TWI558715B - 新穎異配位基銥錯合物 - Google Patents
新穎異配位基銥錯合物 Download PDFInfo
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- TWI558715B TWI558715B TW101142289A TW101142289A TWI558715B TW I558715 B TWI558715 B TW I558715B TW 101142289 A TW101142289 A TW 101142289A TW 101142289 A TW101142289 A TW 101142289A TW I558715 B TWI558715 B TW I558715B
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- alkyl
- organic
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- 150000002503 iridium Chemical class 0.000 title description 2
- 239000010410 layer Substances 0.000 claims description 89
- 150000001875 compounds Chemical class 0.000 claims description 83
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- 239000012044 organic layer Substances 0.000 claims description 33
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 125000001072 heteroaryl group Chemical group 0.000 claims description 16
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- 150000004696 coordination complex Chemical group 0.000 claims description 12
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 239000002019 doping agent Substances 0.000 claims description 11
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 10
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 10
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 9
- 229910052805 deuterium Inorganic materials 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 6
- 235000010290 biphenyl Nutrition 0.000 claims description 6
- 229910052711 selenium Inorganic materials 0.000 claims description 6
- 238000006467 substitution reaction Methods 0.000 claims description 6
- 125000005580 triphenylene group Chemical group 0.000 claims description 6
- 239000004305 biphenyl Substances 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 229930192474 thiophene Natural products 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 95
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 94
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 85
- 239000000463 material Substances 0.000 description 57
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 40
- 238000006243 chemical reaction Methods 0.000 description 37
- 235000019439 ethyl acetate Nutrition 0.000 description 35
- 239000000047 product Substances 0.000 description 32
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 239000000203 mixture Substances 0.000 description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 230000015572 biosynthetic process Effects 0.000 description 23
- 239000011541 reaction mixture Substances 0.000 description 23
- 238000003786 synthesis reaction Methods 0.000 description 23
- 239000003446 ligand Substances 0.000 description 22
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 20
- 229910052757 nitrogen Inorganic materials 0.000 description 20
- 239000012043 crude product Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- -1 arylkyl Chemical group 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- 238000000859 sublimation Methods 0.000 description 14
- 230000008022 sublimation Effects 0.000 description 14
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 14
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 150000003384 small molecules Chemical class 0.000 description 12
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 11
- 238000002347 injection Methods 0.000 description 11
- 239000007924 injection Substances 0.000 description 11
- 229910052751 metal Inorganic materials 0.000 description 11
- 239000002184 metal Substances 0.000 description 11
- 229920001296 polysiloxane Polymers 0.000 description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 10
- 238000004440 column chromatography Methods 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 229910004298 SiO 2 Inorganic materials 0.000 description 9
- 230000004888 barrier function Effects 0.000 description 9
- 230000005525 hole transport Effects 0.000 description 9
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
- 238000001704 evaporation Methods 0.000 description 8
- 230000008020 evaporation Effects 0.000 description 8
- 238000004770 highest occupied molecular orbital Methods 0.000 description 8
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- 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 7
- 239000000706 filtrate Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 229910000160 potassium phosphate Inorganic materials 0.000 description 7
- 235000011009 potassium phosphates Nutrition 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 239000004575 stone Substances 0.000 description 7
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 7
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 230000005693 optoelectronics Effects 0.000 description 6
- 239000011368 organic material Substances 0.000 description 6
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- ARSLWGHFZUGJTK-UHFFFAOYSA-K ruthenium(3+);trifluoromethanesulfonate Chemical compound [Ru+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F ARSLWGHFZUGJTK-UHFFFAOYSA-K 0.000 description 6
- 229940126062 Compound A Drugs 0.000 description 5
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 5
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 5
- 125000003342 alkenyl group Chemical group 0.000 description 5
- 125000000304 alkynyl group Chemical group 0.000 description 5
- 239000000412 dendrimer Substances 0.000 description 5
- 229920000736 dendritic polymer Polymers 0.000 description 5
- 238000000151 deposition Methods 0.000 description 5
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 5
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 5
- 239000012299 nitrogen atmosphere Substances 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 4
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 4
- XLTFRTTTZWMJJQ-UHFFFAOYSA-N 4-methyldibenzofuran Chemical compound O1C2=CC=CC=C2C2=C1C(C)=CC=C2 XLTFRTTTZWMJJQ-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 150000001412 amines Chemical group 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 4
- 125000004104 aryloxy group Chemical group 0.000 description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 4
- VYLVYHXQOHJDJL-UHFFFAOYSA-K cerium trichloride Chemical compound Cl[Ce](Cl)Cl VYLVYHXQOHJDJL-UHFFFAOYSA-K 0.000 description 4
- 125000004122 cyclic group Chemical group 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
- 150000002148 esters Chemical group 0.000 description 4
- 150000004820 halides Chemical group 0.000 description 4
- 125000004404 heteroalkyl group Chemical group 0.000 description 4
- 150000002527 isonitriles Chemical group 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 230000007246 mechanism Effects 0.000 description 4
- 150000002825 nitriles Chemical group 0.000 description 4
- 150000002894 organic compounds Chemical class 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- 150000003852 triazoles Chemical class 0.000 description 4
- KHCHJJRKNOYKOB-UHFFFAOYSA-N 2-(6-propan-2-yldibenzofuran-4-yl)pyridine Chemical compound C=12OC=3C(C(C)C)=CC=CC=3C2=CC=CC=1C1=CC=CC=N1 KHCHJJRKNOYKOB-UHFFFAOYSA-N 0.000 description 3
- OKDGRDCXVWSXDC-UHFFFAOYSA-N 2-chloropyridine Chemical compound ClC1=CC=CC=N1 OKDGRDCXVWSXDC-UHFFFAOYSA-N 0.000 description 3
- ACEYZYYNAMWIIE-UHFFFAOYSA-N 4-iododibenzofuran Chemical compound O1C2=CC=CC=C2C2=C1C(I)=CC=C2 ACEYZYYNAMWIIE-UHFFFAOYSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 229940125782 compound 2 Drugs 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 3
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical class C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 description 3
- 239000011241 protective layer Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 3
- 238000002207 thermal evaporation Methods 0.000 description 3
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 3
- DYBULZBYAHWAMM-UHFFFAOYSA-N (6-methyldibenzofuran-4-yl)boronic acid Chemical compound C12=CC=CC(B(O)O)=C2OC2=C1C=CC=C2C DYBULZBYAHWAMM-UHFFFAOYSA-N 0.000 description 2
- UYZXLKMREZFZPU-UHFFFAOYSA-N (6-phenyldibenzofuran-4-yl)boronic acid Chemical compound C=12OC=3C(B(O)O)=CC=CC=3C2=CC=CC=1C1=CC=CC=C1 UYZXLKMREZFZPU-UHFFFAOYSA-N 0.000 description 2
- BDAOWASUQQPPES-UHFFFAOYSA-N (6-propan-2-yldibenzofuran-4-yl)boronic acid Chemical compound C12=CC=CC(B(O)O)=C2OC2=C1C=CC=C2C(C)C BDAOWASUQQPPES-UHFFFAOYSA-N 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 2
- XWIYUCRMWCHYJR-UHFFFAOYSA-N 1h-pyrrolo[3,2-b]pyridine Chemical compound C1=CC=C2NC=CC2=N1 XWIYUCRMWCHYJR-UHFFFAOYSA-N 0.000 description 2
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 description 2
- HIPHGIQOCYCDAA-UHFFFAOYSA-N 2-(6-phenyldibenzofuran-4-yl)pyridine Chemical compound C1=CC=CC=C1C1=CC=CC2=C1OC1=C(C=3N=CC=CC=3)C=CC=C12 HIPHGIQOCYCDAA-UHFFFAOYSA-N 0.000 description 2
- QMEQBOSUJUOXMX-UHFFFAOYSA-N 2h-oxadiazine Chemical compound N1OC=CC=N1 QMEQBOSUJUOXMX-UHFFFAOYSA-N 0.000 description 2
- BWCDLEQTELFBAW-UHFFFAOYSA-N 3h-dioxazole Chemical compound N1OOC=C1 BWCDLEQTELFBAW-UHFFFAOYSA-N 0.000 description 2
- YKRKDAJLGCBLOE-UHFFFAOYSA-N 4-chloro-2-(6-propan-2-yldibenzofuran-4-yl)pyridine Chemical compound C=12OC=3C(C(C)C)=CC=CC=3C2=CC=CC=1C1=CC(Cl)=CC=N1 YKRKDAJLGCBLOE-UHFFFAOYSA-N 0.000 description 2
- PVCISOSAKGBAFO-UHFFFAOYSA-N 4-methyl-2-(6-propan-2-yldibenzofuran-4-yl)pyridine Chemical compound C=12OC=3C(C(C)C)=CC=CC=3C2=CC=CC=1C1=CC(C)=CC=N1 PVCISOSAKGBAFO-UHFFFAOYSA-N 0.000 description 2
- JQIHNXZEJUGOSG-UHFFFAOYSA-N 4-phenyldibenzofuran Chemical compound C1=CC=CC=C1C1=CC=CC2=C1OC1=CC=CC=C12 JQIHNXZEJUGOSG-UHFFFAOYSA-N 0.000 description 2
- KOVYEDZFIBSSOT-UHFFFAOYSA-N 4-prop-1-en-2-yldibenzofuran Chemical compound C12=CC=CC=C2OC2=C1C=CC=C2C(=C)C KOVYEDZFIBSSOT-UHFFFAOYSA-N 0.000 description 2
- YSQKKBZIXJXHJZ-UHFFFAOYSA-N 4-propan-2-yl-2-(6-propan-2-yldibenzofuran-4-yl)pyridine Chemical compound CC(C)C1=CC=NC(C=2C=3OC4=C(C(C)C)C=CC=C4C=3C=CC=2)=C1 YSQKKBZIXJXHJZ-UHFFFAOYSA-N 0.000 description 2
- IFIGYYUIGXGCJA-UHFFFAOYSA-N 4-propan-2-yldibenzofuran Chemical compound C12=CC=CC=C2OC2=C1C=CC=C2C(C)C IFIGYYUIGXGCJA-UHFFFAOYSA-N 0.000 description 2
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- BCMKFVHGZUOLBQ-UHFFFAOYSA-N C(C)(C)C1=CC=CC=2C3=C(OC21)C(=CC=C3)OB(O)O Chemical compound C(C)(C)C1=CC=CC=2C3=C(OC21)C(=CC=C3)OB(O)O BCMKFVHGZUOLBQ-UHFFFAOYSA-N 0.000 description 2
- 229910004664 Cerium(III) chloride Inorganic materials 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical group [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 2
- WIUZHVZUGQDRHZ-UHFFFAOYSA-N [1]benzothiolo[3,2-b]pyridine Chemical compound C1=CN=C2C3=CC=CC=C3SC2=C1 WIUZHVZUGQDRHZ-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
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- MABNMNVCOAICNO-UHFFFAOYSA-N selenophene Chemical compound C=1C=C[se]C=1 MABNMNVCOAICNO-UHFFFAOYSA-N 0.000 description 1
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- 239000002356 single layer Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
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- 238000005476 soldering Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
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- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- JPJIEXKLJOWQQK-UHFFFAOYSA-K trifluoromethanesulfonate;yttrium(3+) Chemical compound [Y+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F JPJIEXKLJOWQQK-UHFFFAOYSA-K 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
- C07F15/0033—Iridium compounds
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- C09K11/07—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials having chemically interreactive components, e.g. reactive chemiluminescent compositions
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- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
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- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
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Description
本發明係關於異配位基銥錯合物(heteroleptic iridium complex),且特定言之係關於含有苯基吡啶及二苯并配體之錯合物。該等錯合物適用於OLED裝置。
所主張之發明由簽署大學-企業聯合研究協議的各方中之一方或多方進行、以各方中之一方或多方為名義進行,或與以下各方中之一方或多方聯合進行:密歇根大學(University of Michigan)、普林斯頓大學(Princeton University)、南加利福尼亞大學(The University of Southern California)的校董,及通用顯示器公司(Universal Display Corporation)。該協議在作出所主張之發明的當日或之前便生效,且所主張之發明係由於在該協議範疇之內進行的活動而進行。
利用有機材料之光電裝置由於多種原因而變得愈發合意。用於製造此等裝置之許多材料相對便宜,因此有機光電裝置具有優於無機裝置之成本優勢的潛力。此外,有機材料之固有特性,諸如其可撓性,可使其充分適合於特定應用,諸如在一可撓性基板上之製作。有機光電裝置之實例包括有機發光裝置(OLED)、有機光電晶體、有機光伏電池,及有機光偵測器。對於OLED而言,有機材料可具有優於習知材料之效能優勢。例如,使用適當摻雜劑通常可而容易地調諧有機發射層發光之波長。
OLED利用當在裝置上施加電壓時發光之薄有機膜。
OLED變成一種日益受關注之用於諸如平板顯示器、照明,及背光照明之應用中的技術。數種OLED材料及構型經描述於美國專利第5,844,363號、第6,303,238號及第5,707,745號中,其係以引用的方式全部併入本文中。
磷光發射分子之一應用為全彩色顯示器。此顯示器之行業標準要求像素適配成發射稱為「飽和」色之特定顏色。詳言之,此等標準要求飽和紅、綠,及藍色像素。顏色可使用在此項技術中熟知之CIE坐標來量測。
綠色發射分子之一實例為參(2-苯基吡啶)銥,表示為Ir(ppy)3,其具有以下結構:
在此圖及本文之後的圖中,將自氮至金屬(此處為Ir)之配位鍵描繪為直線。
如本文所使用,術語「有機」包括聚合材料以及小分子有機材料,此等材料可用於製作有機光電裝置。「小分子」係指不為聚合物之任何有機材料,且「小分子」可能實際上相當大。在一些情況下,小分子可包括重複單元。舉例而言,使用長鏈烷基作為取代基不會將分子自「小分子」類別排除。亦可將小分子併入聚合物中,例如作為聚合物主鏈上之側基或作為主鏈之一部分。小分子亦可充當樹枝狀聚合物之核心部分,該樹枝狀聚合物包括建立在核心部
分之上的一系列化學外殼。樹枝狀聚合物之核心部分可為螢光或磷光小分子發射體。樹枝狀聚合物可為「小分子」,且相信目前OLED領域中所使用之所有樹枝狀聚合物均為小分子。
如本文所使用,「頂部」意謂距離基板最遠,而「底部」意謂距離基板最近。當第一層經描述為「佈置於第二層之上」時,則第一層經進一步遠離基板佈置。在第一層與第二層之間可存在其他層,除非說明第一層與第二層「接觸」。例如,陰極可經描述為「佈置於陽極之上」,即使兩者之間存在各種有機層。
如本文所使用,「溶液可加工」意謂能夠在液體介質(溶液或懸浮液形式)中溶解、分散,或輸送及/或自液體介質沈積。
當據信配體對發射材料之光敏特性有直接貢獻時,該配體可稱為「光敏的」。當據信配體對發射材料之光敏特性無貢獻時,該配體可稱為「輔助的」,儘管輔助配體可能改變光敏配體之特性。
如本文所使用,且如熟習此項技術者通常所理解,若第一能級更接近真空能級,則第一「最高佔據分子軌道」(HOMO)或「最低未佔據分子軌道」(LUMO)之能級「大於」或「高於」第二HOMO或LUMO之能級。由於電離電位(IP)經量測為相對真空能級之負能量,因此較高HOMO能級對應具有較小絕對值之IP(較低負性之IP)。類似地,較高LUMO能級對應具有較小絕對值之電子親和力(EA)(較低負
性之EA)。在習知能級圖上,其中真空能級在頂部,材料之LUMO能級高於相同材料之HOMO能級。「較高」HOMO或LUMO能級比「較低」HOMO或LUMO能級看起來更接近此圖的頂部。
如本文所使用,且如熟習此項技術者通常所理解,若第一逸出功具有較高絕對值,則第一逸出功「大於」或「高於」第二逸出功。因為逸出功通常經量測為相對真空能級之負數,因此此點意謂「較高」逸出功之負性更大。在習知能級圖上,其中真空能級在頂部,「較高」逸出功經說明為在向下方向上進一步遠離真空能級。因此,HOMO及LUMO能級之定義遵循與逸出功不同之約定。
關於OLED之更多細節及以上描述之定義可見美國專利第7,279,704號,該專利係以引用的方式全部併入本文中。
提供一種具有下式之化合物:。在式I化合物中,R1、R2、R3、R4、RA、RB以及RC獨立地選自由以下各項組成之群:氫、氘、烷基、環烷基、芳基、雜芳基及其組合。RA、RB以及RC可以表示單取代、二取代、三取代或四取代,且R1、R2、R3以及R4中之至少一者不为氫或氘。兩個相鄰的
取代基R1、R2、R3、R4、RA、RB以及RC視情況接合形成稠環。X選自由以下各項組成之群:O、S以及Se,且m為1或2。
在一態樣中,R1為烷基。在一態樣中,RC及R1皆為烷基。在一態樣中,R1及R3皆為烷基。在一態樣中,RC及R3皆為烷基。在一態樣中,X為O。在一態樣中,RA及RB皆為氫。在一態樣中,m為2。在另一態樣中,RC表示單烷基取代且RC係與N成對位。
在一態樣中,R1、R2、R3以及R4獨立地選自由以下各項組成之群:甲基、CH(CH3)2以及苯基。在一態樣中,R1、R2、R3以及R4獨立地選自由以下各項組成之群:烷基、氫以及氘。
在另一態樣中,該化合物於10-7至10-8托壓力下之昇華溫度為約180℃至約240℃。
在一態樣中,該化合物具有下式:
在一態樣中,該化合物選自由以下各項組成之群:化合物1-化合物63。
在一態樣中,提供一第一裝置。該裝置包括一第一有機發光裝置,該第一有機發光裝置進一步包括:一陽極、一陰極以及一佈置於該陽極與該陰極之間的有機層,該有機層包含具有下式之化合物:
。在式I化合物中,R1、R2、R3、R4、RA、RB以及RC獨立地選自由以下各項組成之群:氫、氘、烷基、環烷基、芳基、雜芳基及其組合。RA、RB以及RC可以表示單取代、二取代、三取代或四取代,且R1、R2、R3以及R4中之至少一者不为氫或氘。兩個相鄰的取代基R1、R2、R3、R4、RA、RB以及RC視情況接合形成稠環。X選自由以下各項組成之群:O、S以及Se,且m為1或2。
在一態樣中,該第一裝置為一消費品。在另一態樣中,該第一裝置為一有機發光裝置。在一態樣中,該第一裝置包括一照明板。
在一態樣中,該有機層為一發射層且該化合物為一非發射摻雜劑。在一態樣中,該有機層進一步包括主體。
在一態樣中,該主體包含含有苯并稠合噻吩或苯并稠合呋喃之三亞苯,其中該主體中之任何取代基獨立地選自由以下各項組成之群的未經稠合之取代基:CnH2n+1、OCnH2n+1、OAr1、N(CnH2n+1)2、N(Ar1)(Ar2)、CH=CH-CnH2n+1、C≡CHCnH2n+1,Ar1、Ar1-Ar2、CnH2n-Ar1,或無取代。Ar1及Ar2獨立地選自由以下各項組成之群:苯、聯苯、萘、三亞苯、咔唑以及其雜芳族類似物,且n為1至10。
在一態樣中,該主體具有下式:。
在一態樣中,該主體選自由以下各項組成之群:
、及其組合。
在一態樣中,該主體為金屬錯合物。
通常,OLED包含至少一佈置於陽極與陰極之間,且電連接至陽極及陰極之有機層。當施加電流時,陽極將電洞注
入有機層,且陰極將電子注入有機層。注入之電洞及電子各自向帶相反電荷之電極遷移。當電子及電洞定位在相同分子上時,將形成「激子」,該激子為具有激發能態之定位電子-電洞對。當激子經由光電發射機理弛豫時將會發光。在某些情況下,激子可定位在激基締合物或激基複合物上。亦可發生非輻射機理,諸如熱弛豫,但通常認為非輻射機理不合意。
最初之OLED使用可自分子之單線態發光(「螢光」)的發射分子,如例如美國專利第4,769,292號所揭示,該專利係以引用的方式全部併入。螢光發射通常發生在小於10納秒的時間幀內。
最近,已經顯示具有發射材料之OLED,此等發射材料可自三線態發射光(「磷光」)。Baldo等人,「Highly Efficient Phosphorescent Emission from Organic Electroluminescent Devices,」Nature,第395卷,151-154,1998;(「Baldo-I」)及Baldo等人,「Very high-efficiency green organic light-emitting devices based on electrophosphorescence,」Appl.Phys.Lett.,第75卷,第3版,4-6(1999)(「Baldo-II」),該等文獻係以引用的方式全部併入。磷光經更詳細地描述於美國專利第7,279,704號,第5-6欄中,該專利係以引用的方式併入。
第1圖展示有機發光裝置100。圖式不必按比例繪製。裝置100可包括基板110、陽極115、電洞注入層120、電洞傳輸層125、電子阻擋層130、發射層135、電洞阻擋層140、
電子傳輸層145、電子注入層150、保護層155及陰極160。陰極160為具有第一導電層162及第二導電層164的化合物陰極。裝置100可藉由按順序沈積所描述層來製作。此等不同層以及實例材料之特性及功能經更詳細地描述在US 7,279,704,第6-10欄中,US 7,279,704係以引用的方式併入。
可得到此等層之每一者的更多實例。舉例而言,美國專利第5,844,363號中揭示一種可撓性且透明之基板-陽極組合,該專利係以引用的方式全部併入。p型摻雜之電洞傳輸層之實例為在50:1的摩爾比下用F.sub.4-TCNQ摻雜之m-MTDATA,如在美國專利申請公開案第2003/0230980號中所揭示,該專利係以引用的方式全部併入。發射及主體材料之實例揭示於Thompson等人之美國專利第6,303,238號中,該專利係以引用的方式全部併入。n型摻雜之電子傳輸層之實例為在1:1的摩爾比下用Li摻雜之BPhen,如在美國專利申請公開案第2003/0230980號中所揭示,該專利係以引用的方式全部併入。美國專利第5,703,436號及第5,707,745號揭示陰極之實例,該等陰極包括具有金屬薄層之化合物陰極,諸如上面覆蓋有透明、導電、濺射沈積之ITO層的Mg:Ag金屬薄層,該等專利係以引用的方式全部併入。阻擋層之理論及用途經更詳細地描述於美國專利第6,097,147號及美國專利申請公開案第2003/0230980號中,該等專利係以引用的方式全部併入。注入層之實例經提供於美國專利申請公開案第2004/0174116號中,該專利係以引用的方式全部併入。保護層之描述可見美國專利申請公
開案第2004/0174116號,該專利係以引用的方式全部併入。
第2圖展示經倒置之OLED 200。該裝置包括基板210、陰極215、發射層220、電洞傳輸層225及陽極230。裝置200可藉由按順序沈積所描述層來製作。因為最常見之OLED構型具有陰極佈置於陽極上,且裝置200具有陰極215佈置於陽極230下,因此裝置200可稱作「倒置」之OLED。類似於關於裝置100所描述之材料的材料可用於裝置200之相對應層中。第2圖提供如何自裝置100之結構中省略一些層之一實例。
藉由非限制性實例提供第1圖及第2圖中所說明之簡單層狀結構,且應理解,本發明之實施例可與廣泛多種其他結構相關聯使用。所描述之特定材料及結構實際上為例示性的,且可使用其他材料及結構。功能化之OLED可藉由以不同方式組合所描述之各種層來實現,或可基於設計、效能及成本因素完全地省略多個層。亦可包括其他未明確描述之層。可使用除明確描述之材料以外的材料。雖然本文提供之許多實例將各種層描述為包含單一材料,但應理解,可使用材料之組合,諸如主體與摻雜劑之混合物,或更通常地混合物。層亦可具有各種子層。本文給予各種層之名稱並不意欲嚴格地限制。舉例而言,在裝置200中,電洞傳輸層225傳輸電洞且將電洞注入發光層220中,且可經描述為電洞傳輸層或電洞注入層。在一實施例中,OLED可經描述為具有「有機層」,該有機層佈置於陰極與陽極之間。此有機層可包含單層,或可進一步包含多個如例如關於第1
圖及第2圖所描述之不同有機材料之層。
亦可使用未明確描述之結構及材料,諸如包含諸如揭示於Friend等人之美國專利第5,247,190號中的聚合物材料之OLED(PLED),該專利係以引用的方式全部併入。進一步舉例而言,可使用具有單一有機層之OLED。OLED可為堆疊的,例如,如在Forrest等人之美國專利第5,707,745號中所描述,該專利係以引用的全部方式併入。OLED結構可偏離第1圖及第2圖中所說明的簡單層狀結構。舉例而言,基板可包括成角度之反射表面以提高出光,諸如在Forrest等人之美國專利第6,091,195號中所描述之檯面結構,及/或如在Bulovic等人之美國專利第5,834,893號中所描述之坑形結構,該等專利係以引用的方式全部併入。
除非另外指出,否則各種實施例之任一層可藉由任何適合的方法來沈積。對於有機層而言,較佳方法包括熱蒸發、噴墨,諸如在美國專利第6,013,982號及第6,087,196號中所描述,該等專利係以引用的方式全部併入;有機氣相沈積(OVPD),諸如在Forrest等人之美國專利第6,337,102號中所描述,該專利係以引用的方式全部併入;及藉由有機蒸汽噴印(OVJP)沈積,諸如在美國專利申請序號10/233,470中所描述,該專利係以引用的方式全部併入。其他適合的沈積方法包括旋塗及其他基於溶液之方法。基於溶液之方法較佳地在氮氣或惰性氣氛下進行。對於其他層而言,較佳方法包括熱蒸發。較佳圖案化方法包括經由遮罩沈積、冷焊,諸如在美國專利第6,294,398號及第6,468,819號中所描述,
該等專利係以引用的方式全部併入,及與一些沈積方法,諸如噴墨及OVJD,相關聯之圖案化。亦可使用其他方法。可改質待沈積之材料以使其與特定沈積方法相容。舉例而言,在小分子中可使用諸如烷基及芳基、支鏈或直鏈、且較佳地含有至少3個碳原子之取代基,藉此提高其經受溶液加工之能力。可使用具有20個或20個以上碳之取代基,且3至20個碳為較佳範圍。具有不對稱結構之材料可比具有對稱結構之材料有更好之溶液加工性,因為不對稱材料可具有較低之再結晶趨勢。可使用樹枝狀聚合物取代基來提高小分子經受溶液加工之能力。
根據本發明之實施例製作的裝置可經併入廣泛多種消費品中,包括:平板顯示器、電腦顯示器、醫療顯示器、電視、廣告牌、用於室內或室外照明及/或信號傳導之燈、平視顯示器、完全透明之顯示器、可撓性顯示器、激光列印機、電話、手機、個人數位助理(PDA)、便攜式電腦、數碼相機、攝像機、探視器、微顯示器、車輛、大面積牆壁、劇場或運動場屏幕或招牌。可使用各種控制機理來控制根據本發明製作之裝置,包括無源矩陣及有源矩陣。許多裝置意欲在對人體舒適之溫度範圍內使用,諸如18攝氏度至30攝氏度,且更佳地在室溫下(20攝氏度至25攝氏度)使用。
本文描述之材料及結構可在除OLED之外的裝置中應用。例如,其他光電裝置,諸如有機太陽能電池及有機光偵測器,可採用該等材料及結構。更通常地,有機裝置,諸如有機電晶體,可採用該等材料及結構。
術語鹵基、鹵素、烷基、環烷基、烯基、炔基、芳烷基(arylkyl)、雜環基、芳基、芳族基團及雜芳基為此項技術所已知,且經定義在US 7,279,704第31-32欄中,該專利係以引用的方式併入本文中。
提供一種具有下式之化合物:。在式I化合物中,R1、R2、R3、R4、RA、RB以及RC獨立地選自由以下各項組成之群:氫、氘、烷基、環烷基、芳基、雜芳基及其組合。RA、RB以及RC可以表示單取代、二取代、三取代或四取代,且R1、R2、R3以及R4中之至少一者不为氫或氘。兩個相鄰的取代基R1、R2、R3、R4、RA、RB以及RC視情況接合形成稠環。X選自由以下各項組成之群:O、S以及Se,且m為1或2。
已出乎意料地發現在位置R1至R4中之一或多個位置處的烷基取代產生具有所需特性之式I化合物。該等特性使得併入了式I化合物的OLED裝置能夠具有改良之特性,諸如較高的效率及更長的壽命。在位置R1至R4中之一或多個位置處的烷基取代亦產生具有降低的昇華溫度的化合物,儘管該等化合物具有比在R1至R4處全部具有氫取代之化合物高的分子量。在不受理論束縛情況下,咸信昇華溫度的此種降低可能是固態時分子堆砌效率降低或減小之結果,進而
降低了破壞晶格所需的能量且導致昇華溫度降低。低昇華溫度有利地允許更容易地純化式I化合物以及於製造中更好之熱穩定性。
在另一實施例中,該化合物於10-7至10-8托壓力下之昇華溫度為約180℃至約240℃。
在一實施例中,R1為烷基。在一實施例中,RC及R1皆為烷基。在一實施例中,R1及R3皆為烷基。在一實施例中,RC及R3皆為烷基。在一實施例中,X為O。在一實施例中,RA及RB皆為氫。在一實施例中,m為2。在另一實施例中,RC表示單烷基取代且RC係與N成對位。
在一實施例中,R1、R2、R3以及R4獨立地選自由以下各項組成之群:甲基、CH(CH3)2以及苯基。在一實施例中,R1、R2、R3以及R4獨立地選自由以下各項組成之群:烷基、氫以及氘。
在一實施例中,化合物具有下式:
在一實施例中,該化合物選自由以下各項組成之群:
以及。
在一實施例中,化合物選自由以下各項組成之群:
、以及
在一實施例中,提供一第一裝置。該裝置包括一第一有機發光裝置,該第一有機發光裝置進一步包括:一陽極、一陰極以及一佈置於該陽極與該陰極之間的有機層,該有機層包含具有下式之化合物:
。在式I化合物中,R1、R2、R3、R4、RA、RB以及RC獨立地選自由以下各項組成之群:氫、氘、烷基、環烷基、芳基、雜芳基及其組合。RA、RB以及RC可以表示單取代、二取代、三取代或四取代,且R1、R2、R3以及R4中之至少一者不为氫或氘。兩個相鄰的取代基R1、R2、R3、R4、RA、RB以及RC視情況接合形成稠環。X選自由以下各項組成之群:O、S以及Se,且m為1或2。
在一實施例中,該第一裝置為一消費品。在另一實施例中,該第一裝置為一有機發光裝置。在一態樣中,該第一裝置包括一照明板。
在一實施例中,該有機層為一發射層且該化合物為一非發射摻雜劑。在一實施例中,該有機層進一步包括一主體。
在一實施例中,該主體包含含有苯并稠合噻吩或苯并稠合呋喃之三亞苯,其中該主體中的任何取代基獨立地選自由以下各項組成之群的未經稠合之取代基:CnH2n+1、OCnH2n+1、OAr1、N(CnH2n+1)2、N(Ar1)(Ar2)、CH=CH-CnH2n+1、C≡CHCnH2n+1、Ar1、Ar1-Ar2、CnH2n-Ar1,或無取代。Ar1及Ar2獨立地選自由以下各項組成之群:苯、聯苯、萘、三亞苯、咔唑以及其雜芳族類似物,且n為1至10。
在一實施例中,該主體具有下式:。
在一實施例中,該主體選自由以下各項組成之群:
、及其組合。
在一態樣中,該主體為金屬錯合物。
所有實例裝置藉由高真空(<10-7托)熱蒸發來製作。陽極電極為1200 Å的氧化銦錫(ITO)。陰極由10 Å的LiF,接著
1,000 Å的Al組成。在製作後,所有裝置立即用密封有環氧樹脂的玻璃蓋封裝於氮氣手套箱中(<1 ppm的H2O及O2),且將吸濕劑併入於包裝內。
裝置實例的有機堆疊連續地由以下組成:ITO表面、100 Å的化合物B或C作為電洞注入層(HIL)、300 Å的4,4'-雙[N-(1-萘基)-N-苯基氨基]聯苯(NPD)作為電洞傳輸層(HTL)、摻雜300 Å的本發明化合物之化合物D作為主體、7、10、13 wt%的Ir磷光化合物作為發射層(EML)、50 Å的化合物D作為阻擋層(BL)、450 Å的Alq3(三-8-羥基喹啉鋁)作為ETL。使用化合物A及B比較實例係類似於裝置實例來製作,例外為化合物A或B係用作EML中的發射極。
裝置結構及來自彼等裝置的數據總結於表1、表2以及表3中。如本文所使用,化合物A、B、C、D具有下列結構:
表2為裝置數據之總結。於1000尼特下量測發光效率(LE)、外量子效率(EQE)及功率效率(PE),而壽命(LT80%)經定義為裝置於40 mA/cm2之恆定電流密度下,衰減至其初始亮度的80%所需要的時間。
自表2之裝置結果可見,三種不同摻雜濃度7%、10%、13%
的化合物2的外量子效率(EQE)為18%、18.6%、17.9%,該等外量子效率全部均比其於相同摻雜濃度下的相應比較化合物A的EQE效率(分別為15.9%、15.4%以及14.1%)更大。比較化合物A在位置R1處缺少烷基。對其發光效率(LE)而言亦得到此結果。當與比較化合物A及B比較時,對化合物1、3、4以及5得到類似的較高EQE及LE結果。此外,化合物2及1之LT80%壽命顯著比不同摻雜濃度的比較化合物A及B的壽命長。
表3說明於位置R1至R4中之一個位置處的烷基化對式I化合物之昇華溫度的作用。式I化合物,如化合物1、2、4以及5為比較化合物A的烷基化類似物。化合物1、2、4以及5之昇華溫度比顯著比較化合物A之昇華溫度低。如以上所討論,該等化合物之較低昇華溫度可能歸因於烷基化,此種烷基化可以阻止固態時的分子堆砌,並因此減少分子間相互作用進而降低昇華溫度。該等所需的裝置結果表明比較化合物A之二苯并呋喃片段上的烷基取代將顯著改良裝置於以下方面的效能:裝置壽命、效率以及昇華溫度。
本文描述成可用於有機發光裝置中之特定層的材料可與存在於裝置中之廣泛多種其他材料組合使用。例如,本文揭示之發射摻雜劑可聯合廣泛多種主體、傳輸層、阻擋層、注入層、電極及可能存在之其他層使用。以下描述或提及的材料為可用於與本文揭示之化合物組合的材料之非限制
性實例,且熟習此項技術者可容易地查閱文獻來鑒別可用於組合之其他材料。
在本發明中使用之電洞注入/傳輸材料不特定限制,且可使用任何化合物,只要該化合物典型地用作電洞注入/傳輸材料。材料之實例包括,但不限於:酞菁或卟啉衍生物;芳族胺衍生物;吲哚并咔唑衍生物;含有氟代烴之聚合物;具有導電型摻雜劑之聚合物;導電聚合物,諸如PEDOT/PSS;由化合物諸如膦酸及矽烷(sliane)衍生物衍生之自組裝單體;金屬氧化物衍生物,諸如MoOx;p型半導體有機化合物,諸如1,4,5,8,9,12-六氮雜聯伸三苯六腈;金屬錯合物,及可交聯之化合物。
在HIL或HTL中使用之芳族胺衍生物之實例包括,但不限於以下通用結構:
Ar1至Ar9各自選自由以下各項組成之群:芳族烴環狀化合物,諸如苯、聯苯基、三苯基、聯伸三苯、萘、蒽、非
那烯、菲、茀、芘、、苝、薁;各自選自由以下各項組成之群:芳族雜環化合物,諸如二苯并噻吩、二苯并呋喃、二苯并硒吩、呋喃、噻吩、苯并呋喃、苯并噻吩、苯并硒吩、咔唑、吲哚并咔唑、吡啶基吲哚、吡咯并吡啶、吡唑、咪唑、三唑、噁唑、噻唑、噁二唑、噁三唑、二噁唑、噻二唑、吡啶、噠嗪、嘧啶、吡嗪、三嗪、噁嗪、噁噻嗪、噁二嗪、吲哚、苯并咪唑、吲唑、吲哚噁嗪、苯并噁唑、苯并異噁唑、苯并噻唑、喹啉、異喹啉、啉、喹唑啉、喹諾啉、啶、酞嗪、蝶啶、呫噸、吖啶、吩嗪、吩噻嗪、吩噁嗪、苯并呋喃并吡啶、呋喃并二吡啶(furodipyridine)、苯并噻吩并吡啶、噻吩并二吡啶、苯并硒吩并吡啶(benzoselenophenopyridine),及硒吩并二吡啶;且各自選自由以下各項組成之群:2至10個環狀結構單元,其為選自芳族烴環狀基團及芳族雜環基團之相同類型或不同類型的基團,且彼此直接或經由氧原子、氮原子、硫原子、矽原子、磷原子、硼原子、鏈結構單元及脂族環狀基團中之至少一者鍵合。其中各Ar進一步經選自由以下各項組成之群的取代基取代:氫、氘、鹵化物、烷基、環烷基、雜烷基、芳烷基、烷氧基、芳氧基、胺基、矽烷基、烯基、環烯基、雜烯基、炔基、芳基、雜芳基、醯基、羰基、羧酸、酯、腈、異腈、硫烷基、亞磺醯基、磺醯基、膦基,及其組合。
在一態樣中,Ar1至Ar9獨立地選自由以下各項組成之群:
k為1至20之整數;X1至X8為C(包括CH)或N;Ar1具有與以上所定義相同之基團。
HIL或HTL中使用之金屬錯合物的實例包括(但不限於)以下通式:
M為金屬,原子量大於40;(Y1-Y2)為二齒配體,Y1及Y2獨立地選自C、N、O、P及S;L為輔助配體;m為1至可附接至金屬之配體最大數的整數值;且m+n為可附接至金屬之配體的最大數。
在一態樣中,(Y1-Y2)為2-苯基吡啶衍生物。
在另一態樣中,(Y1-Y2)為碳烯配體。
在另一態樣中,M選自Ir、Pt、Os及Zn。
在另一態樣中,金屬錯合物在溶液中相對於Fc+/Fc電對之最小氧化電勢為小於約0.6 V。
本發明之有機EL裝置的發光層較佳含有至少一種金屬錯合物作為發光材料,且可含有使用該金屬錯合物作為摻雜
劑材料之主體材料。主體材料之實例不特定限制,且可使用任何金屬錯合物或有機化合物,只要主體之三線態能量大於摻雜劑之三線態能量。儘管下表將主體材料歸類為較佳用於發射各種顏色之裝置,但可與任何摻雜劑一起使用任何主體材料,只要滿足三線態標準即可。
用作主體之金屬錯合物的實例較佳具有以下通式:
M為金屬;(Y3-Y4)為二齒配體,Y3及Y4獨立地選自C、N、O、P及S;L為輔助配體;m為1至可附接至金屬之配體最大數的整數值;且m+n為可附接至金屬之配體的最大數。
在一態樣中,金屬錯合物為:
(O-N)為二齒配體,使金屬配位至原子O及N。
在另一態樣中,M選自Ir及Pt。
在另一態樣中,(Y3-Y4)為碳烯配體。
用作主體之有機化合物的實例選自由以下各項組成之群:芳族烴環狀化合物,諸如苯、聯苯基、三苯基、聯伸三苯、萘、蒽、非那烯、菲、茀、芘、、苝、薁;選自由以下各項組成之群:芳族雜環化合物,諸如二苯并噻吩、
二苯并呋喃、二苯并硒吩、呋喃、噻吩、苯并呋喃、苯并噻吩、苯并硒吩、咔唑、吲哚并咔唑、吡啶基吲哚、吡咯并吡啶、吡唑、咪唑、三唑、噁唑、噻唑、噁二唑、噁三唑、二噁唑、噻二唑、吡啶、噠嗪、嘧啶、吡嗪、三嗪、噁嗪、噁噻嗪、噁二嗪、吲哚、苯并咪唑、吲唑、吲哚噁嗪、苯并噁唑、苯并異噁唑、苯并噻唑、喹啉、異喹啉、啉、喹唑啉、喹諾啉、啶、酞嗪、蝶啶、呫噸、吖啶、吩嗪、吩噻嗪、吩噁嗪、苯并呋喃并吡啶、呋喃并二吡啶、苯并噻吩并吡啶、噻吩并二吡啶、苯并硒吩并吡啶及硒吩并二吡啶;且選自由以下各項組成之群:2至10個環狀結構單元,其為選自芳族烴環狀基團及芳族雜環基團之相同類型或不同類型的基團,且彼此直接或經由氧原子、氮原子、硫原子、矽原子、磷原子、硼原子、鏈結構單元及脂肪族環狀基團中之至少一者鍵合。其中各基團進一步經選自由以下各項組成之群的取代基取代:氫、氘、鹵化物、烷基、環烷基、雜烷基、芳烷基、烷氧基、芳氧基、胺基、矽烷基、烯基、環烯基、雜烯基、炔基、芳基、雜芳基、醯基、羰基、羧酸、酯、腈、異腈、硫烷基、亞磺醯基、磺醯基、膦基及其組合。
在一態樣中,主體化合物分子中含有以下基團中之至少一者:
R1至R7獨立地選自由以下各項組成之群:氫、氘、鹵化物、烷基、環烷基、雜烷基、芳烷基、烷氧基、芳氧基、胺基、矽烷基、烯基、環烯基、雜烯基、炔基、芳基、雜芳基、醯基、羰基、羧酸、酯、腈、異腈、硫烷基、亞磺醯基、磺醯基、膦基及其組合,當R1至R7為芳基或雜芳基時,其具有與以上提及之Ar類似的定義。
k為0至20之整數。
X1至X8選自C(包括CH)或N。
Z1及Z2選自NR1、O,或S。
電洞阻擋層(HBL)可用於降低離開發射層之電洞及/或激子之數量。裝置中此阻擋層之存在使得效率比缺少阻擋層之類似裝置明顯較高。阻擋層亦可用於將發射限制在OLED之所需區域內。
在一態樣中,HBL使用之化合物含有以上描述之用作主體之相同的分子或相同的官能團。
在另一態樣中,HBL使用之化合物分子中含有以下基團中之至少一者:
k為0至20之整數;L為輔助配體,m為1至3之整數。
電子傳輸層(ETL)可包括能夠傳輸電子之材料。電子傳輸層可為本征的(未摻雜的),或摻雜的。摻雜可用於加強導電性。ETL材料之實例不特定限制,且可使用任何金屬錯合物或有機化合物,只要其典型地用於傳輸電子。
在一態樣中,ETL使用之化合物分子中含有以下基團中之至少一者:
R1選自由以下各項組成之群:氫、氘、鹵化物、烷基、環烷基、雜烷基、芳烷基、烷氧基、芳氧基、胺基、矽烷基、烯基、環烯基、雜烯基、炔基、芳基、雜芳基、醯基、
羰基、羧酸、酯、腈、異腈、硫烷基、亞磺醯基、磺醯基、膦基,及其組合,當R1為芳基或雜芳基時,其具有與以上提及之Ar類似的定義。
Ar1至Ar3具有與以上提及之Ar類似的定義。
k為0至20之整數。
X1至X8選自C(包括CH)或N。
在另一態樣中,ETL中使用之金屬錯合物含有(但不限於)以下通式:
(O-N)或(N-N)為二齒配體,使金屬配位至原子O、N或N、N;L為輔助配體;m為1至可附接至金屬之配體之最大數的整數值。
在任何以上提及之用於OLED裝置的各層中之化合物中,氫原子可經部分或完全氘化。
除本文揭示之材料之外,及/或與本文揭示之材料組合,亦可在OLED中使用許多電洞注入材料、電洞傳輸材料、主體材料、摻雜材料、激子/電洞阻擋層材料、電子傳輸及電子注入材料。可在OLED中與本文揭示之材料組合使用的材料之非限制性實例經列在下表4中。表4列出材料之非限制性類別,各類別的化合物之非限制性實例,及揭示所述材料之參考文獻。
本文通篇使用之化學縮寫如下:Cy為環己基,dba為二苯亞甲基丙酮,EtOAc為乙酸乙酯,DME為二甲氧基乙烷,dppe為1,2-雙(二苯基膦基)乙烷,THF為四氫呋喃,DCM為二氯甲烷,S-Phos為二環己基(2',6'-二甲氧基-[1,1'-聯苯]-2-基)膦。
合成4-碘苯并[b,d]呋喃:將300 mL的THF中之2,4-二苯并[b,d]呋喃(25 g,149 mmol)裝入1 L圓底燒瓶,冷卻至-78℃。向燒瓶非常緩慢地添加正丁基鋰(102 mL,164 mmol)。將反應升溫至室溫,並使其攪拌五小時。隨後,使反應冷卻回-78℃。向反應非常緩慢地添加溶於50 mL的THF中之碘(37.7 g,149 mmol)的溶液。將反應升溫至室溫隔夜。向反應添加碳酸氫鈉水溶液(300 mL)。在該等層分離後,將水層用乙酸乙酯(2×100 mL)萃取。在真空移除溶劑後,對粗產物進行柱層析法(SiO2,己烷中之3%乙酸乙酯,v/v),隨後自己烷中結晶以產生30 g(68.6%)純產物。
合成4-甲基二苯并[b,d]呋喃:使4-碘二苯并[b,d]呋喃(10 g,34.0 mmol)及磷酸鉀(23.49 g,102 mmol)溶於200 mL的甲苯及20 mL的水中。將反應用氮沖洗20分鐘,隨後添加2,4,6-三甲基-1,3,5,2,4,6-三氧雜硼環己烷(5.34 mL,5.94 mmol)、Pd2(dba)3(0.311 g,0.34 mmol)以及S-Phos(0.558 g,1.36 mmol)。使反應回流18小時。在使反應冷卻至室溫後,添加100 mL的水,使有機層及水層分離,且將水層用100 mL的甲苯萃取兩次。使該等有機層通過矽膠塞,用DCM溶離。在溶劑蒸發後,對粗產物進行柱層析法(SiO2,己烷中之3%乙酸乙酯至己烷中之5%乙酸乙酯,v/v)以產生6 g(96.7%)純產物,其藉由GC確認。
合成(6-甲基二苯并[b,d]呋喃-4基)硼酸:在-78℃下,向4-甲基二苯并[b,d]呋喃(4-methylldibenzo[b,d]furan)(6 g,32.9 mmol)的100 mL無水THF溶液緩慢地添加正丁基鋰(51.4 mL,82 mmol)。將反應在室溫下攪拌5小時,隨後冷卻回-78℃。向反應混合物非常緩慢地添加硼酸三甲酯(12.85 mL,115 mmol)。使反應物加熱至室溫隔夜,隨後倒
入100 mL的帶冰NH4OH溶液中。將混合物用3×100 mL之乙酸乙酯萃取並由硫酸鈉乾燥。將產物自DCM/己烷中結晶以產生6.5 g(87%),其藉由NMR確認。
合成2-(6-甲基二苯并[b,d]呋喃-4-基)吡啶:使(6-甲基二苯并[b,d]呋喃-4-基)硼酸(6.4 g,28.3 mmol)及磷酸鉀(19.56 g,85 mmol)溶於燒杯中的200 mL的甲苯及20 mL的水中。將反應用氮沖洗20分鐘,隨後添加2-氯吡啶(2.66 mL,28.3 mmol)、Pd2(dba)3(0.778 g,0.849 mmol)以及S-Phos(1.046 g,2.55 mmol)。使反應回流18小時。在使反應冷卻至室溫後,向混合物添加50 mL的水並使有機層及水層分離。將水層用100 mL的DCM萃取兩次。使該等有機層通過矽膠塞子,用DCM溶離。在溶劑蒸發後,使粗產物進行柱層析法(SiO2,己烷中之5%乙酸乙酯至己烷中之10%乙酸乙酯,v/v)。對產物進行第二柱層析法(SiO2,己烷中之50%至100% DCM,v/v)以產生3 g(40.9%)純產物。
合成化合物1:使三氟甲磺酸銥錯合物(2.8 g,3.85 mmol)與2-(6-異丙基二苯并[b,d]呋喃-4-基)吡啶(2.99 g,11.54
mmol)在EtOH(25 mL)及MeOH(25 mL)中之混合物於氮氣氛下回流20小時。使反應混合物冷卻回室溫,用乙醇稀釋,並添加Celite®。將混合物攪拌10分鐘並在一小塊矽膠塞上過濾且用乙醇(3至4次)及己烷(3至4次)洗滌。廢棄濾液。隨後用二氯甲烷洗滌Celite®/矽石塞以溶離產物。用己烷中的30% DCM對粗產物進行的矽膠層析分離(用己烷中之20%三乙胺預處理)。使產物自己烷中結晶並藉由昇華進一步純化以產生0.6 g(20.5%)化合物1,其藉由LC/MS確認。
合成4-(丙-1-烯-2-基)二苯并[b,d]呋喃:使4-碘二苯并[b,d]呋喃(25 g,85.0 mmol)及磷酸鉀(58.7 g,255 mmol)溶於500 mL的甲苯及50 mL的水中。將反應用氮沖洗20分鐘,隨後添加4,4,5,5-四甲基-2-(丙-1-烯-2-基)-1,3,2-二氧雜硼(15.98 mL,85 mmol)、Pd2(dba)3(1.55 g,1.7 mmol)以及S-Phos(2.79 g,6.8 mmol)。使反應回流18小時。在使反應冷卻至室溫後,添加100 mL的水,使有機層及水層分離,且將水層用100 mL乙酸乙酯萃取兩次。使該等有機層通過矽膠塞,用DCM溶離。在溶劑蒸發後,對粗產物進行柱層析法(SiO2,己烷中之3%乙酸乙酯至己烷中之5%乙酸乙酯,v/v)以產生14.5 g(82%)純產物。
合成4-異丙基二苯并[b,d]呋喃:向具有EtOH(100 mL)的氫化器瓶添加4-(丙-1-烯-2-基)二苯并[b,d]呋喃(14.5 g,69.6 mmol)。藉由使N2鼓泡10分鐘來使反應混合物脫氣。添加Pd/C(1.14 g,1.39 mmol)及Pt/C(2.72 g,0.7 mmol)。將反應混合物於Parr氫化器上置放2小時(H2約72 psi,基於計算值)。在密堆Celite®床上過濾反應混合物並用二氯甲烷洗滌。GC/MS確認完全轉化。用己烷中之2% DCM(v/v)對粗產物進行矽膠層析分離,以產生10.9 g(74%)所需產物。產物藉由GC/MS確認。
合成(6-異丙基二苯并[b,d]呋喃-4基)硼酸:在-78℃下,向100 mL的無水THF中的4-異丙基二苯并[b,d]呋喃(10.9 g,51.8 mmol)緩慢地添加正丁基鋰(81 mL,130 mmol)。使此混合物在室溫下攪拌5小時,隨後冷卻回-78℃。向反應緩慢地添加硼酸三甲酯(20.23 mL,181 mmol)並使反應升溫至室溫隔夜。將反應倒入100 mL的帶冰NH4OH溶液中。將混合物用3×100 mL之乙酸乙酯萃取,由硫酸鈉乾燥,自DCM/己烷中蒸發並結晶以產生10.1 g(77%)所需產物,其藉由NMR確認。
合成2-(6-異丙基二苯并[b,d]呋喃-4-基)吡啶:將(6-異丙基二苯并[b,d]呋喃-4-基)硼酸(4 g,15.74 mmol)及磷酸鉀(10.88 g,47.2 mmol)溶於200 mL的甲苯及20 mL的水中。將反應用氮沖洗20分鐘,隨後添加2-氯吡啶(1.481 mL,15.74 mmol)、Pd2(dba)3(0.432 g,0.472 mmol)以及S-Phos(0.582 g,1.417 mmol)。使反應回流18小時。在使反應冷卻至室溫後,添加50 mL水,使有機層及水層分離,並將水層用100 mL之乙酸乙酯萃取兩次。使該等有機層通過矽膠塞,用DCM溶離。在溶劑蒸發後,對粗產物進行柱層析法(SiO2,己烷中之5%乙酸乙酯至己烷中之10%乙酸乙酯,v/v)以產生2.3 g(50.8%)純產物。
合成化合物2:使三氟甲磺酸銥錯合物(1.8 g,2.47 mmol)與與2-(6-異丙基二苯并[b,d]呋喃-4-基)吡啶(2.13 g,7.42 mmol)在EtOH(25 mL)及MeOH(25 mL)中之混合物於氮氣氛下回流20小時。使反應混合物冷卻回室溫,並用乙醇稀釋。添加Celite®並將混合物攪拌10分鐘。在一小塊矽膠塞
上過濾混合物並用乙醇(3至4次)及己烷(3至4次)洗滌。廢棄濾液。隨後用二氯甲烷洗滌Celite®/矽石塞以溶離產物。用己烷中之33% DCM(v/v)對粗產物進行矽膠層析分離。使產物自己烷/乙酸乙酯中結晶並昇華以產生0.6 g(30.8%)化合物2,其藉由LC/MS確認。
合成4-苯基二苯并[b,d]呋喃:將4-碘二苯并[b,d]呋喃(4 g,13.60 mmol)、苯基硼酸(1.99 g,16.32 mmol)、二環己基(2',6'-二甲氧基-[1,1'-聯苯]-2-基)膦(0.447 g,1.08 mmol)、Pd2(dba)2(0.250 g,0.272 mmol)、K3PO4(10.1 g,47.6 mmol)、150 mL的甲苯以及15 mL的水裝入250 mL燒瓶中。藉由使N2鼓泡30分鐘來使反應混合物脫氣,隨後在N2下加熱至回流隔夜。使反應冷卻至室溫並藉由矽膠柱純化粗產物以產生3.3 g(99%),其藉由GC-MS確認。
合成(6-苯基二苯并[b,d]呋喃-4基)硼酸:在-78℃下向80 mL的無水THF中的4-苯基二苯并[b,d]呋喃(3.3 g,13.51 mmol)逐滴滴加正丁基鋰(13.51 mL,33.8 mmol)。使此混合
物在室溫下攪拌5小時,隨後再次冷卻至-78℃。向反應緩慢地添加硼酸三甲酯(4.52 mL,40.5 mmol)。在攪拌下,使反應混合物逐漸升溫至室溫隔夜。將混合物倒入50 mL的帶冰NH4OH溶液中。將混合物水溶液用3×80 mL之乙酸乙酯萃取並藉由硫酸鈉乾燥,且使有機層蒸發以獲得產量3.3 g(85%)產物,該產物無需純化即可使用,並藉由NMR確認。
合成2-(6-苯基二苯并[b,d]呋喃-4-基)吡啶:使(6-苯基二苯并[b,d]呋喃-4-基)硼酸(3.3 g,11.45 mmol)及磷酸鉀(6.63 g,31.2 mmol)溶於150 mL的甲苯及15 ml的水中。將反應用氮沖洗20分鐘,隨後添加2-溴吡啶(1.64 g,10.4 mmol)、Pd2(dba)3(0.2 g,0.208 mmol)以及S-Phos(0.342 g,0.833 mmol)。使反應回流18小時。在冷卻後,添加50 mL的水,使有機層及水層分離,並將水層用100 mL之乙酸乙酯萃取兩次。使該等有機層通過矽膠塞。在溶劑蒸發後,對粗產物進行柱層析法以獲得2.5 g(75%)純產物。
合成化合物3:使三氟甲磺酸銥錯合物(1.5 g,2.0 mmol)
與2-(6-苯基二苯并[b,d]呋喃-4-基)吡啶(2.0 g,6.22 mmol)在EtOH(50 mL)中的混合物在氮氣氛下回流48小時。使反應混合物冷卻至室溫並用乙醇稀釋。添加Celite®並將混合物攪拌10分鐘。在一小塊矽膠塞上過濾混合物並用乙醇(3至4次)及己烷(3至4次)洗滌。廢棄濾液。隨後用二氯甲烷洗滌Celite®/矽石塞以溶離產物。用己烷中之60% DCM(v/v)對粗產物進行矽膠層析分離以產生1.5 g(88%)化合物3,其藉由LC/MS確認。
合成2-(6-異丙基二苯并[b,d]呋喃-4-基)-4-氯吡啶:使(6-異丙基二苯并[b,d]呋喃-4-基)硼酸(12 g,47.2 mmol)及碳酸鉀(19.58 g,142 mmol)溶於100 mL的DME及100 mL的水中。將反應用氮沖洗20分鐘,隨後添加2,4-二氯吡啶(5.61 mL,52 mmol)、Pd(PPh3)4(1.637 g,1.417 mmol)。使反應回流5小時。在使反應冷卻回室溫後,使有機層及水層分離並將水層用100 mL之乙酸乙酯萃取兩次。在溶劑蒸發後,對粗產物進行柱層析法(SiO2,己烷中之30%至60%乙酸乙酯,v/v)以產生10.5 g(70%)純產物。
合成2-(6-異丙基二苯并[b,d]呋喃-4-基)-4-(丙-1-烯-2-基)吡啶:使4-氯-2-(6-異丙基二苯并[b,d]呋喃-4-基)吡啶(10.5 g,32.6 mmol)及磷酸鉀(22.54 g,98 mmol)溶於500 mL的甲苯及50 mL的水中。將反應用氮沖洗20分鐘,隨後添加4,4,5,5-四甲基-2-(丙-1-烯-2-基)-1,3,2-二氧雜硼(6.13 mL,32.6 mmol)、Pd2(dba)3(0.598 g,0.653 mmol)以及二環己基(2',6'-二氧甲基-[1,1'-聯苯]-2-基)膦(1.072 g,2.61 mmol)。使反應回流18小時。在使反應冷卻至室溫後,向反應混合物添加100 mL的水。將水層用100 mL之乙酸乙酯萃取兩次。使該等有機層通過矽膠塞,用DCM溶離。在溶劑蒸發後,對粗產物進行柱層析法(SiO2,己烷中之3%乙酸乙酯至己烷中之5%乙酸乙酯,v/v)以產生6.3 g(60.1%)純產物。
合成4-異丙基-2-(6-異丙基二苯并[b,d]呋喃-4-基)吡啶:向具有EtOH(100 mL)之氫化器瓶添加2-(6-異丙基二苯并
[b,d]呋喃-4-基)-4-(丙-1-烯-2-基)吡啶(8.33 g,25.4 mmol)。藉由使N2鼓泡10分鐘來使反應混合物脫氣。添加Pd/C(0.812 g,0.763 mmol)及Pt/C(1.489 g,0.382 mmol)。將反應混合物於Parr氫化器上置放2小時。在密堆Celite®床上過濾反應混合物並用二氯甲烷洗滌。用己烷中之2% DCM(v/v)對粗產物進行矽膠層析分離並產生7.2 g(87%)所需純產物,其藉由GC/MS確認。
合成化合物4:使三氟甲磺酸銥錯合物(2.5 g,3.44 mmol)與4-異丙基-2-(6-異丙基二苯并[b,d]呋喃-4-基)吡啶(3.39 g,10.31 mmol)在EtOH(25 mL)及MeOH(25 mL)中的混合物於氮氣氛下回流20小時。使反應混合物冷卻回室溫並用乙醇稀釋。向混合物添加Celite®並攪拌10分鐘。在一小塊矽膠塞上過濾混合物並用乙醇(3至4次)及己烷(3至4次)洗滌。廢棄濾液。隨後用二氯甲洗滌Celite®/矽石塞以溶離產物。用己烷中之40%至100%的DCM(v/v)對粗產物進行矽膠層析分離(利用己烷中之20%三乙胺預處理)。使產物自DCM/己烷中結晶,隨後昇華以產生1.37 g(48%)的化合物4,其於昇華後獲得。
合成2-(6-異丙基二苯并[b,d]呋喃-4-基)4-甲基吡啶:使(6-異丙基二苯并[b,d]呋喃-4-基)硼酸(5.5 g,21.65 mmol)及磷酸鉀(11.25 g,64.9 mmol)溶於80 mL的甲苯及8 mL的水中。將反應用氮沖洗20分鐘,隨後添加2-氯吡啶(2.418 ml,21.65 mmol)、Pd2(dba)3(0.595 g,0.649 mmol)以及S-Phos(0.8 g,1.948 mmol)。使反應回流18小時。在使反應冷卻至室溫後,向反應混合物中添加50 mL的水。將水層用100 mL的DCM萃取兩次。使該等有機層通過矽膠塞,用DCM溶離。在溶劑蒸發後,對粗產物進行柱層析法(SiO2,己烷中之5%乙酸乙酯至己烷中之10%乙酸乙酯,v/v)以產生4.3 g(66%)純產物。
合成化合物5:使三氟甲磺酸銥錯合物(1.5 g,2.06 mmol)與2-苯基吡啶(3 g,6.18 mmol)在EtOH(25 mL)及MeOH(25 mL)中之混合物於氮氣氛下回流20小時。使反應混合物冷卻回室溫,用乙醇稀釋,添加Celite®,並將混合物攪拌10分鐘。在一小塊矽膠塞上過濾混合物並用乙醇(3至4次)及己烷(3至4次)洗滌。廢棄濾液。隨後用二氯甲烷洗滌Celite®/矽
石塞以溶離產物。用己烷中之70%二氯甲烷(v/v)對粗產物進行矽膠層析分離以產生0.45 g(28%)所需產物,其藉由LC/MS確認。
合成氯橋二聚物(chloro-bridged dimer):在氮氣氛下,將2-(6-異丙基二苯并[b,d]呋喃-4-基)-4-異丙基吡啶(3.27 g,9.92 mmol)及氯化銥(III)(1.66 g,3.31 mmol)放入含有2-乙氧基乙醇(45 mL)及水(15 mL)的200 mL燒瓶中。使所得反應混合物於130℃下回流18小時。在冷卻回室溫後,將此反應混合物過濾,並用3×己烷,接著用3×甲醇洗滌。將所獲得之產物真空乾燥以產生2.5 g(60%)所需產物。
合成三氟甲磺酸銥鹽:使銥二聚物(2.5 g,1.41 mmol)溶於300 mL的二氯甲烷中。在一個單獨的燒杯中,使三氟甲磺酸銀(I)(0.799 g,3.11 mmol)溶於MeOH(150 mL)中,並
在室溫下,在黑暗處連續攪拌隔夜的情況下,緩慢地添加到二氯甲烷溶液中。經由頂部置放有密堆Celite®床的矽膠過濾反應混合物。在溶劑移除後,獲得呈暗黃色固體的產物,產量2.5 g(78%),並其無需進一步純化即可使用。
合成化合物6:使三氟甲基磺酸銥錯合物(2.5 g,2.01 mmol)與2-苯基吡啶(0.862 g,6.03 mmol)在EtOH(25 mL)及MeOH(25 mL)中的混合物在氮氣氛下回流20小時。使反應冷卻回室溫並用乙醇稀釋。向混合物添加Celite®並將其攪拌10分鐘,隨後在一小塊矽膠塞上過濾並用乙醇(3至4次)及己烷(3至4次)洗滌。廢棄濾液。隨後用二氯甲烷洗滌Celite®/矽石塞以溶離產物。用己烷中之40% DCM(v/v)對粗產物進行矽膠層析分離(利用己烷中之20%三乙胺預處理),以產生0.8 g(40%)化合物6,其藉由LC-MS確認。
合成氯橋二聚物:將2-(6-異丙基二苯并[b,d]呋喃-4-基)-4-甲基吡啶(2.1 g,6.97 mmol)及氯化銥(III)(1.229 g,3.48 mmol)放入200 mL燒瓶中,在氮氣氛下,向該燒瓶添加2-乙氧基乙醇(45 mL)及水(15 mL)。使所得反應混合物於130℃下回流18小時。在冷卻回室溫後,過濾此反應混合物並用3×甲醇及3×己烷洗滌。將所獲得之產物真空乾燥以產生2.9 g(70.1%)所需產物以用於下一步反應。
合成三氟甲磺酸銥鹽:使銥二聚物(2.9 g,1.75 mmol)溶於300 mL的二氯甲烷中。在一單獨燒杯中,使三氟甲磺酸銀(I)(0.944 g,3.36 mmol)溶於MeOH(150 mL)中,並在室溫下,在黑暗中連續攪拌7小時的情況下,緩慢地添加到二氯甲烷溶液中。經由頂部放置有密堆Celite®床的矽膠過濾反應混合物,並真空移除溶劑以產生呈暗黃色固體的3.1 g(80.1%)產物。該產物無需進一步純化即可使用。
合成化合物7:使三氟甲基磺酸銥錯合物(3.0 g,2.99 mmol)與2-苯基吡啶(1.85 g,11.95 mmol)在EtOH(25 mL)及MeOH(25 mL)中的混合物在氮氣氛下回流20小時。使反應混合物冷卻回室溫,用乙醇稀釋,並添加Celite®。將混合物攪拌10分鐘並在一小塊矽膠塞上過濾且用乙醇(3至4次)及己烷(3至4次)洗滌。廢棄濾液。隨後用二氯甲烷洗滌Celite®/矽石塞以溶離產物。用己烷中之30% DCM(v/v)對粗產物進行矽膠層析分離(利用己烷中的20%三乙胺預處理),以產生1 g(35.3%)化合物7,其藉由LC-MS確認。
應理解,本文描述之各種實施例僅為舉例而已,且不意圖限制本發明之範疇。舉例而言,本文描述之許多材料及結構可在不偏離本發明之精神的情況下經其他材料及結構取代。因此,如對熟習此項技術者而言顯而易見,所主張之發明可包括本文描述之特定實例及優選實施例之變化。應理解,不意圖限制關於本發明因何生效的各種理論。
100‧‧‧有機發光裝置
110‧‧‧基板
115‧‧‧陽極
120‧‧‧電洞注入層
125‧‧‧電洞傳輸層
130‧‧‧電子阻擋層
135‧‧‧發射層
140‧‧‧電洞阻擋層
145‧‧‧電子傳輸層
150‧‧‧電子注入層
155‧‧‧保護層
160‧‧‧陰極
162‧‧‧第一導電層
164‧‧‧第二導電層
200‧‧‧經倒置之OLED
210‧‧‧基板
215‧‧‧陰極
220‧‧‧發射層
225‧‧‧電洞傳輸層
230‧‧‧陽極
第1圖展示一種有機發光裝置。
第2圖展示一種不具有獨立電子傳輸層之經倒置的有機
發光裝置。
第3圖展示式I化合物。
Claims (25)
- 一種具有下式之化合物,
- 如請求項1之化合物,其中R1為烷基。
- 如請求項1之化合物,其中RC及R1皆為烷基。
- 如請求項1之化合物,其中R1及R3皆為烷基。
- 如請求項1之化合物,其中RC及R3皆為烷基。
- 如請求項1之化合物,其中X為O。
- 如請求項3之化合物,其中RA及RB皆為氫。
- 如請求項1之化合物,其中m為2。
- 如請求項1之化合物,其中RC表示單烷基取代且RC係與N成對位。
- 如請求項1之化合物,其中R1、R2、R3以及R4獨立地選自由以下各項組成之群:甲基、CH(CH3)2以及苯基。
- 如請求項1之化合物,其中R1、R2、R3以及R4獨立地選自由以下各項組成之群:烷基、氫以及氘。
- 如請求項1之化合物,其中該化合物於10-7至10-8托壓力下之昇華溫度為180℃至240℃。
- 如請求項1之化合物,其具有下式:
- 如請求項1之化合物,其中該化合物選自由以下各項組成之群:
- 如請求項1之化合物,其中該化合物選自由以下各項組成之群:
- 一種包括一第一有機發光裝置的第一裝置,該第一有機發光裝置進一步包括:一陽極;一陰極;以及一有機層,其佈置於該陽極與該陰極之間,該有機層包含具有下式之化合物:
- 如請求項16之第一裝置,其中該第一裝置為一消費品。
- 如請求項16之第一裝置,其中該第一裝置為一有機發光裝置。
- 如請求項16之第一裝置,其中該第一裝置包括一照明板。
- 如請求項16之第一裝置,其中該有機層為一發射層並且該化合物為一非發射摻雜劑。
- 如請求項16之第一裝置,其中該有機層進一步包括一主體。
- 如請求項21之第一裝置,其中該主體包含含有苯并稠合 噻吩或苯并稠合呋喃之三亞苯;其中該主體中之任何取代基獨立地選自由以下各項組成之群的未經稠合之取代基:CnH2n+1、OCnH2n+1、OAr1、N(CnH2n+1)2、N(Ar1)(Ar2)、CH=CH-CnH2n+1、C≡CCnH2n+1、Ar1、Ar1-Ar2及CnH2n-Ar1;其中n為1至10;且其中Ar1及Ar2獨立地選自由以下各項組成之群:苯、聯苯、萘、三亞苯、咔唑以及其雜芳族類似物。
- 如請求項22之第一裝置,其中該主體具有下式:
- 如請求項21之第一裝置,其中該主體選自由以下各項組成之群:
- 如請求項21之第一裝置,其中該主體為金屬錯合物。
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KR101961842B1 (ko) | 2019-03-26 |
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CN108164565A (zh) | 2018-06-15 |
EP3971197A1 (en) | 2022-03-23 |
KR102531325B1 (ko) | 2023-05-10 |
US20130119354A1 (en) | 2013-05-16 |
JP5982264B2 (ja) | 2016-08-31 |
CN108424423A (zh) | 2018-08-21 |
EP3578564A1 (en) | 2019-12-11 |
TW201326183A (zh) | 2013-07-01 |
KR20210150329A (ko) | 2021-12-10 |
EP3578564B1 (en) | 2021-11-24 |
US9193745B2 (en) | 2015-11-24 |
EP4329431A2 (en) | 2024-02-28 |
EP3281944A1 (en) | 2018-02-14 |
TWI567083B (zh) | 2017-01-21 |
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