CN111253396B - Organic compound, mixture, composition, high polymer and application - Google Patents
Organic compound, mixture, composition, high polymer and application Download PDFInfo
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- CN111253396B CN111253396B CN202010175998.4A CN202010175998A CN111253396B CN 111253396 B CN111253396 B CN 111253396B CN 202010175998 A CN202010175998 A CN 202010175998A CN 111253396 B CN111253396 B CN 111253396B
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- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 32
- 239000000203 mixture Substances 0.000 title claims description 31
- 229920000642 polymer Polymers 0.000 title claims description 12
- 239000000463 material Substances 0.000 claims abstract description 44
- 150000001875 compounds Chemical class 0.000 claims description 63
- 239000010410 layer Substances 0.000 claims description 42
- 238000002347 injection Methods 0.000 claims description 25
- 239000007924 injection Substances 0.000 claims description 25
- 125000003118 aryl group Chemical group 0.000 claims description 23
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
- 239000002346 layers by function Substances 0.000 claims description 14
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
- 230000005525 hole transport Effects 0.000 claims description 13
- 125000006413 ring segment Chemical group 0.000 claims description 13
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
- 125000000018 nitroso group Chemical group N(=O)* 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 4
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000000468 ketone group Chemical group 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 239000000975 dye Substances 0.000 claims description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
- 125000005067 haloformyl group Chemical group 0.000 claims description 3
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 239000012948 isocyanate Substances 0.000 claims description 3
- 150000002513 isocyanates Chemical class 0.000 claims description 3
- 125000002462 isocyano group Chemical group *[N+]#[C-] 0.000 claims description 3
- 150000002540 isothiocyanates Chemical class 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 3
- AFYPFACVUDMOHA-UHFFFAOYSA-N chlorotrifluoromethane Chemical compound FC(F)(F)Cl AFYPFACVUDMOHA-UHFFFAOYSA-N 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims 1
- 239000002019 doping agent Substances 0.000 abstract description 7
- 230000015572 biosynthetic process Effects 0.000 description 202
- 238000003786 synthesis reaction Methods 0.000 description 202
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 78
- 238000001308 synthesis method Methods 0.000 description 46
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- 229910052757 nitrogen Inorganic materials 0.000 description 15
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 12
- 230000000903 blocking effect Effects 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 239000012074 organic phase Substances 0.000 description 9
- 125000004429 atom Chemical group 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 4
- -1 monocyclic compound Chemical class 0.000 description 4
- WEOKHGKSYLOTPP-UHFFFAOYSA-N 2-methylbutanedinitrile Chemical compound N#CC(C)CC#N WEOKHGKSYLOTPP-UHFFFAOYSA-N 0.000 description 3
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- ASGMFNBUXDJWJJ-JLCFBVMHSA-N (1R,3R)-3-[[3-bromo-1-[4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-N,1-dimethylcyclopentane-1-carboxamide Chemical compound BrC1=NN(C2=NC(=NC=C21)N[C@H]1C[C@@](CC1)(C(=O)NC)C)C1=CC=C(C=C1)C=1SC(=NN=1)C ASGMFNBUXDJWJJ-JLCFBVMHSA-N 0.000 description 2
- UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 description 2
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 2
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 2
- GCTFTMWXZFLTRR-GFCCVEGCSA-N (2r)-2-amino-n-[3-(difluoromethoxy)-4-(1,3-oxazol-5-yl)phenyl]-4-methylpentanamide Chemical compound FC(F)OC1=CC(NC(=O)[C@H](N)CC(C)C)=CC=C1C1=CN=CO1 GCTFTMWXZFLTRR-GFCCVEGCSA-N 0.000 description 2
- IUSARDYWEPUTPN-OZBXUNDUSA-N (2r)-n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-[3-(1,3-thiazol-2-yl)phenyl]butan-2-yl]-2-methoxypropanamide Chemical compound C([C@H](NC(=O)[C@@H](C)OC)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C(C=1)=CC=CC=1C1=NC=CS1 IUSARDYWEPUTPN-OZBXUNDUSA-N 0.000 description 2
- YJLIKUSWRSEPSM-WGQQHEPDSA-N (2r,3r,4s,5r)-2-[6-amino-8-[(4-phenylphenyl)methylamino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1CNC1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O YJLIKUSWRSEPSM-WGQQHEPDSA-N 0.000 description 2
- VIJSPAIQWVPKQZ-BLECARSGSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-acetamido-5-(diaminomethylideneamino)pentanoyl]amino]-4-methylpentanoyl]amino]-4,4-dimethylpentanoyl]amino]-4-methylpentanoyl]amino]propanoyl]amino]-5-(diaminomethylideneamino)pentanoic acid Chemical compound NC(=N)NCCC[C@@H](C(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(C)=O VIJSPAIQWVPKQZ-BLECARSGSA-N 0.000 description 2
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 2
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 2
- UDQTXCHQKHIQMH-KYGLGHNPSA-N (3ar,5s,6s,7r,7ar)-5-(difluoromethyl)-2-(ethylamino)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazole-6,7-diol Chemical compound S1C(NCC)=N[C@H]2[C@@H]1O[C@H](C(F)F)[C@@H](O)[C@@H]2O UDQTXCHQKHIQMH-KYGLGHNPSA-N 0.000 description 2
- HUWSZNZAROKDRZ-RRLWZMAJSA-N (3r,4r)-3-azaniumyl-5-[[(2s,3r)-1-[(2s)-2,3-dicarboxypyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]amino]-5-oxo-4-sulfanylpentane-1-sulfonate Chemical compound OS(=O)(=O)CC[C@@H](N)[C@@H](S)C(=O)N[C@@H]([C@H](C)CC)C(=O)N1CCC(C(O)=O)[C@H]1C(O)=O HUWSZNZAROKDRZ-RRLWZMAJSA-N 0.000 description 2
- MPDDTAJMJCESGV-CTUHWIOQSA-M (3r,5r)-7-[2-(4-fluorophenyl)-5-[methyl-[(1r)-1-phenylethyl]carbamoyl]-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoate Chemical compound C1([C@@H](C)N(C)C(=O)C2=NN(C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C2C(C)C)C=2C=CC(F)=CC=2)=CC=CC=C1 MPDDTAJMJCESGV-CTUHWIOQSA-M 0.000 description 2
- OMBVEVHRIQULKW-DNQXCXABSA-M (3r,5r)-7-[3-(4-fluorophenyl)-8-oxo-7-phenyl-1-propan-2-yl-5,6-dihydro-4h-pyrrolo[2,3-c]azepin-2-yl]-3,5-dihydroxyheptanoate Chemical compound O=C1C=2N(C(C)C)C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C(C=3C=CC(F)=CC=3)C=2CCCN1C1=CC=CC=C1 OMBVEVHRIQULKW-DNQXCXABSA-M 0.000 description 2
- YQOLEILXOBUDMU-KRWDZBQOSA-N (4R)-5-[(6-bromo-3-methyl-2-pyrrolidin-1-ylquinoline-4-carbonyl)amino]-4-(2-chlorophenyl)pentanoic acid Chemical compound CC1=C(C2=C(C=CC(=C2)Br)N=C1N3CCCC3)C(=O)NC[C@H](CCC(=O)O)C4=CC=CC=C4Cl YQOLEILXOBUDMU-KRWDZBQOSA-N 0.000 description 2
- KKHFRAFPESRGGD-UHFFFAOYSA-N 1,3-dimethyl-7-[3-(n-methylanilino)propyl]purine-2,6-dione Chemical compound C1=NC=2N(C)C(=O)N(C)C(=O)C=2N1CCCN(C)C1=CC=CC=C1 KKHFRAFPESRGGD-UHFFFAOYSA-N 0.000 description 2
- MHSLDASSAFCCDO-UHFFFAOYSA-N 1-(5-tert-butyl-2-methylpyrazol-3-yl)-3-(4-pyridin-4-yloxyphenyl)urea Chemical compound CN1N=C(C(C)(C)C)C=C1NC(=O)NC(C=C1)=CC=C1OC1=CC=NC=C1 MHSLDASSAFCCDO-UHFFFAOYSA-N 0.000 description 2
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 2
- WGFNXGPBPIJYLI-UHFFFAOYSA-N 2,6-difluoro-3-[(3-fluorophenyl)sulfonylamino]-n-(3-methoxy-1h-pyrazolo[3,4-b]pyridin-5-yl)benzamide Chemical compound C1=C2C(OC)=NNC2=NC=C1NC(=O)C(C=1F)=C(F)C=CC=1NS(=O)(=O)C1=CC=CC(F)=C1 WGFNXGPBPIJYLI-UHFFFAOYSA-N 0.000 description 2
- PYRKKGOKRMZEIT-UHFFFAOYSA-N 2-[6-(2-cyclopropylethoxy)-9-(2-hydroxy-2-methylpropyl)-1h-phenanthro[9,10-d]imidazol-2-yl]-5-fluorobenzene-1,3-dicarbonitrile Chemical compound C1=C2C3=CC(CC(C)(O)C)=CC=C3C=3NC(C=4C(=CC(F)=CC=4C#N)C#N)=NC=3C2=CC=C1OCCC1CC1 PYRKKGOKRMZEIT-UHFFFAOYSA-N 0.000 description 2
- FMKGJQHNYMWDFJ-CVEARBPZSA-N 2-[[4-(2,2-difluoropropoxy)pyrimidin-5-yl]methylamino]-4-[[(1R,4S)-4-hydroxy-3,3-dimethylcyclohexyl]amino]pyrimidine-5-carbonitrile Chemical compound FC(COC1=NC=NC=C1CNC1=NC=C(C(=N1)N[C@H]1CC([C@H](CC1)O)(C)C)C#N)(C)F FMKGJQHNYMWDFJ-CVEARBPZSA-N 0.000 description 2
- VVCMGAUPZIKYTH-VGHSCWAPSA-N 2-acetyloxybenzoic acid;[(2s,3r)-4-(dimethylamino)-3-methyl-1,2-diphenylbutan-2-yl] propanoate;1,3,7-trimethylpurine-2,6-dione Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O.CN1C(=O)N(C)C(=O)C2=C1N=CN2C.C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 VVCMGAUPZIKYTH-VGHSCWAPSA-N 0.000 description 2
- YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 description 2
- TVTJUIAKQFIXCE-HUKYDQBMSA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynyl-1H-purine-6,8-dione Chemical compound NC=1NC(C=2N(C(N(C=2N=1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C)=O TVTJUIAKQFIXCE-HUKYDQBMSA-N 0.000 description 2
- LFOIDLOIBZFWDO-UHFFFAOYSA-N 2-methoxy-6-[6-methoxy-4-[(3-phenylmethoxyphenyl)methoxy]-1-benzofuran-2-yl]imidazo[2,1-b][1,3,4]thiadiazole Chemical compound N1=C2SC(OC)=NN2C=C1C(OC1=CC(OC)=C2)=CC1=C2OCC(C=1)=CC=CC=1OCC1=CC=CC=C1 LFOIDLOIBZFWDO-UHFFFAOYSA-N 0.000 description 2
- QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 description 2
- UUZLADCDKJUECN-UHFFFAOYSA-N 4-(cyanomethyl)-2,3,5,6-tetrafluorobenzonitrile Chemical compound FC1=C(F)C(C#N)=C(F)C(F)=C1CC#N UUZLADCDKJUECN-UHFFFAOYSA-N 0.000 description 2
- WYFCZWSWFGJODV-MIANJLSGSA-N 4-[[(1s)-2-[(e)-3-[3-chloro-2-fluoro-6-(tetrazol-1-yl)phenyl]prop-2-enoyl]-5-(4-methyl-2-oxopiperazin-1-yl)-3,4-dihydro-1h-isoquinoline-1-carbonyl]amino]benzoic acid Chemical compound O=C1CN(C)CCN1C1=CC=CC2=C1CCN(C(=O)\C=C\C=1C(=CC=C(Cl)C=1F)N1N=NN=C1)[C@@H]2C(=O)NC1=CC=C(C(O)=O)C=C1 WYFCZWSWFGJODV-MIANJLSGSA-N 0.000 description 2
- SDTHIDMOBRXVOQ-UHFFFAOYSA-N 5-[bis(2-chloroethyl)amino]-6-methyl-1h-pyrimidine-2,4-dione Chemical compound CC=1NC(=O)NC(=O)C=1N(CCCl)CCCl SDTHIDMOBRXVOQ-UHFFFAOYSA-N 0.000 description 2
- XFJBGINZIMNZBW-CRAIPNDOSA-N 5-chloro-2-[4-[(1r,2s)-2-[2-(5-methylsulfonylpyridin-2-yl)oxyethyl]cyclopropyl]piperidin-1-yl]pyrimidine Chemical compound N1=CC(S(=O)(=O)C)=CC=C1OCC[C@H]1[C@@H](C2CCN(CC2)C=2N=CC(Cl)=CN=2)C1 XFJBGINZIMNZBW-CRAIPNDOSA-N 0.000 description 2
- RSIWALKZYXPAGW-NSHDSACASA-N 6-(3-fluorophenyl)-3-methyl-7-[(1s)-1-(7h-purin-6-ylamino)ethyl]-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound C=1([C@@H](NC=2C=3N=CNC=3N=CN=2)C)N=C2SC=C(C)N2C(=O)C=1C1=CC=CC(F)=C1 RSIWALKZYXPAGW-NSHDSACASA-N 0.000 description 2
- JQUCWIWWWKZNCS-LESHARBVSA-N C(C1=CC=CC=C1)(=O)NC=1SC[C@H]2[C@@](N1)(CO[C@H](C2)C)C=2SC=C(N2)NC(=O)C2=NC=C(C=C2)OC(F)F Chemical compound C(C1=CC=CC=C1)(=O)NC=1SC[C@H]2[C@@](N1)(CO[C@H](C2)C)C=2SC=C(N2)NC(=O)C2=NC=C(C=C2)OC(F)F JQUCWIWWWKZNCS-LESHARBVSA-N 0.000 description 2
- KCBAMQOKOLXLOX-BSZYMOERSA-N CC1=C(SC=N1)C2=CC=C(C=C2)[C@H](C)NC(=O)[C@@H]3C[C@H](CN3C(=O)[C@H](C(C)(C)C)NC(=O)CCCCCCCCCCNCCCONC(=O)C4=C(C(=C(C=C4)F)F)NC5=C(C=C(C=C5)I)F)O Chemical compound CC1=C(SC=N1)C2=CC=C(C=C2)[C@H](C)NC(=O)[C@@H]3C[C@H](CN3C(=O)[C@H](C(C)(C)C)NC(=O)CCCCCCCCCCNCCCONC(=O)C4=C(C(=C(C=C4)F)F)NC5=C(C=C(C=C5)I)F)O KCBAMQOKOLXLOX-BSZYMOERSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
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- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000006574 non-aromatic ring group Chemical group 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
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- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
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- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
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- H10K85/649—Aromatic compounds comprising a hetero atom
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Abstract
The organic compound has excellent hole injecting performance and stability, and may be used as hole injecting material for organic electroluminescent device and doped in hole injecting layer or hole transporting layer as dopant.
Description
Technical Field
The invention relates to the technical field of organic electroluminescence, in particular to an organic compound, a mixture, a composition and application thereof in the field of organic electronic devices, in particular electroluminescent devices.
Background
Organic Light Emitting Diodes (OLEDs) have great potential for applications in optoelectronic devices, such as flat panel displays and lighting, due to their advantages of being versatile, low cost to manufacture, and good in optical and electrical performance. The basic principle of light emission of the organic light emitting diode is as follows: when a voltage is applied between the two electrodes, the positive electrode injects holes into the organic layer, the negative electrode injects electrons into the organic layer, and the injected holes and electrons meet to form excitons, which emit light when they transition back to the ground state. In order to improve the recombination efficiency of the injected holes and electrons, further improvement in the structure, material, and the like of the organic light emitting diode is required. To obtain a high performance organic light emitting diode, hole injection and efficient transport are critical. Currently, in OLED light emitting devices, triarylamine derivatives or carbazole derivatives are generally used as hole injection materials, however, further improvements in lifetime, efficiency and operating voltage are still needed. Therefore, there is still a need for further development of hole injection materials capable of improving the efficiency and lifetime of organic light emitting diodes.
Disclosure of Invention
In view of the defects of the prior art, the invention aims to provide an organic compound and application thereof, and aims to provide a novel organic photoelectric functional material, and improve the efficiency and the service life of a device.
The technical scheme of the invention is as follows:
the invention provides an organic compound, the structure of which is shown as general formula (I) or (II):
wherein M is selected from N atom or B atom;
Y1、Y2、Y3each independently selected from the group consisting of:
R4、R5independently selected from cyano, nitro, nitroso, CF3、OCF3Cl, B, I or F; or by cyano, nitro, nitroso, CF3、OCF3A Cl, B, I or F substituted aromatic or heteroaromatic group;
m and n are independently selected from integers of 0-5;
denotes the connection location;
z is selected from single bond, CR6R7、NR6、O、S、SiR6R7、PR6、P(＝O)R6、S＝O、S(＝O)2Or C ═ O; r is 0 or 1;
R1-R3、R6-R7independently at each occurrence selected from H, D, or a straight chain alkyl, alkoxy or thioalkoxy group having 1 to 20C atoms, or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20C atoms, or a silyl group, or a keto group having 1 to 20C atoms, or an alkoxycarbonyl group having 2 to 20C atoms, or an aryloxycarbonyl group having 7 to 20C atoms, a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate, a thiocyanate or isothiocyanate, a hydroxyl group, a nitro group, a CF group3A Cl, Br, F, I crosslinkable group, or a substituted or unsubstituted aromatic or heteroaromatic group having 5 to 60 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 60 ring atoms, or a combination of these systems; adjacent R1-R3、R6-R7May combine with each other to form a substituted or unsubstituted ring;
u, v, w are independently selected from integers from 0 to 3.
The invention further relates to a polymer comprising a repeating unit selected from the group of organic compounds as described above.
The invention further relates to a mixture comprising an organic compound as described above and at least one organic functional material selected from the group consisting of hole injection materials, hole transport materials, electron injection materials, electron blocking materials, hole blocking materials, emitters, host materials or organic dyes.
The invention further relates to a composition comprising an organic compound, a mixture, as described above, and at least one organic solvent.
The invention further relates to an organic electronic device comprising a functional layer, the functional layer material comprising an organic compound or a polymer or a mixture as described above, or being prepared from a composition as described above. Preferably, the functional layer is selected from a hole injection layer or a hole transport layer.
Has the advantages that:
the organic compound is easy to synthesize, and when a hole injection layer or a hole transport layer used for an organic electronic device is used as p-dopant, the service life and the efficiency of the device can be effectively improved, and meanwhile, the working voltage is reduced.
Drawings
Fig. 1 is a structural view of a light emitting device of the present invention, in which 101 is a substrate, 102 is an anode, 103 is a Hole Injection Layer (HIL), 104 is a Hole Transport Layer (HTL), 105 is a light emitting layer, 106 is an Electron Injection Layer (EIL) or an Electron Transport Layer (ETL), and 107 is a cathode.
Detailed Description
The invention provides an organic compound and application thereof in an organic electronic device. In order to make the objects, technical solutions and effects of the present invention clearer and clearer, the present invention is described in further detail below. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
In the present invention, "substituted" means that a hydrogen atom in a substituent is substituted by a substituent. In the present invention, when the same substituent is present in multiple times, it may be independently selected from different groups. If the formula contains multiple M, M can be independently selected from different groups. In the present invention, the "number of ring atoms" represents the number of atoms among atoms constituting the ring itself of a structural compound (for example, a monocyclic compound, a condensed ring compound, a crosslinked compound, a carbocyclic compound, and a heterocyclic compound) in which atoms are bonded in a ring shape. When the ring is substituted with a substituent, the atoms contained in the substituent are not included in the ring-forming atoms. The "number of ring atoms" described below is the same unless otherwise specified. For example, the number of ring atoms of the benzene ring is 6, the number of ring atoms of the naphthalene ring is 10, and the number of ring atoms of the thienyl group is 5.
An aromatic group refers to a hydrocarbon group containing at least one aromatic ring. A heteroaromatic group refers to an aromatic hydrocarbon group that contains at least one heteroatom. The heteroatoms are preferably selected from Si, N, P, O, S and/or Ge, particularly preferably from Si, N, P, O and/or S. By fused ring aromatic group is meant that the rings of the aromatic group may have two or more rings in which two carbon atoms are shared by two adjacent rings, i.e., fused rings. The fused heterocyclic aromatic group means a fused ring aromatic hydrocarbon group containing at least one hetero atom. For the purposes of the present invention, aromatic or heteroaromatic groups include not only aromatic ring systems but also non-aromatic ring systems. Thus, for example, systems such as pyridine, thiophene, pyrrole, pyrazole, triazole, imidazole, oxazole, oxadiazole, thiazole, tetrazole, pyrazine, pyridazine, pyrimidine, triazine, carbene, and the like, are also considered aromatic or heterocyclic aromatic groups for the purposes of this invention. For the purposes of the present invention, fused-ring aromatic or fused-heterocyclic aromatic ring systems include not only systems of aromatic or heteroaromatic groups, but also systems in which a plurality of aromatic or heterocyclic aromatic groups may also be interrupted by short non-aromatic units (< 10% of non-H atoms, preferably less than 5% of non-H atoms, such as C, N or O atoms). Thus, for example, systems such as 9, 9' -spirobifluorene, 9, 9-diarylfluorene, triarylamines, diaryl ethers, etc., are also considered fused aromatic ring systems for the purposes of this invention.
The invention provides an organic compound, the structure of which is shown as general formula (I) or (II):
wherein M is selected from N atom or B atom; in some preferred embodiments, M is selected from B atoms.
Y1、Y2、Y3Each independently selected from the group consisting of:
R4、R5independently selected from cyano, nitro, nitroso, CF3、OCF3Cl, B, I or F; or by cyano, nitro, nitroso, CF3、OCF3Cl, B, I or F substituted aromatic or heteroaromatic groups. In some preferred embodiments, R4、R5Independently selected from F, cyano, CF3、OCF3(ii) a In some preferred embodiments, R4、R5The same is true.
m and n are selected from integers from 0 to 5; in some preferred embodiments, m and n are the same and are any integer from 1 to 5; in some preferred embodiments, m, n are the same and are 1; in some preferred embodiments, m, n are the same and are 2; in some preferred embodiments, m, n are the same and are 5;
denotes the connection location;
z is selected from single bond, CR6R7、NR6、O、S、SiR6R7、PR6、P(＝O)R6、S＝O、S(＝O)2Or C ═ O;
r is 0 or 1; in some preferred embodiments, r is 0; in some preferred embodiments, r is 1, and Z is selected from a single bond; in some preferred embodiments, r is 1 and Z is selected from O.
R1-R3、R6-R7At the time of each occurrence of the event,independently selected from H, D, or a straight chain alkyl, alkoxy or thioalkoxy group having 1 to 20C atoms, or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20C atoms, or a silyl group, or a ketone group having 1 to 20C atoms, or an alkoxycarbonyl group having 2 to 20C atoms, or an aryloxycarbonyl group having 7 to 20C atoms, a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate, a thiocyanate or isothiocyanate, a hydroxyl group, a nitro group, a CF3A Cl, Br, F, I crosslinkable group, or a substituted or unsubstituted aromatic or heteroaromatic group having 5 to 60 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 60 ring atoms, or a combination of these systems; adjacent R1-R3、R6-R7May combine with each other to form a substituted or unsubstituted ring;
u, v, w are selected from integers from 0 to 3; in some preferred embodiments, u, v, w are 0; in some preferred embodiments, one of u, v, w is 1 and the other is 0; in some preferred embodiments, two of u, v, w are 1, and the others are 0; in some preferred embodiments, u, v, and w are all 1.
The organic compounds according to the invention are characterized in that: y is1、Y2、Y3Each independently selected from the group consisting of:
denotes the connection position.
The organic compound according to the present invention is characterized in that: r1-R3Selected from cyano, nitro, nitroso, CF3、OCF3Cl, B, I or F or by cyano, nitro, nitroso, CF3、OCF3Cl, B, I or F substituted aromatic or heteroaromatic groups. In some preferred embodiments, R1-R3Selected from cyano, F, CF3、OCF3(ii) a In some preferred embodiments, R1-R3Is selected fromBy cyano group, F, CF3、OCF3A substituted aromatic or heteroaromatic group.
In some preferred embodiments, by cyano, nitro, nitroso, CF3、OCF3Cl, B, I or F substituted aromatic or heteroaromatic groups selected from the group consisting of:
wherein: x is independently selected from CR at each occurrence8Or N;
w is independently selected from CR at each occurrence9R10、NR9、O、S、SiR9R10、PR9、P(＝O)R9、S＝O、S(＝O)2Or C ═ O;
R8-R10independently at each occurrence, H, D, or a straight chain alkyl group having 1 to 20C atoms, or a branched or cyclic alkyl group having 3 to 20C atoms, or a keto group having 1 to 20C atoms, or an alkoxycarbonyl group having 2 to 20C atoms, or an aryloxycarbonyl group having 7 to 20C atoms, cyano, carbamoyl, cyano, nitro, nitroso, CF3Cl, B, I or F, or a substituted or unsubstituted aromatic or heteroaromatic group having 5 to 60 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 60 ring atoms, or a combination of these systems. Further, by cyano, nitro, nitroso, CF3、OCF3The Cl, B, I or F substituted aromatic or heteroaromatic group is preferably selected from the group consisting of:
specific examples of the organic compound according to the present invention include, but are not limited to, the following:
the organic compound according to the invention can be used as a functional material in a functional layer of an electronic device. The organic functional layer includes, but is not limited to, a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), an Electron Transport Layer (ETL), an Electron Injection Layer (EIL), an Electron Blocking Layer (EBL), a Hole Blocking Layer (HBL), and an emission layer (EML). In a particularly preferred embodiment, the organic compounds according to the invention are used in Hole Injection Layers (HIL) or p-dots.
The invention also provides a mixture, which is characterized by comprising at least one organic compound and at least another organic functional material, wherein the at least another organic functional material can be selected from a Hole Injection Material (HIM), a Hole Transport Material (HTM), an Electron Transport Material (ETM), an Electron Injection Material (EIM), an Electron Blocking Material (EBM), a Hole Blocking Material (HBM), a luminescent material (Emitter), a Host material (Host) and an organic dye. Various organic functional materials are described in detail, for example, in WO2010135519a1, US20090134784a1 and WO2011110277a1, the entire contents of this 3 patent document being hereby incorporated by reference.
In some preferred embodiments, the mixture, wherein the another organic functional material is selected from a Hole Injection Material (HIM), a Hole Transport Material (HTM), and a Host material (Host).
In one embodiment, the mixture comprises at least one Hole Injection Material (HIM) or hole transport material and one dopant, the dopant being the above organic compound, the molar ratio of dopant to host being 1:1 to 1: 100000.
Details of HIM/HTM/EBM, and Host (Host material/matrix material) are described in WO2018095395A 1.
It is another object of the present invention to provide a material solution for printing OLEDs.
In certain embodiments, the compounds according to the invention have a molecular weight of 800g/mol or more, preferably 900g/mol or more, very preferably 1000g/mol or more, more preferably 1100g/mol or more, most preferably 1200g/mol or more.
In other embodiments, the compounds according to the invention have a solubility in toluene of 2mg/ml or more, preferably 3mg/ml or more, more preferably 4mg/ml or more, most preferably 5mg/ml or more at 25 ℃.
The invention also relates to a composition comprising at least one organic compound or mixture as described above, and at least one organic solvent; the at least one organic solvent is selected from aromatic or heteroaromatic, ester, aromatic ketone or aromatic ether, aliphatic ketone or aliphatic ether, alicyclic or olefinic compound, or boric acid ester or phosphoric acid ester compound, or a mixture of two or more solvents.
The compositions of the embodiments of the present invention may contain 0.01 to 10 wt% of the organic compound or polymer or mixture according to the present invention, preferably 0.1 to 15 wt%, more preferably 0.2 to 5 wt%, and most preferably 0.25 to 3 wt%.
The invention also relates to the use of said composition as a coating or printing ink for the production of organic electronic devices, particularly preferably by a printing or coating production process.
The present invention also provides the use of a compound, mixture or composition as described above in an Organic electronic device, which may be selected from, but not limited to, Organic Light Emitting Diodes (OLEDs), Organic photovoltaic cells (OPVs), Organic light Emitting cells (OLEECs), Organic Field Effect Transistors (OFETs), Organic light Emitting field effect transistors (effets), Organic lasers, Organic spintronic devices, Organic sensors and Organic Plasmon Emitting diodes (Organic plasma Emitting diodes), etc., particularly preferably OLEDs. In the embodiment of the present invention, the organic compound or the high polymer is preferably used for a hole injection layer of an OLED device.
The invention further relates to an organic electronic device comprising at least one organic compound or mixture or polymer as described above or prepared from the above composition. Furthermore, the organic electronic device comprises at least one functional layer, wherein the functional layer comprises an organic compound or a mixture or a high polymer as described above, or is prepared from the above composition. The functional layer is selected from a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), an emission layer (EML), an Electron Blocking Layer (EBL), an Electron Injection Layer (EIL), an Electron Transport Layer (ETL), and a Hole Blocking Layer (HBL).
In a preferred embodiment, the organic electronic device according to the invention comprises at least one hole injection layer or hole transport layer comprising an organic compound as described above.
In general, the organic electronic device of the present invention comprises at least a cathode, an anode and a functional layer disposed between the cathode and the anode, wherein the functional layer comprises at least one organic compound as described above.
In certain preferred embodiments, the electroluminescent device comprises a hole injection layer or a hole transport layer comprising an organic compound as described above.
In the above-mentioned light emitting device, especially an OLED, it comprises a substrate, an anode, at least one light emitting layer, and a cathode.
The OLED may also comprise further functional layers, such as a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), an Electron Blocking Layer (EBL), an Electron Injection Layer (EIL), an Electron Transport Layer (ETL), a Hole Blocking Layer (HBL). Suitable materials for use in these functional layers are described in detail above and in WO2010135519a1, US20090134784a1 and WO2011110277a1, the entire contents of these 3 patent documents being hereby incorporated by reference.
The invention also relates to the use of the electroluminescent device according to the invention in various electronic devices, including, but not limited to, display devices, lighting devices, light sources, sensors, etc.
The present invention will be described in connection with the preferred embodiments without limiting to the embodiments described below, it being understood that the appended claims outline the scope of the invention and those skilled in the art who have the benefit of this teaching will appreciate that certain changes can be made to the embodiments of the invention without departing from the spirit and scope of the invention as defined by the appended claims.
DETAILED DESCRIPTION OF EMBODIMENT (S) OF INVENTION
The synthesis of the compounds according to the invention is illustrated, but the invention is not limited to the following examples.
Synthesis example 1: synthesis of Compound 1:
adding the intermediate compound 1-1(3.23g, 10mmol) into a 100ml three-neck flask, adding 50ml anhydrous toluene, adding DMAP (12.1g, 100mmol) and titanium tetrachloride (15.12g, 80mmol) under the protection of nitrogen, refluxing for 6 hours, cooling, pouring the reaction solution into water, concentrating to remove toluene, separating EA and water, combining organic phases, concentrating, purifying EA and PE by passing through a column to obtain a light yellow solid 1.49g, and yield%
Synthesis example 2: synthesis of Compound 2:
the synthesis method of compound 2 was the same as in synthesis example 1, except that compound 2-1 was used as an intermediate, and the yield was 28%.
Synthesis example 3: synthesis of Compound 3:
the synthesis method of Compound 3 was the same as that of Synthesis example 1, except that the intermediate used was Compound 3-1, the yield was 30%
Synthesis example 4: synthesis of Compound 4:
the synthesis method of compound 4 was the same as in synthesis example 1, except that the intermediate used was compound 4-1, and the yield was 29% synthesis example 5: synthesis of Compound 5:
the synthesis method of compound 5 was the same as in synthesis example 1, except that compound 5-1 was used as an intermediate, and the yield was 29%.
Synthesis example 6: synthesis of Compound 6:
the synthesis method of compound 6 was the same as in synthesis example 1, except that compound 6-1 was used as an intermediate, and the yield was 25%.
Synthesis example 7: synthesis of compound 7:
the synthesis method of compound 7 was the same as in synthesis example 1, except that compound 7-1 was used as an intermediate, and the yield was 30%.
Synthesis example 8: synthesis of compound 8:
the synthesis method of compound 8 was the same as in synthesis example 1, except that the intermediate used was compound 8-1, and the yield was 20%.
Synthesis example 9: synthesis of compound 9:
the synthesis method of compound 9 was the same as in synthesis example 1, except that compound 9-1 was used as an intermediate, and the yield was 18%.
Synthesis example 10: synthesis of compound 10:
the synthesis method of compound 10 was the same as in synthesis example 1, except that compound 10-1 was used as an intermediate, and the yield was 17%.
Synthesis example 11: synthesis of compound 11:
the synthesis method of compound 11 was the same as in synthesis example 1, except that compound 11-1 was used as an intermediate, and the yield was 37%.
Synthesis example 12: synthesis of compound 12:
the synthesis method of compound 12 was the same as in synthesis example 1, except that compound 12-1 was used as an intermediate, and the yield was 38%.
Synthesis example 13: synthesis of compound 13:
the intermediate compound 13-1(3.71g, 10mmol) and pentafluorobenzyl cyanide (16.56g, 80mmol) were charged into a 100ml three-necked flask, then 50ml of anhydrous toluene was added, DMAP (9.7g, 80mmol) and titanium tetrachloride (12.4g, 60mmol) were added under nitrogen protection and refluxed for 6 hours, cooled, the reaction solution was poured into water, toluene was concentrated to remove the aqueous layer, the organic layers were combined, concentrated, EA and PE were column purified to give a pale yellow solid 2.39g, yield 32%.
Synthesis example 14: synthesis of compound 14:
intermediate J Compound 1-1(3.21g, 10mmol) and 3.5-trifluoromethoxybenzyl cyanide (22.8g, 80mmol) were charged to a 100ml three-necked flask, then 50ml of anhydrous toluene was added, DMAP (12.1g, 100mmol) and titanium tetrachloride (12.4g, 80mmol) were added under nitrogen for reflux reaction for 6 hours, the reaction solution was cooled, poured into water, concentrated to remove toluene, the EA and water separated, the organic phases were combined, concentrated, and EA and PE were purified by column chromatography to give 3.37g of a white solid, yield 30%.
Synthesis example 15: synthesis of compound 15:
compound 15-1(5.27g, 10mmol) and cyanamide (3.36g, 80mmol) were added to a 100ml three-necked flask, then 50ml of anhydrous toluene was added, DMAP (12.1g, 100mmol) and titanium tetrachloride (12.4g, 80mmol) were added under nitrogen protection and refluxed for 6 hours, cooled, the reaction was poured into water, the toluene was concentrated to remove the EA and water layers, the organic phases were combined, concentrated, EA and PE were purified on a column to give 1.49g of a white solid, yield 25%.
Synthesis example 16: synthesis of compound 16:
the synthesis method of compound 16 was the same as in synthesis example 1, except that compound 16-1 was used as an intermediate, and the yield was 22%.
Synthesis example 17: synthesis of compound 17:
the synthesis method of compound 17 was the same as in synthesis example 1, except that compound 17-1 was used as an intermediate, and the yield was 21%.
Synthesis example 18: synthesis of compound 18:
the synthesis method of compound 18 was the same as in synthesis example 1, except that compound 18-1 was used as an intermediate, and the yield was 19%.
Synthesis example 19: synthesis of compound 19:
the synthesis method of compound 19 was the same as in synthesis example 1, except that compound 19-1 was used as an intermediate, and the yield was 24%.
Synthesis example 20: synthesis of compound 20:
the synthesis method of compound 20 was the same as in synthesis example 1, except that compound 20-1 was used as an intermediate, and the yield was 22%.
Synthesis example 21: synthesis of compound 21:
the synthesis method of compound 21 was the same as in synthesis example 1, except that compound 21-1 was used as an intermediate, and the yield was 19%.
Synthesis example 22: synthesis of compound 22:
the synthesis method of compound 22 was the same as in synthesis example 1, except that compound 22-1 was used as an intermediate, and the yield was 19%.
Synthesis example 23: synthesis of compound 23:
the synthesis method of compound 23 was the same as in synthesis example 1, except that the intermediate used was compound 23-1, and the yield was 24%.
Synthesis example 24: synthesis of compound 24:
the synthesis method of compound 24 was the same as in synthesis example 1, except that compound 24-1 was used as an intermediate, and the yield was 23%.
Synthesis example 25: synthesis of compound 25:
the synthesis method of compound 25 was the same as in synthesis example 1, except that compound 25-1 was used as an intermediate, and the yield was 17%.
Synthesis example 26: synthesis of compound 26:
the synthesis method of compound 26 was the same as in synthesis example 1, except that compound 26-1 was used as an intermediate, and the yield was 15%.
Synthesis example 27: synthesis of compound 27:
the synthesis method of compound 27 was the same as in synthesis example 1, except that compound 27-1 was used as an intermediate, and the yield was 18%.
Synthesis example 28: synthesis of compound 28:
the synthesis method of compound 28 was the same as in synthesis example 1, except that compound 28-1 was used as an intermediate, and the yield was 22%.
Synthesis example 29: synthesis of compound 29:
the synthesis method of compound 29 was the same as in synthesis example 1, except that compound 29-1 was used as an intermediate, and the yield was 19%.
Synthesis example 30: synthesis of compound 30:
adding the compound 30-1(5.27g, 10mmol) and propylene cyanide (3.96g, 60mmol) into a 100ml three-neck flask, then adding 50ml anhydrous toluene, adding DMAP (9.7g, 80mmol) and titanium tetrachloride (9.3g, 60mmol) under the protection of nitrogen, refluxing for 6 hours, cooling, pouring the reaction solution into water, concentrating to remove toluene, separating EA and water, combining organic phases, concentrating, and purifying EA and PE through a column to obtain a light yellow solid 1.53g, and yield 25%.
Synthesis example 31: synthesis of compound 31:
adding the compound 31-1(8.06g, 10mmol) and propylene cyanide (3.96g, 60mmol) into a 100ml three-neck flask, then adding 50ml of anhydrous toluene, adding DMAP (9.7g, 80mmol) and titanium tetrachloride (9.3g, 60mmol) under the protection of nitrogen, refluxing for 6 hours, cooling, pouring the reaction liquid into water, concentrating to remove toluene, separating EA and water, combining organic phases, concentrating, purifying EA and PE by passing through a column to obtain a light yellow solid 2.26g, and yield 25%.
Synthesis example 32: synthesis of compound 32:
adding the compound 32-1(3.68g, 10mmol) and 3.5-dicyanobenzyl cyanide (10.02g, 60mmol) into a 100ml three-neck flask, then adding 50ml of anhydrous toluene, adding DMAP (9.7g, 80mmol) and titanium tetrachloride (9.3g, 60mmol) under the protection of nitrogen, refluxing for 6 hours, cooling, pouring the reaction solution into water, concentrating to remove toluene, separating EA from water, combining organic phases, concentrating, purifying EA and PE by passing through a column to obtain a light yellow solid 2.00g, and yueld ═ 30%
Synthesis example 33: synthesis of compound 33:
compound 16-1(3.2g, 10mmol) and 4-cyanomethyl-2, 3,5, 6-tetrafluorobenzonitrile (10.02g, 80mmol) were charged into a 100ml three-necked flask, then 50ml of anhydrous toluene was added, DMAP (12.1g, 100mmol) and titanium tetrachloride (12.4g, 80mmol) were added under nitrogen atmosphere and refluxed for 6 hours, cooled, the reaction solution was poured into water, toluene was concentrated to remove, the EA and water layers were separated, the organic layers were combined, concentrated, EA and PE were purified by column chromatography to obtain a pale yellow solid 2.00g, and yield 22%.
Synthesis example 34: synthesis of compound 34:
the synthesis method of compound 34 was the same as in synthesis example 33, except that 3.5-trifluoromethoxybenzyl cyanide, which is an intermediate, was used in a yield of 19%.
Synthesis example 35: synthesis of compound 35:
compound 35-1(6.98g, 10mmol) and cyanamide (3.36g, 80mmol) were added to a 100ml three-necked flask, then 50ml of anhydrous toluene was added, DMAP (12.1g, 100mmol) and titanium tetrachloride (12.4g, 80mmol) were added under nitrogen protection and refluxed for 6 hours, cooled, the reaction was poured into water, the toluene was concentrated to remove the aqueous layer, the organic layers were combined, concentrated, EA and PE were purified on a column to give 1.31g of a white solid, yield 17%.
Synthesis example 36: synthesis of compound 36:
compound 36-1(8.06g, 10mmol) and propylene cyanide (3.96g, 60mmol) were added to a 100ml three-necked flask, then 50ml of anhydrous toluene was added, DMAP (9.7g, 80mmol) and titanium tetrachloride (9.3g, 60mmol) were added under nitrogen protection and refluxed for 6 hours, cooled, the reaction solution was poured into water, toluene was concentrated to remove, the EA and water separated, the organic phases were combined, concentrated, EA and PE were column purified to give 1.38g of gray solid, and yield was 35%.
Synthesis example 37: synthesis of compound 37:
synthesis of compound 37 was carried out in the same manner as in Synthesis example 36, except that intermediate 37-1 was used in a yield of 32%.
Synthesis example 38: synthesis of compound 38:
the synthesis method of compound 38 was the same as in synthesis example 36, except that intermediate 38-1 was used, and the yield was 29%.
Synthesis example 39: synthesis of compound 39:
the synthesis method of compound 39 was the same as in synthesis example 36, except that intermediate 39-1 was used, and the yield was 19%.
Synthesis example 40: synthesis of compound 40:
the synthesis method of compound 40 was the same as in synthesis example 36, except that intermediate 40-1 was used, and the yield was 22%.
Synthesis example 41: synthesis of compound 41:
the synthesis method of compound 41 was the same as in synthesis example 36, except that intermediate 41-1 was used, and the yield was 24%.
Synthesis example 42: synthesis of compound 42:
the synthesis method of compound 42 was the same as in synthesis example 36, except that intermediate 42-1 was used, and the yield was 19%.
Synthesis example 43: synthesis of compound 43:
compound 43-1(2.97g, 10mmol) and 4-cyanomethyl-2, 3,5, 6-tetrafluorobenzonitrile (12.84g, 60mmol) were charged into a 100ml three-necked flask, then 50ml of anhydrous toluene was added, DMAP (9.7g, 80mmol) and titanium tetrachloride (9.3g, 60mmol) were added under nitrogen protection and refluxed for 6 hours, cooled, the reaction solution was poured into water, toluene was concentrated to remove, EA and water were separated, the organic phases were combined, concentrated, EA and PE were column purified to obtain a gray solid 1.72g, yield 25%.
Synthesis example 44: synthesis of compound 44:
the synthesis method of compound 44 was the same as in synthesis example 36, except that intermediate 42-1 was used, and the yield was 19%.
Synthesis example 45: synthesis of compound 45:
synthesis of Compound 45 was carried out in the same manner as in Synthesis example 36, except that intermediate 45-1 was used in a yield of 19%.
Synthesis example 46: synthesis of compound 46:
synthesis of compound 46 was carried out in the same manner as in Synthesis example 36, except that intermediate 46-1 was used in a yield of 32%.
Synthesis example 47: synthesis of compound 47:
synthesis of Compound 47 was carried out in the same manner as in Synthesis example 36, except that intermediate 47-1 was used in a yield of 26%.
Synthesis example 48: synthesis of compound 48:
synthesis of Compound 48 was carried out in the same manner as in Synthesis example 36, except that intermediate 48-1 was used in a yield of 19%.
Synthesis example 49: synthesis of compound 49:
the synthesis method of compound 49 was the same as in synthesis example 36, except that intermediate 49-1 was used, the yield was 18%.
Synthesis example 50: synthesis of compound 50:
the synthesis method of compound 50 was the same as in synthesis example 36, except that intermediate 49-1 was used, and the yield was 21%.
Synthesis example 51: synthesis of compound 51:
synthesis of Compound 51 was carried out in the same manner as in Synthesis example 36, except that intermediate 51-1 was used in a yield of 25%.
Synthesis example 52: synthesis of compound 52:
the synthesis method of compound 52 was the same as in synthesis example 43, except that intermediate 52-1 was used, and the yield was 17%.
Synthesis example 53: synthesis of compound 53:
the synthesis method of compound 53 was the same as in synthesis example 36, except that intermediate 53-1 was used, and the yield was 33%.
Synthesis example 54: synthesis of compound 54:
synthesis of compound 54 was carried out in the same manner as in Synthesis example 36, except that intermediate 54-1 was used in a yield of 19%.
Synthesis example 55: synthesis of compound 55:
the synthesis method of compound 55 was the same as in synthesis example 36, except that intermediate 55-1 was used, and the yield was 17%.
Synthesis example 56: synthesis of compound 56:
synthesis of compound 56 was carried out in the same manner as in Synthesis example 36, except that intermediate 56-1 was used in a yield of 24%.
Synthesis example 57: synthesis of compound 57:
synthesis of compound 57 was carried out in the same manner as in Synthesis example 36, except that intermediate 57-1 was used in a yield of 26%.
Synthesis example 58: synthesis of compound 58:
the synthesis method of compound 58 was the same as in synthesis example 36, except that intermediate 58-1 was used, and the yield was 20%.
Synthesis example 59: synthesis of compound 59:
the synthesis method of compound 59 was the same as in synthesis example 36, except that intermediate 59-1 was used, and the yield was 21%.
Synthesis example 60: synthesis of compound 60:
the synthesis method of compound 60 was the same as in synthesis example 36, except that intermediate 60-1 was used, and the yield was 18%.
Synthesis example 61: synthesis of compound 61:
the synthesis method of compound 61 was the same as in synthesis example 36, except that intermediate 61-1 was used, and the yield was 32%.
Synthesis example 62: synthesis of compound 62:
the synthesis method of compound 62 was the same as in synthesis example 36, except that intermediate 62-1 was used, and the yield was 30%.
Synthesis example 63: synthesis of compound 63:
synthesis of Compound 63 was carried out in the same manner as in Synthesis example 36, except that intermediate 63-1 was used in a yield of 27%.
Synthesis example 64: synthesis of compound 64:
the synthesis method of compound 64 was the same as in synthesis example 36, except that intermediate 64-1 was used, and the yield was 22%.
Synthesis example 65: synthesis of compound 65:
synthesis of compound 65 was carried out in the same manner as in Synthesis example 36, except that intermediate 65-1 was used in a yield of 19%.
Synthesis example 66: synthesis of compound 66:
the synthesis method of compound 66 was the same as in synthesis example 36, except that intermediate 66-1 was used, and the yield was 18%.
Synthesis example 67: synthesis of compound 67:
the synthesis method of compound 67 was the same as in synthesis example 36, except that intermediate 67 was used, and the yield was 17%.
Synthesis example 68: synthesis of compound 68:
the synthesis method of compound 68 was the same as in synthesis example 36, except that intermediate 68-1 was used, and the yield was 22%.
Synthesis example 69: synthesis of compound 69:
compound 69-1(2.92g, 10mmol) and 3.5-trifluoromethyl-benzyl cyanide (15.1g, 60mmol) were charged into a 100ml three-necked flask, then 50ml of anhydrous toluene was added, DMAP (9.7g, 80mmol) and titanium tetrachloride (9.3g, 60mmol) were added under nitrogen protection and refluxed for 6 hours, cooled, the reaction was poured into water, the toluene was concentrated to remove the toluene, the EA and water separated liquids were combined, the organic phases were concentrated, EA and PE were purified over a column to give 1.68g of a white solid, yield 22%.
Comparative compound 1 was F4 TCNQ; comparative compound 2 was HATCN; comparative compound 3 was NDP 9.
Preparation and characterization of OLED device
The device structure is as follows: has an ITO/p-dopat: HTL (3:100,10nm)/HTL (120 nm)/Host: 10% Dopan (40 nm)/ETL: the preparation steps of the OLED device with Liq (30nm)/Liq (1nm)/Al (100 nm)/cathode are as follows:
a. cleaning the conductive glass substrate, namely cleaning the conductive glass substrate by using various solvents such as chloroform, ketone and isopropanol when the conductive glass substrate is used for the first time, and then carrying out ultraviolet ozone plasma treatment; b. HIL (10nm), HTL (120nm), EML (40nm), ETL (30 nm): under high vacuum (1X 10)-6Mbar, mbar). c. Cathode LiQ/Al (1nm/100nm) in high vacuum (1X 10)-6Millibar) hot evaporation; d. encapsulation the devices were encapsulated with uv curable resin in a nitrogen glove box.
Wherein: the EML material is selected from Host: 10% Dopan (40 nm); the ETL material is selected from ETL: liq (30 nm).
Wherein: p-dopant was selected from the synthetic compounds of the present invention and comparative compounds 1-3.
The current-voltage (J-V) characteristics of each OLED device were characterized by a characterization device, while recording important parameters such as efficiency, lifetime, and external quantum efficiency. It was determined that the efficiency and lifetime of the devices obtained using the synthetic compounds of the present invention as p-dopats are superior to those of the comparative examples, as detailed in table 1.
TABLE 1
As can be seen from table 1, the efficiency and lifetime of the compound according to the present invention as a p-type dopant in the hole injection layer of the organic electronic device are greatly improved compared to comparative examples 1 and 2 and 3.
The technical features of the embodiments described above may be arbitrarily combined, and for the sake of brevity, all possible combinations of the technical features in the embodiments described above are not described, but should be considered as being within the scope of the present specification as long as there is no contradiction between the combinations of the technical features.
The above-mentioned embodiments only express several embodiments of the present invention, and the description thereof is more specific and detailed, but not construed as limiting the scope of the invention. It should be noted that, for a person skilled in the art, several variations and modifications can be made without departing from the inventive concept, which falls within the scope of the present invention. Therefore, the protection scope of the present patent shall be subject to the appended claims.
Claims (8)
1. An organic compound having a structure represented by general formula (I) or (II):
wherein M is selected from B atoms;
Y1、Y2、Y3each independently selected from the group consisting of:
R4、R5independently selected from cyano, nitro, nitroso, CF3、OCF3Cl, B, I or F;
m and n are independently selected from integers of 0-5;
denotes the connection location;
z is selected from a single bond, O or S;
r is 0 or 1;
R1-R3each occurrence is independently selected from H, D, or has 1 to 20C atomsOr a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 20C atoms, or a silyl group, or a keto group having 1 to 20C atoms, or an alkoxycarbonyl group having 2 to 20C atoms, or an aryloxycarbonyl group having 7 to 20C atoms, a cyano group, a carbamoyl group, a haloformyl group, a formyl group, an isocyano group, an isocyanate, a thiocyanate or isothiocyanate, a hydroxyl group, a nitro group, a CF, or a salt thereof3A Cl, Br, F, I crosslinkable group, or a substituted or unsubstituted aromatic or heteroaromatic group having 5 to 60 ring atoms, or an aryloxy or heteroaryloxy group having 5 to 60 ring atoms, or a combination of these systems; adjacent R1-R3、R6-R7May combine with each other to form a substituted or unsubstituted ring;
u, v, w are independently selected from integers from 0 to 3.
2. An organic compound according to claim 1, characterized in that: y is1、Y2、Y3Each independently selected from the group consisting of:
denotes the connection position.
3. According to claimThe organic compound of claim 1, wherein: r1-R3Selected from cyano, nitro, CF3Cl, B, I or F.
4. A high polymer characterized by: comprising a repeating unit selected from the organic compounds according to any one of claims 1 to 3.
5. A mixture, characterized by: comprising a compound according to any one of claims 1 to 3, or a polymer according to claim 4, and at least one organic functional material selected from hole-injecting materials, hole-transporting materials, electron-injecting materials, electron-blocking materials, hole-blocking materials, light-emitting bodies, host materials or organic dyes.
6. A composition comprising a compound according to any one of claims 1 to 3, a polymer according to claim 4 or a mixture according to claim 5, and at least one organic solvent.
7. An organic electronic device comprising a functional layer material comprising a compound according to any one of claims 1 to 3, a polymer according to claim 4 or a mixture according to claim 5, or prepared from a composition according to claim 6.
8. The organic electronic device of claim 7, which is an organic electroluminescent device, wherein the functional layer is selected from a hole injection layer or a hole transport material.
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