system which takes the ring [3.3.3] azine or the ring [2.2.3] azine as the center, and the rigid structure has strong excitation state stability and good carrier transmission property. The target molecule has both high luminous efficiency and stable chemical properties (long material life), and simultaneously the carrier transport efficiency of the compound structure of the invention is improved (because N atoms are introduced into a condensed ring structure, the hole transport efficiency is improved). Therefore, the compound has good carrier transmission performance and TADF property, and has high fluorescence quantum efficiency, and when the compound is used as an OLED luminescent layer material, the rigid planar structure containing N atoms enhances the hole transmission capability of the material, is beneficial to balancing the carrier transmission of the luminescent layer, reduces the voltage and prolongs the service life of the device.
The compound of the invention can form a ring or not between the ring E and the ring F, and can form a ring or not between the ring D and the ring C, and the applicant has found that the structure which does not form a ring has more advantages through experimental verification.
When the compound provided by the invention is used as a luminescent material, especially as a blue dye, the compound has good luminescent performance, and the compound is used as an OLED luminescent layer material, so that the voltage is reduced, and the service life of a device is prolonged.
The compound of the invention is suitable for being used as a functional material of an organic light-emitting device. However, the application of the compound of the present invention is not limited to organic light emitting devices. Such organic electronic devices include, but are not limited to, organic electroluminescent devices, optical sensors, solar cells, lighting elements, information labels, electronic artificial skin sheets, sheet scanners or electronic papers, preferably organic electroluminescent devices.
The invention also provides an organic electroluminescent device, which comprises a first electrode, a second electrode and at least one or more luminescent functional layers inserted between the first electrode and the second electrode, wherein the luminescent functional layers contain at least one compound shown as the general formula (I) in the 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 scheme of the invention is further more specifically described below. It should be apparent to those skilled in the art that the detailed description, as well as the examples, are merely intended to facilitate an understanding of the invention and are not intended to limit the invention to the particular forms disclosed.
The compounds of the invention are obtained:
the compounds of formula (I) according to the invention can be obtained by known methods, for example by synthesis by known organic synthesis methods. Exemplary synthetic routes are given below, but may be obtained by other methods known to those skilled in the art. The representative synthetic route for the compounds of the general formula of the present invention is as follows:
wherein Z is 1 -Z 8 Are independently selected from CR 1 Or N, the R 1 Independently selected from one of hydrogen, halogen, cyano, nitro, hydroxy, 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 alkylsilyl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C6-C60 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, said R1 and the attached aromatic ring or the attached heteroaromatic ring may each independently be attached to each other by a chemical bond.
Specific synthetic examples
The present invention provides, by way of example, specific synthetic methods for representative compounds, such as solvents and reagents, intermediates, ethyl acetate, methanol, ethanol, and other chemical reagents used in the following synthesis examples, all of which may be purchased or customized from the domestic chemical product market.
Synthetic example (1): synthesis of intermediate A1
Experimental operation: raw material 1-aminocyclo [2.2.3] azine (30 g,192.08 mmol) was added to a 1L three-necked flask, 500ml of N, N-dimethylformamide was added thereto, bromosuccinimide (85.47 g,480.19 mmol) was slowly added thereto, the reaction was carried out at-20℃for 3 hours, and after that, the system was added to 2L of water, a large amount of solids was precipitated, filtered, and the solids were recrystallized 2 times from toluene+ethanol to obtain the objective intermediate A154.32g.
Synthetic example (2): synthesis of intermediate B1
Experimental operation: raw material 1-aminocyclo [3.3.3] azine (30 g,164.63 mmol) was added to a 1L three-necked flask, 500ml of N, N-dimethylformamide was added thereto, bromosuccinimide (73.25 g,411.58 mmol) was slowly added thereto, the reaction was carried out at-20℃for 3 hours, and after that, the system was added to 2L of water, a large amount of solids was precipitated, filtered, and the solids were recrystallized 2 times from toluene+ethanol to obtain the objective intermediate B148.56g.
Synthetic example (3): synthesis of intermediate A2
Experimental operation: adding intermediate A1 (40 g,127.40 mmol) and cuprous chloride (37.84 g,382.19 mmol) into A1L three-neck flask, adding 200ml acetonitrile, heating to 60 ℃ under the protection of nitrogen gas for reaction for 2h, slowly adding tert-butyl nitrite (40 g,382.19 mmol), heating to 60 ℃ for reaction for 3h, stopping heating, filtering, concentrating under reduced pressure to dryness, purifying by column chromatography to obtain a target product 36.24g
Synthetic example (4): synthesis of intermediate B2
Experimental operation: adding intermediate B1 (40 g,127.40 mmol) and cuprous chloride (36.39 g,352.92 mmol) into a 1L three-neck flask, adding 200ml acetonitrile, heating to 60 ℃ under the protection of nitrogen gas for reaction for 2 hours, slowly adding tert-butyl nitrite (36.39 g,352.92 mmol), heating to 60 ℃ for reaction for 3 hours, stopping heating, filtering, concentrating under reduced pressure to dryness, purifying by column chromatography to obtain a target product 34.21g
Synthetic example (5): synthesis of intermediate A3
Experimental operation: intermediate A2 (25 g,74.98 mmol), 4' -di-tert-butyldiphenylamine (46.43 g,146.96 mmol), pd 2 (dba) 3 (3.43 g,3.75 mmol), tri-tert-butylphosphine tetrafluoroborate (3.26 g,11.25 mmol), sodium tert-butoxide (21.62 g,224.95 mmol) were put into a 1L three-necked flask, 200ml toluene was added, the reaction was carried out at 110℃under nitrogen protection for 2 hours, then the heating was stopped, the filtration was carried out, the concentration was carried out under reduced pressure until it was dry, and the purification by column chromatography was carried out to obtain 45.21g of the target product
Synthetic example (6): synthesis of intermediate A4
Experimental operation: intermediate A2 (25 g,74.98 mmol), 4' -tertiarypentylbiphenyl amine (51.06 g,164.96 mmol), pd 2 (dba) 3 (3.43 g,3.75 mmol), tri-tert-butylphosphine tetrafluoroborate (3.29 g,11.25 mmol), sodium tert-butoxide (21.62 g,224.95 mmol) were put into a 1L three-necked flask, 200ml toluene was added, the reaction was carried out at 110℃under nitrogen protection for 2 hours, then the heating was stopped, the filtration was carried out, the concentration was carried out under reduced pressure until it was dry, and the column chromatography was carried out to obtain 30.14g of the target product
Synthetic example (7): synthesis of intermediate A5
Experimental operation: 4 '-methyl (1, 1' -biphenyl) -4-amine (25.8 g,140.77 mmol), 3-tert-butylbromobenzene (30 g,140.77 mmol), sodium tert-butoxide (27.06 g,281.53 mmol), DPPF palladium dichloride (5.11 g,7.04 mmol) were added to a 1L single port flask, 300ml toluene was added, after reacting at 110℃for 10 hours, heating was stopped, water washing and filtration were performed, and after drying under reduced pressure, toluene + methanol was used for recrystallization 2 times to give the target intermediate A5, 30.65g.
Synthetic example (8): synthesis of intermediate A6
Experimental operation: intermediate A2 (10 g,29.99 mmol), intermediate A5 (20.82 g,65.99 mmol), pd 2 (dba) 3 (1.37 g,1.50 mmol), tri-tert-butylphosphine tetrafluoroborate (1.31 g,4.5 mmol), sodium tert-butoxide (7.21 g,74.98 mmol) were put into a 1L single-neck flask, 200ml toluene was added, the reaction was continued for 2 hours at 110℃under nitrogen protection, then heating was stopped, and the mixture was concentrated to dryness under reduced pressure and purified by column chromatography to give the target intermediate A620.72g.
Synthetic example (9): synthesis of intermediate A7
Experimental operation: 2-naphthylamine (20.16 g,140.77 mmol), 3-tert-butylbromobenzene (30 g,140.77 mmol), sodium tert-butoxide (20.29 g,211.15 mmol), DPPF palladium dichloride (5.11 g,7.04 mmol) were added to a 1L single-neck flask, 300ml toluene was added, the reaction was carried out at 110℃for 10 hours, heating was stopped, washing with water was carried out, filtration was carried out, and after evaporation under reduced pressure, toluene+methanol was used for recrystallization 2 times to obtain the objective intermediate A7, 33.21g.
Synthetic example (10): synthesis of intermediate A8
Experimental operation: intermediate A2 (10 g,29.99 mmol), intermediate A5 (18.14 g,65.99 mmol), pd 2 (dba) 3 (1.37 g,1.50 mmol), tri-tert-butylphosphine tetrafluoroborate (1.31 g,4.5 mmol), sodium tert-butoxide (7.21 g,74.98 mmol) were put into a 1L single-neck flask, 200ml toluene was added, the reaction was continued for 2 hours at 110℃under nitrogen protection, then heating was stopped, and the mixture was concentrated to dryness under reduced pressure and purified by column chromatography to give the target intermediate A816.35g.
Synthetic example (10): synthesis of intermediate A9
Experimental operation: para-tert-butylaniline (24.60 g,164.82 mmol), 4-cyanobromobenzene (30 g,164.82 mmol), sodium t-butoxide (23.76 g,247.23 mmol), DPPF palladium dichloride (5.98 g,8.24 mmol) were added to a 1L single-necked flask, 300ml of toluene was added, the reaction was carried out at 110℃for 10 hours, heating was stopped, washing with water was carried out, filtration was carried out, and after evaporation under reduced pressure, toluene + methanol was used for recrystallization 2 times to obtain the objective intermediate A9, 30.21g.
Synthetic example (11): synthesis of intermediate A10
Experimental operation: intermediate A2 (10 g,29.99 mmol), intermediate A9 (16.52 g,65.99 mmol), pd 2 (dba) 3 (1.37 g,1.50 mmol), tri-tert-butylphosphine tetrafluoroborate (1.31 g,4.5 mmol), sodium tert-butoxide (7.21 g,74.98 mmol) were charged into a 1L single-neck flask, 200ml toluene was added, the reaction was continued for 2 hours at 110℃under nitrogen protection, then heating was stopped, concentrated to dryness under reduced pressure, and purified by column chromatography to give the objective intermediate A1017.06g.
Synthetic example (11): synthesis of Material M3
Experimental operation: intermediate A3 (15 g,20.42 mmol) was added to a 500ml three-neck flask, 200ml of ultra-dry xylene was added, tert-butyllithium (32 ml,1.6M,51.06 mmol) was slowly added under nitrogen protection at-40 ℃, then activated at 60℃for 1h, then boron tribromide (15.35 g,61.27 mmol) was added under nitrogen protection at-40℃successively, DIEA (9.24 g,71.48 mmol), then heated at 110℃for 15h, heating was stopped, and column chromatography purification was performed to give the objective 2.1g.
Synthetic example (12): synthesis of Material M146
Experimental operation: intermediate A4 (15 g,18.97 mmol) was added to a 500L three-neck flask, ultra-dry xylene 300ml was added, tert-butyllithium (47.43 mmol,1.6M,34 ml) was slowly added at-40℃under nitrogen protection, then activated at 60℃for 1h, boron tribromide (14.26 g,56.92 mmol) and diisopropylethylamine (9.81 g,75.89 mmol) were slowly added at-40℃and heated at 110℃for 10h, then heating was stopped, concentrated to dryness under reduced pressure, and purified by column chromatography to give 1.97g of the product.
Synthetic example (13): synthesis of Material M71
Experimental operation: intermediate A6 (15 g,18.69 mmol) was added to a 500L three-neck flask, ultra-dry xylene 300ml was added, tert-butyllithium (46.73 mmol,1.6M,30 ml) was slowly added at-40℃under nitrogen protection, then activated at 60℃for 1h, boron tribromide (14.05 g,56.07 mmol) and diisopropylethylamine (8.46 g,65.42 mmol) were slowly added at-40℃and heated at 110℃for 10h, then heating was stopped, concentrated to dryness under reduced pressure, and purified by column chromatography to give 1.45g of the product.
Synthetic example (14): synthesis of Material M113
Experimental operation: intermediate A8 (15 g,20.76 mmol) was added to a 500L three-neck flask, ultra-dry xylene (300 ml) was added, tert-butyllithium (51.91 mmol,1.6M,32 ml) was slowly added at-40℃under nitrogen protection, then activated at 60℃for 1h, boron tribromide (15.61 g,62.29 mmol) and diisopropylethylamine (9.39 g,72.68 mmol) were slowly added at-40℃and heated at 110℃for 10h, then heating was stopped, concentrated to dryness under reduced pressure, and purified by column chromatography to give 1.64g of the product.
Synthetic example (14): synthesis of Material M10
Experimental operation: intermediate A10 (15 g,22.31 mmol) was added to a 500mL three-necked flask, ultra-dry xylene 300mL was added, tert-butyllithium (55.78 mmol,1.6M,34 mL) was slowly added at-40℃under nitrogen protection, then activated at 60℃for 1h, boron tribromide (16.77 g,66.94 mmol) and diisopropylethylamine (10.09 g,78.09 mmol) were slowly added at-40℃and heated at 110℃for 10h, then heating was stopped, and concentrated to dryness under reduced pressure, followed by column chromatography purification to give 1.89g of the product.
Synthetic example (15): synthesis of intermediate B3
Experimental operation: intermediate B2 (10 g,27.82 mmol), 4' -di-tert-butyldiphenylamine (17.23 g,61.21 mmol), pd 2 (dba) 3 (1.27 g,1.39 mmol), tri-tert-butylphosphine tetrafluoroborate (1.21 g,4.17 mmol), sodium tert-butoxide (8.02 g,83.46 mmol) were added to a 500mL single-neck flask, 200mL toluene was added, the reaction was continued for 2 hours at 110℃under nitrogen, heating was stopped, and the mixture was concentrated to dryness under reduced pressure and purified by column chromatography to give the target intermediate B317.74g.
Synthetic example (16): synthesis of intermediate B4
Experimental operation: intermediate B2 (10 g,27.82 mmol), intermediate A9 (15.32 g,61.21 mmol), pd 2 (dba) 3 (1.27 g,1.39 mmol), tri-tert-butylphosphine tetrafluoroborate (1.21 g,4.17 mmol), sodium tert-butoxide (8.02 g,83.46 mmol) were put into a 500mL single-neck flask, 200mL toluene was added, the reaction was continued for 2 hours at 110℃under nitrogen protection, then heating was stopped, concentrated to dryness under reduced pressure, and purified by column chromatography to give the target intermediate B415.33g.
Synthetic example (16): synthesis of intermediate B5
Experimental operation: intermediate B2 (10 g,27.82 mmol), intermediate A5 (19.31 g,61.21 mmol), pd 2 (dba) 3 (1.27 g,1.39 mmol), tri-tert-butylphosphine tetrafluoroborate (1.21 g,4.17 mmol), sodium tert-butoxide (6.68 g,69.55 mmol) were put into a 500mL single-neck flask, 200mL toluene was added, the reaction was continued for 2 hours at 110℃under nitrogen protection, then heating was stopped, concentrated to dryness under reduced pressure, and purified by column chromatography to give the objective intermediate B511.32g.
Synthetic example (17): synthesis of Material M120
Experimental operation: intermediate B3 (15 g,19.72 mmol) was added to a 500mL three-necked flask, ultra-dry xylene (300 mL) was added, tert-butyllithium (49.31 mmol,1.6M,31 mL) was slowly added at-40℃under nitrogen protection, then activated at 60℃for 1h, boron tribromide (14.82 g,59.17 mmol) and diisopropylethylamine (8.92 g,69.03 mmol) were slowly added at-40℃and heated at 110℃for 10h, then heating was stopped, and concentrated to dryness under reduced pressure, followed by column chromatography purification to give 1.13g of the product.
Synthetic example (17): synthesis of Material M129
Experimental operation: intermediate B4 (15 g,21.48 mmol) was added to a 500mL three-necked flask, ultra-dry xylene (300 mL) was added, tert-butyllithium (53.70 mmol,1.6M,33 mL) was slowly added at-40℃under nitrogen protection, then activated at 60℃for 1h, boron tribromide (16.14 g,64.44 mmol) and diisopropylethylamine (9.72 g,75.18 mmol) were slowly added at-40℃and heated at 110℃for 10h, then heating was stopped, concentrated to dryness under reduced pressure, and purified by column chromatography to give 1.24g of the product.
Synthetic example (18): synthesis of Material M134
Experimental operation: intermediate B5 (15 g,18.10 mmol) was added to a 500mL three-necked flask, ultra-dry xylene (300 mL) was added, tert-butyllithium (45.26 mmol,1.6M,29 mL) was slowly added at-40℃under nitrogen protection, then activated at 60℃for 1h, boron tribromide (13.61 g,54.31 mmol) and diisopropylethylamine (8.19 g,63.36 mmol) were slowly added at-40℃and heated at 110℃for 10h, then heating was stopped, concentrated to dryness under reduced pressure, and purified by column chromatography to give 1.10g of the product.
Synthetic example (19): synthesis of Material M160
Experimental operation: intermediate A10 (25 g,31.31 mmol) was added to a 500mL three-necked flask, ultra-dry xylene (300 mL) was added, tert-butyllithium (78.27 mmol,1.6M,46 mL) was slowly added at-40℃under nitrogen protection, then activated at 60℃for 1h, boron tribromide (23.53 g,93.92 mmol) and diisopropylethylamine (16.19 g,125.23 mmol) were slowly added at-40℃and heated at 110℃for 10h, then heating was stopped, concentrated to dryness under reduced pressure, and purified by column chromatography to give 2.06g of the product.
Theoretical calculation
The invention adopts Gaussian03 to carry out quantum chemical calculation on the compounds, adopts a time-dependent density functional method to respectively carry out theoretical calculation on the compounds listed in table 1, and the calculation results are shown in table 1. The specific chemical structure shown in the general formula 1 is regulated, so that materials with different luminescent colors can be obtained, and the materials have better light tone saving scope, and are a molecular design scheme with wide application prospects.
Table 1:
| numbering of compounds | S1/eV | Luminescence peak/nm |
| M1 | 2.95 | 420 |
| M160 | 1.91 | 650 |
Device implementation method
The OLED includes a first electrode and a second electrode, 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 particular embodiments, a substrate may be used below the first electrode or above the second electrode. The substrates are all glass or polymer materials with excellent mechanical strength, thermal stability, water resistance and transparency. 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 serving as the first electrode on the substrate. When the first electrode is used as the anode, an oxide transparent conductive material such as Indium Tin Oxide (ITO), indium Zinc Oxide (IZO), tin dioxide (SnO 2), zinc oxide (ZnO), or the like, and any combination thereof may be used. When the first electrode is used as the cathode, metals or alloys such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), ytterbium (Yb), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and any combinations thereof may be used.
The organic material layer may be formed on the electrode by vacuum thermal evaporation, spin coating, printing, or the like. The compounds used as the organic material layer may be small organic molecules, large organic molecules and polymers, and combinations 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 hole transport layer containing only one compound and a single layer hole transport layer containing a plurality of compounds. The hole transport region may have a multilayer 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 conductive dopant containing polymers such as polystyrene, 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 those shown below as HT-1 through 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 of the compounds HT-1 through HT-51 described above, or one or more of the compounds HI-1-HI-3 described below; one or more compounds from HT-1 to HT-51 may also be used to dope one or more of HI-1-HI-3 described below.
The luminescent layer comprises luminescent dyes (i.e. dopants) that can emit different wavelength spectra, and may also comprise Host materials (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 plurality of monochromatic light emitting layers with different colors can be arranged in a plane according to the pixel pattern, or can be stacked together 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 simultaneously emitting different colors such as red, green, and blue.
According to different technologies, the luminescent layer material can be made of different materials such as fluorescent electroluminescent material, phosphorescent electroluminescent material, thermal activation delayed fluorescence luminescent material and the like. In an OLED device, a single light emitting technology may be used, or a combination of different light emitting technologies may be used. The different luminescent materials classified by the technology can emit light of the same color, and can also emit light of different colors.
In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescence technology. The light-emitting layer host material is selected from, but not limited to, one or more of PH-1 to PH-85.
In the present invention, the light emitting layer used in the organic electroluminescent device includes, in addition to the host material, a first dopant and a second dopant, wherein the first dopant may be selected from, but is not limited to, one or more combinations of TDE1-TDE49 listed below, and the second dopant is selected from one or more combinations of compounds represented by formula I;
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 employ, but is not limited to, one or more compounds of HT-1 through HT-51 described above, or one or more compounds of PH-47 through PH-77 described above; mixtures of one or more compounds of HT-1 through HT-51 and one or more compounds of PH-47 through PH-77 may also be employed, 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 in the organic electroluminescent device may be selected from, but is not limited to, one or more combinations of ET-1 to ET-73 listed below.
In one aspect of the present invention, a Hole Blocking Layer (HBL) in an organic electroluminescent device is located between an electron transport layer and a light emitting layer. The hole blocking layer may employ, but is not limited to, one or more of the compounds ET-1 to ET-73 described above, or one or more of the compounds PH-1 to PH-46; mixtures of one or more compounds of ET-1 to ET-73 with one or more compounds of PH-1 to PH-46 may also be employed, but are not limited to.
The organic electroluminescent device of the present invention may further comprise an electron injection layer between the electron transport layer and the cathode, the electron injection layer material including, but not limited to, one or more of the following combinations:
LiQ、LiF、NaCl、CsF、Li 2 O、Cs 2 CO 3 、BaO、Na、Li、Ca、Mg、Yb。
specific device embodiments
The preparation process of the organic electroluminescent device in this embodiment is as follows:
the glass plate coated with the ITO transparent conductive layer was sonicated in commercial cleaners, rinsed in deionized water, and rinsed in acetone: ultrasonic degreasing in ethanol mixed solvent, baking in clean environment to completely remove water, cleaning with ultraviolet light and ozone, and bombarding surface with low-energy cation beam;
Placing the above glass substrate with anode in vacuum cavity, and vacuumizing to less than 1×10 -5 Pa, vacuum evaporating HT-4:HI-3 (97/3,w/w) mixture on the anode layer film to obtain a hole injection layer, wherein the evaporation rate is 0.1nm/s, and the thickness of the evaporation film is 10nm;
vacuum evaporation HT-4 is carried out on the hole injection layer to serve as a hole transmission layer of the device, the evaporation rate is 0.1nm/s, and the total film thickness of evaporation is 60nm;
vacuum evaporation HT-51 is carried out on the hole transport layer to serve as an electron blocking layer of the device, the evaporation rate is 0.1nm/s, and the total film thickness of evaporation is 5nm;
blue light device light emitting layer (device example 1):
vacuum evaporating a luminescent layer of the device on the electron blocking layer, wherein the luminescent layer comprises a main material and a dye material, and evaporating a ternary mixture of 40nm compound PH-54:TDE23:fluorescent dye (100:40:1, w/w/w) serving as the luminescent layer by utilizing a multi-source co-evaporation method, wherein the fluorescent dye adopts the compound M1;
red light device light emitting layer (device example 19):
vacuum evaporating a luminescent layer of the device on the electron blocking layer, wherein the luminescent layer comprises a main material, a sensitizer and a dye material, and evaporating a ternary mixture of 40nm compound PH-14:TDE42:fluorescent dye (100:50:1, w/w/w) serving as the luminescent layer by utilizing a multi-source co-evaporation method, wherein the fluorescent dye adopts the organic compound M160 provided by the invention;
Vacuum evaporating PH-28 with the thickness of 5nm on the light-emitting layer as a hole blocking layer, and a mixture of compounds ET-69:ET-57 (50/50, w/w) with the thickness of 25nm as an electron transport layer, wherein the evaporation rate is 0.1nm/s;
LiF with the thickness of 1nm is vacuum evaporated on an Electron Transport Layer (ETL) to serve as an electron injection layer, 150nm of metal aluminum is used as a cathode, the total evaporation rate of LiF is controlled to be 0.1 nm/second, and the evaporation rate of a metal electrode is controlled to be 1 nm/second.
Device example 2 to device example 18:
the same procedure as in device example 1 was followed except that the luminescent dye in the luminescent layer was replaced with the inventive compound M1 by the inventive compounds M3, M8, M9, M10, M11, M15, M17, M71, M113, M118, M119, M120, M129, M134, M146, M154 and M155 listed in Table 2, respectively.
The device comparative example 1 and the device comparative example 2 were fabricated by the same method as the device example 1, except that the luminescent dye in the luminescent layer was replaced with the compounds N-2 and N-3 in the prior art by the compound M1 of the present invention, and the corresponding synthetic preparation methods of N-1, N-2 and N-3 were referred to CN111333671A, CN112279872a and CN110790782a, and will not be repeated here.
Device example 20 to device example 24 and device comparative example 3:
prepared in the same manner as in device example 19 except that the luminescent dye in the luminescent layer was replaced with the compound M160 of the present invention as the compound of the present invention shown in Table 3: m161, M166, M167, M175, M177, N-1.
Method for testing a device (including apparatus and test conditions):
the organic electroluminescent device prepared by the above procedure was subjected to the following performance measurement:
measuring the external quantum efficiency of the organic electroluminescent device by using an integrating sphere; the driving voltages of the organic electroluminescent devices prepared in examples 1 to 18 and comparative examples 1 to 3 were measured using a digital source meter and a luminance meter at the same luminance. Specifically, the luminance of the organic electroluminescent device was measured to reach 1000cd/m by increasing the voltage at a rate of 0.1V per second 2 The voltage at that time is the driving voltage. The lifetime test of LT95 is as follows: at 1000cd/m using a luminance meter 2 Under the condition of brightness, constant current is kept, and the brightness of the organic electroluminescent device is measured to be reduced to 950cd/m 2 The lifetime of the device of comparative example 1 was set to 1.0 and the remaining material lifetime properties were all ratios to it, in hours.
The properties of the organic electroluminescent devices prepared in the respective device examples and comparative examples are shown in table 2 below.
Table 2:
testing the light color of the device by testing the fluorescence emission spectrum; measuring the external quantum efficiency of the organic electroluminescent device by using an integrating sphere; the driving voltages of the organic electroluminescent devices prepared in examples 19 to 24 and comparative example 3 were measured using a digital source meter and a luminance meter at the same luminance. Specifically, the luminance of the organic electroluminescent device was measured to reach 1000cd/m by increasing the voltage at a rate of 0.1V per second 2 The voltage at that time is the driving voltage. The lifetime test of LT95 is as follows: at 1000cd/m using a luminance meter 2 Under the condition of brightness, constant current is kept, and the brightness of the organic electroluminescent device is measured to be reduced to 950cd/m 2 The lifetime of device comparative example 3 was set to 1.0 in hours, and the remaining material lifetime properties were all ratios thereto.
Table 3:
as can be seen from table 2, in the case that the material schemes and the preparation processes of the other functional layers in the organic electroluminescent device structure are completely the same, compared with the organic electroluminescent devices prepared in comparative examples 1 to 18, the organic electroluminescent devices prepared in examples 1 to 2 of the device of the present invention can effectively reduce the device voltage by 0.5 to 0.9V. This is probably because the introduction of N-heteroaromatic ring has good carrier transport properties (the rigid planar structure enhances hole transport properties), reducing charge stacking in the light emitting layer, so the voltage is significantly reduced. While all devices prepared in examples 1-18 exhibited significantly higher external quantum efficiencies than comparative examples 1-2, it is likely that the improvement in carrier transport was due. In addition, the device lifetime of all examples is significantly higher than that of the comparative examples, probably due to the rigid structure of the molecular center core of the compounds of the invention and good hole transport.
Two pyridine hetero atoms are arranged below a compound N-1 in the prior art, a plurality of pyridine heterocycles are arranged on the molecule of the compound N-2, and the compound is easy to capture impurities in the environment, including metal ions, water molecules and the like, so that the stability of a device is damaged; the C-O double bond in the N-3 structure of the compound has poor stability, and meanwhile, the compound has steric hindrance with a benzene ring beside the compound to cause the distortion of a molecular structure. Therefore, the devices prepared by the three comparison compounds show the performance characteristics of voltage rise and poor service life compared with the devices prepared by the compounds.
The present invention is described in detail by the above examples, but the present invention is not limited to the above detailed methods, i.e., it does not mean that the present invention must be practiced depending on the above detailed methods. While the invention has been described in connection with the embodiments, it is to be understood that the invention is not limited to the above embodiments, but is capable of numerous modifications and improvements by those skilled in the art under the guidance of the inventive concept, and the scope of the invention is outlined in the appended claims, and equivalent substitutions for various raw materials of the inventive product, addition of auxiliary components, selection of specific modes, etc., are all within the scope of the invention and the scope of the disclosure.
Claims (14)
1. An organic compound having a structure represented by formula (1):
ring A is connected with ring B condensed ring, ring A and ring B independently represent any one of substituted or unsubstituted C5-C60 aromatic ring and substituted or unsubstituted C4-C60 heteroaromatic ring;
ring C, ring D, ring E, ring F each independently represent one of a substituted or unsubstituted C5-C60 aromatic ring, a substituted or unsubstituted C3-C60 heteroaromatic ring; by single bond, -O-, -S-, -CR between ring D and ring C 1 R 2 -or-NR 3 R 4 Linking or ring D toThe rings C are not connected, and the E ring and the F ring are connected through single bonds, -O-, -S-, -CR 1 R 2 -or-NR 3 R 4 The E ring is connected with the F ring or the E ring is not connected with the F ring;
R 1 、R 2 、R 3 、R 4 each independently selected from one or two combinations of halogen, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkyl silicon base, C1-C20 alkyl amino, cyano, nitro, hydroxyl, amino, C6-C30 aryl amino, C3-C30 heteroaryl amino, C6-C30 aryloxy, C3-C30 heteroaryl oxy, C6-C60 aryl and C3-C60 heteroaryl;
the substituent groups in the ring A, the ring B, the ring C, the ring D, the ring E and the ring F are respectively and independently selected from at least one of halogen, unsubstituted or R ' substituted C1-C20 chain alkyl, unsubstituted or R ' substituted C3-C20 cycloalkyl, unsubstituted or R ' substituted C1-C20 alkoxy, unsubstituted or R ' substituted C1-C20 alkyl silicon base, unsubstituted or R ' substituted C1-C20 alkylamino, cyano, nitro, hydroxyl, amino, unsubstituted or R ' substituted C6-C30 arylamino, unsubstituted or R ' substituted C3-C30 heteroaryl amino, unsubstituted or R ' substituted C6-C30 aryloxy, unsubstituted or R ' substituted C3-C30 heteroaryl, unsubstituted or R ' substituted C6-C60 aryl and unsubstituted or R ' substituted C3-C60 heteroaryl;
R' is selected from one or two of halogen, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkyl silicon base, cyano, nitro, hydroxyl, amino, C6-C30 aryl amino, C3-C30 heteroaryl amino, C6-C30 aryloxy, C3-C30 heteroaryl oxy, C6-C60 aryl and C3-C60 heteroaryl;
the substituents in ring A, ring B, ring C, ring D, ring E, ring F are each independently unconnected, or adjacent two substituents are connected by a chemical bond to form a ring.
2. The organic compound according to claim 1, wherein the rings a and B each independently represent any one of a substituted or unsubstituted C5 to C14 aromatic ring and a substituted or unsubstituted C4 to C20 heteroaromatic ring;
the ring C, the ring D, the ring E and the ring F respectively and independently represent one of a substituted or unsubstituted C5-C14 aromatic ring and a substituted or unsubstituted C3-C14 heteroaromatic ring.
3. The organic compound according to claim 1 or 2, wherein at least one of the ring D and the ring E has a structure represented by formula (a), and at least one of the ring C and the ring F has a structure represented by formula (b):
in formula (a), c represents a shared bond position of formula (a) to formula (1), and in formula (b), represents a group attachment site;
The Z is 1 、Z 2 、Z 3 、Z 4 、Z 5 、Z 6 、Z 7 、Z 8 And Z 9 Are independently selected from CR 1 Or N, the R 1 Independently selected from at least one of hydrogen, halogen, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C1-C20 alkylamino, cyano, nitro, hydroxy, amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, said R 1 Are not independently connected, or adjacent two R 1 Is connected into a ring through a chemical bond;
R 1 the substituents of the substituents are each independently selected from the group consisting of chain halogen, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, cyano, nitro, hydroxy, amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60One or two of aryl and C3-C60 heteroaryl.
4. The organic compound according to claim 3, having a structure represented by formula (1-1):
in the formula (1-1), the Z 1’ 、Z 2’ 、Z 3’ 、Z 4’ 、Z 5’ 、Z 6’ 、Z 7’ 、Z 8’ And Z 9’ Definition of (1) and Z 1 、Z 2 、Z 3 、Z 4 、Z 5 、Z 6 、Z 7 、Z 8 And Z 9 Is the same as defined in the specification;
the definition of the ring A and the ring B is the same as that in the formula (1);
the ring D and the ring C are connected through a single bond, -O-, -S-, -CR 1 R 2 -or-NR 3 R 4 Linking or not linking ring D to ring C, said E ring being linked to F ring by a single bond, -O-, -S-, -CR 1 R 2 -or-NR 3 R 4 The E ring and the F ring are connected or not connected.
5. The organic compound according to claim 4, having a structure represented by formula (1-2):
in the formula (1-2), the dotted line represents the connection or disconnection.
6. The organic compound according to claim 4 or 5, wherein the ring a and the ring B are each independently selected from structures represented by the following formula (c) or formula (d):
in the formulas (c) and (d), the dotted line represents the position of the shared chemical bond connected to the formula (1), and "N'" represents "N" in the formula (1);
the Z is 11 、Z 12 、Z 13 、Z 14 、Z 15 Are independently selected from CR 2 Or N, the R 2 At least one selected from the group consisting of hydrogen, halogen, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C1-C20 alkylamino, cyano, nitro, hydroxy, amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl;
The R is 2 Are not independently connected, or adjacent two R 2 Is connected into a ring through a chemical bond;
R 2 the substituted substituents of the above are each independently selected from one or two of halogen, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkyl silicon base, cyano, nitro, hydroxyl, amino, C6-C30 aryl amino, C3-C30 heteroaryl amino, C6-C30 aryloxy, C3-C30 heteroaryl oxy, C6-C60 aryl and C3-C60 heteroaryl.
7. The organic compound according to claim 4, having a structure represented by formula (1-3) or formula (1-4):
in the formula (1-3), the formula (1-4) and the formula (1-3-2), the ring D and the ring C are formed by single bond, -O-, -S-, -CR 1 R 2 -or-NR 3 R 4 Linking or not linking ring D to ring C, said E ring being linked to F ring by a single bond, -O-, -S-, -CR 1 R 2 -or-NR 3 R 4 The E ring is connected with the F ring or the E ring is not connected with the F ring;
the Z is 11 、Z 12 、Z 13 、Z 11’ 、Z 12’ 、Z1 3’ 、Z 14 、Z 15 、Z 14’ 、Z 15’ 、Z 16 、Z 17 、Z 18 Are independently selected from CR 2 Or N, the R 2 At least one selected from the group consisting of hydrogen, halogen, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 alkylsilyl, substituted or unsubstituted C1-C20 alkylamino, cyano, nitro, hydroxy, amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl;
R 2 Wherein each of the substituted substituents is independently selected from one or a combination of two of halogen, C1-C20 chain alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, cyano, nitro, hydroxy, amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, C3-C60 heteroaryl;
preferably, the organic compound has a structure represented by formula (1-5) or formula (1-6):
in the formula (1-5) or the formula (1-6), the dotted line represents the connection or disconnection.
8. The organic compound according to claim 7,the Z is 1 、Z 2 、Z 3 、Z 4 、Z 5 、Z 6 、Z 7 、Z 8 、Z 9 、Z 1’ 、Z 2’ 、Z 3’ 、Z 4’ 、Z 5’ 、Z 6’ 、Z 7’ 、Z 8’ And Z 9’ Are independently selected from CR 1 Or N, said Z 11 、Z 12 、Z 13 、Z 11’ 、Z 12’ 、Z 13’ 、Z 14 、Z 15 、Z 14’ 、Z 15’ Are independently selected from CR 2 Or N;
the R is 1 、R 2 Each independently selected from at least one of hydrogen, halogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C1-C10 alkylsilyl, substituted or unsubstituted C1-C10 alkylamino, cyano, nitro, hydroxy, amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl;
R 1 、R 2 The substituted substituents of the above are each independently selected from one or two of halogen, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 alkyl silicon base, cyano, nitro, hydroxyl, amino, C6-C30 aryl amino, C3-C30 heteroaryl amino, C6-C30 aryloxy, C3-C30 heteroaryl oxy, C6-C30 aryl and C3-C30 heteroaryl.
9. The organic compound according to claim 7, having a structure represented by formula (1-7) or formula (1-8):
in the formulae (1-7) and (1-8), the dotted line represents the connection or disconnection;
R 2 and R is 3 Each independently represents a single substituent up to a maximum allowable number of substituents, R 2 、R 3 At least one of hydrogen, halogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkylamino, cyano, nitro, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl;
R 2 And R is 3 Wherein each of the substituted substituents is independently selected from one or a combination of two of a chain halogen, a C1-C20 chain alkyl, a C3-C20 cycloalkyl, a C1-C20 alkoxy, a C1-C20 alkylsilyl, cyano, nitro, hydroxy, amino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, C3-C60 heteroaryl;
preferably, R 2 、R 3 Each independently selected from hydrogen;
preferably, in the formulas (1-7) and (1-8), the broken line is not connected.
10. The organic compound according to claim 9, wherein in the formulae (1 to 7) and (1 to 8), the Z 1 、Z 2 、Z 3 、Z 4 、Z 1’ 、Z 2’ 、Z 3’ 、Z 4’ Are independently selected from CR 1 ；
Preferably, the Z 1 、Z 2 、Z 3 、Z 4 、Z 1’ 、Z 2’ 、Z 3’ 、Z 4’ Are independently selected from CR 1 The R is 1 Independently selected from at least one of hydrogen, C1-C10 chain alkyl and C3-C10 cycloalkyl;
still preferably, the Z 1 、Z 2 、Z 3 、Z 4 、Z 1’ 、Z 2’ 、Z 3’ 、Z 4’ Are independently selected from CR 1 The R is 1 Independently selected from hydrogen or C1-C10 chain alkyl, said Z 5 、Z 6 、Z 7 、Z 8 、Z 9 、Z 5’ 、Z 6’ 、Z 7’ 、Z 8’ And Z 9’ Are independently selected from CR 1’ Or N, the R 1’ At least one selected from the group consisting of hydrogen, halogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C1-C10 alkylsilyl, substituted or unsubstituted C1-C10 alkylamino, cyano, nitro, hydroxy, amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl;
Further preferably, the Z 1 、Z 2 、Z 3 、Z 4 、Z 1’ 、Z 2’ 、Z 3’ 、Z 4’ Are independently selected from CR 1 The R is 1 Independently selected from hydrogen or C1-C10 chain alkyl, said Z 5 、Z 6 、Z 7 、Z 8 、Z 9 、Z 5’ 、Z 6’ 、Z 7’ 、Z 8’ And Z 9’ Are independently selected from CR 1’ Or N, the R 1’ At least one selected from the group consisting of hydrogen, halogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkylamino, cyano, nitro, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C3-C30 heteroaryloxy, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl;
more preferably, said Z 1 、Z 2 、Z 3 、Z 4 、Z 1’ 、Z 2’ 、Z 3’ 、Z 4’ Are independently selected from CR 1 The R is 1 Independently selected from hydrogen, methyl, ethyl, isopropyl, tert-butyl, isobutyl or tert-pentyl, said Z 5 、Z 6 、Z 7 、Z 8 、Z 9 、Z 5’ 、Z 6’ 、Z 7’ 、Z 8’ And Z 9’ Are independently selected from CR 1’ Or N, the R 1’ Independently selected from at least one of hydrogen, C1-C10 chain alkyl and C3-C10 cycloalkyl.
11. The organic compound according to claim 9, wherein Z 1 、Z 2 、Z 3 、Z 4 One of them is selected from CR 1 The R is 1 Independently selected from at least one of C1-C10 chain alkyl and C3-C10 cycloalkyl, and Z at the same time 1 、Z 2 、Z 3 、Z 4 Three other of (a) are selected from CR 1 Said R is 1 Is hydrogen; and Z 1’ 、Z 2’ 、Z 3’ 、Z 4’ One of them is selected from CR 1’ The R is 1’ Independently selected from at least one of C1-C10 chain alkyl and C3-C10 cycloalkyl, and Z at the same time 1’ 、Z 2’ 、Z 3’ 、Z 4’ Three other of (a) are selected from CR 1’ Said R is 1’ Is hydrogen;
preferably, Z 2 Selected from CR 1 The R is 1 Selected from one of C1-C10 chain alkyl and C3-C10 cycloalkyl, and Z at the same time 1 、Z 3 、Z 4 Selected from CR 1 Said R is 1 Is hydrogen, and Z 2’ Selected from CR 1’ The R is 1’ Selected from one of C1-C10 chain alkyl and C3-C10 cycloalkyl, and Z at the same time 1’ 、Z 3’ 、Z 4’ Selected from CR 1’ Said R is 1’ Is hydrogen;
alternatively, Z 3 Selected from CR 1 The R is 1 Selected from one of C1-C10 chain alkyl and C3-C10 cycloalkyl, and Z at the same time 1 、Z 2 、Z 4 Selected from CR 1 Said R is 1 Is hydrogen, and Z 3’ Selected from CR 1’ The R is 1’ Selected from one of C1-C10 chain alkyl and C3-C10 cycloalkyl, and Z at the same time 1’ 、Z 2’ 、Z 4’ Selected from CR 1’ Said R is 1’ Is hydrogen;
more preferably, Z 2 Selected from CR 1 The R is 1 Selected from methyl, ethyl, isopropyl, tert-butyl, isobutyl or tert-pentyl, and at the same time Z 1 、Z 3 、Z 4 Selected from CR 1 Said R is 1 Is hydrogen, and Z 2’ Selected from CR 1’ The R is 1’ Selected from methyl, ethyl, isopropyl, tert-butyl, isobutyl or tert-pentyl, and at the same time Z 1’ 、Z 3’ 、Z 4’ Selected from CR 1’ Said R is 1’ Is hydrogen;
Alternatively, Z 3 Selected from CR 1 The R is 1 Selected from methyl, ethyl, isopropyl, tert-butyl, isobutyl or tert-pentyl, and at the same time Z 1 、Z 2 、Z 4 Selected from CR 1 Said R is 1 Is hydrogen, and Z 3’ Selected from CR 1’ The R is 1’ Selected from methyl, ethyl, isopropyl, tert-butyl, isobutyl or tert-pentyl, and at the same time Z 1’ 、Z 2’ 、Z 4’ Selected from CR 1’ Said R is 1’ Is hydrogen.
12. The organic compound according to claim 1, having the structure shown below:
13. use of an organic compound according to any one of claims 1 to 12 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 tag, an electronic artificial skin sheet, a sheet scanner or an electronic paper;
preferably, the organic compound is used as a light-emitting layer material in an organic electroluminescent device, more preferably as a light-emitting dye in a light-emitting layer.
14. An organic electroluminescent device comprising a first electrode, a second electrode, and one or more light-emitting functional layers interposed between the first electrode and the second electrode, wherein the light-emitting functional layers contain the organic compound according to any one of claims 1 to 12;
Preferably, the light-emitting functional layer comprises an electron blocking layer and at least one of a hole injection layer, a hole transport layer, a light-emitting layer and an electron transport layer, and the light-emitting layer contains the organic compound according to any one of claims 1 to 12.
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