CN105367605A - 用官能化苯基卡宾配体环金属化的四齿铂(ii)络合物和它们的类似物 - Google Patents
用官能化苯基卡宾配体环金属化的四齿铂(ii)络合物和它们的类似物 Download PDFInfo
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- CN105367605A CN105367605A CN201510441320.5A CN201510441320A CN105367605A CN 105367605 A CN105367605 A CN 105367605A CN 201510441320 A CN201510441320 A CN 201510441320A CN 105367605 A CN105367605 A CN 105367605A
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- complex compound
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- alkyl
- aryl
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- HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical class [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 title description 5
- 239000003446 ligand Substances 0.000 title description 2
- YJLSVCJDMFHEHC-UHFFFAOYSA-N phenylmethylene Chemical class [CH]C1=CC=CC=C1 YJLSVCJDMFHEHC-UHFFFAOYSA-N 0.000 title 1
- 230000003111 delayed effect Effects 0.000 claims abstract description 8
- 150000003057 platinum Chemical class 0.000 claims abstract 3
- 150000001875 compounds Chemical class 0.000 claims description 81
- 125000003118 aryl group Chemical group 0.000 claims description 44
- 229910052760 oxygen Inorganic materials 0.000 claims description 30
- 125000001072 heteroaryl group Chemical group 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 22
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 150000002367 halogens Chemical class 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 13
- 239000000126 substance Substances 0.000 claims description 13
- 230000008859 change Effects 0.000 claims description 11
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
- 125000004122 cyclic group Chemical group 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 6
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 6
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 3
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims description 3
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical class C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 3
- JMANUKZDKDKBJP-UHFFFAOYSA-N imidazo[1,5-a]pyridine Chemical compound C1=CC=CC2=CN=CN21 JMANUKZDKDKBJP-UHFFFAOYSA-N 0.000 claims description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 description 47
- -1 heterocyclic radical Chemical class 0.000 description 39
- 239000000463 material Substances 0.000 description 36
- 125000000753 cycloalkyl group Chemical group 0.000 description 33
- 125000000392 cycloalkenyl group Chemical group 0.000 description 23
- 150000003254 radicals Chemical class 0.000 description 22
- 229910052799 carbon Inorganic materials 0.000 description 20
- 125000002769 thiazolinyl group Chemical group 0.000 description 19
- 125000000304 alkynyl group Chemical group 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 11
- 150000004696 coordination complex Chemical class 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 230000006872 improvement Effects 0.000 description 9
- 230000003287 optical effect Effects 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 125000005842 heteroatom Chemical group 0.000 description 8
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 7
- 125000004429 atom Chemical group 0.000 description 7
- 150000001721 carbon Chemical group 0.000 description 7
- 230000005281 excited state Effects 0.000 description 7
- 239000003550 marker Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 125000004185 ester group Chemical group 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 5
- 150000003851 azoles Chemical class 0.000 description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 5
- 125000000468 ketone group Chemical group 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 150000002894 organic compounds Chemical class 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 238000012545 processing Methods 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- 230000010748 Photoabsorption Effects 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 239000005864 Sulphur Substances 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000013461 design Methods 0.000 description 4
- 238000002372 labelling Methods 0.000 description 4
- 230000031700 light absorption Effects 0.000 description 4
- 125000006574 non-aromatic ring group Chemical group 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 239000011574 phosphorus Substances 0.000 description 4
- 229920000570 polyether Polymers 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 230000005855 radiation Effects 0.000 description 4
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 125000004366 heterocycloalkenyl group Chemical group 0.000 description 3
- 125000004415 heterocyclylalkyl group Chemical group 0.000 description 3
- 150000002460 imidazoles Chemical class 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000005693 optoelectronics Effects 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
- 238000000103 photoluminescence spectrum Methods 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 229920000098 polyolefin Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 150000003217 pyrazoles Chemical class 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 2
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Chemical compound C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 description 2
- KEVMYFLMMDUPJE-UHFFFAOYSA-N 2,7-dimethyloctane Chemical group CC(C)CCCCC(C)C KEVMYFLMMDUPJE-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 125000002015 acyclic group Chemical group 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 description 2
- 125000005233 alkylalcohol group Chemical group 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 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
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 230000005283 ground state Effects 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000007769 metal material Substances 0.000 description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- SBOJXQVPLKSXOG-UHFFFAOYSA-N o-amino-hydroxylamine Chemical compound NON SBOJXQVPLKSXOG-UHFFFAOYSA-N 0.000 description 2
- 125000002524 organometallic group Chemical group 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical class C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- HTJMXYRLEDBSLT-UHFFFAOYSA-N 1,2,4,5-tetrazine Chemical compound C1=NN=CN=N1 HTJMXYRLEDBSLT-UHFFFAOYSA-N 0.000 description 1
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 description 1
- 150000004868 1,2,5-thiadiazoles Chemical class 0.000 description 1
- 150000004869 1,3,4-thiadiazoles Chemical class 0.000 description 1
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 1
- UQRONKZLYKUEMO-UHFFFAOYSA-N 4-methyl-1-(2,4,6-trimethylphenyl)pent-4-en-2-one Chemical group CC(=C)CC(=O)Cc1c(C)cc(C)cc1C UQRONKZLYKUEMO-UHFFFAOYSA-N 0.000 description 1
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 description 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
- FWQHKDXZFCRMOH-UHFFFAOYSA-N C1(=CC=CC=C1)P(=O)(C1=CC=CC=C1)C1=CC=CC=2SC3=C(C=21)C=CC=C3 Chemical compound C1(=CC=CC=C1)P(=O)(C1=CC=CC=C1)C1=CC=CC=2SC3=C(C=21)C=CC=C3 FWQHKDXZFCRMOH-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 241000790917 Dioxys <bee> Species 0.000 description 1
- 229910004373 HOAc Inorganic materials 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical group SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- 101150034699 Nudt3 gene Proteins 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- DPOPAJRDYZGTIR-UHFFFAOYSA-N Tetrazine Chemical compound C1=CN=NN=N1 DPOPAJRDYZGTIR-UHFFFAOYSA-N 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical group 0.000 description 1
- 150000001412 amines Chemical group 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 1
- 150000005347 biaryls Chemical group 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003327 cancerostatic effect Effects 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 125000003636 chemical group Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- CFBGXYDUODCMNS-UHFFFAOYSA-N cyclobutene Chemical compound C1CC=C1 CFBGXYDUODCMNS-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
- WAXSUAIGRGARIT-UHFFFAOYSA-N cycloheptyne Chemical compound C1CCC#CCC1 WAXSUAIGRGARIT-UHFFFAOYSA-N 0.000 description 1
- 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- ZPWOOKQUDFIEIX-UHFFFAOYSA-N cyclooctyne Chemical compound C1CCCC#CCC1 ZPWOOKQUDFIEIX-UHFFFAOYSA-N 0.000 description 1
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- UKPXULFIISGBHG-UHFFFAOYSA-N cyclopropene Chemical compound [CH]1C=C1 UKPXULFIISGBHG-UHFFFAOYSA-N 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000002704 decyl 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])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004915 dibutylamino group Chemical group C(CCC)N(CCCC)* 0.000 description 1
- 125000003438 dodecyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000005525 hole transport Effects 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 150000001261 hydroxy acids Chemical group 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
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Abstract
本发明提供用官能化苯基卡宾配体环金属化的四齿铂(II)络合物和它们的类似物。式I和II的四齿铂络合物适用于显示和照明应用中的磷光或者延迟荧光和磷光发射体。
Description
相关申请的交叉引用
本申请要求2014年7月24日提交的题为“TETRADENTATEPLATINUM(II)COMPLEXESCYCLOMETALATEDWITHFUNCTIONALIZEDPHENYLCARBENELIGANDSANDTHEIRANALOGUES”的U.S.序列号62/028,562的优先权，将其全部通过参考全部引入本文中。
技术领域
本公开内容涉及用于显示和照明应用中的磷光或者延迟荧光和磷光发射体的四齿铂(II)络合物，并具体涉及具有改进的发射光谱的磷光或者延迟荧光和磷光四齿金属络合物。
背景技术
能够吸收和/或发射光的化合物可理想地适合用于各种各样的光学和电致发光器件，包括，例如光吸收器件例如太阳能敏感器件和光敏器件、有机发光二极管(OLED)、光发射器件、以及既能够进行光吸收又能够进行光发射和作为用于生物应用的标志器(marker)的器件。许多研究已致力于发现和优化用于在光学和电致发光器件中使用的有机和有机金属材料。通常，该领域中的研究旨在实现许多目标，包括在吸收和发射效率方面的改善和在器件稳定性方面的改善以及在加工能力方面的改善。
尽管在致力于光学和光电材料的研究中取得了显著的进步(例如，红色和绿色磷光有机金属材料可商购和已经在有机发光二极管(OLED)、照明、和高级显示器中用作磷光体)，但是许多目前可利用的材料呈现出许多缺点，包括尤其是差的加工能力、效率低的发射或吸收、以及不太理想的稳定性。
好的蓝光发射体特别稀少，其中一个挑战是蓝光器件的稳定性。主体材料的选择对于器件的稳定性和效率具有影响。与红色和绿色磷光体的最低三重激发态能量相比，蓝色磷光体的最低三重激发态能量非常高，这意味着，蓝光器件的主体材料的最低三重激发态能量应该甚至更高。因此，问题之一是，用于蓝光器件的主体材料有限。因此，需要新的材料，其在光学发射和吸收应用中呈现出改善的性能。
发明内容
设计和合成了一系列用官能化苯基卡宾配体环金属化的(cyclometalated)四齿铂(II)络合物和它们的类似物(用官能化苯基卡宾配体和它们的类似物环金属化的四齿铂(II)络合物)。这些络合物提供改善的色纯度、增强的操作稳定性、以及减少的或者消除的潜在的强的分子间相互作用，并适用于发光标记物(lable)、用于有机发光二极管(OLED)和照明应用的发射体、和光子降频变换器。
本文中公开了式I和式II的络合物：
其中：
Ar为五元杂芳基、五元卡宾、五元N-杂环卡宾、六元芳基、或者六元杂芳基，
每个R1独立地为 或者
R、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、和R12中的每个独立地为氢、卤素、羟基、硝基、硫醇基；或者取代的或者未取代的：C1-C4烷基、烷氧基、芳基、或者氨基，其中当Ar为五元环时R不存在，
X为O、S、S＝O、O＝S＝O、Se、Se＝O、O＝Se＝O、NR2a、PR2b、AsR2c、CR2dR2e、SiR2fR2g、或者BR2h，
R2a、R2b、R2c、R2d、R2e、R2f、R2g、和R2h中的每个独立地为取代的或者未取代的C1-C4烷基或者芳基，
Y存在或者不存在，以及如果存在，Y为O、S、S＝O、O＝S＝O、Se、Se＝O、O＝Se＝O、NR3a、PR3b、AsR3c、CR3dR3e、SiR3fR3g、或者BR3h、和
R3a、R3b、R3c、R3d、R3e、R3f、R3g、和R3h中的每个独立地为取代的或者未取代的C1-C4烷基或者芳基。
在一些情况中，Ar为吡唑、咪唑、唑、噻唑、吡啶等。在一些情况中，在相同环或者相邻环上的R、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、和R12中的任意两个结合(键合)在一起以形成稠环体系。例如，R和R2、R2和R4、或者R4和R6可结合从而与Ar形成稠环体系，例如苯并咪唑、苯并唑、苯并噻唑、吲唑、喹啉、异喹啉、咪唑并[1,5-a]吡啶等。
本文中还公开了包含一种或者多种本文中公开的络合物的组合物、以及包含本文中公开的一种或者多种化合物或者组合物的器件例如OLED。
因此，已经描述了具体实施方案。所述实施方案和其它实施方案的变型、修饰、和改进可基于所描述和说明的内容作出。另外，一个或者多个实施方案的一个或者多个特征可组合。一个或者多个实施以及各种特征和方面的细节在下面的附图、说明书、和权利要求中阐述。
附图说明
图1描绘了示例性有机发光器件(OLED)的横截面图。
图2显示了Pt7O7-dipr在室温和77K的光致发光光谱。
具体实施方式
通过参考下面的详细描述和其中包括的实例，可以更容易地理解本公开内容。
在公开和描述本络合物、器件、和/或方法之前，将理解，它们不限于具体的合成方法，除非另外说明，或者它们不限于特定的试剂，除非另外说明，因为这些当然可以改变。还将理解，本文中所使用的术语仅为了描述具体方面的目的，且不意图为限制性的。尽管与本文中所描述的那些方法和材料类似或等同的任何方法和材料可用于实践或试验中，但现在描述实例方法和材料。
如本说明书和所附权利要求书中所使用的，单数形式“一个(种)(a,an)”和“该(所述)”包括复数指示物(referent)，除非上下文清楚地另外说明。因此，例如，对“一种组分(组分，acomponent)”的提及包括两种或更多种组分的混合物。
如本文中所使用的，术语“任选的”或“任选地”表示随后描述的事件或情况可发生或可不发生，以及所述描述包括其中所述事件或情况发生的情形和其中所述事件或情况不发生的情形。
公开将用于制备本文中所述的组合物的组分以及将在本文中公开的方法中使用的组合物本身。本文中公开这些和其它材料，并且理解，当这些材料的组合、子集、相互作用、集合等被公开时，虽然这些化合物的各种单独的和共同的组合和排列(permutation)各自的具体指示物不能被明确地公开，但每一种在本文中被具体地设计和描述。例如，如果具体化合物被公开和讨论并且对包括所述化合物的许多分子可进行的许多变化被讨论，则可能的变化以及化合物的每种组合和排列被具体地设计，除非具体地相反说明。因此，如果公开了一类分子A、B和C以及一类分子D、E和F，并且公开了组合分子A-D的实例，则即使每个没有被单独地列举，每个也被单独地和共同地被设计，意味着组合A-E、A-F、B-D、B-E、B-F、C-D、C-E和C-F被公开。同样地，这些的任意子集或组合也被公开。因此，例如，A-E、B-F和C-E的子集将被认为被公开。该概念适用于本申请的所有方面，包括，但不限于，制造和使用组合物的方法中的步骤。因此，如果存在可以被执行的多个额外的步骤，则理解，这些额外的步骤各自可用所述方法的任何具体实施方式或实施方式的组合执行。
如本文中提及的，连接原子或者基团可以连接两个原子，例如N原子和C原子。连接原子或者基团在本文中在一个方面中作为X、Y、Y1、Y2和/或Z公开。如果化合价允许的话，连接原子可以任选地具有连接的其它化学部分。例如，在一个方面中，一旦氧键合到两个基团(例如，N和/或C基团)，由于化合价被满足，氧将不具有连接的任何其它化学基团。在另一方面中，当碳是连接原子时，两个额外的化学部分可以连接到碳上。合适的化学部分包括胺、酰胺、硫醇、芳基、杂芳基、环烷基、和杂环基部分。
本文中使用的术语“环状结构”或者类似术语是指任何环状化学结构，其包括，但不限于，芳基、杂芳基、环烷基、环烯基、杂环基、卡宾、和N-杂环卡宾。
如本文中所使用的，术语“取代的”意图包括有机化合物的所有可允许的取代基。在宽的方面中，可允许的取代基包括有机化合物的无环和环状的、支化和非支化的、碳环和杂环的、以及芳族和非芳族的取代基。说明性的取代基包括，例如，下面描述的那些。对于合适的有机化合物，可允许的取代基可以是一个或多个以及相同或不同的。对于本公开内容来说，杂原子，例如氮，可以具有氢取代基和/或满足杂原子的化合价的本文中所描述的有机化合物的任何可允许的取代基。本公开内容不意图被有机化合物的可允许的取代基以任何方式限制。此外，术语“取代”或“被……取代”包括暗示性条件：这样的取代是根据被取代的原子和取代基的允许的化合价，以及该取代产生稳定的化合物，例如不自发地经历转变(例如通过重排、环化、消除等)的化合物。还设计，在一些方面中，除非明确相反说明，单独的取代基可为进一步任选地被取代的(即，进一步取代的或未取代的)。
在定义各种术语时，“X”和“Y”在本文中用作一般性符号来表示各种具体的取代基。这些符号可以是任何取代基，不限于本文中公开的那些，并且，当它们在一种情形下被定义为一些取代基时，它们在另一情形下可以被定义为一些其它的取代基。
如本文中所使用的术语“烷基”是1-24个碳原子的支化或未支化的饱和烃基，例如甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、正戊基、异戊基、仲戊基、新戊基、己基、庚基、辛基、壬基、癸基、十二烷基、十四烷基、十六烷基、二十烷基、二十四烷基等。烷基可以是环状的或无环的。烷基可以是支化或未支化的。烷基还可以是取代或未取代的。例如，烷基可以被一个或多个基团取代，所述基团包括但不限于，如本文中所描述的烷基、环烷基、烷氧基、氨基、醚基、卤素(卤化物，halide)、羟基、硝基、甲硅烷基、硫-氧代(sulfo-oxo)、或硫醇基。“低级烷基”基团是含有一至六个(例如一至四个)碳原子的烷基。
在整个说明书中，“烷基”被概括性地用来指未取代的烷基和取代的烷基两者；然而，取代的烷基通过确定烷基上的具体取代基也在本文中被具体地提到。例如，术语“卤化烷基”或“卤代烷基”具体地指被一种或多种卤素例如氟、氯、溴、或碘取代的烷基。术语“烷氧基烷基”具体地指被如下所述的一个或多个烷氧基取代的烷基。术语“烷基氨基”具体地指被如下所述的一个或多个氨基等取代的烷基。当在一种情形下使用“烷基”并且在另一种情形下使用具体的术语例如“烷基醇”时，其不意图暗示术语“烷基”并非也是指具体术语例如“烷基醇”等。
该实践还可以用于本文中描述的其它基团。即，尽管术语例如“环烷基”是指未取代的和取代的环烷基部分两者，但取代的部分可以另外在本文中具体地确定；例如，具体的取代的环烷基可以被称为例如“烷基环烷基”。类似地，取代的烷氧基可以被具体称为例如“卤化烷氧基”，具体的取代的烯基可以是例如“烯基醇”等。再次，使用概括性术语例如“环烷基”以及具体术语例如“烷基环烷基”的实践不意图暗示所述概括性术语并非也包括所述具体术语。
如本文中所用的术语“环烷基”是由至少三个碳原子构成的非芳族的基于碳的环。环烷基的实例包括，但不限于，环丙基、环丁基、环戊基、环己基、降冰片基等。术语“杂环烷基”是一类如上定义的环烷基，并且被包括在术语“环烷基”的含义范围内，其中环的碳原子的至少一个被杂原子替代，所述杂原子例如，但不限于氮、氧、硫、或磷。环烷基和杂环烷基可以是取代或未取代的。环烷基和杂环烷基可以被一个或多个基团取代，所述基团包括，但不限于如本文中描述的烷基、环烷基、烷氧基、氨基、醚基、卤素、羟基、硝基、甲硅烷基、硫-氧代、或硫醇基。
如本文中所使用的术语“聚烯烃基团”是具有两个或更多个彼此连接的CH2基团的基团。聚烯烃基团可由式-(CH2)a-表示，其中“a”是2-500的整数。
如本文中所使用的术语“烷氧”和“烷氧基”是指通过醚键键合的烷基或环烷基；即，“烷氧”基团可以定义为-OA1，其中A1是如上定义的烷基或环烷基。“烷氧”还包括如刚才所描述的烷氧基团的聚合物；即，烷氧可以是聚醚，例如-OA1-OA2或-OA1-(OA2)a-OA3，其中“a”是1-200的整数并且A1、A2、和A3是烷基和/或环烷基。
如本文中所用的“烯基”是结构式含有至少一个碳-碳双键的2-24个碳原子的烃基。不对称结构例如(A1A2)C＝C(A3A4)意图包括E和Z异构体两者。这可以从其中存在不对称烯烃的本文中的结构式进行推测，或者其可以通过键符号C＝C明确地指示。烯基可以被一个或多个基团取代，所述基团包括，但不限于如本文中所述的烷基、环烷基、烷氧基、烯基、环烯基、炔基、环炔基、芳基、杂芳基、醛基、氨基、羧酸基、酯基、醚基、卤素、羟基、酮基、叠氮基、硝基、甲硅烷基、硫-氧代、或硫醇基。
如本文中所用的术语“环烯基”是由至少三个碳原子构成并且含有至少一个碳-碳双键即C＝C的非芳族的基于碳的环。环烯基的实例包括，但不限于，环丙烯基、环丁烯基、环戊烯基、环戊二烯基、环己烯基、环己二烯基、降冰片烯基等。术语“杂环烯基”是一类如上定义的环烯基，并且被包括在术语“环烯基”的含义范围内，其中环的碳原子的至少一个被杂原子替代，所述杂原子例如，但不限于氮、氧、硫或磷。环烯基和杂环烯基可以是取代或未取代的。环烯基和杂环烯基可以被一个或多个基团取代，所述基团包括，但不限于如本文中描述的烷基、环烷基、烷氧基、烯基、环烯基、炔基、环炔基、芳基、杂芳基、醛基、氨基、羧酸基、酯基、醚基、卤素、羟基、酮基、叠氮基、硝基、甲硅烷基、硫-氧代、或硫醇基。
如本文中所用的术语“炔基”是结构式含有至少一个碳-碳三键的2-24个碳原子的烃基。炔基可以是未取代的或者被一个或多个基团取代的，所述基团包括，但不限于如本文中描述的烷基、环烷基、烷氧基、烯基、环烯基、炔基、环炔基、芳基、杂芳基、醛基、氨基、羧酸基、酯基、醚基、卤素、羟基、酮基、叠氮基、硝基、甲硅烷基、硫-氧代、或硫醇基。
如本文中所用的术语“环炔基”是由至少七个碳原子构成并且含有至少一个碳-碳三键的非芳族的基于碳的环。环炔基的实例包括，但不限于，环庚炔基、环辛炔基、环壬炔基等。术语“杂环炔基”是一类如上定义的环炔基，并且被包括在术语“环炔基”的含义范围内，其中环的碳原子的至少一个被杂原子替代，所述杂原子例如，但不限于氮、氧、硫、或磷。环炔基和杂环炔基可以是取代的或未取代的。环炔基和杂环炔基可以被一个或多个基团取代，所述基团包括，但不限于如本文中描述的烷基、环烷基、烷氧基、烯基、环烯基、炔基、环炔基、芳基、杂芳基、醛基、氨基、羧酸基、酯基、醚基、卤素、羟基、酮基、叠氮基、硝基、甲硅烷基、硫-氧代、或硫醇基。
如本文中所用的术语“芳基”是含有任何基于碳的芳族基团的基团，包括，但不限于，苯、萘、苯基、联苯基、苯氧基苯等。术语“芳基”还包括“杂芳基”，其被定义为含有如下芳族基团的基团：所述芳族基团具有至少一个引入到所述芳族基团的环中的杂原子。杂原子的实例包括，但不限于，氮、氧、硫、和磷。同样地，术语“非杂芳基”也包括在术语“芳基”的范围内，其定义包含不含杂原子的芳族基团的基团。芳基可以是取代的或未取代的。芳基可以被一个或多个基团取代，所述基团包括，但不限于如本文中描述的烷基、环烷基、烷氧基、烯基、环烯基、炔基、环炔基、芳基、杂芳基、醛基、氨基、羧酸基、酯基、醚基、卤素、羟基、酮基、叠氮基、硝基、甲硅烷基、硫-氧代、或硫醇基。术语“联芳基(biaryl)”是一种特别类型的芳基并且被包括在术语“芳基”的定义范围内。联芳基是指经由稠环结构结合在一起(如在萘中一样)、或者经由一个或多个碳-碳键连接(如在联苯中一样)的两个芳基。
如本文中所用的术语“醛基”由式-C(O)H表示。在整个本说明书中，“C(O)”是羰基即C＝O的简化符号。
如本文中所用的术语“胺基”或“氨基”由式-NA1A2表示，其中A1和A2可以独立地为氢或如本文中描述的烷基、环烷基、烯基、环烯基、炔基、环炔基、芳基或杂芳基。
如本文中所用的术语“烷基氨基”由式-NH(-烷基)表示，其中烷基如本文中所述。代表性的实例包括，但不限于，甲基氨基、乙基氨基、丙基氨基、异丙基氨基、丁基氨基、异丁基氨基、(仲丁基)氨基、(叔丁基)氨基、戊基氨基、异戊基氨基、(叔戊基)氨基、己基氨基等。
如本文中所用的术语“二烷基氨基”由式-N(-烷基)2表示，其中烷基如本文中所述。代表性的实例包括，但不限于，二甲基氨基、二乙基氨基、二丙基氨基、二异丙基氨基、二丁基氨基、二异丁基氨基、二(仲丁基)氨基、二(叔丁基)氨基、二戊基氨基、二异戊基氨基、二(叔戊基)氨基、二己基氨基、N-乙基-N-甲基氨基、N-甲基-N-丙基氨基、N-乙基-N-丙基氨基等。
如本文中所用的术语“羧酸基”由式-C(O)OH表示。
如本文中所用的术语“酯基”由式-OC(O)A1或-C(O)OA1表示，其中A1可为如本文中描述的烷基、环烷基、烯基、环烯基、炔基、环炔基、芳基或杂芳基。如本文中所用的术语“聚酯基”由式-(A1O(O)C-A2-C(O)O)a-或-(A1O(O)C-A2-OC(O))a-表示，其中A1和A2可以独立地为本文中描述的烷基、环烷基、烯基、环烯基、炔基、环炔基、芳基或杂芳基并且“a”是1-500的整数。“聚酯基”作为用来描述通过具有至少两个羧酸基团的化合物与具有至少两个羟基的化合物之间的反应产生的基团的术语。
如本文中所用的术语“醚”由式A1OA2表示，其中A1和A2可以独立地为本文中描述的烷基、环烷基、烯基、环烯基、炔基、环炔基、芳基或杂芳基。如本文中所用的术语“聚醚基”由式-(A1O-A2O)a-表示，其中A1和A2可以独立地为本文中描述的烷基、环烷基、烯基、环烯基、炔基、环炔基、芳基或杂芳基并且“a”是1-500的整数。聚醚基团的实例包括聚氧化乙烯、聚氧化丙烯、以及聚氧化丁烯。
术语“聚合的”包括聚烯烃、聚醚、聚酯和其它具有重复单元的基团，例如但不限于-(CH2O)n-CH3、-(CH2CH2O)n-CH3、-[CH2CH(CH3)]n-CH3、-[CH2CH(COOCH3)]n-CH3、-[CH2CH(COOCH2CH3)]n-CH3、和-[CH2CH(COOtBu)]n-CH3，其中n为整数(例如，n>1或者n>2)。
如本文中所用的术语“卤素”是指卤素氟、氯、溴和碘。
如本文中所用的术语“杂环基”是指单环和多环非芳族环体系且如本文中所用的术语“杂芳基”是指单环和多环芳族环体系：其中环成员的至少一个不同于碳。所述术语包括氮杂环丁烷、二氧六烷、呋喃、咪唑、异噻唑、异唑、吗啉、唑、唑(二唑)(包括1,2,3-二唑、1,2,5-二唑和1,3,4-二唑)、哌嗪、哌啶、吡嗪、吡唑、哒嗪、吡啶、嘧啶、吡咯、吡咯烷、四氢呋喃、四氢吡喃、四嗪(包括1,2,4,5-四嗪)、四唑(包括1,2,3,4-四唑和1,2,4,5-四唑)、噻二唑(包括1,2,3-噻二唑、1,2,5-噻二唑和1,3,4-噻二唑)、噻唑、噻吩、三嗪(包括1,3,5-三嗪和1,2,4-三嗪)、三唑(包括1,2,3-三唑、1,3,4-三唑)等。
如本文中所用的术语“羟基”由式-OH表示。
如本文中所用的术语“酮”由式A1C(O)A2表示，其中A1和A2可以独立地为如本文中描述的烷基、环烷基、烯基、环烯基、炔基、环炔基、芳基或杂芳基。
如本文中所用的术语“叠氮基”由式-N3表示。
如本文中所用的术语“硝基”由式-NO2表示。
如本文中所用的术语“腈基”由式-CN表示。
如本文中所用的术语“甲硅烷基”由式-SiA1A2A3表示，其中A1、A2和A3可以独立地为氢或如本文中描述的烷基、环烷基、烷氧基、烯基、环烯基、炔基、环炔基、芳基或杂芳基。
如本文中所用的术语“硫-氧代”由式-S(O)A1、-S(O)2A1、-OS(O)2A1、或-OS(O)2OA1表示，其中A1可为氢或如本文中描述的烷基、环烷基、烯基、环烯基、炔基、环炔基、芳基或杂芳基。在整个本说明书中，“S(O)”是S＝O的简化符号。如本文中所用的术语“磺酰基”指的是由式-S(O)2A1表示的硫-氧代基团，其中A1可为氢或如本文中描述的烷基、环烷基、烯基、环烯基、炔基、环炔基、芳基或杂芳基。如本文中所用的术语“砜”由式A1S(O)2A2表示，其中A1和A2可以独立地为如本文中描述的烷基、环烷基、烯基、环烯基、炔基、环炔基、芳基或杂芳基。如本文中所用的术语“亚砜”由式A1S(O)A2表示，其中A1和A2可以独立地为如本文中描述的烷基、环烷基、烯基、环烯基、炔基、环炔基、芳基或杂芳基。
如本文中所用的术语“硫醇基”由式-SH表示。
如本文中所用的“R1”、“R2”、“R3”、“Rn”，其中n是整数，可以独立地具有一个或多个上面所列出的基团。例如，如果R1是直链烷基，则所述烷基的氢原子之一可以任选地被羟基、烷氧基、烷基、卤素等取代。取决于所选择的基团，第一基团可以引入到第二基团内，或者替代地，第一基团可以悬挂(即连接)到第二基团上。例如，对于短语“包含氨基的烷基”，氨基可以引入到烷基的骨架内。替代地，氨基可以连接到烷基的骨架。所选择的基团的性质将决定第一基团是嵌入还是连接到第二基团。
本文中所述化合物可以含有“任选地取代的”部分。通常，不管前面是否加上术语“任选地”，术语“取代的”都表示指定部分的一个或多个氢原子被合适的取代基替代。除非另外说明，“任选地取代的”基团可以在所述基团的每个可取代的位置处具有合适的取代基，并且当任意给定结构中的超过一个位置可以被选自规定基团的超过一个取代基取代时，在每个位置处，取代基可以是相同或不同的。由本发明所预期的取代基的组合优选为导致形成稳定的或化学上可行的化合物的那些。还设计，在一些方面中，除非明确地相反说明，否则单独的取代基可以为进一步任选地取代的(即进一步取代的或未取代的)。
在一些方面中，化合物的结构可以由下式表示：
其被理解为与下式等同：
其中n典型地为整数。即，Rn理解为表示五个独立的取代基Rn(a)、Rn(b)、Rn(c)、Rn(d)、Rn(e)。“独立的取代基”表示各R取代基可以被独立地定义。例如，如果在一种情形下Rn(a)是卤素，则Rn(b)在该情形下不一定是卤素。
在本文中公开和描述的化学结构和部分中数次提到了R1、R2、R3、R4、R5、R6等。在本说明书中的R、R1、R2、R3、R4、R5、R6等的任何描述分别可适用于列举R、R1、R2、R3、R4、R5、R6等的任何结构或部分。
由于许多原因，利用有机材料的光电子器件正变得越来越合乎需要。用于制造这样的器件的材料中的许多是相对便宜的，因此有机光电子器件由于成本优势而相对于无机器件具有潜力。此外，有机材料的内在性质，例如它们的柔性，可以使得它们非常适合用于特定的应用例如在柔性基板上的制造。有机光电子器件的实例包括有机发光器件(有机发光二极管)(OLED)、有机光电晶体管、有机光伏电池、和有机光电探测器。对于OLED，有机材料相对于常规的材料可具有性能优势。例如，有机发光层发射光的波长可以通常使用合适的掺杂剂容易地调节。
激子从单重激发态衰变至基态以产生迅速的发光，其为荧光。激子从三重激发态衰变至基态以产生发光，其为磷光。因为重金属原子的强的自旋轨道耦合非常有效地增强在单重和三重激发态之间的系间穿越(ISC)，磷光金属络合物如铂络合物已经显示了它们俘获单重态和三重态激子以实现100％内量子效率的潜力。因此，磷光金属络合物是在有机发光器件(OLED)的发射层中作为掺杂剂的良好候选者且在学术和工业领域中已得到大量关注。
然而，迄今为止，蓝光电致发光器件仍然是这种技术的最富挑战性的领域，这至少部分地是由于蓝光器件的不稳定性。通常理解，主体材料的选择是蓝光器件的稳定性中的一个因素。但是，蓝色磷光体的最低三重激发态(T1)能量高，这通常意味着，蓝光器件的主体材料的最低三重激发态(T1)能量应该甚至更高。这导致在用于蓝光器件的主体材料的开发中的困难。
通过引入桥接到金属络合物的配体的碳类基团(C、Si、Ge)，本公开内容提供了材料设计路线。如本文中所述，发现了与具有相同发射基团的氮桥接Pt络合物相比，碳桥接Pt络合物的光致发光光谱具有显著的蓝移。还发现，可改变发射发光团和配体的化学结构，以及可改变金属以调节金属络合物的单重态能量和三重态能量，其均可影响络合物的光学性质。
可将本文中所述的金属络合物根据由特定的发射或者吸收特性所促进的具体应用进行修整(tailor)或调整。在本公开内容中的金属络合物的光学性质可通过以下方法调整：改变围绕金属中心的配体的结构或者改变配体上的荧光发光团的结构。例如，具有拥有给电子取代基或者吸电子取代基的配体的金属络合物通常可呈现出不同的光学性质，包括发射和吸收光谱。金属络合物的颜色可通过以下方法调整：改变配体和荧光发光团上的共轭基团。
通过例如改变配体或者荧光发光团结构，可将这样的络合物的发射例如从紫外调整至近红外。荧光发光团为在有机分子中的可吸收能量以产生一个或多个单重激发态的原子组(group)。一个或多个单重态激子快速产生衰变以产生迅速的发光。在一个方面中，所述络合物可在可见光谱的大部分范围内提供发射。在一个具体实例中，本文中所述络合物可在约400nm至约700nm的范围内发射光。在另一方面中，所述络合物相对于传统发光络合物具有改善的稳定性和效率。在又一方面中，所述络合物作为在例如生物应用、抗癌剂中的标记物、有机发光二极管(OLED)中的发射体、或者其组合可为有用的。在另一方面中，所述络合物在发光器件，例如，紧凑型荧光灯(CFL)、发光二极管(LED)、白炽灯、及其组合中可为有用的。
本文中公开了铂化合物、化合物络合物、或者络合物。术语化合物、化合物络合物、和络合物在本文中可互换地使用。在一个方面中，本文中公开的化合物具有电中性(neutralcharge)。
本文中公开的化合物可以呈现出期望的性质并且具有可经由合适配体的选择而调整的发射和/或吸收光谱。在另一方面中，可以排除本文中具体叙述的化合物、结构、或其部分的任意一种或多种。
本文中公开的化合物适合用于各种各样的光学和光电器件，包括，但不限于，光吸收器件例如太阳能敏感器件和光敏器件、有机发光二极管(OLED)、光发射器件、或既能够进行光吸收也能够进行光发射和作为用于生物应用的标志器的器件。
如以上简要描述的，所公开的化合物是铂络合物。在一个方面中，本文中公开的化合物可以用作用于OLED应用例如全色显示器的主体材料。
本文中公开的化合物在多种应用中可为有用的。作为发光材料，所述化合物在有机发光二极管(OLED)、发光器件和显示器、以及其它发光器件中可为有用的。
在另一方面中，与常规材料相比，所述化合物可以在照明器件例如有机发光器件中提供改善的效率和/或改善的工作寿命。
本文中所述的化合物可以使用多种方法制造，所述方法包括但不限于实施例中所叙述的那些。
本文中所公开的化合物包括延迟荧光发射体、磷光发射体、或者其组合。在一个方面中，本文中所公开的化合物为延迟荧光发射体。在另一方面中，本文中所公开的化合物为磷光发射体。在又一方面中，本文中所公开的化合物为延迟荧光发射体和磷光发射体两者。
本文中公开了式I和式II的络合物：
其中：
Ar为五元杂芳基、五元卡宾、五元N-杂环卡宾、六元芳基、或者六元杂芳基，
每个R1独立地为 或者
R、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、和R12中的每个独立地为氢、卤素、羟基、硝基、硫醇基；取代的或者未取代的：C1-C4烷基、烷氧基、芳基、或者氨基，其中当Ar为五元环时R不存在，
X为O、S、S＝O、O＝S＝O、Se、Se＝O、O＝Se＝O、NR2a、PR2b、AsR2c、CR2dR2e、SiR2fR2g、或者BR2h，
R2a、R2b、R2c、R2d、R2e、R2f、R2g、和R2h中的每个独立地为取代的或者未取代的C1-C4烷基或者芳基，
Y存在或者不存在，以及如果存在，Y为O、S、S＝O、O＝S＝O、Se、Se＝O、O＝Se＝O、NR3a、PR3b、AsR3c、CR3dR3e、SiR3fR3g、或者BR3h，和
R3a、R3b、R3c、R3d、R3e、R3f、R3g、和R3h中的每个独立地为取代的或者未取代的C1-C4烷基或者芳基。
在一些情况中，Ar为吡唑、咪唑、唑、噻唑、吡啶等。在一些情况中，在相同环或者相邻环上的R、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、和R12中的任意两个结合在一起以形成稠环体系。例如，R和R2、R2和R4、或者R4和R6可结合以与Ar形成稠环体系，例如苯并咪唑、苯并唑、苯并噻唑、吲唑、喹啉、异喹啉、咪唑并[1,5-a]吡啶等。
在一些情况中，X直接连接至R10或者R11。在一些情况中，Y直接连接至R6或者R8。
在本公开内容中的金属络合物包括以下结构中的一种或者多种。在本公开内容中的金属络合物也可包括本文中未具体描述的其它结构或者其部分，并且本公开内容不意图限于具体描述的那些结构或者其部分。在下面的结构中，“Ad”是指“金刚烷基”；“Mes”是指“基(mesityl)”；“Dipp”是指“二异丙基苯基”；“Np”是指“新戊基”；和“Cy”是指“环己基”。
本文中还公开了包含本文中公开的络合物中的一种或者多种的器件。
本文中公开的络合物适合用于各种各样的器件，包括例如光学和光电器件，包括，例如光吸收器件例如太阳能敏感器件和光敏器件、有机发光二极管(OLED)、光发射器件、或既能够进行光吸收也能够进行光发射和作为用于生物应用的标志器的器件。
本文中还公开了包含本文中公开的络合物中的一种或者多种的器件。
本文中公开的络合物适合用于各种各样的器件，包括例如光学和光电器件，包括，例如光吸收器件例如太阳能敏感器件和光敏器件、有机发光二极管(OLED)、光发射器件、或既能够进行光吸收也能够进行光发射和作为用于生物应用的标志器的器件。
本文中所述的络合物可用于OLED。图1描绘OLED100的横截面图。OLED100包含基底102、阳极104、空穴传输材料(HTL)106、光处理材料108、电子传输材料(ETL)110、和金属阴极层112。阳极104典型地为透明材料，例如氧化铟锡。光处理材料108可为包含发射体和主体的发射材料(EML)。
在多个方面中，图1中所描绘的一个或者多个层中的任何层可包含氧化铟锡(ITO)、聚(3,4-亚乙基二氧噻吩)(PEDOT)、聚磺苯乙烯(PSS)、N,N’-二-1-萘基-N,N-二苯基-1,1’-联苯-4,4’-二胺(NPD)、1,1-双((二-4-甲苯基氨基)苯基)环己烷(TAPC)、2,6-双(N-咔唑基)吡啶(mCpy)、2,8-双(二苯基磷酰基)二苯并噻吩(PO15)、LiF、Al、或其组合。
光处理材料108可以包括本公开内容的一种或多种络合物以及主体材料或者没有主体材料。主体材料可以是任何合适的已知的主体材料。OLED的发射颜色由光处理材料108的发射能量(光学能隙)决定，其可以通过调整发光络合物和/或主体材料的电子结构而进行调整。HTL层106中的空穴传输材料和ETL层110中的电子传输材料两者都可以包括任何合适的已知的空穴传输物。
本文中描述的络合物可以呈现出磷光。磷光OLED(即具有磷光发射体的OLED)典型地具有比其它OLED例如荧光OLED高的器件效率。基于电致磷光发射体的发光器件更详细地描述于Baldo等人的WO2000/070655中，由于该文献对于OLED且特别是磷光OLED的教导，将其引入本文中。
实施例
提出下列实施例以向本领域普通技术人员提供如何制造和评价本文中描述的化合物、组合物、制品、器件和/或方法的完整公开内容和描述，并且所述实施例意图仅是示范性的且不意图限制范围。尽管已经进行努力以确保关于数值(例如，量、温度等)的准确性，但是应当考虑一些误差和偏差。除非另外说明，否则份数为重量份，温度是以℃为单位或者在环境温度下，且压力是在大气压下或附近。
在实施例中叙述用于本文中所描述的化合物的制备方法的多种方法。这些方法被提供用于说明多种制备方法，但是不意图限制本文中所叙述的方法的任一种。因此，本公开内容所属领域的技术人员可容易地修改所叙述的方法或利用不同的方法来制备本文中所述化合物的一种或多种。下列方面仅是示例性的，且不意图限制范围、温度、催化剂、浓度、反应物组成、以及其它工艺条件可改变，并且对于期望的络合物，本公开内容所属领域的技术人员可容易地选择合适的反应物和条件。
在VarianLiquidStateNMR仪器上于CDCl3或DMSO-d6溶液中以400MHz记录1H谱，以100MHz记录13CNMR谱，且化学位移参照残留的质子化(protiated)溶剂。如果将CDCl3用作溶剂，则采用四甲基硅烷(δ＝0.00ppm)作为内标记录1HNMR谱；采用CDCl3(δ＝77.00ppm)作为内标记录13CNMR谱。如果将DMSO-d6用作溶剂，则采用残留的H2O(δ＝3.33ppm)作为内标记录1HNMR谱；采用DMSO-d6(δ＝39.52ppm)作为内标记录13CNMR谱。使用下列缩写(或其组合)来说明1HNMR的多重性：s＝单重，d＝双重，t＝三重，q＝四重，p＝五重，m＝多重，br＝宽。
参照下面的对于Pt7O7-dipr的方案1描述用于本文中公开的络合物的示例性合成方法。
方案1
向经烘箱干燥的烧瓶添加Pt7O7-dipr的配体(610mg,0.9mmol)、K2PtCl4(392mg,0.945mmol)、和n-Bu4NBr(29mg,0.09mmol)。将烧瓶用N2排空和回填，然后在N2的保护下添加HOAc(45mL,0.02M)。然后将混合物在120℃加热3天。将所得混合物冷却至室温并在减压下浓缩。通过快速柱色谱法在硅胶上的纯化(DCM/己烷＝1/1至3/1)提供作为淡黄色固体的Pt7O7-dipr(99mg,19％的产率)。1HNMR(DMSO-d6,400MHz)：δ8.04(d,J＝2.0Hz,2H),7.65(d,J＝2.0Hz,2H),7.20(d,J＝7.4Hz,2H),7.11(t,J＝7.8Hz,2H),6.96-6.85(m,2H),4.78(七重峰(sept),J＝6.6Hz,2H),1.47(d,J＝6.6Hz,12H)。Pt7O7-dipr在室温和77K的光致发光光谱在图2中示出。
本文中所述络合物适于作为用于发光器件如OLED(例如，用于全色显示器和照明应用)的发射体。
考虑到本说明书，多个方面的进一步修饰和替代实施方案对于本领域技术人员而言将为明晰的。因此，本说明书将被解释为仅说明性的。将理解，本文中示出和描述的形式将被视为实施方案的实例。要素和材料可代替本文中说明和描述的那些要素和材料，部件和工艺可被颠倒，和一些特征可被独立地利用，所有这些在了解本说明书的益处后对于本领域技术人员而言是明晰的。在不脱离如在以下权利要求中所述的精神和范围的情况下，可对本文中所述要素作出改变。
Claims (16)
1.由式I或者式II表示的络合物：
其中:
Ar为五元杂芳基、五元卡宾、五元N-杂环卡宾、六元芳基、或者六元杂芳基，
每个R1独立地为 或者
R、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、和R12中的每个独立地为氢、卤素、羟基、硝基、硫醇基；取代的或者未取代的：C1-C4烷基、烷氧基、芳基、或者氨基，其中当Ar为五元环时R不存在，
X为O、S、S＝O、O＝S＝O、Se、Se＝O、O＝Se＝O、NR2a、PR2b、AsR2c、CR2dR2e、SiR2fR2g、或者BR2h，
R2a、R2b、R2c、R2d、R2e、R2f、R2g、和R2h中的每个独立地为取代的或者未取代的C1-C4烷基或者芳基，
Y存在或者不存在，以及如果存在，Y为O、S、S＝O、O＝S＝O、Se、Se＝O、O＝Se＝O、NR3a、PR3b、AsR3c、CR3dR3e、SiR3fR3g、或者BR3h，和
R3a、R3b、R3c、R3d、R3e、R3f、R3g、和R3h中的每个独立地为取代的或者未取代的C1-C4烷基或者芳基。
2.权利要求1的络合物，其中X直接连接至R10或者R11。
3.权利要求1或者权利要求2的络合物，其中Y直接连接至R6或者R8。
4.上述权利要求中的任一项的络合物，其中在相同环或者相邻环上的R、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、和R12中的任意两个结合在一起以形成稠环体系。
5.上述权利要求中的任一项的络合物，其中所述稠环体系包括苯并咪唑、苯并唑、苯并噻唑、吲唑、喹啉、异喹啉、或者咪唑并[1,5-a]吡啶。
6.权利要求1的络合物，其具有以下化学结构之一：
7.上述权利要求中的任一项的络合物，其中所述络合物为延迟荧光和磷光发射体。
8.权利要求1-6中的任一项的络合物，其中所述络合物为磷光发射体。
9.权利要求1-6中的任一项的络合物，其中所述络合物为延迟荧光发射体。
10.制备上述权利要求中的任一项的络合物的方法，所述方法包括：
将配体与铂盐、含溴化合物、和乙酸组合以得到混合物；
加热所述混合物；和
将所述混合物冷却至室温。
11.权利要求10的方法，其中所述铂盐为K2PtCl4。
12.权利要求10或者权利要求11的方法，其中所述含溴化合物为n-Bu4NBr。
13.包含权利要求1-9中的任一项的络合物的器件。
14.权利要求13的器件，其中所述器件为发光器件。
15.权利要求14的器件，其中所述器件为有机发光二极管。
16.权利要求14的器件，其中所述器件为全色显示器。
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| CN202010883430.8A Active CN112159432B (zh) | 2014-07-24 | 2015-07-24 | 用官能化苯基卡宾配体环金属化的四齿铂(ii)络合物和它们的类似物 |
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| Publication number | Publication date |
|---|---|
| US10886478B2 (en) | 2021-01-05 |
| US20180219161A1 (en) | 2018-08-02 |
| KR20220115904A (ko) | 2022-08-19 |
| KR20160012941A (ko) | 2016-02-03 |
| US20210091316A1 (en) | 2021-03-25 |
| KR102433486B1 (ko) | 2022-08-17 |
| CN112159432B (zh) | 2024-04-02 |
| CN105367605B (zh) | 2020-09-25 |
| US9923155B2 (en) | 2018-03-20 |
| CN112159432A (zh) | 2021-01-01 |
| US20160028028A1 (en) | 2016-01-28 |
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