CN101896494B - 具有桥连碳烯配体的过渡金属配合物及其在oled中的用途 - Google Patents
具有桥连碳烯配体的过渡金属配合物及其在oled中的用途 Download PDFInfo
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- CN101896494B CN101896494B CN200880120200.3A CN200880120200A CN101896494B CN 101896494 B CN101896494 B CN 101896494B CN 200880120200 A CN200880120200 A CN 200880120200A CN 101896494 B CN101896494 B CN 101896494B
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- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 title claims abstract description 186
- 239000003446 ligand Substances 0.000 title claims description 114
- 229910052723 transition metal Inorganic materials 0.000 title description 19
- 150000003624 transition metals Chemical class 0.000 title description 19
- -1 halogen ion Chemical class 0.000 claims description 127
- 229910052751 metal Inorganic materials 0.000 claims description 66
- 239000002184 metal Substances 0.000 claims description 66
- 239000002243 precursor Substances 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 28
- 229910052760 oxygen Inorganic materials 0.000 claims description 19
- 229910052717 sulfur Inorganic materials 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000001450 anions Chemical class 0.000 claims description 10
- 230000003647 oxidation Effects 0.000 claims description 10
- 238000007254 oxidation reaction Methods 0.000 claims description 10
- 238000005286 illumination Methods 0.000 claims description 7
- 230000000007 visual effect Effects 0.000 claims description 6
- 150000002500 ions Chemical class 0.000 claims description 4
- 230000003068 static effect Effects 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 239000010410 layer Substances 0.000 description 121
- 239000000463 material Substances 0.000 description 80
- 125000004429 atom Chemical group 0.000 description 54
- 239000002585 base Substances 0.000 description 49
- 239000000975 dye Substances 0.000 description 36
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 27
- 125000001072 heteroaryl group Chemical group 0.000 description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 22
- 125000005843 halogen group Chemical group 0.000 description 21
- 125000000217 alkyl group Chemical group 0.000 description 20
- 239000000758 substrate Substances 0.000 description 18
- 229910052741 iridium Inorganic materials 0.000 description 17
- 238000001465 metallisation Methods 0.000 description 17
- 229910052757 nitrogen Inorganic materials 0.000 description 16
- 229910052697 platinum Inorganic materials 0.000 description 16
- 239000000460 chlorine Substances 0.000 description 15
- 229910052731 fluorine Inorganic materials 0.000 description 15
- 229910052799 carbon Inorganic materials 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 14
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 14
- 125000003118 aryl group Chemical group 0.000 description 13
- 230000005540 biological transmission Effects 0.000 description 13
- 125000004432 carbon atom Chemical group C* 0.000 description 13
- 229920006395 saturated elastomer Polymers 0.000 description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- 125000004366 heterocycloalkenyl group Chemical group 0.000 description 12
- 229910052762 osmium Inorganic materials 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 12
- 125000005842 heteroatom Chemical group 0.000 description 10
- 125000002577 pseudohalo group Chemical group 0.000 description 10
- 229910052782 aluminium Inorganic materials 0.000 description 9
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 229910052801 chlorine Inorganic materials 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 9
- 230000027756 respiratory electron transport chain Effects 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 239000004411 aluminium Substances 0.000 description 8
- 125000004415 heterocyclylalkyl group Chemical group 0.000 description 8
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 8
- 229910052703 rhodium Inorganic materials 0.000 description 8
- 229910052707 ruthenium Inorganic materials 0.000 description 8
- 125000003342 alkenyl group Chemical group 0.000 description 7
- 125000000304 alkynyl group Chemical group 0.000 description 7
- 229910052794 bromium Inorganic materials 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 230000000737 periodic effect Effects 0.000 description 7
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 7
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 6
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- BRTALTYTFFNPAC-UHFFFAOYSA-N boroxin Chemical compound B1OBOBO1 BRTALTYTFFNPAC-UHFFFAOYSA-N 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 238000004020 luminiscence type Methods 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 238000001228 spectrum Methods 0.000 description 6
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 5
- 229910019142 PO4 Inorganic materials 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 5
- 125000003368 amide group Chemical group 0.000 description 5
- 229910000085 borane Inorganic materials 0.000 description 5
- BGECDVWSWDRFSP-UHFFFAOYSA-N borazine Chemical compound B1NBNBN1 BGECDVWSWDRFSP-UHFFFAOYSA-N 0.000 description 5
- 239000004327 boric acid Substances 0.000 description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 5
- 229910052802 copper Inorganic materials 0.000 description 5
- 239000010949 copper Substances 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- 239000003085 diluting agent Substances 0.000 description 5
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 229910000078 germane Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 5
- 125000005597 hydrazone group Chemical group 0.000 description 5
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 5
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 239000010452 phosphate Substances 0.000 description 5
- 125000004076 pyridyl group Chemical group 0.000 description 5
- KXCAEQNNTZANTK-UHFFFAOYSA-N stannane Chemical group [SnH4] KXCAEQNNTZANTK-UHFFFAOYSA-N 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 5
- 229940124530 sulfonamide Drugs 0.000 description 5
- 150000003462 sulfoxides Chemical class 0.000 description 5
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 5
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 5
- 229910006400 μ-Cl Inorganic materials 0.000 description 5
- AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 4
- DJHGAFSJWGLOIV-UHFFFAOYSA-K Arsenate3- Chemical compound [O-][As]([O-])([O-])=O DJHGAFSJWGLOIV-UHFFFAOYSA-K 0.000 description 4
- 229910052684 Cerium Inorganic materials 0.000 description 4
- 229910052693 Europium Inorganic materials 0.000 description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
- 229910052771 Terbium Inorganic materials 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 229940000489 arsenate Drugs 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 239000004020 conductor Substances 0.000 description 4
- 230000021615 conjugation Effects 0.000 description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 description 4
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 229910052737 gold Inorganic materials 0.000 description 4
- 230000005525 hole transport Effects 0.000 description 4
- 230000006872 improvement Effects 0.000 description 4
- 229910052759 nickel Inorganic materials 0.000 description 4
- 229910052763 palladium Inorganic materials 0.000 description 4
- TZMFJUDUGYTVRY-UHFFFAOYSA-N pentane-2,3-dione Chemical compound CCC(=O)C(C)=O TZMFJUDUGYTVRY-UHFFFAOYSA-N 0.000 description 4
- 150000005053 phenanthridines Chemical class 0.000 description 4
- 239000004065 semiconductor Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 4
- 125000001544 thienyl group Chemical group 0.000 description 4
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 4
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 3
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 3
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
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- 125000002541 furyl group Chemical group 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 125000002883 imidazolyl group Chemical group 0.000 description 3
- 238000006317 isomerization reaction Methods 0.000 description 3
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
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- 125000003367 polycyclic group Chemical group 0.000 description 3
- 238000007639 printing Methods 0.000 description 3
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- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 description 3
- 125000003944 tolyl group Chemical group 0.000 description 3
- RRKODOZNUZCUBN-CCAGOZQPSA-N (1z,3z)-cycloocta-1,3-diene Chemical compound C1CC\C=C/C=C\C1 RRKODOZNUZCUBN-CCAGOZQPSA-N 0.000 description 2
- YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical class C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 description 2
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
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- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
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- BCRJHHFLBOQAMG-YNRRLODASA-N [(1e,3e)-penta-1,3-dienyl]benzene Chemical compound C\C=C\C=C\C1=CC=CC=C1 BCRJHHFLBOQAMG-YNRRLODASA-N 0.000 description 2
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- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 2
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 244000309464 bull Species 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
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- 125000000753 cycloalkyl group Chemical group 0.000 description 2
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- 238000000151 deposition Methods 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
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- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 2
- 230000001815 facial effect Effects 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- APPOKADJQUIAHP-UHFFFAOYSA-N hexa-2,4-diene Chemical class CC=CC=CC APPOKADJQUIAHP-UHFFFAOYSA-N 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- HLYTZTFNIRBLNA-LNTINUHCSA-K iridium(3+);(z)-4-oxopent-2-en-2-olate Chemical compound [Ir+3].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O HLYTZTFNIRBLNA-LNTINUHCSA-K 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 2
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- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- JGOAZQAXRONCCI-SDNWHVSQSA-N n-[(e)-benzylideneamino]aniline Chemical compound C=1C=CC=CC=1N\N=C\C1=CC=CC=C1 JGOAZQAXRONCCI-SDNWHVSQSA-N 0.000 description 2
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 2
- 125000002347 octyl 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])[H] 0.000 description 2
- 125000002524 organometallic group Chemical group 0.000 description 2
- 125000002971 oxazolyl group Chemical group 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
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- PLOCPSZUSGEEMU-UHFFFAOYSA-N phenanthridin-1-amine Chemical class C1=CC=CC2=C3C(N)=CC=CC3=NC=C21 PLOCPSZUSGEEMU-UHFFFAOYSA-N 0.000 description 2
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 2
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
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- 239000002966 varnish Substances 0.000 description 2
- HMTSWYPNXFHGEP-UHFFFAOYSA-N (4-methylphenyl)methanamine Chemical compound CC1=CC=C(CN)C=C1 HMTSWYPNXFHGEP-UHFFFAOYSA-N 0.000 description 1
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- VEJOYRPGKZZTJW-FDGPNNRMSA-N (z)-4-hydroxypent-3-en-2-one;platinum Chemical compound [Pt].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O VEJOYRPGKZZTJW-FDGPNNRMSA-N 0.000 description 1
- MBVAQOHBPXKYMF-LNTINUHCSA-N (z)-4-hydroxypent-3-en-2-one;rhodium Chemical compound [Rh].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O MBVAQOHBPXKYMF-LNTINUHCSA-N 0.000 description 1
- BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0033—Iridium compounds
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Abstract
本发明涉及桥连的环金属化碳烯配合物,一种制备桥连的环金属化碳烯配合物的方法,桥连的环金属化碳烯配合物在有机发光二极管中的用途,包含至少一种本发明的桥连的环金属化碳烯配合物的有机发光二极管,包含至少一种本发明的桥连的环金属化碳烯配合物的发光层,包含至少一种本发明的发光层的有机发光二极管以及包含至少一种本发明的有机发光二极管的器件。
Description
本发明涉及桥连的环金属化(cyclometalated)碳烯配合物,一种制备桥连的环金属化碳烯配合物的方法,桥连的环金属化碳烯配合物在有机发光二极管中的用途,包含至少一种本发明桥连的环金属化碳烯配合物的有机发光二极管,包含至少一种本发明桥连的环金属化碳烯配合物的发光层,包含至少一种本发明发光层的有机发光二极管以及包含至少一种本发明有机发光二极管的器件。
有机发光二极管(OLED)利用了材料在受到电流激发时的发光性能。作为阴极射线管和液晶显示器的替代品以生产平面可视显示单元,OLED尤其受到关注。包含OLED的器件由于非常紧密的构造和固有的低能耗,它们特别适于移动应用,例如用于移动电话、笔记本电脑等。
OLED工作方式的基本原理和合适的OLED构造(层)例如描述于WO2005/113704和其中引用的文献中。
现有技术已经提出了许多在受到电流激发时发光的材料。
WO 2005/019373首次公开包含至少一种碳烯配体的不带电荷的过渡金属配合物在OLED中的用途。根据WO 2005/019373,这些过渡金属配合物可用于OLED的任何层,其中配体结构或中心金属是可变化的,以用于调节至过渡金属配合物的所需性能。例如,过渡金属配合物可用于OLED的电子阻挡层、激子阻挡层、空穴阻挡层或发光层,其中优选将过渡金属配合物作为发光体分子用于OLED。
WO 2006/056418公开了不带电荷的过渡金属碳烯配合物的用途,其中所用碳烯配体可以是桥连的碳烯配体。合适的桥连碳烯配体具有如下通式:
其中星号表示n-键接的乙烯碳原子α位的桥A的碳原子或合适的杂原子,和B表示由烷基、链烯基、炔基、芳基或杂芳基(Y1)和化学单键,C(Y4)2、C(O)、O、S、S(O)、SO2或NY5组成的桥。
WO 2005/113704涉及用于OLED的碳烯-金属配合物。在所述许多合适的碳烯配体中,提及了两种桥连配体:
具有较早优先权日但在本申请的优先权日还未公开的申请PCT/EP2007/053262公开了包含碳烯配体和杂环非碳烯配体的杂(heteroleptic)碳烯配合物。碳烯配体可以是桥连的碳烯配体,和所述桥连碳烯配体包括具有下式的那些:
WO 2007/095118涉及环金属化咪唑并[1,2-f]菲啶和二咪唑并[1,2-a:1’,2’-c]喹唑啉配体的金属配合物,及其等电子体和苯并稠合类似物。根据WO 2007/095118,提供了具有延长寿命的发蓝色磷光的OLED。
尽管特别是作为发光物质适用于OLED的桥连碳烯配合物是已知的,提供可在工业上使用的更稳定和/或更有效的化合物还是需要的。
在本发明上下文中,电致发光应理解为指电致发荧光(electrofluorescence)和电致发磷光(electrophosphorescence)两者。
因此,本申请的目的是提供适用于OLED的桥连碳烯配合物。尤其需要提供具有比现有过渡金属配合物改善的性能谱,如改善的效率和/或改善的寿命/稳定性的过渡金属配合物。
该目的通过提供通式(Ⅰ)的桥连的环金属化碳烯配合物而实现:
其中符号各自如下所定义:
M为选自元素周期表(CAS版)第IB、IIB、IIIB、IVB、VB、VIB、VIIB、VIIIB族,镧系元素和第IIIA族金属的金属原子,它们处于合适金属原子可能的任何氧化态;更特别优选Fe、Os、Co、Rh、Ir、Ni、Ru、Pd和Pt、Cu、Au、Ce、Tb、Eu,甚至更特别优选Os、Ru、Rh、Ir和Pt,非常特别优选Ir、Os和Pt;
K为不带电荷的单齿或双齿配体;
L为单阴离子或双阴离子配体,优选单阴离子配体,其可以是单齿或双齿的;
X为CH、CR1或N;
Y为S、O、PR2或SiR2 2;
A、D、G、E、A’、D’、G’和E’各自独立地为CH、CR3或N;
R1、R2、R3各自独立地为取代或未取代的C1-C20烷基、取代或未取代的C5-C20环烷基、取代或未取代的C5-C20环烯基、具有5-30个环原子的取代或未取代的杂环烷基、具有5-30个环原子的取代或未取代的杂环烯基、取代或未取代的C2-C20链烯基、取代或未取代的C2-C20炔基、取代或未取代的C6-C30芳基、具有5-30个环原子的取代或未取代的杂芳基或选自如下的具有给体或受体作用的取代基:C1-C20烷氧基、C6-C30芳氧基、C1-C20烷硫基、C6-C30芳硫基、SiR4R5R6、卤素基团、卤代C1-C20烷基、羰基(-CO(R4))、羰硫基(-C=O(SR4))、羰氧基(-C=O(OR4))、氧羰基(-OC=O(R4))、硫羰基(-SC=O(R4))、氨基(-NR4R5)、OH、拟卤素基团、酰胺基(-C=O(NR4R5))、-NR4C=O(R5)、膦酸根(-P(O)(OR4)2)、磷酸根(-OP(O)(OR4)2)、膦(-PR4R5)、氧化膦(-P(O)R4 2)、硫酸根(-OS(O)2OR4)、亚砜(-S(O)R4)、磺酸根(-S(O)2OR4)、磺酰基(-S(O)2R4)、磺酰胺(-S(O)2NR4R5)、NO2、有机硼酸酯(-B(OR4)2)、亚氨基(-C=NR4R5)、硼烷基团、锡烷基团、肼基、腙基、肟基、亚硝基、重氮基、乙烯基、亚砜亚胺、铝烷、锗烷、环硼氧烷(boroxine)和环硼氮烷;
或
R1和R2基团一起形成饱和或不饱和、取代或未取代的包含3-6个原子的桥,以使R1和R2基团与X-Y基团一起形成5-8元环;
或
两个相邻R3基团一起形成饱和或不饱和、取代或未取代的包含3-6个原子的桥,以使R3基团与单元A=D、D-E、A’=D’、D’-E’、E’=G’之一一起形成5-8元环;
或
位于G’和A位置的R3基团一起形成饱和或不饱和、取代或未取代的包含1-4个原子的桥,以使R3基团与单元-G’-C-C-A-一起形成5-8元环;
R4、R5、R6各自独立地为H、取代或未取代的C1-C20烷基或取代或未取代的C6-C30芳基或具有5-30个环原子的取代或未取代的杂芳基;
n为碳烯配体的数目,其中n至少为1,并且当n>1时,式Ⅰ配合物中的碳烯配体可以相同或不同;
m是配体K的数目,其中m可以为0或≥1,并且当m>1时,配体K可以相同或不同;
o是配体L的数量,其中o可以为0或≥1,并且当o>1时,配体L可以相同或不同;
其中n+m+o之和取决于所用金属原子的氧化态和配位数,取决于配体L和K的齿数以及取决于配体L上的电荷,条件是n至少为1。
本发明式Ⅰ的桥连环金属化碳烯配合物的显著之处在于它们具有碳烯配体桥,以及在Y位置具有选自S、O、PR2或SiR2 2的基团。已经发现式Ⅰ的本发明桥连碳烯配合物的显著之处在于良好稳定性以及借助式Ⅰ的本发明碳烯配合物,可得到具有改进的性能谱,例如改进的效率和/或改进的寿命的OLED。
取代或未取代的C1-C20烷基应理解为指具有1-20个碳原子的烷基。优选C1-C10烷基,特别优选C1-C6烷基。烷基可为直链或支化的。此外,烷基可被一个或多个选自如下的取代基取代:C1-C20烷基、C1-C20烷氧基,卤素,优选F,C1-C20卤代烷基,如CF3,以及C6-C30芳基,其又可以是取代或未取代的。合适的芳基取代基和合适的烷氧基和卤素取代基如下所述。合适的烷基的实例为甲基、乙基、丙基、丁基、戊基、己基、庚基和辛基,以及由C1-C20烷基、C1-C20卤代烷基、C6-C30芳基、C1-C20烷氧基和/或卤素,特别是F,取代的所述烷基的衍生物,例如CF3。还包括所述基团的正异构体,以及支化异构体如异丙基、异丁基、异戊基、仲丁基、叔丁基、新戊基、3,3-二甲基丁基、3-乙基己基等。优选烷基为甲基、乙基、异丙基、叔丁基和CF3。
取代或未取代的C5-C20环烷基应理解为指在基础骨架(环)中具有5-20,优选5-10,更优选5-8个碳原子的环烷基。合适的取代基为对烷基提及的取代基。合适的可未被取代或被对烷基所述的基团取代的环烷基的实例为环戊基、环己基、环庚基、环辛基、环壬基和环癸基。合适的话,它们也可以是多环体系如十氢化萘基、降冰片烷基、莰烷基或金刚烷基。
取代或未取代的C5-C20环烯基应理解为指在基础骨架(环)中具有5-20,优选5-10,更优选5-8个碳原子的环烯基。合适的取代基为对烷基提及的取代基。在环烯基环中,环烯基可具有一个双键或取决于环尺寸可具有超过一个双键。双键可以是共轭或非共轭的。优选环烯基在环烯基环内具有一个双键。合适的环烯基的实例为环戊烯基、环己烯基、环庚烯基、环辛烯基、环壬烯基和环癸烯基,它们可以未被取代或被对烷基所述的基团取代。合适的话,它们也可为多环体系,此时至少一个环为环烯基环。
具有5-30个环原子的取代或未取代的杂环烷基应理解为指具有5-30,优选5-10,更优选5-8个环原子的杂环烷基,其中在杂环烷基基础骨架中的至少一个碳原子被杂原子替换。优选杂原子为N、O和S。合适的取代基为对烷基提及的取代基。可未被取代或被对烷基所述的基团取代的合适的杂环烷基的实例为源自如下杂环的基团:吡咯烷、四氢噻吩(thiolane)、四氢呋喃、1,2-氧硫杂环戊烷(1,2-oxathiolane)、噁唑烷、哌啶、硫杂环己烷(thiane)、噁烷、二噁烷、1,3-二噻烷、吗啉、哌嗪。合适的话,它们也可以是多环体系。
具有5-30个环原子的取代或未取代的杂环烯基应理解为指具有5-30,优选5-10,更优选5-8个环原子的杂环烯基,其中在杂环烯基基础骨架中的至少一个碳原子被杂原子替换且至少一个双键存在于杂环烯基基础骨架中。在杂环烯基环中,杂环烯基可具有一个双键或取决于环尺寸可具有超过一个双键。双键可以是共轭或非共轭的。优选杂环烯基在杂环烯基环内具有一个双键。优选杂原子为N、O和S。合适的取代基为对烷基提及的取代基。
取代或未取代的C2-C20链烯基应理解为指具有2-20个碳原子的链烯基。优选C2-C10链烯基,特别优选C2-C6链烯基。链烯基可以是直链或支化的。此外,链烯基可被一个或多个对烷基提及的取代基取代。取决于链长度,链烯基可具有一个或多个双键,此时双键可以相互共轭或相互独立。合适的链烯基的实例为乙烯基、丙烯基、丁烯基、戊烯基、己烯基、庚烯基和辛烯基,其中双键可存在于上述基团的任意位置,还有被C1-C20烷基、C1-C20卤代烷基、C6-C30芳基、C1-C20烷氧基和/或卤素,尤其是F取代的所述链烯基的衍生物。
取代或未取代的C2-C20炔基应理解为指具有2-20个碳原子的炔基。优选C2-C10炔基,特别优选C2-C6炔基。炔基可以是直链或支化的。此外,炔基可被一个或多个对烷基提及的取代基取代。取决于链长度,炔基可具有一个或多个叁键,此时叁键可以相互共轭或相互独立。合适的炔基的实例为乙炔基、丙炔基、丁炔基、戊炔基、己炔基、庚炔基和辛炔基,其中叁键可存在于上述基团的任意位置,还有被C1-C20烷基、C1-C20卤代烷基、C6-C30芳基、C1-C20烷氧基和/或卤素,尤其是F取代的所述炔基的衍生物。
合适的C1-C20烷氧基和C1-C20烷硫基相应衍生于上述C1-C20烷基。此处,实例包括OCH3、OC2H5、OC3H7、OC4H9和OC8H17,和SCH3、SC2H5、SC3H7、SC4H9和SC8H17。C3H7、C4H9和C8H17包括正异构体和支化异构体,如异丙基、异丁基、仲丁基、叔丁基和2-乙基己基。特别优选的烷氧基或烷硫基为甲氧基、乙氧基、正辛基氧基、2-乙基己氧基和SCH3。
在本发明上下文中,合适的卤素基团或卤素取代基为氟、氯、溴和碘,优选氟、氯和溴,更优选氟和氯,最优选氟。
在本发明上下文中,合适的拟卤素基团为CN、SCN、OCN、N3和SeCN,优选CN和SCN。非常特别优选CN。
在本发明中,C6-C30芳基指衍生自单环、双环或三环芳烃的不含任何环杂原子的基团。当体系不是单环体系时,术语“芳基”中的第二环也可以为饱和形式(全氢化形式)或部分不饱和形式(例如二氢化形式或四氢化形式),其中具体形式已知且稳定。这意味着在本发明中术语芳基例如还包括其中两个或所有三个基团均为芳族的双环或三环基团,以及其中仅有一个环为芳族的双环或三环基团,以及其中两个环为芳族的三环基团。芳基的实例为:苯基、萘基、2,3-二氢化茚基、1,2-二氢萘次甲基、1,4-二氢萘次甲基、茚基、蒽基、菲基或1,2,3,4-四氢萘基。特别优选C6-C10芳基,例如苯基或萘基,非常特别优选C6芳基,如苯基。
C6-C30芳基可以是未取代的或被一个或多个其它基团取代。合适的其它基团选自C1-C20烷基、C6-C30芳基或具有给体或受体作用的取代基,其中具有给体或受体作用的合适取代基如下所述。C6-C30芳基优选未取代或被一个或多个C1-C20烷基、C1-C20烷氧基、CN、CF3、F或氨基(NR4R5,其中合适的R4和R5基团如上所述)取代。C6-C30芳基的其它优选取代基取决于通式(Ⅰ)的化合物的最终用途且如下所述。
合适的C6-C30芳氧基、C6-C30芳硫基相应衍生于上述C6-C30芳基。特别优选苯氧基和苯硫基。
具有5-30个环原子的未取代或取代的杂芳基应理解为指可部分衍生于上述芳基的单环、双环或三环杂芳族基团,其中芳基基础骨架中的至少一个碳原子被杂原子替代。优选杂原子为N、O和S。杂芳基更优选具有5-13个环原子。特别优选杂芳基的基础骨架选自如下体系:如吡啶和五元杂芳族化合物如噻酚、吡咯、咪唑、噻唑、噁唑或呋喃。该基础骨架可任选与一个或两个六元芳基稠合。合适的稠合的杂芳基为咔唑基、苯并咪唑基、苯并呋喃基、苯并噻唑基、苯并噁唑基、二苯并呋喃基或二苯并噻吩基。
基础骨架可在一个、多于一个或所有可被取代的位置被取代,其中合适的取代基与在定义C6-C30芳基时描述的取代基相同。然而,杂芳基优选未被取代。合适的杂芳基例如为吡啶-2-基、吡啶-3-基、吡啶-4-基、噻酚-2-基、噻酚-3-基、吡咯-2-基、吡咯-3-基、呋喃-2-基、呋喃-3-基、噻唑-2-基、噁唑-2-基和咪唑-2-基,以及相应的苯并稠合基团,特别是咔唑基、苯并咪唑基、苯并呋喃基、苯并噻唑基、苯并噁唑基、二苯并呋喃基或二苯并噻吩基。
对本申请而言,具有给体或受体作用的基团应理解为指如下基团:
C1-C20烷氧基、C6-C30芳氧基、C1-C20烷硫基、C6-C30芳硫基、SiR4R5R6、卤素基团、卤代C1-C20烷基、羰基(-CO(R4))、羰硫基(-C=O(SR4))、羰氧基(-C=O(OR4))、氧羰基(-OC=O(R4))、硫羰基(-SC=O(R4))、氨基(-NR4R5)、OH、拟卤素基团、酰胺基(-C=O(NR4R5))、-NR4C=O(R5)、膦酸根(-P(O)(OR4)2)、磷酸根(-OP(O)(OR4)2)、膦(-PR4R5)、氧化膦(-P(O)R4 2)、硫酸根(-OS(O)2OR4)、亚砜(-S(O)R4)、磺酸根(-S(O)2OR4)、磺酰基(-S(O)2R4)、磺酰胺(-S(O)2NR4R5)、NO2、有机硼酸酯(-OB(OR4)2)、亚氨基(-C=NR4R5)、硼烷基团、锡烷基团、肼基、腙基、肟基、亚硝基、重氮基、乙烯基、亚砜亚胺、铝烷、锗烷、环硼氧烷和环硼氮烷。
优选的具有给体或受体作用的取代基选自:
C1-C20烷氧基,优选C1-C6烷氧基,更优选乙氧基或甲氧基;C6-C30芳氧基,优选C6-C10芳氧基,更优选苯氧基;SiR4R5R6,其中R4、R5和R6优选各自独立地为取代或未取代的烷基或取代或未取代的苯基,中合适的取代基如上所述;卤素基团,优选F、Cl、Br,更优选F或Cl,最优选F,卤代C1-C20烷基,优选卤代C1-C6烷基,最优选氟代C1-C6烷基,如CF3、CH2F、CHF2或C2F5;氨基,优选二甲基氨基、二乙基氨基或二苯基氨基;OH、拟卤素基团,优选CN、SCN或OCN,更优选CN、-C(O)OC1-C4烷基,优选-C(O)OMe、P(O)R2,优选P(O)Ph2,和SO2R2,优选SO2Ph。
非常特别优选的具有给体或受体作用的取代基选自如下:甲氧基、苯氧基,卤代C1-C4烷基,优选CF3、CH2F、CHF2、C2F5、卤素,优选F、CN,其中合适的R4、R5和R6基团已经被提及的SiR4R5R6,二苯基氨基、-C(O)OC1-C4烷基,优选-C(O)OMe、P(O)Ph2和SO2Ph。
上述具有给体或受体作用的基团并没有排除也可具有给体或受体作用的其它上述基团的可能性。例如,上述杂芳基同样具有给体或受体作用,而C1-C20烷基具有给体作用。
在上述具有给体或受体作用的基团中提及的基团R4、R5和R6各自如上文所定义,即R4、R5和R6各自独立地为:
氢、取代或未取代的C1-C20烷基或取代或未取代的C6-C30芳基或具有5-30个环原子的取代或未取代的杂芳基,合适和优选的烷基和芳基如上所述。更优选R4、R5和R6基团各自为C1-C6烷基,如甲基、乙基、异丙基或叔丁基,或者苯基或吡啶基。
在通式Ⅰ的本发明桥连环金属化碳烯配合物中的金属原子M选自元素周期表(CAS版)第IB、IIB、IIIB、IVB、VB、VIB、VIIB、VIIIB族,镧系元素和第IIIA族金属,它们处于合适金属原子可能的任何氧化态;优选Fe、Os、Co、Rh、Ir、Ni、Ru、Pd和Pt、Cu、Au、Ce、Tb、Eu,更优选Os、Ru、Rh、Ir和Pt,最优选Ir、Os和Pt,它们处于合适金属原子可能的任何氧化态。
更优选金属M选自Ir、Os和Pt,优选Os(Ⅱ)、Ir(Ⅲ)和Pt(Ⅱ)。特别优选Ir(Ⅲ)。
碳烯配体数目n和任何存在的配体K和L的数目m和o取决于金属M的氧化态和配位数以及取决于配体L的齿数和电荷,其中至少一个碳烯配体存在于本发明式Ⅰ的碳烯配合物中,即n至少为1。
取决于所用金属M的电荷和配位数的式Ⅰ的本发明碳烯配合物的优选实施方案如下所述:
在M为具有配位数4的金属(如Pt(Ⅱ)或Pd(Ⅱ)、Ir(Ⅰ)、Rh(I))的情况下,本发明的式Ⅰ碳烯配合物具有一个或两个碳烯配体,即n为1或2,其中在n为1和M为具有配位数4的金属的情况下,在本发明碳烯配合物中存在一个单阴离子双齿配体L以及碳烯配体,即o为1。在M为具有配位数6的金属(如Ir(Ⅲ)、Co(Ⅱ)、Co(Ⅲ)、Rh(Ⅲ)、Os(Ⅱ)、Pt(Ⅳ))的情况下,本发明的式Ⅰ碳烯配合物取决于它们的电荷优选具有1、2或3个,优选2或3个通式Ⅰ的碳烯配体(它们可以是相同或不同的),即n为1、2或3,优选2或3。例如,在Ir(Ⅲ)、Co(Ⅲ)或Rh(Ⅲ)的情况下,n通常为1、2或3,其中在n=1的情况下,存在两个额外的单阴离子双齿配体L,即o为2。在n=2的情况下,上述碳烯配合物具有一个额外的单阴离子双齿配体L,即o为1。在特别优选的n=3的情况下,上述碳烯配合物不具有任何其它配体K和L,即m和o各自为0。在Os(Ⅱ)的情况下,n通常为1或2,其中在n=1的情况下,存在一个额外的单阴离子双齿配体L和一个额外的不带电荷的双齿配体K,即o为1且m为1。在特别优选的n=2的情况下,上述碳烯配合物具有一个额外的不带电荷的双齿配体K,即m为1。当金属原子M具有配位数8或更高时,本发明通式Ⅰ的碳烯配合物,除了1、2或3个碳烯配体外可具有一个或多个其它碳烯配体和/或一个或多个额外的配体K和/或L。在优选实施方案中,本发明涉及通式Ⅰ的桥连环金属化碳烯配合物,其具有配位数6的金属M,优选优选Ir(Ⅲ),其中n=3且m和o各自为0。
取决于所用金属M的配位数、所用碳烯配体的数目n和可使用的额外配体K和L的数目m和o,可以存在具有相同金属M和相同性质的所用碳烯配体和额外配体的相应金属配合物的不同异构体。例如在配合物具有的金属M的配位数为6(即八面体配合物)的情况下,例如对于Ir(Ⅲ)配合物,当配合物为具有通用组成M(AB)3的那些时,面式/经式异构体是可能的,其中AB为双齿配体。在本申请上下文中,“面式-经式异构体”应理解为指如下所示的异构体:
面式异构体 经式异构体
在具有配位数4的金属M的正方平面配合物如Pt(Ⅱ)配合物的情况下,当配合物为具有通用组成M(AB)2的那些时,顺/反异构体是可能的,其中AB为双齿配体。在本申请上下文中,“异构体”理解为指如下所示的异构体:
反式异构体 顺式异构体
符号A和B各自为配体的一个连接位置,其中仅存在双齿配体。根据上述通用组成,双齿配体具有2个基团A和两个基团B。
本领域熟练技术人员原则上理解顺式/反式和面-经式异构体的意义。在组成为MA3B3的配合物情况下,相同类型的三个基团可以占据一个八面体面的角(面式异构体)或者占据经线,即三个配体的结合点中的两个相互呈反式(经式异构体)。对于八面体金属配合物中顺式/反式异构体和面-经式异构体的定义,例如参见J.Huheey,E.Keiter,R.Keiter,AnorganischeChemie:Prinzipien von Struktur und[无机化学:结构和反应性原理],第2版,新修订版,被翻译成德文并且由Ralf Steudel扩展,Berlin;New York:de Gruyter,1995,第575、576页。
在正方平面配合物的情况下,顺式异构体是指在组成为MA2B2的配合物中,两个A基团和两个B基团均占据正方形的相邻角,而在反式异构体的情况下,两个A基团和两个B基团各自占据正方形的两个相互的斜对角。对于正方平面金属配合物中顺式/反式异构体的定义,例如参见J.Huheey,E.Keiter,R,Keiter,Anorganische Chemie:Prinzipien von Struktur und第2版,新修订版,被翻译成德文并且由Ralf Steudel扩展,Berlin;New York:de Gruyter,1995,第557-559页。
通常而言,本发明的式Ⅰ的碳烯配合物的不同异构体可以通过本领域熟练技术人员已知的方法,例如通过色谱法、升华或结晶而分离。
本发明因此涉及式Ⅰ的碳烯配合物的在每种情况下的单个异构体以及不同异构体以任何混合比的混合物。
在其中过渡金属M具有配位数6且氧化态Ⅲ的本发明式Ⅰ的桥连环金属化碳烯配合物中,碳烯配体数目n优选3,其中对于过渡金属M特别优选为Ir(Ⅲ),并且在这些配合物中额外配体K和L的数目m和o优选各自为0。
在其中过渡金属M具有配位数6且氧化态Ⅱ的本发明式Ⅰ的桥连环金属化碳烯配合物中,碳烯配体数目n优选2,其中对于过渡金属M特别优选为Os(Ⅱ),此时存在一个额外的不带电荷的双齿配体K,即m优选为1。在这些配合物中o优选为0。
在其中过渡金属M具有配位数4的本发明式Ⅰ的桥连环金属化碳烯配合物(对于过渡金属M特别优选为Pt(Ⅱ))中,碳烯配体数目n优选为1或2,其中在n=1的情况下,优选存在一个额外的单阴离子双齿配体L,即o同样优选为1且m优选为0。在n=2的情况下,m和o优选各自为0。
在非常特别优选的实施方案中,式Ⅰ碳烯配合物中的M为Ir(Ⅲ),n为3且m和o各自为0。
在碳烯配合物中,当n>1时n个碳烯配体可以相同或不同。它们优选相同,即在M=Ir(Ⅲ)和n=3的情况下,三个碳烯配体优选相同。
合适的可以是单齿或双齿的单阴离子或双阴离子配体L,优选单阴离子配体L为通常作为单齿或双齿的单阴离子或双阴离子配体使用的配体。
合适的单阴离子单齿配体例如为卤离子,尤其是Cl-和Br-,拟卤离子,尤其是CN-,环戊二烯基(Cp-),氢离子,烷氧基,芳氧基,经由σ键键接于过渡金属M1上的烷基,例如CH3,经由σ键键接于过渡金属M1上的烷基芳基,例如苄基。
合适的单阴离子二齿配体例如为乙酰丙酮酸根及其衍生物、甲基吡啶酸根、席夫碱、氨基酸、芳基唑类,如苯基吡啶,以及WO 02/15645中所述的其它二齿单阴离子配体,其中优选乙酰丙酮酸根和甲基吡啶酸根。
合适的双阴离子二齿配体例如为二醇盐离子、二碳酸根、二羧酸根、二酰胺、二酰亚胺、二硫醇盐离子、双环戊二烯基、二膦酸根、二磺酸根和3-苯基吡唑。
合适的不带电荷的单齿或二齿配体K优选选自膦(单膦和双膦两者);磷酸酯(单磷酸酯和双磷酸酯两者)及其衍生物,砷酸酯(单砷酸酯和双砷酸酯两者)及其衍生物;亚磷酸酯(单亚磷酸酯和双亚磷酸酯两者),CO,吡啶类(单吡啶和联吡啶两者),腈,二腈,烯丙基,二亚胺,与M1形成π-配合物的非共轭二烯和共轭二烯。特别优选的不带电荷的单齿或二齿配体K选自膦,包括单膦和双膦,优选三烷基膦、三芳基膦或烷基芳基膦,更优选PAr3,其中Ar为取代或未取代的芳基并且PAr3中的三个芳基可相同或不同,更优选PPh3、PEt3、PnBu3、PEt2Ph、PMe2Ph、PnBu2Ph;膦酸酯及其衍生物,砷酸酯及其衍生物,亚磷酸酯,CO;吡啶,包括单吡啶和联吡啶,其中吡啶可被烷基或芳基取代;与M1形成π-配合物的腈和二烯,优选η4-联苯-1,3-丁二烯、η4-1,3-戊二烯、η4-1-苯基-1,3-戊二烯、η4-1,4-二苄基-1,3-丁二烯、η4-2,4-己二烯、η4-3-甲基-1,3-戊二烯、η4-1,4-二甲苯基-1,3-丁二烯、η4-1,4-双(三甲基甲硅烷基)-1,3-丁二烯和η2-或η4-环辛二烯(在每种情况下1,3和在每种情况下1,5),更优选1,4-联苯-1,3-丁二烯、1-苯基-1,3-戊二烯、2,4-己二烯、丁二烯、η2-环辛烯、η4-1,3-环辛二烯和η4-1,5-环辛二烯。非常特别优选的不带电荷的单齿配体选自PPh3、P(OPh)3、AsPh3、CO、吡啶、腈及其衍生物。合适的不带电荷的单齿或双齿配体优选为1,4-联苯-1,3-丁二烯、1-苯基-1,3-戊二烯、2,4-己二烯、η4-环辛二烯和η2-环辛二烯(在每种情况下1,3和在每种情况下1,5)。
在式Ⅰ的桥连环金属化碳烯配合物中的R1、R2和R3基团各自独立地为取代或未取代的C1-C20烷基、取代或未取代的C5-C20环烷基、取代或未取代的C5-C20环烯基、具有5-30个环原子的取代或未取代的杂环烷基、具有5-30个环原子的取代或未取代的杂环烯基、取代或未取代的C2-C20链烯基、取代或未取代的C2-C20炔基、取代或未取代的C6-C30芳基、具有5-30个环原子的取代或未取代的杂芳基或选自如下的具有给体或受体作用的取代基:C1-C20烷氧基、C6-C30芳氧基、C1-C20烷硫基、C6-C30芳硫基、SiR4R5R6、卤素基团、卤代C1-C20烷基、羰基(-CO(R4))、羰硫基(-C=O(SR4))、羰氧基(-C=O(OR4))、氧羰基(-OC=O(R4))、硫羰基(-SC=O(R4))、氨基(-NR4R5)、OH、拟卤素基团、酰胺基(-C=O(NR4R5))、-NR4C=O(R5)、膦酸根(-P(O)(OR4)2、磷酸根(-OP(O)(OR4)2)、膦(-PR4R5)、氧化膦(-P(O)R4 2)、硫酸根(-OS(O)2OR4)、亚砜(-S(O)R4)、磺酸根(-S(O)2OR4)、磺酰基(-S(O)2R4)、磺酰胺(-S(O)2NR4R5)、NO2、有机硼酸酯(-B(OR4)2)、亚氨基(-C=NR4R5)、硼烷基团、锡烷基团、肼基、腙基、肟基、亚硝基、重氮基、乙烯基、亚砜亚胺、铝烷、锗烷、环硼氧烷和环硼氮烷;
或
R1和R2基团一起形成饱和或不饱和、取代或未取代的包含3-6个原子,优选3或4个原子的桥,以使R1和R2基团与X-Y基团一起形成5-8元环,优选5或6元环;
或
两个相邻R3基团一起形成饱和或不饱和、取代或未取代的包含3-6个原子,优选3或4个原子的桥,以使R3基团与单元A=D、D-E、A’=D’、D’-E’、E’=G’之一一起形成5-8元环,优选5或6元环;
或
位于G’和A位置的R3基团一起形成饱和或不饱和、取代或未取代的包含1-4个原子的桥,以使R3基团与单元-G’-C-C-A-一起形成5-8元环;
桥优选未被取代(即所有可取代位置被氢取代)或被一个或多个选自如下的基团取代:C1-C4烷基,更优选甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基或叔丁基,取代或未取代的苯基,优选未取代的苯基,甲苯基,二甲基苯基,三甲基苯基,F-、CN-、甲氧基-和/或CF3-取代的苯基,取代或未取代的具有5-13个环原子的杂芳基,优选吡啶基、噻吩基、吡咯基、呋喃基或咪唑基,C1-C4烷氧基,更优选甲氧基、C6-C10芳氧基,特别是苯氧基,C1-C4烷硫基,优选SCH3、C6-C10芳硫基,优选SPh、SiR4R5R6,优选SiMe3或SiPh3、F、Cl、Br,优选F、卤代C1-C10烷基,优选CF3,和拟卤素基团,优选CN;其中桥优选由碳原子和任选1或2个杂原子,优选1或2个氮原子形成。
在优选实施方案中,R1、R2和R3各自独立地选自取代或未取代的C1-C20烷基、取代或未取代的C2-C20链烯基、取代或未取代的C2-C20炔基、取代或未取代的C6-C30芳基、具有5-30个环原子的取代或未取代的杂芳基、C1-C20烷氧基、C6-C30芳氧基、C1-C20烷硫基、C6-C30芳硫基、SiR4R5R6、卤素基团、卤代C1-C20烷基和拟卤素基团。更优选R1、R2和R3各自独立地选自取代或未取代的C1-C20烷基,优选C1-C4烷基,更优选甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基或叔丁基、取代或未取代的C6-C30芳基,优选取代或未取代的苯基,更优选未取代的苯基、甲苯基、二甲基苯基、三甲基苯基、F-、CN-、甲氧基-和/或CF3-取代的苯基,具有5-30个环原子的取代或未取代的杂芳基,优选取代或未取代的具有5-13个环原子的杂芳基,更优选吡啶基、噻吩基、吡咯基、呋喃基、噻唑基、噁唑基、吡唑基或咪唑基,C1-C20烷氧基,优选C1-C4烷氧基,更优选甲氧基、C6-C30芳氧基,优选C6-C10芳氧基,更优选苯氧基、C1-C20烷硫基,优选C1-C4烷硫基,更优选SCH3、C6-C30芳硫基,优选C6-C10芳硫基,更优选SPh、SiR4R5R6,优选SiMe3或SiPh3、卤素基团,优选F、Cl、Br,更优选F、卤代C1-C20烷基,优选卤代C1-C10烷基,更优选CF3,和拟卤素基团,优选CN;
或
R1和R2基团一起形成饱和或不饱和的,甲基-、苯基-、甲氧基-、SiMe3-、SiPh3-、F-、CF3-或CN-取代或未取代的,包含3或4个碳原子的桥以使R1和R2基团与X-Y基团一起形成5或6元环;
或
两个相邻R3基团一起形成饱和或不饱和的,甲基-、甲氧基-、SiMe3-、SiPh3-、F-、CF3-或CN-取代或未取代的,包含3或4个碳原子的桥,以使R3基团与单元A=D、D-E、A’=D’、D’-E’、E’=G’之一一起形成5或6元环;
或
在G’和A位置的R3基团一起形成饱和或不饱和的,甲基-、苯基-、甲氧基-、SiMe3-、SiPh3-、F-、CF3-或CN-取代或未取代的,包含1或2个碳原子的桥,以使R3基团与单元-G’-C-C-A-一起形成5或6元环。
在特别优选的实施方案中,R1和R3各自如上所定义且R2选自取代或未取代的C1-C20烷基,其在1-位支化,优选异丙基、异丁基、异戊基、仲丁基或叔丁基;取代或未取代的C6芳基,优选未取代的苯基或在2-和/或6-位被取代的苯基,优选被甲基、甲氧基、CF3、CN和/或F取代;更优选2-甲苯基、2-甲氧基苯基、2-氰基苯基、2-三氟甲基苯基、2,6-二氟苯基,2,3-、2,4-、2,5-或2,6-二甲基苯基或2,4,6-、2,3,4-或2,3,5-三甲基苯基;取代或未取代的具有5-13个环原子的杂芳基,优选吡啶-2-基、吡啶-3-基、吡啶-4-基、噻吩-2-基、噻吩-3-基、吡咯-2-基、吡咯-3-基、呋喃-2-基、呋喃-3-基、噻唑-2-基、噁唑-2-基、吡唑-3-基或咪唑-2-基和相应的苯并稠合基团;F、Cl、Br;CF3和CN。
已经发现具有上述特别优选的R2基团的式Ⅰ的碳烯配合物具有特别好的稳定性。
在优选实施方案中,本发明涉及其中X为CH或N,优选N的式Ⅰ的桥连的环金属化碳烯配合物。Y优选为S或O。因此特别优选如下式Ⅰ的碳烯配合物,其中:
X为CH或N,优选N,和
Y为S或O。
在式Ⅰ碳烯配合物中的A、D、G、E、A’、D’、G’和E’基团各自独立地为CH、CR3或N。优选0、1或2个,更优选0或1个选自A、D、G和E基团或选自A’、D’、G’和E’基团的基团为N。在特别优选的实施方案中,A、D、G、E、A’、D’、G’和E’基团各自为CH或CR3,最优选CH。合适的R3基团如上所述。
特别优选的式Ⅰ的碳烯配合物选自式Ia和Ib的碳烯配合物:
其中:
A、D、G、E、A’、D’、G’和E’各自独立地为CH、CR3或N,优选CH或CR3,更优选CH;
X为CH或CR1;
R1为F、CN、C1-C20烷氧基、C6-C30芳氧基、C1-C20烷硫基、C6-C30芳硫基、取代或未取代的C6-C30芳基或具有5-30个环原子的取代或未取代的杂芳基,优选F、CN、C1-C4烷氧基,更优选甲氧基,C6-C10芳氧基,更优选苯氧基,C1-C4烷硫基,更优选SCH3、C6-C10芳硫基、取代或未取代的苯基,更优选未取代的苯基,甲苯基,二甲基苯基,三甲基苯基,F-、CN-、甲氧基-和/或CF3-取代的苯基或取代或未取代的具有5-13个环原子的杂芳基,更优选吡啶基、噻吩基、吡咯基、呋喃基、噻唑基、噁唑基、吡唑基或咪唑基,最优选F、CN或甲氧基、苯基、吡啶基;
R2、R3各自独立地为取代或未取代的C1-C20烷基、取代或未取代的C5-C20环烷基、取代或未取代的C5-C20环烯基、具有5-30个环原子的取代或未取代的杂环烷基、具有5-30个环原子的取代或未取代的杂环烯基、取代或未取代的C2-C20链烯基、取代或未取代的C2-C20炔基、取代或未取代的C6-C30芳基、具有5-30个环原子的取代或未取代的杂芳基或选自如下的具有给体或受体作用的取代基:C1-C20烷氧基、C6-C30芳氧基、C1-C20烷硫基、C6-C30芳硫基、SiR4R5R6、卤素基团、卤代C1-C20烷基、羰基(-CO(R4))、羰硫基(-C=O(SR4))、羰氧基(-C=O(OR4))、氧羰基(-OC=O(R4))、硫羰基(-SC=O(R4))、氨基(-NR4R5)、OH、拟卤素基团、酰胺基(-C=O(NR4R5))、-NR4C=O(R5)、膦酸根(-P(O)(OR4))2、磷酸根(-OP(O)(OR4)2)、膦(-PR4R5)、氧化膦(-P(O)R4 2)、硫酸根(-OS(O)2OR4)、亚砜(-S(O)R4)、磺酸根(-S(O)2OR4)、磺酰基(-S(O)2R4)、磺酰胺(-S(O)2NR4R5)、NO2、有机硼酸酯(-B(OR4)2)、亚氨基(-C=NR4R5)、硼烷基团、锡烷基团、肼基、腙基、肟基、亚硝基、重氮基、乙烯基、亚砜亚胺、铝烷、锗烷、环硼氧烷和环硼氮烷;
或
两个相邻R3基团一起形成饱和或不饱和、取代的,优选甲基-、苯基-、甲氧基-、SiMe3-、SiPh3-、F-、CF3-或CN-取代的,或未取代的包含3-6个原子的桥,以使R3基团与单元A=D、D-E、A’=D’、D’-E’、E’=G’之一一起形成5-8元环;
或
位于G’和A位置的R3基团一起形成饱和或不饱和、取代的,优选甲基-、苯基-、甲氧基-、SiMe3-、SiPh3-、F-、CF3-或CN-取代的,或未取代的包含1-4个原子的桥,以使R3基团与单元-G’-C-C-A-一起形成5-8元环;
其中R2优选选自取代或未取代的C1-C20烷基,其在1-位支化,优选异丙基、异丁基、异戊基、仲丁基或叔丁基;取代或未取代的C6芳基,优选未取代的苯基或在2-和/或6-位被取代的苯基,优选被甲基、甲氧基、CF3、CN和/或F取代;更优选2-甲苯基、2-甲氧基苯基、2-氰基苯基、2-三氟甲基苯基、2,6-二氟苯基,2,3-、2,4-、2,5-或2,6-二甲基苯基或2,4,6-、2,3,4-或2,3,5-三甲基苯基;取代或未取代的具有5-13个环原子的杂芳基,优选吡啶-2-基、吡啶-3-基、吡啶-4-基、噻吩-2-基、噻吩-3-基、吡咯-2-基、吡咯-3-基、呋喃-2-基、呋喃-3-基、噻唑-2-基、噁唑-2-基、吡唑-3-基或咪唑-2-基和相应的苯并稠合基团;F、Cl、Br;CF3和CN;
R4、R5、R6各自独立地为H、取代或未取代的C1-C20烷基或取代或未取代的C6-C30芳基,或具有5-30个环原子的取代或未取代的杂芳基;
Y为S或O;
M为Ir、Os或Pt;优选Ir(Ⅲ)、Os(Ⅱ)或Pt(Ⅱ),更优选Ir(Ⅲ);
K为不带电荷的双齿配体;
L为单阴离子双齿配体;
n为碳烯配体数目,其中在Ir的情况下n为3,在Os的情况下n为2,在Pt情况下n为1或2,并且在式Ia、Ib、Ic和Id的配合物中的碳烯配体可以相同或不同;
在M=Ir或Pt的情况下m为0,在Os的情况下,m为1;
在M=Ir或Os的情况下以及在Pt且n=2的情况下o为0,在Pt的情况下且在n=1的情况下o为1。
特别优选的基团和指数M、R1、R2、R3、R4、R5、R6、A、D、G、E、A’、D’、G’、E’、Y、M、K、L、n、m和o如上所述。最优选,在式Ia、Ib、Ic和Id的碳烯配体中的M为Ir(Ⅲ),n为3和m和o各自为0。
非常特别优选下式的碳烯配合物:
上述化合物可根据通式Ⅰ的定义任选被一个或多个的其它取代基取代。
本发明的式Ⅰ的桥连的环金属化碳烯配合物原则上可以类似于本领域熟练技术人员已知的方法制备。合适的制备碳烯配合物的方法例如详述于综述文章W.A.Hermann等,Advances in Organometallic Chemistry(有机金属化学进展),2001,第48卷,第1-69页,W.A.Hermann等,Angew.Chem.1997,109,第2256-2282页和G.Bertrand等,Chem.Rev.2000,100,第39-91页以及其中所引用的文献中,以及描述于WO 2005/113704、WO 2005/019373和WO 2007/088093。
在一个实施方案中,本发明的式Ⅰ的桥连环金属化碳烯配合物由对应于碳烯配体的配体前体和包含所需金属的合适的基体配合物制备。
合适的碳烯配体的配体前体对本领域熟练技术人员是已知的。它们优选为通式Ⅲ的碳烯配体的阳离子前体:
其中
Q-为单阴离子抗衡离子,优选卤离子,拟卤离子,BF4 -、BPh4 -、PF6 -、AsF6 -或SbF6 -;
和
在通式Ⅲ的配体前体中的其它基团、符号和指数各自如上所定义。
通式Ⅲ的配体前体可类似于本领域熟练技术人员已知的方法制备。合适的方法如下所述。
在优选实施方案中,本发明涉及一种制备本发明的通式Ⅰ的桥连环金属化碳烯配合物的方法,其中该制备包括如下步骤:
使至少一种通式(Ⅲ)的配体前体与包含至少一种金属M的金属配合物反应:
其中
Q-为单阴离子抗衡离子,优选卤离子,拟卤离子,BF4 -,BPh4 -,PF6 -,AsF6 -或SbF6 -;
和
在通式Ⅲ的配体前体中的其它符号各自如下所定义:
X为CH、CR1或N;
Y为S、O、PR2或SiR2 2,优选S或O;
A、D、G、E、A’、D’、G’或E’各自独立地为CH、CR3或N;
R1、R2、R3各自独立地为取代或未取代的C1-C20烷基、取代或未取代的C5-C20环烷基、取代或未取代的C5-C20环烯基、具有5-30个环原子的取代或未取代的杂环烷基、具有5-30个环原子的取代或未取代的杂环烯基、取代或未取代的C2-C20链烯基、取代或未取代的C2-C20炔基、取代或未取代的C6-C30芳基、具有5-30个环原子的取代或未取代的杂芳基或选自如下的具有给体或受体作用的取代基:C1-C20烷氧基、C6-C30芳氧基、C1-C20烷硫基、C6-C30芳硫基、SiR4R5R6、卤素基团、卤代C1-C20烷基、羰基(-CO(R4))、羰硫基(-C=O(SR4))、羰氧基(-C=O(OR4))、氧羰基(-OC=O(R4))、硫羰基(-SC=O(R4))、氨基(-NR4R5)、OH、拟卤素基团、酰胺基(-C=O(NR4R5))、-NR4C=O(R5)、膦酸根(-P(O)(OR4)2)、磷酸根(-OP(O)(OR4)2)、膦(-PR4R5)、氧化膦(-P(O)R4 2)、硫酸根(-OS(O)2OR4)、亚砜(-S(O)R4)、磺酸根(-S(O)2OR4)、磺酰基(-S(O)2R4)、磺酰胺(-S(O)2NR4R5)、NO2、有机硼酸酯(-B(OR4)2)、亚氨基(-C=NR4R5)、硼烷基团、锡烷基团、肼基、腙基、肟基、亚硝基、重氮基、乙烯基、亚砜亚胺、铝烷、锗烷、环硼氧烷和环硼氮烷;
或
R1和R2基团一起形成饱和或不饱和、取代或未取代的包含3-6个原子的桥,以使R1和R2基团与X-Y基团一起形成5-8元环;
或
两个相邻R3基团一起形成饱和或不饱和、取代或未取代的包含3-6个原子的桥,以使R3基团与单元A=D、D-E、A’=D’、D’-E’、E’=G’之一一起形成5-8元环;
或
位于G’和A位置的R3基团一起形成饱和或不饱和、取代或未取代的包含1-4个原子的桥,以使R3基团与单元-G’-C-C-A-一起形成5-8元环;
和
R4、R5、R6各自独立地为H、取代或未取代的C1-C20烷基或取代或未取代的C6-C30芳基或具有5-30个环原子的杂芳基;
其中M如下所定义:
M为选自元素周期表(CAS版)第IB、IIB、IIIB、IVB、VB、VIB、VIIB、VIIIB族,镧系元素和第IIIA族金属的金属原子,它们处于合适金属原子可能的任何氧化态;优选Fe、Os、Co、Rh、Ir、Ni、Ru、Pd和Pt、Cu、Au、Ce、Tb、Eu,更优选Os、Ru、Rh、Ir和Pt,最优选Ir、Os和Pt。
特别优选的基团和指数M、R2、R3、R4、R5、R6、A、D、G、E、A’、D’、G’、E’、Y、M、K、L、n、m和o如上所述。
如果式Ⅰ的碳烯配合物中的m和/或o不为0,合适的话,式Ⅲ的配体前体与金属配合物的本发明反应在合适的配体K和/或L的配体前体存在下进行(“一锅法”)。配体K和L的合适的配体前体对本领域熟练技术人员是已知的。或者,如果m和/或o不为0,进行顺序反应。顺序反应可通过在第一步中使金属配合物与至少一种通式Ⅲ的碳烯配体前体反应而进行,此时具有至少一个呈环金属化或非环金属化形式的碳烯配体且具有至少一个用于至少一个其它二齿配体K和/或L的其它配位方式(此时其它配位方式通过金属M上的自由配位位置或通过其它配体的脱离而存在)的碳烯配合物首先作为中间体制备;或通过在第一步中使金属配合物与至少一种用于配体K和/或L的配体前体反应而进行,此时具有至少一个配体K和/或L和至少一个用于至少一个二齿碳烯配体的其它配位方式(此时其它配位方式通过金属M’上的自由配位位置或通过其它配体的脱离而存在)的配合物首先作为中间体制备。在第一步之后的第二步中,使第一步中得到的特定配合物与配K和/L的至少一种配体前体(当至少一种碳烯配体前体已经用于第一步时),或与至少一种通式Ⅲ的碳烯配体前体(当配体K和/或L的至少一种配体前体用于第一步时)反应而进行。
在特别优选的情况中,本发明式Ⅰ的碳烯配合物中的金属M为配位数是6的Ir(Ⅲ)且n=3以及m和o各自为0,用式Ⅲ的一种碳烯配体前体或不同的碳烯配体前体进行反应。当使用式Ⅲ的不同的碳烯配体前体时,反应可以“一锅法反应”或顺序(如上所述使用碳烯配体前体和用于配体K和L的配体前体)的形式进行。在式Ⅰ的碳烯配合物中的碳烯配体优选相同,以使式Ⅲ的碳烯配体前体的反应用合适的金属配合物进行。
对于非常特别优选的情况(M=Ir(Ⅲ),n=3),金属∶配体前体的化学计量通常为1∶3-1∶9,优选1∶3-1∶6。
在碳烯配体存在于本发明式Ⅰ碳烯配合物且金属原子为Ir(Ⅲ)(M=Ir(Ⅲ),n=1)的情况下,金属∶配体前体的化学计量通常为1∶1-1∶3,优选1∶1-1∶2。
包含至少一种金属M的金属配合物为包含至少一种选自下列的金属的金属配合物:元素周期表(CAS版)第IB、IIB、IIIB、IVB、VB、VIB、VIIB、VIIIB族,镧系元素和第IIIA族金属,它们处于合适金属原子可能的任何氧化态;优选Fe、Os、Co、Rh、Ir、Ni、Ru、Pd和Pt、Cu、Au、Ce、Tb、Eu,更优选Os、Ru、Rh、Ir和Pt,最优选Ir、Os和Pt。优选在金属配合物中使用Pt(Ⅱ)、Os(Ⅱ)、Ir(Ⅰ)或Ir(Ⅲ)以用于本发明方法,特别优选Ir(Ⅰ)和Ir(Ⅲ),非常特别优选Ir(Ⅰ)。合适的金属配合物对本领域熟练技术人员是已知的。合适的金属配合物的实例为Pt(cod)Cl2、Pt(cod)Me2、Pt(acac)2、Pt(PPh3)2Cl2、PtCl2、[Rh(cod)Cl]2、Rh(acac)CO(PPh3)、Rh(acac)(CO)2、Rh(cod)2BF4、RhCl(PPh3)3、RhCl3x n H2O、Rh(acac)3、[Os(CO)3I2]2、[Os3(CO)12]、OsH4(PPH3)3、CP2Os、Cp*2Os、H2OsCl6x 6H2O、OsCl3x H2O)和[(μ-Cl)Ir(η4-1,5-cod)]2、[(μ-Cl)Ir(η2-coe)2]2、Ir(acac)3、IrCl3x n H2O、(tht)3IrCl3、Ir(η3-烯丙基)3、Ir(η3-甲代烯丙基)3,其中cod为环辛二烯,coe为环辛烯,acac为乙酰丙酮酸根以及tht为四氢噻吩。金属配合物可通过本领域熟练技术人员已知的方法制备或可市购。
在制备通式Ⅰ的铱(Ⅲ)配合物的情况下(式Ⅰ中的M为Ir)(根据本申请这是特别优选的),可使用上述铱(Ⅰ)或(Ⅲ)配合物,特别是[(μ-Cl)Ir(η4-1,5-cod)]2、[(μ-Cl)Ir(η2-coe)2]2、Ir(acac)3、IrCl3x n H2O、(tht)3IrCl3、Ir(η3-烯丙基)3、Ir(η3-甲代烯丙基)3,非常特别优选使用[(μ-Cl)Ir(η4-1,5-cod)]2,其中cod为环辛二烯,coe为环辛烯,acac为乙酰丙酮酸根以及tht为四氢噻吩。
特别优选在碱和辅助试剂或碱性辅助试剂存在下使式Ⅲ的碳烯配体前体与合适的金属配合物进行本发明反应,此时碱性辅助试剂或辅助试剂包含至少一种选自Ag、Hg、Sb、Mg、B和Al的金属;优选在Ag2O存在下进行本发明反应。可相应用于制备本发明的式Ⅰ碳烯配合物的合适方法例如公开于WO 2007/088093。
在Y为S或O的情况下,合适的式Ⅲ的配体前体例如由式IVa或IVb的配体前体进行:
其中符号各自如上所定义,
上述制备例如通过用H2O2脱硫而进行,这例如在下文中描述。
在Y为O的情况下,合适的式Ⅲ的配体前体可额外例如由式IVc的配体前体,例如通过环化而制备:
其中符号各自如上所定义。
其中Y为PR2或SiR2 2的式Ⅰ的碳烯配合物可通过相应方法制备。
上述式IVa、IVb和IVc的化合物可通过本领域熟练技术人员已知的方法制备,合适的方法(合适的话,本领域技术人员取决于待制备的式IVa、IVb和IVc的化合物而根据其知识变化)例如描述于Reese,J.Chem.Soc.1958,895;F.Gug,S.Bach,M.Blondel,J.-M.Vierfond,A.-S.Martin,H.Galons,Tetrahedron 2004,60,4705和A.G.Mikhailovskii,V.S.Shklyaev,Chem.Heterocycl.Comp.1992,445。
制备非常特别优选的本发明的式Ⅰ碳烯配合物的制备方法例如在下文中描述,下文中实例包括由市售化合物或可通过本领域熟练技术人员已知的方法制备的那些化合物来制备合适的式IVa、IVb和IVc的化合物和制备合适的式Ⅲ的配体前体。下述实例中所述的化合物是阐述性的并且可根据式Ⅰ化合物的取代方式取代和/或根据式Ⅰ化合物在它们的环体系中具有杂原子。
由6-氨基菲啶合成基于噻二唑并菲啶的配合物1(a)Reese,J.Chem.Soc.1958,895;b)F.Gug,S.Bach,M.Blondel,J.-M.Vierfond,A.-S.Martin,H.Galons,Tetrahedron 2004,60,4705):
合成基于噁二唑并菲啶的配合物2:
在反应之后,将本发明的式Ⅰ的环金属化桥连碳烯配合物后处理,以及合适的话通过本领域熟练技术人员已知的方法纯化。后处理和纯化通常通过本领域熟练技术人员已知的萃取、柱色谱法和/或再结晶方法进行。
本发明的式Ⅰ环金属化桥连碳烯配合物极其适合作为发磷光物质,因为它们在电磁光谱的可见区,优选在电磁光谱的蓝光区发光(电致发光)。借助作为发光体物质的本发明式Ⅰ的碳烯配合物,可以提供具有良好效率的电致发光的化合物,本发明碳烯配合物的显著之处在于在器件中的良好稳定性。同时,量子产率高。
此外,本发明的式Ⅰ碳烯配合物适合在OLED中作为电子阻挡剂、激子阻挡剂或空穴阻挡剂或空穴导体、电子导体、空穴注入层或基质材料,这通常取决于所用配体和所用中心金属。
因此,本发明进一步提供了本发明的式Ⅰ的环金属化桥连碳烯配合物在有机发光二极管中,优选作为发光体材料、基质材料、电荷阻挡材料和/或电荷传输材料,更优选作为发光体材料,最优选作为蓝光发光体的用途。
有机发光二极管(OLED)原则上由几层组成,例如:
1.阳极(1)
2.空穴传输层(2)
3.发光层(3)
4.电子传输层(4)
5.阴极(5)
然而,OLED还可以不具有所有所述层;例如具有层(1)(阳极)、(3)(发光层)和(5)(阴极)的OLED同样是合适的,此时层(2)(空穴传输层)和(4)(电子传输层)的功能由相邻层承担。具有层(1)、(2)、(3)和(5)或层(1)、(3)、(4)和(5)的OLED同样是合适的。
本发明式Ⅰ的环金属化桥连碳烯配合物可用于OLED的不同层。式Ⅰ的碳烯配合物可用于OLED的一个层中,但是同样可将两种或更多种不同的式Ⅰ的碳烯配合物用于OLED的一个或多个层中。例如,OLED发光层中的发光体材料和基质材料均可包括式Ⅰ碳烯配合物,此时用作发光体材料的式Ⅰ碳烯配合物和用作基质材料的式Ⅰ碳烯配合物通常是不同的。发光体材料和空穴导体材料同样可包含式Ⅰ碳烯配合物,此时式Ⅰ碳烯配合物通常是不同的。不同碳烯配合物的其它组合也是可行的并且可由本领域熟练技术人员确定。因此,本发明进一步提供了包含至少一种本发明式Ⅰ的环金属化桥连碳烯配合物的OLED。本发明式Ⅰ的环金属化桥连碳烯配合物优选用于发光层,如作为基质分子或发光体分子,更优选作为发光体分子。因此,本发明进一步提供了包含至少一种本发明式Ⅰ的环金属化桥连碳烯配合物(优选作为发光体分子)的发光层。优选的本发明式Ⅰ的环金属化桥连碳烯配合物如上所述。
本发明的式Ⅰ环金属化桥连碳烯配合物可以直接,即没有其他添加剂,存在于OLED的发光层或另一层中,优选存在于发光层中。然而,同样可能且优选的是除了按照本发明的式Ⅰ环金属化桥连碳烯配合物外,其他化合物可以存在于包含至少一种本发明的式Ⅰ环金属化桥连碳烯配合物的层中,优选存在于发光层中。例如,发光层中可以存在荧光染料以改变用作发光体分子的式Ⅰ环金属化桥连碳烯配合物的发光颜色。此外,在优选实施方案中,可以使用稀释剂材料。该稀释剂材料可以是聚合物,例如聚(N-乙烯基咔唑)或聚硅烷。然而,稀释剂材料同样可以是小分子,例如4,4’-N,N’-二咔唑基联苯(CDP=CBP)或叔芳族胺。此外,发光层中的式Ⅰ碳烯配合物可与基质材料一起使用,合适的基质材料如上所述。本发明的式Ⅰ碳烯配合物作为基质材料(与将式Ⅰ的碳烯配合物用作发光体材料的用途一起(此时用作基质材料的碳烯配合物和用作发光体材料的碳烯配合物通常不同))的用途已经在上文描述。
OLED的上述各层又可以由两层或更多层形成。例如,空穴传输层可以由将空穴从电极注入其中的层和将空穴从空穴注入层传输到发光层的层形成。电子传输层同样可以由多层组成,例如由通过电极将电子注入其中的层和从电子注入层接收电子并将它们传输到发光层中的层组成。本领域熟练技术人员能够选择OLED的结构,以使其与根据本发明使用的本发明式Ⅰ碳烯配合物最佳匹配,其中式Ⅰ碳烯配合物优选用作发光体物质。
为了得到特别有效的OLED,应使空穴传输层的HOMO(最高被占分子轨道)与阳极的功函匹配并使电子传输层的LUMO(最低未占分子轨道)与阴极的功函匹配。
本申请还提供了一种包含至少一种本发明的发光层的OLED。该OLED中的其他层可以由任何常用于该类层中且为本领域熟练技术人员已知的材料组成。
适用于上述层的材料(阳极、阴极、空穴和电子注入材料、空穴和电子传输材料以及空穴和电子阻挡剂材料、基质材料、荧光和磷光发光体)对本领域熟练技术人员是已知的并且例如描述于H.Meng,N.Herron,OrganicSmall Molecule Materials for Organic Light-Emitting Devices in OrganicLight-Emitting Materials and Devices(在有机发光材料和器件中用于有机发光器件的有机小分子材料),编辑:Z.Li,H.Meng,Taylor & Francis,2007,第3章,第295-411页。
阳极(1)是提供正电荷载体的电极。它例如可以由包含金属、不同金属的混合物、金属合金、金属氧化物或不同金属氧化物的混合物的材料构成。或者,阳极可以是导电聚合物。合适的金属包括元素周期表第11、4、5和6族金属以及第8-10族过渡金属。当阳极要透明时,则通常使用元素周期表第12、13和14族的混合金属氧化物,例如铟-锡氧化物(ITO)。阳极(1)同样可以包含有机材料,如聚苯胺,例如如Nature,第357卷,第477-479页(1992年6月11日)所述。阳极或阴极中的至少一种应至少部分透明以使所产生的光能被发射。
用于本发明OLED的层(2)的合适空穴传输材料例如公开于Kirk-Othmer Encyclopedia of Chemical Technology,第4版,第18卷,第837-860页,1996中。空穴传输分子或聚合物可以用作空穴传输材料。通常使用的空穴传输分子选自4,4’-双[N-(1-萘基)-N-苯基氨基]联苯(α-NPD)、N,N’-二苯基-N,N’-双(3-甲基苯基)[1,1’-联苯基]-4,4’-二胺(TPD)、1,1-双[(二-4-甲苯基氨基)苯基]环己烷(TAPC)、N,N’-双(4-甲基苯基)-N,N’-双(4-乙基苯基)-[1,1’-(3,3’-二甲基)联苯基]-4,4’-二胺(ETPD)、四(3-甲基苯基)-N,N,N’,N’-2,5-苯二胺(PDA)、α-苯基-4-N,N-二苯基氨基苯乙烯(TPS)、对-(二乙氨基)苯甲醛二苯基腙(DEH)、三苯基胺(TPA)、双[4-(N,N-二乙氨基)-2-甲基苯基](4-甲基苯基)甲烷(MPMP)、1-苯基-3-[对-(二乙氨基)苯乙烯基]-5-[对-(二乙氨基)苯基]吡唑啉(PPR或DEASP)、1,2-反式-双(9H-咔唑-9-基)环丁烷(DCZB)、N,N,N’,N’-四(4-甲基苯基)-(1,1’-联苯基)-4,4’-二胺(TTB)、4’,4’,4”-三(N,N-二苯基氨基)三苯基胺(TDTA)、4,4′,4″-三(N-3-甲基苯基-N-苯基氨基)三苯基胺(m-MTDATA)、2,2,7,7-四(二苯基胺)-9,9-螺二芴(Spiro-TAD)、4,4′,4″-三(咔唑-9-基)三苯基胺(TCTA)和卟啉化合物,以及酞菁如酞菁铜。常用的空穴传输聚合物选自聚乙烯基咔唑、(苯基甲基)聚硅烷,PEDOT(聚(3,4-亚乙二氧基噻吩)),优选掺杂有PSS(聚苯乙烯磺酸盐)的PEDOT,以及聚苯胺。同样可以通过将空穴传输分子掺杂到聚合物如聚苯乙烯和聚碳酸酯中而得到空穴传输聚合物。合适的空穴传输分子是上述分子。
用于本发明OLED的层(4)的合适电子传输材料包括与oxinoid化合物螯合的金属如三(8-羟基喹啉根合)铝(Alq3)或二(2-甲基-8-喹啉根合)-(对苯基喹啉根合)铝(BALq),基于菲咯啉的化合物如2,9-二甲基-4,7-二苯基-1,10-菲咯啉(DDPA=BCP)或4,7-二苯基-1,10-菲咯啉(BPhen)以及唑类化合物如2-(4-联苯基)-5-(4-叔丁基苯基)-1,3,4-噁二唑(PBD)和3-(4-联苯基)-4-苯基-5-(4-叔丁基苯基)-1,2,4-***(TAZ)、1,3-二(4-叔丁基苯基-1,3,4-噁二唑基)苯(OXD7)、2,2′,2″-(1,3,5-苯三基)-三(1-苯基苯并咪唑)(TPBI)。层(4)可以同时用于促进电子传输和用作缓冲层或阻挡层以防止激子在OLED各层的界面处的猝灭。该层(4)优选改进电子的迁移性并降低激子的猝灭。
在上述作为空穴传输材料和电子传输材料的材料中,某些可以满足多种功能。例如,导电材料中的一些在具有低位HOMO时同时为空穴阻挡材料。
还可以将电荷传输层进行电子掺杂以改善所用材料的传输性能,首先使层厚更大(避免针孔/短路),其次使器件的操作电压降至最小。例如,空穴传输材料可以掺杂电子受体;例如,酞菁或芳基胺如TPD或TDTA可以掺杂有四氟四氰基醌二甲烷(F4-TCNQ)。电子传输材料例如可以掺杂碱金属,例如用锂掺杂Alq3。电子掺杂对本领域熟练技术人员是已知的且例如公开于W.Gao,A.Kahn,J.Appl.Phys.,第94卷,第1期,2003年7月1日(p-掺杂的有机层);A.G.Werner,F.Li,K.Harada,M.Pfeiffer,T.Fritz,K.Leo,Appl.Phys.Lett.,第82卷,第25期,2003年6月23日和Pfeiffer等,Organic Electronics 2003,4,89-103和K.Walzer,B.Maennig,M.Pfeiffer,K.Leo,Chem.Soc.Rev.2007,107,1233。
合适的基质材料原则上为作为空穴和电子传输材料提及的材料,以及碳烯配合物,如式Ⅰ碳烯配合物或WO 2005/019373中提及的碳烯配合物。特别合适的基质材料为咔唑衍生物,如4,4′-二(咔唑-9-基)-2,2′-二甲基联苯(CDBP)、4,4′-二(咔唑-9-基)联苯(CBP)、1,3-二(N-咔唑基)苯(mCP),以及在本申请的优先权日还未公开且具有如下申请号PCT/EP2007/059648,EP07 111 824.4.的申请中提及的基质材料。
在至少一种发光体材料与至少一种基质材料一起用于本发明OLED的发光层中的情况下,本发明OLED的发光层中的至少一种基质材料的比例通常为10-99重量%,优选50-99重量%,更优选70-97重量%。发光层中的至少一种发光体材料的比例通常为1-90重量%,优选1-50重量%,更优选3-30重量%,其中至少一种基质材料和至少一种发光体材料的比例之和为100重量%。然而,除了至少一种基质材料和至少一种发光体材料外,发光层也可包含其它物质,如其它稀释剂材料,其中其它稀释剂材料如上所述。
阴极(5)是用于引入电子或负电荷载体的电极。阴极可以是具有比阳极低的功函的任何金属或非金属。合适的阴极材料选自元素周期表第1族碱金属,如Li、Cs,第2族碱土金属,第12族金属,其包括稀土金属和镧系和锕系元素。此外,还可以使用诸如铝、铟、钙、钡、钐和镁的金属及其组合。此外,还可以在有机层和阴极之间施加含锂的有机金属化合物或LiF以降低操作电压。
本发明的OLED可以额外包含本领域熟练技术人员已知的其他层。例如,可以在层(2)和发光层(3)之间施加促进传输正电荷和/或使各层的带隙相互匹配的层。或者,该其他层可以用作保护层。以类似方式可以在发光层(3)和层(4)之间存在额外层,以促进传输负电荷和/或使各层的带隙相互匹配。或者,该层可以用作保护层。
在优选实施方案中,本发明的OLED除了层(1)-(5)外还包含至少一个下述其他层:
-在阳极(1)和空穴传输层(2)之间的空穴注入层;
-在空穴传输层(2)和发光层(3)之间的电子和/或激子阻挡层;
-在发光层(3)和电子传输层(4)之间的空穴和/或激子阻挡层;
-在电子传输层(4)和阴极(5)之间的电子注入层。
然而,如上所述还可能的是OLED不具有所有的所述层(1)-(5);例如,具有层(1)(阳极)、(3)(发光层)和(5)(阴极)的OLED同样是合适的,此时层(2)(空穴传输层)和(4)(电子传输层)的功能由相邻层承担。具有层(1)、(2)、(3)和(5)或层(1)、(3)、(4)和(5)的OLED同样是合适的。
本领域熟练技术人员知道如何选择合适的材料(例如基于电化学研究)。用于各层的合适材料和合适的OLED的结构对本领域熟练技术人员是已知的且例如公开于WO 2005/113704中。
此外,本发明OLED的上述各层可以由两层或更多层组成。此外,层(1)、(2)、(3)、(4)和(5)中的一些或所有可以进行表面处理以增加电荷载体的传输效率。所述各层的材料选择优选应通过得到具有高效率的OLED而确定。
本发明的OLED可以通过本领域熟练技术人员已知的方法生产。通常通过在合适的基材上依次气相沉积各层而生产OLED。合适的基材例如包括玻璃或聚合物膜。对于气相沉积,可以使用常规技术如热蒸发、化学气相沉积和其他技术。在替换方法中,可以由在合适溶剂中的溶液或分散体而施涂有机层,此时使用本领域熟练技术人员已知的涂敷技术。在OLED的各层之一,优选发光层中通常将除了至少一种本发明的式Ⅰ的环金属化桥连碳烯配合物外还具有聚合材料的组合物借助溶液加工方法作为层施加。
通常而言,不同层具有如下厚度:阳极(2)500-5000优选1000-2000空穴传输层(3)50-1000优选200-800发光层(4)10-1000优选100-800电子传输层(5)50-1000优选200-800阴极(7)200-10000优选300-5000在本发明的OLED中空穴和电子的复合区的位置以及因此OLED的发光光谱可能受各层的相对厚度的影响。这意味着电子传输层的厚度的选择优选应使电子/空穴复合区位于发光层中。OLED中各层的层厚之比取决于所用材料。任何所用额外层的层厚对本领域熟练技术人员是已知的。
式Ⅰ的本发明环金属化桥连碳烯配合物在本发明OLED的至少一层中的使用,优选在本发明OLED的发光层中作为发光体分子的使用,使得可以得到具有高效率和长寿命的OLED。此外,本发明OLED的效率可以通过优化其他层而得以额外改进。例如,可以使用高效的阴极如Ca、Ba或LiF。同样可以在本发明OLED中使用降低操作电压或增加外部量子效率的成型基材和新型空穴传输材料。此外,在OLED中可以存在额外层以调节不同层的能级并促进电致发光。
本发明OLED可以用于其中电致发光是有用的所有器件中。合适的器件优选选自静止和移动可视显示单元以及照明装置。静止的可视显示单元例如为计算机、电视的可视显示单元,打印机、厨房用具、广告板、照明和信息板中的可视显示单元。移动可视显示单元例如包括移动电话、手提电脑、数码相机、车辆以及公共汽车和火车上的目的地显示中的可视显示单元。照明装置例如为LCD的背景照明、发光表面,如发光壁纸。
此外本发明的式Ⅰ的环金属化桥连碳烯配合物可用于具有反转结构的OLED中。本发明的式Ⅰ的环金属化桥连碳烯配合物可优选在这些反转OLED中又用于发光层中。反转OLED的结构和常用于其中的材料对本领域熟练技术人员是已知的。
上述本发明的式Ⅰ的环金属化桥连碳烯配合物除了用于OLED中外还可以用作着色剂,其在光辐照时在电磁光谱的可见区发光(光致发光)。
本发明因此进一步提供了上述本发明的式Ⅰ的环金属化桥连碳烯配合物在聚合物材料整体着色中的用途。
合适的聚合物材料是聚氯乙烯、乙酸纤维素、聚碳酸酯、聚酰胺、聚氨酯、聚酰亚胺、聚苯并咪唑、蜜胺树脂、聚硅氧烷、聚酯、聚醚、聚苯乙烯、聚甲基丙烯酸甲酯、聚乙烯、聚丙烯、聚乙酸乙烯酯、聚丙烯腈、聚丁二烯、聚氯丁二烯、聚异戊二烯以及所列单体的共聚物。
此外,上述本发明的式Ⅰ的环金属化桥连碳烯配合物可以用于下列应用中:
-本发明的式Ⅰ的环金属化桥连碳烯配合物作为翁染料或在翁染料中的用途,例如用于对天然材料着色;实例是纸张、木材、稻草、皮革、毛皮或天然纤维材料如棉花、羊毛、丝、黄麻、剑麻、***、亚麻或动物毛发(例如马毛)及其转化产品如粘胶纤维、硝化丝或铜氨螺萦。
-本发明的式Ⅰ的环金属化桥连碳烯配合物作为着色剂的用途,例如用于对油漆、清漆和其他表面涂料组合物、纸张油墨、印刷油墨、其他油墨以及用于绘画和书写目的的着色剂的着色。
-本发明的式Ⅰ的环金属化桥连碳烯配合物作为着色染料的用途,例如用于对油漆、清漆和其他表面涂料组合物、纸张油墨、印刷油墨、用于绘画和书写目的的油墨和其他着色剂的着色。
-本发明的式Ⅰ的环金属化桥连碳烯配合物在静电复印中作为颜料的用途:例如用于干式复印***(Xerox方法)和激光打印机。
-本发明的式Ⅰ的环金属化桥连碳烯配合物在安全标记目的中的用途,对该目的而言物质的高化学和光化学稳定性以及合适的话还有发光性是重要的。这优选用于检查、检查卡片、支票、联票、文件、识别纸等,其中必需实现特殊的不会弄错的颜色印记。
-本发明的式Ⅰ的环金属化桥连碳烯配合物作为其他着色剂的添加剂的用途,其中需要实现特殊色调;优选特别亮的着色。
-本发明的式Ⅰ的环金属化桥连碳烯配合物在制备使用发光而在机器中识别的制品中的用途,优选机器识别用于分类的制品,包括例如用于塑料再循环的制品。
-本发明的式Ⅰ的环金属化桥连碳烯配合物作为机器可读标记的发光染料的用途;优选字母数字标记或条形码。
-本发明的式Ⅰ的环金属化桥连碳烯配合物在调节光频率中的用途,例如将短波长光转化成更长波长的可见光。
-本发明的式Ⅰ的环金属化桥连碳烯配合物在任何种类的显示、信息和标记目的的显示元件中的用途,例如用于无源显示元件、信息信号和交通信号如交通灯。
-本发明的式Ⅰ的环金属化桥连碳烯配合物在喷墨打印机中的用途,优选作为发光油墨用于均相溶液中。
-本发明的式Ⅰ的环金属化桥连碳烯配合物作为超导有机材料的原料的用途。
-本发明的式Ⅰ的环金属化桥连碳烯配合物在固态发光标记中的用途。
-本发明的式Ⅰ的环金属化桥连碳烯配合物在装饰性目的中的用途。
-本发明的式Ⅰ的环金属化桥连碳烯配合物在示踪剂目的中的用途,例如用于生物化学、药物、工程和自然科学中。在该用途中,染料可以共价键合于基材上或经由次级价键如氢键或疏水性相互作用(吸附)而键合。
-本发明的式Ⅰ的环金属化桥连碳烯配合物在高感度检测方法中作为发光染料的用途(参见C.Aubert,J.Fünfschilling,I.Zschocke-和H.Langhals,Z.Analyt.Chem.320(1985)361)。
-本发明的式Ⅰ的环金属化桥连碳烯配合物在闪烁器件中作为发光染料的用途。
-本发明的式Ⅰ的环金属化桥连碳烯配合物在光学光聚集***中作为染料或发光染料的用途。
-本发明的式Ⅰ的环金属化桥连碳烯配合物在发光太阳能聚光器中作为染料或发光染料的用途(参见Langhals,Nachr.Chem.Tech.Lab.28(1980)716)。
-本发明的式Ⅰ的环金属化桥连碳烯配合物在发光活化的显示中作为染料或发光染料的用途(参见W.Greubel和G.Baur,Elektronik 26(1977)6)。
-本发明的式Ⅰ的环金属化桥连碳烯配合物在用于光诱导聚合以生产塑料的冷光源中作为染料或发光染料的用途。
-本发明的式Ⅰ的环金属化桥连碳烯配合物作为材料测试用染料或发光染料的用途,例如在半导体电路的生产中。
-本发明的式Ⅰ的环金属化桥连碳烯配合物作为集成半导体组件的微结构研究用染料或发光染料的用途。
-本发明的式Ⅰ的环金属化桥连碳烯配合物在光电导体中作为染料或发光染料的用途。
-本发明的式Ⅰ的环金属化桥连碳烯配合物在照相工艺中作为染料或发光染料的用途。
-本发明的式Ⅰ的环金属化桥连碳烯配合物在显示、照明或图象转换***中作为染料或发光染料的用途,其中借助电子、离子或UV辐射激发,例如用于发光显示器、Braun管或荧光管中。
-本发明的式Ⅰ的环金属化桥连碳烯配合物作为染料或发光染料用作集成半导体电路的一部分的用途,其中染料直接使用或与其他半导体结合使用,例如以外延形式。
-本发明的式Ⅰ的环金属化桥连碳烯配合物在化学发光***中作为染料或发光染料的用途,例如在化学发光照明棒、发光免疫分析或其他发光检测方法中。
-本发明的式Ⅰ的环金属化桥连碳烯配合物作为染料或发光染料用作信号着色剂的用途,优选用于题词和图画或其他图形产品的光学强调,用于个性化信号和其中需要实现特殊光学颜色印记的其他制品。
-本发明的式Ⅰ的环金属化桥连碳烯配合物在染料激光中作为染料或发光染料的用途,优选作为产生激光光束的发光染料。
-本发明的式Ⅰ的环金属化桥连碳烯配合物作为非线性镜片的活性物质的用途,例如用于激光的频率倍增和频率三倍增。
-本发明的式Ⅰ的环金属化桥连碳烯配合物作为流变改进剂的用途。
-本发明的式Ⅰ的环金属化桥连碳烯配合物在将电磁辐射转化成电能的光伏阵列中作为染料的用途。
下列实施例对本发明提供额外说明。
实施例
具有噻二唑菲啶配体的配合物(1)
将6-氨基菲啶(a)Reese,J.Chem.Soc.1958,895;b)F.Gug,S.Bach,M.Blondel,J.-M.Vierfond,A.-S.Martin,H.Galons,Tetrahedron 2004,60,4705)(A)通过与全氯甲硫醇(Cl3C-S-Cl,Na2CO3,Et2O,H2O)(类似于:J.A.Mitchell,D.H.Reid,J.Chem.Soc.,Perkin Trans.1,1982,499)反应而转化为6-三氯甲硫基氨基菲啶(B)。接着用氢硫化钠NaSH环化得到1,2,4-噻二唑并[4,3-f]菲啶-5-硫酮(C)(类似于:K.T.Potts,R.Armbruster,J.Org.Chem.1971,36,1846)。在酸性水溶液中与过氧化氢反应(类似于:a)A.Takamizawa,H.Harada,Chem.Pharm.Bull.1974,22,2818;b)J.L.Charlton等,Can.J.Chem.1974,52,302;c)Y.Yano,Y.Tamura,W.Tagaki,Bull.Chem.Soc.Jpn.1980,53,740)得到1,2,4-噻二唑并[4,3-f]菲啶鎓氯化物(D),将其通过WO 2007/088093中所公开的方法(用于配合物合成的方法B)转化为配合物1(Ag2O,MeOH→[Ir(cod)Cl]2,1,3,5-三甲基苯)。
ESI-MS:m/z=898(计算,对于M+H+:898)。
具有噁二唑菲啶配体的配合物(2)
用羟胺将6(5H)-菲啶酮E转化为肟E(类似于:Baltrushis,R.S.;Mitskyavichyus,V.Yu.;Bilinskaite,I.Ch.;Zolotoyabko,R.M.;Liepin′sh,E.E.;Chem.Heterocycl.Compd.1990,26,918)。接着用原甲酸三乙酯和四氟硼酸铵环化为1,2,4-噁二唑并[4,3-f]菲啶鎓盐G(类似于WO 2005/019373)。通过WO 2007/088093中所公开的方法(用于配合物合成的方法B)(Ag2O,MeOH→[Ir(cod)Cl]2,1,3,5-三甲基苯)将该配体前体转化为配合物2。
ESI-MS:m/z=850(计算,对于M+H+:850)。
Claims (10)
1.一种通式(I)的环金属化碳烯配合物:
其中符号各自如下所定义:
M为Ir;
K为不带电荷的单齿或双齿配体;
L为单阴离子或双阴离子配体;
X为N;
Y为S或O;
A、D、G、E、A’、D’、G’和E’各自独立地为CH或CR3;
R3为C1-C6烷基、C5-C10环烷基、C6-C10芳基或C1-C6烷氧基;
n为碳烯配体的数目,其中n至少为1,并且当n>1时,式I配合物中的碳烯配体可以相同或不同;
m是配体K的数目,其中m可以为0或≥1,并且当m>1时,配体K可以相同或不同;
o是配体L的数量,其中o可以为0或≥1,并且当o>1时,配体L可以相同或不同;
其中n+m+o之和取决于所用金属原子的氧化态和配位数,取决于配体L和K的齿数以及取决于配体L上的电荷,条件是n至少为1。
2.根据权利要求1的碳烯配合物,其中:
M为Ir(III),
n为3,和
m、o各自为0。
3.根据权利要求1或2的碳烯配合物,其中
R3选自C1-C6烷基、C6芳基和C1-C6烷氧基。
4.一种制备根据权利要求1或2的碳烯配合物的方法,包括:
使至少一种式(III)的配体前体与包含至少一种金属M的金属配合物反应:
其中
Q-为单阴离子抗衡离子;
和
在通式III的配体前体中的其它符号各自如下所定义:
X为N;
Y为S或O;
A、D、G、E、A’、D’、G’或E’各自独立地为CH或CR3;
R3为C1-C6烷基、C5-C10环烷基、C6-C10芳基或C1-C6烷氧基;
其中M如下所定义:
M为Ir。
5.根据权利要求4的方法,其中Q-为卤离子,拟卤离子,BF4 -,BPh4 -。
6.根据权利要求1或2的碳烯配合物在有机发光二极管中的用途。
7.一种包含至少一种根据权利要求1或2的碳烯配合物的有机发光二极管。
8.一种包含至少一种根据权利要求1或2的碳烯配合物的发光层。
9.一种包含至少一个根据权利要求8的发光层的有机发光二极管。
10.一种包含至少一个根据权利要求7的有机发光二极管的选自静止可视显示单元、移动可视显示单元以及照明装置的器件。
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